Phenolic metal salts and their phenolic acids as polymer stabilizers

Description The current invention relates to a composition comprising a polymer and a specific phenolic metal salt or its phenolic acid, which act as a stabilizer for the polymer. A further embodiment is a process for manufacturing a stabilized polymer by adding the specific phenolic metal salt or its phenolic acid to the polymer followed by heating. Furthermore, an additive mixture comprising the specific phenolic metal salt or its phenolic acid, specific phenolic metal salts and the use of the specific phenolic metal salts or their phenolic acids for stabilizing the polymer against oxidative, thermal or light-induced degradation are additional embodiments.

Polymers are susceptible to degradation, which can be induced by heat, light and / or oxidation. For reducing such degradation, numerous solutions for stabilizers, which are incorporated to the organic polymer in a relative small amount, are proposed. However, there is still a need for further technical solutions towards stabilisation of polymers against the detrimental impact of heat, light and / or oxidation.

EP 0780730 A2 discloses positive-type light sensitive lithographic printing plates, which com- prises a grained and anodized aluminium plate with a layer formed of a light-sensitive composition. The composition contains inter alia an o-naphtoquinonediazide compound, an alkaline water-soluble and water-insoluble resin, a compound which generates an acid by light, a blue dye the tone of which is changed with an acid, and a yellow dye having a specific structure and the absorbance of which at 417 nm is at least 70% of the absorbance at 436 nm. As a specific ex- ample of a yellow dye according to its formula III, curcurmin as depicted below

is contained in the coating layer at two examples of coated aluminium plates.

WO 2010/132815 A discloses curcurmin derivatives, for example (1 E,6E)-1 ,7-bis(4-hydroxy-3- methoxyphenyl)4-methoxycarbonylhepta-1 ,6-diene-3,5-dione as depicted below

as inhibitors of matrix metalloproteinases and pro-inflammatory cytokine production.

US 2003/0228268 A discloses 1 ,7-bisphenyl heptane-3,5-dione derivatives as depicted below

some derivatives thereof being tetrahydrocurcumins. The use in cosmetic or dermatological compositions intended particularly for tanning and/or browning the skin is described. One specific composition is disclosed, which contains 2 g hydroxypropylmethylcellulose, 5 g glycerol, 10 g propylene glycol, 10 g absolute ethanol, 4 g dihydroxyacetone, 1 g of a mixture of tetrahydro- curcumoids CG from Sabinsa corporation and 100 g demineralized water.

US 7521580 B discloses the synthesis of (1 E,6E)-1 ,7-bis(3,5-ditert-butyl-4-hydroxyphenyl)- hepta-1 ,6-diene-3,5-dione as depicted below

and therapeutic applications for cystic fibrosis thereof in correcting altered CFTR trafficking and the associated impaired chloride ion transport.

CN 102293762 A discloses the application of inter alia the compound (1 E,6E)-1 ,7-bis(3,5-ditert- butyl-4-hydroxyphenyl)hept

for the preparation of medicines for resisting diabetes and complications thereof. Proposed are further medicaments, which comprises between 1 % by weight up to 99% by weight of a pharmaceutically acceptable form of said compound and a carrier or excipient selected inter alia from polyvinylpyrrolidone, poloxamer 188 (Pluronic F68 RTM BASF), urea, organic acids, sugars, alcohols, starch and derivatives thereof, cellulose and derivatives thereof, acrylics, ethylene oxides and other pharmaceutically acceptable polymer material. The pharmaceutical dosage forms might be prepared using methods like a pharmaceutically melting method, solvent method, solvent-melting method, grinding method, spray drying, vacuum drying or freeze-drying method. The curcumin-inspired derivative is applied in mice experiments to demonstrate physiological effects.

CAS Registry No. 1 161728-40-0 discloses the compound 1 ,7-bis(3,5-ditert-butyl-4-hydroxy- phenyl)heptane-3,5-dione as depicted below

CAS Registry No. 1 1841 10-04-0 discloses the compound 1 ,7-bis(4-hydroxy-3,5-dimethyl- phenyl)heptane-3,5-dione a

It has now been found that a group of specific phenolic metal salts or their phenolic acids suitable for stabilization of polymers against degradation by heat, light and / or oxidation.

The present invention relates to a composition, which comprises the components

a) a polymer, and

b) (i) a phenolic metal salt of formula I

wherein

n is 1 , 2 or 3,

M ⁿ⁺ is a metal ion and Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ , Cs ⁺ , Be ⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , La ³⁺ , Ce ³⁺ , Nd ³⁺ , Eu ³⁺ , Gd ³⁺ , Yb ³⁺ , Sc ²⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ti ³⁺ , Zr ⁺ , Zr ²⁺ , Zr ³⁺ , ΗΡ ⁺ , Hf ³⁺ , V ²⁺ , V ³⁺ , Nb ²⁺ , Nb ³⁺ , Ta ²⁺ , Ta ³⁺ , Cr ²⁺ , Cr ³⁺ , Mo ²⁺ , Mo ³⁺ , W ²⁺ , W ³⁺ , Mn ²⁺ , Mn ³⁺ , Re ³⁺ , Fe ²⁺ , Fe ³⁺ , Ru ³⁺ , 0 ²⁺ , Os ³⁺ , Co ²⁺ , Rh ³⁺ , lr ³⁺ , Ni ²⁺ , Pd ²⁺ , Pt ²⁺ , Cu ²⁺ , Cu ²⁺ , Ag ⁺ , Au ⁺ , Au ³⁺ , Zn ²⁺ , Cd ²⁺ , Hg ⁺ , Hg ²⁺ , Al ³⁺ , Ga ²⁺ , Ga ³⁺ , ln ²⁺ , ln ³⁺ , Tl ⁺ , Tl ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ ,

- is an anion of formula II

wherein

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH ₂ -CH ₂ - and A ² is -CH ₂ -,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl, or

(ii) a bisphenolic compound of formula III

wherein

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH ₂ -CH ₂ - and A ² is -CH ₂ -,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). The phenolic metal salt of formula I is neutral, i.e. the cationic charge of the metal ion M ⁿ⁺ is equalized by a respective amount of anionic ligand(s) l_- of formula II.

M ⁿ⁺ is a metal ion of the metal M with an oxidation number I for n = 1 , an oxidation number II for n = 2 or an oxidation number III for n = 3.

Preferred is a metal ion M ⁿ⁺ , which is Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ , Cs ⁺ , Be ²⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , La ³⁺ , Ce ³⁺ , Nd ³⁺ , Eu ³⁺ , Gd ³⁺ , Yb ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , ΗΡ ⁺ , Hf ³⁺ , V ²⁺ , V ³⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , W ²⁺ , W ³⁺ , Mn ²⁺ , Mn ³⁺ , Re ³⁺ , Fe ²⁺ , Fe ³⁺ , Ru ³⁺ , Os ³⁺ , Co ²⁺ , Rh ³⁺ , lr ³⁺ , Ni ²⁺ , Pd ²⁺ , Pt ²⁺ , Cu ⁺ , Cu ²⁺ , Ag ⁺ , Au ⁺ , Au ³⁺ , Zn ²⁺ , Cd ²⁺ , Hg ⁺ , Hg ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Tl ⁺ , Tl ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ . In partic- ular preferred is a metal ion M ⁿ⁺ , which is Be ²⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , La ³⁺ , Ce ³⁺ , Nd ³⁺ , Eu ³⁺ , Gd ³⁺ , Yb ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , ΗΡ ⁺ , Hf ³⁺ , V ²⁺ , V ³⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , W ²⁺ , W ³⁺ , Mn ²⁺ , Mn ³⁺ , Re ³⁺ , Fe ²⁺ , Fe ³⁺ , Ru ³⁺ , Os ³⁺ , Co ²⁺ , Rh ³⁺ , lr ³⁺ , Ni ²⁺ , Pd ²⁺ , Pt ²⁺ , Cu ²⁺ , Au ³⁺ , Zn ²⁺ , Cd ²⁺ , Hg ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Tl ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ and n is 2 or 3. Very particular preferred is a metal ion M ⁿ⁺ , which is Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ , Cs ⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Ag ⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ . Especially preferred is a metal ion M ⁿ⁺ , which is Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ and n is 2 or 3. Very especially preferred is a metal ion M ⁿ⁺ , which is Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ and n is 2 or 3.

The phenolic metal salt of formula I as a pure material can be in solid form at a temperature of 25°C and 101 .325 KPa. The solid form can be a crystalline form, an amorphous form or a semi- crystalline form. At the semi-crystalline form, the solid contains crystalline parts and amorphous parts.

If the phenolic metal salt of formula I is in a crystalline form, which is crystallized out of an aqueous solvent system, water molecules might be contained in the crystals of the phenolic metal salt of formula I as hydrates. These water molecules are considered herein as water of crystallization. This water of crystallization serves to stabilize the crystalline form by filling empty spaces or is coordinated to the metal ion M ⁿ⁺ or to the anion L. If the phenolic metal salt of formula I is isolated from an aqueous solvent system in a semi-crystalline form or in an amorphous form, water of crystallization and additional water molecules might be contained in the isolated material. The content of water of crystallization and the content of additional water molecules depend on the isolation process from the aqueous solvent system, e.g. duration of drying, and afterwards on the storage conditions, e.g. temperature or humidity of the environment. If the phenolic metal salt of formula I is in a crystalline form, which is crystallized out of a nonaqueous solvent system, solvent molecules might be contained in the crystals of the phenolic metal salt of formula I as solvates. These solvent molecules are considered herein as solvent of crystallization. This solvent of crystallization serves to stabilize the crystalline form by filling empty spaces or is coordinated to the metal ion M ⁿ⁺ or to the anion l_-. If the phenolic metal salt of formula I is isolated from a non-aqueous solvent system in a semi-crystalline form or in an amorphous form, solvent of crystallization and additional solvent molecules might be contained in the isolated material. The content of solvent of crystallization and the content of additional solvent molecules depend on the isolation process from the non-aqueous solvent system, e.g. duration of drying, and afterwards on the storage conditions, e.g. temperature or humidity of the environment.

The phenolic metal salt of formula I is preferably in the form of a phenolic metal complex of formula l-C

[(H ₂ 0)u M" ⁺ (L-)n] (l-C)

wherein

n is 1 , 2 or 3,

M ⁿ⁺ is a metal ion and Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ , Cs ⁺ , Be ⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , La ³⁺ , Ce ³⁺ , Nd ³⁺ , Eu ³⁺ , Gd ³⁺ , Yb ³⁺ , Sc ²⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ti ³⁺ , Zr ⁺ , Zr ²⁺ , Zr ³⁺ , Hf^, Hf ³⁺ , V ²⁺ , V ³⁺ , Nb ²⁺ , Nb ³⁺ , Ta ²⁺ , Ta ³⁺ , Cr ²⁺ , Cr ³⁺ , Mo ²⁺ , Mo ³⁺ , W ²⁺ , W ³⁺ , Mn ²⁺ , Mn ³⁺ , Re ³⁺ , Fe ²⁺ , Fe ³⁺ , Ru ³⁺ , 0 ²⁺ , Os ³⁺ , Co ²⁺ , Rh ³⁺ , lr ³⁺ , Ni ²⁺ , Pd ²⁺ , Pt ²⁺ , Cu ²⁺ , Cu ²⁺ , Ag ⁺ , Au ⁺ , Au ³⁺ , Zn ²⁺ , Cd ²⁺ , Hg ⁺ , Hg ²⁺ , Al ³⁺ , Ga ²⁺ , Ga ³⁺ , ln ²⁺ , ln ³⁺ , Tl ⁺ , Tl ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ ,

u is 0, 1 , 2, 3 or 4,

when n is 1 ,

u is 0, 1 , 2, 3 or 4,

when n is 2 or 3,

u is 0, 1 or 2,

l_- is an anion of formula II

wherein

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH ₂ -CH ₂ - and A ² is -CH ₂ -,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl.

If the phenolic metal salt of formula I is in the form of a phenolic metal complex of formula l-C, l_- is an anion of formula II and at the same time also a bidentate ligand of the metal ion M ⁿ⁺ .

The amount of water molecules, which coordinate to the metal ion M ⁿ⁺ as a further ligand in addition to the anion Ι_-, is described by the parameter u. These water molecules are part of the water of crystallization. A phenolic metal complex of formula l-C can be free of water molecules, which coordinates to the metal ion M ⁿ⁺ as a further ligand in addition to a ligand Ι_-, i.e. u is 0. In this case, the coordination positions of a specific metal ion M ⁿ⁺ are occupied solely by one or more ligands l_- or by one or more ligands l_- and another coordinating molecule different to H ₂ 0, for example a polar but uncharged solvent molecule different to H ₂ 0, which is present during the complex synthesis. In contrast to u = 0, the central metal ion M ⁿ⁺ might be further coordinated by water molecules, i.e. u is 1 , 2, 3 or 4. In case of n = 1 , i.e. one anion l_- of formula II, u is 0, 1 , 2, 3 or 4, in particular 0, 1 , 2 or 4. In case of n = 2 or 3, i.e. two or three anions l_- of formula II, u is 0, 1 or 2. Due to the heating for incorporation into the polymer, a phenolic metal complex of formula l-C with a low content of coordinated water is desirable. Preferably, u is 0, 1 or 2. Very preferably, u is 0. If the synthesis of the phenolic metal complex of formula l-C is conducted under water-free conditions, water molecules, which coordinate to the metal ion M ⁿ⁺ , can be avoided. If the synthesis conducted under water-free conditions comprises uncharged polar solvent molecules other than water molecules, said uncharged polar solvent molecules might occupy the positions of the coordinated water molecules in the phenolic metal complex of formula l-C. Preferably, a phenolic metal complex of formula l-C contains only coordinated water molecules or an anion of formula II as ligands.

C1-C4 alkyl is for example methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -methylpropyl or tert- butyl. Preferred is methyl or tert-butyl, in particular tert-butyl.

The anion l_- of formula II, wherein R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl, and R ³ is H or C1-C4 alkyl, is represented

- for A ¹ and A ² being both -CH ₂ -CH ₂ - by formula IV-1

- for A ¹ and A ² being both -CH ₂ - by formula IV-3

- for A ¹ is -CH=CH- and A ² is -CH ₂ - by formulae IV-4E or IV-4Z - for A ¹ is -CH

E/Z-lsomers (trans/cis-isomers) exist for an anion L-, if at least one of A ¹ and A ² is -CH=CH-. Preferred are E-isomers. For example, for A ¹ and A ² being both -CH=CH-, l_- is of formulae IV- 2EE or IV-2EZ and for A ¹ being -CH ₂ - and A ² being -CH=CH-, L- is of formula IV-4E.

Preferred is an anion l_- of formula II, wherein A ¹ and A ² are both -CH2-CH2- or A ¹ and A ² are both -CH=CH-. In particular preferred is an anion L, wherein A ¹ and A ² are both -CH2-CH2- or A ¹ and A ² are both -CH=CH- with l_- being of formula IV-2EE.

Preferred is an anion l_- of formula II, wherein R ¹ , R ² , R ⁴ and R ⁵ are independently from each other Ci alkyl or C ₄ alkyl and R ³ is H or C1-C4 alkyl. Particularly preferred is an anion l_- of formu- la II, wherein R ¹ , R ² , R ⁴ and R ⁵ are all Ci alkyl or C ₄ alkyl and R ³ is H or Ci-C ₄ alkyl, especially H. Very preferred is an anion l_- of formula II, wherein R ¹ , R ² , R ⁴ and R ⁵ are all C ₄ alkyl and R ³ is H. Very especially preferred is an anion l_- of formula IV-1 , wherein R ¹ , R ² , R ⁴ and R ⁵ are all tert- butyl and R ³ is H, or an anion l_- of formula IV-2EE, wherein R ¹ , R ² , R ⁴ and R ⁵ are all tert-butyl and R ³ is H.

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -, in particular -CH ₂ -CH ₂ - or

-CH=CH-,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -, in particular -CH ₂ -CH ₂ - or -CH=CH-,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -, in particular -CH ₂ -CH ₂ - or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -, in particular -CH ₂ -CH ₂ - or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and b) (i) a phenolic metal salt of formula I,

wherein at formula II

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein at formula II

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ ,

Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

u is 0, 1 , or 2, wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ ,

Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -, in particular -CH ₂ -CH ₂ - or -CH=CH-,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

u is 0, 1 , or 2,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -, in particular -CH ₂ -CH ₂ - or -CH=CH-,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ ,

Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

wherein at formula II

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , In ³ Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

u is 0, 1 , or 2,

wherein at formula II

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , In ³ Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

wherein at formula II

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl,

R ³ is H, wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ ,

Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

u is 0, 1 , or 2,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -, in particular -CH ₂ -CH ₂ - or

-CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or AI ³⁺ ,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ - or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or AI ³⁺ , u is 0, 1 , or 2,

wherein at formula II

A ¹ and A ² are both -CH ₂ -CH ₂ - or -CH=CH-,

R ¹ , R2, R ⁴ and R ⁵ are tert-butyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal salt of formula I,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or AI ³⁺ ,

wherein the anion l_- is of formula IV-1 , wherein R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl, R ³ is H, or the anion l_- is of formula IV-2EE, wherein R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl, R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (i) a phenolic metal complex of formula l-C,

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or AI ³⁺ ,

u is 0, 1 , or 2,

wherein the anion l_- is of formula IV-1 , wherein R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl, R ³ is H, or the anion l_- is of formula IV-2EE, wherein R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl, R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

The bisphenolic compound of formula III, which represents the protonated anion l_- of formula II, might have spontaneous tautomeric forms. In cases, wherein a compound exists in tautomeric forms, such as keto-enol tautomers, each tautomeric form is contemplated as being included within this invention whether existing in equilibrium or predominantly in one form.

The bisphenolic compound of formula III, wherein R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl, and R ³ is H or C1-C4 alkyl, is represented for A ¹ and A ² being both -CH ₂ -CH ₂ - by formula V-1

- for A ¹ and A r V-2ZZ

- for A ¹ and A ² being both -CH ₂ - by formula V-3

for A ¹ is -CH=CH- and A ² is -CH ₂ - by formulae V-4E or V-4Z

- for A ¹ is -CH2-CH2- and A ² is -CH ₂ - by formula V-5

E/Z-lsomers (trans/cis-isomers) exist for a bisphenolic compound of formula III, if at least one of A ¹ and A ² is -CH=CH-. Preferred are E-isomers. For example, for A ¹ and A ² being both - CH=CH-, L- is of formulae V-2EE or V-2EZ and for A ¹ being -CH ₂ - and A ² being -CH=CH-, l_- is of formula V-4E. Preferred is a bisphenolic compound of formula III, wherein A ¹ and A ² are both -CH2-CH2- or A ¹ and A ² are both -CH=CH-. In particular preferred is a bisphenolic compound, wherein A ¹ and A ² are both -CH2-CH2- or A ¹ and A ² are both -CH=CH- with the bisphenolic compound being of formula V-2EE. Preferred is a bisphenolic compound of formula III, wherein R ¹ , R ² , R ⁴ and R ⁵ are independently from each other Ci alkyl or C ₄ alkyl and R ³ is H or Ci-C ₄ alkyl. In particular preferred is a bisphenolic compound of formula III, wherein R ¹ , R ² , R ⁴ and R ⁵ are all Ci alkyl or C ₄ alkyl and R ³ is H or Ci-C ₄ alkyl, especially H. Very preferred is a bisphenolic compound of formula III, wherein R ¹ , R ² , R ⁴ and R ⁵ are all C ₄ alkyl and R ³ is H.

Preferred is a bisphenolic compound of formula III, which is compound (101 ) or compound (102). The structures of these compounds are depicted in the respective synthetic example S-1 or S-2. Preferred is a composition, which comprises

a) a polymer, and

b) (ii) a bisphenolic compound of formula III,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and b) (ii) a bisphenolic compound of formula III,

wherein

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (ii) a bisphenolic compound of formula III,

wherein

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (ii) a bisphenolic compound of formula III,

wherein

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ -, in particular -CH2-CH2- or -CH=CH-,

R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl,

R ³ is H,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, and

b) (ii) a bisphenolic compound of formula III, which is of formula V-1 , wherein R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl, R ³ is H, or

which is of formula V-2EE, wherein R ¹ , R ² , R ⁴ and R ⁵ are tert-butyl, R ³ is H, wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

For calculation of the weight of component b) in the composition, a content of water or solvent different to water at a metal salt of formula I is excluded. Accordingly, the weight of a deter- mined content of water or solvent is subtracted from the actual weight of component b). In case of a phenolic metal complex of formula l-C, the coordinated water and any coordinated solvent molecules are accordingly also excluded. For calculation of the weight of component b) in the composition, the weight of all phenolic metal salts of formula I and the weight of all bisphenolic compounds of formula III are added to obtain the weight of component b). For calculation of the weight of component a), the weight of all polymers in the composition are added. Preferably, the amount of component b) is from 0.0005 to 0.8% by weight based on the weight of component a), particularly from 0.001 to 0.7% by weight, very particular from 0.01 to 0.5% by weight, especially from 0.05 to 0.3 % by weight and very especially from 0.07 to 0.28% by weight. The content of water in the composition is the sum of the weight of all water molecules in the composition, e.g. including the water of crystallization of a phenolic metal salt of formula I and the additional water of a phenolic metal salt of formula I.

Preferably, the content of water in the composition is below 10% by weight based on the total weight of the composition. Particularly, the content of water is below 0.9% by weight, very particularly below 0.2% by weight, especially below 0.1 % by weight.

A polymer herein means a polymer, which contains repeating units comprising a carbon- hydrogen group, i.e. a C-H bond. Such a polymer, which is considered herein an organic poly- mer, is susceptible to oxidative, thermal or light-induced degradation. An organic polymer can be natural, semi-synthetic or synthetic. A natural organic polymer is isolated from a natural source without further synthetic modifications. A synthetic organic polymer does not contain a polymer part isolated from a natural source. A semi-synthetic organic polymer contains at least one natural polymer part, wherein the natural polymer part can be synthetically modified and / or reacted with monomers to form the semi-synthetic polymer.

A polymer can be thermoplastic, i.e. it can be shaped into a new form at an elevated temperature, for example at a temperature in the range from 135°C to 360°C, especially from 150°C to 340°C.

A copolymer is a polymer, wherein at least two different monomers are co-polymerized. Preferred are copolymers, wherein the weight content of one monomer is above 50% by weight based on the weight of all monomers. Preferably, a polymer is a substance consisting of molecules characterized by the sequence of one or more types of monomer units and comprising a simple weight majority of molecules containing at least three monomer units which are covalently bound to at least one other monomer unit or other reactant and consists of less than a simple weight majority of molecules of the same molecular weight. Such molecules must be distributed over a range of molecular weights wherein differences in the molecular weight are primarily attributable to differences in the number of monomer units. In the context of this definition a monomer unit means the reacted form of a monomer in a polymer. Examples of a polymer are:

1 . Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut- 1 -ene, poly-4-methylpent-1 -ene, polyvinylcyclohexane, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or nor-bornene, polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE).

Polyolefins, i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:

a) radical polymerisation (normally under high pressure and at elevated temperature). b) catalytic polymerisation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, Vlb (for example chromium) or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alco- holates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either π- or σ- coordinated. These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(lll) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups la, lla and/or Ilia of the Periodic Table. The activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).

2. Mixtures of the polymers mentioned under 1 ), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of different types of polyethylene (for example LDPE/HDPE). 3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, for example ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/but-1 -ene copolymers, propyl- ene/isobutylene copolymers, ethylene/but-1 -ene copolymers, ethylene/hexene copolymers, eth- ylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/octene copolymers, ethylene/vinylcyclohexane copolymers, ethylene/cycloolefin copolymers (e.g. eth- ylene/norbornene like COC), ethylene/1 -olefins copolymers, where the 1 -olefin is generated in- situ; propylene/butadiene copolymers, isobutylene/isoprene copolymers, eth- ylene/vinylcyclohexene copolymers, ethylene/alkyl acrylate copolymers, ethylene/alkyl methac- rylate copolymers, ethylene/vinyl acetate copolymers or ethylene/acrylic acid copolymers and their salts (ionomers) as well as terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or ethylidene-norbornene; and mixtures of such copolymers with one another and with polymers mentioned in 1 ) above, for example polypropylene/ethylene- propylene copolymers, LDPE/ethylene-vinyl acetate copolymers (EVA), LDPE/ethylene-acrylic acid copolymers (EAA), LLDPE/EVA, LLDPE/EAA and alternating or random poly- alkylene/carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides.

A special copolymer of two monoolefins is a pipe grade polypropylene random copolymer, which is obtainable from the polymerization of more than 90% by weight of propylene and of less than 10% by weight, typically between 2 and 6% by weight, of ethylene. 4. Hydrocarbon resins (for example C5-C9) including hydrogenated modifications there-of (e.g. tackifiers) and mixtures of polyalkylenes and starch.

Homopolymers and copolymers from 1.) - 4.) may have any stereostructure including syndiotac- tic, isotactic, hemi-isotactic or atactic; where isotactic polymers are preferred. Stereoblock poly- mers are also included.

5. Polystyrene, poly(p-methylstyrene), poly(a-methylstyrene).

6. Aromatic homopolymers and copolymers derived from vinyl aromatic monomers including styrene, a-methylstyrene, all isomers of vinyl toluene, especially p-vinyl-toluene, all isomers of ethyl styrene, propyl styrene, vinyl biphenyl, vinyl naphthalene, and vinyl anthracene, and mixtures thereof. Homopolymers and copolymers may have any stereostructure including syndio- tactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.

6a. Copolymers including aforementioned vinyl aromatic monomers and comonomers selected from ethylene, propylene, dienes, nitriles, acids, maleic anhydrides, maleimides, vinyl acetate and vinyl chloride or acrylic derivatives and mixtures thereof, for example styrene/butadiene, styrene/acrylonitrile, styrene/ethylene (interpolymers), styrene/alkyl methacrylate, sty- rene/butadiene/alkyl acrylate, styrene/butadiene/alkyl methacrylate, styrene/maleic anhydride, styrene/acrylonitrile/methyl acrylate; mixtures of high impact strength of styrene copolymers and another polymer, for example a polyacrylate, a diene polymer or an ethylene/propylene/diene terpolymer; and block copolymers of styrene such as styrene/butadiene/styrene, sty- rene/isoprene/styrene, styrene/ethylene/butylene/styrene or styrene/ethylene/propylene/styrene. 6b. Hydrogenated aromatic polymers derived from hydrogenation of polymers mentioned under

6. ), especially including polycyclohexylethylene (PCHE) prepared by hydrogenating atactic polystyrene, often referred to as polyvinylcyclohexane (PVCH). 6c. Hydrogenated aromatic polymers derived from hydrogenation of polymers mentioned under 6a.).

Homopolymers and copolymers may have any stereostructure including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.

7. Graft copolymers of vinyl aromatic monomers such as styrene or a-methylstyrene, for example styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-acrylonitrile copolymers; styrene and acrylonitrile (or methacrylonitrile) on polybutadiene; styrene, acryloni- trile and methyl methacrylate on polybutadiene; styrene and maleic anhydride on polybutadiene; styrene, acrylonitrile and maleic anhydride or maleimide on polybutadiene; styrene and malei- mide on polybutadiene; styrene and alkyl acrylates or methacrylates on polybutadiene; styrene and acrylonitrile on ethylene/propylene/diene terpolymers; styrene and acrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile on acrylate/butadiene copolymers, as well as mixtures thereof with the copolymers listed under 6), for example the copolymer mixtures known as ABS, MBS, ASA or AES polymers.

8. Halogen-containing polymers such as fluoropolymers such as copolymers of difluoroethylene and hexafluoropropylene, polychloroprene, chlorinated rubbers, chlorinated and brominated copolymer of isobutylene-isoprene (halobutyl rubber), chlorinated or sulfochlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, epichlorohydrin homo- and copolymers, especially polymers of halogen-containing vinyl compounds, for example polyvinyl chloride, pol- yvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof such as vinyl chloride/vinylidene chloride, vinyl chloride/vinyl acetate or vinylidene chloride/vinyl acetate copolymers. Halogen-containing polymers do not comprise perhalogenated polymers such as perfluorinated polyethylene (Teflon), since they do not contain repeating units comprising a carbon-hydrogen group, i.e. a C-H bond.

9. Polymers derived from α,β-unsaturated acids and derivatives thereof such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles, impact-modified with butyl acrylate.

10. Copolymers of the monomers mentioned under 9) with each other or with other unsaturated monomers, for example acrylonitrile/ butadiene copolymers, acrylonitrile/alkyl acrylate copoly- mers, acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halide copolymers or acrylonitrile/ alkyl methacrylate/butadiene terpolymers. 1 1. Polymers derived from unsaturated alcohols and amines or the acyl derivatives or acetals thereof, for example polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine; as well as their copolymers with olefins mentioned in 1 ) above.

12. Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with bisglycidyl ethers.

13. Polyacetals such as polyoxymethylene and those polyoxymethylenes which contain eth- ylene oxide as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.

14. Polyphenylene oxides and sulfides, and mixtures of polyphenylene oxides with styrene polymers or polyamides.

15. Polyurethanes, for example polyurethanes synthesized from a polyol and an aliphatic or aromatic polyisocyanate such as polyurethanes derived from hydroxyl-terminated polyethers, polyesters or polybutadienes on the one hand and aliphatic or aromatic polyisocyanates on the other, as well as precursors thereof.

Hydroxyl-terminated polyethers are known and are prepared, for example, by polymerizing epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin with themselves, for example in the presence of BF3, or by addition reaction of these epoxides, alone or as a mixture or in succession, with starting components con- taining reactive hydrogen atoms, such as water, alcohols, ammonia or amines, for example ethylene glycol, propylene 1 ,3- and 1 ,2-glycol, trimethylolpropane, 4,4'-dihydroxydiphenylpropane, aniline, ethanolamine or ethylenediamine. Sucrose polyethers are also suitable in accordance with the invention. In many cases preference is given to those polyethers which predominantly (up to 90% by weight, based on all the OH groups present in the polyether) contain primary OH groups. Furthermore, polyethers modified by vinyl polymers, as are formed, for example, by polymerizing styrene and acrylonitrile in the presence of polyethers, are suitable, as are polybutadienes containing OH groups.

In particular, a polyol compound has a molecular weight of 400-10000, especially 800 to 10000, and is a compound containing several hydroxyl groups, especially containing from 2 to 8 hy- droxyl groups, especially from 2 to 4.

Suitable polyisocyanates are aliphatic or aromatic, for example ethylene diisocyanate, 1 ,4- tetramethylene diisocyanate, 1 ,6-hexamethylene diisocyanate, 1 ,12-dodecane diisocyanate, cyclobutane 1 ,3-diisocyanate, cyclohexane 1 ,3- and -1 ,4-diisocyanate and also any desired mixtures of these isomers, 1 -isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4- and 2,6-hexahydrotolylene diisocyanate and also any desired mixtures of these isomers, hexa- hydro-1 ,3- and/or -1 ,4-phenylene diisocyanate, perhydro-2,4'- and/or -4,4'- diphenylmethanediisocyanate, 1 ,3- and 1 ,4-phenylene diisocyanate, 2,4- and 2,6-tolylene diisocyanate, and also any desired mixtures of these isomers, diphenylmethane 2,4'- and/or

-4,4'-diisocyanate, naphthylene 1 ,5-diisocyanate, triphenylmethane 4,4',4"-triisocyanate, poly- phenyl-polymethylene polyisocyanates as are obtained by aniline-formaldehyde condensation followed by phosgenization, m- and p-isocyanatophenylsulfonyl isocyanates, perchlorinated aryl polyisocyanates, polyisocyanates containing carbodiimide groups, polyisocyanates containing allophanate groups, polyisocyanates containing isocyanurate groups, polyisocyanates containing urethane groups, polyisocyanates containing acylated urea groups, polyisocyanates con- taining biuret groups, polyisocyanates containing ester groups, reaction products of the above- mentioned isocyanates with acetals, and polyisocyanates containing polymeric fatty acid radicals.

It is also possible to employ the isocyanate group-containing distillation residues, as they are or dissolved in one or more of the abovementioned polyisocyanates, which are obtained in the course of the industrial preparation of isocyanates. It is additionally possible to use any desired mixtures of the abovementioned polyisocyanates.

Preferred are 2,4- or 2,6-tolylene diisocyanate and any desired mixtures of these isomers ("TDI"), polyphenyl-polymethylene-polyisocyanates as prepared by aniline-formaldehyde condensation followed by phosgenization ("crude MDI") or polyisocyanates containing carbodiimide, urethane, allophanate, isocyanurate, urea or biuret groups ("modified polyisocyanates").

The polyurethanes can be homogeneous polyurethanes or cellular.

16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or the corresponding lactams, for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 1 1 , polyamide 12, aromatic polyamides starting from m-xylene diamine and adipic acid; polyamides prepared from hexamethylenedia- mine and isophthalic or/and terephthalic acid and with or without an elastomer as modifier, for example poly-2,4,4,-trimethylhexamethylene terephthalamide or poly-m-phenylene

isophthalamide; and also block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, e.g. with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; as well as poly- amides or copolyamides modified with EPDM or ABS; and polyamides condensed during processing (RIM polyamide systems).

17. Polyureas, polyimides, polyamide-imides, polyetherimides, polyesterimides, polyhydantoins and polybenzimidazoles.

18. Polyesters derived from dicarboxylic acids and diols and/or from hydroxycarboxylic acids or the corresponding lactones or lactides, for example polyethylene terephthalate, polybutylene terephthalate, poly-1 ,4-dimethylolcyclohexane terephthalate, polyalkylene naphthalate and pol- yhydroxybenzoates as well as copolyether esters derived from hydroxyl-terminated polyethers, and also polyesters modified with polycarbonates or MBS. Copolyesters may comprise, for example - but are not limited to - polybutylenesuccinate/terephtalate, polybutylenead- ipate/terephthalate, polytetramethyleneadipate/terephthalate, polybutylensuccinate/adipate, polybutylensuccinate/carbonate, poly-3-hydroxybutyrate/octanoate copolymer, poly-3- hydroxybutyrate/hexanoate/de-canoate terpolymer. Furthermore, aliphatic polyesters may comprise, for example - but are not limited to - the class of poly(hydroxyalkanoates), in particular, poly(propiolactone), poly(butyrolactone), poly(pivalolactone), poly(valerolactone) and

poly(caprolactone), polyethylenesuccinate, polypropylenesuccinate, polybutylenesuccinate, pol- yhexamethylenesuccinate, polyethyleneadipate, polypropyleneadipate, polybutyleneadipate, polyhexamethyleneadipate, polyethyleneoxalate, polypropyleneoxalate, polybutyleneoxalate, polyhexamethyleneoxalate, polyethylenesebacate, polypropylenesebacate, polybutyleneseba- cate and polylactic acid (PLA) as well as corresponding polyesters modified with polycarbonates or MBS. The term "polylactic acid (PLA)" designates a homo-polymer of preferably poly-L- lactide and any of its blends or alloys with other polymers; a co-polymer of lactic acid or lactide with other monomers, such as hydroxy-carboxylic acids, like for example glycolic acid, 3- hydroxy-butyric acid, 4-hydroxy-butyric acid, 4-hydroxy-valeric acid, 5-hydroxy-valeric acid, 6- hydroxy-caproic acid and cyclic forms thereof; the terms "lactic acid" or "lactide" include L-lactic acid, D-lactic acid, mixtures and dimers thereof, i.e. L-lactide, D-lactide, meso-lactide and any mixtures thereof.

19. Polycarbonates and polyester carbonates. 20. Polyketones.

21. Polysulfones, polyether sulfones and polyether ketones.

22. Crosslinked polymers derived from aldehydes on the one hand and phenols, ureas and melamines on the other hand, such as phenol/formaldehyde resins, urea/formal-dehyde resins and melamine/formaldehyde resins.

23. Drying and non-drying alkyd resins. 24. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicar- boxylic acids with polyhydric alcohols and vinyl compounds as crosslinking agents, and also halogen-containing modifications thereof of low flammability.

25. Crosslinkable acrylic resins derived from substituted acrylates, for example epoxy acrylates, urethane acrylates or polyester acrylates. 26. Alkyd resins, polyester resins and acrylate resins crosslinked with melamine resins, urea resins, isocyanates, isocyanurates, polyisocyanates or epoxy resins.

27. Crosslinked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic or aromatic glycidyl compounds, e.g. products of diglycidyl ethers of bisphenol A and bisphenol F, which are crosslinked with customary hardeners such as anhydrides or amines, with or without accelerators.

28. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof, for example cellulose acetates, cellulose propionates and cellulose butyr- ates, or the cellulose ethers such as methyl cellulose; as well as rosins and their derivatives.

29. Blends of the aforementioned polymers (polyblends), for example PP/EPDM, poly- amide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylate,

POM/MBS, PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS or PBT/PET/PC.

30. Aqueous emulsions of natural or synthetic rubber, e.g. natural latex or latices of carboxylat- ed styrene/butadiene copolymers.

Preferred is a polymer, which is a synthetic or semisynthetic organic polymer and very particular a synthetic or semisynthetic thermoplastic organic polymer. Especially preferred is a synthetic organic polymer, very especially a thermoplastic organic polymer. Preferred is a polymer, which is a polyolefin or a copolymer thereof, a polystyrene or a copolymer thereof, a polyurethane or a copolymer thereof, a polyether, which is obtainable by the polymerization of an epoxide, an ox- etane or tetrahydrofuran, or a copolymer thereof, a polyester or a copolymer thereof, a polycarbonate or a copolymer thereof, a polyvinyl chloride) or a copolymer thereof, a poly(vinylidene chloride) or a copolymer thereof, a polysulfone or a copolymer thereof, a polybutadiene or a copolymer thereof, a polyvinyl acetate) or a copolymer thereof, a polyvinyl alcohol) or a copolymer thereof, a polyvinyl acetal) or a copolymer thereof, or a polyamide or a copolymer thereof. In particular preferred is a polymer, which is a polyolefin or a copolymer thereof, very particular an poly(alpha-olefin) or a copolymer thereof, especially a polyethylene or a copolymer thereof or a polypropylene or a copolymer thereof.

Preferred is a composition, which comprises

a) a polymer, which is a synthetic organic polymer, and

b) (i) a phenolic metal salt of formula I, or

(ii) a bisphenolic compound of formula III,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a) Preferred is a composition, which comprises

a) a polymer, which is a polyolefin or a copolymer thereof, a polystyrene or a copolymer thereof, a polyurethane or a copolymer thereof, a polyether, which is obtainable by the polymerization of an epoxide, an oxetane or tetrahydrofuran, or a copolymer thereof, a polyester or a copolymer thereof, a polycarbonate or a copolymer thereof, a polyvinyl chloride) or a copolymer thereof, a poly(vinylidene chloride) or a copolymer thereof, a polysulfone or a copolymer thereof, a poly- butadiene or a copolymer thereof, a polyvinyl acetate) or a copolymer thereof, a polyvinyl alcohol) or a copolymer thereof, a polyvinyl acetal) or a copolymer thereof, or a polyamide or a copolymer thereof, and

b) (i) a phenolic metal salt of formula I, or

(ii) a bisphenolic compound of formula III,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). Preferred is a composition, which comprises

a) a polymer, which is a polyolefin or a copolymer thereof, a polystyrene or a copolymer thereof, or a polyurethane or a copolymer thereof, in particular wherein the organic material is a polyolefin or a copolymer thereof, a polystyrene or a copolymer thereof, or a polyurethane or a copolymer thereof, and very particular wherein the organic material is a polyolefin or a copolymer thereof, or a polystyrene or a copolymer thereof, and

b) (i) a phenolic metal salt of formula I, or

(ii) a bisphenolic compound of formula III,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer, which is a polyolefin or a copolymer thereof, in particular an poly(alpha-olefin), very particular a polyethylene or a copolymer thereof or a polypropylene or a copolymer thereof, and

b) (i) a phenolic metal salt of formula I, or

(ii) a bisphenolic compound of formula III,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). Optionally, a composition comprising a polymer as component a) and a phenolic metal salt of formula I, or a bisphenolic compound of formula III, contains a further additive as component c), wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). A further additive can be selected from the following list:

1 . Antioxidants 1 .1 . Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-di- methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl- 4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(a-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethyl- phenol, nonylphenols which are linear or branched in the side chains, for example 2,6-di-nonyl- 4-methylphenol, 2,4-dimethyl-6-(1 '-methylundec-1 '-yl)phenol, 2,4-dimethyl-6-(1 '-methylhepta- dec-1 '-yl)phenol, 2,4-dimethyl-6-(1 '-methyltridec-1 '-yl)phenol, 2,4-dimethyl-6-(1 '-methyl-1 '-tetra- decyl-methyl)-phenol and mixtures thereof.

1 .2. Alkylthiomethylphenols, for example 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthio- methyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonyl- phenol. 1 .3. Hydroquinones and alkylated hydroquinones, for example 2,6-di-tert-butyl-4-methoxy- phenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyl- oxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4- hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.

1 .4. Tocopherols, for example a-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and mixtures thereof (vitamin E), vitamin E acetate.

1 .5. Hydroxylated thiodiphenyl ethers, for example 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'- thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methyl- phenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl)disulfide.

1 .6. Alkylidenebisphenols, for example 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'- methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(a-methylcyclohexyl)- phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-methyl- phenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis[6-(a-methylbenzyl)-4-nonyl- phenol], 2,2'-methylenebis[6-(a,a-dimethylbenzyl)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert- butylphenol), 4,4'-methylenebis(6-tert-butyl-2-methylphenol), 1 ,1 -bis(5-tert-butyl-4-hydroxy-2- methylphenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylpheno l, 1 ,1 ,3-tris- (5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1 , 1 -bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3- n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene , bis[2-(3'-tert-butyl-2'-hydroxy-5'- methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate, 1 ,1 -bis-(3,5-dimethyl-2-hydroxyphenyl)- butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis-(5-tert-butyl-4-hydroxy-2- methylphenyl)-4-n-dodecylmercaptobutane, 1 ,1 ,5,5-tetra(5-tert-butyl-4-hydroxy-2-methyl- phenyl)pentane. 1 .7. Ο-, N- and S-benzyl compounds, for example 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert- butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3- hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate.

1 .8. Hydroxybenzylated malonates, for example dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxy- benzyl)malonate, di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malona te, di-dodecyl- mercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malo nate, bis[4-(1 ,1 ,3,3-tetramethyl- butyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malo nate.

1 .9. Aromatic hydroxybenzyl compounds, for example 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxy- benzyl)-2,4,6-trimethylbenzene, 1 ,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethy l- benzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.

1 .10. Triazine compounds, for example 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxy- anilino)-1 ,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)- 1 ,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)- 1 ,3,5-triazine, 2,4,6-tris(3,5-di-tert- butyl-4-hydroxyphenoxy)-1 ,2,3-triazine, 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1 ,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanu rate, 2,4,6-tris(3,5-di-tert-butyl-4- hydroxyphenylethyl)-1 ,3,5-triazine, 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexa- hydro-1 ,3,5-triazine, 1 ,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate. 1 .1 1. Benzylphosphonates, for example dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxy- benzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate , the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid, (3,5-ditert- butyl-4-hydroxy-phenyl)methylphosphonic acid.

1 .12. Acylaminophenols, for example 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5- di-tert-butyl-4-hydroxyphenyl)carbamate.

1 .13. Esters of p-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric al- cohols, for example with methanol, ethanol, n-octanol, i-octanol, a mixture of linear and branched Cz-Cg-alkanol, octadecanol, a mixture of linear and branched Ci3-Ci5-alkanol, 1 ,6- hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaerythritol, tris(hydroxy- ethyl)isocyanurate, N,N'-bis-(hydroxy-ethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, tri- methylhexanediol, trimethylolpropane, 4-hydroxymethyl-1 -phospha-2,6,7-trioxabicyclo[2.2.2]- octane. 1 .14. Esters of p-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethy- lene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxy- ethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4- hydroxymethyl-1 -phospha-2,6,7-trioxabicyclo[2.2.2]octane; 3,9-bis[2-{3-(3-tert-butyl-4-hydroxy- 5-methylphenyl)propionyloxy}-1 ,1 -dimethylethyl]-2, 4,8,10-tetraoxaspiro[5.5]undecane.

1 .15. Esters of p-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)- oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4- hydroxymethyl-1 -phospha-2,6,7-trioxabicyclo[2.2.2]octane.

1 .16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octanol, octadecanol, 1 ,6-hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3- thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1 - phospha-2,6,7-trioxabicyclo[2.2.2]octane.

1 .17. Amides of p-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, for example N,N'-bis(3,5-di- tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxy- phenylpropionyl)trimethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)- hydrazide, N,N'-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionylox y)ethyl]oxamide (Naugard XL-1 (RTM), supplied by Uniroyal).

1 .18. Ascorbic acid (vitamin C)

1 .19. Aminic antioxidants, for example N,N'-di-isopropyl-p-phenylenediamine, N,N'-di-sec-butyl- p-phenylenediamine, N,N'-bis(1 ,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1 -ethyl-3- methylpentyl)-p-phenylenediamine, N,N'-bis(1 -methylheptyl)-p-phenylenediamine, N,N'-dicyclo- hexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-bis(2-naphthyl)-p-phenyl- enediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1 ,3-dimethylbutyl)-N'-phenyl-p- phenylenediamine, N-(1 -methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl- p-phenylenediamine, 4-(p-toluenesulfamoyl)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p- phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N- phenyl-1 -naphthylamine, N-(4-tert-octylphenyl)-1 -naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4- butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoyl- aminophenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'- diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N\N'-tetramethyl-4,4'-diaminodi- phenylmethane, 1 ,2-bis[(2-methylphenyl)amino]ethane, 1 ,2-bis(phenylamino)propane, (o-tolyl)- biguanide, bis[4-(1 ',3'-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1 -naphthylamine, a mixture of mono- and dialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono- and dialkylated nonyldiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkylated isopropyl/isohexyldiphenylamines, a mixture of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1 ,4-benzothiazine, phenothia- zine, a mixture of mono- and dialkylated tert-butyl/tert-octylphenothiazines, a mixture of mono- and dialkylated tert-octylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1 ,4-di- aminobut-2-ene, N,N-bis(2,2,6,6-tetramethylpiperid-4-yl-hexamethylenediamine , bis(2, 2,6,6- tetramethylpiperid-4-yl)sebacate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethyl- piperidin-4-ol.

2. UV absorbers and light stabilisers

2.1. 2-(2'-Hydroxyphenyl)benzotriazoles, for example 2-(2'-hydroxy-5'-methylphenyl)benzo- triazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-tert-butyl-2'-hydroxyphenyl)- benzotriazole, 2-(2'-hydroxy-5'-(1 ,1 ,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert- butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5- chlorobenzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole , 2-(2'-hydroxy- 4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)benzotriazole, 2-(3',5'- bis(a,a-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyl- oxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonyl- ethyl]-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbon- ylethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)- phenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phen yl)benzotri- azole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hy droxyphenyl)benzotriazole, 2-(3'- dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxy- carbonylethyl)phenylbenzotriazole, 2,2'-methylenebis[4-(1 ,1 ,3,3-tetramethylbutyl)-6-benzo- triazole-2-ylphenol]; the transesterification product of 2-[3'-tert-butyl-5'-(2-methoxycarbonyl-

ethyl)-2'-hydroxyphenyl]-2H-benzotriazole with polyethylene glycol 300;

where R' = 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, 2-[2'-hydroxy-3'-(a,a-dimethyl- benzyl)-5'-(1 ,1 ,3,3-tetramethylbutyl)phenyl]benzotriazole; 2-[2'-hydroxy-3'-(1 ,1 ,3,3-tetramethyl- butyl)-5'-(a,a-dimethylbenzyl)phenyl]benzotriazole.

2.2. 2-Hydroxybenzophenones, for example the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivatives. 2.3. Esters of substituted and unsubstituted benzoic acids, for example 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl)- resorcinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexa- decyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2- methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.

2.4. Acrylates, for example ethyl a-cyano- β,β-diphenylacrylate, isooctyl a-cyano- β,β-diphenyl- acrylate, methyl a-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl a-cyano^-methyl-p-methoxycinnamate, methyl a-carbomethoxy-p-methoxycinnamate, N- (β-carbomethoxy-β-cyanovinyl)-2-methylindoline and neopentyl tetra(a-cyano-p,p-diphenylacryl- ate).

2.5. Nickel compounds, for example nickel complexes of 2,2'-thiobis[4-(1 ,1 ,3,3-tetramethyl- butyl)phenol], such as the 1 :1 or 1 :2 complex, with or without additional ligands such as n-butyl- amine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g. the methyl or ethyl ester, of 4-hydroxy-3,5-di-tert-butylbenzyl- phosphonic acid, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methylphenylundecyl- ketoxime, nickel complexes of 1 -phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands.

2.6. Sterically hindered amines, for example bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1 ,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1 ,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1 -(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamin e and 4-tert-octylamino-2,6-dichloro-1 ,3,5-triazine, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacet- ate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1 ,2,3,4-butanetetracarboxylate, 1 ,1 '-(1 ,2-ethanedi- yl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy- 2,2,6,6-tetramethylpiperidine, bis(1 ,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di - tert-butylbenzyl)malonate, 3-n-octyl-7,7,9,9-tetramethyl-1 ,3,8-triazaspiro[4.5]decane-2,4-dione, bis(1 -octyloxy-2,2,6,6-tetramethylpiperid-4-yl)sebacate, bis(1 -octyloxy-2,2,6,6-tetramethyl- piperid-4-yl)succinate, bis-[2,2,6,6-tetramethyl-1 -(undecyloxy)-piperidin-4-yl] carbonate, linear or cyclic condensates of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylenediami ne and 4- morpholino-2,6-dichloro-1 ,3,5-triazine, the condensate of 2-chloro-4,6-bis(4-n-butylamino-

2,2,6,6-tetramethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis(3-aminopropylamino)ethane, the condensate of 2-chloro-4,6-di-(4-n-butylamino-1 , 2,2,6, 6-pentamethylpiperidyl)-1 ,3,5-triazine and 1 ,2- bis(3-aminopropyl-amino)ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1 ,3,8-triazaspiro[4.5]- decane-2,4-dione, 3-dodecyl-1 -(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione, 3-dodecyl- 1 -(1 ,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4- stearyloxy-2,2,6,6-tetramethylpiperidine, a condensate of N,N'-bis(2,2,6,6-tetramethyl-4-piperid- yl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1 ,3,5-triazine, a condensate of 1 ,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1 ,3,5-triazine as well as 4-butylamino- 2,2,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96-6]); a condensate of 1 ,6-hexanedi- amine and 2,4,6-trichloro-1 ,3,5-triazine as well as Ν,Ν-dibutylamine and 4-butylamino-2,2,6,6- tetramethylpiperidine (CAS Reg. No. [192268 64-7]); reaction products of N6,N6'-hexane-1 ,6- diylbis[N2,N4-dibutyl-N2,N4,N6-tris(2,2,6,6-tetramethylpiper idin-4-yl)-1 ,3,5-tn

triamine], butanal and hydrogen peroxide; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecyl- succinimide, N-(1 ,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide, 2-undecyl-7,7,9,9- tetramethyl-1 -oxa-3,8-diaza-4-oxo-spiro[4,5]decane, a reaction product of 7,7,9, 9-tetramethyl-2- cycloundecyl-1 -oxa-3,8-diaza-4-oxospiro-[4,5]decane and epichlorohydrin, 1 ,1 -bis(1 ,2,2,6,6- pentamethyl-4-piperidyloxycarbonyl)-2-(4-methoxyphenyl)-ethe ne, N,N'-bis-formyl-N,N'- bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, a diester of 4-methoxymethylene- malonic acid with 1 ,2,2,6, 6-pentamethyl-4-hydroxy-piperidine, poly[methylpropyl-3-oxy-4- (2,2,6,6-tetramethyl-4-piperidyl)]siloxane, a reaction product of maleic acid anhydride-a-olefin copolymer with 2,2,6,6-tetramethyl-4-aminopiperidine or 1 , 2,2,6, 6-pentamethyl-4-amino- piperidine, a mixture of oligomeric compounds which are the formal condensation products of N,N'-bis-(2,2,6,6-tetramethyl-1 -propoxy-piperidin-4-yl)-hexane-1 ,6-diamine and 2,4-dichloro-6- {n-butyl-(2,2,6,6-tetramethyl-1 -propoxy-piperidin-4-yl)-amino}-[1 ,3,5]triazine end-capped with 2- chloro-4,6-bis-(di-n-butylamino)-[1 ,3,5]triazine, a mixture of oligomeric compounds which are the formal condensation products of N,N'-bis-(2,2,6,6-tetramethyl-piperidin-4-yl)-hexane-1 ,6-di- amine and 2,4-dichloro-6-{n-butyl-(2,2,6,6-tetramethyl-piperidin-4-yl) -amino}-[1 ,3,5]triazine end- capped with 2-chloro-4,6-bis-(di-n-butylamino)-[1 ,3,5]triazine, (N2,N4-dibutyl-N2,N4- bis(1 ,2,2,6,6-pentamethyl-4-piperidinyl)-6-(1 -pyrrolidinyl)-[1 ,3,5]-triazine-2,4-diamine, 2,4-bis[N- (1 -cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-yl)-N-butylam ino]-6-(2-hydroxyethyl)amino- 1 ,3,5-triazine, 1 -(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetra methylpiperidine, 5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone, Sanduvor (Clariant; CAS Reg. No. [106917-31 -1]), 5-(2-ethylhexanoyl)-oxymethyl-3,3,5-trimethyl-2-morpholinone , the reaction product of 2,4-bis-[(1 -cyclo-hexyloxy-2,2,6,6-piperidine-4-yl)butylamino]-6-chloro -s-triazine with N,N'-bis-(3-amino-propyl)ethylenediamine), 1 ,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethyl- piperazine-3-one-4-yl)amino)-s-triazine, 1 ,3,5-tris(N-cyclohexyl-N-(1 ,2,2,6,6- pentamethylpiperazine-3-one-4-yl)-amino)-s-triazine.

2.7. Oxamides, for example 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'- di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, Ν,Ν'- bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and its mixture with 2- ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.

2.8. 2-(2-Hydroxyphenyl)-1 ,3,5-triazines, for example 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-

1 ,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine, 2-(2,4- dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxy- phenyl)-6-(2,4-dimethylphenyl)-1 ,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methyl- phenyl)-1 ,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl) -1 ,3,5-tri- azine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl )-1 ,3,5-triazine, 2-[2- hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-d imethyl)-1 ,3,5-triazine, 2-[2- hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4 -dimethyl)-1 ,3,5-triazine, 2-[4-(do- decyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6- bis(2,4-dimethylphenyl)-1 ,3,5-tri- azine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bi s(2,4-dimethylphenyl)- 1 ,3,5-triazine, 2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1 ,3,5-triazine, 2-(2-hydroxy-4- methoxyphenyl)-4,6-diphenyl-1 ,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)- phenyl]-1 ,3,5-triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1 ,3,5-triazine, 2-{2- hydroxy-4-[3-(2-ethylhexyl-1 -oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl) -1 ,3,5- triazine.

3. Metal deactivators, for example Ν,Ν'-diphenyloxamide, N-salicylal-N'-salicyloyl hydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazin e, 3- salicyloylamino-1 ,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthaloyl dihy- drazide, sebacoyl bisphenylhydrazide, Ν,Ν'-diacetyladipoyl dihydrazide, N,N'-bis(salicyloyl)oxal- yl dihydrazide, N,N'-bis(salicyloyl)thiopropionyl dihydrazide.

4. Phosphites and phosphonites, for example triphenyl phosphite, diphenylalkyl phosphites, phenyldialkyl phosphites, tris(nonylphenyl) phosphite, C12-C18 alkyl bis[4-(1 -methyl-1 -phenyl- ethyl)phenyl] phosphite, C12-C18 alkenyl bis[4-(1 -methyl-1 -phenyl-ethyl)phenyl] phosphite, bis[4- (1 -methyl-1 -phenyl-ethyl)phenyl] [(E)-octadec-9-enyl] phosphite, decyl bis[4-(1 -methyl-1 -phenyl- ethyl)phenyl] phosphite, didecyl [4-(1 -methyl-1 -phenyl-ethyl)phenyl] phosphite, [4-(1 -methyl-1 - phenyl-ethyl)phenyl] bis[(E)-octadec-9-enyl] phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl pen- taerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-di- cumylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)penta- erythritol diphosphite, bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite, [2-tert-butyl-4- [1 -[5-tert-butyl-4-di(tridecoxy)phosphanyloxy-2-methyl-phenyl] butyl]-5-methyl-phenyl] ditridecyl phosphite, tristearyl sorbitol triphosphite, a mixture of at least two different tris(mono-Ci-C8- alkyl)phenyl phosphites such as for example mentioned in US 7468410 B2 as products of examples 1 and 2, a mixture of phosphites comprising at least two different tris(amylphenyl) phosphites such as for example mentioned in US 8008383 B2 as mixtures 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25 and 26, a mixture of a least four different phosphites comprising tris[4-(1 ,1 - dimethylpropyl)phenyl] phosphite, [2,4-bis(1 ,1 -dimethylpropyl)phenyl] bis[4-(1 ,1 -dimethylpropyl)- phenyl] phosphite, bis[2,4-bis(1 ,1 -dimethylpropyl)phenyl] [4-(1 ,1 -dimethylpropyl)phenyl] phosphite and tris[2,4-bis(1 ,1 -dimethylpropyl)phenyl] phosphite, a mixture of phosphites comprising at least two different tris(butylphenyl) phosphites such as for example mentioned in US 8008383 B2 as mixtures 34, 35, 36, 37, 38, 39 and 40, an oxyalkylene-bridged bis-(di-C6-aryl) diphos- phite or an oligomeric phosphite obtainable by condensation under removal of hydrogen chloride of (i) a trichlorophosphane, with (ii) a dihydroxyalkane interrupted by one or more oxygen atoms and with (iii) a mono-hydroxy-C6-arene such as for example mentioned in US 8304477 B2 as products of examples 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16 and 17, a polymeric phosphite obtainable by transesterification under removal of phenol of (i) triphenyl phosphite with (ii) a dihydroxyalkane optionally interrupted by one or more oxygen atoms and/or a bis- (hydroxyalkyl)(alkyl)amine and with (iii) a mono-hydroxyalkane optionally interrupted by one or more oxygen atoms such as for example mentioned in US 8563637 B2 as products of examples 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10 and 1 1 , tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylene diphosphon- ite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1 ,3,2-dioxaphosphocine, bis(2,4-di- tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1 ,3,2-dioxaphosphocine, 1 ,3,7,9-tetra- tert-butyl-1 1 -octoxy-5H-benzo[d][1 ,3,2]benzodioxaphosphocine, 2,2',2"-nitrilo[triethyltris-

(3,3',5,5'-tetra-tert-butyl-1 ,1 '-biphenyl-2,2'-diyl)phosphite], phosphorous acid, triphenyl ester, polymer with a-hydro^-hydroxypoly[oxy(methyl-1 ,2-ethanediyl)], C10-16-alkyl esters (CAS Reg. No. [1227937-46-3]), 2-ethylhexyl(3,3',5,5'-tetra-tert-butyl-1 ,1 '-biphenyl-2,2'-diyl)phosphite, 5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1 ,3,2-dioxaphosphirane, phosphorous acid, mixed 2,4-bis(1 ,1 -dimethylpropyl)phenyl and 4-(1 ,1 -dimethylpropyl)phenyl triesters (CAS Reg. No.

[939402-02-5]).

The following phosphites are especially preferred: Tris(2,4-di-tert-butylphenyl) phosphite (Irgafos 168, RTM BASF), tris(nonylphenyl) phosphite,

5. Hydroxylamines and amine N-oxides, for example Ν,Ν-dibenzylhydroxylamine, N,N-diethyl- hydroxylamine, Ν,Ν-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-ditetradecylhydroxyl- amine, N,N-dihexadecylhydroxylamine, Ν,Ν-dioctadecylhydroxylamine, N-hexadecyl-N-octa- decylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, Ν,Ν-dialkylhydroxylamine derived from hydrogenated tallow amine , N,N-bis-(hydrogenated rape-oil alkyl)-N-methyl-amine N-oxide or trialkylamine N-oxide.

6. Nitrones, for example N-benzyl-alpha-phenylnitrone, N-ethyl-alpha-methylnitrone, N-octyl- alpha-heptylnitrone, N-lauryl-alpha-undecylnitrone, N-tetradecyl-alpha-tridecylnitrone, N-hexa- decyl-alpha-pentadecylnitrone, N-octadecyl-alpha-heptadecylnitrone, N-hexadecyl-alpha-hepta- decylnitrone, N-octadecyl-alpha-pentadecylnitrone, N-heptadecyl-alpha-heptadecylnitrone, N- octadecyl-alpha-hexadecylnitrone, nitrone derived from Ν,Ν-dialkylhydroxylamine derived from hydrogenated tallow amine.

7. Thiosynergists, for example dilauryl thiodipropionate, dimistryl thiodipropionate, distearyl thi- odipropionate and pentaerythritol tetrakis-[3-(n-lauryl)-propionic acid ester].

8. Peroxide scavengers, for example esters of a-thiodipropionic acid, for example the lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole or the zinc salt of 2-mercaptobenz- imidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis(p-dodecyl- mercapto)propionate.

9. Polyamide stabilizers, for example copper salts in combination with iodides and/or phosphorus compounds and salts of divalent manganese. 10. Acid scavengers, for example melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanu- rate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example calcium stearate, zinc stea- rate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate and zinc pyrocatecholate.

1 1 . Benzofuranones and indolinones, for example those disclosed in US-A-4,325,863; US A- 4,338,244; US-A-5,175,312; US-A-5,216,052; US-A-5,252,643; DE-A-431661 1 ; DE-A-4316622; DE-A-4316876; EP-A-0589839 or EP-A-0591 102, or 5,7-di-tert-butyl-3-(4-hydroxyphenyl)-3H- benzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]-3H-benzofura n-2-one, 5,7-di- tert-butyl-3-[4-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]e thoxy]ethoxy]phenyl]-3H-benzofuran- 2-one, 3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2- one, 5,7-di-tert-butyl-3-[4-(2- stearoyloxyethoxy)phenyl]benzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]- phenyl)benzofuran-2-one], 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, 3-(4-acetoxy- 3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7- di-tert-butylbenzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(2,3- dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(2-acetoxy-4-(1 ,1 ,3,3-tetramethyl-butyl)- phenyl)-5-(1 ,1 ,3,3-tetramethyl-butyl)-benzofuran-2-one, [6-[6-[6-[2-[4-(5,7-di-tert-butyl-2-oxo-3H- benzofuran-3-yl)phenoxy]ethoxy]-6-oxo-hexoxy]-6-oxo-hexoxy]- 6-oxo-hexyl] 6-hydroxyhexan- oate, [4-tert-butyl-2-(5-tert-butyl-2-oxo-3H-benzofuran-3-yl)pheny l] benzoate, [4-tert-butyl-2-(5- tert-butyl-2-oxo-3H-benzofuran-3-yl)phenyl] 3,5-di-tert-butyl-4-hydroxy-benzoate and [4-tert- butyl-2-(5-tert-butyl-2-oxo-3H-benzofuran-3-yl)phenyl] 3-(3,5-di-tert-butyl-4-hydroxy- phenyl)propanoate.

12. Nucleating agents, for example inorganic substances, such as talcum, metal oxides, such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of, preferably, alkaline earth metals; organic compounds, such as mono- or polycarboxylic acids and the salts thereof, e.g. 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds, such as ionic copolymers (ionomers), Irgaclear XT 386 (RTM BASF), 1 ,3:2,4-bis(3',4'-dimethylbenzylidene)-sorbitol, 1 ,3:2,4-di(paramethyldibenzylid- ene)-sorbitol, 1 ,3:2,4-di(benzylidene)sorbitol and bis(4-propylbenzylidene) propyl sorbitol [CAS- No. 882073-43-0].

13. Fillers and reinforcing agents, for example calcium carbonate, silicates, glass fibres, glass beads, asbestos, talc, kaolin, bentonite, mica, hydrotalcite, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic fibers.

14. Polymer processing aids, for example a fluoropolymer such as a copolymer of vinylidene fluoride and hexafluoropropylene or a silicone containing polymer such as a polymer based on ultra-high molecular weight poly(dimethylsiloxane); commercial examples are Dynamar (RTM 3M, chemical class of fluoropolymer), Viton (RTM DuPont, chemical class of fluoropolymer), Kynar Flex (RTM Arkema, chemical class of fluoropolymer) and MB series of Dow Corning (RTM Dow Corning, chemical class of silicones). 15. Other additives, for example plasticisers, lubricants, rheology additives, catalysts, flow- control agents, optical brighteners, flameproofing agents, antistatic agents and blowing agents.

It is understood herein that the further additive is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III. For calculation of the weight relationship of component a) to component b), a further additive, which is a polymeric additive, i.e. an additive fulfilling also the definition of a polymer, for example a polymeric sterically hindered amine such as the condensate of 1 -(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, the weight of the polymeric additive is added to the weight of the polymer intended as component a) to obtain the weight of all polymers in the composition. This weight of all polymers is taken for calculation, whether the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

It has also been surprisingly found that many phenolic metal salts of formula I or bisphenolic compounds of formula III in combination with a further additive are very effective for stabilization of an organic material against degradation by heat, light and / or oxidation, particularly in combination with a phenolic antioxidant or a phosphite or phosphonite as a further additive. It often turns out that the presence of a phenolic metal salt of formula I or a bisphenolic compound of formula III allows to reduce the amount of the further additive further than a mere one to one substitution based on the weight of the further additive.

Preferred is a composition, which comprises a polymer as component a), a phenolic metal salt of formula I or a bisphenolic compound of formula III as component b) and a further additive as component c).

Preferred is a composition, wherein the weight ratio of component b) to component c) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10.

Preferred is a composition, which comprises as component c) a further additive, which is an antioxidant, an UV absorber, a hindered amine light stabilizer, a nickel compound, a metal deactivator, a phosphite or phosphonite, a hydroxylamine or amine N-oxide, a thiosynergist, a peroxide scavenger or a nucleating agent.

Preferred is a composition, which comprises as component c) a further additive, which is a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

Preferred is a composition, which comprises

a) a polymer,

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

c) a further additive, which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, or a phosphite or phosphonite, wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises as component c) a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III.

Preferred is a composition, which comprises as component c) a phenolic antioxidant, which is an ester of p-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid. A phenolic antioxidant of special picted

and for which one chemical name is tetrakis-[p-(3,5-di-tert-butyl-4-hydroxyphenyl)- propionyloxymethyl]methane or alternatively tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)- propionyloxymethyl]methane. It is contained in the commercial product Irganox 1010 (RTM BASF).

Another phenolic antioxidant of special relevance is a compound as depicted

and for which one chemical name is stearyl p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate or alternatively stearyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate. It is contained in the commercial product Irganox 1076 (RTM BASF).

Preferred is a composition, which comprises as component c) a phenolic antioxidant, which is tetrakis-[p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxy methyl]methane or stearyl p-(3,5-di- tert-butyl-4-hydroxyphenyl)-propionate.

Preferred is a composition, which comprises as component c) a phosphite or phosphonite.

A phosphite of special relevance is a compound as depicted

and for which one chemical name is tris-(2,4-di-tert-butylphenyl) phosphite. It is contained in the commercial product Irgafos 168 (RTM BASF). Preferred is a composition, which comprises as component c) a phosphite, which is tris-(2,4-di- tert-butylphenyl) phosphite.

Preferred is a composition, which comprises as component c) a phosphite or a phenolic antioxidant, which is an ester of p-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

Optionally, a composition comprising an organic material susceptible to oxidative, thermal or light-induced degradation as component a), a phenolic metal salt of formula I or a bisphenolic compound of formula III compound as component b) and a further additive as component c) contains a second further additive as component d).

It is understood that the second further additive is different to a phenolic metal salt of formula I, a bisphenolic compound of formula III or the further additive. For calculation of the weight relationship of component a) to component b), a second further additive, which is a polymeric additive, i.e. an additive fulfilling also the definition of a polymer, for example a polymeric sterically hindered amine such as the condensate of 1 -(2-hydroxyethyl)-2,2,6,6-tetramethyl-4- hydroxypiperidine and succinic acid, the weight of the polymeric additive is added to the weight of the polymer intended as component a) to obtain the weight of all polymers in the composition. This weight of all polymers is taken for calculation, whether the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises a polymer as component a), a phenolic metal salt of formula I or a bisphenolic compound of formula III as component b), a further additive, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, as component c), and a second further additive as component d), which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, with the proviso that component d) is a different substance than component c).

Preferred is a composition, wherein the weight ratio of component b) to component d) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10.

Preferred is a composition, wherein the weight ratio of component b) to component c) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10, and wherein the weight ratio of component b) to component d) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10.

Preferred is a composition, which comprises a component a), a component b), as component c) a further additive, which is selected from the group consisting of a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and an aminic antioxidant, and as component d) a second further additive; with the proviso that component d) is a different substance than component c).

Preferred is a composition, which comprises a component a), a component b), a component c) and a component d), wherein component c) and component d) are independently from each other a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, or an aminic anti- oxidant; with the proviso that component d) is a different substance than component c).

Preferred is a composition, which comprises a component a), a component b), as component c) a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and as component d) an aminic antioxidant.

Preferred is a composition, which comprises a component a), a component b), as component c) a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and as component d) a phosphite or phosphonite. Preferred is a composition, which comprises

a) a polymer,

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III,

c) a further additive, which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

d) a second further additive, which is a phosphite or phosphonite,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) a polymer,

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III,

c) a further additive, which is a phenolic antioxidant, which is tetrakis-[p-(3,5-di-tert-butyl-4- hydroxyphenyl)-propionyloxymethyl]methane or stearyl p-(3,5-di-tert-butyl-4-hydroxyphenyl)- propionate, and

d) a second further additive, which is a phosphite or phosphonite,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). Preferred is a composition, which comprises

a) a polymer,

b) a phenolic metal salt of formula I or a bisphenolic compound of formula II I ,

c) a further additive, which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula I I I, and

d) a second further additive, which is a phosphite, which is tris-(2 ,4-d i-tert-butyl phenyl) phosphite,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

Preferred is a composition, which comprises

a) an organic material susceptible to oxidative, thermal or light-induced degradation, b) a phenolic metal salt of formula I or a bisphenolic compound of formula II I ,

c) a further additive, which is a phenolic antioxidant, which is tetrakis-[p-(3,5-di-tert-butyl-4- hydroxyphenyl)-propionyloxymethyl]methane or stearyl p-(3,5-di-tert-butyl-4-hydroxyphenyl)- propionate, and

d) a second further additive, which is a phosphite, which is tris-(2 ,4-d i-tert-butyl phenyl) phosphite,

wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a).

The above described preferences for a polymer as component a) and for a phenolic metal salt of formula I or a bisphenolic compound of formula II I as component b) are described for a com- position. These preferences apply also to the further embodiments. At these further embodiments, the optional presence of a further additive as component c) and the optional presence of a second further additive as component d) are also included. The principles for calculation of the weights of component b) and of component a) as described for a composition apply also for the further embodiments.

A further embodiment is a process for manufacturing a stabilized polymer, which process prises the steps of

(A) providing a component a), which is a polymer,

(B) adding to the provided component a) a component b) to obtain a composition,

wherein component b) is

(i) a phenolic metal salt of formula I

wherein

n is 1 , 2 or 3,

M ⁿ⁺ is a metal ion and Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ , Cs ⁺ , Be ²⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , La ³⁺ , Ce ³⁺ , Nd ³⁺ , Eu ³⁺ , Gd ³⁺ , Yb ³⁺ , Sc ²⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ti ³⁺ , Zr ⁺ , Zr ²⁺ , Zr ³⁺ , HP ⁺ , Hf ³⁺ , V ²⁺ , V ³⁺ , Nb ²⁺ , Nb ³⁺ , Ta ²⁺ , Ta ³⁺ , Cr ²⁺ , Cr ³⁺ , Mo ²⁺ , Mo ³⁺ , W ²⁺ , W ³⁺ , Mn ²⁺ , Mn ³⁺ , Re ³⁺ , Fe ²⁺ , Fe ³⁺ , Ru ³⁺ , Os ²⁺ , Os ³⁺ , Co ²⁺ , Rh ³⁺ , lr ³⁺ , Ni ²⁺ , Pd ²⁺ , Pt ²⁺ , Cu ²⁺ , Cu ²⁺ , Ag ⁺ , Au ⁺ , Au ³⁺ , Zn ²⁺ , Cd ²⁺ , Hg ⁺ , Hg ²⁺ , Al ³⁺ , Ga ²⁺ , Ga ³⁺ , ln ²⁺ , ln ³⁺ , ^" I , Tl ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ ,

- is an anion of formula II

wherein

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH2-CH2- and A ² is -CH ₂ - R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl, or

wherein

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH2-CH2- and A ² is -CH ₂ -,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl,

wherein the amount of component b) is from 0.0005 to 0.9% by weight based on the weight of component a),

(C) heating the obtained composition to a temperature between 135° C and 360°C to obtain the stabilized polymer, and

(D) optionally cooling the stabilized polymer.

It is understood that at the obtained stabilized polymer, the amount of component b) is from 0.0005 to 0.9% by weight based on the weight of component a). For example, in case of two steps of adding, the overall weight ratio remains obeyed.

The step of heating the obtained composition serves to distribute the component b) evenly in the component a). The step of heating is conducted in a processing apparatus. A suitable pro- cessing apparatus is for example a heated container, which can preferably be closed, equipped with a stirrer. Examples thereof are a kneader, an extruder, a mixer or a stirred vessel. More specific examples for an extruder are a single-screw extruder, a contrarotating or corotating twin-screw extruder, a planetary-gear extruder or a ring extruder. A more specific example for a kneader is a co-kneader. The processing apparatus might contain at least one gas removal compartment to which a vacuum can be applied and / or which can be set under an atmosphere, wherein the oxygen content is low or oxygen is absent, for example under a nitrogen atmosphere. The step of adding the component b) can be performed in spatial separation to the step of heating or performed in close spatial and chronological proximity to the step of heating. For example, the steps of adding and heating can be carried out in one processing apparatus, particularly in a heated container equipped with a stirrer, very particular a kneader or an extruder. For example, the component b) is added directly into the processing apparatus, which contains already component a). At the step of heating, the temperature is preferably from 180°C to 330°C, especially from 190°C to 320°C and very especially from 250°C to 310°C.

Preferably, the step of heating occurs in an extruder or a co-kneader, especially an extruder. Very preferably, the step of adding and the step of heating occurs in an extruder or a co- kneader, especially an extruder.

Component b) can be added to component a) at a stage, where the provided component a) is already heated above room temperature. Component b) can be added during or directly after the polymerization of the corresponding starting materials, e.g. monomers, of component a). If added during polymerization, only a part of component a) is already provided, whereas another part of component a) is still formed. An example for addition directly after the polymerization of component a) is spraying during the deactivation of an polymerization catalyst. If a crosslinking takes place during formation of com- ponent a), component b) is preferably added prior to completion of crosslinking.

Component b) can be added in the form of a free-flowing powder, in the form of a compacted powder, the form of a melt, in encapsulated form or in the form of a wet mixture. A compacted powder is obtained by pressing the components together for example in a pellet mill or an ex- truder. At the pressing, heat is generated either by the pressing itself or by additional external heating. The heat leads to an at least partial melting at the surface of the powder particles or of at least one component, which serves as binder during compaction. A melt is obtained by a complete melting of all components and cooling afterwards. An encapsulated form is for example a masterbatch (concentrate), which contains the component b) and a masterbatch polymer or a masterbatch wax as an auxiliary component. The masterbatch polymer or masterbatch wax is compatible to the component a) and serves as binder for component b). Examples for a wet mixture are a solution, a dispersion or a suspension for example in an inert solvent, water or oil. In case of a dispersion or a suspension, the inert solvent, the water or the oil is preferably removed prior to the step of heating of the composition. Particularly, if the boiling point or the vapour pres- sure is detrimental for heating the composition. A dispersing or suspension agent can be present in the case of a wet mixture of component b). The form of a compacted powder, the form of a melt and an encapsulated form are preferably provided as pellets or granules. This allows a simplified dosing and limits dust formation.

After the step of heating and prior to the optional step of cooling, the process can comprise a step of shaping the stabilized polymer to obtain a shaped article. The shaped article is a stabilized polymer in a solid, pre-defined three-dimensional form. If a step of shaping of the stabilized polymer is included, the processing apparatus is preferably a heated container with a stirrer, which is an extruder or a kneader. The shaping step is preferably a molding process, in particular an injection-molding, blow-molding, compression-molding, roto-molding, slush-molding or extrusion-molding. Particularly preferred is extrusion-molding, especially extrusion-molding resulting in pellets of the stabilized polymer after a cutting step.

Examples for a shaped article are in particular pellets or granules. Furthermore, shaped articles comprises also:

1-1 ) Floating devices, marine applications, pontoons, buoys, plastic lumber for decks, piers, boats, kayaks, oars, and beach reinforcements.

I-2) Automotive applications, in particular bumpers, dashboards, battery, rear and front linings, moldings parts under the hood, hat shelf, trunk linings, interior linings, air bag covers, electronic moldings for fittings (lights), panes for dashboards, headlamp glass, instrument panel, exterior linings, upholstery, automotive lights, head lights, parking lights, rear lights, stop lights, interior and exterior trims; door panels; gas tank; glazing front side; rear windows; seat backing, exterior panels, wire insulation, profile extrusion for sealing, cladding, pillar covers, chassis parts, ex- haust systems, fuel filter / filler, fuel pumps, fuel tank, body side mouldings, convertible tops, exterior mirrors, exterior trim, fasteners / fixings, front end module, glass, hinges, lock systems, luggage / roof racks, pressed/stamped parts, seals, side impact protection, sound deadener / insulator and sunroof. I-3) Road traffic devices, in particular sign postings, posts for road marking, car accessories, warning triangles, medical cases, helmets, tires.

I-4) Devices for plane, railway, motor car (car, motorbike, trucks) including furnishings. I-5) Devices for space applications, in particular rockets and satellites, e.g. reentry shields.

I-6) Devices for architecture and design, mining applications, acoustic quietized systems, street refuges, and shelters. 11-1 ) Appliances, cases and coverings in general and electric/electronic devices (personal computer, telephone, portable phone, printer, television-sets, audio and video devices), flower pots, satellite TV bowl, and panel devices. 11-2) Jacketing for other materials such as steel or textiles.

11-3) Devices for the electronic industry, in particular insulation for plugs, especially computer plugs, cases for electric and electronic parts, printed boards, and materials for electronic data storage such as chips, check cards or credit cards.

11-4) Electric appliances, in particular washing machines, tumblers, ovens (microwave oven), dish-washers, mixers, and irons.

II-5) Covers for lights (e.g. street-lights, lamp-shades).

II- 6) Applications in wire and cable (semi-conductor, insulation and cable-jacketing). II-7) Foils for condensers, refrigerators, heating devices, air conditioners, encapsulating of electronics, semi-conductors, coffee machines, and vacuum cleaners.

I I I- 1 ) Technical articles such as cogwheel (gear), slide fittings, spacers, screws, bolts, handles, and knobs.

III-2) Rotor blades, ventilators and windmill vanes, solar devices, swimming pools, swimming pool covers, pool liners, pond liners, closets, wardrobes, dividing walls, slat walls, folding walls, roofs, shutters (e.g. roller shutters), fittings, connections between pipes, sleeves, and conveyor belts.

III-3) Sanitary articles, in particular shower cubicles, lavatory seats, covers, and sinks.

III-4) Hygienic articles, in particular diapers (babies, adult incontinence), feminine hygiene articles, shower curtains, brushes, mats, tubs, mobile toilets, tooth brushes, and bed pans.

III-5) Pipes (cross-linked or not) for water, waste water and chemicals, pipes for wire and cable protection, pipes for gas, oil and sewage, guttering, down pipes, and drainage systems.

III-6) Profiles of any geometry (window panes) and siding.

III-7) Glass substitutes, in particular extruded or co-extruded plates, glazing for buildings (monolithic, twin or multiwall), aircraft, schools, extruded sheets, window film for architectural glazing, train, transportation, sanitary articles, and greenhouse. III-8) Plates (walls, cutting board), extrusion-coating (photographic paper, tetrapack and pipe coating), silos, wood substitute, plastic lumber, wood composites, walls, surfaces, furniture, decorative foil, floor coverings (interior and exterior applications), flooring, duck boards, and tiles.

111-9) Intake and outlet manifolds.

III- 10) Cement-, concrete-, composite-applications and covers, siding and cladding, hand rails, banisters, kitchen work tops, roofing, roofing sheets, tiles, and tarpaulins.

IV- 1 ) Plates (walls and cutting board), trays, artificial grass, synthetic (such as AstroTurf (RTM)), artificial covering for stadium rings (athletics), artificial floor for stadium rings (athletics), and tapes.

IV-2) Woven fabrics continuous and staple, fibers (carpets / hygienic articles / geotextiles / monofilaments; filters; wipes / curtains (shades) / medical applications), bulk fibers (applications such as gown / protection clothes), nets, ropes, cables, strings, cords, threads, safety seat- belts, clothes, underwear, gloves; boots; rubber boots, intimate apparel, garments, swimwear, sportswear, umbrellas (parasol, sunshade), parachutes, paraglides, sails, "balloon-silk", camping articles, tents, airbeds, sun beds, bulk bags, and bags. Non-woven fabrics such as medical fabrics and related apparel such as medical garment and as face masks, as industrial apparel, as outdoor fabrics, as in-home furnishing, as construction fabrics, for example as house wrapping or as roofing inter layer, as diaper backings and as house wraps. Non-woven fabrics are in view of their method of production for example solution spun fabrics, spun bond fabrics or melt blown fabrics. IV-3) Membranes, insulation, covers and seals for roofs, tunnels, dumps, ponds, walls roofing membranes, geomembranes, swimming pools, curtains (shades) / sun-shields, awnings, canopies, wallpaper, food packing and wrapping (flexible and solid), medical packaging (flexible & solid), airbags/safety belts, arm- and head rests, carpets, centre console, dashboard, cockpits, door, overhead console module, door trim, headliners, interior lighting, interior mirrors, parcel shelf, rear luggage cover, seats, steering column, steering wheel, textiles, and trunk trim.

V) Films (packaging, dump, laminating, agriculture and horticulture, greenhouse, mulch, tunnel, silage), bale wrap, swimming pools, waste bags, wallpaper, stretch film, raffia, desalination film, batteries, and connectors.

VI-1 ) Food packing and wrapping (flexible and solid), bottles.

VI-2) Storage systems such as boxes (crates), luggage, chest, household boxes, pallets, shelves, tracks, screw boxes, packs, and cans.

VI-3) Cartridges, syringes, medical applications, containers for any transportation, waste baskets and waste bins, waste bags, bins, dust bins, bin liners, wheely bins, container in general, tanks for water / used water / chemistry / gas / oil / gasoline / diesel; tank liners, boxes, crates, battery cases, troughs, medical devices such as piston, ophthalmic applications, diagnostic devices, and packing for pharmaceuticals blister. VI 1-1 ) Extrusion coating (photo paper, tetrapack, pipe coating), household articles of any kind (e.g. appliances, thermos bottle / clothes hanger), fastening systems such as plugs, wire and cable clamps, zippers, closures, locks, and snap-closures.

VII-2) Support devices, articles for the leisure time such as sports and fitness devices, gymnas- tics mats, ski-boots, inline-skates, skis, big foot, athletic surfaces (e.g. tennis grounds); screw tops, tops and stoppers for bottles, and cans.

VII-3) Furniture in general, foamed articles (cushions, impact absorbers), foams, sponges, dish clothes, mats, garden chairs, stadium seats, tables, couches, toys, building kits (boards / figures / balls), playhouses, slides, and play vehicles.

VII-4) Materials for optical and magnetic data storage.

VII-5) Kitchen ware (eating, drinking, cooking, storing).

VII-6) Boxes for CD's, cassettes and video tapes; DVD electronic articles, office supplies of any kind (ball-point pens, stamps and ink-pads, mouse, shelves, tracks), bottles of any volume and content (drinks, detergents, cosmetics including perfumes), and adhesive tapes. VII-7) Footwear (shoes / shoe-soles), insoles, spats, adhesives, structural adhesives, food boxes (fruit, vegetables, meat, fish), synthetic paper, labels for bottles, couches, artificial joints (human), printing plates (flexographic), printed circuit boards, and display technologies.

VII-8) Devices of filled polymers (talc, chalk, china clay (kaolin), wollastonite, pigments, carbon black, ΤΊΟ2, mica, nanocomposites, dolomite, silicates, glass, asbestos).

Preferred is a shaped article, which is a pellet, a granulate, a film, a pipe, a profile, a bottle, a tank, a container or a fiber, especially a pellet or a granulate. Preferred is a shaped article, which results from a molding. Particularly, the molding is effected by injection, blowing, compression, roto-molding, slush-molding or extrusion. Very particularly, the molding is effect by extrusion.

A further embodiment to the invention is the use of a phenolic metal salt of formula I or a bi- sphenolic compound of formula III, i.e. component b), for stabilizing a polymer, i.e. component a), against degradation by oxidation, heat or light, wherein the amount of component b) is from 0.0005 to 0.9 % by weight based on the weight of component a). Preferred is the use of component b) for stabilizing a polyurethane in the form of a foam against scorching. Preferred is the use of a phenolic metal salt of formula I or a bisphenolic compound of formula III in combination with a further additive, i.e. component c), for stabilizing a polymer against degradation by oxidation, heat or light.

Preferred is the use of a phenolic metal salt of formula I or a bisphenolic compound of formula III in combination with a further additive, i.e. component c), which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, or a phosphite or phosphonite, for stabilizing a polymer against degradation by oxidation, heat or light. Preferred is the use of a phenolic metal salt of formula I or a bisphenolic compound of formula III in combination with a further additive, i.e. component c), which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and a second further additive, i.e. component d), which is a phosphite or phosphonite, for stabilizing a polymer against degradation by oxidation, heat or light.

Processing of a component a) is characterized as short-term exposure of the component a) to heat, for example to a temperature in the range of 135°C to 360°C, particularly from 180°C to 330°C, very particularly from 190°C to 320°C and especially from 250°C to 310°C, during the time of processing of component a). The time of processing is short in comparison to for exam- pie the possible time of usage, for example below 1 hour versus above 1 week. Usage takes typically place at a temperature, for example 0°C to 50°C, which is below the temperature during processing.

Preferred is the use of component b) for stabilizing a component a) against oxidative or thermal degradation during processing.

There are several ways how a polymer can get into contact with a metal, metal ions or metal- containing compounds. For example, metallic catalysts are consciously used during preparation of the polymer. Surfaces of an article obtained from a polymer may come in direct contact with metallic surfaces, for example in cable sheathings, pipes comprising metallic layers and electronic components. The result of such a contact with metals, metal ions or metal-containing compounds can be a metal-accelerated decomposition. A bisphenolic compound of formula III is a bidentate potential ligand, particularly if transformed into its deprotonated form, i.e. an anion l_- of formula II. The transformation into its deprotonated form can be assisted by an acid scav- enger. Preferred is the use of component b), which is a bisphenolic compound of formula III, for stabilizing a polymer, i.e. component a), against degradation by oxidation, heat or light, wherein the degradation is accelerated by contact with a metal, a metal-ion or a metal-containing compound, which is different to a phenolic metal salt of formula I.

Preferred is the use of component b), which is a bisphenolic compound of formula III, in combination with a further additive as component c), which is an acid stabilizer, for stabilizing a polymer, i.e. component a), against degradation by oxidation, heat or light, wherein the degradation is accelerated by contact with a metal, a metal-ion or a metal-containing compound, which is different to a phenolic metal salt of formula I.

Preferred is the use of component b) for stabilizing a component a) in combination with an acid scavenger against metal-compound-accelerated decomposition. A further embodiment of the invention is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

c) a further additive selected from a group consisting of a phosphite or phosphonite, an UV absorber, a hindered amine light stabilizer, a hydroxylamine or amine N-oxide, an acid scavenger, a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and an aminic antioxidant.

Preferred is a further additive selected from a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and an aminic antioxidant

Preferred is a composition, wherein the weight ratio of component b) to component c) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10.

Preferred is an additive mixture, wherein the weight ratio of component b) to component c) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10.

Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

c) a further additive, which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, or a phosphite or phosphonite.

Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

c) a further additive, which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III.

Preferred is an additive mixture, which comprises b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and c) a further additive, which is a phenolic antioxidant, which is an ester of p-(3,5-di-tert-butyl-4- hydroxyphenyl)propionic acid. Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

c) a further additive, which is tetrakis-[p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxy - methyl]methane, stearyl p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate or tris-(2,4-di-tert- butylphenyl) phosphite.

Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

c) a further additive, which is a phosphite or phosphonite. Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

c) a further additive, which is tris-(2,4-di-tert-butylphenyl) phosphite.

Preferred is an additive mixture, which comprises as component d) a second further additive.

Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III,

c) a further additive selected from a group consisting of a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III and an aminic antioxidant, and

d) a second further additive selected from a group consisting of a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III and an aminic antioxidant; with the proviso that component c) is a different substance than component d).

Preferred is an additive mixture, wherein the weight ratio of component b) to component c) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10, and wherein the weight ratio of component b) to component d) is from 10 : 1 to 1 : 30, in particular from 4 : 1 to 1 : 20, especially from 2 : 1 to 1 : 10.

Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III,

c) a further additive, which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

d) a second further additive, which is a phosphite or phosphonite.

Preferred is an additive mixture, which comprises b) a phenolic metal salt of formula I or a bisphenolic compound of formula III,

c) a further additive, which is tetrakis-[p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxy methyl]- methane or stearyl p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate, and

d) a second further additive, which is a phosphite or phosphonite.

Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III,

c) a further additive, which is a phenolic antioxidant, which is different to a phenolic metal salt of formula I or a bisphenolic compound of formula III, and

d) a second further additive, which is tris-(2 ,4-d i-tert-butyl phenyl) phosphite.

Preferred is an additive mixture, which comprises

b) a phenolic metal salt of formula I or a bisphenolic compound of formula III,

c) a further additive, which is tetrakis-[p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxy methyl]- methane or stearyl p-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate, and

d) a second further additive, which is tris-(2 ,4-d i-tert-butyl phenyl) phosphite.

A further embodiment of the invention is a phenolic metal salt of formula I

wherein

n is 1 , 2 or 3,

M ⁿ⁺ is a metal ion and Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ , Cs ⁺ , Be ⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , La ³⁺ , Ce ³⁺ , Nd ³⁺ , Eu ³⁺ , Gd ³⁺ , Yb ³⁺ , Sc ²⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ti ³⁺ , Zr ⁺ , Zr ²⁺ , Zr ³⁺ , Hf^, Hf ³⁺ , V ²⁺ , V ³⁺ , Nb ²⁺ , Nb ³⁺ , Ta ²⁺ , Ta ³⁺ , Cr ²⁺ , Cr ³⁺ , Mo ²⁺ , Mo ³⁺ , W ²⁺ , W ³⁺ , Mn ²⁺ , Mn ³⁺ , Re ³⁺ , Fe ²⁺ , Fe ³⁺ , Ru ³⁺ , 0 ²⁺ , Os ³⁺ , Co ²⁺ , Rh ³⁺ , lr ³⁺ , Ni ²⁺ , Pd ²⁺ , Pt ²⁺ , Cu ²⁺ , Cu ²⁺ , Ag ⁺ , Au ⁺ , Au ³⁺ , Zn ²⁺ , Cd ²⁺ , Hg ⁺ , Hg ²⁺ , Al ³⁺ , Ga ²⁺ , Ga ³⁺ , ln ²⁺ , ln ³⁺ , ^" I , Tl ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ ,

- is an anion of formula II

wherein

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH ₂ -CH ₂ - an A ² is -CH ₂ -,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl.

Preferred is a phenolic metal salt of formula I, which is a phenolic metal complex of formula l-C

[(H ₂ 0)u M" ⁺ (L-)n] (l-C)

wherein n is 1 , 2 or 3,

M ⁿ⁺ is a metal ion and Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ , Cs ⁺ , Be ⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , La ³⁺ , Ce ³⁺ , Nd ³⁺ , Eu ³⁺ , Gd ³⁺ , Yb ³⁺ , Sc ²⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ti ³⁺ , Zr ⁺ , Zr ²⁺ , Zr ³⁺ , HP ⁺ , Hf ³⁺ , V ²⁺ , V ³⁺ , Nb ²⁺ , Nb ³⁺ , Ta ²⁺ , Ta ³⁺ , Cr ²⁺ , Cr ³⁺ , Mo ²⁺ , Mo ³⁺ , W ²⁺ , W ³⁺ , Mn ²⁺ , Mn ³⁺ , Re ³⁺ , Fe ²⁺ , Fe ³⁺ , Ru ³⁺ , 0 ²⁺ , Os ³⁺ , Co ²⁺ , Rh ³⁺ , lr ³⁺ , Ni ²⁺ , Pd ²⁺ , Pt ²⁺ , Cu ²⁺ , Cu ²⁺ , Ag ⁺ , Au ⁺ , Au ³⁺ , Zn ²⁺ , Cd ²⁺ , Hg ⁺ , Hg ²⁺ , Al ³⁺ , Ga ²⁺ , Ga ³⁺ , ln ²⁺ , ln ³⁺ , Tl ⁺ , Tl ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ ,

u is 0, 1 , 2, 3 or 4,

when n is 1 ,

u is 0, 1 , 2, 3 or 4,

when n is 2 or 3,

u is 0, 1 or 2,

l - is an anion of formula II

wherein

A ¹ and A ² are both -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH ₂ -CH ₂ - an A ² is -CH ₂ -,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl.

A further embodiment of this invention is a process for manufacturing of a phenolic metal salt of formula I, which comprises the steps of

- deprotonating a bisphenolic compound of formula III with a base in a first reaction medium to obtain an anion l_- of formula II,

- reacting the obtained anion l_- of formula II with a metal ion M ⁿ⁺ in a second reaction medium to obtain a phenolic metal salt of formula I in a reaction mass,

- separating the obtained phenolic metal salt of formula I in the reaction mass from the reaction mass to obtain a phenolic metal salt of formula I.

Preferably, the deprotonating step occurs at a first temperature between 0°C and the reflux temperature of the first reaction medium. Especially, the first temperature is between 25°C and the reflux temperature of the first reaction medium, very especially between 55°C and the reflux temperature of the first reaction medium. Preferably, the reacting step occurs at a second temperature between 0°C and the reflux temperature of the second reaction medium. Especially, the first temperature is between 25°C and the reflux temperature of the second reaction medium, very especially between 55°C and the reflux temperature of the second reaction medium. Preferably, the base is LiOH, NaOH, KOH, RbOH or CsOH, particularly LiOH, NaOH or KOH, especially NaOH or KOH. Preferably, the first reaction medium comprises water or a C1-C4 alkanol. Especially, the amounts of water and C1-C4 alkanol summarizes in the first reaction medium to an amount from 60% to 100% by weight based on the weight of the total first reaction medium. Very especially, the amount is from 70% or 80% or 90% or 95% to 100% by weight. Particularly preferred are water, methanol and ethanol, very particularly water and methanol.

Preferably, the second reaction medium comprises water or a C1-C4 alkanol. Especially, the amounts of water and C1-C4 alkanol summarizes in the second reaction medium to an amount from 60% to 100% by weight based on the weight of the total first reaction medium. Very especially, the amount is from 70% or 80% or 90% or 95% to 100% by weight. Particularly preferred are water, methanol and ethanol, very particularly water and methanol.

Preferably, at least parts of the first reaction medium become at least parts of the second reaction medium. Very preferably, the weight majority of the first reaction medium becomes part, particularly the majority part by weight, of the second reaction medium. Especially, the step of reacting occurs directly after the step of deprotonating without the isolation of the anion l_- of formula II . Very especially, the both steps occur in a same reaction container.

Preferred is a process for manufacturing of a phenolic metal salt of formula I

wherein

n is 2 or 3,

M ⁿ⁺ is a metal ion and Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , La ³⁺ , Nd ³⁺ , Ce ³⁺ , Eu ³⁺ , Sc ³⁺ , Y ³⁺ , Lu ³⁺ , Ti ²⁺ , Ta ²⁺ , Ta ³⁺ , Cr ³⁺ , Mo ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Al ³⁺ , Ga ³⁺ , ln ³⁺ , Ge ²⁺ , Sn ²⁺ , Pb ²⁺ , Sb ³⁺ or Bi ³⁺ , in particular Ca ²⁺ , Ce ³⁺ , Eu ³⁺ , Cr ³⁺ , Mn ²⁺ , Mn ³⁺ , Fe ²⁺ , Fe ³⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ or Al ³⁺ ,

l - is an anion of formula I I

wherein

A ¹ and A ² are both -CH2-CH2-, -CH=CH- or -CH ₂ - or

A ¹ is -CH=CH- and A ² is -CH ₂ - or A ¹ is -CH2-CH2- an A ² is -CH ₂ -,

R ¹ , R ² , R ⁴ and R ⁵ are independently from each other C1-C4 alkyl,

R ³ is H or C1-C4 alkyl,

which comprises the steps - deprotonating a bisphenolic compound of formula II I

wherein

A ¹ , A ² , R ¹ , R ² , R ³ , R ⁴ and R ⁵ are the same as the ones at the anion l_- of the phenolic metal salt,

with a base, which is LiOH, NaOH, KOH, RbOH or CsOH, in the first reaction medium,

- reacting the obtained anion l_- of formula II with a metal ion M ⁿ⁺ , wherein the metal ion M ⁿ⁺ originates from the chloride, nitrate, sulfate or acetate salt of the metal ion M ⁿ⁺ , in the second reaction medium,

- separating the obtained phenolic metal salt of formula I in the reaction mass from the reaction mass by filtration.

The following examples illustrate further the invention without limiting it. Percentage values are percentage by weight if not stated differently.

Synthetic examples

If not otherwise stated, the starting materials are commercially available, for example from Al- drich Corp.

Dichloromethane is abbreviated as DCM.

At the structures of the synthetic examples, hydrogen atoms bonded to carbon atoms are not shown. For example, compound (101 ) as depicted below

is shown without hydrog

Furthermore, a phenolic metal salt is shown with an abbreviated anion For example, com- pound (103) as depicted below

(103)

is shown without hydrogen atoms at carbon atoms and with abbreviated anion l_- as depicted below.

Example S-1 : Synthesis of compound (101 )

(101 )

A mixture of acetylacetone (6.13 g, 0.061 mol) and powdered boron trioxide (3.00 g, 0.043 mol) is stirred in 90 mL of dry DCM for 30 min. Tri-/7-butyl borate (27.6 g) is added and the reaction mixture is stirred for a further 1 h. This mixture is then added to a mixture of 3,5-di-fe/£butyl-4- hydroxybenzaldehyde (28.15 g, 0.120 mol) and tri-/7-butyl borate (27.2 g) in 210 mL of dry DCM and stirred for 5 min. n-Butylamine (1 ml.) dissolved in 4 ml. of dry DCM is added dropwise within 30 min and then the reaction mixture is stirred at room temperature for 96 h. 180 ml. of water and 30 ml. of acetic acid are added and the mixture is heated under reflux at 47 °C for 1 h. After cooling down to room temperature, a yellow precipitate is removed by filtration. The aqueous phase is separated. The DCM phase is dried over sodium sulfate and then evaporated to dryness under reduced pressure. The crude orange product is recrystallized from isopropyl alcohol twice to obtain 12.83 g (40% of theory) of compound (101 ) as yellow crystals.

H NMR (CDCIs): 7.62 (d, J= 15.8 Hz, 2H, Ar-CH=C), 7.40 (s, 4H, Ar), 6.49 (d, J= 15.8 Hz, 2H, Ar-C=CH), 5.86 (s, 1 H, 0-C=CH), 5.52 (s, 2H, OH), 1.47 (s, 36H, CH ₃ ) ppm

IR (KBr): 361 1 (s), 3448 (br), 2958 (m), 1617 (s), 1566 (m), 1525 (m), 1422 (m), 1206 (m), 1 130 (m), 952 (m), 852 (s) cm- ¹

Example S-2: Synthesis of compound (102)

To a solution of compound (101 ) (15.16 g, 0.028 mol) in 200 ml. of THF, 10 % Pt/C (1 .01 g) is added. After degassing, the mixture is hydrogenated at room temperature and normal pressure for 2 h. The catalyst is removed by filtration, washed with THF and the solution is concentrated. The resulting crude product is slowly recrystallized from cyclohexane multiple times at room temperature. 12.62 g (83% of theory) colorless crystals of compound (102) are collected by fil- tration, washed with cyclohexane and dried in vacuum.

¹ H NMR (CDCIs): 6.99 (s, 4H, Ar), 6.96 (s, 1 H, C=C-OH), 5.52 (s, 1 H, 0-C=CH), 5.07 (s, 2H, Ar- OH), 2.85 (m, 4H, CH ₂ ), 2.57 (m, 4H, CH ₂ ), 1.43 (s, 36H, CH ₃ ) ppm

1 ³ C NMR (CDCIs): 193.7 (C=0), 152.1 (Ar-OH), 136.0 (Ar), 131 .2 (Ar), 124.8 (Ar), 99.6

(CH ₂ (C=0) ₂ ), 40.6 (CH ₂ (C=0)(CH ₂ )), 34.3 (Ar-CH ₂ ), 31 .8 (C(CH ₃ ) ₃ ), 30.3 (CH ₃ ) ppm

IR (KBr): 3638 (s), 3446 (br), 2958 (m), 2929 (m), 2869 (m), 1610 (s), 1433 (m), 1393 (w), 1362 (w), 1318 (w), 1230 (m), 1 164 (m), 1 121 (w), 872 (w) cm ^"1

Elemental analysis: calcd. for C ₃ 5H ₅₂ 04 ((102)): C 78.31 , H 9.76; found: C 74.68, H 9.16 MS (FT): 537 ([M+H] ⁺ ) Example S-3: Synthesis of compound (103)

A solution of compound (101 ) (2.55 g, 4.786 mmol) in 1200 mL of methanol is treated with 50 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. FeC -6 H2O (0.45 g, 1.655 mmol), dissolved in 150 mL of water, is added and the resulting brown suspension is heated under reflux at 85 °C for 3 h. After evaporating the methanol under reduced pressure, 2.41 g (88% of theory) of compound (103) is collected as a brown solid by filtration and dried in vacuum.

IR (KBr): 3634 (m), 2956 (m), 1621 (m), 1514 (s), 1423 (m), 1390 (m), 1236 (m), 1206 (m), 1 154 (m), 971 (w), 856 (w) cm- ¹

Elemental analysis: calcd. for dosHwFeOis ((103)-3 H ₂ 0 ^* ): C 73.96, H 8.69; found: C 73.94, H 8.17

^* assumed content of water in the obtained material

MS (ESI): 1651 ([M+H] ⁺ ) Example S-4: Synthesis of compound (104)

A solution of compound (101 ) (0.051 g, 0.096 mmol) in 60 mL of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. CrC -6 H2O (0.008 g, 0.030 mmol), dissolved in 10 mL of water, is added and the resulting yellow solution is heated under reflux at 85 °C for 4 h. After evaporating the methanol under reduced pressure, 0.012 g (24% of theory) of compound (104) is collected as a brown solid by filtration and dried in vacuum. IR (KBr): 3635 (m), 3616 (m), 2959 (s), 1619 (s), 1580 (m), 1433 (s), 1363 (w), 1299 (w), 1237 (w), 1206 (m), 1 156 (w), 1 130 (m), 969 (w), 853 (w) cm ^"1

Elemental analysis: calcd. for dosHwCrOis ((104)-3 H ₂ 0 ^* ): C 74.13, H 8.71 ; found: C 74.48, H 8.74

*assumed content of water in the obtained material

Example S-5: Synthesis of compound (105)

(105)

A solution of compound (101 ) (0.051 g, 0.096 mmol) in 60 mL of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. AlC (0.004 g, 0.030 mmol), dissolved in 10 mL of water, is added and the resulting yellow suspension is heated under reflux at 85 °C for 4 h. After cooling down to room temperature, 0.026 g (52% of theory) of compound (105) is collected as a brown solid by filtration and dried in vacuum.

IR (KBr): 3631 (m), 2957 (m), 1625 (m), 1523 (s), 1422 (m), 1299 (w), 1236 (m), 1206 (m), 1 157 (m), 972 (w), 858 (w) cm- ¹

Elemental analysis: calcd. for C105H145AIO14 ((105)-2 H ₂ 0 ^* ): C 76.05, H 8.81 ; found: C 76.31 , H

8.51

^* assumed content of water in the obtained material

MS (ESI): 1623 ([M+H] ⁺ )

Example S-6: Synthesis of compound (106)

A solution of compound (101 ) (0.510 g, 0.957 mmol) in 600 mL of methanol is treated with 10 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. CeC -7 H2O (0.1 18 g, 0.317 mmol), dissolved in 100 mL of water, is added and the resulting dark suspension is heated under reflux at 85 °C for 4 h. After cooling down to room temperature, a yellow solid is removed by filtration. After evaporating the methanol under reduced pressure, 0.458 g (81 % of theory) of compound (106) is collected as a brown solid by filtration and dried in vacuum.

IR (KBr): 3637 (m), 2958 (s), 1618 (s), 1585 (m), 1435 (s), 1363 (w), 1238 (m), 1206 (m), 1 158 (m), 1 1 19 (w), 885 (w) cm- ¹

Elemental analysis: calcd. for Cio ₅ Hi5 ₅ CeOi9 ((106)-7 H ₂ 0 ^* ): C 67.75, H 8.39; found: C 67.70, H 7.69

^* assumed content of water in the obtained material Example S-7: Synthesis of compound (107)

(107)

A solution of compound (101 ) (0.051 g, 0.096 mmol) in 60 ml. of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. NiC -6 H2O (0.01 1 g, 0.046 mmol), dissolved in 10 mL of water, is added and the resulting dark suspension is heated under reflux at 85 °C for 4 h. After cooling down to room temperature, 0.033 g (59% of theory) of compound (107) is collected as a brown solid by filtration and dried in vacuum.

IR (KBr): 3632 (m), 3423 (br) 2958 (s), 1626 (s), 1512 (s), 1427 (s), 1301 (w), 1237 (m), 1206 (m), 1 156 (m), 1 1 19 (w), 854 (w) cm- ¹

Elemental analysis: calcd. for C70H104N1O13 ((107)-5 H ₂ 0 ^* ): C 69.35, H 8.65; found: C 69.73, H 8.39

^* assumed content of water in the obtained material

Example S-8: Synthesis of compound (108)

(108)

A solution of compound (101 ) (0.052 g, 0.098 mmol) in 60 mL of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. CoC -6 H2O (0.01 1 g, 0.046 mmol), dissolved in 10 mL of water, is added and the resulting orange suspension is heated under reflux at 85 °C for 4 h. After evaporating the methanol under reduced pressure, 0.026 g (47% of theory) of compound (108) is collected as a brown solid by filtration and dried in vacuum.

IR (KBr): 3636 (m), 2959 (s), 1623 (s), 1584 (m), 1509 (m), 1434 (s), 1363 (w), 1238 (m), 1206 (m), 1 158 (m), 1 1 19 (w), 886 (w) cm- ¹ Elemental analysis: calcd. for C70H104C0O13 ((108)-5 H ₂ 0 ^* ): C 69.34, H 8.65; found: C 69.24, H 7.94

^* assumed content of water in the obtained material Example S-9: Synthesis of compound (109)

(109)

A solution of compound (101 ) (0.054 g, 1 .014 mmol) in 60 ml. of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. MnC -4 H2O (0.009 g, 0.045 mmol), dissolved in 10 mL of water, is added and the resulting brown suspension is heated under reflux at 85 °C for 3 h. After evaporating the methanol under reduced pressure, 0.054 g (88% of theory) of compound (109) is collected as a brown solid by filtration and dried in vacuum.

IR (KBr): 3638 (m), 2958 (s), 1615 (s), 1436 (s), 1364 (m), 1238 (m), 1203 (m), 1 159 (m), 1 1 19 (w), 885 (w) cm- ¹

Elemental analysis: calcd. for C ₇ oHio4MnOi ₃ ((109)-5 H ₂ 0 ^* ): C 69.57, H 8.67; found: C 69.37, H 7.74

^* assumed content of water in the obtained material

Example S-10: Synthesis of compound (1 10)

(110)

A solution of compound (101 ) (0.050 g, 0.094 mmol) in 60 mL of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. ZnC (0.006 g, 0.044 mmol), dissolved in 10 mL of water, is added and the resulting yellow suspension is heated under reflux at 85 °C for 4 h. After evaporating the methanol under reduced pressure, 0.007 g (14% of theory) of compound (1 10) is collected as a orange solid by filtration and dried in vacuum.

IR (KBr): 3634 (m), 2958 (s), 1669 (m), 1622 (m), 1580 (m), 151 1 (m), 1431 (s), 1363 (w), 1298 (w), 1238 (m), 1203 (m), 1 158 (m), 1 103 (w), 970 (w), 888 (w) cm ^"1

Elemental analysis: calcd. for C ₇ oHio ₂ ZnOi2 ((1 10)-4 H ₂ 0 ^* ): C 70.01 , H 8.56; found: C 70.21 , H 7.79

^* assumed content of water in the obtained material

Example S-1 1 : Synthesis of compound (1 1 1 )

A solution of compound (101 ) (0.510 g, 0.957 mmol) in 600 mL of methanol is treated with 10 mL 0.1 M sodium hydroxide solution and the resulting dark solution is stirred for 5 min. CuC -2 H2O (0.081 g, 0.475 mmol), dissolved in 100 mL of water, is added and the resulting green suspension is heated under reflux at 85 °C for 4 h. After cooling down to room temperature, 0.461 g (83% of theory) of compound (1 1 1 ) is collected as a brown solid by filtration and dried in vacuum.

IR (KBr): 3629 (m), 2958 (s), 1621 (s), 1517 (s), 1424 (s), 1238 (m), 1207 (m), 1 157 (m), 1 1 19 (w), 857 (w) cm- ¹

Elemental analysis: calcd. for C ₇ oH ₉ 8CuOio ((1 1 1 )-2 H ₂ 0 ^* ): C 72.29, H 8.49; found: C 72.46, H 8.24

^* assumed content of water in the obtained material

Example S-12: Synthesis of compound (1 12)

(1 12)

A solution of compound (102) (0.365 g, 0.680 mmol) in 70 mL of methanol is treated with 7.2 mL 0.1 M sodium hydroxide solution and the resulting colorless solution was stirred for 5 min. AICI3 (0.045 g, 0.337 mmol), dissolved in 8 mL of water, is added and the resulting colorless suspension is heated under reflux at 85 °C for 2 h. After cooling down to room temperature, 0.222 g (55% of theory) of compound (1 12) is collected as a colorless solid by filtration and dried in vacuum.

IR (KBr): 3645 (m), 2958 (m), 1587 (s), 1525 (s), 1434 (s), 1361 (w), 1315 (w), 1231 (m), 1 160 (m), 1024 (w), 874 (w), 768 (w) cm ^"1

Elemental analysis: calcd. for C105H171AIO21 ((1 12) 9 H ₂ 0 ^* ): C 70.20, H 9.59; found: C 70.02, H 8.66

^* assumed content of water in the obtained material

Example S-13: Synthesis of compound (1 13)

A solution of compound (102) (0.052 g, 0.097 mmol) in 10 mL of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting colorless solution was stirred for 5 min. CeC -7 H2O (0.012 g, 0.032 mmol), dissolved in 1 mL of water, is added and the resulting colorless suspension is heated under reflux at 85 °C for 4 h. After cooling down to room temperature, 0.050 g (84% of theory) of compound (1 13) is collected as a colorless solid by filtration and dried in vacuum.

IR (KBr): 3645 (m), 2959 (m), 1579 (s), 1518 (s), 1435 (s), 1363 (w), 1314 (w), 1231 (m), 1 161 (m), 1021 (w), 874 (w), 769 (w) cm ^"1

Elemental analysis: calcd. for Cio ₅ Hi6iCeOi ₆ ((1 13)-4 H ₂ 0 ^* ): C 69.31 , H 8.92; found: C 69.64, H 8.96

^* assumed content of water in the obtained material

Example S-14: Synthesis of compound (1 14)

(114)

A solution of compound (102) (0.050 g, 0.093 mmol) in 10 mL of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting colorless solution is stirred for 5 min. CaC (0.005 g, 0.045 mmol), dissolved in 1 mL of water, is added and the resulting colorless suspension is heated under reflux at 85 °C for 4 h. After cooling down to room temperature, 0.036 g (69% of theory) of compound (1 14) is collected as a colorless solid by filtration and dried in vacuum.

IR (KBr): 3646 (m), 2957 (m), 1597 (s), 1513 (s), 1434 (s), 1363 (w), 1315 (w), 1231 (m), 1 161 (m), 1022 (w), 874 (w), 768 (w) cm ^"1

Elemental analysis: calcd. for CroHioeCaOio ((114)-2 H ₂ 0 ^* ): C 73.26, H 9.31 ; found: C 73.31 , H 8.85

^* assumed content of water in the obtained material

Example S-15: Synthesis of compound (1 15)

A solution of compound (102) (2.39 g, 4.45 mmol) in 500 ml. of methanol is treated with 50 ml_ 0.1 M sodium hydroxide solution and the resulting colorless solution is stirred for 5 min. MgC -6 H2O (0.474 g, 2.33 mmol), dissolved in 50 ml. of water, is added and the resulting colorless suspension is heated under reflux at 85 °C for 2 h. After cooling down to room temperature, 2.30 g (87% of theory) of compound (1 15) is collected as a colorless solid by filtration and dried in vacuum.

IR (KBr): 3645 (m), 2958 (m), 1593 (s), 1518 (s), 1435 (s), 1363 (w), 1321 (w), 1231 (m), 1 160 (m), 874 (w), 768 (w) cm ^"1

Elemental analysis: calcd. for C ₇ oHii ₂ MgOi3 ((1 15)-5 H ₂ 0 ^* ): C 70.89, H 9.52; found: C 71 .24, H 9.03

^* assumed content of water in the obtained material

Example S-16: Synthesis of compound (1 16)

(116)

A solution of compound (102) (0.052 g, 0.097 mmol) in 10 mL of methanol is treated with 1 ml_ 0.1 M sodium hydroxide solution and the resulting colorless solution is stirred for 5 min. MnC -4 H2O (0.009 g, 0.045 mmol), dissolved in 1 mL of water, is added and the resulting colorless suspension is heated under reflux at 85 °C for 4 h. After cooling down to room temperature, 0.041 g (76% of theory) of compound (1 16) is collected as a pale brown solid by filtration and dried in vacuum.

IR (KBr): 3644 (m), 2958 (m), 1582 (s), 1515 (s), 1434 (s), 1364 (w), 1315 (w), 1232 (m), 1 161 (m), 1021 (w), 875 (w), 769 (w) cm ^"1

Elemental analysis: calcd. for C ₇ oHii ₂ MnOi3 ((1 16)-5 H ₂ 0 ^* ): C 69.1 1 , H 9.28; found: C 68.68, H 8.72

^* assumed content of water in the obtained material

Example S-17: Synthesis of compound (1 17)

(117) A solution of compound (102) (2.43 g, 4.53 mmol) in 250 mL of methanol is treated with 50 mL 0.1 M sodium hydroxide solution and the resulting colorless solution is stirred for 5 min. ZnC (0.33 g, 2.42 mmol), dissolved in 10 mL of water, is added and the resulting colorless suspension is heated under reflux at 85 °C for 3 h. After cooling down to room temperature, 2.15 g (78% of theory) of compound (1 17) is collected as a colorless solid by filtration and dried in vacuum.

IR (KBr): 3645 (m), 2958 (m), 1582 (s), 1517 (s), 1435 (s), 1364 (w), 1314 (w), 1231 (m), 1 161 (m), 1021 (w), 873 (w), 768 (w) cm ^"1

Elemental analysis: calcd. for C ₇ oHiioOi ₂ Zn ((1 17)-4 H ₂ 0 ^* ): C 69.54, H 9.17; found: C 69.1 1 , H 8.76

^* assumed content of water in the obtained material

Example S-18: Synthesis of compound (1 18)

(118)

A solution of compound (102) (0.051 g, 0.095 mmol) in 10 mL of methanol is treated with 1 mL 0.1 M sodium hydroxide solution and the resulting colorless solution is stirred for 5 min. CuC -2 H2O (0.008 g, 0.047 mmol), dissolved in 1 mL of water, is added and the resulting green suspension is heated under reflux at 85 °C for 2 h. After cooling down to room temperature, 0.044 g (82% of theory) of compound (1 18) is collected as a pale green solid by filtration and dried in vacuum.

IR (KBr): 3645 (m), 2958 (m), 1571 (s), 1518 (s), 1434 (s), 1315 (w), 1232 (m), 1 162 (m), 1024 (w), 874 (w), 769 (w) cm ^"1

Example S-19: Synthesis of compound (1 19)

A solution of compound (102) (0.510 g, 0.950 mmol) in 100 mL of methanol is treated with 10 mL 0.1 M sodium hydroxide solution and the resulting colorless solution iss stirred for 5 min.

EuC -6 H2O (0.1 17 g, 0.319 mmol), dissolved in 10 mL of water, is added and the resulting colorless suspension is heated under reflux at 85 °C for 2 h. After cooling down to room temperature, 0.415 g (73% of theory) of compound (1 19) is collected as a colorless solid by filtration and dried in vacuum. IR (KBr): 3651 (m), 2958 (m), 1597 (s), 1517 (s), 1433 (s), 1363 (w), 1315 (w), 1231 (m), 1 161 (m), 1020 (w), 875 (w), 768 (w) cm ^"1

Application examples

The following known stabilizers are employed in addition to the inventive compounds:

Irganox 1010 (RTM BASF), which contains pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4- hydroxyphenyl)propionate).

Irgafos 168 (RTM BASF), which contains tris(2,4-di-tert-butylphenyl) phosphite.

Irganox B 215 (RTM BASF), which is a blend of 67% Irgafos 168 and 33% Irganox 1010.

CaSt is commercially available calcium stearate, which acts as acid scavenger.

Example A-1 : Stabilization of a Ziegler-Natta polypropylene homopolymer

Polymer processing experimental (DSM Miniextruder)

The employed DSM miniextruder enables a flow of the melted polymer in a circle. Two screws in a twin-screw arrangement press the melted polymer to the outlet, which is connected to the inlet zone of the extruder. The temperature of the steel barrel of the mini-extruder can be regulated and the inlet zone of the extruder can be purged with a gas, which allows the removal of entrapped air originating from the loading of the polymer sample. Furthermore, a sensor deter- mines the force, which is exerted by the melted polymer onto the barrel during rotation of the two screws. A change in the viscosity of the melted polymer leads to a change of the force. During the experiment, the steel housing of the extruder is set at a temperature of 280°C and the inlet zone is set under a nitrogen flow of 20 ml. / min. At a screw speed of 100 rpm, 10 g of a mixture, which consists of 99.975% of a polypropylene homopolymer and 0.025% of a com- pound as stated in table A-1 , is loaded. After loading, the test is conducted for 10 min and the force exerted on the barrel is recorded. The linear decrease of the force is quantified as slope of the force-to-time curve, wherein the slope is calculated between the time period of 4 and 10 minutes. The decrease of the force with time is taken as degree of polymer degradation of the sample. Desired is a minimum of degradation, which is expressed by a small value for the slope of the curve. No degradation would mean zero slope. The results are shown in table A-1 .

Table A-1

composition No. tested composition type of metal polymer degradasalt or bi- tion / slope sphenolic

compound ^c >

0 without addition of a com-0.39

pound according to the

invention ^a >

1 Irganox 1010 ^a > - -0.30

2 compound (101 ) ^b > [(H); =] -0.22

3 compound (103) ^b > [Fe ³⁺ ; =] -0.14 4 compound (104) ^b > [Cr ³⁺ ; =] -0.29

5 compound (106) ^b > [Ce ³⁺ =] -0.25

6 compound (107) ^b > [Ni ²⁺ ; =] -0.24

7 compound (108) ^b > [Co ²⁺ =] -0.25

8 compound (109) ^b > [Mn ²⁺ =] -0.19

9 compound (1 10) ^b > [Zn ²⁺ =] -0.26

10 compound (1 1 1 ) ^b > [Cu ²⁺ =] -0.17

1 1 compound (1 12) ^b > [Al ³⁺ -] -0.26

12 compound (1 13) ^b > [Ce ³⁺ ; -] -0.13

13 compound (1 15) ^b > [Mg ²⁺ ; -] -0.16

14 compound (1 16) ^b > [Mn ²⁺ ; -] -0.17

15 compound (1 17) ^b > [Zn ²⁺ ; -] -0.25

Footnotes: a) reference;

b) inventive;

c) ["metal ion" or "(H)"; "=" for A ¹ = A ² = -CH=CH- or "-" for A ¹ = A ² = -CH ₂ -CH ₂ -] Compared to the reference compositions, which contain no stabilizer or contain the phenolic antioxidant Irganox 1010, test compositions with the stated compounds show better stabilization performances.

Examples A-2-1 and A-2-2: Stabilization of a Ziegler-Natta polypropylene homopolymer

Polymer processing experimental (Multiple pass extrusion)

A Ziegler-Natta polypropylene homopolymer from a bulk/slurry phase polymerization process is evaluated. The processing conditions are described below. The various additives are blended according to table A-2-1 and A-2-2 with the granular polymer, which is essentially free of any stabilization additives. The blending is carried out using a M 10 FU mixer from MTI. The thoroughly blended formulations are then melt compounded in a single screw extruder (Teach-Line Extruder E20T SCD 15 from Dr. Collin; L/D=25) at a lower temperature of 200°C under nitrogen, which is denoted as the zero pass extrusion. This ensures good melt mixing with minimal damage to the polymer due to oxidative degradation. The resultant zero pass extrudate is then ex- truded multiple times in a single screw extruder at a higher temperature (280°C). Pelletized samples of zero, first, third and fifth pass extrudate are collected and stored in sealed plastic bags at room temperature.

Melt Flow Rates: The samples are tested for retention of molecular mass (weight). This is measured by melt flow rate retention (according to ASTM-1238) on a MD-P melt index tester from Goettfert at the test conditions of 230°C and 2.16 kg. Melt flow rates are measured in grams of polymer that flow out of a defined orifice in 10 minutes and are stated as grams / 10 minutes (decigrams per minute). Example A-2-1 : The multiple pass extrusions are performed at 280°C and under nitrogen. The results are shown in table A-2-1.

Table A-2-1

Footnotes: a) reference

b) inventive

c) type of phenolic metal salt or bisphenolic compound

["metal ion" or "(H)"; "=" for A ¹ = A ² = -CH=CH- or "-" for A ¹ = A ² = -CH ₂ -CH ₂ -]: compound (102) [(H); -], compound (1 17) [Zn ²⁺ ; -], compound (1 15) [Mg ²⁺ ; -], compound (103) [Fe ³⁺ ; =]

In general, the ternary blends comprising an inventive compound (125 ppm) provide as good or better performance in comparison to the common binary blends. The addition of 125 ppm of the inventive compound (103) at formulation No. 6 clearly improves the melt stability compared to the common binary blend.

Example A-2-2:

The multiple pass extrusions are performed at 280°C and open to air. Extrusion at higher temperatures in combination with the presence of oxygen (air) enhances the rate of polymer degradation. The results are shown in table A-2-2.

Table A-2-2

composition No. 1 a) 2 ^a) 3 ^b > 4 b) 5 > 6 > PP 99.8400 99.7900 99.8400 99.8275 99.8275 99.8275

CaSt 0.0600 0.0600 0.0600 0.0600 0.0600 0.0600

Irganox 1010 ^c > 0.0330 0.0500 - 0.0330 0.0330 0.0330

Irgafos 168 ^c > 0.0670 0.1000 - 0.0670 0.0670 0.0670 compound (1 17) ^d > - - 0.1000 0.0125 - - compound (1 15) ^d > - - - - 0.0125 - compound (103) ^d > - - - - - 0.0125 total additives con0.1600 0.2100 0.1600 0.1725 0.1725 0.1725 tent

Melt flow rates at 280°C melt processing

zero pass 10.2 10.2 10.7 10.6 10.1 10.3

1 ^st pass 15.3 12.9 15.2 13.3 14.0 12.9

3 ^rd pass 26.3 20.3 25.1 23.3 25.1 17.6

5 ^th pass 44.9 30.6 36.3 37.2 36.9 23.8

Footnotes: a) reference

b) inventive

c) added in the form of Irganox B 215

d) type of phenolic metal salt

["metal ion"; "=" for A ¹ = A ² = -CH=CH- or "-" for A ¹ = A ² = -CH ₂ -CH ₂ -]:

compound (1 17) [Zn ²⁺ ; -], compound (1 15) [Mg ²⁺ ; -], compound (103) [Fe ³⁺ ; =]

1000 ppm of compound (1 17) provide better performance in comparison to the common binary blend of Irganox 1010 and Irgafos 168 (in the form of Irganox B 215) at the same concentration (1000 ppm). The ternary blends comprising an inventive compound (125 ppm) provide as good or better performance in comparison to the common binary blend Irganox B 215. The addition of 125 ppm of the inventive compound (103) at formulation No. 6 clearly improves the melt stability compared to the common binary blend (1000 or 1500 ppm).