FR3036034A1 - COMPOSITION COMPRISING SALICYLIC ACID DERIVATIVES AND A PARTICULATE SOLVENT - Google Patents

Abstract

The invention relates to a composition comprising; a) at least one compound of formula (I), at least one of its salts of formula (II), or of a mixture comprising at least one compound of formula (I) and at least one compound of formula (II): the) at least one compound selected from; lipophilic derivatives of amino acids, isosorbide ethers, glycols chosen from pentylene glycol and hexylene glycol, and fatty alcohols comprising a branched and / or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms. carbon, the oils of formulas R1COOR2 and R1OR2, and mixtures thereof. Application to the care, makeup and / or cleaning of keratin materials, especially the skin.

Description

The present invention relates to a composition, preferably a cosmetic composition, comprising certain salicylic acid derivatives, and at least one particular compound that promotes the solubilization of said derivatives. These derivatives of salicylic acid in the context of the present invention correspond to at least one compound of formula (I), at least one of its salts of formula (II), or of a mixture comprising at least one compound of formula (I) and at least one compound of formula (II): ## STR1 ## as defined in detail below. These compounds, which are in solid form at room temperature, are difficult to solubilize. In particular, they are poorly soluble in water and glycerine. However, it is necessary for this compound and / or one of its salts to be formulated in a solubilized form, and in particular at a high content, such as greater than or equal to 0.50% by weight in a composition, in order to make the best profit from its activity, and it is also preferable that its solubilization is maintained over time to avoid any recrystallization phenomenon during the storage of compositions comprising such a compound. In fact the solubilized forms lead to a better bioavailability in the skin than crystallized forms whose crystal size is poorly controlled.

For the purposes of this application, the term "bioavailability" refers to the molecular penetration of the active agent into the living layers of the skin and in particular of the epidermis. It will be sought that the penetrated concentration is as high as possible, so as to increase the rate of asset reaching the living layers of the skin.

By "solubilized form" is meant a dispersion of the derivatives according to the invention in a liquid, in the free molecular state, in particular in uncomplexed form. No crystallization of the salicylic acid derivatives according to the invention is visible in the open eye or in cross-polarized optical microscopy. The object of the present invention is precisely to propose a new galenic formulation of the salicylic acid derivatives according to the invention making it possible to overcome the abovementioned disadvantages, and thus to incorporate these compounds in a solubilized and durable form. in time. This new galenic formulation of the salicylic acid derivatives according to the invention makes it possible in particular to improve the efficacy of the active ingredient for the treatment of keratin materials such as the skin. The compositions according to the invention make it possible in particular to formulate salicylic acid derivatives in a solubilized form at a high content, without using large amounts of glycols in the composition. The inventors have, in fact, unexpectedly discovered that the combination of at least one salicylic acid derivative as defined below (a), compounds of formula (I) and / or compounds of formula ( II), with at least one compound as defined below (b)) makes it possible to improve the solubility of these salicylic acid derivatives and / or their salts while avoiding their recrystallization, in particular after a storage period of 2 months at room temperature (25 ° C) and / or at 4 ° C and / or at 45 ° C. More specifically, the subject of the invention is a composition, in particular a cosmetic composition, comprising; A) at least one compound of formula (I), at least one of its salts of formula (II), or a mixture comprising at least one compound of formula (I) and at least one compound of formula (II): OH In which: R is independently a linear or branched alkyl radical comprising from 12 to 20 carbon atoms, saturated or unsaturated, said radical R possibly comprising one or more ethylenic unsaturations; and Cat + represents a cation or mixture of cations, organic or inorganic, making it possible to achieve the electroneutrality of the compound of formula (II), or of the mixture of compounds of formulas (I) and (II), b) at least one compound selected from; lipophilic derivatives of amino acids, isosorbide ethers, glycols chosen from pentylene glycol and hexylene glycol, and fatty alcohols comprising a branched and / or unsaturated hydrocarbon-based chain containing from 8 to 20 carbon atoms. with 26 carbon atoms, 5 - the oils of formulas R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms, and wherein R 2 represents a hydrocarbon chain of 4 to 30 carbon atoms when R 1 represents the residue of a fatty acid having 8 to 14 carbon atoms, and mixtures thereof. The invention also relates to a process for preparing such a composition comprising the following steps: 1) solubilization of at least one compound a) as defined above by mixing said compound (s) a) with at least one compound b) as defined above, 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 carried out by heating at a temperature of 40 ° to 60 ° C., preferably at 70 ° C., with stirring (for example magnetic stirring), in particular for about 10 minutes. More particularly, the step of said process is also carried out at a temperature of 40-60 ° C. A) DERIVATIVES OF SALICYLIC ACID The invention relates to compositions comprising, at least one compound of formula (I), at least one of its salts of formula (II), or a mixture comprising at least one compound of formula ( I) and at least one compound of formula (II): ## STR2 ## 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. Within the meaning of the invention, the term "cosmetically acceptable compound" is intended to mean any compound that is suitable for administering a composition containing it topically. A cosmetically acceptable compound is preferably a compound without odor, or unpleasant appearance, and which is perfectly compatible with the topical route of administration. 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 (s) according to the invention is used topically, that is to say by surface application of the targeted keratin material, said keratinous material being preferentially the skin of the face and / or the body and more particularly the skin of the face and / or the neck. The radical R denotes in formulas (I) and (II), independently, a linear or branched, saturated or unsaturated alkyl radical comprising from 12 to 20 carbon atoms, preferably from 14 to 18 carbon atoms, in particular 14, 15, 16, 17 or 18 carbon atoms, preferably 14 to 16 carbon atoms, and may comprise one or more ethylenic unsaturations. According to a first variant, the radical R of the compounds according to the invention does not comprise 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, comprises one, two or three ethylenic unsaturations. Cat + represents a cation or mixture of cations, organic or inorganic, making it possible to achieve the electroneutrality of the compound of formula (II), or of the mixture of compounds of formula (I) and (II). Cat + can be single-charge or multi-charge. Preferably, Cat + represents a cation or a mixture of monocharge cations, preferably a single-charge cation.

According to one embodiment, Cat + represents an inorganic cation. Among the inorganic cations, particular mention may be made of alkali metal cations such as sodium or potassium salts, alkaline earth metal salts such as calcium, strontium or magnesium salts, or salts of transition metals such as copper, zinc, iron or manganese salts. According to one embodiment, Cat + is chosen from alkali metal salts, alkaline earth metal salts, and transition metal salts.

According to a particular embodiment, Cat + is selected 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. Among the organic cations, mention may be made of primary, secondary or tertiary amines in their cationic form, as well as quaternary ammoniums. In particular, Cat + may designate the cationic form of triethanolamine, monoethanolamine, di-ethanolamine, hexadecylamine, N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine or else tris (hydroxymethyl) aminomethane.

According to a particular embodiment, Cat + is organic, 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-CO2H, wherein R 1, R 2 and R 3, which are identical or different, denote a linear saturated alkyl radical comprising from 1 to 12 carbon atoms and L denotes a hydrocarbon radical saturated linear divalent comprising from 1 to 6 carbon atoms. According to a first embodiment, the cation Cat + represents the cationic form of an amino acid of L or D form, and preferably the cationic form of the lysine, arginine, alanine or tryptophan, more preferably lysine. According to a second embodiment, Cat + represents a quaternary ammonium N + R1R2R3-L-CO2H, in which; R1, R2 and R3, which may be identical or different, preferably represent a linear saturated alkyl radical comprising from 1 to 4 carbon atoms, and in particular represent a methyl radical, R1, R2 and R3 are preferably identical; and / or L preferably denotes a C1-C4 saturated linear divalent hydrocarbon radical, in particular a divalent -OH2- radical. According to this embodiment, Cat + preferably denotes a quaternary ammonium salt N + R 1 R 2 R 3 -L-CO2H in which R 1, R 2 and R 3 are identical and denote a linear saturated alkyl radical comprising from 1 to 4 carbon atoms and L denotes a C1-C4 saturated linear divalent hydrocarbon 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 radical -CH 2. 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 a mixture of compounds of formula (I). According to one embodiment, the compound of formula (I) denotes the compound (A '): OH O (A') In a particular embodiment of the invention, a composition according to the invention is anhydrous and comprises at least a compound of formula (I) as defined above, preferably the compound (A '). According to another embodiment, the present invention relates to the use of a compound of formula (II).

According to a very particularly preferred embodiment of the invention, the compound of formula (II) is chosen from the following compounds (A), (B), (C) and (D): ## STR2 ## ## STR5 ## Preferably, the compound of formula (II) is (A). Preferably, the compound of formula (II) is (A) and Cat + is selected 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 compound (E) and / or (F): ## STR2 ## and preferably denotes 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) comprises at least one compound having at least one ethylenic unsaturation, preferably at least one compound comprising ethylenic unsaturation and at least one compound not comprising unsaturation. ethylenically.

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

Preferably these compounds have a radical R having the same number of carbon atoms. The compounds of formula (II) according to this embodiment can 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, designated 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 radical comprising from 14 to 18 carbon atoms, preferably from 14 to 16 carbon atoms, and more preferably 15 carbon atoms, and have the same number of carbon atoms in each of the compounds (1), (2), (3) and (4); and the radicals R of each of the compounds (1), (2), (3) and (4) contain, respectively, 0, 1, 2 or 3 ethylenic unsaturations; and Cat + has the same meaning for each of the compounds (1), (2), (3) and (4).

Preferably, according to this embodiment, in the mixture of compounds (1), (2), (3) and (4): the proportion of compound (1) varies from 0.001 to 5 (:) / 0, preferably from 0.5 to 1%, the proportion of compound (2) varies from 20 to 45%, preferably from 30 to 35%, the proportion of compound (3) varies from 5 to 35% preferably from 15 to 25%, the proportion of compound (4) varies from 25 to 50%, preferably from 35 to 40%, the percentages being by weight relative to the total mass of the mixture of the 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 preferably the A mixture of compounds (A), (B), (C) and (D) for which Cat + is selected 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 above. According to this embodiment, the compound of formula (I) preferably denotes compound (A '): OH O (A') and compound (II) preferably denotes compound (E) and / or ( 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, preferably comprises the compound (A ') and the compound (F) or the compound (A') and the compound (E). PREPARATION OF SALICYLIC ACID DERIVATIVES 1: Preparation of Compounds of Formula (I) The compounds of formula (I) can be obtained in 2 or 3 stages from compounds A2 and B1 illustrated in US Pat. schematic diagram below. A2 B2 Al = Br 1: F.F.I .:. ## STR2 ## Compound A2, with x representing an integer between 1 and 9, can be obtained by synthesis in 8 steps starting from the compound Al (Chem Pharm Bull 2001, 49, 18-22). Compound B1 can be obtained in four steps from 3-butynol as described in Chem. Pharm. Bull. 2001, 49, 18-22. Compound B2 can be obtained by Wittig coupling between compounds A2 and B1 in the presence of butyl lithium in a hexane-type apolar solvent, for example, at room temperature under an inert atmosphere. In the compound B2, M denotes a C6-C15 saturated alkyl radical, such as C6I-113; or a monounsaturated alkyl radical of formula C, 1-12, + 1 with n ranging from 5 to 15, such as -CH2 = C5H11, or -CH2-CH = CH-C3H7; or an alkyl radical having two unsaturations of formula CmH2m + 1, with m representing an integer ranging from 5 to 15, such as -CH2-CH = CH-CH2-CH = C1-12. Compound G can be obtained from compound B2 by reaction with BBr3 in dichloromethane, for example, then treatment with sodium hydroxide in a protic solvent such as ethanol. In the compounds A1, A2, B1, B2 and G, x represents an integer between 1 and 9.

According to the nature of the radical M, the compound G obtained contains 1, 2 or 3 unsaturations (the compound G corresponds to the compounds of formula (I) mono-, di or tri-unsaturated). To obtain the corresponding compounds of formula (I) saturated, a saturated 5 M radical is preferably used and the double bond introduced during the Wittig reaction is reduced by catalytic hydrogenation, for example using Pd / C in a protic solvent, this hydrogenation which can be carried out either on the compound B2 or after the reaction with BBr3 / NaOH, on the compound G. 2 2: Preparation of the compounds of formula (II) The compounds of formula (II) can be obtained: from raw material of natural origin (as illustrated in section 2.1 below); or 2- by salifying the compounds of formula (I) obtained according to Part 1 above (as illustrated in section 2.2 below). 2.1 From Raw Material of Natural Origin A mixture of compounds of formula (II) for which R denotes a linear hydrocarbon chain at 015 shown below can be obtained in 2 steps from the anacardic acid mixture. Anacardic acid is a mixture of four 6-15 alkylsalicylic acid compounds: 6-pentadecylsalicylic acid (A '), 6 [8 (Z) -pentadecenyl] salicylic acid (B'), acid 648 ( Z), 11 (Z) -pentadecadienyl] salicylic acid (C '), and 6- [8 (Z), 11 (Z), 14-pentadecatrienyl] salicylic acid (D') of formulas: 3036034 12 A This is a "C15 mixture" of natural origin. In a first step, the anacardic acid mixture, or "C15 mixture", can be obtained from raw or natural raw material, called CNSL 5 ("Cashew Nut ShelI Liquid"), extracted from the cashew shell (Anacardium western), usually containing 60 to 80% of anacardic acid. This isolation of the anacardial mixture can in particular be carried out according to the method described in J. Agric. Food Chem. 2001, 49, 2548-2551.

In particular, the compound (A ') described above in the description, for which R denotes a linear chain saturated at 015, can be obtained by catalytic hydrogenation of the anacardic mixture of the compounds A', B ', C' and D '. 2.2 - Salification The preparation of the sodium salt of the "C15 mixture", or mixture of acidic acid, 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) can be obtained by adding an equivalent of the salifying compound compound (I), or the mixture of compounds (I).

In particular, the salts of formula (II) can be obtained by adding an equivalent of the salifying compound in the form of an aqueous solution to a solution in an alcohol such as isopropanol of the compound (I), or a mixture of compounds ( I). The salts of formula (II) are isolated by evaporation of the solvent.

In the present text, the sodium (E) and lysine (F) salts of formulas: ## STR2 ## described previously in the description, and corresponding to the salts of the compound Aacallic acid was obtained by addition of aqueous solutions of sodium hydroxide and lysine (one equivalent) to compound A 'dissolved in methanol, followed by evaporation of the solvent. The compound (s) a) are present at a total content of compounds (I) and / or (II) ranging from 0.01% to 30% by weight, more preferably 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 SOLUBILIZATION OF THE DERIVATIVES OF SALICYLIC ACID The composition according to the invention comprises at least one compound promoting the solubilization of at least one compound of formula (I), at least one of its salts of formula (II), or 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 (s) in (b) being chosen from among; lipophilic derivatives of amino acids, isosorbide ethers, glycols chosen from pentylene glycol and hexylene glycol, and fatty alcohols comprising a branched and / or unsaturated hydrocarbon-based chain containing from 8 to 26 atoms. of carbon, - the oils of formulas R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms. carbon, and in which R2 represents a hydrocarbon chain of 4 to 30 carbon atoms when R1 represents the residue of a fatty acid having 8 to 14 carbon atoms, and mixtures thereof. I) The lipophilic amino acid derivatives are in particular the C6-C22 N-acyl amino acid esters. These derivatives are in particular those described in the patent application EP 1 269 986. The N-acylated amino acid ester or esters are generally of formula 11: R'1 (CO) N (R'2) CH (R'3 ) (CH2) n (CO) OR'4 in which: n is in an integer of 0.1 or 2, R'1 represents a linear or branched C5 to 021 alkyl or alkenyl radical; R'2 represents a hydrogen atom or a C 1 -C 3 alkyl group, R '3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group or a linear or branched C 3 or C 4 alkyl radical; R'4 represents a linear or branched C 1 -C 10 alkyl or C 2 -C 10 alkenyl radical, or a sterol residue.

Preferably, the R'1 (CO) - group is an acyl group of an acid selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, acid, and the like. stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids, palm kernel. These fatty acids may further have a hydroxyl group. Even more preferably, it will be lauric acid. The portion -N (R'2) CH (R'3) (CH2), (CO) - of the amino acid ester is preferably chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine threonine, proline, hydroxyproline, 3-alanine, aminobutyric acid, aminocaproic acid, sarcosine, or N-methyl-11-alanine.

Even more preferably, it will be sarcosine. The part of the amino acid esters corresponding to the group OR '4 can be obtained from the 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-ethyl hexanol, decanol, lauryl alcohol, myristic alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleic alcohol, behenyl alcohol, jojoba alcohol , 2-hexadecyl alcohol, 2-octyldodecanol and isostearyl alcohol.

These amino acid esters can in particular be obtained from natural sources of amino acids. In this case, the amino acids come from hydrolysis of natural plant proteins (oats, wheat, soybean, palm, coconut) and then necessarily lead to mixtures of amino acids which will then 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 use in the present invention is isopropyl N-lauroylsarcosinate of the formula: ## STR5 ## such as the product sold under the name ELDEW SL-205 by the company AJIMOTO. The amino acid esters preferably used in the sense of the present invention, as well as their synthesis are described in the patent applications EP 1 044 676 and EP 0 928 608 from the company AJINOMOTO CO. Ii) An isosorbide ether may especially be dimethylisosorbide; in particular, the dimethyl isosorbide marketed under the name ARLASOLVE DMI by the company UNIQEMA will be used. Iii) The glycols according to the invention are chosen from pentylene glycol and hexylene glycol, preferably pentylene glycol. iv) Fatty alcohols comprising a branched and / or unsaturated hydrocarbon chain containing from 8 to 26 carbon atoms may be chosen from cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), octyldodecanol, 2 butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol. More particularly, fatty alcohols comprising a branched and / or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms, and in particular may be chosen from octyldodecanol, 2-butyloctanol, 2-hexyldecanol and 2-undecylpentadecanol. preferably, the fatty alcohol having from 8 to 26 carbon atoms is octyldodecanol or 2-octyl dodecanol marketed under the name ISOFOL N / F by the company SASOL. (V) oils of formulas R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms and wherein R2 represents a hydrocarbon chain of 4 to 30 carbon atoms when R1 represents the remainder of a fatty acid having 8 to 14 carbon atoms may be selected from; Purcellin oil, isononyl isononanoate, 2-ethylhexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isostearyl isostearate ; hydroxyl esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate; heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate.

Preferably, the oils v) are chosen from: isononyl isononanoate, isopropyl palmitate and 2-ethylhexyl palmitate, and mixtures thereof. Isononyl isononanoate is marketed under the name ISONONYLE DUONONYLE ISONONYATE DUB INN by STEARINERIE DUBOIS.

Ethyl-2-hexyl palmitate is marketed under the name ETHYL 2 HEXYL PALMITATE (DUB PO) by the company STEARINERIE DUBOIS. Isopropyl palmitate is marketed under the name PALMITATE D 25 ISOPROPYL (DUB I PP) by the company STEARINERIE DUBOIS. The compounds (i) to (v) described above may be used alone or as a mixture in the compositions according to the invention.

More particularly the said compound (s) defined in (b) is chosen from: - isopropyl N-lauroylsarcosinate, - dimethyl isosorbide, - pentylene glycol, - the octyldodecanol, isononyl isononanoate, isopropyl palmitate, and / or 2-ethylhexyl palmitate, and mixtures thereof.

In particular, the ingredient promoting the solubilization 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) wherein the compound of formula (A ') as defined above, and at least one a lipophilic derivative of amino acid, in particular isopropyl N-lauroylsarcosinate marketed in particular by AJINOMOTO under the name ELDEW SL 205.

Isopropyl N-lauroylsarcosinate, pentylene glycol and / or dimethyl isosorbide will be advantageous for solubilizing large quantities 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. % by weight% of compound (s) of formula (I), preferably compound (A '), present in a formulation containing only said compounds (b) as defined above. Isopropyl N-lauroylsarcosinate, pentylene glycol and / or dimethyl isosorbide will be advantageous for solubilizing large quantities 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% of compound (s) of formula (I), preferably the compound (A '), 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 composed 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 composed of formula (A ') 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 at 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), the ingredient (s) promoting the solubilization of the compound (s) defined in (a), may be present (s) at a content ranging from 0.01% to 99% by weight, particularly ranging from 0.1% to 20% by weight, more particularly from 1% to 15% by weight relative to the total weight of the composition . The mass ratio of said compound (s) promoting the solubilization defined in (b) with respect to the compound (s) defined in (a) of formula (I) and / or 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 compound (s) defined in (b) are chosen from: lipophilic derivatives of amino acids, isopropyl, isosorbide ethers, preferably dimethyl isosorbide, glycols selected from pentylene glycol and hexylene glycol, pentylene glycol, and mixtures thereof. Preferably, the composition is anhydrous, and the said N-lauroyl sarcosinate (s), 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 the compound (A '), and the 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 selected 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 selected 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 formulas R 1 COOR 2 and R 1 OR 2 in which R 1 represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R 2 represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms, and wherein R 2 represents a hydrocarbon chain of 4 to 30 carbon atoms when R 1 represents the residue of a fatty acid having 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) the compound (A ') and / or the compound (F) or the compound (E), and the (s) said compound (b) are chosen from: - lipophilic amino acid derivatives, preferably isopropyl N-lauroylsarcosinate, - fatty alcohols comprising a branched and / or unsaturated hydrocarbon-based chain containing 8 to 26 carbon atoms, preferably octyldodecanol; - the oils of formulas R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid having from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or not, containing from 3 to 30 carbon atoms, and wherein R 2 represents a hydrocarbon chain of 4 to 30 carbon atoms when R 1 represents the residue of a fatty acid having 8 to 14 carbon atoms, preferably isononyl isononanoate, isopropyl palmitate, and / or palm 2-ethylhexyl tate, and mixtures thereof. The compositions used according to the invention may comprise a physiologically acceptable medium, that is to say a medium which is suitable for the administration of a composition by the topical route, that is to say, it is compatible with keratin materials. human beings such as skin, scalp, hair, nails. In a particular embodiment of the invention the compositions, preferably cosmetic, comprise a physiologically acceptable medium.

According to the invention a physiologically acceptable medium is preferably a cosmetically acceptable medium, that is to say without odor, or unpleasant appearance, and which is perfectly compatible with the topical route of administration.

The term "keratin materials" according to the invention is intended to mean the skin, the body, the face and / or the eye contour, the lips, the nails, the mucous membranes, the eyelashes, the eyebrows, the hairs, the scalp and / or the skin. hair, or any other skin area of the body. 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 materials according to the invention is the skin.

By "the skin" is meant all of the skin of the body, and preferably the skin of the face, décolleté, neck, arms and forearms, or even more preferably, the skin. face, including forehead, nose, cheeks, chin, eye area. As specified below, the compound of formula (I) and / or of formula (II) is advantageously present in the compositions according to the invention in a solubilized form. By way of example, the composition according to the invention may be intended to be administered topically, that is to say by surface application of the keratin material in question, such as the skin under consideration. The composition of the invention may be a cosmetic composition (either intended for cosmetic use) or dermatological. Preferably, according to the invention, the composition is a cosmetic composition and even more preferentially a cosmetic composition for topical application. The term "cosmetic composition" is understood to mean 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 hair and hair systems, the nails, the lips and the oral mucosa, in particular seen, exclusively or mainly, to clean, embellish, perfume, change the appearance, protect, maintain in good condition or correct body odor. The composition according to the invention may be in any of the galenical forms conventionally used for topical application.

In a particular embodiment, the compositions according to the invention may be anhydrous. By anhydrous composition is meant a composition containing less than 2% by weight of water, or even less than 0.5% of water, and in particular water-free, the water not being added 3036034 21 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 can be solid, in particular in the form of a stick or a stick.

By "solid composition" it is meant that the measurement of the maximum force measured in texturometry during the insertion of a probe into the sample of formula must be at least 0.25 Newton, in particular at least equal to at 0.30 Newton, especially at least 0.35 Newton, appreciated under precise measurement conditions as follows.

The formulas are heat cast in pots 4 cm in diameter and 3 cm in depth. Cooling is done at room temperature. The hardness of the formulas is measured after 24 hours of waiting. The pots containing the samples are characterized in texturometry using a texturometer such as that marketed by Rhéo TA-XT2, according to the following protocol: a 15 mm diameter stainless steel ball-type probe is brought into contact of the sample at a speed of 1 mm / s. The measuring system detects the interface with the sample with a detection threshold of 0.005 newtons. The probe sinks 0.3 mm into the sample at a rate of 0.1 mm / s. The meter records the evolution of the force measured in compression over time, during the penetration phase. The hardness of the sample corresponds to the average of the maximum values of the force detected during the penetration, on at least 3 measurements. In another particular embodiment, the compositions according to the invention may comprise water, and may therefore be aqueous. The compositions according to the invention may be in the form of aqueous solutions, hydroalcoholic solutions, oil-in-water (O / W) or water-in-oil (W / O) or multiple (triple: E) emulsions. / H / E or H / E / H), 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 in general other solvents soluble or miscible in water, which are additional and different from the compounds b) according to the invention as defined above. These additional solvents which are soluble or miscible with water include short-chain monohydric alcohols, for example C 1 -C 4, such as ethanol or isopropanol; diols or polyols such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol mono-methyl ether, triethylene glycol monomethyl ether and sorbitol. Propylene glycol, glycerin and / or 1,3-propane can be used.

In particular, 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, based on total weight of the composition.

The composition according to the invention may further comprise at least one oil, which is an additional oil and different from the compounds b) according to the invention as defined above. As additional oils that may be used, mention may be made, for example, of: hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, such as heptanoic or octanoic acid triglycerides, or by for example, sunflower, corn, soybean, squash, grape seed, sesame, hazelnut, apricot, macadamia, arara, castor oil, avocado, caprylic acid triglycerides / capric such as those sold by the company Stearineries Dubois or those sold under the names "Miglyol 810", "812" and "818" by the company Dynamit Nobel, oil of 20 jojoba, shea butter oil; esters and synthetic ethers, in particular of fatty acids, such as the oils of formulas R 1 COOR 2 and R 1 OR 2 in which R 1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R 2 represents a hydrocarbon-based chain , branched or unbranched, containing from 3 to 30 carbon atoms, such as, for example, purcellin oil, isopropyl myristate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate isostearyl isostearate; hydroxyl esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate; heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate; linear or branched hydrocarbons of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as parleam oil; Fatty alcohols having from 8 to 26 additional carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol; Silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl-dimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes; Their mixtures. The term "hydrocarbon-based oil" in the list of oils mentioned above, any oil predominantly comprising carbon and hydrogen atoms, and optionally ester, ether, fluoro, carboxylic acid and / or alcohol groups.

The composition according to the invention may comprise solid bodies at room temperature (25 ° C.), for example fatty acids containing from 8 to 30 carbon atoms, such as stearic acid, lauric acid and the acid. palmitic and oleic acid; waxes such as lanolin, beeswax, carnauba or candellila wax, paraffin waxes, microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer waxes -Tropsch. These fatty substances may be chosen in a varied manner by those skilled in the art in order to prepare a composition having the desired properties, for example 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, especially chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W). The emulsifier and the co-emulsifier 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 the 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 Dow Corning, and alkyl dimethicone. copolyols such as Laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning and Cetyl dimethicone copolyol sold under the name Abil EM 90® by the company Goldschmidt. Examples of O / W emulsions which may be mentioned as emulsifiers are nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated); oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); 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 especially include conventional aqueous gelling agents. In a known manner, the composition according to the invention may also contain adjuvants which are usual in the cosmetic or dermatological field, such as gelling agents, film-forming polymers, preservatives, perfumes, fillers, UV filters, bactericides, absorbers odor, dyestuffs, plant extracts, cosmetic and dermatological active ingredients, and salts. The amounts of these various adjuvants are those conventionally used in the field under consideration, and for example from 0.001 to 20% of the total weight of the composition. More particularly, the subject of the invention is also a process for the cosmetic treatment of skincare, makeup, and / or cleaning of keratinous substances, in particular the skin, comprising the application on said keratin materials, in particular the skin, of a composition according to the invention as described above. Said method of cosmetic treatment of care, makeup, and / or cleansing of the skin is non-therapeutic. The invention also relates to a cosmetic method for preventing and / or treating cutaneous signs of aging, comprising at least one step of topical application to keratin materials, such as the skin, of a composition according to the invention. invention as described above. The cutaneous signs of the aging to be prevented and / or treated in the cosmetic process according to the invention may be chosen from the lines and wrinkles, and / or to combat the skin which is wilted, soft and / or thinned. The invention also relates to the cosmetic use of a composition according to the invention as defined above, for the care, makeup and / or cleaning of keratin materials. In another embodiment, the invention relates to a cosmetic treatment method for the care, makeup, and / or cleaning of keratinous substances, in particular the skin, comprising the administration, topically, to an individual, of a composition as defined above. The expressions "between ... and ..." and "from ... to ...", or "at least ..", or "at least .." must be understood as inclusive, unless the opposite is specified. The following examples of compositions according to the invention are given by way of illustration and without limitation. The compounds are indicated in chemical name or INCI name. The contents of the ingredients are expressed in percentage by weight.

EXAMPLES Example 1: Preparation of compounds of the invention The compounds (A '), (F) and (E) according to the invention were prepared according to the methods described below. 5 1.1. Preparation of the compound (A ') OH 117 g (0.33 mol) of the anacardic mixture of the compounds A', B ', C' and D 'in 1 L of EtOH are placed in a glass hydrogenation tank. 2 L, in the presence of 10 12 g (0.0057 mol) of Pd / C (10% wt). After 3 purges of nitrogen and then hydrogen the medium is stirred for 20 hours under 2 bar of hydrogen at room temperature. After 3 purges of nitrogen, a proton NMR made from an aliquot shows that the reaction is complete. The medium is filtered on celite and the celite is rinsed with ethanol. The filtrate is concentrated and then dried under vacuum at 40 ° C to yield the desired product (113 g, 98% yield) which is a light gray solid. NMR and LC / MS analyzes confirm the obtaining of the expected compound. 1.2. Preparation of the lysine salt (F) NH 2 H 3 N 3 O 33.5 g (0.23 mol, 1 equivalent) of L-lysine (reference Aldrich L5501) in 150 ml of water are added slowly to 80 g ( 0.23 mol) of compound A 'solubilized in 500 ml of methanol at a temperature 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 yield 113 g of a beige powder, with a yield of 99%.

NMR analysis and elemental analysis confirm the obtaining of the expected compound (F). OH O 3036034 27 1.3. Preparation of the sodium salt (E) OH (E) 9.2 g (0.23 mol, 1 equivalent) of sodium hydroxide (NaOH) in 100 ml of water are slowly added to 80 g of compound A '(0, 23 mol) solubilized in 500 mL of methanol at a temperature 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 yield 89 g of a beige powder, with a yield of 98%. NMR analysis and elemental analysis confirm the obtaining of the expected compound (E).

Example 2: Solubility test Example 2.1: Solubilization tests of a salicylic acid derivative of formula (I) Protocol: The compound (A '): OH ( A ') This compound is weighed and placed in an airtight container.

Several solubilizers are tested: 10 ml of solubilizer are placed in a beaker and the compound of formula (I) is added mg per mg. The suspension, optionally heated to 70 ° C., is stirred by magnetic stirring for half an hour. Dissolution or non-dissolution of the compound (A '), as well as its evolution over time are then followed.

The non-solubility of the compound (A ') in the solubilizer is characterized macroscopically by a precipitate or a hazy solution, and microscopically by the presence of crystals of geometric birefringent shape.

Results: The results of solubilization are presented in the following table: 3036034 29 Test compound solubilization rate of the compound (A ') (% by weight) Macroscopic control at 24 hours - temperature am- Croscopic control N -lauroylsarcosinate 26% transparent liquid, no geometric isopropyl crystals (ELDEW SL 205 birefringent AJIN OMOTO) Dimethyl isosorbide 26% transparent liquid no crystals (ARLASOLVE Geometric DMI UNIQEMA) birefringent pentylene glycol or 36% transparent liquid no crystals 1,2-Pentanediol geometric birefringent ethanol 24% powder crystals suspension Geometrical form birefringent Propylene glycol 5% Solid crystals geo- (1,2-metric bire- PROPYLENEGLYC fringents OL CARE® from DUPONT DUPONT TATE AND LYLE BIO PRODUCTS) This test shows that the most effective solubilizers are isopropyl N-lauroylsarcosinate, dimethylisosorbide, and pentylene glycol, which have made it possible to solubilize more than 25% by weight of compound of formula (I) (the rest of the solution being constituted by the solubilizer).

EXAMPLE 2.2 Solubilization Tests of a Salicylic Acid Derivative of Formula (I) or of Formula (II) in a Composition Comprising Water Protocol: It is used as a compound; - Let the compound of formula (I) which is the compound (A '): OH O (A') 10 - Let the compound of formula (II) which the compound (F): NH 2 OH O H 3 N 0 (F) compound is weighed and placed in an airtight container.

Several solubilizers are tested: 10 ml of solubilizer are placed in a beaker and the compound (A ') or the compound (F) is added mg per mg. The suspension, optionally heated to 70 ° C., is stirred with magnetic stirring for a period of one hour. half hour. The dissolution or non-dissolution of the compound (A '), as well as its evolution in time are then followed. The non solubility of the compound (A ') in the solubilizer is characterized macroscopically by a precipitate or a hazy solution, and microscopically by the presence of geometric crystals birefringent Results: The results of solubilization are presented in the following table: for the compound of formula (A '): 3036034 31 SOLUTION CONTROLS Compound tested compound test ratio (% by weight) rate of water content% (weight) weight) Macroscopic pH) Mposé (A') By weight) 24 hours Temperature-microscopic ambient temperature N- 10 0.5 89.5 0 <pH solution biphase transparent no geometric creep-birefringent lauroylsarcosi- <isopropyl iodate 14 (ELDEW SL 205 0 of AJIN OMOTO) ethanol 0.5 89.5 0 <H Monophase Lazy Solution Geometric Birefringent Crystals ethanol <14 It has thus been found that isopropyl N-lauroylsarcosinate makes it possible to solubilize a compound of formula (I), the compound (A '), in a compo a composition comprising water, in contrast to ethanol for which the composition has a cloudy 24H solution, with the presence of birefringent geometric crystals. for the compound of formula (F): SOLUTION CONTROLS compound tested rate of compost-test (% by weight) rate of rate of pH microscopic 24 hours of water (°) / lution Microscopic temperature: F ) (/ ° Yo oste in weight am- weight) by weight) biante N- 5 5 90 0 <pH <biphase solution transparent no squiggle-geometric rate birefringent isopropyl lauroylsarco-14 sinate (ELDEW SL 205® from AJIN OMOTO) dipropylene 5 90 0 <pH <solid geometric crystals birefringent glycol 14 (Dl RPOPYLE NE GLYCOL LO + 0 from Dow Chemical) 3036034 32 It has thus been found that isopropyl N-lauroylsarcosinate allows for good solubilizing a compound of formula (II), compound (F), in a composition comprising water, in contrast to dipropylene glycol for which the composition is solid at 24H, with the presence of geometrically birefringent crystals. Example 3: Anhydrous Composition According to the Invention A skin care composition having the following composition was prepared: Ingredients content ingredient (% by weight) ACRYLIC TRIGLYCERIDES Qsp100 CAPRYLIC / CAPRIQUE (TRIGLYCERIDES C8C10 70/30 (DUB MCT 7030) ® from STEARINERIE DUBOIS) compound (A ') (prepared according to example 1.1) 0.5 DIOCTYL CARBONATE (CETIOL CC® from Cognis) 30 isononyl isononate (ISONONYL ISONONYLATE (DUB ININ) ® from STEARINERIE DUBOIS) 19 Production method: The compound (A ') is solubilized in ISONONYL ISONONANOATE, with magnetic stirring, heating at 70 ° C, this preparation is clear and without crystals. This prealization is then added to the other components of the formula heated at 65 ° C with rotor-stator stirring. The composition is stable, homogeneous and without birefringent geometric crystals after storage for 2 months at 4 ° C. and 45 ° C.

This composition can be applied regularly to the skin of the face for the care of the latter, in particular to reduce the signs of skin aging.

Example 4: Skin Care Composition According to the Invention A skin care composition (oil-in-water emulsion gel) was prepared having the following composition: Ingredients content ingredient (% by weight) t phases WATER Qsp100 TO PHENOXYETHANOL 0.7 TETRACETIC ETHYLENE DIAMINE ACID, DISODIUM SALT, 2 H2O 0.1 COPOLYMER ACRYLAMIDO-2-METHYL PROPANE SODIUM SULFONATE / HYDROXYETHYLACRYLATE (SEPINOV EMT 100 from Seppic) 2 Sodium hydroxide 0.01 preservatives 0 , 3 POLYETHYLENE GLYCOL (80E) or PEG-8 (GLYCOL 400 DUB PEG 8® from STEARINERIE DUBOIS) 6 MONO / DISTEARATE MIXTURE OF 0.6 B1 GLYCERYLE / POLYETHYLENE GLYCOL STEARATE (100 OE) (ARLACEL® 165 FL from Uniqma) L-ARGININE 0.04 CETYL ALCOHOL (NANOL 16-98® from Sasol) 1 N-LAUROYL ISOPROPYL SARCOSINATE (ELDEW SL-205® from AJINOMOTO) B2 B2 Compound (A ') (prepared according to Example 1.1 Preparation process: Compound (A ') is solubilized in ISOPROPYL N-LAUROYL SARCOSINATE, with stirring mag When heated to 70 ° C., this B2 solution is clear and without any crisp. This solution B2 is then added to the fatty phase B1 of the formula heated to 70 ° C. Aqueous phase A is heated to 70 ° C. The emulsion is done under rotor-stator stirrer by pouring the fatty phase on the aqueous phase.

The composition is stable, homogeneous and free of birefringent geometric crystals after storage for 2 months at 4 ° C and 45 ° C. This composition can be applied regularly to the skin of the face for the care of the latter, in particular to reduce the signs of skin aging.

Claims (18)

REVENDICATIONS1. Composition comprising: a) at least one compound of formula (I), at least one of its salts of formula (II), or a mixture comprising at least one compound of formula (I) and at least one compound of formula (II) In which: R denotes independently a linear or branched alkyl radical comprising from 12 to 20 carbon atoms, saturated or unsaturated, said radical R possibly comprising one or more ethylenic unsaturations; and Cat + represents a cation or a mixture of cations, organic or inorganic, making it possible to achieve the electroneutrality of said compound (s) of formula (II), or of the mixture of compounds of formulas (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 hydrocarbon chain and or unsaturated containing from 8 to 26 carbon atoms, the oils of formulas R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched. , containing from 3 to 30 carbon atoms, and wherein R2 represents a hydrocarbon chain of 4 to 30 carbon atoms when R1 represents the remainder of a fatty acid having 8 to 14 carbon atoms, and mixtures thereof. 2. Composition according to claim 1, wherein R comprises from 14 to 18 carbon atoms, preferably from 14 to 16 carbon atoms. 3. Composition according to any one of the preceding claims, in which the compound of formula (I) denotes compound (A '): ## STR3 ## 4. Composition according to any one of the preceding claims, characterized in that: The inorganic Cat + cation is chosen from alkali metals, such as sodium salt, alkaline earth metals, and transition metals; and the organic Cat + cation is chosen from the cationic form of a primary, secondary or tertiary amine, and a quaternary ammonium. A composition according to any one of the preceding claims, wherein the Cat + cation represents an organic cation, or a mixture of organic cations, selected from: (i) the cationic form of an L or D-form amino acid and (ii) a quaternary ammonium N + R 1 R 2 R 3 -L-CO2H, wherein R 1, R 2, 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 hydrocarbon radical saturated linear divalent comprising from 1 to 6 carbon atoms. 6. A composition according to any one of the preceding claims, wherein Cat + represents the cationic form of an L- or D-form amino acid, and preferably the cationic form of lysine, arginine, alanine or tryptophan, more preferably lysine. 7. A composition according to any one of claims 1 to 6, wherein the compound of formula (II) is selected from the following compounds (A), (B), (C) and (D), alone or in a mixture: ## STR1 ## in which Cat + is as defined in any one of Claims 1 and 3. at 5. 8. Composition according to claim 7, wherein the compound of formula (II) is the compound of formula (F) or the compound of formula (E): ## STR2 ## 9. Composition according to one of claims 1 to 8, characterized in that the (s) said (s) compound (s) defined (b) is selected from: - the N-lauroylsarcosinate isopropyl, 3036034 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, the compound (s) defined in (a) is a compound of formula (I) such that defined in one of claims 1 to 3, and / or 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 selected from pentylene glycol and hexylene glycol, preferably pentylene glycol, and mixtures thereof. 11. Composition according to one of claims 1 to 9, characterized in that the composition comprises water, and that (s) said (s) compound (s) defined (b) are chosen 20 among; 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, the oils of formulas R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or unbranched, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon chain of 4 to 30 carbon atoms when R1 represents the remainder of a fatty acid having 8 to 14 carbon atoms, preferably isononyl isononanoate, isopropyl palmitate, and / or ethyl-2-hexyl palmitate, and mixtures thereof. 12. Composition according to claim 11, characterized in that the 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%. relative to the total weight of the composition. 3036034 39 13. Composition according to any one of claims 11 to 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. . 5 14. Composition according to any one of the preceding claims, characterized in that the compound (s) defined in (a) is present (s) at a total content of compounds of formula (I) and / or or of formula (II) ranging from 0.01% to 40% by weight especially 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% by weight % to 5% by weight, based on 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) is present in a content ranging from 0.01% to 99% by weight. preferably 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) with respect 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. 25 18. A process for the cosmetic treatment of keratin materials comprising the application to keratin materials, such as the skin, of a composition according to any one of the preceding claims. 30