DIBENZYLIDENE PENTOSE DERIVATIVES, COMPOSITION COMPRISING THEM, AND THEIR USE IN COSMETICS

Abstract

Title DIBENZYLIDENE PENTOSE DERIVATIVES, COMPOSITION COMPRISING THEM, AND THEIR USE IN COSMETICS The present invention relates to a composition comprising at least one particular dibenzilidene alditol derivative of formula (I), a cosmetic treatment process comprising said derivative, new dibenzildene pentose derivatives, their preparation process and their use in cosmetics, in particular in “cosmetic sticks” or “sticks” such as lip sticks. (I) Formula (I) in which: R, R 1 to R' 5, and X are as defined in the description Figures

Description

Title of the invention: DIBENZYLIDENE PENTOSE DERIVATIVES, COMPOSITION COMPRISING THEM, AND THEIR USE IN COSMETICS

[0001] The subject of the present invention is a composition comprising at least one particular dibenzylidene pentose derivative of formula (I), a cosmetic treatment process comprising said derivative, new dibenzylidene pentose derivatives, their preparation process and their use in cosmetics, in particular for thickening lipophilic media such as oils.

[0002] Cosmetic compositions are generally thickened to allow easy application. The formulator has numerous possibilities for thickening and gelling both hydrophilic media and lipophilic media such as oils. Thus, to thicken oils in particular until sticks are obtained which have both a sufficient consistency, acceptable stability over time and a suitable disintegration capacity, those skilled in the art generally use crystallizable compounds which are essentially waxes, such as polyethylene waxes, Candelilla waxes, Carnauba waxes, beeswax, as well as pasty compounds mainly lanolins. Generally, a mixture consisting of 50-70% oils and pasty compounds can be brought to a level of consistency allowing a disintegrating "stick" to be manufactured by adding 12-20% waxes.However, the sticks thus obtained have the disadvantages of being dull and brittle.

[0003] Dibenzylidene alditol derivatives are known in the literature, for example, as gelling agents for hydrocarbons or polar media (xylitol based phase selective organogelators for potential oil spillage recovery, RSC Adv., 2017, 7, p. 37175, WO 2018 / 002947, and JP63304079). These dibenzylidene alditols are not, however, known as gelling agents for cosmetic oily media.

[0004] It is also known to use sorbitol dibenzylidene esters as thickeners for lipophilic media, but their implementation generally requires a high temperature (approximately 120°C), which is not always compatible with the formulated media to be thickened, in particular for reasons of instability or degradation of certain ingredients (EP 2 542 556 A1). In addition, the thickened medium obtained may lack uniformity of thickening, such as, for example, a liquid part and / or the presence of a solid, or even lead to opaque thickened media, which may be a handicap in certain applications. Thus, there remains a real need to provide compounds for gelling lipophilic media, particularly oily media, at a temperature compatible with the various constituents and in particular at a temperature below 120 C, preferably less than or equal to 100 C, or even less than or equal to 80 C. In addition, the sorbitol dibenzylidene esters are generally used in high concentration to obtain a stick (greater than 10% by weight relative to the total weight of the composition). It would therefore be desirable to reduce the content, particularly for economic reasons. In addition, it is difficult to be able to generate gels that are more or less opaque, or more or less translucent, depending on the fatty substance to be gelled. In addition, unlike the waxes usually used, the compounds of the invention lead to thickened lipophilic media and translucent and shiny sticks.

[0005] These problems have been solved by the use in cosmetics of i) dibenzylidene pentose compound(s), of formula (I) as well as their optical, geometric isomers, and their acid or base salts, organic or mineral, and their solvates such as hydrates: [Chem.l] (I)

[0006] Formula (I) in which: • R1 to R'5, which may be identical or different, represent a hydrogen atom, a halogen atom such as fluorine, chlorine or bromine; or a group chosen from: i) linear or branched (Ci-C6)alkyl, ii) -O-Ra, iii) -C(X)O-Rb or -OC(X)-Rb, iv) -NRcRd, and v) -C(X)-NRcRd or -N(Rc)-C(X)-Rd, with Ra representing a hydrogen atom, or a (Ci-C4)alkyl group such as methyl, aryl(Ci-C4)alkyl such as benzyl, (C3-C8)cycloalkyl such as cyclohexyl; Rb representing a hydrogen atom or a (Ci-C4)alkyl group; Rc, and Rd, identical or different, representing a hydrogen atom, or a (Ci-C4)alkyl group such as methyl, or (C3-C8)cycloalkyl such as cyclohexyl and X representing an oxygen or sulfur atom or an NRC group, preferably X represents an oxygen atom; it being understood that two adjacent radicals Ri to R's can also form together with the carbon atoms which carry them an unsaturated (C5-C8) ring such as benzo; • R represents a radical chosen from i) -OXi; ii) -OC(X)-Xi; iii) -N(RC)-Xi; iv) -SXi; with X as defined above, preferably X represents an oxygen atom; and Xi representing a) a (C4-C8)cycloalkyl group such as cyclohexyl; or b) a hydrocarbon chain comprising from 6 to 24 carbon atoms, saturated or unsaturated, linear or branched, said chain being: - optionally interrupted by one or more heteroatoms or divalent radicals chosen from: O, S, N(RC), C(O) or their combinations such as -OC(O)-, -C(O)-O-, -C(O)-N(Rc)-, -N(Rc)-C(O)-; and / or - optionally substituted by one or more halogen atoms and / or groups, identical or different, chosen from: -O-Ra, -C(O)-O-Rb, -NRcRd, and (C4-C8)cycloalkyl with Ra, Rb, Rc and Rd as defined above, preferably Ra and Rb represent a (Ci-C4)alkyl group such as methyl and Rc and Rd independently represent a hydrogen atom or (Ci-C4)alkyl group such as methyl.

[0007] It has been discovered that the compounds of formula (I) of the invention make it possible to structure, thicken, ii) lipophilic media or liquid fatty substances, in particular oils, and thus lead to compositions, in particular thickened cosmetic compositions, or even to the production of translucent sticks, colored or not, and non-brittle.

[0008] Another subject of the invention is a cosmetic treatment process using one or more compounds of formula (I) as defined above.

[0009] Another subject of the invention is the compounds of formula (I) as defined above.

[0010] Another subject of the invention is a process for preparing compounds of formula (I) as defined above.

[0011] Another subject of the invention is a composition, preferably cosmetic, comprising one or more compounds of formula (I) as defined above.

[0012] For the purposes of the present invention, and unless otherwise indicated: - For the purposes of the present invention, the term "fatty substance" means an organic compound insoluble in water at ordinary temperature (25°C) and atmospheric pressure (760 mm Hg) (solubility less than 5%, and preferably 1%, even more preferably 0.1%); in addition, fatty substances are soluble in organic solvents under the same temperature and pressure conditions, such as, for example, in halogenated solvents such as chloroform, dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene. - By "organic or mineral acid salt" is meant more particularly the salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid, x) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH3C(O)OH; xiv) triflic acid CF3SO3H and xv) tetrafluoroboric acid HBF4; - By "salts of organic or mineral bases" we mean salts of bases or alkaline agents as defined below as alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines. - an “alkyl radical” is a saturated hydrocarbon radical in CrC8, linear or branched, preferably in Ci-C6, more preferably CrC4 such as methyl, or ethyl; - an “alkoxy radical” is an alkyloxy radical for which the alkyl radical is a hydrocarbon radical, linear or branched, in CrCi6, preferably in CrC8. The expression “at least one” is equivalent to “one or more”; and - The expression "inclusive" for a concentration range means that the limits of the range are part of the defined interval.

[0013] i) Compounds of formula (I)

[0014] According to a particular embodiment of the invention, the dibenzylidene pentose compound(s), of formula (I) as well as their optical and geometric isomers, and their organic or mineral acid or base salts, and their solvates such as hydrates: [Chem. 2] (I)

[0015] Formula (I) in which: • R1 to R'5, which may be identical or different, represent a hydrogen atom, a halogen atom such as fluorine, chlorine or bromine; or a group chosen from: i) linear or branched (Ci-C6)alkyl, ii) -O-Ra, iii) -C(X)O-Rb or -OC(X)-Rb, iv) -NRcRd, and v) -C(X)-NRcRd or -N(Rc)-C(X)-Rd, with Ra representing a hydrogen atom, or a (Ci-C4)alkyl group such as methyl, aryl(Ci-C4)alkyl such as benzyl, (C3-C8)cycloalkyl such as cyclohexyl; Rb representing a hydrogen atom or a (CrC4)alkyl group; Rc, and Rd, identical or different, representing a hydrogen atom, or a (Ci-C4)alkyl group such as methyl, or (C3-C8)cycloalkyl such as cyclohexyl and X representing an oxygen or sulfur atom or an NRC group, preferably X represents an oxygen atom; it being understood that two adjacent radicals Ri to R's can also form together with the carbon atoms which carry them an unsaturated (C5-C8) cycle such as benzo; • R represents a radical chosen from i) -OXi; ii) -OC(X)-Xi; iii) -N(RC)-Xi; iv) -SXi; with X as defined above, preferably X represents an oxygen atom; and Xi representing a) a (C4-C8)cycloalkyl group such as cyclohexyl; or b) a hydrocarbon chain comprising from 6 to 24 carbon atoms, saturated or unsaturated, linear or branched, said chain being: - optionally interrupted by one or more heteroatoms or divalent radicals chosen from: O, S, N(RC), C(O) or their combinations such as -OC(O)-, -C(O)-O-, -C(O)-N(Rc)-, -N(Rc)-C(O)-; and / or - optionally substituted by one or more halogen atoms and / or groups, identical or different, chosen from: -O-Ra, -C(O)-O-Rb,oo-NRcRd, and (C4-C8)cycloalkyl with Ra, Rb, Rc and Rd as defined above, preferably Ra and Rb represent a (CrC4)alkyl group such as methyl and Rc and Rd independently represent a hydrogen atom or (CrC4)alkyl group such as methyl.

[0016] In particular, the compounds of formula (I) of the invention are of formula (Ia), as well as their acid or base salts, organic or mineral, and their solvates such as hydrates: [Chem. 3] (there)

[0017] Formula (la) with R, R1 to R'5 as defined previously. Preferably, the compounds of formula (I) or (Ia) of the invention are such that R1 is identical to R'1, R2 is identical to R'2, R3 is identical to R'3, R4 is identical to R'4, and R5 is identical to R'5. According to a particular embodiment of the invention, the compounds of formula (I) or (Ia) are such that the radicals R1 to R'5, identical or different, represent i) a hydrogen atom, or a group ii) (Ci-C6)alkyl; iii) -O-Ra, or iv) -C(O)-O-Rb with Ra and Rb as defined above, preferably Ra represents a hydrogen atom, a (Ci-C4)alkyl group, or benzyl; and Rb represents a hydrogen atom or a (Ci-C4)alkyl group.

[0018] According to a particular embodiment of the invention, the compounds of formula (I) or (Ia) are such that R is as defined above and X1 preferably represents a) a (C4-C8)cycloalkyl radical, b) a saturated or unsaturated, linear or branched C10-C24 hydrocarbon chain, said chain being optionally interrupted by one or more heterotoms or divalent radicals chosen from -O-, -N(RC)-, -C(O)- and their combinations such as -OC(O)-, -C(O)-O-, -C(O)-N(Rc)-, -N(Rc)-C(O)-, and / or said chain being optionally substituted by one or more identical or different radicals chosen from the radicals -O-Ra, -C(O)-O-Rb with Rarerepresenting a (CrC4)alkyl group, Rbrrepresenting a (CrC4)alkyl group, Rc being as defined above and preferably a hydrogen atom.

[0019] In particular, the compounds of formula (I) or (Ia) of the invention are such that R1 to R'5, identical or different, represent a hydrogen atom, or a group chosen from (Ci-C6)alkyl, -O-Rawith Rarerepresenting a (CrC4)alkyl group, preferably a hydrogen atom.

[0020] In particular, the compounds of formula (I) or (Ia) of the invention are such that Rb represents a hydrogen atom, or a (CrC4)alkyl group; more preferably, Rb represents a (CrC4)alkyl group.

[0021] In particular, the compounds of formula (I) or (Ia) of the invention are such that Rc represents a hydrogen atom or a (Ci-C4)alkyl group such as methyl, preferably a hydrogen atom and Rd represents a (Ci-C4)alkyl group such as methyl.

[0022] In particular, the compounds of formula (I) or (Ia) of the invention are such that R is as defined above, preferably represents -OX,.

[0023] According to another particular embodiment of the invention, the compounds of formula (I) or (Ia) of the invention are such that R represents a radical -N(RC)-Xi with Xi preferably representing a saturated or unsaturated, linear or branched C10-C24 hydrocarbon chain, preferably linear or branched C10-C24, Rc being as defined above and preferably a hydrogen atom.

[0024] In particular, the compounds of formula (I) or (Ia) of the invention are such that Xi represents a hydrocarbon chain, saturated or unsaturated, linear or branched, comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms, said chain being optionally interrupted by one or more heteroatoms or divalent radicals chosen from -O-, -N(RC)-, -C(O)- and their combinations such as -OC(O)-, -C(O)-O-, -C(O)-N(Rc)-, -N(Rc)-C(O)-, and / or said chain being optionally substituted by one or more identical or different radicals chosen from the radicals -O-Ra, -C(O) O-Rb with Ra representing a (Ci-C4)alkyl group and R representing a (CrC4)alkyl group, Rc preferably representing a hydrogen atom;

[0025] More preferably, the compounds of formula (I) or (Ia) of the invention are such that Xi represents a hydrocarbon chain, saturated or unsaturated, linear or branched, comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms.

[0026] According to a particular embodiment of the invention, the compounds of formula (I) or (Ia) are such that R1 to R'5 are identical. More particularly, the compounds of formula (I) or (Ia) of the invention are such that R1 to R5 and R'1 to R'5 represent a hydrogen atom, or a linear or branched (CrC4)alkyl group. Even more preferably, the compounds of formula (I) or (Ia) of the invention are such that R1 to R'5 represent a hydrogen atom.

[0027] According to a particular embodiment of the invention, the compounds of formula (I) or (Ia) are such that R1 to R'5 represent a hydrogen atom and R represents a radical -OXi with Xi denoting a hydrocarbon chain as defined above and in particular with Xi denoting a linear or branched, saturated or unsaturated C10-C24 hydrocarbon chain.

[0028] More preferably, the compounds of formula (I) of the invention are chosen from those of formula (1-1) following, as well as its optical, geometric isomers, and its solvates such as hydrates: [Chem. 4] (1-1)

[0029] Formula (1-1) with Xi as defined previously.

[0030] Even more preferably, the compounds of formula (I), (I-1) or (Ia) of the invention are chosen from those of formula (Ia) following as well as its geometric isomers, and solvated such as hydrates: [Chem. 5]

[0031] Formula (la) with Xi as defined previously.

[0032] According to one embodiment, the compounds of formula (I), (I-1), (Ia) or (Ia) of the invention are such that Xi is as defined above, and preferably Xi represents a hydrocarbon chain, linear or branched, preferably linear, comprising from 1 to 3 unsaturations, in particular 1 unsaturation, and comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms. According to a particular embodiment, the compounds of formula (I), (I-1), (Ia) or (Ia) of the invention are such that Xi is chosen from the following linear alkenyl groups: -(CH2)m-CH=CH-(CH2)nH with m and n, identical or different, preferably identical, representing an integer inclusively between 0 and 20, it being understood that the sum of n+m is inclusively between 8 and 20, preferably n+m is inclusively between 10 and 18, and more preferably inclusively between 12 and 18 such that 16. More preferably m=n.

[0033] According to a particular embodiment, the compounds of formula (I), (I-1), (Ia) or (Ia) of the invention are such that Xi represents a saturated, linear or branched hydrocarbon chain comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms. According to this embodiment, Xi represents a -(CH2)p-CH-RiR2 chain with Ri and R2, identical or different, representing a hydrogen atom or a (Ci-C6)alkyl group such as methyl, and p represents an integer between 9 and 21 inclusive, preferably between 11 and 19, more particularly between 13 and 17 such as 15.

[0034] According to another particular embodiment, the compounds of formula (I), (I-1), (Ia) or (Ia) of the invention are such that Xi represents an unsaturated, linear or branched (preferably linear) hydrocarbon chain, comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms.

[0035] More particularly, the compounds of formula (I) of the invention are chosen from the following compounds (1) to (2) and very particularly compound (1): [Chem. 6] (1)

[0036] [Chem.7] (2)

[0037] Compounds (1) and (2) as well as their optical and geometric isomers, and their solvates such as hydrates.

[0038] Even more particularly, the compounds of formula (I) of the invention are chosen from the following compounds (Ia) and (2a), in particular compound (Ia): [Chem. 8] (there)

[0039] [Chem.9] (2a)

[0040] Compounds (la) and (2a) as well as their geometric isomers, and their solvates such as hydrates.

[0041] Process for the preparation of compounds of formula (I)

[0042] Another object of the invention is a preparation process according to the schemes of synthesis [Chem. 9] and [Chem. 10] of compounds of formula (I): for which when R^R'1, R2=R'2, R3=R'3, R4=R'4 and R5=R'5 the preparation process comprises a first step in which a lactone derivative (AJ or acyclic (A2) which may be in any enantiomeric or racemic form, is reacted with at least 2 molar equivalents of aldehyde (B) in the presence of a catalyst chosen in particular from organic or mineral acids, such as hydrochloric acid or paratoluenesulfonic acid; - from the lactone derivative (Ai), the reaction is carried out at room temperature or by heating to a temperature inclusively between 30 and 80°C, preferably at room temperature, with or without solvent, for at least one hour, preferably for a duration of between 3h and 48h; - from the acyclic derivative (A2), the reaction is carried out at a temperature of between 30 and 80°C inclusive, in particular between 40 and 70°C inclusive, under a vacuum preferably at a pressure of between 20 mbar and 500 mbar, in particular between 30 mbar and 400 mbar, for a duration preferably of several hours, particularly between 3 hours and 2 days; the compound (C) is optionally purified and optionally isolated, for example by precipitation, and is subjected to: ** Pathway A: to a (thio)esterification reaction to lead to the compounds of formula (I') of the invention; this (thio)esterification step can be carried out chemically, for example by reaction with a thiol XrSH or an alcohol XrOH, Xi being as defined previously, by acid catalysis, or by any other (thio)esterification method known to those skilled in the art such as, for example, those described in Advanced Organic Chemistry 6th Ed. Jerry March at Wiley interscience (see in particular p. 16-64, and p. 16-69); According to another embodiment, the (thio)sterification reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a solvent, preferably polar aprotic such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyltetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification reaction of (C) to (I') is carried out with a supported lipase which allows the recycling of the enzyme at the end of the reaction; or ** Route B: to an amidation reaction to lead to the compounds (I”) of the invention; this step can be carried out chemically, for example by reaction with an amine such as XrNH(Rc), Xi being as defined previously, or by any other amidation method known to those skilled in the art as described in Advanced Organic Chemistry 6th Ed. Jerry March at Wiley interscience (see in particular p. 16-75).According to a particular embodiment, the amidation reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a solvent, preferably polar aprotic such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyltetrahydrofuran, in the presence of an enzyme; in particular, the amidation reaction of (C) into (I”) is carried out with a supported lipase which allows the recycling of the enzyme at the end of the reaction; or. ** Route C: to an anhydrification reaction to lead to the compounds (I'”) of the invention; this step can be carried out chemically, for example by the condensation of (C) with an acid XrC(O)-OH, Xi being as defined previously, in an acidic medium and in the presence of a dehydrating agent such as phosphorus pentoxide or by activating the compound (C) with for example a thionyl halide such as SOCl2 then by reacting the latter activated compound (C) with an acid XrC(O)-OH or by any other method of anhydride synthesis known to those skilled in the art as described in Advanced Organic Chemistry 6th Ed. Jerry March at Wiley interscience (see in particular pp. 16-66, 16-67, 16-90); or The lactone derivatives (Ai) denote in particular D-(+)-Ribonic y-lactone, D-Xylono-1,4-lactone and D-Arabino-1,4-lactone and in particular D-Xylono-1,4-lactone; and the acyclic derivatives (A2) denote in particular ribonic acid, xylonic acid and arabonic acid and in particular xylonic acid;

[0043] [Chem. 10] (H Another object of the invention is a process for preparing compounds of formula (I) when R1 is different from R'1, and / or R2 is different from R'2, and / or R3 is different from R'3, and / or R4 is different from R'4 and / or R5 is different from R'5, the preparation process comprises a first step 1), in which the lactone derivative (Ai) or the acyclic derivative (A2) as defined above reacts with a molar equivalent of aldehyde (B) in dimethyl acetal form, preferably in the presence of a catalyst chosen in particular from organic or mineral acids, such as hydrochloric acid or paratoluenesulfonic acid; - from the lactone derivative (Ai), the reaction is carried out at room temperature or the medium is heated to a temperature of between 30°C and 80°C inclusive, in particular between 40°C and 70°C inclusive, preferably at room temperature, with or without solvent, for a period of several hours, preferably between 3 hours and 2 days; - from the acyclic derivative (A2), the reaction is carried out at a temperature of between 30°C and 80°C inclusive, between 40°C and 70°C inclusive, preferably under vacuum, particularly at a pressure of between 20 mbar and 500 mbar, in particular between 30 mbar and 400 mbar, with or without solvent, for a duration preferably of between 3 hours and 2 days, followed 2) by the addition of at least one molar equivalent of protected aldehyde (B') in methyl acetal form under the same conditions as in step 1) with (B) to yield the compound (Cb), said compound (Cb) being able to be isolated by precipitation and is subjected: ** Route A': to a (thio)esterification reaction to yield the compounds of formula (I'b) of the invention;this (thio)esterification step can be carried out chemically, for example by reaction with a thiol XrSH or an alcohol Xr0H, Xi being as defined previously, by acid catalysis, or by any other (thio)esterification method as mentioned previously; ; According to a particular embodiment, the (thio)esterification reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a preferably polar aprotic solvent such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyltetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification reaction of (Cb) to (I'b) is carried out with a supported lipase which allows the recycling of the enzyme at the end of the reaction; or ** Route B': to the amidation reaction to lead to the compounds (I”b) of the invention; this step can be carried out chemically, for example by reaction with an amine XrNH(Rc), Xi being as defined previously, or by or by any other amidation method as mentioned previously; According to one embodiment, the amidation reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a preferably polar aprotic solvent such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyltetrahydrofuran, in the presence of an enzyme; in particular, the amidation reaction of (Cb) to (I”b) is carried out with a supported lipase which allows the recycling of the enzyme at the end of the reaction; or ** Route C': to the anhydrification reaction to lead to the compounds (I”'b) of the invention; this step can be carried out chemically, for example by the condensation of (Cb) with an acid Xi-C(O)-OH, Xi being as defined previously, in an acid medium and in the presence of a dehydrating agent such as phosphorus pentoxide or equal to 100°C or by activating the compound (Cb) for example in the form of acid chloride by reaction of (Cb) with a thionyl halide such as SOC12 then reaction of this last compound (Cb) activated with an acid XrC(O)-OH or by any other method known to those skilled in the art, in particular those described in 'Advanced Organic Chemistry 6th Ed. Jerry March at Wiley interscience (see especially pp. 16-66, 16-67, 16-90). [Chem. 11] (rb)

[0044] The composition

[0045] Another subject of the invention is a composition comprising one or more compounds of formula (I), (I-1), (Ia), (Ia), (Ia), (Ia), (2), (Ia), or (2a), as defined above, as well as their acid or base salts, organic or mineral, their optical, geometric isomers, and their solvates such as hydrates.

[0046] The quantity of the compound(s) of formula (I), (I-1), (Ia), (Ia), (Ia), (Ia), (2), (Ia), or (2a), of the invention present in the compositions obviously depends on the texture desired texture of said composition, said texture being able to range from a fluid gel to a stick, and / or the desired properties.

[0047] Preferably the amount of compounds of formula (I), (I-1), (Ia), (Ia), (Ia), (Ia), (2), (Ia) or (2a), is less than or equal to 15%, more preferably less than or equal to 10% by weight and in particular less than or equal to 8% by weight relative to the total weight of the cosmetic composition; it may be between 0.005% and 15% by weight, preferably between 0.01% and 13% by weight, in particular between 0.1% and 10% by weight, or even between 0.15% and 9% by weight, and better still between 0.2% and 8% by weight, relative to the total weight of the composition.

[0048] The composition of the invention designates in particular a cosmetic composition. By cosmetic composition is meant a physiologically acceptable composition in particular intended to be applied topically to keratin materials.

[0049] The term “physiologically acceptable composition” means a composition compatible with the keratin materials of human beings such as the skin, in particular of the body and face, the lips, the scalp, the hair, the eyelashes, the eyebrows and the nails.

[0050] The compounds of formula (I), (1-1), (la), (la), (1), (2), (la) or (2a) as defined previously according to the invention make it possible to structure lipophilic media such as fatty substances, preferably liquid ii), such as oils.

[0051] ii) one or more liquid fatty substances:

[0052] According to a particular embodiment of the invention, the composition of the invention further comprises ii) one or more liquid fatty substances.

[0053] Preferably, the fatty substances of the invention are chosen from hydrocarbons, fatty alcohols, fatty esters, silicones and fatty ethers or mixtures thereof. More particularly, the fatty substances of the invention are not (poly)oxyalkylenated.

[0054] For the purposes of the present invention, liquid fatty substances are understood to mean fatty substances that are liquid at room temperature (25°C) and at atmospheric pressure (760 mm Hg; i.e. 1,013.105 Pa).

[0055] The liquid fatty substances of the invention have in particular a viscosity less than or equal to 2 Pa.s, more particularly less than or equal to 1 Pa.s and even more particularly less than or equal to 0.1 Pa.s, more preferably less than or equal to 0.09 Pa.s at a temperature of 25°C and at a shear rate of 1 s1.

[0056] According to a particular embodiment of the invention, they have a viscosity of between 0.001 Pa.s and 2 Pa.s, more particularly inclusively between 0.01 and 1 Pa.s and even more particularly inclusively between 0.014 and 0.1 Pa.s, more preferably inclusively between 0.015 and 0.09 Pa.s at a temperature of 25°C and at a shear rate of 1 s1.

[0057] By "liquid hydrocarbon" is meant a hydrocarbon composed solely of carbon atoms and liquid hydrogen at room temperature (25°C) and atmospheric pressure (760 mm Hg; or 1,013.105 Pa).

[0058] More particularly, the liquid hydrocarbons are chosen from: - linear or branched C6-C16 alkanes, possibly cyclic. Examples include hexane, undecane, dodecane, tridecane, isoparaffins such as isohexadecane, isododecane and isodecane. - linear or branched hydrocarbons, of mineral, animal or synthetic origin with more than 16 carbon atoms, such as paraffin oils, vaseline oil, polydecenes, hydrogenated polyisobutene such as Parléam®, squalane.

[0059] In a preferred variant, the liquid hydrocarbon(s) are chosen from paraffin oils and vaseline oil.

[0060] By “liquid fatty alcohol” is meant a non-glycerolated and non-oxyalkylenated fatty alcohol which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mm Hg; i.e. 1,013.105 Pa).

[0061] Preferably, the liquid fatty alcohols of the invention comprise from 8 to 30 carbon atoms, more preferably C10-C22, even more preferably C14-C20, better still C16-C18.

[0062] The liquid fatty alcohols of the invention may be saturated or unsaturated.

[0063] The saturated liquid fatty alcohols are preferably branched. They can even must include in their structure at least one aromatic or non-aromatic cycle. Preferably, they are acyclic.

[0064] More particularly, the liquid saturated fatty alcohols of the invention are chosen from octyldodecanol, isostearyl alcohol, 2-hexyldecanol.

[0065] According to another variant of the invention, the fatty substance(s) are chosen from liquid unsaturated fatty alcohols. These liquid unsaturated fatty alcohols have at least one double or triple bond in their structure. Preferably, the fatty alcohols of the invention have one or more double bonds in their structure. When several double bonds are present, they are preferably 2 or 3 in number and they may or may not be conjugated.

[0066] These unsaturated fatty alcohols can be linear or branched.

[0067] They may optionally comprise in their structure at least one aromatic or non-aromatic cycle. Preferably, they are acyclic.

[0068] More particularly, the liquid unsaturated fatty alcohols of the invention are chosen from oleic (or oleyl) alcohol, linoleic (or linoleyl) alcohol, linolenyl (or linolenyl) alcohol, undecylenic alcohol.

[0069] Oleic alcohol is particularly preferred.

[0070] By "liquid fatty esters" is meant an ester derived from a fatty acid and / or a fatty alcohol and liquid at room temperature (25°C) and atmospheric pressure (760 mm of Hg; or 1,013.105 Pa).

[0071] The esters are preferably liquid esters of saturated or unsaturated, linear or branched C1-C26 aliphatic mono or polyacids and of saturated or unsaturated, linear or branched C1-C26 aliphatic mono or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.

[0072] Preferably, for the monoalcohol esters, at least one of the alcohol or acid from which the esters of the invention are derived is branched.

[0073] Among the monoesters of monoacids and monoalcohols, mention may be made of ethyl and isopropyl palmitates, alkyl myristates such as isopropyl myristate, ethyl myristate, alkyl laurates such as isoamyl laurate, isocetyl stearate, ethyl-2-hexyl isononanoate, isodecyl neopentanoate, isostearyl neopentanoate, and C10-C22, preferably C12-C20, alkyl (iso)stearates such as isopropyl isostearate.

[0074] It is also possible to use esters of C4-C22 di or tricarboxylic acids and C1-C22 alcohols and esters of mono di or tricarboxylic acids and non-sugar di, tri, tetra or pentahydroxy C4-C26 alcohols.

[0075] Mention may in particular be made of: diethyl sebacate; diisopropyl sebacate; di(2-ethylhexyl) sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; di(2-ethylhexyl) adipate; diisostearyl adipate; di(2-ethylhexyl) maleate; triisopropyl citrate; triisocetyl citrate; trisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; neopentyl glycol diheptanoate; diethylene glycol diisononate.

[0076] The composition may also comprise, as liquid fatty ester, esters and diesters of sugars of C6-C30 fatty acids, preferably C12-C22. It is recalled that the term "sugar" means oxygenated hydrocarbon compounds which have several alcohol functions, with or without aldehyde or ketone function, and which comprise at least 4 carbon atoms. These sugars may be monosaccharides, oligosaccharides or polysaccharides.

[0077] Suitable sugars include, for example, sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose, and their derivatives, in particular alkylated ones, such as methylated derivatives such as methylglucose.

[0078] The esters of sugars and fatty acids may be chosen in particular from the group comprising the esters or mixtures of esters of sugars described above and of C6-C30, preferably C12-C22, linear or branched, saturated or unsaturated fatty acids. If they are unsaturated, these compounds may comprise one to three carbon-carbon double bonds, conjugated or not.

[0079] The esters according to this variant can also be chosen from mono-, di-, tri- and tetra-esters, polyesters and their mixtures.

[0080] These esters may be, for example, oleate, laurate, palmitate, myristate, behenate, cocoate, stearate, linoleate, linolenate, caprate, arachidonates, or mixtures thereof, such as in particular the mixed esters oleo-palmitate, oleo-stearate, palmito-stearate.

[0081] More particularly, mono- and di-esters are used, and in particular mono- or di-oleate, stearate, behenate, oleopalmitate, linoleate, linolenate, oleostearate, of sucrose, glucose or methylglucose.

[0082] An example of this is the product sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.

[0083] Finally, natural or synthetic esters of mono, di or triacids with glycerol can also be used.

[0084] Among these, we can cite vegetable oils.

[0085] As oils of vegetable origin or synthetic triglycerides, which can be used in the composition of the invention as liquid fatty esters, we can cite for example: - triglyceride oils of vegetable or synthetic origin, such as liquid triglycerides of fatty acids containing 6 to 30 carbon atoms such as triglycerides of heptanoic or octanoic acids or, for example, sunflower, corn, soybean, pumpkin, grape seed, sesame, hazelnut, apricot, macadamia, arara, sunflower, castor, avocado oils, triglycerides of caprylic / capric acids 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, jojoba oil, shea butter oil.

[0086] Preferably, liquid fatty esters derived from monoalcohols will be used as esters according to the invention.

[0087] Isopropyl myristate or palmitate as well as isoamyl laurate are preferred, in particular isoamyl laurate.

[0088] The liquid fatty ethers are chosen from liquid dialkyl ethers such as dica-prylylether.

[0089] The compositions of the invention contain ii) one or more fatty substances which are liquid at room temperature (25°C) and at atmospheric pressure (760 mm Hg; i.e. 1,013.105 Pa). These liquid fatty substances can therefore be of natural or synthetic origin.

[0090] In particular, the liquid fatty substance(s) ii) of the invention are chosen from a) linear or branched hydrocarbons, of more than 16 carbon atoms, such as paraffin oils, vaseline oil, polydecenes, hydrogenated polyisobutene such as squalane, preferably squalane, b) saturated liquid fatty alcohols or unsaturated, linear or branched, such as octyldodecanol, c) linear or branched C6-Ci6 alkanes, preferably branched such as isododecane, isohexadecane, preferably isododecane, and d) liquid fatty esters in particular derived from saturated C8-C26 aliphatic monoacids such as Ci2 and more particularly derived from saturated C8-C26 monoacids with a branched monoalcohol, preferably C3-C9 such as C5, preferably isoamyl laurate.

[0091] Preferably the compound(s) of formula (I), (I-1), (Ia) or (Ia) of the invention make it possible to structure ii) the liquid cosmetic fatty substances usually used, and in particular the liquid fatty substances as defined above.

[0092] The liquid fatty substance(s) ii) used in the composition according to the present invention may be present in the composition in an amount varying from 1% to 99% by weight, preferably in an amount varying from 5% to 99% by weight, and even more preferably in an amount varying from 10% to 99% by weight relative to the total weight of the composition.

[0093] The compounds of formula (I), (I-1), (Ia) or (Ia) according to the invention can also find an application in the field of the paint, varnish and glue industry, as a structuring, thickening or even gelling agent.

[0094] Said medium may comprise one or more additional ingredient(s), distinct from the compounds of formula (I), (I-1), (Ia) or (Ia) as defined previously.

[0095] Thus, the composition of the invention may comprise one or more organic solvents.

[0096] By “organic solvent” is meant an organic substance capable of dissolving another substance without chemically modifying it.

[0097] As organic solvent, mention may be made, for example, of a) C2-C6 alkanols, such as ethanol and isopropanol; b) polyols miscible with water at room temperature (25°C), in particular chosen from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, diglycerin; (c) polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and (d) aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0098] According to a particular embodiment, the composition further comprises one or more polyols, notably chosen from polyols having notably from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerin.

[0099] The composition of the invention may comprise additional compounds such as cosmetic active ingredients such as humectants, moisturizing agents, anti-aging active ingredients, sunscreens, vitamins, thickeners, gelling agents other than the compounds of the invention, trace elements, softeners, sequestrants, perfumes, alkalizing or acidifying agents, preservatives, surfactants, antioxidants, propellants, ceramides, film-forming auxiliaries, polymers, coloring agents such as dyes and pigments, deodorant agents, antiperspirant agents or mixtures thereof.

[0100] Of course, those skilled in the art will take care to choose this or these possible additional ingredients and / or their quantity, in such a way that the advantageous properties of the composition according to the invention are not, or not substantially, altered by the envisaged addition.

[0101] The composition according to the invention may in particular be presented in the form: - a makeup product, in particular for the skin of the face, body or lips or eyelashes such as lip balm, concealer, foundation, blemish masking product or stick; - an aftershave gel or lotion; a shaving product, particularly in stick form; - a deodorant or antiperspirant like a stick - in the form of a body hygiene composition such as a shower gel or shampoo, preferably in stick form; - a solid composition such as a soap or a cleaning bar, preferably in stick form; - a skin care or cleansing composition, preferably in stick form.

[0102] iii) one or more coloring agents:

[0103] According to a particular embodiment of the invention, the composition further comprises one or more coloring agents chosen in particular from pigments and dyes, preferably direct ones.

[0104] According to a more particular embodiment of the invention, the composition comprises one or more coloring agents chosen from powdery colorants such as pigments, fillers, pearlescent agents and glitter, and / or liposoluble or water-soluble colorants.

[0105] According to one embodiment of the invention, the composition comprises one or more coloring agents chosen from pigments, direct dyes and their mixtures.

[0106] Preferably, the composition according to the invention comprises one or more pigments.

[0107] By "pigment" is meant all pigments providing color to keratin materials, of synthetic or natural origin. The solubility of the pigments in water at 25°C and at atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01%.

[0108] These are solid particles, white or colored, naturally insoluble in the liquid hydrophilic and lipophilic phases usually used in cosmetics or made insoluble by formulation in the form of a lacquer, where appropriate. More particularly pigments that are poorly or not at all soluble in hydroalcoholic media.

[0109] The pigments that can be used are in particular chosen from organic and / or mineral pigments known in the art, in particular those described in Kirk-Othmer's Encyclopedia of Chemical Technology and in Ullmann's Encyclopedia of Industrial Chemistry. Mention may in particular be made, as pigments, of organic and inorganic pigments such as those defined and described in Ullmann's Encyclopedia of Industrial Chemistry "Pigment organics", 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002 / 14356007.a20 371 and ibid, "Pigments, Inorganic, 1. General” 2009 Wiley-VCH Verlag GmbH & Co. KGaA, W einheiml0.1002 / 14356007.a20_243.pub 3

[0110] These pigments can be in the form of powder or pigment paste. They can be coated or uncoated.

[0111] The pigments may for example be chosen from mineral pigments, organic pigments, lakes, special effect pigments such as mother-of-pearl or glitter, and mixtures thereof.

[0112] The pigment may be a mineral pigment. By mineral pigment is meant any pigment which meets the definition of the Ullmann encyclopedia in the inorganic pigment chapter. Among the mineral pigments useful in the present invention, mention may be made of iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.

[0113] The pigment may be an organic pigment. By organic pigment is meant any pigment which meets the definition of the Ullmann encyclopedia in the organic pigment chapter. The organic pigment may in particular be chosen from nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, metal complex type compounds, isoindolinone, isoindoline, quinacridone, perinone, perylene, di-ketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane, quinophthalone.

[0114] In particular, the white or colored organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Color Index under the references Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Color Index under the references Cl 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 15510, 45370, 71105, red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 17200, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indolic, phenolic derivatives as described in patent FR 2 679 771.

[0115] According to a particular embodiment of the invention, pigment pastes of organic pigments such as the products sold by the company HOECHST under the name: - COSMENYL YELLOW IOG: Pigment YELLOW 3 (Cl 11710); - COSMENYL YELLOW G: Pigment YELLOW 1 (Cl 11680); - COSMENYL ORANGE GR: Pigment ORANGE 43 (Cl 71105); - COSMENYL RED R: Pigment RED 4 (Cl 12085); - COSMENYL CARMINE FB: Pigment RED 5 (Cl 12490); - COSMENYL VIOLET RL: Pigment VIOLET 23 (Cl 51319); - COSMENYL BLUE A2R: Pigment BLUE 15.1 (Cl 74160); - VERT COSMENYL GG: Pigment GREEN 7 (Cl 74260); - COSMENYL BLACK R: Pigment BLACK 7 (Cl 77266).

[0116] The pigments in accordance with the invention may also be in the form of composite pigments as described in patent EP 1 184 426. These composite pigments may be composed in particular of particles comprising: - an inorganic core, - at least one binder ensuring the fixing of the organic pigments on the core, and - at least one organic pigment at least partially covering the core.

[0117] By "lake" is meant dyes adsorbed onto insoluble particles, the resulting mixture remaining insoluble during use. The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum. Among the organic dyes, cochineal carmine may be mentioned.

[0118] Examples of lakes include products known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 7 (CI 15 850:1), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985), D & C Green (CI 61 570), D & C Yellow 10 (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 (CI 42090).

[0119] The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.

[0120] Among the colorants, mention may be made of cochineal carmine. Mention may also be made of the colorants known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985), D & C Green (CI 61 570), D & C Yellow 1 O (CI 77 002), D & C Green 3 (CI 42 053), D & C Bine 1 (CI 42 090).

[0121] As examples of lacquers, mention may be made of the product known under the following name: D & C Red 7 (CI 15 850:1).

[0122] The pigment(s) may also be special effect pigments.

[0123] By "special effect pigments" is meant pigments which generally create a colored appearance (characterized by a certain shade, a certain liveliness and a certain clarity) which is non-uniform and changes depending on the observation conditions (light, temperature, observation angles, etc.). They are thus opposed to colored pigments which provide a conventional uniform opaque, semi-transparent or transparent shade.

[0124] There are several types of special effect pigments, those with a low refractive index such as fluorescent, photochromic or thermochromic pigments, and those with a higher refractive index such as pearls or glitter.

[0125] Examples of special effect pigments that may be mentioned are pearlescent pigments such as titanium mica coated with iron oxide, mica coated with iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic colorant, in particular of the aforementioned type, as well as pearlescent pigments based on bismuth oxychloride. They may also be mica particles on the surface of which at least two successive layers of metal oxides and / or organic coloring materials are superimposed.

[0126] The mother-of-pearls can more particularly have a yellow, pink, red, bronze, orange, brown, gold and / or coppery color or reflection.

[0127] As an illustration of the mother-of-pearls that can be used in the context of the present invention, mention may in particular be made of gold-colored mother-of-pearls marketed in particular by the company ENGELHARD under the name Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); bronze mother-of-pearls marketed in particular by the company MERCK under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona), by the company Eckart under the name Prestige Bronze and by the company ENGELHARD under the name Super bronze (Cloisonne); orange mother-of-pearls marketed in particular by the company ENGELHARD under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company MERCK under the name Passion orange (Colorona) and Matte orange (17449) (Microna);brown mother-of-pearl, notably marketed by the company ENGELHARD under the name Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); mother-of-pearl with reflections; copper, notably marketed by the company ENGELHARD under the name Copper 340A (Timica) and by the company Eckart under the name Prestige Copper; mother-of-pearl with a red sheen, notably marketed by the company MERCK under the name Sienna fine (17386) (Colorona); mother-of-pearl with a yellow sheen, notably marketed by the company ENGELHARD under the name Yellow (4502) (Chromalite); mother-of-pearl with a red tint and a gold sheen, notably marketed by the company ENGELHARD under the name Sunstone G012 (Gemtone);black mother-of-pearl with a gold sheen, notably marketed by the company ENGELHARD under the name Nu antique bronze 240 AB (Timica), blue mother-of-pearl notably marketed by the company MERCK under the name Matte blue (17433) (Microna), Dark Blue (117324) (Colorona), white mother-of-pearl with a silver sheen, notably marketed by the company MERCK under the name Xirona Silver and orange-pinkish-golden-green mother-of-pearl notably marketed by the company MERCK under the name Indian summer (Xirona) and their mixtures.;

[0128] In addition to pearlescent pigments on a mica support, multilayer pigments based on synthetic substrates such as alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum can be considered.

[0129] Mention may also be made of interference effect pigments not fixed on a substrate such as liquid crystals (Helicones HC from Wacker), interference holographic flakes (Geometry Pigments or Spectra f / x from Spectratek). Special effect pigments also include fluorescent pigments, whether they are substances that fluoresce in daylight or that produce ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, marketed for example by the company Quantum Dots Corporation.

[0130] The variety of pigments that can be used in the present invention makes it possible to obtain a rich palette of colors, as well as particular optical effects such as metallic and interference effects.

[0131] The size of the pigment used in the cosmetic composition according to the present invention is generally between 10 nm and 200 qm, preferably between 20 nm and 80 qm, and more preferably between 30 nm and 50 qm.

[0132] The pigments can be dispersed in the product using a dispersing agent.

[0133] By “dispersing agent” we mean a compound which makes it possible to protect the particles dispersed against their agglomeration or flocculation. This dispersing agent may be a surfactant, an oligomer, a polymer or a mixture of several of them, carrying one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they can attach physically or chemically to the surface of the pigments. These dispersing agents also have at least one group functionally compatible or soluble in the continuous medium. Said agent can be charged, it can be anionic, cationic, zwitterionic or neutral.

[0134] According to a particular embodiment of the invention, the dispersing agents used are chosen from esters of 12-hydroxystearic acid, more particularly of C8 to C2o fatty acid and of polyol such as glycerol, diglycerin, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g / mol such as that sold under the name Solsperse 21 000 by the company Avecia, poly-lygyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel or polyhydroxystearic acid such as that sold under the reference Arlacel P100 by the company Uniqema and mixtures thereof.

[0135] As another dispersant that can be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17 000 sold by the company Avecia, poly dimethylsiloxane / oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185, DC2-5225 C.

[0136] The pigments used in the cosmetic composition according to the invention may be surface-treated with an organic agent. Thus, the previously surface-treated pigments useful in the context of the invention are pigments which have undergone totally or partially a surface treatment of a chemical, electronic, electrochemical, mechanochemical or mechanical nature, with an organic agent such as those described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, p. 53-64 before being dispersed in the composition in accordance with the invention. These organic agents may be chosen, for example, from amino acids; waxes, for example camauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; anionic surfactants; lecithins;sodium, potassium, magnesium, iron, titanium, zinc or aluminium salts of fatty acids, for example aluminium stearate or laurate; metal alkoxides; polysaccharides, for example chitosan, cellulose and its derivatives; polyethylene; (meth)acrylic polymers, for example polymethylmethacrylates; polymers and copolymers containing acrylate units; proteins; alkanoamines; silicone compounds, for example silicones, polydimethylsiloxanes, alkoxysilanes, alkylsilanes, siloxysilicates; fluorinated organic compounds, for example perfluoroalkyl ethers; fluorosilicon compounds.

[0137] The surface-treated pigments useful in the cosmetic composition according to the invention may also have been treated with a mixture of these compounds and / or have undergone several surface treatments.

[0138] The surface-treated pigments useful in the context of the present invention can be prepared according to surface treatment techniques well known to those skilled in the art or found as such commercially.

[0139] Preferably, the surface-treated pigments are covered by an organic layer.

[0140] The organic agent with which the pigments are treated can be deposited on the pigments by solvent evaporation, chemical reaction between the molecules of the surfactant or creation of a covalent bond between the surfactant and the pigments. The surface treatment can thus be carried out for example by chemical reaction of a surfactant with the surface of the pigments and creation of a covalent bond between the surfactant and the pigments or fillers. This method is described in particular in US patent 4,578,266.

[0141] Preferably, an organic agent covalently bound to the pigments will be used.

[0142] The surface treatment agent may represent from 0.1 to 50% by weight of the total weight of the surface-treated pigments, preferably from 0.5 to 30% by weight, and even more preferably from 1 to 10% by weight.

[0143] Preferably, the surface treatments of the pigments are chosen from the following treatments: - a PEG-Silicone treatment like the AQ surface treatment marketed by LCW; - a Chitosan treatment such as the CTS surface treatment marketed by LCW; - a Triethoxycaprylylsilane treatment such as the AS surface treatment marketed by LCW; - a Methicone treatment such as the SI surface treatment marketed by LCW - a Dimethicone treatment such as the Covasil 3.05 surface treatment marketed by LCW; - a Dimethicone / Trimethylsiloxysilicate treatment such as the Covasil 4.05 surface treatment marketed by LCW; - a Lauroyl Lysine treatment such as the LL surface treatment marketed by LCW - a Lauroyl Lysine Dimethicone treatment such as the LL / SI surface treatment marketed by LCW; - a Magnesium Myristate treatment such as the MM surface treatment marketed by LCW; - an Aluminum Dimyristate treatment such as the MI surface treatment marketed by Miyoshi; - a Perfluoropolymethylisopropyl ether treatment such as the FHC surface treatment marketed by LCW; - an Isostearyl Sebacate treatment like the HS surface treatment marketed by Miyoshi; - a Disodium Stearoyl Glutamate treatment such as the NAI surface treatment marketed by Miyoshi; - a Dimethicone / Disodium Stearoyl Glutamate treatment like the SA / NAI surface treatment marketed by Miyoshi; - a Perfluoroalkyl Phosphate treatment such as the PF surface treatment marketed by Daito; - an acrylate / Dimethicone and Perfluoroalkyl Phosphate Copolymer treatment like the FSA surface treatment marketed by Daito; - a Polymethylhydrogen siloxane / Perfluoroalkyl Phosphate treatment such as the FS01 surface treatment marketed by Daito; - a Lauryl Lysine / Aluminum Tristearate treatment such as the LL-StAI surface treatment marketed by Daito; - an Octyltriethylsilane treatment such as the OTS surface treatment marketed by Daito; - an Octyltriethylsilane / Perfluoroalkyl Phosphate treatment such as the FOTS surface treatment marketed by Daito; - an Acrylate / Dimethicone Copolymer treatment such as the ASC surface treatment marketed by Daito; - an Isopropyl Titanium Triisostearate treatment like the ITT surface treatment marketed by Daito; - a Microcrystalline Cellulose and Carboxymethyl Cellulose treatment such as the AC surface treatment marketed by Daito; - a Cellulose treatment such as the C2 surface treatment marketed by Daito - an Acrylate copolymer treatment such as the APD surface treatment marketed by Daito; - a Perfluoroalkyl Phosphate / Isopropyl Titanium Triisostearate treatment like the PF + ITT surface treatment marketed by Daito

[0144] The composition in accordance with the present invention may further comprise one or more non-surface-treated pigments.

[0145] According to a particular embodiment of the invention, the pigment(s) are mineral pigments.

[0146] According to another particular embodiment of the invention, the pigment(s) are chosen from nacres.

[0147] According to a particular embodiment of the invention, the agent of dispersion is present with organic pigments in the composition of the invention in particulate form of submicron size.

[0148] By "sub-micronic" or in English "sub-micronic" is meant pigments whose particle size has been micronized by micronization method and whose average particle size is less than one micronmeter (qm), in particular between 0.1 and 0.9 qm, and preferably between 0.2 and 0.6 qm.

[0149] According to one embodiment, the dispersing agent and the pigment(s) are present in an amount (dispersant: pigment) of between 0.5:1 and 2:1, particularly between 0.75:1 and 1.5:1 or better between 0.8:1 and 1.2:1.

[0150] According to a particular embodiment, the dispersing agent is suitable for dispersing the pigments and is compatible with a condensation-curable formulation.

[0151] By "compatible" is meant, for example, that said dispersing agent is miscible in the oily phase of the composition or dispersion containing the pigment(s), it does not delay or reduce hardening. The dispersing agent is preferably cationic.

[0152] The dispersing agent(s) may therefore have a silicone backbone, such as silicone polyether and amino-silicone type dispersants. Suitable dispersing agents include: - amino-silicones, i.e. silicones comprising one or more amino groups such as those marketed under the names and references: BYK LPX 21879, by BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, marketed by Genesee polymers, - silicone acrylates such as Tego ® RC 902, Tego ® RC 922, Tego ® RC 1041, and Tego ® RC 1043, marketed by Evonik, - polydimethylsiloxane (PDMS) silicones with carboxylic groups such as X-22162 and X-22370 by Shin-Etsu, silicone epoxy such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682, and GP-695, by Genesee Polymers, or Tego ® RC 1401, Tego ® RC 1403, Tego ® RC 1412, by Evonik.

[0153] According to a particular embodiment, the dispersing agent(s) are of the amino-silicone type and are positively charged.

[0154] Dispersing agents having chemical groups capable of reacting with the reactants of the oil phase and thus are capable of improving the 3D network formed from the amino-silicones may also be mentioned. For example, silicone epoxy pigment dispersing agents may chemically react with the amino-silicone prepolymer amino group(s) to increase the cohesion of the amino-silicone film comprising the pigment(s).

[0155] Preferably, the pigment(s) iii) of the invention are chosen from carbon black, iron oxides, in particular red and black, and micas coated with iron oxide. iron, triarylmethane pigments, particularly blue and violet pigments such as BLUE 1 LAKE, azo pigments, particularly red pigments, such as D&C RED 7, alkali metal salt of lithol red, such as the calcium salt of lithol red B, more preferably D&C RED 7.

[0156] According to a particular embodiment of the invention, the quantity of pigments varies from 0.5% up to 40%, and preferably from 1 to 20% relative to the weight of the composition and dispersion comprising them.

[0157] The composition may comprise one or more direct dye(s).

[0158] By "direct dye" we mean natural and / or synthetic dyes, different from oxidation dyes. These are dyes which will diffuse superficially on keratin materials, in particular keratin fibers.

[0159] They can be ionic or non-ionic, in particular cationic, anionic or non-ionic.

[0160] Examples of suitable direct dyes that may be mentioned include azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or as mixtures.

[0161] According to one embodiment of the invention, the coloring agent(s), in particular pulverulent ones, are present in the composition in a content of 0.01 to 50% by weight, relative to the weight of the composition, preferably 0.1 to 40% by weight, or even 1 to 30% by weight.

[0162] The pigments may be white or colored, mineral and / or organic, interference-prone or not. Among the mineral pigments, mention may be made of titanium dioxide, optionally surface-treated, zirconium or cerium oxides, as well as iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue. Among the organic pigments, mention may be made of carbon black, D & C type pigments, and lakes based on cochineal carmine, barium, strontium, calcium, aluminum. The pearlescent pigments may be chosen from white pearlescent pigments such as mica coated with titanium or bismuth oxychloride, colored pearlescent pigments such as titanium mica with iron oxides, titanium mica with in particular ferric blue or chromium oxide, titanium mica with an organic pigment of the aforementioned type as well as pearlescent pigments based on bismuth oxychloride.

[0163] By “fillers” is meant colorless or white particles, mineral or synthetic, lamellar or non-lamellar, intended to give body or rigidity to the composition, and / or softness, mattness and uniformity to the ma keel. The fillers can be mineral or organic of any shape, platelet, spherical or oblong. Examples include talc, mica, silica, kaolin, nylon and polyethylene powders, poly-[3-alanine and polyethylene powders, Teflon, lauroyl-lysine, starch, boron nitride, tetrafluoroethylene polymer powders, hollow microspheres such as Expancel (Nobel Industrie), polytrap (Dow Corning) and silicone resin microbeads (Tospearls from Toshiba, for example), precipitated calcium carbonate, magnesium carbonate and hydrocarbonate, hydroxyapatite, hollow silica microspheres (SILICA BEADS from MAPRECOS), glass or ceramic microcapsules, metal soaps derived from organic carboxylic acids having from 8 to 22 carbon atoms, preferably from 12 to 18 carbon atoms, for example zinc, magnesium or lithium, zinc laurate, magnesium myristate.

[0164] Liposoluble colorants are, for example, Sudan red, DC Red 17, DC Green 6, [3-carotene, soybean oil, Sudan brown, DC Yellow 11, DC Violet 2, DC orange 5, quinoline yellow. They can represent 0.01 to 20% of the weight of the composition and better still 0.1 to 6%.

[0165] The water-soluble colorants are, for example, beetroot juice, methylene blue and can represent 0.01 to 6% of the total weight of the composition.

[0166] According to a preferred embodiment of the invention, the composition comprises i) one or more compounds of formula (I), (I-1), (Ia) or (Ia) as defined above, ii) one or more liquid fatty substances as defined above and iii) one or more pigments as defined above.

[0167] The composition according to the invention may be in the form of a suspension, a dispersion in particular of oil in water using vesicles; an oil-in-water, water-in-oil or multiple emulsion; a gel or a mousse; an oily or emulsified gel; a dispersion of vesicles in particular lipidic; a two-phase or multi-phase lotion; a loose, compact or cast powder; an anhydrous paste. This composition may have the appearance of a lotion, a cream, an ointment, a soft paste, an ointment, a mousse, a cast or molded solid and in particular in a stick or cup, or even a compacted solid.

[0168] A person skilled in the art will be able to choose the appropriate galenic form, as well as its method of preparation, on the basis of his general knowledge, taking into account on the one hand the nature of the constituents used, in particular their solubility in the support, and on the other hand the application envisaged for the composition.

[0169] The cosmetic composition according to the invention may be in the form of a care and / or makeup product for the skin of the body or face, lips, nails, eyelashes, eyebrows and / or hair, a sun or self-tanning product, a hair product for care, treatment, cleaning, conditioning, styling, makeup or hair coloring.

[0170] It can thus be presented in the form of a makeup composition, in particular a complexion product such as a foundation, a blush or eyeshadow; a lip product such as a lipstick, a gloss or a lip care product; a concealer product; a blush, a mascara, an eyeliner; an eyebrow makeup product, a lip or eye pencil; a nail product such as a nail polish or a nail care product; a body makeup product; a hair makeup product (hair mascara).

[0171] It can also be presented in the form of a composition for protection, cleaning, hygiene or care of the skin of the face, neck, hands or body, in particular an anti-wrinkle composition, a moisturizing or treatment composition; a sun or artificial tanning composition (self-tanner); a deodorant or antiperspirant composition.

[0172] It can also be presented in the form of a hair product, in particular for coloring, maintaining the hairstyle, shaping the hair, caring for, treating or cleaning the hair, such as shampoos, gels, styling lotions, blow-drying lotions, fixing and styling compositions such as hairsprays or sprays.

[0173] Preferably, the cosmetic composition according to the invention is in the form of a makeup product for the body, lips, eyelashes, hair, nails, possibly having care and / or non-therapeutic treatment properties.

[0174] It is particularly presented in the form of a lipstick or lip gloss, a lip balm, a blush or eyeshadow, a foundation, a tattoo product, a mascara, an eyeliner, a nail polish, an antiperspirant, a deodorant agent, a hair coloring or care product.

[0175] The invention also relates to a method for the cosmetic treatment of keratin materials such as the skin of the body or face, lips, nails, hair, eyebrows and / or eyelashes, comprising the application to said materials of a composition, in particular a cosmetic composition as defined above.

[0176] Preferably, it is a method for making up the skin, lips, eyelashes, nails, eyebrows, hair and / or lips; more preferably a method for treating the lips, even more preferably for making up the lips.

[0177] In particular, the composition is in the form of a stick, preferably comprising a quantity of less than 7% by weight of water, preferably less than 5% by weight of water, even more preferably less than 3% by weight of water, better still less than 1% by weight of water, relative to the total weight of the composition, even more preferably the composition is anhydrous or free of water.

[0178] The compounds according to the invention can also find an application in the field of the paint, varnish and glue industry, as a structuring, thickening or even gelling agent, preferably in cosmetics.

[0179] The invention is illustrated in more detail in the following examples. EXAMPLES

[0180] Examples of synthesis:

[0181] Synthesis of intermediate (C): 1,3:2,4-Di-benzylidene-xylonate methyl ester with R1, R'1, R2, R'2, R3, R'3, R4, R'4, R5 and R'5 represent a hydrogen atom: [Chem. 12]: ëHj (C)

[0182] 4.1 g of benzaldehyde dimethylacetate (27 mmol) (Sigma-Aldrich) are added to 1 g of D-xylono-1,4-lactone (6.8 mmol) (Sigma-Aldrich). 0.22 g of 37% hydrochloric acid (Sigma-Aldrich) are then added. The reaction medium is stirred for 2 days at room temperature and then diluted with acetonitrile (5 mL). Compound (C) precipitates and is filtered on a Buchner funnel, washed twice with 10 mL of acetonitrile and twice with 10 mL of distilled water. The solid thus obtained is dried in an oven (50°C) to yield compound (C) in the form of a white solid.

[0183] Spectroscopic analyses (NMR *H) are consistent with the expected structure (C).

[0184] Example 1: Synthesis of 1,3:2,4-Di-benzylidene-xylonate mono-isostearyl ester of formula (I) with R representing -(CH2)15-CH(CH3)2; R1,R'1, R2, R'2, R3, R'3, R4, R'4, R5, R'5 represent a hydrogen atom: [Chem. 13]

[0185] 1 g of intermediate (C) is mixed with 10 mL of methyltetrahydrofuran (Sigma-Aldrich, anhydrous), 0.83 g of isostearyl alcohol (Sigma-Aldrich, previously dried) and finally, 50 mg of anhydride sulfuric acid (Sigma-Aldrich, anhydrous). The mixture is stirred at 60 C under a vacuum of 380 mbar and the progress of the reaction is monitored by 'H NMR. The mixture is then concentrated on a rotary evaporator. The residue is dissolved in a mixture of 10 mL of dichloromethane and 10 mL of brine immediately neutralized to pH 7 with sodium hydroxide. The organic phase is dried over Na2SO4 and concentrated on a rotary evaporator. In order to remove excess fatty alcohol, the crude is taken up in 10 mL of methanol and 10 mL of heptane, an insoluble intermediate product precipitates and is filtered and separated. The methyl phase is concentrated on a rotary evaporator to yield the expected compound in the form of a pasty solid.

[0186] Spectroscopic analyses are consistent with the expected structure.

[0187] Evaluation of the compounds of the invention vs. comparative: The comparisons are according to example 2: synthesis of diben-zylidene-d-sorbitol monoisostearate (outside the invention)

[0188] The gelation process is as follows: the product to be evaluated is weighed to obtain a concentration of 2% m / V (i.e. 20 mg in 1 mL of oil). The oil is added at room temperature. The mixture is magnetically stirred and heated at 60°C or 75 C or 90 C for one hour in a 20 ml vial (SCREW VIALS 24 mm CLEAR GLASS 27.5X57 mm). The vial is then left to cool at room temperature without specific action for at least 2 hours. The evaluation of the gelation was carried out by visual observation of a magnetic bar present in the gel when the vial is turned upside down. [Tables 1] i) Compound of formula (I) Visual results ii) Liquid fatty substance Octyl-2-dodecanol Squalane 60C / 2%* Example 1 (Invention) The mixture gels homogeneously with the presence of a portion of the unsolubilized starting product. The mixture gels homogeneously with a translucent appearance with the presence of a portion of the unsolubilized starting product. Example 2 (outside the invention) The mixture does not gel and the entire product remains insoluble. The mixture does not gel and the entire product remains insoluble. * % m / V Additional tests were carried out with example 1 by varying the temperature and / or the concentration. [Tables 2] i) Compound of formula (I) Visual results ii) Liquid fatty substance Octyl-2-dodecan 01 Squalane Isoamyl laurate Isododecane 60C / 2%* Example 1 (Invention) The mixture gels homogeneously with the presence of a portion of the unsolubilized starting material. The mixture gels homogeneously with a translucent appearance and the presence of a portion of the unsolubilized starting material. The mixture gels homogeneously with an opaque appearance. The mixture becomes more viscous and flows. 75C / 2%* Example 1 (Invention) The mixture gels homogeneously and opaque. The mixture gels homogeneously with the presence of a portion of the unsolubilized starting material. The mixture gels homogeneously and translucent. The mixture becomes more viscous and flows.60 C, concentration indicated for each test Example 1 (Invention) The mixture becomes viscous at a concentration of 1.5%* The mixture gels homogeneously at a concentration of 0.5%*, with a translucent appearance and the presence of a part of the unsolubilized starting product. Test not carried out Test not carried out. * % m / V i) Compound of formula (I) Visual results ii) Liquid fatty substance Squalane 75 C / 0.3%* Example 1 (Invention) The mixture gels homogeneously with a translucent appearance Example 2 (outside the invention) The mixture remains liquid with the presence of a solid * % m / V

[0189] Examples of sticks:

[0190] From example 1, in octyl-2-dodecanol, we carried out the preparation of three cosmetic sticks under the following implementation conditions: 5% concentration by weight and heating at 80°C for 30 minutes.

[0191] Without pigment: Stick 1

[0192] Procedure: In a 10 mL bottle, 50 mg of Example 1 are mixed with 1 mL of octyl-2-dodecanol (5% w / v). This mixture is heated to 80°C for 30 minutes with magnetic stirring. The solution is added to a previously cut 2.5 mL syringe. The syringe is left to stand for 1 hour at room temperature, then pressed to carry out the evaluation. The gelled product comes out easily from the syringe and remains structured, cylindrical without change in the internal diameter of the cylinder in which it is located (cylinder of the syringe), nor in general appearance even after several minutes (15 minutes). In addition, it appears that during application the stick does not break, and does not crumble during application to the substrate (see [Fig.l] in the appendix).

[0193] With pigments: Sticks 2 and 3

[0194] In a 10 mL bottle, 50 mg of Example 1 (5% w / v) are mixed with 50 mg of pigment (Red7 Lake) (5% w / v) and 1 mL of octyl-2-dodecanol. This mixture is heated to 80°C for 30 min with magnetic stirring. The solution is added to a previously cut 2.5 mL syringe. The syringe is left to stand for 1 hour at room temperature to yield stick 2, then pressed to perform the evaluation. Stick 3 was prepared in the same way as stick 2 except that the Red 7 Lake was replaced by the same quantity by weight of DC RED 7 (Stick 3) (see [Fig. 2] and 3 in the appendix).

[0195] These three sticks are shiny and easily disintegrate during use after applying sticks 1 to 3 to the substrate (a sheet of paper). It is observed that the gelled products come out easily from the syringes and remain structured, cylindrical without visual change in the internal diameter of the cylinder in which it is located (syringe cylinder), nor in the general appearance even after several minutes (15 minutes). In addition, the sticks do not break when applied to the substrate (see [Fig.3] in the appendix).

Claims

Claims

1. Compound of formula (I) as well as its optical, geometric isomers, its acid or base salts, organic or mineral, and its solvates such as hydrates: (I) Formula (I) in which: R1 to R'5, which may be identical or different, represent a hydrogen atom, a halogen atom such as fluorine, chlorine or bromine; or a group chosen from: i) linear or branched (Ci-C6)alkyl, ii) -O-Ra, iii) -C(X)O-Rb or -OC(X)-Rb, iv) -NRC Rd, and v) -C(X)-NRcRd or -N(Rc)-C(X)-Rd, with Ra representing a hydrogen atom, or a (Ci-C4)alkyl group such as methyl, aryl(Ci-C4)alkyl such as benzyl, (C3-C8)cycloalkyl such as cyclohexyl; Rb representing a hydrogen atom or a (Ci-C4)alkyl group; Rc, and Rd, identical or different, representing a hydrogen atom, or a (Ci-C4)alkyl group such as methyl, or (C3-C8)cycloalkyl such as cyclohexyl and X representing an oxygen or sulfur atom or an NRC group, preferably X represents an oxygen atom; it being understood that two adjacent radicals Ri to R's can also form together with the carbon atoms which carry them a cycle (C5 -C8)unsaturated such as benzo; • R represents a radical chosen from i) -OXi; ii) -OC(X)-Xi; iii) -N(RC)-Xi; iv) -SXi. with X as defined above, preferably X represents an oxygen atom; and Xi representing a) a (C4-C8)cycloalkyl group such as cy- clohexyl; or b) a hydrocarbon chain comprising from 6 to 24 carbon atoms, saturated or unsaturated, linear or branched, said chain being: optionally interrupted by one or more heteroatoms or divalent radicals chosen from: O, S, N(RC), C(O) or combinations thereof such as -OC(O)-, -C(O)-O-, -C(O)-N(R c)-, -N(Rc)-C(O)-; and / or optionally substituted by one or more halogen atoms and / or groups, identical or different, chosen from: -O-Ra, -C(O)-O-Rb,oo-NRcRd, and (C4-C8)cycloalkyl with Ra, Rb, Rc and Rd as defined above, preferably Ra and Rb represent a (Ci-C4)alkyl group such as methyl and Rc and Rd independently represent a hydrogen atom or (Ci-C4)alkyl group such as methyl.

2. preferably R1 is identical to R'1, R2 is identical to R'2, R3 is identical to R'3, R4 is identical to R'4, and R5 is identical to R'5 Compound of formula (I) as defined in the preceding claim chosen from those of formula (Ia), as well as its acid or base salts, organic or mineral, and its solvates such as hydrates:

3. Formula (Ia) with R, R1 to R'5 as defined in the preceding claim; preferably R1 is identical to R'1, R2 is identical to R'2, R3 is identical to R'3, R4 is identical to R'4, and R5 is identical to R'5 Compound of formula (I) or (Ia) as defined in claim 1 or 2 which is such that: * R1 to R'5, identical or different, preferably identical, represent i) a hydrogen atom, or a group ii) (Ci-C6)alkyl; iii)

4.

5. -O-Ra, or°iv) -C(O)-O-Rb with Ra and Rb as defined above, preferably Rarerepresents a hydrogen atom, a (CrC4)alkyl group, or benzyl; and Rb represents a hydrogen atom or a (Ci-C4)alkyl group; and / or * R is as defined in claim 1 and Xi preferably represents a) a (C4-C8)cycloalkyl radical, b) a saturated or unsaturated, linear or branched C10-C24 hydrocarbon chain, said chain being optionally interrupted by one or more heterotoms or divalent radicals chosen from -O-, -N(RC)-, -C(O)- and their combinations such as -OC(O)-, -C(O)-O-, -C(O)-N(Rc)-, -N(Rc)-C(O)-, said chain being optionally substituted by one or more identical or different radicals chosen from the radicals -O-Ra, -C(O)-O-Rb with Rarerepresenting a (C1-C4)alkyl group, Rb representing a (C1-C4)alkyl group and Rc being as defined above and preferably a hydrogen atom;. Compound of formula (I) or (Ia) as defined in any one of the preceding claims which is such that:R represents a radical -OX1 with Xi as defined in any one of the preceding claims, preferably Xi representing a saturated or unsaturated, linear or branched Cio-C24 hydrocarbon chain; more preferably Xi represents a saturated or unsaturated, linear or branched hydrocarbon chain comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms. Compound of formula (I) or (Ia) as defined in any one of the preceding claims which is chosen from those of formula (I-1) following, as well as its optical, geometric isomers, and its solvates such as hydrates: (ID / Formula (1-1) with Xi as defined in any one of the claims- preceding indications; more preferably the compounds of formula (I), (ID) or (la) of the invention are chosen from those of formula (la) following as well as its geometric isomers, and solvated such as hydrates:

6.

7.

8. Formula (a) with Xi as defined previously. Compound of formula (I), (I-1), (la) or (la) as defined in any one of the preceding claims which is such that Xi represents a hydrocarbon chain, linear or branched, preferably linear, comprising from 1 to 3 unsaturations, in particular 1 unsaturation and comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms, more particularly Xi is chosen from the following linear alkenyl groups: -(CH2)m-CH=CH-(CH2)nH with m and n, identical or different, preferably identical, representing an integer between 0 and 20 inclusively, it being understood that the sum of n+m is between 8 and 20 inclusively, preferably n+m is between 10 and 18 inclusively, and more preferably between 12 and 18 inclusively such as 16, again more preferably m=n. Compound of formula (I), (I-1), (la) or (la) as defined in any one of claims 1 to 5, which is such that Xi represents a saturated, linear or branched hydrocarbon chain, comprising from 10 to 22 carbon atoms, preferably from 12 to 20 carbon atoms, more preferably from 14 to 20, such as 18 carbon atoms, more particularly Xi represents a -(CH2)p-CH-RiR2 chain with Ri and R2, identical or different, representing a hydrogen atom or a (Ci-C6)alkyl group such as methyl, and p represents an integer between 9 and 21 inclusive, preferably between 11 and 19, more particularly between 13 and 17 such as 15. A compound of formula (I), (I-1), (Ia) or (Ia) as defined in a any of the preceding claims, which is chosen from and in particular the compound (1) Compounds (1) or (2) as well as their optical and geometric isomers, and their solvates such as hydrates; particularly chosen from the following compounds (la) and (2a):

9. And in particular compound (la), compounds (la) and (2a) as well as their geometric isomers, and their solvates such as hydrates. Process for the preparation according to the synthesis schemes [Chem. 10] and [Chem. 11] of the compounds of formula (I), as defined in any one of the preceding claims for which: * when R^R'1, R2=R'2, R3=R'3, R4=R'4 and R5=R'5 the preparation process comprises a first step in which a lactonel (Ai) or acyclic (A2) derivative which can be in any enantiomeric or racemic form, is reacted with at least 2 molar equivalents of aldehyde (B) in the presence of a catalyst chosen in particular from organic or mineral acids, such as hydrochloric acid or paratoluenesulfonic acid; - from the lactone derivative (AJ, the reaction is carried out at room temperature or by heating to a temperature inclusively between 30°C and 80°C, preferably at room temperature, with or without solvent, for at least one hour, preferably for a duration of between 3 h and 48 h; - from the acyclic derivative (A2), the reaction is carried out at a temperature of between 30 and 80°C inclusive, in particular between 40 and 70°C inclusive, under a vacuum preferably at a pressure of between 20 mbar and 500 mbar, in particular between 30 mbar and 400 mbar, for a duration preferably of several hours, particularly between 3 hours and 2 days; the compound (C) is optionally purified and optionally isolated, for example by precipitation, and is subjected to: ** Route A: to a (thio)esterification reaction to lead to the compounds of formula (I') of the invention; this (thio)esterification reaction is carried out chemically, by reaction with a thiol Xi-SH or an alcohol Xi-OH, Xi being as defined in any one of the preceding claims, by acid catalysis, or by any other (thio)esterification method known to those skilled in the art; or this (thio)sterification reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a solvent, preferably polar aprotic such as for example acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyl-tetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification reaction of (C) to (I') is carried out with a supported lipase which allows the recycling of the enzyme at the end of the reaction; or ** Route B: to an amidation reaction to lead to the compounds (I”) of the invention; this amidation reaction is carried out chemically, by reaction with an amine such as XrNH(Rc) or by any other amidation method known to those skilled in the art; or this amidation reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a solvent, preferably polar aprotic such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyl- tetrahydrofuran, in the presence of an enzyme; in particular, the amidation reaction of (C) to (I”) is carried out with a supported lipase which allows the recycling of the enzyme at the end of the reaction; or ** Route C: to an anhydrification reaction to lead to the compounds (I'”) of the invention; this step is carried out chemically, by the condensation of (C) with an acid XrC(O)-OH in an acidic medium and in the presence of a dehydrating agent such as phosphorus pentoxide or by activating the compound (C) with, for example, a thionyl halide such as SOCl2 and then by reacting the latter activated compound (C) with an acid XrC(O)-OH or by any other anhydride synthesis method known to those skilled in the art; The lactone derivatives (AJ denote in particular D-(+)-Ribonic y-lactone, D-Xylono-1,4-lactone and D-Arabino-1,4-lactone and in particular D-Xylono-1,4-lactone; and the acyclic derivatives (A2) denote in particular ribonic acid, ribonic acid xylonic and arabonic acid and in particular xylonic acid; [Chem. 10] * when the compounds of formula (I) are such that R1 is different from R' and / or R2 is different from R'2, and / or R3 is different from R'3, and / or R4 is different from R'4 and / or R5 is different from R'5, the preparation process comprises a first step 1), in which the lactone derivative (AJ or the acyclic derivative (A2) as defined previously reacts with a molar equivalent of aldehyde (B) in dimethyl acetal form, preferably in the presence of a catalyst chosen in particular from organic or mineral acids, such as hydrochloric acid or paratoluenesulfonic acid; - from the lactone derivative (Ai), the reaction is carried out at room temperature or the medium is heated to a temperature of between 30°C and 80°C inclusive, in particular between 40°C and 70°C inclusive, preferably at room temperature, with or without solvent, for a period of several hours, preferably between 3 hours and 2 days; - from the acyclic derivative (A2), the reaction is carried out at a temperature of between 30°C and 80°C inclusive, between 40°C and 70°C inclusive, preferably under vacuum, particularly at a pressure of between 20 mbar and 500 mbar, in particular between 30 mbar and 400 mbar, with or without solvent, for a duration preferably of between 3 hours and 2 days, followed 2) by the addition of at least one molar equivalent of protected aldehyde (B') in methyl acetal form under the same conditions as in step 1) with (B) to yield the compound (Cb), said compound (Cb) being able to be isolated by precipitation and is subjected to: ** Route A': to a (thio)esterification reaction to lead to the compounds of formula (I'b) of the invention; this (thio)esterification step can be carried out chemically, for example by reaction with a thiol XrSH or an alcohol Xr0H, Xi being as defined previously, in acid catalysis, or by any other (thio)esterification method as mentioned previously; according to a particular embodiment the (thio)esterification reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a preferably polar aprotic solvent such as for example acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyltetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification reaction of (Cb) to (l'b) is made with a supported lipase; or ** Route B': to the amidation reaction to lead to the compounds (I”b) of the invention; this step can be carried out chemically, for example by reaction with an amine XrNH(Rc), or by any other amidation method as mentioned previously; according to one embodiment the amidation reaction is carried out biocatalytically, in particular with a lipase, supported or not, in a preferably polar aprotic solvent such as for example acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran, methyltetrahydrofuran, in the presence of an enzyme; in particular, the amidation reaction of (Cb) to (I”b) is carried out with a supported lipase which allows the recycling of the enzyme at the end of the reaction; or ** Route C': to the anhydridification reaction to lead to the compounds (I”'b) of the invention; this step can be carried out chemically, for example by the condensation of (Cb) with an acid Xi-C(O)-OH, Xi being as defined previously, in an acidic medium and in the presence of a dehydrating agent such as phosphorus pentoxide or equal to 100°C or by activating the compound (Cb) for example in the form of acid chloride by reaction of (Cb) with a thionyl halide such as SOCl2 then reaction of the latter activated compound (Cb) with an acid Xi -C(O)-OH, Xi being as defined previously, or by any other method known to those skilled in the art;

10. [Chem. 11] Composition comprising: i) one or more compounds of formula (I), (I-1), (Ia), (Ia), (Ia), (Ia), (2), (Ia) or (2a) as defined in any one of claims 1 to 10; 8.

11.

12. Composition according to the preceding claim in which the quantity of compounds of formula (I), (1-1), (la), (la), (1a), (1), (2), (la) or (2a), is less than or equal to 15% by weight, preferably less than or equal to 10% by weight and more preferably less than or equal to 8% by weight relative to the total weight of the cosmetic composition; it may be between 0.005 and 15% by weight, preferably between 0.01 and 13% by weight, in particular between 0.1 and 10% by weight, or even between 0.15 and 9% by weight, and better still between 0.2 and 8% by weight, relative to the total weight of the composition. Composition according to any one of claims 10 or 11 which comprises ii) one or more liquid fatty substances, particularly chosen from a) linear or branched hydrocarbons, in particular with more than 16 carbon atoms, such as paraffin oils, vaseline oil, polydecenes, hydrogenated polyisobutene such as squalane, preferably squalane, b) saturated or unsaturated, linear or branched liquid fatty alcohols, such as octyldodecanol c) linear or branched C6-C16 alkanes, preferably branched such as isododecane, isohexadecane, preferably isododecane, and d) liquid fatty esters, in particular derived from saturated C8-C26 aliphatic monoacids such as C12 and more particularly derived from saturated C8-C26 monoacids with a branched monoalcohol, preferably C3-C9 such as C5, preferably isoamyl laurate.

13. Composition according to any one of claims 10 to 12 which comprises one or more liquid fatty substances ii) as defined in the preceding claim in an amount varying from 1 to 99% by weight, preferably in an amount varying from 5 to 99% by weight, and even more preferably in an amount varying from 10 to 99% by weight relative to the total weight of the composition.

14. Composition according to any one of claims 12 to 13 which comprises iii) one or more coloring agents in particular chosen from powdered dyes such as pigments, fillers, pearlescent agents and glitter, and / or liposoluble or water-soluble dyes; preferably iii) are chosen from pigments in particular chosen from carbon black, iron oxides in particular red and black and micas coated with iron oxide, triarylmethane pigments in particular blue and violet such as BLUE 1 LAKE, azo pigments in particular red such as D&C RED 7 alkali metal salt of lithol red such as the calcium salt of lithol red B; even more preferably D&C RED 7.

15. A method of treating keratin materials comprising the application to said keratin materials of a composition according to any one of claims 11 to 14.

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