A method for treating keratinous materials using at least one acetoacetate-functional oil and at least one crosslinking agent.

Abstract

The present invention relates to a method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, comprising the steps of: i) one or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, or compositions comprising said compounds [Formula 1] JPEG2026502186000111.jpg29170 where, in formula (I), A K2, Y, R4, R a , R b , p, m, n, t, q and u are as defined in claim 1; ii) at least one cross-linking agent in one or more sequential steps.

Description

[Technical Field]

[0001] The invention relates more particularly to the cosmetics field, in particular for caring for and / or making up keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0002] The object of the present invention is therefore to propose new treatment methods, in particular cosmetic treatment methods, comprising applying an acetoacetate-functional oil and at least one crosslinking agent to keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, which methods are most particularly advantageous in terms of their technical performance, in particular in terms of the durability of the deposits obtained thereby and the sensory experience they provide to the user. [Background technology]

[0003] Cosmetics conventionally require the use of one or more film-forming polymers to obtain a good deposition of these cosmetics on keratinous materials, in particular to meet the requirements detailed below.

[0004] Therefore, in the field of skin and / or lip makeup, it is most particularly expected that the deposit formed does not transfer even when it comes into contact with fingers or clothes.It should also have good staying power when it comes into contact with water, especially rain, when it comes into contact with water during showering or even sweating, and even when it comes into contact with sebum, or even when it comes into contact with fatty foods, especially food oils when this deposit is formed on the lips.In addition, this deposit should be comfortable or glossy.

[0005] For this purpose, dispersions of nanometer-sized polymer particles are used as film formers in makeup products, such as mascara, eyeliner, eyeshadow or lipstick, and in hair care products, more particularly in their organic phase, especially the oily phase.

[0006] However, the compositions of the prior art have insufficient staying power over time.A composition, particularly a film-forming cosmetic composition, is known that comprises at least one fatty phase and at least one copolymer obtained by polymerization with ethylene-based monomers, some of which have specific groups (see, for example, International Publication No. WO2022 / 136104).Nevertheless, such a composition requires the presence of a fatty phase, which may limit its application to certain fields.In addition, these compositions do not necessarily meet the naturalness needs of some consumers.

[0007] From EP 1,392,222 it is also known to use a cosmetic composition for the care and / or treatment of keratinous materials, said cosmetic composition comprising a supramolecular polymer comprising a polymer backbone and at least two groups capable of forming at least three hydrogen bonds. However, alternatives to this composition still have insufficient performance in terms of staying power over time or water resistance.

[0008] Compositions and methods for forming deposits on keratin substrates with good staying power over time using compounds with an acetoacetate function and functionalized active agents that are covalently bonded to the keratin materials are also known from WO 2014 / 099108.

[0009] Moreover, WO 06 / 042169 describes tissue adhesives for medical and veterinary use, which are formed by the reaction of polyhydroxy compounds derived from acetoacetate groups and / or polyamine compounds derived from acetoacetamide groups with amino-functional crosslinking compounds.

[0010] The synthesis of acetoacetate diester triglycerides is also described in International Publication No. WO2016 / 164870.

[0011] However, in general, the treatments and methods described above do not make it possible to obtain a deposit on keratinous materials, and in particular on the skin and / or lips, that meets all of the requirements described above (i.e., very good resistance to water and / or to fatty substances, especially on the lips, and also comfortable to wear for the user, the ability to adjust the gloss of the deposit, or not producing visually unsightly, transparent, and / or invisible deposits if not pigmented).

[0012] Additionally, there is high consumer demand for compositions that have a reduced impact on the environment. Summary of the Invention [Problem to be solved by the invention]

[0013] There is therefore still a need for a treatment method, in particular a cosmetic treatment method, intended to be applied to keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, which makes it possible to obtain a film-forming, non-sticky, almost transfer-free, glossy, comfortable and persistent deposit.

[0014] There also remains a need for treatment methods, especially cosmetic treatment methods, which make it possible to obtain deposits that have very good staying power over time and are resistant to water and lipids, especially sebum.

[0015] Additionally, there remains a need for treatments, particularly cosmetic treatments, that provide deposits that have shiny and / or invisibility properties.

[0016] The present invention is specifically directed to meeting these needs in whole or in part. [Means for solving the problem]

[0017] These problems are solved by a method for treating, in particular cosmetically treating, keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, which comprises applying to the keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows at least i) one or more compounds of formula (I) below, their optical isomers or geometric isomers, and / or solvates thereof, such as hydrates, or compositions comprising said compounds: [ka] Here, in formula (I), Z is a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic, polyvalent C2-C 40 , especially C3~C 36 , where Z is optionally -O-, -N(R a )-, -S-, -C(O)-, (hetero)cyclic rings and combinations thereof; AK1 is a divalent, saturated or unsaturated, linear or branched C1-C 12 , preferably a C1-C6, more preferably a saturated C1-C6 hydrocarbon-based chain; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4)v linear or branched, saturated or unsaturated C1-C, optionally substituted with one or more identical or different moieties selected from 40 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O- and / or -(hetero)cycle-O-(hetero)cycle-; AK3 is a divalent, linear or branched, saturated or unsaturated C1-C 12 , preferably C1-C6, more preferably saturated C1-C6, even more preferably C1-C4 hydrocarbon-based chain; R is a hydrogen atom, a linear or branched, saturated or unsaturated C1 to C6, preferably C1 to C4 alkyl moiety, in particular a methyl moiety, or -C(O)-C(R a )(R b )-C(O)-R4 moiety; X represents -O-, -S-, -OC(O)- or -C(O)-O-; Y represents -OC(O)- or -C(O)-O-; R4 represents a linear or branched, saturated or unsaturated C1-C6 monovalent hydrocarbon-based moiety, preferably a (C1-C4) alkyl group, in particular methyl or tert-butyl, more preferably methyl; R a and R b may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group, preferably a hydrogen atom; p represents an integer equal to 0 or 1; m represents an integer equal to 0, 1, 2, 3, or 4; it is understood that when m is greater than 1, the -Y-AK2 moieties are the same or different; n represents an integer equal to 0, 1, 2, 3, or 4; when n is greater than 1, -(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) uThe parts are understood to be the same or different; t represents an integer equal to 0 or 1; q represents an integer equal to 0 or 1; u represents an integer equal to 1, 2, or 3; v represents an integer equal to 1, 2, or 3; When q is equal to 0, t is equal to 0, (m+n) is equal to or greater than 1, and one or more compounds of formula (I) contain at least two -C(O)-C(R a )(R b )—C(O)—R groups; and ii) at least one cross-linking agent in one or more sequential steps.

[0018] According to a preferred embodiment, the treatment method according to the invention also comprises applying to the keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows, at least iii) a cosmetic active agent.

[0019] According to a preferred embodiment, the method according to the invention comprises applying to keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows: i) at least one compound as defined above, an optical isomer or geometric isomer thereof, and / or a solvate thereof, such as a hydrate, or a composition comprising said compound; ii) applying at least one crosslinking agent; and iii) applying at least one cosmetic active agent.

[0020] Cosmetic active agent iii), if present, may be applied simultaneously with i) and / or ii).

[0021] According to one particular embodiment, the keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, may be damp or wet before the application of i) and / or ii), and optionally iii), e.g., steps i), ii) and optionally iii) may be carried out on damp skin.

[0022] According to one embodiment, the method comprises applying i), ii) and optionally iii) to moist or wet keratinous material, in particular moist or wet skin and / or lips and / or eyelashes and / or eyebrows.

[0023] According to another embodiment, the method comprises applying i), ii) and optionally iii) to dry keratinous materials, in particular dry skin and / or lips and / or eyelashes and / or eyebrows.

[0024] The inventors have therefore surprisingly discovered that by applying component i), component ii) and optionally component iii) to keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, it is possible to obtain a deposit on the keratinous materials, in particular the skin, which has good resistance to external attacking agents, such as water, oil, in particular food oils, sweat and / or sebum, and therefore has very good staying power over time.

[0025] Advantageously, the deposits obtained via the method according to the invention are also very comfortable: they are not sticky and do not transfer.

[0026] Application of component i), component ii), and optionally component iii) to keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, advantageously provides a shiny deposit.

[0027] definition

[0028] For purposes of this invention, throughout the specification, including the claims, the following terms have the following meanings unless otherwise specified.

[0029] The term "cosmetic active agent" means an organic or organosilicon compound or a mineral compound that can be incorporated into a cosmetic composition to provide an effect on keratinous materials, whether this effect is immediate or is provided by repeated application. As examples of cosmetic active agents, mention may be made of colored or uncolored, fluorescent or non-fluorescent compounds, such as optical brighteners or UVA and / or UVB blockers, care active agents, such as anti-aging active agents, or active agents intended to provide a benefit to keratinous materials, in particular to the skin, such as active agents acting on the barrier function, deodorant active agents, antiperspirant active agents, exfoliating active agents, antioxidant active agents, moisturizing active agents, sebum-regulating active agents, active agents intended to combat the effects of pollution, antibacterial or bactericidal active agents, fragrances, and dyes, such as direct dyes or pigments, preferably pigments.

[0030] Preferably, the cosmetic active agent is selected from a) dyes selected from pigments, direct dyes, and combinations thereof, b) active agents for caring for keratinous materials, preferably skin, c) UV-blocking agents, and d) combinations thereof.

[0031] For the purposes of the present invention, the term "fatty substance" means an organic compound that is insoluble in water at room temperature (25°C) and atmospheric pressure (760 mmHg) (solubility less than 5%, preferably less than 1%, even more preferably less than 0.1%); in addition, said fatty substance is soluble under the same temperature and pressure conditions in organic solvents, such as halogenated solvents, for example chloroform or dichloromethane, lower alcohols, for example ethanol, or aromatic solvents, for example benzene or toluene.

[0032] The term "(hetero)aryl" refers to an aryl group or a heteroaryl group.

[0033] The term "(hetero)cycloalkyl" means a cycloalkyl group or a heterocycloalkyl group.

[0034] An "aryl" radical or a "heteroaryl" moiety, or an "aryl" or "heteroaryl" part of such a moiety, is C1-C6, preferably C1-C4, (poly)(hydroxy)alkyl moieties; halogen atoms, such as chlorine, fluorine or bromine atoms; hydroxyl groups; C1-C2 alkoxy moiety; C2-C4 (poly)hydroxyalkoxy moiety; Amino moiety; an amino moiety substituted by one or two identical or different C1-C6, preferably C1-C4, alkyl moieties; an acylamino moiety (-N(R)-C(O)-R'), where the R moiety is a hydrogen atom; the C1-C4 alkyl moiety, and the R' moiety is a C1-C4 alkyl moiety; a carbamoyl moiety ((R)2N-C(O)-), where the R moieties may be the same or different and represent a hydrogen atom or a C1-C4 alkyl moiety; an alkylsulfonylamino moiety (R'-S(O)2-N(R)-), where the R moiety represents a hydrogen atom or a C1-C4 alkyl moiety, and the R' moiety represents a C1-C4 alkyl moiety or a phenyl moiety; an aminosulfonyl moiety ((R)2N-S(O)2-), where the R moieties may be the same or different and represent a hydrogen atom or a C1-C4 alkyl moiety; carboxyl moieties in acid or salified form (preferably with alkali metals or substituted or unsubstituted ammonium); cyano group (CN); Polyhalo(C1-C4)alkyl groups, preferably trifluoromethyl (CF3) and optionally substituted with at least one substituent carried by a carbon atom selected from:

[0035] The cyclic or heterocyclic portion of the non-aromatic moiety is hydroxyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy; alkylcarbonylamino ((RC(O)—NR′—), where the R′ moiety is a hydrogen atom or a C1-C4 alkyl moiety, and the R moiety is a C1-C2 alkyl moiety, amino substituted with one or two of the same or different C1-C4 alkyl groups; alkylcarbonyloxy ((RC(O)—O—), where the R moiety is a C1-C4 alkyl moiety, amino substituted with one or two of the same or different C1-C4 alkyl groups; Alkoxycarbonyl ((ROC(O)-), where the R group is a C1-C4 alkyl moiety, amino substituted with one or two of the same or different C1-C4 alkyl groups; may be substituted with at least one substituent carried by a carbon atom selected from the group:

[0036] The cyclic or heterocyclic moiety, or the non-aromatic portion of an aryl or heteroaryl moiety, may also be substituted with one or more oxo groups.

[0037] The hydrocarbon-based chain is unsaturated if it contains one or more double bonds and / or one or more triple bonds.

[0038] An "aryl" moiety is a monocyclic or fused or unfused polycyclic hydrocarbon-based group containing from 6 to 14 carbon atoms, in which at least one ring is aromatic; preferably, the aryl moiety is phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl.

[0039] The "heteroaryl" moiety refers to a monocyclic or fused or non-fused polycyclic, 5-14 membered ring group containing 1-6 heteroatoms selected from nitrogen, oxygen, sulfur, and selenium atoms, in which at least one ring is aromatic, and preferably the heteroaryl moiety is selected from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothia ... and is selected from among azolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthoxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrrylyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, and xanthryl.

[0040] A "cyclic" or "cycloalkyl" moiety is a monocyclic or fused or non-fused polycyclic, non-aromatic, cyclic hydrocarbon-based moiety having 5 to 14 carbon atoms, which may contain one or more unsaturated groups. The cycloalkyl is preferably a cyclohexyl group.

[0041] A "heterocyclic" or "heterocycloalkyl" moiety is a monocyclic or fused or non-fused polycyclic, 3- to 9-membered non-aromatic cyclic moiety having 1 to 4 heteroatoms selected from nitrogen, oxygen, sulfur, and selenium atoms, preferably wherein the heterocycloalkyl is selected from epoxide, piperazinyl, piperidyl, morpholinyl, and dithiolane.

[0042] An "alkyl" moiety is a saturated hydrocarbon-based moiety, linear or branched, especially C1 to C6, preferably C1 to C4.

[0043] An "alkoxy" moiety is an alkyl-oxy moiety in which the alkyl portion is a linear or branched C1 to C6, preferably C1 to C4, hydrocarbon-based moiety.

[0044] A "(poly)(hydroxy)alkyl" moiety refers to a C1-C6, preferably C1-C4, alkyl moiety optionally substituted with one or more hydroxyl moieties, preferably 1-4, more particularly 1-3, hydroxyl groups.

[0045] A "sugar" moiety is a monosaccharide or disaccharide moiety. Sugar moieties that may be mentioned include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose.

[0046] The term "monosaccharide" refers to a sugar having the formula C containing at least five carbon atoms. x (H2O) x where x is an integer of 5 or greater, preferably x is 6 or greater, particularly x is 5 to 7, preferably x is 6. The monosaccharides may be in the D or L configuration, and may be alpha or beta anomers, as well as salts thereof, and solvates thereof, such as hydrates.

[0047] The term "disaccharide" refers to a di-oside sugar, which is a compound in which two sugars are linked together via an O-oside bond, where the compound is composed of two monosaccharide units (also known as mono-osides). The monosaccharide units contain at least five, preferably six, carbon atoms. In particular, the monosaccharide units are linked via a 1,4 or 1,6 bond as α (alpha) or β (beta) anomers, and each oside unit may be in the L or D configuration, as well as salts thereof and solvates thereof, such as hydrates of the monosaccharides. More particularly, they are represented by the following general formula: -[C x (H2O) y )]2- or -[(CHO)x ]2- (where x is an integer of 5 or more, preferably x is 6 or more, particularly x is 5 to 7, preferably x is 6, and y is an integer representing x-1).

[0048] The term "polysaccharide" refers to a polysaccharide sugar, which is a polymer of multiple sugars linked together via O-oside bonds, wherein the polymer is composed of monosaccharide units (also known as mono-oside) as defined above. The monosaccharide units contain at least 5, preferably 6, carbon atoms. In particular, the monosaccharide units are linked via 1,4 or 1,6 bonds as α (alpha) or β (beta) anomers, and each oside unit may be in the L or D configuration, as well as salts thereof and solvates thereof, such as hydrates of the monosaccharides. More particularly, they are represented by the following general formula: -[C x (H2O) y )] w -or-[(CHO) x ] w - (where x is an integer of 5 or more, preferably x is 6 or more, particularly x is 5 to 7, preferably x is 6, y is an integer representing x-1, and w is an integer of 2 or more, particularly an integer of 3 to 3000, more particularly an integer of 5 to 2500, preferably an integer of 10 to 2300, particularly an integer of 15 to 1000, more particularly an integer of 20 to 500, preferably an integer of 25 to 200).

[0049] An "anionic counterion" is an anion or anionic group associated with a cationic charge. More particularly, anionic counterions include: i) halides, such as chloride or bromide; ii) nitrates; and iii) sulfonates, such as C1-C6 alkylsulfonates: Alk-S(O)2O.- , for example, methanesulfonate or mesylate, and ethanesulfonate; iv) arylsulfonate: Ar—S(O)O - For example, benzenesulfonate or toluenesulfonate, tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfate: Alk-OS(O)O - x) aryl sulfate: Ar—OS(O)O - 1) alkoxy sulfates, such as benzene sulfate and toluene sulfate; 2) Alkoxy sulfates, such as Alk-OS(O)O - xii) aryloxy sulfates: Ar—OS(O)O - xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borate, for example tetrafluoroborate.

[0050] "Solvates" refers to hydrates and also to combinations with linear or branched C1-C4 alcohols, such as ethanol, isopropanol or n-propanol.

[0051] The term "UV-A screening agent" refers to a chromophore derived from a compound that blocks (or absorbs) UV-A rays with wavelengths of 320 to 400 nm. UV-A screening agents can be divided into short-wavelength UV-A screening agents (which absorb UV rays with wavelengths of 320 to 340 nm) and long-wavelength UV-A screening agents (which absorb UV rays with wavelengths of 340 to 400 nm).

[0052] The term "UV-B blocker" refers to a chromophore derived compound that blocks (or absorbs) UV-B ultraviolet rays in the wavelength range of 280 to 320 nm.

[0053] The term "chromophore" means a radical derived from a colorless or colored compound, which exhibits a wavelength λ between 250 and 800 nm. abs The term "chromophore" refers to a dye capable of absorbing ultraviolet and / or visible light at wavelengths within the visible light range, preferably from 400 to 800 nm. Preferably, the chromophore has a visible color, especially in the range from 400 to 700 nm (Ullmann's Encyclopedia, 2005, Wiley-VcH, Verlag "Dyes, General Survey", § 2.1 Basic Principle of Color).

[0054] The term "anhydrous composition" means that the composition contains less than 5% by weight of water, preferably less than 3% by weight of water, and even better less than 1% by weight of water, relative to the total weight of the composition under consideration. Even more preferably, the composition under consideration does not contain water.

[0055] The terms "coloring agent" and "dyestuff" are equivalent.

[0056] The expression "comprises" should be understood as being synonymous with "comprises at least one," unless otherwise specified.

[0057] The expressions "... up to...", "including... up to...", "formed from... up to..." and "ranging from... to..." are to be understood as including the limits stated, unless otherwise specified.

[0058] It will be understood that the methods of treatment according to the present invention, and also the compositions used, are non-therapeutic. DETAILED DESCRIPTION OF THE INVENTION

[0059] Treatment method

[0060] The first subject of the present invention is a method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, especially the skin, with i) at least one or more compounds of formula (I) as described hereinabove and hereinafter or compositions comprising said compounds; ii) at least one cross-linking agent, in particular the cross-linking agents described herein below; and iii) optionally at least one cosmetic active agent, in particular a cosmetic active agent as described hereinafter; The method is a method of treating in one or more steps using

[0061] According to a particular embodiment of the invention, the method of treatment according to the invention comprises the simultaneous administration of component i), component ii) and, optionally, component iii).

[0062] According to another particular embodiment of the invention, the treatment method according to the invention comprises at least two steps in which component i), component ii) and, optionally, component iii) are applied in separate, sequential steps to keratinous materials, in particular to the skin and / or the lips and / or the eyelashes and / or the eyebrows, wherein said one or more cosmetic active agents iii) may be present together with one or more components i) and / or one or more components ii).

[0063] According to one particular embodiment, one or more of the components i) are applied to the keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, and then one or more of the components ii) are applied to the keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, it being understood that component iii), if present, may be applied together with component i) and / or component ii).

[0064] According to another particular embodiment, one or more of said components ii) are applied to keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, and then one or more of said components i) are applied to said keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, it being understood that component iii), if present, may be applied together with component i) and / or component ii).

[0065] According to a particular embodiment of the invention, the method for treating, in particular cosmetically treating, keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, is a cosmetic treatment method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows.

[0066] According to one embodiment of the invention, the method of treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, according to the invention using component i), component ii) and optionally component iii) is a skin care process.

[0067] According to one embodiment of the invention, the method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, is a method for making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, which comprises at least one cosmetic active agent selected from dyes, preferably pigments.

[0068] When the method of treatment includes several steps, including one step using one or more compounds of Formula (I), (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie) without a cross-linking agent, the one or more compounds of Formula (I), (Ia), (Ib), (Ic), (Id), (Ie), (IIc), (IId) and / or (IIe) may be used as they are (pure) or may be used in composition "C1" as described hereinafter.

[0069] According to one embodiment of the invention, the method according to the invention is a method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, in particular for cosmetic treatment, in particular a method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, which comprises applying to said keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows at least: A composition designated "C1", comprising: i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter, and optionally, iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; preferably, composition "C1" does not comprise iii) a crosslinker; A composition designated "C2" comprising: i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter; ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinabove and hereinafter; and, optionally, iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; preferably, composition "C2" does not comprise iv) a cosmetic active agent; a composition designated "C3", comprising: i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter; ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinabove and hereinafter; and iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; a composition designated "C4", said composition "C4" comprising ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinafter, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described above and hereinafter; preferably, composition "C4" does not i) comprise at least one compound of formula (I), or formula (Ia), formula (Ib), formula (Ic), formula (Id) and / or formula (Ie), as described above and hereinafter; and / or a composition designated "C5", said composition "C5" comprising iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; preferably, composition "C5" i) does not comprise at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter, and ii) does not comprise at least one crosslinker; administering the method comprising the use of i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described herein above and hereinafter, together or separately, and ii) at least one cross-linking agent, in particular at least one cross-linking agent as described herein below; and it is understood that composition "C1", composition "C2", composition "C3", composition "C4" and composition "C5" may be anhydrous, aqueous, for example hydroalcoholic, and / or may comprise one or more fatty substances iv), in particular one or more fatty substances iv) as described herein below, The above method.

[0070] According to one particular embodiment, the method according to the invention is a method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, in particular for cosmetic treatment, in particular a method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, which comprises applying to said keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, at least i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; A composition designated "C2" comprising: i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter; ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinabove and hereinafter; and, optionally, iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; preferably, composition "C2" does not comprise iv) a cosmetic active agent; a composition designated "C3", comprising: i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter; ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinabove and hereinafter; and iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; a composition designated "C4", said composition "C4" comprising ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinafter, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described above and hereinafter; preferably, composition "C4" does not i) comprise at least one compound of formula (I), or formula (Ia), formula (Ib), formula (Ic), formula (Id) and / or formula (Ie), as described above and hereinafter; and / or a composition designated "C5", said composition "C5" comprising iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; preferably, composition "C5" i) does not comprise at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter, and ii) does not comprise at least one crosslinker; administering the method comprising the use of i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as described hereinabove and hereinafter, together or separately, and ii) at least one cross-linking agent, in particular at least one cross-linking agent as described hereinabove; and it is understood that composition "C2", composition "C3", composition "C4" and composition "C5" may be anhydrous, aqueous, for example hydroalcoholic, and / or may comprise one or more fatty substances iv), in particular one or more fatty substances iv) as described hereinabove, The above method.

[0071] According to one aspect of the present invention, a method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, in particular a method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, uses a composition designated "C3", which composition "C3" comprises: i) a compound represented by formula (I), or at least one of formulas (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie), as described herein above and hereinafter; ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinabove and hereinafter, and iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove, in particular at least one cosmetic active agent as described hereinabove, in particular at least one cosmetic active agent selected from a) colorants, such as pigments, direct dyes and combinations thereof, b) active agents for caring for keratinous materials, preferably skin, c) UV-blocking agents, and d) combinations thereof, especially at least one colorant, more in particular at least one pigment.

[0072] According to another aspect, a method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, in accordance with the present invention, in particular a method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprises the use of a composition designated "C1" and a composition designated "C4", wherein composition "C1" comprises: i) a compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ij), (Ij), (Ik), (Ik), (Im ... and composition "C4" comprises ii) at least one crosslinking agent, particularly at least one crosslinking agent described hereinafter, and optionally iii) at least one cosmetic active agent, particularly at least one cosmetic active agent described hereinafter.

[0073] According to another aspect, a method for treating keratinous materials, especially the skin and / or lips and / or eyelashes and / or eyebrows, in accordance with the present invention, in particular a method for caring for and / or making up keratinous materials, especially the skin, lips, eyelashes and / or eyebrows, comprises i) using at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie), as described hereinabove and hereinafter, and a composition designated "C4", wherein composition "C4" comprises ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinabove and hereinafter, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter.

[0074] According to another aspect, a method for treating keratinous materials, especially the skin and / or lips and / or eyelashes and / or eyebrows, in particular for caring for and / or making up keratinous materials, especially the skin, lips, eyelashes and / or eyebrows, according to the present invention, comprises the use of a composition designated "C1" or i) at least one compound of formula (I) or formula (Ia), formula (Ib), formula (Ic), formula (Id), formula (Ie), formula (c), formula (Iid) and / or formula (Iie) as described hereinabove and hereinafter, a composition designated "C4", and a composition designated "C5", wherein the composition "C1" comprises i) at least one compound of formula (I) or formula (Ia), formula (Ib), formula (Ic), formula (Id), formula (Ie), formula (c), formula (Iid) and / or formula (Iie) as described hereinabove and hereinafter, (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie), and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described herein above and hereinafter, composition "C4" comprises ii) at least one crosslinker, in particular at least one crosslinker as described herein below, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described herein above and hereinafter, and composition "C5" comprises iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described herein above and hereinafter.

[0075] According to another aspect, a method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, in accordance with the present invention, in particular a method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprises the use of a composition designated "C2" and a composition designated "C5", wherein composition "C2" comprises: i) a compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id), (Ie), as described hereinabove and hereinafter; and composition "C5" comprises at least one compound of formula (Iic), formula (Iid) and / or formula (Iie), ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinafter, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described above and hereinafter.

[0076] According to one variant of the method of the invention, one or more of said components i) and optionally component iii) are applied together, i.e. simultaneously, to keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, during a first step, and then, during a subsequent step, one or more of said components ii) and, optionally, component iii) are applied to the keratinous materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows.

[0077] According to one particular embodiment, the method according to the invention comprises two successive steps in which two different compositions, preferably composition "C1" and then composition "C4", are applied to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0078] According to a particular embodiment of the method, during a first step, composition "C1", or i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie), as described herein above and hereinafter, is applied to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, and then composition "C4" is applied to the keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0079] According to yet another variant of the method of the invention, one or more of the components ii) and, optionally, component iii) are applied to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, and then one or more of the components i) and, optionally, iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described above, are applied to the keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows. In particular, composition "C4" is applied to the keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, and then composition "C1", or i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie), as described herein above and hereinafter, is applied.

[0080] According to another variant of the method according to the invention, i) a composition "C1" comprising at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie) as described hereinabove and hereinafter, or component i) and optionally component iii), is applied, and sequentially a composition "C4" comprising component ii) and optionally component iii), preferably component i), or composition "C1", is applied before composition "C4".

[0081] Composition "C1", composition "C2", composition "C3", composition "C4" and / or composition "C5" of the method according to the invention comprises at least one fatty substance iv), in particular at least one oil, and may be in the form of a direct emulsion or an inverse emulsion.

[0082] Thus, composition "C1", composition "C2", composition "C3", composition "C4" and / or composition "C5" of the method according to the present invention may be applied directly to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, or may even be formed directly on the surface of keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0083] Therefore, according to the invention, a distinction is made between three application methods known as "one-gesture application mode", "two-gesture application mode" and "three-gesture application mode".

[0084] According to one embodiment of the method of the invention, the method is carried out in one gesture by applying composition "C2" or composition "C3" as defined above to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0085] Thus, according to one embodiment, the treatment method according to the invention comprises a single step of applying composition "C2" or composition "C3" to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0086] The term "one-gesture application mode" refers to the direct application of a single composition according to the present invention, i.e., composition "C2" or composition "C3", to the subject's keratinous material, in particular the subject's skin and / or lips and / or eyelashes and / or eyebrows.

[0087] After applying composition "C2" or composition "C3", a long-lasting, non-sticky deposit is advantageously obtained. The deposit obtained is also resistant to food oils, water, sebum and / or abrasion.

[0088] According to another embodiment of the method of the invention, the method is performed with two gestures.

[0089] The term "two-gesture application mode" means the sequential application of two different compositions, for example, "C1" and "C4", or "C2" and "C4", or "C3" and "C4", preferably "C1" and then "C4", "C2" and then "C4", or "C3" and then "C4", to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0090] The term "two-gesture application mode" also refers to the sequential application to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, of i) at least one compound of formula (I), or formula (Ia), formula (Ib), formula (Ic), formula (Id), formula (Ie), formula (Iic), formula (Iid) and / or formula (Iie) as described herein above and hereinafter, and composition "C4", preferably component i) and then composition "C4".

[0091] According to another embodiment, the method of the invention is performed with three gestures.

[0092] The term "three-gesture application mode" refers to the sequential application of three different compositions selected from composition "C1", composition "C2", composition "C4" and composition "C5". According to this application mode in accordance with the present invention, for example, the sequential application of α) composition "C1" or composition "C2", then β) composition "C4", then γ) composition "C5", preferably composition "C1", then composition "C4" or, respectively, composition "C5", is carried out on keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows.

[0093] The term "three-gesture administration mode" also refers to the sequential administration of i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie) as described herein above and below, of composition "C4", and of composition "C5", preferably wherein component i) is administered before administration of composition "C4".

[0094] According to another embodiment, the sequential application means the sequential application onto keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, of α) a composition, such as composition “C4”, and β) composition “C1”, or i) at least one compound of formula (I), or formula (Ia), formula (Ib), formula (Ic), formula (Id), formula (Ie), formula (Iic), formula (Iid) and / or formula (Iie), as described herein above and below, or composition “C2”, and also γ) composition “C5”, preferably the application of composition “C4” before composition “C1” or component i) or composition “C2” or composition “C5”.

[0095] In the two-gesture application mode or three-gesture application mode, the composition applied first, e.g., composition "C1" or composition "C2," preferably composition "C1," is conventionally referred to as the "base coat," and one or more compositions superimposed thereon, e.g., composition "C4," are generally referred to as the "top coat."

[0096] In the two-gesture application mode or the three-gesture application mode, i) at least one compound of formula (I), or formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie), as described hereinabove and hereinafter, is used, and if this compound or these compounds, component i) is applied first, then this application of component i) is also conventionally referred to as a "base coat," and one or more compositions superimposed thereon, such as composition "C4," are generally referred to as a "top coat."

[0097] After application of the various compositions "C1" or component i) and compositions "C2" to "C5", a long-lasting, non-sticky deposit is advantageously obtained. The resulting deposit is also resistant to food oils and water.

[0098] According to one particular embodiment, composition "C1" or component i) and compositions "C2" to "C5" are applied to dry keratinous materials, in particular dry skin and / or lips and / or eyelashes and / or eyebrows.

[0099] According to one particular embodiment, composition "C1" or component i) and compositions "C2" to "C5" are applied to moist or wet keratinous materials, in particular moist or wet skin and / or lips and / or eyelashes and / or eyebrows, i.e. to keratinous materials containing moisture on their surface, in particular skin and / or lips and / or eyelashes and / or eyebrows containing moisture on their surface.

[0100] According to one aspect, the present invention relates to a method for treating, in particular cosmetically treating, keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, in particular a method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprising the step of applying to said keratinous materials, in particular the skin or lips or eyelashes or eyebrows, a composition "C3", in particular a composition "C3" comprising at least one dye, in particular the dyes described above, more in particular at least one pigment.

[0101] According to another aspect of the invention, the invention relates to a cosmetic treatment method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprising at least i) at least one compound of formula (I), or formula (Ia), formula (Ib), formula (Ic), formula (Id) and / or formula (Ie), as described hereinabove and hereinafter, or a composition designated "C1", wherein the composition designated "C1" comprises the same compounds as above and optionally, iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter; and then a composition designated "C4", comprising ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinafter, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described above and hereinafter, and administering sequentially at least one of composition "C1" and / or composition "C4" comprises at least one dye, in particular at least one dye as described herein above and below, preferably at least one pigment, more preferably composition "C1" comprises at least one pigment; The above relates to the cosmetic treatment method.

[0102] According to another aspect of the invention, the invention relates to a method for the cosmetic treatment of keratinous materials, in particular for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprising at least i) at least one compound of formula (I), or formula (Ia), formula (Ib), formula (Ic), formula (Id), formula (Ie), formula (Iic), formula (Iid) and / or formula (Iie), as described hereinabove and hereinafter, or composition "C1" as described above; and Composition "C4" as described above; and Composition "C5" as described above and It is understood that compositions "C1" and / or "C4" and / or "C5" comprise at least one dye, in particular at least one dye as described hereinafter, preferably at least one pigment, Regarding the above cosmetic treatment method, preferably, composition "C5" comprises at least one pigment.

[0103] Compound i): Oil functionalized with acetoacetate functional groups

[0104] As indicated above, the treatment method according to the invention comprises applying to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, at least one compound of formula (I) or a composition comprising said compound.

[0105] The treatment method according to the invention therefore comprises applying to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, at least one or more compounds of formula (I) below, their optical and geometric isomers, and / or solvates thereof, such as hydrates, or a composition comprising said compounds: [ka] Here, in formula (I), Z is a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic, polyvalent C2-C 40 , especially C3~C 36 , where Z optionally represents a hydrocarbon-based moiety of -O-, -N(R a )-, -S-, -C(O)-, one or more (hetero)cyclic rings and / or combinations thereof; AK1 is a divalent, saturated or unsaturated, linear or branched C1-C 12 , preferably a C1-C6, more preferably a saturated C1-C6 hydrocarbon-based chain; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v linear or branched, saturated or unsaturated C1-C, optionally substituted with one or more identical or different moieties selected from 40 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular from O-(CO)-, -(CO)-O- or -(hetero)cycle-O-(hetero)cycle-; AK3 is a divalent, linear or branched, saturated or unsaturated C1-C 12 , preferably C1-C6, more preferably saturated C1-C6, even more preferably C1-C4 hydrocarbon-based chain; R is a hydrogen atom, a linear or branched, saturated or unsaturated C1 to C6, preferably C1 to C4 alkyl moiety, in particular a methyl moiety, or -C(O)-C(R a )(R b )-C(O)-R4 moiety; X represents -O-, -S-, -OC(O)- or -C(O)-O-; Y represents -OC(O)- or -C(O)-O-; R4 represents a linear or branched, saturated or unsaturated C1-C6 monovalent hydrocarbon-based moiety, preferably a (C1-C4) alkyl group, in particular methyl or tert-butyl, more preferably methyl; R a and R b may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group, preferably a hydrogen atom; p represents an integer equal to 0 or 1; m represents an integer equal to 0, 1, 2, 3, or 4; it is understood that when m is greater than 1, the -Y-AK2 moieties are the same or different; n represents an integer equal to 0, 1, 2, 3, or 4; when n is greater than 1, -(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u The parts are understood to be the same or different; t represents an integer equal to 0 or 1; q represents an integer equal to 0 or 1; u represents an integer equal to 1, 2, or 3; v represents an integer equal to 1, 2, or 3; When q is equal to 0, t is equal to 0, (m+n) is equal to or greater than 1, and one or more compounds of formula (I) contain at least two -C(O)-C(R a )(R b )—C(O)—R4 groups.

[0106] According to a preferred embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, are those in which Z is a) -O-, -N(R a )-, -S-, -C(O)- and / or one or more (hetero) rings, in particular -CH2-(CH2) f moiety (wherein f represents an integer of 1 to 10, preferably 1 to 5) or -(CH2) g -(heterocycle)-O-(CH2) h-(heterocycle)-(CH2) j - moiety (wherein h is 0, 1 or 2, preferably 0 or 1, and g and j are each independently an integer from 1 to 3, preferably 1), optionally interrupted by one or more heteroatoms or groups selected from the group consisting of C2-C 30 portion; b) a trivalent moiety, preferably C3 to C6, in particular -CH2-CH-CH2-; and c) a tetravalent moiety, preferably C3 to C 12 , in particular -CH2-C-CH2-CH2-CH2- or -CH2-C-CH2-, or -(CH2) a -CH-CH-(CH2) b - moiety, wherein a and b independently represent integers equal to 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; preferably, a is greater than b, It indicates a moiety selected from:

[0107] According to a preferred embodiment, the (hetero)cycle denotes a heterocyclic, divalent moiety (i.e., heterocycle), preferably a heterocycloalkyl moiety, more particularly a divalent, 3-, 5- or 6-membered heterocycloalkyl moiety, such as a divalent epoxide moiety, a divalent tetrahydrofuran moiety or a divalent tetrahydropyran moiety, wherein the (hetero)cycle denotes a -OR (where R is as defined above), in particular -OH or -OC(O)-C(R a )(R b )—C(O)—R4.

[0108] According to a preferred embodiment, AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and optionally substituted with one or more identical or different moieties selected from one or more identical or different moieties selected from 12 ~C 28and / or said chain may be interrupted by -OC(O)- or -C(O)-O-.

[0109] According to one particular embodiment, one or more compounds of formula (I), or of formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) or (Iie), as defined hereinabove and hereinafter, are present in the composition in a content ranging from 0.1% to 99% by weight, preferably from 1% to 98% by weight, more preferably from 5% to 96% by weight, even better from 10% to 90% by weight, and even better from 20% to 88% by weight, relative to the total weight of the composition under consideration.

[0110] According to one particular embodiment, when the treatment method according to the invention comprises several steps, one or more compounds of formula (I), or of formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) or (Iie) as described herein above and below, may be used pure (single).

[0111] According to a first variant of embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, Z represents a trivalent -CH2-CH-CH2- moiety; p equals 0; n equals 0; m equals 3; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v C, linear or branched, saturated or unsaturated, optionally substituted with one or more identical or different moieties selected from 12 ~C 24 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxide and combinations thereof, in particular from O-(CO)- or (CO)-O-; Y, AK3, v, R, X, R4, R a and R b is as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties, It is a place.

[0112] According to a preferred embodiment, AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v C, linear or branched, saturated or unsaturated, optionally substituted with one or more identical or different moieties selected from 12 ~C 24 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)- and combinations thereof, in particular -OC(O)- or -C(O)-O-.

[0113] According to a variant of this embodiment, the one or more compounds of formula (I) are in particular chosen from Compound (1), Compound (2), Compound (3), Compound (4), Compound (7), Compound (8), Compound (9) and Compound (11), their optical or geometric isomers, and / or solvates thereof, such as hydrates, as described hereinafter. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0114] According to a second variant of embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, p equals 0; Z is a linear or branched, saturated or unsaturated, preferably saturated, acyclic, polyvalent C4-C 24 , especially C6~C 20 , more particularly C 14 ~C 20 , especially C 17 , wherein Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n may be substituted by a moiety; n represents an integer equal to 0, 1, 2, 3, or 4; when n is greater than 1, -(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u It is understood that the moieties may be the same or different; preferably, n is not zero; m equals 1; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) vand / or the chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-; Y, AK1, AK3, t, q, u, v, R, X, R4, R a and R b is as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties, It is a place.

[0115] According to a variant of this embodiment, the one or more compounds of formula (I) are in particular chosen from compounds (5) and (6), their optical or geometric isomers, and / or solvates thereof, such as hydrates, as described hereinafter. [ka] [ka]

[0116] According to a third variant of embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, p equals 0; n+m is equal to 4, and m is not zero; Z is an unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated, and acyclic C-C 24 , especially C3~C 10 , particularly C3, represents a tetravalent hydrocarbon-based moiety; AK2 independently represents -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and preferably one or more -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v C may be linear or branched, saturated or unsaturated, preferably saturated, optionally substituted by a moiety 12 ~C 24 , preferably C 16 ~C 20 , especially C 18 and / or said chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-; AK3 is a linear or branched, saturated or unsaturated C1-C 12 , preferably C1 to C6, more preferably saturated C1 to C6, even more preferably C2 to C4, even better C3, divalent hydrocarbon-based chain; v is as defined above for formula (I); preferably, v is equal to 2; X is as defined above for formula (I); preferably, X represents a sulfur atom; Y, AK1, u, t, q, R, R4, R a and R b is as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties, It is a place.

[0117] According to a preferred embodiment, m is equal to 3, n is equal to 1 and u is equal to 1.

[0118] According to a preferred embodiment, t is equal to 0.

[0119] According to a preferred embodiment, q is equal to 0.

[0120] According to a preferred embodiment, Y represents -C(O)-O.

[0121] According to a preferred embodiment, there is no interruption in any of the AK2 moieties.

[0122] According to a preferred embodiment, the AK2 moiety is saturated.

[0123] According to a preferred embodiment, the AK2 moiety is not substituted with -OR.

[0124] According to a preferred embodiment, AK3 represents a divalent, linear or branched, saturated or unsaturated C1 to C6, more preferably saturated C1 to C6, even more preferably saturated C1 to C4, and even better saturated C3 hydrocarbon-based chain.

[0125] According to a variant of this embodiment, the one or more compounds of formula (I) are in particular chosen from compound (10), as described hereinafter, their optical or geometric isomers, and / or their solvates, such as hydrates. [ka]

[0126] According to a fourth variant of embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, p equals 1; Z is a linear or branched, saturated or unsaturated, preferably saturated, and acyclic, polyvalent C 14 ~C 24 , especially C 16 ~C 20 , more particularly C 17, wherein Z also represents one or more moieties -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n may be substituted with a moiety, but is preferably unsubstituted; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v C is linear or branched, saturated or unsaturated, preferably saturated, substituted by one or more identical or different moieties selected from 14 ~C 30 , especially C 20 ~C 29 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-; X is as defined above for formula (I); preferably, X represents a sulfur atom; Y, AK1, AK3, n, m, v, t, q, u, R, R4, R a and R b is as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties, It is a place.

[0127] According to a preferred embodiment, n is equal to 0 and m is equal to 1.

[0128] According to a preferred embodiment, Z is a divalent radical.

[0129] According to a preferred embodiment, when Z is an unsaturated chain, AK2 is an unsaturated chain, and when Z is a saturated chain, AK2 is a saturated chain.

[0130] According to a variant of this embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, are in particular compounds of formula (Iic) below: HZY-AK4-Y'-ZH (Iic) Here, in formula (Iic), Y is as defined above for formula (I); Z is linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 24 , especially C 16 ~C 20 , preferably C 17 , representing a divalent hydrocarbon-based moiety; Y' represents -C(O)-O- or -OC(O)-, where it is understood that when Y represents -OC(O)-, Y' represents -C(O)-O-, and when Y represents -C(O)-O-, Y' represents -OC(O)-; AK4 represents a saturated divalent hydrocarbon-based moiety having 5 or 6 carbon atoms substituted by at least two -OR moieties, where R is as previously defined in formula (I); The compound of formula (Iic) has at least two —C(O)—C(R a )(R b )-C(O)-R4 moiety, preferably four -C(O)-C(R a )(R b )—C(O)—R4 moieties.

[0131] According to a variant of this embodiment, the one or more compounds of formula (I) are in particular chosen from the following compounds (12), their optical or geometric isomers, and / or their solvates, such as hydrates: [ka]

[0132] According to a fifth variant of embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, p equals 0; Z is a linear or branched, saturated or unsaturated, preferably saturated, and acyclic C2-C 24 , especially C3~C 10 , preferably C4 or C5, and Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n substituted by the moiety, wherein n is preferably equal to 1; n+m is equal to 4, preferably m is equal to 3; AK2 independently represents a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 16 ~C 24 , preferably C 17 , wherein the chain is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and / or the chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-; X is as defined above for formula (I); preferably, X represents a sulfur atom; Y, AK1, AK3, u, t, q, v, n, m, R, R4, R a and Rb is as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties, It is a place.

[0133] According to a preferred embodiment, t is equal to 0 and u is equal to 1.

[0134] According to a preferred embodiment, all of the AK2 moieties are the same, and preferably all of the Y moieties are the same.

[0135] According to a preferred embodiment, Y represents -OC(O)-.

[0136] According to one particular embodiment, the compounds according to this variant are of the following general formula (Iid), their optical or geometric isomers, and / or their solvates, such as hydrates: [AK'2-OCO-CH2]3-C-CH2-OC(O)-C(R a )(R b )-C(O)-R4(Iid) wherein, in formula (Iid), AK′2 is a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 16 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, where the chain is -OR, -S-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and AK3, v, R, R4, R a and R b is as previously defined in formula (I), and the compound has at least two —C(O)—C(R a )(R b)-C(O)-R4 moieties.

[0137] According to a sixth variant of embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, p equals 0; m is not zero; Z is a divalent C2-C alkyl group that is linear or branched, saturated or unsaturated, conjugated or non-conjugated, preferably non-conjugated, acyclic or cyclic, aromatic or non-aromatic, preferably non-aromatic. 24 , especially C3~C 12 , wherein the Z moiety also represents a hydrocarbon-based moiety of —O—, —N(R a )-, -S-, -C(O)-, one or more heteroatoms or groups selected from one or more heterocycloalkyl of 5- or 6-membered rings, and combinations thereof; AK2 is a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 14 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, where the chain is selected from the group consisting of -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and / or the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-, more preferably uninterrupted; X is as defined above for formula (I); preferably, X represents a sulfur atom; Y, AK1, AK3, v, t, q, u, R, R4, R a and R bis as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties, It is a place.

[0138] According to a preferred embodiment of this variant, Z is a divalent -(CH2) g -(heterocycle)-O-(CH2) h -(heterocycle)-(CH2) j - moiety, where h is equal to 0, 1 or 2, preferably 0 or 1, g and j independently represent an integer from 1 to 3, preferably 1, and (heterocycle) represents a divalent 5- or 6-membered heterocycloalkyl moiety, in particular a divalent tetrahydrofuran moiety or a divalent tetrahydropyran moiety, the heterocycle being selected from the group consisting of -OR (where R is as previously defined in formula (I)), in particular -OH or -OC(O)-C(R a )(R b )—C(O)—R4.

[0139] According to one particular embodiment, the compounds according to this variant are of the following general formula (Iie), their optical or geometric isomers, and / or their solvates, such as hydrates: AK''2-C(O)-O-(CH2) g -(heterocycle)-O-(CH2) h -(heterocycle)-(CH2) j -O-CO-AK''2 (Iie) Here, in formula (Iie), h is equal to 0, 1 or 2, preferably equal to 0; g and j independently represent an integer of 1 to 3, preferably 1; (heterocycle) is -OR (where R is as previously defined in formula (I)), especially -OH or -OC(O)-C(R a )(R b)—C(O)—R4; AK''2 is a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 14 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, where the chain is -OH, -OC(O)-C(R a )(R b )-C(O)-R4 and -S-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and / or the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-, more preferably uninterrupted; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties.

[0140] According to a variant of this embodiment, the compound of formula (I) or formula (Iie) is selected from compound (14), as described herein below, its optical and geometric isomers and / or solvates thereof, such as hydrates. [ka] where W is a hydrogen atom or -C(O)-C(R a )(R b )—C(O)—R4, and the compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 group.

[0141] According to a seventh variant of embodiment, one or more compounds of formula (I), their optical or geometric isomers, and / or their solvates, such as hydrates, p equals 0; Z is a linear or branched, saturated or unsaturated, preferably saturated, and acyclic C2-C 24 , especially C3~C 10 , preferably C4 or C5, tetravalent hydrocarbon-based moiety, wherein Z is also substituted by one or more -[(O)t-(AK1)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u] moieties; n+m is equal to 6, preferably m is equal to 2; AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, C3 to C8, in particular C4, C5 or C6, monovalent hydrocarbon-based chain; Y, AK1, AK3, t, q, u, v, R, X, R4, R a and R b is as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties, It is a place.

[0142] According to a variant of this embodiment, the compound of formula (I) is in particular chosen from compound (15), as described hereinafter, their optical and geometric isomers and / or their solvates, such as hydrates. [ka]

[0143] According to a preferred embodiment, the one or more compounds of formula (I) are selected from the following compounds (1) to (15), their optical isomers or geometric isomers, and / or solvates thereof, such as hydrates: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] where W is a hydrogen atom or -C(O)-C(R a )(R b )—C(O)—R4, and the compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 group.

[0144] According to a preferred embodiment, one or more compounds of formula (I) are selected from the above compounds (1) to (14), their optical isomers or geometric isomers, and / or their solvates, such as hydrates.

[0145] According to a preferred embodiment, the one or more compounds of formula (I) are in particular selected from Compound (1), Compound (3), Compound (4), Compound (8), Compound (9), Compound (10), Compound (11) and Compound (15), their optical or geometric isomers, and / or solvates thereof, such as hydrates, as described herein below. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0146] According to a preferred embodiment, the one or more compounds of formula (I) are in particular selected from the above-mentioned compounds (1), (3), (4), (8), (9), (10) and (11), their optical or geometric isomers, and / or their solvates, such as hydrates.

[0147] According to one particular embodiment, the treatment method according to the invention comprises applying to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, at least one compound of formula (I), an optical or geometric isomer thereof, and / or a solvate thereof, such as a hydrate, as described herein above, or a composition comprising said compound, with the exception of the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0148] According to one particular embodiment, the method of treatment according to the invention comprises applying to keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows, at least one compound of formula (I), its optical or geometric isomers, and / or solvates thereof, such as hydrates, or a composition comprising said compounds, for example Compounds (8), (9), (10), (11), (12), (13) and (14) below, its optical or geometric isomers, and / or solvates thereof, such as hydrates. [ka] [ka] [ka] [ka] [ka] [ka] [ka] where W is a hydrogen atom or -C(O)-C(R a )(R b )—C(O)—R4, and the compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 group.

[0149] According to one particular embodiment, the treatment method according to the invention comprises applying to keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows, at least one compound of formula (I), its optical or geometric isomers and / or solvates thereof, such as hydrates, or a composition comprising said compounds, for example the compound of formula (Ia) below, and also its optical or geometric isomers and / or solvates thereof, such as hydrates. Z-(Y-AK2)3(Ia) wherein in formula (Ia): Z represents -CH2-CH-CH2-; AK2 independently represents -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v C, linear or branched, saturated or unsaturated, optionally substituted with one or more identical or different moieties selected from 12 ~C 24 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxide and combinations thereof, in particular from -OC(O)- and -C(O)-O-; Y, AK3, v, R, X, R4, R a and R b as defined above in formula (I); preferably, Y represents -OC(O); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties; In particular, the present invention excludes Compound (1), Compound (2), Compound (3), Compound (4) and Compound (7), as defined above, their optical isomers or geometric isomers, and / or solvates thereof, such as hydrates.

[0150] According to one particular embodiment, the one or more compounds of formula (Ia) are chosen in particular from compounds (8), (9) and (11), their optical or geometric isomers, and / or their solvates, such as hydrates, as defined above.

[0151] According to one particular embodiment, one or more compounds of formula (Ia), their optical and geometric isomers and / or their solvates, such as hydrates, are the following compounds: a) At least one of the three AK2 moieties is -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v branched, saturated or unsaturated C optionally substituted with one or more of the same or different moieties selected from 12 ~C 24 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles, in particular epoxides, and combinations thereof, in particular -OC(O)- or -C(O)-O-; A K3, v, R, X, R4, R a and R b is as defined above; the compound has at least two —C(O)—C(R a )(R b)-C(O)-R4; preferably, Y represents -OC(O); preferably, X represents S; preferably, the three AK2 chains contain 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably, none of the three AK2 moieties is interrupted; or b) the three AK2 moieties are independently substituted with at least one moiety selected from —OH and —OR′, and —OC(O)—C(R a )(R b )-C(O)-R4 and -X'-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v linear, saturated, optionally substituted with one or more of the same or different moieties selected from 12 ~C 24 R' represents a C2-C6 alkyl moiety, particularly ethyl; A K3, v, R, R4, R a and R b is as defined above, preferably Y represents -OC(O)-; and X' represents -O- or -C(O)-O-; the compound has at least two -C(O)-C(R a )(R b )-C(O)-R4 moieties; preferably, the three AK2 chains contain 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably, none of the three AK2 moieties is interrupted; or c) the AK2 moieties are independently -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v linear, saturated, optionally substituted with one or more of the same or different moieties selected from 12 ~C 24which chain may be interrupted by one or more heteroatoms or groups selected from -O- and / or -S- and / or -C(O)-, one or more (hetero)cycles, in particular one or more epoxides, and combinations thereof, preferably from -OC(O)-, -C(O)-O- and -(hetero)cycle-O-(hetero)cycle-; A K3, v, R, X, R4, R a and R b is as defined above; and the compound has at least two —C(O)—C(R a )(R b )-C(O)-R4; preferably, Y represents -OC(O)-; preferably, X represents S; preferably, the three AK2 chains comprise 15 to 21 carbon atoms, more preferably 17 carbon atoms; or d) the three AK2 moieties are linear or branched, unsaturated C2 alkyl groups, wherein at least one of the three AK2 moieties is optionally substituted with one or more of the same or different moieties selected from -OR; 12 ~C 24 wherein the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular from -OC(O)-, -C(O)-O- or (hetero)cycle-O-(hetero)cycle; and at least one of the three AK2 moieties is -S-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and optionally, one or more same or different moieties selected from -OR, 12 ~C 24 represents a monovalent hydrocarbon-based chain; A K3, v, R, R4, R a and R b is as defined above; preferably, Y represents —OC(O)—; and the compound has at least two —C(O)—C(R a )(R b)-C(O)-R4 moieties; preferably, Y represents -OC(O)-; preferably, X represents S; preferably, the three AK2 chains contain 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably, none of the three AK2 moieties is interrupted; or e) The three AK2 moieties are selected from the group consisting of AK2 -S-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v saturated, linear C substituted with one or more identical or different moieties selected from 12 ~C 24 which may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, such as -OC(O)-, -C(O)-O-, (hetero)cycle-O-(hetero)cycle; AK3 represents a linear or branched, saturated or unsaturated C3-C 12 , preferably C3 to C6, more preferably saturated C3 to C6, especially C3, divalent hydrocarbon-based chain; a and R b is as defined above; preferably, Y represents —OC(O)—; and the compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moiety; preferably, Y represents -OC(O)-; preferably, v is equal to 2; preferably, the three AK2 chains comprise from 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably, none of the three AK2 moieties is interrupted; preferably, the AK2 moieties are saturated; preferably, AK3 represents a trivalent -CH2-CH-CH2- moiety; or f) the three AK2 moieties are -OC(O)-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v linear, saturated, C 12 ~C 24represents a monovalent hydrocarbon-based chain of the formula: -OR and -S-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and / or the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-; A K3, v, R4, R a and R b is as defined above; preferably, Y represents —OC(O)—; the compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties; preferably, Y represents -OC(O)-; preferably, v is equal to 1 or 2, more preferably equal to 1; preferably, the three AK2 chains contain 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably, none of the three AK2 moieties is interrupted; preferably, the AK2 moieties are saturated; preferably, the AK2 moieties contain at least one -OR moiety, preferably at least one -OC(O)-C( a )(R b )-C(O)-R4 moiety; preferably, AK2 is substituted by -S-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v Preferably, AK3 represents a linear or branched, saturated or unsaturated C1 to C6, more preferably saturated C1 to C6, even more preferably C2 hydrocarbon-based chain.

[0152] According to one particular embodiment, the method of treatment according to the invention comprises applying to keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows, at least one compound of formula (I), its optical or geometric isomers, and / or solvates thereof, such as hydrates, or a composition comprising said compound, for example a compound of formula (Ib) below, its optical or geometric isomers, and / or solvates thereof, such as hydrates: m (AK2-Y)-Z-[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n (Ib) Here, in formula (Ib), n+m is equal to 4 and m is not zero; m and n are as defined above for compounds of formula (I); Z is an unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated, and acyclic C-C 24 , especially C3~C 10 , preferably C3, representing a tetravalent hydrocarbon-based moiety; AK2 independently represents -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and preferably one or more -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v C may be linear or branched, saturated or unsaturated, preferably saturated, optionally substituted by a moiety 12 ~C 24 , preferably C 16 ~C 20 , preferably C 18and / or said chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular from -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-; AK3 is a linear or branched, saturated or unsaturated C1-C 12 , preferably C1-C6, more preferably saturated C1-C6, even more preferably C2-C4, preferably C3, divalent hydrocarbon-based chain; v is as defined above; preferably, v is equal to 2; X is as defined above; preferably, X represents a sulfur atom; Y, AK1, u, t, q, R, R4, R a and R b is as defined above; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties.

[0153] According to a preferred embodiment, m is equal to 3, n is equal to 1 and u is equal to 1.

[0154] According to a preferred embodiment, t is equal to 0 and q is equal to 0.

[0155] According to a preferred embodiment, Y represents —C(O)—O—.

[0156] According to a preferred embodiment, none of the AK2 moieties are interrupted. Preferably, the AK2 moieties are saturated. Preferably, the AK2 moieties are not substituted by -OR.

[0157] According to a preferred embodiment, AK3 represents a linear or branched, saturated or unsaturated C1 to C6, more preferably saturated C1 to C6, even more preferably C1 to C4, and even better C3, hydrocarbon-based chain.

[0158] According to a variant of this embodiment, the compound of formula (I) or formula (Ib) is chosen in particular from compound (10) as defined above, its optical or geometric isomers, and / or its solvates, such as hydrates.

[0159] According to one particular embodiment, the treatment method according to the invention comprises applying to keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows, at least one compound of formula (I), its optical or geometric isomers, and / or solvates thereof, such as hydrates, or a composition comprising said compound, for example a compound of formula (Ic) below, its optical or geometric isomers, and / or solvates thereof, such as hydrates: m (AK2-Y)-ZH-[(O)t-(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n (I C) Here, in formula (Ic), Z is a linear or branched, saturated or unsaturated, preferably saturated, and acyclic, polyvalent C 14 ~C 24 , especially C 16 ~C 20 , e.g. C 17 , wherein Z also represents one or more moieties -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n may be substituted by a moiety, preferably unsubstituted; AK2 is -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) vC is linear or branched, saturated or unsaturated, preferably saturated, substituted by one or more identical or different moieties selected from 14 ~C 30 , preferably C 20 ~C 29 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-; X is as defined above and preferably represents a sulfur atom; Y, AK1, AK3, n, m, v, t, q, u, R, R4, R a and R b is as defined above; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties.

[0160] According to a preferred embodiment, n is equal to 0 and m is equal to 1.

[0161] According to a preferred embodiment, Z is a divalent radical.

[0162] According to a preferred embodiment, when Z is an unsaturated chain, AK2 is an unsaturated chain, and when Z is a saturated chain, AK2 is a saturated chain.

[0163] According to a variant of this embodiment, one or more compounds of formula (Ic), their optical or geometric isomers, and / or their solvates, such as hydrates, are in particular of formula (Iic) as defined above.

[0164] According to a variant of this embodiment, the one or more compounds of formula (Iic) are in particular chosen from compound (12) as defined above, their optical or geometric isomers, and / or their solvates, such as hydrates.

[0165] According to one particular embodiment, the method of treatment according to the invention comprises applying to keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows, at least one compound of formula (I), its optical and geometric isomers, and / or solvates thereof, such as hydrates, or a composition comprising said compound, for example a compound of formula (Id), its optical or geometric isomers, and / or solvates thereof, such as hydrates: m (AK2-Y)-Z-[(O)t-(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n (Id) Here, in formula (Id), n+m is equal to 4, preferably m is equal to 3; Z is linear or branched, saturated or unsaturated, preferably saturated or acyclic, C2-C 24 , especially C3~C 10 , particularly C4 or C5, tetravalent hydrocarbon-based moiety, and Z may also be one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n substituted by the moiety, wherein n is preferably equal to 1; AK2 independently represents a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 16 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, which may be selected from the group consisting of -OR and -X-AK3-(OC(O)-C(R a )(Rb )-C(O)-R4) v and / or the chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-; X is as defined above, preferably X represents a sulfur atom; Y, AKI, AKI, u, v, R, R, R a and R b is as defined above, These compounds have at least two -C(O)-C(R a )(R b )-C(O)-R4 moieties.

[0166] According to a preferred embodiment, t is equal to 0 and u is equal to 1.

[0167] According to a preferred embodiment, all AK2 moieties are the same. Preferably, all Y moieties are the same.

[0168] According to a preferred embodiment, Y represents -OC(O)-.

[0169] According to a variant of this embodiment, the compounds of formula (Id) as defined above, their optical or geometric isomers, and / or their solvates, such as hydrates, are in particular compounds of formula (Iid) as defined above.

[0170] According to a preferred embodiment, the method of treatment according to the invention comprises applying to keratinous materials, in particular the skin and / or the lips and / or the eyelashes and / or the eyebrows, at least one compound of formula (I), its optical and geometric isomers, and / or solvates thereof, such as hydrates, or a composition comprising said compound, for example a compound of formula (Ie), its optical or geometric isomers, and / or solvates thereof, such as hydrates: m (AK2-Y)-Z-[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R4) u ] n (Ie) Here, in formula (Ie), n+m is equal to 2, m is not zero, preferably m is equal to 2; n is as defined above for compounds of formula (I); preferably n is zero; Z is linear or branched, saturated or unsaturated, conjugated or non-conjugated, preferably non-conjugated, acyclic or cyclic, aromatic or non-aromatic, preferably non-aromatic, C2-C 24 , especially C3~C 12 , represents a divalent hydrocarbon-based moiety, the Z moiety also being -O-, -N(R a and Z is interrupted by one or more heteroatoms or groups selected from the group consisting of -(CH)-, -S-, -C(O)-, one or more (hetero)cyclic rings, and combinations thereof; preferably, Z is a divalent -(CH) g -(heterocycle)-O-(CH2) h -(heterocycle)-(CH2) j- moiety, where h is 0, 1 or 2, preferably 0 or 1, and g and j are independently integers from 1 to 3, preferably 1; (heterocycle) represents a divalent heterocyclic moiety (i.e., heterocycle), preferably a heterocycloalkyl moiety, more particularly a divalent 5- or 6-membered heterocycloalkyl moiety, especially a divalent tetrahydrofuran moiety or a divalent tetrahydropyran moiety, where the heterocycle is selected from the group consisting of -OR (where R is as defined above), especially -OH or -OC(O)-C(R a )(R b )—C(O)—R4; AK2 is a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 14 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, where the chain is selected from the group consisting of -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R4) v and / or the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-, more preferably uninterrupted; X is as defined above; preferably, X represents a sulfur atom; Y, AK1, AK3, v, t, q, u, R, R4, R a and R b is as defined above; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R4 moieties.

[0171] According to a variant of this embodiment, the compounds of formula (Ie), their optical or geometric isomers, and / or their solvates, such as hydrates, are in particular compounds of formula (Iie) as defined above.

[0172] Another subject of the present invention are compounds of formula (I) as defined above, their salts, isomers and / or solvates thereof, such as hydrates, which differ from compounds (1) to (7) as defined above.

[0173] Another subject of the invention are compounds of formula (Ia), formula (Ib), formula (Ic), formula (Id) and formula (Ie), their salts, isomers and / or solvates thereof, such as hydrates, as defined above, and more particularly compounds of formula (Iic), formula (Iid) and formula (Iie), as defined above.

[0174] In particular, another subject of the present invention is compounds (8), (9), (10), (11), (12), (13) and (14), as defined above, their salts, isomers and solvates thereof.

[0175] Preparation of Compounds of Formula (I)

[0176] In particular, compounds of formula (I), or one or more of formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) or (Iie) may be prepared via the following reaction sequence:

[0177] First step

[0178] In the first step, a commercially available polyol, preferably a natural commercially available polyol, of formula (H) p -Z(OH) m’ is reacted with m equivalents of a fatty acid derivative R'CO-AK'2 under conditions known by a person skilled in the art to form an ester bond Y according to the following scheme: where m' is equal to or greater than m and m is as defined above. (H) p -Z(OH) m’ +m×R'CO-AK'2→ (H) p -Z(OH) m’-m (YAK'2) m wherein, in the scheme: Y represents -OC(O)-; R' especially denotes -OH or -Cl; preferably R' denotes -OH; AK'2 is a linear or branched, unsaturated, C1-C 40 , preferably C 14 ~C 20 , wherein the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular from -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably by -O- or -S-, more preferably uninterrupted.

[0179] According to a preferred embodiment, m is equal to m'.

[0180] The polyol (H) p -Z(OH) m’ can be cyclic or acyclic.

[0181] The cyclic polyol (H) p -Z(OH) m’ As examples there may be mentioned maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose or sorbitan.

[0182] Acyclic polyol (H) p -Z(OH) m’As examples there may be mentioned ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butanediol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethane, mannitol or trimethylolpropane.

[0183] According to a preferred embodiment, polyol (H) p -Z(OH) m’ is selected from glycerol, mannitol, sucrose, ethylene glycol, sorbitan or trimethylolpropane, more preferably polyol (H) p -Z(OH) m’ indicates glycerol.

[0184] The compounds R'CO-AK'2 are preferably unsaturated fatty acids containing from 15 to 36 carbon atoms, preferably from 15 to 24 carbon atoms. They can be mono- or polyunsaturated.

[0185] The monounsaturated fatty acids are in particular chosen from palmitoleic acid, oleic acid, 9-eicosenoic acid, 11-eicosenoic acid, erucic acid, and nervonic acid.

[0186] The polyunsaturated fatty acids are selected, inter alia, from linoleic acid, α-linolenic acid, γ-linolenic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, luminic acid, and hydroxyl monounsaturated fatty acids, in particular 10-hydroxy-cis-12-octadecenoic acid, 10-hydroxy-trans-11-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, 13-hydroxy-cis-9-octadecenoic acid, ricinoleic acid, isoricinoleic acid, and hydroxyl monounsaturated fatty acids selected from polyunsaturated hydroxyl fatty acids, and polyunsaturated fatty acids, in particular densipolic acid, auricolic acid, dimorphecolic acid.

[0187] More preferably, the unsaturated fatty acids are selected from ricinoleic acid, oleic acid, palmitoleic acid, erucic acid, and combinations thereof.

[0188] Second step

[0189] In a second step, all or part of one or more unsaturated groups of one or more AK'2 moieties are converted a) via an epoxidation reaction to give derivatives (III) shown in the scheme described below, e.g., starting compound a1, or b) via a thiol-ene reaction with a (poly)hydroxylated thiol or a thiol bearing one or more acid functional groups to give derivatives (IV) shown in the scheme described below, e.g., compound b3.

[0190] The thiol-ene reaction b) is carried out by the synthesis of (poly)hydroxylated thiols, e.g. of the formula HS-(CH) kThis can be carried out using linear hydroxylated thiols with -OH (where k is an integer from 1 to 12, preferably from 1 to 6), such as 2-mercaptoethanol, 3-mercapto-1-propanol, 6-mercapto-1-hexanol, 4-mercapto-1-butanol, or for example branched hydroxylated thiols, preferably containing 1 to 6 carbon atoms, such as 3-mercapto-3-methylbutanol, 3-mercapto-2-butanol, or for example polyhydroxylated thiols, preferably containing 1 to 6 carbon atoms, such as 3-mercapto-1,2-propanediol HS-CH(OH)-CHOH.

[0191] Therefore, the resulting compound (IV) is -S-AK3-(OH) v wherein v is greater than 1, for example 2, if the thiol is hydroxylated; and wherein A K and v are as defined above for compounds of formula (I).

[0192] The third step

[0193] In the third step, all or some of the epoxy groups of the compound of formula (III) are ring-opened with a nucleophilic compound, in particular i) with an alcohol, preferably a C1-C4 alcohol, such as methanol or ethanol or a polyol, to give a compound of formula (IIIi), such as compound b2 shown in the scheme described later in this specification, or ii) with a carboxylic acid, preferably a C1-C6 carboxylic acid, such as lactic acid, pyruvic acid, benzoic acid, glycolic acid or 2,2-bishydroxymethylpropionic acid, more preferably a carboxylic acid substituted with at least one hydroxyl moiety, such as lactic acid, to give a compound of formula (IIIii), such as compound b1 shown in the scheme described later in this specification.

[0194] According to a preferred embodiment, the carboxylic acid ii) is selected from lactic acid, glycolic acid or 2,2-bishydroxymethylpropionic acid (epoxy acid reaction), the reaction being carried out in the presence of a catalyst, such as imidazole, 1-methylimidazole, N,N-dimethylbenzylamine or caffeine.

[0195] According to a preferred embodiment, the alcohol i) is chosen from ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butanediol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethane and trimethylolpropane, more preferably butylene glycol or trimethylolethane.

[0196] Fourth step

[0197] In the fourth step, all or part of the alcohol functional groups -OH of the compound (IIIi) or the compound (IIIii) and the polyol (H) used in the first step are p -Z(OH) m’ All or part of the alcohol functional groups that may still be present resulting from a )(R b )-C(O)-R4 (wherein Gp preferably represents a hydroxyl moiety or a (C1-C4) alkoxy moiety such as methoxy, ethoxy, isobutoxy or t-butoxy) to form -OC(O)-C(R a )(R b )-C(O)-R4 moiety.

[0198] According to a preferred embodiment, Gp-C(O)-C(R a )(R b )-C(O)-R4 represents an ester selected from ethyl acetoacetate, ethyl 2-methylacetoacetate and tert-butyl acetoacetate, preferably tert-butyl acetoacetate.

[0199] Compounds of formula (Ia) and formula (Ic), such as compounds of formula (Iic), as well as compounds of formula (Id) and formula (Ie), can be obtained according to this process.

[0200] For example, step 4 may be carried out according to the protocol described in Trevino, AS, and Trumbo, DL (2002). Acetoacetylated castor oil in coating applications. Progress in Organic Coatings, 44(1), 49-54. [ka]

[0201] In some cases, the compound (H) resulting from the first step p -Z(OH) m’-m (YAK'2) m are commercially available products. In particular, certain compounds (where m' is equal to m, p is equal to 0, and Z preferably represents -CH2-CH-CH2-) are commercially available products. When p is equal to 0 and m' is equal to m, the compound is an ester of an optionally hydroxylated unsaturated fatty acid, in particular a triglyceride of castor oil, soybean oil, canola oil, or linseed oil. The synthesis of compounds (Ia) to (Ie) begins with the second step described above.

[0202] For example, starting from unsaturated triglycerides, a thiol-ene reaction can be carried out to give (poly)hydroxyl thiols, e.g., SH—(CH) xOH (where x is preferably an integer from 1 to 4), and then the transesterification reaction (as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R. and Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489-2500) was carried out. [ka] [ka]

[0203] For example, starting from an unsaturated triglyceride, a total or partial epoxidation reaction is carried out, followed by ring-opening of one or more resulting epoxy groups, thereby generating alcohol functional groups, and (trans)esterification. Commercial epoxidized triglycerides, such as those sold by Arkema under the trade names Vikoflex 7170 or Vikoflex 7190, may also be used as raw materials.

[0204] For example, the following reaction scheme may be used, in which all epoxies are ring-opened with lactic acid, and then each hydroxyl is esterified with t-Bu-OCOCH2CH3 according to the following scheme: [ka]

[0205] For example, the following reaction scheme may also be used, in which all epoxies are ring-opened with, for example, methanol, and then each hydroxyl is esterified with t-Bu-OCOCH2CH3. [ka]

[0206] Compounds of formula (Ia) to formula (Ie) may also be prepared via the following reaction sequence: In the first step, preferably commercially available natural polyacid (H) p -Z(COOH) m’ (where m' is greater than or equal to m, and m is as defined above) is reacted with m equivalents of a fatty alcohol HO-AK'2 under conditions known by those skilled in the art to form an ester bond Y according to the following scheme: (H) p -Z(COOH) m’ +m×HO-AK'2 → (H) p -Z(COOH) m’-m (YAK'2) m where Y represents -C(O)-O-, and AK'2 represents a linear or branched, unsaturated, C1-C 40 , preferably C 14 ~C 20 represents a monovalent hydrocarbon-based chain, wherein the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular from -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably by -O- or -S-, and more preferably uninterrupted.

[0207] According to a preferred embodiment, m is equal to m'.

[0208] The polyacid (H) p -Z(COOH) m’ can be cyclic or acyclic.

[0209] The polyacid may preferably represent an optionally hydroxylated dicarboxylic acid, an optionally hydroxylated tricarboxylic acid, or an optionally hydroxylated tetracarboxylic acid.

[0210] The non-hydroxylated dicarboxylic acids are selected especially from maleic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, decanedioic acid, dodecanedioic acid, cyclopropanedicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, suberic acid, oxalic acid, malonic acid, succinic acid, phthalic acid, terephthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pimelic acid, sebacic acid, azelaic acid, glutaric acid, adipic acid, fumaric acid and itaconic acid, preferably propanedioic acid, butanedioic acid and pentanedioic acid.

[0211] The hydroxylated dicarboxylic acids are selected in particular from tartaric acid, malic acid, aleuritic acid, 7,18-dihydroxytetracos-15-enoic acid and avenic acid B, preferably malic acid and tartaric acid.

[0212] The (hydroxy)tricarboxylic acid is especially selected from 2-oxaloglutaric acid, oxalosuccinic acid, 3-carboxymethylmuconic acid, 2-methylcitric acid, citric acid, isocitric acid, aconitic acid, transaconitic acid, 1,2,3-propanetricarboxylic acid, 1,2,5-pentanetricarboxylic acid, 1,3,5-benzenetricarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, 3-butene-1,2,3-tricarboxylic acid, 3-butene-1,1,3-tricarboxylic acid, trimethyl acid, 1,2,3-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid and agaric acid, preferably citric acid and aconitic acid.

[0213] The tetracarboxylic acid is selected from 1,2,3,4-butanetetracarboxylic acid, pyromellitic acid, oxydisuccinic acid, thiodisuccinic acid, N-[1,2-dicarboxyethyl]-L-aspartic acid, ethylenediaminetetraacetic acid, ethylenediaminetetrapropionic acid and N,N'-ethylenebis(L-aspartic acid).

[0214] According to a preferred embodiment, the fatty alcohol HO-AK'2 is chosen from fatty alcohols containing from 15 to 36 carbon atoms, preferably from 15 to 24 carbon atoms.

[0215] The fatty alcohol HO-AK'2 can be mono- or polyunsaturated (presence of one or more ethylenic double bonds).

[0216] The fatty alcohol HO-AK'2 may contain several alcohol functional groups.

[0217] The monounsaturated fatty alcohol is selected from, inter alia, oleyl alcohol, docosenol, or an unsaturated fatty alcohol ether, such as polyoxyethylene monooleyl ether, preferably oleyl alcohol. The unsaturated monounsaturated fatty alcohol with multiple alcohol functions is selected from 9-octadecene-1,12-diol.

[0218] The polyunsaturated fatty alcohols are chosen in particular from linoleic alcohol, 2,4-dodecadien-1-ol and dolucol (n is ≧3 and ≦5).

[0219] According to a preferred embodiment, the fatty alcohol HO-AK'2 is selected from oleyl alcohol, linoleyl alcohol or a combination thereof.

[0220] The following steps are identical to those previously described: In a second step, all or part of one or more unsaturated groups of one or more AK'2 moieties are a) converted to an epoxide via an epoxidation reaction to give derivative (III') as shown in the scheme below, e.g., compound a4, or b) via a thiol-ene reaction with a (poly)hydroxylated thiol or a thiol bearing one or more acid functional groups to give derivative (IV') as shown in the scheme below, e.g., compound b5. In the third step, all or part of the epoxy groups of the compound of formula (III') are ring-opened with a nucleophilic compound, for example i) preferably with a C1-C4 alcohol, such as methanol or ethanol or a polyol, to give compound (III'i), for example, compound b4 shown in the scheme below; ii) with a carboxylic acid, preferably a C1-C6 carboxylic acid, for example, lactic acid, pyruvic acid or benzoic acid, more preferably a carboxylic acid substituted with at least one hydroxyl moiety, for example, lactic acid, to give compound (III'ii), for example, compound b6 shown in the scheme below. In the fourth step, all or part of the alcohol functional groups -OH of the compound (III'i) or the compound (III'ii) and the polyol (H) used in the first step are p -Z(OH) m’ All or part of the alcohol functional groups that may still be present resulting from a )(R b )-C(O)-R4 (where Gp preferably represents a hindered alkoxy moiety, e.g., tBu-O-), to form -OC(O)-C(R a )(R b )—C(O)—R4 moiety to give the corresponding compound of formula (I).

[0221] Compounds of formula (Ia) to formula (Ie) in which p is equal to 1, Y represents —C(O)—O—, and m is equal to 1 can also be prepared from unsaturated fatty acids, such as oleic acid, by combining the above-described steps 2, 3, and 4, as described in “The synthesis of Bio-based Michael donors from tall oil fatty acids for polymer development”, Polymers, 2022, 14, 4107.

[0222] For example, the following reaction scheme may be used, in which all epoxies are ring-opened with methanol, and then each hydroxyl is esterified with t-Bu-OCOCH2CH3. [ka]

[0223] For example, the following reaction scheme may also be used, in which the unsaturated oil is converted into a (poly)hydroxyl thiol, such as SH—(CH) x OH (where x is an integer, preferably 1 to 4), followed by transesterification (as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R. and Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489-2500). [ka]

[0224] For example, the following reaction scheme may be used, in which all epoxies are ring-opened with lactic acid, and then each hydroxyl is esterified with t-Bu-OCOCH2CH3. [ka]

[0225] Crosslinker ii)

[0226] The aforementioned treatment method according to the invention comprises applying to keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, (i) at least one compound of formula (I) as defined above and (ii) at least one crosslinking agent.

[0227] For purposes of the present invention, the term "crosslinker," also referred to as "R," refers to a compound that is capable of establishing at least one covalent bond with at least one acetoacetate functional group of one or more compounds of formula (I) used in the treatment methods according to the present invention, thereby crosslinking this or these compounds.

[0228] Preferably, the term "crosslinker," also referred to as "R," refers to a compound that is capable of establishing at least one covalent bond with the acetoacetate functional group of one or more compounds of formula (I) used in the treatment methods according to the present invention, thereby crosslinking this or these compounds.

[0229] For the purposes of the present invention, the terms "crosslinking agent" and "crosslinker" are understood to be equivalent.

[0230] Compositions "C2", "C3" and "C4" as defined above contain at least ii) a crosslinking agent. The compositions of the present invention may contain a fatty phase, an aqueous phase or may be in the form of a direct emulsion or an inverse emulsion. Composition "C4" may be an aqueous composition.

[0231] According to one aspect, the treatment method of the present invention uses a composition designated "C3", in particular a cosmetic composition for keratinous materials, especially the skin and / or lips and / or eyelashes and / or eyebrows, in particular a cosmetic composition for caring for and / or making up keratinous materials, especially the skin, lips, eyelashes and / or eyebrows, comprising: i) at least one compound of formula (I) as described hereinabove and hereinafter; ii) at least one crosslinking agent, in particular at least one crosslinking agent as described hereinabove and hereinafter; and iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as described hereinabove and hereinafter.

[0232] The one or more crosslinking agents of ii) may preferably be present in a mass content ranging from 0.2% to 60% by weight, in particular from 0.5% to 40% by weight, more in particular from 1% to 35% by weight, and even more in particular from 1% to 30% by weight, relative to the total weight of the composition containing them.

[0233] In particular, in composition "C2" or composition "C3", the one or more crosslinkers ii) and the one or more compounds i) as defined above may preferably be present in a mass content of 1% to 35% by weight, relative to the total weight of the composition containing them.

[0234] When the method of treatment includes several steps, including one step using one or more compounds of Formula (Ia), Formula (Ib), Formula (Ic), Formula (Id), Formula (Ie), Formula (Iic), Formula (Iid) and / or Formula (Iie) without a cross-linking agent, the one or more compounds of Formula (I), Formula (Ia), Formula (Ib), Formula (Ic), Formula (Id), Formula (Ie), Formula (Iic), Formula (Iid) or Formula (Iie) may be used by themselves (pure) or may be used in the composition "C1" described previously.

[0235] More precisely, the one or more crosslinking agents ii) suitable for use in the present invention may be selected from compounds having amine, thiol, acrylate and / or carbonyl functions, such as compounds having ketone or aldehyde functions. The crosslinking agent R may also represent a metal alkoxide.

[0236] Thus, according to one particular embodiment, the crosslinker ii) is chosen from (poly)amine, (poly)thiol, (poly)carbonyl, (poly)acrylate and metal alkoxide compounds, and combinations thereof, preferably chosen from (poly)amine compounds.

[0237] The terms "(poly)amine compounds, (poly)thiol compounds, (poly)carbonyl compounds and (poly)acrylate compounds" are intended to denote compounds that contain at least one primary or secondary amine, thiol, carbonyl (e.g., ketone or aldehyde functional group) or acrylate functional group, respectively.

[0238] The metal alkoxide compound is defined below.

[0239] A) (Poly)amine Compounds

[0240] According to a preferred embodiment, the crosslinking agent R is chosen from (poly)amine compounds.

[0241] The (poly)amine compounds may be chosen in particular from polyamine compounds having several primary and / or secondary amine groups or from aminoalkoxysilanes, more in particular from aminoalkoxysilane compounds, diamine compounds, triamine compounds, and combinations thereof.

[0242] The (poly)amine compound is a compound containing 2 to 20 carbon atoms, and may in particular be a nonpolymeric compound. The (poly)amine compound may be acyclic or cyclic, linear or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, and may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -Si(R')2-, -N(R'')-, preferably -O-, -Si(R')2-, or combinations thereof, such as -Si(R')2-O- or -O-Si(R')2-, where R' may be the same or different and represents a (C1-C4) alkyl group, such as methyl, and R'' represents a hydrogen atom or a (C1-C4) alkyl group, preferably a hydrogen atom.

[0243] The term "non-polymeric compound" means a compound that is not obtained directly via a monomer polymerization reaction.

[0244] (Poly)amine compounds which may be mentioned in particular are N-methyl-1,3-diaminopropane, N-propyl-1,3-diaminopropane, N-isopropyl-1,3-diaminopropane, N-cyclohexyl-1,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methylbis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylene Triamine, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-trioxa-1,13-tridecanediamine, spermidine, and C 36 -Alkylenediamines (respectively, Priamine 商標1071, 1073, 1074, 1075), preferably 4,7,10-trioxa-1,13-tridecanediamine.

[0245] According to a particular embodiment of the invention, the (poly)amine compound is a monoamine compound, i.e. it contains only one primary and / or secondary amine group, preferably a primary amine group (NH2).

[0246] One or more of the (poly)amine compounds may be aminoalkoxysilanes, in particular those of the formula R'1Si(OR'2) z (R'3) x and the aminoalkoxysilane may be selected from the group consisting of R'1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C6 hydrocarbon-based chain substituted by a group selected from a primary amine group NH2 or a secondary amine group -N(H)R, where R represents a C1-C4 alkyl, aryl or benzyl substituted by an amino group or by a C1-C4 aminoalkyl group, R'1 may be interrupted in its chain by heteroatoms (O, S, NH) or carbonyl groups (CO), R'1 is linked directly to the silicon atom via a carbon atom, R'2 and R'3 may be the same or different and represent a linear or branched (C1-C6) alkyl group; z represents an integer ranging from 1 to 3, and x represents an integer ranging from 0 to 2; Here, z+x=3.

[0247] In particular, R'1 is an acyclic chain. Preferably, R'1 is a linear or branched, saturated or unsaturated C1-C6 hydrocarbon-based chain substituted by an amine -NH2 or -N(H)R group, where R represents a C1-C6 alkyl, C3-C6 cycloalkyl or C6 aromatic group. More preferably, R'1 is a saturated, linear C1-C6 hydrocarbon-based chain substituted by an amine group NH2. Even more preferably, R'1 is a saturated, linear C2-C4 hydrocarbon-based chain substituted by an amine group NH2.

[0248] In particular, R'2 represents an alkyl group containing 1 to 4 carbon atoms, preferably R'2 represents a linear alkyl group containing 1 to 4 carbon atoms, more preferably R'2 represents an ethyl group.

[0249] In particular, R'3 represents an alkyl group containing 1 to 4 carbon atoms; preferably, R'3 represents a linear alkyl group containing 1 to 4 carbon atoms, more preferably, R'3 represents a methyl or ethyl group. Preferably, z is equal to 3.

[0250] In particular, the one or more (poly)amine compounds are selected from aminoalkoxysilanes containing one primary and / or secondary amine group, preferably a primary (NH) amine group, such as 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, and N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.

[0251] Preferably, the one or more (poly)amine compounds are selected from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, more preferably 3-aminopropyltriethoxysilane (APTES), in particular the products sold by Sigma Aldrich.

[0252] The (poly)amine compounds also include amino polymers, especially those having a molecular weight of 500 g.mol -1 ~1,000,000 g.mol -1 , preferably 500 g.mol -1 ~500,000 g.mol -1 , preferably 500 g.mol -1 ~100,000 g.mol -1 The amino polymer may be selected from amino polymers having a weight average molecular weight in the range of .

[0253] According to a particular embodiment of the invention, the (poly)amine compound is a monoamine compound and is chosen from polydialkylsiloxanes, especially polydialkylsiloxanes of formula (IV): H2N-ALK-Si(R'2)(R'3)-O-[Si(R'2)(R'3)-O] n -Si(R'2)(R'3)-R'4(IV) Here, in formula (IV), ALK represents a linear or branched, preferably linear, (C1-C4) alkylene group, such as propylene; R'2 and R'3 may be the same or different, preferably the same, and represent a (C1-C4) alkyl group, such as methyl; and R'4 represents a linear or branched (C1-C6) alkyl group, preferably C4, for example, n-butyl, and n represents an integer of 2 or more, preferably the value of n is such that the weight average molecular weight of the polydimethylsiloxane is 500 to 3000 g.mol -1As examples of polydimethylsiloxanes (V), mention may be made of the products sold by the company Gelest under the names MCR-A11 and MCR-A12.

[0254] According to a particular embodiment of the present invention, the (poly)amine compound is a diamine compound, i.e., the (poly)amine compound comprises two primary and / or secondary amine groups, preferably primary amine groups (NH).

[0255] More particularly, the (poly)amine compound is selected from compounds of formula (V) or (VI) below: ALK[(O-ALK') m -NH2]2(V) Or, H2N-ALK-Si(R')2-[O-Si(R')2] m -O-Si(R)2-ALK'-NH2(VI) Here, in formula (V) and formula (VI), ALK and ALK′ may be the same or different and represent a linear or branched (C1-C6) alkylene group, preferably a linear group, such as propylene; R' may be the same or different and represents a (C1-C4) alkyl group, such as methyl, and m represents an integer equal to or greater than 0; preferably, the value of m is such that the weight average molecular weight of compound (V) or compound (VI) is 500 g.mol -1 ~55,000 g.mol -1 The range is as follows:

[0256] As examples of compounds of formula (VI), mention may be made of those sold by the company Gelest under the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS-A32 and DMS-A35.

[0257] The (poly)amine compounds which are diamines are in particular polyether diamines, especially those of the formula HN-ALK-O-[ALK'-O] mPolyetherdiamines of the formula -ALK''-NH2 (wherein ALK, ALK' and ALK'' may be the same or different and represent a linear or branched (C1-C6) alkylene group, and m represents an integer equal to or greater than 0), such as 4,7,10-trioxa-1,13-tridecanediamine, or compounds known under the name Jeffamine from the company Hunstman, more particularly α,ω-diamino polyethylene glycols and / or polypropylene glycols (with amine functions at the chain ends), such as the products sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000 and ED-2003.

[0258] According to a particular embodiment of the present invention, the one or more (poly)amine compounds are triamine compounds, i.e. the one or more (poly)amine compounds comprise three primary and / or secondary amine groups, preferably primary amine groups (NH). More particularly, the one or more (poly)amine compounds are polyether triamines, in particular of the formula ALK''' [(O-ALK') m -NH2]3 polyethertriamines (wherein ALK' is as defined above, and ALK''' represents a linear or branched trivalent (C1-C6) alkylene group, and m represents an integer of 0 or greater).

[0259] As (poly)amine compounds which are triamine compounds, mention may be made in particular of polyethertriamines, especially α,ω-diamino polyethylene glycols and / or polypropylene glycols (with amine functional groups at the chain ends), such as the product sold under the reference Jeffamine T-403.

[0260] According to another particular embodiment of the invention, said (poly)amine compound(s) comprise more than three primary and / or secondary amine groups, preferably primary amine groups (NH2).

[0261] In this variant, the one or more (poly)amine compounds are selected from poly(meth)acrylates or poly(meth)acrylamides having primary or secondary amine functional groups in the side chains, such as poly(3-aminopropyl) methacrylamide and poly(2-aminoethyl) methacrylate.

[0262] Preferably, the (poly)amine compound is selected from chitosan (especially poly(D-glucosamine)) and polydimethylsiloxanes containing primary amine groups at the chain ends and / or in the side chains.

[0263] According to this variant, the (poly)amine compound(s) are in particular poly((C2-C5) alkyleneimines), preferably polyethyleneimines and polypropyleneimines, especially poly(ethyleneimines), in particular the products sold under the reference number 408700 by Aldrich Chemical or under the trade name Lupasol by BASF, in particular those having a molecular weight of 1200 to 25,000; poly(allylamines), in particular the products sold under the reference number 479136 by Aldrich Chemical; polyvinylamines and copolymers thereof, in particular those with vinylamides, in particular vinylamine / vinylformamide copolymers, such as Lupasol by BASF; 登録商標 9030; polyamine acids containing NH groups, such as polylysine, in particular the products sold by JNC Corporation (formerly Chisso Corporation); aminodextrans, in particular the products sold by CarboMer Inc.; aminopolyvinyl alcohols, in particular the products sold by CarboMer Inc.; acrylamide (C1-C6) alkylamine-based copolymers, in particular acrylamidopropylamine-based copolymers; and poly(D-glucosamine), for example Kionutrime CSG by Kytozyme. 登録商標 The product is selected from those sold under the name

[0264] According to one particular embodiment, the polydimethylsiloxanes containing primary amine groups at the chain ends and / or in the side chains are chosen from compounds of formula (VII) below: R a -Si(R b )(R c )-O-[Si(R b )(R c )-O] m -[Si(ALK 1 -NH2)(R a )-O] n -Si(R b )(R c )-R a (VII) Wherein, in formula (VII), R a may be the same or different and represent a hydroxyl group or a (C1-C4) alkyl group; R b and R c may be the same or different, preferably the same, and represent a (C1-C4) alkyl group, for example, methyl; ALK 1 represents a linear or branched (C1-C6) alkylene group optionally interrupted by an N(H) group, m and n are integers equal to or greater than 1; preferably, m and n are integers equal to or greater than 1, so that the weight average molecular weight of the compound of formula (VII) is 1000 g.mol -1 ~500,000 g.mol -1 The range is as follows:

[0265] According to a preferred variant, formula (VII) is R a , R b and R c represents a methyl group, and ALK 1 represents a propylene group, and n and m are the values ​​that indicate the weight average molecular weight of the polydimethylsiloxane is 1,000 g / mol. -1 ~55,000 g.mol -1 The range is as follows:

[0266] As examples of polydimethylsiloxanes of formula (VI), mention may be made of those sold by Gelest under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203.

[0267] According to another variant, formula (VII) can be represented by R a represents hydroxyl or a (C1-C4) alkyl group, such as methyl, and ALK 1 represents a (C5-C6) alkylene group substituted with an NH group; preferably, ALK 1 represents -(CH2)3-N(H)-(CH2)2-, and m and n are the numbers indicating that the weight average molecular weight of the compound of formula (VI) is 5,000 g.mol -1 ~500,000 g.mol -1 The range is as follows:

[0268] As amine polymers, mention may be made of α,ω-diaminopolytetrahydrofuran (or polytetramethylene glycol) and α,ω-diaminopolybutadiene.

[0269] According to a particular embodiment of the invention, the (poly)amine compound is chosen from hyperbranched polymers containing at least one amino group and dendrimers having at least one amino group, such as PAMAM polyamidoamine dendrimers having an ethylenediamine core and terminal amine functional groups.

[0270] According to a preferred embodiment, the composition comprises a crosslinking agent R, which is chosen from (poly)amine compounds, in particular chitosan, aminoalkoxysilanes, polydimethylsiloxanes containing primary amine groups at the chain end or in the side chain, amodimethicone, polyglucosamine, spermidine and combinations thereof.

[0271] More preferably, the composition comprises a crosslinker selected from chitosan, aminoalkoxysilanes, and polydialkylsiloxanes containing primary amine groups at the chain ends or in the side chains, such as amodimethicone, and even more preferably selected from poly(D-glucosamine), 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, spermidine, and polydimethylsiloxanes containing terminal amino groups at the chain ends, such as bis-cetearyl amodimethicone.

[0272] B) (Poly)thiol Compounds

[0273] According to a preferred embodiment, the crosslinking agent R is chosen from (poly)thiol compounds, also known as "(poly)mercapto" compounds.

[0274] The (poly)thiol compound may in particular be organic or inorganic, preferably organic.

[0275] In a preferred embodiment, the (poly)thiol compound is silicon-based, i.e., the (poly)thiol compound comprises one or more thiol groups, and the (poly)thiol compound also comprises at least one siloxane chain.

[0276] In certain embodiments, the (poly)thiol compound is inorganic. For example, polythiol silicones can be mentioned.

[0277] The (poly)thiol compound may in particular be chosen from non-polymeric (poly)thiol compounds.

[0278] For the purposes of the present invention, the term "non-polymeric compound" means a compound that is not obtained directly via a monomer polymerization reaction.

[0279] According to one embodiment of the invention, the one or more (poly)thiol compounds are organic, non-polymeric compounds of formula (VIII) below, as well as solvates, such as hydrates, thereof: L(SH) q (VIII) Here, in formula (VIII), q represents an integer of 2 or more; preferably, q is 2 to 10, more preferably 2 to 5; L represents a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, polyvalent (at least divalent) group, in particular containing 1 to 500 carbon and / or silicon atoms, more in particular 2 to 40 carbon and / or silicon atoms, even more in particular 3 to 30 carbon and / or silicon atoms, preferably 6 to 20 carbon atoms; L is selected from O, S, N, Si, C(X) and combinations thereof, such as, for example, -O-, -OC(X)-, -N(R)-C(X)-, -Si(R c )(R d )-O-, where R represents a hydrogen atom or a (C1-C6) alkyl group, in particular methyl; and / or L may be interrupted and / or terminated by one or more heteroatoms or groups selected from -N(R a )R b and -(X') a -C(X)-(X'') b -R a wherein X, X' and X'' may be the same or different and are substituted with one or more groups selected from an oxygen atom or a sulfur atom, or N(R b a and b are 0 or 1, preferably the sum of a+b is 1; R a and R b may be the same or different and represent a hydrogen atom or a (C1-C6) alkyl or aryl(C1-C4) alkyl group, such as benzyl, preferably R a and R b represents a hydrogen atom; and R c and R dmay be the same or different and represent a (C1-C6) alkyl, aryl(C1-C4) alkyl or (C1-C6) alkoxy group.

[0280] According to a particular embodiment of the invention, the (poly)thiol compound(s) are chosen from polythiol compounds, especially polythiol compounds containing from 2 to 20 carbon atoms.

[0281] According to a preferred embodiment, the one or more (poly)thiol compounds are non-polymeric, in particular compounds of formula (VIII) as defined above, where q is an integer greater than or equal to 2, preferably q is an integer between 2 and 10, preferably between 2 and 5.

[0282] The (poly)thiol compounds suitable for use in the present invention are preferably dithiol compounds.

[0283] Preferably, L is C to C 18 The polythiol preferably represents a polyvalent moiety of the formula: 18 Dithiol. Preferably, C8 to C 18 The chain is a hydrocarbon-based chain, i.e., formed from carbon atoms and hydrogen atoms. In particular, the lipophilic polythiol is a linear C8-C 16 , among others, C 10 ~C 14 As the (poly)thiol compound of formula (VII), more particularly mention may be made of 1,8-octanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol, 1,16-hexadecanedithiol and 1,18-octadecanedithiol. Preferably, 1,10-decanedithiol, 1,12-dodecanedithiol and / or 1,14-tetradecanedithiol, preferably 1,12-dodecanedithiol, may be used.

[0284] According to another particular embodiment of the invention, the one or more (poly)thiol compounds are chosen from thiolated alkoxysiloxanes, such as compounds of formula (VIII') below: R'1-Si(OR'2)z(R'3) x (VIII') Here, in formula (VIII'), R'1 is a C1-C alkyl group that is linear or branched, saturated or unsaturated, cyclic or acyclic, substituted with one or more groups selected from a thiol group, aryl, aryloxy, arylthio, and arylamino. 12 a hydrocarbon-based chain, wherein the aryl group is substituted by one or more thiol groups or thiol(C1-C6)alkyl, preferably thiol(C1-C6)alkyl; and R'1 may be interrupted in the hydrocarbon-based chain by one or more heteroatoms, such as O, S, N, a carbonyl group C(O) or a combination thereof, such as an ester -C(O)-O- or an amide -C(O)-N(H)-, and R'1 is bonded directly to the silicon atom via a carbon atom, R'2 and R'3 may be the same or different and represent a linear or branched alkyl group containing 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as methyl; z represents an integer ranging from 1 to 3, and x represents an integer ranging from 0 to 2; Here, z+x=3.

[0285] Preferably, R'2 represents a linear or branched, preferably linear, alkyl group containing 1 to 4 carbon atoms, such as ethyl.

[0286] Preferably, R'3 represents a linear or branched, preferably linear, alkyl group containing 1 to 4 carbon atoms, such as methyl or ethyl.

[0287] Preferably, R'1 is an acyclic chain, in particular R'1 is a linear or branched, saturated or unsaturated, preferably saturated, C1 to C6 hydrocarbon-based chain substituted with one or more thiol groups, preferably substituted with one thiol group.

[0288] Preferably, R'1 is a saturated, linear hydrocarbon-based chain substituted with a thiol group, and R'2 represents an alkyl group containing 1 to 4 carbon atoms.

[0289] Preferably, R'3 represents an alkyl group containing 1 to 4 carbon atoms.

[0290] Preferably, z is equal to 3.

[0291] According to a more particular embodiment of the present invention, the thiolated alkoxysiloxane is selected from compounds of formula (IX): (R 1 O)(R 2 )(R 3 )Si-[CH(R 4 )] t -[N(R' 4 )-L 1 ] p -SH (IX) Here, in formula (IX), p is 0 or 1; t is an integer from 1 to 4, preferably 2; R 1 represents a (C1-C6) alkyl moiety; R 2 and R 3 may be the same or different, preferably the same, and are selected from (C1-C6) alkyl groups, in particular C1-C4 alkyl groups, such as methyl, and (C1-C6) alkoxy groups, in particular (C1-C4) alkoxy groups, such as methoxy; R 4 and R' 4 may be the same or different and represent a hydrogen atom or a (C1-C6) alkyl group, such as methyl; L1 is a saturated, linear or branched, divalent C1-C 20 represents a hydrocarbon-based moiety.

[0292] According to a particular embodiment of the invention, the thiolated alkoxysiloxane is chosen from compounds of formula (IX') below: (R' 1 O)(R' 2 )(R' 3 )Si-CH(R 4 )-CH(R 5 )-(L 2 ) q -SH (IX') Here, in formula (IX'), q is equal to 0 or 1; X represents an oxygen atom or a sulfur atom, preferably a sulfur atom; R' 1 represents a (C1-C6) alkyl moiety; R' 2 and R' 3 may be the same or different, preferably the same, and are selected from (C1-C6)alkoxy groups, in particular C1-C4 alkoxy groups, and (C1-C6)alkyl moieties; R 5 represents a hydrogen atom or a C1-C4 alkyl group optionally substituted by an amino, thiol or hydroxyl group; R 4 represents a hydrogen atom or a C1-C4 alkyl group, particularly methyl; L 2 is a linear or branched, saturated C1-C alkyl group optionally interrupted by heteroatoms, e.g., —N(H)—, and / or optionally substituted by one or more hydroxyl, thiol, or amino groups; 20 represents a divalent hydrocarbon-based group of the formula:

[0293] Preferably, the one or more thiolated alkoxysilanes are selected from 4-(trimethoxysilyl)-1-butanol, 3-(trimethoxysilyl)-1-propanol, 3-(triethoxysilyl)-1-propanol, 11-(trimethoxysilyl)-1-undecanethiol, 4-(trimethoxysilyl)-2-butanethiol, 2-(triethoxysilyl)ethanethiol, 3-(triethoxysilyl)-1-propanethiol, 2-(trimethoxysilyl)ethanethiol, 3-(trimethoxysilyl)-1-propanethiol, and 3-(dimethoxymethylsilyl)-1-propanethiol.

[0294] More preferably, the one or more thiolated alkoxysilanes are selected from 2-(triethoxysilyl)ethanethiol (18236-15-2) and 3-(triethoxysilyl)-1-propanethiol (14814-09-6).

[0295] According to a preferred embodiment of the present invention, the one or more (poly)thiol compounds are selected from polymeric (poly)thiol compounds.

[0296] The polymeric (poly)thiol compounds can be star, comb, brush, and dendritic homopolymers or copolymers containing thiol units. The polymers can be of natural origin, such as polysaccharides or polypeptides, or of synthetic origin, such as acrylic polymers, polyesters, or polyglycols. The thiol units can be present as terminal and / or side groups.

[0297] Examples that may be mentioned include the polymers described in the following documents: Polymers containing groups of biological activity, C.G. Overberger et al., Polytechnic Institute of Brooklyn, http: / / pac.iupac.org / publications / pac / pdf / 1962 / pdf / 0402x0521.pdf; European Patent Application Publication No. EP 1,247,515 A2; U.S. Pat. No. 3,676,440; and European Patent Application No. EP 1,572,778.

[0298] The polymeric (poly)thiol compounds of the present invention are preferably organic and / or silicone compounds, more preferably compounds of formula (X): POLY(SH) q (X) Here, in formula (X), Q is 2 or more, preferably 3 or more; POLY is a polymer-based moiety, preferably a carbon-based or silicon-based compound; POLY is selected from O, S, N, Si, C(X) and combinations thereof, such as -O-, -OC(X)-, -N(R)-C(X)-, -Si(R)- c )(R d )—O—, where R represents a hydrogen atom or a (C1-C6) alkyl group, such as methyl; and / or POLY represents one or more halogen atoms or R a (R b )N- and -(X') a -C(X)-(X'') b -R a X, X' and X'' may be the same or different and may be substituted by an oxygen atom or a sulfur atom, or N(R b a and b are 0 or 1, preferably the sum of a+b is 1; R a and R bmay be the same or different and are a hydrogen atom or (C1 to C 10 ) alkyl or aryl(C1-C4) alkyl group, such as benzyl, preferably R a and R b represents a hydrogen atom; and R c and R d may be the same or different, (C1 to C 10 ) alkyl, aryl(C1-C4) alkyl or (C1-C 10 ) represents an alkoxy group.

[0299] Methods for preparing the polymeric (poly)thiol compounds used according to the present invention are known to those skilled in the art; some methods are reported herein below in a non-limiting manner. The polymeric (poly)thiol compounds used according to the present invention can be obtained by polymerization or polycondensation of monomer units bearing a thiol or protected thiol functional group, optionally as copolymerization or copolycondensation of monomer units not bearing a thiol or protected thiol functional group.

[0300] According to one embodiment of the invention, the polymeric (poly)thiol compounds used according to the invention are polymers that are soluble in cosmetic media, in particular in aqueous or aqueous alcoholic media, and are more preferably derived from aminopolymers and their ammonium salts, or polyhydroxylated polymers.

[0301] According to another embodiment of the invention, the thiolated polymer used according to the invention is a polymer that is soluble in a lipophilic medium.

[0302] According to one embodiment of the present invention, the polythiol compound is a polymer compound of formula (X), wherein q represents an integer equal to or greater than 2, and POLY represents a carbon-based and / or silicon-based, preferably silicon-based, polymer moiety, wherein POLY also comprises one or more heteroatoms selected from O, N, or S, and / or one or more functional groups selected from (thio)ester functional groups, (thio)ketone functional groups, (thio)amide functional groups, (thio)urea functional groups, and (thio)carbamate functional groups, and / or one or more linear or branched (C1-C 10 ) alkyl group or a straight-chain or branched (C1-C 10 ) alkoxy groups. When POLY is substituted, it is understood that the thiol functionality may be carried by one or more substituents.

[0303] The weight average molecular weight of the polythiol polymer compound, e.g., the polythiol polymer compound of formula (X), is generally 500 to 400,000 g.mol -1 , preferably 500 to 150,000 g.mol -1 , is.

[0304] According to a particular embodiment of the invention, the polythiol compound is chosen from polyorganosiloxanes having thiol groups at the terminal chains, such as compounds of formula (XI) below: HS-L 4 -Si(R a )(R b )-O-[Si(R a )(R b )-O] n -Si(R a )(R b )-L 5 -SH (XI) Wherein, in formula (XI), R a and R bmay be the same or different, preferably the same, and represent a group selected from (C1-C4) alkyl, such as methyl, (C1-C4) alkoxy, such as methoxy, aryl, such as phenyl, aryloxy, such as phenoxy, aryl(C1-C4) alkyl, such as benzyl, or aryl(C1-C4) alkoxy, such as benzoxy, preferably (C1-C4) alkyl, such as methyl; n represents an integer of 1 or greater, and more particularly, the value of n is such that the weight average molecular weight of the silicone is 500 to 55,000 g / mol -1 in particular, n is an integer in the range of 1 to 100, preferably in the range of 5 to 50, preferably in the range of 10 to 30, and L 4 and L 5 may be the same or different, preferably the same, and represent a linear or branched, saturated or unsaturated, optionally cyclic, hydrocarbon-based chain having 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen atoms, in particular oxygen atoms, and in particular a covalent bond or a (C1-C6)alkylene, (C1-C6)alkyleneoxy, oxy(C1-C6)alkylene, (C1-C6)alkyleneoxy(C1-C6)alkylene, (C1-C6)alkyleneoxy(C1-C6)alkyleneoxy or oxy(C1-C6)alkyleneoxy(C1-C6)alkylene group, preferably a (C1-C6)alkylene, (C1-C6)alkyleneoxy, oxy(C1-C6)alkylene or (C1-C6)alkyleneoxy(C1-C6)alkylene group.

[0305] Preferably, the (poly)thiol compound is a polythiol polyorganosiloxane, more preferably a polythiol polydimethylsiloxane, especially one selected from compounds of formula (XII) below: HS-L 4 -Si(CH3)2-O-[Si(CH3)2-O] n -Si(CH3)2-L 5 -SH (XII) Here, in formula (XII), L 4 and L 5 is as defined above in formula (IX), in particular L 4 and L 5 represents a divalent group selected from a (C1-C6)alkylene, (C1-C6)alkyleneoxy, oxy(C1-C6)alkylene or (C1-C6)alkyleneoxy(C1-C6)alkylene group, more preferably -R2-, -O-R2-, -R2-O- and -R2-O-R2-, preferably -R2-O-R2-, where R2 represents a linear or branched, preferably linear, (C2-C6)alkylene group, for example, ethylene or n-propylene, preferably n-propylene; and n is as defined in formula (XI).

[0306] As polythiol compounds of formula (XII), mention may be made of mercaptosiloxanes or thiolated siloxanes in which the thiol function is at the chain end, such as those sold by Shin-Etsu Chemical Co., Ltd. under the reference number X-22-167B, and mercaptosiloxanes in which the mercapto function is attached to the side chain, such as those sold by Shin-Etsu Chemical Co., Ltd. under the reference number KF-2001, or polydimethylsiloxanes in which the thiol function is at the chain end via a thio-n-propyl group, such as those sold by the company Gelest under the name DMS-SM 21.

[0307] Preferably, the polythiol compound is a polyorganosiloxane having a thiol group in a side chain, such as a compound of the following formula (XIII): R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALK1-SH)-O] n -Si(R b )(R d )-Ra (XIII) Here, in formula (XIII), R a and R b is as defined in formula (XI), and R d is R a and R b and preferably R a , R b and R d are the same and represent a (C1-C6) alkyl group, for example, methyl; R d may also be a (C1-C6) alkyl group, preferably a (C1-C4) alkyl group, such as methyl, substituted with a (C1-C4) alkylamino or amino or thiol group; ALK1 represents a linear or branched, optionally cyclic, saturated or unsaturated, divalent hydrocarbon-based chain having 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen atoms, in particular oxygen atoms, or (thio)carbonyl groups C(X) (wherein X represents O or S or combinations thereof, such as -O-, -OC(O)- or -C(O)-O-); preferably, ALK1 represents a (C1-C6) alkylene, more preferably a (C1-C4) alkylene group, such as propylene; n and m may be the same or different and represent integers greater than 2, and more particularly, the values ​​of m and n are such that the weight average molecular weight of the polyorganosiloxane is 1,000 to 55,000 g.mol -1 It is of the type.

[0308] As examples of polythiol compounds of formula (XIII), mention may be made of those sold under the names GP-367, GP-71-SS, GP-800 and GP-710s, preferably GP-367, sold by Genesee Polymers.

[0309] The polythiol compounds are in particular polydimethylsiloxanes having at least two thiol groups, such as the products SMS-022, SMS-042 and SMS-992 sold by the company Gelest (https: / / www.gpcsilicones.com / products / silicone-fluids / mercapto-functional, https: / / www.shinetsusilicone-global.com / products / type / oil / detail / search / deg07.shtml, and 1053_ReactiveSilicones_Silanes / Silicones(Gelest)).

[0310] According to a particular embodiment of the invention, the (poly)thiol compound is selected from hyperbranched polymers containing at least one thiol group and dendrimers carrying at least one thiol group, such as thiolated PAMAM dendrimers.

[0311] Preferably, the (poly)thiol compounds used according to the invention are selected from polydiallylsiloxanes, especially polydimethylsiloxanes containing at least two thiol groups, such as compounds of formula (XIII):

[0312] C) (Poly)acrylate Compounds

[0313] According to one particular embodiment, the crosslinking agent is a (poly)acrylate compound.

[0314] The term "(poly)acrylate" refers to a (poly)acrylate having at least one acrylate ester group H2C=C(R e )—C(O)—Y—, where R e represents a hydrogen atom or a (C1-C4) alkyl group, such as methyl, and preferably R e represents a hydrogen atom, and Y represents an oxygen atom or an amino group -N(H)-, preferably an oxygen atom.

[0315] More particularly, the (poly)acrylate of the present invention is a compound of formula (XIV): L[-YC(O)-C(R e )=CH2] q (XIV) where, in formula (XIV), q and L are as defined in formula (VIII), and Y and R e is as defined above, preferably Y=O and R e =H.

[0316] According to a preferred embodiment, the compounds of formula (XIV) are those in which L represents a divalent or trivalent, preferably trivalent, hydrocarbon-based chain having 1 to 8 carbon atoms, q is 2 or 3, preferably 3, Y represents O, and R e represents a hydrogen atom.

[0317] According to one particular embodiment, the (poly)acrylate compound is chosen from polyorganosiloxanes comprising at least one acrylate group in the side chain, such as compounds of formula (XV) below: R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALK1-YC(O)-C(R e )=CH2)-O] n -Si(R b )(R d )-R a (XV) Here, in formula (XV), R a , R b and R d is as defined for formula (XIII), preferably R a , R b and R d represents a (C1-C6) alkyl group, for example, methyl, ALK1 is as defined for formula (XIII), preferably ALK1 represents a (C1-C6) alkylene group, more preferably a (C1-C4) alkylene group, for example propylene; n and m may be the same or different and represent integers greater than 2, and more particularly, the values ​​of m and n are such that the weight average molecular weight of the polyorganosiloxane is between 1,000 and 55,000 g.mol -1 and Y is as defined above, preferably an oxygen atom.

[0318] More particularly, the (poly)acrylate compounds are 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, bis(trimethylolpropane) triacrylate, glyceryl 1,3-diglycerolate diacrylate, glyceryl propoxylate (1PO / OH) triacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol ethoxylate diacrylate, hydroxypivalyl hydroxypivalate, neopentyl glycol diacrylate, neopentyl glycol propoxylate (1PO / OH) diacrylate, pentaerythritol methyl acrylate, pentyl glycol di ... It may be selected from taerythrityl tetraacrylate, pentaerythrityl triacrylate, poly(propylene glycol) diacrylate, tricyclo[5.2.1.02,6]decane dimethanol diacrylate, trimethylolpropane ethoxylate (1EO / OH) methyl ether diacrylate, trimethylolpropane propoxylate triacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tri(propylene glycol) diacrylate, and tris[2-(acryloyloxy)ethyl]isocyanurate.

[0319] The (poly)acrylate compound may also be selected from N,N'-methylenebisacrylamide.

[0320] According to this embodiment, the (poly)acrylate compound is combined with an amine catalyst in the process, as described, for example, in Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019). Preferably, the one or more amine catalysts are selected from piperidine, DMAP (dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene), more preferably selected from DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

[0321] More particularly, the (poly)acrylate compound is chosen from compounds of formula (XIV), especially trimethylolpropane triacrylate, and compounds of formula (XV), especially copolymers of dimethylsiloxane and acryloxypropylmethylsiloxane.

[0322] D) Metal alkoxide

[0323] According to one particular embodiment, the crosslinker R is of the following formula (XIV) a ), formula (XIV b ), formula (XIV c ) and formula (XIV d ), and combinations thereof, are selected from the group consisting of metal alkoxides of: M-(OR1) n (XIV a ) RM-(OR1) n-1 (XIV b ) (R1O) n-1 -M-R''-M'-(OR1') n’-1 (XIVc ) RM(R')-(OR1) n-2 (XIV d ) Here, formula (XIV a ), formula (XIV b ), formula (XIV c ) and formula (XIV d ) in M and M' may be the same or different and are selected from alkaline earth metals, transition metals, metals of the lanthanide series, post-transition metals such as aluminum or tin, and metalloids such as boron, preferably transition metals such as titanium and post-transition metals such as aluminum, n and n' represent the valence of the atoms represented by M and M', respectively; R1 and R1' may be the same or different and represent a linear or branched, saturated or unsaturated hydrocarbon-based group containing 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms, which may be interrupted by 1 to 20 heteroatoms selected from O, N, S and P, in particular O or N; and / or which may be substituted by one or more hydroxyl or carbonyl groups; R and R' may be the same or different and represent a hydrogen atom or a linear or branched, acyclic or cyclic, saturated or unsaturated, hydrocarbon-based group containing 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms, optionally interrupted by 1 to 20 heteroatoms selected from O, N, S and / or P, especially O or N, and / or said hydrocarbon-based group may be substituted by one or more hydroxyl or carbonyl groups; R″ represents —O—, —N(R2)—, —S—, or a linear, cyclic or branched, saturated or unsaturated, divalent hydrocarbon-based group containing 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms, optionally interrupted by 1 to 20 heteroatoms selected from O, N, S and P, especially O or N, wherein R2 represents a linear, cyclic or branched, saturated or unsaturated hydrocarbon-based group containing 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms.

[0324] Preferably, M and M', which may be the same or different, represent an atom selected from a transition metal, such as titanium or zirconium, or an alkaline earth metal, such as magnesium, more preferably selected from a transition metal, such as titanium or zirconium, even more preferably titanium.

[0325] Preferably, the one or more organometallic compounds are of formula (XIV) as defined above. a According to this preferred embodiment, the one or more organometallic compounds are more particularly selected from the alkoxides of formula (XIV a ), where M represents an atom selected from transition metals, metals of the lanthanide series, post-transition metals such as aluminum or tin, and metalloids such as boron, or alkaline earth metals such as magnesium or calcium; n represents the valence of the atom represented by M; and R1 represents a saturated, linear or branched, hydrocarbon-based group containing 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms.

[0326] According to another more preferred embodiment, the one or more organometallic compounds are represented by the formula (XIV a), where M represents an atom selected from transition metals, such as zirconium or titanium, metals of the lanthanide series, post-transition metals, such as aluminum or tin, metalloids, such as boron, alkaline earth metals, such as magnesium, preferably M represents a titanium atom, n represents the valence of the atom represented by M, especially 1, 2, 3 or 4, in particular 4; R represents a methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or t-butyl group.

[0327] According to an even more preferred embodiment, the one or more organometallic compounds are zirconium ethoxide (Zr(OC2H5)4), zirconium propoxide (Zr(OCH2CH2CH3)4), zirconium isopropoxide (Zr(OCH(CH3)2)4), zirconium butoxide Zr(OCH2CH2CH2CH3)4, zirconium tert-butoxide (Zr(OC(CH3)3)4), titanium ethoxide (Ti(OC2H5)4), titanium propoxide (Ti(OCH2CH2CH H3)4), titanium isopropoxide (Ti(OCH(CH3)2)4), titanium butoxide (Ti(OCH2CH2CH2CH3)4), titanium tert-butoxide (Ti(OC(CH3)3)4), titanium 2-ethylhexyloxide (Ti(OCH2CH(C2H5)(CH2)3CH3)4), and combinations thereof, and more preferably selected from zirconium propoxide, titanium propoxide, titanium butoxide, and combinations thereof.

[0328] More preferably, the crosslinker R is represented by the formula (XIV a ), where M represents an atom selected from the transition metals, especially titanium, for example titanium butoxide.

[0329] E) (Poly)carbonyl compounds

[0330] According to one particular embodiment, the crosslinking agent R is a (poly)carbonyl compound.

[0331] In particular, the (poly)carbonyl compound is terephthalaldehyde, 5,5-dimethyl-1,3-cyclohexanedione, phenylglyoxal, isophthalaldehyde, 4-acetylbenzaldehyde, 4,4-diformyltriphenylamine, 2-acetylbenzaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, The (poly)carbonyl compounds are selected from the group consisting of methyl ketone, ...

[0332] According to one particular embodiment, the (poly)carbonyl compound(s) are chosen from nonionic or anionic oxidized polysaccharides, which contain one or more aldehyde groups and, optionally, one or more anionic groups.

[0333] These anionic groups are preferably carboxyl or carboxylate groups.

[0334] The nonionic or anionic oxidized polysaccharides according to the present invention may be represented by the following formula (II): P-(CHO) m (COOQ) n (II) Here, in formula (II), P represents a polysaccharide chain consisting of monosaccharides containing 5 or more carbon atoms, preferably 6 or more carbon atoms, more particularly 6 carbon atoms; Q is selected from a hydrogen atom, an ion derived from an alkali metal or alkaline earth metal, such as sodium or potassium, ammonia, organic amines, such as monoethanolamine, diethanolamine, triethanolamine and 3-amino-1,2-propanoenol, and basic amino acids, such as lysine, arginine, sarcosine, ornithine and citrulline; m+n is greater than or equal to 1; m is the degree of substitution of the polysaccharide with one or more aldehyde groups (DS(CHO)) in the range of 0.001 to 2, preferably in the range of 0.005 to 1.5; n is a value such that the degree of substitution of the polysaccharide with one or more carboxy groups (DS(COOX)) is within the range of 0 to 2, preferably within the range of 0.001 to 1.5.

[0335] The expression "degree of substitution DS(CHO) or DS(COOX) of a polysaccharide according to the invention" means the ratio of the number of carbons oxidized to give aldehyde or carboxy groups to the number of basic monosaccharides (including those ring-opened by prior oxidation) that make up the polysaccharide, for all repeating units that make up the polysaccharide. CHO and COOX groups can be obtained during oxidation of specific carbon atoms, for example on carbon atoms 2, 3 or 6 of a sugar unit containing six carbon atoms.

[0336] Preferably, the oxidation can occur at the 2- and 3-positions of the carbon atoms, more particularly at a ratio of 0.01% to 75% of the number of rings in the open ring, preferably at a ratio of 0.1% to 50% of the number of rings.

[0337] The polysaccharide chains represented by P are preferably selected from cellulose, starch, maltodextrin, guar gum, xanthan gum, pullulan gum, agar-agar gum, carrageenan gum, gellan gum, acacia gum, polyxylan and tragacanth gum, and derivatives thereof.

[0338] The term "derivative" means a compound obtained by chemical modification of the compounds described above. The derivative may be an ester, amide or ether of the compounds described above.

[0339] The oxidation can be carried out according to methods known in the art, for example, according to the methods described in French Patent No. FR 2,842,200, French Patent No. FR 2,854,161 or in the article "Hydrophobic films from maize bran hemicelluloses" by E. Fredon et al., Carbohydrate Polymers 49, pages 1-12 (2002).

[0340] Another oxidation method is described in the article "Water soluble oxidized starches by peroxide reaction extrusion", Industrial Crops and Products 7, REWing, JL Willet, 45-52 (1997).

[0341] According to this embodiment, the (poly)carbonyl compound is combined with an amine catalyst in its implementation, as described in the documents Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019). Preferably, the one or more amine catalysts are selected from piperidine, DMAP (dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene), more preferably selected from DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

[0342] According to a preferred embodiment, the crosslinking agent is selected from (poly)amine compounds A), (poly)thiol compounds B), (poly)acrylate compounds C), metal alkoxides D) and (poly)carbonyl compounds E), preferably from (poly)amine compounds A).

[0343] In particular, the (poly)amine compound A) is selected from a) chitosan, such as poly(D-glucosamine), b) polyetherdiamines, in particular polyethylene glycol α,ω-diamines (having amine functions at the chain ends), c) polyethertriamines, such as polyetheramine (i.e. Jeffamine), d) aminoalkoxysilanes, such as APTES, and e) polydialkylsiloxanes containing primary amine groups at the chain ends or in the side chains, in particular polydimethylsiloxanes containing primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2), and amodimethicones with amine groups in the side chains, such as bis-cetearyl amodimethicone, in particular the products sold by Momentive Performance Materials.

[0344] According to a preferred embodiment, the (poly)amine compound A) is chosen from a) chitosan, such as poly(D-glucosamine), c) polyethertriamines, such as polyetheramine (i.e. Jeffamine), and e) polydialkylsiloxanes containing terminal or pendant primary amine groups, in particular polydimethylsiloxanes containing primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2), and amodimethicones with pendant amine groups, such as bis-cetearyl amodimethicone, especially the products sold by Momentive Performance Materials.

[0345] In particular, the (poly)thiol compound B) is selected from a) polydialkylsiloxanes having thiol functional groups and b) alkoxysilanes having thiol functional groups, in particular a) polydialkylsiloxanes having thiol functional groups, preferably polydimethylsiloxanes (e.g. mercaptopropyl) having thiol groups in the side chains, especially compounds of formula (XIII):

[0346] In particular, the (poly)acrylate compound C) is selected from compounds of formula (XIV), especially trimethylolpropane triacrylate, and compounds of formula (XV), especially copolymers of dimethylsiloxane and acryloxypropylmethylsiloxane, preferably trimethylolpropane triacrylate.

[0347] According to a preferred embodiment, the one or more cross-linking agents are selected from: A) a (poly)amine compound, ia) chitosan, e.g. poly(D-glucosamine), ib) polyetherdiamines, in particular polyethylene glycol α,ω-diamines, which have amine functional groups at the chain ends; ic) polyethertriamines, especially polyetheramines (i.e., Jeffamine); id) aminoalkoxysilanes, in particular APTES, ie) 4,7,10-trioxa-1,13-tridecanediamine, and if) polydialkylsiloxanes containing primary amine groups at the chain end or in the side chain, in particular polydimethylsiloxanes containing primary amine groups, more in particular bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2), and amodimethicones containing amine groups in the side chain, more in particular bis-cetearyl amodimethicone; the (poly)amine compound selected from: B) a (poly)thiol compound, iia) a polydialkylsiloxane having thiol functional groups, and iib) alkoxysilanes with thiol functional groups is selected from In particular, iia) polydialkylsiloxanes containing thiol functional groups, preferably polydimethylsiloxanes containing thiol groups in the side chains, in particular mercaptopropyl, and more particularly compounds of formula (XIII): R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALK1-SH)-O] n -Si(R b )(R d )-R a (XIII) Here, in formula (XIII), R a and R b may be the same or different, preferably the same, and represent a (C1-C4) alkyl group, in particular methyl, a (C1-C4) alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(C1-C4) alkyl group, in particular benzyl, or an aryl(C1-C4) alkoxy group, in particular benzoxy, preferably a (C1-C4) alkyl group, more preferably methyl; R d represents a (C1-C4) alkyl group, particularly methyl, a (C1-C4) alkoxy group, particularly methoxy, an aryl group, particularly phenyl, an aryloxy group, particularly phenoxy, an aryl(C1-C4) alkyl group, particularly benzyl, an aryl(C1-C4) alkoxy group, particularly benzoxy, or a (C1-C4) alkylamino group, a (C1-C6) alkyl group substituted with an amino group or a thiol group, preferably a (C1-C4) alkyl group, more preferably methyl; and preferably R a , R b and R dare the same and represent a (C1-C6) alkyl group, more preferably methyl; ALK1 represents a linear or branched, optionally cyclic, saturated or unsaturated, divalent hydrocarbon-based chain having 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen atoms, in particular oxygen atoms, (thio)carbonyl groups C(X) (wherein X represents O or S), or combinations thereof, in particular -O-, -OC(O)- or -C(O)-O-; preferably, ALK1 represents a (C1-C6) alkylene, more preferably a (C1-C4) alkylene group, even more preferably propylene, n and m may be the same or different and represent integers greater than 2, and in particular, the values ​​of m and n are such that the weight average molecular weight of the polyorganosiloxane is 1,000 to 55,000 g / mol -1 That which is, the (poly)thiol compound selected from the group consisting of: C) a (poly)acrylate compound of formula (XIV): L[-YC(O)-C(R e )=CH2] q (XIV) Here, in formula (XIV), q represents an integer of 2 or more, and particularly, n is 2 to 10, preferably 2 to 5; L represents a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, polyvalent (at least divalent) group, in particular containing 1 to 500 carbon and / or silicon atoms, more in particular 2 to 40 carbon and / or silicon atoms, even more in particular 3 to 30 carbon and / or silicon atoms, preferably 6 to 20 carbon atoms; L is selected from O, S, N, Si, C(X) and combinations thereof, in particular -O-, -OC(X)-, -N(R)-C(X)-, -Si(R c )(R d )-O-, where R represents a hydrogen atom or a (C1-C6) alkyl group, in particular methyl; and / or L may be interrupted and / or terminated by one or more heteroatoms or groups selected from -N(Ra )R b and -(X') a -C(X)-(X'') b -R a wherein X, X' and X'' may be the same or different and are substituted with one or more groups selected from an oxygen atom or a sulfur atom, or N(R b a and b are 0 or 1, preferably the sum of a+b is 1; R a and R b may be the same or different and represent a hydrogen atom, a (C1-C6) alkyl group or an aryl(C1-C4) alkyl group, in particular benzyl, preferably R a and R b represents a hydrogen atom, and R c and R d may be the same or different and represent a (C1-C6) alkyl, aryl(C1-C4) alkyl or (C1-C6) alkoxy group; R e represents a hydrogen atom or a (C1-C4) alkyl group, in particular methyl; preferably, R e represents a hydrogen atom, and Y represents an oxygen atom or an amino group -N(H)-, preferably an oxygen atom; Preferably, Y is an oxygen atom and R e is a hydrogen atom, preferably L represents a divalent or trivalent, preferably trivalent, hydrocarbon-based chain having 1 to 8 carbon atoms, q is 2 or 3, preferably 3, and More preferably, the compound of formula (XIV) is trimethylolpropane triacrylate. D) Metal alkoxides, such as zirconium ethoxide (Zr(OC2H5)4), zirconium propoxide (Zr(OCH2CH2CH3)4), zirconium isopropoxide (Zr(OCH(CH3)2)4), zirconium butoxide Zr(OCH2CH2CH2CH3)4, zirconium tert-butoxide (Zr(OC(CH3)3)4), titanium ethoxide (Ti(OC2H5)4), titanium propoxide (Ti(OCH2CH2CH3)4), titanium iso the metal alkoxide is selected from titanium propoxide (Ti(OCH(CH3)2)4), titanium butoxide (Ti(OCH2CH2CH2CH3)4), titanium tert-butoxide (Ti(OC(CH3)3)4), titanium 2-ethylhexyloxide (Ti(OCH2CH(C2H5)(CH2)3CH3)4), and combinations thereof, more preferably selected from zirconium propoxide, titanium propoxide, titanium butoxide, and combinations thereof; E) (Poly)carbonyl compounds, for example, (poly)carbonyl compounds containing saturated or unsaturated, aromatic C5-C7 carbon rings, preferably aromatic, for example phenyl, or non-aromatic, and saturated, for example cyclohexyl, more preferably unsaturated and aromatic, for example terephthalaldehyde.

[0348] Cosmetic active agents iii)

[0349] According to one particular embodiment, the method of the invention also comprises iii) applying at least one cosmetic active agent to the keratinous materials, in particular to the skin and / or the lips and / or the eyelashes and / or the eyebrows.

[0350] More particularly, in the treatment methods according to the present invention, at least one of composition "C1", composition "C2", composition "C3", composition "C4" or composition "C5" used comprises one or more cosmetic active agents.

[0351] In particular, one or more of said cosmetic active agents iii) a) dyes (or colorants), in particular dyes selected from pigments, direct dyes and combinations thereof; b) active agents for caring for keratinous materials, preferably skin c) UV blocking agents, and d) a combination of these is selected from.

[0352] According to one particular embodiment, the at least one cosmetic active agent iii) is chosen from dyes, preferably from pigments, direct dyes and combinations thereof, more preferably from pigments.

[0353] According to another embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used comprises a) one or more cosmetic active agents iii) selected from dyes (or colorants), in particular selected from pigments, direct dyes and combinations thereof, preferably selected from pigments.

[0354] According to one particular embodiment, composition "C1" comprises at least one cosmetic active agent iii) as described hereinabove and hereinafter, preferably selected from a) dyes, more preferably selected from pigments.

[0355] According to one particular embodiment, composition "C2" comprises at least one cosmetic active agent iii) as described hereinabove and hereinafter, preferably selected from a) dyes, more preferably selected from pigments.

[0356] According to one particular embodiment, composition "C3" comprises at least one cosmetic active agent iii) as described hereinabove and hereinafter, preferably selected from a) dyes, more preferably selected from pigments.

[0357] Of course, the skilled artisan will take care to select this or any one or more cosmetic active agents and / or amounts thereof such that the advantageous properties of the corresponding composition according to the invention are not adversely affected or are not substantially adversely affected by the intended addition.

[0358] dye

[0359] According to one particular embodiment, the method of the invention makes use of one or more dyes.

[0360] More particularly, in the method of the present invention, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used comprises at least one particulate or non-particulate, water-soluble or water-insoluble dye, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition under consideration.

[0361] For obvious reasons, this amount can vary significantly depending on the strength of the color effect desired and the intensity of the shade provided by the dye under consideration, adjustments of which are clearly within the skill of one in the art.

[0362] Preferably, at least one of Composition "C1", Composition "C2", Composition "C3", Composition "C4", or Composition "C5" comprises at least one dye selected from pigments, direct dyes, and combinations thereof, more preferably pigments.

[0363] More preferably, the one or more pigments of the present invention are selected from carbon black, iron oxides, in particular yellow, red and black iron oxides, and mica coated with iron oxide, triarylmethane pigments, in particular blue and purple triarylmethane pigments, in particular Blue 1 Lake, azo pigments, in particular red azo pigments, more in particular D&C Red 7, alkali metal salts of littoral red, in particular the calcium salt of littoral red B, and even more preferably red iron oxide, iron pyrite and azo pigments, in particular red azo pigments, more in particular D&C Red 7.

[0364] pigment

[0365] For the purposes of the present invention, the term "pigment" means any compound capable of imparting color to keratinous materials, which has a solubility in water at 25°C and atmospheric pressure (760 mmHg) of less than 0.05% by weight, preferably less than 0.01% by weight. is.

[0366] As pigments suitable for use in the present invention, mention may be made in particular of 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."

[0367] These pigments may be synthetic or natural.

[0368] These pigments may be in the form of a pigment powder or a paste.

[0369] These pigments may be coated or uncoated.

[0370] These pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, special effect pigments such as nacre or glitter flake, and combinations thereof.

[0371] Pigments suitable for use in the present invention may be selected from mineral pigments.

[0372] The term "mineral pigment" means any pigment that meets the definition in the chapter on inorganic pigments of the Ullmann Encyclopedia. Among the mineral pigments useful in the present invention, mention may be made of manganese violet, ultramarine blue, chromium hydrate, ferric blue, oxides or dioxides of titanium, zirconium or cerium, and also oxides of zinc, iron or chromium.

[0373] The mineral pigment may also be a pigment having a structure that may be, for example, of the sericite / brown iron oxide / titanium dioxide / silica type. Such a pigment is, for example, sold by Chemicals and Catalysts under the reference number Coverleaf NS or JS and has a contrast ratio of about 30. Such a pigment may also be a pigment having a structure of, for example, silica microsphere type containing iron oxide. An example of a pigment having this structure is the product sold by Miyoshi under the reference number PC Ball PC-LL-100 P, which is composed of silica microspheres containing yellow iron oxide.

[0374] Advantageously, the pigment may be iron oxide and / or titanium oxide.

[0375] Pigments suitable for use in the present invention may be selected from organic pigments.

[0376] The term "organic pigment" means any pigment that meets the definition in the chapter on organic pigments in Ullmann's Encyclopedia. Among the organic pigments useful in the present invention, mention may be made of nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluoran, phthalocyanine, metal complexes, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane, and quinophthalone compounds. In particular, white or colored organic pigments are carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, blue pigments classified in the Color Index under the reference numbers CI 42090, 69800, 69825, 74100, 74160, yellow pigments classified in the Color Index under the reference numbers CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, green pigments classified in the Color Index under the reference numbers CI 61565, 61570, 74260, orange pigments classified in the Color Index under the reference numbers CI 11725, 45370, 71105, and the like. The red pigments may be selected from the red pigments designated in the Colour Index under 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, as well as the pigments obtained by oxidative polymerization of indole or phenol derivatives, as described in French Patent No. FR 2,679,771.

[0377] Examples that may also be mentioned include pigment pastes of organic pigments, such as the products sold by Hoechst: Cosmenyl Yellow 10G: Yellow 3 pigment (CI 11710); Cosmenyl G yellow: Yellow 1 pigment (CI 11680); Cosmenyl GR Orange: Orange 43 pigment (CI 71105); Cosmenyl R Red: Red 4 pigment (CI 12085); Cosmenyl FB Carmine: Red 5 pigment (CI 12490); Cosmenyl RL Violet: Violet 23 pigment (CI 51319); Cosmenyl A2R Blue: Blue 15.1 pigment (CI 74160); Cosmenyl GG Green: Green 7 pigment (CI 74260); Cosmenyl R Black: Black 7 pigment (CI 77266).

[0378] The pigments according to the invention may also be in the form of composite pigments, as described in EP 1 184 426. These composite pigments may in particular consist of particles comprising an inorganic core, at least one binder for adhering an organic pigment to the core, and at least one organic pigment at least partially covering the core.

[0379] The organic pigment may also be a lake.

[0380] The term "lake" refers to dye adsorbed onto insoluble particles, the resulting mass remaining insoluble during use.

[0381] Inorganic substrates onto which dyes are adsorbed include, for example, alumina, silica, calcium sodium borosilicate or calcium aluminum borosilicate, and aluminum.An example of a dye adsorbed onto an organic substrate is carminic acid. Mention may also be made of dyes 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 5 (CI 61 570), D&C Yellow 10 (CI 77 002), D&C Green 3 (CI 42 053), D&C Blue 1 (CI 42 090), FDC Red 4, D&C Red 6, D&C Red 22, D&C Red 28, D&C Red 30, D&C Orange 4, D&C Yellow 8, D&C Green 5, D&C Red 17, D&C Green 6, D&C Yellow 11, D&C Violet 2, Sudan red, carotenes (beta-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin, betanin (beet), carmine, copper chlorophyll, methylene blue, anthocyanins (enocyanin, black carrot, hibiscus, elderberry), caramel, riboflavin, beet juice, and caramel.

[0382] An example of a lake that may be mentioned is the product known under the following name: D&C Red 7 (CI 15 850:1).

[0383] The pigment may also be a special effect pigment.

[0384] The term "special effect pigments" refers to pigments that generally exhibit a non-uniform colored appearance (characterized by a particular hue, a particular vibrancy, and a particular brightness level) that varies with viewing conditions (light, temperature, viewing angle, etc.), thereby differing from colored pigments that exhibit standard uniform opaque, translucent, or transparent shades.

[0385] There are several types of special effect pigments: those with a low refractive index, such as fluorescent pigments or photocolor shifting pigments, and those with a high refractive index, such as nacre, interference pigments or glitter flakes.

[0386] The particle size of the pigment used in the composition according to the present invention is generally 10 nm to 200 μm, preferably 20 nm to 80 μm, and more preferably 30 nm to 50 μm.

[0387] The pigment may be dispersed in the composition by a dispersant.

[0388] The dispersant may be a surfactant, an oligomer, a polymer, or some combination thereof, and has one or more functional groups that have a strong affinity for the surface of the particles to be dispersed. In particular, these dispersants may be physically or chemically attached to the surface of the pigment. These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium. In particular, esters of 12-hydroxystearic acid, especially C8-C6 20Esters of fatty acids with polyols (e.g., glycerol or diglycerol), such as poly(12-hydroxystearic acid) stearate having a molecular weight of approximately 750 g / mol, such as the product sold by Avecia under the name Solsperse 21000, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold by Henkel under the reference number Dehymyls PGPH, or polyhydroxystearic acid sold by Uniqema under the reference number Arlacel P100, and combinations thereof, can be used. Other dispersants that may be used in the compositions of the present invention include quaternary ammonium derivatives of polycondensed fatty acids, such as Solsperse 17000 sold by Avecia, and polydimethylsiloxane / oxypropylene mixtures sold by Dow Corning under the reference numbers DC2-5185 and DC2-5225 C. The pigment used in the composition may be surface-treated with an organic agent. In certain embodiments, the one or more dispersants are aminosilicone-type dispersants other than the alkoxysilanes described above and are cationic. Preferably, the one or more pigments are selected from inorganic pigments, inorganic-organic mixed pigments, or organic pigments.

[0389] According to one particular embodiment, the pigment or pigments also in accordance with the invention are organic pigments, preferably organic pigments that have been surface-treated with an organic agent chosen from silicone compounds.

[0390] According to another embodiment of the present invention, the one or more pigments according to the present invention are mineral pigments.

[0391] direct dye

[0392] According to a particular embodiment of the invention, the cosmetic active agent is a dye chosen from one or more direct dyes.

[0393] The term "direct dyes" refers to natural and / or synthetic dyes other than oxidation dyes. These are dyes that spread widely on the fiber. Direct dyes may be ionic or non-ionic, preferably cationic or non-ionic.

[0394] As direct dyes suitable for use in the present invention, mention may be made of azo direct dyes; (poly)methylene dyes, such as cyanine, hemicyanine and styryl; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, either alone or in the form of a mixture.

[0395] The direct dyes are preferably cationic direct dyes. Mention may be made of hydrazonocationic dyes of formula (A) and (B) below and azocationic dyes of formula (C) and (D) below: Het + -C(Ra)=NN(Rb)-Ar,Q - (A) Het + -N(Ra)-N=C(Rb)-Ar,Q - (B) Het + -N=N-Ar,Q - (C) Ar + -N=N-Ar'',Q - (D) Here, in formulas (A) to (D), Het + represents a heteroaryl moiety, preferably a heteroaryl moiety having an intracyclic cationic charge, such as imidazolium, indolium or pyridinium, which may be substituted, preferably with at least one (C1-C8) alkyl group, such as methyl; Ar + represents an aryl moiety, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferably ammonium, and in particular is tri(C1-C8)alkylammonium, such as trimethylammonium; Ar represents an aryl group, in particular phenyl, which may be substituted, preferably with one or more electron-donating groups, such as optionally substituted (C1-C8) alkyl, optionally substituted (C1-C8) alkoxy, (di)(C1-C8) (alkyl) amino optionally substituted on one or more alkyl groups by hydroxyl groups, aryl(C1-C8) alkylamino, and optionally substituted N—(C1-C8) alkyl-N-aryl(C1-C8) alkylamino, or alternatively Ar represents a julolidine group; Ar" represents an optionally substituted (hetero)aryl group, such as phenyl or pyrazolyl, which may be substituted, preferably by one or more (C1-C8) alkyl groups, hydroxyl groups, (di)(C1-C8) (alkyl) amino groups, (C1-C8) alkoxy groups or phenyl groups; Ra and Rb may be the same or different and represent a hydrogen atom or a (C1-C8) alkyl group, which may be substituted, preferably by a hydroxyl group; Or, Het + and / or Rb having a substituent of Ar, taken together with the atom carrying them, form a (hetero)cycloalkyl; in particular, Rb and Rb represent a hydrogen atom or a (C1-C4) alkyl group optionally substituted by a hydroxyl group; Q - represents an organic or inorganic anionic counterion, such as a halide or alkyl sulfate.

[0396] Mention may in particular be made of the azo and hydrazono direct dyes having an internal cationic ring charge of the formulae (A) to (D) defined above, more in particular the cationic direct dyes having an internal cationic ring charge described in WO 95 / 15144, WO 95 / 01772 and EP 714954.

[0397] Preferably, the direct dye is selected from the compounds of formula (E) and formula (F) below: [ka] Here, in formula (E) and formula (F), R 1 is a (C1-C4) alkyl group, for example, methyl; R 2 and R 3 may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group, such as methyl; R 4 represents a hydrogen atom or an electron-donating group, such as optionally substituted (C1-C8) alkyl, optionally substituted (C1-C8) alkoxy, or (di)(C1-C8)(alkyl)amino optionally substituted on one or more alkyl groups by a hydroxyl group; in particular R 4 is a hydrogen atom; Z represents a CH group or a nitrogen atom, preferably CH; Q - is an anionic counterion as defined above, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesyl.

[0398] In particular, the dyes of formula (E) and formula (F) are selected from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof, where Q' is an anionic counterion as defined above, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesyl. The direct dyes may be selected from anionic direct dyes. The anionic direct dyes of the present invention are those dyes commonly referred to as "acid" direct dyes because of their affinity for alkaline substances.

[0399] The term "anionic direct dye" means a direct dye containing at least one CO2R' or SO3R' substituent in its structure, where R' represents a hydrogen atom, or a cation derived from a metal or an amine, or an ammonium ion.

[0400] The anionic direct dyes may be selected from direct nitro acid dyes, azo acid dyes, azine acid dyes, triarylmethanoic acid dyes, indoamine acid dyes, anthraquinonic acid dyes, indigoid dyes and natural acid dyes.

[0401] Examples of natural direct dyes that can be used in the present invention include lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatecholaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin, and orcein. Extracts or decoctions containing these natural dyes, particularly henna-based poultices or extracts, can also be used.

[0402] Preferably, the direct dye is selected from anionic direct dyes.

[0403] The dyes, preferably the pigments, may be present in concentrations ranging from 0.01% to 30% by weight, from 0.02% to 20% by weight, and more particularly from 0.05% to 15% by weight relative to the total weight of the composition containing them.

[0404] The direct dye(s) may be present in a concentration ranging from 0.001% to 10% by weight, and preferably from 0.005% to 5% by weight, relative to the total weight of the composition containing them.

[0405] Preferably, the one or more cosmetic active agents, in particular the one or more dyes, more in particular the one or more pigments, are incorporated into at least one of Composition "C1", Composition "C2", Composition "C3", Composition "C4" or Composition "C5".

[0406] Care activator

[0407] According to one particular embodiment, the method of the invention makes use of one or more care actives.

[0408] More particularly, in the method of the invention, according to one embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used preferably comprises one or more care actives, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition under consideration, in particular said care actives being at least one hydrophilic and / or one lipophilic active, preferably a hydrophilic care active.

[0409] The term "hydrophilic active agent" means a water-soluble or water-dispersible active agent capable of forming hydrogen bonds.

[0410] The one or more cosmetic care active agents may be chosen, in particular, from: a) vitamins and derivatives thereof, in particular their esters, in particular tocopherol (vitamin E) and its esters (e.g. tocopheryl acetate), ascorbic acid (vitamin C) and its derivatives; b) moisturizers, in particular urea, hydroxyurea, glycerol, polyglycerol, glycerol glucoside, diglycerol glucoside, polyglyceryl glucoside and xylityl glucoside, in particular glycerol; c) C-glycoside compounds; d) antioxidant compounds; e) anti-ageing active agents, in particular hyaluronic acid compounds, in particular sodium hyaluronate, retinol and its derivatives. derivatives of salicylic acid compounds, in particular n-octanoyl-5-salicylic acid (capryloyl salicylic acid), caffeine, adenosine, C-β-D-xylopyranoside-2-hydroxypropane, and the sodium salt of 3-hydroxy-2-pentylcyclopentylacetic acid; f) skin care agents selected from allantoin, panthenol, and protein hydrolysates; g) polyphenols, in particular escin, ruscus, diosmin, hesperidin, and resveratrol, and h) combinations thereof.

[0411] In particular, in the method of the present invention, according to one embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used comprises a moisturizer (also known as a humectant agent). Preferably, the skin care active is a moisturizer, in particular glycerin (glycerol).

[0412] The one or more care active agents may in particular be present in the composition containing them in an amount ranging from 0.01% to 30% by weight, preferably from 0.02% to 25% by weight relative to the weight of the composition.

[0413] UV blockers

[0414] According to one embodiment of the method of the present invention, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used comprises, as a cosmetic active agent, at least one UV-blocking agent.

[0415] The UV blocking agent is a UV blocking agent commonly used in cosmetics.

[0416] The UV-screening agent may be selected from the positive list set out in Annex VI of (EC) Regulation No. 1223 / 2009, which specifies the permitted list of UV-screening agents permitted in cosmetic products.

[0417] The UV blocking agents suitable for use in the present invention can be of a variety of nature.

[0418] The UV blocking agent can be a lipophilic, hydrophilic, or insoluble organic agent.

[0419] The term "lipophilic UV screening agent" means any cosmetic or dermatological screening agent which can be completely dissolved in molecular form in a liquid fatty phase or which can be dissolved in colloidal form (e.g. in micellar form) in a liquid fatty phase.

[0420] The term "hydrophilic UV screening agent" means any cosmetic or dermatological screening agent that can be completely dissolved in molecular form in a liquid aqueous phase or that can be dissolved in colloidal form (e.g., in micellar form) in a liquid aqueous phase.

[0421] The term "insoluble UV-screening agent" means any cosmetic or dermatological screening agent which does not fall under the category of lipophilic or hydrophilic UV-screening agents and which is present in the form of particles in an aqueous or liquid fatty phase. The UV-screening agents of the composition according to the invention may provide UVA and / or UVB photoprotection.

[0422] According to a preferred embodiment, the composition, preferably the cosmetic composition, may comprise at least one organic and / or inorganic UV-blocking agent (to block UV radiation from sunlight).

[0423] In particular, the one or more UV blocking agents are selected from bis-resorcinyl triazine derivatives, dibenzoylmethane derivatives, benzylidene camphor derivatives, and combinations thereof.Organic UV-screening agents also include anthranilic derivatives; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenylbenzotriazole derivatives; benzalmalonate derivatives, especially those described in U.S. Pat. No. 5,624,663; phenylbenzimidazole derivatives; imidazolines; 4,4-diarylbutadiene derivatives; bis-benzazolyl derivatives. , as described in European Patent No. EP 6,693,23 and U.S. Patent No. US 2,463,264; p-aminobenzoic acid (PABA) derivatives; methylenebis(hydroxyphenylbenzotriazole) derivatives, as described in U.S. Patent Nos. US 5,237,071, US 5,166,355, British Patent No. GB ​​2,303,549, German Patent No. DE 19726184 and European Patent No. EP 893,119; benzoxazole derivatives, e.g. For example, those described in European Patent Nos. EP 0,832,642, EP 1,027,883, EP 1,300,137 and German Patent No. DE 10162844; screening polymers and screening silicones, for example, those described in International Publication No. WO 93 / 04665; α-alkylstyrene-based dimers, for example, those described in German Patent No. DE 19855649; 4,4-diarylbutadienes, for example, those described in European Patent Nos. E P0,967,200, DE19746654, DE19755649, EP1,008,586, EP1,133,980 and EP133,981; other merocyanine derivatives, such as those described in WO04 / 006878, WO05 / 058269 and WO06 / 032741, and combinations thereof.

[0424] According to one particular embodiment, the concentration of organic UV-screening agent in the composition ranges from 1% to 50% by weight, preferably from 1% to 40% by weight, for example from 5% to 35% by weight, relative to the total weight of the composition.

[0425] The one or more UV-blocking agents may be mineral UV-screening agents, which are generally pigments, which may be coated or uncoated.

[0426] Thus, the mineral UV blocker may be selected from coated or uncoated pigments, in particular coated titanium oxide pigments, silicone treated titanium oxide pigments, uncoated titanium oxide pigments, uncoated zinc oxide pigments, coated zinc oxide pigments, uncoated cerium oxide pigments, uncoated iron oxide pigments, coated iron oxide pigments, and combinations thereof.

[0427] According to one particular embodiment, compositions "C1" to "C5" do not contain a mineral UV blocker.

[0428] According to one particular embodiment, the amount of one or more mineral UV-screening agents present in Composition "C1", "C2", "C3", "C4" or "C5" according to the invention may range from 0.01% to 20% by weight, relative to the total weight of the composition containing them. The amount of one or more mineral UV-screening agents may, for example, range from 1% to 15% by weight, relative to the total weight of the composition.

[0429] According to one particular embodiment, at least one of compositions "C1" to "C5" also includes one or more organic UV-screening agents and one or more mineral UV-screening agents.

[0430] According to one particular embodiment, the composition comprises a combination of UV-blocking agents as described in French Patent No. FR 2,977,490, International Publication No. WO 2013 / 004777 or US Patent Application Publication No. US 2014 / 0134120.

[0431] Preferably, the method for treating keratinous materials, especially the skin and / or lips and / or eyelashes and / or eyebrows, uses one or more dyes selected from pigments, direct dyes and combinations thereof, preferably pigments, and the used composition Composition "C1", Composition "C2", Composition "C3", Composition "C4" or Composition "C5" comprises one or more dyes selected from pigments, direct dyes and combinations thereof, preferably pigments; more preferably, the one or more pigments of the present invention are selected from carbon black, iron oxides, especially yellow, red and black iron oxides, and mica coated with iron oxide, triarylmethane pigments, especially blue and purple triarylmethane pigments, such as Blue 1 Lake, azo pigments, especially red azo pigments, such as D&C Red 7, alkali metal salts of litho red, for example the calcium salt of litho red B, and even more preferably red iron oxides, iron pyrite and azo pigments, especially red azo pigments, such as D&C Red 7.

[0432] Fat phase - fatty substances

[0433] According to one particular embodiment, the method of the invention also makes use of iv) one or more fatty substances, in particular one or more oils, preferably volatile oils.

[0434] In particular, at least one of composition "C1", composition "C2", composition "C3", composition "C4" or composition "C5" used in the methods of the present invention comprises a fatty phase.

[0435] In particular, at least one of composition "C1", composition "C2", composition "C3", composition "C4" or composition "C5" used in the method of the present invention comprises one or more fatty substances different from compound i), in particular one or more oils, preferably volatile oils.

[0436] The term "oil" refers to a fatty substance that is liquid at room temperature (20°C) and atmospheric pressure (760 mmHg).

[0437] The term "hydrocarbon-based oil" means an oil essentially formed or composed of carbon and hydrogen atoms, which may contain oxygen and nitrogen atoms, but which does not contain silicon or fluorine atoms. The hydrocarbon-based oil may contain alcohol, ester, ether, carboxylic acid, amine, and / or amide groups.

[0438] According to one embodiment of the invention, the one or more oils iv) are chosen from volatile oils, and in particular from: Hydrocarbon-based oils having 8 to 16 carbon atoms, especially branched C8-C 16 Alkanes, especially isoalkanes, more especially isoalkanes (also known as isoparaffins), preferably C 13 ~C 16 Isoparaffins, isododecane, isodecane, isohexadecane, for example oils sold under the trade name Isopar or Permethyl, alone or in combination, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular C 11 ~C 16 Alkanes, alone or in combination, in particular hexane, decane, undecane, tridecane, isoparaffins, in particular n-dodecane (C 12 ) and n-tetradecane (C 14 ), undecane-tridecane mixture, n-undecane (C 11 ) and n-tridecane (C 13 ), and combinations thereof, and also n-undecane (C 11) and n-tridecane (C 13 ) and mixtures with volatile C5-C 12 cyclic, non-aromatic alkanes; short-chain esters having a total of 3 to 8 carbon atoms, in particular ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate; carbonate hydrocarbon-based oils of the structure R'1-OC(O)-O-R'2, where R'1 and R'2 independently represent a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously and more preferably selected from dibutyl carbonate or dipentyl carbonate; ether oils of the formula R1-O-R2, where R1 and R2 independently represent a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group; Silicone oils, in particular those containing 2 to 7 silicon atoms and optionally containing alkyl or alkoxy groups having 1 to 10 carbon atoms, with a viscosity of 5 to 6 cSt, such as dimethicone, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and combinations thereof; More preferably, the one or more volatile oils iv) are C8 to C 16 It is selected from alkanes, in particular branched alkanes, preferably isododecane.

[0439] In particular, at least one of composition "C1", composition "C2", composition "C3", composition "C4" or composition "C5" used in the methods of the present invention comprises one or more non-volatile oils, preferably non-volatile fluorinated oils, in particular non-volatile fluorinated oils selected from fluorinated polyethers, fluorosilicone oils and fluorosilicones; non-volatile silicone oils, in particular chosen from the non-volatile silicones with the following INCI names: dimethicone, dimethiconol, trimethylpentaphenyltrisiloxane, tetramethyltetraphenyltrisiloxane, diphenyldimethicone, trimethylsiloxyphenyldimethicone, phenyltrimethicone, diphenylsiloxyphenyltrimethicone; and also combinations thereof; Non-volatile non-polar hydrocarbon-based oils, in particular selected from linear or branched compounds of mineral or synthetic origin: i) liquid paraffin, ii) squalane, isoeicosane, iii) linear, saturated hydrocarbons, more particularly C 15 ~C 28 Hydrocarbons, mixtures of hydrocarbons, especially those with the INCI name (C 15 ~C 19 ) alkanes, (C 18 ~C 21 ) alkanes, (C 21 ~C 28 ) a mixture of alkanes, iv) hydrogenated or non-hydrogenated polybutene; v) hydrogenated or non-hydrogenated polyisobutene, preferably hydrogenated polyisobutene, vi) hydrogenated or non-hydrogenated polydecene, vii) decene / butene copolymers, butene / isobutene copolymers, and viii) combinations thereof; Non-volatile polar hydrocarbon-based oils, which may be selected from: i) saturated, unsaturated, linear or branched C 10 ~C 26 Fatty alcohols, preferably monoalcohols; in particular C 10 ~C 26The alcohol is a fatty alcohol, which is preferably branched, if it has at least 16 carbon atoms; preferably, the fatty alcohol contains 10 to 24 carbon atoms, more preferably 12 to 22 carbon atoms, in particular, for example, lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyloctanol, 2-undecylpentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol, and combinations thereof; ii) Triglycerides consisting of fatty acid esters of glycerol, in particular those in which the fatty acids are C4 to C 36 , especially C 18 ~C 36 , ... Mention may be made of: laurel oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passion flower oil, musk rose oil, peanut oil, coconut oil, argan oil, passion flower oil, kaya oil, the liquid fraction of shea butter and the liquid part of cocoa butter, and combinations thereof: iii) linear aliphatic hydrocarbon-based esters of the formula RC(O)-OR', where RC(O)-O- represents a carboxylic acid residue containing 2 to 40 carbon atoms and R' represents a hydrocarbon-based chain containing 1 to 40 carbon atoms, aliphatic hydrocarbon-based esters of alkylene glycols, in particular ethylene glycol or propylene glycol; those in which the total number of carbon atoms is in particular at least 10; in particular isoamyl laurate, cetostearyl octanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate or isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, octanoate, decanoate or alkenyl esters. Ricinoleates of chol or polyalcohols, such as propylene glycol dioctanoate, cetyl octanoate or tridecyl octanoate, 2-ethylhexyl palmitate, alkyl benzoates, polyethylene glycol diheptanoate, propylene glycol bis(2-ethylhexanoate) and combinations thereof, hexyl laurate, neopentanoic acid esters, such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate or 2- octyldodecyl neopentanoate, isononanoic acid esters, in particular isononyl isononanoate, isotridecyl isononanoate or octyl isononanoate, oleyl erucate, isopropyl lauroyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate or myristyl myristate; iv) hydroxylated esters, in particular polyglyceryl-2 triisostearate; v) aromatic esters, in particular tridecyl trimellitate, C 12 ~C 15 alcohol benzoate, 2-phenylethyl ester of benzoic acid, and butyloctyl salicylate; vi) linear fatty acid esters having a carbon number in the range of 35 to 70, in particular pentaerythrityl tetrapelargonate; vii) C 24 ~C 28 esters of branched fatty acids or fatty alcohols, in particular triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2-decyltetradecanoate), pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetrakis(2-decyltetradecanoate); viii) polyesters obtained by condensation of dimers and / or trimers of unsaturated fatty acids with diols, in particular polyesters with the INCI names "Dilinoleic Acid / Butanediol Copolymer" or "Dilinoleic Acid / Propanediol Copolymer"; polyesters obtained by condensation of fatty acid dimers with diol dimers, in particular dimer dilinoleyl dimer dilinoleate; ix) synthetic ethers containing 10 to 40 carbon atoms, in particular dicaprylyl ether; x) dialkyl carbonates, where the two alkyl chains may be the same or different, in particular dicaprylyl carbonate; xi) vinylpyrrolidone copolymers, in particular vinylpyrrolidone / 1-hexadecene copolymers; and xii) combinations thereof is selected from Here, non-volatile carbonate oils are represented by the formula R8-OC(O)-O-R9, where R8 and R9 may be the same or different, and are linear or branched C4-C 12 , preferably C6 to C 10 , representing an alkyl chain); the carbonated oil may be dicaprylyl carbonate (or dioctyl carbonate), bis(2-ethylhexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate or dinonyl carbonate, preferably dioctyl carbonate; Oils known as non-volatile ether oils of the formula R1-O-R2, where R1 and R2 are independently linear, branched or cyclic C6-C 24 Alkyl groups, preferably C6 to C 18 Alkyl groups, preferably C8 to C 12It may be preferable that R1 and R2 are the same. Straight-chain alkyl groups that may be mentioned include hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, behenyl, docosyl, tricosyl, and tetracosyl groups. Branched alkyl groups that may be mentioned include 1,1-dimethylpropyl, 3-methylhexyl, 5-methylhexyl, ethylhexyl, 2-ethylhexyl, 5-methyloctyl, 1-ethylhexyl, 1-butylpentyl, 2-butyloctyl, isotridecyl, 2-pentylnonyl, 2-hexyldecyl, isostearyl, 2-heptylundecyl, 2-octyldodecyl, 1,3-dimethylbutyl, 1-(1-methylethyl)-2-methylpropyl, 1,1,3,3-tetramethylbutyl, 3,5,5-trimethylhexyl, 1-(2-methylpropyl)-3-methylbutyl, 3,7-dimethyloctyl, and 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyloctyl. As cyclic alkyl groups, mention may be made of cyclohexyl, 3-methylcyclohexyl and 3,3,5-trimethylcyclohexyl groups, dilauryl ether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyl dimethyl butyl ether, cetyl dimethyl butyl ether and combinations thereof.

[0440] Preferably, the one or more non-volatile oils are hydrogenated or non-hydrogenated polyisobutene, especially hydrogenated polyisobutene, especially Parleam 登録商標 range of non-volatile compounds; C 15 ~C 19 It is selected from a mixture of alkanes and from linear aliphatic hydrocarbon-based esters of the formula RC(O)-OR', where RC(O)-O represents a carboxylic acid residue containing 2 to 40 carbon atoms and R' represents a hydrocarbon-based chain containing 1 to 40 carbon atoms as defined above, in particular isononyl isononanoate.

[0441] More preferably, the method of the present invention is directed to one or more hydrocarbon-based oils having 8 to 16 carbon atoms, especially branched C8-C 16 Alkanes, especially isoalkanes, preferably C 13 ~C 16 Isoparaffin, isododecane, isodecane, isohexadecane may be used alone or in combination, and isododecane is more preferred.

[0442] According to a preferred embodiment, the process of the invention uses one or more fatty substances iv) different from the compound of formula (I), in particular at least one oil, preferably at least one volatile oil, more preferably at least one hydrocarbon-based volatile oil.

[0443] In particular, the one or more oils different from compound i) in at least one of composition "C1", "C2", "C3", "C4" or "C5" used in the method according to the invention range from 1% to 99% by weight, more particularly from 2% to 98% by weight, preferably from 3% to 97% by weight, and even better from 5% to 96% by weight, relative to the total weight of the composition.

[0444] According to another particular embodiment, the method of the invention does not use any fatty substance iv) different from the compound of formula (I).

[0445] According to yet another embodiment, at least one of composition "C1", composition "C2", composition "C3", composition "C4" or composition "C5" used in the method according to the invention comprises a mixture of compound i) and a different fatty substance v) and is selected from a mixture of at least one volatile oil, preferably a hydrocarbon-based oil, and at least one non-volatile oil, such as octyldodecanol.

[0446] composition

[0447] Another object of the present invention is a composition, in particular a cosmetic composition, comprising at least one compound chosen from compounds of formula (Ia), formula (Ib), formula (Ic), formula (Id) and formula (Ie), their salts, isomers and / or solvates thereof, such as hydrates, as defined above, and more particularly a composition, especially a cosmetic composition, comprising at least one compound of formula (Iic), formula (Iid) and formula (Iie) as defined above.

[0448] Another subject of the present invention is a composition, in particular a cosmetic composition, comprising at least one compound chosen from compounds (8), (9), (10), (11), (12), (13) and (14), their salts, isomers and solvates thereof, as defined above.

[0449] Another subject of the present invention is a composition, in particular a cosmetic composition, comprising at least one compound selected from the compounds of formula (I), (Ia), (Ib), (Ic), (Id) and / or (Ie), their salts, isomers and / or solvates thereof, such as hydrates, other than compounds (1) to (7) as defined above.

[0450] According to one particular embodiment, the method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, according to the invention uses water. Thus, according to this variant, at least one of the compositions "C1" to "C5" used in the method of the invention comprises water. According to this variant, composition "C1", composition "C2", composition "C3", composition "C4" and / or composition "C5" is an aqueous composition or an aqueous-alcoholic composition.

[0451] According to a preferred embodiment, the method for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, according to the present invention does not use any water. Thus, according to this variant, composition "C1", composition "C2", composition "C3", composition "C4" and / or composition "C5" are anhydrous compositions.

[0452] According to one particular embodiment, at least one of composition "C1", composition "C2", composition "C3", composition "C4" and / or composition "C5" comprises an isododecane / ethanol mixture, particularly in a volume ratio ranging from 1 / 99 to 99 / 1, more particularly from 5 / 95 to 95 / 5.

[0453] According to one particular embodiment, at least one of composition "C1", composition "C2", composition "C3", composition "C4" and / or composition "C5" comprises an isododecane / octyldodecanol mixture, particularly in a volume ratio ranging from 1 / 99 to 99 / 1, more particularly from 5 / 95 to 95 / 5.

[0454] According to one particular embodiment, at least one of composition "C1", composition "C2", composition "C3", composition "C4" or composition "C5" may be in the form of a water-in-oil emulsion or an oil-in-water emulsion.

[0455] According to one particular embodiment, composition "C1", composition "C4" or composition "C5" may be in the form of anhydrous, a water-in-oil emulsion or an oil-in-water emulsion.

[0456] According to one particular embodiment, composition "C4" is anhydrous. In particular, composition "C4" is anhydrous and comprises at least one oil, in particular a volatile oil, preferably isododecane.

[0457] According to another particular embodiment, composition "C4" comprises water. In particular, composition "C4" comprises water, and optionally at least one volatile or non-volatile oil and / or at least one C1-C4 alcohol, such as ethanol or isopropanol, and / or at least one non-volatile oil.

[0458] Compositions "C1" through "C5" used in the methods of the present invention may also contain one or more solvents other than water.

[0459] According to a particular embodiment of the invention, one or more compounds of formula (I) as defined above are used in a medium comprising at least one solvent other than water, preferably at least one polar and / or protic solvent.

[0460] According to this embodiment, Composition "C1", Composition "C2", Composition "C3", Composition "C4" and / or Composition "C5" used in the method of the present invention comprises one or more solvents other than water, preferably one or more polar and / or protic solvents.

[0461] Preferably, Composition "C1", Composition "C2", Composition "C3", Composition "C4" and / or Composition "C5" used in the process of the present invention comprises at least one polar and / or protic solvent selected from monoalcohols containing 2 to 6 carbon atoms, in particular ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanols and hexanols, preferably n-butanol or ethanol, even more preferably ethanol.

[0462] According to one embodiment, composition "C1", composition "C2", composition "C3", composition "C4" and / or composition "C5" used in the method of the present invention comprises one or more solvents other than water in a content of less than 95% by weight, more preferably less than 92% by weight, based on the total weight of the composition.

[0463] Organic solvents that may also be mentioned include polyols that are miscible with water at room temperature (25°C), including one or more polyols, chosen in particular from polyols containing 2 to 10 carbon atoms, preferably 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; polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether or diethylene glycol monomethyl ether; and also aromatic alcohols, such as benzyl alcohol, and combinations thereof.

[0464] According to one particular embodiment, the composition also comprises one or more polyols, especially chosen from polyols, especially polyols containing from 2 to 10 carbon atoms, preferably containing from 2 to 6 carbon atoms, preferably glycerol.

[0465] Composition "C1", "C2", "C3", "C4" or "C5" used in the method of the present invention may also comprise one or more adjuvants commonly used in cosmetics, in particular additives selected from thickeners, film-forming agents, gelling agents, trace elements, emollients, chelating agents, fragrances, alkalizing or acidifying agents, dispersing agents, preservatives, fillers, surfactants, propellants, polar additives and polymers, or combinations thereof.

[0466] Another subject of the present invention is a composition "C3" comprising i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) and / or (Iie), as defined above, ii) at least one crosslinking agent, in particular at least one crosslinking agent as defined above, and iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as defined above.

[0467] Another subject of the present invention is the cosmetic use of composition "C3" as defined above for the treatment of keratinous substances, in particular the skin and / or lips and / or eyelashes and / or eyebrows, for caring for and / or making up the keratinous substances.

[0468] Composition "C1", "C2", "C3", "C4" or "C5" is generally suitable for application to keratinous materials, in particular to the skin and / or lips, and therefore generally comprises a physiologically acceptable medium, i.e. a medium that is compatible with keratinous materials, in particular a medium that is suitable for application to the skin and / or lips.

[0469] It is preferably a cosmetically acceptable medium, i.e., one that has a pleasant color, scent and feel and does not cause unacceptable discomfort, i.e., stinging or tightness, that would discourage the user from applying the composition.

[0470] Composition "C1", "C2", "C3", "C4" or "C5" may be in the form of a make-up product, in particular a colour make-up product for the skin, such as a foundation, blush, face powder, eyeshadow, concealer, eyeliner, which may also have care effects; a lip make-up product, such as a lipstick, lip gloss or lip pencil, which may also have care effects; a make-up product for the skin, for example for the nails or eyelashes, in particular a make-up product in the form of a cake mascara, or a make-up product for the eyebrows, or a product for a temporary tattoo on the skin of the body.

[0471] According to one particular embodiment, composition "C1", composition "C2", composition "C3", composition "C4" or composition "C5" is lip coloring products; or Tintable skin care products, especially creams or fluids with moisturizing and / or filling and / or tensor properties It is in one of the following forms:

[0472] kit

[0473] According to yet another aspect of the present invention, there is also provided a multi-compartment kit or device, in particular a cosmetic kit or device, comprising: at least one compartment comprising i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as defined above, and optionally iii) at least one cosmetic active agent, at least one cosmetic active agent as defined above, in particular at least one cosmetic active agent comprising composition "C1" as defined above; at least one compartment different from that comprising i) and comprising ii) at least one cross-linking agent, in particular at least one cross-linking agent as defined above, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as defined above, in particular at least one cosmetic active agent comprising composition "C4" as defined above; and Optionally, at least one compartment different from those containing i) and ii), said at least one compartment containing iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as defined above, said at least one cosmetic active agent being the same as or different from the at least one cosmetic active agent optionally contained in the compartments containing i) and ii), respectively. The present invention is directed to the multi-compartment kit or device as described above, comprising:

[0474] Preferably, at least the compartment containing i), in particular composition "C1", does not contain any cross-linking agent ii).

[0475] Preferably, the compartment containing at least one cross-linking agent ii), in particular composition "C4", does not contain i) any compound of formula (I).

[0476] The present invention is further illustrated in more detail by the examples presented below. The amounts given are expressed as weight percent unless otherwise specified.

[0477] Example

[0478] Methods and Measurements

[0479] Application to the skin

[0480] a) One-step protocol

[0481] The compound of formula (I) having acetoacetate functionality and the crosslinker are mixed together prior to application, and the system remains fluid long enough to allow application to a substrate.

[0482] The composition is applied (wet thickness 100 μm) using a film spreader to a Bioskin type vitro support (Bioskin plate #10) from Maprecos (elastomeric skin-simulating support). The deposit is allowed to dry for 24 hours.

[0483] After 24 hours of drying, the deposits are evaluated according to the protocol set out later in this specification.

[0484] b) Two-step protocol

[0485] The first composition (called base coat) is applied (wet thickness 100 μm) using a film spreader to a Bioskin type vitro support (Bioskin plate #10) from Maprecos (elastomeric skin-simulating support). The deposit is allowed to dry for 24 hours.

[0486] After this initial gesture, a second composition (called the top coat) is applied in the same manner.

[0487] The deposit is allowed to dry for 24 hours.

[0488] After 24 hours of drying, the deposits are evaluated according to the protocol described later in the specification.

[0489] Resistance to adhesive tapes

[0490] 1 piece of adhesive tape (Scotch 登録商標 Magic 商標 A strip of adhesive tape (810, manufactured by 3M; width = 19 mm, length = 5 cm) is applied to the deposit. A weight of approximately 1070 g is placed on one piece of the adhesive tape for 30 seconds. The adhesive tape is then peeled off and fixed to a slide holder to properly observe the results. The adhesion of the film to the substrate is thus evaluated.

[0491] Resistant to olive oil, sebum and water

[0492] 0.5 mL of olive oil, sebum or water is applied to the film of the formulation. After 5 minutes, the olive oil, sebum or water is wiped off 15 times with absorbent cotton and removed. Thus, the film is examined for deterioration after contact with a drop of an attacking agent. Resistance is evaluated according to the following scale: +++: No attack of deposits, remains in its original state; ++: slight movement, but deposits remain intact; +: slight changes in the deposits, some migration observed; 0: The deposits are completely decomposed and a lot of transfer is observed on the absorbent cotton.

[0493] Fragmentation test of formulations in Bioskin

[0494] For the olive oil / sebum / water and adhesive tape resistance test, the film is applied to a sample of Bioskin. After drying for 1 day, the Bioskin plate is stretched manually 10 times.

[0495] The result on the film (debris or no debris) is then observed.

[0496] The evaluation will be carried out as follows: +++: Cosmetic properties rated as very effective; ++: Cosmetic properties were evaluated as moderately effective; +: Cosmetic properties were evaluated as somewhat effective; 0: The cosmetic properties were rated as ineffective.

[0497] Example 1: Synthesis of castor oil with acetoacetate functionality (compound 1)

[0498] The synthesis is represented by the following preparative scheme: [ka]

[0499] 50 g of castor oil (sold by Interchimie) and 25.40 g of tert-butyl acetoacetate were added to a 250 mL SVL equipped with a mechanical stirrer, thermometer, and distillation column. 登録商標 The reaction mixture is heated to 130°C in an oil bath. After 7 hours, the reaction mixture is cooled, placed in a 250 mL pear-shaped flask, and heated in a rotavapor under continuous vacuum at 120°C for 1 hour.

[0500] Example 2: Synthesis of hydroxylated castor oil with acetoacetate functionality (compound 2)

[0501] The synthesis is represented by the following preparative scheme:

[0502] Step a): [ka]

[0503] Step b): [ka]

[0504] In step a), hydroxylated castor oil is prepared: 10 g of castor oil (sold by Interchimie), 9 g of 3-mercapto-1,2-propanodiol (sold by Sigma-Aldrich), and 0.7 g of 2-hydroxy-2-methylpropiophenone (sold by Sigma-Aldrich) are added to 20 mL of ethyl acetate in a 250 mL round-bottom flask equipped with a magnetic stirrer and stirred for 5 minutes under argon. The reaction medium is irradiated for 4 hours under a UV lamp (100 W, 365 nm) and then washed three times with water saturated with NaCl.

[0505] The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. Finally, the solvent and traces of thiol and photoinitiator (2-hydroxy-2-methylpropiophenone) are removed by distillation under reduced pressure. The product obtained is used directly in the next step.

[0506] In step b), the hydroxylated castor oil is functionalized with acetoacetate groups: 10 g of the hydroxylated castor oil obtained in step a) and 12 g of tert-butyl acetoacetate are placed in a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction medium is heated to 130 °C in an oil bath. After 4 hours, the reaction medium is placed under continuous vacuum for 1 hour. A yellow, viscous oil is obtained.

[0507] Example 3: Synthesis of epoxidized oil with acetoacetate functionality (compound 3)

[0508] The synthesis is represented by the following preparative scheme:

[0509] Step a): [ka]

[0510] Step b): [ka]

[0511] In step a), 200 g of epoxidized oil (Vikoflex 7170 sold by Arkema), 50.4 g of lactic acid, and 6.52 g of caffeine were added to a 500 mL SVL equipped with a mechanical stirrer, an argon inlet, and a distillation column. 登録商標 The reaction mixture is placed in a reactor and heated to 120°C for 5 hours to obtain a polyhydroxylated compound. A slightly yellow viscous oil is obtained.

[0512] In step b), 165 g of the polyhydroxylated compound obtained in step a) and 116.74 g of tert-butyl acetoacetate are added to a 500 mL SVL equipped with a mechanical stirrer, an argon inlet and a distillation column. 登録商標 The reaction mixture is heated to 130-140°C for 5 hours. After 5 hours of heating, the medium is placed under vacuum at 140°C and 50 mbar. An orange viscous oil is obtained.

[0513] The oil obtained is diluted with ethyl acetate and washed three times with saturated sodium bicarbonate solution and then twice with water. The organic phase is filtered over MgSO4, and the ethyl acetate is then distilled off under reduced pressure at 100°C in a rotavapor. A slightly orange viscous oil is obtained.

[0514] Example 4: Synthesis of soybean oil with acetoacetate functionality (compound 4)

[0515] The synthesis is represented by the following preparative scheme:

[0516] Step a): [ka]

[0517] Step b): [ka] [ka]

[0518] In step a), 10 g of soybean oil (Henry Lamotte Oils), 10 g of 3-mercapto-1,2-propanediol (sold by Sigma-Aldrich), and 0.8 g of 2-hydroxy-2-methylpropiophenone (sold by Sigma-Aldrich) are added to 25 mL of ethyl acetate in a 250 mL round-bottom flask equipped with a magnetic stirrer and stirred for 5 minutes under argon. The reaction medium is then irradiated for 4 hours under a UV lamp (100 W, 365 nm) and then washed three times with NaCl-saturated water. The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. The solvent and traces of thiol and photoinitiator are removed by distillation under reduced pressure.

[0519] In step b), 10 g of the hydroxylated soybean oil obtained in step a) and 14 g of tert-butyl acetoacetate are placed in a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction medium is heated to 130°C in an oil bath. After 4 hours, the reaction medium is cooled and the excess tert-butyl acetoacetate is removed under continuous vacuum for 1 hour. A yellow, viscous oil is obtained.

[0520] Example 5: Synthesis of an "acid" oil with acetoacetate functionality (compound 5)

[0521] The synthesis is represented by the following preparative scheme:

[0522] Step a): [ka]

[0523] Step b): [ka]

[0524] Process c): [ka]

[0525] In step a), 100 g of citric acid and 419 g of oleyl alcohol are added to a 500 mL SVL equipped with a mechanical stirrer and a distillation column. 登録商標 The reaction medium is heated using a heating mantle at 190°C for 7 hours and then at 220°C for 5 hours. The reaction is monitored by acid number. When the acid number is less than 5, the reaction is stopped.

[0526] In step b), 100 g of the acid oil obtained in step a), 70 g of 3-mercapto-1,2-propanediol (sold by Sigma-Aldrich), and 5 g of 2-hydroxy-2-methylpropiophenone (sold by Sigma-Aldrich) are added to 15 mL of ethyl acetate in a 250 mL round-bottom flask equipped with a magnetic stirrer and stirred for 5 minutes under argon. The reaction medium is then irradiated for 4 hours under a UV lamp (100 W, 365 nm) and then washed three times with water saturated with NaCl. The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. The solvent and traces of thiol and photoinitiator (2-hydroxy-2-methylpropiophenone) are removed by distillation under reduced pressure.

[0527] In step c), 100 g of the hydroxylated acid oil obtained in step b) and 100 g of tert-butyl acetoacetate are placed in a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction medium is heated to 130° C. in an oil bath. After 4 hours of reaction, the reaction medium is placed under continuous vacuum for 1 hour. A brown, viscous oil is obtained.

[0528] Example 6: Synthesis of castor oil with acetoacetate functionality (compound 6)

[0529] The synthesis is represented by the following preparative scheme:

[0530] Step a): [ka]

[0531] Step b): [ka]

[0532] In step a), 100 g of castor oil (sold by Interchimie), 17 g of 3-mercapto-1,2-propanediol (sold by Sigma-Aldrich), and 1 g of 2-hydroxy-2-methylpropiophenone (sold by Sigma-Aldrich) are added to 20 mL of ethyl acetate in a 250 mL round-bottom flask equipped with a magnetic stirrer and stirred for 5 minutes under argon. The reaction medium is irradiated for 4 hours under a UV lamp (100 W, 365 nm) and then washed three times with NaCl-saturated water. The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. The solvent and traces of thiol and photoinitiator (2-hydroxy-2-methylpropiophenone) are removed by distillation under reduced pressure.

[0533] In step b), 100 g of the hydroxylated castor oil obtained in step a) and 99 g of tert-butyl acetoacetate are placed in a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction medium is then heated to 130° C. in an oil bath (rated temperature of the oil bath: 140° C.). After 4 hours, the reaction medium is placed under continuous vacuum for 1 hour. A yellow, viscous oil is obtained.

[0534] Example 7: Synthesis of mannitol dihexanoate with acetoacetate functionality (compound 7)

[0535] The synthesis is represented by the following preparative scheme:

[0536] Step a): [ka]

[0537] Step b): [ka]

[0538] In step a), mannitol dihexanoate is obtained from mannitol under the conditions described in Angew. Chem. Int. Ed. 2010, 49, 7695-7698.

[0539] After 64 hours at 45° C., the reaction medium is filtered and then concentrated under reduced pressure. The crude compound obtained after filtration and evaporation is then triturated in dichloromethane.

[0540] In step b), 4 equivalents of 2,2,6-trimethyl-1,3-dioxin-4-one in p-xylene are heated for 2 hours at 140° C. Purification by silica gel chromatography gives mannitol dihexanoate acetoacetate.

[0541] Example 8: Preparation of Compositions A to E

[0542] Composition A containing the compound of formula (I) according to the present invention, and compositions B to E containing the compound of formula (I) according to the present invention are prepared using the contents shown in the table below, which are expressed as weight percentages relative to the total weight of the composition.

[0543] [Table 1]

[0544] Compositions A to E are prepared by simply mixing the ingredients detailed in Table 1 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at room temperature for 2 minutes at 3500 rpm.

[0545] Example 9: One-step skin application of Compositions A to E

[0546] Compositions A through E are applied according to the one-step skin application protocol previously described.

[0547] The deposit is then evaluated according to protocols for resistance to olive oil, sebum and water, for resistance to adhesive tape, and for the fragmentation test of the formulation on Bioskin.

[0548] The evaluation results are summarized in the table below.

[0549] [Table 2]

[0550] It can be seen that by applying Compositions B through E according to the method of the present invention, substantivity to olive oil, water and sebum is very significantly improved compared to application of Composition A, and the adhesive tape test and debris distribution test are also very impressive, thus indicating that Compositions B through E are cohesive and adhere to the substrate.

[0551] By applying compositions B to E according to the method of the invention, a deposit is obtained which is resistant to everyday chemical attacks (water / sebum / olive oil) and therefore very resistant to mechanical stress (fracture).

[0552] Example 10: Preparation of Compositions F to H

[0553] Composition F containing a compound of formula (I), and compositions G and H containing a compound of formula (I) and a crosslinker are prepared using the contents shown in the table below, expressed as weight percentages relative to the total weight of the composition.

[0554] [Table 3]

[0555] Compositions F through H are prepared by simply mixing the ingredients detailed in Table 3 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at room temperature for 2 minutes at 3500 rpm.

[0556] Example 11: One-step skin application of Compositions F through H

[0557] Compositions F-H are applied according to the previously described one-step skin application protocol.

[0558] The deposits are then evaluated according to protocols for resistance to olive oil, sebum and water, as well as for the fragmentation test of the formulations on Bioskin.

[0559] The evaluation results are summarized in the table below.

[0560] [Table 4]

[0561] By applying compositions G and H according to the method of the present invention, it can be seen that substantivity to olive oil, water and sebum is improved compared to application of composition F, and the debris distribution test is also very impressive.

[0562] By applying compositions G and H according to the method of the invention, deposits are obtained which are resistant to everyday chemical attacks (water / sebum / olive oil) and therefore very resistant to mechanical stress (fracture).

[0563] Example 12: Preparation of Compositions I and J

[0564] Composition I containing a compound of formula (I) and composition J containing a compound of formula (I) and a crosslinker are prepared using the contents shown in the table below, expressed as weight percentages relative to the total weight of the composition.

[0565] [Table 5]

[0566] Compositions I and J are prepared by simply mixing the ingredients detailed in Table 5 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at 3500 rpm for 2 minutes at room temperature.

[0567] Example 13: One-step skin application of compositions I and J

[0568] Composition I and Composition J are applied according to the one-step skin application protocol previously described.

[0569] The deposits are then evaluated according to protocols for resistance to olive oil, sebum and water, as well as for the fragmentation test of the formulations on Bioskin.

[0570] The evaluation results are summarized in the table below.

[0571] [Table 6]

[0572] By applying Composition J according to the method of the present invention, it can be seen that substantivity to olive oil, water, and sebum is improved compared to application of Composition I, and the debris distribution test is also very impressive.

[0573] By applying composition J according to the method of the invention, a deposit is obtained which is resistant to everyday chemical attacks (water / sebum / olive oil) and therefore very resistant to mechanical stress (fracture).

[0574] Example 14: Preparation of Compositions K and L

[0575] Composition K comprising a compound of formula (I) and composition L comprising a compound of formula (I) and a crosslinker are prepared using the contents shown in the table below, expressed as weight percentages relative to the total weight of the composition.

[0576] [Table 7]

[0577] Compositions K and L are prepared by simply mixing the ingredients detailed in Table 7 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at room temperature for 2 minutes at 3500 rpm.

[0578] Example 15: One-step skin application of compositions K and L

[0579] Composition K and Composition L are applied according to the one-step skin application protocol previously described.

[0580] The deposit is then evaluated according to protocols for resistance to olive oil, sebum and water, for resistance to adhesive tape, and for the fragmentation test of the formulation on Bioskin.

[0581] The evaluation results are summarized in the table below.

[0582] [Table 8]

[0583] It can be seen that by applying composition L according to the method of the present invention, the substantivity to olive oil, water and sebum is very significantly improved compared to the application of composition K, and the adhesive tape test and the debris distribution test are also very impressive, thus showing that composition L is cohesive and adheres to the substrate.

[0584] By applying composition L according to the method of the invention, a deposit is obtained which is resistant to everyday chemical attacks (water / sebum / olive oil) and therefore very resistant to mechanical stress (fracture).

[0585] Example 16: Preparation of Composition M and Composition N

[0586] Composition M containing a compound of formula (I) and composition N containing a compound of formula (I) and a crosslinker are prepared using the contents shown in the table below, expressed as weight percentages relative to the total weight of the composition.

[0587] [Table 9]

[0588] Compositions M and N are prepared by simply mixing the ingredients detailed in Table 9 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at 3500 rpm for 2 minutes at room temperature.

[0589] Example 17: One-step skin application of Composition M and Composition N

[0590] Composition M and Composition N are applied according to the previously described one-step skin application protocol.

[0591] The deposits are then evaluated according to protocols for resistance to olive oil, sebum and water, as well as for the fragmentation test of the formulations on Bioskin.

[0592] The evaluation results are summarized in the table below.

[0593] [Table 10]

[0594] It can be seen that by applying Composition N according to the method of the present invention, substantivity to olive oil, water and sebum is very significantly improved compared to the application of Composition M, and that the adhesive tape test and crush test are also very impressive, thus showing that Composition N is cohesive and adheres to the substrate.

[0595] By applying composition N according to the method of the invention, a deposit is obtained which is resistant to everyday chemical attacks (water / sebum / olive oil) and therefore very resistant to mechanical stress (fracture).

[0596] Example 18: Preparation of Compositions O to R

[0597] Compositions O to R are prepared using the contents shown in the table below, expressed as a weight percentage relative to the total weight of the composition under consideration.

[0598] [Table 11]

[0599] The "base coat" and "top coat" compositions are prepared by simply mixing the ingredients detailed in Table 11 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at 3500 rpm for 2 minutes at room temperature.

[0600] Example 19: One-step or two-step skin application of Compositions O through R

[0601] Compositions O through R are applied according to the one-step or two-step skin application protocols previously described.

[0602] The deposit is then evaluated according to protocols for resistance to olive oil, sebum and water, for resistance to adhesive tape, and for the fragmentation test of the formulation on Bioskin.

[0603] The evaluation results are summarized in the table below.

[0604] [Table 12]

[0605] It can be seen that by applying Compositions P through R according to the method of the present invention, substantivity to olive oil, water and sebum is very significantly improved compared to application of Composition O, and that the adhesive tape test and crush test are also very impressive, thus indicating that Compositions P through R are cohesive and adhere to the substrate.

[0606] By applying formulas P to R according to the method of the invention, a deposit is obtained which is resistant to everyday chemical attacks (water / sebum / olive oil) and therefore has a tensile effect on Bioskin.

[0607] Example 20: Preparation of Composition S and Composition T

[0608] Composition S containing a compound of formula (I) and composition T containing a compound of formula (I) and a crosslinker are prepared using the contents shown in the table below, expressed as weight percentages relative to the total weight of the composition.

[0609] [Table 13]

[0610] Compositions S and T are prepared by simply mixing the ingredients detailed in Table 13 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at room temperature for 2 minutes at 3500 rpm.

[0611] Example 21: One-step skin application of composition S and composition T

[0612] Compositions S and T are applied according to the one-step skin application protocol previously described.

[0613] The deposit is then evaluated according to protocols for resistance to olive oil, sebum and water, for resistance to adhesive tape, and for the fragmentation test of the formulation on Bioskin.

[0614] The evaluation results are summarized in the table below.

[0615] [Table 14]

[0616] It can be seen that by applying Composition T according to the method of the present invention, substantivity to olive oil, water and sebum is very significantly improved compared to the application of Composition S, and that the adhesive tape test and debris distribution test are also very impressive, thus indicating that Composition T is cohesive and adheres to the substrate.

[0617] By applying composition T according to the method of the invention, a deposit is obtained which is resistant to everyday chemical attacks (water / sebum / olive oil) and therefore very resistant to mechanical stress (fracture).

[0618] Example 22: Preparation of Composition U and Composition V

[0619] Composition U comprising a compound of formula (I) and composition V comprising a compound of formula (I) and a crosslinker are prepared using the contents shown in the table below, expressed as weight percentages relative to the total weight of the composition.

[0620] [Table 15]

[0621] Compositions U and V are prepared by simply mixing the ingredients detailed in Table 15 using a Speed ​​Mixer (a mixing device that uses centrifugal force) at 3500 rpm for 2 minutes at room temperature.

[0622] Example 23: One-step skin application of Composition U and Composition V

[0623] Composition U and Composition V are applied according to the one-step skin application protocol previously described.

[0624] The deposit is then evaluated according to protocols for resistance to olive oil, sebum and water, for resistance to adhesive tape, and for the fragmentation test of the formulation on Bioskin.

[0625] The evaluation results are summarized in the table below.

[0626] [Table 16]

[0627] By applying composition V according to the method of the present invention, it can be seen that substantivity to olive oil, water and sebum is improved compared to application of composition U, and the debris distribution test is also very impressive.

[0628] By applying composition V according to the method of the invention, a deposit is obtained which is resistant to everyday chemical attacks (water / sebum / olive oil) and therefore very resistant to mechanical stress (fracture).

Claims

1. 1. A method for treating, in particular cosmetically treating, keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, comprising applying to said keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, at least i) one or more compounds of formula (I) below, their optical isomers or geometric isomers, and / or solvates thereof, such as hydrates, or compositions comprising said compounds: 【Chemistry 1】 Here, in formula (I), Z is a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic, polyvalent C 2 ~C 40 , especially C 3 ~C 36 , where Z optionally represents a hydrocarbon-based moiety of -O-, -N(R a -C(O)-, -S-, -C(O)-, (hetero)cyclic rings, and combinations thereof; AK1 is a divalent, saturated or unsaturated, linear or branched C 1 ~C 12 , preferably C 1 ~C 6 , preferably saturated C 1 ~C 6 , represents a hydrocarbon-based chain; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C, linear or branched, saturated or unsaturated, optionally substituted with one or more identical or different moieties selected from 1 ~C 40 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular from -OC(O)-, -C(O)-O- and / or -(hetero)cycle-O-(hetero)cycle-; AK3 is a divalent, linear or branched, saturated or unsaturated C 1 ~C 12 , preferably C 1 ~C 6 , preferably saturated C 1 ~C 6 , and even more preferably C 1 ~C 4 , representing a hydrocarbon-based chain; R is a hydrogen atom, a linear or branched, saturated or unsaturated C 1 ~C 6 , preferably C 1 ~C 4 the alkyl portion, especially the methyl portion, of —C(O)—C(R a )(R b )-C(O)-R 4 represents a part; X represents -O-, -S-, -OC(O)- or -C(O)-O-; Y represents -OC(O)- or -C(O)-O-; R 4 is a linear or branched, saturated or unsaturated C 1 ~C 6 A monovalent hydrocarbon-based moiety, preferably (C 1 ~C 4 ) an alkyl group, in particular methyl or tert-butyl, more preferably methyl; R a and R b may be the same or different and are hydrogen atoms or (C 1 ~C 4 ) an alkyl group, preferably a hydrogen atom; p represents an integer equal to 0 or 1; m represents an integer equal to 0, 1, 2, 3 or 4; when m is greater than 1, -Y-AK 2 It is understood that the moieties may be the same or different; n represents an integer equal to 0, 1, 2, 3, or 4; when n is greater than 1, -(O) t -(AK 1 ) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u It is understood that the moieties may be the same or different; t represents an integer equal to 0 or 1; q represents an integer equal to 0 or 1; u represents an integer equal to 1, 2, or 3; v represents an integer equal to 1, 2, or 3; When q is equal to 0, t is equal to 0, (m+n) is equal to or greater than 1, and one or more compounds of formula (I) contain at least two -C(O)-C(R a )(R b )-C(O)-R 4 It is understood that this includes groups; and ii) at least one cross-linking agent in one or more sequential steps.

2. One or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, Z is trivalent -CH 2 -CH-CH 2 -represents a part; p is equal to 0; n equals 0; m is equal to 3; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C, linear or branched, saturated or unsaturated, optionally substituted with one or more identical or different moieties selected from 12 ~C 24 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxide and combinations thereof, in particular from O-(CO)- or (CO)-O-; Y, AK3, v, R, X, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 2. The method of claim 1, wherein

3. One or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, p is equal to 0; Z is a linear or branched, saturated or unsaturated, preferably saturated, acyclic, polyvalent C 4 ~C 24 , especially C 6 ~C 20 , more particularly C 14 ~C 20 , especially C 17 , wherein Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u ] n may be substituted by a moiety; n represents an integer equal to 0, 1, 2, 3, or 4; when n is greater than 1, -(O) t -(AK 1 ) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u It is understood that the moieties may be the same or different; preferably, n is not zero; m is equal to 1; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C is linear or branched, saturated or unsaturated, preferably saturated, substituted by one or more identical or different moieties selected from 3 ~C 8 , especially C 4 or C 6 and / or said chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-; Y, AK1, AK3, t, q, u, v, R, X, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 be understood to include parts 2. The method of claim 1, wherein

4. One or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, p is equal to 0; n+m is equal to 4, and m is not zero; Z is unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated, and acyclic; 2 ~C 24 , especially C 3 ~C 10 , especially C 3 represents a tetravalent hydrocarbon-based moiety of AK2 independently represents -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v and preferably one or more -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C may be linear or branched, saturated or unsaturated, preferably saturated, optionally substituted by a moiety 12 ~C 24 , preferably C 16 ~C 20 , especially C 18 and / or said chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-; AK3 is a linear or branched, saturated or unsaturated C 1 ~C 12 , preferably C 1 ~C 6 , preferably saturated C 1 ~C 6 , and even more preferably C 2 ~C 4 , or even better C 3 represents a divalent hydrocarbon-based chain of the formula: v is as defined in claim 1; preferably, v is equal to 2; X is as defined in claim 1; preferably, X represents a sulfur atom; Y, AK1, u, t, q, R, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 2. The method of claim 1, wherein

5. One or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, p is equal to 1; Z is a linear or branched, saturated or unsaturated, preferably saturated, and acyclic, polyvalent C 14 ~C 24 , especially C 16 ~C 20 , preferably C 17 , wherein Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u ] n may be substituted with a moiety, but is preferably unsubstituted; AK2 is -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C is linear or branched, saturated or unsaturated, preferably saturated, substituted by one or more identical or different moieties selected from 14 ~C 30 , especially C 20 ~C 29 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-; X is as defined in claim 1; preferably, X represents a sulfur atom; Y, AK1, AK3, n, m, v, t, q, u, R, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 2. The method of claim 1, wherein

6. One or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, p is equal to 0; Z is linear or branched, saturated or unsaturated, preferably saturated, and acyclic, C 2 ~C 24 , especially C 3 ~C 10 , preferably C 4 or C 5 , wherein Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u ] n substituted by the moiety, n preferably equals 1; n+m is equal to 4, preferably m is equal to 3; AK2 independently represents a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 16 ~C 24 , preferably C 17 , which represents a hydrocarbon-based chain of the formula: -OR, -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v and / or the chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-; X is as defined in claim 1, preferably X represents a sulfur atom; Y, AK1, AK3, u, t, q, v, n, m, R, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 2. The method of claim 1, wherein

7. One or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, p is equal to 0; m is not zero; Z is a divalent C which is linear or branched, saturated or unsaturated, conjugated or non-conjugated, preferably non-conjugated, acyclic or cyclic, aromatic or non-aromatic, preferably non-aromatic. 2 ~C 24 , especially C 3 ~C 12 , wherein the Z moiety also represents a hydrocarbon-based moiety of —O—, —N(R a )-, -S-, -C(O)-, one or more heterocycloalkyls of 5- or 6-membered rings, and combinations thereof; AK2 is a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 14 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, said chain being selected from the group consisting of -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v and / or the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-, more preferably uninterrupted; X is as defined in claim 1, preferably X represents a sulfur atom; Y, AK1, AK3, v, t, q, u, R, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 2. The method of claim 1, wherein

8. One or more compounds of formula (I), their optical or geometric isomers, and / or solvates thereof, such as hydrates, p is equal to 0; Z is linear or branched, saturated or unsaturated, preferably saturated, and acyclic, C 2 ~C 24 , especially C 3 ~C 10 , preferably C 4 or C 5 , wherein Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u ] n is substituted by a moiety; n+m is equal to 6, preferably m is equal to 2; AK2 is a linear or branched, saturated or unsaturated, preferably saturated, C 3 ~C 8 , especially C 4 , C 5 or C 6 represents a monovalent hydrocarbon-based chain of Y, AK1, AK3, t, q, u, v, R, X, R 4 , R a and R b is as defined above for formula (I); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 2. The method of claim 1, wherein

9. The one or more compounds of formula (I) are selected from the compounds of formula (Ia) below, and also their optical or geometric isomers and / or solvates thereof, such as hydrates: Z-(Y-AK2) 3 (Ia) wherein in formula (Ia): Z is -CH 2 -CH-CH 2 - represents; AK2 independently represents -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C, linear or branched, saturated or unsaturated, optionally substituted with one or more identical or different moieties selected from 12 ~C 24 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxide and combinations thereof, in particular from -OC(O)- and -C(O)-O-; Y, AK3, v, R, X, R 4 , R a and R b is as defined in claim 1; preferably, Y denotes -OC(O); The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 10. The method of treatment according to claim 1.

10. The one or more compounds of formula (I) are selected from the compounds of formula (Ib) below, and also their optical or geometric isomers, and / or solvates, such as hydrates, thereof: m (AK2-Y)-Z-[(O) t -(AK1) q -(O-C(O)-C(R a )(R b )-C(O)-R 4 ) u ] n (Ib) Here, in formula (Ib), n+m is equal to 4, m is not zero; m and n are as defined in claim 1; Z is unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated, and acyclic; 2 ~C 24 , especially C 3 ~C 10 , preferably C 3 represents a tetravalent hydrocarbon-based moiety of AK2 independently represents -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v and preferably one or more -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C may be linear or branched, saturated or unsaturated, preferably saturated, optionally substituted by a moiety 12 ~C 24 , preferably C 16 ~C 20 , preferably C 18 and / or said chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular from -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-; AK3 is a linear or branched, saturated or unsaturated C 1 ~C 12 , preferably C 1 ~C 6 , preferably saturated C 1 ~C 6 , and even more preferably C 2 ~C 4 , preferably C 3 represents a divalent hydrocarbon-based chain of the formula: v is as defined in claim 1; preferably, v is equal to 2; X is as defined in claim 1; preferably, X represents a sulfur atom; Y, AK1, u, t, q, R, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 10. The method of treatment according to claim 1.

11. The one or more compounds of formula (I) are selected from the compounds of formula (Ic) below, their optical or geometric isomers, and / or solvates thereof, such as hydrates: m (AK 2 -Y)-ZH-[(O)t-(AK1) q -(O-C(O)-C(R a )(R b )-C(O)-R 4 ) u ] n (Ic) Here, in formula (Ic), Z is a linear or branched, saturated or unsaturated, preferably saturated, and acyclic, polyvalent C 14 ~C 24 , especially C 16 ~C 20 , e.g. C 17 , wherein Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u ] n may be substituted with a moiety, preferably unsubstituted; AK2 is -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v C is linear or branched, saturated or unsaturated, preferably saturated, substituted by one or more identical or different moieties selected from 14 ~C 30 , preferably C 20 ~C 29 and / or said chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-; X is as defined in claim 1, preferably X represents a sulfur atom; Y, AK1, AK3, n, m, v, t, q, u, R, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts 10. The method of treatment according to claim 1.

12. The one or more compounds of formula (I) are selected from compounds of formula (Id) below, their optical or geometric isomers, and / or solvates thereof, such as hydrates: m (AK 2 -Y)-Z-[(O)t-(AK1) q -(O-C(O)-C(R a )(R b )-C(O)-R 4 ) u ] n (Id) Here, in formula (Id), n+m is equal to 4, preferably m is equal to 3; Z is linear or branched, saturated or unsaturated, preferably saturated or acyclic, C 2 ~C 24 , especially C 3 ~C 10 , especially C 4 or C 5 , wherein Z also represents one or more -[(O) t -(AK1) q -(OC(O)-C(R a )(R b )-C(O)-R 4 ) u ] n substituted by the moiety, n preferably equals 1; AK2 independently represents a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 16 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, said chain being selected from the group consisting of -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v and / or the chain may be interrupted, preferably uninterrupted, by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, one or more (hetero)cycles and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-; X is as defined in claim 1, preferably X represents a sulfur atom; Y, AKI, AKI, u, v, R, R 4 , R a and R b is as defined in claim 1, These compounds have at least two -C(O)-C(R a )(R b )-C(O)-R 4 It is understood to include the moiety, 10. The method of treatment according to claim 1.

13. the one or more compounds of formula (I) are selected from compounds of formula (Ie) below, their optical or geometric isomers, and / or solvates thereof, such as hydrates, m (AK2-Y)-Z-[(O) t -(AK1) q -(O-C(O)-C(R a )(R b )-C(O)-R 4 ) u ] n (Ie) Here, in formula (Ie), n+m is equal to 2, m is not zero, preferably m is equal to 2; n is as defined in claim 1; preferably n is zero; Z is linear or branched, saturated or unsaturated, conjugated or non-conjugated, preferably non-conjugated, acyclic or cyclic, aromatic or non-aromatic, preferably non-aromatic, C 2 ~C 24 , especially C 3 ~C 12 , represents a divalent hydrocarbon-based moiety, and the Z moiety also represents —O—, —N(R a )-, -S-, -C(O)-, one or more (hetero)cyclic rings and combinations thereof; preferably, Z is a divalent -(CH 2 ) g -(heterocycle)-O-(CH 2 ) h -(heterocycle)-(CH 2 ) j - moiety, where h is 0, 1 or 2, preferably 0 or 1, and g and j are independently an integer from 1 to 3, preferably 1; (heterocycle) denotes a divalent heterocyclic moiety (i.e. heterocycle), preferably a heterocycloalkyl moiety, more particularly a divalent 5- or 6-membered heterocycloalkyl moiety, in particular a divalent tetrahydrofuran moiety or a divalent tetrahydropyran moiety, said heterocycle being selected from the group consisting of -OR (where R is as defined in claim 1), in particular -OH or -OC(O)-C(R a )(R b )-C(O)-R 4 and optionally substituted with one or more moieties selected from: AK2 is a linear or branched, saturated or unsaturated, preferably saturated, C 14 ~C 30 , preferably C 14 ~C 24 , preferably C 17 represents a monovalent hydrocarbon-based chain, said chain being selected from the group consisting of -OR and -X-AK3-(OC(O)-C(R a )(R b )-C(O)-R 4 ) v and / or the chain may be interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably by -OC(O)- or -C(O)-O-, more preferably uninterrupted; X is as defined in claim 1; preferably, X represents a sulfur atom; Y, AK1, AK3, v, t, q, u, R, R 4 , R a and R b is as defined in claim 1; The compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 is understood to include parts A method of treatment according to any one of claims 1 to 12.

14. 14. The method of treatment according to any one of claims 1 to 13, wherein the one or more compounds of formula (I) are selected from the following compounds, their optical or geometric isomers, and / or solvates, such as hydrates, thereof: 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 where W is a hydrogen atom or -C(O)-C(R a )(R b )-C(O)-R 4 and the compound has at least two —C(O)—C(R a )(R b )-C(O)-R 4 Contains a group.

15. The one or more crosslinking agents in ii) are selected from (poly)amine, (poly)thiol, (poly)carbonyl, (poly)acrylate and metal alkoxide compounds, and combinations thereof, preferably selected from (poly)amine compounds; Preferably, the one or more crosslinking agents in ii) are A) a (poly)amine compound, ia) chitosan, e.g., poly(D-glucosamine); ib) polyetherdiamines, in particular polyethylene glycol α,ω-diamines, which have amine functional groups at the chain ends; ic) polyethertriamines, especially polyetheramines (i.e., Jeffamine); id) aminoalkoxysilanes, in particular APTES, ie) 4,7,10-trioxa-1,13-tridecanediamine, and if) polydialkylsiloxanes containing primary amine groups at the chain end or in the side chain, especially polydimethylsiloxanes containing primary amine groups, more especially poly(dimethoxysiloxanes) terminated with bis(3-aminopropyl) (PDMS-diNH 2 ), and amodimethicones having an amine group in the side chain, more particularly bis-cetearyl amodimethicone the (poly)amine compound selected from the group consisting of: B) a (poly)thiol compound, iia) a polydialkylsiloxane having thiol functional groups, and iib) alkoxysilanes with thiol functionality is selected from In particular, iia) selected from polydialkylsiloxanes having thiol functional groups, preferably polydimethylsiloxanes having thiol groups in the side chains, in particular mercaptopropyl, and more particularly from compounds of formula (XIII) R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALK 1 -SH)-O] n -Si(R b )(R d )-R a (XIII) Here, in formula (XIII), R a and R b may be the same or different, preferably the same, (C 1 ~C 4 ) alkyl groups, especially methyl, (C 1 ~C 4 ) alkoxy groups, especially methoxy, aryl groups, especially phenyl, aryloxy groups, especially phenoxy, aryl (C 1 ~C 4 ) alkyl groups, especially benzyl, or aryl (C 1 ~C 4 ) alkoxy groups, especially benzoxy, preferably (C 1 ~C 4 ) an alkyl group, more preferably methyl; R d is (C 1 ~C 4 ) alkyl groups, especially methyl, (C 1 ~C 4 ) alkoxy groups, especially methoxy, aryl groups, especially phenyl, aryloxy groups, especially phenoxy, aryl (C 1 ~C 4 ) alkyl groups, especially benzyl, aryl (C 1 ~C 4 ) alkoxy groups, in particular benzoxy, or (C 1 ~C 4 ) alkylamino group, amino group or thiol group substituted (C 1 ~C 6 ) alkyl group, preferably (C 1 ~C 4 ) an alkyl group, more preferably methyl; and preferably R a , R b and R d , are identical, and (C 1 ~C 6 ) an alkyl group, more preferably methyl; ALK 1 represents a divalent hydrocarbon-based chain, linear or branched, optionally cyclic, saturated or unsaturated, having 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen atoms, in particular oxygen atoms, (thio)carbonyl groups C(X) (wherein X represents O or S), or combinations thereof, in particular -O-, -OC(O)- or -C(O)-O-; preferably ALK 1 is (C 1 ~C 6 ) alkylene, more preferably (C 1 ~C 4 ) an alkylene group, even more preferably propylene, n and m may be the same or different and represent integers greater than 2, and in particular the values ​​of m and n are such that the weight average molecular weight of the polyorganosiloxane is between 1,000 and 55,000 g.mol -1 That which is, The (poly)thiol compound is selected from the group consisting of: C) a (poly)acrylate compound of the following formula (XIV): L[-Y-C(O)-C(R e )=CH 2 ] q (XIV) Here, in formula (XIV), q represents an integer of 2 or more, in particular, n is 2 to 10, preferably 2 to 5; L represents a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, polyvalent (at least divalent) group, in particular containing 1 to 500 carbon and / or silicon atoms, more in particular 2 to 40 carbon and / or silicon atoms, even more in particular 3 to 30 carbon and / or silicon atoms, preferably 6 to 20 carbon atoms; L is selected from O, S, N, Si, C(X) and combinations thereof, in particular -O-, -OC(X)-, -N(R)-C(X)-, -Si(R c )(R d )-O- (wherein R is a hydrogen atom or (C 1 ~C 6 ) alkyl groups, in particular methyl; and / or L may be interrupted and / or terminated by one or more heteroatoms or groups selected from -N(R a )R b and -(X') a -C(X)-(X'') b -R a wherein X, X' and X'' may be the same or different and are substituted with one or more groups selected from an oxygen atom or a sulfur atom, or N(R b a and b are 0 or 1, preferably the sum of a and b is 1; R a and R b may be the same or different, and may be a hydrogen atom, (C 1 ~C 6 ) alkyl group or aryl (C 1 ~C 4 ) alkyl group, in particular benzyl, preferably R a and R b represents a hydrogen atom, and R c and R d may be the same or different, (C 1 ~C 6 ) alkyl, aryl (C 1 ~C 4 ) alkyl or (C 1 ~C 6 ) represents an alkoxy group, R e is a hydrogen atom or (C 1 ~C 4 ) alkyl group, in particular methyl; preferably R e represents a hydrogen atom, and Y represents an oxygen atom or an amino group -N(H)-, preferably an oxygen atom; Preferably, Y is an oxygen atom and R e is a hydrogen atom, preferably L represents a divalent or trivalent, preferably trivalent, hydrocarbon-based chain having 1 to 8 carbon atoms, q is 2 or 3, preferably 3, and More preferably, the compound of formula (XIV) is trimethylolpropane triacrylate; D) Metal alkoxides, such as zirconium ethoxide (Zr(OC) 2 H 5 ) 4 ), zirconium propoxide (Zr(OCH 2 CH 2 CH 3 ) 4 ), zirconium isopropoxide (Zr(OCH(CH 3 ) 2 ) 4 ), zirconium butoxide Zr(OCH 2 CH 2 CH 2 CH 3 ) 4 , zirconium tert-butoxide (Zr(OC(CH 3 ) 3 ) 4 ), titanium ethoxide (Ti(OC 2 H 5 ) 4 ), titanium propoxide (Ti(OCH 2 CH 2 CH 3 ) 4 ), titanium isopropoxide (Ti(OCH(CH 3 ) 2 ) 4 ), titanium butoxide (Ti(OCH 2 CH 2 CH 2 CH 3 ) 4 ), titanium tert-butoxide (Ti(OC(CH 3 ) 3 ) 4 ), titanium 2-ethylhexyl oxide (Ti(OCH 2 CH(C 2 H 5 )(CH 2 ) 3 CH 3 ) 4 ) and combinations thereof, more preferably selected from zirconium propoxide, titanium propoxide, titanium butoxide, and combinations thereof; E) (Poly)carbonyl compounds, such as saturated or unsaturated, aromatic C 5 ~C 7 The (poly)carbonyl compounds contain carbocyclic rings, preferably aromatic, e.g., phenyl, or non-aromatic, and saturated, e.g., cyclohexyl, more preferably unsaturated and aromatic, e.g., terephthalaldehyde. The method of treatment according to any one of claims 1 to 14, wherein the

16. One or more cosmetic active agents iii) are also preferably applied to the keratin materials, in particular to the skin and / or lips and / or eyelashes and / or eyebrows, said one or more cosmetic active agents iii) preferably being a) dyes, in particular dyes selected from pigments, direct dyes and combinations thereof; b) active agents for caring for keratinous materials, preferably skin; c) UV blocking agents, and d) a combination of them is selected from Preferably, the one or more cosmetic active agents iii) are selected from a) dyes, preferably selected from pigments, direct dyes and combinations thereof; more preferably, the one or more pigments are selected from carbon black, iron oxides, in particular yellow, red and black iron oxides and mica coated with iron oxides, triarylmethane pigments, in particular blue and purple triarylmethane pigments, in particular Blue 1 Lake, azo pigments, in particular red azo pigments, more in particular D&C Red 7, alkali metal salts of litol red, in particular the calcium salt of litol red B, and Even more preferably, they are selected from red iron oxide, iron pyrite and azo pigments, in particular red azo pigments, more in particular D&C Red 7. A method of treatment according to any one of claims 1 to 15.

17. iv) at least one fatty substance, in particular at least one oil, preferably at least one volatile oil, more preferably Hydrocarbon-based oils having 8 to 16 carbon atoms, especially branched C 8 ~C 16 Alkanes, especially isoalkanes, more especially isoalkanes (also known as isoparaffins), preferably C 13 ~C 16 Isoparaffins, isododecane, isodecane, isohexadecane, for example oils sold under the tradename Isopar or Permethyl, alone or in combination, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular C 11 ~C 16 Alkanes, alone or in combination, in particular hexane, decane, undecane, tridecane, isoparaffins, in particular n-dodecane (C 12 ) and n-tetradecane (C 14 ), undecane-tridecane mixture, n-undecane (C 11 ) and n-tridecane (C 13 ), and combinations thereof, and also n-undecane (C 11 ) and n-tridecane (C 13 ) and volatile C 5 ~C 12 Cyclic, non-aromatic alkanes; short-chain esters having a total of 3 to 8 carbon atoms, in particular ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate; Structure R' 1 -OC(O)-O-R' 2 a carbonate hydrocarbon-based oil, where R' 1 and R' 2 are independently linear, branched or cyclic C 4 ~C 8 Alkyl groups, preferably C 4 ~C 8 alkyl group, advantageously and more preferably selected from dibutyl carbonate or dipentyl carbonate; formula R 1 -OR 2 ether oil, where R 1 and R 2 are each independently a linear, branched or cyclic C 4 ~C 8 Alkyl groups, preferably C 4 ~C 8 alkyl group; Silicone oils, in particular those containing 2 to 7 silicon atoms and optionally containing alkyl or alkoxy groups having 1 to 10 carbon atoms, in particular dimethicone, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and combinations thereof, with a viscosity of 5 to 6 cSt; More preferably, the one or more volatile oils iv) are selected from the group consisting of C 8 ~C 16 Alkanes, in particular branched alkanes, preferably isododecane; 17. The method of treatment according to any one of claims 1 to 16, wherein at least one oil selected from the group consisting of:

18. 18. A method for treating, in particular cosmetically treating, keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, according to any one of claims 1 to 17, for the care and / or make-up of keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprising applying to said keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows at least a composition designated "C1", comprising i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as defined in any one of claims 1 to 14, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as defined in claim 16; a composition designated "C2", which comprises i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as defined in any one of claims 1 to 14, ii) at least one crosslinking agent, in particular at least one crosslinking agent as defined in claim 15, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as defined in claim 16; a composition designated "C3", comprising i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as defined in any one of claims 1 to 14, ii) at least one crosslinking agent, in particular at least one crosslinking agent as defined in claim 15, and iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as defined in claim 16; a composition designated "C4", said composition comprising ii) at least one crosslinking agent, in particular at least one crosslinking agent according to claim 15, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent according to claim 16; and / or A composition designated "C5", comprising iii) at least one cosmetic active agent, in particular at least one cosmetic active agent according to claim 16. administering where: The method comprises the use, together or separately, of i) at least one compound of formula (I) or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie) according to any one of claims 1 to 14, and ii) at least one crosslinking agent, in particular at least one crosslinking agent according to claim 15; and Compositions "C1", "C2", "C3", "C4" and "C5" may be anhydrous, aqueous, e.g., hydroalcoholic, and / or may comprise one or more fatty substances iv), in particular one or more fatty substances according to claim 17. is understood, The method.

19. 19. A method of treatment according to any one of claims 1 to 18, characterized in that it comprises either a single step of applying composition "C2" or composition "C3" to the keratinous material, or two successive steps of applying two different compositions to the keratinous material, preferably composition "C1" and then composition "C4".

20. A cosmetic treatment method for caring for and / or making up keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprising at least i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie) according to any one of claims 1 to 14, or a composition designated "C1" according to claim 18, or a composition "C1" comprising such a compound and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent according to claim 16; and then a composition designated "C4", comprising ii) at least one crosslinking agent, in particular at least one crosslinking agent according to claim 15, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent according to claim 16; at least one of the compositions "C1" and / or "C4" comprises at least one dye, in particular a dye according to claim 16, preferably at least one pigment, more preferably composition "C1" comprises at least one pigment, The cosmetic treatment method comprises the sequential administration of

21. A compound of formula (I) according to any one of claims 1 to 13, wherein m is an integer equal to 1, 2, 3 or 4 and differs from compounds (1) to (7) according to claim 14, their salts, isomers and / or solvates, such as hydrates.

22. A composition, preferably a cosmetic composition, comprising at least one compound selected from the compounds of formula (I), formula (Ia), formula (Ib), formula (Ic), formula (Id) and / or formula (Ie), their salts, isomers and / or solvates, such as hydrates, according to any one of claims 1 to 13, wherein m represents an integer equal to 1, 2, 3 or 4 and differs from compounds (1) to (7) according to claim 14.

23. 1. Cosmetic use of a composition designated "C3" for treating keratinous materials, in particular the skin and / or lips and / or eyelashes and / or eyebrows, for the care and / or makeup thereof, said composition comprising: i) at least one compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie), as defined in any one of claims 1 to 14; ii) at least one crosslinking agent, in particular at least one crosslinking agent as defined in claim 15; and iii) at least one cosmetic active agent, in particular at least one cosmetic active agent as defined in claim 16.

24. A multi-compartment kit or device, especially a cosmetic kit or device, comprising: at least one compartment comprising i) a compound of formula (I), or of formula (Ia), (Ib), (Ic), (Id) and / or (Ie) according to any one of claims 1 to 14, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent according to claim 16, in particular at least one cosmetic active agent comprising composition "C1" according to claim 18; at least one compartment different from the one containing i) and containing ii) at least one cross-linking agent, in particular at least one cross-linking agent according to claim 15, and optionally iii) at least one cosmetic active agent, in particular at least one cosmetic active agent according to claim 16, in particular at least one cosmetic active agent comprising composition "C4" according to claim 18; and Optionally, at least one compartment different from those containing i) and ii), said at least one compartment containing iii) at least one cosmetic active agent, in particular at least one cosmetic active agent according to claim 16, said at least one cosmetic active agent being the same as or different from the at least one cosmetic active agent optionally contained in the compartments containing i) and ii), respectively. The multi-compartment kit or device,

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