Process for making up keratin materials, comprising the application of at least one polysaccharide acetoacetate compound and a crosslinking agent
A two-composition process using polysaccharide acetoacetate and crosslinking agents enhances the persistence and resistance of cosmetic deposits on keratin materials, addressing the limitations of existing compositions by providing a non-tacky, transfer-resistant, and glossy finish.
Patent Information
- Application Number
- PCT/EP2025/066361
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-06-14
- Filing Date
- 2025-06-12
- Publication Date
- 2025-12-18
AI Technical Summary
Existing cosmetic compositions for keratin materials, such as skin, lips, and eyelashes, fail to provide a non-tacky, transfer-resistant, long-lasting, and glossy deposit that withstands mechanical and chemical attacks, including water, sebum, and edible fats.
A process involving the application of two distinct compositions: (A) comprising a polysaccharide acetoacetate compound and a monoalcohol, and (B) a crosslinking agent like aminoalkylpoly alkoxy silanes, which are applied separately or together to enhance the persistence and resistance of the deposit.
The process results in a persistent, non-tacky, and glossy deposit that resists transfer and chemical attacks, providing long-lasting color and sheen on keratin materials.
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Abstract
Description
[0001] Title: Process for making up keratin materials, comprising the application of at least one polysaccharide acetoacetate compound and a crosslinking agent
[0002] Technical field
[0003] The present invention relates more particularly to the cosmetic field of keratin materials, and notably to that of making up the skin and / or lips and / or eyelashes and / or eyebrows. It thus aims to provide 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). The invention also relates to a kit for making up keratin materials comprising at least two compositions (A) and (B) packaged separately.
[0004] Prior art
[0005] Cosmetic products conventionally require the use of one or more film-forming polymers in order to obtain a quality deposit of these products on keratin materials, and in particular to satisfy the expectations detailed below.
[0006] Thus, in the field of skin and lip makeup, it is most particularly expected that the deposit formed does not transfer on contact with the fingers or clothing.
[0007] It must also have good resistance to contact with water, notably rain or during showering or even perspiration, and also resistance to sebum, or even to contact with edible fats, notably edible oils when this deposit is formed on the lips. Moreover, this deposit must be comfortable or even glossy.
[0008] For this purpose, dispersions of polymer particles of nanometric size are used in makeup products such as mascaras, eyeliners or eyeshadows, and more particularly in their organic and notably oily phases, as film-forming agent.
[0009] Thus, document FR 2 741 530 for example proposes for this purpose, for the temporary colouring of keratin fibres, the use of a dispersion of film-forming polymer particles including at least one acidic function and at least one pigment dispersed in the continuous phase of said dispersion. The colourings obtained via this dyeing method are not always satisfactory in terms of persistence, notably with respect to shampoo washing. Specifically, in general, these polymers do not afford deposits on keratin materials that satisfy all the abovementioned requirements, namely very good water resistance, in particular with respect to shampoo washing for the hair, which make it possible to adjust the gloss or invisibility qualities and which, in the case of haircare use, provide very satisfactory styling hold.
[0010] Document EP 3 250 177 Al describes the use of acetoacetylated compounds in the field of keratin fibres. The keratin materials treated with said acetoacetylated compounds do not always give satisfactory results, especially in terms of persistence with respect to water and shampoo washing.
[0011] These documents do not make it possible to obtain deposits that are non-tacky, transfer little, are comfortable, and are long-lasting.
[0012] Disclosure of the invention
[0013] There is thus still a need for cosmetic compositions intended for application to the skin and / or lips and / or eyelashes and / or eyebrows which make it possible to obtain a deposit that is non-tacky, which transfers little, if at all, and which is glossy, comfortable and long- lasting.
[0014] There is also still a need for compositions which are resistant to various mechanical and chemical attacks, for example make-up removing compositions such as biphase waters.
[0015] There also remains a need for compositions that afford sheen and colour persistence qualities.
[0016] The present invention is specifically directed to meeting some or all of these needs.
[0017] Summary of the invention
[0018] These problems are solved by performing 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):
[0019] - said composition (A) comprising at least: i) at least one compound of formula (I) comprising at least two acetoacetate functions, including the optical or geometrical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates:
[0020] [Chem 1] in which formula (I):
[0021] - R1represents a polysaccharide unit, notably a disaccharide unit, on which n hydroxy groups have been substituted with n -O-C(O)-CH2-C(O)-R2groups;
[0022] R1also being: a) optionally substituted with one or more hydroxyl OH or amine -N(R)2 groups with R representing a (Ci-C4)alkyl group such as methyl, carboxyl -C(O)-OH, a vinyl group, and / or b) optionally interrupted with one or more heteroatoms or groups chosen from O, S, carbonyl -C(O)-, amine -N(R’), or combinations thereof 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, an alkyl group containing from 1 to 4 carbon atoms optionally substituted with at least one hydroxyl group (OH), or optionally substituted with -X-C(O)-C(Ra)(Rb)-C(O)-R2; preferably, R’ represents a hydrogen atom or a (Ci-C4)alkyl group;
[0023] - R2represents a linear or branched, saturated or unsaturated Ci to Ce monovalent hydrocarbon-based radical, preferably a (Ci-C4)alkyl group such as methyl or tert-butyl, more preferentially methyl;
[0024] - Raand Rb, which may be identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably hydrogen;
[0025] - 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;
[0026] - n denotes an integer ranging from 2 to 10, particularly from 3 to 8; and ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and iv) at least one particulate colorant;
[0027] - said composition (B) comprising at least v) a crosslinking agent chosen from (poly)amine compounds, notably aminoalkylpoly alkoxy silanes, a,co-diaminooxaalkanes, chitosans, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains.
[0028] The inventors have thus found, surprisingly, that the application of ingredients i), ii), iii), iv) and v) to keratin materials makes it possible to improve the persistence of the coloured deposit on the keratin materials treated with this combination, notably with respect to liquid fatty substances such as oils and water.
[0029] For the purposes of the present invention and unless otherwise indicated:
[0030] The term “cosmetic active agent” means an organic or organosilicon compound or a mineral compound which can be incorporated into a cosmetic composition to give an effect on keratin fibres, whether this effect is immediate or provided by repeated applications. As examples of cosmetic active agents, mention may be made of coloured or uncoloured, fluorescent or non-fluorescent compounds such as optical brighteners, or UVA and / or UVB screening agents, anti-ageing active agents or active agents intended for providing a benefit to the skin such as active agents having action on the barrier function, deodorant active agents, antiperspirant active agents, desquamating active agents, antioxidant active agents, moisturizing active agents, sebum-regulating active agents, active agents intended for combating the effects of pollution, antimicrobial or bactericidal active agents, fragrances and colorants such as direct dyes or pigments, preferably pigments.
[0031] Preferentially, the cosmetic active agents are chosen from a) colorants chosen from pigments, direct dyes, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, and c) mixtures thereof.
[0032] The term “fatty substance” is understood, for the purposes of the present invention, to mean an organic compound insoluble in water at ordinary temperature (25 °C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1% and even more preferentially less than 0.1%); in addition, the fatty substances are soluble in organic solvents under the same temperature and pressure conditions, for instance in halogenated solvents such as chloroform or dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene.
[0033] An “aryl” radical represents a monocyclic or fused or non-fused polycyclic hydrocarbonbased group comprising from 6 to 14 carbon atoms, and at least one ring of which is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl.
[0034] A “heteroaryl” radical represents a monocyclic or fused or non-fused polycyclic, 5- to 14-membered group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl, triazolyl and xanthylyl.
[0035] The term “(hetero)aryl” means aryl or heteroaryl groups.
[0036] The term “(hetero)cycloalkyl” means cycloalkyl or heterocycloalkyl groups.
[0037] The “aryl” or “heteroaryl” radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from:
[0038] * a Ci-C6and preferably C1-C4 (poly)(hydroxy)alkyl radical;
[0039] * a halogen atom such as chlorine, fluorine or bromine;
[0040] * a hydroxyl group;
[0041] * a C1-C2 alkoxy radical; a C2-C4 (poly)hydroxyalkoxy radical;
[0042] * an amino radical;
[0043] * an amino radical substituted with one or two identical or different Ci-Ce, preferably C1-C4, alkyl radicals;
[0044] * an acylamino radical (-NR-COR’) in which the radical R is a hydrogen atom;
[0045] * a C1-C4 alkyl radical and the radical R’ is a C1-C4 alkyl radical; a carbamoyl radical ((R)2N-C0-) in which the radicals R, which may be identical or different, represent a hydrogen atom, or a C1-C4 alkyl radical;
[0046] * an alkylsulfonylamino radical (R’SCh-NR-) in which the radical R represents a hydrogen atom, or a C1-C4 alkyl radical and the radical R’ represents a C1-C4 alkyl radical, or a phenyl radical;
[0047] * an aminosulfonyl radical ((R)2N-SO2-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical; * a carboxylic radical in acid form or salified (preferably with an alkali metal or a substituted or unsubstituted ammonium) form;
[0048] * a cyano group (CN);
[0049] * a polyhalo(Ci-C4)alkyl group, preferentially trifluoromethyl (CF3);
[0050] The cyclic or heterocyclic part of a non-aromatic radical may be substituted with at least one substituent borne by a carbon atom, chosen from the following groups:
[0051] * hydroxyl;
[0052] * C1-C4 alkoxy, C2-C4 (poly )hydroxy alkoxy;
[0053] * alkylcarbonylamino ((RCO-NR’-) in which the radical R’ is a hydrogen atom, or a Ci- C4 alkyl radical ; and the radical R is a C1-C2 alkyl radical, or an amino radical substituted with one or two identical or different C1-C4 alkyl groups;
[0054] * alkylcarbonyloxy ((RCO-O-) in which the radical R is a C1-C4 alkyl radical, or an amino radical substituted with one or two identical or different C1-C4 alkyl groups;
[0055] * alkoxycarbonyl ((RO-CO-) in which the radical R is a C1-C4 alkyl radical, or an amino radical substituted with one or two identical or different C1-C4 alkyl groups; a cyclic or heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical, may also be substituted with one or more oxo groups; a hydrocarbon-based chain is unsaturated when it includes one or more double bonds and / or one or more triple bonds; an “aryl” radical represents a monocyclic or fused or non-fused polycyclic hydrocarbonbased group comprising from 6 to 14 carbon atoms, and at least one ring of which is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl; a “heteroaryl” radical represents a monocyclic or fused or non-fused polycyclic, 5- to 14-membered group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydro thiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl, triazolyl and xanthylyl; a “cyclic” or “cycloalkyl” radical is a monocyclic or fused or non-fused polycyclic, nonaromatic cyclic hydrocarbon-based radical containing from 5 to 14 carbon atoms, which may include one or more unsaturations; the cycloalkyl is preferably a cyclohexyl group; a “heterocyclic” or “heterocycloalkyl” radical is a monocyclic or fused or non-fused polycyclic 3- to 9-membered non-aromatic cyclic radical, including 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; an “alkyl” radical is a linear or branched, in particular Ci-Ce and preferably C1-C4 saturated hydrocarbon-based radical; an “alkoxy” radical is an alkyl-oxy radical for which the alkyl radical is a linear or branched Ci-Ce and preferentially C1-C4 hydrocarbon-based radical; a “(poly) (hydroxy) alkyl” radical refers to a Ci-Ce, preferably C1-C4, alkyl radical optionally substituted with one or more hydroxyl radicals, preferably substituted with from 1 to 4 hydroxy groups, more particularly between 1 and 3; a “sugar” radical is a monosaccharide or disaccharide radical. Sugar radicals that may be mentioned include: sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose;
[0056] The term “monosaccharide” refers to a monosaccharide sugar comprising at least 5 carbon atoms of formula Cx(HiO)xwith 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 may be of D or L configuration, and of alpha or beta anomer, including the salts thereof and the solvates thereof such as the hydrates.
[0057] The term “disaccharide” refers to a disaccharide sugar which is a compound constituted of two saccharides bonded together via O-glycosidic bonds, said compounds being constituted of two monosaccharides as defined previously, said monosaccharide units comprising at least 5, preferably 6, carbon atoms; in particular, the monosaccharide units are linked together via a 1,4 or 1,6 bond as a (alpha) or P (beta) anomer, it being possible for each monosaccharide unit to be of L or D configuration, including the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from two saccharides (or monosaccharides) having the general formula: -[Cx(H2O)y)]2- or -[(CthO h-, with x being 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 is an integer representing x - 1;
[0058] The term “polysaccharide” refers to a polysaccharide sugar which is a polymer constituted of several saccharides bonded together via O-glycosidic bonds, said polymers being constituted of monosaccharide units as defined previously, said monosaccharide units comprising at least 5, preferably 6, carbon atoms; in particular, the monosaccharide units are linked together via a 1,4 or 1,6 bond as a (alpha) or P (beta) anomer, it being possible for each saccharide unit to be of L or D configuration, including the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from a certain number of saccharides (or monosaccharides) having the general formula: -[Cx(H20)y)]w- or -[(CH20)x]w-, where x is 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 and preferably x = 6, and y is an integer which represents x - 1, and w is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferentially between 10 and 2300, particularly between 15 and 1000 inclusive, more particularly between 20 and 500, preferentially between 25 and 200;
[0059] - A “salt of an organic or mineral acid” is understood as meaning more particularly a) addition salts with an organic or mineral acid, in particular ones selected from a salt derived from i) hydrochloric acid HC1, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4 or iv) alkylsulfonic acids: Alk-S(O)2OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) alkoxysulfinic acids: Alk-O-S(O)OH, such as methoxysulfinic acid and ethoxysulfinic acid; vii) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; viii) phosphoric acid H3PO4; ix) triflic acid CF3SO3H and x) tetrafluoroboric acid HBF4; xi) organic carboxylic acids R°-C(O)-OH (I’z), in which formula (I’z) R° represents a (hetero)aryl group such as phenyl, a (hetero)aryl(Ci- C4)alkyl group such as benzyl, or a (Ci-Cio)alkyl group, said alkyl group being optionally substituted preferably with one or more hydroxyl groups or amino or carboxyl radicals, R° preferably denoting a (Ci-C6)alkyl group optionally substituted with 1, 2 or 3 hydroxyl or carboxyl groups; more preferentially, the monocarboxylic acids of formula (I’z) are chosen from acetic acid, glycolic acid, lactic acid, and mixtures thereof, and more particularly from acetic acid and lactic acid; and the polycarboxylic acids are chosen from tartaric acid, succinic acid, fumaric acid, citric acid and mixtures thereof; and xii) amino acids including more carboxylic acid radicals than amino groups, such as y-carboxyglutamic acid, aspartic acid or glutamic acid, in particular y-carboxyglutamic acid; or b) addition salts with an organic or mineral base such as alkali metal or alkaline- earth metal hydroxides, alkali metal or alkaline-earth metal carbonates, alkali metal or alkaline-earth metal bicarbonates, addition salts with basic amino acids such as arginine or lysine, addition salts with optionally hydroxylated amines; an “anioiuc counterion” is an anion or an anionic group associated with the cationic charge; more particularly, the anionic counterion is chosen from: i) halides such as chloride or bromide; ii) nitrates; iii) sulfonates, including Ci-Ce alkylsulfonates: Alk- S(O)2O’ such as methyl sulfonate or mesylate and ethyl sulfonate; iv) arylsulfonates: Ar- S(O)2O’ such as benzenesulfonate and toluene sulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-O-S(O)O" such as methyl sulfate and ethyl sulfate; x) aryl sulfates: Ar-O-S(O)O" such as benzene sulfate and toluene sulfate; xi) alkoxy sulfates: Alk-O-S(O)2O" such as methoxy sulfate and ethoxy sulfate; xii) aryloxy sulfates: Ar-O-S(O)2O"; xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate; the “solvates” represent hydrates and also the combination with linear or branched Ci- C4 alcohols such as ethanol, isopropanol or n-propanol;
[0060] The term “chromophore” means a radical derived from a colourless or coloured compound that is capable of absorbing in the UV and / or visible radiation range at a wavelength Abs of between 250 and 800 nm. Preferably, the chromophore is coloured, i.e. it absorbs wavelengths in the visible range, i.e. preferably between 400 and 800 nm. Preferably, the chromophores appear coloured to the eye, particularly between 400 and 700 nm (Ullmann’s Encyclopedia, 2005, Wiley-VcH, Verlag “Dyes, General Survey”, § 2.1 Basic Principle of Color);
[0061] The term “UV-A screening agent” is understood to mean a chromophore derived from a compound which screens out (or absorbs) UV-A ultraviolet rays at a wavelength of between 320 and 400 nm. A distinction may be made between short UV-A screening agents (which absorb rays at a wavelength of between 320 and 340 nm) and long UV-A screening agents (which absorb rays at a wavelength of between 340 and 400 nm).
[0062] The term “UV-B screening agent” means a chromophore derived from a compound which screens out (or absorbs) UV-B ultraviolet rays at a wavelength of between 280 and 320 nm.
[0063] The term “anhydrous” means an amount of less than 5% by weight of water, preferentially less than 3% by weight of water, better still less than 1% by weight of water, relative to the total weight of composition Cl, C2, C3 or C4 in question; even more preferentially, the composition is free of water.
[0064] The terms “colouring agent” and “colorant” are equivalent.
[0065] Unless otherwise indicated, the limits delimiting the extent of a range of values are included in that range of values.
[0066] Unless otherwise indicated, the amounts indicated are expressed as percentages by weight.
[0067] Detailed description
[0068] PROCESS FOR MAKING UP KERATIN MATERIALS
[0069] The first subject of the invention is a process for making up keratin materials, notably the skin and / or lips and / or eyelashes and / or eyebrows, comprising at least the application to said keratin materials of at least two distinct compositions (A) and (B):
[0070] - said composition (A) comprising at least: i) at least one compound of formula (I) comprising at least two acetoacetate functions as described previously, including the optical or geometrical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates; ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and iv) at least one particulate colorant;
[0071] - said composition (B) comprising at least v) a crosslinking agent chosen from (poly)amine compounds, notably aminoalkylpoly alkoxy silanes, a,co-diaminooxaalkanes, chitosans, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains.
[0072] Preferably, in the process of the invention, the compositions (A) and (B) are not simultaneously : - a composition (A) comprising a raffinose polysaccharide bearing an acetoacetate function (especially a raffinose polysaccharide as prepared in example 3 of WO 2024 / 126625) and;
[0073] - a composition (B) comprising spermidine as a crosslinking agent.
[0074] Especially, according to a preferred embodiment, the compositions used in the process of the invention are not simultaneously: an aqueous composition (A) consisting in: 10% by weight of a raffinose polysaccharide as prepared in example 3 of WO 2024 / 126625; 6% by weight of red iron oxide (such as Sunpuro Red Iron 6 Oxide C33-8001 sold by Sun) ; and water qs 100% ; and a composition (B) consisting in: 5% by weight of spermidine; and water qs 100%.
[0075] According to a particular embodiment of the invention, the process of the invention comprises the simultaneous application of ingredients i), v) and iv).
[0076] According to another particular embodiment of the invention, the process comprises at least two steps in which ingredients i), and v) and iv) (the latter ingredient may be present together with ingredient i) and / or with the ingredient(s) v)) are applied in separate, successive steps to the keratin materials, independently of the order of application.
[0077] According to a particular embodiment, the ingredient(s) i) are applied to the keratin materials, and the ingredient(s) v) are then applied to the keratin materials, it being understood that the ingredient(s) iv) may be applied together with i) and / or v).
[0078] According to another particular embodiment, the ingredient(s) v) are applied to the keratin materials, and the ingredient(s) i) are then applied to the keratin materials, it being understood that the ingredient(s) iv) may be applied together with i) and / or v).
[0079] According to one particular embodiment, composition (A) and composition (B) are applied simultaneously or sequentially, independently of the order of application, to the keratin materials.
[0080] In a preferred variant of the invention, a composition obtained by extemporaneous mixing, at the time of application, of composition (A) and composition (B) as defined above is applied.
[0081] In another variant, composition (A) and composition (B) are applied sequentially to the keratin materials, composition (A) possibly being applied to the keratin materials before composition (B), or vice versa. Thus, according to this variant, the process according to the invention comprises two successive steps of applying, to said keratin materials, composition (A) and then composition (B), or composition (B) and then composition (A).
[0082] According to a particular embodiment of the invention, the process for making up keratin materials is a process for making up the skin, lips, eyelashes and / or eyebrows, preferably for making up the skin, eyelashes and / or eyebrows.
[0083] Compositions (A) and (B) may be anhydrous, aqueous such as aqueous-alcoholic and / or comprise one or more fatty substances, notably one or more preferably volatile oils as defined hereinbelow.
[0084] After application of compositions (A) and (B), a persistent, non-tacky coloured deposit is advantageously obtained. The deposit obtained is also resistant to oils, water, sebum and friction.
[0085] According to a particular embodiment, the compositions are applied to dry keratin materials. According to a particular embodiment, the keratin materials are dried after application of compositions (A) and (B), in particular after application of each different composition. i) Compound of formula (I)
[0086] As indicated above, a composition (A) according to the invention comprises at least one compound of formula (I), including the optical or geometrical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates:
[0087] [Chem 2] in which formula (I):
[0088] - R1represents a polysaccharide unit, preferably a disaccharide unit;
[0089] R1also being: a) optionally substituted with one or more hydroxyl OH or dialkylamino -N(R)2 groups with R representing a (Ci-C4)alkyl group such as methyl, carboxyl -C(O)-OH, a vinyl group, and / or b) optionally interrupted with one or more heteroatoms or groups chosen from O, S, carbonyl -C(O)-, amine -N(R’), or combinations thereof 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, a linear or branched alkyl group containing from 1 to 4 carbon atoms optionally substituted with at least one hydroxyl group (OH), or optionally substituted with -X-C(O)-C(Ra)(Rb)-C(O)-R2; preferably, R’ represents a hydrogen atom or a (Ci-C4)alkyl group;
[0090] - R2represents a linear or branched, saturated or unsaturated Ci to Ce monovalent hydrocarbon-based radical, preferably a (Ci-C4)alkyl group such as methyl or tert-butyl, more preferentially methyl;
[0091] - Raand Rb, which may be identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably hydrogen;
[0092] - X is a heteroatom or group chosen from O, S, N(R’) or -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;
[0093] - n denotes an integer ranging from 2 to 10, particularly from 3 to 8.
[0094] According to a particular embodiment of the invention, the compound of formula (I) is chosen from those of formula (la) including the optical or geometrical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates:
[0095] [Chem 3] in which formula (la):
[0096] - R1represents a polysaccharide unit, preferably a disaccharide unit;
[0097] R1also being: a) optionally substituted with one or more hydroxyl groups OH, and / or b) optionally interrupted with one or more heteroatoms or groups chosen from O, S, -N(R’), preferably interrupted with one or more oxygen atoms, in which R’ is as defined in formula (i); - R2is as defined previously, preferably R2represents a linear or branched (Ci-C6)alkyl group, preferably a (Ci-C4)alkyl group, particularly methyl or tert-butyl, such as methyl; and
[0098] - n being as defined previously; preferably, n denotes an integer ranging from 2 to 8.
[0099] According to a preferred embodiment, the compounds of formula (I) and (la) are such that R1represents a disaccharide unit on which n hydroxyl groups have been substituted with n - O-C(O)-CH2-C(O)-R2groups, with R2and n being as defined previously.
[0100] According to a particular embodiment, the disaccharides are chosen from cellobiose, maltose, lactose, raffinose, saccharose (sucrose), trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose and 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 (la) 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 one variant of the invention, the compound of formula (I) or (la) as defined previously is a mixture of compounds of different chemical structures.
[0104] More particularly, the compound(s) of formula (I) and (la) are chosen from the following compounds, including the optical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates:
[0105] in which R1are chosen, independently of one another, from -C(O)-CH2-C(O)-CH3 and H with at least two radicals R1representing -C(O)-CH2-C(O)-CH3, preferably at least three radicals represent -C(O)-CH2-C(O)-CH3. More preferentially, the compounds (I) or (la) are chosen from the compounds of formula (3).
[0106] The compound(s) of formula (I) or (la) as defined previously are preferably present in a content ranging from 0.2% to 99% by weight, particularly from 0.5% to 80%, more particularly from 2% to 70%, relative to the total weight of composition (A) containing same. The compound(s) of formula (I) may be obtained by (poly)condensation(s) of n equivalents of dicarbonyl reagent with a nucleophilic reagent R1(H)nincluding n equivalents of nucleophilic functions according to the following scheme:
[0107] [Chem 4] in which scheme:
[0108] - R1, R2, Ra, Rband n are as defined for the compound of formula (I); and
[0109] - R3represents a hydrogen atom, a (Ci-C4)alkyl group such as methyl, ethyl, isobutyl, t- butyl, or an electrofugal group such as CHah, or HakC-SOi- such as triflate, with Hal, which may be identical or different, representing a halogen atom;
[0110] - X and X’ represent, independently of one another, an oxygen or sulfur atom, preferably O. These (poly)condensation methods are known to those 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.
[0111] According to a particular embodiment of the invention, R1(H)nis chosen from acyclic polyols R1(H)nnotably 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-l,3-pentanediol, 1,6-hexanediol, 1,2-octanediol, 1,8- octanediol, 1,10-decanediol, 2-methyl- 1,3-propanediol, hexylene glycol and isoprene glycol.
[0112] According to another variant, 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 R1(NH2)nincluding n equivalents of -NH2 nucleophilic functions according to the following scheme:
[0113] [Chem 5] in which scheme:
[0114] R1, R2, Raand n are as defined for the compound of formula (I);
[0115] Rband Rc, which may be identical or different, represent a hydrogen atom or a (Ci -Chalky 1 group.
[0116] This type of synthesis process is known to those skilled in the art: for example, mention may be made of “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).
[0117] According to another variant, the compound(s) of formula (I) or (la) are obtained by (poly)condensation(s) of n equivalents of diketene reagent with a nucleophilic reagent R1(H)nincluding n equivalents of nucleophilic functions according to the following scheme: [Chem 6] in which scheme R1, X and n are as defined in formula (I) described above.
[0118] This type of process is known to those skilled in the art. Mention may be made, for example, of “Acetoacetamides, 2-hydroximinoacetoacetamides, and 2,3- bis(hydroximino)butyramides”, Journal filr Praktische Chemie (Leipzig), 323(2), 337-44, (1981) or Angewandte Makromolekulare Chemie, 9, 96-105, (1969). ii) C2-C4 Monoalcohol
[0119] As indicated above, a composition (A) according to the invention comprises at least one monoalcohol comprising from 2 to 4 carbon atoms.
[0120] 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.
[0121] In particular, the monoalcohol(s) may be chosen from ethanol, isopropanol, n-propanol, tertbutanol, butanol, and mixtures thereof.
[0122] Advantageously, composition (A) comprises the C2-C4 monoalcohols in a content ranging from 1% to 75% by weight, preferably from 5% to 65% by weight, more preferentially from 10% to 55% by weight, relative to the total weight of the composition (A). ill) Water
[0123] As indicated above, a composition (A) according to the invention comprises at least water. Preferably, the water used in the process of the invention is deionized water, sterilized water, or osmosed water.
[0124] Advantageously, the composition (A) comprises water in a content ranging from 1% to 75% by weight, preferably from 5% to 65% by weight, and more preferentially from 10% to 55% by weight, relative to the total weight of composition (A). iv) Particulate colorant
[0125] As mentioned previously, a composition (A) according to the invention comprises at least one particulate colorant.
[0126] More particularly, composition (A) of the invention comprises at least one water-soluble or water-insoluble particulate colorant, and preferably in a proportion of at least 0.01% by weight, relative to the total weight of the composition under consideration.
[0127] For obvious reasons, this amount is liable to vary significantly with regard to the intensity of the desired colour effect and the colour intensity afforded by the colorants under consideration, and its adjustment clearly falls within the competence of a person skilled in the art.
[0128] Preferably, composition (A) comprises at least one colorant chosen from pigments, direct dyes and mixtures thereof, more preferentially pigments; more preferentially, the pigment(s) of the invention is (are) chosen from carbon black, iron oxides, notably yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, notably blue and violet triarylmethane pigments, such as Blue 1 Lake, azo pigments, notably red azo pigments, such as D&C Red 7, an alkali metal salt of lithol red, such as the calcium salt of lithol red B, even more preferentially red iron oxides, yellow iron oxides and azo pigments, notably red azo pigments, such as D&C Red 7.
[0129] Pigments
[0130] For the purposes of the invention, the term 'pigmen ' means any compound that is 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 less than 0.01% by weight.
[0131] As pigments that are suitable for use in the invention, mention may notably be made of the organic and / or mineral pigments known in the art, notably those described in Kirk-Othmer’s Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry. These pigments may be synthetic or natural. These pigments may be in pigment powder or paste form. They may be coated or uncoated. These pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, pigments with special effects such as nacres or glitter flakes, and mixtures thereof.
[0132] A pigment that is suitable for use in the invention may be chosen from mineral pigments.
[0133] The term "mineral pigment" means any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on inorganic pigments. Among the mineral pigments that are useful in the present invention, mention may be made 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.
[0134] They may also be pigments having a structure that may 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 the company Chemicals and Catalysts, and has a contrast ratio in the region of 30. They may also be pigments having a structure that may be, for example, of silica microsphere type containing iron oxide. An example of a pigment having this structure is the product sold by the company Miyoshi under the reference PC Ball PC- LL-100 P, this pigment being constituted of silica microspheres containing yellow iron oxide. Advantageously, the pigments may be iron oxides and / or titanium dioxides.
[0135] A pigment that is suitable for use in the invention may be chosen from organic pigments.
[0136] The term “organic pigment” means any pigment that satisfies the definition in Ullmann’s encyclopaedia in the chapter on organic pigments. Among the organic pigments that are useful in the present invention, mention may be made of nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal-complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds. In particular, the white or coloured organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 45370, 71105, the red pigments codified 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 or phenol derivatives as described in patent FR 2 679 771.
[0137] Examples that may also be mentioned include pigment pastes of organic pigments, such as the products sold by the company Hoechst under the names: Cosmenyl Yellow IOG: Yellow 3 pigment (CI 11710); Cosmenyl G yellow: Yellow 1 pigment (CI 11680); Cosmenyl GR orange: Orange 43 pigment (CI 71105); Cosmenyl R red: Red 4 pigment (CI 12085); Cosmenyl FB carmine: Red 5 pigment (CI 12490); Cosmenyl RL violet: Violet 23 pigment (CI 51319); Cosmenyl A2R blue: Blue 15.1 pigment (CI 74160); Cosmenyl GG green: Green 7 pigment (CI 74260); Cosmenyl R black: Black 7 pigment (CI 77266).
[0138] The pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426. These composite pigments may notably be composed of particles including an inorganic core, at least one binder for attaching the organic pigments to the core, and at least one organic pigment which at least partially covers the core.
[0139] The organic pigment may also be a lake. The term “lake" refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
[0140] The mineral substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate and aluminium. Among the dyes adsorbed on organic substrates, mention may be made 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 5 (CI 61 570), D & C Yellow 10 (CI 77 002), 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 (P-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin, betanin (beet), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocianine, black carrot, hibiscus, elderberry), caramel, riboflavin, beet juice and caramel.
[0141] An example of a lake that may be mentioned is the product known under the following name: D&C Red 7 (CI 15 850:1).
[0142] The pigment may also be a special-effect pigment.
[0143] The term “pigments with special effects” refers to pigments that generally create a coloured appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is non-uniform and that changes as a function of the conditions of observation (light, temperature, angles of observation, etc.). They thereby differ from coloured pigments, which afford a standard uniform opaque, semi-transparent or transparent shade.
[0144] Several types of special-effect pigments exist: those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacres, interference pigments or glitter flakes.
[0145] The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 pm, preferably between 20 nm and 80 pm and more preferentially between 30 nm and 50 pm.
[0146] The pigments may be dispersed in the composition by means of a dispersant. This dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof, bearing one or more functionalities with strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigments. These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium. In particular, esters of 12- hydroxystearic acid in particular and of Cs to C20 fatty acid and of polyols such as glycerol or diglycerol are used, such as poly(12-hydroxy stearic acid) stearate with a molecular weight of approximately 750 g / mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or polyhydroxystearic acid such as the product sold under the reference Arlacel Pl 00 by the company Uniqema, and mixtures thereof. As other dispersants that may be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, for instance Solsperse 17 000 sold by the company Avecia, and polydimethylsiloxane / oxypropylene mixtures such as those sold by the company Dow Coming under the references 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 dispersant(s) are of amino silicone type other than the alkoxysilanes described previously and are cationic. Preferably, the pigment(s) is (are) chosen from mineral, mixed mineral-organic, or organic pigments.
[0147] 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.
[0148] According to another embodiment of the invention, the pigment(s) according to the invention are mineral pigments.
[0149] According to a particular embodiment of the invention, the cosmetic active agent is a colorant chosen from one or more direct dyes.
[0150] The term “direct dye” means natural and / or synthetic dyes, other than oxidation dyes. These are dyes that will spread superficially on the fibre. They may be ionic or nonionic, preferably cationic or nonionic.
[0151] Among the direct dyes that are suitable for use in the invention, mention may be made of azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.
[0152] The direct dyes are preferably cationic direct dyes. Mention may be made of the hydrazono cationic dyes of formulae (A) and (B) below and the azo cationic dyes of formulae (C) and (D) below:
[0153] [Chem 7]
[0154] Het+-C(Ra)=N-N(Rb)-Ar, Q Het+-N(Ra)-N=C(Rb)-Ar, Q
[0155] (A)
[0156] Het*-N=N-Ar, Q
[0157] (C) in which formulae (A) to (D):
[0158] Het+represents a cationic heteroaryl radical, preferentially bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, which is optionally substituted, preferentially with at least one (Ci-Cs)alkyl group such as methyl;
[0159] Ar+represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferentially ammonium, particularly tri(Ci-C8)alkylammonium, such as trimethylammonium;
[0160] Ar represents an aryl group, notably phenyl, which is optionally substituted, preferentially with one or more electron-donating groups such as optionally substituted (Ci- Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, (di)(Ci-C8)(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, aryl(Ci-C8)alkylamino, and optionally substituted N-(Ci-C8)alkyl-N-aryl(Ci-C8)alkylamino or alternatively Ar represents a julolidine group;
[0161] Ar” represents an optionally substituted (hetero)aryl group, such as phenyl or pyrazolyl, which are optionally substituted, preferentially with one or more (Ci-C8)alkyl, hydroxyl, (di)(Ci-C8)(alkyl)amino, (Ci-C8)alkoxy or phenyl groups;
[0162] Ra and Rb, which may be identical or different, represent a hydrogen atom or a (Ci- Cs)alkyl group, which is optionally substituted, preferentially with a hydroxyl group; or else the substituent Ra with a substituent of Het+and / or Rb with a substituent of Ar form, together with the atoms that bear them, a (hetero)cycloalkyl; in particular, Ra and Rb represent a hydrogen atom or a (Ci-C4)alkyl group optionally substituted with a hydroxyl group; Q" represents an organic or mineral anionic counterion, such as a halide or an alkyl sulfate.
[0163] In particular, mention may be made of the azo and hydrazono direct dyes bearing an endocyclic cationic charge of formulae (A) to (D) as defined previously. More particularly the cationic direct dyes bearing an endocyclic cationic charge described in patent applications WO 95 / 15144, WO 95 / 01772 and EP 714 954. Preferentially the direct dyes of formulae (E) and (F) below: [Chem 8] in which formulae (E) and (F):
[0164] R1represents a (Ci-C4)alkyl group such as methyl;
[0165] R2and R3, which may be identical or different, represent a hydrogen atom or a (Ci- C4)alkyl group, such as methyl;
[0166] R4represents a hydrogen atom or an electron-donating group such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, or (di)(Ci-Cs)(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group; in particular, R4is a hydrogen atom;
[0167] Z represents a CH group or a nitrogen atom, preferentially CH;
[0168] Q" is an anionic counterion as defined previously, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesyl.
[0169] In particular, the dyes of formulae (E) and (F) are chosen from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof with Q’ being an anionic counterion as defined previously, particularly a halide such as chloride, or an alkyl sulfate such as methyl sulfate or mesyl. The direct dyes may be chosen from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly referred to as “acid” direct dyes owing to their affinity for alkaline substances.
[0170] The term “anionic direct dye” means any direct dye including in its structure at least one CO2R’ or SO3R’ substituent with R’ denoting a hydrogen atom or a cation originating from a metal or an amine, or an ammonium ion. The anionic direct dyes may be chosen from direct nitro acid dyes, azo acid dyes, azine acid dyes, triarylmethane acid dyes, indoamine acid dyes, anthraquinone acid dyes, indigoid dyes and natural acid dyes.
[0171] Among the natural direct dyes that may be used according to the invention, mention may be made of lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orceins. It is also possible to use extracts or decoctions containing these natural dyes and especially hennabased poultices or extracts.
[0172] Preferably, the direct dyes are chosen from anionic direct dyes.
[0173] The colorants, preferably the pigments, may 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% relative to the total weight of the composition containing them.
[0174] The direct dye(s) may be present in concentrations ranging from 0.001% to 20% by weight relative to the total weight of the composition, preferably from 0.005% to 15% by weight relative to the total weight of the composition containing them.
[0175] Preferably, the particulate colorant(s) is (are) chosen from pigments, direct dyes and mixtures thereof, preferably pigments; more preferentially, the pigment(s) of the invention is (are) chosen from carbon black, iron oxides, notably yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, notably blue and violet triarylmethane pigments, such as Blue 1 Lake, azo pigments, notably red azo pigments, such as D&C Red 7, an alkali metal salt of lithol red, such as the calcium salt of lithol red B, even more preferentially red iron oxides, yellow iron oxides and azo pigments, notably red azo pigments, such as D&C Red 7.
[0176] Advantageously, the process for making up keratin materials is a process for making up the skin, eyelashes and / or eyebrows, in particular a lip makeup process, or a process of making up with a mascara, an eyeliner, an eye shadow or a foundation.
[0177] (v) Crosslinking agent
[0178] As stated previously, a composition (B) according to the invention comprises at least one crosslinking agent. For the purposes of the invention, the term “crosslinking agent”, also termed “R”, denotes a compound that is capable of establishing with at least one acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention: at least one covalent bond, at least one donor- acceptor (dative) bond, and / or at least one coordination bond, and thus of crosslinking this or these compounds.
[0179] Preferably, the term “crosslinking agent” refers to a compound that is capable of establishing at least one covalent bond with an acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention and thus of crosslinking this or these compounds.
[0180] For the purposes of the present invention, it is understood that the terms “crosslinking agent” and “crosslinker” are equivalent.
[0181] The crosslinking agent(s) is (are) preferably present in a weight content ranging from 0.5% to 95% by weight, in particular ranging from 1% to 90% by weight, more particularly from 10% to 85% by weight, even more particularly from 15% to 80% relative to the total weight of the composition containing same.
[0182] More precisely, the crosslinking agent(s) suitable for the invention may be chosen from compounds containing amine functions, referred to as (poly)amine compounds.
[0183] The term “poly(amine) compounds” is understood to denote respectively compounds containing at least one primary or secondary amine function.
[0184] The (poly)amine compound(s) may be chosen in particular from polyamine compounds bearing several primary amine and / or secondary amine groups or else from amino alkoxysilanes, and more particularly from amino alkoxysilane compounds, diamine compounds, triamine compounds, and mixtures thereof.
[0185] The (poly)amine compound may be a compound comprising from 2 to 20 carbon atoms, notably a non-polymeric compound. It may be acyclic or cyclic, linear or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -Si(R’)2- and - N(R”)-, preferably -O-, -Si(R’)2-, or combinations thereof such as -Si(R’)2-O- or-O-Si(R’)2- , with R’, which may be identical or different, representing a (Ci-C4)alkyl group such as methyl, and R’ ’ representing a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom.
[0186] The term “non-polymeric compound” means a compound which is not directly obtained via a monomer polymerization reaction. (Poly)amine compounds that may be mentioned in particular include N-methyl-1,3- diaminopropane, N-propyl-l,3-diaminopropane, N-isopropyl-l,3-diaminopropane, N- cyclohexyl- 1 ,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2- aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methylbis(3- aminopropyl)amine, N-(3-aminopropyl)-l,4-diaminobutane, N,N- dimethyldipropylenetriamine, 1 ,2-bis(3-aminopropylamino)ethane, N,N’ -bis(3- aminopropyl)-l,3-propanediamine, ethylenediamine, 1,3-propylenediamine, 1,4- butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, 1,3- bis(aminomethyl)cyclohexane, 1 ,4-bis(aminomethyl)cyclohexane, diaminopropanol,
[0187] 4,7,10-trioxa-l,13-tridecanediamine, spermidine and C36-alkylenediamines (Priamine™ 1071, 1073, 1074, 1075, respectively), preferably spermidine and / or 4,7,10-trioxa-l,13- tridecanediamine.
[0188] According to a particular embodiment of the invention, the (poly)amine compounds are monoamine compounds, i.e. they contain only one primary and / or secondary amine group, preferably a primary amine group (NH2).
[0189] The (poly)amine compound(s) may be chosen from amino alkoxysilanes, notably of formula RTSi(OR’2)z(R’3)x in which:
[0190] - RT is a linear or branched, saturated or unsaturated, cyclic or acyclic Ci-Ce hydrocarbon-based chain substituted with a group chosen from primary amine groups NH2 or secondary amine groups -N(H)R with R representing a C1-C4 alkyl, an aryl or a benzyl substituted with an amino group or with a C1-C4 aminoalkyl group; RT may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R being linked to the silicon atom directly via a carbon atom,
[0191] - R’2 and R , which may be identical or different, represent a linear or branched (Ci- Ce)alkyl group,
[0192] - z denotes an integer ranging from 1 to 3, and
[0193] - x denotes an integer ranging from 0 to 2, with z + x = 3. In particular, R’ i is an acyclic chain. Preferably, R’ i is a linear or branched, saturated or unsaturated Ci-Ce hydrocarbon-based chain substituted with an amine -NH2 or -N(H)R group, with R representing a Ci-Ce alkyl, a C3-C6 cycloalkyl or a Ce aromatic group. More preferentially, R’i is a saturated linear Ci-Ce hydrocarbon-based chain substituted with an amine group NH2. Even more preferentially, R’ 1 is a saturated linear C2-C4 hydrocarbonbased chain substituted with an amine group NH2.
[0194] In particular, R’2 represents an alkyl group comprising from 1 to 4 carbon atoms; preferably, R’2 represents a linear alkyl group comprising from 1 to 4 carbon atoms and more preferentially R’2 represents an ethyl group.
[0195] In particular, R’3 represents an alkyl group comprising from 1 to 4 carbon atoms; preferably, R’3 represents a linear alkyl group comprising from 1 to 4 carbon atoms and more preferentially R’3 represents methyl or ethyl groups.
[0196] Preferably, the (poly)amine compound(s) is (are) chosen from aminoalkylpolyalkoxysilanes, compounds according to the preceding formula in which z is equal to 2 and x is equal to 1, or in which z is equal to 3 and x is equal to 0. Preferably, z is equal to 3.
[0197] In particular, the (poly)amine compound(s) are chosen from amino alkoxysilanes including only one primary and / or secondary, preferably primary (NH2), amine group, such as 3- aminopropyltriethoxysilane (APTES), 3 -aminoethyltriethoxy silane (AETES), 3- aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m- aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, and N-(2- aminoethylaminomethyl)phenethyltrimethoxysilane.
[0198] Preferably, the (poly)amine compound(s) is (are) chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, and more preferentially 3- aminopropyltriethoxysilane (APTES), in particular the product sold by Sigma- Aldrich.
[0199] The (poly)amine compounds may also be chosen from amino polymers, notably having a weight- average molecular weight ranging from 500 g.mor1to 1 000000 g.mol'1, preferably ranging from 500 g.mol'1to 500000 g.mol'1, and preferentially ranging from 500 g.mol'1to 100000 g.mol'1.
[0200] According to a particular embodiment of the invention, the (poly)amine compound(s) is (are) monoamine compounds and are chosen from polydialkylsiloxanes notably of formula (III): H2N-ALK-Si(R’2)(R’3)-O-[Si(R’2)(R’3)-O]n-Si(R’2)(R’3)-R’4(HI) in which formula (III):
[0201] - Aik represents a (C1-C4) alkylene group which is linear or branched, preferably linear, such as propylene,
[0202] - R’2 and R’3, which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, such as methyl, and
[0203] - R’4 represents a linear or branched (Ci-C6)alkyl group, preferably a C4 alkyl group, such as n-butyl, n represents an integer greater than or equal to 2, preferably the value of n is such that the weight-average molecular weight of the polydimethylsiloxane ranges from 500 to SOOO g.mok1. As examples of poly dimethylsiloxanes (III), mention may be made of the products sold under the names MCR-A11 and MCR-A12 by the company Gelest.
[0204] According to a particular embodiment of the invention, the (poly)amine compound(s) is (are) diamine compounds, i.e. they contain two primary and / or secondary amine groups, preferably primary amine groups (NH2).
[0205] More particularly, they are chosen from the compounds of formula (IV) or (V):
[0206] . ALK[(O-ALK’)m-NH2]2 (IV) or
[0207] . H2N-ALK-Si(R’)2-[O-Si(R’)2]m-O-Si(R)2-ALK’-NH2 (V) in which formulae (IV) and (V):
[0208] - ALK and ALK’, which may be identical or different, represent a linear or branched (Ci- C6)alkylene group, preferably a linear group such as propylene,
[0209] - R’, which may be identical or different, represent a (Ci-C4)alkyl group, such as methyl,
[0210] - m represents an integer greater than or equal to 0; preferably, the value of m is such that the weight-average molecular weight of compound (IV) or (V) ranges from 500 g.mor1to 55 OOO g.mol’1.
[0211] As examples of compounds of formula (V), mention may be made of those sold under the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS-A32 and DMS-A35 by the company Gelest.
[0212] The (poly)amine compound(s) that are diamines is (are) particularly polyether diamines notably of formula H2N-ALK-O-[ALK’-O]m-ALK”-NH2 with ALK, ALK’ and ALK”, which may be identical or different, representing a linear or branched (Ci-C6)alkylene group, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-l,13- tridecanediamine or the compounds known under the reference Jeffamine from the company Hunstman, and more particularly polyethylene glycol and / or polypropylene glycol a, co- diamines (bearing a chain-end amine function) such as the products sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000 and ED-2003.
[0213] The (poly)amine compound(s) which is (are) diamine compound(s) may be chosen more particularly from 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane and 1,9- diaminononane, from a,co-diaminooxaalkanes such as l,8-diamino-3,6-oxaoctane, 1,12- diamino-4,9-dioxadodecane, and l,13-diamino-4,7,10-trioxatridecane (also called 4,7,10- trioxa- 1 , 13-tridecanediamine), preferably 4,7, 10-trioxa- 1 , 13-tridecanediamine.
[0214] According to a particular embodiment of the invention, the (poly)amine compound(s) are triamine compounds, i.e. they contain three primary and / or secondary amine groups, preferably primary amine groups (NH2). More particularly, they are chosen from polyether triamines notably of formula ALK”’[(O-ALK’)m-NH2]3 with ALK’ as defined previously and ALK”’ representing a linear or branched trivalent (Ci-C6)alkylene group, and m representing an integer greater than or equal to 0.
[0215] As (poly)amine compounds that are triamine compounds, mention may be made in particular of poly ether triamines, and notably polyethylene glycol and / or polypropylene glycol a, codiamines (bearing a chain-end amine function) such as the products sold under the names Jeffamine T-403.
[0216] According to another particular embodiment of the invention, the (poly)amine compound(s) include(s) more than three primary and / or secondary amine groups, preferably primary amine groups (NH2).
[0217] In this variant, the (poly)amine compound(s) is (are) chosen from poly(meth)acrylates or poly(meth)acrylamides bearing lateral primary or secondary amine functions, such as poly(3-aminopropyl)methacrylamide and poly (2- aminoethyl) methacrylate.
[0218] More particularly, the polyamine compounds are chosen from chitosans (notably polypglucosamine)) and polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains.
[0219] According to another variant, the (poly)amine compound(s) is (are) chosen from poly((C2- C5)alkyleneimines), and preferably polyethyleneimines and polypropyleneimines, notably poly(ethyleneimines), in particular the product sold under reference 408700 by the company Aldrich Chemical or under the trade name Lupasol by BASF, notably with a molecular weight ranging from 1200 g.mor1to 25 000 g.moT1; poly(allylamine), in particular the product sold under reference 479136 by the company Aldrich Chemical; polyvinylamines and copolymers thereof, notably with vinylamides, in particular vinylamine / vinylformamide copolymers such as those sold under the name Lupamin® 9030 by the company BASF; polyamine acids containing NH2 groups, such as polylysine, in particular the product sold by the company JNC Corporation (formerly Chisso); amino dextran, in particular the product sold by the company CarboMer Inc; amino polyvinyl alcohol, in particular the product sold by the company CarboMer Inc; acrylamido(Ci-C6)alkylamine-based copolymers, notably acrylamidopropylamine-based copolymers; and poly(D-glucosamine), for example sold under the reference Kionutrime CSG® by the company Kytozyme.
[0220] According to a particular embodiment, the polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains are chosen from the compounds of formula (VI) below:
[0221] Ra-Si(Rb)(Rc)-O-[Si(Rb)(Rc)-O]m-[Si(ALK1-NH2)(Ra)-O]n-Si(Rb)(Rc)-Ra(VI) in which formula (VI):
[0222] - Ra, which may be identical or different, represent a hydroxy or (Ci-C4)alkyl group,
[0223] - Rb and Rc, which may be identical or different, preferably identical, represent a (Ci-C4)alkyl group, such as methyl,
[0224] - ALK1represents a linear or branched (Ci-Ce) alkylene group, optionally interrupted with an N(H) group,
[0225] - m and n are integers greater than or equal to 1 ; preferably, m and n are such that the weightaverage molecular mass of the compound of formula (VI) ranges from 1000 g.mol'1to 500 000 g.mol'1.
[0226] According to a preferred variant, formula (VI) is such that Ra, Rb and Rcrepresent a methyl group, ALK1represents a propylene group, the values of n and m are such that the weightaverage molecular weight of the polydimethylsiloxane ranges from 1000 g.mol'1to 55 000 g.mol'1.
[0227] As examples of polydimethylsiloxanes of formula (VI), mention may be made of those sold under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203 by the company Gelest.
[0228] According to another variant, formula (VI) is such that Rarepresents a hydroxyl or (Ci- C4)alkyl group, such as methyl, ALK1represents a (C5-C6)alkylene group substituted with an NH group; preferably, ALK1represents -(CH2)3-N(H)-(CH2)2-, and m and n are such that the weight- average molecular mass of the compound of formula (VI) ranges from 5000 g.mor1to 500 000 g.mol’1.
[0229] As amine polymer, mention may also be made of a,co-diamino polytetrahydrofurans (or polytetramethylene glycols) and a,co-diamino polybutadienes.
[0230] According to a particular embodiment of the invention, the (poly)amine compounds are chosen from hyperbranched polymers comprising at least one amino group and dendrimers bearing at least one amino group, such as PAMAM polyamidoamine dendrimers with an ethylenediamine core and a terminal amine function.
[0231] According to a particular embodiment, the composition comprises a crosslinking agent R chosen from (poly)amine compounds, in particular chosen from chitosans, aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, amodimethicones, polyglucosamines, and mixtures thereof.
[0232] More preferentially, the composition comprises a crosslinking agent R chosen from aminoalkoxysilanes and polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains such as amodimethicones, and even more preferentially chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3- aminopropylmethyldiethoxysilane, V-(2-aminocthyl)-3-aminopropyltricthoxysilanc and polydimethylsiloxanes comprising terminal amino groups at the end of the chain, such as bis-cetearyl amodimethicone.
[0233] In particular, said (poly)amine compounds are chosen from a) chitosans, such as polypglucosamine), b) polyether diamines, particularly polyethylene glycol a,co-diamines (bearing a chain-end amine function), c) a,co-diaminooxaalkanes such as 4,7,10-trioxa-l,13- tridecanediamine, d) polyether triamines, such as polyetheramine (or Jeffamine), e) aminoalkoxysilanes, such as APTES, f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNHi) and amodimethicones comprising amine groups on side chains, such as bis-cetearyl amodimethicone, notably the product sold by Momentive Performance Materials, and g) poly amine compounds NHi-alk-NHi, in which alk denotes a divalent C2-C20 hydrocarbon-based chain, optionally interrupted with one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a C1-C4 alkyl radical, such as spermidine. According to a preferred embodiment, said (poly)amine compound(s) is (are) chosen from b) poly ether diamines, particularly polyethylene glycol a,co-diamines (bearing a chain-end amine function), d) polyether triamines, such as polyetheramine (or Jeffamine), e) aminoalkoxysilanes, such as APTES, f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNHi) and amodimethicones comprising amine groups on side chains, such as bis-cetearyl amodimethicone, notably the product sold by Momentive Performance Materials, and even more preferentially from f) poly dialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)- terminated poly(dimethoxysiloxane) (PDMS-diNHi) and amodimethicones comprising amine groups on side chains, such as bis-cetearyl amodimethicone.
[0234] According to a preferred embodiment, the (poly)amine compound(s) is (are) chosen from: a) polyether diamines, in particular polyethylene glycol a,co-diamines, bearing a chain-end amine function, b) polyether triamines, in particular polyetheramines (or Jeffamine), c) aminoalkoxysilanes, in particular APTES, d) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNHi) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone .
[0235] Fatty phase - fatty substances
[0236] According to a particular embodiment, composition (A) and / or composition (B) also comprises one or more fatty substances, particularly one or more oils, preferably volatile oils.
[0237] More particularly, in the process of the invention, at least one of the compositions (A) and (B) contains a fatty phase.
[0238] In particular, at least one of the compositions (A) or (B) comprises one or more fatty substances, in particular one or more oils, preferably volatile oils. The term “oil” refers to a fatty substance that is liquid at room temperature (20°C) and atmospheric pressure (760 mmHg).
[0239] The term “hydrocarbon-based oil” means an oil formed essentially from, or even constituted of, carbon and hydrogen atoms, and possibly oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.
[0240] According to one embodiment of the invention, the oil(s) is (are) chosen from volatile oils, in particular:
[0241] * hydrocarbon oils containing from 8 to 16 carbon atoms, and notably:
[0242] - branched Cs-Ci6 alkanes, for instance isoalkanes (also known as isoparaffins) such as C13- Ci6 isoparaffin, isododecane, isodecane, isohexadecane, and for example the oils sold under the Isopar or Permethyl trade names, alone or as mixtures, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), more preferentially isododecane;
[0243] - linear alkanes, for example C11-C16 alkanes, alone or as mixtures, for instance hexane, decane, undecane, tridecane, isoparaffins, or n-dodecane (C12) and n-tetradecane (C14), the undecane-tridecane mixture, mixtures of n-undecane (Cl l) and n-tridecane (Cl 3), and mixtures thereof and also mixtures of n-undecane (Cl l) and n-tridecane (Cl 3);
[0244] - volatile, non-aromatic cyclic C5-C12 alkanes;
[0245] * short-chain esters containing from 3 to 8 carbon atoms in total, such as ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate;
[0246] * carbonate hydrocarbon-based oils of structure RT-O-C(O)-O-R’2 in which RT and R’2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen from dibutyl carbonate or dipentyl carbonate;
[0247] * ether oils of formula R1-O-R2 in which Ri and R2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;
[0248] * silicone oils comprising in particular from 2 to 7 silicon atoms, these silicone oils optionally including alkyl or alkoxy groups containing 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 mixtures thereof; more preferentially, the volatile oil(s) are chosen from Cs-Ci6 alkanes, notably branched alkanes such as isododecane.
[0249] In particular, at least one of the compositions (A) or (B) comprises one or more non-volatile oils, notably chosen from:
[0250] * non-volatile fluoro oils, notably chosen from fluorinated polyethers and also from fluorosilicone oils, fluorosilicones;
[0251] * non-volatile silicone oils, notably chosen from non-volatile silicones having the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyl trimethicone, diphenylsiloxy phenyl trimethicone; and also mixtures thereof;
[0252] * non-volatile apolar hydrocarbon-based oils notably chosen from linear or branched compounds of mineral or synthetic origin: i) liquid paraffin, ii) squalane, isoeicosane, iii) mixtures of linear, saturated hydrocarbons, more particularly C15-C28 hydrocarbons, such as mixtures whose INCI names are (Ci5-Ci9)Alkane, (C18-C21) Alkane, (C21-C28) Alkane, iv) hydrogenated or non-hydrogenated polybutenes; v) hydrogenated or non-hydrogenated polyisobutenes, preferably hydrogenated, vi) hydrogenated or non-hydrogenated polydecenes, vii) decene / butene copolymers, butene / isobutene copolymers and viii) mixtures thereof;
[0253] * non-volatile polar hydrocarbon-based oils, which may be chosen from: i) saturated, unsaturated, linear or branched C10-C26 fatty alcohols, preferably monoalcohols; advantageously, the C10-C26 alcohols 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, notably such as lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyloctanol, 2-undecylpentadecanol, 2- hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof; ii) triglycerides consisting of fatty acid esters of glycerol, in particular the fatty acids of which may have chain lengths ranging from C4 to C36, and notably from Cis to C36, these oils possibly being linear or branched, and saturated or unsaturated; by way of example, mention may notably be made of heptanoic or octanoic triglycerides, caprylic / capric acid triglycerides; plant oils such as wheatgerm oil, sunflower oil, grapeseed oil, sesame seed oil, corn 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, groundnut oil, coconut oil, argan oil, kaya oil; the liquid fraction of shea butter, and the liquid fraction of cocoa butter; and also mixtures thereof; iii) linear aliphatic hydrocarbon-based esters of formula R-C(O)-OR’ in which R-C(O)-O- represents the carboxylic acid residue containing from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, aliphatic hydrocarbon-based esters of alkylene glycol, in particular ethylene glycol or propylene glycol; the total number of carbon atoms being advantageously at least 10; notably chosen 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 poly alcohols, such as propylene glycol dioctanoate, cetyl octanoate or tridecyl octanoate, 2-ethylhexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol bis(2-ethylhexanoate) and mixtures thereof, hexyl laurate, neopentanoic acid esters, such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate or 2-octyldodecyl neopentanoate, isononanoic acid esters, such as isononyl isononanoate, isotridecyl isononanoate or octyl isononanoate, oleyl erucate, isopropyl lauroyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate or myristyl myristate; iv) hydroxylated esters such as polyglyceryl-2 triisostearate; v) aromatic esters such as tridecyl trimellitate, C12-C15 alcohol benzoate, the 2-phenylethyl ester of benzoic acid, and butyloctyl salicylate; vi) linear fatty acid esters with a total carbon number ranging from 35 to 70, for instance pentaerythrityl tetrapelargonate; vii) esters of C24-C28 branched fatty acids or fatty alcohols such as triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2- decyltetradecanoate), pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetrakis(2-decyltetradecanoate) ; viii) 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; ix) synthetic ethers containing from 10 to 40 carbon atoms, such as dicaprylyl ether; x) dialkyl carbonates, the two alkyl chains possibly being identical or different, such as dicaprylyl carbonate; xi) vinylpyrrolidone copolymers such as vinylpyrrolidone / 1 -hexadecene copolymer; and xii) mixtures thereof;
[0254] * the non-volatile carbonate oils may be chosen from the carbonates of formula Rs-O-C(O)- O-R9, with Rs and R9, which may be identical or different, representing a linear or branched C4 to C12 and preferentially Ce to C10 alkyl chain; the carbonate oils may be dicaprylyl carbonate (or dioctyl carbonate), bis(2-ethylhexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate or dinonyl carbonate and preferably dioctyl carbonate;
[0255] * oils known as non-volatile ether oils of formula R1-O-R2 in which Ri and R2 independently denote a linear, branched or cyclic C6-C24 alkyl group, preferably a Ce-Cis alkyl group, and preferably a Cs-Ci2 alkyl group. It may be preferable for Ri and R2 to be identical. Linear alkyl groups that may be mentioned include a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, a behenyl group, a docosyl group, a tricosyl group and a tetracosyl group. Branched alkyl groups that may be mentioned include a 1,1 -dimethylpropyl group, a 3-methylhexyl group, a 5-methylhexyl group, an ethylhexyl group, a 2-ethylhexyl group, a 5-methyloctyl group, a 1-ethylhexyl group, a 1-butylpentyl group, a 2-butyloctyl group, an isotridecyl group, a 2-pentylnonyl group, a 2-hexyldecyl group, an isostearyl group, a 2-heptylundecyl group, a 2-octyldodecyl group, a 1,3-dimethylbutyl group, a 1-(1- methylethyl)-2-methylpropyl group, a 1,1,3,3-tetramethylbutyl group, a 3,5,5- trimethylhexyl group, a l-(2-methylpropyl)-3-methylbutyl group, a 3,7-dimethyloctyl group and a 2-(l,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group. As cyclic alkyl groups, mention may be made of a cyclohexyl group, a 3-methylcyclohexyl group and a 3,3,5- trimethylcyclohexyl group, dilauryl ether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyl dimethyl butyl ether, cetyl dimethyl butyl ether, cetyl isobutyl ether and mixtures thereof; more preferentially c) the non-volatile oil(s) is (are) chosen from: hydrogenated or nonhydrogenated polyisobutenes, preferably hydrogenated, for instance the non-volatile compounds of the Parleam® range; mixtures of C15-C19 alkanes, and from linear aliphatic hydrocarbon-based esters of formula R-C(O)-OR’ in which R-C(0)-0 represents a carboxylic acid residue containing from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, as defined previously, notably isononyl isononanoate.
[0256] Very preferentially, the process of the invention comprises the application of one or more hydrocarbon-based oils containing from 8 to 16 carbon atoms, and notably branched Cs-Ci6 alkanes, for instance isoalkanes such as C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, alone or as mixtures, preferably isododecane.
[0257] Particularly, the amount of oil(s) in at least one of the compositions (A) or (B) is between 1% and 99% by weight relative to the total weight of the composition, more particularly between 10% and 90% by weight, preferentially between 20% and 75%, better still between 25% and 70% by weight relative to the total weight of the composition.
[0258] As indicated above, a composition (A) and a composition (B) according to the invention are separate.
[0259] According to one embodiment, the compositions (A) and (B) are packaged separately. The expression “packaged separately” is understood to mean that the compositions (A) and (B) are packaged inside two compartments formed by two separate containers.
[0260] According to a particular embodiment, composition (B) comprises an aqueous phase, and in particular comprises water.
[0261] According to an advantageous variant, composition (B) is aqueous or aqueous-alcoholic.
[0262] According to another particular embodiment of the invention, composition (B) is an anhydrous composition. In particular, composition (B) is anhydrous, and it comprises at least one oil, notably a volatile oil such as isododecane.
[0263] Composition (B) may also comprise one or more organic solvents. The term “organic solvent" means an organic substance that is capable of dissolving another substance without chemically modifying it.
[0264] Examples of organic solvents that may be mentioned include a) C2-C6 alkanols, such as ethanol and isopropanol; b) polyols that are miscible with water at room temperature (25°C), notably chosen from polyols notably containing from 2 to 10 carbon atoms, preferably containing 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; c) polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether or diethylene glycol monomethyl ether; and also d) aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
[0265] According to a particular embodiment, the composition also comprises one or more polyols notably chosen from polyols notably containing from 2 to 10 carbon atoms, preferably containing from 2 to 6 carbon atoms, such as glycerol.
[0266] In particular, composition (B) is aqueous or aqueous-alcoholic (an ethanol / water mixture, in particular one with a volume ratio ranging from 1 / 99 to 99 / 1, more particularly ranging from 10 / 90 to 90 / 10, even more particularly ranging from 20 / 80 to 80 / 20, preferably ranging from 40 / 60 to 60 / 40, such as 50 / 50).
[0267] The composition can be in an anhydrous form, or in the form of a water-in-oil emulsion or an oil-in-water emulsion.
[0268] Kit and application
[0269] According to yet another of its aspects, the present invention also relates to a multicompartment kit or device, notably a cosmetic kit or device, for making up keratin materials, in particular the skin, lips, eyelashes and / or eyebrows, 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; and iv) at least one particulate colorant; at least one second compartment distinct from said first compartment, and containing at least the composition (B) comprising: v) a crosslinking agent chosen from (poly)amine compounds, notably aminoalkylpoly alkoxy silanes, a,co-diaminooxaalkanes, chitosans, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains.
[0270] Any type of applicator may be used for depositing the first and / or second composition.
[0271] The respective applicators of the first and second compositions may be identical or different. According to a variant of the invention, the first and second compositions may be applied by means of two distinct applicator portions of the same applicator.
[0272] According to another variant, the makeup kit according to the present invention comprises one or more means for applying the first and second compositions.
[0273] The first and second cosmetic compositions included in the makeup kit of the invention may be applied in particular to the eyelashes and / or the eyebrows, 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.
[0274] In this case, the first composition may be applied using any applicator provided that it allows a localized deposit on a portion of the length of the keratin fibre and, when it is an eyelash, over at most 2 / 3 of its length.
[0275] The threaded stem may be made of plastic or metal or any other suitable material.
[0276] The pen equipped with a notched wheel is more particularly described in patent US 5851019 or FR2588733.
[0277] This pen allows precise metering of the product to be applied at the outlet of the pen after actuation of a notched wheel or of a pushbutton which advances a piston with each rotation / press.
[0278] In actual fact, the keratin materials can be made up according to two processes. The first route consists of multiple actions 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 completely or partially on the first “basecoat” composition and on the keratin materials.
[0279] According to a particularly advantageous embodiment, this packaging article is provided with two distinct applicators.
[0280] The second route consists in premixing the two compositions, just before applying the resulting composition on the keratin materials.
[0281] Whatever the route chosen 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 may also comprise means for combining the two compositions before application, such as a container and a stirrer.
[0282] The applicator may optionally be rigidly connected to the container. Advantageously, the applicator is rigidly connected to a stem which, itself, is rigidly connected to the closing member.
[0283] The closing member may be coupled to the container by screwing. Alternatively, the coupling between the closing member and the container occurs other than by screwing, notably via a bayonet mechanism, by click-fastening or by gripping. The term “clickfastening” in particular means any system involving the crossing of a bead or cord of material by elastic deformation of a portion, notably of the closing member, followed by return to the elastically unconstrained position of said portion after the bead or cord has been crossed.
[0284] The container, advantageously comprising the compartment(s) or reservoir(s), and also the mixing container, may be at least partly made of thermoplastic material. Examples of thermoplastic materials that may be mentioned include polypropylene and polyethylene.
[0285] Alternatively, the containers are made of non-thermoplastic material, notably of glass or metal (or alloy).
[0286] 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 possibly the stem to which it may be rigidly connected. Such a wiper is described, for example, in patent FR 2 792 618.
[0287] The invention is illustrated in greater detail in the examples that follow. The amounts are indicated as weight percentages.
[0288] Example
[0289] Compound 1: Sucrose bearing acetoacetate functions
[0290] Compound 1 was synthesized according to the scheme below: [Chem 9]
[0291] in which scheme R1, which may be identical or different, represents a hydrogen atom or a - C(O)-CH2-C(O)-CH3 group, it being understood that at least two R1radicals represent - C(O)-CH2-C(O)-CH3. 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 a distillation column. The reaction medium is heated using an oil bath (oil bath temperature 140°C-150°C) for 4 hours. After 4 hours, NMR confirms the grafting of the acetoacetate function. The reaction medium is then concentrated on a rotary evaporator at 150°C under continuous vacuum. An orangey- yellow viscous liquid is obtained, corresponding after analysis to the expected product.
[0292] Compound 2: Glucose bearing acetoacetate functions (5 eq)
[0293] Compound 1 was synthesized according to the scheme below: [Chem 10] in which scheme Rl, which may be identical or different, represents a hydrogen atom or a - methylcarbonylmethylcarbonyl group -C(O)-CH2-C(O)-CH3, it being understood that at least two Rl radicals represent -C(O)-CH2-C(O)-CH3. 100 g of D-glucose and 482.90 g of tert-butyl acetoacetate are placed in a 1 -litre three-necked round-bottomed flask equipped with a mechanical stirrer and a distillation column. The reaction medium is heated using an oil bath (oil bath temperature 150°C-160°C) for 5 hours. After 5 hours, NMR confirms the grafting of the acetoacetate function. The reaction medium is then concentrated on a rotary evaporator at 150°C under continuous vacuum. A dark brown, highly viscous liquid is obtained, corresponding after analysis to the expected product.
[0294] Preparation of compositions A, (1) and B
[0295] Compositions A, (1) and B are prepared using the contents indicated in the tables below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
[0296] [Table 2]
[0297] [Table 3]
[0298] The compositions are prepared by simple mixing of 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).
[0299] Formulations to be applied Composition (A) according to the invention and composition (B) on the one hand, and comparative composition (1) and composition (B) on the other hand, were mixed in a 1:1 weight ratio using a SpeedMixer® (Hauschild DAC 150.1 FVZ) (10 grams, 1 cycle, 2 minutes 30 seconds, 2500 rpm).
[0300] Application
[0301] Each formulation ((A) + (B)) or ((1) + (B)) was applied with a spatula on a Supplale® support (SOUDOTIC reference RLXSUPNOIR, format: 30000 x 1200 mm x 0.7 mm) with dimensions of 2 cm x 5 cm, in a proportion of 0.02 g / cm2.
[0302] Drying is carried out at room temperature for 24 hours.
[0303] Resistance to biphase water
[0304] Once dry, the SUPPLALE® thus treated are immersed in biphase water (La Roche Posay Respectissime waterproof eye makeup remover) for 3 minutes.
[0305] After the immersion, the SUPPLALE® were rubbed against a towel (Chicopee® VERACLEAN™ Polish PLUS 34x32cm) 10 times with a weight of 660 g, over a length of 34 cm.
[0306] In order to measure the wear property of the colour, a colour difference (delta E) is measured between the initial deposit and the deposit after attack.
[0307] Persistence protocol
[0308] The persistence of the colour of the deposits was evaluated in the CIE L*a*b* system, using a Konica 700d® spectrophotometer from Minolta (illuminant D65, angle 10°, specular component included).
[0309] 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.
[0310] The persistence of the colour of the deposits is evaluated by the colour difference AE between the coloured SUPPLALE® before attack, then after having undergone an attack according to the protocol described above. The lower the AE value, the more persistent the colour with respect to the attacks.
[0311] The AE value is calculated according to the following equation:
[0312] [Math 1]
[0313] In this equation, L*a*b* represent the values measured after colouring the SUPPLALE® and after having undergone an attack, and LO*ao*bo* represent the values measured after colouring the SUPPLALE® but before attack.
[0314] Results
[0315] The evaluation results are summarized in the table below:
[0316] [Table 4] It is seen that the application of the formulation according to the invention makes it possible to obtain a significantly improved resistance to biphase water relative to the application of the comparative formulation.
Claims
Claims1. Process for making up keratin materials, notably the skin and / or lips and / or eyelashes and / or eyebrows, comprising at least the application to said keratin materials of at least two distinct compositions (A) and (B):- said composition (A) comprising at least: i) one or more compounds of formula (I) including the optical or geometrical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates:in which formula (I):- R1represents a polysaccharide unit, preferably a disaccharide unit, on which n hydroxy groups have been substituted with n -O-C(O)-CH2-C(O)-R2groups;R1also being: a) optionally substituted with one or more hydroxyl OH or amine -N(R)2 groups with R representing a (Ci-C4)alkyl group such as methyl, carboxyl -C(O)-OH, a vinyl group, and / or b) optionally interrupted with one or more heteroatoms or groups chosen from O, S, carbonyl -C(O)-, amine -N(R’), or combinations thereof 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, an alkyl group containing from 1 to 4 carbon atoms optionally substituted with at least one hydroxyl group (OH), or optionally substituted with -X-C(O)-C(Ra)(Rb)-C(O)-R2; preferably, R’ represents a hydrogen atom or a (Ci-C4)alkyl group;- R2represents a linear or branched, saturated or unsaturated Ci to Ce monovalent hydrocarbon-based radical, preferably a (Ci-C4)alkyl group such as methyl or tert-butyl, more preferentially methyl;- Raand Rb, which may be identical or different, represent a hydrogen atom or a (Ci- C4)alkyl group, preferably hydrogen;- X is a heteroatom or group chosen from O, S, N(R’), -S-CH2-C(O)-O-, -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; and ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and iv) at least one particulate colorant;- said composition (B) comprising at least v) a crosslinking agent chosen from (poly)amine compounds, notably aminoalkylpoly alkoxy silanes, a,co-diaminooxaalkanes, chitosans, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains.
2. Process according to the preceding claim, in which the compound(s) of formula (I) is (are) chosen from those of formula (la) including the optical or geometrical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates:in which formula (la):- R1represents a polysaccharide unit, preferably a disaccharide unit;R1also being: a) optionally substituted with one or more hydroxyl groups OH, and / or b) optionally interrupted with one or more heteroatoms or groups chosen from O, S, - N(R’), preferably interrupted with one or more oxygen atoms, in which R’ is as defined in formula (I);- R2is as defined in Claim 1, and preferably R2represents a linear or branched (Ci- Ce)alkyl group, preferably a (Ci-C4)alkyl group, more particularly methyl or tert-butyl, such as methyl; and- n being as defined in Claim 1, and preferably n denotes an integer ranging from 2 to 8.
3. Process according to either one of the preceding claims, in which the compound(s) of formula (I) or (la) is (are) such that R1represents a disaccharide unit onwhich n hydroxy groups have been substituted with n -O-C(O)-CH2-C(O)-R2groups, with R2and n being as defined in either one of Claims 1 and 2.
4. Process according to any one of the preceding claims, in which R1represents a disaccharide unit chosen from cellobiose, maltose, lactose, raffinose, saccharose (sucrose), trehalose, melibiulosis, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose, preferably sucrose.
5. Process according to any one of the preceding claims, in which the compound(s) of formula (I) or (la) is (are) chosen from the following compounds, including the optical isomers thereof, the salts thereof, and the solvates thereof, such as the hydrates:in which R1are chosen, independently of one another, from -C(O)-CH2-C(O)-CH3 and H with at least two radicals R1representing -C(O)-CH2-C(O)-CH3, preferably at least three radicals represent -C(O)-CH2-C(O)-CH3; more preferentially, the compounds of formula (I) and (la) are chosen from the compounds of formula (3).
6. Process according to any one of the preceding claims, in which the crosslinking agent(s) v) is (are) chosen from: a) chitosans such as poly(D-glucosamine), b) poly ether diamines, particularly polyethylene glycol a,co-diamines (bearing a chain-end amine function), c) a,co-diaminooxaalkanes such as 4, 7, 10-trioxa- 1,13 -tridecanediamine, d) polyether triamines, such as polyetheramines (or Jeffamine), e) aminoalkoxysilanes such as APTES and f) polydialkylsiloxanes comprising primary amine groups at the chain end or on side chains, particularly polydimethylsiloxanes comprising primary amine groups such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNfE) and amodimethicones comprising amine groups on side chains such as bis-cetearyl amodimethicone; preferably, the crosslinking agent(s) v) is (are) chosen from b) polyether diamines, particularly polyethylene glycol a,co-diamines (bearing a chain-end amine function), d) polyethers triamines such as polyetheramines (or Jeffamine), e) aminoalkoxysilanes such as APTES and f) polydialkylsiloxanes comprising primary amine groups at the chain end or on side chains, particularly polydimethylsiloxanes comprising primary amine groups such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNth) and amodimethicones comprising amine groups on side chains such as bis- cetearyl amodimethicone; and even more preferentially from f) polydialkylsiloxanes comprising primary amine groups at the chain end or on side chains, particularly polydimethylsiloxanes comprising primary amine groups such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNth) and amodimethicones comprising amine groups on side chains such as bis-cetearyl amodimethicone.
7. Process according to any one of the preceding claims, in which the particulate colorants are chosen from pigments, direct dyes and mixtures thereof, preferably pigments; more preferentially, the pigment(s) of the invention is (are) chosen from carbon black, iron oxides, notably yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, notably blue and violet triarylmethane pigments, such as Blue 1 Lake, azo pigments, notably red azo pigments, such as D&C Red 7, an alkali metal salt of lithol red, such as the calcium salt of lithol red B, even more preferentially red iron oxides, yellow iron oxides and azo pigments, notably red azo pigments, such as D&C Red 7.
8. Process according to any one of the preceding claims, in which said composition (A) and / or said composition (B) also comprises one or more fatty substances, particularly one or more oils, preferably volatile oils.
9. Process according to any one of the preceding claims, in which said composition (A) and / or said composition (B) also comprises one or more volatile oils, in particular chosen from:* hydrocarbon oils containing from 8 to 16 carbon atoms, and notably:- branched Cs-Ci6 alkanes, for instance isoalkanes such as C13-C16 isoparaffins, isododecane, isodecane and isohexadecane, alone or as mixtures, preferably isododecane, more preferentially isododecane;- linear alkanes, for example C11-C16 alkanes, alone or as mixtures, for instance hexane, decane, undecane, tridecane, isoparaffins, or n-dodecane (C12) and n-tetradecane (C14), the undecane-tridecane mixture, mixtures of n-undecane (Cl 1) and n-tridecane (Cl 3), and mixtures thereof and also mixtures of n-undecane (Cl l) and n-tridecane (Cl 3);- volatile, non-aromatic cyclic C5-C12 alkanes;* short-chain esters containing from 3 to 8 carbon atoms in total, such as ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate;* carbonate hydrocarbon-based oils of structure R’ I-O-C(O)-O-R’2 in which R’i and R’2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen from dibutyl carbonate or dipentyl carbonate;* ether oils of formula R1-O-R2 in which Ri and R2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;* silicone oils comprising in particular from 2 to 7 silicon atoms, these silicone oils optionally including alkyl or alkoxy groups containing 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 mixtures thereof; more preferentially, the volatile oil(s) are chosen from Cs-Ci6 alkanes, notably branched alkanes such as isododecane.
10. Process according to any one of the preceding claims, characterized in that it comprises two successive steps of applying, to said keratin materials, composition (A) and then composition (B), or composition (B) and then composition (A).
11. Process according to any one of Claims 1 to 9, characterized in that it comprises a step of applying to said keratin materials a composition obtained by extemporaneous mixing, at the time of application, of said composition (A) and said composition (B).
12. Multi-compartment kit or device, notably a cosmetic kit or device, for making up keratin materials, in particular the skin, lips, eyelashes and / or eyebrows, 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 in any one of Claims 1 to 5, ii) at least one monoalcohol comprising from 2 to 4 carbon atoms; iii) water; and iv) at least one particulate colorant;- at least one second compartment distinct from the first compartment, and containing at least the composition (B) comprising: v) a crosslinking agent chosen from (poly)amine compounds, notably aminoalkylpoly alkoxy silanes, a,co-diaminooxaalkanes, chitosans, polyetheramines, polydimethylsiloxanes comprising primary amine groups at the chain end or on side chains, in particular as defined in Claim 6.
Citation Information
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