A method for making up keratinous materials comprising the application of at least one acetoacetate polysaccharide compound and a crosslinking agent

Abstract

Title: Process for making up keratin materials comprising the application of at least one acetoacetate polysaccharide compound and a crosslinking agent. Process for making up keratin materials comprising at least the application on said keratin materials of at least two distinct compositions (A) and (B): - said composition (A) comprising i) at least one compound of formula (I) comprising at least two acetoacetate functions; and ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and iv) at least one particulate coloring matter; and said composition (B) comprising at least v) a crosslinking agent selected from (poly)amine compounds, in particular aminoalkylpolyalkoxysilanes, α,Ω-diaminooxaalkanes, chitosanes, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains. Figure for the abridged version: None

Description

Title of the invention: A method for making up keratinous materials comprising the application of at least one acetoacetate polysaccharide compound and a crosslinking agent. Technical field

[0001] The present invention relates more particularly to the cosmetic field of keratinous materials, and especially to that of makeup for the skin and / or lips and / or eyelashes and / or eyebrows. It aims to provide a method for applying makeup to keratinous materials comprising at least the application to said keratinous materials of at least two distinct compositions (A) and (B). The invention also relates to a makeup kit for keratinous materials comprising at least two compositions (A) and (B) packaged separately. Previous technique

[0002] Cosmetic products classically require the implementation of one or more film-forming polymers in order to obtain a quality deposit of these products on keratinous materials, and in particular giving satisfaction to the expectations detailed below.

[0003] Thus, in the field of skin and lip makeup, it is particularly expected that the deposit formed will not transfer upon contact with fingers or clothing.

[0004] It must also exhibit good resistance to water, particularly rain or during showering, as well as to perspiration and sebum, and even to food fats, particularly cooking oils, when this deposit forms on the lips. Furthermore, this deposit must be comfortable and even glossy.

[0005] To achieve this, it is used in makeup products such as mascaras, eyeliners, eyeshadows, and more particularly in their organic and especially oily phases, dispersions of nanometric polymer particles, as a film-forming agent.

[0006] Thus, for example, document FR 2 741 530 proposes, for this purpose, for the temporary coloring of keratin fibers, the use of a dispersion of film-forming polymer particles comprising at least one acid function and at least one pigment dispersed in the continuous phase of said dispersion. The colors obtained by this coloring method are not always satisfactory in terms of permanence, particularly with shampooing. In fact, generally speaking, these polymers do not allow access to deposits on keratin materials that would give satisfaction with all the aforementioned requirements, namely very good water resistance, particularly to hair shampoos, which allow adjustment of shine or invisibility qualities and which, in the case of hair use, provide very satisfactory styling hold.

[0007] Document EP 3 250 177 A1 describes the use of acetoacetylated compounds in the field of keratin fibers. Keratin materials treated with said acetoacetylated compounds do not always give satisfactory results, particularly in terms of resistance to water and shampoos.

[0008] These documents do not allow for obtaining non-sticky deposits, which transfer little, are comfortable, and are persistent. Description of the invention

[0009] There therefore remains a need for cosmetic compositions intended for application on the skin and / or lips and / or eyelashes and / or eyebrows which provide a non-sticky deposit, which transfers little or not at all, is shiny, comfortable, and long-lasting.

[0010] There also remains a need for compositions that are resistant to various mechanical and chemical aggressions, for example makeup-removing compositions such as two-phase waters.

[0011] There also remains a need for compositions that provide qualities of brilliance and color retention.

[0012] The present invention is specifically aimed at meeting all or part of these needs. Summary of the invention

[0013] These problems are solved by implementing a process for making up keratinous materials comprising at least the application to said keratinous materials of at least two distinct compositions (A) and (B): - said composition (A) comprising at least: (i) at least one compound of formula (I) comprising at least two acetoacetate functions, as well as its optical isomers, geometric isomers, salts, and solvates such as hydrates:

[0014] [Chem.l]

[0015] formula (I) in which: - R1 represents a polysaccharide motif, in particular a disaccharide, on which n hydroxy groups have been substituted by n -OC(O)-CH2-C(O)-R2 groups; R1 being further: a) possibly substituted by one or more hydroxyl groups OH, amine -N(R)2 with R representing a (Ci-C4)alkyl group such as methyl, carboxy -C(O)-OH, a vinyl group, and / or b) possibly interrupted by one or more heteroatoms or groups selected from O, S, carbonyl -C(O)-, amine -N(R'), or their combinations such as ester -C(O)-O-, -OC(O)-, amide -C(O)-N(R')-, -N(R')-C(O)-, methane -N(R')-C(O)-O- or -OC(O)-N(R')-, urea -N(R')-(CO)-N(R')-, or carbonate -OC(O)-O-, wherein R' represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms possibly substituted by at least one hydroxyl group (OH), or possibly substituted by -XC(O)-C(Ra)(Rb)-C(O)-R2; preferably R' represents a hydrogen atom, a (Ci-C4)alkyl group; - R2 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably a (CrC4)alkyl group such as methyl or tert-butyl, more preferably methyl; - Ra, and Rb, identical or different, represent a hydrogen atom or a (CrC4)alkyl group, preferably hydrogen; - X is a heteroatom or group chosen from O, S, N(R'), -S-CH2-C(O)-O-, -OC(O)-CH2-S-, -OC(O)-N(R')-, -N(R')-C(O)-O-, -N(R')-C(O)-N(R')-, preferably X represents O; - n denotes an integer from 2 to 10, particularly from 3 to 8; and ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and (iv) at least one particulate coloring matter; - said composition (B) comprising at least v) a crosslinking agent selected from (poly)amine compounds, in particular aminoalkylpolyalkoxysilanes, α,Q-diaminooxaalkanes, chitosanes, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains.

[0016] The inventors have thus found, surprisingly, that the application of ingredients i), ii), iii), iv) and v) to keratinous materials improves the adhesion of the colored deposit to keratinous materials treated with this combination, particularly with regard to liquid fats such as oils and water.

[0017] For the purposes of the present invention, and unless otherwise indicated: - By "cosmetic active ingredient": this refers to an organic or organosilicon compound, or a mineral compound that can be incorporated into a cosmetic composition to have an effect on keratinous materials, whether this effect is immediate or achieved through repeated applications. Examples of cosmetic active ingredients include colored or non-colored, fluorescent or non-fluorescent compounds such as optical brighteners, or UVA and / or UVB filters; anti-aging active ingredients or those intended to provide benefits to the skin such as those acting on the skin barrier function, deodorant active ingredients, antiperspirant active ingredients, desquamating active ingredients, antioxidant active ingredients, moisturizing active ingredients, sebum-regulating active ingredients, active ingredients intended to combat the effects of pollution, antimicrobial or bactericidal active ingredients, perfumes, and coloring materials such as direct dyes or pigments, preferably pigments.

[0018] Preferably the cosmetic actives are chosen from a) colouring materials chosen from pigments, direct colorants, and their mixtures, b) care actives of keratinous materials, preferably of the skin, and c) their mixtures. - By "fatty substance", we mean, for the purposes of the present invention, an organic compound insoluble in water at ordinary temperature (25 °C) and atmospheric pressure (760 mm Hg) (solubility less than 5%, and preferably 1%, even more preferably 0.1%); in addition, fatty substances are soluble in organic solvents under the same conditions of temperature and pressure, such as halogenated solvents such as chloroform, dichloromethane, inferior alcohols such as ethanol or aromatic solvents such as benzene or toluene. - an "aryl" radical represents a mono- or polycyclic hydrocarbon group, condensed or not, comprising 6 to 14 carbon atoms, and of which at least one ring is aromatic; preferably the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl; - a "heteroaryl" radical represents a mono- or polycyclic group, condensed or not, comprising 5 to 14 links, 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and of which at least one ring is aromatic; preferably a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, xanthylyl; - By "(hetero)aryl" we mean the aryl or heteroaryl groups; - By "(hetero)cycloalkyl" we mean cycloalkyl groups or heterocycloalkyl; - The "aryl" or "heteroaryl" radicals, or the aryl or heteroaryl part of a radical, can be substituted by at least one substituent attached to a carbon atom, chosen from:

[0019] * a (poly)(hydroxy)alkyl radical in Ci-C6, preferably in Ci-C4;

[0020] * a halogen atom such as chlorine, fluorine or bromine;

[0021] * a hydroxy group;

[0022] * a C1-C2 alkoxy radical; a C2-C4 (poly)-hydroxyalkoxy radical;

[0023] * an amino radical;

[0024] * an amino radical substituted by one or two alkyl radicals, identical or different, in Ci-C6, Ci-C6, preferably in CrC4;

[0025] * an acylamino radical (-NR-COR') in which the radical R is an atom of hydrogen,

[0026] * an alkyl radical in CrC4 and the radical R' is an alkyl radical in Ci-C4; a radical carbamoyl ((R)2N-CO-) in which the R radicals, identical or not, represent a hydrogen atom, an alkyl radical in CrC4;

[0027] * an alkylsulfonylamino radical (R'SO2-NR-) in which the radical R represents a hydrogen atom, an alkyl radical in CrC4 and the radical R' represents an alkyl radical in CrC4, a phenyl radical;

[0028] * an aminosulfonyl radical ((R)2N-SO2-) in which the R radicals, identical or no, they represent a hydrogen atom, an alkyl radical in CrC4;

[0029] * a carboxylic radical in acidic or sal form (preferably with a metal alkaline or an ammonium, substituted or not);

[0030] * a cyano group (CN);

[0031] * a polyhalogeno(Ci-C4)alkyl group, preferably trifluoromethyl (CF3); - The cyclic or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent attached to a carbon atom chosen from the following groups:

[0032] * hydroxy,

[0033] * C2-C4 alkoxy, (poly)hydroxyalkoxy C2-C4,

[0034] * alkylcarbonylamino ((RCO-NR'-) in which the radical R' is an atonic of hydrogen, * an alkyl radical in C1-C4 and the radical R is an alkyl radical in Ci-C2, amino substituted by one or two identical or different alkyl groups in C1-C4;

[0035] * alkylcarbonyloxy ((RCO-O-) in which the radical R is a C1-C4 alkyl radical, amino substituted by one or two identical or different alkyl groups in C1-C4;

[0036] * alkcoxycarbonyl ((RO-CO-) in which the radical R is a C1-C4 alkyl radical , amino substituted by one or two identical or different alkyl groups in Ci-C4; - a cyclic radical, heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical, can also be substituted by one or more oxo groups; - a hydrocarbon chain is unsaturated when it contains one or more double bonds and / or one or more triple bonds; - an "aryl" radical represents a mono- or polycyclic hydrocarbon group, condensed or not, comprising 6 to 14 carbon atoms, and of which at least one ring is aromatic; preferably the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl; - a "heteroaryl" radical represents a mono- or polycyclic group, condensed or not, comprising 5 to 14 links, 1 to 6 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atoms, and of which at least one ring is aromatic; preferably a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, xanthylyl; - a "cyclic" or "cycloalkyl" radical is a non-aromatic cyclic hydrocarbon radical, mono or polycyclic, condensed or not, containing 5 to 14 carbon atoms, which may have 1 to several unsaturations, preferably the cycloalkyl is a cyclohexyl group; - A "heterocyclic" or "heterocycloalkyl" radical is a non-aromatic mono- or polycyclic cyclic radical, condensed or not, containing 3 to 9 groups, comprising 1 to 4 selected heteroatoms among the nitrogen, oxygen, sulfur and selenium atoms, preferably the heterocycloalkyl is chosen from epoxide, piperazinyl, piperidinyl, morpholinyl, or dithiolane; an "alkyl" radical is a saturated hydrocarbon radical, linear or branched, particularly in C1-C6, preferably in C1-C4; an "alkoxy" radical is an alkyl-oxy radical for which the alkyl radical is a hydrocarbon radical, linear or branched, in C1-C6 preferably in C1-C4; a "(poly)(hydroxy)alkyl" radical designates an alkyl radical in Cr C6, preferably in Ci-C4 possibly substituted by one or more hydroxy radicals, preferably substituted by 1 to 4 hydroxy groups, more particularly between 1 and 3; A "sugar" radical is a monosaccharide or disaccharide radical. Examples of sugar radicals include: sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, or lactose; by "monosaccharide" is meant a monosaccharide sugar comprising at least 5 carbon atoms of formula CX(H2O)X, with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusively between 5 and 7, preferably x = 6, they may be of D or L configuration, and of alpha or beta anomer, as well as their salts and solvates such as hydrates; By "disaccharide" we mean a di-osidic sugar which is a compound consisting of two oses linked together by O-osidic bonds said compounds being made up of two monosaccharides (also called mono-osidics) as defined above said mono-saccharide units comprising at least 5 carbon atoms, preferably 6, particularly the mono-osidic units being linked together in 1,4 or 1,6 in anomer a (alpha) or [3 (beta), each osidic unit being able to be of L or D configuration, as well as its salts and solvates such as the hydrates of said monosaccharides; more specifically, these are polymers formed from two sugars (or monosaccharides) having the general formula: -[Cx(H2O)y )]2- or -[(CH2O)x]2-, with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusively between 5 and 7, preferably x = 6, and y an integer which represents x - 1; By "polysaccharide", we mean a polysaccharide sugar which is a polymer made up of several monosaccharides linked together by O- bonds glycosidic, said polymers being made up of monosaccharide units (also called mono-osidics) as defined above, said mono-saccharide units comprising at least 5 carbon atoms, preferably 6, particularly the mono-osidic units are linked together in 1,4 or 1,6 in anomer a (alpha) or [3 (beta), each glycosidic unit being able to be of L or D configuration, as well as its salts and solvates such as the hydrates of said monosaccharides;more specifically, these are polymers formed from a certain number of sugars (or monosaccharides) having the general formula: -[Cx(H2O)y)]w- or -[(CH2O)X]W-, with x an integer greater than or equal to 5, preferably x greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x = 6, and y an integer representing x - 1, and w is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferably between 10 and 2300, particularly between 15 and 1000 inclusive, more particularly between 20 and 500, preferably between 25 and 200; ; by "salt of organic or mineral acid", more particularly means a) addition salts with a particular organic or mineral acid selected from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; vii) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; viii) of phosphoric acid H3PO4; ix) of triflic acid CF3SO3H and x) of tetrafluoroboric acid HBF4;xi) of organic carboxylic acids R°-C(O)-OH (l'z) formula (Fz) in which R° represents a (hetero)aryl group such as phenyl, (hetero)aryl(Ci-C4)alkyl such as benzyl, or (Ci-Cio)alkyl said alkyl group optionally being substituted preferably by one or more hydroxy groups, amino radicals, or carboxy groups, R° preferably designating a (Ci-C6)alkyl group optionally substituted by 1, 2 or 3 hydroxy groups, or more preferably the monocarboxylic acids of formula (l'z) are chosen from acetic acid, glycolic acid, lactic acid, and mixtures thereof, and more particularly from acetic acid and lactic acid; and the polycarboxylic acids are chosen from tartaric acid, acid; succinic acid, fumaric acid, citric acid and mixtures thereof; and xii) amino acids having more carboxylic acid radicals than amino groups such as gamma-carboxyglutamic acid, aspartic acid, glutamic acid, in particular gamma-carboxyglutamic acid; or b) addition salts with an organic or mineral base such as hydroxides of alkali metals, alkaline earth metals, carbonates of alkali metals or alkaline earth metals, bicarbonates of alkali metals or alkaline earth metals, addition salts with so-called basic amino acids such as arginine, lysine, addition salts with amines possibly hydroxylated; An "anionic counterion" is an anion or anionic group associated with the cationic charge; more particularly, the anionic counterion is chosen from i) halides such as chloride, bromide; ii) nitrates; iii) sulfonates, including the Ci-C6 alkylsulfonates: Alk-S(O)2O such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S(O)2O such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-OS(O)O such as methyl sulfate and ethyl sulfate; x) arylsulfates: Ar-OS(O)O such as benzene sulfate and toluene sulfate; xi) alkoxysulfates: Alk-OS(O)2O such as methoxy sulfate and ethoxysulfate; xii) aryloxysulfates: Ar-OS(O)2O, xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate. The "solvates" represent the hydrates as well as the association with linear or branched C1-C4 alcohols such as ethanol, isopropanol, n-propanol; By "chromophore" we mean a radical derived from a colorless or colored compound capable of absorbing in the UV and / or visible radiation at a wavelength Xabs between 250 and 800 nm; Preferably the chromophore is colored i.e. it absorbs wavelengths in the visible range i.e. preferably between 400 and 800 nm. Preferably chromophores appear colored to the eye; particularly between 400 and 700 nm (Ullmann's Encyclopedia, 2005, Wiley-VcH, Verlag "Dies, General Survey", § 2.1 Basic Principle of Color); A "UV-A filter" is a chromophore made from a compound that filters (or absorbs) UV-A ultraviolet rays at a wavelength between 320 and 400 nm. Short-wave UV-A filters (absorbing the rays at a wavelength between 320 and 340 nm), long UV-A filters (absorbing rays at a wavelength between 340 and 400 nm). - By "UV-B filter" we mean a chromophore made from a compound that filters (or absorbs) UV-B ultraviolet rays at a wavelength between 280 and 320 nm. - By "anhydrous" we mean a quantity of less than 5% by weight of water, preferably less than 3% by weight of water, better less than 1% by weight of water, relative to the total weight of the composition in question Cl, C2, C3 or C4 even more preferably the composition is free of water. - The terms "coloring agent" and "coloring matter" are equivalent;

[0037] Unless otherwise specified, the bounds delimiting the extent of a range of values ​​are included in that range of values.

[0038] Unless otherwise indicated, the quantities shown are expressed as mass percentages. Detailed description

[0039] METHOD FOR MAKING UP KERATINIC MATERIALS

[0040] The first object of the invention is a method of making up keratinous materials, in particular of the skin and / or lips and / or eyelashes and / or eyebrows, comprising at least the application on said keratinous materials of at least two distinct compositions (A) and (B): - said composition (A) comprising at least: (i) at least one compound of formula (I) comprising at least two acetoacetate functions as described above, as well as its optical isomers, geometric isomers, salts, and solvates such as hydrates; ii) at least one monoalcohol comprising 2 to 4 carbon atoms; iii) water; and (iv) at least one particulate coloring matter; - said composition (B) comprising at least v) a crosslinking agent selected from (poly)amine compounds, in particular aminoalkylpolyalkoxysilanes, α,Q-diaminooxaalkanes, chitosanes, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains.

[0041] According to a particular embodiment of the invention, the process of the invention comprises the simultaneous application of ingredients i), v), and iv).

[0042] According to another particular embodiment of the invention, the process comprises at least 2 steps in which ingredients i), and v), and iv), (the latter ingredient being able to be found together with ingredient i) and / or with ingredient(s) v)) are applied in separate and successive stages to keratinous materials, regardless of the order of application.

[0043] According to a particular embodiment, ingredient(s) i) are applied to the keratin materials, then ingredient(s) v) are applied to the keratin materials, it being understood that ingredient(s) iv) may be applied together with i) and / or v).

[0044] According to another particular embodiment, the ingredient(s) v) are applied to the keratin materials, then the ingredient(s) i) are applied to the keratin materials, it being understood that the ingredient(s) iv) may be applied together with i) and / or v).

[0045] According to a particular embodiment, composition (A) and composition (B) are applied simultaneously or sequentially, regardless of the order of application, to the keratinous materials.

[0046] In a preferred embodiment of the invention, a composition obtained by an extemporaneous mixture, at the time of application, of composition (A) and composition (B) as defined above is applied.

[0047] In another embodiment, composition (A) and composition (B) are applied sequentially to the keratinous materials, with composition (A) being applied to the keratinous materials before composition (B) or vice versa. Thus, according to this embodiment, the process according to the invention comprises two successive application steps to said keratinous materials, of composition (A) then composition (B), or of composition (B) then composition (A).

[0048] According to a particular embodiment of the invention, the process of making up keratinous materials is a process of making up the skin, lips, eyelashes and / or eyebrows, preferably of making up the skin, eyelashes and / or eyebrows.

[0049] Compositions (A) and (B) may be anhydrous, aqueous such as hydroalcoholic and / or comprise one or more fatty substances, in particular one or more oils, preferably volatile, as defined below.

[0050] After application of compositions (A) and (B), a permanent, non-sticky colored deposit is advantageously obtained. The deposit obtained is also resistant to oils, water, sebum, and friction.

[0051] According to a particular embodiment, the compositions are applied to dry keratinous materials.

[0052] According to a particular embodiment, the keratin materials are dried after application of compositions (A) and (B), in particular after application of each different composition. i) Compound of formula (I)

[0053] As previously stated, a composition (A) according to the invention comprises at least one compound of formula (I), as well as its optical isomers, geometric isomers, salts, and solvates, such as hydrates:

[0054] [Chem.2]

[0055] formula (I) in which: - R1 represents a polysaccharide motif, preferably a disaccharide; R1 being further: a) possibly substituted by one or more hydroxy groups OH, dialkylamino-N(R)2, with R representing a (Ci-C4)alkyl group, such as methyl, carboxy-C(O)-OH, a vinyl group, and / or b) possibly interrupted by one or more heteroatoms or groups selected from O, S, carbonyl -C(O)-, amine -N(R'), or their combinations such as ester -C(O)-O-, -OC(O)-, amide -C(O)-N(R')-, -N(R')-C(O)-, methane -N(R')-C(O)-O- or -OC(O)-N(R')-, urea -N(R')-(CO)-N(R')-, or carbonate -OC(O)-O-, in which R' represents a hydrogen atom, a linear or branched alkyl group having from 1 to 4 carbon atoms possibly substituted by at least one hydroxyl group (OH), or possibly substituted by -XC(O)-C(Ra)(Rb)-C(O)-R2; preferably R' represents a hydrogen atom, a (Ci-C4)alkyl group; - R2 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably an alkyl (CrC4) group, such as methyl or tert-butyl more preferably methyl; - Ra, and Rb, identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably hydrogen; - X is a heteroatom or group chosen from O, S, N(R') or -S-CH2-C(O)-O-, -OC(O)-CH2-S-, -OC(O)-N(R')-, -N(R')-C(O)-O-, -N(R')-C(O)-N(R')-, preferably X represents O; - n denotes an integer ranging from 2 to 10, particularly from 3 to 8.

[0056] According to a particular embodiment of the invention, the compound of formula (I) is chosen from those of formula (la) as well as their optical isomers, geometric isomers, their salts, and their solvates such as hydrates:

[0057] [Chem.3]

[0058] formula (the) in which: - R1 represents a polysaccharide motif, preferably a disaccharide; R1 being further: a) possibly substituted by one or more hydroxyl groups OH, and / or b) possibly interrupted by one or more heteroatoms or groups chosen from O, S, -N(R'), preferably interrupted by one or more oxygen atoms, in which R' is as defined in formula (I); - R2 is as defined previously, preferably R2 represents a (Ci-C6)alkyl group, linear or branched, preferably a (Ci-C4)alkyl group, particularly methyl or tert-butyl such as methyl; and - n being as defined previously, preferably n denotes an integer from 2 to 8.

[0059] According to a preferred embodiment, the compounds of formula (I) and (la) are such that R1 represents a disaccharide motif on which n hydroxy groups have been substituted by n -OC(O)-CH2-C(O)-R2 groups, with R2 and n being as defined previously.

[0060] According to a particular embodiment, the disaccharides are selected from cellobiose, maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose, preferably sucrose.

[0061] According to a preferred embodiment, the disaccharides are sucrose.

[0062] According to a particular embodiment, the compounds of formula (I) and (la) are such that n denotes an integer from 2 to 8, more particularly n denotes an integer from 3 to 8, more particularly from 4 to 8.

[0063] In one variant of the invention, the compound of formula (I) or (la) as defined above is a mixture of compounds of different chemical structures.

[0064] More specifically, the compound(s) of formula (I) and (la) are chosen from the following compounds, as well as their optical isomers, their salts, and solvates such as hydrates:

[0065] [Tables 1] Compound CAS No Chemical Name Chemical Structure (1) 1236300-10-9 2.3.4,-oxobutasioate) of aD-Glùeopwaîioside, 1,3,4,6-tehakis-Of 1,3 -dioxobutyi)-Pd-fiiictofiiranosyl! "“If ¢) 2254710-49-9 - ...¾. * ÿ xb r (3) Sucrose pofyacetoacetate û /

[0066] in which R1 are chosen, independently of each other, from -C(0)-CH2-C(0)-CH3 and H with at least two radicals R1 representing -C(O)-CH2-C(O)-CH3, preferably at least three radicals representing -C(O)-CH2-C(O)-CH3.

[0067] More preferably, compounds (I) or (la) are chosen from among the compounds of formula (3).

[0068] The compound(s) of formula (I) or (la) as defined above are preferably present in a content ranging from 0.2% to 99% by weight, particularly from 0.5% to 80%, more particularly from 2% to 70% relative to the total weight of the composition (A) containing them.

[0069] The compound(s) of formula (I) can be obtained by (poly)condensation(s) of n equivalents of dicarbonyl reagent with a nucleophilic reagent R'(H)n comprising n equivalents of nucleophilic functions according to the following scheme:

[0070] [Chem.4]

[0071] diagram in which: - R1, R2, Ra, Rb and n are such as defined for the compound of formula (I) and ; - R3 represents a hydrogen atom, an (Ci-C4)alkyl group such as methyl, ethyl, isobutyl, t-butyl, or an electrofuge group such as CHal3, or Hal3C-SO2- as triflate, with Hal, identical or different, representing a halogen atom; - X and X' represent, independently of each other, an oxygen atom, or sulfur, preferably O.

[0072] These (poly)condensation methods are known to those skilled in the art; examples include “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 patent application PL159100: Method for manufacturing acetylacetate esters.

[0073] According to a particular embodiment of the invention, R'(H)n is selected from the acyclic polyols R'(H)n selected in particular from 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, hexandediol, 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-l,3-pentanediol, 1,6-hexanediol, 1,2 octanediol, 1,8 octane diol, 1,10-decanediol, 2-methyl-l,3-propane diol, hexylene glycol, isoprene glycol.

[0074] According to another embodiment, the compound(s) of formula (I) or (la) are obtained by (poly)condensation(s) of n equivalents of propylenedioxy carbonyl reagent with a polyamine nucleophilic reagent R'(NH2)n comprising n equivalents of -NH2 nucleophilic functions according to the following scheme:

[0075] [Chem.5] K

[0076] diagram in which: -R1, R2, Ra, and n are such as defined for the compound of formula (I); -Rb and Rc', identical or different, represent a hydrogen atom, a (Ci-C4)alkyl group.

[0077] This type of synthesis process is known to those skilled in the art; for example, "Acetoacetylation with 2,2,6-trimethyl-4H-l,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).

[0078] According to another embodiment, the compound(s) of formula (I) or (la) are obtained by (poly)condensation(s) of n equivalents of diketene reagent with a nucleophilic reagent R'(H)n comprising n equivalents of nucleophilic functions according to the following scheme:

[0079] [Chem.6]

[0080] scheme in which R1, X and n are such as defined in formula (I) described above.

[0081] This type of process is known to those skilled in the art. For example, one might cite “Acetoacetamides, 2-hydroximinoacetoacetamides, and 2,3-bis(hydroxymino)-bu tyramides”, Journal fur Praktische Chemie (Leipzig), 323(2), 337-44, (1981) or Angewandte Makromolekulare Chemis, 9, 96-105, (1969). ii) C2-C4 monoalcohol

[0082] As previously stated, a composition (A) according to the invention comprises at least one monoalcohol comprising 2 to 4 carbon atoms.

[0083] Preferably, the monoalcohol(s) of the invention are chosen from among saturated or unsaturated, linear or branched monoalcohols comprising 2 to 4 carbon atoms.

[0084] In particular, the monoalcohol(s) may be chosen from ethanol, isopropanol, n-propanol, tert-butanol, butanol, and mixtures thereof.

[0085] Advantageously, composition (A) comprises the C2-C4 monoalcohol(s) in a content ranging from 1% to 75% by weight, preferably from 5% to 65% by weight, more preferably from 10% to 55% by weight, relative to the total weight of composition (A). iii) Water

[0086] As previously stated, a composition (A) according to the invention comprises at least water.

[0087] Preferably, the water used in the process of the invention is deionized water, sterilized water, or osmosis water.

[0088] Advantageously, the composition (A) comprises water in a content ranging from 1% to 75% by weight, preferably from 5% to 65% by weight, more preferably from 10% to 55% by weight, relative to the total weight of the composition (A). (iv) Particulate coloring matter

[0089] As previously stated, a composition (A) according to the invention comprises at least one particulate coloring matter.

[0090] More particularly, the composition (A) of the invention comprises at least one particulate coloring matter, water-soluble or not, and preferably at a rate of at least 0.01% by weight, relative to the total weight of the composition considered.

[0091] For obvious reasons, this quantity is likely to vary significantly with regard to the intensity of the color effect sought and the colonic intensity provided by the coloring materials considered and its adjustment clearly falls within the competence of the person skilled in the art.

[0092] Preferably, the composition (A) comprises at least one coloring material selected from pigments, direct dyes and their mixtures, more preferably pigments; more preferably the pigment(s) of the invention are selected from carbon black, iron oxides, in particular yellow, red and black, and iron oxide-coated micas, triarylmethane pigments, in particular blue and violet such as BLUE 1 LAKE, azo pigments, in particular red such as D&C RED 7, and an alkali metal salt of lithol red such as the calcium salt of lithol red. B, even more preferentially red iron oxides, yellow iron oxides and azo pigments, especially red ones such as D&C RED 7.

[0093] Pigments

[0094] For the purposes of this invention, "pigment" means any compound capable of imparting color to keratinous materials. These compounds have a solubility in water at 25 °C and atmospheric pressure (760 mmHg) of less than 0.05% by weight, and preferably less than 0.01% by weight.

[0095] Suitable pigments for the invention include, in particular, organic and / or mineral pigments known in the art, especially those described in Kirk-Othmer's Encyclopedia of Chemical Technology and Ullmann's Encyclopedia of Industrial Chemistry. These pigments may be synthetic or natural. They may be in powder or paste form. They may be coated or uncoated. These pigments may, for example, be selected from mineral pigments, organic pigments, lacquers, special effect pigments such as mother-of-pearl or glitter, and mixtures thereof.

[0096] A pigment suitable for the invention can be chosen from among mineral pigments.

[0097] By "mineral pigment" is meant any pigment that meets the definition of Ullmann's encyclopedia in the chapter on inorganic pigments. Among the mineral pigments useful in the present invention, we can cite manganese violet, ultramarine blue, chromium hydrate, ferric blue, and oxides or dioxides of titanium, zirconium, or cerium, as well as oxides of zinc, iron, or chromium.

[0098] It may also be a pigment having a structure that is, for example, of the sericite / brown iron oxide / titanium dioxide / silica type. Such a pigment is marketed, for example, under the reference Coverleaf NS or JS by Chemicals And Catalysts and has a contrast ratio close to 30. It may also be a pigment having a structure that is, for example, of the silica microspheres containing iron oxide type. An example of a pigment with this structure is that marketed by Miyoshi under the reference PC Bail PC-LL-100 P, this pigment being composed of silica microspheres containing yellow iron oxide.

[0099] Advantageously, the pigments may be iron oxides and / or titanium dioxides.

[0100] A pigment suitable for the invention can be chosen from among organic pigments.

[0101] By "organic pigment" is meant any pigment that meets the definition in the Ullmann Encyclopedia in the chapter on organic pigments. Examples of organic pigments useful in the present invention include nitroso, nitro, azo, xanthene, pyrene, quinoline, quinoline, anthraquinone, and triphenylmethane. fluorane, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone.In particular, white or colored organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, blue pigments coded in the Color Index under references CI 42090, 69800, 69825, 74100, 74160, yellow pigments coded in the Color Index under references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, green pigments coded in the Color Index under references CI 61565, 61570, 74260, orange pigments coded in the Color Index under reference CI 11725, 45370, 71105, the red pigments coded in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indole, phenolic derivatives as described in patent FR 2 679 771. .

[0102] By way of example, one can also cite organic pigment pastes such as the products sold by the company HOECHST under the name: COSMENYL YELLOW IOG: Pigment YELLOW 3 (CI 11710); COSMENYL YELLOW G: Pigment YELLOW 1 (CI 11680); COSMENYL ORANGE GR: Pigment ORANGE 43 (CI 71105); COSMENYL RED R: Pigment RED 4 (CI 12085); COSMENYL CARMINE FB: Pigment RED 5 (CI 12490); COSMENYL VIOLET RL: Pigment VIOLET 23 (CI 51319); COSMENYL BLUE A2R: Pigment BLUE 15.1 (CI 74160); COSMENYL GREEN GG: Pigment GREEN 7 (CI 74260); COSMENYL BLACK R: Pigment BLACK 7 (CI 77266).

[0103] The pigments according to the invention can also be in the form of composite pigments as described in patent EP 1 184 426. These composite pigments can be composed in particular of particles comprising an inorganic core, at least one binder ensuring the fixation of organic pigments on the core, and at least one organic pigment covering at least partially the core.

[0104] The organic pigment can also be a lacquer.

[0105] By "lacquer" is meant dyes adsorbed onto insoluble particles, the whole thus obtained remaining insoluble during use.

[0106] Examples of inorganic substrates onto which dyes are adsorbed include alumina, silica, calcium sodium borosilicate or calcium aluminum borosilicate, and aluminum. Carminic acid is one example of a dye adsorbed onto organic substrates. Other examples include 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), and D&C Red. 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green (CI 61 570), D&C Yellow 10 (CI 77 002), D&C Green 3 (CI 42 053), D&C Bine 1 (CI 42 090), FDC Red 4, D&C Red 6, D&C Red 22, D&C Red 28, D&C Red 30, D&C Orange 4, D&C Yellow 8, D&C Green 5, D&C Red 17, D&C Green 6, D&C Yellow 11, D&C Violet 2, Sudan Red, carotenes (beta-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocianin, black carrot, hibiscus, elderberry), caramel, riboflavin, beetroot juice and caramel.

[0107] As examples of lacquers, one may cite the product known under the following name: D & C Red 7 (CI 15850:1).

[0108] The pigment can also be a special effects pigment.

[0109] By "special effect pigments" is meant pigments which generally create a colored appearance (characterized by a certain shade, a certain vibrancy and a certain clarity) that is non-uniform and changes depending on the viewing conditions (light, temperature, viewing angles, etc.). They are thus distinguished from colored pigments which provide a uniform opaque, semi-transparent or conventional transparent tint.

[0110] There are several types of special effect pigments, those with a low refractive index such as fluorescent or photochromic pigments, and those with a higher refractive index such as mother-of-pearl, interference pigments or glitter.

[0111] The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 µm, preferably between 20 nm and 80 µm, and more preferably between 30 nm and 50 µm.

[0112] The pigments can be dispersed within the composition by means of a dispersing agent.

[0113] This dispersing agent may be a surfactant, an oligomer, a polymer, or a mixture of several of these, possessing one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they may adhere physically or chemically to the surface of the pigments. These dispersants further possess at least one functional group that is compatible with or soluble in the continuous medium.In particular, esters of 12-hydroxystearic acid are used, especially C8 to C2o fatty acids and polyols such as glycerol, diglycerin, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g / mol such as that sold under the name Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (name CTFA) sold under the reference Dehymyls PGPH by Henkel or polyhydroxystearic acid such as that sold under the reference Arlacel P100 by Uniqema and their mixtures. Other dispersants that can be used in the compositions of the 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 composition may be surface-treated with an organic agent. In one particular embodiment, the dispersing agent(s) are amino-silicone type, different from the alkoxysilanes described above, and are cationic. Preferably, the pigment(s) is / are selected from mineral, mineral-organic, or organic pigments.

[0114] According to a particular embodiment, the pigment(s) according to the invention are organic pigments, preferably organic pigments treated on the surface by an organic agent chosen from silicone compounds.

[0115] According to another embodiment of the invention, the pigment(s) according to the invention are mineral pigments.

[0116] According to a particular embodiment of the invention, the cosmetic active ingredient is a coloring material chosen from one or more direct colorant(s).

[0117] By "direct dye," we mean natural and / or synthetic dyes, different from oxidation dyes. These are dyes that diffuse superficially onto the fiber. They can be ionic or non-ionic, preferably cationic or non-ionic.

[0118] Among the direct dyes suitable for the invention, mention may be made of azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.

[0119] Direct dyes are preferably cationic direct dyes. Examples include hydrazono cationic dyes of formulas (A) and (B) below and azo cationic dyes of formulas (C) and (D) below:

[0120] [Chem.7] Het+-C(Ra)=NN(Rb)-Ar / Q. (HAS) Hef-N=N-Ar, Q' (C) Het+-N(Ra)-N=C(Rb)-Ar / CT (B) Ar+-N=N-Ar”. Q' (D)

[0121] formulas (A) to (D) in which:

[0122] - Het+ represents a cationic heteroaryl radical, preferentially charged endocyclic cationic such as imidazolium, indolium, or pyridinium, possibly preferentially substituted by at least one (CrC8)alkyl group such as methyl;

[0123] - Ar+ represents an aryl radical, such as phenyl or naphthyl, with a cationic charge exocyclic preferentially ammonium particularly tri(Ci-C8)alkyl-ammonium such as trimethylammonium;

[0124] - Ar represents an aryl group, in particular phenyl, possibly substituted, preferably by one or more electron-donating groups such as (CrC8)alkyl possibly substituted, (CrC8)alkoxy possibly substituted, (di)(Ci-C8)(alkyl)amino possibly substituted on the alkyl group(s) by a hydroxyl group, aryl(Ci-C8)alkylamino, and N-(Ci-C8)alkyl-N-aryl(Ci-C8)alkylamino possibly substituted or else Ar represents a julolidine group;

[0125] - Ar” represents a (hetero)aryl group, possibly substituted such that phenyl or pyrazolyl possibly substituted, preferably by one or more (Ci-C8)alkyl, hydroxyl, (di)(Ci-C8)(alkyl)amino, (Ci-C8)alkoxy or phenyl groups;

[0126] - Ra and Rb, identical or different, representing a hydrogen atom or a (CrC8)alkyl group possibly substituted, preferably by a hydroxyl group;

[0127] or the substituent Ra with a substituent of Het+ and / or Rb with a substituent of Ar together form with the atoms which bear them a (hetero)cycloalkyl; particularly Ra and Rb, representing a hydrogen atom or a (Cr C4)alkyl group possibly substituted by a hydroxyl group;

[0128] - Q represents an organic or mineral anionic counterion such as a halide or an alkyl sulfate.

[0129] In particular, mention may be made of endocyclic cationic azo and hydrazono direct dyes of formula (A) to (D) as defined above. More particularly, the endocyclic cationic direct dyes described in patent applications WO 95 / 15144, WO 95 / 01772 and EP-714954. Preferably the following direct dyes of formulas (E) and (F):

[0130] [Chem. 8]

[0131] formulas (E) or (F) in which:

[0132] - R1 represents an (Ci-C4)alkyl group such as methyl; - R2 and R3, whether identical or different, represent a hydrogen atom or an (Ci-C4)alkyl group such as methyl;

[0133] - R4 represents a hydrogen atom or an electron-donating group such as (Ci -C8)alkyl possibly substituted, (CrC8)alkoxy possibly substituted, (di)(C i-C8)(alkyl)amino possibly substituted on the alkyl group(s) by a hydroxyl group; particularly R4 is a hydrogen atom; - Z represents a CH group or a nitrogen atom, preferably CH; - Q is an anionic counter ion as defined previously, particularly a halide such as chloride or an alkyl sulfate such as methyl sulfate or mesytyl.

[0134] In particular, the dyes of formula (E) and (F) are selected from Basic Red 51, Basic Yellow 87, and Basic Orange 31, or their derivatives, with Q being an anionic counterion as defined above, particularly a halide such as chloride or an alkyl sulfate such as methyl sulfate or mesytyl. The direct dyes may be selected from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly referred to as "acid" direct dyes because of their affinity for alkaline substances.

[0135] By "anionic direct dyes" means any direct dye comprising in its structure at least one CO2R' or SO3R' substituent with R' designating a hydrogen atom or a cation from a metal or an amine, or an ammonium ion.

[0136] Anionic direct dyes can be selected from acidic nitro direct dyes, acidic azo dyes, acidic azinic dyes, acidic triarylmethanic dyes, acidic indoamine dyes, acidic anthraquinone dyes, indigoids and acidic natural dyes.

[0137] Among the natural direct dyes that can be used according to the invention are lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine, and orceins. Extracts or decoctions containing these natural dyes, and in particular henna-based poultices or extracts, can also be used.

[0138] Preferably, the direct dyes are chosen from anionic direct dyes.

[0139] Colouring materials, preferably pigments, may be present in concentrations ranging from 0.01% to 50% by weight, preferably from 0.02% to 40% by weight, more particularly from 0.05% to 30% relative to the total weight of the composition which contains them.

[0140] The direct colorant(s) may be present in concentrations ranging from 0.001% to 20% by weight of the total weight of the composition, preferably from 0.005% to 15% by weight of the total weight of the composition which contains them.

[0141] Preferably, the particulate colouring material(s) are chosen from pigments, direct dyes and their mixtures, preferably pigments; more preferably the pigment(s) of the invention are chosen from carbon black, iron oxides in particular yellow, red and black and micas coated with iron oxide, triarylmethane pigments in particular blue and violet such as BLUE 1 LAKE, azo pigments in particular red such as D&C RED 7 alkali metal salt of lithol red such as the calcium salt of lithol red B, even more preferably red iron oxides, yellow iron oxides and azo pigments in particular red such as D&C RED 7.

[0142] Advantageously, the process for applying makeup to keratinous materials is a process for applying makeup to the skin, eyelashes and / or eyebrows, in particular a process for applying makeup to the lips, mascara, eyeliner, eyeshadow, foundation, v) Crosslinking agent

[0143] As previously stated, a composition (B) according to the invention comprises at least one crosslinking agent.

[0144] For the purposes of the invention, the term "crosslinking agent", also referred to as "R", designates a compound capable of forming with at least one acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention: - at least one covalent bond, - at least one donor-acceptor (dative) bond, and / or - at least one coordination link,

[0145] and thus to crosslink this or these compound(s).

[0146] Preferably, the term "crosslinking agent" designates a compound capable of establishing at least one covalent bond with an acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention and thus crosslinking this or these compound(s).

[0147] For the purposes of the present invention, it is understood that the terms “crosslinking agent” and “crosslinking agent” are equivalent.

[0148] The crosslinking agent(s) are preferably present in a mass content ranging from 0.5 to 95% by weight, in particular from 1 to 90% by weight, and more particularly from 10 to 85% by weight, even more particularly from 15 to 80% relative to the total weight of the composition containing them.

[0149] More specifically, the crosslinking agent(s) suitable for the invention can be chosen from among compounds with amine functions, known as (poly)amine compounds.

[0150] By “(poly)amine” compounds, we mean compounds comprising respectively at least one primary or secondary amine function.

[0151] The (poly)amine compounds may in particular be chosen from among polyamine compounds having several primary and / or secondary amine groups or from among the amino alkoxysilanes, and more particularly from among the amino alkoxysilane compounds, the diamine compounds, the triamine compounds, and mixtures thereof.

[0152] The (poly)amine compound may be a compound comprising from 2 to 20 carbon atoms, in particular a non-polymeric compound. It may be acyclic, or cyclic, linear or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -Si(R')2-, -N(R')- preferably -O-, -Si(R')2-, or their combinations such as -Si(R')2-O- or -O-Si(R')2-, with R', identical or different, representing a (Ci-C4)alkyl group such as methyl, and R' representing a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom.

[0153] By "non-polymer compound" is meant a compound that is not directly obtained by a polymerization reaction of monomers.

[0154] Examples of (poly)amine compounds include 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, methyl bis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylene triamine, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, l,3-bis(aminomethyl)cyclohexane, l,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-Trioxa-l,13-tri decanediamine, spermidine and C36-alkylenediamines (respectively Priamine™ 1071, 1073, 1074, 1075), preferably spermidine and / or 4,7,10-Trioxa-l,13-tri decanediamine.

[0155] According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine, namely they contain a single primary and / or secondary amine group, preferably primary (NH2).

[0156] The (poly)amine compound(s) may be chosen from among the amino alkoxysilanes, in particular those of formula R'iSi(OR'2)z(R'3)x, in which:

[0157] - R' i is a linear or branched Ci-C6 hydrocarbon chain, saturated or unsaturated, cyclic or acyclic substituted by a group chosen from among the primary amine groups NH2 or secondary -N(H)R with R representing a C1-C4 alkyl, an aryl, a benzyl substituted by an amino group or by an aminoalkyl group in C1-C4; R can be interrupted in its chain by a heteroatom (O, S, NH) or a carbonyl group C(O), R being linked to the silicon atom directly via a carbon atom,

[0158] - R'2 and R'3, whether identical or different, represent a linear (Ci-C6)alkyl group or branched,

[0159] - z denotes an integer from 1 to 3, and

[0160] - x denotes an integer from 0 to 2,

[0161] with z + x = 3.

[0162] 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 group -NH2 or -N(H)R, where R represents a C1-C6 alkyl, a C3-C6 cycloalkyl, or a C6 aromatic. More preferably, R'1 is a linear, saturated C1-C6 hydrocarbon chain substituted with an amine group NH2. Even more preferably, R'1 is a linear, saturated C2-C4 hydrocarbon chain substituted with an amine group NH2.

[0163] In particular, R'2 represents an alkyl group comprising 1 to 4 carbon atoms, preferably R'2 represents a linear alkyl group comprising 1 to 4 carbon atoms, and more preferably R'2 represents the ethyl group.

[0164] In particular, R'3 represents an alkyl group comprising from 1 to 4 carbon atoms, preferably, R'3 represents a linear alkyl group comprising from 1 to 4 carbon atoms, and more preferably R'3 represents the methyl or ethyl group

[0165] Preferably, the (poly)amine compound(s) are chosen from aminoalkylpolyalkoxysilanes, compounded according to the preceding formula in which z is equal to 2 and x is equal to 1, or in which z is equal to 3 and x is equal to 0. Preferably, z is equal to 3.

[0166] In particular, the (poly)amine compound(s) are selected from amino alkoxysilanes having only one primary and / or secondary amine group, preferably primary (NH2), such as 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxy-silane, p-aminophenyltrimethoxysilane, and N-(2-aminoethylaminomethyl)-phenethyltrimethoxysilane.

[0167] Preferably, the (poly)amine compound(s) are selected from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, and more preferably 3-aminopropyltriethoxysilane (APTES), in particular that marketed by Sigma Aldrich.

[0168] The (poly)amine compound(s) may also be selected from amine polymers, in particular having a weight average molecular weight ranging from 500 g.mol1 to 1,000,000 g.mol1, preferably ranging from 500 g.mol' to 500,000 g.mol1, and preferably ranging from 500 g.mol1 to 100,000 g.mol1.

[0169] According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine and selected from polydialkylsiloxanes, in particular of formula (III):

[0170] H2N-ALK-Si(R'2)(R'3)-O-[ Si(R'2)(R'3)-O]n- Si(R'2)(R'3)-R'4(in)

[0171] formula (III) wherein:

[0172] - ALK represents a (Ci-C4)alkylene group, linear or branched, preferably linear, such as propylene,

[0173] - R'2, and R'3, identical or different, preferably identical, represent a (CrC4)alkyl group such as methyl, and

[0174] - R'4 represents a (Ci-C6)alkyl group, linear or branched, preferably at C4, such that n-butyl, n represents an integer greater than or equal to 2, preferably the value of n is such that the average molecular weight by weight of the polydimethylsiloxane ranges from 500 to 3000 g.mol'. As an example of polydimethylsiloxanes (III), we can cite those sold under the names "MCR-A11" and "MCR-A12" by the company Gelest.

[0175] According to a particular embodiment of the invention, the (poly)amine compound(s) are diaminized, namely they contain two primary and / or secondary amine groups, preferably primary (NH2).

[0176] More specifically, they are chosen from compounds of formulas (IV) or (V): • ALK[(O-ALK')m-NH2]2 (IV) or • H2N-ALK-Si(R')2-[O-Si(R')2]mO-Si(R)2-ALK'-NH2 (V)

[0177] formulas (IV) and (V) in which:

[0178] - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene,

[0179] - R', identical or different, represent a (Ci-C4)alkyl group, such as methyl,

[0180] - m represents an integer greater than or equal to 0, preferably the value of m is such that the average molecular weight by weight of compound (IV) or (V) ranges from 500 g.mol1 to 55,000 g.mol1.

[0181] Examples of compounds of formula (V) include those sold under the names “DMS-A11”, “DMS-A12”, “DMS-A15”, “DMS-A21”, “DMS-A31”, “DMS-A32” and “DMS-A35” by the company Gelest.

[0182] The (poly)amine compound(s) which are diaminized are particularly diaminized polyethers in particular of formula H2N-ALK-O-[ALK'-O]m-ALK”-NH2 with ALK, ALK' and ALK”, identical or different representing a (Ci-C6)alkylene group, linear or branched, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-l,13-tridecanediamine or the compounds known under the reference Jeffamine of the Huntsman company, and more particularly polyethylene glycol and / or polypropylene glycol a, co-diamine (with amine function at the end of the chain) such as those sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000, ED-2003.

[0183] The (poly)amine compound(s) which are diamined may be more particularly chosen from 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, among the α,co-diaminooxaalkanes such as 1,8-diamino-3,6-oxaoctane, α,12-diamino-4,9-dioxadodecane, and α,13-diamino-4,7,10-trioxatridecane (also called 4,7,10-Trioxa-α,13-tridecanediamine), preferably 4,7,10-Trioxa-α,13-tridecanediamine.

[0184] According to a particular embodiment of the invention, the (poly)amine compound(s) are triamine, namely they contain three primary and / or secondary amine groups, preferably primary (NH2). More particularly, they are selected from triamine polyethers, notably those of formula ALK'”[(O-ALK')m-NH2]3, with ALK' as defined above and ALK”' representing a trivalent (Ci-C6)alkylene group, linear or branched, and m representing an integer greater than or equal to 0.

[0185] As (poly)amine compounds which are triamined, triamine polyethers are particularly cited, and in particular polyethylene glycol and / or polypropylene glycol a, co-diamine (with amine function at the end of the chain) such as those sold under the names Jeffamine T-403.

[0186] According to another particular embodiment of the invention, the (poly)amine compound(s) comprise more than three primary and / or secondary amine groups, preferably primary (NH2).

[0187] In this variant, the (poly)amine compound(s) are chosen from poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary lateral amine functions, such as poly(3-aminopropyl) methacrylamide and poly(2-aminoethyl) methacrylate.

[0188] More specifically, the polyamine compounds are chosen from chitosans (in particular poly(D-glucosamine)), and polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains.

[0189] According to another embodiment, the (poly)amine compound(s) are chosen from poly(alkylene (C2-C5)imines), and preferably polyethyleneimines and polypropyleneimines, in particular poly(ethyleneimine), especially that sold under reference 408700 by Aldrich Chemical or under the trade name Lupasol by BASF, in particular with molecular weights ranging from 1,200 g.mol1 to 25,000 g.poly(allylamine), in particular that sold under reference 479136 by Aldrich Chemical; polyvinylamines and their copolymers, particularly with vinylamides, especially vinylamine / vinylformamide copolymers such as those marketed under the name Lupamin® 9030 by BASF; polyamino acids containing NH2 groups such as polylysine, in particular that sold by JNC Corporation (formerly Chisso); amino dextran, in particular that sold by CarboMer Inc; polyvinyl amino alcohol, in particular that sold by CarboMer Inc; acrylamido(Ci-C6)alkylamine-based copolymers, in particular acrylamidopropylamine-based copolymers; and poly(D-Glucosamine), for example, sold under the reference Kionutrime CSG® by Kytozyme.

[0190] According to a particular embodiment, polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains are selected from the compounds of the following formula (VI):

[0191] Ra-Si(Rb)(Rc)-O-[Si(Rb)(Rc)-O]m-[Si(ALK1-NH2)(Ra)-O]n-Si(Rb)(Rc)-Ra(VI)

[0192] formula (VI) wherein:

[0193] - Ra, identical or different, represent a hydroxy or (Ci-C4)alkyl group,

[0194] - Rb and Rc, identical or different, preferably identical, represent a group (Ci-C4)alkyl, such as methyl;

[0195] - ALK1 represents a (Ci-C6)alkylene group, linear or branched, possibly interrupted by a group N(H);

[0196] - m and n are integers greater than or equal to 1, preferably m and n are such that the The average molecular mass by weight of the compound with formula (VI) ranges from 1,000 g.mol1 to 500,000 g.mol1.

[0197] According to a preferred variant, formula (VI) is such that Ra, Rb, and Rc represent a methyl group, ALK1 represents a propylene group, and the values ​​of n and m are such that the weight-average molecular weight of polydimethylsiloxane ranges from 1,000 g.mol1 to 55,000 g.mol1.

[0198] Examples of polydimethylsiloxanes of formula (VI) include those sold under the names "AMS-132", "AMS-152", "AMS-162", "AMS-163", "AMS-191" and "AMS-1203" by the company Gelest.

[0199] According to another variant, formula (VI) is such that Ra represents a hydroxyl or (CrC4) alkyl group, such as methyl, ALK1 represents a (C5-C6) group alkylene substituted by an NH group, preferably ALK1 represents -(CH2)3-N(H)-(CH2)2-, and m and n are such that the average molecular mass by weight of the compound of formula (VI) ranges from 5,000 g.mol1 to 500,000 g.mol1.

[0200] As an amino polymer, polytetrahydrofuran (or polytetramethylene glycol) α, co-diamine, and polybutadienes α, co-diamine may also be cited.

[0201] According to a particular embodiment of the invention, the (poly)amine compounds are chosen from hyperbranched polymers comprising at least one amino group and dendrimers bearing at least one amino group, such as PAMAM polyamidoamine dendrimers with an ethylenediamine core and a terminal amine function.

[0202] According to a particular embodiment, the composition comprises a crosslinking agent R selected from (poly)amine compounds, in particular selected from chitosans, aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, amodimethicones, polyglucosamines, and mixtures thereof.

[0203] More preferably, the composition comprises a crosslinking agent R selected from aminoalkoxysilanes and polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains such as amodimethicones, and even more preferably selected from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, V-(2-aminoethyl)-3-aminopropyltriethoxysilane and polydimethylsiloxanes comprising terminal amino groups at the end of the chain, such as Bis-Cetearyl Amodimethicone.

[0204] In particular, said (poly)amine compounds are selected from a) chitosans, such as poly(D-Glucosamine), b) diamine polyethers, particularly polyethylene glycol α,co-diamine (with an amine function at the chain end), c) α,co-diaminooxaalkanes such as 4,7,10-Trioxa-1,13-tridecanediamine, d) triamine polyethers, such as Polyetheramine (or jeffamine), e) aminoalkoxysilanes, such as APTES, f) polydialkylsiloxanes comprising primary amine groups at the chain ends or on side chains, particularly polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amodimethicones including amine groups on side chains such as Bis-Cetearyl Amodimethicone, notably that marketed by Momentive Performance Materials, and g) NH2-alk-NH2 polyamine compounds,in which alk denotes a divalent hydrocarbon chain in C2-C20, possibly interrupted by one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a Ci-C4 alkyl radical, such as spermidine.

[0205] According to a preferred embodiment, said (poly)amine compounds are selected from b) diamine polyethers, particularly polyethylene glycol a, co-diamine (with amine function at the end of the chain), d) triamine polyethers, such as Polyetheramine (or jeffamine), e) aminoalkoxysilanes, such as APTES, f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, particularly polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains such as Bis-Cetearyl Amodimethicone, in particular that marketed by Momentive Performance Materials;and even more preferentially among f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, particularly polydimethylsiloxanes comprising primary amine groups such as poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains such as Bis-Cetearyl Amodimethicone. ;

[0206] According to a preferred embodiment, the (poly)amine compound(s) is / are chosen from:

[0207] a) diamine polyethers, in particular polyethylene glycol α, co-diamine, with an amine function at the end of the chain,

[0208] b) triamine polyethers, in particular polyetheramine (or jeffamine),

[0209] c) aminoalkoxysilanes, in particular APTES,

[0210] d) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains, more particularly Bis-Cetearyl Amodimethicone. Fatty phase - fatty substances

[0211] According to a particular embodiment, composition (A) and / or composition (B) further comprises one or more fats, particularly one or more oils, preferably volatile.

[0212] More particularly, in the process of the invention at least one of the compositions (A), (B) contains a fatty phase.

[0213] In particular, at least one of the compositions (A) or (B) comprises one or more fatty substances, particularly one or more oils, preferably volatile.

[0214] By "oil" is meant a liquid fat at room temperature (20 °C) and atmospheric pressure (760 mm Hg).

[0215] The term “hydrocarbon oil” means an oil formed essentially, or even composed, of carbon and hydrogen atoms, and possibly of oxygen and nitrogen atoms, and not containing silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0216] According to one embodiment of the invention, the oil(s) is / are chosen from volatile oils, in particular:

[0217] * hydrocarbon oils having 8 to 16 carbon atoms, and in particular:

[0218] - C8-Ci6 branched alkanes such as isoalkanes such as isoalkanes (also called isoparaffins) such as Ci3-Ci6 Isoparaffin, isododecane, isodecane, isohexadecane, and for example oils sold under the trade names Isopars or Permetyls, alone or in mixtures, preferably isododecane (also called 2,2,4,4,6-pentamethylheptane), more preferably isododecane;

[0219] - linear alkanes, for example Cn-Cl6, alone or in mixtures, for example such as hexane, decane, undecane, tridecane, isoparaffins such as, or n-dodecane (C12) and n-tetradecane (C14), the undecane-tridecane mixture, mixtures of n-undecane (Cl1) and n-tridecane (Cl3), and their mixtures as well as mixtures of n-undecane (C11) and n-tridecane (C13);

[0220] - cyclic, non-aromatic, volatile C5-Ci2 alkanes;

[0221] * short-chain esters having from 3 to 8 carbon atoms in total such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate;

[0222] * hydrocarbon oils carbonate of structure R'i-OC(O)-O-R'2 in which R'i and R'2 independently designate a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen from dibutylcarbonate or dipentylcarbonate;

[0223] * ether oils of formula RrO-R2 in which Ri and R2 denote independently a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;

[0224] *silicone oils comprising, in particular, from 2 to 7 silicon atoms, these silicone oils optionally comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms, such as dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof;

[0225] more preferably the volatile oil(s) are chosen from among the C8-Ci6 alkanes, in particular branched ones such as isododecane.

[0226] In particular, at least one of the compositions (A) or (B) comprises one or more non-volatile oils, in particular selected from:

[0227] * non-volatile fluorinated oils, in particular selected from fluorinated polyethers, as well as among fluorosilicone oils, fluorinated silicones;

[0228] * non-volatile silicone oils, in particular selected from silicones non-volatile substances with the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyltrimethicone, diphenylsiloxy phenyl trimethicone; as well as their mixtures.

[0229] * non-volatile non-polar hydrocarbon oils, in particular selected from linear or branched compounds, of mineral or synthetic origin: i) paraffin oil, ii) squalane, isoeicosane, iii) mixtures of linear hydrocarbons, saturated, more particularly in Ci5-C28, such as mixtures whose INCI names are (Ci5-Ci9)alkane, (Ci8-C2i)alkane, (C2i-C28)alkane, iv) polybutenes, hydrogenated or not; v) polyisobutenes, hydrogenated or not, preferably hydrogenated, vi) polydecenes, hydrogenated or not, vii) decene / butene copolymers, butene / isobutene copolymers and viii) their mixtures;

[0230] * non-volatile polar hydrocarbon oils that may be selected from:

[0231] i) fatty alcohols, saturated, unsaturated, linear or branched, in the form of C10-C26, preferably mono-alcohols; advantageously, the C10-C26 alcohols are fatty alcohols, preferably branched when they comprise at least 16 carbon atoms; preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms, such as in particular lauric, isostearyl, oleic alcohol, 2-butyloctanol, 2-undecyl pentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof;

[0232] ii) triglycerides consisting of esters of fatty acids and glycerol, in particular those whose fatty acids may have chain lengths ranging from C4 to C36, and especially from C8 to C36, these oils being linear or branched, saturated or unsaturated; by way of example, heptanoic or octanoic triglycerides, caprylic / capric acid triglycerides; vegetable oils such as wheat germ, sunflower, grapeseed, sesame, corn, apricot kernel, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, squash, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, rosehip, peanut, coconut, argan, passionflower, kaya; the liquid fraction of shea butter, and the liquid fraction of cocoa butter; as well as mixtures thereof;

[0233] iii) linear aliphatic hydrocarbon esters of formula RC(O)-OR' in which RC(O)-O- represents the carboxylic acid remainder comprising from 2 to 40 carbon atoms, and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, aliphatic hydrocarbon esters of alkylene glycol, in particular ethylene glycol or propylene glycol; the total number of carbon atoms advantageously being at least 10;in particular selected from isoamyl laurate, cetostearyl octanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate or isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, ethyl 2-hexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol diethyl 2-hexanoate and mixtures thereof, hexyl laurate, neopentanic acid esters such as isodecyl neopentanate, isotridecyl neopentanate, isostearyl neopentanate, octyl-2-docecyl neopentanate, isononanoic acid esters such as isononyl isononanoate, isotridecyl isononanoate, octyl isononanoate, oleyl erucate;lauroyl isopropyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate, myristyl myristate;

[0234] iv) hydroxylated esters such as polyglycerol-2 triisostearate;

[0235] v) aromatic esters such as tridecyl trimellitate, benzoate of Ci2- alcohols C15, 2-phenyl ethyl ester of benzoic acid, butyl octyl salicylate;

[0236] vi) linear fatty acid esters having a total number of carbons from 35 to 70 such as pentaerythrityl tetrapelargonate;

[0237] vii) C24-C28 branched fatty acid or fatty alcohol esters such as triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tridecyl-2-tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetradecanoate;

[0238] viii) polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and diol such as those with INCI name dilinoleic acid / butanediol copolymer, dilinoleic acid / propanediol copolymer; polyesters obtained by condensation of fatty acid dimer and diol dimer such as dilinoleyl dimer dilinoleate;

[0239] ix) synthetic ethers having 10 to 40 carbon atony such as dicaprylyl ether;

[0240] x) di-alkyl carbonates, the 2 alkyl chains being either identical or different, such as dicaprylyl carbonate;

[0241] xi) vinylpyrrolidone copolymers such as vinylpyrrolidone / 1-hexadecene copolymer; and

[0242] xii) their mixtures;

[0243] * non-volatile carbonate oils may be selected from carbonates of formula R8-OC(O)-O-R9, with R8 and R9, identical or different, represent an alkyl chain from C4 to C12, and preferably from C6 to C10, linear or branched; the carbonate oils can be dicaprylyl carbonate (or dioctyl carbonate), di(ethyl-2-hexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate; di-neopentyl carbonate; dipentyl carbonate; dineoheptyl carbonate; di-heptyl carbonate; di-isononyl carbonate; or di-nonyl carbonate; and preferably dioctyl carbonate;

[0244] * oils called non-volatile ether oil of formula RrO-R2 in which Ri and R2 independently denote a linear, branched, or cyclic C6-C24 alkyl group, preferably a C6-Ci8 alkyl group, and preferably a C8-Ci2 alkyl group. It may be preferable for Ri and R2 to be identical. Examples of linear alkyl groups include hexyl, heptyl, octyl, nonyl, decyl, undodyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, behenyl, docosyl, tricosyl, and tetracosyl groups.Examples of branched alkyl groups include 1,1-dimethylpropyl, 3-methylhexyl, 5-methylhexyl, ethylhexyl, 2-ethylhexyl, 5-methyloctyl, 1-ethylhexyl, 1-butylpentyl, 2-butyloctyl, isotridecyl, 2-pentylnonyl, 2-hexyldecyl, isostearyl, 2-heptylundecyl, 2-octyldodecyl, 1,3-dimethylbutyl, 1-(l-methylethyl)-2-methylpropyl, 1,1,3,3-tetramethylbutyl, 3,5,5-trimethylhexyl, 1-(2-methylpropyl)-3-methylbutyl, and a group 3,7-dimethyloctyl, and a 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group. Examples of cyclic alkyl groups include a cyclohexyl group, a 3-methylcyclohexyl group, and a 3,3,5-trimethylcyclohexyl group., dilaury ether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyl dimethyl butyl ether, cetyl dimethyl butyl ether, cetyl isobutyl ether and mixtures thereof; .

[0245] more preferably c) the non-volatile oil(s) is / are chosen from among the polyisobutenes, hydrogenated or not, preferably hydrogenated such as for example the non-volatile compounds of the Parléam® range; the mixtures of C15-C19 Alkane, and from among the linear aliphatic hydrocarbon esters of formula RC(O)-OR' in which RC(O)-O represents a carboxylic acid remainder comprising from 2 to 40 carbon atoms, and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, such as defined above in particular isononyl isononanoate.

[0246] Most preferably the process of the invention comprises the application of one or more hydrocarbon oils having 8 to 16 carbon atoms, and in particular C8-Ci6 branched alkanes such as iso-alkanes such as C13-C16 Isoparaffin, isododecane, isodecane, isohexadecane, alone or in mixtures, preferably isododecane.

[0247] Particularly the quantity of oil(s) in at least one of the compositions (A) or (B) is between 1% and 99% by weight relative to the total weight of the composition, more particularly between 10% and 90% by weight, preferably between 20% and 75%, better between 25% and 70% by weight relative to the total weight of the composition. Compositions

[0248] As previously stated, a composition (A) and a composition (B) according to the invention are distinct.

[0249] According to one embodiment, compositions (A) and (B) are packaged separately. By "packaged separately", it is meant that compositions (A) and (B) are packaged inside two compartments, formed by two separate containers.

[0250] According to a particular embodiment, composition B comprises an aqueous phase, and in particular comprises water.

[0251] According to an advantageous variant, the composition (B) is aqueous or hydroalcoholic.

[0252] According to another particular embodiment of the invention, composition (B) is an anhydrous composition. In particular, composition (B) is anhydrous and comprises at least one oil, in particular a volatile oil such as isododecane.

[0253] Composition (B) may further comprise one or more organic solvents.

[0254] By "organic solvent" is meant an organic substance capable of dissolving another substance without chemically altering it.

[0255] Examples of organic solvents include: a) C2-C6 alkanols, such as ethanol and isopropanol; b) water-miscible polyols at room temperature (25 °C), in particular polyols having, in particular, 2 with 10 carbon atoms, preferably having 2 to 6 carbon atoms, such as glycerin, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, diglycerin; c) polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and d) aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0256] According to a particular embodiment, the composition further comprises one or more polyols, in particular chosen from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerin.

[0257] In particular, the composition (B) is aqueous or hydroalcoholic (ethanol / water mixture, in particular in volume ratios from 1 / 99 to 99 / 1, more particularly from 10 / 90 to 90 / 10, even more particularly from 20 / 80 to 80 / 20, preferably from 40 / 60 to 60 / 40, such as 50 / 50).

[0258] The composition may be in anhydrous form, water-in-oil emulsion or oil-in-water emulsion. Kit and application

[0259] According to yet another aspect, the present invention also relates to a multi-compartment kit or device, particularly cosmetic, for the makeup of keratinous materials, in particular skin, lips, eyelashes, and / or eyebrows, comprising at least two compositions (A) and (B) packaged separately with:

[0260] - at least one first compartment containing at least the composition (A) comprising: i) at least one compound of formula (I) or (la) as defined above, ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and iv) at least one particulate coloring matter;

[0261] - at least one second compartment separate from said first compartment, and containing at least composition (B) comprising: v) a crosslinking agent selected from (poly)amine compounds, in particular aminoalkylpolyalkoxysilanes, α,Q-diaminooxaalkanes, chitosanes, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains.

[0262] Any type of applicator can be used for the application of the first and / or second composition.

[0263] The respective applicators of the first and second composition may be identical or distinct.

[0264] According to a variant of the invention, the first and second compositions can be applied by means of two separate applicator portions of the same applicator.

[0265] According to another variant, the makeup kit according to the present invention comprises one or more means of applying the first and second compositions.

[0266] The first and second cosmetic compositions included in the makeup kit of the invention can in particular be applied to the eyelashes and / or eyebrows, using a sponge, a flocked applicator, a brush, a paintbrush, a comb, a threaded rod or a pen equipped with a notched wheel. They can also be applied with a finger.

[0267] In this case, the first composition can be applied using any applicator provided that it allows localized deposition on part of the length of the keratin fiber and, when it is a lash, on no more than 2 / 3 of its length.

[0268] The threaded rod may be made of plastic or metal or any other suitable material.

[0269] The pen with a notched wheel is more particularly described in US application 5851019 or FR2588733.

[0270] This pen allows precise dosing of product to be applied at the outlet of the pen after actuating a notched wheel or a push button which advances a piston with each rotation / pressure.

[0271] In reality, the makeup of keratinous materials can be carried out according to two methods. The first method consists of a multi-step process by the user, namely at least two steps, the first consisting of the application of the "basecoat" composition and the second consisting of the application of the "topcoat" composition in whole or in part over the first composition called "basecoat" and over the keratinous materials.

[0272] According to a particularly advantageous embodiment, this packaging article is provided with two separate applicators.

[0273] The second method consists of pre-mixing the two compositions, just before applying the resulting composition to the keratinous materials.

[0274] Regardless of the method chosen by the user, the packaging kit comprises two separate compartments or reservoirs for each of compositions (A) and (B), each reservoir or compartment being closed by a closure element, and optionally at least one suitable applicator, preferably two applicators. It should be noted that the packaging kit may also include means for combining the two compositions prior to application, such as a container and a stirrer.

[0275] The applicator may optionally be integral with the container. Advantageously, the applicator is integral with a rod which, itself, is integral with the closing element.

[0276] The closure element can be coupled to the container by screwing. Alternatively, the coupling between the closure element and the container is achieved by means other than screwing, in particular via a bayonet mechanism, by snap-fitting, or by clamping. "Snap-fitting" refers in particular to any system involving the passage of a bead or a band of material by elastic deformation of a portion, in particular of the closure element, and then by the return of said portion to its elastically unconstrained position after passing the bead or band.

[0277] The container, advantageously comprising the compartment(s) or reservoir(s), as well as the mixing container, may be at least partially made of thermoplastic material. Examples of thermoplastic materials include polypropylene and polyethylene.

[0278] Alternatively, the containers are made of non-thermoplastic material, in particular glass or metal (or alloy).

[0279] The containers are preferably equipped with a wringer located near at least one opening of the container. Such a wringer allows the applicator and, optionally, the rod to which it may be attached, to be wiped. Such a wringer is described, for example, in French patent FR 2 792 618.

[0280] The invention is illustrated in more detail in the following examples. Quantities are indicated as a percentage by weight. Compound 1#: Sucrose with acetoacetate functions

[0281] Compound 1 was synthesized according to the scheme below:

[0282] [Chem.9] SU

[0283] scheme wherein R1, identical or different, represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1 radicals represent -C(O)-CH2-C(O)-CH3.

[0284] 100 g of sucrose and 406.55 g of tert-butyl acetoacetate are placed in A 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column is used. The reaction mixture is heated in an oil bath (oil bath temperature 140°C–150°C) for 4 hours. After 4 hours, NMR confirms the incorporation of the acetoacetate group. The reaction mixture is then concentrated on a rotary evaporator at 150°C under continuous vacuum. A viscous yellow-orange liquid is obtained, which, upon analysis, corresponds to the expected product. Compound 2#: Glucose with acetoacetate function (5eq)

[0285] Compound 1 was synthesized according to the scheme below:

[0286] [Chem. 10]

[0287] scheme wherein identical or different RI represents a hydrogen atom or a -methylcarbonylmethylcarbonyl group -C(O)-CH2-C(O)-CH3, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3.

[0288] 100 g of D-glucose and 482.90 g of tert-butyl acetoacetate are placed in a balloon A 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column. The reaction mixture is heated in an oil bath (oil bath temperature 150°C–160°C) for 5 hours. After 5 hours, NMR confirms the grafting of the acetoacetate group. The reaction mixture is then concentrated on a rotary evaporator at 150°C under continuous vacuum. A highly viscous, dark brown liquid is obtained, which, upon analysis, corresponds to the expected product. Preparation of compositions A, (1) and B

[0289] Compositions A, (1) and B are prepared from the contents indicated in the tables below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[0290] [Tables2] Ingredients Composition (A) invention Composition (1) comparative Compound 1 36 - Compound 2 w 36 Water A. 7 27 Isopropanol 27 77 Black iron oxide 10 10

[0291] [Tables3] Ingredients Composition (B) Bis-C eteary 1 AmMimethicone (SILSOFT AX from Momentive Performance Materials) 60 Isododecane 40

[0292] The compositions are prepared by simply mixing the ingredients detailed in the tables above using a SpeedMixer® (Hauschild DAC 150.1 FVZ) (10 grams, 1 cycle, 2 minutes 30 seconds, 2500 rpm). Formulas to apply

[0293] Composition (A) according to the invention and composition (B) on the one hand, and comparative composition (1) and composition (B) on the other hand, were mixed in a mass ratio 1:1, using a SpeedMixer® Hauschild DAC 150.1 FVZ) (10 grams, 1 cycle, 2 minutes 30 seconds, 2500 rpm). Application

[0294] Each formula ((A) + (B)) or ((1) + (B)) was applied with a spatula to a supplale® support (SOUDOTIQUE reference RLXSUPNOIR, format: 30000 X 1200 MM X 0.7 MM) measuring 2 cm x 5 cm, at a rate of 0.02 g / cm2.

[0295] Drying takes place at room temperature for 24 hours. Two-phase water resistance

[0296] Once dry, the Supplale® thus treated are immersed in biphasic water (La Roche Posay Respectissime waterproof eye makeup remover) for 3 minutes.

[0297] Once the immersion was finished, the Supplale® were rubbed against a towel (Chicopee® VERACLEAN™ Polish Plus 34x32cm) 10 times with a mass of 660 g, over a length of 34 cm.

[0298] To measure color fastness, a color difference (delta E) is measured between the initial deposit and the deposit after aggression. Persistence Protocol

[0299] The persistence of the color of the deposits was evaluated in the CIE L*a*b* system, using a Minolta Konica CM 700d® Spectrophotometer (illuminant D65, angle 10°, specular component included).

[0300] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green / red color axis and b* the blue / yellow color axis.

[0301] The color retention of the deposits is evaluated by the color difference AE between Supplale® colored deposits before and after exposure according to the protocol described above. The lower the AE value, the more resistant the color is to exposure.

[0302] The value of AE is calculated according to the following equation:

[0303] [Math.l] AE =

[0304] In this equation, L*a*b* represent the values ​​measured after staining the Supplale® and after having undergone an aggression, and Lo*ao*bo* represent the values ​​measured after staining the Supplale® but before aggression. Results

[0305] The evaluation results are summarized in the table below:

[0306] [Tables4] Properties Two-phase water resistance AE values ​​Standard deviation Comparative formula ((1) + (B)) 39.3127 3.5228 Formula according to the invention ((A) + (B)) 7.9302 9.8549

[0307] It appears that the application of the formula according to the invention makes it possible to obtain a significantly improved two-phase water retention compared to the application of the comparative formula.

Claims

1. Demands A method for applying makeup to keratinous materials, particularly skin and / or lips and / or eyelashes and / or eyebrows, comprising at least the application to said keratinous materials of at least two distinct compositions (A) and (B): - said composition (A) comprising at least: (i) one or more compounds of formula (I) as well as its optical isomers, geometric isomers, salts, and solvates such as hydrates: ro si RRJ s formula (I) in which: - R1 represents a polysaccharide motif, in particular a disaccharide, on which n hydroxy groups have been substituted by n -OC(O)-CH2-C(O)-R2 groups; R1 being further: a) possibly substituted by one or more hydroxyl groups OH, amine -N(R)2 with R representing a (Ci-C4)alkyl group such as methyl, carboxy -C(O)-OH, a vinyl group, and / or b) possibly interrupted by one or more heteroatoms or groups selected from O, S, carbonyl -C(O)-, amine -N(R'), or their combinations 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-, in which R' represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms possibly substituted by at least one hydroxyl group (OH), or possibly substituted by -XC(O)-C(Ra)(R b)-C(O)-R2; preferably R' represents a hydrogen atom, a (Ci-C4)alkyl group; - R2 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably a (C rC4)alkyl group such as methyl or tert-butyl, more preferably methyl;

2. - Ra, and Rb, identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably hydrogen; - X is a heteroatom or group chosen from O, S, N(R'), -S-CH2 -C(O)-O-, -OC(O)-CH2-S-, -OC(O)-N(R')-, -N(R')-C(O)-O-, -N(R')-C(O)-N(R')-, preferably X represents O; - n denotes an integer ranging from 2 to 10, particularly from 3 to 8; and ii) at least one monoalcohol comprising 2 to 4 carbon atoms; iii) water; and (iv) at least one particulate coloring matter; - said composition (B) comprising at least v) a crosslinking agent selected from (poly)amine compounds, in particular aminoalkylpolyalkoxysilanes, α,Q-diaminooxaalkanes, chitosanes, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains. A method according to the preceding claim, wherein the compound(s) of formula (I) is / are selected from those of formula (la) as well as their optical isomers, geometric isomers, their salts, and their solvates such as hydrates: formula (the) in which: - R1 represents a polysaccharide motif, preferably a disaccharide; R1 being further: a) possibly substituted by one or more hydroxyl groups OH, and / or b) possibly interrupted by one or more heteroatoms or groups chosen from O, S, -N(R'), preferably interrupted by one or more oxygen atoms, in which R' is as defined in formula (I); - R2 is as defined in claim 1, preferably R2 represents a linear or branched (Ci-C6)alkyl group, preferably a (Ci-C4)alkyl group particularly methyl or tert-butyl such as methyl; and - n being as defined in claim 1, preferably n denotes an integer from 2 to 8.

3. A method according to any one of the preceding claims, wherein the compound(s) of formula (I) or (a) is / are such that R1 represents a disaccharide motif on which n hydroxyl groups have been substituted by n -OC(O)-CH2-C(O)-R2 groups, with R2 and n being as defined according to any one of claims 1 or

4. Z. A method according to any one of the preceding claims, wherein R1 represents a disaccharide motif selected from cellobiose, maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose, preferably sucrose.

5. A method according to any one of the preceding claims, wherein the compound(s) of formula (I) and (la) are selected from the following compounds, as well as their optical isomers, their salts, and solvates such as hydrates:

6. in which R1 are chosen, independently of each other, from -C(O)-CH2-C(O)-CH3 and H with at least two radicals R1 representing -C(O)-CH2-C(O)-CH3, preferably at least three radicals representing -C(O)-CH2-C(O)-CH3; More preferably, compounds of formula (I) and (la) are chosen from among compounds of formula (3). A method according to any one of the preceding claims, wherein the crosslinking agent(s) v) is / are selected from: a) chitosans such as poly(D-Glucosamine), b) diamine polyethers, particularly polyethylene glycol α,co-diamine (with an amine function at the chain end), c) α,co-diaminooxaalkanes such as 4,7,10-Trioxa-1,13-tridecanediamine, d) triamine polyethers such as Polyetheramine (or jeffamine), e) aminoalkoxysilanes such as APTES, and f) polydialkylsiloxanes comprising primary amine groups

7.

8. at the end of the chain or on side chains particularly polydimethylsiloxanes comprising primary amine groups such as poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains such as Bis-Cetearyl Amodimethicone;preferably, the crosslinking agent(s) v) is / are chosen from b) diamine polyethers particularly polyethylene glycol a, co-diamine (with amine function at the end of the chain), d) triamine polyethers such as Polyetheramine (or jeffamine), e) aminoalkoxysilanes such as APTES and f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains particularly polydimethylsiloxanes comprising primary amine groups such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains such as Bis-Cetearyl Amodimethicone;and even more preferentially among f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, particularly polydimethylsiloxanes comprising primary amine groups such as poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains such as Bis-Cetearyl Amodimethicone.; A method according to any one of the preceding claims, wherein the particulate coloring materials are selected from pigments, direct dyes and mixtures thereof, preferably pigments; more preferably the pigment(s) of the invention are selected from carbon black, iron oxides in particular yellow, red and black and micas coated with iron oxide, triarylmethane pigments in particular blue and violet such as BLUE 1 LAKE, azo pigments in particular red such as D&C RED 7, alkali metal salt of lithol red such as the calcium salt of lithol red B, even more preferably red iron oxides, yellow iron oxides and azo pigments in particular red such as D&C RED 7. A method according to any one of the preceding claims, wherein said composition (A) and / or said composition (B) comprises in addition one or more fatty substances, particularly one or more oils, preferably volatile.

9. A process according to any one of the preceding claims, wherein said composition (A) and / or said composition (B) further comprises one or more volatile oil(s), in particular selected from: * hydrocarbon oils having 8 to 16 carbon atoms, and in particular: - C8-Ci6 branched alkanes such as isoalkanes such as Ci3-Ci6 Isoparaffin, isododecane, isodecane, isohexadecane, alone or in mixtures, preferably isododecane, more preferably isododecane; - linear alkanes for example in Cn-Cl6, alone or in mixtures, for example such as hexane, decane, undecane, tridecane, isoparaffins such as, or n-dodecane (Cl2) and n-tetradecane (C14), the undecane-tridecane mixture, mixtures of n-undecane (Cl1) and n-tridecane (Cl3), and their mixtures as well as mixtures of n-undecane (C11) and n-tridecane (C13);- volatile non-aromatic cyclic C5-Ci2 alkanes; * short-chain esters having a total of 3 to 8 carbon atoms such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate; * carbonate hydrocarbon oils of structure R'i-OC(O)-O-R'2 in which R'i and R'2 independently designate 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 of formula RrO-R2 in which Ri and R2 independently designate a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;*siliconized oils comprising in particular, from 2 to 7 silicon atoms, these silicone oils possibly comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms, such as dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane,; heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof; more preferably the volatile oil(s) are chosen from among C8-Ci6 alkanes, especially branched ones such as isododecane.

10. A method according to any one of the preceding claims, characterized in that it comprises two successive application steps on said keratin materials, of composition (A) and then of composition (B), or of composition (B) and then of composition (A).

11. A method according to any one of claims 1 to 9, characterized in that it comprises a step of applying to said keratinous materials a composition obtained by an extemporaneous mixture, at the time of application, of said composition (A) and said composition (B).

12. A multi-compartment kit or device, in particular cosmetic, for the makeup of keratinous materials, in particular skin, lips, eyelashes and / or eyebrows, comprising at least two compositions (A) and (B) packaged separately with: - at least a first compartment containing at least composition (A) comprising: i) at least one compound of formula (I) or (la) as defined in any one of claims 1 to 5, ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and iv) at least one particulate coloring matter;- at least one second compartment separate from said first compartment, and containing at least composition (B) comprising: v) a crosslinking agent selected from (poly)amine compounds, in particular aminoalkylpolyalkoxysilanes, α,Q-diaminooxaalkanes, chitosanes, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular as defined in claim 6.;