Process for making up keratin materials, comprising the application of at least one polysaccharide acetoacetate compound and a crosslinking agent

Abstract

The present invention relates to a process for making up keratin materials, comprising the application, to said keratin 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 functions, at least one monoalcohol comprising from 2 to 4 carbon atoms, and water, and said composition (B) comprising at least one amine crosslinking agent, at least one of the compositions (A) and (B) comprising at least one particulate colorant.

Description

Process for making up keratin materials, comprising the application of at least one polysaccharide acetoacetate compound and a crosslinking agent

[0001] The present invention relates to the cosmetics field of keratin materials, and mo especially to the making up of the eyebrows, including the eyebrow hairs, the skin for implantation of said hairs, and their outlines.

[0002] The invention especially aims at providing a process for making up keratin materials, comprising at least the application, to said keratin materials, of at least two distinct compositions (A) and (B).

[0003] Another subject-matter of the invention is a kit for making up keratin materials comprising at least two separately packaged compositions (A) and (B).Prior art

[0004] In the field of the making up of the eyebrows, consumers have access to a variety of products and solutions which, although partially meeting aesthetic and functional needs, exhibit significant limitations in terms of wear property and of resistance.

[0005] Among these solutions, pens and pigment-based eyebrow pencils often composed of aqueous formulae containing dyes, although appreciated for their ease of use, guarantee only a limited wear property, lasting only one day, due to their formulation, which is sensitive to environmental factors, in particular sebum. Sebum, a lipid substance produced by the sebaceous glands, detrimentally affects the stability and the fixing of pigments deposited on the skin, thus reducing the duration and the appearance of the make-up.

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

[0007] Moreover, anhydrous gels, for example based on pigments in combination with hydrophobic polymers and resins, provide a prolonged wear property but can nevertheless exhibit certain limitations as regards comfort, flexibility and resistance to transfer or to mechanical and chemical attacks.

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

[0009] These formulations must guarantee a better adhesion of the product, a prolonged wear property, in particular an increased resistance to sebum, and a resistance to transfer during daily mechanical or chemical interactions, such as exposure to water or to make-up removers.Disclosure of the invention

[0010] There thus remains a need to find novel cosmetic compositions for making up keratin materials, in particular eyebrows and skin around the eyes and eyebrows, which make it possible to obtain a make-up having a better wear property of the deposit over time, in particular a better resistance to sebum, a better adhesion and flexibility of the deposit, and a better resistance to transfer of the deposit.

[0011] There also exists a need for compositions which are resistant to various mechanical and chemical attacks, for example water or make-up-removing compositions, such as biphasic waters.

[0012] There also remains a need for compositions which are safe and easy to use. These compositions must also be respectful of skin sensitivity and offer practical application at home.

[0013] The present invention especially aims at meeting all or part of these needs.Summary of the invention

[0014] These problems are solved by a process for making up keratin materials, in particular the eyebrows, including eyebrow hairs, the skin for implantation of said hairs and their outlines, comprising at least the application, to said keratin materials, of at least two distinct compositions (A) and (B):

[0015] - said composition (A) comprising at least:

[0016] i) at least one compound selected from the compounds of formula (I) below comprising at least two acetoacetate functions, and also their optical isomers, geometrical isomers, their salts and their solvates, such as the hydrates: (I)

[0017] in which formula (I):

[0018] - R1represents a polysaccharide unit, in particular a disaccharide unit, on which n hydroxyl groups have been replaced by n -X-C(O)-C(Ra)(Rb)-C(O)-R2groups;

[0019] R1additionally being:

[0020] a) optionally substituted by one or more hydroxyl -OH, amine -N(R)2, with R representing a (C1-C4)alkyl group, such as methyl, or carboxyl -C(O)-OH groups, a vinyl group, and / or

[0021] b) optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, carbonyl -C(O)-, amine -N(R’) or their combinations, such as ester -C(O)-O-, -O-C(O)-, amide -C(O)-N(R’)-, -N(R’)-C(O)-, urethane -N(R’)-C(O)-O- or -O-C(O)-N(R’)-, urea -N(R’)-(CO)-N(R’)-, or carbonate -O-C(O)-O-, in which R’ represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms optionally substituted by at least one hydroxyl (-OH) group or optionally substituted by -X-C(O)-C(Ra)(Rb)-C(O)-R2; preferably, R’ represents a hydrogen atom or a (C1-C4)alkyl group;

[0022] - R2represents a saturated or unsaturated, linear or branched, monovalent C1to C6hydrocarbon radical, preferably a (C1-C4)alkyl group, such as methyl ortert-butyl, more preferentially methyl;

[0023] - Raand Rb, which are identical or different, represent a hydrogen atom or a (C1-C4)alkyl group, preferably hydrogen;

[0024] - X is a heteroatom or group chosen from -O-, -S-, -N(R’)-, -S-CH2-C(O)-O-, -O-C(O)-CH2-S-, -O-C(O)-N(R’)-, -N(R’)-C(O)-O- or -N(R’)-C(O)-N(R’)-; preferably, X represents O;

[0025] - n denotes an integer ranging from 2 to 10, particularly from 3 to 8; and

[0026] ii) at least one monoalcohol comprising from 2 to 4 carbon atoms;

[0027] iii) water; and

[0028] - said composition (B) comprising iv) at least one amine crosslinking agent of following formula:

[0029] H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)

[0030] in which:

[0031] - ALK and ALK’, which are identical or different, represent a linear or branched, preferably linear, (C1-C6)alkylene group, such as propylene,

[0032] - R, which are identical or different, represent a (C1-C4)alkyl group, such as methyl,

[0033] - R', which are identical or different, represent a phenyl group,

[0034] - m and n, which are identical or different, represent an integer greater than or equal to 0, m + n being strictly greater than 0; preferably, n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30;

[0035] v) at least one of the compositions (A) and (B) comprising at least one particulate colorant.

[0036] The inventors have thus found, surprisingly, that the application, to keratin materials, of the ingredients i) to v) makes it possible to improve the wear property of the coloured deposit on the keratin materials treated with this combination, in particular with regard to liquid fatty substances, such as oils, and water.

[0037] Within the meaning of the present invention and unless otherwise indicated:

[0038] - the term “keratin materials” is understood to mean the eyebrows, including the eyebrow hairs, the skin for implantation of said hairs and their outlines. This term of “keratin materials”, within the meaning of the present invention, also extends to synthetic false eyebrows;

[0039] - an “aryl” radical represents a monocyclic or fused or non-fused polycyclic hydrocarbon group comprising from 6 to 14 carbon atoms, at least one ring of which is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl;

[0040] - a “heteroaryl” radical represents a monocyclic or fused or non-fused polycyclic group comprising from 5 to 14 ring members and from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, at least one ring of which is aromatic; preferentially, 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, phenoxazolyl, pyrazinyl, pyrazolyl, pyrylyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyrylyl, triazolyl or xanthylyl;

[0041] - the term “(hetero)aryl” is understood to mean aryl or heteroaryl groups;

[0042] - the term “(hetero)cycloalkyl” is understood to mean cycloalkyl or heterocycloalkyl groups;

[0043] - a cyclic or heterocyclic radical or a non-aromatic part of an aryl or heteroaryl radical can also be substituted by one or more oxo groups;

[0044] - a hydrocarbon chain is unsaturated when it comprises one or more double bonds and / or one or more triple bonds;

[0045] - a “cyclic” or “cycloalkyl” radical is a monocyclic or fused or non-fused polycyclic, non-aromatic cyclic hydrocarbon radical containing from 5 to 14 carbon atoms which can comprise one or more unsaturations; preferably, the cycloalkyl is a cyclohexyl group;

[0046] - a “heterocyclic” or “heterocycloalkyl” radical is a monocyclic or fused or non-fused polycyclic, non-aromatic cyclic radical containing form 3 to 9 ring members and comprising from 1 to 4 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms; preferably, the heterocycloalkyl is chosen from epoxide, piperazinyl, piperidyl, morpholinyl and dithiolane;

[0047] - an “alkyl” radical is a saturated, linear or branched, in particular C1-C6, preferably C1-C4, hydrocarbon radical;

[0048] - an “alkoxy” radical is an alkyl-oxy radical for which the alkyl radical is a linear or branched C1-C6, preferentially C1-C4, hydrocarbon radical;

[0049] - a “sugar” radical is a monosaccharide or disaccharide radical. Mention may be made, as sugar radical, of: sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose or lactose;

[0050] - the term “monosaccharide” is understood to mean a simple 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 between 5 and 7 inclusive, preferably x = 6; they can be of D or L configuration and of α or β anomer, and also their salts and their solvates, such as the hydrates;

[0051] - the term “disaccharide” is understood to mean a double sugar which is a compound constituted of two simple sugars bonded together by O-glycosidic bonds, said compounds being constituted of two monosaccharides (also referred to as simple sugars) as defined above, said monosaccharide units comprising at least 5, preferably 6, carbon atoms; in particular, the simple sugar units are linked together in 1,4 or 1,6 fashion as α (alpha) or β (beta) anomer, it being possible for each sugar unit to be of L or D configuration, and also its salts and its solvates, such as the hydrates of said monosaccharides; it more particularly concerns polymers formed from two simple 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 between 5 and 7 inclusive, preferably x = 6, and y an integer which represents x - 1;

[0052] - the “solvates” represent the hydrates and also the combination with linear or branched C1-C4alcohols, such as ethanol, isopropanol or n-propanol;

[0053] - the term “anhydrous” is understood to mean having an amount of less than 5% by weight of water, preferentially of less than 3% by weight of water, better still of less than 1% by weight of water, with respect to the total weight of the composition in question; more preferentially still, the composition is devoid of water;

[0054] - the terms “colouring agent” and “colorant” are equivalent.

[0055] Unless otherwise indicated, the limits delimiting the extent of a range of values are included in this range of values.

[0056] Unless otherwise indicated, the amounts indicated are expressed as percentages by weight.Detailed descriptionProcess for making up keratin materials

[0057] The first subject-matter of the invention is a process for making up keratin materials, in particular the eyebrows, including eyebrow hairs, the skin for implantation of said hairs and their outlines, comprising at least the application, to said keratin materials, of at least two distinct compositions (A) and (B):

[0058] - said composition (A) comprising at least:

[0059] i) at least one compound of formula (I) comprising at least two acetoacetate functions as described above, and also its optical isomers, geometrical isomers, its salts and its solvates, such as the hydrates:

[0060] ii) at least one monoalcohol comprising from 2 to 4 carbon atoms;

[0061] iii) water; and

[0062] - said composition (B) comprising iv) at least one amine crosslinking agent of following formula:

[0063] H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)

[0064] in which:

[0065] - ALK and ALK’, which are identical or different, represent a linear or branched, preferably linear, (C1-C6)alkylene group, such as propylene,

[0066] - R, which are identical or different, represent a (C1-C4)alkyl group, such as methyl,

[0067] - R', which are identical or different, represent a phenyl group,

[0068] - m and n, which are identical or different, represent an integer greater than or equal to 0, m + n being strictly greater than 0; preferably, n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30;

[0069] v) at least one of the compositions (A) and (B) comprising at least one particulate colorant.

[0070] According to a particular embodiment of the invention, the process of the invention comprises the simultaneous application of the ingredients i), iv) and v).

[0071] According to another particular embodiment of the invention, the process comprises at least two stages in which the ingredients i), and iv) and v) (it being possible for the last ingredient to be present together with the ingredient i) and / or with the ingredient(s) iv)), are applied in separate and successive stages to the keratin materials, independently of the order of application.

[0072] According to a particular embodiment, the ingredient(s) i) are applied to the keratin materials and then the ingredient(s) iv) are applied to the keratin materials, it being understood that the ingredient(s) v) can be found applied together with i) and / or iv).

[0073] According to another particular embodiment, the ingredient(s) iv) are applied to the keratin materials and then the ingredient(s) i) are applied to the keratin materials, it being understood that the ingredient(s) v) can be found applied together with i) and / or iv).

[0074] According to a particular embodiment, the composition (A) and the composition (B) are applied simultaneously or sequentially, independently of the order of application, to the keratin materials.

[0075] In a preferred alternative form of the invention, a composition obtained by an extemporaneous mixing, at the time of the application, of the composition (A) and of the composition (B) as are defined above is applied to the keratin materials.

[0076] In another alternative form, the composition (A) and the composition (B) are applied sequentially to the keratin materials, it being possible for the composition (A) to be applied to the keratin materials before the composition (B), orvice versa.

[0077] Thus, according to this alternative form, the process according to the invention comprises two successive stages of application, to said keratin materials, of the composition (A) and then of the composition (B) or of the composition (B) and then of the composition (A).

[0078] According to a particular embodiment of the invention, the process for making up keratin materials is a process for making up the eyebrows, including the eyebrow hairs, the skin for implantation of said hairs and their outlines.

[0079] After application of the compositions (A) and (B), a persistent, flexible and adherent coloured deposit is advantageously obtained. The deposit obtained is additionally resistant to water, to biphasic water, to sebum and to dry rubbing.

[0080] According to a particular embodiment, the compositions are applied to dry keratin materials.i) Compound of formula (I)

[0081] As indicated above, a composition (A) according to the invention comprises at least one compound of formula (I), and also its optical or geometrical isomers, its salts and its solvates, such as the hydrates: (I)

[0082] in which formula (I):

[0083] - R1represents a polysaccharide unit, preferably a disaccharide unit, on which n hydroxyl groups have been replaced by n -X-C(O)-C(Ra)(Rb)-C(O)-R2groups;

[0084] R1additionally being:

[0085] a) optionally substituted by one or more hydroxyl -OH, dialkylamine -N(R)2, with R representing a (C1-C4)alkyl group, such as methyl, or carboxyl -C(O)-OH groups, a vinyl group, and / or

[0086] b) optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, carbonyl -C(O)-, amine -N(R’) or their combinations, such as ester -C(O)-O-, -O-C(O)-, amide -C(O)-N(R’)-, -N(R’)-C(O)-, urethane -N(R’)-C(O)-O- or -O-C(O)-N(R’)-, urea -N(R’)-(CO)-N(R’)-, or carbonate -O-C(O)-O-, in which R’ represents a hydrogen atom or a linear or branched alkyl group having from 1 to 4 carbon atoms optionally substituted by at least one hydroxyl (-OH) group or optionally substituted by -X-C(O)-C(Ra)(Rb)-C(O)-R2; preferably, R’ represents a hydrogen atom or a (C1-C4)alkyl group;

[0087] - R2represents a saturated or unsaturated, linear or branched, monovalent C1to C6hydrocarbon radical, preferably a (C1-C4)alkyl group, such as methyl ortert-butyl, more preferentially methyl;

[0088] - Raand Rb, which are identical or different, represent a hydrogen atom or a (C1-C4)alkyl group, preferably hydrogen;

[0089] - X is a heteroatom or group chosen from -O-, -S-, -N(R’)-, -S-CH2-C(O)-O-, -O-C(O)-CH2-S-, -O-C(O)-N(R’)-, -N(R’)-C(O)-O- or -N(R’)-C(O)-N(R’)-; preferably, X represents O;

[0090] - n denotes an integer ranging from 2 to 10, particularly from 3 to 8.

[0091] According to a particular embodiment of the invention, the compound of formula (I) is chosen from those of formula (Ia) and also their optical or geometrical isomers, their salts and their solvates, such as the hydrates:

[0092] in which formula (Ia):

[0093] - R1represents a polysaccharide unit, preferably a disaccharide unit;

[0094] R1additionally being:

[0095] a) optionally substituted by one or more hydroxyl -OH groups, and / or

[0096] b) optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S- or -N(R’)-, preferably interrupted by one or more oxygen atoms, in which R’ is as defined in the formula (I);

[0097] - R2is as defined above; preferably, R2represents a linear or branched (C1-C6)alkyl group, preferably a (C1-C4)alkyl group, particularly methyl ortert-butyl, such as methyl; and

[0098] - n being as defined above; preferably, n denotes an integer ranging from 2 to 8.

[0099] According to a preferred embodiment, the compounds of formulae (I) and (Ia) are such that R1represents a disaccharide unit on which n hydroxyl groups have been replaced by n -O-C(O)-CH2-C(O)-R2groups, with R2and n being as defined above.

[0100] According to a particular embodiment, the disaccharide units are chosen from cellobiose, maltose, lactose, raffinose, saccharose (sucrose), trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose or xylobiose, preferably sucrose.

[0101] According to a preferred embodiment, the disaccharides are sucrose.

[0102] According to a particular embodiment, the compounds of formula (I) and (Ia) are such that n denotes an integer ranging from 2 to 8; more particularly, n denotes an integer ranging from 3 to 8, more particularly from 4 to 8.

[0103] In an alternative form of the invention, the compound of formula (I) or (Ia) as defined above is a mixture of compounds of different chemical structures.

[0104] More particularly, the compound(s) of formulae (I) and (Ia) are chosen from the group consisting of the compounds defined in table 1 below, and also their optical isomers, their salts and their solvates, such as the hydrates:

[0105] CAS compound No.Chemical nameChemical structure(1) 1236300-10-91,3,4,6-tetrakis-O-(1,3-dioxobutyl)-β-D-fructofuranosyl-α-D-glucopyranoside 2,3,4,6-tetrakis(3-oxobutanoate) (2) 2254710-49-9- (3)sucrose polyacetoacetate

[0106] in which R1are chosen, independently of one another, from -C(O)-CH2-C(O)-CH3and H with at least two R1radicals representing -C(O)-CH2-C(O)-CH3; preferably, at least three radicals represent -C(O)-CH2-C(O)-CH3.

[0107] More preferentially, the compounds (I) or (Ia) are chosen from the compounds of formula (3).

[0108] The compound(s) of formula (I) or (Ia) 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, for example from 1% to 60% by weight, with respect to the total weight of the composition (A) containing them.

[0109] The compound(s) of formula (I) can be obtained by (poly)condensation(s) of n equivalents of dicarbonyl reactant with a nucleophilic reactant R1(H)ncomprising n equivalents of nucleophilic functions, according to the following scheme:

[0110] in which scheme:

[0111] - R1, R2, Ra, Rband n are as defined for the compound of formula (I); and

[0112] - R3represents a hydrogen atom, a (C1-C4)alkyl group, such as methyl, ethyl, isobutyl or t-butyl, or an electrofuge group, such as CHal3, or Hal3C-SO2-, such as triflate, with Hal, which are identical or different, representing a halogen atom;

[0113] - X and X’ represent, independently of one another, an oxygen or sulfur atom, preferably an oxygen atom.

[0114] These (poly)condensation methods are known to a person skilled in the art; mention may be made, for example, of “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.

[0115] According to a particular embodiment of the invention, R1(H)nis chosen from acyclic polyols R1(H)nin particular chosen 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, hexanediol, neopentyl glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 2,4-butanediol, 3,4-butanediol, 1,4-pentanediol, 1,5-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,6-hexanediol, 1,2-octanediol, 1,8-octanediol, 1,10-decanediol, 2-methyl-1,3-propanediol, hexylene glycol or isoprene glycol.

[0116] According to another alternative form, the compound(s) of formula (I) or (Ia) are obtained by (poly)condensation(s) of n equivalents of propylenedioxy carbonyl reactant with a polyamine nucleophilic reactant R1(NH2)ncomprising n equivalents of -NH2nucleophilic functions, according to the following scheme:

[0117] in which scheme:

[0118] - R1, R2, Raand n are as defined for the compound of formula (I);

[0119] - Rb’and Rc’, which are identical or different, represent a hydrogen atom or a (C1-C4)alkyl group.

[0120] This type of synthesis process is known to a person skilled in the art; mention may be made, for example, of “Acetoacetylation with 2,2,6-Trimethyl-4H-1,3-dioxin-4-one: A Convenient Alternative to Diketene”,Journal of Organic Chemistry, 50(14), 2431-5 (1985) or “Synthesis of New Biginelli Polycondensates: Renewable Materials with Tunable High Glass Transition Temperatures”,Polymer International, 70(5), 506-513 (2021).

[0121] According to another alternative form, the compound(s) of formula (I) or (Ia) are obtained by (poly)condensation(s) of n equivalents of diketene reactant with a nucleophilic reactant R1(H)ncomprising n equivalents of nucleophilic functions, according to the following scheme:

[0122] in which scheme R1, X and n are as defined in the formula (I) described above.

[0123] This type of process is known to a person skilled in the art. Mention may be made, for example, of “Acetoacetamides, 2-Hydroximinoacetoacetamides, and 2,3-Bis(hydroximino)butyramides”,Journal fürPraktischeChemie(Leipzig), 323(2), 337-44 (1981) orAngewandteMakromolekulareChemie, 9, 96-105 (1969).ii) C2-C4 Monoalcohol

[0124] As indicated above, the composition (A) according to the invention comprises at least one monoalcohol comprising from 2 to 4 carbon atoms.

[0125] Preferably, the monoalcohol(s) of the invention is(are) chosen from saturated or unsaturated, linear or branched, monoalcohols comprising from 2 to 4 carbon atoms.

[0126] In particular, the monoalcohol(s) can be chosen from ethanol, isopropanol, n-propanol, tert-butanol, butanol and their mixtures, and preferably the composition (A) comprises at least ethanol.

[0127] In particular, the composition (A) comprises the C2-C4monoalcohol(s) in a content ranging from 1% to 70% by weight, preferably from 5% to 60% by weight, more preferentially from 10% to 50% by weight, with respect to the total weight of the composition (A).iii) Water

[0128] As indicated above, the composition (A) according to the invention comprises at least water.

[0129] Preferably, the water used in the process of the invention is deionized water, sterilized water, or osmosis water.

[0130] In particular, the composition (A) comprises water in a content ranging from 10% to 80% by weight, preferably from 20% to 70% by weight and more preferentially from 25% to 65% by weight, with respect to the total weight of the composition (A).iv) Crosslinking agent

[0131] As indicated above, the composition (B) according to the invention comprises at least one amine crosslinking agent of following formula:

[0132] H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)

[0133] in which:

[0134] - ALK and ALK’, which are identical or different, represent a linear or branched, preferably linear, (C1-C6)alkylene group, such as propylene,

[0135] - R, which are identical or different, represent a (C1-C4)alkyl group, such as methyl,

[0136] - R', which are identical or different, represent a phenyl group,

[0137] - m and n, which are identical or different, represent an integer greater than or equal to 0, m + n being strictly greater than 0; preferably, n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30.

[0138] Within the meaning of the invention, the term “crosslinking agent”, also referred to as “R”, denotes a compound capable of establishing a covalent bounding with at least one acetoacetate function of the compound(s) of formula (I) employed in the treatment process according to the invention.

[0139] Within the meaning of the present invention, it is understood that the terms “crosslinking agent” and “crosslinker” are equivalent.

[0140] Preferably, the composition (B) according to the invention comprises at least one amine crosslinking agent of following formula:

[0141] H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)

[0142] in which:

[0143] - ALK and ALK’ represent a propylene,

[0144] - R represent a methyl,

[0145] - R' represent a phenyl group,

[0146] - n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30.

[0147] The crosslinking agent(s) is (are) preferably present in a content by weight ranging from 1% to 80% by weight, in particular ranging from 5% to 70% by weight and more particularly ranging from 7% to 60% by weight, with respect to the total weight of the composition containing it or them.

[0148] Mention may be made, as examples of compounds of formula (II), of those sold under the names "X-22-9409" and "X-22-1660B-3" by Shin Etsu.v) Particulate colorant

[0149] As indicated above, at least one of the composition (A) and of the composition (B) according to the invention comprises at least one particulate colorant.

[0150] More particularly, the composition (A) or the composition (B) of the invention, advantageously the composition (A), comprises at least one water-soluble or water-insoluble particulate colorant, and preferably in a proportion of at least 0.01% by weight, with respect to the total weight of the composition under consideration.

[0151] For obvious reasons, this amount is liable to vary significantly from the viewpoint of the intensity of the desired colour effect and of the colour intensity afforded by the colorants under consideration, and its adjustment clearly falls within the competence of a person skilled in the art.

[0152] Preferably, the composition (A) and / or the composition (B) comprise(s) at least one colorant chosen from pigments, direct dyes and their mixtures, more preferentially pigments; more preferentially, the pigment(s) of the invention are chosen from iron oxides, in particular yellow, red and black iron oxides, and titanium oxides and dioxides, more preferentially still red iron oxides, yellow iron oxides, black iron oxides and titanium oxides and dioxides.

[0153] Additional oils

[0154] The composition (A) and / or the composition (B) can also comprise one or more additional oils, different from the crosslinking agent, and preferably volatile.

[0155] The term “oil” is understood to mean a fatty substance which is liquid at ambient temperature (20°C) and atmospheric pressure (760 mmHg).

[0156] The term “hydrocarbon oil” is understood to mean an oil formed essentially of, indeed even constituted of, carbon and hydrogen atoms, and possibly of oxygen and nitrogen atoms, and not containing a silicon or fluorine atom. It can contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0157] The term “volatile oil” denotes an oil having a non-zero vapour pressure, at ambient temperature and atmospheric pressure, ranging in particular from 2.66 Pa to 40 000 Pa, in particular ranging to 13 000 Pa and more particularly ranging to 1300 Pa.

[0158] The term “non-volatile oil” denotes an oil, the vapour pressure of which 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 vapour pressure can be measured according to the static method or by the effusion method by isothermal thermogravimetry, according to the vapour pressure (OCDE Standard 104).

[0159] According to one embodiment of the invention, the oil(s) is (are) chosen from volatile oils, in particular:

[0160] * hydrocarbon oils having from 8 to 16 carbon atoms, and in particular:

[0161] - branched C8-C16alkanes, for example isoalkanes (also referred to as isoparaffins), such as C13-C16Isoparaffin, isododecane, isodecane, isohexadecane, and for example the oils sold under the Isopar or Permethyl trade names, alone or as mixtures, preferably isododecane (also referred to as 2,2,4,4,6-pentamethylheptane);

[0162] - linear alkanes, for example C11-C16alkanes, alone or as mixtures, for example such as hexane, decane, undecane, tridecane, n-dodecane (C12) and n-tetradecane (C14), mixtures of n-undecane (C11) and of n-tridecane (C13), and their mixtures;

[0163] - volatile non-aromatic cyclic C5-C12alkanes;

[0164] * short-chain esters having from 3 to 8 carbon atoms in total, such as ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate;

[0165] * carbonate hydrocarbon oils of structure R’1-O-C(O)-O-R’2in which R’1and R’2independently denote a linear, branched or cyclic C4-C8alkyl group, preferably a C4-C8alkyl group, advantageously chosen from dibutyl carbonate or dipentyl carbonate;

[0166] * ether oils of formula R1-O-R2in which R1and R2independently denote a linear, branched or cyclic C4-C8alkyl group, preferably a C4-C8alkyl group;

[0167] * 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, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and their mixtures.

[0168] At least one of the compositions (A) and / or (B) can optionally comprise one or more non-volatile oils chosen in particular from:

[0169] * non-volatile silicone oils chosen in particular from non-volatile silicones having the following INCI names: dimethicone (in particular with a viscosity of greater than 6 cSt), dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyl trimethicone, diphenylsiloxy phenyl trimethicone; and also their mixtures;

[0170] * non-volatile non-polar hydrocarbon oils chosen in particular from linear or branched compounds of mineral or synthetic origin: i) paraffin oil, ii) squalane, isoeicosane, iii) mixtures of saturated linear hydrocarbons, more particularly C15-C28hydrocarbons, such as the mixtures, the INCI names of which are (C15-C19)alkane, (C18-C21)alkane, (C21-C28)alkane, iv) polybutenes, which are or are not hydrogenated, v) polyisobutenes, which are or are not hydrogenated, preferably hydrogenated, vi) polydecenes, which are or are not hydrogenated, vii) decene / butene copolymers, butene / isobutene copolymers and viii) their mixtures;

[0171] * non-volatile polar hydrocarbon oils which can be chosen from:

[0172] i) saturated or unsaturated, linear or branched, C10-C26fatty alcohols, preferably monoalcohols; advantageously, the C10-C26alcohols are fatty alcohols, which are preferably branched when they comprise at least 16 carbon atoms; preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferentially from 12 to 22 carbon atoms, such as in particular lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyloctanol, 2-undecylpentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and their mixtures;

[0173] ii) triglycerides constituted of esters of fatty acids and of glycerol, in particular the fatty acids of which can have chain lengths varying from C4to C36and in particular from C18to C36, it being possible for these oils to be linear or branched and saturated or unsaturated; mention may in particular be made, by way of examples, of heptanoic or octanoic triglycerides, caprylic / capric acid triglycerides, vegetable oils, such as wheatgerm oil, sunflower oil, grapeseed oil, sesame seed oil, maize oil, apricot kernel oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, peanut oil, coconut oil, argan oil, kaya oil; the liquid fraction of shea butter and the liquid fraction of cocoa butter; and also their mixtures;

[0174] iii) linear aliphatic hydrocarbon esters of formula R-C(O)-OR’ in which R-C(O)-O- represents the carboxylic acid residue 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 being advantageously at least 10; chosen in particular 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 of polyalcohols, such as propylene glycol dioctanoate, cetyl octanoate or tridecyl octanoate, 2-ethylhexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol bis(2-ethylhexanoate) and their mixtures, hexyl laurate, neopentanoic acid esters, such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate or 2-octyldodecyl neopentanoate, isononanoic acid esters, such as isononyl isononanoate, isotridecyl isononanoate or octyl isononanoate, oleyl erucate, isopropyl lauroyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate or myristyl myristate;

[0175] iv) hydroxylated esters, such as polyglyceryl-2 triisostearate;

[0176] v) aromatic esters such as tridecyl trimellitate, the benzoate of C12-C15alcohols, the 2-phenylethyl ester of benzoic acid, or butyloctyl salicylate;

[0177] vi) esters of linear fatty acids having a total carbon number ranging from 35 to 70, such as pentaerythrityl tetrapelargonate;

[0178] vii) esters of C24-C28branched fatty acids or fatty alcohols, such as triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2-decyltetradecanoate), pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetrakis(2-decyltetradecanoate);

[0179] viii) the polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and of diol, such as those with the INCI name Dilinoleic Acid / Butanediol Copolymer or Dilinoleic Acid / Propanediol Copolymer; the polyesters obtained by condensation of fatty acid dimer and of diol dimer, such as Dimer Dilinoleyl Dimer Dilinoleate;

[0180] ix) ethers of formula R1-O-R2in which R1and R2, which are identical or different, denote a linear, branched or cyclic C6-C24alkyl group, preferably a C6-C18alkyl group and in a preferred way a C8-C12alkyl group. Mention may be made, by way of example of ether, of dilauryl ether, diisostearyl ether, dicaprylyl ether, nonyl phenyl ether, dodecyl dimethylbutyl ether, cetyl dimethylbutyl ether, cetyl isobutyl ether and their mixtures, preferably dicaprylyl ether;

[0181] x) carbonates of formula R8-O-C(O)-O-R9, with R8and R9, which are identical or different, representing a linear or branched C4to C12and preferentially C6to C10alkyl chain; the carbonate oils can be dicaprylyl carbonate (or dioctyl carbonate), bis(2-ethylhexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate or dinonyl carbonate and preferably dioctyl carbonate;

[0182] xi) vinylpyrrolidone copolymers, such as vinylpyrrolidone / 1-hexadecene copolymer; and

[0183] xii) their mixtures.

[0184] More particularly, the non-volatile oil is chosen from hydrogenated or non-hydrogenated polyisobutenes, preferably hydrogenated polyisobutenes, such as, for example, the non-volatile compounds of the Parleam®range; C15-C19alkane mixtures, and from linear aliphatic hydrocarbon esters of formula R-C(O)-OR' in which R-C(O)-O represents a carboxylic acid residue comprising from 2 to 40 carbon atoms and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, as are defined above, in particular isononyl isononanoate, and also their mixtures.

[0185] More particularly, if at least one of the compositions (A) and / or (B) comprises at least one additional oil, the latter is chosen from volatile oils, more preferentially chosen from hydrocarbon oils having from 8 to 16 carbon atoms, and in particular branched C8-C16alkanes, for example isoalkanes, such as C13-C16Isoparaffin, isododecane, isodecane, isohexadecane, alone or as mixtures, preferably isododecane.

[0186] In particular, if at least one of the compositions (A) and / or (B) comprises it / them, the amount of oil(s), preferably volatile oil(s), varies from 0.1% to 90% by weight, with respect to the total weight of the composition, more particularly from 0.5% to 70% by weight, preferentially from 1% to 50% by weight, better still from 2.5% to 30% by weight, with respect to the total weight of the composition concerned.

[0187] Pigments

[0188] Within the meaning of the invention, the term “pigment” is understood to mean any compound capable of imparting colour to keratin materials. These compounds have a solubility in water at 25°C and at atmospheric pressure (760 mmHg) of less than 0.05% by weight and preferably of less than 0.01% by weight.

[0189] Mention may in particular be made, as pigments suitable for the invention, of the organic and / or inorganic pigments known in the art, in particular those which are described in Kirk-Othmer’s Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry. These pigments can be synthetic or natural. These pigments can be provided in the form of a pigment paste or powder. They can be coated or uncoated. These pigments can, for example, be chosen from inorganic pigments, organic pigments, lakes, special effect pigments, such as pearlescent agents or glitter flakes, and their mixtures.

[0190] A pigment suitable for the invention can be chosen from inorganic pigments.

[0191] The term “inorganic pigment” is understood to mean any pigment which corresponds to the definition of Ullmann’s Encyclopedia in the "Pigments, Inorganic" chapter. Mention may be made, among the inorganic pigments of use in the present invention, of manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium, zirconium or cerium oxides or dioxides, and also of zinc, iron or chromium oxides.

[0192] It can also concern a pigment having a structure which can be, for example, of sericite / brown iron oxide / titanium dioxide / silica type. Such a pigment is sold, for example, under the reference Coverleaf NS or JS by Chemicals and Catalysts, and exhibits a contrast ratio in the vicinity of 30. It can also concern pigments having a structure which can be, for example, of the type of silica microspheres containing iron oxide. An example of a pigment exhibiting this structure is that sold by Miyoshi under the reference PC Ball PC-LL-100 P, this pigment being constituted of silica microspheres containing yellow iron oxide.

[0193] Advantageously, the pigments can be iron oxides and / or titanium dioxides.

[0194] A pigment suitable for the invention can be chosen from organic pigments.

[0195] The term “organic pigment” is understood to mean any pigment which corresponds to the definition of Ullmann’s Encyclopedia in the "Pigments, Organic" chapter. Mention may be made, among the organic pigments of use in the present invention, of nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal-complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine and quinophthalone compounds. In particular, the white or coloured organic pigments can be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Colour Index under the references CI 42090, 69800, 69825, 74100 and 74160, the yellow pigments codified in the Colour Index under the references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000 and 47005, the green pigments codified in the Colour Index under the references CI 61565, 61570 and 74260, the orange pigments codified in the Colour Index under the references CI 11725, 45370 and 71105, the red pigments codified in the Colour 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 and 75470, and the pigments obtained by oxidative polymerization of indole or phenol derivatives as are described in Patent FR 2 679 771.

[0196] Mention may also be made, by way of example, of pigment pastes of organic pigments, such as the products sold by Hoechst under the names: 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 (Cl 74160); Cosmenyl Green GG: Pigment Green 7 (CI 74260); Cosmenyl Black R: Pigment Black 7 (CI 77266).

[0197] The pigments in accordance with 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 providing the fixing of the organic pigments to the core and at least one organic pigment at least partially covering the core.

[0198] The organic pigment can also be a lake.

[0199] The term “lake” is understood to mean dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.

[0200] The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium. Mention may be made, among the dyes adsorbed onto organic substrates, of carminic acid. Mention may also be made of the dyes known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985) D & C Green (CI 61 570), D & C Yellow 10 (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 (CI 42 090), FDC Red 4, D & C Red 6, D & C Red 22, D & C Red 28, D & C Red 30, D & C Orange 4, D & C Yellow 8, D & C Green 5, D & C Red 17, D & C Green 6, D & C Yellow 11, D & C Violet 2, Sudan red, carotenes (β-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocyanin, black carrot, hibiscus, elderberry), riboflavin, beet juice and caramel.

[0201] Mention may be made, by way of example of lakes, of the product known under the following name: D & C Red 7 (CI 15 850:1).

[0202] The pigment can also be a special effect pigment.

[0203] The term “special effect pigments” is understood to mean pigments which create in a general way a coloured appearance (characterized by a certain shade, a certain vividness and a certain brightness) which is non-uniform and which changes as a function of the conditions of observation (light, temperature, angles of observation, and the like). They thereby contrast with coloured pigments, which provide a conventional uniform opaque, semi-transparent or transparent colour.

[0204] Several types of special effect pigments exist: those having a low refractive index, such as fluorescent or photochromic pigments, and those having a higher refractive index, such as pearlescent agents, interference pigments or glitter flakes.

[0205] 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 preferentially between 30 nm and 50 µm.

[0206] The pigments can be dispersed in the composition by virtue of a dispersant.

[0207] This dispersant can be a surfactant, an oligomer, a polymer or a mixture of several of them, carrying one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they can become attached physically or chemically to the surface of the pigments. These dispersants additionally exhibit at least one functional group compatible with or soluble in the continuous medium. In particular, esters of 12-hydroxystearic acid in particular and of C8to C20fatty acid and of polyols, such as glycerol or diglycerol, are used, 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 (CTFA name), sold under the reference Dehymyls PGPH by Henkel, or also polyhydroxystearic acid, such as that sold under the reference Arlacel P100 by Uniqema, and their mixtures. Mention may be made, as other dispersants which can be used in the compositions of the invention, of quaternary ammonium derivatives of polycondensed fatty acids, such as Solsperse 17 000 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 can be surface-treated with an organic agent. According to a particular embodiment, the dispersant(s) are of aminosilicone type, different from the (poly)amino compounds described subsequently, and are cationic. Preferably, the pigment(s) is (are) chosen from inorganic, mixed inorganic / organic or organic pigments.

[0208] According to a particular embodiment, the pigment(s) according to the invention are organic pigments, preferentially organic pigments surface-treated with an organic agent chosen from silicone compounds.

[0209] According to another embodiment of the invention, the pigment(s) according to the invention are inorganic pigments.

[0210] The colorants, preferably the pigments, can be present in concentrations ranging from 0.01% to 50% by weight, preferably from 0.02% to 40% by weight and more particularly from 0.05% to 30% by weight, with respect to the total weight of the composition which contains them.

[0211] Preferably, the particulate colorant(s) is (are) chosen from pigments, direct dyes and their mixtures, preferably pigments; more preferentially, the pigment(s) of the invention are chosen from iron oxides, in particular yellow, red and black iron oxides, and titanium oxides and dioxides, more preferentially still red iron oxides, yellow iron oxides, black iron oxides and titanium oxides and dioxides.

[0212] In particular, the process for making up keratin materials is a process for making up the eyebrows, including the eyebrow hairs, the skin for implantation of said hairs and their outlines.

[0213] Preferably, it concerns an eyebrow mascara, an eyebrow gel, an eyebrow pencil or an eyebrow pen.Compositions

[0214] As indicated above, the composition (A) and the composition (B) according to the invention are distinct.

[0215] According to one embodiment, the compositions (A) and (B) are packaged separately. The term “packaged separately” is understood to mean that the compositions (A) and (B) are packaged inside two compartments formed by two distinct containers.

[0216] According to a particular embodiment, the composition (B) comprises an aqueous phase and in particular comprises water.

[0217] According to an advantageous alternative form, the composition (B) is aqueous or aqueous / alcoholic.

[0218] According to another particular embodiment of the invention, the composition (B) is an anhydrous composition. In particular, the composition (B) is anhydrous and comprises at least one C2-C6, preferably C2-C4, monoalcohol, in particular ethanol, isopropanol and their mixtures.

[0219] If the composition (B) comprises it, the content of water varies more particularly from 0.5% to 40% by weight, with respect to the total weight of the composition (B).

[0220] If the composition (B) comprises it, the content of monoalcohol varies more particularly from 0.5% to 95% by weight, with respect to the total weight of the composition (B).

[0221] The composition (B), the composition (A) or alternatively both can additionally comprise one or more organic solvents, different from the abovementioned monoalcohols.

[0222] The term “organic solvent” is understood to mean an organic substance capable of dissolving another substance without chemically modifying it.

[0223] Mention may be made, as organic solvent, for example, of: a) polyols which are miscible with water at ambient temperature (25°C) chosen in particular from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerol, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol or diglycerol; b) polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and diethylene glycol monomethyl ether; and also c) aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and their mixtures.

[0224] Preferably, the polyol is chosen from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerol.

[0225] Advantageously, if the composition (B) and / or the composition (A) comprise(s) it / them, the content of organic solvent(s), and more particularly of polyol, can vary from 0.5% to 30% by weight, with respect to the total weight of the composition which contains it / them.

[0226] The composition (B) can be in anhydrous, water-in-oil emulsion or oil-in-water emulsion form.Kit and application

[0227] According to yet another of its aspects, the present invention is also targeted at a multi-compartment kit or device, in particular a cosmetic kit or device, for making up keratin materials, in particular the eyebrows, including the eyebrow hairs, the skin for implantation of said hairs and their outlines, comprising at least two compositions (A) and (B) packaged separately with:

[0228] - at least one first compartment containing at least the composition (A) comprising: i) at least one compound of formula (I) or (Ia) as defined above, ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water;

[0229] - at least one second compartment distinct from said first compartment and containing at least the composition (B) comprising iv) at least one amine crosslinking agent of following formula:

[0230] H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)

[0231] in which:

[0232] - ALK and ALK’, which are identical or different, represent a linear or branched, preferably linear, (C1-C6)alkylene group, such as propylene,

[0233] - R, which are identical or different, represent a (C1-C4)alkyl group, such as methyl,

[0234] - R', which are identical or different, represent a phenyl group,

[0235] - m and n, which are identical or different, represent an integer greater than or equal to 0, m + n being strictly greater than 0; preferably, n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30;

[0236] v) at least one of the compositions (A) and (B) comprising at least one particulate colorant.

[0237] Any type of applicator can be used for the purpose of the deposition of the first and / or of the second composition.

[0238] The respective applicators of the first and of the second composition can be identical or distinct.

[0239] According to an alternative form of the invention, the first and second compositions can be applied by means of two distinct applicative portions of the same applicator.

[0240] According to another alternative form, the make-up kit according to the present invention comprises one or more means of application of the first and second compositions.

[0241] The first and second cosmetic compositions comprised in the make-up kit of the invention can be applied in particular to the eyebrows, including the eyebrow hairs, the skin for implantation of said hairs and their outlines, using a sponge, a flocked applicator, a coarse brush, a fine brush, a comb, a threaded stem or a pen equipped with a notched wheel. They can also be applied with the fingers.

[0242] In this case, the first composition can be applied using any applicator provided that it makes possible a deposit localized over a portion of the length of the keratin material.

[0243] The threaded stem can be made of plastic or of metal or any other suitable material.

[0244] The pen equipped with a notched wheel is more particularly described in Application US 5 851 019 or FR 2 588 733.

[0245] This pen makes possible precise metering of the product to be applied at the outlet of the pen after actuation of a notched wheel or of a push button which causes a piston to advance at each rotation / pressing action.

[0246] Keratin materials can be made up according to two processes. The first route consists of a multifaceted action by the user, namely at least in two stages, the first consisting of the application of the "base coat" composition and the second consisting of the application of the "top coat" composition, in all or part, to the first "base coat" composition and to the keratin materials.

[0247] According to a particularly advantageous embodiment, this packaging article is equipped with two distinct applicators.

[0248] The second route consists in premixing the two compositions, just before applying the resulting composition to the keratin materials.

[0249] Whatever the route selected by the user, the packaging kit comprises two separate compartments or reservoirs for each of the compositions (A) and (B), each reservoir or compartment being closed by a closing member, and optionally at least one suitable applicator, preferably two applicators. It should be noted that the packaging kit can also comprise means for combining the two compositions before application, such as a container and a stirrer.

[0250] The applicator can optionally be integral with the container. In particular, the applicator is integral with a stem which, itself, is integral with the closing member.

[0251] The closing member can be coupled to the container by screwing. Alternatively, the coupling between the closing member and the container is carried out other than by screwing, in particular via a bayonet mechanism, by click-fastening or by clamping. The term “click-fastening” is understood in particular to mean any system involving the crossing of a bead or of a collar of material by elastic deformation of a portion, in particular of the closing member, followed by return to the elastically unconstrained position of said portion after the crossing of the bead or of the collar.

[0252] The container, advantageously comprising the compartment(s) or reservoir(s), and also the mixing container, can be at least partly made of thermoplastic material. Mention may be made, as examples of thermoplastic materials, of polypropylene or polyethylene.

[0253] Alternatively, the containers are made of non-thermoplastic material, in particular of glass or of metal (or alloy).

[0254] The containers are preferably equipped with a wiper positioned in the vicinity of at least one opening of the container. Such a wiper makes it possible to wipe the applicator and optionally the stem, with which it may be integral. Such a wiper is described, for example, in Patent FR 2 792 618.

[0255] The invention is illustrated in greater detail in the following examples. The amounts are indicated as percentages by weight.Compound 1: Sucrose having acetoacetate functions

[0256] Compound 1 was synthesized according to the scheme below:

[0257] in which scheme R1, which are identical or different, represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3group, it being understood that at least two R1radicals represent -C(O)-CH2-C(O)-CH3.

[0258] 100 g of sucrose and 406.55 g of tert-butyl acetoacetate are placed in a 1-litre three-necked round-bottomed flask equipped with a mechanical stirrer and with a distillation column. The reaction medium is heated using an oil bath (temperature of the oil bath 140°C-150°C) for 4 hours. After 4 hours, NMR confirms the grafting of the acetoacetate function. The reaction medium is subsequently concentrated on a rotary evaporator at 150°C under continuous vacuum. A viscous orange-yellow liquid is obtained, corresponding after analysis to the expected product.Preparation of the compositions A and B

[0259] The compositions A and B are prepared from the contents indicated in the tables below. The contents are expressed as percentages by weight, with respect to the total weight of the composition under consideration.Table 2:

[0260] IngredientsComposition ACompound 113.92% AM*Waterq.s. for 100Ethanol29.63Red iron oxide1.44Yellow iron oxide2.43Black iron oxide4.70Titanium oxide3.43

[0261] *AM = active materialTable 3:

[0262] IngredientsComposition BAminosilicone (X-22-9409 from Shin Etsu)13.92Ethanolq.s. for 100

[0263] The compositions are prepared by simple mixing of the ingredients described in detail in the tables above using a SpeedMixer®(Hauschild DAC 150.1 FVZ) (10 grams, 1 cycle, 2 minutes 30 seconds, 2500 rpm).Formula to be applied

[0264] The composition A and the composition B are mixed in a 1:1 ratio by weight using a SpeedMixer®(Hauschild DAC 150.1 FVZ) (10 grams, 1 cycle, 2 minutes 30 seconds, 2500 rpm).Application

[0265] The formula thus obtained was applied with a spatula to fourSupplale®supports (Soudotique, reference RLXSUPNOIR, format: 30 000 × 1200 mm × 0.7 mm) with dimensions of 2.5 cm × 5 cm, at a rate of 0.02 g / cm².

[0266] Drying takes place at ambient temperature for 24 hours.

[0267] Dry strength, resistance to sebum, resistance to water and resistance to biphasic water

[0268] Once dry, three of theSupplale®items thus treated are immersed in 3 chemical aggressors:

[0269] - hot soapy water (temperature: 65°C) comprising 10% by weight of a DOP shower soap for 10 minutes;

[0270] - sebum for 15 minutes; or

[0271] - biphasic water (La Roche Posay Respectissime waterproof eye make-up remover) for 3 minutes.

[0272] After the immersion, theSupplale®items were rubbed against a cloth (Chicopee®Veraclean™ Polish Plus 34 × 32 cm) 10 times with a weight of 660 g, over a length of 34 cm.

[0273] The fourthSupplale®item is also rubbed against a cloth (Chicopee®Veraclean™ Polish Plus 34 x 32 cm) 10 times with a weight of 660 g, over a length of 34 cm (dry strength).

[0274] In order to measure the wear property of the colour, a colour difference (ΔE) is measured between the initial deposit and the deposit after attack.Persistence protocol

[0275] The persistence of the colour of the deposits was evaluated in the CIE L*a*b* system, using a Konica CM 700d®spectrophotometer from Minolta (illuminant D65, angle 10°, specular component included).

[0276] In this L*a*b* system, L* represents the intensity of the colour, a* indicates the green / red colour axis and b* the blue / yellow colour axis.

[0277] The persistence of the colour of the deposits is evaluated by the colour difference ΔE between the colouredSupplale®items before attack, then after having undergone an attack according to the protocol described above. The smaller the ΔE value, the more persistent the colour is with regard to the attacks.

[0278] The ΔE value is calculated according to the following equation:

[0279] In this equation, L*, a* and b* represent the values measured after colouring theSupplale®items and after having undergone an attack, and L0*, a0* and b0* represent the values measured after colouring theSupplale®items but before attack.Results

[0280] The results of the evaluations are summarized in the table below:

[0281] Table 4:ΔEStandard deviationDry strength2.31.3Resistance to water1.01.4Resistance to biphasic water5.96.9Resistance to sebum1.42.2

[0282] The compositions illustrated in the above examples are especially suitable for application to the eyebrow area.

Claims

Process for making up keratin materials, for example the eyebrows, including eyebrow hairs, the skin for implantation of said hairs and their outlines, said process comprising at least the application, to said keratin materials, of at least two distinct compositions (A) and (B), wherein:- said composition (A) comprising at least:i) at least one compound of formula (I) below comprising at least two acetoacetate functions, and also its optical isomers, geometrical isomers, its salts and its solvates, such as the hydrates:(I)wherein:- R1represents a polysaccharide unit, preferably a disaccharide unit, on which n hydroxyl groups have been replaced by n -X-C(O)-C(Ra)(Rb)-C(O)-R2groups;wherein R1may be:a)optionallysubstituted by one or more hydroxyl -OH, amine -N(R)2, with R representing a (C1-C4)alkyl group, such as methyl, or carboxyl -C(O)-OH groups, a vinyl group, and / orb)optionallyinterrupted by one or more heteroatoms or groups chosen from -O-, -S-, carbonyl -C(O)-, amine -N(R’) or their combinations, such as ester -C(O)-O-, -O-C(O)-, amide -C(O)-N(R’)-, -N(R’)-C(O)-, urethane -N(R’)-C(O)-O- or -O-C(O)-N(R’)-, urea -N(R’)-(CO)-N(R’)-, or carbonate -O-C(O)-O-, in which R’ represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms optionally substituted by at least one hydroxyl (-OH) group or optionally substituted by -X-C(O)-C(Ra)(Rb)-C(O)-R2; preferably, R’ represents a hydrogen atom or a (C1-C4)alkyl group;- R2represents a saturated or unsaturated, linear or branched, monovalent C1to C6hydrocarbon radical, preferably a (C1-C4)alkyl group, such as methyl ortert-butyl, more preferentially methyl;- Raand Rb, which are identical or different, represent a hydrogen atom or a (C1-C4)alkyl group, preferably hydrogen;- X is a heteroatom or group chosen from -O-, -S-, -N(R’)-, -S-CH2-C(O)-O-, -O-C(O)-CH2-S-, -O-C(O)-N(R’)-, -N(R’)-C(O)-O- or -N(R’)-C(O)-N(R’)-; preferably, X represents O;- n denotes an integer ranging from 2 to 10, particularly from 3 to 8; andii) at least one monoalcohol comprising from 2 to 4 carbon atoms;iii) water; and- said composition (B) comprising iv) at least one amine crosslinking agent of following formula:H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)in which:- ALK and ALK’, which are identical or different, represent a linear or branched, preferably linear, (C1-C6)alkylene group, such as propylene,- R, which are identical or different, represent a (C1-C4)alkyl group, such as methyl,- R', which are identical or different, represent a phenyl group,- m and n, which are identical or different, represent an integer greater than or equal to 0, m + n being strictly greater than 0; preferably, n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30;v) at least one of the compositions (A) and (B) comprising at least one particulate colorant.Process according to the preceding claim, in which the compound(s) of formula (I) is (are) chosen from those of formula (Ia) and also their optical or geometrical isomers, their salts and their solvates, such as the hydrates:in which formula (Ia):- R1represents a polysaccharide unit, preferably a disaccharide unit;R1additionally being:a) optionally substituted by one or more hydroxyl -OH groups, and / orb) optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S- or -N(R’)-, preferably interrupted by one or more oxygen atoms, in which R’ is as defined according to Claim 1;- R2is as defined according to Claim 1; preferably, R2represents a linear or branched (C1-C6)alkyl group, preferably a (C1-C4)alkyl group, particularly methyl ortert-butyl, such as methyl; and- n being as defined according to Claim 1; preferably, n denotes an integer ranging from 2 to 8.Process according to either one of the preceding claims, in which the compound(s) of formula (I) or (Ia) is (are) such that R1represents a disaccharide unit on which n hydroxyl groups have been replaced by n -O-C(O)-CH2-C(O)-R2groups, with R2and n being as defined according to either one of Claims 1 and 2.Process according to any one of the preceding claims, in which R1represents a disaccharide unit chosen from cellobiose, maltose, lactose, raffinose, saccharose (sucrose), trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose or xylobiose, preferably sucrose.Process according to any one of the preceding claims, in which the compound(s) of formulae (I) and (Ia) are chosen from the following compounds, and also their optical isomers, their salts and their solvates, such as the hydrates:CAS compound No.Chemical nameChemical structure(1) 1236300-10-91,3,4,6-tetrakis-O-(1,3-dioxobutyl)-β-D-fructofuranosyl-α-D-glucopyranoside 2,3,4,6-tetrakis(3-oxobutanoate)(2) 2254710-49-9-(3)sucrose polyacetoacetatein which R1are chosen, independently of one another, from -C(O)-CH2-C(O)-CH3and H with at least two R1radicals representing -C(O)-CH2-C(O)-CH3; preferably, at least three radicals represent -C(O)-CH2-C(O)-CH3;more preferentially, the compounds of formulae (I) and (Ia) are chosen from the compounds of formula (3).Process according to any one of the preceding claims, in which said composition (B) comprises at least one amine crosslinking agent of following formula:H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)in which:- ALK and ALK’ represent a propylene,- R represent a methyl,- R' represent a phenyl group,- n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30.Process according to any one of the preceding claims, in which the particulate colorants are chosen from pigments, direct dyes and their mixtures, more preferentially pigments; more preferentially, the pigment(s) are chosen from iron oxides, in particular yellow, red and black iron oxides, and titanium oxides and dioxides, more preferentially still red iron oxides, yellow iron oxides, black iron oxides and titanium oxides and dioxides.Process according to any one of the preceding claims, in which said composition (B) is anhydrous and comprises at least one C2-C6, preferably C2-C4, monoalcohol, in particular ethanol, isopropanol and their mixtures.Process according to any one of the preceding claims, characterized in that it comprises two successive stages of application, to said keratin materials, of the composition (A) and then of the composition (B) or of the composition (B) and then of the composition (A).Process according to any one of Claims 1 to 9, characterized in that it comprises a stage of application, to said keratin materials, of a composition obtained by an extemporaneous mixing, at the time of the application, of said composition (A) and of said composition (B).Multi-compartment kit or device, in particular a cosmetic kit or device, for making up keratin materials, in particular the eyebrows, including the eyebrow hairs, the skin for implantation of said hairs and their outlines, 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 (Ia) as defined according to any one of Claims 1 to 5, ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water;- at least one second compartment distinct from said first compartment and containing at least the composition (B) comprising iv) at least one amine crosslinking agent of following formula:H2N-ALK-Si(R)2-[O-Si(R)2]m-[O-Si(R’)2]n-O-Si(R)2-ALK’-NH2(II)in which:- ALK and ALK’, which are identical or different, represent a linear or branched, preferably linear, (C1-C6)alkylene group, such as propylene,- R, which are identical or different, represent a (C1-C4)alkyl group, such as methyl,- R', which are identical or different, represent a phenyl group,- m and n, which are identical or different, represent an integer greater than or equal to 0, m + n being strictly greater than 0; preferably, n represents a mean integer ranging from 1 to 20 and m represents a mean integer ranging from 1 to 30;v) at least one of the compositions (A) and (B) comprising at least one particulate colorant.

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