Description

Title: DIBENZYLIDENE ALDITOL DERIVATIVES, COMPOSITION COMPRISING THEM, AND THEIR USE IN COSMETICS

[0001 ] A subject matter of the present invention is a composition comprising at least one specific dibenzylidene alditol derivative of formula (I), a cosmetic treatment process comprising said derivative, novel dibenzylidene alditol derivatives, their process of preparation and their use in cosmetics, in particular for thickening lipophilic media, such as oils, and more particularly in "cosmetic sticks", such as lipsticks.

[0002] Cosmetic compositions are generally thickened in order to make possible easy application. The formulator has available numerous possibilities for thickening and gelling both hydrophilic media and lipophilic media, such as oils. Thus, in order to thicken oils until sticks simultaneously having a sufficient consistency, an acceptable stability over time and a suitable disintegratability are obtained, a person skilled in the art generally uses crystallizable compounds which are essentially waxes, such as polyethylene waxes, candelilla waxes, carnauba waxes or beeswaxes, and also pasty compounds, predominantly lanolins. Generally, a mixture consisting of 50-70% of oils and of pasty compounds can be brought to the level of consistency making it possible to manufacture a disintegratable "stick" by addition of 12-20% of 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 for polar media (Xylitol Based Phase Selective Organogelators for Potential Oil Spillage Recovery, RSC Adv., 2017, 7, p. 37175, WO 2018/002947, and JP63304079). On the other hand, these dibenzylidene alditols are not 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 use 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 of degradation of certain ingredients (EP 2 542556 A1). Furthermore, the thickened medium may lack uniformity of thickness, such as, for example, a liquid part and/or the presence of a solid, or also result in opaque thickened media, which can be a handicap in certain applications. Thus, there remains a real need to make available compounds making it possible to gel lipophilic media, in particular oily media, at a temperature compatible with the various constituents and in particular at a temperature of less than 120°C, preferably of less than or equal to 100°C, indeed even of less than or equal to 80°C. In addition, sorbitol dibenzylidene esters are generally employed at a high concentration in order to obtain a stick (greater than 10% by weight, with respect to the total weight of the composition). It would thus be desirable to reduce the content for in particular economic reasons. In addition, it is difficult to be able to generate more or less opaque gels, or more or less translucent gels, as a function of the fatty substance to be gelled. Furthermore, unlike the waxes normally used, the compounds of the invention result in thickened lipophilic media and translucent and glossy sticks.

[0005] These problems have been solved by the use, in cosmetics, of i) dibenzylidene alditol compound(s), of formula (I), and also their optical or geometrical isomers, and their organic or inorganic acid or base salts, and their solvates, such as hydrates:

[Chem. 1] in which formula (I):

• R ¹ to R' ⁵ , which are 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-Ce)alkyl, ii) -0-R _a , iii) -C(X)-0-Rbor-0-C(X)-Rb, iv) - NRcR _d and v) -C(X)-NR _c R _d or -N(R _c )-C(X)-R _d , with R _a representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, an aryl(Ci-C4)alkyl group, such as benzyl, or a (C3-C8)cycloalkyl group, such as cyclohexyl; R representing a hydrogen atom or a (Ci-C4)alkyl group; R _c and R _d , which are identical or different, representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, or a (C3-C8)cycloalkyl group, such as cyclohexyl, and X representing an oxygen or sulfur atom or an NR _C group; preferably, X represents an oxygen atom; it being understood that two adjacent Ri to R' ₅ radicals can also form, together with the carbon atoms which carry them, an unsaturated (Cs-Cs) ring, such as benzo;

• R represents a radical chosen from i) -Xi; ii) -C(X)-Xi; iii) -C(X)-0-Xi; iv) -C(X)-N(Rc)-Xi; with X as defined above; preferably, X represents an oxygen atom; and Xi representing a) a (C ₄ -C ₈ )cycloalkyl group, such as cyclohexyl; or b) a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 6 to 24 carbon atoms, said chain being:

- optionally interrupted by one or more heteroatoms or divalent radicals chosen from: O, S, N(R _C ), C(O) or their combinations, such as -O-C(O)-, - C(0)-0-, -C(0)-N(Rc)- or -N(R _c )-C(0)-; and/or

- optionally substituted by one or more halogen atoms and/or groups, which are identical or different, chosen from: -0-R _a , -C(0)-0-R _b ,

-NRcR _d and (C4-C8)cycloalkyl with R _a and R _b as defined above; preferably, R _a and R _b represent a (Ci-C4)alkyl group, such as methyl.

[0006] It has been discovered that the compounds of formula (I) of the invention make it possible to structure and thicken ii) liquid lipophilic media or fatty substances, in particular oils, and to thus result in thickened compositions, in particular cosmetic compositions, indeed even to result in coloured or colourless, and non-brittle, translucent sticks being obtained.

[0007] Another subject-matter of the invention is a cosmetic treatment process employing one or more compounds of formula (I) as defined above.

[0008] Another subject-matter of the invention is the compounds of formula (I) as defined above.

[0009] Another subject-matter of the invention is a process for the preparation of compounds of formula (I) as defined above.

[0010] Another subject-matter of the invention is a composition, preferably a cosmetic composition, comprising one or more compounds of formula (I) as defined above.

[0011] Within the meaning of the present invention and unless otherwise indicated:

- within the meaning of the present invention, " fatty substance " is understood to mean an organic compound which is insoluble in water at ordinary temperature (25 °C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, and preferably of less than 1%, more preferentially still of less than 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 or dichloromethane, lower alcohols, such as ethanol, or aromatic solvents, such as benzene or toluene.

- "organic or inorganic acid salt' is understood more particularly to mean the salts chosen from a salt derived i) from hydrochloric acid HCI, ii) from hydrobromic acid HBr, iii) from sulfuric acid H2SO4, iv) from alkylsulfonic acids: Alk-S(0) ₂ 0H, such as from methylsulfonic acid and from ethylsulfonic acid; v) from arylsulfonic acids: Ar- S(0) ₂ 0H, such as from benzenesulfonic acid and from toluenesulfonic acid; vi) from citric acid; vii) from succinic acid; viii) from tartaric acid; ix) from lactic acid; x) from alkoxysulfinic acids: Alk-0-S(0)0H, such as from methoxysulfinic acid and from ethoxysulfinic acid; xi) from aryloxysulfinic acids, such as from tolueneoxysulfinic acid and from phenoxysulfinic acid; xii) from phosphoric acid H3PO4; xiii) from acetic acid CH ₃ C(0)OH; xiv) from triflic acid CF3SO3H; and xv) from tetrafluoroboric acid HBF ₄ ;

- " salts of organic or inorganic bases " is understood to mean salts of alkaline bases or agents as defined below, such as alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, aqueous ammonia, amines or alkanolamines.

- an "alkyl radical' it is saturated, linear or branched, C-i-Cs, preferably C ₁ -C6, more preferentially C ₁ -C ₄ , hydrocarbon radical, such as methyl or ethyl;

- an "alkoxy radicaf' is an alkyl-oxy radical for which the alkyl radical is a linear or branched C1-C16, preferentially C-i-Cs, hydrocarbon radical;- The expression "at least one" is equivalent to "one or more"; and

- The expression "inclusively" for a range of concentrations means that the limits of the range form part of the interval defined.

[0012] i) Compounds of formula (I)

[0013] According to a specific embodiment of the invention, the dibenzylidene alditol compound(s), of formula (I), and also their optical or geometrical isomers, and their organic or inorganic acid or base salts, and their solvates, such as hydrates: ) in which formula (I):

* R ¹ to R' ⁵ , which are 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) -0-R _a , iii) -C(0)-0-R _b or -0-C(0)-R _b , iv) -NR _c R _d and v) - C(0)-NR _c RdOr -N(R _c )-C(0)-R , with:

- R _a representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, an aryl(Ci-C4)alkyl group, such as benzyl, or a (C3-C8)cycloalkyl group, such as cyclohexyl;

- R representing a hydrogen atom or a (Ci-C4)alkyl group;

- R _c and R _d , which are identical or different, representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, or a (C3-C8)cycloalkyl group, such as cyclohexyl; two adjacent Ri to R' ₅ radicals can also form, together with the carbon atoms which carry them, an unsaturated (Cs-Cs) ring, such as benzo;

* R represent a radical chosen from i) -Xi; ii) -C(0)-Xi; iii) -C(0)-0-Xi; iv) -C(O)- N(Rc)-Xi; with Xi representing a) a (C4-C8)cycloalkyl group, such as cyclohexyl; or b) a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 6 to 24 carbon atoms (particularly from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atom), 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 -O-C(O)-, -C(0)-0-, -C(0)-N(R _c )- or -N(Rc)-C(0)-, and/or

- optionally substituted by one or more halogen atoms or groups, which are identical or different, chosen from: -0-R _a , -C(0)-0-R _b , -NR _c R _d and (C4-C8)cycloalkyl with R _a and R _b as defined above; preferably, R _a and R _b represent a (Ci-C4)alkyl group, such as methyl.

[0014] In particular, the compounds of formula (I) of the invention are of formula (la), and also their organic or inorganic acid or base salts, and their solvates, such as hydrates:

[Chem. 3]

Formula (la) with R and R ¹ to R' ⁵ as defined above.

Preferably, the compounds of formula (I) or (la) of the invention are such that R ¹ is identical to R' ¹ , R ² is identical to R' ² , R ³ is identical to R' ³ , R ⁴ is identical to R' ⁴ and R ⁵ is identical to R' ⁵ .

According to a specific embodiment of the invention, the compounds of formula (I) or (la) are such that the R ¹ to R' ⁵ radicals, which are identical or different, represent i) a hydrogen atom or ii) a (Ci-Ce)alkyl group; iii) an -0-R _a group or iv) a -C(0)-0-R _b group with R _a and R as defined above; preferably, R _a represents a hydrogen atom, a (Ci-C ₄ )alkyl group or a benzyl group; and R _b represents a hydrogen atom or a (Ci-C ₄ )alkyl group.

[0015] According to a specific embodiment of the invention, the compounds of formula (I) or (la) are such that R is as defined above and Xi preferably represents a) a (C ₄ -C ₈ )cycloalkyl radical, b) a saturated or unsaturated and linear or branched C ₁₀ -C ₂₄ hydrocarbon chain, said chain optionally being interrupted by one or more heteroatoms or divalent radicals chosen from -0-, -N(R _C )-, -C(O)- and their combinations, such as -O-C(O)-, -C(0)-0-, -C(0)-N(R _c )- or -N(R _C )- C(O)-, and/or said chain optionally being substituted by one or more identical or different radicals chosen from the -0-R _a or -C(0)-0-R _b radicals with R _a representing a (Ci-C ₄ )alkyl group and R _b representing a (Ci-C ₄ )alkyl group.

[0016] In particular, the compounds of formula (I) or (la) of the invention are such that R ¹ to R' ⁵ , which are identical or different, represent a hydrogen atom or a group chosen from (Ci-Ce)alkyl or -0-R _a with R _a representing a hydrogen atom or (Ci-C ₄ )alkyl group, preferably R ¹ to R' ⁵ represent a hydrogen atom. [0017] In particular, the compounds of formula (I) or (la) of the invention are such that R _b represents a hydrogen atom or a (Ci-C ₄ )alkyl group; more preferentially, R _b represents a (Ci-C ₄ )alkyl group.

[0018] In particular, the compounds of formula (I) or (la) of the invention are such that R _c and R _d , which are identical or different, represent a (Ci-C ₄ )alkyl group. [0019] In particular, the compounds of formula (I) or (la) of the invention are such that R is as defined above, preferably represents X-i.

[0020] According to another specific embodiment of the invention, the compounds of formula (I) or (la) of the invention are such that R represents a -C(0)-Xi radical with Xi preferably representing a saturated or unsaturated and linear or branched C10-C24 hydrocarbon chain, preferably a linear or branched C10-C24 hydrocarbon chain.

[0021] In particular, the compounds of formula (I) or (la) of the invention are such that Xi represents a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms, said chain optionally being interrupted by one or more heteroatoms or divalent radicals chosen from -0-, -N(R _C )-, -C(O)- and their combinations, such as -O-C(O)-, - C(0)-0-, -C(0)-N(Rc)- or -N(R _c )-C(0)-, and/or said chain optionally being substituted by one or more identical or different radicals chosen from -0-R _a or - C(0)-0-R _b radicals with R _a representing a (Ci-C4)alkyl group and R _b representing a (Ci-C4)alkyl group.

[0022] More preferentially, the compounds of formula (I) or (la) of the invention are such that Xi represents a saturated or unsaturated and linear or branched hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms.

[0023] According to a specific embodiment of the invention, the compounds of formula (I) or (la) are such that R ¹ to R' ⁵ are identical. More particularly, the compounds of formula (I) or (la) of the invention are such that R ¹ to R ⁵ and R' ¹ to R' ⁵ represent a hydrogen atom or a linear or branched (Ci-C4)alkyl group. More preferentially still, the compounds of formula (I) or (la) of the invention are such that R ¹ to R' ⁵ represent a hydrogen atom.

[0024] According to a specific embodiment of the invention, the compounds of formula (I) or (la) are such that R ¹ to R' ⁵ represent a hydrogen atom and R represents a -C(0)-Xi radical with Xi denoting a hydrocarbon chain as defined above and in particular with Xi denoting a linear or branched C10-C24 hydrocarbon chain.

[0025] More preferentially, the compounds of formula (I) of the invention are chosen from those of following formula (1-1), and also its optical or geometrical isomers, and its solvates, such as hydrates:

[Chem. 4]

Formula (1-1) with Xi as defined above.

[0026] More preferentially still, the compounds of formula (I), (1-1) or (la) of the invention are chosen from those of following formula (I'a), and also its geometrical isomers, and solvates, such as hydrates:

[Chem. 5]

Formula (I'a) with Xi as defined above.

[0027] According to one embodiment, the compounds of formula (I), (1-1), (la) or (I'a) of the invention are such that Xi is as defined above, and preferentially Xi represents a linear or branched, preferably linear, hydrocarbon chain comprising from 1 to 3 unsaturations, in particular 1 insaturation, and comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms. According to a specific embodiment, the compounds of formula (I), (1-1), (la) or (I'a) of the invention are such that Xi is chosen from the following linear alkenyl groups: -(CFl2)m-CFI=CFI-(CFl2)n-FI with m and n, which are identical or different, preferably identical, representing an integer of between 0 and 20 inclusively, it being understood that the sum of n + m is of between 8 and 20 inclusively, preferably n + m is of between 10 and 18 inclusively and more preferentially of between 12 and 16 inclusively, such as 14. More preferentially, m = n. [0028] According to a specific embodiment, the compounds of formula (I), (1-1), (la) or (I'a) of the invention are such that Xi represents a saturated, linear or branched, hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms. According to this embodiment, Xi represents a -(ChhVCH- R1R2 chain with Ri and R2, which are identical or different, representing a hydrogen atom or a (Ci-Ce)alkyl group, such as methyl, and p representing an integer of inclusively between 9 and 21, preferably between 11 and 19, more particularly between 13 and 17, such as 14 or 15. [0029] According to another specific embodiment, the compounds of formula (I), (I-

1), (la) or (I'a) of the invention are such that Xi represents an unsaturated, linear or branched (preferably linear), hydrocarbon chain comprising from 10 to 22 carbon atoms, preferentially from 12 to 20 carbon atoms, more preferentially from 14 to 18, such as 17, carbon atoms. [0030] More particularly, the compounds of formula (I) of the invention are chosen from the following compounds (1) to (3):

[Chem. 6]

[Chem. 7]

Compounds (1) to (3), and also their optical or geometrical isomers, and their solvates, such as hydrates.

[0031] More particularly still, the compounds of formula (I) of the invention are chosen from the following compounds (1a) to (3a):

[Chem. 8]

[Chem. 9]

[0032] Compounds (1a) to (3a), and also their geometrical isomers, and their solvates, such as hydrates.

[0033] Process for the preparation of the compounds of formula ( I )

[0034] Another subject-matter of the invention is a process for the preparation of the compounds of formula (I) for which R ¹ = R' ¹ , R ² = R' ² , R ³ = R' ³ , R ⁴ = R' ⁴ and R ⁵ = R' ⁵ comprising a first stage in which the alditol (A), which can be in the enantiomeric (D or L) or racemic form, is reacted with at least 2 molar equivalents of aldehyde (B) in a solvent, preferably a polar protic solvent, such as water, in the presence of a catalyst chosen in particular from organic or inorganic acids, such as hydrochloric acid or para-toluenesulfonic acid, and preferably the medium is heated to a temperature of inclusively between 30°C and 80°C, in particular of inclusively between 40°C and 70°C, for a period of time preferentially of between 30 minutes and 2 days; after cooling the medium down to ambient temperature (25°C), the compound (C) can be precipitated and isolated and is subjected:

* Route A: to a (thio)esterification reaction in order to result in the compounds of formula (G) of the invention; this (thio)esterification stage can be carried out by the chemical route, for example by reaction with a (thio)acid Xi-C(X)-OH in acid catalysis, or also by a trans(thio)esterification reaction with a (thio)ester, such as X-i- C(X)-0-R3, with R3 representing a (Ci-C ₄ )alkyl group, such as methyl, preferably in acid catalysis, or also by reaction of (C) with a (thio)acid halide Xi-C(X)-Hal with Xi as defined above and Hal representing a halogen atom, such as chlorine or iodine, preferably chloride: Xi-C(0)-Cl, or by any other (thio)esterification method, such as, for example, those described in Advanced Organic Chemistry, 6 ^th Ed., Jerry March, from Wiley Interscience (see in particular p. 16, and p. 61 to 63); This (thio)esterification reaction can in particular be carried out by the biocatalytic route with a supported or unsupported lipase in a solvent, preferably a polar aprotic solvent, such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran or methyltetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification of (C) to give (G) is carried out with a supported lipase, which makes possible the recycling of the enzyme on conclusion of the reaction; or

* Route B: to the synthesis of a (thio)carbonate in order to result in the compounds (I") of the invention; this stage can be carried out by the chemical route, for example by the reaction with an activator composed of a (Ci-Ce)alkyl 1 ,3-dicarbonyl derivative in the presence of magnesium perchlorate, or with a 4,5-dichloro-6-oxopyridazin- 1(6/-/)-carboxylate derivative in the presence of a base, such as potassium tert- butoxide, or, for example, by any method described in Advanced Organic Chemistry, 6 ^th Ed., Jerry March, from Wiley Interscience (see in particular pp. 10, 16, 19 and 58).

* Route C: to the synthesis of a (thio)carbamate or (thio)urethane in order to result in the compounds (G") of the invention; this stage can be carried out by the chemical route, for example by the reaction with a C1-C6 alkyl iso(thio)cyanate, obtained by the treatment of an aliphatic alcohol with a phosphine, such as triphenylphosphine/2,3- dichloro-5,6-dicyanobenzoquinone/Bu ₄ NOCN, or, for example, by any method described in Advanced Organic Chemistry, 6 ^th Ed., Jerry March, from Wiley Interscience (see in particular pp. 8, 10, 16 and 17).

* Route D: to the synthesis of an ether oxide in order to result in the compounds (I"") of the invention; this stage can be carried out by the chemical route, for example by the reaction with a halide X-i-Hal, for example the alkyl iodide Xi I, in the presence of a strong base, such as a reducing metal (Li, Na, K) or a sodium or potassium hydride, or also by reaction of (C) with an alcohol, of XiOH type, in the presence of an acid, preferably an inorganic acid, such as sulfuric acid, with removal of water, or by reaction of (C) with an organomagnesium compound of R-MgHal type, followed by condensation with a halide Xi-Hal as defined above, or by any method described in Advanced Organic Chemistry, 6 ^th Ed., Jerry March, from Wiley Interscience (see, in particular pp. 8 and 10).

[0035] The alditols (A) denote in particular xylitol or ribitol.

[Chem. 10]

[0036] Another subject-matter of the invention is a process for the preparation of the compounds of formula (I) for which R ¹ is different from R' ¹ , and/or R ² is different from R' ² , and/or R ³ is different from R' ³ , and/or R ⁴ is different from R' ⁴ and/or R ⁵ is different from R' ⁵ comprising a first stage 1 ) in which the alditol (A) as defined above is reacted with a molar equivalent of aldehyde (B) as defined above in a solvent, preferably a polar protic solvent, such as water, in the presence of a catalyst chosen in particular from organic or inorganic acids, such as hydrochloric acid or para-toluenesulfonic acid, and preferably the medium is heated to a temperature of inclusively between 30°C and 80°C, in particular of inclusively between 40°C and 70°C, for a period of time preferentially of between 30 minutes and 2 days; after cooling the medium down to ambient temperature (25°C), followed 2) by the addition of at least one molar equivalent of aldehyde (B') under the same conditions as in stage 1) with (B) to result in the compound (Cb); said compound (Cb) can be precipitated and isolated and is subjected:

* Route A': to a (thio)esterification reaction in order to result in the compounds of formula (I'b) of the invention; this (thio)esterification stage can be carried out by the chemical route, for example by reaction with a (thio)acid Xi-C(X)-OH in acid catalysis, or also by a trans(thio)esterification reaction with a (thio)ester, such as X-i- C(X)-0-R3, with R3 representing a (Ci-C ₄ )alkyl group, such as methyl, preferably in acid catalysis, or also by reaction of (Cb) with a (thio)acid halide Xi-C(X)-Hal with Xi as defined above and Hal representing a halogen atom, such as chlorine or iodine, preferably chloride: Xi-C(0)-Cl, or by any (thio)esterification method as mentioned above;

* This (thio)esterification reaction is in particular carried out by the biocatalytic route with a supported or unsupported lipase in a solvent, preferably a polar aprotic solvent, such as, for example, acetonitrile, ethyl acetate, isopropyl acetate, tetrahydrofuran or methyltetrahydrofuran, in the presence of an enzyme; in particular, the (thio)esterification of (Cb) to give (I'b) is carried out with a supported lipase, which makes possible the recycling of the enzyme on conclusion of the reaction; or

* Route B': to the synthesis of a (thio)carbonate in order to result in the compounds (l"b) of the invention; this stage can be carried out by the chemical route, for example by the reaction with an activator composed of a (Ci-Ce)alkyl 1 ,3-dicarbonyl derivative in the presence of magnesium perchlorate, or with a 4,5-dichloro-6- oxopyridazin-1(6/-/)-carboxylate derivative in the presence of a base, such as potassium tert- butoxide, or, for example, by any method described in Advanced Organic Chemistry, 6 ^th Ed., Jerry March, from Wiley Interscience (see in particular pp. 10, 16, 19 and 58).

* Route C: to the synthesis of a (thio)carbamate or (thio)urethane in order to result in the compounds (l'"b) of the invention; this stage can be carried out by the chemical route, for example by the reaction with a C ₁ -C ₆ alkyl iso(thio)cyanate, obtained by the treatment of an aliphatic alcohol with a phosphine, such as triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu ₄ NOCN, or, for example, by any method described in Advanced Organic Chemistry, 6 ^th Ed., Jerry March, from Wiley Interscience (see in particular pp. 8, 10, 16 and 17).

* Route D': to the synthesis of an ether oxide in order to result in the compounds (l""b) of the invention; this stage can be carried out by the chemical route, for example by the reaction with a halide Xi-Hal, for example the alkyl iodide Xi I, in the presence of a strong base, such as a reducing metal (Li, Na, K) or a sodium or potassium hydride, or also by reaction of (Cb) with an alcohol, of X ₁ OH type, in the presence of an acid, preferably an inorganic acid, such as sulfuric acid, or by reaction of (Cb) with an organomagnesium compound of R-MgHal type, followed by condensation with a halide Xi-Hal as defined above, or by any method described in Advanced Organic Chemistry, 6 ^th Ed., Jerry March, from Wiley Interscience (see, in particular pp. 8 and 10). [Chem. 11]

[0037] The composition

[0038] Another subject-matter of the invention is a composition comprising one or more compounds of formula (I), (1-1), (la), (I'a), (1), (2), (3), (1a), (2a) or (3a) as defined above, and also their organic or inorganic acid or base salts, their optical or geometrical isomers, and their solvates, such as hydrates.

[0039] The amount of the compound(s) of formula (I), (1-1), (la), (I'a), (1), (2), (3), (1a), (2a) or (3a) of the invention present in the composition depends, of course, on the texture desired for said composition, which can range from a fluid gel to a stick, and/or on the properties desired. [0040] Preferably, the amount of compounds of formula (I), (1-1), (la), (I'a), (1), (2),

(3), (1a), (2a) or (3a) is less than or equal to 15%, more preferentially less than or equal to 10% by weight and in particular less than or equal to 8% by weight, with respect to the total weight of the cosmetic composition; it can 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, indeed even between 0.2% and 9% by weight and better still between 0.5% and 8% by weight, with respect to the total weight of the cosmetic composition.

[0041] The composition of the invention denotes in particular a cosmetic composition. Cosmetic composition is understood to mean a physiologically acceptable composition.

[0042] The term " hysiologically acceptable composition " is understood to mean a composition compatible with the keratin materials of human beings, such as the skin, in particular of the body and of the face, lips, the scalp, the hair, the eyelashes, the eyebrows and the nails.

[0043] The compounds of formula (I), (1-1), (la), (I'a), (1), (2), (3), (1a), (2a) or (3a) as defined above according to the invention make it possible to structure lipophilic media, such as fatty substances, preferably liquid fatty substances, such as oils.

[0044] ii) one or more liquid fatty substances:

[0045] According to a specific embodiment of the invention, the composition of the invention additionally comprises ii) one or more liquid fatty substances.

[0046] Preferably, the fatty substances of the invention are chosen from hydrocarbons, fatty alcohols, fatty esters, silicones and fatty ethers, or their mixtures. More particularly, the fatty substances of the invention are not (poly)oxyalkylenated.

[0047] Within the meaning of the present invention, liquid fatty substances is understood to mean fatty substances which are liquid at ambient temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 ⁵ Pa).

[0048] The liquid fatty substances of the invention exhibit in particular a viscosity of less than or equal to 2 Pa.s, more particularly of less than or equal to 1 Pa.s and more particularly still of less than or equal to 0.1 Pa.s, more preferentially of less than or equal to 0.09 Pa.s at a temperature of 25°C and at a shear rate of 1 s ¹ .

[0049] According to a specific embodiment of the invention exhibit in a viscosity of between 0.001 Pa.s and 2 Pa.s, more particularly of inclusively between 0.01 and 1 Pa.s and more particularly still of inclusively between 0.014 and 0.1 Pa.s, more preferentially of inclusively between 0.015 and 0.09 Pa s, at a temperature of 25°C and at a shear rate of 1 s ^-1 .

[0050] The term " liquid hydrocarbon " is understood to mean a hydrocarbon composed solely of carbon and hydrogen atoms which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 ⁵ Pa).

[0051] More particularly, the liquid hydrocarbons are chosen from:

- linear or branched, optionally cyclic, C6-C16 alkanes. Mention may be made, by way of examples, of hexane, undecane, dodecane, tridecane or isoparaffins, such as isohexadecane, isododecane and isodecane.

- linear or branched hydrocarbons of mineral, animal or synthetic origin of more than 16 carbon atoms, such as liquid paraffins, liquid petrolatum, polydecenes, hydrogenated polyisobutene, such as Parleam®, or squalane.

[0052] In a preferred alternative form, the liquid hydrocarbon(s) are chosen from liquid paraffins and liquid petrolatum.

[0053] The term " liquid fatty alcohof' Is understood to mean a non-glycerolated and non-oxyalkylenated fatty alcohol which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 ⁵ Pa).

[0054] Preferably, the liquid fatty alcohols of the invention comprise 8 to 30 carbon atoms, more preferentially C10-C22, more preferentially still C14-C20 and better still C16-C18 liquid fatty alcohols.

[0055] The liquid fatty alcohols of the invention can be saturated or unsaturated.

[0056] The liquid saturated fatty alcohols are preferably branched. They can optionally comprise, in their structure, at least one aromatic or non-aromatic ring. Preferably, they are acyclic.

[0057] More particularly, the liquid saturated fatty alcohols of the invention are chosen from octyldodecanol, isostearyl alcohol or 2-hexyldecanol.

[0058] According to another alternative form of the invention, the fatty substance(s) are chosen from liquid unsaturated fatty alcohols. These liquid unsaturated fatty alcohols exhibit, in their structure, at least one double or triple bond. Preferably, the fatty alcohols of the invention have, in their structure, one or more double bonds. When several double bonds are present, they are preferably 2 or 3 in number and they can be conjugated or non-conjugated.

[0059] These unsaturated fatty alcohols can be linear or branched.

[0060] They can optionally comprise, in their structure, at least one aromatic or non aromatic ring. Preferably, they are acyclic. [0061] More particularly, the liquid unsaturated fatty alcohols of the invention are chosen from oleyl alcohol, linoleyl alcohol, linolenyl alcohol or undecylenyl alcohol.

[0062] Oleyl alcohol is very particularly preferred.

[0063] The term " liquid fatty ester"' is understood to mean an ester resulting from a fatty acid and/or from a fatty alcohol which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg, i.e. 1.013 x 10 ⁵ Pa).

[0064] The esters are preferably liquid esters of saturated or unsaturated and linear or branched C1-C26 aliphatic mono- or polyacids and of saturated or unsaturated and 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.

[0065] Preferably, for the esters of monoalcohols, one at least of the alcohol or of the acid from which the esters of the invention result is branched.

[0066] Mention may be made, among the monoesters of monoacids and of monoalcohols, of ethyl palmitate, isopropyl palmitate, alkyl myristates, such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isodecyl neopentanoate, isostearyl neopentanoate and C10-C22, preferably C12-C20, alkyl (iso)stearates, such as isopropyl isostearate.

[0067] Use may also be made of esters of C4-C22 di- or tricarboxylic acids and of Ci- C22 alcohols and esters of mono-, di- or tricarboxylic acids and of non-sugar di-, tri-, tetra- or pentahydroxy C4-C26 alcohols.

[0068] 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, triisostearyl citrate, glyceryl trilactate, glyceryl trioctanoate, trioctyldodecyl citrate, trioleyl citrate, neopentyl glycol diheptanoate or diethylene glycol diisononanoate.

[0069] The composition can also comprise, as liquid fatty ester, sugar esters and diesters of C6-C30, preferably C12-C22, fatty acids. It should be remembered that the term "sugar" is understood to mean oxygen-carrying hydrocarbon compounds which have several alcohol functional groups, with or without an aldehyde or ketone functional group, and which comprise at least 4 carbon atoms. These sugars can be monosaccharides, oligosaccharides or polysaccharides.

[0070] Mention may be made, as suitable sugars, for example, of sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose, and their derivatives, in particular alkylated derivatives, such as methylated derivatives, for example methylglucose. [0071 ] The esters of sugars and of fatty acids can in particular be chosen from the group consisting of the esters and mixtures of esters of sugars described above and of saturated or unsaturated and linear or branched C6-C30, preferably C12- C22, fatty acids. If they are unsaturated, these compounds can comprise one to three conjugated or non-conjugated carbon-carbon double bonds.

[0072] The esters according to this alternative form can also be chosen from mono-, di-, tri- and tetraesters, polyesters and their mixtures.

[0073] These esters can, for example, be oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates or arachidonates, or their mixtures, such as, in particular, mixed oleate/palmitate, oleate/stearate and palmitate/stearate esters.

[0074] More particularly, use is made of mono- and diesters and in particular of mono- or dioleate, -stearate, -behenate, -oleate/palmitate, -linoleate, -linolenate or -oleate/stearate of sucrose, glucose or methylglucose.

[0075] Mention may be made, by way of example, of the product sold under the name Glucate® DO by Amerchol, which is a methylglucose dioleate.

[0076] Finally, use may also be made of natural or synthetic esters of mono-, di- or triacids with glycerol.

[0077] Mention may be made, among these, of vegetable oils.

[0078] Mention may be made, as oils of vegetable origin or synthetic triglycerides which can be used in the composition of the invention as liquid fatty esters, for example, of:

- triglyceride oils of vegetable or synthetic origin, such as liquid triglycerides of fatty acids comprising from 6 to 30 carbon atoms, such as triglycerides of heptanoic or octanoic acids, or also, for example, sunflower oil, maize oil, soybean oil, pumpkin oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, such as those sold by Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by Dynamit Nobel, jojoba oil or shea butter oil.

[0079] Preferably, liquid fatty esters resulting from monoalcohols will be used as esters according to the invention.

[0080] Isopropyl myristate or isopropyl palmitate are preferred.

[0081] The liquid fatty ethers are chosen from liquid dialkyl ethers, such as dicaprylyl ether.

[0082] The compositions of the invention contain ii) one or more fatty substances which are liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 x 10 ⁵ Pa). These liquid fatty substances can thus be of natural or synthetic origin.

[0083] 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 liquid paraffins, liquid petrolatum, polydecenes or hydrogenated polyisobutylene, such as squalane, preferably squalane, b) liquid saturated or unsaturated and linear or branched fatty alcohols, such as octyldodecanol, and c) vegetable oils, such as olive oil, wheat germ oil, maize oil, sunflower oil, shea oil, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy oil, red kuri squash oil, sesame oil, pumpkin oil, avocado oil, hazelnut oil, grape seed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, jojoba oil, palm oil or calophyllum oil, preferably olive oil.

[0084] Preferably, the compound(s) of formula (I), (1-1), (la) or (l'a) of the invention make it possible to structure ii) the cosmetic liquid fatty substances normally employed, and in particular the liquid fatty substances as defined above.

[0085] The liquid fatty substance(s) ii) used in the composition according to the present invention can 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 more preferentially still in an amount varying from 10% to 99% by weight, with respect to the total weight of the composition.

[0086] The compounds of formula (I), (1-1 ), (la) or (I'a) according to the invention can also find an application in the field of the industry of paints, varnishes and adhesives, as structuring or thickening, indeed even gelling, agent.

[0087] Said medium can comprise one or more additional ingredients, distinct from the compounds of formula (I), (1-1), (la) or (I'a) as defined above.

[0088] Thus, the composition of the invention can comprise one or more organic solvents.

[0089] The term " organic solvent' is understood to mean an organic substance capable of dissolving another substance without chemically modifying it.

[0090] Mention may be made, as organic solvent, for example, of a) C2-C6 alkanols, such as ethanol and isopropanol; b) polyols miscible with water at ambient temperature (25°C) chosen in particular from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerol, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol or diglycerol; c) polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether or diethylene glycol monomethyl ether; and also d) aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and their mixtures.

[0091] According to a specific embodiment, the composition additionally comprises one or more polyols chosen in particular from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerol.

[0092] The composition of the invention can comprise additional compounds, such as cosmetic active principles, such as humectant agents, moisturizing agents, anti-ageing active principles, sunscreens, vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, surfactants, antioxidants, cosmetic active principles, propellants, ceramides, additional film-film agents, polymers or their mixtures.

[0093] Of course, a person skilled in the art will take care to choose this or these optional additional ingredients and/or their amounts so that the advantageous properties of the composition according to the invention are not, or not substantially, detrimentally affected by the envisaged addition.

[0094] The composition according to the invention can in particular be provided in the form:

- of a make-up product, in particular for the skin of the face, the body or the lips or the eyelashes, such as a lipstick, concealer, foundation, product for concealing imperfections or stick;

- of an aftershave gel or lotion; shaving product, in particular in stick form;

- of a deodorant or of an antiperspirant, such as a stick;

- in the form of a body hygiene composition, such as a shower gel or a shampoo, preferably in stick form;

- of a solid composition such as a soap or a cleansing bar, preferably in stick form;

- of a composition for caring for or cleaning the skin, preferably in stick form.

[0095] iii) one or more colouring agents:

[0096] According to a specific embodiment of the invention, the composition additionally comprises one or more colouring agents chosen in particular from pigments and dyes, preferably direct dyes.

[0097] According to a more specific embodiment of the invention, the composition comprises one or more colouring agents chosen from pulverulent colourants, such as pigments, fillers, pearlescent agents and glitter, and/or fat-soluble or water-soluble dyes. [0098] According to one embodiment of the invention, the composition comprises one or more colouring agents chosen from pigments, direct dyes and their mixtures.

[0099] Preferably, the composition according to the invention comprises one or more pigments.

[0100] The term " igment' is understood to mean any pigment, of synthetic or natural origin, which gives colour to keratin materials. 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%.

[0101 ] They are white or coloured solid particles which are naturally insoluble in the liquid hydrophilic and lipophilic phases usually employed in cosmetics or which are rendered insoluble by formulation in the form of a lake, if appropriate. More particularly, the pigments have little or no solubility in aqueous/alcoholic media.

[0102] The pigments which can be used are chosen in particular from the organic and/or inorganic pigments known in the art, in particular those which are described in the Kirk-Othmer 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, "Pigments, Organic", 2005, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a20371 et ibid., "Pigments, Inorganic, 1. General", 2009, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a20_243.pub3.

[0103] These pigments can be provided in the pigment powder or paste form. They can be coated or uncoated.

[0104] The pigments can, for example, be chosen from inorganic pigments, organic pigments, lakes, special effect pigments, such as pearlescent agents or glitter, and their mixtures.

[0105] The pigment can be an inorganic pigment. The term "inorganic pigment" is understood to mean any pigment which satisfies the definition of Ullmann’s Encyclopedia in the chapter "Pigments, Inorganic". Mention may be made, among the inorganic pigments of use in the present invention, of iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.

[0106] The pigment can be an organic pigment. The term "organic pigment" is understood to mean any pigment which satisfies the definition of Ullmann’s Encyclopedia in the chapter "Pigments, Organic". The organic pigment can in particular be chosen from nitroso, nitro, azo, xanthene, quinoline, anthraquinone, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane or quinophthalone compounds.

[0107] In particular, the white or coloured organic pigments can be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Colour Index under the references Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Colour Index under the references Cl 11680, 11710, 15985,

19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Colour Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Colour Index under the references Cl 11725, 15510, 45370,

71105, the red pigments codified in the Colour Index under the references Cl 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 indole or phenol derivatives as are described in Patent FR 2679771.

[0108] According to a specific embodiment of the invention, use is made, as pigment(s), of pigment pastes of organic pigments, such as the products sold by 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);

- Cosmenyl Green GG: Pigment Green 7 (Cl 74260);

- Cosmenyl Black R: Pigment Black 7 (Cl 77266).

[0109] The pigments in accordance with the invention can also be in the form of composite pigments, such as are described in Patent EP 1 184426. These composite pigments can be composed in particular of particles comprising:

- an inorganic core,

- at least one binder providing the fixing of the organic pigments to the core, and

- at least one organic pigment at least partially covering the core.

[0110] The term "lake" is understood to mean dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use. The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium. Mention may be made, among the organic dyes, of cochineal carmine. [0111] Mention may be made, as examples of lakes, of the products known under the following names: D & C Red 21 (Cl 45380), D & C Orange 5 (Cl 45370), D & C Red 27 (Cl 45410), D & C Orange 10 (Cl 45425), D & C Red 3 (Cl 45430), D & C Red 7 (Cl 15850:1), D & C Red 4 (Cl 15510), D & C Red 33 (Cl 17200), D & C Yellow 5 (Cl 19140), D & C Yellow 6 (Cl 15985), D & C Green (Cl 61570), D & C Yellow 10 (Cl 77002), D & C Green 3 (Cl 42053) or D & C Blue 1 (Cl 42090).

[0112] The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.

[0113] Mention may be made, among the dyes, of cochineal carmine. Mention may also be made of the dyes known under the following names: D & C Red 21 (Cl 45380), D & C Orange 5 (Cl 45370), D & C Red 27 (Cl 45410), D & C Orange 10 (Cl 45425), D & C Red 3 (Cl 45430), D & C Red 4 (Cl 15510), D & C Red 33 (Cl 17200), D & C Yellow 5 (Cl 19140), D & C Yellow 6 (Cl 15985), D & C Green (Cl 61570), D & C Yellow 10 (Cl 77002), D & C Green 3 (Cl 42053) or D & C Blue 1 (Cl 42090).

[0114] Mention may be made, as an example of a lake, of the product known under the following name: D&C Red 7 (Cl 15850:1).

[0115] The pigment(s) can also be special effect pigments.

[0116] The term " special effect pigments " is understood to mean pigments which create in a general way a coloured appearance (characterized by a certain shade, a certain vividness and a certain brightness) which is non-uniform and which changes as a function of the conditions of observation (light, temperature, angles of observation, and the like). They thereby contrast with coloured pigments, which provide a conventional uniform opaque, semi-transparent or transparent shade.

[0117] Several types of special effect pigments exist: those having a low refractive index, such as fluorescent, photochromic or thermochromic pigments, and those having a higher refractive index, such as pearlescent agents or glitter.

[0118] Mention may be made, as examples of special effect pigments, of pearlescent pigments, such as titanium oxide-coated mica covered with an iron oxide, mica covered with an iron oxide, mica covered with bismuth oxychloride, titanium oxide-coated mica covered with chromium oxide, titanium oxide-coated mica covered with an organic dye, in particular of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride. They can also be mica particles, at the surface of which are superimposed at least two successive layers of metal oxides and/or of organic dyestuffs. [0119] The pearlescent agents can more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or glint.

[0120] Mention may in particular be made, by way of illustration of the pearlescent agents which can be employed in the context of the present invention, of gold- coloured pearlescent agents sold in particular by Engelhard under the names Gold 222C (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch Gold 233X (Cloisonne); bronze pearlescent agents sold in particular by Merck under the names Bronze Fine (17384) (Colorona) and Bronze (17353) (Colorona), by Eckart under the name Prestige Bronze and by Engelhard under the name Super Bronze (Cloisonne); orange pearlescent agents sold in particular by Engelhard under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by Merck under the names Passion Orange (Colorona) and Matte Orange (17449) (Microna); brown-coloured pearlescent agents sold in particular by Engelhard under the names Nu-Antique Copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); pearlescent agents with a copper glint sold in particular by Engelhard under the name Copper 340A (Timica) and by Eckart under the name Prestige Copper; pearlescent agents with a red glint sold in particular by Merck under the name Sienna Fine (17386) (Colorona); pearlescent agents with a yellow glint sold in particular by Engelhard under the name Yellow (4502) (Chromalite); red-coloured pearlescent agents with a gold glint sold in particular by Engelhard under the name Sunstone G012 (Gemtone); black pearlescent agents with a gold glint sold in particular by Engelhard under the name Nu-Antique Bronze 240 AB (Timica); blue pearlescent agents sold in particular by Merck under the names Matte Blue (17433) (Microna) and Dark Blue (117324) (Colorona); white pearlescent agents with a silvery glint sold in particular by Merck under the name Xirona Silver; and the golden green pinkish orangey pearlescent agents sold in particular by Merck under the name Indian Summer (Xirona), and their mixtures.

[0121] In addition to pearlescent agents on a mica support, multilayer pigments based on synthetic substrates, such as alumina, silica, sodium calcium borosilicate or calcium aluminium borosilicate, and aluminium, can be envisaged.

[0122] Mention may also be made of pigments with an interference effect which are not attached to a substrate, such as liquid crystals (Flelicones HC from Wacker) or interference holographic glitter (Geometric Pigments or Spectra f/x from Spectratek). Special effect pigments also comprise fluorescent pigments, whether these are substances which are fluorescent in daylight or which produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, for example sold by Quantum Dots Corporation. [0123] The variety of the pigments which can be used in the present invention makes it possible to obtain a rich palette of colours and also specific optical effects, such as metallic effects or interference effects.

[0124] The size of the pigment used in the cosmetic composition according to the present invention is generally between 10 nm and 200 pm, preferably between 20 nm and 80 pm and more preferentially between 30 nm and 50 pm.

[0125] The pigments can be dispersed in the product by virtue of a dispersing agent.

[0126] The term " dispersing agent' is understood to mean a compound which makes it possible to protect the dispersed particles from their agglomeration or flocculation. This dispersing agent can 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 become attached physically or chemically to the surface of the pigments. These dispersing agents additionally exhibit at least one functional group compatible with or soluble in the continuous medium. Said agent can be charged: it can be anionic, cationic, zwitterionic or neutral.

[0127] According to a specific embodiment of the invention, the dispersing agents used are chosen from esters of 12-hydroxystearic acid, more particularly, and of Ce to C20 fatty acid and of polyol, for instance glycerol or diglycerol, such as poly( 12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name of Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name), sold under the reference Dehymyls PGPH by Henkel, or also polyhydroxystearic acid, such as the product sold under the reference Arlacel P100 by Uniqema, and their mixtures.

[0128] Mention may be made, as other dispersing agents which can be used in the compositions of the invention, of quaternary ammonium derivatives of polycondensed fatty acids, such as Solsperse 17000, sold by Avecia, and polydimethylsiloxane/oxypropylene mixtures, such as those sold by Dow Corning under the references DC2-5185 and DC2-5225 C.

[0129] The pigments used in the cosmetic composition according to the invention can be surface-treated with an organic agent. Thus, the pigments surface-treated beforehand of use in the context of the invention are pigments which have been completely or partially subjected to a surface treatment of chemical, electronic, electrochemical, mechanochemical or mechanical nature with an organic agent, such as those which are described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, pages 53-64, before being dispersed in the composition in accordance with the invention. These organic agents can, for example, be chosen from amino acids; waxes, for example carnauba 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 polymethyl methacrylates; polymers and copolymers containing acrylate units; proteins; alkanolamines; silicone compounds, for example silicones, polydimethylsiloxanes, alkoxysilanes, alkylsilanes or siloxysilicates; organofluorine compounds, for example perfluoroalkyl ethers; fluorosilicone compounds.

[0130] The surface-treated pigments of use in the cosmetic composition according to the invention may also have been treated with a mixture of these compounds and/or may have undergone several surface treatments.

[0131] The surface-treated pigments of use in the context of the present invention can be prepared according to surface-treatment techniques well known to a person skilled in the art or found as such commercially.

[0132] Preferably, the surface-treated pigments are covered with an organic layer.

[0133] 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 surface agent or creation of a covalent bond between the surface agent and the pigments. The surface treatment can thus be carried out, for example, by chemical reaction of a surface agent with the surface of the pigments and creation of a covalent bond between the surface agent and the pigments or the fillers. This method is described in particular in Patent US 4578266.

[0134] Preferably, use will be made of an organic agent covalently bonded to the pigments.

[0135] The agent for the surface treatment can 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 more preferentially still from 1% to 10% by weight.

[0136] Preferably, the surface treatments of the pigments are chosen from the following treatments:

- a PEG-silicone treatment, such as the AQ surface treatment sold by LCW;

- a chitosan treatment, such as the CTS surface treatment sold by LCW;

- a triethoxycaprylylsilane treatment, such as the AS surface treatment sold by LCW;

- a methicone treatment, such the SI surface treatment sold by LCW - a dimethicone treatment, such as the Covasil 3.05 surface treatment sold by LCW;

- a dimethicone/trimethylsiloxysilicate treatment, such as the Covasil 4.05 surface treatment sold by LCW;

- a lauroyl lysine treatment, such as the LL surface treatment sold by LCW

- a lauroyl lysine dimethicone treatment, such as the LL/SI surface treatment sold by LCW;

- a magnesium myristate treatment, such as the MM surface treatment sold by LCW;

- an aluminium dimyristate treatment, such as the Ml surface treatment sold by Miyoshi;

- a perfluoropolymethylisopropyl ether treatment, such as the FHC surface treatment sold by LCW;

- an isostearyl sebacate treatment, such as the HS surface treatment sold by Miyoshi;

- a disodium stearoyl glutamate treatment, such as the NAI surface treatment sold by Miyoshi;

- a dimethicone/disodium stearoyl glutamate treatment, such as the SA/NAI surface treatment sold by Miyoshi;

- a perfluoroalkyl phosphate treatment, such as the PF surface treatment sold by Daito;

- an acrylate/dimethicone copolymer and perfluoroalkyl phosphate treatment, such as the FSA surface treatment sold by Daito;

- a polymethylhydrosiloxane/perfluoroalkyl phosphate treatment, such as the FS01 surface treatment sold by Daito;

- a lauroyl lysine/aluminium tristearate treatment, such as the LL-StAI surface treatment sold by Daito;

- an octyltriethylsilane treatment, such as the OTS surface treatment sold by Daito;

- an octyltriethylsilane/perfluoroalkyl phosphate treatment, such as the FOTS surface treatment sold by Daito;

- an acrylate/dimethicone copolymer treatment, such as the ASC surface treatment sold by Daito;

- an isopropyl titanium triisostearate treatment, such as the ITT surface treatment sold by Daito;

- a microcrystalline cellulose and carboxymethyl cellulose treatment, such as the AC surface treatment sold by Daito;

- a cellulose treatment, such as the C2 surface treatment sold by Daito

- an acrylate copolymer treatment, such as the APD surface treatment sold by Daito; - a perfluoroalkyl phosphate/isopropyl titanium triisostearate treatment, such as the PF + ITT surface treatment sold by Daito.

[0137] The composition in accordance with the present invention can furthermore comprise one or more pigments which are not surface-treated.

[0138] According to a specific embodiment of the invention, the pigment(s) are inorganic pigments.

[0139] According to another specific embodiment of the invention, the pigment(s) are chosen from pearlescent agents.

[0140] According to a specific embodiment of the invention, the dispersing agent is present with organic pigments in the composition of the invention in particulate form of submicronic size.

[0141] The term " submicronic " is understood to mean pigments, the particle size of which has been micronized by a micronization method and the mean particle size of which is less than a micrometre (mίp), in particular between 0.1 and 0.9 mhp and preferably between 0.2 and 0.6 mGh.

[0142] According to one embodiment, the dispersing agent and the pigment(s) are present in a (dispersing agentpigment) amount of between 0.5: 1 and 2: 1 , particularly between 0.75: 1 and 1.5: 1 or better still between 0.8: 1 and 1.2: 1.

[0143] According to a specific embodiment, the dispersing agent is suitable for dispersing the pigments and is compatible with a formulation curable by condensation.

[0144] The term " compatible " is understood to mean, for example, that said dispersing agent is miscible in the oily phase of the composition or of the dispersion containing the pigment(s), and it does not delay or reduce the curing. The dispersing agent is preferably cationic.

[0145] The dispersing agent(s) can thus have a silicone backbone, such as silicone polyether and dispersing agents of aminosilicone type. Mention may be made, among the suitable dispersing agents, of:

- aminosilicones, i.e. silicones comprising one or more amino groups, such as those sold 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 , sold by Genesee Polymers,

- silicone acrylates, such as Tego® RC 902, Tego® RC 922, Tego® RC 1041 and Tego® RC 1043, sold by Evonik,

- polydimethylsiloxane (PDMS) silicones having carboxyl groups, such as X- 22162 and X-22370, sold by Shin-Etsu, epoxy silicones, such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682 and GP-695, sold by Genesee Polymers, orTego® RC 1401, Tego® RC 1403 and Tego® RC 1412, sold by Evonik.

[0146] According to a specific embodiment, the dispersing agent(s) are of aminosilicone type and are positively charged.

[0147] Mention may also be made of dispersing agents having chemical groups which are capable of reacting with the reactants of the oily phase and thus are capable of improving the 3D network formed from the aminosilicones. For example, dispersing agents of epoxy silicone pigments can react chemically with the aminosilicone prepolymer amino group(s) to increase the cohesion of the aminosilicone film comprising the pigment(s).

[0148] Preferably, the pigment(s) iii) of the invention are chosen from carbon black, iron oxides, in particular red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, in particular blue and purple triarylmethane pigments, such as Blue 1 Lake, azo pigments, in particular red azo pigments, such as D&C Red 7, or an alkali metal salt of Lithol Red, such as the calcium salt of Lithol Red B.

[0149] According to a specific embodiment of the invention, the amount of pigments varies from 0.5% up to 40% and preferably from 1 % to 20%, with respect to the weight of the composition and dispersion comprising them.

[0150] The composition can comprise one or more direct dye(s).

[0151] The term " direct dye " is understood to mean natural and/or synthetic dyes, other than oxidation dyes. These are dyes which will diffuse superficially over keratin materials, in particular keratin fibres.

[0152] They can be ionic or non-ionic, in particular cationic, anionic or non-ionic.

[0153] Examples of suitable direct dyes which may be mentioned comprise 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 in the form of mixtures.

[0154] According to one embodiment of the invention, the dye(s), in particular pulverulent dye(s), are present in the composition in a content of from 0.01% to 50% by weight, with respect to the weight of the composition, preferably from 0.1% to 40% by weight, indeed even from 1% to 30% by weight.

[0155] The pigments can be white or coloured, inorganic and/or organic, and interference or non-interference pigments. Mention may be made, among the inorganic pigments, of titanium dioxide, optionally surface-treated, zirconium oxide or cerium oxide, and also iron oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue. Mention may be made, among the organic pigments, of carbon black, pigments of D & C type, and lakes based on cochineal carmine and on barium, strontium, calcium or aluminium. The pearlescent pigments can be chosen from white pearlescent pigments, such as mica covered with titanium or with bismuth oxychloride, coloured pearlescent pigments, such as titanium oxide-coated mica with iron oxides, titanium oxide- coated mica with in particular ferric blue or chromium oxide or titanium oxide- coated mica with an organic pigment of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride.

[0156] The term "fillers" should be understood as meaning colourless or white, mineral or synthetic and lamellar or non-lamellar particles which are intended to give body or stiffness to the composition, and/or softness, mattness and uniformity to the make-up. The fillers can be inorganic or organic of any shape: platelet, spherical or oblong. Mention may be made of talc, mica, silica, kaolin, powders of Nylon and of polyethylene, of poly-p-alanine and of polyethylene, Teflon, lauroyllysine, starch, boron nitride, powders of tetrafluoroethylene polymers, hollow microspheres, such as Expancel (Nobel Industrie), Polytrap (Dow Corning) and silicone resin microbeads (for example, Tospearls from Toshiba), precipitated calcium carbonate, magnesium carbonate, magnesium hydrocarbonate, hydroxyapatite, hollow silica microspheres (Silica Beads from Maprecos), glass or ceramic microcapsules, or metal soaps derived from organic carboxylic acids having from 8 to 22 carbon atoms and preferably from 12 to 18 carbon atoms, for example zinc stearate, magnesium stearate or lithium stearate, zinc laurate or magnesium myristate.

[0157] The fat-soluble dyes are, for example, Sudan red, DC Red 17, DC Green 6, b- carotene, soybean oil, Sudan brown, DC Yellow 11 , DC Violet 2, DC Orange 5 or quinoline yellow. They can represent from 0.01 % to 20% of the weight of the composition and better still from 0.1% to 6%.

[0158] The water-soluble dyes are, for example, beetroot juice or methylene blue and can represent from 0.01 % to 6% of the total weight of the composition.

[0159] According to a preferred embodiment of the invention, the composition comprises i) one or more compounds of formula (I) as defined above, ii) one or more liquid fatty substances as defined above and iii) one or more pigments as defined above.

[0160] The composition according to the invention can be provided in the form of a suspension, a dispersion, in particular of oil in water, by virtue of vesicles; an oil- in-water, water-in-oil or multiple emulsion; a gel or a foam; an oily or emulsified gel; a dispersion of vesicles, in particular lipid vesicles; a two-phase or multi phase lotion; a loose, compact or cast powder; an anhydrous paste. This composition can have the appearance of a lotion, a cream, a pomade, a soft paste, an ointment, a foam, a cast or moulded solid, in particular in stick or dish form, or a compacted solid.

[0161] A person skilled in the art can choose the appropriate presentation form, and also 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.

[0162] The cosmetic composition according to the invention can be provided in the form of a product for caring for and/or making up the skin of the body or face, the lips, the nails, the eyelashes, the eyebrows and/or the hair, an antisun or self tanning product, or a hair product for caring for, treating, cleaning, conditioning, shaping, making up or colouring the hair.

[0163] It can thus be provided in the form of a make-up composition, in particular a product for the complexion, such as a foundation, a face powder or an eyeshadow; a product for the lips, such as a lipstick, a lip gloss or a lip care product; a concealer product; a blusher, a mascara or an eyeliner; a product for making up the eyebrows, a lip or eye pencil; a product for the nails, such as a nail varnish or a nail care product; a product for making up the body; a product for making up the hair (hair mascara).

[0164] It can also be provided in the form of a composition for the protection, cleaning, hygiene or care of the skin of the face, the neck, the hands or the body, in particular an anti-wrinkle composition; a moisturizing or treating composition; an antisun or artificial tanning (self-tanning) composition; a deodorant or antiperspirant composition.

[0165] It can also be provided in the form of a hair care product, in particular for colouring, form retention of the hairstyle, shaping the hair, caring for, treating or cleaning the hair, such as shampoos, gels, lotions for hairsetting, blow-drying lotions, or fixing and styling compositions, such as lacquers or sprays.

[0166] Preferably, the cosmetic composition according to the invention is provided in the form of a product for making up the body, lips, eyelashes, hair or nails, optionally having non-therapeutic care and/or treatment properties.

[0167] It is very particularly provided in the form of a lipstick or a lip gloss, a lip balm, a blusher or eyeshadow, a foundation, a tattooing product, a mascara, an eyeliner, a nail varnish, an antiperspirant, a deodorant agent, or a product for colouring or caring for the hair.

[0168] Another subject-matter of the invention is a process for the cosmetic treatment of keratin materials, such as the skin of the body or face, the lips, the nails, the hair, the eyebrows and/or the eyelashes, comprising the application, to said materials, of a composition, in particular a cosmetic composition, as defined above.

[0169] Preferably, it is a process for making up the skin, lips, eyelashes, nails, eyebrows, hair and/or lips, more preferentially a process for treating the lips, more preferentially still for making up the lips.

[0170] In particular, the composition occurs in the form of a stick preferably comprising an amount of less than 7% by weight of water, preferably of less than 5% by weight of water, more preferentially still of less than 3% by weight of water, better still of less than 1% by weight of water, with respect to the total weight of the composition; more preferentially still, the composition is anhydrous or devoid of water.

[0171] The compounds according to the invention can also find an application in the field of the industry of paints, varnishes and adhesives, as structuring or thickening, indeed even gelling, agent, preferably in the cosmetics industry.

[0172] The invention is illustrated in greater detail in the following examples.

EXAMPLES

[0173] Synthesis examples:

[0174] Synthesis of the intermediate (C): Dibenzylidene xylitol with R ¹ , R' ¹ , R ² , R' ² , R ³ , R' ³ , R ⁴ , R' ⁴ , R ⁵ and R' ⁵ representing a hydrogen atom:

[Chem. 12]:

[0175] 7 g of benzaldehyde (66 mmol) (Sigma-Aldrich) are added to a solution of 5 g of xylitol (6.58 mmol) (Sigma-Aldrich) comprising 70% of distilled water. 0.33 g of para-toluenesulfonic acid (0.2 mmol) (Sigma-Aldrich) at 10% in water is subsequently added. The reaction medium is stirred at 60°C for 1 hour and is then cooled. The expected product precipitates. The reaction medium is adjusted to pH 7 with sodium hydroxide and then the precipitate is filtered on a BOchner funnel, washed 3 times with 25 ml of distilled water and 2 times with 12.5 ml of ethanol. The solid is dried in an oven (50°C, overnight). A white solid is obtained.

[0176] The spectroscopic and spectrometric analyses are in accordance with the expected structure (C).

[0177] Example 1 : Synthesis of the mono-oleate of formula (I) with R representing -C(0)-(CH ₂ ) ₇ -CH=CH-(CH ₂ ) ₇ -CH ₃ and R ¹ , R' ¹ , R ² , R' ² , R ³ , R' ³ , R ⁴ , R' ⁴ , R ⁵ and R' ⁵ representing a hydrogen atom:

[Chem. 13]

[0178] 1 .2 g of the enzyme Candida antarctica B (Sigma Aldrich) (60% w/w with respect to the dibenzylidene xylitol derivative) are added to a solution of 2 g of dibenzylidene xylitol (6.12 mmol), 3.46 g of oleic acid (12.2 mmol) (Sigma Aldrich) and 10 g of molecular sieve (Sigma Aldrich) (500% w/w with respect to the dibenzylidene xylitol derivative) in 200 ml of methyltetrahydrofuran (Sigma Aldrich). The mixture is stirred at 60°C for 4 days and then cooled. The solution is separated from the molecular sieve and from the enzyme by centrifugation (5000 revolutions per minute, 10 minutes). The solution is concentrated to dryness on a rotary evaporator under reduced pressure. The crude product is purified on an ion-exchange resin IRA67 (2 g w/w) in dichloromethane (10V) for 1 hour. The mixture is filtered and the solution is concentrated on a rotary evaporator under reduced pressure to result in a white solid having a melting point of 105°C.

[0179] The spectroscopic analyses are in agreement with the expected structure.

[0180] Example 2: Synthesis of the monostearate of formula (I) with R representing -C(0)-(CH ₂ )i6-CH ₃ and R ¹ , R' ¹ , R ² , R' ² , R ³ , R' ³ , R ⁴ , R' ⁴ , R ⁵ and R' ⁵ representing a hydrogen atom: [Chem. 14]

[0181] 1.2 g of the enzyme Candida antarctica B (Sigma Aldrich) (60% w/w with respect to the dibenzylidene xylitol derivative) are added to a solution of 2 g of dibenzylidene xylitol (6.12 mmol), 3.48 g of stearic acid (12.2 mmol) (Sigma

Aldrich) and 10 g of molecular sieve (Sigma Aldrich) (500% w/w with respect to the dibenzylidene xylitol derivative) in 200 ml of methyltetrahydrofuran (Sigma Aldrich). The mixture is stirred at 60°C for 4 days and then cooled. The solution is separated from the molecular sieve and from the enzyme by centrifugation (5000 revolutions per minute, 10 minutes). The solution is concentrated to dryness on a rotary evaporator under reduced pressure. The crude product is purified on an ion-exchange resin IRA67 (2 g w/w) in dichloromethane (10V) for 1 hour. The mixture is filtered and the solution is concentrated on a rotary evaporator under reduced pressure in order to obtain a white solid having a melting point of 134°C. [0182] The spectroscopic analyses are in agreement with the expected structure.

[0183] Example 3: Synthesis of the monoisostearate of formula (I) with R representing -C(0)-(CH ₂ )i ₃ -C(H)(CH ₃ ) ₂ and R ¹ , R ² , R ³ , R ⁴ and R ⁵ representing a hydrogen atom: [Chem. 15]

[0184] 1.2 g of the enzyme Candida antarctica B (Sigma Aldrich) (60% w/w with respect to the dibenzylidene xylitol derivative) are added to a solution of 2 g of dibenzylidene xylitol (6.12 mmol), 3.49 g of isostearic acid (12.2 mmol) (Sigma Aldrich) and 10 g of molecular sieve (Sigma Aldrich) (500% w/w with respect to the dibenzylidene xylitol derivative) in 200 ml of methyltetrahydrofuran (Sigma Aldrich). The mixture is stirred at 60°C for 4 days and then cooled. The solution is separated from the molecular sieve and from the enzyme by centrifugation (5000 revolutions per minute, 10 minutes). The solution is concentrated to dryness on a rotary evaporator under reduced pressure. The crude product is purified on an ion-exchange resin IRA67 (2 g w/w) in dichloromethane (10V) for 1 hour. The mixture is filtered and the solution is concentrated on a rotary evaporator under reduced pressure in order to obtain a white solid corresponding to the expected product.

[0185] The spectroscopic analyses are in agreement with the expected structure.

[0186] Evaluation of the compounds of the invention vs. comparative:

The comparatives are according to Examples 1 , 2 and 3 starting from sorbitol:

Example 4 (outside the invention): Dibenzylidene-d-sorbitol mono-oleate

Example 5 (outside the invention): dibenzylidene-d-sorbitol monostearate

Example 6 (outside the invention): dibenzylidene-d-sorbitol monoisostearate

Intermediate C (outside the invention): Dibenzylidene xylitol

Example 7 (outside the invention): Synthesis of the monoisostearate of formula (I) with R representing -C(0)-(CH ₂ ) ₄ -CH3 and R ¹ , R ² , R ³ , R ⁴ and R ⁵ representing a hydrogen atom. [0187] The gelling process is as follows: the product to be evaluated is weighed in order to obtain a concentration of 2% w/V (i.e. 20 mg in 1 ml of oil). The oil is added at ambient temperature. The mixture is stirred magnetically and heated at 60°C for one hour in a 20 ml flask (Screw Vials 24 mm Clear Glass 27.5 x 57 mm). The flask is subsequently allowed to cool to ambient temperature without specific action for at least 2 hours. The gelling was evaluated by visual observation of the magnetic bar present in the gel when the flask is inverted.

[Table 1]

* % w/V

[0188] By increasing the concentration of the concentrations (for example up to 5%), more or less opaque gels are obtained.

[0189] Study of opaquenes by inverting the flask on a sheet (see appended Fig. 1 ). [0190] Examples of sticks:

[0191 ] The preparation of four cosmetic sticks was carried out, starting from Example 3, in squalane, under in tubo operating conditions: 2% concentration by weight and heating at 60°C for 1 h.

[0192] Without pigment: Stick 1 [0193] Procedure: 10 mg of Example 3 are mixed with 2 ml of squalane (0.5% w/V) in a 10 ml flask. This mixture is heated at 60°C for one hour under magnetic stirring. The solution is added to a 2.5 ml precut syringe. The syringe is left standing at ambient temperature for 2 hours and then pressed in order to carry out the evaluation. The gelled product exits easily from the syringe and remains structured, cylindrical without change in internal diameter of the cylinder in which it is found (cylinder of the syringe) or 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 appended Fig. 2). [0194] With pigments: Sticks 2, 3 and 4

[0195] 10 mg of Example 3 (2% w/V) are mixed with 0.1 g of DC Red 7 (5% w/V) and 2 ml of squalane in a 10 ml flask. This mixture is heated at 60°C for one hour under magnetic stirring. The solution is added to a 2.5 ml precut syringe. The syringe is left standing at ambient temperature for 2 hours, in order to result in the Stick 2, and then pressed in order to carry out the evaluation. Sticks 3 and 4 were prepared in the same way as Stick 2 except that the DC Red 7 was replaced by the same amount by weight of iron oxide (Stick 3) and of Red 7 Lake (Stick 4) (see appended Fig. 3 and Fig. 4). [0196] These four sticks are glossy and readily disintegrate during use after application of Sticks 1 to 4 to the substrate (a paper sheet). It is observed that the gelled products exit easily from the syringes and remain structured, cylindrical without visual change in internal diameter of the cylinder in which they are found (cylinders of the syringe) or in general appearance, even after several minutes (15 minutes). In addition, the sticks do not break during their applications to the substrate (see appended Fig. 5).