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 Makeup of Keratinous Materials Comprising the Application of at Least One Acetoacetate Polysaccharide Compound and a Crosslinking Agent. The present invention relates to a process for makeup of 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 one compound of formula (I) comprising at least two acetoacetate functional groups, at least one monoalcohol comprising 2 to 4 carbon atoms, and water, and said composition (B) comprising at least one amine crosslinking agent, with at least one of compositions (A) and (B) comprising at least one particulate coloring agent. Figure for the abstract: 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 in particular to that of eyebrow makeup, including eyebrow hairs, the skin of implantation of said hairs, and their contours.

[0002] It aims to propose a process for making up keratinous materials comprising at least the application on said keratinous materials of at least two distinct compositions (A) and (B).

[0003] The invention also relates to a makeup kit for keratinous materials comprising at least two compositions (A) and (B) packaged separately. Prior art

[0004] In the field of eyebrow makeup, consumers have access to a variety of products and solutions which, although partially meeting aesthetic and functional needs, have notable limitations in terms of hold and resistance.

[0005] Among these solutions, pigment-based eyebrow pencils and pens, often composed of aqueous formulas containing dyes, while appreciated for their ease of use, only guarantee limited hold, lasting only a day, due to their formulation being sensitive to environmental factors, particularly sebum. Sebum, a lipid substance produced by the sebaceous glands, alters the stability and adhesion of pigments deposited on the skin, thus reducing the duration and appearance of the makeup.

[0006] Other alternatives, such as semi-permanent tattoo services in salons, although offering a long-lasting solution, are often considered painful and invasive by users.

[0007] Furthermore, anhydrous gels, for example based on pigments associated with hydrophobic polymers and resins, ensure prolonged hold, but may nevertheless present certain limitations in terms of comfort, flexibility and resistance to transfer or to mechanical and chemical aggressions.

[0008] Users, concerned with obtaining more durable and resistant makeup for eyebrows and skin around the eye and eyebrows, are thus expressing a growing need for innovative cosmetic formulations.

[0009] These formulations must guarantee better product adhesion, prolonged hold, in particular increased resistance to sebum, and resistance to transfer during daily mechanical or chemical interactions, such as exposure to water or makeup removers. Description of the invention

[0010] There therefore remains a need to find new cosmetic compositions for making up keratinous materials, in particular eyebrows and skin around the eye and eyebrows, which allow for makeup with better hold of the deposit over time, in particular better resistance to sebum, better adhesion and flexibility of the deposit, and better resistance to transfer of the deposit.

[0011] There also remains a need for compositions that are resistant to various mechanical and chemical aggressions, for example water or makeup-removing compositions such as two-phase waters.

[0012] There also remains a need for compositions that are safe and easy to use. These compositions must also be kind to skin sensitivity and offer convenient application at home.

[0013] The present invention is specifically designed to meet all or part of these needs. Summary of the invention

[0014] These problems are solved by implementing a process for applying makeup to keratinous materials, particularly eyebrows including eyebrow hairs, the skin in which said hairs are implanted and their contours, 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:

[0015] [Chem.l]

[0016] formula (I) in which: - R1 represents a polysaccharide motif, specifically a disaccharide, on which n hydroxyl groups have been substituted by n -XC(O)-C(Ra)(Rb)-C(O)-R2 groups; R1 being further: a) possibly substituted by one or more hydroxy 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-, 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)(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 (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 - said composition (B) comprising at least iv) at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) in which: - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R, whether identical or different, represents an (CrC4)alkyl group, such as methyl; - R', whether identical or different, represents a phenyl group. - m and n, identical or different, represent an integer greater than or equal to 0, m+n being strictly greater than 0, preferably n represents an average integer from 1 to 20 and m represents an average integer from 1 to 30; (v) at least one of the compositions (A) and (B) comprising at least one particulate coloring matter.

[0017] The inventors have thus found, surprisingly, that applying ingredients i) to v) to keratinous materials improves the adhesion of the deposit colored on keratinous materials treated with this association, particularly with respect to liquid fatty substances, such as oils, and water.

[0018] For the purposes of the present invention, and unless otherwise indicated: - By "keratinous materials," we mean eyebrows including eyebrow hairs, the skin in which said hairs are implanted, and their contours. This term "keratinous materials," as used in the present invention, also extends to synthetic false eyebrows; - 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; - By "(hetero)aryl" we mean the aryl or heteroaryl groups; - By "(hetero)cycloalkyl" we mean cycloalkyl groups or heterocycloalkyl; - 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; - 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 links, comprising 1 to 4 heteroatoms chosen from 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, especially in Ci-C6, preferably in Ci-C4; an "alkoxy" radical is an alkyl-oxy radical for which the alkyl radical is a hydrocarbon radical, linear or branched, in Ci-C6 preferably in Ci-C4; 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; The "solvates" represent the hydrates as well as the association with linear or branched C1-C4 alcohols such as ethanol, isopropanol, n-propanol; - 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, even more preferably the composition is free of water. - The terms "coloring agent" and "coloring material" are equivalent.

[0019] Unless otherwise specified, the bounds delimiting the extent of a range of values ​​are included in that range of values.

[0020] Unless otherwise indicated, the quantities shown are expressed as mass percentages. Detailed description Makeup process for keratinous materials

[0021] The first object of the invention is a method for applying makeup to keratinous materials, particularly eyebrows, including eyebrow hairs, the skin from which said hairs are implanted and their contours, 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 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 - said composition (B) comprising (iv) at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) in which: - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R, whether identical or different, represents an (Ci-C4)alkyl group, such as methyl; - R', whether identical or different, represents a phenyl group. - m and n, identical or different, represent an integer greater than or equal to 0, m+n being strictly greater than 0, preferably n represents an average integer from 1 to 20 and m represents an average integer from 1 to 30; (v) at least one of the compositions (A) and (B) comprising at least one particulate coloring matter.

[0022] According to a particular embodiment of the invention, the process of the invention comprises the simultaneous application of ingredients i), iv) and v).

[0023] According to another particular embodiment of the invention, the process comprises at least 2 steps in which ingredients i), and iv) and v), (the latter ingredient being able to be found together with ingredient i) and / or with ingredient or ingredients iv)) are applied in separate and successive steps to the keratin materials, regardless of the order of application.

[0024] According to a particular embodiment, ingredient(s) i) are applied to the keratin materials, then ingredient(s) iv) are applied to the keratin materials, it being understood that ingredient(s) v) may be applied together with i) and / or iv).

[0025] According to another particular embodiment, ingredient(s) iv) are applied to the keratin materials, then ingredient(s) i) are applied to the keratin materials, it being understood that ingredient(s) v) may be applied together with i) and / or iv).

[0026] 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.

[0027] 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 to the keratinous materials.

[0028] In another variant, composition (A) and composition (B) are applied sequentially to the keratinous materials, composition (A) being able to be applied to the keratinous materials before composition (B) or vice versa.

[0029] Thus, according to this variant, the process according to the invention comprises two successive application steps on said keratinous materials, of composition (A) then of composition (B), or of composition (B) then of composition (A).

[0030] According to a particular embodiment of the invention, the process of making up keratinous materials is a process of making up eyebrows including eyebrow hairs, the skin of implantation of said hairs and their contours.

[0031] After application of compositions (A) and (B), a durable, flexible, and adherent colored deposit is advantageously obtained. The resulting deposit is also resistant to water, two-phase water, sebum, and dry rubbing.

[0032] According to a particular embodiment, the compositions are applied to dry keratinous materials. i) Compound of formula (I)

[0033] 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:

[0034] [Chem.2]

[0035] formula (I) in which: - R1 represents a polysaccharide motif, preferably a disaccharide, on which n hydroxy groups have been substituted by n -XC(O)-C(Ra)(Rb)-C(O)-R2 groups; 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 Ci to C6, linear or branched, saturated or unsaturated, preferably a (Ci-C4)alkyl 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.

[0036] 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:

[0037] [Chem.3]

[0038] 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.

[0039] 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.

[0040] According to a particular embodiment, the disaccharide motifs are selected from cellobiose, maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose, preferably sucrose.

[0041] According to a preferred embodiment, the disaccharides are sucrose.

[0042] 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.

[0043] 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.

[0044] 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:

[0045] [Tables 1] Compound CAS No. Chemical Name Chemical Structure 1236300-10-9 2,3,4,6-tetrakis(3-oxobutanoate) of α-D-Glucopyraiiasid, 1,3,4,6-tetrakis-O-(1,3-disxobutyl)-pd-hiKtoforanosyl (2) 2254710-49-9 - „:æ. ,1' y*" (3) Sticrose polyacetoacetate JW".".'.'.".'.'' ... / A *— a X

[0046] 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.

[0047] More preferably, compounds (I) or (la) are chosen from among the compounds of formula (3).

[0048] The compound(s) of formula (I) or (la) as defined above are preferably present in a content ranging from 0.5% to 90% by weight, more particularly from 1% to 80% by weight, from 1% to 60% by weight, relative to the total weight of the composition (A) containing them.

[0049] 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:

[0050] [Chem.4]

[0051] diagram in which: - R1, R2, Ra, Rb and n are as defined for the compound of formula (I); and - R3 represents a hydrogen atom, a (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 an oxygen atom.

[0052] 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.

[0053] According to a particular embodiment of the invention, R'(H)n is selected from acyclic polyols R'(H)n, in particular selected 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 octanediol, 1,10-decanediol, 2-methyl-l,3-propane diol, hexylene glycol, isoprene glycol.

[0054] 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:

[0055] [Chem.5] K

[0056] 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.

[0057] 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).

[0058] 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:

[0059] [Chem.6]

[0060] scheme in which R1, X and n are such as defined in formula (I) described above.

[0061] This type of process is known to those skilled in the art. For example, one can cite "Acetoacetamides, 2-hydroximinoacetoacetamides, and 2,3-bis(hydroxymino)-butyramides", Journal für Praktische Chemie (Leipzig), 323(2), 337-44, (1981) or Angewandte Makromolekulare Chemis, 9, 96-105, (1969). ii) C2-C4 monoalcohol

[0062] As previously stated, the composition (A) according to the invention comprises at least one monoalcohol comprising 2 to 4 carbon atoms.

[0063] Preferably, the monoalcohol(s) of the invention are chosen from among saturated or unsaturated, linear or branched monoalcohols comprising 2 to 4 carbon atoms.

[0064] In particular, the monoalcohol(s) may be chosen from ethanol, isopropanol, n-propanol, tert-butanol, butanol, and mixtures thereof, and preferably composition (A) includes at least ethanol.

[0065] In particular, composition (A) comprises the C2-C4 monoalcohol(s) in a content ranging from 1% to 70% by weight, preferably from 5% to 60% by weight, more preferably from 10% to 50% by weight, relative to the total weight of composition (A). iii) Water

[0066] As previously stated, the composition (A) according to the invention comprises at least water.

[0067] Preferably, the water used in the process of the invention is deionized water, sterilized water, or osmosis water.

[0068] In particular, composition (A) comprises water in a content ranging from 10% to 80% by weight, preferably from 20% to 70% by weight, more preferably from 25% to 65% by weight, relative to the total weight of composition (A). iv) Crosslinking agent

[0069] As stated above, the composition (B) according to the invention comprises at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) wherein: - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R, whether identical or different, represents an (Ci-C4)alkyl group, such as methyl; - R', whether identical or different, represents a phenyl group. - m and n, identical or different, represent an integer greater than or equal to 0, m+n being strictly greater than 0, preferably n represents an average integer from 1 to 20 and m represents an average integer from 1 to 30.

[0070] For the purposes of the invention, the term “crosslinking agent”, also referred to as “R”, designates a compound capable of establishing a covalent function with at least one acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention.

[0071] For the purposes of the present invention, it is understood that the terms “crosslinking agent” and “crosslinking agent” are equivalent.

[0072] Preferably, the composition (B) according to the invention comprises at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) wherein: - ALK and ALK' represent a propylene, - R represents a methyl group, - R' represents a phenyl group, - n represents an average integer ranging from 1 to 20 and m represents an average integer ranging from 1 to 30.

[0073] The crosslinking agent(s) is / are preferably present in a mass content ranging from 1% to 80% by weight, in particular ranging from 5% to 70% by weight, and more particularly from 7% to 60% by weight, relative to the total weight of the composition containing it or them.

[0074] Examples of compounds of formula (II) include those sold under the names "X-22-9409", "X-22-1660B-3", by the company Shin Etsu. (v) Particulate coloring matter

[0075] As previously stated, at least one of the compositions (A) and (B) according to the invention comprises at least one particulate coloring matter.

[0076] More particularly, composition (A) or composition (B) of the invention, advantageously composition (A), 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.

[0077] 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 skills of a person skilled in the art.

[0078] Preferably, composition (A) and / or composition (B) comprises at least one colouring material selected from pigments, direct dyes and their mixtures, more preferably pigments; more preferably the pigment(s) of the invention are selected from iron oxides, in particular yellow, red and black, titanium oxides and dioxides, even more preferably red iron oxides, yellow iron oxides, black iron oxides and titanium oxides and dioxides.

[0079] Additional oils

[0080] Composition (A) and / or composition (B) may further comprise one or more additional oils, different from the crosslinking agent, and preferably volatile.

[0081] By "oil" we mean a liquid fat at room temperature (20°C) and atmospheric pressure (760 mm of Hg).

[0082] By "hydrocarbon oil" is meant 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.

[0083] By "volatile oil" is meant an oil having a non-zero vapor pressure, at ambient temperature and atmospheric pressure, ranging in particular from 2.66 Pa to 40,000 Pa, in particular going to 13,000 Pa, and more particularly going to 1300 Pa.

[0084] By "non-volatile oil" is meant one whose vapor pressure at 20 °C is non-zero and less than 2.66 Pa, more particularly less than or equal to 0.13 Pa. By way of example, the vapor pressure can be measured according to the static method or by the isothermal thermogravimetric effusion method, according to the vapor pressure (OECD standard 104).

[0085] According to one embodiment of the invention, the oil(s) is / are chosen from volatile oils, in particular:

[0086] * hydrocarbon oils having 8 to 16 carbon atoms, and in particular:

[0087] - 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);

[0088] - linear alkanes, for example Cn-Cl6, alone or in mixtures, for example such as hexane, decane, undecane, tridecane, n-dodecane (Ci2) and n-tetradecane (CM), mixtures of n-undecane (Cn) and n-tridecane (Cn), and mixtures thereof;

[0089] - cyclic, non-aromatic, volatile C5-Ci2 alkanes;

[0090] * short-chain esters having from 3 to 8 carbon atoms in total, such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate;

[0091] * 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;

[0092] * 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;

[0093] *silicone oils comprising in particular, from 2 to 7 silicon atoms, these silicone oils having, optionally, 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.

[0094] At least one of the compositions (A) and / or (B) may optionally include one or more non-volatile oils, in particular selected from:

[0095] * non-volatile silicone oils, in particular selected from silicones non-volatile of the following INCI names: dimethicone (especially of viscosity greater than 6 cSt), dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyltrimethicone, diphenylsiloxy phenyl trimethicone; and their mixtures.

[0096] * 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, (C2rC28)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;

[0097] * non-volatile polar hydrocarbon oils that may be selected from:

[0098] 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;

[0099] ii) triglycerides consisting of esters of fatty acids and glycerol, in particular where the fatty acids may have chain lengths ranging from C4 to C36, and particularly from C[8 to C36, these oils can be linear or branched, saturated or unsaturated; examples include 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;

[0100] 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, 2-ethylhexyl palmitate, alkyl benzoate,polyethylene glycol diheptanoate, propylene glycol diethyl 2-hexanoate and mixtures thereof, hexyl laurate, neopentanoic acid esters such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, octyl-2-docecyl neopentanoate, 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;

[0101] iv) hydroxylated esters, such as polyglycerol-2 triisostearate;

[0102] v) aromatic esters, such as tridecyl trimellitate, benzoate of Ci2 alcohols -Ci5, 2-phenyl ethyl ester of benzoic acid, butyl octyl salicylate;

[0103] vi) linear fatty acid esters having a total carbon number from 35 to 70, such as pentaerythrityl tetrapelargonate;

[0104] vii) fatty alcohol esters or C24-C28 branched fatty acids, such as triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tridecyl-2-tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetradecanoate;

[0105] 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;

[0106] ix) ethers of formula RrO-R2 in which Ri and R2, identical or different, denote a linear, branched or cyclic C6-C24 alkyl group, preferably a C6-Ci8 alkyl group, and preferably a C8-Ci2 alkyl group. Examples of ethers include dilaury ether, diisostearyl ether, dicaprylyl ether, nonylphenyl ether, dodecyl dimethyl butyl ether, cetyl dimethyl butyl ether, cetyl isobutyl ether and mixtures thereof, preferably dicaprylyl ether;

[0107] x) 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 may be dicaprylyl carbonate (or dioctyl carbonate), di(ethyl-2-hexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, di-neopentyl carbonate, di-pentyl carbonate, di-neoheptyl carbonate, di-heptyl carbonate, di-isononyl carbonate, or di-nonyl carbonate; and preferably dioctyl carbonate;

[0108] xi) vinylpyrrolidone copolymers, such as vinylpyrrolidone / 1-hexadecene copolymer; and

[0109] xii) their mixtures.

[0110] More particularly, the non-volatile oil is 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 Ci5-Ci9 Alkane, and 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, as well as mixtures thereof.

[0111] More particularly, if at least one of the compositions (A) and / or composition (B) includes at least one additional oil, this is chosen from volatile oils, more preferably chosen from hydrocarbon oils having 8 to 16 carbon atoms, and in particular C8-Ci6 branched alkanes such as iso-alkanes such as Ci3-Ci6 Isoparaffin, isododecane, isodecane, isohexadecane, alone or in mixtures, preferably isododecane.

[0112] In particular, if at least one of the compositions (A) and / or (B) includes it, the quantity of oil(s), preferably volatile oil(s), varies from 0.1% to 90% by weight relative to the total weight of the composition, more particularly from 0.5% to 70% by weight, preferably from 1% to 50%, better from 2.5% to 30% by weight, relative to the total weight of the composition concerned.

[0113] Pigments

[0114] 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.

[0115] 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.

[0116] A pigment suitable for the invention can be chosen from among mineral pigments.

[0117] 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.

[0118] 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.

[0119] Advantageously, the pigments may be iron oxides and / or titanium dioxides.

[0120] A pigment suitable for the invention can be chosen from among organic pigments.

[0121] 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, 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 FR2679771.

[0122] 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).

[0123] The pigments according to the invention can also be in the form of composite pigments as described in patent EPI 184426. 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.

[0124] The organic pigment can also be a lacquer.

[0125] By "lacquer" is meant dyes adsorbed onto insoluble particles, the whole thus obtained remaining insoluble during use.

[0126] The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or borosilicate of calcium and aluminum, and aluminum. Among the dyes adsorbed onto organic substrates, carminic acid can be mentioned. Other colorants known by the following names include: D&C Red 21 (CI 45380), D&C Orange 5 (CI 45370), D&C Red 27 (CI 45410), D&C Orange 10 (CI 45425), D&C Red 3 (CI 45430), D&C Red 4 (CI 15510), D&C Red 33 (CI 17200), D&C Yellow 5 (CI 19140), D&C Yellow 6 (CI 15985), D&C Green (CI 61570), D&C Yellow 10 (CI 77002), D&C Green 3 (CI 42053), D&C Blue 1 (CI 42090), FDC Red 4, D&C Red 6, D&C Red 22, D&C Red 28, D&C Red 30, D&C Orange 4, D&C Yellow 8, D&C Green 5, D&C Red 17, D&C Green 6, D&C Yellow 11, D&C Violet 2, Sudan Red, carotenes (beta-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan Brown, quinoline yellow, annatto, curcumin, betanin (beetroot), carmine, copper chlorophyllin,Methylene blue, anthocyanins (enocianin, black carrot, hibiscus, elderberry), caramel, riboflavin, beetroot juice, and caramel.

[0127] As examples of lacquers, we can cite the product known under the following name: D & C Red 7 (CI 15 850 :1).

[0128] The pigment can also be a special effects pigment.

[0129] By "special effect pigments" is meant pigments which generally create a colored appearance (characterized by a certain shade, vibrancy and 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.

[0130] 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.

[0131] 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.

[0132] The pigments can be dispersed in the composition by means of a dispersing agent.

[0133] This dispersing agent may be a surfactant, an oligomer, a polymer, or a mixture of several of these, bearing 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 have at least one functional group that is compatible or soluble in the continuous medium. In particular, esters of 12-hydroxystearic acid, and of C8 to C2O fatty acids and polyols such as glycerol and diglycerin, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g / Mole, such as that sold under the name Solsperse 21000 by Avecia, polygyceryl-2 dipolyhydroxystearate (CTFA), sold under the name Dehymyls PGPH by Henkel, or polyhydroxystearic acid, such as that sold under the name Arlacel P100 by Uniqema, and mixtures thereof. Other dispersants usable 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 names DC2-5185 and DC2-5225 C. The pigments used in the composition may be surface-treated with an organic agent. According to a particular embodiment, the dispersing agent(s) are of the amino-silicone type, different from the (poly)amine compounds described later and are cationic.Preferably, the pigment(s) is / are chosen from mineral, mixed mineral-organic, or organic pigments.

[0134] 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.

[0135] According to another embodiment of the invention, the pigment(s) according to the invention are mineral pigments.

[0136] 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.

[0137] 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 iron oxides, in particular yellow, red and black, titanium oxides and dioxides, even more preferably red iron oxides, yellow iron oxides, black iron oxides and titanium oxides and dioxides.

[0138] In particular, the process of making up keratinous materials is a process of making up eyebrows including eyebrow hairs, the skin of implantation of said hairs and their contours.

[0139] Preferably, this is an eyebrow mascara, eyebrow gel, eyebrow pencil or eyebrow pen. Compositions

[0140] As previously stated, composition (A) and composition (B) according to the invention are distinct.

[0141] According to one embodiment, compositions (A) and (B) are packaged separately. By "packed separately," it is meant that compositions (A) and (B) are packaged inside two compartments, formed by two separate containers.

[0142] According to a particular embodiment, the composition (B) comprises an aqueous phase, and in particular comprises water.

[0143] According to an advantageous embodiment, the composition (B) is aqueous or hydroalcoholic.

[0144] 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 C2-C6 monoalcohol, preferably C2-C4, in particular ethanol, isopropanol and mixtures thereof.

[0145] If composition (B) includes it, the water content varies more particularly from 0.5% to 40% by weight, relative to the total weight of composition (B).

[0146] If composition (B) includes it, the monoalcohol content varies more particularly from 0.5% to 95% by weight, relative to the total weight of composition (B).

[0147] Composition (B), composition (A) or both, may further comprise one or more organic solvents, different from the aforementioned monoalcohols.

[0148] By "organic solvent" is meant an organic substance capable of dissolving another substance without chemically altering it.

[0149] Examples of organic solvents include: a) water-miscible polyols at room temperature (25 °C), in particular polyols having from 2 to 10 carbon atoms, preferably from 2 to 6 carbon atoms, such as glycerin, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, diglycerin; b) polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether; and c) aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0150] Preferably, the polyol is chosen from polyols having in particular 2 to 10 carbon atoms, preferably having 2 to 6 carbon atoms, such as glycerin.

[0151] Advantageously, if composition (B) and / or composition (A) includes it, the content of organic solvent(s), and more particularly of polyol, can vary from 0.5% to 30% by weight, relative to the total weight of the composition which contains it.

[0152] Composition (B) may be in anhydrous form, water-in-oil emulsion or oil-in-water emulsion. Kit and application

[0153] According to yet another aspect, the present invention also relates to a multi-compartment kit or device, particularly cosmetic, for applying makeup to keratinous materials, especially eyebrows, including eyebrow hairs, the skin from which said hairs are implanted and their contours, comprising at least two compositions (A) and (B) packaged separately with: - 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; - at least one second compartment separate from said first compartment, and containing at least composition (B) comprising (iv) at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) wherein: - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R, whether identical or different, represents an (Ci-C4)alkyl group, such as methyl; - R', whether identical or different, represents a phenyl group. - m and n, identical or different, represent an integer greater than or equal to 0, m+n being strictly greater than 0, preferably n represents an average integer from 1 to 20 and m represents an average integer from 1 to 30; (v) at least one of the compositions (A) and (B) comprising at least one particulate coloring matter.

[0154] Any type of applicator can be used for the deposition of the first and / or second composition.

[0155] The respective applicators of the first and second composition may be identical or distinct.

[0156] According to one embodiment of the invention, the first and second compositions can be applied by means of two separate applicator portions of the same applicator.

[0157] According to another variant, the makeup kit according to the present invention comprises one or more means of applying the first and second compositions.

[0158] The first and second cosmetic compositions included in the makeup kit of the invention can in particular be applied to the eyebrows, including the eyebrow hairs, the skin on which said hairs are implanted and their contours, 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.

[0159] In this case, the first composition can be applied using any applicator provided that it allows localized deposition over a part of the length of the keratinous material.

[0160] The threaded rod can be made of plastic or metal or any other suitable material.

[0161] The pen with a notched wheel is more particularly described in application US5851019 or FR2588733.

[0162] 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.

[0163] The makeup of keratinous materials can be carried out according to two methods. The first method consists of a multiple action 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 on the first composition called "basecoat" and on the keratinous materials.

[0164] According to a particularly advantageous embodiment, this packaging article is provided with two separate applicators.

[0165] The second method consists of pre-mixing the two compositions, just before applying the resulting composition to the keratinous materials.

[0166] 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 before application, such as a container and a stirrer.

[0167] The applicator may optionally be attached to the container. In particular, The applicator is attached to a rod which, in turn, is attached to the closing element.

[0168] 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.

[0169] The container, advantageously comprising the compartment(s) or reservoir(s), as well as the mixing container, may be at least partly made of Thermoplastic material. Examples of thermoplastic materials include polypropylene and polyethylene.

[0170] Alternatively, the containers are made of non-thermoplastic material, in particular glass or metal (or alloy).

[0171] 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 patent FR2792618.

[0172] 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

[0173] Compound 1 was synthesized according to the scheme below:

[0174] [Chem.7]

[0175] 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.

[0176] 100 g of sucrose and 406.55 g of tert-butyl acetoacetate are placed in a 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 140–150 °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. Preparation of compositions A and B

[0177] Compositions A 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. [Tables 2] Ingredients Composition A Compound 1 13.92% MA* Water Qsp 100 Ethanol 29.63 Red iron oxide 1.44 Yellow iron oxide 2.43 Black iron oxide 4.70 Titanium oxide 3.43 = Active ingredient

[0178] [Tables3] Ingredients Composition B Amino silicone (X-22-9409 from Shin Etsu) 13.92 Ethanol Qsp 100

[0179] 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). Formula to apply

[0180] Composition A and composition B are mixed in a mass ratio of 1:1, using a SpeedMixer® Hauschild DAC 150.1 FVZ) (10 grams, 1 cycle, 2 minutes 30 seconds, 2500 rpm). Application

[0181] The formula thus obtained was applied with a spatula to four Supplale® supports (SOUDOTIQUE reference RLXSUPNOIR, format: 30000 X 1200 MM X 0.7 MM) measuring 2.5 cm x 5 cm, at a rate of 0.02 g / cm2.

[0182] Drying takes place at room temperature for 24 hours.

[0183] Resistance to dryness, sebum, water, and two-phase water

[0184] Once dry, three of the Supplale® thus treated are immersed in 3 aggressors chemicals: - hot soapy water (temperature: 65 °C) containing 10% by weight of a DOP shower soap for 10 minutes; - sebum for 15 minutes; or - bi-phase water (La Roche Posay Respectissime waterproof eye makeup remover) for 3 minutes.

[0185] 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.

[0186] The fourth Supplale® is also rubbed against a towel (Chicopee® VERACLEAN™ Polish Plus 34x32cm) 10 times with a mass of 660 g, over a length of 34 cm (dry strength).

[0187] To measure color fastness, a color difference (AE) is measured between the initial deposit and the deposit after aggression. Persistence Protocol

[0188] 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).

[0189] 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.

[0190] The color retention of the deposits is evaluated by the color difference AE between Supplale® colored samples before and after exposure according to the protocol described above. The lower the AE value, the more resistant the color is to exposure.

[0191] The value of AE is calculated according to the following equation:

[0192] [Math.l] AE =

[0193] In this equation, L*a*b* represent the values ​​measured after staining of Supplale® and after having undergone an aggression, and Lo*ao*bo* represent the values ​​measured after staining of Supplale® but before aggression. Results

[0194] The evaluation results are summarized in the table below:

[0195] [Tables4] AE Standard deviation Dry resistance 2.3 1.3 Water resistance 1.0 1.4 Two-phase water resistance 5.9 6.9 Sebum resistance 1.4 9 7

Claims

1. Demands A method for making up keratinous materials, in particular eyebrows including eyebrow hairs, the skin in which said hairs are implanted and their contours, 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: formula (I) in which: - R1 represents a polysaccharide motif, in particular a disaccharide, on which n hydroxy groups have been substituted by n -XC(O)-C(Ra)(Rb)-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, carboxyl group -C(O)-OH, a vinyl group, and / or b) possibly interrupted by one or more heteroatoms or groups selected from -O-, -S-, carbonyl group -C(O)-, amine group -N(R'), or their combinations such as ester group -C(O)-O-, -OC(O)-, amide group -C(O)-N(R')-, -N(R')-C(O)-, urethane group -N(R')-C(O)-O- or -OC(O)-N(R')-, urea group -N(R')-(CO)-N(R')-, or carbonate group -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) group

2. rC4)alkyl, 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'), -S-CH 2-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 - said composition (B) comprising at least iv) at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) in which: - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R, whether identical or different, represents an (CrC4)alkyl group, such as methyl, - R', identical or different, represent a phenyl group, - m and n, identical or different, represent an integer greater than or equal to 0, m+n being strictly greater than 0, preferably n represents an average integer from 1 to 20 and m represents an average integer from 1 to 30; (v) at least one of the compositions (A) and (B) comprising at least one particulate coloring matter. 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 further being: a) optionally substituted by one or more hydroxy groups -OH, and / or b) optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -N(R'), preferably interrupted by one or more oxygen atoms, in which R' is as defined according to claim 1; - R2 is as defined according to claim 1, 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 according to 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 process according to any one of the preceding claims, wherein said composition (B) comprises at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) in which: - ALK and ALK' represent a propylene, - R represents a methyl group, - R' represents a phenyl group, - n represents an average integer ranging from 1 to 20 and m represents an average integer ranging from 1 to 30.

7. A method according to any one of the preceding claims, wherein the particulate coloring materials are selected from pigments, direct dyes and mixtures thereof, more preferably pigments; more preferably the pigment(s) are selected from iron oxides, in particular yellow, red and black, titanium oxides and dioxides, even more preferably red iron oxides, yellow iron oxides, black iron oxides and titanium oxides and dioxides.

8. A process according to any one of the preceding claims, wherein said composition (B) is anhydrous and comprises at least one C2-C6 monoalcohol, preferably C2-C4, in particular ethanol, isopropanol and mixtures thereof.

9. 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).

10. 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).

11. A multi-compartment kit or device, particularly cosmetic, for applying makeup to keratinous materials, especially eyebrows, including eyebrow hairs, the skin from which said hairs are implanted, and their contours, 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 according to any one of claims 1 to 5, ii) at least one monoalcohol comprising 2 to 4 carbon atoms; iii) water; - at least a second compartment separate from said first compartment, and containing at least composition (B) comprising iv) at least one amine crosslinking agent of the following formula: H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R')2]nO-Si(R)2-ALK'-NH2 (II) in which: - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R, whether identical or different, represents an (Ci-C4)alkyl group, such as methyl, - R', identical or different, represent a phenyl group, - m and n, identical or different, represent an integer greater than or equal to 0, m+n being strictly greater than 0, preferably n represents an average integer from 1 to 20 and m represents an average integer from 1 to 30; (v) at least one of the compositions (A) and (B) comprising at least one particulate coloring matter.