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Title:
COMPOSITION COMPRISING SALICYLIC ACID DERIVATIVES AND A PARTICULAR SOLVENT
Document Type and Number:
WIPO Patent Application WO/2016/180979
Kind Code:
A1
Abstract:
The invention relates to a composition comprising: a) at least one compound of formula (I), at least one salt thereof of formula (II) or a mixture comprising at least one compound of formula (I) and at least one compound of formula (II); b) at least one compound chosen from: lipophilic derivatives of amino acids, isosorbide ethers, glycols chosen from pentylene glycol and hexylene glycol, fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms, oils of formulae R1COOR2 and R1OR2, and mixtures thereof. Use in caring for, making up and/or cleansing keratin materials, especially the skin.

Inventors:
SZESTAK MAGALI (FR)
JOUY CHANTAL (FR)
Application Number:
PCT/EP2016/060912
Publication Date:
November 17, 2016
Filing Date:
May 13, 2016
Export Citation:
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Assignee:
OREAL (FR)
International Classes:
A61K8/33; A61K8/34; A61K8/368; A61K8/37; A61K8/39; A61K8/44; A61K8/49; A61Q19/00
Domestic Patent References:
WO2007093375A12007-08-23
WO2015071374A12015-05-21
Foreign References:
FR2826273A12002-12-27
EP1269986A22003-01-02
FR2796550A12001-01-26
EP1044676A22000-10-18
EP0928608A21999-07-14
Other References:
CHEM. PHARM. BULL., vol. 49, 2001, pages 18 - 22
J. AGRIC. FOOD CHEM., vol. 49, 2001, pages 2548 - 2551
J. AM. MOSQUITO CONTROL ASSOCIATION, vol. 25, 2009, pages 386 - 389
PROCEEDINGS OF THE INSTITUTION OF CHEMISTS, 1961, pages 81 - 85
Attorney, Agent or Firm:
HUGODOT, Yannick (25-29 Quai Aulagnier, Asnières-sur-Seine Cedex, FR)
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Claims:
CLAIMS

1 . Composition comprising:

a) at least one compound of formula (I), at least one salt thereof of formula (II) or a mixture comprising at least one compound of formula (I) and at least one compound of formula

(I) (I I)

in which:

R independently denotes a saturated or unsaturated and linear or branched alkyl radical comprising from 12 to 20 carbon atoms, it being possible for said radical R to comprise one or more ethylenic unsaturations, and

Cat+ represents an organic or inorganic cation or mixture of organic or inorganic cations which makes it possible to achieve electrical neutrality of said compound(s) of formula (II) or of the mixture of compounds of formulae (I) and (II), b) at least one compound chosen from:

- lipophilic derivatives of amino acids,

- isosorbide ethers,

- glycols chosen from pentylene glycol and hexylene glycol,

- fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms,

- oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms,

and mixtures thereof.

2. Composition according to Claim 1 , in which R comprises from 14 to 18 carbon atoms, preferably from 14 to 16 carbon atoms.

3. Composition according to either of the preceding claims, in which the compound of formula (I) denotes compounds (Α'):

4. Composition according to any one of the preceding claims, characterized in that:

- the inorganic cation Cat+ is chosen from alkali metals, such as the sodium salt, alkaline- earth metals and transition metals; and

- the organic cation Cat+ is chosen from the cationic form of a primary, secondary or tertiary amine, and a quaternary ammonium.

5. Composition according to any one of the preceding claims, in which the cation Cat+ represents an organic cation or a mixture of organic cations chosen from:

(i) the cationic form of an amino acid of L or D form, and

(ii) a quaternary ammonium N+R1 R2R3-L-C02H, in which R1 ; R2 and R3, which may be identical or different, denote a saturated linear alkyl radical comprising from 1 to 12 carbon atoms and L denotes a saturated linear divalent hydrocarbon-based radical comprising from 1 to 6 carbon atoms.

6. Composition according to any one of the preceding claims, in which Cat+ represents the cationic form of an amino acid of L or D form and preferably the cationic form of lysine, arginine, alanine or tryptophan, more preferentially of lysine.

7. Composition according to any one of Claims 1 to 6, in which the compound of formula (II) is chosen from the following compounds (A), (B), (C) and (D), alone or as a mixture:

in which Cat+ is as defined in any one of Claims 1 and 3 to 5. 8. Composition according to Claim 7, in which the compound of formula (II) is the compound of formula (F) or the compound of formula (E):

9. Composition according to one of Claims 1 to 8, characterized in that said compound(s) defined in b) are chosen from:

- isopropyl N-lauroylsarcosinate,

- dimethyl isosorbide, - pentylene glycol,

- octyldodecanol,

- isononyl isononanoate, isopropyl palmitate and/or 2-ethylhexyl palmitate,

and mixtures thereof.

10. Composition according to one of Claims 1 to 3, characterized in that the composition is anhydrous, in that the compound(s) defined in a) is a compound of formula (I) as defined in any one of Claims 1 to 3, and/or in that said compound(s) defined in b) are chosen from:

- lipophilic derivatives of amino acids, preferably isopropyl N-lauroylsarcosinate,

- isosorbide ethers, preferably dimethyl isosorbide,

- glycols chosen from pentylene glycol and hexylene glycol, preferably pentylene glycol, and mixtures thereof.

1 1 . Composition according to one of Claims 1 to 9, characterized in that the composition comprises water, and in that said compound(s) defined in b) are chosen from:

- lipophilic derivatives of amino acids, preferably isopropyl N-lauroylsarcosinate,

- fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms, preferably octyldodecanol,

- oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms, preferably isononyl isononanoate, isopropyl palmitate and/or 2-ethylhexyl palmitate,

and mixtures thereof.

12. Composition according to Claim 1 1 , characterized in that water is present in a content ranging from 10% to 99% by weight, preferably ranging from 20% to 80% by weight or ranging from 40% to 75% by weight relative to the total weight of the composition.

13. Composition according to either of Claims 1 1 and 12, characterized in that it is in the form of a water-in-oil or oil-in-water emulsion, preferably an oil-in-water emulsion. 14. Composition according to any one of the preceding claims, characterized in that the compound(s) defined in a) are present in a total content of compounds (I) and/or (II) ranging from 0.01 % to 40% by weight, in particular ranging from 0.1 % to 10% by weight, more particularly ranging from 0.2% to 8% by weight and in particular ranging from 0.5% to 5% by weight, relative to the total weight of the composition.

15. Composition according to any one of the preceding claims, characterized in that the compound(s) defined in b) are present in a content ranging from 0.01 % to 99% by weight, preferably ranging from 0.1 % to 20% by weight and in particular ranging from 1 % to 15% by weight relative to the total weight of the composition.

16. Composition according to any one of the preceding claims, in which the mass ratio of said compound(s) defined in b) relative to the compound(s) defined in a) of formula (I) and/or of formula (II) is greater than or equal to 2, in particular ranging from 2.5 to 40 and preferably ranging from 5 to 20.

17. Composition according to any one of the preceding claims, characterized in that it is a cosmetic composition.

18. Cosmetic process for treating keratin materials, comprising the application to the keratin materials, such as the skin, of a composition according to any one of the preceding claims.

Description:
Composition comprising salicylic acid derivatives and a particular solvent

The present invention relates to a composition, preferably a cosmetic composition, comprising certain salicylic acid derivatives, and at least one particular compound promoting the dissolution of these said derivatives.

In the context of the present invention, these salicylic acid derivatives correspond to at least one compound of formula (I), at least one of the salts thereof of formula (II) or a mixture comprising at least one compound of formula (I) and at least one compound of formula

(I) (I I)

as defined in detail below.

These compounds, which are in solid form at room temperature, are difficult to dissolve, and especially are sparingly soluble in water and glycerol. Now, it is necessary for this compound and/or a salt thereof to be formulated in a dissolved form, and especially in a high content, such as greater than or equal to 0.50% by weight in a composition, in order to fully exploit its activity, and it is also preferable for its solubilization to be maintained over time in order to avoid any recrystallization during the storage of compositions comprising such a compound.

The reason for this is that the dissolved forms lead to better bioavailability in the skin than crystalline forms, the crystal size of which is poorly controlled.

For the purposes of the present application, the term "bioavailability" means the molecular penetration of the active agent concerned into the live layers of the skin and in particular of the epidermis. It will be sought for the penetrated concentration to be as high as possible, so as to increase the amount of active agent reaching the live layers of the skin.

The term "dissolved form" means a dispersion of the derivatives according to the invention in a liquid, in the free molecular state, in particular in non-complexed form. No crystallization of the salicylic acid derivatives according to the invention is visible to the naked eye or under cross-polarized light microscopy. The object of the present invention is, precisely, to propose a novel galenical formulation of the salicylic acid derivatives according to the invention that enables the abovementioned drawbacks to be overcome, and thus enables these compounds to be incorporated in a long-lasting dissolved form. This novel galenical formulation of the salicylic acid derivatives according to the invention makes it possible especially to improve the efficacy of the active agent for the treatment of keratin materials such as the skin. The compositions according to the invention make it possible especially to formulate salicylic acid derivatives in a dissolved form in a high content, without using large amounts of glycols in the composition.

This novel galenical formulation of the salicylic acid derivatives according to the invention makes also it possible in particular sensory properties experienced ( a touch or feeling with better freshness, penetration, sliding or softness, and/or less greasy) in the application on keratin materials such as the skin of said formulation.

The inventors have in fact discovered, unexpectedly, that the combination of at least one salicylic acid derivative (a) as defined below, compounds of formula (I) and/or compounds of formula (II), with at least one compound (b) as defined later, makes it possible to improve the solubility of these salicylic acid derivatives and/or salts thereof while at the same time avoiding their recrystallization, especially after storage for 2 months at room temperature (25°C) and/or at 4°C and/or at 45°C.

The inventors have discovered in particular, unexpectedly, that novel galenical formulation comprising the combination of at least one salicylic acid derivative (a) as defined below, compounds of formula (I) and/or compounds of formula (II), with at least one compound (b) as defined later, makes it possible especially to improve sensory properties experienced in the application on keratin materials such as the skin of said formulation, in particular makes it possible a touch or feeling with better freshness, better sliding or softness, and/or less greasy.

More specifically, one subject of the invention is a composition, especially a cosmetic composition, comprising:

a) at least one compound of formula (I), at least one salt thereof of formula (II) or a mixture comprising at least one compound of formula (I) and at least one compound of formula (II):

(I) (I I)

in which:

R independently denotes a saturated or unsaturated and linear or branched alkyl radical comprising from 12 to 20 carbon atoms, it being possible for said radical R to comprise one or more ethylenic unsaturations, and

Cat+ represents an organic or inorganic cation or a mixture of organic or inorganic cations which makes it possible to achieve electrical neutrality of the compound of formula (II) or of the mixture of compounds of formulae (I) and (II), b) at least one compound chosen from:

- lipophilic derivatives of amino acids,

- isosorbide ethers,

- glycols chosen from pentylene glycol and hexylene glycol,

- fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms,

- oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms,

and mixtures thereof.

A subject of the invention is also a process for preparing such a composition, comprising the following steps:

1 ) dissolving at least one compound a) as defined above by mixing said compound(s) a) with at least one compound b) as defined above, and then

2) adding said mixture prepared in step 1 ) to the other ingredients of said composition as defined below. Preferably, step 1 of said process is performed by heating to a temperature of 40-60°C, preferably at 70°C, with stirring (for example magnetic stirring), especially for about 10 minutes. More particularly, the step of said process is likewise performed at a temperature of 40- 60°C. a) SALICYLIC ACID DERIVATIVES

The invention relates to compositions comprising at least one compound of formula (I), at least one salt thereof of formula (II) or a mixture comprising at least one compound of formula (I) and at least one compound of formula (II):

(I) (I I)

The compounds of formula (I) and the salts of formula (II) are cosmetically acceptable.

Within the meaning of the present invention, the terms "cosmetically acceptable" and "physiologically acceptable" are equivalent.

For the purposes of the invention, the term "cosmetically acceptable compound" is intended to denote any compound suitable for the topical administration of a composition in which it is present.

A cosmetically acceptable compound is preferentially a compound which has no odour or unpleasant appearance, and which is entirely compatible with the topical administration route.

In the present case, a compound according to the invention, a mixture of compounds according to the invention or a composition comprising one or more compound^) according to the invention is employed topically, i.e; by application at the surface of the keratin material targeted, said keratin material preferably being the skin of the face and/or body and more particularly the skin of the face and/or neck.

The radical R independently denotes, in the formulae (I) and (II), a saturated or unsaturated and linear or branched alkyl radical which comprises from 12 to 20 carbon atoms, preferably from 14 to 18 carbon atoms, in particular 14, 15, 16, 17 or 18 carbon atoms, preferably from 14 to 16 carbon atoms, and which may comprise one or more ethylene unsaturations. According to a first variant, the radical R of the compounds according to the invention does not comprise an ethylenic unsaturation.

According to a second variant, the radical R of the compounds according to the invention comprises at least one ethylenic unsaturation, preferably one, two or three ethylenic unsaturations.

According to a third variant, the radical R of the compounds of the invention comprises from 14 to 18 carbon atoms, preferably from 14 to 16 carbon atoms, and comprises one, two or three ethylenic unsaturations.

Cat+ represents an organic or inorganic cation or a mixture of organic or inor- ganic cations which makes it possible to achieve electrical neutrality of the compound of formula (II) or of the mixture of compounds of formulae (I) and (II).

Cat+ can be mono-charge or multi-charge.

Preferably, Cat+ represents a mono-charge cation or a mixture of mono- charge cations, preferably a mono-charge cation.

According to one embodiment, Cat+ represents an inorganic cation.

Mention may in particular be made, among inorganic cations, of alkali metal cations, such as sodium or potassium salts, alkaline-earth metal salts, such as calcium, strontium or magnesium salts, or also transition metal salts, such as copper, zinc, iron or manganese salts.

According to one embodiment, Cat+ is chosen from alkali metal, alkaline-earth metal and transition metal salts.

According to a specific embodiment, Cat+ is chosen from the group consisting of sodium, potassium, calcium, strontium, magnesium, copper, zinc, iron and manganese salts. Preferably, Cat+ represents the sodium salt.

According to one embodiment, Cat+ represents an organic cation.

Mention may be made, among organic cations, of primary, secondary or tertiary amines in their cationic form, and also quaternary ammoniums.

In particular, Cat+ may denote the cationic form of triethanolamine, monoeth- anolamine, diethanolamine, hexadecylamine, N,N,N',N'-tetrakis(2-hydroxypropyl) ethylenediamine or also tris(hydroxymethyl)aminomethane.

According to a specific embodiment, Cat+ is an organic cation or a mixture of organic cations chosen from:

(i) the cationic form of an amino acid of L or D form, and

(ii) a quaternary ammonium N + R 1 R 2 R 3 -L-C0 2 H, in which R 1 ; R 2 and R 3 , which may be identical or different, denote a saturated linear alkyl radical comprising from 1 to 12 carbon atoms and L denotes a saturated linear divalent hydrocarbon-based radical comprising from 1 to 6 carbon atoms.

According to a first embodiment, the Cat+ cation represents the cationic form of an amino acid of L or D form and preferably the cationic form of lysine, arginine, alanine or tryptophan, more preferentially of lysine.

According to a second embodiment, Cat+ represents a quaternary ammonium N + R 1 R 2 R 3 -L-C0 2 H, in which:

Ri , R 2 and R 3 , which may be identical or different, preferentially represent a saturated linear alkyl radical comprising from 1 to 4 carbon atoms and in particular repre- sent a methyl radical; R 1 ; R 2 and R 3 are preferably identical; and/or

L preferably denotes a saturated linear divalent C C 4 hydrocarbon-based radical, in particular a divalent -CH 2 - radical.

According to this embodiment, Cat+ preferably denotes a quaternary ammonium N + R 1 R 2 R 3 -L-C0 2 H salt, in which R 1 ; R 2 and R 3 are identical and denote a saturated linear alkyl radical comprising from 1 to 4 carbon atoms and L denotes a saturated linear divalent C C 4 hydrocarbon-based radical.

According to this second embodiment, particularly preferably, R 1 ; R 2 and R 3 are identical and denote a methyl radical and L denotes a divalent -CH 2 radical.

According to one embodiment, Cat+ represents a sodium salt or the cationic form of lysine, preferably the cationic form of lysine.

According to one embodiment, the present invention relates to the use of a compound of formula (I) or of a mixture of compounds of formula (I).

According to one embodiment, the compound of formula (I) denotes the compound

In a particular embodiment of the invention, a composition according to the invention is anhydrous and comprises at least one compound of formula (I) as defined above, preferably compound (Α').

According to another embodiment, the present invention relates to the use of a compound of formula (II). According to a most particularly preferred embodiment of the invention, the compound of formula (II) is chosen from compounds (A), (B), (C) and (D) below:

Preferably, the compound of formula (II) is (A).

Preferably, the compound of formula (II) is (A) and Cat+ is chosen from an alkali metal salt, preferably a sodium salt, and the cationic form of an amino acid of L or D form, preferably the cationic form of lysine, and preferably represents the cationic form of lysine.

Thus, according to a preferred embodiment, the compound of formula (II) denotes the compound (E) and/or (F):

(E)

and preferably denotes the compound (F).

According to another embodiment, the present invention relates to the use of a mixture of compounds of formula (II).

According to this embodiment, the mixture of compounds of formula (II) com- prises at least one compound possessing at least one ethylenic unsaturation, preferably at least one compound comprising an ethylenic unsaturation and at least one compound not comprising an ethylenic unsaturation.

Preferably, the present invention relates to the use of a mixture of compounds of formula (II) comprising at least one compound not comprising an ethylenic unsaturation, at least one compound comprising an ethylenic unsaturation, at least one compound comprising two ethylenic unsaturations and at least one compound comprising three ethylenic unsaturations.

Preferably, these compounds contain a radical R bearing the same number of carbon atoms.

The compounds of formula (II) according to this embodiment may be chosen from compounds (A), (B), (C) and (D) indicated above.

According to one embodiment, a mixture of at least 4 compounds of formula (II) is used, denoted compounds (1), (2), (3) and (4), in which:

the radicals R of each of the compounds (1 ), (2), (3) and (4) denote a linear hydrocarbon-based radical comprising from 14 to 18 carbon atoms, preferably from 14 to 16 carbon atoms and more preferentially 15 carbon atoms, and contain the same number of carbon atoms in each of the compounds (1), (2), (3) and (4); and

Preferably, according to this embodiment, in the mixture of the compounds (1 ),

(2), (3) and (4):

- the proportion of compound (1) ranges from 0.001 % to 5%, preferably from 0.5% to 1 %,

- the proportion of compound (2) ranges from 20% to 45%, preferably from 30% to 35%,

- the proportion of compound (3) ranges from 5% to 35%, preferably from 15% to 25%,

- the proportion of compound (4) ranges from 25% to 50%, preferably from 35% to 40%, the percentages being by mass, relative to the total weight of the mixture of compounds (1), (2), (3) and (4).

According to a particular embodiment, the mixture of compounds (1), (2), (3) and (4) denotes the mixture of compounds (A), (B), (C) and (D) and more preferentially the mixture of compounds (A), (B), (C) and (D) for which Cat+ is chosen from an alkali metal salt, preferably a sodium salt, and the cationic form of an amino acid of L or D form, preferably the cationic form of lysine, and preferably represents the cationic form of lysine.

According to one embodiment, the present invention relates to the use of a mixture of compounds of formula (I) and of compounds of formula (II), especially as defined previously.

According to this embodiment, the compound of formula (I) preferably denotes compound (Α'):

and compound (II) preferably denotes compound (E) and/or (F):

preferably the compound (F).

In a particular embodiment of the invention, a composition according to the invention comprises water and comprises at least one compound of formula (I) and at least one compound of formula (II) as defined above, and preferably comprises compound (Α') and compound (F) or compound (Α') and compound (E). PREPARATION OF THE SALICYLIC ACID DERIVATIVES

1 : Preparation of the compounds of formula (I)

The compounds of formula (I) may be obtained in 2 or 3 steps starting from compounds A2 and B1 illustrated in the synthetic scheme below.

Compound A2, with x representing an integer between 1 and 9, may be obtained by synthesis in 8 steps starting from compound A1 (Chem. Pharm. Bull., 2001 , 49, 18-22).

Compound B1 may be obtained in four steps starting from 3-butynol, as de- scribed in Chem. Pharm. Bull., 2001 , 49, 18-22.

Compound B2 may be obtained by Wittig coupling between compounds A2 and B1 in the presence of butyllithium in an apolar solvent such as hexane, for example, at room temperature, under an inert atmosphere.

In compound B2, M denotes a saturated C 6 -C 15 alkyl radical, such as C 6 H 13 ; or a monounsaturated alkyl radical of formula C n H 2 n + i with n ranging from 5 to 15, such as - CH 2 =C 5 Hn or -CH 2 -CH=CH-C 3 H7; or an alkyl radical comprising two unsaturations of formula C m H 2m+ i with m representing an integer ranging from 5 to 15, such as -CH 2 -CH=CH-

Compound G may be obtained from compound B2 by reaction with BBr 3 in di- chloromethane, for example, followed by treatment with sodium hydroxide in a protic solvent such as ethanol.

In compounds A1 , A2, B1 , B2 and G, x represents an integer between 1 and

9. Depending on the nature of the radical M, compound G obtained includes 1 , 2 or 3 unsaturations (compound G corresponds to the mono-, di- or tri unsaturated compounds of formula (I)).

In order to obtain the corresponding saturated compounds of formula (I), a saturated radical M is preferentially used and the double bond introduced during the Wittig reaction is reduced by catalytic hydrogenation, for example using Pd/C in a protic solvent, it being possible for this hydrogenation to be performed either on compound B2 or, after the reaction with BBr 3 /NaOH, on compound G. 2: Preparation of the compounds of formula (II)

The compounds of formula (II) may be obtained:

1 - as a mixture from starting material of natural origin (as illustrated in part 2.1 below); or

2- by salification of the compounds of formula (I) obtained in accordance with part 1 above (as illustrated in part 2.2 below).

2.1 From starting material of natural origin

A mixture of compounds of formula (II) for which R denotes a linear C 15 hydrocarbon-based chain presented below may be obtained in 2 steps starting from the ana- card ic acid mixture.

Anacardic acid is a mixture of four 6-15 alkylsalicylic acid compounds: 6- pentadecylsalicylic acid (Α'), 6-[8(Z)-pentadecenyl]salicylic acid (Β'), 6-[8(Z),-1 1 (Z)- pentadecadienyl]salicylic acid (C) and 6-[8(Z),1 1 (Z),-14-pentadecatrienyl]salicylic acid (D'), of formulae:

It is a "C15 mixture" of natural origin.

In a first step, the anacardic acid mixture, or "C15 mixture", may be obtained from raw or natural starting material, known as CNSL ("Cashew Nut Shell Liquid"), ex- tracted from the cashew (Anacardium occidentale) nut shell, generally containing from 60% to 80% of anacardic acid. This isolation of the anacardic mixture may in particular be performed according to the method described in J. Agric. Food Chem., 2001 , 49, 2548- 2551 . In particular, compound (Α') described above in the description, for which R denotes a saturated linear C 15 chain, may be obtained by catalytic hydrogenation of the anacardic mixture of compounds A', B', C and D'

2.2 Salification

The preparation of the sodium salt of the "C15 mixture", or anacardic acid mixture, is described in J. Am. Mosquito Control Association, 2009, 25, 386-389, and in Proceedings of the Institution of Chemists, 1961 , 81 -85.

The salts of formula (II) may be obtained by adding one equivalent of the sali- fying compound to compound (I) or to the mixture of compounds (I).

In particular, the salts of formula (II) may be obtained by adding one equivalent of the salifying compound in the form of an aqueous solution to a solution in an alcohol, such as isopropanol, of compound (I) or of the mixture of compounds (I). The salts of formula (II) are isolated by evaporation of the solvent. In the present text, the sodium salt (E) and the lysine salt (F) of formulae:

described previously in the description, and corresponding to the salts of com- pound A' of anacardic acid, were obtained by addition of aqueous solutions, respectively, of sodium hydroxide and lysine (one equivalent) to compound A' dissolved in methanol, followed by evaporation of the solvent.

Compound(s) a) are present in a total content of compounds (I) and/or (II) ranging from 0.01 % to 30% by weight, better still from 0.1 % to 10% by weight, more particularly from 0.2% to 8% by weight and in particular from 0.5% to 5% by weight, relative to the total weight of the composition.

b) COMPOUNDS PROMOTING THE DISSOLUTION OF THE SALICYLIC

ACID DERIVATIVES

The composition according to the invention comprises at least one compound that promotes the dissolution of at least one compound of formula (I), of at least one salt thereof of formula (II), or of at least one mixture comprising said compound of formula (I) and said compound of formula (II) according to the invention, this or these compound(s) defined in b) being chosen from:

- lipophilic derivatives of amino acids,

- isosorbide ethers,

- glycols chosen from pentylene glycol and hexylene glycol,

- fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms,

- oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms,

and mixtures thereof. i) The lipophilic derivatives of amino acids are especially C6-C22 N-acylamino acid esters. These derivatives are especially those described in patent application EP 1 269 986.

The N-acylamino acid ester(s) are generally of formula II:

R , i(CO)N(R , 2 )CH(R , 3 )(CH 2 )n(CO)OR , 4 in which:

n is an integer equal to 0, 1 or 2,

R'i represents a linear or branched C 5 -C 2 i alkyl or alkenyl radical,

R' 2 represents a hydrogen atom or a Ci to C 3 alkyl group,

R' 3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C 3 or C 4 alkyl radical,

R' 4 represents a linear or branched Ci to Ci 0 alkyl or C 2 to Ci 0 alkenyl radical, or a sterol residue.

Preferably, the group R'i(CO)- is an acyl group of an acid chosen from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids and palm kernel oil fatty acids. These fatty acids may also contain a hydroxyl group. Even more preferably, it will be lauric acid.

The -N(R' 2 )CH(R' 3 )(CH 2 ) n (CO)- part of the amino acid ester is preferably chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, β-alanine, aminobutyric acid, aminocaproic acid, sarcosine, or N- methyl-B-alanine.

Even more preferably, it will be sarcosine.

The part of the amino acid esters corresponding to the group OR' 4 may be obtained from alcohols chosen from the group formed by methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, isobutanol, 3-methyl-1 -butanol, 2-methyl-1 -butanol, fusel oil, pentanol, hexanol, cyclohexanol, octanol, 2-ethylhexanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, jojoba alcohol, 2-hexadecyl alcohol, 2-octyldodecanol and isostearyl alcohol.

These amino acid esters may be obtained in particular from natural sources of amino acids. In this case, the amino acids originate from the hydrolysis of natural plant proteins (oat, wheat, soybean, palm or coconut) and then necessarily lead to mixtures of amino acids that subsequently need to be esterified and then N-acylated. The preparation of such amino acids is more particularly described in patent application FR 2 796 550, which is incorporated herein by reference.

The amino acid ester more particularly preferred for its use in the present invention is isopropyl N-lauroylsarcosinate of formula:

O O

II II CH 3 (CH 2 ) 10 C— NCH 2 C OCHCH g

CH 3 CH 3 such as the product sold under the name Eldew SL-205 by the company Ajinomoto.

The amino acid esters that are preferably used for the purposes of the present invention, and the synthesis thereof, are described in patent applications EP 1 044 676 and EP 0 928 608 from the company Ajinomoto Co. ii) An isosorbide ether may especially be dimethyl isosorbide; in particular, use will be made of dimethyl isosorbide sold under the name Arlasolve DMI by the company Uniqema. iii) The glycols according to the invention are chosen from pentylene glycol and hexylene glycol; the glycol is preferably pentylene glycol. iv) The fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms may be chosen from cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol.

More particularly, the fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms may be chosen especially from octyldodecanol, 2-butyloctanol, 2-hexyldecanol and 2-undecylpentadecanol. Preferably, the fatty alcohol containing from 8 to 26 carbon atoms is octyldodecanol or 2- octyldodecanol sold under the name Isofol N/F by the company Sasol. v) the oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms may be chosen from: Purcellin oil, isononyl isononanoate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate or triisocetyl citrate; fatty alcohol heptanoates, octanoates or decanoates; polyol esters, for instance propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters, for instance pentaerythrityl tetraisostearate.

Preferably, the oils v) are chosen from: isononyl isononanoate, isopropyl palmitate, 2- ethylhexyl palmitate, and mixtures thereof. Isononyl isononanoate is sold under the name Isononyl isononanoate DUB INN by the company Stearineries Dubois.

2-Ethylhexyl palmitate is sold under the name 2-Ethylhexyl palmitate (DUB PO) by the company Stearineries Dubois.

Isopropyl palmitate is sold under the name Isopropyl palmitate (DUB IPP) by the company Stearineries Dubois.

Compounds (i) to (v) described previously may be used alone or as a mixture in the compositions according to the invention.

More particularly, said compound(s) defined in b) are chosen from:

- isopropyl N-lauroylsarcosinate,

- dimethyl isosorbide,

- pentylene glycol,

- octyldodecanol,

- isononyl isononanoate, isopropyl palmitate and/or 2-ethylhexyl palmitate,

and mixtures thereof.

In particular, the ingredient that promotes the dissolution of said compounds a) defined above is isopropyl N-lauroylsarcosinate.

According to a preferred embodiment, the composition according to the invention comprises (a) at least one compound of formula (I)

preferably the compound of formula (Α') as defined above, and at least one lipophilic derivative of an amino acid, in particular Isopropyl N-lauroylsarcosinate sold especially by Ajinomoto under the name Eldew SL 205.

Isopropyl N-lauroylsarcosinate, pentylene glycol and/or dimethyl isosorbide will be advantageous for dissolving large amounts of compound of formula (I), which may be greater than or equal to 25% by weight, preferably greater than or equal to 30% by weight percentage of compound(s) of formula (I), preferably compound (Α'), present in a formulation containing only these said compounds (b) as defined above.

Isopropyl N-lauroylsarcosinate, pentylene glycol and/or dimethyl isosorbide will be advantageous for dissolving large amounts of compound of formula (I), which may be greater than or equal to 0.5% by weight, preferably greater than or equal to 5% by weight percentage of compound(s) of formula (I), preferably compound (Α'), present in an anhydrous composition according to the invention as defined above.

According to another preferred embodiment, the composition according to the invention comprises:

(a) at least one compound of formula (I), which is a compound of formula (A), and at least one compound of formula (II), which is the compound of formula (E), and

(b) at least one lipophilic derivative of amino acids.

According to another preferred embodiment, the composition according to the invention comprises:

(a) at least one compound of formula (I), which is a compound of formula (Α'), and at least one compound of formula (II), which is the compound of formula (F), and

(b) at least one lipophilic derivative of amino acids. In the compositions according to the invention, the compound(s) defined in a) are present in a total content of compounds (I) and/or (II) ranging from 0.01 % to 40% by weight, in particular from 0.1 % to 10% by weight, more particularly from 0.2% to 8% by weight and in particular from 0.5% to 5% by weight, relative to the total weight of the composition. The compound(s) defined in b), i.e. the ingredient(s) that promote the dissolution of the compound(s) defined in a), may be present in a content ranging from 0.01 % to 99% by weight, particularly ranging from 0.1 % to 20% by weight and more particularly from 1 % to 15% by weight relative to the total weight of the composition.

The mass ratio of said compound(s) that promote dissolution defined in b) relative to the compound(s) defined in a) of formula (I) and/or of formula (II) present in the composition according to the invention is generally greater than or equal to 2, for example ranging from 2.5 to 40 and preferably ranging from 5 to 20.

In a particular embodiment of the invention, the composition is anhydrous, and said compound(s) defined in b) are chosen from:

- lipophilic derivatives of amino acids, preferably isopropyl N-lauroylsarcosinate,

- isosorbide ethers, preferably dimethyl isosorbide,

- glycols chosen from pentylene glycol and hexylene glycol, preferably pentylene glycol, and mixtures thereof.

More particularly, a composition according to the invention is anhydrous, comprises as compound(s) defined in a) at least one compound of formula (I), preferably compound (Α'), and said compound(s) defined in b) which are chosen from:

- lipophilic derivatives of amino acids, preferably isopropyl N-lauroylsarcosinate,

- isosorbide ethers, preferably dimethyl isosorbide,

- glycols chosen from pentylene glycol and hexylene glycol, preferably pentylene glycol, and mixtures thereof.

In another particular embodiment of the invention, the composition comprises water, and said compound(s) defined in b) are chosen from:

- lipophilic derivatives of amino acids, preferably isopropyl N-lauroylsarcosinate,

- fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms, preferably octyldodecanol,

- oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms, preferably isononyl isononanoate, isopropyl palmitate and/or 2-ethylhexyl palmitate,

and mixtures thereof. More particularly, a composition according to the invention comprises water, comprises as compound(s) defined in a) compound (Α') and/or compound (F) or compound (E), and said compound(s) b) are chosen from:

- lipophilic derivatives of amino acids, preferably isopropyl N-lauroylsarcosinate,

- fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms, preferably octyldodecanol,

- oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms, preferably isononyl isononanoate, isopropyl palmitate and/or 2-ethylhexyl palmitate,

and mixtures thereof.

The compositions used according to the invention may comprise a physiologically acceptable medium, i.e. a medium that is suitable for the topical administration of a composition, i.e. that is compatible with human keratin materials such as the skin, the scalp, the hair and the nails.

In a particular embodiment of the invention, the compositions, preferably cosmetic compositions, comprise a physiologically acceptable medium.

According to the invention, a physiologically acceptable medium is preferentially a cosmetically acceptable medium, that is to say a medium which is devoid of unpleasant odour or appearance and which is entirely compatible with the topical administration route.

According to the invention, the term "keratin materials" means the skin, of the body, face and/or area around the eyes, the lips, the nails, mucous membranes, the eyelashes, the eyebrows, bodily hair, the scalp and/or head hair, or any other area of bodily skin. More particularly, the keratin materials according to the invention are the scalp, the hair and/or the skin.

Preferably, the keratin materials according to the invention are the scalp and/or the hair. Preferably, the keratin material according to the invention is the skin.

The term "skin" means all of the skin of the body, and preferably the skin of the face, neckline, neck, arms and forearms, or even more preferably still the skin of the face, in particular of the forehead, nose, cheeks, chin and area around the eyes. As specified hereinbelow, the compound of formula (I) and/or of formula (II) is advantageously present in the compositions in accordance with the invention in a dissolved form. By way of example, the composition according to the invention may be intended to be administered topically, that is to say by application at the surface of the keratin material under consideration, such as the skin under consideration.

The composition of the invention may be a cosmetic composition (i.e. intended for cosmetic purposes) or a dermatological composition. Preferentially, according to the invention, the composition is a cosmetic composition and even more preferentially a cosmetic composition for topical application.

The term "cosmetic composition" especially means a substance or a preparation intended to be brought into contact with the various superficial parts of the human body, in particular the epidermis, the bodily-hair and head-hair systems, the nails, the lips and the oral mucous membranes, with a view, exclusively or mainly, to cleansing them, making them more attractive, fragrancing them, modifying their appearance, protecting them, keeping them in good condition, or correcting body odours. The composition according to the invention may be in any galenical form conventionally used for topical application.

In a particular embodiment, the compositions according to the invention may be anhydrous.

The term "anhydrous composition" means a composition containing less than 2% by mass of water, or even less than 0.5% of water, and especially free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients.

According to another particular form of the invention, the compositions according to the invention may be solid, in particular in wand or stick form.

The term "solid composition" means that the measurement of the maximum force measured by texturometry during the penetration of a probe into the sample of formulation must be at least equal to 0.25 newtons, in particular at least equal to 0.30 newtons and especially at least equal to 0.35 newtons, assessed under precise measurement condi- tions as follows.

The formulations are poured hot into jars 4 cm in diameter and 3 cm deep. Cooling is performed at room temperature. The hardness of the formulations produced is measured after an interval of 24 hours. The jars containing the samples are characterized by texturometry using a texture analyser such as the machine sold by the company Rheo TA- XT2, according to the following protocol: a stainless-steel ball probe 5 mm in diameter is brought into contact with the sample at a speed of 1 mm/s. The measurement system detects the interface with the sample, with a detection threshold equal to 0.005 newtons. The probe penetrates 0.3 mm into the sample, at a speed of 0.1 mm/s. The measuring machine records the change in force measured in compression over time, during the penetration phase. The hardness of the sample corresponds to the average of the maximum force values detected during penetration, over at least three measurements. In another particular embodiment, the compositions according to the invention may comprise water, and may thus be aqueous.

The compositions according to the invention may be in the form of aqueous solutions, aqueous-alcoholic solutions, oil-in-water (O/W) emulsions, water-in-oil (W/O) emulsions or multiple emulsions (triple: W/O/W or 0/W/O), aqueous gels, more particularly an oil-in-water emulsion. These compositions are prepared according to the usual methods.

These compositions comprise an aqueous phase. The aqueous phase of said compositions contains water and generally other water-miscible or water-soluble solvents, which are additional and different from the compounds b) according to the invention as defined above. These additional water-soluble or water-miscible solvents comprise short- chain, for example C1 -C4, monoalcohols, such as ethanol or isopropanol; diols or polyols, such as ethylene glycol, 1 ,2-propylene glycol, 1 ,3-butylene glycol, diethylene glycol, di- propylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol. Use may be made especially of propylene glycol, glycerol and/or 1 ,3-propanediol.

Particularly, the composition according to the invention has a pH ranging from 3 to 7. Preferably, the pH of the composition ranges from 4 to 6.

The amount of water is not limited, and may range from 10% to 99% by weight, preferably from 20% to 80% by weight and more preferably from 40% to 75% by weight relative to the total weight of the composition.

The composition according to the invention may also comprise at least one oil, which is an additional oil different from the compounds b) according to the invention as defined above. As additional oils that may be used, examples that may be mentioned include: - hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil;

- synthetic esters and ethers, especially of fatty acids, for instance the additional oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon- based chain containing from 3 to 30 carbon atoms, for instance Purcellin oil, isopropyl myristate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate or triisocetyl citrate; fatty alcohol heptanoates, octanoates or decanoates; polyol esters, for instance propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters, for instance pentaerythrityl tetraisostearate;

- linear or branched hydrocarbons of mineral or synthetic origin, such as volatile or nonvolatile liquid paraffins, and derivatives thereof, petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam oil;

- additional fatty alcohols containing from 8 to 26 carbon atoms, for instance cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol;

- silicone oils, for instance volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, especially cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenylsilicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxy silicates, and polymethylphenylsiloxanes;

- mixtures thereof. In the list of oils mentioned above, the term "hydrocarbon-based oil" means any oil mainly comprising carbon and hydrogen atoms, and possibly ester, ether, fluoro, carboxylic acid and/or alcohol groups. The composition according to the invention may comprise substances that are solid at room temperature (25°C), for instance fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, carnauba wax or candelilla wax, paraffin waxes, microcrystalline waxes, ceresin or ozokerite, and synthetic waxes such as polyethylene waxes and Fischer-Tropsch waxes.

These fatty substances may be chosen in a varied manner by a person skilled in the art so as to prepare a composition having the desired properties, for example in terms of consistency or texture.

According to one particular embodiment of the invention, the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion. The proportion of the oily phase of the emulsion may range from 1 % to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.

The emulsions generally contain at least one emulsifier chosen especially from amphoteric, anionic, cationic and nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are chosen in an appropriate manner according to the emulsion to be obtained (W/O or O/W emulsion). The emulsifier and the coemulsifier are generally present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight relative to the total weight of the composition.

For W/O emulsions, examples of emulsifiers that may be mentioned include dimethicone copolyols, such as the mixture of cyclomethicone and dimethicone copolyol sold under the name DC 5225 C by the company Dow Corning, and alkyl dimethicone copolyols such as the lauryl methicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning, and the cetyl dimethicone copolyol sold under the name Abil EM 90® by the company Goldschmidt.

For the O/W emulsions, examples of emulsifiers that may be mentioned include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers; sugar esters such as sucrose stearate; and mixtures thereof, such as the mixture of glyceryl stearate and PEG-100 stearate. The composition may be an aqueous gel, and may especially comprise common aqueous gelling agents.

In a known manner, the composition according to the invention may also contain adjuvants that are common in cosmetics or dermatology, such as gelling agents, film- forming polymers, preserving agents, fragrances, fillers, UV-screening agents, bactericides, odour absorbers, dyestuffs, plant extracts, cosmetic and dermatological active agents, and salts. The amounts of these various adjuvants are those conventionally used in the field under consideration, for example from 0.001 % to 20% of the total weight of the composition.

More particularly, a subject of the invention is also a cosmetic treatment process for caring for, making up and/or cleansing keratin materials, especially the skin, comprising the application to said keratin materials, especially the skin, of a composition according to the invention as described previously.

Said cosmetic treatment process for caring for, making up and/or cleansing the skin is non-therapeutic.

A subject of the invention is also a cosmetic process for preventing and/or treating the signs of ageing of the skin, comprising at least one step of topical application to the keratin materials, such as the skin, of a composition according to the invention as described previously.

The signs of ageing of the skin to be prevented and/or treated in the cosmetic process according to the invention may be chosen from wrinkles and fine lines, and/or for combating wizened, flaccid and/or thinned skin.

A subject of the invention is also the cosmetic use of a composition according to the invention as defined previously, for caring for, making up and/or cleansing keratin materials. In another embodiment, the invention relates to a cosmetic treatment process for caring for, making up and/or cleansing keratin materials, especially the skin, comprising the topical administration, to an individual, of a composition as defined previously.

The expressions "between... and..." and "ranging from... to..." or "at least..." or "at the least..." should be understood as being limits inclusive, unless otherwise specified. The examples below of compositions according to the invention are given as illustrations with no limiting nature. The compounds are indicated as their chemical name or their INCI name.

The amounts of the ingredients are expressed as weight percentages.

EXAMPLES

Example 1 : Preparation of compounds of the invention

Compounds (Α'), (F) and (E) according to the invention were prepared according to the processes described below.

1.1 Preparation of compound (A)

1 17 g (0.33 mol) of the anacardic mixture of compounds A', B', C and D' in 1 I of EtOH are placed in a 2 I glass hydrogenation vessel in the presence of 12 g (0.0057 mol) of Pd/C (10 wt%). After purging three times with nitrogen and then with hydrogen, the medium is stirred under 2 bar of hydrogen at room temperature for 20 hours. After purging three times with nitrogen, a proton NMR spectrum produced using an aliquot shows that the reaction is complete. The medium is filtered through Celite and the Celite is rinsed with ethanol. The filtrate is concentrated and then dried under vacuum at 40°C to result in the desired product (1 13 g, yield 98%), which exists in the form of a light-grey solid.

The NMR and LC/MS analyses confirm that the expected compound has been obtained.

1 .2 Preparation of the lysine salt (F)

33.5 g (0.23 mol, 1 equivalent) of L-lysine (reference Aldrich L5501 ) in 150 ml of water are slowly added to 80 g (0.23 mol) of compound A dissolved in 500 ml of methanol at a temperature of between 10 and 15°C. Checking the pH of the solution at the end of the addition shows that pH = 7.0. The solution is evaporated to dryness to result in 1 13 g of a beige powder, with a yield of 99%.

The NMR analysis and the elemental analysis confirm that the expected compound (F) has been obtained. 1 .3 Preparation of the sodium salt (E)

9.2 g (0.23 mol, 1 equivalent) of sodium hydroxide (NaOH) in 100 ml of water are slowly added to 80 g (0.23 mol) of compound A' dissolved in 500 ml of methanol at a temperature of between 10 and 15°C. Checking the pH of the solution at the end of the addition shows that pH = 7.4. The solution is evaporated to dryness to result in 89 g of a beige powder, with a yield of 98%.

The NMR analysis and the elemental analysis confirm that the expected com- pound (E) has been obtained.

Example 2: Solubility test

Example 2.1 : Tests of solubilization of a salicylic acid derivative of formula (I)

Protocol:

Compound (Α') is used as compound of formula (I):

This compound is weighed out and placed in a hermetic pillbox.

Several solubilizers are tested: 10 ml of solubilizer are placed in a beaker and the compound of formula (I) is added mg by mg. The suspension, optionally brought to 70°C, is stirred by magnetic stirring for 30 minutes.

The dissolution or non-dissolution of compound (Α') and its evolution over time are then monitored.

The insolubility of compound (A) in the solubilizer is characterized macroscopically by a precipitate or a cloudy solution, and microscopically by the presence of birefringent crystals of geometric form.

Results:

The solubilization results are given in the following table

Degree of

solubilizaMacroscopic

tion of control at 24 Microscopic

Test compound

compound hours - room control

(Α') temperature

(weight%)

Isopropyl N- lauroylsarcosinate no birefringent

transparent

(Eldew SL205 from 26% geometric crysliquid

Ajinomoto) tals

Dimethyl isosorbide no birefringent

transparent

(Arlasolve DM I from 26% geometric crysliquid

Uniqema) tals no birefringent

Pentylene glycol or transparent

36% geometric crys1 ,2-pentanediol liquid

tals

Birefringent powder in

Ethanol 24% crystals of gesuspension

ometric form

Propylene glycol

(1 ,2-Propylene glyBirefringent

col Care® from 5% opaque solid geometric crysDupont Tate & Lyle tals Bio Products)

This test shows that the most efficient solubilizers are isopropyl N-lauroylsarcosinate, dimethyl isosorbide and pentylene glycol, which made it possible to dissolve more than 25% by weight of compound of formula (I) (the rest of the solution being constituted of the solubilizer).

Example 2.2: Tests of solubilization of a salicylic acid derivative of formula (I) or of formula (II) in a composition comprising water Protocol:

The following is used as compound:

- either the compound of formula (I) which is compound (Α'):

- or the compound of formula (II) which is compound (F)

The compound is weighed out and placed in a hermetic pillbox. Several solubilizers are tested: 10 ml of solubilizer are placed in a beaker and compound (Α') or compound (F) is added mg by mg. The suspension, optionally brought to 70°C, is stirred by magnetic stirring for 30 minutes.

The dissolution or non-dissolution of compound (Α') and its evolution over time are then monitored.

The insolubility of compound (Α') in the solubilizer is characterized macroscopically by a precipitate or a cloudy solution, and microscopically by the presence of birefringent crystals of geometric form. Results:

The solubilization results are given in the following table:

- for the compound of formula (Α'):

It was thus found that isopropyl N-lauroylsarcosinate does indeed make it possible to dissolve a compound of formula (I), compound (A), in a composition comprising water, unlike ethanol for which the composition has a cloudy solution at 24 hours, with the presence of birefringent crystals of geometric form.

- for the compound of formula (F):

It was thus found that isopropyl N-lauroylsarcosinate does indeed make it possible to dissolve a compound of formula (II), compound (F), in a composition comprising water, unlike dipropylene glycol for which the composition is solid at 24 hours, with the presence of birefringent crystals of geometric form.

Example 3: Anhydrous composition according to the invention

A skincare composition having the following composition was prepared:

Ingredients ingredient content

(weight%)

Caprylic/capric acid triglycerides (70/30 C8-C10 qs 100

triglycerides (DUB MCT 7030) ® from Stearineries

Dubois)

compound (Α') (prepared according to Example 0.5 1 .1 )

Dioctyl carbonate (Cetiol CC® from Cognis) 30

Isononyl isononanoate (isononyl isononanoate 19

(DUB ININ) ® from Stearineries Dubois)

Manufacturing process:

Compound (Α') is dissolved in isononyl isononanoate, with magnetic stirring, while heating to 70°C. This preparation is clear and free of crystals. This preparation is then added to the other components of the formula heated to 65°C with rotor-stator stirring.

The composition is stable and homogeneous and free of birefringent geometric crystals after storage for 2 months at 4°C and 45°C. This composition may be applied regularly to facial skin to care for the same, especially in order to attenuate the signs of ageing of the skin.

Example 4: Skincare composition according to the invention

A skincare composition (oil-in-water gel emulsion) having the following composition was prepared:

Ingredients ingredient phases

content

(weight%)

Water qs 100

Phenoxyethanol 0.7

Disodium ethylenediaminetetraacetate dihydrate 0.1

Sodium acrylamido-2- 2

methylpropanesulfonate/hydroxyethyl acrylate A

copolymer (Sepinov EMT 10® from SEPPIC)

Sodium hydroxide 0.01

Preserving agents 0.3

Polyethylene glycol (8 OE) or PEG-8 (Glycol 400 6

DUB PEG 8® from Stearineries Dubois) Glyceryl mono/distearate/polyethylene glycol 0.6

stearate mixture (100 OE) (Arlacel® 165 FL from

Uniqema) B1

L-Arginine 0.04

Cetyl alcohol (Nanol 16-98® from Sasol) 1

Isopropyl N-lauroylsarcosinate (Eldew SL-205® 10 B2

from Ajinomoto)

Compound (Α') (prepared according to Example 5

1 .1 )

Preparation process:

Compound (Α') is dissolved in isopropyl N-lauroylsarcosinate, with magnetic stirring, while heating to 70°C. This solution B2 is clear and free of crystals. This solution B2 is then added to the fatty phase B1 of the formula heated to 70°C. The aqueous phase A is heated to 70°C. The emulsion is prepared using a rotor-stator stirrer by pouring the fatty phase into the aqueous phase.

The composition is stable and homogeneous and free of birefringent geometric crystals after storage for 2 months at 4°C and 45°C.

This composition may be applied regularly to facial skin to care for the same, especially in order to attenuate the signs of ageing of the skin.

This composition may be applied regularly to facial skin to care for the same and allow good sensory properties experienced in the application on keratin materials such as the skin of said formulation, in particular a touch or feeling with better softness, and/or less greasy.