Method for treating keratinous materials using compounds derived from the condensation of poly(thio)ols with acetoacetate and crosslinking agents - Patent Application 20070122993

Abstract

The present invention relates more particularly to the field of cosmetics for keratinous materials, in particular to the field of cosmetics for the care and / or makeup of the skin, and / or lips, and / or eyelashes, and / or eyebrows. The present invention is therefore directed to proposing a method for the use, in one or more steps, of i) at least one compound of formula (I) derived from the condensation of a poly(thio)ol with acetoacetate (ACAC), and ii) at least one crosslinking agent on keratinous materials. The present invention also relates to a composition comprising components i) and ii) and also to a kit comprising i) and ii).

Description

[Technical Field]

[0001] The present invention relates more particularly to the field of cosmetics for keratinous materials, in particular to the field of cosmetics for the care and / or makeup of the skin, and / or lips, and / or eyelashes, and / or eyebrows. The present invention is therefore directed to proposing a method for the use, in one or more steps, of i) at least one compound of formula (I) derived from the condensation of a poly(thiol) with acetoacetate (ACAC), and ii) at least one crosslinking agent on keratinous materials. The present invention also relates to a composition comprising components i) and ii) and also to a kit comprising i) and ii). [Background technology]

[0002] Traditionally, cosmetic products require the use of one or more film-forming polymers in order to obtain a good coating of such products on keratinous materials, in particular to meet the expectations detailed below.

[0003] Thus, in the field of skin and lip make-up, it is most particularly expected that the coating formed will not transfer to fingers or clothing upon contact.

[0004] Furthermore, in addition to having good resistance to contact with moisture, in particular rain or showering, or even perspiration, it must also be resistant to sebum or, if this coating is formed on the lips, to edible fats, in particular edible oils, with which it comes into contact. Furthermore, this coating must be comfortable to wear or even shiny.

[0005] For this purpose, dispersions of nanometer-sized polymer particles are used as film-forming agents in makeup products such as mascara, eyeliner, eyeshadow, or lipstick, more particularly in their organic phase, especially in their oily phase. Thus, Patent Document 1 proposes the use of a dispersion in a hydrocarbon-based oil of an acrylic polymer stabilized with a polystyrene / copoly(ethylene-propylene) diblock copolymer. Meanwhile, Patent Document 2 describes the use of a dispersion in a hydrocarbon-based oil of surface-stabilized polymer particles. Meanwhile, Patent Document 3 proposes a dispersion in isododecane of an acrylic polymer stabilized with a stabilizing polymer.

[0006] Furthermore, Patent Document 4 describes a medical polymeric tissue adhesive in the form of a hydrogel, which comprises a polyvinyl alcohol polymer having ACAC groups bonded to a polyamine. The document does not describe the use of a poly(thiol) ACAC bonded to a crosslinker and optionally a cosmetic active agent for application to keratinous materials in order to produce a non-sticky, relatively transfer-resistant, glossy, comfortable, and long-lasting coating on the keratinous materials. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] European Patent No. 749747 [Patent Document 2] French Patent No. 1362795 [Patent Document 3] International Publication No. 2010 / 046229 Brochure [Patent Document 4] US Patent Application Publication No. 2006 / 0079599 Summary of the Invention [Problem to be solved by the invention]

[0008] There remains a need for cosmetic compositions intended to be applied to the skin, and / or lips, and / or eyelashes, and / or eyebrows, which are non-sticky, relatively transfer-resistant, or even completely transfer-resistant, and make it possible to obtain a glossy, comfortable, and long-lasting coating.

[0009] There is also a need for compositions that are resistant to water and fatty substances, especially sebum.

[0010] There also remains a need for compositions that impart shine and clarity qualities. [Means for solving the problem]

[0011] In particular, the present invention is directed to meeting these needs in whole or in part.

[0012] These challenges involve the keratin material being i) Poly(thio)ols obtained by condensation with acetoacetate (ACAC), of formula (I): [ka] (In formula (I), -R 1 is a C2-C linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic 14 , especially C3~C 12 represents a polyvalent hydrocarbon group, R 1 Also, a) optionally substituted with one or more hydroxyl-OH or amine-N(R) groups (wherein R represents a (C1-C4) alkyl group such as methyl), carboxyl-C(O)-OH, vinyl groups; and / or b) O, S, carbonyl-C(O)—, amine-N(R′), or combinations thereof, such as ester-C(O)—O—, —OC(O)—, amide-C(O)—N(R′)—, —N(R′)—C(O)—, urethane-N(R′)—C(O)—O— or —OC(O)—N(R′)—, urea-N(R′)—(CO)—N(R′)— or carbonate-OC(O)—O— (wherein R′ is optionally substituted with a hydrogen atom, at least one hydroxyl group (OH), or is —XC(O)—C(R a )(R b )-C(O)-R 2 and optionally interrupted by one or more heteroatoms or groups selected from: (R' represents a hydrogen atom or a (C1-C4) alkyl group); -R 2 represents a linear or branched, saturated or unsaturated C1-C6 monovalent hydrocarbon-based group, preferably a (C1-C4) alkyl group such as methyl or tert-butyl, more preferentially methyl; -R a and R b may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group, preferably hydrogen; - X is O, S, N(R') or a heteroatom or group selected from -S-CH2-C(O)-O-, -OC(O)-CH2-S-, -OC(O)-N(R')-, -N(R')-C(O)-O- or -N(R')-C(O)-N(R')-; preferably, X represents O; - n represents an integer ranging from 2 to 10, in particular from 3 to 8 and also optical or geometric isomers thereof, salts thereof and solvates thereof, such as hydrates; ii) at least one crosslinker; iii) optionally at least one cosmetic active agent; The above-mentioned problems are solved by carrying out a method of treating the material by applying a DETAILED DESCRIPTION OF THE INVENTION

[0013] The inventors have therefore surprisingly found that applying components i), ii) and optionally iii) to keratinous materials confers resistance to keratinous materials treated with this combination, in particular resistance to liquid fatty substances such as oils and to water.

[0014] For purposes of this invention, unless otherwise specified: - the term "cosmetic active agent" means an organic or organosilicon compound or an inorganic compound that can be incorporated into a cosmetic composition to provide some effect on keratin materials, whether the effect is immediate or is obtained by repeated applications. Examples of cosmetic active agents include colored or colorless, fluorescent or non-fluorescent compounds, such as optical brighteners, or UVA and / or UVB screening agents, anti-aging active agents, or active agents intended to benefit the skin, such as active agents acting on the barrier function, deodorant active agents, antiperspirant active agents, desquamating active agents, antioxidant active agents, moisturizing active agents, sebum-regulating active agents, active agents intended to combat the effects of pollution, antimicrobial or bactericidal active agents, fragrances, and coloring agents such as direct dyes or pigments, preferably pigments.

[0015] Preferentially, the cosmetic active agents are selected from a) colorants selected from pigments, direct dyes and mixtures thereof, b) active agents for caring for keratinous materials, preferably the skin, c) UV filters, and d) mixtures thereof.

[0016] - the term "fatty substance" for the purposes of the present invention means an organic compound that is insoluble in water (solubility less than 5%, preferably less than 1%, and even preferentially less than 0.1%) at room temperature (25°C) and atmospheric pressure (760 mmHg); in addition, fatty substances are soluble under the same temperature and pressure conditions in organic solvents, for example halogenated solvents such as chloroform or dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene.

[0017] - The term "(hetero)aryl" means an aryl group or a heteroaryl group.

[0018] - The term "(hetero)cycloalkyl" means a cycloalkyl or heterocycloalkyl group.

[0019] - An "aryl" or "heteroaryl" group or an aryl or heteroaryl portion of a group can be substituted with at least one substituent attached to a carbon atom selected from: C1-C6, preferably C1-C4 (poly)(hydroxy)alkyl groups; Halogen atoms such as chlorine, fluorine or bromine; · Hydroxyl groups; · C1-C2 alkoxy groups; C2-C4 (poly)hydroxyalkoxy groups; · Amino group; an amino group substituted with one or two identical or different C1-C6, preferably C1-C4 alkyl groups; acylamino groups (-NR-COR') (wherein the R group is a hydrogen atom; a C1-C4 alkyl group, and the R' group is a C1-C4 alkyl group; a carbamoyl group ((R)2N-CO-) (wherein the R groups may be the same or different and represent a hydrogen atom or a C1-C4 alkyl group); alkylsulfonylamino group (R'SO2-NR-) (wherein the R group represents a hydrogen atom or a C1-C4 alkyl group, and the R' group represents a C1-C4 alkyl group or a phenyl group); aminosulfonyl groups ((R)2N—SO2—) (wherein the R groups can be identical or different and represent a hydrogen atom or a C1-C4 alkyl group); carboxyl groups in acid form or in the form of salts (preferably with alkali metals or substituted or unsubstituted ammonium); · Cyano group (CN); Polyhalo(C1-C4) alkyl groups, preferentially trifluoromethyl (CF3).

[0020] The cyclic or heterocyclic moiety of the non-aromatic group may be substituted with at least one substituent attached to a carbon atom selected from the following groups: · Hydroxyl; · C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy; alkylcarbonylamino (R—CO—NR′—) (wherein the R′ group is a hydrogen atom or a C1-C4 alkyl group, and the R group is a C1-C2 alkyl group or an amino group substituted with one or two identical or different C1-C4 alkyl groups); alkylcarbonyloxy (R—CO—O—) (wherein R is a C1-C4 alkyl group, amino substituted with one or two identical or different C1-C4 alkyl groups); Alkoxycarbonyl (RO-CO-), where the R group is a C1-C4 alkyl group or amino substituted with one or two identical or different C1-C4 alkyl groups.

[0021] The non-aromatic moieties of a cyclic or heterocyclic group or an aryl or heteroaryl group may also be substituted with one or more oxo groups.

[0022] The hydrocarbon-based chain is unsaturated if it contains one or more double bonds and / or one or more triple bonds.

[0023] - "aryl" group denotes a monocyclic or fused or non-fused polycyclic hydrocarbon chain containing 6 to 14 carbon atoms, at least one ring of which is aromatic; preferentially, the aryl group is phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl.

[0024] - "heteroaryl" group denotes a 5-14 membered monocyclic or fused or non-fused polycyclic group containing 1 to 6 heteroatoms selected from nitrogen, oxygen, sulfur and selenium atoms, at least one ring of which is aromatic; preferentially, heteroaryl groups are acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazolyl, and is selected from among isopyridyl, imidazolyl, indolyl, isoquinolyl, naphthimidazolyl, naphthoxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrrylyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, and xanthryl.

[0025] - a "cyclic" or "cycloalkyl" group is a monocyclic or fused or non-fused polycyclic non-aromatic cyclic hydrocarbon group containing 5 to 14 carbon atoms, which may contain one or more unsaturations, preferably cycloalkyl is a cyclohexyl group.

[0026] - a "heterocyclic" or "heterocycloalkyl" group is a 3- to 9-membered monocyclic or fused or non-fused polycyclic non-aromatic group containing 1 to 4 heteroatoms selected from nitrogen, oxygen, sulfur, and selenium atoms; preferably, heterocycloalkyl is selected from epoxide, piperazinyl, piperidyl, morpholinyl, and dithiolane.

[0027] - "Alkyl" group is a saturated hydrocarbon-based group, linear or branched, in particular C1 to C6, preferably C1 to C4.

[0028] - an "alkoxy" group is an alkyloxy group, in which the alkyl group is a linear or branched C1-C6, preferentially C1-C4 hydrocarbon-based group.

[0029] - "(poly)(hydroxy)alkyl" group refers to a C1-C alkyl group optionally substituted with one or more hydroxyl groups, preferably substituted with 1 to 4, more particularly substituted with 1 to 3 hydroxyl groups. 6、 Preferably, it refers to a C1 to C4 alkyl group.

[0030] - a "sugar" group is a monosaccharide or disaccharide group, and can include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, and lactose.

[0031] The term "monosaccharide" refers to a sugar of formula C x (H2O) x (where x is an integer of 5 or more, preferably x is 6 or more, and in particular x is 5 to 7 (inclusive), preferably x=6) refers to sugars that are monosaccharides containing at least 5 carbon atoms, which may be in the D- or L-configuration and in the α- or β-anomers, as well as salts and solvates such as hydrates thereof.

[0032] - the term "disaccharide" refers to a sugar that is a disaccharide, which is a compound composed of two sugars linked via an O-sugar bond (said compound being composed of two sugar units (also known as monosaccharides) as defined above, said monosaccharide units containing at least 5, preferably 6 carbon atoms; in particular the monosaccharide units are linked via a 1,4 or 1,6 bond as α (alpha) or β (beta) anomers, each sugar unit being capable of being in the L or D configuration), as well as to salts thereof and solvates thereof, such as hydrates of said monosaccharides; more particularly these refer to compounds of the general formula: -[C x (H2O) y )]2- or -[(CHO) x ]2- (wherein x is an integer of 5 or more, preferably x is 6 or more, and particularly x is 5 to 7 (inclusive), preferably x=6, and y is an integer representing x-1).

[0033] - the term "polysaccharide" refers to polysaccharide sugars, which are polymers made up of several sugars linked together via O-sugar bonds (said polymers being made up of monosaccharide units (also known as monosaccharides) as defined above, said monosaccharide units comprising 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, each sugar unit being capable of being in the L or D configuration), as well as to salts thereof and solvates thereof, such as hydrates of said monosaccharides; more particularly, these refer to polysaccharides of the general formula: -[C x (H2O) y )] w -or-[(CHO) x ] w - (wherein x is an integer of 5 or more, preferably x is 6 or more, particularly x is 5 to 7 (inclusive), preferably x=6; y is an integer representing x-1; and w is an integer of 2 or more, particularly 3 to 3000 (inclusive), more particularly 5 to 2500, preferentially 10 to 2300, particularly 15 to 1000 (inclusive), more particularly 20 to 500, preferentially 25 to 200), and is a polymer formed from a certain number of sugars (i.e., monosaccharides).

[0034] - the term "organic or inorganic acid salts" refers more particularly to a) addition salts with organic or inorganic acids, in particular i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH, such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH, such as benzenesulfonic acid and toluenesulfonic acid; vi) alkoxysulfinic acids: Alk-OS(O)OH, such as methoxysulfinic acid vii) aryloxysulfinic acids, such as tolueneoxysulfinic acid and phenoxysulfinic acid; viii) phosphoric acid: H3PO4; ix) triflic acid: CF3SO3H; and x) tetrafluoroboric acid: HBF4; xi) organic carboxylic acids: R°-C(O)-OH(I'z) (wherein R° is a (hetero)aryl group such as phenyl, a (hetero)aryl(C1-C4) alkyl group such as benzyl, or a (C1-C 10 ) alkyl, said alkyl group being optionally substituted, preferably with one or more hydroxyl or amino or carboxyl groups, R° preferably representing a (C1-C6) alkyl group optionally substituted with one, two or three hydroxyl or carboxyl groups; more preferentially, the monocarboxylic acid of formula (I'z) is selected from acetic acid, glycolic acid, lactic acid and mixtures thereof, more particularly from acetic acid and lactic acid; the polycarboxylic acid is selected from tartaric acid, succinic acid, fumaric acid, citric acid and mixtures thereof; and xii) amino acids containing more carboxylic acid groups than amino groups, such as γ-carboxyglutamic acid, aspartic acid or glutamic acid, in particular γ-carboxyglutamic acid. or b) addition salts with organic or inorganic bases, such as alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal bicarbonates, addition salts with basic amino acids, such as arginine or lysine, and optionally addition salts with hydroxylated amines. means.

[0035] - "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; iii) sulfonates, such as C1-C6 alkyl sulfonates: Alk-S(O)2O - , such as methanesulfonates, i.e. mesylates and ethanesulfonates; iv) arylsulfonates: Ar—S(O)O - benzenesulfonates and toluenesulfonates, i.e. tosylates; v) citrates; vi) succinates; vii) tartrates; viii) lactates; ix) alkyl sulfates: Alk-OS(O)O - x) aryl sulfates: Ar—OS(O)O - , for example, benzene sulfate and toluene sulfate; xi) alkoxy sulfates: Alk-OS(O)O - xii) aryloxysulfates: Ar—OS(O)O - xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borate, for example tetrafluoroborate.

[0036] - "solvates" refers to hydrates as well as combinations with linear or branched C1-C4 alcohols, such as ethanol, isopropanol or n-propanol.

[0037] - The term "chromophore" refers to the UV and / or visible radiation range with wavelengths λ between 250 and 800 nm. absThe term "chromophore" refers to a group derived from a colorless or colored compound capable of absorbing light. Preferably, the chromophore is colored, i.e., it absorbs in the visible range, i.e., preferably at wavelengths between 400 and 800 nm. Preferably, the chromophore appears colored to the naked eye, especially between 400 and 700 nm (Ullmann's Encyclopedia, 2005, Wiley-VcH, Verlag "Dyes, General Survey", §2.1 Basic Principle of Color).

[0038] - The term "UV-A filter" refers to a chromophore derived from a compound that filters (or absorbs) UV-A ultraviolet rays with a wavelength between 320 and 400 nm. A distinction is sometimes made between short-wave UV-A filter agents (which absorb light with a wavelength between 320 and 340 nm) and long-wave UV-A filter agents (which absorb light with a wavelength between 340 and 400 nm).

[0039] The term "UV-B filter" means a chromophore derived from a compound that blocks (or absorbs) UV-B ultraviolet radiation of wavelengths between 280 and 320 nm.

[0040] - the term "anhydrous" means that the amount of water is less than 5% by weight, preferentially less than 3% by weight and better still less than 1% by weight, relative to the total weight of the composition C1, C2, C3 or C4 in question; even more preferentially, the composition does not contain water.

[0041] The terms "colorant" and "color material" are synonymous.

[0042] Unless otherwise specified, the boundaries defining the width of a numerical range are included in the numerical range.

[0043] Unless otherwise stated, amounts given are expressed as mass percentages.

[0044] Method for treating keratinous materials The first subject of the present invention is to provide a method for treating keratinous materials, in particular on the skin, i) at least one compound of formula (I) as defined above and below; ii) at least one crosslinker as defined below; iii) optionally at least one cosmetic active agent as defined above; The method is a one or more step method using

[0045] According to a particular embodiment of the invention, the method of the invention comprises applying components i), ii) and optionally iii) simultaneously.

[0046] According to another particular embodiment of the invention, the method comprises at least two steps of applying components i) and ii) and optionally iii) (the latter component may be present together with component i) and / or component ii)) to keratinous materials in separate and successive steps.

[0047] It is understood that according to certain embodiments, component i) is applied to the keratinous material, then component ii) is applied to the keratinous material, and if component iii) is present, it may be applied together with i) and / or ii).

[0048] According to other particular embodiments, component ii) is applied to the keratinous material, then component i) is applied to the keratinous material, and it is understood that component iii), if present, may be applied together with i) and / or ii).

[0049] According to a particular embodiment of the invention, the method for treating keratinous materials is a method for making up the skin, lips, eyelashes and / or eyebrows, preferably for making up the skin and lips.

[0050] According to another embodiment of the present invention, the method for treating keratinous materials is a skin care method.

[0051] According to one aspect of the invention, the method of the invention for treating keratinous materials using components i), ii) and optionally iii) is a skin care treatment.

[0052] According to another aspect of the invention, the method of treating keratinous materials using components i), ii) and optionally iii) is a method for making up the skin, lips, eyelashes and / or eyebrows.

[0053] According to one embodiment of the present invention, a method for treating keratinous materials comprises the steps of: - a composition designated "C1" comprising i) at least one compound of formula (I) or (Ia) as defined above and below, and optionally iii) at least one cosmetic active agent as defined above and below, said composition preferably not containing a crosslinker; - a composition designated "C2" comprising i) at least one compound of formula (I) or (Ia) as defined above and below, ii) at least one crosslinking agent as defined below, and optionally iii) at least one cosmetic active agent as defined above and below; - a composition designated "C3" comprising i) at least one compound of formula (I) or (Ia) as defined above and below, ii) at least one crosslinking agent as defined below, and iii) at least one cosmetic active agent as defined above; and / or - a composition "C4" comprising ii) at least one crosslinking agent as defined below and, optionally, iii) at least one cosmetic active agent as defined above and below, preferably composition "C4" not comprising a compound of formula (I) or (Ia); - iii) a composition "C5" comprising at least one cosmetic active agent as defined above and below, preferably without a compound of formula (I) or ii) a crosslinker as defined below; Use This method comprises the steps of: i) using, together or separately, at least one compound of formula (I) or (Ia) as defined above and below, and ii) at least one crosslinking agent as defined below; Compositions C1, C2, C3, C4 and C5 may be aqueous, such as anhydrous or aqueous-alcoholic, and / or may comprise one or more fatty substances iv), in particular one or more preferably volatile oils as defined below; is understood.

[0054] According to one aspect of the present invention, the method of treating keratinous materials, in particular the method of caring for and / or making up the skin, lips, eyelashes and / or eyebrows, of the present invention uses a composition designated "C1" comprising i) as defined above and below and optionally iii), in particular at least one cosmetic active agent, in particular at least one colorant, more particularly at least one pigment, as defined below, selected from a) colorants such as pigments, direct dyes and mixtures thereof, b) active agents for caring for keratinous materials, preferably the skin, c) UV filters, and d) mixtures thereof.

[0055] According to another aspect, the method of treating keratinous materials of the invention, in particular for caring for and / or making up the skin, lips, eyelashes and / or eyebrows, uses a composition designated "C2" comprising: i) at least one compound of formula (I) as defined above and below; ii) at least one crosslinking agent as defined below; and, optionally, iii) at least one cosmetic active agent as defined above.

[0056] According to another aspect, the method of treating keratinous materials of the invention, in particular for caring for and / or making up the skin, lips, eyelashes and / or eyebrows, uses a composition designated "C3" comprising: i) at least one compound of formula (I) as defined above and below; ii) at least one crosslinking agent as defined below; and iii) at least one cosmetic active agent as defined above.

[0057] According to another aspect, the method of treating keratinous materials of the invention, in particular for caring for and / or making up the skin, lips, eyelashes and / or eyebrows, uses a composition designated "C1" and a composition designated "C4", said composition "C1" comprising i) at least one compound of formula (I) as defined above and below and, optionally, iii) at least one cosmetic active agent as defined above, and said composition "C4" comprising ii) at least one crosslinking agent as defined below and, optionally, iii) at least one cosmetic active agent as defined above.

[0058] According to another variant of the method of the invention, components i) and optionally iii) are applied together (i.e. simultaneously) to the keratinous material in a first step, then components ii) and optionally iii) are applied to said material in a subsequent step. According to a particular embodiment of this method, composition "C1" is applied to the keratinous material in a first step, then composition "C4" comprising ii) at least one crosslinking agent and optionally iii) at least one cosmetic active agent as defined above is applied to said material.

[0059] According to yet another variant of the method of the invention, components ii) and optionally iii) are applied to a keratinous material, then components i) and optionally iii) at least one cosmetic active agent as defined above are applied to said material. In particular, composition C4 is applied to the keratinous material, then composition C1 is applied.

[0060] The compositions C1, C2, C3, C4 and / or C5 of the method of the invention comprising at least one fatty substance, in particular at least one oil, and water may be in the form of a normal or reverse emulsion.

[0061] Thus, the compositions C1, C2, C3, C4 and / or C5 of the method according to the invention can be applied as such to the keratinous materials in question or can even be formed directly on the surface of these keratinous materials.

[0062] According to the invention, a distinction is made accordingly between application methods known as "one-action application scheme", "two-action application scheme" and "three-action application scheme".

[0063] According to one embodiment of the method of the invention, the method is carried out in one operation by applying the composition C2 or C3 defined above to the keratinous materials.

[0064] The term "single action application method" means that a single composition according to the invention, ie composition C2 or C3, is applied directly to the keratinous material in question.

[0065] After applying composition C2 or C3, a long-lasting, non-sticky coating is advantageously obtained, which is also resistant to edible oils, water, sebum and abrasion.

[0066] According to another embodiment of the method of the invention, the method is carried out in two operations.

[0067] The term "two-action application regime" refers to the sequential application of two different compositions to the target keratinous material, such as C1 and C4, or C2 and C4, or C3 and C4, preferably C1 then C4, C2 then C4, or C3 then C4.

[0068] According to another embodiment, the method of the invention is carried out in three operations.

[0069] The term "three-step application method" means the sequential application of three different compositions C1 to C5. This application method is carried out, for example, in one embodiment, by applying to the keratinous substance α) composition C1, then β) composition C4, then γ) composition C5, preferably C1, then C4 or C5, respectively, or C5 or C4, respectively. In another alternative, α) for example composition C4 and β) composition C1 or C2 and then γ) composition C5 are sequentially applied to the keratinous substance, preferably composition C4 is applied before composition C1.

[0070] In a two- or three-action application system, the composition applied first, eg, C1, is conventionally called the "basecoat," and the composition applied over it is generally called the "topcoat."

[0071] After applying the different compositions C1 to C5, a long-lasting, non-greasy coating is advantageously obtained, which is resistant to cooking oils, water and shampoo washing.

[0072] According to a particular embodiment, the composition is applied to dry keratinous materials.

[0073] According to a particular embodiment, the keratinous materials are dried after applying the compositions C1 to C5, and in particular after each application of a different composition.

[0074] According to one aspect, the invention relates to a method for making up the skin, in particular the lips, the eyelashes or the eyebrows, comprising the step of applying to the skin or to said lips, or the eyelashes or the eyebrows, a composition C2 or C3, in particular a composition C2 or C3 comprising at least one colorant, more particularly at least one pigment, as defined above.

[0075] According to another aspect, the invention relates to a method for making up keratinous materials, in particular the skin, in particular the lips, eyelashes or eyebrows, comprising at least - composition C1 as defined above; then - composition C4 as defined above; It is understood that compositions C1 and / or C4 comprise at least one colorant, preferably at least one pigment, as defined below. Preferably, composition C1 comprises at least one pigment.

[0076] According to another aspect, the invention relates to a method for making up keratinous materials, in particular the skin, in particular the lips, eyelashes or eyebrows, comprising at least - composition C1 as defined above; then - composition C4 as defined above; then - composition C5 as defined above; It is understood that compositions C1, C4 and / or C5 comprise at least one colorant, preferably at least one pigment, as defined below. Preferably, composition C5 comprises at least one pigment.

[0077] According to another aspect, the invention relates to a method for making up keratinous materials, in particular the skin, in particular the lips, eyelashes or eyebrows, comprising at least - with composition C2 or C3 as defined above; - composition C4 as defined above; wherein composition C2 or C3 comprises at least iii) one colorant as defined below, and / or composition C4 comprises at least one colorant as defined below; it is understood that preferably composition C2 or C3 comprises at least one pigment.

[0078] i) a compound of formula (I) The first component i) of the process of the present invention is selected from compounds of formula (I) as defined above.

[0079] According to a particular embodiment of the invention, component i) is of formula (Ia): [ka] (In formula (Ia), -R 1 is as defined above and in particular is a C2-C linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic 14 , especially C3~C 12 , preferably C4 to C 10 represents a polyvalent hydrocarbon group, and R 1 Also, a) optionally substituted with one or more hydroxyl groups OH, and / or b) optionally interrupted by one or more heteroatoms or groups selected from O, S, —N(R′), preferably interrupted by one or more oxygen atoms, wherein R′ is as defined in formula (I); -R 2 is as defined above, preferably R 2 represents a linear or branched (C1-C6) alkyl group, preferably a (C1-C4) alkyl group such as methyl or t-butyl, preferably methyl; and - n is as defined above; preferably, n represents an integer from 2 to 8. and also optical isomers, geometric isomers, salts and solvates thereof, such as hydrates thereof.

[0080] According to one embodiment, the compounds of formula (I) and (Ia) are R 1 represents a linear or branched, unsaturated, monocyclic or bicyclic, preferably monocyclic, C6 to C8 polyvalent hydrocarbon group and an aromatic group such as phenyl.

[0081] According to another embodiment, the compounds of formula (I) and (Ia) are 1 optionally interrupted by one or more heteroatoms or groups selected from O, S and -N(R')- (wherein R' represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms), preferably interrupted by one or more oxygen atoms; 12 Preferably, R 1 is a compound in which n hydroxyl groups are -OC(O)-CH2-C(O)-R 2 group (where R 2 represents a mono- or polysaccharide unit, in particular a disaccharide, substituted with 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30,

[0082] Suitable monosaccharides according to the present invention include, but are not limited to, ribose, glucose, mannose, galactose, fructose and sorbose.

[0083] According to one embodiment, the disaccharide is selected from cellobiose, maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose and xylobiose.

[0084] According to another preferred embodiment of the present invention, the compounds of formula (I) and (Ia) are 1 is a linear or branched, saturated or unsaturated, preferably saturated acyclic C2-C 12 , preferably C3 to C 10 It is intended to represent a polyvalent hydrocarbon-based group.

[0085] According to particular embodiments of the present invention, the compounds of formula (I) and (Ia) are such that n represents an integer from 2 to 8; more particularly, n represents an integer from 3 to 6, even more particularly, an integer from 3 to 5. According to one embodiment, the compounds of formula (I) and (Ia) are such that n is 2. According to another embodiment, the compounds of formula (I) and (Ia) are such that n is 3. According to another embodiment, the compounds of formula (I) and (Ia) are such that n is 4. According to another embodiment, the compounds of formula (I) and (Ia) are such that n is 5. According to another embodiment, the compounds of formula (I) and (Ia) are such that n is 6.

[0086] In one variant of the invention, the compound of formula (I) or (Ia) as defined above is a mixture of (poly)acetoacetylated compounds with different structures.

[0087] More particularly, the compounds of formula (I) and (Ia) are selected from the following compounds and also their optical isomers, salts and solvates thereof, such as hydrates:

[0088] [Table 1]

[0089] Table 2

[0090] Table 3

[0091] Table 4

[0092] Table 5

[0093] Table 6

[0094] Table 7

[0095] Table 8

[0096] Table 9

[0097] Table 10

[0098] wherein R1 may be identical or different and represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, with at least two R1 groups representing -C(O)-CH2-C(O)-CH3, preferably at least three R1 groups representing -C(O)-CH2-C(O)-CH3, more preferentially the compounds are selected from (18), (21), (38), (41), (44) and (50), better from (21), (38), (41), (44) and (50). Even more preferentially the compounds are selected from (18), (21), (38), (41) and (44), better from (21), (38), (41) and (44). Advantageously, the compound is selected from (18), (21), (41) and (44), more advantageously from (21), (41) and (44).

[0099] The compound of formula (I) or (Ia) as defined above is preferably present in a weight ratio of 0.2% to 100%, in particular 0.5% to 60%, more particularly 5% to 40%, relative to the total weight of the composition C1, C2 or C3 containing it. In particular, the crosslinker and the compound of formula (I) or (Ia) are preferably present in a weight ratio of 7% to 35% relative to the total weight of the composition containing them.

[0100] The compounds of formula (I) or (Ia) can be prepared by reacting n equivalents of a dicarbonyl reagent with n equivalents of a nucleophilic reagent R containing a nucleophilic functional group -XH. 1 (XH) n and (poly)condensation according to the following scheme: [ka] During the scheme, -R 1 , R 2 , R a , R b and n is as defined for compounds of formula (I); -R 3represents a hydrogen atom, a (C1-C4) alkyl group such as methyl, ethyl, isobutyl, t-butyl, etc., or an electron-withdrawing group such as CHal3 or Hal3C-SO2- (wherein Hal may be the same or different and represents a halogen atom), e.g., triflate; X' represents an oxygen or sulfur atom, preferably O.

[0101] These (poly)condensation methods are known to those skilled in the art and are described, for example, in "From rigid and flexible foams to elastomers via Michael addition chemistry", Polymer, 106, 128-139, (2016), "Dynamic Curing Agents for Amine-Hardened Epoxy Vitrimers with Short (Re)processing Times", Macromolecules, 53(7), 2485-2495 (2020), "Super photo-base initiated organic-inorganic hybrid coatings by plural-cure mechanisms", Progress in Organic Coatings, 127, 222-230 (2019) or in the specification of patent application PL159100: Method for manufacturing acetylacetate esters.

[0102] According to a particular embodiment of the present invention, R 1 (XH) n is the acyclic polyol R 1 (OH) nIn particular, glycerol, trimethylolpropane, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, trimethylolethane, pentamethylene glycol, trimethylpentanediol, pentyl glycol, isosorbide, pentaerythritol, dipentaerythritol, hexamethylene glycol, hexylene glycol, hexanediol, neopentyl glycol, 1,2-propanediol, 1,3-propanediol; 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol; 2,4-butanediol, 3,4-butanediol; 1,4-pentanediol; 1,5-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,6-hexanediol, 1,2-octanediol, 1,8-octanediol, 1,10-decanediol, 2-methyl-1,3-propanediol, hexylene glycol, and isoprene glycol.

[0103] In one variation, R 1 (XH) n is a cyclic polyol R 1 (OH) n and in particular, alone or in mixtures, from the monosaccharides and disaccharides defined above.

[0104] Preferentially, R 1 (XH) n Polyol R, either alone or in mixtures 1 (OH) n In particular, trimethylolethane, glycerol, trimethylolpropane, pentaerythritol, glycerol, glucose, sucrose and sorbitol.

[0105] According to another variant, R 1 (XH) n Diamine R 1(NH2)2, in particular hydroxyalkylated aliphatic diamines such as o,o'-bis(diethanolaminomethyl)-p-nonylphenol, N,N,N,N'-tetrakis(2-hydroxypropyl)ethylenediamine (Quadrol L available from BASF) and N,N,N,N-tetrakis(2-hydroxyethyl)ethylenediamine, and mixtures thereof.

[0106] According to another advantageous variant, compounds of formula (I) or (Ia) can be prepared by reacting n equivalents of a propylenedioxycarbonyl reagent with n equivalents of a polyamine nucleophile R containing -NH2 nucleophilic functional groups, according to the following scheme: 1 (NH) n It is obtained by (poly)condensation with [ka] During the scheme, -R 1 , R 2 , R a and n is as defined for compounds of formula (I); -R 1 -NH2 is in particular selected from ethylenediamine, 1,3-diaminopropane, cadaverine, hexamethylenediamine, 1,2-diaminopropane, 1,2-diaminocyclohexane and phenylenediamine; -R b’ and R c The ' may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group.

[0107] This type of synthesis according to Scheme 2 is known to those skilled in the art and can be found, for example, in "Acetoacetylation with 2,2,6-trimethyl-4H-1,3-dioxin-4-one: a convenient alternative to diketene", Journal of Organic Chemistry, 50(14), 2431-5, (1985) or "Synthesis of new Biginelli polycondensates: renewable materials with tunable high glass transition temperatures", Polymer International, 70(5), 506-513 (2021).

[0108] According to another advantageous variant, compounds of formula (I) or (Ia) can be prepared by reacting n equivalents of a diketene reagent with n equivalents of a nucleophilic reagent R containing a nucleophilic functional group according to the following scheme: 1 (X) n It is obtained by (poly)condensation with [ka] During the scheme, R 1 and n is as defined for compounds of formula (I); X' represents an oxygen or sulfur atom or N(R') (where R'=H).

[0109] This type of method is known to those skilled in the art, and can be found, for example, in "Acetoacetamides, 2-hydroximinoacetoacetamides, and 2,3-bis(hydroximino)butyramides", Journal fur Praktische Chemie (Leipzig), 323(2), 337-44, (1981) or Angewandte Makromolekulare Chemie, 9, 96-105, (1969).

[0110] ii) Crosslinking Agent The method of the present invention uses ii) one or more cross-linking agents. For the purposes of the present invention, the term "cross-linking agent", also referred to as "R", refers to at least one ACAC group in a compound of formula (I) or (Ia), - at least one covalent bond, - at least one donor-acceptor (coordination) bond, and / or - at least one coordinate bond and thus can bridge compounds of formula (I) or (Ia).

[0111] Preferably, the term "crosslinker" refers to a compound capable of establishing at least one covalent bond with the ACAC group of a compound of formula (I) or (Ia).

[0112] For the purposes of the present invention, the terms "crosslinking agent" and "crosslinker" are understood to be equivalent.

[0113] Compositions C2, C3 and C4 contain at least one crosslinking agent. The compositions of the present invention may contain a fatty phase, an aqueous phase or be in the form of a normal or reverse emulsion. Composition C4 may be an aqueous composition.

[0114] According to one aspect, the method of the invention uses a composition designated "C3", in particular a cosmetic composition for caring for and / or making up and / or caring for keratinous materials, in particular the skin, lips, eyelashes and / or eyebrows, comprising i) at least one compound of formula (I) as defined above, ii) at least one crosslinking agent, and iii) at least one cosmetic active agent as defined above, in particular at least one colorant, more particularly at least one pigment.

[0115] The crosslinker as defined above is preferably present in a weight ratio of 0.2% to 60%, in particular 0.5% to 40%, more particularly 5% to 40% relative to the total weight of the composition containing it. In particular, the crosslinker and the compound of formula (I) or (Ia) are preferably present in a weight ratio of 7% to 35% relative to the total weight of the composition containing them.

[0116] More precisely, crosslinkers R suitable for use in the present invention can be selected from compounds bearing amine, thiol, acrylate and / or carbonyl groups, such as ketone or aldehyde groups. Crosslinker R can also refer to metal alkoxides.

[0117] Thus, according to a particular embodiment, the crosslinker R is selected from (poly)amine, (poly)thiol, (poly)carbonyl, (poly)acrylate and / or metal alkoxide compounds and mixtures thereof, preferably selected from (poly)amine, (poly)thiol and (poly)acrylate compounds and mixtures thereof.

[0118] The terms "(poly)amine, (poly)thiol, (poly)carbonyl and (poly)acrylate compounds" are intended to refer to compounds comprising at least one primary or secondary amine group, a thiol group, a carbonyl group (such as a ketone or aldehyde group) or an acrylate group, respectively.

[0119] A) (Poly)amine Compounds According to a preferred embodiment, the crosslinking agent R is chosen from (poly)amine compounds.

[0120] The (poly)amine compounds can be chosen from polyamine compounds having several primary and / or secondary amine groups or from aminoalkoxysilanes, more particularly from aminoalkoxysilane compounds, diamine compounds, triamine compounds and mixtures thereof.

[0121] The (poly)amine compounds may be compounds, in particular non-polymeric compounds, containing 2 to 20 carbon atoms, which may be acyclic or cyclic, straight-chain or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted by one or more heteroatoms 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- (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 hydrogen).

[0122] "Non-polymeric compound" means a compound that does not result directly from the polymerization reaction of monomers.

[0123] Examples of the (poly)amine compounds include, in particular, 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-dimethyldipropylenetriamine, 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 C36-alkylenediamine (Priamine TM 1071, 1073, 1074, 1075).

[0124] According to a particular embodiment of the present invention, the (poly)amine compounds are monoamine compounds, i.e. they contain only one primary and / or secondary amine group, preferably a primary amine group (NH2).

[0125] The (poly)amine compounds are aminoalkoxysilanes, in particular those of the formula R'1Si(OR'2) z (R'3) x (In the formula, - R'1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C6 hydrocarbon chain substituted with a group selected from primary amine NH2 groups or secondary amine -N(H)R groups, where R represents C1-C4 alkyl, aryl or benzyl substituted with an amino group or a C1-C4 aminoalkyl group; R'1 may be interrupted within the chain by heteroatoms (O, S, NH) or carbonyl groups (CO), and R'1 is directly bonded to the silicon atom via a carbon atom, R'2 and R'3 may be identical or different and represent a linear or branched (C1-C6) alkyl group; - z represents an integer ranging from 1 to 3; - x represents an integer ranging from 0 to 2; z+x=3) can be selected from those having the following structure:

[0126] In particular, R'1 is an acyclic chain. Preferably, R'1 is a linear or branched, saturated or unsaturated C1-C6 hydrocarbon chain substituted with an amine -NH2 or -N(H)R group, where R is a C1-C6 alkyl, C3-C6 cycloalkyl or C6 aromatic group. More preferentially, R'1 is a saturated linear C1-C6 hydrocarbon chain substituted with an amine group NH2. Even more preferentially, R'1 is a saturated linear C2-C4 hydrocarbon chain substituted with an amine group NH2.

[0127] In particular, R'2 represents an alkyl group containing from 1 to 4 carbon atoms; preferably, R'2 represents a linear alkyl group containing from 1 to 4 carbon atoms, and more preferentially, R'2 represents an ethyl group.

[0128] 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, and more preferentially, R'3 represents a methyl or ethyl group. Preferably, z is 3.

[0129] In particular, the (poly)amine compound is selected from aminoalkoxysilanes containing only one primary and / or secondary, preferably 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.

[0130] Preferably, the (poly)amine compound is selected from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, more preferentially 3-aminopropyltriethoxysilane (APTES).

[0131] (Poly)amine compounds, in particular, have a mass average molecular weight of 500 gmol -1 ~1,000,000 g.mol -1 in the range of 500 g.mol -1 ~500000g.mol -1 in the range of 500 g.mol -1 ~100000g.mol -1 The amino polymer may also be selected from the amino polymers in the range of

[0132] According to a particular embodiment of the present invention, the (poly)amine compound is a monoamine compound, a polydialkylsiloxane, in particular a compound 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) (In formula (IV), ALK represents a linear or branched, preferably linear, (C1-C4) alkylene group, for example, 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; R'4 represents a linear or branched, (C1-C6) alkyl group, preferably a C4 group such as n-butyl; n represents an integer of 2 or more; preferably, the value of n is such that the mass average molecular weight of the polydimethylsiloxane is in the range of 500 to 3000 g / mol -1 (It is something like this) Examples of polydimethylsiloxane (IV) include the products sold by Gelest under the names MCR-A11 and MCR-A12.

[0133] According to a particular embodiment of the present invention, the (poly)amine compounds are diamine compounds, i.e., they contain two primary and / or secondary amine groups, preferably primary amine groups (NH2). More particularly, they are represented by the formulae (V) and (VI): 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) (In formulas (V) and (VI), ALK and ALK′ may be the same or different and represent a linear or branched, preferably linear, (C1-C6) alkylene group, such as propyl; R′ may be the same or different and represent a (C1-C4) alkyl group, such as methyl; and m represents an integer of 0 or greater; preferably, the value of m is such that the mass average molecular weight of compound (V) or (VI) is 500 g / mol -1 ~55000g.mol -1 (The range is Examples of compounds of formula (VI) include those sold by Gelest under the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS-A32 and DMS-A35.

[0134] The (poly)amine compounds which are diamines are in particular polyetherdiamines, in particular those of the formula HN-ALK-O-[ALK'-O] m -ALK"-NH2 (ALK, ALK' and ALK" may be identical or different and represent a linear or branched (C1-C6) alkylene group, and m represents an integer greater than or equal to 0), such as 4,7,10-trioxa-1,13-tridecanediamine or in particular compounds from the company Hunstman known under the reference Jeffamine, and more particularly α,ω-diamino polyethylene glycols and / or polypropylene glycols in which the amine function is located at the chain end, such as the products sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000 and ED-2003.

[0135] According to a particular embodiment of the invention, the (poly)amine compounds are triamine compounds, i.e. they contain three primary and / or secondary amine groups, preferably primary amine groups (NH). More particularly, polyether triamines are in particular compounds of the formula ALK''' [(O-ALK') m -NH2]3 (n and ALK' are as defined above, ALK''' represents a linear or branched trivalent (C1-C6) alkylene group, and m represents an integer of 0 or greater).

[0136] As the (poly)amine compound which is a triamine compound, mention may be made in particular of polyethertriamines, in particular α,ω-diamino polyethylene glycols and / or polypropylene glycols (in which the amine functional groups are located at the chain ends), such as the product sold under the name Jeffamine T-403.

[0137] According to another particular embodiment of the invention, the (poly)amine compound comprises more than three primary and / or secondary amine groups, preferably primary amine groups (NH2).

[0138] In this variant, the (poly)amine compound is chosen from poly(meth)acrylates or poly(meth)acrylamides having primary or secondary amine groups in the side chain, such as poly(3-aminopropyl) methacrylamide and poly(2-aminoethyl) methacrylate.

[0139] Preferably, the (poly)amine compound is selected from chitosan (especially poly(D-glucosamine)) and polydimethylsiloxanes containing primary amine groups at the ends of the chains and / or in the side chains.

[0140] According to this variant, the (poly)amine compounds are in particular amino and poly((C2-C5) alkyleneimines), preferably polyethyleneimines and polypropyleneimines, in particular poly(ethyleneimines), in particular the products sold by Aldrich Chemical under the reference 408700 or by BASF under the trade name Lupasol, in particular those with a molecular weight of 1200 to 25000; poly(allylamine), in particular the product sold by Aldrich Chemical under the reference 479136; polyvinylamine and its copolymers, in particular copolymers with vinylamides, in particular vinylamine / vinylformamide copolymers, such as those sold under the name Lupamin® 9030 by BASF; polyamino acids containing NH groups, such as polylysine, in particular the products sold by JNC Corporation (formerly Chisso); aminodextrans, in particular the products sold by CarboMer Inc; aminopolyvinyl alcohols, in particular CarboMer Inc.; acrylamide (C1-C6) alkylamine copolymers, in particular acrylamidopropylamine copolymers; and poly(D-glucosamine), such as those sold under the reference Kionutrime CSG® by Kytozyme.

[0141] According to one embodiment, the polydimethylsiloxane containing terminal and / or pendant primary amine groups has the following formula (VII): 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) (In formula (VII), R a may be the same or different and represent a hydroxyl 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 N(H) groups, and m and n are integers equal to or greater than 1; preferably, m and n are such that the weight average molecular weight of the compound of formula (VII) is 1000 g.mol -1 ~500000g.mol -1 (The range is The compound is selected from those having the following structure:

[0142] According to an advantageous variant, formula (VII) is R a , R b and R c represents a methyl group, and ALK 1 represents a propylene group, and the values ​​of n and m are such that the mass average molecular weight of the polydimethylsiloxane is 1000 g.mol -1 ~55000g.mol -1 Examples of polydimethylsiloxanes of formula (VI) include the products sold by Gelest under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203.

[0143] According to another variant, formula (VII) is R a represents a (C1-C4) alkyl group such as hydroxyl or 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 such that the weight average molecular weight of the compound of formula (VI) is 5000 g.mol -1 ~500000g.mol -1 The range is as follows:

[0144] Amine polymers can also include α,ω-diaminopolytetrahydrofuran (or polytetramethylene glycol) and α,ω-diaminopolybutadiene.

[0145] According to a particular embodiment of the present invention, the (poly)amine compound is selected from hyperbranched polymers containing at least one amino group and dendrimers containing at least one amino group, such as PAMAM polyamidoamine dendrimers having an ethylenediamine core and terminal amine groups.

[0146] Thus, according to a preferred embodiment, the composition according to the invention comprises a crosslinker R chosen from (poly)amine compounds, in particular chosen from chitosan, aminoalkoxysilanes, polydimethylsiloxanes containing terminal or pendant primary amine groups, amodimethicones, polyglucosamines and mixtures thereof.

[0147] More preferentially, the composition according to the invention comprises a crosslinker R chosen from chitosan, aminoalkoxysilanes and polydialkylsiloxanes containing primary amine groups at the ends of their chains or in side chains, and even more preferentially chosen from poly(D-glucosamine), 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane and polydimethylsiloxanes containing terminal aminopropyl groups at the ends of their chains, and even more preferentially 3-aminopropyltriethoxysilane (APTES).

[0148] B) (Poly)thiol Compounds According to a preferred embodiment, the crosslinker R is chosen from (poly)thiol compounds, also known as "(poly)mercapto" compounds.

[0149] The (poly)thiol compound may in particular be an organic or inorganic, preferably an organic compound.

[0150] In a preferred embodiment, the (poly)thiol compound is silicon-based, i.e. it contains one or more thiol groups and also contains at least one siloxane chain.

[0151] In certain embodiments, the (poly)thiol compound is an inorganic compound, such as a polythiol silicone.

[0152] The (poly)thiol compounds used in the composition according to the invention are chosen in particular from non-polymeric (poly)thiol compounds.

[0153] The term "non-polymeric compound" for the purposes of the present invention means a compound that is not obtained directly by the polymerization reaction of a monomer.

[0154] According to one embodiment of the present invention, the (poly)thiol compound has the following formula (VIII): L(SH) q (VIII) (In formula (VIII), - q represents an integer equal to or greater than 2; preferably, n is 2 to 10, preferably 2 to 5, inclusive; - L represents a linear or branched, saturated or unsaturated or (hetero)cyclic, saturated or unsaturated, polyvalent (at least divalent) group, in particular containing from 1 to 500 carbon and / or silicon atoms, more particularly from 2 to 40 carbon and / or silicon atoms, even more particularly from 3 to 30 carbon and / or silicon atoms, preferably from 6 to 20 carbon atoms; L represents O, S, N, Si, C(X) and combinations thereof, such as -O-, -OC(X)-, -N(R)-C(X)-, -Si(R c )(R d )-O- (wherein R represents a hydrogen atom or a (C1-C6) alkyl group such as methyl); and / or L is -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 represent an oxygen or 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 represent a hydrogen atom or a (C1-C6) alkyl group or an aryl(C1-C4) alkyl group such as benzyl, preferably R a and R b represents a hydrogen atom); R c and R d may be the same or different and represent a (C1-C6) alkyl group, an aryl(C1-C4) alkyl group or a (C1-C6) alkoxy group. and solvates thereof, such as hydrates thereof.

[0155] According to a particular embodiment of the invention, the (poly)thiol compound is chosen from polythiol compounds, in particular polythiol compounds containing from 2 to 20 carbon atoms.

[0156] According to a preferred embodiment, the (poly)thiol compound is non-polymeric, in particular of formula (VIII) as defined above, where q is 2 or more, preferably p is an integer between 2 and 10, preferably between 2 and 5 inclusive.

[0157] The (poly)thiol compounds suitable for use in the present invention are preferably dithiol compounds.

[0158] Preferably, L is C to C 18 Preferentially, the lipophilic polythiol is a polyvalent radical, which is in particular linear. 18 Advantageously, C8-C 18 The chain is a hydrocarbon chain, i.e., formed from carbon and hydrogen. In particular, the fat-soluble polythiol is a linear C8-C 16 , especially C 10 ~C 14 Dithiols. More specifically, the (poly)thiol compounds of formula (VII) include 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, or 1,14-tetradecanedithiol is used, with 1,12-dodecanedithiol being preferred.

[0159] According to another particular embodiment of the invention, the (poly)thiol compound is chosen from thiolated alkoxysiloxanes, such as those having the following formula (VIII): R'1-Si(OR'2)z(R'3) x (VIII') (In formula (VIII'), R'1 is - thiol groups and an aryl group, an aryloxy group, an arylthio group or an arylamino group, wherein the aryl group is substituted with one or more thiol or thio(C1-C6)alkyl groups, preferably thio(C1-C6)alkyl groups; a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C substituted with one or more groups selected from 12 It is a hydrocarbon chain, - R'1 is optionally interrupted in its hydrocarbon chain by one or more heteroatoms such as O, S, N, carbonyl groups C(O) or combinations thereof, such as ester -C(O)-O- or amide -C(O)-N(H)-, and R'1 is directly bonded to the silicon atom via a carbon atom; R'2 and R'3 may be identical 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, x represents an integer ranging from 0 to 2, and z+x=3. is.

[0160] Preferably, R'2 represents a linear or branched, preferably linear, alkyl group containing 1 to 4 carbon atoms, such as ethyl.

[0161] Preferably, R'3 represents a straight or branched, preferably straight chain alkyl group containing 1 to 4 carbon atoms, such as methyl or ethyl.

[0162] 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 chain substituted with one or more thiol groups, preferably substituted with one thiol group.

[0163] Preferably, R'1 is a saturated linear C1-C6 hydrocarbon chain substituted with a thiol group, and R'2 represents an alkyl group containing 1 to 4 carbon atoms.

[0164] R'3 represents an alkyl group containing 1 to 4 carbon atoms. Preferably, z is 3.

[0165] According to a more specific embodiment of the present invention, the thiolated alkoxysiloxane is selected from those having the following formula (IX): (R 1 O)(R 2 )(R 3 )Si-[CH(R 4 )] t -[N(R' 4 )-L 1 ] p -SH (IX) (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 group; ·R 2 and R 3 may be the same or different, preferably the same; - (C1-C6) alkyl groups, in particular C1-C4 alkyl groups, for example methyl; - (C1-C6)alkoxy groups, in particular (C1-C4)alkoxy groups, for example methoxy is selected from ·R 4 and R' 4 may be the same or different and represent a hydrogen atom or a (C1-C6) alkyl group, for example methyl; L 1 is a divalent saturated straight-chain or branched C1-C 20 represents a hydrocarbon group).

[0166] According to a particular embodiment of the invention, the thiolated alkoxysiloxane is chosen from those having the following formula (IX'): (R' 1 O)(R' 2 )(R' 3 )Si-CH(R 4 )-CH(R 5 )-(L 2 ) q -SH (IX') (In formula (IX'), q is 0 or 1; X represents an oxygen or sulfur atom, preferably a sulfur atom; R' 1 represents a (C1-C6) alkyl group; R' 2 and R' 3 may be the same or different, preferably the same; - (C1-C6)alkoxy groups, especially C1-C4; - (C1-C6) alkyl group is selected from ·R 5 represents a hydrogen atom or a C1-C4 alkyl group optionally substituted with an amino, thiol or hydroxyl group; ·R 4 represents a hydrogen atom or a C1-C4 alkyl group, particularly methyl; L 2 is a divalent linear or branched saturated C1-C alkyl group optionally interrupted by heteroatoms such as -N(H)- and / or optionally substituted with one or more hydroxyl, thiol or amino groups; 20 represents a hydrocarbon group).

[0167] Preferably, the thiolated alkoxysilane is 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.

[0168] More preferentially, the thiolated alkoxysilane is chosen from 2-(triethoxysilyl)ethanethiol (18236-15-2) and 3-(triethoxysilyl)-1-propanethiol (14814-09-6).

[0169] According to a preferred embodiment of the present invention, the (poly)thiol compound is selected from polymeric (poly)thiol compounds.

[0170] Polymeric (poly)thiol compounds can be star-, comb-, brush-, and dendritic homopolymers or copolymers containing hydroxyl and / or 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 pendant groups.

[0171] Mention may be made, for example, of the polymers described in the following scientific publications: 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; EP 1247515 A2; U.S. Pat. No. 3,676,440; and EP 1,572,778.

[0172] The polymeric (poly)thiol compounds of the present invention are preferably organic and / or silicone compounds, more preferentially those having the formula (X): POLY(SH) q (X) (In formula (X), q is 2 or more, preferably 3 or more; POLY represents a polymeric group, which is preferably carbon-based or silicon-based; POLY is O, S, N, Si, and C(X) and combinations thereof, such as -O-, -OC(X)-, -N(R)-C(X)-, or -Si(R c )(R d )-O- (wherein R represents a hydrogen atom or a (C1-C6) alkyl group such as methyl); and / or POLY is one or more halogen atoms or R a (R b )N- and -(X') a -C(X)-(X'') b -R a optionally substituted with a group selected from X, X' and X'' may be identical or different and are oxygen or sulfur atoms or N(R b ) group; 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 are hydrogen atoms or (C1-C 10 ) alkyl or aryl(C1-C4) alkyl group, for example, benzyl; preferably, R a and R b represents a hydrogen atom; -R c and R d may be the same or different, (C1 to C 10 ) alkyl group, aryl(C1-C4) alkyl group or (C1-C 10 ) represents an alkoxy group).

[0173] Methods for preparing the polymeric (poly)thiol compounds used according to the present invention are known to those skilled in the art, and some methods are described 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 having a thiol group or a protected thiol group, which is optionally copolymerized or copolycondensed with monomer units not having a thiol group or a protected thiol group.

[0174] According to one embodiment of the present invention, the polymeric (poly)thiol compounds used according to the invention are polymers soluble in a cosmetic medium, in particular in an aqueous or aqueous-alcoholic medium, and more preferentially obtained from aminopolymers and their ammonium salts or from polyhydroxylated polymers.

[0175] 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.

[0176] 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, POLY represents a carbon-based and / or silicon-based, preferably silicon-based, polymer group, and POLY may also contain one or more heteroatoms selected from O, N, or S and / or one or more groups selected from (thio)ester groups, (thio)ketone groups, (thio)amide groups, (thio)urea groups, and (thio)carbamate groups, and / or one or more linear or branched (C1-C 10 ) alkyl group or linear or branched (C1-C 10 ) alkoxy group, and it is understood that when POLY is substituted, a thiol group may be attached to this substituent.

[0177] The weight average molecular weight of polythiol polymer compounds such as those of formula (X) is generally between 500 and 400,000 g.mol -1 , preferably 500 to 150,000 g.mol -1 According to a particular embodiment of the present invention, the polythiol compound is selected from polyorganosiloxanes containing thiol groups at the terminal chains, such as those having the following formula (XI): 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) In formula (XI), ·R a and R b may be identical or different, preferably identical, and represent a group in (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 benzooxy, preferably a group in (C1-C4)alkyl, such as methyl, n represents an integer of 1 or more, and more specifically, the value of n is set so that the mass average molecular weight of the silicone is 500 to 55,000 g / mol -1 in particular n is an integer ranging from 1 to 100, preferably from 5 to 50 and preferentially from 10 to 30, 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 chain containing 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, and in particular a covalent bond or a (C1-C6)alkylene group, a (C1-C6)alkyleneoxy group, an oxy(C1-C6)alkylene group, a (C1-C6)alkyleneoxy(C1-C6)alkyleneoxy group or an oxy(C1-C6)alkyleneoxy(C1-C6)alkylene group, preferably a (C1-C6)alkylene group, a (C1-C6)alkyleneoxy group, an oxy(C1-C6)alkylene group or a (C1-C6)alkyleneoxy(C1-C6)alkylene group.

[0178] Preferentially, the (poly)thiol compounds are polythiol polyorganosiloxanes, more preferentially polythiol polydimethylsiloxanes, chosen in particular from those having formula (XII): HS-L 4 -Si(CH3)2-O-[Si(CH3)2-O] n-Si(CH3)2-L 5 -SH (XII) In formula (XII), L 4 and L 5 is as defined above in formula (XI), in particular L 4 and L 5 represents a divalent radical selected from a (C1-C6)alkylene group, a (C1-C6)alkyleneoxy group, an oxy(C1-C6)alkylene group or a (C1-C6)alkyleneoxy(C1-C6)alkylene group, more preferentially -R2-, -O-R2-, -R2-O- and -R2-O-R2-, preferably -R2-O-R2- (R2 is a linear or branched, preferably linear, (C2-C6)alkylene group, such as ethylene or n-propylene, preferably n-propylene); ·n is as defined in formula (XI).

[0179] Examples of polythiol compounds of formula (XII) include mercaptosiloxanes or thiolated siloxanes with thiol functional groups at the chain ends, sold by Shin-Etsu Chemical Co., Ltd. under the reference X-22-167B, and mercaptosiloxanes with pendant mercapto groups, sold by Shin-Etsu Chemical Co., Ltd. under the reference KF-2001, or polydimethylsiloxanes with thiol functional groups at the chain ends via thio-n-propyl 80-120 groups, sold by Gelest under the name DMS-SM 21.

[0180] Preferentially, the polythiol compound is a polyorganosiloxane containing thiol groups in the side chain, such as that 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 )-Ra (XIII) 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 such as methyl; ·R d may also represent a (C1-C4) alkylamino group or a (C1-C6) alkyl group substituted with an amino group or a thiol group, preferably a (C1-C4) alkyl such as methyl; ALK1 represents a linear or branched, optionally cyclic, divalent saturated or unsaturated hydrocarbon-based chain containing 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen (in particular O), (thio)carbonyl groups C(X) (X represents O or S or combinations thereof, such as -O-, -OC(O)- or -C(O)-O-); preferably, ALK1 represents a (C1-C6) alkylene group, more preferentially a (C1-C4) alkylene group, for example propylene; n and m may be the same or different and represent an integer greater than 2, and more particularly, the values ​​of m and n are determined so that the mass average molecular weight of the polyorganosiloxane is in the range of 1000 to 55000 g / mol -1 It is something like this.

[0181] Examples of the polythiol compound of formula (XIII) include those sold by Genesee Polymers under the names GP-367, GP-71-SS, GP-800, and GP-710, preferably GP-367 sold by Genesee Polymers.

[0182] In particular, the polythiol compound is a polydimethylsiloxane containing at least two thiol groups, such as the products SMS-022, SMS-042 and SMS-992 sold by Gelest under https: / / www.gpcsilicones.com / products / silicone-fluids / mercapto-functional, https: / / www.shinetsusilicone-global.com / products / type / oil / detail / search / deg07.shtml and 1053_Reactive Silicones_Silanes / Silicones-Gelest.

[0183] 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 bearing at least one thiol group, such as thiolated PAMAM dendrimers.

[0184] Preferably, the (poly)thiol compounds used according to the invention are selected from polydiallylsiloxanes, in particular polydimethylsiloxanes, containing at least two thiol groups, such as those having the formula (XIII):

[0185] C) (Poly)carbonyl compounds According to a particular embodiment, the crosslinking agent R is a (poly)carbonyl compound.

[0186] In particular, the (poly)carbonyl compound is selected from 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, 3-acetylbenzaldehyde, 9-(2-ethylhexyl)carbazole-3,6-dicarboxaldehyde, phthaldialdehyde, 1,3-cyclohexanedione, 4,4'-biphenyldicarboxaldehyde, benzene-1,3,5-tricarboxaldehyde and nonionic or anionic oxidized polysaccharides, such as oxidized inulin, in particular those of formula (II) as defined below. In particular, the (poly)carbonyl compound contains a saturated or unsaturated, aromatic C5-C7 carbon ring, preferably aromatic, e.g., phenyl, or non-aromatic and saturated, e.g., cyclohexyl, more preferentially unsaturated and aromatic, e.g., terephthalaldehyde.

[0187] According to a particular embodiment, the (poly)carbonyl compound is chosen from non-ionic or anionic oxidized polysaccharides comprising one or more aldehyde groups and optionally one or more anionic groups.

[0188] These anionic groups are preferably carboxyl or carboxylate groups.

[0189] The nonionic or anionic oxidized polysaccharides according to the present invention can be represented by the following formula (II): P-(CHO) m (COOQ) n (II). In formula (II), P represents a polysaccharide chain consisting of a monosaccharide preferably containing 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms, more particularly 6 carbon atoms; Q is selected from the group consisting of a hydrogen atom, 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-propanediol, and ions derived from basic amino acids, such as lysine, arginine, sarcosine, ornithine and citrulline; m+n is greater than or equal to 1, m is such that the degree of substitution of the polysaccharide with one or more aldehyde groups (DS(CHO)) is in the range of 0.001 to 2, preferably in the range of 0.005 to 1.5; ·n is such that the degree of substitution of the polysaccharide with one or more carboxyl groups (DS(COOX)) is in the range of 0 to 2, preferably 0.001 to 1.5.

[0190] The expression "degree of substitution DS(CHO) or DS(COOX) of the polysaccharide of the invention" means the ratio of the number of carbons oxidized to obtain aldehyde or carboxyl groups in all repeating units to the number of monosaccharides (including those ring-opened by pre-oxidation) that constitute the polysaccharide. The CHO and COOX groups can be obtained on specific carbon atoms during oxidation, for example, on carbon atoms 2, 3, or 6 of sugars containing six carbon atoms.

[0191] Preferably, oxidation can occur at the 2- and 3-position carbons of the ring, which may already be opened, more specifically at 0.01% to 75%, preferably 0.1% to 50%, based on the number of carbon atoms.

[0192] The polysaccharide chains represented by P are preferably selected from cellulose, starch, maltodextrin, guar gum, xanthan gum, pullulan gum, agar gum, carrageenan gum, gellan gum, acacia gum, polyxylan and tragacanth gum and derivatives thereof.

[0193] The term "derivatives" means compounds obtained by chemical modification of the compounds mentioned. These may be esters, amides or ethers of said compounds.

[0194] The oxidation can be carried out according to methods known in the art, for example according to the method described in French Patent No. 2842200, in the literature French Patent No. 2854161 or in the article "Hydrophobic films from maize bran hemicelluloses" by E. Fredon et al., Carbohydrate Polymers 49, pages 1 to 12 (2002).

[0195] 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).

[0196] According to this embodiment, the (poly)carbonyl compound is a compound as described in Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019), in which an amine catalyst is used in its implementation; preferably, the amine catalyst is 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), in particular the catalyst is DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

[0197] D) (Poly)acrylate Compounds According to a particular embodiment, the crosslinking agent is a (poly)acrylate compound.

[0198] The term "(poly)acrylate" refers to a (poly)acrylate having at least one acrylate ester group H2C=C(R e )-C(O)-Y-(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 O).

[0199] More particularly, the (poly)acrylates of the present invention are those having the formula (XIV): L[-YC(O)-C(R e )=CH2] q (XIV). 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). According to a preferred embodiment, the compound of formula (XIV) is such that L represents a di- or trivalent, preferably trivalent, hydrocarbon-based chain containing 1 to 8 carbon atoms, q is 2 or 3, preferably 3, Y represents O, and R e represents a hydrogen atom.

[0200] According to a particular embodiment, the (poly)acrylate compound is chosen from polyorganosiloxanes comprising at least one acrylate group in the side chain, such as those having the following formula: 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) In formula (XV), ·R a , R b and R dis as defined for formula (XIII) and preferably 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 preferentially a (C1-C4) alkylene group, for example propylene; n and m may be the same or different and represent an integer greater than 2, and more particularly, the values ​​of m and n are determined so that the mass average molecular weight of the polyorganosiloxane is in the range of 1000 to 55000 g / mol -1 It is something like this, Y is as defined above and is preferably O.

[0201] More particularly, the (poly)acrylate compound may be 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, bis(trimethylolpropane)tetraacrylate, 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, pentaerythrityl tetraacrylate, acrylate, pentaerythrityl triacrylate, poly(propylene glycol) diacrylate, tricyclo[5.2.1.02,6]decanedimethanol diacrylate, trimethylolpropane ethoxylate (1EO / OH) methyl ether diacrylate, trimethylolpropane propoxylate triacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tri(propylene glycol) diacrylate, trimethylolpropane triacrylate, and tris[2-(acryloyloxy)ethyl]isocyanurate.

[0202] The (poly)acrylate compound may also be selected from N,N'-methylenebisacrylamide.

[0203] According to this embodiment, (poly)acrylate compounds are used in combination with amine catalysts in the implementation thereof, as described, for example, in Progress in Coating 129, 21-25 (2019) and Progress in Coating 135, 510-516 (2019). Preferably, the amine catalyst is 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 preferentially 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), in particular the catalyst is DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

[0204] More particularly, the (poly)acrylate compounds are chosen from those of formula (XIV), in particular trimethylolpropane triacrylate, and those of formula (XV), in particular copolymers of dimethylsiloxane and acryloxypropylmethylsiloxane.

[0205] E) Metal alkoxide According to another particular embodiment, the crosslinker R has the formula (XIV) shown below: a ), (XIV b ), (XIV c ) and (XXIV d ) and mixtures thereof. M-(OR1) n (XIV a ) RM-(OR1) n-1 (XIV b ) (R1O) n-1 -M-R''-M'-(OR1') n’-1 (XIV c ) RM(R')-(OR1) n-2 (XXIV d ) Formula (XIV a ), (XIV b ), (XIV c ) and (XIV d ) inside, M and M' may be identical or different and are selected from alkaline earth metals, transition metals, metals of the lanthanide group, post-transition metals such as aluminum or tin and metalloids such as boron; preferably represent an atom selected from transition metals such as Ti and post-transition metals such as aluminum; n and n' represent the valences of the atoms represented by M and M', respectively; - R1 and R1' may be identical 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, optionally interrupted by 1 to 20 heteroatoms selected from O, N, S and P, in particular O or N; and / or said hydrocarbon-based group is optionally substituted by one or more hydroxyl or carbonyl groups; - R and R', which may be identical or different, represent a hydrogen atom or a linear, 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, in particular O or N, and / or said hydrocarbon-based group is optionally 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 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, in particular O or N (R2 represents a linear, cyclic or branched, saturated or unsaturated hydrocarbon group containing 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms).

[0206] Preferably, M and M', which may be identical or different, represent an atom selected from transition metals such as titanium or zirconium or alkaline earth metals such as magnesium, more preferentially an atom selected from transition metals such as titanium or zirconium, and even more preferentially titanium.

[0207] Preferably, the organometallic compound has the formula (XIV) defined above. a According to this preferred embodiment, the organometallic compound is more particularly an alkoxide of formula (XIV a ) inside, - M represents an atom selected from transition metals, metals of the lanthanide group, post-transition metals such as aluminum and tin, metalloids such as boron, or alkaline earth metals such as magnesium or calcium; - n represents the valence of the atom represented by M; - selected from alkoxides in which R1 represents a saturated, linear or branched hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms.

[0208] According to another more preferred embodiment, the organometallic compound is of formula (XIV a), M represents an atom selected from transition metals such as zirconium or titanium, metals of the lanthanide group, post-transition metals such as aluminum or tin, metalloids such as boron, and alkaline earth metals such as magnesium, preferably M represents a titanium atom; n represents the valence of the atom represented by M, in particular 1, 2, 3, or 4, in particular 4; and R1 is selected from alkoxides representing a methyl group, an ethyl group, a 2-ethylhexyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, or a t-butyl group. According to a more preferred embodiment, the organometallic compound is selected from the group consisting of 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(OCH2C H2CH3)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 mixtures thereof, more preferentially selected from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof. More preferentially, the crosslinking agent R is preferably selected from the group consisting of ... a ) compounds such as titanium butoxide.

[0209] According to a preferred embodiment, the crosslinking agent is selected from (poly)amine compounds A), (poly)thiol compounds B), (poly)carbonyl compounds C) and (poly)acrylate compounds D), preferably selected from (poly)amine compounds A) and (poly)thiol compounds B).

[0210] Said (poly)amine compounds A) are chosen in particular from a) chitosans such as poly(D-glucosamine), b) polyetherdiamines, in particular polyethylene glycol α,ω-diamine (having amine functions at the chain ends) and 4,7,10-trioxa-1,1-tridecanediamine, c) polyethertriamines, such as polyetheramine (or Jeffamine), d) aminoalkoxysilanes, such as APTES, 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-diNH) and amodimethicones containing amine groups in the side chains, such as biscetearyl amodimethicone.

[0211] The (poly)thiol compound B) is in particular selected from a) polydialkylsiloxanes having thiol groups and b) alkoxysilanes having thiol groups, in particular a) polydialkylsiloxanes having thiol groups, preferentially polydimethylsiloxanes having thiol groups in the side chains (such as mercaptopropyl), in particular those of formula (XIII):

[0212] The (poly)acrylate D) compounds are in particular selected from those of formula (XIV), in particular trimethylolpropane triacrylate, and those of formula (XV), in particular copolymers of dimethylsiloxane and acryloxypropylmethylsiloxane, preferably trimethylolpropane triacrylate.

[0213] iii) Cosmetic active agents According to a particular embodiment, the method of the present invention makes use of one or more cosmetic active agents.

[0214] More particularly, in the method of the present invention, at least one of the compositions C1, C2, C3, C4 or C5 used comprises one or more cosmetic active agents, in particular the cosmetic active agents of the present invention are selected from a) colorants (or coloring agents) selected from pigments, direct dyes and mixtures thereof, b) active agents for caring for keratinous materials, preferably the skin, c) UV filters and d) mixtures thereof.

[0215] According to a particular embodiment, the at least one cosmetic agent is chosen from colorants, preferably chosen from pigments, direct dyes and mixtures thereof, more preferentially pigments.

[0216] Of course, the skilled person will take care to select this or these optional 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 envisaged addition.

[0217] color material According to a particular embodiment, the method of the present invention uses one or more colorants.

[0218] More particularly, at least one of the compositions C1, C2, C3, C4 or C5 used in the method of the present invention comprises at least one particulate or non-particulate water-soluble or water-insoluble colorant, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition in question.

[0219] For obvious reasons, this amount is subject to wide variation depending on the strength of the color effect desired and the color strength achieved by the colorant under consideration, and adjustment thereof is clearly within the capabilities of one skilled in the art.

[0220] Preferably, at least one of compositions C1, C2, C3, C4 or C5 comprises at least one colorant selected from pigments, direct dyes and mixtures thereof, more preferentially from pigments; more preferentially, the pigments of the present invention are selected from carbon black, iron oxides, in particular yellow, red and black iron oxides and iron oxide-coated mica, triarylmethane pigments, in particular blue and purple triarylmethane pigments such as Blue 1 Lake, azo pigments, in particular red azo pigments, for example D&C Red 7, alkali metal salts of lithol red, for example calcium salt of lithol red B, and even more preferentially red iron oxides, yellow iron oxides and azo pigments, in particular red azo pigments, for example D&C Red 7.

[0221] pigment The term "pigment" for the purposes of the present invention means any compound capable of imparting color to keratinous materials, the solubility of which in water at 25°C and atmospheric pressure (760 mmHg) is less than 0.05% by weight, preferably less than 0.01% by weight.

[0222] Pigments suitable for use in the present invention include organic and / or mineral pigments known in the art, particularly those described in Kirk-Othmer's Encyclopedia of Chemical Technology and Ullmann's Encyclopedia of Industrial Chemistry. These pigments can be synthetic or natural. They can be in powder pigment form or in pigment paste form. They can be coated or uncoated. These pigments can be selected from, for example, mineral pigments, organic pigments, special effect pigments such as lakes, pearlescent pigments, or glitter flakes, and mixtures thereof.

[0223] Pigments suitable for use in the present invention may be selected from mineral pigments.

[0224] The term "mineral pigment" refers to any pigment that meets the definition in the chapter on inorganic pigments of Ullmann's encyclopedia. Among the mineral pigments useful in the present invention, mention may be made of manganese violet, ultramarine blue, chromium hydroxide, ferric blue, and zinc oxide, iron oxide, or chromium oxide, as well as titanium, zirconium, or cerium oxides.

[0225] These may also be pigments having, for example, a sericite / brown iron oxide / titanium dioxide / silica structure. Such pigments are sold, for example, by Chemicals and Catalysts under the references Coverleaf NS or JS, and have a hiding power of around 30. These may also be pigments having, for example, a silica microsphere structure containing iron oxide. An example of a pigment having this structure is the product sold by Miyoshi Kasei Co., Ltd. under the reference PC Ball PC-LL-100 P, which is composed of silica microspheres containing yellow iron oxide.

[0226] Advantageously, the pigment may be iron oxide and / or titanium dioxide.

[0227] Pigments suitable for use in the present invention may be selected from organic pigments.

[0228] The term "organic pigment" refers to any pigment that meets the definition in the chapter on organic pigments of Ullmann's encyclopaedia. 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, red ... The red pigments may be selected from those classified under the reference numbers 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, and from the pigments obtained by oxidative polymerization of indole or phenol derivatives described in French Patent No. 2 679 771.

[0229] Examples of organic pigment pastes include those sold by Hoechst under the following names: Cosmenyl Yellow 10G: Pigment Yellow 3 (CI 11710); Cosmenyl G yellow: Pigment Yellow 1 (CI 11680); Cosmenyl GR orange: Pigment Orange 43 (CI 71105); Cosmenyl R red: Pigment Red 4 (CI 12085); Cosmenyl FB carmine: Pigment Red 5 (CI 12490); Cosmenyl RL violet: Pigment Violet 23 (CI 51319); Cosmenyl A2R blue: Pigment Blue 15.1 (CI 74160); Cosmenyl GG green: Pigment Green 7 (CI 74260); Cosmenyl R black: Pigment Black 7 (CI 77266).

[0230] 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 binding an organic pigment to the core, and at least one organic pigment covering at least a part of the core.

[0231] The organic pigment may also be a lake.

[0232] The term "lake" refers to a dye that has been adsorbed onto insoluble particles, the resulting mass remaining insoluble during use.

[0233] Inorganic substrates onto which dyes are adsorbed include, for example, alumina, silica, calcium / sodium borosilicate, calcium / aluminium borosilicate and aluminium. Among the dyes adsorbed onto organic substrates, carminic acid can be mentioned. Mention may also be made of dyes known by the following names: D&C Red 21(CI 45380), D&C Orange 5(CI 45370), D&C Red 27(CI 45410), D&C Orange 10(CI 45425), D&C Red 3(CI 4530), D&C Red 4(CI 15510), D&C Red. 33(CI 17200), D&C Yellow 5(CI 19140), D&C Yellow 6(CI 15985), D&C Green 5(CI 61570), D&C Yellow 10(CI 77002), D&C Green 3(CI 42053), D&C Blue 1(CI 42090), 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 Chlorophyllin, Methylene Blue, Anthocyanins (Enocyanin, Black Carrot, Hibiscus, Elderberry), Caramel, Riboflavin, Beet Juice and Caramel.

[0234] An example of a lake is the product known as: D&C Red 7 (CI 15850:1).

[0235] The pigment may also be a special effect pigment.

[0236] The term "special effect pigments" generally refers to pigments that produce a colored appearance (characterized by a specific hue, a specific vividness, and a specific brightness) that is not uniform but changes depending on the viewing conditions (light, temperature, viewing angle, etc.) and therefore differs from standard colored pigments that exhibit a uniform opaque, translucent, or transparent hue.

[0237] There are several types of special effect pigments: those with a low refractive index, such as fluorescent or photochromic pigments, and those with a high refractive index, such as pearlescent agents, interference pigments or glitter flakes.

[0238] The size of the pigments used in the composition according to the invention is generally between 10 nm and 200 μm, preferably between 20 nm and 80 μm, and more preferentially between 30 nm and 50 μm.

[0239] The pigment may be dispersed in the composition by a dispersant.

[0240] The dispersant may be a surfactant, oligomer, polymer, or mixture of several thereof, having one or more functional groups with a strong affinity for the surface of the particles to be dispersed. In particular, they can be physically or chemically bonded to the pigment surface. The dispersant also contains at least one functional group that is miscible with or soluble in the continuous medium. In particular, 12-hydroxystearic acid and C8-C 20Esters of fatty acids with polyols such as glycerol or diglycerol, such as poly(12-hydroxystearic acid) stearate having a molecular weight of about 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 Dehymyls PGPH, or polyhydroxystearic acid, such as the product sold by Uniqema under the reference Arlacel P100, and mixtures thereof, can be used. Other dispersants that can 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, such as those sold by Dow Corning under the references DC2-5185 and DC2-5225 C. The pigments used in the compositions can be surface-treated with organic agents. According to a particular embodiment, the dispersant is of the aminosilicone type other than the silicones mentioned above and is cationic. Preferably, the pigment is chosen from mineral pigments, mixed mineral-organic pigments or organic pigments.

[0241] According to a particular embodiment, the pigment according to the invention is an organic pigment, preferentially an organic pigment surface-treated with an organic agent chosen from silicone compounds.

[0242] According to another embodiment of the invention, the pigment according to the invention is a mineral pigment.

[0243] According to a particular embodiment of the invention, the cosmetic active agent is a colorant chosen from one or more direct dyes.

[0244] The term "direct dyes" refers to natural and / or synthetic dyes other than oxidation dyes. These are dyes that will spread on the surface of the fiber. They can be ionic or non-ionic, preferably cationic or non-ionic.

[0245] Among the direct dyes suitable for use in the present invention, mention may be made, alone or in mixtures, of azo direct dyes; (poly)methine dyes, such as cyanine, hemicyanine and styryl; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes; natural direct dyes.

[0246] The direct dye is preferably a cationic direct dye, such as hydrazonocationic dyes of the formulae (A) and (B) and azocationic dyes of the formulae (C) and (D) shown 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) In formulas (A) to (D), - Het + represents a cationic heteroaryl group, such as imidazolium, indolium or pyridinium, preferentially having a cationic charge in the ring and preferentially optionally substituted with at least one (C1-C8) alkyl group, such as methyl; - Ar + represents an aryl group such as phenyl or naphthyl bearing an exocyclic cationic charge, preferentially ammonium, in particular tri(C1-C8)alkylammonium such as trimethylammonium; - Ar represents an aryl group, in particular phenyl, optionally substituted with one or more electron-donating groups, such as optionally substituted (C1-C8) alkyl, optionally substituted (C1-C8) alkoxy, (di)(C1-C8) (alkyl) amino, in which the alkyl groups are optionally substituted with 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, preferentially optionally substituted with one or more (C1-C8)alkyl, hydroxyl, (di)(C1-C8)(alkyl)amino, (C1-C8)alkoxy or phenyl groups; Ra and Rb may be identical or different and represent a hydrogen atom or a (C1-C8) alkyl group optionally substituted (preferentially by a hydroxyl group); or Otherwise, Het + the substituents Ra bearing a substituent and / or the substituents Rb bearing an Ar substituent together with the atoms carrying them form a (hetero)cycloalkyl; in particular Ra and Rb represent a hydrogen atom or a (C1-C4) alkyl group optionally substituted with a hydroxyl group, - Q - represents an organic or inorganic anionic counterion such as a halide or alkyl sulfate.

[0247] Mention may in particular be made of the azo and hydrazono direct dyes with an endocyclic cationic charge of the formulae (A) to (D) defined above, more particularly the cationic direct dyes with an endocyclic cationic charge described in patent applications WO 95 / 15144, WO 95 / 01772 and EP 714954, preferentially the following direct dyes:

[0248] [ka] (In formulas (E) and (F), -R 1 represents a (C1-C4) alkyl group such as 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 an optionally substituted (C1-C8) alkyl, an optionally substituted (C1-C8) alkoxy or a (di)(C1-C8)(alkyl)amino in which the alkyl group is optionally substituted with a hydroxyl group; in particular R 4 is a hydrogen atom, Z represents a CH group or a nitrogen atom, preferentially CH, - Q - is an anionic counterion as defined above, especially a halide such as chloride or an alkyl sulfate such as methyl sulfate or mesyl).

[0249] In particular, the dyes of formula (E) and (F) are selected from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof, and 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 dye can be selected from anionic direct dyes. The anionic direct dyes of the present invention are dyes commonly referred to as "acid" direct dyes, due to their affinity for alkaline substances.

[0250] The term "anionic direct dye" means a direct dye containing in its structure at least one CO2R or SO3R substituent, where R represents a hydrogen atom or a cation or ammonium ion derived from a metal or an amine.

[0251] 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.

[0252] Among the natural direct dyes that can be used according to the invention, mention may be made of lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechualdehyde, indigo, isatin, curcumin, spinulosin, apigenidin, orcein. It is also possible to use extracts or decoctions containing these natural dyes, in particular poultices or extracts based on henna dye.

[0253] Preferably, the direct dye is selected from anionic direct dyes.

[0254] The colorant, preferably a pigment, may be present in a concentration of 0.01% to 30% by weight, preferably 0.02% to 20% by weight, more particularly 0.05% to 15% by weight, relative to the total weight of the composition containing it.

[0255] The direct dyes may be present in a concentration ranging from 0.001% to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight relative to the total weight of the composition containing it.

[0256] Preferably, the cosmetic active agent, in particular the colorant, more particularly the pigment, is incorporated at least in compositions C1, C2, C3, C4 or C5.

[0257] Care activator According to a particular embodiment, the method of the present invention makes use of one or more care actives.

[0258] 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 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 in question. In particular, the care actives may be at least one hydrophilic and / or one lipophilic active, preferably a hydrophilic care active.

[0259] The term "hydrophilic active agent" means a water-soluble or water-dispersible active agent capable of forming hydrogen bonds.

[0260] Cosmetic care active agents are in particular: a) vitamins and their derivatives, in particular their esters, in particular tocopherol (vitamin E) and its esters (such as tocopheryl acetate), ascorbic acid (vitamin C) and its derivatives; b) humectants, in particular urea, hydroxyurea, glycerol, polyglycerol, glycerol glucoside, diglycerol glucoside, polyglyceryl glucoside and xylyl glucoside, in particular glycerol; c) C-glycoside compounds; d) antioxidant compounds; e) anti-ageing active agents, in particular hyaluronic acid compounds, in particular hyaluronic acid compounds. sodium salts of sodium hydroxybenzoate, retinol and its derivatives, salicylic acid compounds, in particular n-octanoyl-5-salicylic acid (capryloyl salicylic acid), caffeine, adenosine, c-β-d-xylopyranoside-2-hydroxypropane and (3-hydroxy-2-pentylcyclopentyl)acetic acid; f) skin care agents selected from allantoin, panthenol and protein hydrolysates; g) polyphenols, in particular escin, ruscus, diosmin, hesperidin and resveratrol; and h) mixtures thereof.

[0261] According to a particular embodiment of the invention, in the method of the invention, at least one of the compositions C1, C2, C3, C4 or C5 used comprises a moisturizer (also known as a humectant). Preferably, the care active is a moisturizer, in particular glycerin (glycerol).

[0262] The care active may be present, in particular in the composition containing it, in a content ranging from 0.01% to 30% by weight, preferably from 0.02% to 25% by weight relative to the weight of the composition.

[0263] UV screening agents According to one embodiment of the present invention, in the method of the present invention, at least one of the compositions C1, C2, C3, C4, or C5 used contains at least one UV filter as a cosmetic active agent. The UV filter is a UV filter commonly used in cosmetics. It may be selected from the positive list included in Annex VI of (EC) Regulation No. 1223 / 2009, which sets out the list of UV filters permitted in cosmetics. UV filters suitable for use in the present invention may be of various natures. They may be lipophilic, hydrophilic, or insoluble organic agents.

[0264] The term "lipophilic UV screening agent" means any cosmetic or dermatological screening agent that can be completely dissolved in molecular form in a liquid fatty phase or that can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.

[0265] The term "hydrophilic UV filter" means any cosmetic or dermatological filter that can be completely dissolved in molecular form in a liquid aqueous phase or that can be dissolved in colloidal form (e.g., micellar form) in a liquid aqueous phase.

[0266] The term "insoluble UV filter" refers to any cosmetic or dermatological filter that is neither a lipophilic nor a hydrophilic UV filter and that is in particulate form in an aqueous or liquid fatty phase. The UV filter of the composition according to the invention is capable of providing photoprotection against UVA and / or UVB rays.

[0267] According to a preferred embodiment, the composition according to the invention, which is preferably a cosmetic composition, may comprise at least one organic and / or inorganic UV filter (for filtering the ultraviolet radiation of sunlight).

[0268] In particular, the UV filter is selected from bis-resorcinyltriazine derivatives, dibenzoylmethane derivatives, benzylidene camphor derivatives and mixtures thereof. Organic UV filter agents include anthranilic acid derivatives, cinnamic acid derivatives, salicylic acid derivatives, benzophenone derivatives, phenylbenzotriazole derivatives, benzalmalonate derivatives, in particular those described in patent US Pat. No. 5,624,663, phenylbenzimidazole derivatives, imidazolines, 4,4-diarylbutadiene derivatives, and bis-benzazol derivatives described in patents EP 669,323 and US Pat. No. 2,463,264. p-aminobenzoic acid (PABA) derivatives; methylenebis(hydroxyphenylbenzotriazole) derivatives as described in patent applications U.S. Pat. No. 5,237,071, U.S. Pat. No. 5,166,355, British Patent No. 2,303,549, German Patent No. 19,726,184 and European Patent No. 893,119; and patent applications EP No. 0,832,642, EP No. 1,027,883 and EP No. 130,013. benzoxazole derivatives such as those described in patent applications WO 93 / 04665 and DE 10162844; shielding polymers and shielding silicones, in particular those described in patent application WO 93 / 04665; α-alkylstyrene dimers such as those described in patent application DE 19855649; 4,4-diarylbutadienes such as those described in patent applications EP 0967200, DE 19746654, DE 19755649, EP 1008586, EP 1133980 and EP 133981; other merocyanine derivatives such as those described in patent applications WO 04 / 006878, WO 05 / 058269 and WO 06 / 032741, and mixtures thereof.

[0269] According to a particular embodiment, the concentration of organic UV filters in the composition according to the invention is in the range of 1% to 50% by weight, preferably in the range of 1% to 40% by weight and better still, for example, in the range of 5% to 35% by weight relative to the total weight of the composition.

[0270] The UV filter may be an inorganic UV filter, which is generally a pigment. The pigment may be coated or uncoated.

[0271] Thus, the inorganic UV filter may be selected from coated or uncoated pigments, in particular coated titanium oxide pigments, silicone-treated titanium oxide, 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 mixtures thereof.

[0272] According to a particular embodiment, compositions C1 to C5 according to the invention are free of inorganic UV filters.

[0273] According to a particular embodiment, the amount of inorganic UV filters present in the compositions according to the invention may range from 0.01% to 20% by weight relative to the total weight of the compositions C1 to C5 that contain them, for example from 1% to 15% by weight relative to the total weight of the composition.

[0274] According to a particular embodiment, at least one of the compositions C1 to C5 according to the invention may also comprise one or more organic UV filters and one or more inorganic UV filters.

[0275] According to a particular embodiment, the composition according to the invention comprises a combination of UV filters as described in patent FR 2977490, patent application WO 2013 / 004777 or patent application US 2014 / 0134120.

[0276] Preferably, the methods and compositions C1, C2, C3, C4 or C5 for treating keratinous materials, in particular skin, use or contain one or more colorants, preferably pigments, selected from pigments, direct dyes and mixtures thereof; more preferentially, the pigments of the present invention are selected from carbon black, iron oxides, in particular yellow, red and black iron oxides and iron oxide-coated mica, triarylmethane pigments, in particular blue and purple triarylmethane pigments, such as Blue 1 Lake, azo pigments, in particular red azo pigments, such as D&C Red 7, alkali metal salts of lithol red, for example calcium salt of lithol red B, and even more preferentially red iron oxides, yellow iron oxides and azo pigments, in particular red azo pigments, such as D&C Red 7.

[0277] Advantageously, the method for treating keratinous materials is in particular a method for making up the skin, in particular a method for making up the lips, mascara, eyeliner, eyeshadow or foundation.

[0278] iv) Fatty phase - fatty substances According to a particular embodiment, the method of the invention makes use of one or more fatty substances, in particular one or more oils, preferably volatile oils.

[0279] More particularly, in the method of the invention, at least one of the compositions C1, C2, C3, C4 or C5 used in the method of the invention comprises a fatty phase.

[0280] In particular, at least one of the compositions C1, C2, C3, C4 or C5 used in the method of the invention comprises one or more fatty substances, in particular one or more oils, preferably volatile oils.

[0281] The term "oil" refers to a fatty substance that is liquid at room temperature (20°C) and atmospheric pressure (760 mmHg).

[0282] The term "hydrocarbon-based oil" means an oil that is essentially formed from or further consists of carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and does not contain silicon or fluorine atoms, and may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0283] According to one embodiment of the present invention, the oil is a volatile oil, in particular *Hydrocarbon oils containing 8 to 16 carbon atoms, especially - Branch C8~C 16 Alkanes, such as isoalkanes, e.g., C 13 ~C 16 isoalkanes (also known as isoparaffins), such as isoparaffins, isododecane, isodecane, isohexadecane, and oils sold, alone or in mixtures, for example, under the trade names Isopar or Permethyl, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), more preferentially isododecane; - linear alkanes, such as C alone or as a mixture 11 ~C 16 Alkanes, such as hexane, decane, undecane, tridecane, isoparaffins, etc., or n-dodecane (C12) and n-tetradecane (C14), undecane-tridecane mixtures, mixtures of n-undecane (C11) and n-tridecane (C13) and mixtures thereof, and mixtures of n-undecane (C11) and n-tridecane (C13); - Volatile non-aromatic cyclic C5-C 12 Alkanes; *Short-chain esters containing a total of 3 to 8 carbon atoms, such as methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate or isobutyl acetate; * carbonate hydrocarbon-based oils having 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 chosen from dibutyl carbonate or dipentyl carbonate; * ether oils having 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; * In particular silicone oils containing 2 to 7 silicon atoms, optionally containing alkyl or alkoxy groups containing 1 to 10 carbon atoms, such as dimethicone with a viscosity of 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and mixtures thereof. More preferentially, the volatile oil b) is selected from the group consisting of C8 to C 16 It is selected from alkanes, especially branched alkanes such as isododecane.

[0284] In particular, at least one of the compositions C1, C2, C3, C4 or C5 used in the method according to the invention comprises one or more non-volatile oils chosen in particular from: * non-volatile fluorinated oils, in particular those selected from fluorinated polyethers and fluorosilicone oils, fluorosilicones; *Non-volatile silicone oils, in particular those chosen from the non-volatile silicones with the following INCI names: dimethicone, dimethiconol, trimethylpentaphenyltrisiloxane, tetramethyltetraphenyltrisiloxane, diphenyldimethicone, trimethylsiloxyphenyldimethicone, phenyltrimethicone, diphenylsiloxyphenyltrimethicone; and mixtures thereof; * Non-volatile apolar hydrocarbon oils, in particular those 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 Mixtures of hydrocarbons, e.g., those with INCI names (C 15 ~C19 ) alkanes, (C 18 ~C 21 ) alkanes, (C 21 ~C 28 ) mixtures of alkanes, iv) hydrogenated or non-hydrogenated polybutenes; v) hydrogenated or non-hydrogenated, preferably hydrogenated polyisobutenes, vi) hydrogenated or non-hydrogenated polydecenes, vii) decene / butene copolymers, butene / isobutene copolymers and viii) mixtures thereof; *Non-volatile polar hydrocarbon-based oils that may be selected from: i) Saturated, unsaturated, linear or branched C 10 ~C 26 Fatty alcohols, preferably monoalcohols; advantageously C 10 ~C 26 The alcohols are fatty alcohols, preferably branched, if they contain at least 16 carbon atoms; preferably, the fatty alcohols contain from 10 to 24 carbon atoms, more preferentially from 12 to 22 carbon atoms, in particular lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyloctanol, 2-undecylpentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol, etc., and mixtures thereof; ii) In particular, the fatty acids are C4 to C 36 range, especially C 18 ~C 36triglycerides consisting of fatty acid esters of glycerol, which may have chain lengths in the range of 0 to 100 rpm, and which may be linear or branched and saturated or unsaturated; examples thereof include, in particular, heptanoic or octanoic acid triglycerides, caprylic / capric triglyceride; wheat germ oil, sunflower oil, grape seed oil, sesame seed oil, corn oil, apricot kernel oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, almond oil, palm oil, Vegetable oils such as rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy seed oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, rose moschata oil, peanut oil, palm oil, argan oil, passionflower oil, kaya oil; the liquid fraction of shea butter, the liquid fraction of cocoa butter; and mixtures thereof; iii) linear aliphatic hydrocarbon 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 chain containing 1 to 40 carbon atoms, aliphatic hydrocarbon esters of alkylene glycols, in particular ethylene glycol or propylene glycol; the total number of carbon atoms is advantageously at least 10; in particular isoamyl laurate, cetostearyl octanoate, isopropyl myristate, isopropyl palmitate, stearic acid or isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, octanoates, decanoates or ricinoleates of alcohols or polyalcohols, for example propyl ethylene glycol dioctanoate, cetyl or tridecyl octanoate, 2-ethylhexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol bis(2-ethylhexanoate) and mixtures thereof, hexyl laurate, neopentanoic acid esters such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate or 2-octyldodecyl neopentanoate, isononanoic acid esters such as 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, such as polyglyceryl-2 triisostearate; v) aromatic esters, such as tridecyl trimellitate, C 12 ~C 15 Alcohol benzoate, 2-phenylethyl ester of benzoic acid and butyloctyl salicylate; vi) linear fatty acid esters having a total carbon number ranging from 35 to 70, such as pentaerythrityl tetrapelargonate; vii) C 24 ~C 28Esters of branched fatty acids or fatty alcohols, such as 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, such as those with the INCI names dilinoleic acid / butanediol copolymer or dilinoleic acid / propanediol copolymer; polyesters obtained by condensation of fatty acid dimers with diol dimers, such as dimer dilinoleyl dimer dilinoleate; ix) synthetic ethers containing 10 to 40 carbon atoms, such as dicaprylyl ether; x) dialkyl carbonates, in which the two alkyl chains are optionally the same or different, such as dicaprylyl carbonate; xi) vinylpyrrolidone copolymers, such as (vinylpyrrolidone / 1-hexadecene) copolymer; and xii) mixtures of these; * Non-volatile carbonate oils are of 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 , with priority given to C6~C 10 representing an alkyl chain), this carbonate 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 of the formula R1-O-R2, known as non-volatile ether oils, 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 12represents an alkyl group). In some cases, it is preferable that R1 and R2 are the same. Examples of linear alkyl groups include a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, a behenyl group, a docosyl group, a tricosyl group, and a tetracosyl group. Examples of branched alkyl groups include a 1,1-dimethylpropyl group, a 3-methylhexyl group, a 5-methylhexyl group, an ethylhexyl group, a 2-ethylhexyl group, a 5-methyloctyl group, a 1-ethylhexyl group, a 1-butylpentyl group, a 2-butyloctyl group, an isotridecyl group, a 2-pentylnonyl group, a 2-hexyldecyl group, an isostearyl group, a 2-heptylundecyl group, a 2-octyldodecyl group, a 1,3-dimethylbutyl group, a 1-(1-methylethyl)-2-methylpropyl group, a 1,1,3,3-tetramethylbutyl group, a 3,5,5-trimethylhexyl group, a 1-(2-methylpropyl)-3-methylbutyl group, a 3,7-dimethyloctyl group, and a 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group. Cyclic alkyl groups include 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, cetyl isobutyl ether, and mixtures thereof; More preferentially, c) the non-volatile oil is hydrogenated or non-hydrogenated, preferably hydrogenated polyisobutene, such as the non-volatile compounds of the Parleam® series; 15 ~C 19 It is selected from a mixture of alkanes and linear aliphatic hydrocarbon esters of the formula RC(O)-OR' as defined above, where RC(O)-O represents a carboxylic acid residue containing from 2 to 40 carbon atoms and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, in particular isononyl nonanoate.

[0285] Very preferentially, the process of the invention is carried out on one or more hydrocarbon-based oils containing from 8 to 16 carbon atoms, in particular branched C8-C, alone or in mixtures. 16 Alkanes, such as isoalkanes, e.g., C 13 ~C 16 Isoparaffin, isododecane, isodecane, isohexadecane, preferably isododecane, is used.

[0286] In particular, the amount of at least one oil in the composition C1, C2, C3, C4 or C5 used in the method is between 1% and 99% by weight, more particularly between 10% and 90% by weight, preferentially between 25% and 75% and better still between 30% and 70% by weight, relative to the total weight of the composition.

[0287] Composition: According to one embodiment, the method for treating keratinous materials uses water, and the compositions C1 to C5 used in the method of the invention comprise water.

[0288] According to an advantageous variant, C1 is aqueous or aqueous-alcoholic.

[0289] According to an advantageous variant, C2 is aqueous or aqueous-alcoholic.

[0290] According to an advantageous variant, C3 is aqueous or aqueous-alcoholic.

[0291] According to an advantageous variant, C4 is aqueous or aqueous-alcoholic.

[0292] According to an advantageous variant, C5 is aqueous or aqueous-alcoholic.

[0293] According to another particular embodiment of the present invention, C1 is an anhydrous composition. According to another variant, C2 is anhydrous. According to another variant, C3 is anhydrous. According to yet another particular variant, C4 is anhydrous. According to another variant, C5 is anhydrous. In particular, C1 and / or C4 are anhydrous. In particular, C4 is anhydrous and comprises at least one oil, in particular a volatile oil such as isododecane.

[0294] Compositions C1 to C5 used in the method of the present invention may also contain one or more organic solvents.

[0295] The term "organic solvent" means an organic substance that can dissolve other substances without chemically altering them.

[0296] Examples of organic solvents that may be mentioned include a) C2-C6 alkanols, such as ethanol and isopropanol; b) polyols that are miscible with water at room temperature (25°C), in particular those selected 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; c) polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether or diethylene glycol monomethyl ether; and d) aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0297] According to a particular embodiment, the composition also comprises one or more polyols, in particular chosen from polyols, in particular polyols containing from 2 to 10 carbon atoms, preferably from 2 to 6 carbon atoms, such as glycerol.

[0298] In particular, compositions C1, C2, C3, C4 or C5 (preferably C2 or C3) are aqueous or aqueous-alcoholic (in particular ethanol / water mixtures in a volume ratio of 1 / 99 to 99 / 1, more particularly 10 / 90 to 90 / 10, even more particularly 20 / 80 and 80 / 20, preferably 40 / 60 to 60 / 40, for example 50 / 50).

[0299] Compositions C1, C2, C3, C4 or C5 may be in the form of anhydrous, water-in-oil emulsion or oil-in-water emulsion.

[0300] adjuvants Compositions C1, C2, C3, C4 or C5 used in the methods of the present invention may also comprise one or more adjuvants selected from fragrances, preservatives, fillers, free radical scavengers, polymers, thickeners or film formers, surfactants, trace elements, emollients, sequestering agents and propellants.

[0301] Another subject of the present invention is a composition C1, preferably aqueous or aqueous-alcoholic, comprising i) at least one compound of formula (I) or (Ia), iii) optionally at least one active agent as defined above, preferably at least one colorant, such as at least one pigment as defined above, and optionally iv) one or more fatty substances as defined above.

[0302] Another subject of the invention is a composition C2, preferably aqueous or aqueous-alcoholic, comprising i) at least one compound of formula (I) or (Ia) as defined above, ii) at least one crosslinking agent as defined above, iii) optionally at least one active agent as defined above, and optionally iv) one or more fatty substances as defined above.

[0303] Another subject of the invention is a composition C3, preferably aqueous or aqueous-alcoholic, comprising i) at least one compound of formula (I) or (Ia) as defined above, ii) at least one crosslinking agent as defined above, iii) at least one active agent as defined above and, optionally, iv) one or more fatty substances as defined above.

[0304] Another subject of the present invention is the cosmetic use of a composition C1, C2 or C3 comprising iii) one or more cosmetic active agents as defined above and, optionally, iv) one or more fatty substances as defined above, in particular for treating keratinous materials, in particular for making up keratinous materials, in particular the skin, such as the lips, eyelashes or eyebrows.

[0305] kit According to yet another of its aspects, the present invention relates to a multi-compartment kit or device, in particular a cosmetic kit or device for caring for and / or making up keratinous substances, in particular the skin and / or the lips, eyelashes or eyebrows, comprising: - at least one compartment containing i) at least one component of formula (I) or (Ia) as defined above and, optionally, iii) at least one cosmetic active agent, in particular a composition C1 as defined above; - at least one compartment different from the compartment containing i) and containing ii) at least one crosslinking agent as defined above and, optionally, iii) at least one cosmetic active agent, in particular containing composition C4; - optionally at least one compartment different from the compartments comprising i) and ii), and iii) containing at least one cosmetic active agent identical or different from the cosmetic active agent optionally contained in the compartments defined above comprising i) and ii), in particular containing composition C5; The present invention relates to a kit comprising:

[0306] The invention is explained in more detail in the following examples, in which amounts are expressed as percentages by weight. [Example]

[0307] Compound 1: KFLEX 7301 available from King Industries [ka]

[0308] Compound 2: Glucose containing acetoacetate groups (5 eq) Compound 2 was synthesized according to the following scheme. [ka] (In the scheme, R1 may be the same or different and represent a hydrogen atom or a -methylcarbonylmethylcarbonyl group -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 groups represent -C(O)-CH2-C(O)-CH3).

[0309] 100 g of D-glucose and 482.90 g of tert-butyl acetoacetate are placed in a 1-liter three-neck flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated for 5 hours using an oil bath (oil bath temperature 140-150 °C). After 5 hours, NMR confirms that the acetoacetate groups have been grafted. The reaction medium is then concentrated at 150 °C using a rotary evaporator under continuous vacuum. A very viscous, dark brown liquid is obtained, whose analysis corresponds to the expected product.

[0310] Compound 3: Mannose containing acetoacetate groups (5 eq) Compound 3 was synthesized according to the following scheme. [ka] (In the schemes, R1 may be the same or different and represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 groups represent -C(O)-CH2-C(O)-CH3).

[0311] 100 g of D-mannose and 482.90 g of tert-butyl acetoacetate are placed in a 1-liter three-neck flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated for 5 hours using an oil bath (oil bath temperature 140-150 °C). After 5 hours, NMR confirms that the acetoacetate groups have been grafted. The reaction medium is then concentrated at 150 °C using a rotary evaporator under continuous vacuum. A viscous yellow liquid is obtained, whose analysis corresponds to the expected product.

[0312] Compound 4: Xylitol containing acetoacetate groups (5 eq) Compound 4 was synthesized according to the following scheme. [ka] (In the schemes, R1 may be the same or different and represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 groups represent -C(O)-CH2-C(O)-CH3).

[0313] 25 g of xylitol and 142.69 g of tert-butyl acetoacetate are placed in a 500 ml three-neck flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated using an oil bath (oil bath temperature 140-150 °C) for 5 hours. After 5 hours, NMR confirms that the acetoacetate groups have been grafted. The reaction medium is then concentrated at 150 °C using a rotary evaporator under continuous vacuum. A very viscous brown liquid is obtained, whose analysis corresponds to the expected product.

[0314] Compound 5: Sorbitol containing acetoacetate groups (6 eq) Compound 5 was synthesized according to the following scheme. [ka] (In the schemes, R1 may be the same or different and represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 groups represent -C(O)-CH2-C(O)-).

[0315] 100 g of sorbitol and 573.20 g of tert-butyl acetoacetate are placed in a 1-liter three-neck flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated for 5 hours using an oil bath (oil bath temperature 140-150 °C). After 5 hours, NMR confirms that the acetoacetate groups have been grafted. The reaction medium is then concentrated at 150 °C using a rotary evaporator under continuous vacuum. A viscous yellow-orange liquid is obtained, whose analysis corresponds to the expected product.

[0316] Compound 6: Sorbitol containing acetoacetate groups (3 eq) Compound 6 was synthesized according to the following scheme. [ka] (In the schemes, R1 may be the same or different and represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 groups represent -C(O)-CH2-C(O)-CH3).

[0317] 100 g of sorbitol and 260.54 g of tert-butyl acetoacetate are placed in a 1-liter three-neck flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated using an oil bath (oil bath temperature 140-150 °C) for 5 hours. After 5 hours, NMR confirms that the acetoacetate groups have been grafted. The reaction medium is then concentrated at 150 °C using a rotary evaporator under continuous vacuum. A viscous yellow liquid is obtained, whose analysis corresponds to the expected product.

[0318] Compound 7: Dipentaerythritol containing acetoacetate groups (6 eq) Compound 7 was synthesized according to the following scheme. [ka] (In the schemes, R1 may be the same or different and represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 groups represent -C(O)-CH2-C(O)-CH3).

[0319] 50 g of dipentaerythritol and 195.33 g of tert-butyl acetoacetate are placed in a 1-liter three-neck flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated for 4 hours using an oil bath (oil bath temperature 140-150 °C). After 4 hours, NMR confirms that the acetoacetate groups have been grafted. The reaction medium is then concentrated at 150 °C using a rotary evaporator under continuous vacuum. A viscous orange-brown liquid is obtained, whose analysis corresponds to the expected product.

[0320] Compound 8: Sucrose containing acetoacetate groups (8 eq) Compound 8 was synthesized according to the following scheme. [ka] (In the schemes, R1 may be the same or different and represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 groups represent -C(O)-CH2-C(O)-CH3).

[0321] 100 g of sucrose and 406.55 g of tert-butyl acetoacetate are placed in a 1-liter three-neck flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated using an oil bath (oil bath temperature 140-150 °C) for 4 hours. After 4 hours, NMR confirms that the acetoacetate groups have been grafted. The reaction medium is then concentrated at 150 °C using a rotary evaporator under continuous vacuum. A viscous orange-yellow liquid is obtained, whose analysis corresponds to the expected product.

[0322] [Table 11]

[0323] [Table 12]

[0324] Implementation of the invention 1 Action applied: Compounds 1-6 of formula (I) containing acetoacetate groups and crosslinkers 1-10 are mixed and then applied to Bioskin artificial skin (Bioskin plate #10) from MapreCos (a skin-equivalent elastic support). The system remains fluid long enough for application to a substrate. After application to the Bioskin artificial skin and evaporation of the volatile solvent, a coating is obtained that is transfer-resistant, non-greasy, and resistant to food oils, sebum, and water.

[0325] Two-step application: Apply base coat A followed by top coat A or apply base coat B followed by top coat B. A "base coat" type composition containing a compound with acetoacetate groups is prepared using a Speed ​​Mixer (3500 rpm for 2 minutes). This "base coat" is then applied to a Bioskin type in vitro support (elastic support simulating skin) using a film coater (wet thickness 100 μm). The coating is allowed to dry naturally for 24 hours.

[0326] A "topcoat" composition containing a crosslinking agent is then applied, and after drying for 24 hours, the resulting coating is evaluated.

[0327] Base coat A: a coating of compounds 1 to 6 containing acetoacetate groups, either on their own or diluted in a volatile solvent such as ethanol, water, isododecane or isododecane / ethanol mixtures or ethanol / water mixtures. Optionally, a crosslinking agent can be introduced into this phase to carry out pre-crosslinking. or Base coat B: Coatings of crosslinkers 1-10. Topcoat A: A coating containing crosslinkers 1-10. or Topcoat B: A coating of compounds 1-6 containing acetoacetate groups, either on their own or diluted in a volatile solvent such as ethanol, water, isododecane or isododecane / ethanol mixtures or ethanol / water mixtures.

[0328] A base coat composition containing acetoacetate group-containing compounds 1 to 6 (Base Coat A) or a base coat composition containing crosslinkers 1 to 10 (Base Coat B) was applied to Bioskin-type vitro support using a film coater (wet thickness 100 μm). The coating was allowed to dry naturally for 24 hours.

[0329] After evaporation of the volatile solvent, the newly formed material makes it possible to obtain a coating that is transfer-resistant, non-greasy, resistant to edible oils, sebum and water when applied to the skin.

[0330] Resistance to adhesive tape A strip of adhesive tape (SCotCh® MagicC from 3M) TM A strip of adhesive tape (810; w=19 mm, L=5 cm) is applied to the coating. A weight of approximately 1070 g is placed on the strip of adhesive tape for 30 seconds. The strip of adhesive tape is then removed and attached to a slide holder so that the results can be properly observed. In this way, the adhesion of the coating to the support is evaluated.

[0331] Resistant to olive oil, water and sebum 0.5 ml of olive oil or water is applied to the film of the formulation. After 5 minutes, the olive oil, water or sebum is removed by wiping 15 times with cotton wool. In this way, the deterioration of the film after contact with the erosive agent droplets is evaluated.

[0332] Fracture testing of formulations on BioSkin For the olive oil and adhesive tape resistance tests, the films are applied to BioSkin test strips. After drying for one day, the BioSkin plates are peeled off by hand 10 times.

[0333] The results can then be observed on the coating of the formulation (fracture or otherwise).

[0334] After the base coat alone had dried and after the base coat + top coat system had dried, each combination was evaluated. The evaluation was carried out as follows: +++: Cosmetic properties are rated as very effective ++: Cosmetic properties are rated as moderately effective +: Cosmetic properties are not considered to be very effective 0: Cosmetic properties are rated as ineffective

[0335] Resistant to olive oil, sebum and water 0.5 mL of olive oil or water is applied to the coating. After 5 minutes, the olive oil or water is removed by wiping 15 times with cotton wool. In this way, the deterioration of the coating due to contact with olive oil or water is observed. The resistance is evaluated according to the following scale: +++: the coating is not eroded and remains intact; ++: slight color transfer, but coating remains intact; +: The coating has changed slightly, and some color transfer is observed; 0: The coating is completely deteriorated and the color has transferred considerably to the absorbent cotton.

[0336] Example 1: Compound 1 - 1 working with an ACAC group in combination with amino crosslinker 1 in ethanol

[0337] [Table 13]

[0338] 1Result of applying the action.

[0339] [Table 14]

[0340] It can be seen that when composition A is applied according to the method of the invention, the resistance to olive oil, sebum and water is significantly improved, and in addition, the destructive test results are significantly better than those of the reference composition A°.

[0341] Example 2: Molecules 1-1 crosslinked with amino crosslinker 1 in isododecane / ethanol

[0342] [Table 15]

[0343] 1Result of applying the action.

[0344] [Table 16]

[0345] It can be seen that application of Composition B according to the method of the present invention provides very effective cosmetic properties.

[0346] Example 3: Compound 1-1 behavior in conjunction with amino crosslinker 2 in aqueous-alcoholic media

[0347] [Table 17]

[0348] 1Result of applying the action.

[0349] [Table 18]

[0350] It can be seen that application of composition C according to the method of the invention provides very effective resistance to water, olive oil and sebum.

[0351] Example 4: Compound 6 containing ACAC groups in combination with polyacrylate crosslinker 8 + catalyst - 1 operation

[0352] [Table 19]

[0353] 1Result of applying the action.

[0354] [Table 20]

[0355] It can be seen that when composition D is applied according to the method of the invention, the resistance to olive oil and water is significantly improved, and in addition, the adhesive tape test and the destructive test give significantly better results than the reference composition D°.

[0356] Example 5: Compound 6 - 1 operation in combination with dicarbonyl crosslinker 9 + catalyst

[0357] [Table 21]

[0358] 1Result of applying the action.

[0359] [Table 22]

[0360] Application of composition E according to the method of the present invention provides very effective olive oil resistance and is also found to be very effective against adhesive tape and puncture tests.

[0361] Example 6: Compound 3-2 containing ACAC groups using amino crosslinker 3 followed by amino crosslinker 6

[0362] [Table 23]

[0363] [Table 24]

[0364] The result of applying one action or two actions.

[0365] [Table 25]

[0366] It can be seen that applying compositions F and then G in two steps according to the method of the invention gives a very effective resistance to olive oil and sebum, which is also effective in the adhesive tape test and the destructive test.

[0367] Example 7: Compound 3-2 containing ACAC groups using amino crosslinker 3 followed by amino crosslinker 4

[0368] [Table 26]

[0369] [Table 27]

[0370] 2 Results of applying the action.

[0371] [Table 28]

[0372] It can be seen that applying compositions F and then H in two movements according to the method of the invention provides effective resistance to olive oil and sebum, as also seen in the destructive tests.

[0373] Example 8: Compound 3-2 containing ACAC groups using amino crosslinker 3 followed by thiol crosslinker 7 This method was carried out in the same manner as in Example 7, except that the second run was carried out using composition I instead of composition H, and the first run was carried out using composition F.

[0374] [Table 29]

[0375] 2 Results of applying the action.

[0376] [Table 30]

[0377] Example 9: Compounds 1-2 containing ACAC groups worked with amino crosslinker 3 followed by amino crosslinker 3

[0378] [Table 31]

[0379] [Table 32]

[0380] [Table 33]

[0381] Results of applying action 1 and action 2.

[0382] [Table 34]

[0383] It can be seen that the application of compositions J and then K in two passes according to the method of the invention provides resistance to olive oil, sebum and water that is significantly more effective than that obtained with a single pass treatment using composition J°, as also shown in the destructive test and the adhesive tape test.

[0384] Long-lasting gloss Gloss durability test A composition containing an acetoacetate group-containing compound, a crosslinker, and a solvent is applied to a Leneta plate using an applicator to a wet thickness of 100 μm. Using a glossmeter, the gloss of the card is measured at an angle of incidence of 20°, and then the gloss of the coating is measured 2 hours after application and 24 hours after application. Subsequently, 0.5 ml of water is applied to the coating, and after 5 minutes, the gloss of the affected area is measured after wiping with absorbent cotton (15 double strokes).

[0385] Example 10: Compound 1 containing an ACAC group in combination with amino crosslinker 3

[0386] [Table 35]

[0387] [Table 36]

[0388] It can be seen that the gloss of the film effectively persists even after exposure to water or scrubbing.

[0389] Example 11: Compound 7 - 2 containing ACAC groups using amino crosslinker 10 followed by amino crosslinker 6

[0390] [Table 37]

[0391] [Table 38]

[0392] The result of applying one action or two actions.

[0393] [Table 39]

[0394] It can be seen that the application of compositions M and then N in two strokes according to the method of the invention provides resistance to olive oil, sebum and water that is significantly more effective than that obtained with composition M° in one stroke, as also shown in the destructive test and adhesive tape test.

[0395] Example 12: Compound 7-2 containing an ACAC group in combination with amino crosslinker 10 amine followed by amino crosslinker 4 This method was carried out in the same manner as in Example 11, except that the second run was carried out using composition O instead of composition N, and the first run was carried out using composition M.

[0396] [Table 40]

[0397] The result of applying one action or two actions.

[0398] [Table 41]

[0399] It can be seen that the application of compositions M and then O in two strokes according to the method of the invention provides resistance to olive oil, sebum and water that is significantly more effective than that obtained with composition M° in one stroke, as also shown in the destructive test and adhesive tape test.

[0400] Example 13: Compound 7 - 2 containing ACAC groups using amino crosslinker 10 followed by thiol crosslinker 7 This method was carried out in the same manner as in Example 11, except that the second run was carried out using composition P instead of composition N, and the first run was carried out using composition M.

[0401] [Table 42]

[0402] [Table 43]

[0403] It can be seen that the application of compositions M and then P in two strokes according to the method of the invention provides resistance to olive oil, sebum and water that is significantly more effective than that obtained with composition M° in one stroke, as also shown in the destructive test and adhesive tape test.

[0404] Example 14: Compound 7 containing ACAC groups in combination with amino crosslinker 1 - 1 behavior

[0405] [Table 44]

[0406] 1Result of applying the action.

[0407] [Table 45]

[0408] It can be seen that the application of composition Q in one action according to the method of the invention significantly improves the resistance to olive oil and water, and in addition, the adhesive tape test and the destructive test give significantly better results than the reference composition Q°.

[0409] Example 15: Compound 8 containing ACAC groups in combination with amino crosslinker 1 amine in ethanol

[0410] [Table 46]

[0411] 1Result of applying the action.

[0412] [Table 47]

[0413] It can be seen that the application of composition R in one movement according to the method of the invention significantly improves the resistance to olive oil and water, and in addition, the adhesive tape test and the destructive test give significantly better results than the reference composition R°.

[0414] Example 16: Compound 8 - 2, containing an ACAC group, using amino crosslinker 10 amine followed by thiol crosslinker 7 The method was carried out as described in Example 13, except that the first run was carried out using composition S instead of composition M, and the second run was carried out using composition P.

[0415] [Table 48]

[0416] 1Result of applying the action.

[0417] [Table 49]

[0418] It can be seen that the application of compositions S and then P in two strokes according to the method of the invention provides resistance to olive oil, sebum and water that is significantly more effective than that obtained with composition S° in one stroke, as also shown in the destructive test and the adhesive tape test.

[0419] Example 17: Comparison of aqueous polyvinylpyrrolidone / isobornyl acrylate / 2-ethylhexyl acrylate / acetoacetoxyethyl methacrylate dispersion (2 / 59 / 29 / 10) with compounds containing ACAC groups in combination with crosslinker 9 - 1 operation Preparation of aqueous polyvinylpyrrolidone / isobornyl acrylate / 2-ethylhexyl acrylate / acetoacetoxyethyl methacrylate dispersion (2 / 59 / 29 / 10) (Polymer 1) 5 g of poly 1-vinyl-2-pyrrolidinone, 150 g of ethanol, 350 g of water and 1.2 g of KPS initiator are placed in a 1 liter reactor, the medium is degassed with argon and then heated to 80° C. while stirring (150 rpm).

[0420] Once the temperature of the stock solution has reached 80° C., a mixture of 25 g of acetoacetoxyethyl methacrylate, 147.5 g of isobornyl acrylate and 72.5 g of 2-ethylhexyl acrylate is introduced by injection over 1 hour using a controlled pump.

[0421] The polymerization is continued for 7 hours at 80° C. and then cooled to room temperature, and the reaction medium is then stripped by distilling off the ethanol completely.

[0422] Finally, the polymer is in the form of an aqueous dispersion with a solids content (dry extraCt) of 43% by weight relative to the total weight of the aqueous dispersion.

[0423] The polymer in aqueous dispersion is characterized by GPC, the results of which are detailed in the following table.

[0424] [Table 50]

[0425] [Table 51]

[0426] 1Result of applying the action.

[0427] [Table 52]

[0428] The compositions according to the present invention have significantly higher oil resistance than the comparative compositions.

[0429] Example 18: Comparison of aqueous polyvinylpyrrolidone / isobornyl acrylate / 2-ethylhexyl acrylate / acetoacetoxyethyl methacrylate dispersion (2 / 59 / 29 / 10) with compounds containing ACAC groups in combination with crosslinker 8 - 1 run

[0430] [Table 53]

[0431] 1Result of applying the action.

[0432] [Table 54]

[0433] The compositions according to the invention have significantly higher oil and water resistance than the comparative compositions.

Claims

1. Keratin substances, i) Formula (I): 【Chemistry 1】 (In formula (I), -R １ is a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic C ２ ~C １４ represents a polyvalent hydrocarbon group, R １ Also, a) one or more hydroxyl OH or amine -N(R) ２ group (wherein R is a C １ ~C ４ ) alkyl group) or carboxyl -C(O)-OH, optionally substituted with vinyl groups, and / or b) O, S, carbonyl-C(O)-, amine-N(R'), or a combination thereof, where R' is optionally substituted with a hydrogen atom, at least one hydroxyl group (OH), or -X-C(O)-C(R ａ ) (R ｂ )-C(O)-R ２ optionally interrupted by one or more heteroatoms or groups selected from: -R ２ is a linear or branched, saturated or unsaturated C １ ~C ６ Monovalent hydrocarbon-based groups, preferably (C １ ~C ４ ) represents an alkyl group, more preferentially methyl; -R ａ and R ｂ may be the same or different and are hydrogen atoms or (C １ ~C ４ ) represents an alkyl group, preferably hydrogen; X is O, S, N(R') or -S-CH ２ -C(O)-O-, -OC(O)-CH ２ a heteroatom or group selected from —S—, —O—C(O)—N(R′)—, —N(R′)—C(O)—O— or —N(R′)—C(O)—N(R′)—; n represents an integer ranging from 2 to 10, in particular from 3 to 8. and also optical or geometric isomers thereof, salts thereof and solvates thereof, such as hydrates; ii) at least one crosslinker; iii) optionally at least one cosmetic active agent; to the material in one or more steps.

2. The compound of formula (I) has the formula (Ia): 【Chemistry 2】 (In formula (Ia), -R １ is as defined in claim 1 and is in particular a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic C ２ ~C １４ , especially C ３ ~C １２ , preferably C ４ ~C １０ represents a polyvalent hydrocarbon group, R １ Also, a) optionally substituted with one or more hydroxyl groups OH; and / or b) optionally interrupted by one or more heteroatoms or groups selected from O, S, -N(R'), preferably interrupted by one or more oxygen atoms, wherein R' is as defined in claim 1; -R ２ is as defined in claim 1, preferably R ２ is a linear or branched (C １ ~C ６ ) alkyl group, preferably (C １ ~C ４ ) represents an alkyl group, preferably methyl; and n is as defined in claim 1, preferably n represents an integer ranging from 2 to 8. and also optical isomers thereof, geometric isomers thereof, salts thereof and solvates thereof, such as hydrates thereof.

3. The compound of formula (I) or (Ia) is R １ is a linear or branched, unsaturated, monocyclic or bicyclic, preferably monocyclic C ６ ~C ８ represents polyvalent hydrocarbon-based groups and aromatic groups such as phenyl, or R １ is optionally interrupted by one or more heteroatoms or groups selected from O, S, —N(R′), where R′ represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, and preferably interrupted by one or more oxygen atoms; ５ ~C １２ represents a polyvalent hydrocarbon group; preferably, R １ However, in the monosaccharide or polysaccharide unit, in particular, n hydroxyl groups are n -O-C(O)-CH ２ -C(O)-R ２ group (where R ２ and n represents a disaccharide substituted with as defined in claim 1 or 2), or R １ is a linear or branched, saturated or unsaturated, preferably saturated acyclic C ２ ~C １２ , preferably C ３ ~C １０ represents a polyvalent hydrocarbon group; Preferably, R １ However, in the monosaccharide or polysaccharide unit, in particular, n hydroxyl groups are n -O-C(O)-CH ２ -C(O)-R ２ group (where R ２ is as defined above and n is as defined above).

4. 4. The method according to any one of claims 1 to 3, wherein the compound of formula (I) or (Ia) is such that n represents an integer in the range of from 2 to 8, more particularly, n represents an integer in the range of from 3 to 6, more particularly, from 3 to 5.

5. The compound of formula (I) or (Ia) is the following compound: Table 1 Table 2 Table 3 Table 4 Table 5 Table 6 Table 7 Table 8 Table 9 Table 10 (wherein R1 may be the same or different and is a hydrogen atom or —C(O)—CH ２ —C(O)—CH ３ group, and at least two R groups are —C(O)—CH ２ —C(O)—CH ３ and preferably at least three R groups represent -C(O)-CH ２ —C(O)—CH ３ (It is understood that and also optical isomers thereof, salts thereof and solvates thereof, such as hydrates thereof, More preferentially, the compound is selected from (18), (41) and (44), more preferentially from (18), (21), (38), (41), (44) and (50), even better from (21), (38), (41), (44) and (50), even more preferentially from (18), (21), (38), (41) and (44), even better from (21), (38), (41) and (44), advantageously from (18), (21), (41) and (44), more advantageously from (21), (41) and (44). Method according to any one of claims 1 to 4, wherein the compound is selected from (18), (21), (41) and (44),

6. 6. The method according to any one of claims 1 to 5, wherein the crosslinking agent ii) is selected from (poly)amine, (poly)thiol, (poly)carbonyl, (poly)acrylate and / or metal alkoxide compounds and mixtures thereof, preferably selected from (poly)amine, (poly)thiol and (poly)acrylate compounds and mixtures thereof.

7. The crosslinking agent is a) chitosan, for example poly(D-glucosamine), b) polyetherdiamines, in particular polyethylene glycol α,ω-diamine (with amine functions at the chain ends) and 4,7,10-trioxa-1,1-tridecanediamine, c) polyethertriamines, for example polyetheramine (or Jeffamine), d) aminoalkoxysilanes, for example APTES, and e) polydialkylsiloxanes containing primary amine groups at the chain ends or in the side chains, in particular polydimethylsiloxanes containing primary amine groups, for example bis(3-aminopropyl) terminated poly(dimethoxysiloxane) (PDMS-diNH ２ ) and amodimethicones containing an amine group in the side chain, such as biscetearyl amodimethicone; and (poly)amine compounds selected from selected from a) polydialkylsiloxanes containing thiol functional groups and b) alkoxysilanes containing thiol functional groups, in particular a) polydialkylsiloxanes containing thiol functional groups, preferentially polydimethylsiloxanes (such as mercaptopropyl) containing thiol groups in the side chain, in particular those 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) (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 (C １ ~C ６ ) represents an alkyl group; ・R ｄ is (C １ ~C ４ ) alkylamino, or amino, or thiol group-substituted (C １ ~C ６ ) alkyl group, preferably methyl, １ ~C ４ ) alkyl; ・ALK １ represents a linear or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon-based chain containing 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen (especially O), (thio)carbonyl groups C(X) (where X represents O or S or combinations thereof, such as -O-, -O-C(O)- or -C(O)-O-); preferably ALK １ is (C １ ~C ６ ) alkylene, more preferentially (C １ ~C ４ ) represents an alkylene group, for example, propylene; n and m may be the same or different and represent an integer greater than 2, more particularly the values ​​of m and n are such that the weight average molecular weight of the polyorganosiloxane is between 1000 and 55000 g.mol －１ It is as if (Poly)thiol compounds selected from the following: - Formula (XIV): L[-Y-C(O)-C(R ｅ )=CH ２ ｑ (XIV)​ (In formula (XIV), q represents an integer equal to or greater than 2; preferably, n is 2 to 10, preferably 2 to 5 (both inclusive); L represents a linear or branched, saturated or unsaturated or (hetero)cyclic, saturated or unsaturated, polyvalent (at least divalent) group, in particular containing from 1 to 500 carbon and / or silicon atoms, more particularly from 2 to 40 carbon and / or silicon atoms, even more particularly from 3 to 30 carbon and / or silicon atoms, preferably from 6 to 20 carbon atoms; L is O, S, N, Si, C(X) and combinations thereof, such as —O—, —O—C(X)—, —N(R)—C(X)—, —Si(R ｃ ) (R ｄ )-O-(wherein R is a hydrogen atom or a (C １ ~C ６ Optionally interrupted and / or terminated by one or more heteroatoms or groups selected from: L is, -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 oxygen or sulfur atoms or N(R ｂ ) group; a and b are equal to 0 or 1; preferably, the sum of a+b is equal to 1; R ａ and R ｂ may be the same or different and are hydrogen atoms or (C １ ~C ６ ) alkyl or aryl (C １ ~C ４ ) represents an alkyl group, such as benzyl, preferably R ａ and R ｂ represents a hydrogen atom) optionally substituted with one or more groups selected from 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 a (C １ ~C ４ ) alkyl group; preferably, R ｅ represents a hydrogen atom; and Y represents an oxygen atom or an amino group -N(H)-, preferably O as defined above, preferably Y=O, and R ｅ =H, preferably L represents a di- or trivalent, preferably trivalent, hydrocarbon-based chain containing 1 to 8 carbon atoms, q is 2 or 3, preferably 3, Y represents O, and R ｅ represents a hydrogen atom) (Poly)acrylate The method according to any one of claims 1 to 6, wherein the compound of formula (XIV) is selected from the group consisting of:

8. iii) The method according to any one of claims 1 to 7, wherein one or more cosmetic agents are used, selected from a) coloring materials such as pigments, direct dyes and mixtures thereof, b) active agents for caring for keratin substances, preferably the skin, c) UV filters, and d) mixtures thereof; preferably, the at least one cosmetic agent is selected from coloring materials, preferably selected from pigments, direct dyes and mixtures thereof; more preferentially, the 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, such as Blue 1 Lake, azo pigments, in particular red azo pigments, such as D&C Red 7, alkali metal salts of lithol red, for example calcium salt of lithol red B, and even more preferentially red iron oxides, yellow iron oxides and azo pigments, in particular red azo pigments, such as D&C Red 7.

9. iv) A method according to any one of claims 1 to 8, in which one or more fatty substances are used, in particular one or more oils, preferably volatile oils.

10. iv) *Hydrocarbon-based oils containing 8 to 16 carbon atoms, in particular - Branched C alone or in mixtures ８ ~C １６ Alkanes, such as isoalkanes, e.g., C １３ ~C １６ isoparaffins, isoalkanes, isododecane, isodecane and isohexadecane, preferably isododecane and more preferentially isododecane; - linear alkanes, alone or in mixtures, e.g. C １１ ~C １６ Alkanes, such as hexane, decane, undecane, tridecane, isoparaffins, etc., or n-dodecane (C12) and n-tetradecane (C14), undecane-tridecane mixtures, mixtures of n-undecane (C11) and n-tridecane (C13) and mixtures thereof, and also mixtures of n-undecane (C11) and n-tridecane (C13); - volatile non-aromatic cyclic C ５ ~C １２ Alkanes; *short-chain esters containing a total of 3 to 8 carbon atoms, such as ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate; *Structure R', advantageously chosen from dibutyl carbonate or dipentyl carbonate １ -O-C(O)-OR' ２ (In the formula, R' １ and R' ２ are independently linear, branched or cyclic C ４ ~C ８ Alkyl group, preferably C ４ ~C ８ a carbonate hydrocarbon oil in which the alkyl group is a carboxylic acid or a carboxylic acid; *Formula R １ -O-R ２ (In the formula, R １ and R ２ are independently linear, branched or cyclic C ４ ~C ８ Alkyl group, preferably C ４ ~C ８ alkyl group); * In particular silicone oils containing 2 to 7 silicon atoms, optionally containing alkyl or alkoxy groups containing 1 to 10 carbon atoms, such as dimethicone with a viscosity of 5 and 6 CSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and mixtures thereof. and more preferentially, said volatile oil iv) is selected from C ８ ~C １６ The method according to any one of claims 1 to 9, wherein the alkanes are selected from alkanes, in particular branched alkanes such as isododecane.

11. In particular for caring for and / or making up the skin, lips, eyelashes and / or eyebrows, a composition designated "C1" comprising i) at least one compound of formula (I) or (Ia) according to any one of claims 1 to 5 and, optionally, iii) at least one cosmetic active agent according to claim 1 or 8; a composition designated "C2" comprising i) at least one compound of formula (I) or (Ia) according to any one of claims 1 to 5, ii) at least one crosslinking agent according to any one of claims 1, 6 or 7, and optionally iii) at least one activator according to claim 1 or 8; a composition designated "C3" comprising i) at least one compound of formula (I) or (Ia) according to any one of claims 1 to 5, ii) at least one crosslinking agent according to any one of claims 1, 6 or 7, and iii) at least one cosmetic active agent according to claim 1 or 8; and / or a composition "C4" comprising ii) at least one crosslinking agent according to any one of claims 1, 6 or 7 and, optionally, iii) at least one cosmetic active agent according to claim 1 or 8; - iii) a composition "C5" comprising at least one cosmetic active agent according to claim 1 or 8 and as described below. using; - the method comprises the use of i) at least one compound of formula (I) or (Ia) according to any one of claims 1 to 5, together or separately, and ii) at least one crosslinker according to any one of claims 1, 6 or 7; and The method according to any one of claims 1 to 10, it being understood that compositions C1, C2, C3, C4 and C5 may be anhydrous, aqueous, such as aqueous-alcoholic, and / or may comprise one or more fatty substances iv) according to claim 9 or 10.

12. 12. The method according to claim 11, carried out in one operation by applying the composition C2 or C3 according to claim 11 to the keratinous materials.

13. 12. The method according to claim 11, which is carried out in two operations by successively applying to the keratinous material two different compositions, for example C1 and C4, or C2 and C4, or C3 and C4, preferably C1, then C4, C2, then C4 or C3, then C4, as described in claim 11.

14. The keratinous material comprises α) composition C1 according to claim 11, then β) composition C4, then γ) composition C5, preferably C1, then C4 or C5, respectively, then C5 or C4, respectively; or α) composition C4, and β) composition C1 or C2, and then γ) composition C5 according to claim 11 12. The method according to claim 11, wherein the composition C4 is applied before the composition C1 in three successive steps.

15. 1. A method for making up keratinous materials, in particular the skin, in particular the lips, eyelashes or eyebrows, said method comprising: - composition C1 according to claim 11; Next, composition C4 according to claim 11; wherein compositions C1 and / or C4 contain at least one colorant, preferably at least one pigment, according to claim 8; more preferentially, it is understood that composition C1 contains at least one pigment; or the method comprises: - composition C1 according to claim 11; Next, - composition C4 according to claim 11; Next, composition C5 according to claim 11; 14. The method according to claim 11 or 13, comprising the sequential application of compositions C1, C4 and / or C5, which contain at least one colorant, preferably at least one pigment, according to claim 8; more preferentially, it is understood that composition C5 contains at least one pigment.

16. Composition C1 according to claim 11, which is preferably aqueous or aqueous-alcoholic, comprising i) at least one compound of formula (I) or (Ia) according to any one of claims 1 to 5, iii) optionally at least one active agent, preferably at least one colorant, such as at least one pigment, according to claim 1 or 8; and optionally iv) one or more fatty substances according to claim 9 or 10.

17. Composition C2 according to claim 11, which is preferably aqueous or aqueous-alcoholic, comprising i) at least one compound of formula (I) or (Ia) according to any one of claims 1 to 5, ii) at least one crosslinking agent according to any one of claims 1, 6 or 7, iii) optionally at least one active agent according to claim 1 or 8; and optionally iv) one or more fatty substances according to claim 9 or 10.

18. Composition C3 according to claim 11, comprising iii) one or more cosmetic active agents according to claim 1 or 8, and optionally iv) one or more fatty substances according to claim 9 or 10.

19. Cosmetic use of a composition C1, C2 or C3 according to any one of claims 16 to 18, in particular for treating keratinous materials, in particular for making up keratinous materials, in particular the skin, for example the lips, eyelashes or eyebrows.

20. A multi-compartment kit, in particular a cosmetic kit, comprising: at least one compartment containing i) at least one component of formula (I) or (Ia) according to any one of claims 1 to 5 and, optionally, at least iii) a cosmetic active agent according to claim 1 or 8, in particular a composition C1 according to claim 11; - at least one compartment different from that containing i) that contains ii) at least one crosslinking agent according to any one of claims 1, 6 or 7, and optionally iii) at least one cosmetic active agent according to claim 1 or 8, in particular a composition C4 according to claim 11; optionally at least one compartment different from that comprising i) and ii), wherein iii) i) at least one compartment containing at least one cosmetic active agent according to claim 1 or 8, which may be the same or different from that optionally contained in said compartment comprising a compound of formula (I) or (Ia) according to any one of claims 1 to 5, and ii) at least one crosslinking agent according to any one of claims 1, 6 or 7; Multi-compartment kits, especially cosmetic kits, comprising:

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