A dispersant for coating system

Field of the I nvention

The present invention relates to a branched modified polyetheramine polyol having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol that is used as a universal dispersant for coating system, in ks and color filters.

Backgrou nd of the I nvention

Dispersions containing solid dispersible particles, such as organic or inorganic pigments and fillers, and polymer additives, namely dispersants, are used in an almost unlimited number of different technical applications, e.g. as coating materials, for printing in ks, colou ring plastic materials, including fibres, glasses, or ceramic products, for formu lations in cosmetics, or for the preparation of paint systems, in particu lar automotive, industrial and decorative paints.

The function of the polymeric dispersant in such dispersions is manifold. Mainly, they act as stabilizers for the solid particulate materials, i.e. the dispersant separates the particles of the solid particulate material and thus prevents them from coagu lation or clumping and settling from the liquid phase. They also may act as solubilizers in the given carrier liquid, e.g. water or organic solvents. The polymer additives may also improve the gloss of the dispersion or enhance its rheology. Depending on the type and the polarity of the dispersing agent, e.g. water, organic solvents or mixtures thereof, polymers of variable structure are chosen. I n view of ecological requirements, the use of the aqueous pigment dispersions is particularly preferred, as wel l as the dispersions based on organic solvents with high solids content.

WO 92/13911A1 relates to an acetoacetanilide functionalized poly(alkylene glycol), which are prepared by reacting a poly(alkylene glycol) monoamine, diamine or triamine with isatoic anhydride followed by acetoacetylation of the resultant aminobenzamide. WO 92/13911A1 suggests using said acetoacetanilide functionalized poly(alkylene glycol)s for preparing the improved diarylide pigment com positions, which in turn are usefu l for preparing the storage stable printing inks, especially of the publication gravu re type inks.

WO 00/40630 discloses pigment dispersions containing block copolymers as dispersants prepared by the ATRP method (atom transfer radical polymerisation) of ethy lenical ly unsaturated monomers. The block copolymers consist of defined hyd rophobic and hyd rophilic polymer blocks. WO 03/046029 discloses block copolymers as dispersants, which are similar to those of WO 00/40630 but which are subsequently neutralized with specific salt forming com pounds.

W02008107326 and the literatu re cited therein relates to poly(alkylene imine) grafted polymers of the acrylate, polyether or polyester type, which are usefu l as pigment dispersants. Polymers having pending anthranilate or anthranilamide groups, which may be attached directly or via a bivalent spacer to the polymer back-bone or to the termini of the polymers have been described several times as crosslinkers or chain extenders for polyurethanes or epoxies, e.g. from the following patent documents:

Anthranilate functionalized poly(alkylene oxide)s are e.g. known from US 4,180,644, US 4,191,706, US 4,191,835, US 4,247,677, US 4,260,729 and US 2003/212291. Anthranilate functionalized poly(alkylene oxide)s are used as a crosslinker agent for polyu rethane or epoxy coatings.

Anthranilate fu nctionalized polyesters are e.g. known from EP 21569. They are used as a chain extender in the production of polyurea and polyu rea-polyurethane.

Anth ranilate fu nctionalized polycarbonates are e.g. known from US 5,231,149.

They are used for the production of graft or block copolymers having im proved impact and solvent resistance.

WO 2018/162403 discloses the use of hydrophobically modified polyalkanolamines obtainable by condensing at least one trialkanolamine and optionally further condensable monomers and reacting at least one of the terminal OH grou ps with suitable reactants capable of reacting with OH grou ps and comprising long chain hyd rocarbon grou ps as wax in hibitors, pour point depressant and additive for lubricants.

WO 2017/125290 discloses a dispersant composition comprising: a) at least one oligomeric acid A, which has i) at least one acidic group selected from COOH and P0 ₃ H ₂ , and ii) at least one polyoxyalkylene-ether radical of the formula (I): R-(0-A) _x O-G-, where A is an C ₂ - C ₄ -a I ka n - 1,2-d iy I radical; X is an integer havi ng a number average value in the range from 2 to 20; and R is hyd rocarbon radical having from 1 to 30 carbon atoms; G is a chemical bond or a carbonyl group; and b) at least one polyamine B, which is selected from the group consisting of polyvinylamines, poly-C ₂ -C ₃ -alkyleneimines, modified poly-C ₂ -C ₃ - alkyleneimines, melamine compounds, modified melamine compounds, poly-(C ₂ -C ₄ - alkyleneether) amines, polyetheramine polyols, and modified polyetheramine polyols.

US 2014/014004 discloses branched polyetheramine polyols with a Hazen colour number in the range of from 100 to 600 (APHA), based on a polycondensation product of at least one trialkanolamine.

I n view of the almost u nlimited range of different tech nical applications, there remains a growing need for the dispersants of improved pigment affinity and rheology behaviou r, as expressed by the viscosity of the millbase at a given shear rate and improved gloss of su rface coatings.

It has now surprisingly found that the use of branched polyetheramine polyol modified with at least one component B having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol has beneficial properties while using as a dispersant in coating compositions, such as superior pigment affinity, show improved rheology behaviour and improved gloss of surface coatings.

Therefore, present invention discloses a branched polyetheramine polyol modified with at least one com ponent B having many beneficial properties. The present invention further discloses a branched polyetheramine polyol modified with at least one component B mixed with at least one polymeric carboxylic acid or at least one polymeric phosphoric acid to exhibit many beneficial properties.

Sum mary of the Invention

Su rprisingly, it was found that the use of a branched polyetheramine polyol modified with at least one component B having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol has beneficial properties while using as a dispersant in coating compositions, such as superior pigment affinity, show im proved rheology behaviour and im proved gloss of su rface coatings.

Thus, in first aspect, the presently claimed invention is directed to a branched modified polyetherami ne polyol havi ng a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, preferably determined by gel permeation chromatography in accordance with DI N 55672-1, which is obtained by reacting a mixture comprising, a) at least one branched polyetheramine polyol P containing at least one hydroxyl grou p, having a weight average molecu lar weight M _w in the range of > 500 g/mol to < lOOOOg/mol, preferably determined by gel permeation ch romatography in accordance with DIN 55672-1, and b) at least one compound B selected from- i) compounds of formula (I)

R-Fg (l) wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy; linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and Ci-C ₄ -alkoxy; a cycloaliphatic radical having at least 5 carbon atoms, wherein the

cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected, from OH, Ci-C ₄ -alkyl and CrC ₄ -alkoxy; and

aryl and aryl-Ci-C ₄ -alkyl, wherein the aryl part is u nsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, NH ₂ , N HCrC^alkyl, N (CrC ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and Fg is selected from the group consisting of carboxylic acid, carboxylic acid anhydride, carboxylic acid ester, isocyanate, and mixtures thereof;

(ii) compounds of the formulae (I I) and (II I)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N HCrC ₄ -alkyl, N (C _I -C ₄ - alkyl) ₂ , C ₁ -C ₄ -alkyl and CZ-CZ-alkoxy; and

R ² is selected from the group consisting of hydrogen and CrC ₄ -alkyl;

(iii) lactones of the formula (IV)

wherein A is a C ₃ -C ₁₂ -alkylene, which is u nsubstituted or substituted by 1 or 2 radicals

selected from OH, Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; iv) internal anhydride of the formu la (V)

wherein D is a C ₂ -C ₆ -alkylene, which is u nsubstituted or substituted by 1 or 2 radicals selected from OH, C _j -C ₄ -alkyl and -CValkoxy.

I n a second aspect, the presently claimed invention is directed to a branched modified polyetherami ne having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100,000 g/mol, which is obtained by reacting a mixtu re comprising a) at least one branched modified polyetheramine polyol is fu rther modified with b) at least one compound B selected from i) compounds of formula (I)

R-Fg (l) wherein R is selected from the grou p consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy; linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy; a cycloaliphatic radical having at least 5 carbon atoms, wherein the

cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected, from OH, Ci-C ₄ -alkyl and C _j -C^alkoxy; and

aryl and aryl-Ci-C ₄ -alkyl, wherein the aryl part is unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, NH ₂ , N HCrC^alkyl, N (CrC ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

Fg is independently of one another, selected from the grou p consisting of carboxylic acid, hyd roxy carboxylic acid, carboxylic acid anhydride, carboxylic acid ester, isocyanate, and mixtures thereof;

(ii) compounds of the formu lae (II) and (I II)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N HCrC ₄ -alkyl, N (C _I -C ₄ - alkyl) ₂ , Ci-C ₄ -alkyl and C^C^alkoxy; and

R ² is selected from the group consisting of hydrogen and C _r C ₄ -alkyl;

(iii) lactones of the formula (IV) o

A A _ O

(IV)

wherein A is a C ₃ -C ₁₂ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; iv) internal anhydride of the formu la (V)

wherein D is selected from the grou p consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2- phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a Ci-Ci ₈ alkyl or Ci-Ci ₈ alkenyl radical and 1,2-phenylene is u nsubstituted or substituted by 1 or 2 radicals selected from the group consisting of 1 or 2 radicals selected from OH, C ₁ -C ₄ -alkyl and Cr C ₄ -alkoxy, -COOH or halogen.

I n a third aspect, the presently claimed invention is directed to a liquid composition in the form of a dispersion com prising, a branched modified polyetheramine and/or a branched modified polyetheramine which is further modified with an at least one component B and a particulate solid material selected from the group consisting of pigments and fillers and a liquid diluent, wherein the particu late solid material is dispersed in the liquid diluent.

I n a fou rth aspect, the presently claimed invention is directed to the use of a branched modified polyetheramine and/or a branched modified polyetheramine which is further modified with an at least one component B and salts thereof as a dispersant for the particulate solid material selected from the grou p consisting of pigments and fillers.

Detailed description of the I nvention

Before the present compositions and formu lations of the presently claimed invention are described, it is to be understood that this invention is not limited to particu lar com positions and formulations described, since such compositions and formulation may, of course, vary. It is also to be u nderstood that the terminology used herein is not intended to be limiting, si nce the scope of the presently claimed invention will be limited only by the appended claims. If hereinafter a group is defined to comprise at least a certain nu mber of embodiments, this is meant to also encompass a grou p which preferably consists of these embodiments only. Fu rthermore, the terms 'first', 'second', 'third' or 'a', 'b', 'c', etc. and the like in the description and in the claims, are used for distinguishing between simi lar elements and not necessari ly for describing a sequential or chronological order. It is to be understood that the terms so used are interchangeable u nder appropriate circumstances and that the embodiments of the presently claimed invention described herein are capable of operation in other sequences than described or illustrated herein. In case the terms 'first', 'second', 'third' or ’(A)', '(B)' and '(C)' or '(a)', '(b)', '(c)', '(d)', U, 'ϋ' etc. relate to steps of a method or use or assay there is no time or ti me interval coherence between the steps, that is, the steps may be carried out simultaneously or there may be time intervals of seconds, minutes, hou rs, days, weeks, months or even years between such steps, unless otherwise indicated in the application as set forth herein above or below.

Fu rthermore, the ranges defined throughout the specification include the end values as well i.e. a range of 1 to 10 im plies that both 1 and 10 are included in the range. For the avoidance of doubt, applicant shall be entitled to any equivalents according to applicable law.

I n the following passages, different aspects of the presently claimed invention are defined in more detail. Each aspect so defined may be combined with any other aspect or aspects un less clearly indicated to the contrary. I n particu lar, any feature indicated as being preferred or advantageous may be combined with any other feature or featu res indicated as being preferred or advantageous.

Reference throughout this specification to 'one embodiment' or 'an embodiment' means that a particu lar featu re, structure or characteristic described in con nection with the embodiment is included in at least one embodiment of the presently claimed invention. Thus, appearances of the phrases 'in one embodiment' or 'in an embodiment' in various places th roughout this specification are not necessarily all referring to the same embodiment, but may.

Furthermore, the particu lar featu res, structu res or characteristics may be combined in any suitable man ner, as would be apparent to a person skilled in the art from this disclosure, in one or more embodiments. Fu rthermore, while some embodiments described herei n include some but not other featu res included in other embodiments, combinations of features of different embodi ments are meant to be within the scope of the presently claimed invention, and form different embodiments, as wou ld be understood by those in the art. For example, in the appended claims, any of the claimed embodiments can be used in any combination.

I n one embodiment, the presently claimed invention is directed to a branched modified polyetherami ne having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is obtained by reacting a mixture comprising, a) at least one branched polyetheramine polyol P containing at least one hydroxyl group, having a weight average molecular weight M _w in the range of > 500 g/mol to < 10000 g/mol and b) at least one compound B selected from- i) compounds of formula (I)

R-Fg (l) wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy; linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and Ci-C ₄ -alkoxy; a cycloaliphatic radical having at least 5 carbon atoms, wherein the

cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected, from OH, Ci-C ₄ -alkyl and CrC ₄ -alkoxy; and

aryl and aryl-Ci-C ₄ -alkyl, wherein the aryl part is unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, NH ₂ , NHC _j -C^alkyl, N(CrC ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

Fg is independently of one another, selected from the group consisting of carboxylic acid, carboxylic acid anhydride, isocyanate, and mixtures thereof;

(ii) compounds of the formulae (II) and (III)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , NHCrC ₄ -alkyl, N(0 ₄ -0 ₄ - alkyl) ₂ , Ci-C ₄ -alkyl and C _r C ₄ -alkoxy; and

R ² is selected from the group consisting of hydrogen and C C^alkyl;

(iii) lactones of the formula (IV) (IV)

wherein A is a C ₃ -C ₁₂ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and (VC^alkoxy; iv) internal anhydride of the formu la (V)

wherein D is selected from the group consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2- phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a C _j -C/g alkyl or C _j -C _jg alkenyl radical and 1,2-phenylene is u nsubstituted or substituted by 1 or 2 radicals selected from the group consisting of 1 or 2 radicals selected from OH, C C^alkyl and C/- C ₄ -alkoxy, -COOH or halogen.

I n a preferred embodiment, the branched modified polyetheramine has a weight average molecu lar weight M _w in the range of > 1,000 g/mol to < 100,000 g/mol, more preferably in the range of > 1,000 g/mol to < 80,000 g/mol, most preferably in the range of > 1,000 g/mol to < 50,000 g/mol, and particular preferably in the range of > 1,000 g/mol to < 30,000 g/mol.

I n one embodiment of the present invention, the at least one branched polyetheramine polyol has at least one, preferably at least three, more preferably at least six, most preferably at least ten terminal fu nctional groups per molecule. The functional groups in the context of the at least one branched polyetheramine polyol are, for exam ple, amino groups, preferably secondary or tertiary amino groups, and hyd roxyl groups. I n principle there is no upper limit on the number of terminal or pendent fu nctional groups. I n one embodiment of the present invention, the at least one branched polyetheramine polyol (B) has no more than 500 terminal functional groups per molecule, preferably no more than 100.

I n another preferred embodiment, the at least one branched polyetheramine polyol P containing at least one hydroxyl group, more preferably at least two hydroxyl groups, even more preferably at least three hydroxyl grou ps, still more preferably at least four hyd roxyl grou ps and most preferably at least 5 hydroxyl grou ps. I n another preferred embodiment, the at least one branched polyetherami ne polyol P contains preferably > 1 to < 50 hyd roxyl grou ps and most preferably > 3 to < 30 hydroxyl groups. I n a preferred embodiment, the at least one branched polyetheramine polyol P has a weight average molecular weight M _w in the range of > 500 g/mol to < 10,000g/mol, more preferably > 500 g/mol to < 8,000 g/mol, most preferably > 500 g/mol to < 5,000g/mol, and most preferably > 500 g/mol to < 3,000g/mol.

I n a preferred embodiment, the branched polyetheramine polyol is prepared by subjecting at least one trialkanolamine and/or at least one dialkanolamine to polycondensation in presence of a catalysis at a tem perature in the range of 100 to 500 °C, and that said polycondensation is carried out, optionally in an atmosphere of an inert gas.

I n a preferred embodiment, the at least one trialkanolamines will be subjected to polycondensation, for example selected from tri-C ₂ -C ₄ -alkanol-amines, with the alkanol grou ps in trialkanolamine being different or preferably identical. Trialkanolamine can be subjected to the polycondensation or to the co-polycondensation, either with one or more trialkanolamine or with one or more dialkanolamines. Examples for the suitable trialkanolamines are triethanolamine, tripropanolamine, triisopropanolamine and tributanolamine. Examples for the suitable dialkanolamines are N,N-diethanolamine, N,N- di-n-propanolamine, N,N-diisopropanolamine, N,N-di-n-butanolamine, N,N' -C ₂ -C ₈ - cu - hyd roxya Iky I piperidine.

I n a preferred embodiment, the branched polyetheramine polyol (B) can be obtained by the polycondensation of at least one of triethanolamine and/or diethanolamine, triisopropanolamine and/or tri-n-propanolamine, or mixtures of at least two of triethanolamine, triisopropanolamine and/or tri-n-propanolamine. Preference is given to make polyetheramine polyol (B) by the polycondensation of either triethanolamine or triisopropanolamine or a mixture of triethanolamine and triisopropanolamine.

I n a preferred embodiment, the catalyst used is an acid. The acid is an inorganic or an organic acid, more preferably the acid is an inorganic acid.

I n another preferred embodiment the inorganic acid is a mineral acid or a Lewis acid, more preferably, the acid is a mineral acid.

I n another preferred embodiment, the mineral acid is selected from the grou p consisting of su lfuric acid, hydroch loric acid, phosphoric acid (H ₃ P0 ₄ ), phosphorous acid (HgPOg/ phosphinic acid (H ₃ P0 ₂ ), perch loric acid, nitric acid, nitrous acid, sulphu rous acid, chloric acid, chlorous acid and hypoch lorous acid, more preferably the mineral acid is selected from su lfuric acid, phosphoric (H ₃ P0 ₄ ), phosphorous acid (H ₃ P0 ₃ / phosphinic acid (H ₃ P0 ₂ ) and hyd rochloric acid, even more preferably the mineral acid is sulfuric acid and phosphorous acid (H ₃ P0 ₃ ) _, phosphinic acid (H ₃ P0 ₂ ).

I n another preferred embodiment, the Lewis acid is a metal-containing compound selected from the group consisting of a) ASX ₃ , GaX ₃ , BX ₃ , BX ₃ -(C ₂ H ₅ ) ₂ 0, BX ₃ -S(CH ₃ ) ₂ , AIX ₃ , (C ₂ H ₅ ) ₂ AIX, SbX ₃ , SbX ₅ , SnX ₂ , MgX ₂ , MgX ₂ -0(C ₂ H ₅ ) ₂ , ZnX ₂ , B iX ₃ , FeX ₂ , TiX ₂ , TiX ₄ , NbX ₅ , NiX ₂ , CoX ₂ , HgX ₂ , whereby X in each case denotes F, Cl, Br, S0 ₃ , CF ₃ -S0 ₃ , CH ₃ -S0 ₃ , or I;

b) BH ₃ , B(CH ₃ ) ₃ , GaH ₃ , AIH ₃ , AI(acetate)(OH) ₂ , AI[OCH (CH ₃ ) ₂ ] ₃ , AI(OCH ₃ ) ₃ , AI(OC ₂ H ₅ ) ₃ , Al ₂ 0 ₃ , (CH ₃ ) ₃ AI, Ti [OCH(CH ₃ ) ₂ ] ₃ CI, Ti [OCFH (CH ₃ ) ₂ ] ₄ , methylaluminu m di-(2,6-di-tert-butyl-4- methylphenoxide), methylalu minu m di-(4-brom-2,6-di-tert-butylphenoxide), LiCI0 ₄ ;

c) Mg(acetate) ₂ , Zn (acetate) ₂ , Ni(acetate) ₂ , Ni(N0 ₃ ) ₂ , Co(acetate) ₂ , Co(N0 ₃ ) ₂ ,

Cu (acetate) ₂ , CU (N0 ₃ ) _2I Li(acetate), Zr(acetylacetonate) ₄ , Si(acetate) ₄ , K(acetate),

Na(acetate), Cs(acetate), Rb(acetate), M n (acetate) ₂ , Fe(acetate) ₂ , Bi(acetate) ₃ ,

Sb(acetate) ₃ , Sr(acetate) ₂ , Sn(acetate) ₂ , Zr(acetate) ₂ , Ba(acetate) ₂ , Flg(acetate) ₂ ,

Ag(acetate), Tl(acetate) ₃ , Sc(fluoromethansu lfonate) ₃ , l_n (fluoromethanesulfonate) ₃ , Ni(fluoromethanesulfonate) ₂ , Ni(tosylate) ₂ , Co(fluoromethanesu lfonate) ₂ , Co(tosylate) ₂ , Cu (fluoromethanesulfonate) ₂ and Cu (tosylate) ₂ .

I n preferred embodiment, the branched polyetherami ne polyol is prepared at a temperature in the range of 100 to 500°C, more preferably in the range of 100 to 400°C, most preferably in the range of 200 to 400°C, and particu lar preferably in the range of 200 to 300°C.

I n another preferred embodiment, the inert gas is selected from nitrogen and noble gases such as argon.

I n an embodiment, the at least one compou nd B is a compound of formula (I)

R-Fg (l)

wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C ₁ -C ₄ -alkoxy;

linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy;

a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected, from OH, Ci-C ₄ -alkyl and C _j -04-alkoxy; and

aryl and aryl-Ci-C ₄ -alkyl, wherein the aryl part is u nsubstituted or substituted by 1, 2,

3, 4 or 5 radicals selected from halogen, OH, NH ₂ , N HCrC^alkyl, N (C ₁ -C ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and C _j -C^alkoxy;

more preferably R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted; linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted;

a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by Ci-C ₄ -alkyl and Ci-C ₄ -; and

aryl and aryl-Ci-C ₄ -alkyl, wherein the aryl part is u nsubstituted or substituted by 1, 2,

3, 4 or 5 radicals selected from halogen, OH, NH ₂ , N HC _j -C^alkyl, N (C ₁ -C ₄ -alkyl) ₂ , C ₁ -C ₄ -alkyl and C _j -C^alkoxy;

most preferably R is selected from the group consisting of linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted; linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted;

a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by C ₁ -C ₄ -alkyl and Ci-C ₄ -; and

particular preferably R is selected from the grou p consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted; and

linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted.

I n a preferred embodiment, R is a linear or a branched alkyl having at least 6 carbon atoms, wherein the alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j - C ₄ -alkoxy. More preferably R is a linear or a branched alkyl having 6 to 40 carbon atoms, wherein the alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j - C ₄ -alkoxy, even more preferably, R is a linear or a branched alkyl having 6 to 30 carbon atoms, wherein the alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy, most preferably, R is a linear or a branched alkyl having 10 to 30 carbon atoms, wherein the alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C ₁ -C ₄ -alkoxy, and in particu lar preferably R is a linear or a branched alkyl having 6 to 30 carbon atoms.

Within the context of the presently claimed invention, the term "alkyl", as used herein, refers to an acylic saturated aliphatic groups, including a linear or a branched alkyl satu rated hyd rocarbon radical denoted by a general formu la C _n H _2n+1 and wherein n is the number of carbon atoms 1, 2, 3, 4 etc. The examples of the linear and the branched unsubstituted alkyl having at least 6 carbon atoms are, but not limited to, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, nonadecyl and eicosyl; more preferably selected from the group consisting of hexyl, heptyl, octyl, nonyl, decyl, u ndecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl- decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso- hexadecyl, iso-octadecyl and iso-eicosyl, more preferably selected from the group consisting of 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso- hexadecyl, iso-octadecyl and iso-eicosyl.

I n another preferred embodiment, the com pou nd of formula R-Fg (I) does not include stearic acid (C ₁₇ H ₃₅ COOH).

The representative examples of the linear or the branched alkyl having at least 6 carbon atoms, substituted by 1 or 2 radicals selected from OH and C _! -C ₄ -alkoxy are, but not limited to, 2-hydroxy-hexyl, 2,3-dihydroxy-hexyl, 3-hydroxy-2-methoxyhexyl, 2-hydroxy-heptyl, 2,3- dihydroxy-heptyl, 3-hyd roxy-2-methoxyheptyl, 2,3-dimethoxyheptyl, 2-ethoxy-3-methoxy- heptyl, 2-isopropoxy-3-methoxy-heptyl, 2,3-diisopropoxyheptyl, 3-hydroxy-2-methoxyoctyl,

2.3-dimethoxyoctyl, 2-ethoxy-3-methoxy-octyl, 2-isopropoxy-3-methoxy-octyl, 2,3- diisopropoxyoctyl, 3-hydroxy-5-methoxyoctyl, 2,5-dimethoxyoctyl, 5-ethoxy-3-methoxy- octyl, 5-isopropoxy-5-methoxy-octyl, 4,7-diisopropoxyoctyl, 3-hydroxy-2-methoxynonayl,

2.3-dimethoxynonayl, 2-ethoxy-3-methoxy-nonayl, 2-isopropoxy-3-methoxy-nonayl, 2,3- diisopropoxynonayl, 3-hydroxy-2-methoxy dodecyl, 2,3-dimethoxy dodecyl, 2-ethoxy-3- methoxy- dodecyl, 2-isopropoxy-3-methoxy- dodecyl, 2,3-diisopropoxy dodecyl, 3-hydroxy-

2-methoxy dodecyl, 2,3-dimethoxy octadecyl, 2-ethoxy-3-methoxy- octadecyl, 2-isopropoxy-

3-methoxy- octadecyl, 2,3-diisopropoxy octadecyl, 3-hydroxy-5-methoxy octadecyl, 2,5- dimethoxy octadecyl, 5-ethoxy-3-methoxy- octadecyl, 5-isopropoxy-5-methoxy- octadecyl,

4.7-diisopropoxy octadecyl, 3-hydroxy-2-methoxy octadecyl, 2,3-dimethoxy octadecyl, 2- ethoxy-3-methoxy- octadecyl, 2-isopropoxy-3-methoxy- octadecyl, 2,3-diisopropoxy octadecyl, 4-hydroxy-8-methoxydodecyl, 12,3-dimethoxydodecyl, 2-ethoxy-13-methoxy- dodecyl, 12-isopropoxy-3-methoxy-dodecyl, 2,3-diisopropoxydodecyl, 3-hydroxy-2- methoxydodecyl, 2,3-dimethoxyoctadecyl, 2-ethoxy-13-methoxy-octadecyl, 12-isopropoxy- 3-methoxy-octadecyl, 15,13-diisopropoxyoctadecyl, 13-hydroxy-5-methoxyoctadecyl, 2,15- dimethoxyoctadecyl, 15-ethoxy-3-methoxy-octadecyl, 15-isopropoxy-15-methoxy-octadecyl,

14.7-diisopropoxyoctadecyl, 3-hydroxy-12-methoxyoctadecyl, 2,13-dimethoxyoctadecyl, 12- ethoxy- 15- methoxy-octadecy I, 7-isopropoxy-31-methoxy-octadecyl, 16,15- diisopropoxyoctadecyl.

I n a preferred embodiment, R is a linear or a branched alkenyl having at least 6 carbon atoms, wherein the alkenyl is u nsubstituted or substituted by 1 or 2 radicals selected from OH and Ci-C ₄ -alkoxy. Within the context of the presently claimed invention, the term "alkenyl" , as used herein, refers to an acylic unsatu rated aliphatic grou ps, including linear or branched alkenyl unsaturated hydrocarbon radical having at least one double bond. The alkenyl can have more than one double bond such as 2, 3, 4 etc. The double bonds may be conjugated (-C=C-C=C-) or isolated (-C=C-C-C-C=C-) or the double bonds can be on same carbon (-C-C=C=C-C).

I n a preferred embodiment, R is a linear or a branched alkenyl having at least 6 carbon atoms, wherein the alkenyl is u nsubstituted or substituted by 1 or 2 radicals selected from OH and C^C^alkoxy. More preferably R is a linear or a branched alkenyl having 6 to 40 carbon atoms, wherein the alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C^C^alkoxy, even more preferably, R is a linear or a branched alkenyl having 6 to 30 carbon atoms, wherein the alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and Ci-C ₄ -alkoxy, most preferably, R is a linear or a branched alkenyl having 10 to 30 carbon atoms, wherein the alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C C^alkoxy, and in particu lar preferably R is a linear or a branched alkenyl having 6 to 30 carbon atoms.

The representative examples of the linear and the branched alkenyl containing at least one double bond include, but are not limited to, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1-u ndecenyl, 2- undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2- tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2-hexadecenyl, 1- heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1-nonadecenyl, 2- nonadecenyl, 1-eicosenyl 2-eicosenyl, 1,4-hexadienyl, 1,3-hexadienyl, 2,5-hexadienyl, 3,5- hexadienyl, 2,4-hexadienyl, 1,3,5-hexatrienyl, 1 ,3,6- h eptatrie ny I, 1,4,7-octatrienyl or 2- methyl-l,3,5hexatrienyl, 1,3,5,7-octatetraenyl, 1,3,5,8-nonatetraenyl, 1,4,7,10- undecatetraenyl, 2-ethyl-l ,3,6,8-nonatetraenyl, 2-ethenyl-l,3,5,8-nonatetraenyl, 1, 3, 5,7,9- decapentaenyl, 1,4,6,8,10-undecapentaenyl, 1,4,6,9,11 -dodecapentaenyl, 1-hexenyl, 2- hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2- decenyl, 1-u ndecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2- hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1- nonadecenyl, 2-nonadecenyl, 1-eicosenyl 2-eicosenyl, 1,4-hexadienyl, 1,3-hexadienyl, 2,5- hexadienyl, 3,5-hexadienyl, 2,4-hexadienyl, 1,3,5-hexatrienyl, 1,3,6-heptatrienyl, 1,4,7- octatrienyl or 2-methyl-l,3,5hexatrienyl, 1,3,5,7-octatetraenyl, 1,3,5,8-nonatetraenyl, 1,4,7,10-u ndecatetraenyl, 2-ethyl-l ,3,6,8-nonatetraenyl, 2-ethenyl-l,3,5,8-nonatetraenyl, 1,3,5,7,9-decapentaenyl, 1,4,6,8,10-undecapentaenyl, 1,4,6,9,11 -dodecapentaenyl, 2-ethyl- hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso-hexadecyl, iso-octadecyl and iso-eicosyl.

The examples of the linear or the branched alkenyl having at least 6 carbon atoms, substituted by 1 or 2 radicals selected from OH and C^C^alkoxy are, but not limited to, 2- hyd roxy-hex-3-en-3-yl, 2,3-dihydroxy-hex-5-en-l-yl, 3-hyd roxy-5-methoxyhex-l-en-2-yl, 2- hyd roxy-hept-6-en-3-yl, 2,3-dihydroxy-hept-4-en-6-yl, 2,3-dihydroxy-hept-4-en-l-yl, 3- hyd roxy-2-methoxyhept-4-en-l-yl, 2,3-dimethoxyhept-5-en-4-yl, 2 -ethoxy-3 -m ethoxy- hept- 6-en-6-yl, 2-isopropoxy-3-methoxy-hept-4-en-7-yl, 2,3-diisopropoxyhept-6-en-5-yl, 3- hyd roxy-2-methoxyoct-5-en-7-yl, 2,3-dimethoxyoct-7-en-5-yl, 2-ethoxy-3-methoxy-oct-6- en-8-yl, 2-isopropoxy-3-methoxy-oct-6-en-8-yl, 2,3-diisopropoxyoct-5-en-8-yl, 3-hydroxy- 5-methoxyoct-4-en-l-yl, 2,5-dimethoxyoct-3-en-7-yl, 5-ethoxy-3-methoxy-oct-2-en-7-yl, 5- isopropoxy-5-methoxy-oct-2-en-l-yl, 4,7-diisopropoxyoct-3-en-l-yl, 3-hydroxy-2- methoxynon-5-en-9-yl, 2,3-dimethoxynon-4-en-5-yl, 2-ethoxy-3-methoxy-non-6-en-9-yl, 2- isopropoxy-3-methoxy-non-4-en-7-yl, 10-ethoxy-3-methoxy-dodec-5-enyl, 8-propoxy-3- methoxy-dodec-ll-enyl, 8-isopropoxy-3-methoxy-dodec-ll-enyl, 2,3-diisopropoxydodec-4- en-8-yl, 3-hydroxy-2-methoxydodec-7-en-12-yl, 2,3-dimethoxy octadic-5-en-ll-yl, 2- ethoxy-3-methoxy-octadec-6-en-17-yl, 2-isopropoxy-3-methoxy- octadic-12-en-l-yl, 2,3- diisopropoxyoctadec-5-en-18-yl, 3-hydroxy-5-methoxyoctadec-17-en-10-yl, 2,5- dimethoxyoctadec-2-en-18-yl, 5-ethoxy-3-methoxy-octadec-2-en-18-yl, 5-isopropoxy-5- methoxy-octadec-16-en-l-yl, 4,7-diisopropoxy octadic-3-en-l-yl, 14,7- diisopropoxyoctadec-3-en-l-yl.

I n a preferred embodiment, R is a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected, from OH, C _j -C^alkyl and C^C^alkoxy. The cycloaliphatic can be a monocyclic and a bicyclic. The representative exam ples of the u nsubstituted and the branched cycloaliphatic are, but not limited to cyclopentyl, cyclohexyl, cycloheptyl, bicyclo [2.2.1] heptyl and bicyc lo [3.1.1] he pty I. The representative examples of cycloaliphatic substituted with OH include, but are not limited to 2-hydroxy-pentyl, 2,4-dihydroxycyclohexyl, 3,6- dihydrocycloheptyl, etc. The cycloaliphatic that are optionally substituted with Ci-C ₄ -alkyl. The representative examples of the cycloaliphatic substituted with C _j -CT, alkyl include, but are not limited to methyl cyclohexyl, dimethyl cyclohexyl etc. The term "alkoxy" as used herein denotes in each case, is a straight-chain or branched alkyl grou p usually having from 1 to 4 carbon atoms ("C ₁ -C ₄ -alkoxy") which is bound to the remainder of the molecu le via an oxygen atom. C _j -CVAIkoxy is methoxy or ethoxy. The C^ -Alkoxy is additionally, for exam ple, is selected from, but not limited to, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). The representative examples of the cycloaliphatic substituted with C _! -C ₄ alkoxy include, but are not limited to methoxycyclohexyl, 2,3-dimethoxy cyclohexyl, 2,3- diethoxy cyclohexyl, 2,4-dimethoxy cyclohexyl, 2,5-diethoxy cyclohexyl, 2,3-dipropoxy cyclohexyl etc. Further examples include, but not limited to, are 2-hydroxy-4-methoxy cyclohexyl, 3-hydroxy-5-methylcyclohexyl, 2-methyl-4-methoxy cyclohexyl etc.

I n a preferred embodiment, R is an aryl and an aryl-Cr^-alkyl, wherein the aryl part is unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, NH ₂ , N HC _! -C ₄ -alkyl, N(C ₁ -C ₄ -alkyl) ₂ , C _j -C^alkyl and C _! -C ₄ -alkoxy. The representative examples of the aryl and the aryl-Ci-C ₄ -a Ikyl, wherein the aryl part is u nsubstituted are phenyl, 1- phenylmethyl, 1-phenylethyl, 1-phenylpropyl, 1-phenylbutyl, 1-methyl-l-phenyl-propyl, 3- phenylpropyl, 4-phenylbutyl, 3 - phe ny I butyl, 2-methyl-3-phenyl-propyl etc. The representative examples of the aryl and the aryl-C _j -CValkyl substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, NH ₂ , N H-CrC^alkyl, N(CrC ₄ -alkyl) ₂ , CrCfralkyl and C _j -0 ₄ -alkoxy include, but not limited to, 3-hyd roxyphenyl, 2,5-dihydroxyphenyl, 5-amino-2- hyd roxy-phenyl, 3 -(dimethylamino)-2- hydroxy- phenyl, 5-(dimethy la mi no) -3 -hydroxy- phenyl,

3- (diethyla mi no) -4- hyd roxy-phenyl, 5- methylami no-2- hydroxy- phenyl, 5-(dimethylamino)-

2- hydroxy-4- methyl -phenyl, 2- hydroxy-4 -ethyl -5- (methylami no) phenyl, 2- hydroxy-5 - methoxy-4-methyl-phenyl, 3-methoxy-4-methyl-phenyl, 2-methoxy-4-methyl-phenyl, 3- isopropoxyphenyl, 3-(isopropylamino)phenyl, 3-amino-5-(isopropylamino) phenyl, 3-hydroxy- 5-(isopropylamino)phenyl, 3-hydroxy-2-(isopropylamino) phenyl, 3-ch loro-5 -

(isopropylamino) phenyl, 2,3-dichloro-5-(isopropylamino)phenyl, 2,3-dich loro-5-isopropoxy- phenyl, 2,3-dich lorophenyl, 3-chloro-2-hydroxy-phenyl, 3-chloro-2-methoxy-phenyl, 2-(4- hyd roxy-2-methoxy-phenyl)ethyl, 2-(4-hydroxy-2-methoxy-phenyl)butyl, 2-(2,4- dimethoxyphenyl)ethyl, 2-(2,6-dimethoxyphenyl)ethyl, 2-(2,4-dimethoxyphenyl)propyl, 2- [4- methoxy-2-(methyla mi no) phenyl] ethyl, 2- [2- (di methylami no) -4- methoxy- phenyl] ethyl, 2- [2- (di m ethy la mi no)-4- (methylami no) phenyl] ethyl, 2 - [2- (di methylami no)-4-m ethoxy- phenyl] ethyl, 2- [3- (di methylami no) -4-ethyl -phenyl] ethy I, 2-[5-methoxy-2-

(methyla mi no) phenyl] propyl, 2 - [2 -(di methylami no) -4- methoxy- phenyl] methyl, 2- [2 -

(di m ethy la mi no)-5- (methylami no) phenyl] butyl, 2 - [2- (di methylami no) -3- m ethoxy- phenyl] methyl, 2 -[2-(di methylami no) -3 -ethy I- phenyl] propyl, 2-[2-(dimethylamino)-5-sec- butyl-phenyl]ethyl, 2 - [2- (di methylami no) -5 -sec-butyl-phenyl] methyl, 2-[2-(dimethylamino)-

4-sec-butyl-phenyl] butyl, 2-(2-chloro-4-sec-butyl-phenyl)ethyl, 2-(2-chloro-4-sec-butyl- phenyl)butyl, etc. I n a preferred embodiment the Fg is at least one functional grou p selected from the group consisting of a carboxylic acid, a carboxylic acid anhydride, carboxylic acid ester, an isocyanate, and mixtu res thereof; more preferably Fg is at least functional group selected from a carboxylic acid, and a carboxylic acid anhydride.

The representative examples of the compounds of formula (I) are, but not limited to, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, tricosylic acid, a -linolenic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic, eicosenoic acid, erucic acid, linoleic acid, eicosadienoic acid, docosadienoic acid, a -linolenic acid, -linolenic acid, pinolenic acid, eleostearic acid, b -eleostearic acid, mead acid, dihomo- g -linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, eicosatetraenoic acid, adrenic acid, bosseopentaenoic acid, eicosapentaenoic acid, ozubondo acid, sardine acid, tetracosanolpentaenoic acid, docosahexaenoic acid, herring acid, myristic acid, palmitic acid, arachidic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, and mixtures of acids based on natural products such as sunflower oil, tallow oil and tall oil fatty acids, benzoin acid, 2-methyl benzoic acid, 2,3-diisopropoxy octadecanoic acid, 3-hydroxy-5-methoxy octadecanoic acid, 2,5-dimethoxy octadecanoic acid, 5-ethoxy- 3-methoxy- octadecanoic acid, 5-isopropoxy-5-methoxy- octadecanoic acid, 4,7- diisopropoxy octadecanoic acid, 3-hyd roxy-2-methoxy octadecanoic acid, 2,3-dimethoxy octadecanoic acid, 2-ethoxy-3-methoxy- octadecanoic acid, 2-isopropoxy-3-methoxy- octadic-12-en-l-oic acid, 2,3-diisopropoxyoctadec-5-en-18-oic acid, 3-hydroxy-5- methoxyoctadec-17-en-10-oic acid, 2,5-dimethoxyoctadec-2-en-18-oic acid, 5-ethoxy-3- methoxy-octadec-2-en-18-oic acid, 5-isopropoxy-5-methoxy-octadec-16-en-l-oic acid, 4,7- diisopropoxy octadic-3-en-l-oic acid, 14,7-diisopropoxyoctadec-3-en-l-oic acid, cyclopentanoic acid, cyclohexanoic acid, cycloheptanoic acid, bicyclo[2.2.1] heptanoic acid, bicyclo[3.1.1] heptanoic acid, 2-hydroxy-4-methoxy cyclohexanoic acid, 3-hyd roxy-5- methylcyclohexanoic acid, 2-methyl-4-methoxy cyclohexanoic acid, 1-phenylmethanoic acid, 1-phenylethanoic acid, 1-phenylpropanoic acid, 1-phenylbutanoic acid, 1-methyl-l- phenyl-propanoic acid, 3-phenylpropanoic acid, 4-phenylbutanoic acid, 3-phenylbutanoic acid, 2-methyl-3-phenyl-propanoic acid, 3-methoxy-4-methyl-phenanoic acid, 2-methoxy-4- methyl-phenanoic acid, 3-isopropoxyphenanoic acid, 3-(isopropylamino)phenanoic acid, 3- amino-5-(isopropylamino) phenanoic acid, 3-hyd roxy-5-(isopropylamino)phenanoic acid, 3- hyd roxy-2-(isopropylamino)phenanoic acid, 3-chloro-5-(isopropylamino)phenanoic acid, 2,3-dich loro-5-(isopropylamino)phenanoic acid, 2-[2-(dimethylamino)-4-methoxy- phenyl]ethanoic acid, 2- [2-(dimethylamino)-4-(methylamino)phenyl]ethanoic acid, 2-[2- (dimethylamino)-4-methoxy-phenyl]ethanoic acid, 2- [3-(dimethylamino)-4-ethyl- phenyljethanoic acid, 2-[5-methoxy-2-(methylamino) phenyl] propanoic acid, 2- [2 - (dimethylamino)-4-methoxy-phenyl] methanoic acid, 2- [2-(dimethylamino)-5-

(methyla mi no) phenyl] butanoic acid, 2- [2-(dimethylamino)-3-methoxy-phenyl] methanoic acid, 2-[2-(dimethylamino)-3-ethyl-phenyl] proanoic acid, 2-[2-(dimethylamino)-5-sec- butyl-phenyl]ethanoic acid, 2-[2-(dimethylamino)-5-sec-butyl-phenyl] methanoic acid, 2-[2- (dimethy la mi no)-4-sec-buty I- phenyl] butanoic acid, 2-(2-chloro-4-sec-butyl- phenyl)ethanoic acid, 2-(2-chloro-4-sec-butyl-phenyl)butanoic acid. I n an embodiment, the at least one compou nd B is compounds of formulae (I I) and (II I)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N H-C C^alkyl, IXKC _j -C alkyl) ₂ , C ₁ -C ₄ -alkyl and (VC^alkoxy; and

R ^z is selected from the group consisting of hydrogen and CrC ₄ -alkyl; more preferably

k is 0, 1, 2, or 3;

R ¹ is selected from the group consisting of halogen, N (C ₁ -C ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ - alkoxy; and

R ² is selected from the group consisting of hydrogen and CrC ₄ -alkyl; most preferably,

k is 0 or 1;

R ¹ is selected from the group consisting of halogen, Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and R ² is selected from the group consisting of hydrogen and C ₁ -C ₄ -alkyl.

Within the context of the present invention the representative examples of R ¹ substituents of the compounds of the formu lae (I I) and (III) are, but not limited to, N H-CVCValkyl and N (C ₁ -C ₄ -alkyl) ₂ are, but not limited to, methylamino, dimethylamino, ethylamino, diethylamino, propylamino, ethylmethylamino, methylbutylamino, dibutylamino, butylamino etc.

Within the context of the present invention the representative examples of R ¹ substituents of the compounds of the formulae (II) and (I II) are, but not limited to, Ci-C ₄ -alkyl are methyl, ethyl, propyl, isopropyl, butyl, isobutyl and the representative exam ples of the C _j - -alkoxy are methoxy, ethoxy, propoxy, isopropoxy, iosbutoxy, butoxy etc.

Examples for the suitable compounds of the formula I I are isatoic anhydride, fluoroisatoic anhydride, chloroisatoic anhydride, bromoisatoic anhydride, nitroisatoic anhyd ride, hyd roxyisatoic anhyd ride, methoxyisatoic anhydride, N-methylisatoic anhyd ride, N- ethylisatoic anhydride, aminoisatoic anhyd ride, (4-pyridiny l)isatoic anhydride. An example of a suitable compounds of the formula II I is the anhyd ride of anthranilic acid, i.e. k = 0. The representative exam ples of the compounds of the formu lae (II) and (III) are, but not limited to, isatoic anhydride, N-methylisatoic anhyd ride, N-ethylisatoic anhydride, aminoisatoic anhyd ride, fluoroisatoic anhydride, chloroisatoic anhydride, bromoisatoic anhydride, carboxylic isatoic anhyd ride, nitroisatoic anhydride, hyd roxyisatoic anhydride, methoxyisatoic anhydride, l-(methylsulfonylmethyl)isatoic anhydride, (4- pyridi nyl) isatoic anhydride, l-phenyl-2H-3,l-benzoxazine-2,4(l H)-dione, chloro-l-ethyl (methyl)-2H-3,l- benzoxazine-2,4(lH)-dione, isatoic anhyd ride carboxylic acid methyl ester.

I n an embodiment, the at least one compou nd B is lactones of the formu la (IV)

(IV)

wherein

A is a C ₃ -C ₁₂ -alkylene, which is u nsubstituted or substituted by 1 or 2 radicals selected from OH, CrC ₄ -alkyl and C _j -C^alkoxy;

more preferably A is a C ₃ -C ₁₀ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and CrC^alkoxy;

most preferably A is a C ₅ -C ₁₀ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy,

even more preferably A is a C ₅ -C ₈ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and C^C^alkoxy;

particularly A is a C ₅ -C ₈ -alkylene, which is u nsubstituted or substituted by 1 or 2 radicals selected from CrC^alkyl and Ci-C ₄ -alkoxy; and

even particular preferably A is an u nsubstituted C ₅ -C ₈ -alkylene.

Within the context of the present invention, in the lactones of the formula (IV), the term alkylene refers to an acyclic saturated hydrocarbon chains. The representative examples of the C ₃ -C ₁₂ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals are selected from OH, CrC ₄ -al grou ps include, but are not limited to, -CH ₂ -CH ₂ -CH ₂ - , -(CH ₂ ) ₄ -, -(CH ₂ ) ₅ -(CH ₂ ) ₁₀ -, -CH ₂ -CH (CH ₃ )-CH ₂ -, -CH ₂ -CH(CH ₂ CH ₃ )-, - CH ₂ -C(CH ₃ ) ₂ -CH ₂ - ₂ -CH ₂ -, -CH ₂ -CH(OCH ₂ CH ₃ )-CH ₂ -, -CH ₂ -CH (OH)-CH ₂ - , -CH ₂ -CH (OH)-C H)-CH ₂ -CH ₂ - CH ₂ -, , -CH ₂ -C(OH) (CH ₃ )-CH ₂ -, -CH ₂ - CH (CH ₂ CH ₃ ) -CH ₂ - -CH ₂ - [C(CH ₃ ) ₂ ] ₂ -CH ₂ -, -CH ₂ - [C(0CH ₃ ) ₂ ] ₂ -CH ₂ -, -CH ₂ - [C(OCH ₂ CH ₃ ) ₂ ] ₂ -CH ₂ -, etc.

The representative examples of the lactones of the formula (IV) are, but not limited to, oxetan-2-one, 4-methyloxetan-2-one, butyrolactone, caprolactone, 4- methyltetrahydropyran-2-one, valerolactone, tetrahydropyran-2-one, 3- methyltetrahyd ropy ran -2-0 ne, 3,6-dimethyltetrahydropyran-2-one, 6- methyltetrahydropyran-2- one, or a mixture thereof. I n an embodiment, the at least one compou nd B is an internal anhydride of the formu la (V)

wherein D is selected from the group consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2- phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a C _j -C _jg alkyl or Ci-C ₁₈ alkenyl radical and 1,2-phenylene is u nsubstituted or substituted by 1 or 2 radicals selected from the group consisting of 1 or 2 radicals selected from OH, CrC^alkyl and C/- C ₄ -alkoxy, -COOH or halogen; more preferably a C ₂ -C ₆ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, C _j -C^alkyl and C _j -C^alkoxy.

Within the context of the present invention, in the internal anhydride of the formu la (V), the term alkylene refers to an acyclic satu rated hyd rocarbon chains. Representative examples of the C ₂ -C ₆ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from

The preferred acid anhyd rides (V) include the aliphatic acid anhydrides, such as malonic an hydride, succinic anhydride, glutaric anhyd ride, 2-methylglutaric anhydride, 3- methylglutaric anhydride, adipic anhydride, pimelic anhydride, octadecenylsuccinic anhydride, maleic anhydride, itaconic anhydride or citraconic anhydride, the cycloaliphatic acid an hydrides, such as cis- or trans-l,2-cyclohexanedicarboxylic anhydride, and aromatic acid anhyd rides, such as phthalic anhyd ride, 1,2,4-benzenetricarboxylic an hyd ride or pyromel litic dianhydride.

I n another embodiment, the branched modified polyetheramine having a weight average molecular weight M _w in the range of > 1,000 g/mol to < 100,000 g/mol, is obtained by reacting a mixture comprising, a) at least one branched polyetheramine polyol P containing at least one hyd roxyl group having a weight average molecular weight M _w in the range of > 500g/mol to <10,000 g/mol and b) at least one compound B selected from- i) compounds of formula (I)

R-Fg (l) wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is selected from (CH ₂ -C(CH ₃ ) ₂ ) n; or C _n H _2n+1 , wherein n is an integer from 6 to 22, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy;

linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is C _n H _2n-1 , wherein n is an integer from 6 to 22, wherein alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C ₄ - alkoxy;

a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected from OH, CrC^alkyl and C _; rC ₄ -alkoxy; and

aryl and aryl-C ₁ -C ₄ -alkyl, wherein the aryl part is u nsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, N H ₂ , NHC _; rC ₄ -alkyl, N (C ₁ -C ₄ -alkyl) ₂ , C _; rC ₄ -alkyl and C^C^alkoxy; and

Fg is selected from the group consisting of carboxylic acid, carboxylic acid anhydride, carboxylic acid ester, isocyanate, and mixtures thereof;

(ii) compounds of the formulae (I I) and (II I)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N HC^C^alkyl,

N(C ₁ -C ₄ -alkyl) ₂ , C ₁ -C ₄ -alkyl and (VCValkoxy; and

R ² is selected from the group consisting of hydrogen and CrC ₄ -alkyl;

Oii) lactones of the formula (IV)

o

A A _ o (IV)

wherein A is a C ₃ -Ci ₂ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and CrC ₄ -alkoxy; iv) internal anhydride of the formu la (V)

wherein D is is selected from the grou p consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2-phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a C _j -Cig alkyl or Ci-Ci ₈ alkenyl radical and 1,2-phenylene is unsubstituted or substituted by 1 or 2 radicals selected from the grou p consisting of 1 or 2 radicals selected from OH, C _j -C^alkyl and CrC ₄ -alkoxy, -COOH or halogen; more preferably a C ₂ -C ₆ -alkylene, which is u nsubstituted or substituted by 1 or 2 radicals selected from OH, C _j -C^alkyl and C _j -C^alkoxy.

I n this context, the variables R, Fg, R ¹ , k, R ² , A and D used i n the formulae (I), (I I), (I I I), (IV) and (V) are each as defined as given above.

I n another embodiment, the com pou nd B is selected from the group consisting of C ₆ -C ₂₂ - alkenyl succinic anhydrides, C ₆ -C ₂₂ -alkyl succinic anhyd rides, polyisobutene succinic anhydrides (PIBSA), C ₆ -C ₂₂ -alkylisocyanates, C ₆ -C ₂₂ -fatty acids, Ci-C ₄ -alkyl esters of C ₆ -C ₂₂ - fatty acids, isatoic anhydride, and aliphatic C ₄ -Ci ₂ -lactones

I n a preferred embodiment, the C ₆ -C ₂₂ -alkenyl succinic anhydrides are, but not limited to, 3- hexylidenetetrahydrofuran-2,5-dione, 3-hen-l-enyltetrahyd rofuran-2,5-dione, 3-[henicos-l- enyl]tetrahydrofuran-2,5-dione, 3-[henicosa-l,7-dienyl]tetrahyd rofu ran-2,5-dione, 3- [henicosa-l,7,18-trienyl]tetrahyd rofuran-2,5-dione, 3-[pentadeca-l,7- dienyl]tetrahyd rofuran-2,5-dione, 3- [pentadec-4-enyl]tetrahyd rofu ran-2,5-dione, 3-[dodec- 4-enyl]tetrahydrofu ran-2,5-dione, 3-[dec-4-enyl]tetrahydrofu ran-2,5-dione, 3-[hept-4- enyl]tetrahydrofuran-2,5-dione, 3-[octa-2,4-dienyl]tetrahydrofuran-2,5-dione, 3-[octa-2,4- dienyl]tetrahyd rofuran-2,5-dione, 3- [trideca-2,4, 10-trienyl] tetra hyd rof u ran-2,5-dione, 3-[l- hexy Itrid eca -2,4, 10-trienyl] tetra hyd rot u ran-2,5-dione, 3- [l-hexyltridec-2- enyl]tetrahydrofuran-2,5-dione, 3-trideca-2,5,7,10,12-pentaenyltetrahydrofu ran-2,5-dione, 3-dodeca-2,5,7,9,l l-pentaenyltetrahydrofuran-2,5-dione, etc.

The representative structural example of the C ₆ -C ₂₂ alkenyl succinic anhydrides are:

PI BSA Dodecenyl succinic anhydride wherein n is 1 to 40

I n a preferred embodiment, the C ₆ -C ₂₂ alkyl succinic anhyd rides are, but not limited to, 3- docosyltetrahyd rofuran-2,5-dione, 3-icosyltetrahyd rofu ran-2,5-dione, 3- nonadecyltetrahydro-furan-2,5-dione, 3-octadecyltetrah d rofu ran-2,5-dione 3- heptadecyltetrahydrofu ran-2,5-dione, 3-hexadecyltetrahydrofu ran-2,5-dione, 3- pentadecyltetrahydrofu ran-2,5-dione, 3-tetradecyl-tetrahydrofuran-2,5-dione, 3- dodecyltetrahyd rofuran-2,5-dione, 3-decyltetrahydro-furan-2,5-dione, 3- octyltetrahyd rofuran-2,5-dione 3-hexyltetrahydrofu ran-2,5-dione, 3 -(1- propyl hexyl) - tetrahyd rofuran-2,5-dione, 3-(l-propylpentyl)tetrahyd rofuran-2,5-dione, 3-(l-propylbutyl)- tetrahyd rofuran-2,5-dione, 3-(l-ethylbutyl)tetrahydrofuran-2,5-dione, 3-(l- methylpentyl)tetra-hydrofuran-2,5-dione, 3-(l-methylhexyl)tetrahydrofuran-2,5-dione, 3-(l- butylhexyl)tetrahydro-furan-2,5-dione, 3-dodecyltetrahydrofu ran-2,5-dione, etc.

I n a preferred embodiment, the C ₆ -C ₂₂ -alkylisocyanates are, but not limited to, n-hexyl isocyanate, heptyl isocyanate, n-octyl isocyanate, n-decyl isocyanate, cyclohexyl isocyanate, hexamethylene diisocyanate, dodecyl isocyanate, tetradecyl isocyanate, tridecyl isocyanate, pentadecyl isocyanate, 5-isocyanatoundecane, 5-isocyanatononane, 5- isocyanatooctadecane, 8-isocyanatohenicosane, 10-isocyanatohenicosane, 10- isocyanatononadecane, 8-isocyanatoheptadecane, 8-isocyanatopentadecane, 7- isocyanatotetradecane, 7-isocyanatotridecane, 6-isocyanatododecane, 5- isocyanatou ndecane, 5-isocyanatodecane, 4-isocyanatononane, etc.

I n a preferred embodiment, the compound B are C ₆ -C ₂₂ -fatty acids. The C ₆ -C ₂₂ fatty acids can be a saturated or an u nsatu rated fatty acid with one or more double bond. The representative examples of the saturated and unsaturated fatty acids are, but not limited to, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, u ndecylic acid, lau ric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, tricosylic acid, a -linolenic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic, eicosenoic acid, erucic acid, linoleic acid, eicosadienoic acid, docosadienoic acid, a -linolenic acid, -linolenic acid, pinolenic acid, eleostearic acid, b -eleostearic acid, mead acid, dihomo- g -linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, eicosatetraenoic acid, adrenic acid, bosseopentaenoic acid, eicosapentaenoic acid, ozubondo acid, sardine acid, tetracosanolpentaenoic acid, docosahexaenoic acid, herring acid, etc.

I n a preferred embodiment, the compound B are C ₁ -C ₄ -alkyl esters of C ₆ -C ₂₂ -fatty acids. The representative examples of the C ₁ -C ₄ -alkyl esters of C ₆ -C ₂₂ -fatty acids are, but not limited to, methyl decanoate, ethyl decanoate, propyl decanoate, isopropyl decanoate, butyl decanoate, isoproyl palmitate, methyl palmitate, ethyl palmitate, methyl oleate, isopropyl oleate, methyl arachidonate, ethyl gadolenate, isoproyl gadolenate, methyl sapienate, isoproyl sapienate, methyl linoleniate, isoproyl linoleniate, butyl linoleniate, isobutyl linoleniate, etc.

I n another preferred embodiment, the compound B is isatonic anhydride.

Isatonic an hydride

I n another preferred embodiment, the compound B is an aliphatic C ₄ -C ₁₂ -lactone. The representative example of the C ₄ -C _lz -lactones are, but not limited to, tetrahydropyran-2- one, tetrahydrofuran-2-one, oxepan-2-one, oxocan-2-one, oxonan-2-one, oxecan-2-one, oxacycloundecan-2-one, oxacyclododecan-2-one, 3-oxabicyclo[8.2.1]tridecan-4-one, 4- oxabicyclo[7.3.1]tridecan-3-one, 10-oxabicyclo[6.4.1]tridecan-l l-one, 4, 5, 5a, 6, 7, 8, 9, 9a- octahydro-l H-benzo[c]oxepin-3-one, 3,4,4a,5,6,7,8,8a-octahydrochromen-2-one, etc.

I n a preferred embodiment, the at least one compound B reacts with the at least one hyd roxyl group of the at least one branched polyetheramine polyol P, to form at least one lin king group selected from the group consisting of an ester, an urethane and an amide. The at least one hydroxyl grou p of the at least one branched polyetheramine polyol when reacts with the at least one carboxylic acid group of the at least one com pou nd B can lead to the formation of the ester lin kage. The at least one hyd roxyl group of the at least one branched polyetheramine polyol when reacts with the at least one carboxylic acid anhydride group of the at least one compound B can lead to the formation of the ester linkage. The at least one hyd roxyl group of the at least one branched polyetheramine polyol when reacts with the at least one lactone group of the at least one compound B can lead to the formation of the ester linkage. The at least one hydroxyl grou p of the at least one branched polyetheramine polyol when reacts with the at least one isocyanate group of the at least one com pou nd B can lead to the formation of the u rethane linkage. The reaction product of the at least one branched polyetheramine polyol P with the at least one com pound B can have a mixtu re of lin kages, when more than one com pou nd of B is used. For example, when the at least two hyd roxyl group of the at least one branched polyetheramine polyol reacts with the compounds of the formu lae (I I) or (II I) and the com pou nd of formula (I), the resulting product will have a mixture of the ester and the amide linkages. In another example, when the at least two hyd roxyl grou p of the at least one branched polyetheramine polyol reacts with the compound of formu la (I) bearing a carboxylic acid and the com pou nd of formula (V) bearing an anhydride, a mixtu re of ester lin kages is obtai ned. I n yet another example, when the at least two hydroxyl grou p of the at least one branched polyetheramine polyol react with the compou nd of formula (I) bearing an isocyanate group and the compound of formula (V) bearing a cyclic anhydride group, mixtures of the ester and the urethane linkages are obtained. In a further example, when the at least two hydroxyl grou ps of the at least one branched polyetheramine polyol react with the com pou nd of formula (I) bearing an isocyanate group and the compou nd of formu la (I I) and/or (I I I), mixtu res of the ester, the amide and the urethane linkages are obtained.

I n an embodi ment, the at least 5 mol % of the hydroxyl grou ps of the at least one branched polyetherami ne polyol P are reacted with the at least one compound B, more preferably the at least 10 mol % of the hydroxyl groups of the at least one branched polyetheramine polyol P are reacted with the at least one compound B, most preferably the at least 15 mol % of the hydroxyl grou ps of the at least one branched polyetheramine polyol P are reacted with the at least one compou nd B and particular preferably the at least 25 mol % of the hydroxyl grou ps of the at least one branched polyetheramine polyol P are reacted with the at least one compound B.

I n an embodiment, the molar ratio of the functional groups Fg in the at least one compou nd of general formula (I ) to the hyd roxyl groups in the at least one branched polyetheramine polyol P is in the range of > 0.1:1 to < 1:1;

or

the molar ratio of the grou ps in the at least one compound of general formula (I I) and/or (I II) to the hydroxyl groups in the at least one branched polyetheramine polyol P is in the range of > 0.1:1 to < 1:1;

or

the molar ratio of the grou ps in the at least one compound of general formula (IV) to the hyd roxyl groups in the at least one branched polyetheramine polyol P is in the range of > 1:1 to < 10:1

or

the molar ratio of the lactone groups in the at least one compou nd of general formu la (V) to the hydroxyl grou ps in the at least one branched polyetheramine polyol P is in the range from > 0.05:1 to < 2:1.

More preferably, the molar ratio of the functional groups Fg in the at least one com pound of general formula (I ) to the hydroxyl groups in the at least one branched polyetheramine polyol P is in the range of > 0.3:1 to < 1:1;

or

the molar ratio of the grou ps in the at least one compound of general formula (I I) and/or (I II) to the hydroxyl groups in the at least one branched polyetheramine polyol P is in the range of > 0.3:1 to < 1:1;

or

the molar ratio of the grou ps in the at least one compound of general formula (IV) to the hyd roxyl groups in the at least one branched polyetheramine polyol P is in the range of > 1:1 to < 5:1;

or

the molar ratio of the lactone groups in the at least one com pou nd of general formu la (V) to the hydroxyl grou ps in the at least one branched polyetheramine polyol P is in the range from > 0.1:1 to < 2:1. Most preferably, the molar ratio of the functional grou ps Fg in the at least one compound of general formula (I ) to the hydroxyl grou ps in the at least one branched polyetheramine polyol P is in the range of > 0.5:1 to < 1:1;

or

the molar ratio of the grou ps in the at least one compound of general formula (I I) and/or (I II) to the hydroxyl groups in the at least one branched polyetheramine polyol P is in the range of > 0.5:1 to < 1:1;

or

the molar ratio of the grou ps in the at least one compound of general formula (IV) to the hyd roxyl groups in the at least one branched polyetheramine polyol P is in the range of > 1:1 to < 3:1;

or

the molar ratio of the lactone groups in the at least one com pou nd of general formu la (V) to the hydroxyl grou ps in the at least one branched polyetheramine polyol P is in the range from > 0.3:1 to < 2:1.

Preferably, the molar ratio of the functional grou ps Fg in the at least one compou nd of general formula (I ) to the hydroxyl grou ps in the at least one branched polyetheramine polyol P is in the range of > 0.8:1 to < 1:1;

or

the molar ratio of the grou ps in the at least one compound of general formula (I I) and/or (I II) to the hydroxyl groups in the at least one branched polyetheramine polyol P is in the range of > 0.8:1 to < 1:1;

or

the molar ratio of the groups in the at least one compound of general formula (IV) to the hyd roxyl groups in the at least one branched polyetheramine polyol P is in the range of > 1:1 to £ 2:1;

or

the molar ratio of the lactone groups in the at least one com pou nd of general formu la (V) to the hydroxyl grou ps in the at least one branched polyetheramine polyol P is in the range from > 0.5:1 to < 2:1.

I n an embodiment, the weight ratio of the at least one compound B to the at least one branched polyetheramine polyol P is in the range from > 1:3 to < 3:1, more preferably the weight ratio of the at least one compound B to the at least one branched polyetheramine polyol P is in the range from > 1:2.5 to < 2.5:1, most preferably the weight ratio of the at least one compound B to the at least one branched polyetheramine polyol P is in the range from > 1:2 to < 2:1, particular preferably the weight ratio of the at least one compou nd B to the at least one branched polyetheramine polyol P is in the range from > 1:1.5 to < 1.5:1.

I n another embodiment, the branched modified polyetheramine having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100,000 g/mol is obtained by reacting a mixture comprising: a) at least one modified branched polyetheramine;

and

b) at least one compound B selected from

i) compounds of formula (I)

R-Fg (l)

wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and Ci-C ₄ -alkoxy; linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and Ci-C ₄ -alkoxy; a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and C _j -C alkoxy; and

aryl and a ry I -Ci-C ₄ -a I ky I, wherein the aryl part is unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, N H ₂ , N HC C^alkyl, N (C ₁ -C ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

Fg is selected from the group consisting of carboxylic acid, hydroxy carboxylic acid, carboxylic acid anhyd ride, carboxylic acid ester, isocyanate, and mixtures thereof;

(ii) compounds of the formu lae (II) and (II I)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N HCrC ₄ -alkyl, N (C _I -C ₄ - alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

R ² is selected from the group consisting of hydrogen and C ₁ -C ₄ -alkyl;

(iii) lactones of the formula (IV)

wherein A is a C ₃ -C ₁₂ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, C _j -C^alkyl and CrC ₄ -alkoxy; iv) internal anhydride of the formu la (V)

wherein D is selected from the grou p consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2- phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a C _j -C _jg alkyl or C C ₁₈ alkenyl radical and 1,2-phenylene is u nsubstituted or substituted by 1 or 2 radicals selected from the group consisting of 1 or 2 radicals selected from OH, CrC alkyl and Cr C ₄ -alkoxy, -COOH or halogen.

I n this context, the variables R, Fg, R ¹ , R ² , A, D and k used in the formulae (I), (II), (I II), (IV) and (V) are each as defined as given above.

I n a preferred embodiment, the reaction is carried out at a temperatu re is in the range of > 60 to < 300 °C, more preferably the temperature is in the range of > 60 to 250 °C £, most preferably the temperature is in the range of > 70 to 200 °C < and particular preferably the temperatu re is in the range of > 90 to 180 °C £.

I n a preferred embodiment, the product of the reaction is isolated by any method known in the art selected from the group consisting of decantation, chemical separation, acid-base neutralization, distillation, evaporation, colu mn chromatography, filtration, concentration, crystallization and re-crystallization or a combination thereof. A person skilled in the art is aware of such techniques.

I n a preferred embodiment, the at least one branched polyetheramine polyol P has an amine number determined according to ISO 25761 is in the range from > 200 to < 1000 mg KOH/g, more preferably is in the range from > 200 to < 800 mg KOH/g, even more preferably is in the range from > 250 to < 700 mg KOH/g, most preferably is in the range from > 350 to < 650 mg KOH/g, particular preferably is in the range from > 400 to < 600 mg KOH/g.

I n a preferred embodiment, the at least one branched modified polyetheramine has an ami ne number determined according to DI N 53176 is in the range from > 20 to < 600 mg KOH/g, more preferably is in the range from > 20 to < 400 mg KOH/g, even more preferably is in the range from > 25 to < 300 mg KOH/g, most preferably is in the range from > 30 to < 280 mg KOH/g, particular preferably is in the range from > 30 to < 250 mg KOH/g.

I n a preferred embodiment, the modified branched polyetheramine polyols (B) have a glass transition temperatu re of < 50 °C, more preferably < 30 °C, and even more preferably < 10 °C, determined by differential scanning calorimetry (DSC).

I n an embodiment, the branched modified polyetheramine is neutralized with at least one polymeric carboxylic acid or at least one polymeric phosphoric acid.

I n a preferred embodiment, the at least one polymeric carboxylic acid (V) has general formula (VA) or (VB)

formula (VA) wherein

# indicates the point of attach ment to the terminus and/or to the polymer

backbone;

k is 0, 1, 2, 3 or 4, in particular 0, 1 or 2, especially 0 or 1;

m is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, in particular 0, 1 or 2, especially 0 or 1;

A is a chemical bond or a divalent moiety selected from the group consisting of C _j - C ₆ alkylene, -0-(C ₂ -C ₆ alkylene), -C(=0)-0-(C ₂ -C ₆ alkylene),

-N R ³ -(C ₂ -C ₆ alkylene) and C(=0)-NR ³ -(C ₂ -C ₆ alkylene), where the C ₂ -C ₆ alkylene part is attached to Q;

Q is a divalent moiety selected from the grou p consisting of -0-, -N H- and -S-; more preferably -O- and -N H-, most preferably -0-;

R ¹ is independently selected from the grou p consisting of -OH, -COOH,

-COOCH ₃ , -N H ₂ , -NH (0 _! -0 ₆ alkyl), -N ^-Cg alkyl) ₂ , -N0 ₂ , -S(=0) ₂ R ⁴ ,

Ci-C ₂₀ alkyl, Ci-C ₄ alkoxy, halogen, aryloxy, aryl, heteroaryl, where aryl, hetaryl and aryloxy are u nsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the grou p consisting of -OH, -COOH, -COOCH ₃ , -NH ₂ ,

-N H(C C ₆ alkyl), -N(C C ₆ alkyl) ₂ , -N0 ₂ , -S(=0) ₂ R ⁴ , C _r C ₄ alkyl,

C C ₄ alkoxy and halogen;

R ² is selected from the group consisting of hydrogen, -S(=0) ₂ R ⁴ , C _j -C^ alkyl, C ₃ -Ci ₀ cycloalkyl, aryl, heteroaryl, aryl-C _j -C^alkyl and heteroaryl-Ci-C^alkyl, where aryl and hetaryl in the four last mentioned radicals are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of -OH, -COOH, - COOCH ₃ , -N H _2I -NH (C C ₆ alkyl), -N (C C ₆ alkyl) ₂ , -N0 ₂ , -S(=0) ₂ R ⁴ , C C ₄ alkyl, C C ₄ alkoxy and halogen;

X is a divalent moiety selected from the group consisting of Ci-C ₁₀ alkylene, C ₂ -C ₆ alkenylene, C ₄ -C ₇ cycloalkylene, arylene and alkarylene, where the

alkylene, C ₂ -C ₆ alkenylene and C ₄ -C ₇ cycloalkylene are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of CrC ₁₈ alkyl or Ci-Ci ₈ alkenyl, and where arylene and alkarylene are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of C _j -C^ alkyl, C ₄ -C ₄ haloalkyl, aryl, -COOH, -COOCH ₃ , -N0 ₂ or halogen;

R ³ is selected from the group consisting of hydrogen, -S(=0) ₂ R ⁴ , alkyl, C ₃ -Ci ₀ cycloalkyl, aryl and heteroaryl, where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of -OH, - COOH, -COOCH ₃ , - N H _2I -NH (C _! -C ₆ alkyl), -N ^-C ₈ alkyl) ₂ ,

-N0 ₂ , -S(=0) ₂ R ⁴ , 0 ₄ -0 ₄ alkyl, CrC ₄ alkoxy and halogen;

R ⁴ is selected from the group consisting of OH, -N H ₂ , -NH ^ _j -Cg alkyl), -N (q _! -0 ₆ alkyl) ₂ , 0 ₄ -0 ₄ alkyl, 0 ₄ -0 ₄ alkoxy, aryl and heteroaryl, where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of Ci-C ₄ alkyl, CrC ₄ alkoxy and halogen.

Fu rther examples and the means of preparation of the such polymeric carboxylic acid having general formula (VA) can be found in WO2013/124830, which is herein incorporated for the reference for the polymeric carboxylic acid.

I n a preferred embodiment, the at least one polymeric carboxylic acid has general formula (VB)

Formu la (VB)

Z _j is selected from the group consisting of substituted or u nsubstituted linear or branched satu rated or u nsaturated C ₄ to C ₃₀ hydrocarbyl and substituted or unsubstituted saturated or unsaturated cyclohyd rocarbyl;

R is H or substituted or unsubstituted C ₄ to C ₆ alkyl;

X is selected from the group consisting of substituted or unsubstituted C _x to C ₁₀ alkylene and substituted or unsubstituted Ci to C ₁₀ cycloal kylene;

o is 1 to 6; and

m is 1 to 50. Preferably, Z ₁ is selected from the grou p consisting of substituted or u nsubstituted linear or branched saturated or unsaturated C ₃ to C ₃₀ hydrocarbyl, and substituted or unsubstituted satu rated or u nsaturated cyclohydrocarbyl;

R is H or substituted or unsubstituted C ₃ to C ₆ alkyl;

X is selected from the group consisting of substituted or unsubstituted C _x to C ₁₀ alkylene and substituted or unsubstituted Ci to C ₁₀ cycloal kylene;

o is 1 to 6; and

m is 1 to 50.

More preferably, Z ₁ is selected from the grou p consisting of substituted or unsubstituted linear or branched satu rated or unsatu rated Ci to C ₃₀ hydrocarbyl;

R is H or substituted or unsubstituted C ₃ to C ₆ alkyl;

X is selected from the group consisting of substituted or unsubstituted Ci to C ₁₀ alkylene; o is 1 to 6; and

m is 1 to 50.

Most preferably, Z _x is selected from the grou p consisting of substituted or unsubstituted linear or branched satu rated or u nsaturated C ₆ to C ₃₀ hydrocarbyl;

R is H or substituted or unsubstituted C ₃ to C ₆ alkyl;

X is selected from the group consisting of substituted or unsubstituted C ₄ to C ₁₀ alkylene; o is 1 to 6; and

m is 1 to 50.

Yet most preferably Z _x is selected from the group consisting of u nsubstituted linear or branched saturated or unsaturated C ₆ to C ₃₀ hyd rocarbyl;

R is H or unsubstituted C ₂ to C ₄ alkyl;

X is selected from the group consisting of unsubstituted C ₄ to C ₁₀ alkylene;

o is 2 to 6; and

m is 6 to 50.

Particu lar preferably, Z _x is selected from the group consisting of u nsubstituted linear satu rated or u nsaturated C ₈ to C ₃₀ hydrocarbyl;

R is H;

X is selected from the group consisting of unsubstituted C ₄ to C ₁₀ alkylene;

o is 2 to 6; and

m is 10 to 24.

The term hyd rocarbyl denotes a hyd rocarbon chain containing hyd rogen and carbon. The hyd rocarbyl is optionally containing at least one double bond and/or at least one triple bond.

The representative examples of the saturated hydrocarbyl are, but not limited to, isopropyl, iso-butyl, neo-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl- decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso- hexadecyl, iso-octadecyl and iso-eicosyl.

The representative examples of the u nsaturated hydrocarbyl having at least one double bond are, but not limited to 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 2-hexenyl, 1- heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1-decenyl, 2-decenyl, 1- undecenyl, 2-u ndecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2-tridecenyl, 1- tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1-hexadecenyl, 2- hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2-octadecenyl, 1- nonadecenyl, 2-nonadecenyl, 1-eicosenyl and 2-eicosenyl, more preferably selected from 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl, 2-octenyl, 1-nonenyl, 2-nonenyl, 1- decenyl, 2-decenyl, 1-undecenyl, 2-undecenyl, 1-dodecenyl, 2-dodecenyl, 1-tridecenyl, 2- tridecenyl, 1-tetradecenyl, 2-tetradecenyl, 1-pentadecenyl, 2-pentadecenyl, 1- hexadecenyl, 2-hexadecenyl, 1-heptadecenyl, 2-heptadecenyl, 1-octadecenyl, 2- octadecenyl, 1-nonadeceny 1, 2-nonadecenyl, 1-eicosenyl and 2-eicosenyl.

The term substituted or unsubstituted saturated or u nsaturated cyclohydrocarbyl denotes a cyclic hydrocarbon containing the hyd rogen and the carbon. The cyclohydrocarbyl can be monocyclic and bicyclic. The representative examples of the u nsubstituted or the branched C ₃ -C ₁₀ monocyclic and bicyclic cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, bicyc lo [2.2.1] h epty I and bicyclo[3.1.1] heptyl.

I n a preferred embodiment, the at least one polymeric phosphoric acid has the general formula (VI). The compound of general formula (VI) may be a monoester or a mixture of mono- or diester.

O

(OH) _n -3 - ^p- (- ⁰ - ^R s)n

formu la (VI)

wherein R ₅ represents an aliphatic, a cycloaliphatic and/or an aromatic moiety free of any Zerewiti noff hydrogen, containing at least one ether oxygen atom (-0-) and/or at least one carboxylic acid ester grou p (-COO-) or u rethane group (-NHC(O)O-), and having a number average molecu lar weight M _n of 200 to 10,000 g/mol, i n which the aliphatic hydrogen atoms may be partially replaced by halogen atoms, and in which the ratio of the number of the ether oxygen atoms to the nu mber of the carboxylic acid ester grou ps or the urethane groups in each grou p R ₅ is in the range from 1:20 to 20:1, and

n represents 1 or 2,

or a salt thereof.

Preferably, R ₅ represents an aliphatic, a cycloaliphatic and/or an aromatic moiety free of any Zerewitinoff hyd rogen, contai ning at least one ether oxygen atom (-0-) and at least one carboxylic acid ester grou p (-COO-) or u rethane group (-NHC(O)O-), and having a number average molecu lar weight M _n of 200 to 10,000 g/mol, i n which the aliphatic hydrogen atoms may be partially replaced by halogen atoms, and in which the ratio of the number of the ether oxygen atoms to the nu mber of the carboxylic acid ester grou ps or the urethane groups in each group R ₅ is in the range from 1:20 to 20:1, and

n represents 1 or 2,

or a salt thereof.

More preferably, R ₅ represents the residue of an oxalkylated monoalcohol optionally containing carboxylic acid ester grou ps and/or u rethane groups. R ₅ particularly preferably represents the residue of a C/ -C ₆ alkylene oxide optionally containing carboxylic acid ester groups and/or urethane grou ps. R ₅ most preferably represents the residue of an ethoxylated monoalcohol containing carboxylic acid ester grou ps and/or urethane groups.

Most preferably, R ₅ represents the residue of an oxalkylated monoalcohol containing carboxylic acid ester grou ps and/or u rethane groups. R ₅ particularly preferably represents the residue of a C/-C ₄ oxalkylated monoalcohol optionally containing carboxylic acid ester groups and/or urethane grou ps. R ₅ most preferably represents the residue of an ethoxylated monoalcohol containing carboxylic acid ester grou ps and/or urethane grou ps.

I n another preferred embodiment, in case the value of n is 2, then R ₅ is the same or different.

I n a preferred embodiment, the ratio of the number of alkylene oxide oxygen atoms to the nu mber of the carboxylic acid ester groups and/or the u rethane groups in R ₅ is in the range from 1:20 to 20:1, more preferably this ratio is in the range from 1:10 to 10:1, and particularly preferably the range is from 1:5 to 5:1.

I n a preferred embodiment, the polymeric phosphoric acid of general formula (VI) has number average molecu lar weight M _n in the range of 100 to 10,000 g/mol, more preferably from 200 to 5,000 g/mol, and particu larly preferably from 300 to 2,000 g/mol.

I n a preferred embodiment, the monohydroxy compounds which contain at least one alkylene oxide oxygen atom (-0-) and at least one carboxylic acid ester group (-C(O)O-) and/or urethane group (-NHC(O)O-) are mixed with the polyether-polyesters, the polyether- polyu rethanes or the polyether-polyester-polyurethanes. The examples of the polyether- polyester compounds include, but are not limited, to those obtained by polymerizing a lactone such as propiolactone, valerolactone or caprolactone, substituted derivatives thereof, or mixtures thereof with the monohydroxy compounds. The monohydroxy compounds preferably having 1 to 30 carbon atoms, more preferably 1 to 14 carbon atoms, are methanol, ethanol, propanol, n-butanol, longer-chained saturated and unsaturated alcohols such as oxo alcohols, cyclohexanol, phenylethanol, neopentyl alcohol, and also fluorinated alcohols and substituted and unsubstituted phenols can be used as starting materials for the alkoxylation. Processes for preparation of the polymeric phosphoric acid of general formu la (VI) can be found in US 5,130,463, which is herein incorporated by reference for the polymeric phosphoric acid.

I n an embodiment, the at least one polymeric carboxylic acid or the at least one polymeric phosphoric acid comprises a poly-C ₂ -C ₆ -alkyleneoxide radical.

I n a preferred embodiment, the at least one polymeric carboxylic acid of formula (VA) is a compound of formu la

formu la (VA1)

wherein n is 5 to 50.

I n a preferred embodiment, the polyisobutylene succinic anhyd ride reacts with the at least one hydroxyl grou p of the at least one branched polyetheramine polyol P to form a branched polyetherami ne modified with the polyisobutylene succinic anhydride having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formu la (VA1).

I n a preferred embodiment, the dodecenyl succinic anhydride reacts with the at least one hyd roxyl group of the at least one branched polyetheramine polyol P to form a branched polyetherami ne modified with the dodecenyl succinic anhydride having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formu la (VA1).

I n a preferred embodiment, the octadecyl isocyanate reacts with the at least one hyd roxyl grou p of the at least one branched polyetheramine polyol P to form a branched polyetherami ne modified with the octadecyl isocyanate having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the lauric acid reacts with the at least one hyd roxyl group of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the lauric acid having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VA1). I n a preferred embodiment, the tall oil fatty acid reacts with the at least one hydroxyl group of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the tall oil fatty acid having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is fu rther neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the epsilon-caprolactone reacts with the at least one hyd roxyl grou p of the at least one branched polyetheramine polyol P to form a branched polyetherami ne modified with the epsilon-caprolactone having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the valerolactone reacts with the at least one hyd roxyl group of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the valerolactone having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is fu rther neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the gamma-valerolactone reacts with the at least one hyd roxyl grou p of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the gamma-valerolactone having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the epsilon-caprolactone and the gam ma-valerolactone reacts with the at least two hyd roxyl groups of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the epsilon-caprolactone and the gamma- valerolactone having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the epsilon-caprolactone, the gamma-valerolactone and the lauric acid react with the at least th ree hydroxyl groups of the at least one branched polyetherami ne polyol P to form a branched polyetheramine modified with the epsilon- caprolactone, the gamma-valerolactone and the lauric acid having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formu la (VA1).

I n a preferred embodiment, the isatoic an hyd ride reacts with the at least one hyd roxyl group of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the isatoic anhyd ride having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is fu rther neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the isatoic anhyd ride, the epsilon-caprolactone and the gamma- valerolactone react with the at least three hydroxyl groups of the at least one branched polyetherami ne polyol P to form a branched polyetherami ne modified with the isatoic an hydride, the epsilon-caprolactone and the gamma-valerolactone having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formu la (VA1).

I n a preferred embodiment, the isatoic anhydride and the tall oi l fatty acid react with the at least two hyd roxyl groups of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the isatoic anhydride and the tall oil fatty acid having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the tall oil fatty acid and the succinic anhydride react with the at least two hyd roxyl groups of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the tall oil fatty acid and the succinic anhyd ride having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formu la (VA1).

I n a preferred embodiment, the tal l oil fatty acid and the isatoic anhydride react with the at least two hyd roxyl groups of the at least one branched polyetheramine polyol P to form a branched polyetheramine modified with the tall oil fatty acid and the isatoic anhyd ride having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VA1).

I n a preferred embodiment, the tal l oil fatty acid, the epsilon-caprolactone and the gamma- valerolactone react with the at least three hydroxyl groups of the at least one branched polyetherami ne polyol P to form a branched polyetheramine modified with the tall oil fatty acid, the epsilon-caprolactone and the gam ma-valerolactone having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formu la (VA1).

I n a preferred embodiment, the at least one polymeric carboxylic acid of general formula (VB) is a compound of formula (VB1).

formu la (VB1)

I n a preferred embodiment, the polyisobutylene succinic anhyd ride reacts with the at least one hydroxyl grou p of the at least one branched polyetheramine polyol P to form a branched polyetherami ne modified with the polyisobutylene succinic anhydride having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is further neutralized with the carboxylic acid of formula (VB1). I n a preferred embodiment, the at least one polymeric phosphoric acid of general formu la (VI) is a compou nd of formu la (Via). The compound of formu la (Via) may be a monoester or a mixtu re of mono- or diesters.

formula (Via)

I n an embodiment a liquid composition is in the form of a dispersion com prising a branched modified polyetheramine and a particu late solid material selected from the grou p consisting of pigments and fillers and a liquid diluent, wherein the particu late solid material is dispersed in the liquid diluent. The branched modified polyetheramine is as defi ned as above. The pigments are selected from the organic or the inorganic pigments.

I n an embodiment, a liquid composition is in the form of a dispersion com prising a branched modified polyetheramine which is fu rther modified with at least one component B and a particulate solid material selected from the group consisting of pigments and fillers and a liquid diluent, wherein the particu late solid material is dispersed in the liquid diluent. The branched modified polyetheramine which is further modified with at least one component B is as defined as above. The pigments are selected from the organic or the inorganic pigments.

I n an embodiment, a liquid composition is in the form of a dispersion com prising a branched modified polyetheramine which is fu rther modified with at least one component B and a particulate solid material selected from the group consisting of pigments and fillers and a liquid diluent, wherein the particu late solid material is dispersed in the liquid diluent. The branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one com ponent B which is neutralised with an acid of formu la (V) or (VI) is as defined as above. The pigments are selected from the organic or the inorganic pigments.

I n a preferred embodiment, the invention relates in particu lar to a liquid composition in the form of a liquid coating composition, which comprises a particulate solid material, in particular a pigment or a filler and a branched modified polyetheramine and/or a branched modified polyetheramine which is fu rther modified with the at least one component B, which is dispersed in a liquid diluent.

I n a preferred embodiment, the invention relates in particu lar to a liquid composition in the form of a liquid coating composition, which comprises a particulate solid material, in particular a pigment or a filler and a branched modified polyetheramine and/or a branched modified polyetheramine which is fu rther modified with the at least one component B, which is neutralised with an acid of formula (V) or (VI), which is dispersed in a liquid diluent.

I n a preferred embodiment, the invention also relates i n particular to a liquid composition in the form of a liquid ink composition, which comprises a particulate solid material, in particu lar a pigment or a filler, and a branched modified polyetheramine and/or a branched modified polyetheramine which is fu rther modified with the at least one component B, which is dispersed in a liquid diluent.

I n a preferred embodiment, the invention also relates i n particular to a liquid composition in the form of a liquid ink composition, which comprises a particulate solid material, in particu lar a pigment or a filler, and a branched modified polyetheramine and/or a branched modified polyetheramine which is further modified with the at least one component B which is neutralised with an acid of formula (V) or (VI), which is dispersed in a liquid diluent.

I n a preferred embodiment, the suitable solid particu lar materials include, but are not limited to, the group consisting of pigments and fillers. The pigments comprise inorganic or an organic pigments. The pigments can include the colored pigments and the pearlescent flakes.

I n a preferred embodiment, the size of the particulate material is preferably in the micrometre range, e.g. the weight average particle diameter is in the range from 1 mΐti to 2000 mΐti, in particu lar form 2 mΐti to 1000 mΐti or from 5 mΐti to 500 mΐti. The weight average particle diameter can be determined by the sieving analysis. The weight average particle diameter can also be determined by the light scattering methods.

Examples of the suitable organic pigments are the pigments and the pearlescent flakes selected from the group consisting of azo, disazo, naphthol, benzimidazolone, azocondensation, metal com plex, isoindolinone, and isoindoline pigments, the chinophthalon pigment, dioxazine pigment and the polycyclic pigment group consisting of indigo, thioindigo, quinacridones, phthalocyanines, perylenes, perionones, anthraquinones, such as aminoanth raquinones or hydroxyanthraquinones, anthrapyrimidines, indanthrones, flavanthrones, pyranth rones, anthantrones, isoviolanthrones, diketopyrrolopyrroles, and carbazoles, e.g. carbazole violet, and the like. Further examples of the organic pigments can be found in the monograph: W. Herbst, K. Hunger "Industrielle Organische Pigmente" 2 ^d Edition, 1995, VCH Verlagsgesellschaft, ISBN: 3-527-28744-2. Examples of the suitable inorganic pigments are the metallic flakes, such as aluminiu m, aluminium oxide, calciu m carbonate, silicon oxide and silicates, iron (I I l)oxide, chromiu m(ll l)oxide, titaniu m (IV)oxide, zirconium(IV)oxide, zinc oxide, zinc su lphide, zinc phosphate, mixed metal oxide phosphates, molybdenum sulphide, cad mium sulphide, carbon black or graphite, vanadates, such as bismuth vanadate, chromates, such as lead (IV)ch romate, and molybdates, such as lead (IV) molybdate, and mixtu res, crystal forms or modifications thereof, such as rutil, anatas, mica, talcu m or kaolin.

I n a preferred embodiment, the suitable fillers are calcium carbonate, silicates, glass fibres, glass beads, talc, kaolin, mica, bariu m su lphate, metal oxides and hydroxides, carbon black, graphite, wood powders, powders and fibres of other natural products and synthetic fibres.

I n a preferred embodiment, the selection of the liquid diluent that is present in the dispersion will depend on the field of application in a known man ner. The dispersants of the invention are particular usefu l in dispersions, where the di luent is selected from common ly used solvents in coatings technology. For water based formulations the diluent comprises water and may, aside from water, further com prise polar, water-miscible solvents, such as Ci-C ₄ alkanols, e.g. methanol, ethanol, isopropanol, propanol or n-butanol, glycol ethers like butyl glycol, or methoxypropylene glycol, polyols, e.g. glycerol, ethyleneglycol, diethyleneglycol, triethylene, triethylene glycol or propylene glycol. For solvent based formulations, preferably less polar solvents like aliphatic hyd rocarbons, esters like butyl acetate, or glycol ethers like methoxypropylene glycol or glycol ether esters like methoxypropylene glycol acetate and mixtu res thereof are used as liquid diluents.

I n a preferred embodiment, the weight ratio of the particulate solid material to the branched modified polyetheramine is in the range from > 100:1 to < 1:50, more preferably from 50:1 to 1:30, and even more preferably from 30:1 to 1:10.

I n an embodiment, the liquid composition com prises

a) > 1 to < 70 % by weight, based on the total weight of the liquid com position, of the at least one particulate solid material selected from the grou p consisting of the pigments and the fillers;

b) > 0.5 to < 50 % by weight, based on the total weight of the liquid com position, of the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one component B; and

c) > 10 to < 98.5 % by weight, based on the total weight of the liquid composition, of the at least one liquid diluent.

I n an embodiment, the liquid composition com prises

a) > 1 to < 70 % by weight, based on the total weight of the liquid com position, of the at least one particu late solid material selected from the grou p consisting of the pigments and the fillers;

b) > 0.5 to < 50 % by weight, based on the total weight of the liquid com position, of the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one component B which is neutralised with an acid of formula (V) or (VI); and

c) > 10 to < 98.5 % by weight, based on the total weight of the liquid composition, of the at least one liquid diluent.

In a preferred embodiment, the liquid composition may further comprise binders and/or one or more conventional additives depending on the intended use. Conventional additives includee.g. plasticisers, lubricants, emulsifiers, humectants, rheology additives, catalysts, flow auxiliaries, optical brighteners, flame retardants, preservatives, antistatic agents or blowing agents.

In a preferred embodiment, the liquid dispersion may be in the form of a millbase. Such a millbase contains the particulate solid, the branched modified polyetheramine or branched modified polyetheramine which is further modified with at least one component B and the liquid diluent and optionally additives, but generally the millbase will not contain binders.

In a preferred embodiment, the liquid dispersion may be in the form of a millbase. Such a millbase contains the particulate solid, the branched modified polyetheramine or branched modified polyetheramine which is further modified with at least one component B which is is neutralised with an acid of formula (V) or (VI) and the liquid diluent and optionally additives, but generally the millbase will not contain binders.

In a preferred embodiment, the liquid dispersion may also be in the form of a coating composition. Such a coating composition contains the particulate solid, the branched modified polyetheramine or branched modified polyetheramine which is further modified with at least one component B which is neutralised with an acid of formula (V) or (VI) and the liquid diluent and additionally one or more binders, e.g. film-forming polymers or prepolymers which form a film upon curing. The coating composition may optionally contain conventional additives that are used in the coating technology, e.g. plasticisers, lubricants, emulsifiers, rheology additives, catalysts, flow auxiliaries, optical brighteners, flame retardants, preservatives, antistatic agents or blowing agents.

In a preferred embodiment, the liquid dispersion may also be in the form of a coating composition. Such a coating composition contains the particulate solid, the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one component B and the liquid diluent and additionally one or more binders, e.g. film-forming polymers or prepolymers which form a film upon curing. Coating composition may optionally contain conventional additives that are used in the coating technology, e.g. plasticisers, lubricants, emulsifiers, rheology additives, catalysts, flow auxiliaries, optical brighteners, flame retardants, preservatives, antistatic agents or blowing agents.

In a preferred embodiment, the liquid dispersion may also be in the form of a coating composition. Such a coating composition contains the particulate solid, the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one component B which is neutralised with an acid of formula (V) or (VI) and the liquid diluent and additionally one or more binders, e.g. film-forming polymers or prepolymers which form a film upon curi ng. The coating composition may optionally contain conventional additives used in thecoating technology, e.g. plasticisers, lubricants, emu lsifiers, rheology additives, catalysts, flow auxiliaries, optical brighteners, flame retardants, preservatives, antistatic agents or blowing agents.

I n a preferred embodiment, the liquid dispersion may also be in the form of an in k, e.g. a printing ink or a gravu re in k. Such an ink contains the particu late solid, the branched modified polyetheramine or branched modified polyetheramine which is further modified with at least one com ponent B and the liquid diluent and additionally one or more binders conventionally used in the ink technology, e.g. film-forming polymers or prepolymers which form a film upon curing. The coating com position may optionally contain conventional additives, e.g. plasticisers, lubricants, emulsifiers, humectants, rheology additives, hu mectants, preservatives and antistatic agents.

I n a preferred embodiment, the liquid dispersion may also be in the form of an in k, e.g. a printing ink or a gravu re in k. Such an ink contains the particu late solid, the branched modified polyetheramine or branched modified polyetheramine which is further modified with at least one component B which is neutralised with an acid of formula (V) or (VI) and the liquid diluent and additionally one or more binders conventionally used in ink tech nology, e.g. film-forming polymers or prepolymers which form a film upon curing. Coating composition may optionally contain conventional additives, e.g. plasticisers, lubricants, emulsifiers, humectants, rheology additives, humectants, preservatives and antistatic agents.

The suitable binders are the ones customarily used, for example the ones described in UUmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vot. A18, pp. 368-426, VCH, Weinheim 1991, Germany. I n general, the film-forming binder is based on a thermoplastic or thermosetting resin, preferably on a thermosetting resin. Exam ples thereof are alkyd, acrylic, polyester, phenolic, melamine, epoxy and polyurethane resins and mixtures thereof. Also resins curable by radiation or air-drying resins can be used. Binders may also be derived from polyvinylalcohol and polyvinylbutyral.

If cold- or hot-curable binders are used, the addition of a curing catalyst may be advantageous. Suitable catalysts that accelerate the curing of binders are described, for example, in UUmann's, Zoi. A18, ioc. cit, p. 469.

I n another preferred embodiment, the coating compositions comprise a branched modified polyetherami ne or a branched modified polyetheramine, which is fu rther modified with at least one component B and a cross lin kable resin. Examples of coating compositions con taining specific binders are:

• Paints based on cold- or hot-cross linkable alkyd, acrylate, polyester, epoxy or melamine resins or mixtu res of such resins, if desired with addition of a curing catalyst; • Two-com ponent polyu rethane paints based on hydroxyl-containing acrylate, polyester or polyether resins and aliphatic or aromatic isocyanates, isocyanurates or polyisocyanates;

• One-component polyurethane paints based on blocked isocyanates, isocyanurates or polyisocyanates which are deblocked during baking, if desired with addition of a melamine resin;

• One-component polyurethane paints based on a trisalkoxycarbonyl triazine cross linker and a hyd roxyl group containing resin such as acrylate, polyester or polyether resins;

• One-component polyurethane paints based on aliphatic or aromatic urethane acrylates or polyurethane acrylates having free amino groups within the urethane structure and melamine resins or polyether resins, if necessary with curing catalyst;

• Two-com ponent paints based on (poly) ketimines and aliphatic or aromatic isocyanates, isocyanu rates or polyisocyanates;

• Two-com ponent paints based on (poly) ketimines and an u nsatu rated acrylate resin or a polyacetoacetate resin or a methacrylamidoglycolate methyl ester;

• Two-com ponent paints based on carboxyl- or amino-containing polyacrylates and polyepoxides;

• Two-component paints based on acrylate resins containing anhyd ride groups and on a polyhydroxy or polyamino component;

• Two-com ponent paints based on acrylate-containing an hydrides and polyepoxides;

• Two-com ponent paints based on (poly) oxazolines and acrylate resins containing anhyd ride grou ps, or u nsaturated acrylate resins, or aliphatic or aromatic isocyanates, isocyanu rates or polyisocyanates;

• Two-com ponent paints based on unsaturated polyacrylates and polymalonates;

• Thermoplastic polyacrylate paints based on thermoplastic acrylate resins or externally cross lin king acrylate resins in combination with etherified melamine resins; and

• Paint systems based on siloxane-modified or fluorine-modified acrylate resins.

I n another preferred embodiment, the coating composition preferably comprises

0.01 to 100.0 percentage by weight of the combined com ponents !) and ii), i.e. particu late solid and the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one component B in the com position, in particu lar 0.05 to 50.0 w%, especially 0.1 to 20.0 w%, per 100 percentage by weight of solid binder.

I n another preferred embodiment, the coating composition preferably comprises

0.01 to 100.0 percentage by weight of the combined com ponents !) and ii), i.e. particu late solid and the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one com ponent B is neutralised with an acid of formula (V) or (VI), in particular 0.05 to 50.0 percentage by weight, especially 0.1 to 20.0 percentage by weight, per 100 percentage by weight of solid binder.

I n a preferred embodiment, a method for preparing the liquid com position of the invention, the pigments are generally dispersed in the liquid diluent in the presence of the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one component B. The dispersion can be achieved by using conventional techniques, such as high speed mixing, ball milling, sand grinding, attritor grinding or two or three roll milling. The resulting pigment dispersion may have a pigment to dispersant weight ratio in the above range. Thus the obtained dispersion is also termed as a millbase.

In a preferred embodiment, a method for preparing the liquid composition of the invention, the pigments are generally dispersed in the liquid diluent in the presence of the branched modified polyetheramine or the branched modified polyetheramine which is further modified with at least one component B, which is neutralised with an acid of formula (V) or (VI). The dispersion can be achieved by using conventional techniques, such as high speed mixing, ball milling, sand grinding, attritor grinding or two or three roll milling. The resulting pigment dispersion may have a pigment to dispersant weight ratio in the above range. Thus the obtained dispersion is also termed as a millbase.

In another preferred embodiment, the method for preparing the coating composition or an ink the millbase will generally be incorporated, e.g. by mixing, into a liquid composition of the binder. It is, however, also possible to disperse the particulate solid in a solution of the branched modified polyetheramine and/or the salts thereof and/or the branched modified polyetheramine which is further modified with at least one component B and the salts thereof, concentrating the resulting mixture by distilling off the solvents and/or water, preferably to dryness, and optionally further subjecting the resulting concentrate to thermal and/or mechanical treatment to prepare a mixture comprising pigments and modified copolymers which may then be subsequently dispersed in a liquid binder formulation. According to this process, the solid composition of the particulate solid and the branched modified polyetheramine and/or the branched modified polyetheramine which is further modified with at least one component B is easy to disperse and does not require time and energy intensive grinding to be incorporated into e.g. a paint formulation.

In another preferred embodiment, the method for preparing the coating composition or an ink the millbase will generally be incorporated, e.g. by mixing, into a liquid composition of the binder. It is, however, also possible to disperse the particulate solid in a solution of the branched modified polyetheramine and/or the salts thereof and/or the branched modified polyetheramine which is further modified with at least one component B and the salts thereof, is neutralised with an acid of formula (V) or (VI), concentrating the resulting mixture by distilling off the solvents and/or water, preferably to dryness, and optionally further subjecting the resulting concentrate to thermal and/or mechanical treatment to prepare a mixture comprising pigments and modified copolymers which may then be subsequently dispersed in a liquid binder formulation. According to this process, the solid composition of particulate solid and the branched modified polyetheramine and/or the branched modified polyetheramine which is further modified with at least one component B which is neutralised with an acid of formula (V) or (VI) is easy to disperse and does not require time and energy intensive grinding to be incorporated into e.g. a paint formulation. I n another aspect, the presently claimed invention is directed to the use of the branched modified polyetheramine and/or branched modified polyetheramine which is further modified with com ponent B and the salts thereof as a dispersant for particulate solid material selected from the group consisting of pigments and fillers.

I n another aspect, the presently claimed invention is directed to the use of the branched modified polyetheramine and/or branched modified polyetheramine which is further modified with com ponent B and the salts thereof, is neutralised with an acid of formu la (V) or (VI), as a dispersant for particu late solid material selected from the grou p consisting of pigments and fillers.

The presently claimed invention offers one or more of the following advantages:

1. The presently claimed invention provides a universal dispersant prepared by

modifiying a branched polyetheramine polyol with at least one component B or fu rther modifiying a branched modified polyetheramine polyol with at least one component B or a branched modified polyetheramine polyol with at least one component B or a branched modified polyetheramine polyol further modified with at least one component B is neutralised with an acid of formula (V) and/or (VI).

2. The coating composition prepared by using dispersant of present invention display excellent gloss and crater ran king.

I n a preferred embodiment, weight average molecu lar weight is determined by gel permeation chromatography in accordance with DI N 55672-1.

I n a preferred embodiment, nu mber average molecular weight is determined by gel permeation chromatography in accordance with DI N 55672-1.

I n a preferred embodiment, the amine number is determined in accordance with DIN 53176.

I n a preferred embodiment, the acid nu mber is determined in accordance with DI N EN ISO 2114.

I n the following, specific embodiments of the present invention are described:

1. A branched modified polyetheramine having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is obtained by reacting a mixture comprising, a) at least one branched polyetheramine polyol P containing at least one hydroxyl groups having a weight average molecular weight M _w in the range of > 500 g/mol to < lOOOOg/mol and b) at least one compound B selected from-

O compounds of formula (I)

R-Fg (l) wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and Cr C ₄ -alkoxy;

linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is u nsubstituted or substituted by 1 or 2 radicals selected from OH and C _! -C ₄ -alkoxy;

a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected from OH, CrC^alkyl and C _! -C ₄ -alkoxy; and

aryl and aryl-C ₁ -C -alkyl, wherein the aryl part is u nsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, N H ₂ , NHC _j -C _z ralkyl, N (C ₁ -C ₄ -alkyl) ₂ , C _j -C^alkyl and C^C^alkoxy; and

Fg is independently of one another, selected from the group consisting of carboxylic acid, carboxylic acid anhydride, carboxylic acid ester, isocyanate, and mixtures thereof;

(ii) compounds of the formulae (I I) and wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N HC _j -C.ralkyl, N(C ₁ -C ₄ -alkyl) ₂ , C _j -C^alkyl and C^C^alkoxy; and

R ² is selected from the group consisting of hydrogen and CrC alkyl;

(iii) lactones of the formula (IV) (IV)

wherein A is a C ₃ -C ₁₂ -alkylene, which is u nsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and C _j -C^alkoxy; iv) internal anhydride of the formu la (V)

wherein D is selected from the group consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2-phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a C _j -C _jg alkyl or CrCi ₈ alkenyl radical and 1,2-phenylene is unsubstituted or substituted by 1 or 2 radicals selected from the grou p consisting of 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and CrC ₄ -alkoxy, -COOH or halogen. . The branched modified polyetheramine according to embodiment 1, having a weight average molecular weight M _w in the range of > 1000 g/mol to < 100000 g/mol, which is obtained by reacting a mixture com prising, a) at least one branched polyetheramine polyol P containing at least one

hydroxyl grou p having a weight average molecu lar weight M _w in the range of > 500g/mol to <10000 g/mol and b) at least one compound B selected from- i) compounds of formula (I)

R-Fg (l) wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is selected from (CH ₂ -C(CH ₃ ) ₂ )n; or C _n H _2n+1 , wherein n is an integer from 6 to 22, wherein alkyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and C _r C ₄ -alkoxy;

linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is C _n H _2n-1 , wherein n is an integer from 6 to 22, wherein alkenyl is unsubstituted or substituted by 1 or 2 radicals selected from OH and 0 ₄ -0 ₄ - alkoxy; a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected, from OH, Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

aryl and aryl-C ₁ -C ₄ -alkyl, wherein the aryl part is u nsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, N H ₂ , NHC ₁ -C ₄ -alkyl, N (CrC ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

Fg is independently of one another, selected from the group consisting of carboxylic acid, carboxylic acid anhydride, carboxylic acid ester, isocyanate, and mixtures thereof;

(ii) compounds of the formulae (I I) and (II I)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N HCrC ₄ -alkyl, N(CrC ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

R ² is selected from the group consisting of hydrogen and CrC ₄ -alkyl;

(iii) lactones of the formula (IV)

(IV)

wherein A is a C ₃ -Ci ₂ -alkylene, which is u nsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and C _j -C^alkoxy; iv) internal anhydride of the formu la (V)

(V)

wherein D is selected from the group consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2-phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a CrC ₁₈ alkyl or Ci-C ₁₈ alkenyl radical and 1,2-phenylene is unsubstituted or substituted by 1 or 2 radicals selected from the grou p consisting of 1 or 2 radicals selected from OH, C _j -C^alkyl and C^-C^alkoxy, -COOH or halogen. The branched modified polyetheramine according to embodiment 1 or 2, wherein the weight average molecular weight M _w of the branched modified polyetheramine is in the range of > 1000 g/mol to < 50000 g/mol. The branched modified polyetheramine according to one or more of embodiments 1 to 3, wherein the compound B is selected from C ₆ -C ₂₂ -alkenyl succinic an hyd rides, C ₆ -C ₂₂ -alkyl succinic anhydrides, polyisobutene succinic an hyd rides, C ₆ -C ₂₂ - alkylisocyanates, C ₆ -C ₂₂ -fatty acids, C ₁ -C ₄ -alkyl esters of C ₆ -C ₂₂ -fatty acids, isatoic anhyd ride, and aliphatic C ₄ -C ₁₂ -lactones. The branched modified polyetheramine according to one or more of embodiments 1 to 4, wherein the at least one branched polyetheramine polyol P contains > 1 to <

100 hydroxyl groups. The branched modified polyetheramine according to one or more of embodiments 1 to 5, wherein the at least one compound B reacts with at least one hydroxyl group of the at least one branched polyetheramine polyol P by formation of at least one lin king grou p selected from the grou p consisting of ester, u rethane or amide. The branched modified polyetheramine according to one or more of embodiments 1 to 6, wherein at least 5 mol % of the hyd roxyl groups of the at least one branched polyetheramine polyol P are reacted with the at least one com pou nd B. The branched modified polyetheramine according to one or more of embodiments 1 to 7, wherein the molar ratio of functional groups Fg in the at least one compou nd of general formula (I) to hydroxyl groups in the at least one branched polyetheramine polyol P or

the molar ratio of grou ps in the at least one compound of general formu la (I I) and/or (III) to hydroxyl groups in the at least one branched polyetheramine polyol P is in the range of > 0.1:1 to < 1:1

or

the molar ratio of grou ps in the at least one compound of general formu la (IV) to hyd roxyl groups in the at least one branched polyetheramine polyol P is in the range of > 1:1 to < 10:1

or the molar ratio of lactone groups in the at least one compound of general formula (V) to hydroxyl grou ps in the at least one branched polyetheramine polyol P

is in the range from > 0.05:1 to < 2:1.

9. The branched modified polyetheramine according one or more of embodiments 1 to 8, wherein the weight ratio of the at least one compound B to the at least one branched polyetheramine polyol P is in the range from > 1:3 to < 3:1.

10. The branched modified polyetheramine according to one or more of embodiments 1 to 9, wherein the at least one branched polyetheramine polyol P is a

polycondensation product of at least one tri-C ₂ -C ₄ -alkanolamine.

11. A branched modified polyetheramine having a weight average molecu lar weight M _w in the range of > 1000 g/mol to < 100,000 g/mol, which is obtained by reacting a mixture com prising c) at least one modified branched polyetheramine according to one or more of embodiments 1 to 10 and further modified with d) at least one compound B selected from i) com pou nds of formula (I)

R-Fg (l) wherein R is selected from the group consisting of

linear or branched alkyl having at least 6 carbon atoms, wherein alkyl is u nsubstituted or substituted by 1 or 2 radicals selected from OH and C _! -C ₄ -alkoxy;

linear or branched alkenyl having at least 6 carbon atoms, wherein alkenyl is u nsubstituted or substituted by 1 or 2 radicals selected from OH and C _j -C^alkoxy;

a cycloaliphatic radical having at least 5 carbon atoms, wherein the cycloaliphatic radical is unsubstituted or substituted by 1 or 2 radicals selected, from OH, Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

aryl and aryl-Ci-C ₄ -alkyl, wherein the aryl part is unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals selected from halogen, OH, NH ₂ , NHC _j -C^alkyl, N (C ₁ -C ₄ -alkyl) ₂ , C _j -C^alkyl and C^C^alkoxy; and

Fg is independently of one another, selected from the group consisting of carboxylic acid, hydroxy carboxylic acid, carboxylic acid an hydride, carboxylic acid ester, isocyanate, and mixtu res thereof; (ii) compounds of the formulae (I I) and (II I)

wherein

k is 0, 1, 2, 3 or 4;

R ¹ is selected from the group consisting of halogen, OH, NH ₂ , N HC _I -C ₄ - alkyl, N (CrC ₄ -alkyl) ₂ , Ci-C ₄ -alkyl and Ci-C ₄ -alkoxy; and

R ² is selected from the grou p consisting of hydrogen and C _j -CValkyl;

(iii) lactones of the formula (IV)

(IV)

wherein A is a C ₃ -C ₁₂ -alkylene, which is unsubstituted or substituted by 1 or 2 radicals selected from OH, Ci-C ₄ -alkyl and C _j -C^alkoxy; iv) internal anhydride of the formu la (V)

wherein D is selected from the group consisting of C ₂ -C ₆ alkylene, C ₂ -alkenylene and 1,2-phenylene, where C ₂ -C ₆ alkylene and C ₂ alkenylene are unsubstituted or carry a CrC ₁₈ alkyl or 0 ₄ -0 ₁₈ alkenyl radical and 1,2-phenylene is unsubstituted or substituted by 1 or 2 radicals selected from the grou p consisting of 1 or 2 radicals selected from OH, C _j -C^alkyl and C _j -C^alkoxy, -COOH or halogen; e branched modified polyetheramine according to one or more of embodiments 1 to 11, wherein the at least one branched polyetheramine polyol P has an amine number determined according to ISO 25761 in the range from > 200 to < 1000 mg KOH/g.

13. The branched modified polyetheramine according to one or more of embodiments 1 to

12, which is neutralized with at least one polymeric carboxylic acid or at least one polymeric phosphoric acid.

14. The branched modified polyetheramine according to embodiment 13, wherein the at least one polymeric carboxylic acid or the at least one polymeric phosphoric acid comprises a poly-C ₂ -C ₆ -alkyleneoxide radical.

15. A liquid composition in the form of a dispersion com prising, the branched modified polyetheramine according to one or more of embodiments 1 to 14 and a particulate solid material selected from the grou p consisting of pigments and fillers and a liquid diluent, wherein the particulate solid material is dispersed in the liquid diluent.

16. The liquid com position according to embodiment 15, wherein the weight ratio of

particulate solid material to the branched modified polyetheramine is in the range from > 100:1 to < 1:50.

17. The liquid com position according to embodiment 15 or 16, comprising,

a) > 1 to < 70 % by weight, based on the total weight of the liquid composition, of at least one particulate solid material, selected from the group consisting of pigments and fillers;

b) > 0.5 to < 50 % by weight, based on the total weight of the liquid composition, of the branched modified polyetheramine according to one or more of embodiments 1 to 16; and

c) > 10 to < 98.5 % by weight, based on the total weight of the liquid com position, of at least one liquid diluent.

18. The liquid com position according to embodiment 17, which is in the form of a millbase, a coating com position or an in k.

19. Use of the branched modified polyetheramine according to one or more of

embodiments 1 to 16 and the salts thereof as a dispersant for particulate solid material selected from the group consisting of pigments and fillers.

The invention is now fu rther illustrated by the following examples.

EXAMPLES

The presently claimed invention is further illustrated in combination with the following examples. These exam ples are provided to exemplify the presently claimed invention, but are not intended to restrict the scope of the presently claimed invention in any way. The below listed chemicals are used and all are commercially available.

Methods:

The nu mber average molecular weight and weight average molecular weight were determined by gel permeation chromatography in accordance with DI N 55672-1.

The amine number of modified branched polyetheramine was determined in accordance with DI N 53176.

The acid number was determined in accordance with DI N EN ISO 2114.

Example 1: Synthesis of compound of formula (VA1, outside the scope of the invention)

A mixture of 50.0 g (0.1 mol OH) of Pluriol® A500 E, 16.3 g (0.1 mol) of isatoic an hydride (IA) and 0.2 g (0.3 wt.-%) of 4-dimethylaminopyridine were heated to 80 to 140 C u ntil no more C0 ₂ was evolved. Then, 10.0 g (0.1 mol) of succinic anhydride (SSA) was added and the reaction mixtu re was heated at 80 ° C for an additional 3 hours to obtain the desired product. The product obtained was a yellowish liquid with an acid number of 75 mg KOH/g. Mw~810 g/mol, M n~765 g/mol, P D I— 1.05.

Example 2: Synthesis of compound of formu la (VB1, outside the scope of the invention)

A mixture of 84 g of Lutensol ON 70 and 16 g of succinic anhyd ride was stirred at 100 C until the acid number reached 90 mg KOH/g to obtain the desired product. The product obtained is a colorless liquid. Mw~650 g/mol, M n~610 g/mol, PDI-1.06.

Example 3: Synthesis of compound of formu la (VI, outside the scope of the invention)

A mixture of tripropyleneglycol monomethyl ether (1 mol), caprolactone (5.2 mol) and (0.01 mol) of dibutyltin dilaurate were heated to 160° C u nder an inert gas, u ntil a solids content of 97% had been reached to obtain the desired product. The polyether ester thus obtained was reacted with phosphorous pentoxide (0.033 mol) to produce mixtu re of mono and diester mixture as a yellow/colorless liquid with an acid nu mber of 65 mg KOH/g. Mw 920 g/mol, M n 850 g/mol, PDI of 1.08.

Example 4: Lupasol ^® EO-PI BSA

A mixture of 50 g Lu pasol ^® EO (BASF SE) and 60 g polyisobutylene SA F (BASF SE) was cooked at 80 ° C under N ₂ gas for 6 hours to obtain the desired product. The product obtained is a viscous yellowish liquid with an amine nu mber of 190 mg KOH/g. Mw -11000 g/mol, M n~7500 g/mol, PDI -1.5.

Example 5: Lupasol ^® EO-C12SAA

A mixture of 45 g Lu pasol ^® EO and 45 g dodecenylsuccinic an hyd ride was cooked at 80 C under N ₂ gas for 6 hours to obtain the desired product. The product obtained is a viscous yellowish liquid with an ami ne number of 200 mg KOH/g. Mw. 7500 g/mol, M n of 4150 g/mol, PDI of 1.8.

Exam ple 6: Lupasol ^® EO-urethane C18

A mixture of 45 g Lu pasol EO ^® , 40 g octadecyl isocyanate and 0.1 g DBTL was cooked at 80 C under N ₂ gas for 6 hours to obtain the desired product. The product obtained is a viscous yellowish wax with an amine number of 210 mg KOH/g. Mw -9500 g/mol, Mn -5500 g/mol, PDI— 1.7.

Example 7: Lupasol ^® EO-stearic acid

A mixture of 45 g Lupasol ^® EO and 55 g stearic acid was cooked at 170 C u nder N ₂ gas until the acid number is lower than 10 mg KOH/g to obtain the desired product. The product obtained is a yellowish solid with an amine number of 180 mg KOH/g. Mw -10500 g/mol, Mn -6500 g/mol, PDI—1.6.

Example 8: Lupasol ^® EO-lau ric acid

A mixture of 45 g Lu pasol ^® EO and 55 g lauric acid was cooked at 170 ° C u nder N ₂ gas until the acid number is lower than 10 mg KOH/g to obtain the desired product. The product obtained is a yellowish wax with an amine number of 180 mg KOH/g. Mw of 10520 g/mol, Mn of 6570 g/mol PDI of 1.6.

Example 9: Lupasol ^® EO-TOFA

A mixture of 45 g Lupasol ^® EO and 55 g tall oil fatty acid was cooked at 170 ° C under N ₂ gas until the acid number is lower than 10 mg KOH/g to obtain the desired product. The product obtained is a yellowish liquid with an ami ne nu mber of 180 mg KOH/g. Mw -12500 g/mol, M n~8250 g/mol, PDI -1.5.

Example 10: Lupasol ^® EO-CL

A mixture of 15 g Lu pasol ^® EO, 75 g epsilon-caprolactone and O.lg Dibutyltin dilaurate was cooked at 170 ° C until the solid content higher than 97% to obtain the desired product. The product obtained is a yellowish solid with an amine number of 68 mg KOH/g. Mw -17500 g/mol, M n -10250 g/mol, PDI— 1.7. Example 11: Lupasol ^® EO-CL/VL

A mixture of 15 g Lupasol ^® EO, 45 g epsilon-caprolactone, 20 g gamma-valerolactone and O.lg DBTL was cooked at 170 ° C u ntil the solid content higher than 97% to obtain the desired product. The product obtained is a yellowish liquid with an amine number of 77 mg KOH/g. Mw -18000 g/mol, Mn -12500 g/mol, PDI -1.4.

Example 12: Lupasol ^® EO-CL/VL/HSA

A mixture of 15 g Lupasol ^® EO, 45 g epsilon-caprolactone, 20 g gamma-valerolactone and O.lg DBTL was cooked at 170 ° C until the solid content higher than 97% . And then 10 g 12-Hydroxyl stearic acid added and cooked at 170° C until the acid number lower than 10 mg KOH/g to obtain the desi red product. The product obtained is a yellowish liquid with an amine nu mber of 69 mg KOH/g. Mw~14500 g/mol, Mn~9250 g/mol, PD I—1.5.

Example 13: Lupasol ^® EO-IA

A mixture of 70g Lu pasol ^® EO and 20 g isatoic an hydride was slowly heat up to 130° C and keep it at 130° C until no C0 ₂ gas formed to obtain the desired product. The product obtained is a yellowish viscous liquid with an amine number of 390 mg KOH/g. Mw -7550 g/mol, M n~4270 g/mol, PDI-1.8.

Example 14: Lupasol ^® EO-IA and fu rther CL/VL

A mixture of 42g Example 13, 60g epsilon-caprolactone, 30g gamma-valerolactone and 0.15g DBTL was cooked at 170° C u ntil the solid content higher than 97% to obtain the desired product. The product obtained is a yellowish viscous liquid with an amine number of 135 mg KOH/g. Mw~13500 g/mol, Mn~8550 g/mol, PDI-1.6.

Example 15: Lupasol ^® EO-IA and further TOFA

A mixture of 42g Example 13 and 30g tall oil fatty acid was cooked at 170 ° C under N ₂ gas until the acid number is lower than 10 mg KOH/g to obtain the desired product. The product obtained is a yellowish liquid with an amine number of 210 mg KOH/g. Mw~14500 g/mol, Mn~9850 g/mol, PDI-1.5.

Example 16: Lupasol ^® EO-TOFA fu rther SAA

A mixture of 50 g Example 9 and 5 g succinic anhydride was cooked at 100° C until the acid number reached 55 mg KOH/g to obtain the desired product. The product obtained is a yellowish liquid with an amine number of 165 mg KOH/g. Mw~13500 g/mol, M n~8550 g/mol, PDI-1.5.

Example 17: Lupasol ^® EO-TOFA fu rther IA

A mixture of 50 g Exam ple 9 and 5 g isatoic anhydride was slowly heat u p to 130° C and keep it at 130° C until no gas formed to obtain the desired product. The product obtained is a yellowish liquid with an amine number of 200 mg KOH/g. Mw~13700 g/mol, M n~8680 g/mol, PDI-1.5.

Example 18: Lupasol ^® EO-TOFA fu rther CL/VL A mixture of 50 g Example 9, 50g epsilon-caprolactone, 20g gamma-valerolactone and 0.15g DBTL was cooked at 170° C until the solid content higher than 97% to obtain the desired product. The product obtai ned is a yel lowish viscous liquid with an amine number of 75 mg KOH/g. Mw~19500 g/mol, M n~13500 g/mol, PDI-1.4.

Example 19: Lupasol ^® EO-CL/VL + Example 1:

A mixture 40g product of example 11 and 50 g product of example 1 was stirred at 80 C for 30 mi n to obtain the desired product. The product obtained is a yellowish viscous liquid with an amine number of 35 mg KOH/g. Mw~11500 g/mol, M n~6250 g/mol, PDI-1.9.

Example 17 Lupasol ^® EO-CL/VL/HSA + Example 2:

A mixture 40g product of example 12 and 50 g product of Exam ple 2 was stirred at 80 C for 30 mi n to obtain the desired product. The product obtained is a yellowish viscous liquid with an amine number of 33 mg KOH/g. Mw~9500 g/mol, M n~5250 g/mol, PD I ~ 1.8.

Example 18 Lupasol EO ^® -TOFA + Exam ple 3:

The mixtu re 40g product of example 12 and 50g product of Example 3 was stirred at 80 ° C for 30 to obtain the desired product. The product obtained is a yellowish viscous liquid with an amine number of 78 mg KOH/g. Mw~9250 g/mol, M n~3950 g/mol, PDI-2.3.

Performance Testing

I n order to test the dispersion effect of the obtained samples, Resin Free Pigment Concentrates (mill-base) were prepared according to the following Table Millbase Formu lation. The mi ll-base was dispersed in Scandex Shaker for 1 h with the help of glass beads. Afterwards the millbase was filtered and stored at room temperature overnight.

Table 1: Millbase Formu lation:

The performance of the examples above was tested by determining the rheological behavior of the millbase formu lations. The rheological behavior of the millbase was measu red at 23° C with a Thermo-Haake RheoStress 600 rheometer under CR-mode with rotation speed of 1 sec ¹ , respectively, using a cone-plate sensor. The results are summarized in table 2.

Table 2. Dispersion effect in clear coat paint system

Samples Viscosity (mPa.s)

Lu pasol ^® EO raw material without any modification.

The dispersant performance was also tested in clear coating systems with respect to gloss and anti-cratering effect. The let-down formu lations based on a clear coating system were prepared.

Let down formu lation:

Table 3:

Resi n 1: Saturated polyester resin in solvent naphtha/methoxy propanol/xylene (Setal ^® 173 VS-60) from Nuplex;

Resin 2: Mixtu re of 64.8 g of a first cellu lose acetate butyrate (CAB 381.2) and 25.2 g of a second cellulose acetate butyrate (CAB 381.20) in 255 g butyl acetate and 255 g of xylene, commercially available from Eastman Chemical;

Resin 3: Maprenal ^® MF 650: highly reactive isobutylated melamine-formaldehyde resin, commercially available from I neos;

Plasticizer: Resamine ^® H F 480: Polyu rea plasticizer, Carbamic resin based on butylurethane and formaldehyde, commercially available from Cytec.

Then, the colored paint compositions were prepared by mixing 1.0 g of the respective millbase with 9.0 g of the letdown formu lation, respectively, u nder 5 minutes at 2000 rpm. The paint was applied on a polyester film with a 150 miti film thickness. The gloss of the obtained coatings at a 20° angle was determined according to DIN 67530 using a commercial reflectometer (Micro-Tri-Gloss reflectometer from BYK Gardner). The performance resu lts are summarized in table 4.

Table 4. Gloss (20° ) and crater visual ran king (0 = no, 1 = few, 3 = some, 5 = a lot)

Lu pasol ^® EO is the raw material without any modification.

It is evident from the tables 2 and 4 that the dispersant prepared by modifying a branched polyetherami ne polyol with at least one component B or further modifying a branched modified polyetheramine polyol with at least one component B or a branched modified polyetheramine polyol with at least one component B or a branched modified polyetheramine polyol further modified with at least one com ponent B is neutralised with an acid of formula (V) and/or (VI) display excellent gloss and crater ranking.

The advantage of the presently claimed invention is that the dispersant prepared by modifying a branched polyetheramine polyol with at least one com ponent B or further modifying a branched modified polyetheramine polyol with at least one component B or a branched modified polyetheramine polyol with at least one component B or a branched modified polyetheramine polyol further modified with at least one component B which is neutralised with an acid of formula (V) and/or (VI) display excellent gloss and crater ranking.