USE OF A SPECIFIC AMINO SILICONE FOR HAIR CONDITIONING

Abstract

The present invention relates to the use of a specific amino silicone for hair conditioning, and more particularly for individualizing hair to maintain a lightweight feel. The invention relates to a hair coloring process comprising a step of applying a hair coloring composition comprising said specific amino silicone to the hair.

Description

Title of the invention: USE OF A SPECIFIC AMINO SILICONE FOR HAIR CONDITIONING

[0001] The present invention relates to the use of a specific amino silicone for hair conditioning, and more particularly for individualizing hair in order to maintain a lightness of the hair mass.

[0002] The invention relates to a hair coloring process comprising a step of applying to said hair a hair coloring composition comprising said specific amino silicone.

[0003] Hair can be weakened or damaged by the action of external atmospheric agents such as light and inclement weather, or by mechanical or chemical treatments such as brushing, combing, dyeing, bleaching, perming, and / or straightening. To remedy these problems, it is common to use hair care products that condition the hair. These hair care products can be conditioning shampoos or conditioners, which may be in the form of gels, hair lotions, or creams of varying thicknesses.

[0004] To improve the cosmetic properties of these compositions, it is known to introduce into them conditioning agents intended mainly to repair or limit the harmful or undesirable effects induced by the various treatments or aggressions that hair fibers undergo, more or less repeatedly.

[0005] However, it is still possible to improve the performance of hair care, in particular in terms of providing strength, while maintaining a certain lightness (toned and supple hair) as well as in terms of cosmetic properties such as detangling and smoothness to the touch; and this both immediately, when the composition is applied to the hair (at To), but also permanently, that is to say after several shampoos.

[0006] There is therefore a real need to develop a composition or process to improve the strength given to hair (denser, stiffer hair), and in particular to hair weakened or damaged by hair coloring, while maintaining its lightness; and this both immediately, when the composition is applied to the hair (at To), but also permanently, that is to say after several shampoos, for example permanently after at least 5 shampoos.

[0007] It is also of interest that the compositions applied to the hair have good properties of use, in particular that they are easy to apply to the keratin fibers.

[0008] These goals are achieved with the present invention, which notably relates to the use of at least one amino-coated silicone of the following formula (I): (I)

[0009] in which:

[0010] - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms;

[0011] - R2 independently represents a monovalent radical of formula -CqH2qL in where q is a number from 2 to 8, and L is an amine grouping, possibly quantized, chosen from the following groups:

[0012] -N(R3)2; -N+(R3)3 A; -NR3-YN(R3)2 and -NR-Y-N+(R3)3 A, in which R3, identical or different, represents a hydrogen atom, a phenyl group, a benzyl group, or a monovalent saturated hydrocarbon radical, for example a Ci-C20 alkyl group; Y denotes a group of formula CrH2r, linear or branched, r being an integer from 2 to 6, preferably from 2 to 4; and A represents a cosmetically acceptable anion, in particular a halide such as fluoride, chloride, bromide, or iodide; - X represents a radical corresponding to the following formula (II): (II) in which: - A independently represents an alkylene group having from 1 to 10 linear or branched carbon atoms, which may be interrupted by at least one heteroatom chosen from O, S, NH or a carbonyl group (CO), preferably NH, and - Q represents an alkylene group having from 1 to 20 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxyl group or an aminoalkyl group having from 1 to 20 carbon atoms, and - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer from 0 to 500 with n+m+o varying from 250 to 500,

[0013] in a composition C, preferably cosmetic, of permanent hair coloring comprising at least one coloring agent, to improve hair conditioning, in particular to improve hair individualization in order to maintain a lightness of the hair mass.

[0014] It has been observed that the silicone in formula (I) provides excellent conditioning / care for the hair. Hair treated in this way, and particularly hair weakened or damaged by hair coloring, is well individualized, giving it a soft, smooth, and easy-to-detangle feel. The improvement in hair conditioning is particularly significant when the silicone in formula (I) is applied to the hair using a permanent hair coloring composition.

[0015] It has also been observed that treated hair, and in particular hair weakened or damaged by hair coloring, is strengthened with more body and less breakage when combing.

[0016] The invention also relates to a hair coloring process, comprising at least one step of applying to the hair a composition C as described below.

[0017] Other objects, features, aspects and advantages of the invention will become even clearer upon reading the description and example that follows.

[0018] In this description, and unless otherwise indicated: - the expression "at least one" is equivalent to the expression "one or more" and can be substituted for it. - the expression "between... and..." is equivalent to the expression "ranging from... to..." and can be substituted for it, and implies that the limits are included. - By the expression "greater than" and respectively the expression "less than" in the meaning of the present invention, we mean an open interval that is strictly greater than, respectively strictly less than, and therefore that the bounds are not included. - For the purposes of this application, "long-lasting hair color" means a durable hair color that preferably withstands at least four shampoos, more preferably at least five shampoos, and ideally at least ten shampoos. In other words, the treated hair does not return to its natural color (i.e., without artificial coloring), even after preferably at least four shampoos, more preferably five shampoos, and ideally ten shampoos. - For the purposes of this application, "keratin fibers" refers particularly to human keratin fibers such as hair, eyelashes, eyebrows, and body hair, preferably hair, eyebrows and eyelashes, and even more preferably hair. - For the purposes of this invention, "hair" means the hair on the head. This term does not include body hair, eyebrows, or eyelashes. - For the purposes of this application, "fatty acid" means an organic acid comprising in its structure a hydrocarbon chain, linear or branched, saturated or unsaturated, comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, more preferably from 10 to 22 carbon atoms. - For the purposes of this application, "fatty alcohol" means an alcohol comprising in its structure a hydrocarbon chain, linear or branched, saturated or unsaturated, comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, more preferably from 10 to 22 carbon atoms. Amino silicones of formula (I)

[0019] According to the invention, at least one amino silicone of the following formula (I) is used in a permanent hair coloring composition C comprising at least one coloring agent, to improve hair conditioning: x ri: L. □ k. in which: - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms; - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, and L is an amine group possibly quaternized chosen from the groups: -N(R3)2; -N+(R3)3 A; -NR3-YN(R3)2 and -NR-Y-N+(R3)3 A, in which R3, identical or different, represents a hydrogen atom, a phenyl group, a benzyl group, or a monovalent saturated hydrocarbon radical, for example a Ci-C2o alkyl group; Y denotes a group of formula CrH2r, linear or branched, r being an integer from 2 to 6, preferably from 2 to 4; and A represents a cosmetically acceptable anion, in particular a halide such as fluoride, chloride, bromide or iodide; - X represents a radical corresponding to the following formula (II) (II) OJ A "" ' A in which: - A independently represents an alkylene group having from 1 to 10 linear or branched carbon atoms, which may be interrupted by at least one heteroatom chosen from O, S, NH or a carbonyl group (CO), preferably NH, and - Q represents an alkylene group having from 1 to 20 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer from 0 to 500 with n+m+o varying from 250 to 500.

[0020] In particular, at least one amino silicone of formula (I) is used in a permanent hair coloring composition C comprising at least one coloring agent, to improve the individualization of the hair, in order to maintain a lightness of the hair mass.

[0021] The term "amino silicone" means any silicone comprising at least one primary, secondary, tertiary amine or a quaternary ammonium group. The average molecular weights of these amino silicones can be measured by Gel Permeation Chromatography (GPC) at room temperature (25°C) in polystyrene equivalents. The columns used are Styragel p-columns. The eluent is THF, and the flow rate is 1 ml / min. 200 µL of a 0.5% by weight silicone solution is injected into the THF. Detection is performed by refractometry and UV measurement.

[0022] According to a preferred embodiment, the amino silicone(s) of formula (I) are such that:

[0023] - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, and L is an amine group possibly quaternized chosen from the groups: -N(R3)2 ; - N(R3)-CH2-CH2-N(R3)2 ; in which R3, identical or different, represents a hydrogen atom, a phenyl group, a benzyl group, or a monovalent saturated hydrocarbon radical, for example a Ci-C20 alkyl group; - X represents a radical corresponding to the following formula (II) (II) H f| in which: - A independently represents an alkylene group having from 1 to 6 linear or branched carbon atoms, being interrupted by at least one heteroatom chosen from O, S, NH or a carbonyl group (CO), preferably NH, and - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer ranging from 0 to 500 with n+m+o varying from 250 to 500.

[0024] According to a more preferred embodiment, the amino silicone(s) of formula (I) are such that:

[0025] - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms; - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, and L is an amine group of the following formula: - N(R3)-CH2-CH2-N(R3)2; in which R3 represents a hydrogen atom, - X represents a radical corresponding to the following formula (III)

[0026] (III) in which: - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and, - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer ranging from 0 to 500 with n+m+o varying from 250 to 500. According to a more preferred embodiment, the amino silicone used in composition C has the following formula (IV): in which: - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms; - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and, - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer ranging from 0 to 500 with n+m+o varying from 250 to 500.

[0027] According to a particular embodiment, the amino silicone(s) of formula (I) are present in composition C in the form of an emulsion or microemulsion with one or more surfactants, preferably non-ionic such as trideceth-10.

[0028] Among the amino silicones of formula (I) usable in composition C, we can mention the amino silicone with INCI name Bis-Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer. Another example is the commercial product BELSIL® DADM 3240 E sold by Wacker, with the following formula: in which the radicals R represent, independently of each other, preferably identical, a methyl group -CH3, hydroxyl group -OH or -OCH3.

[0029] Preferably, the total content of amino silicone(s) of formula (I) ranges from 0.01% to 25% by weight, more preferably from 0.1% to 20% by weight, more preferably from 0.5% to 20% by weight, better from 1% to 15% by weight, even better from 2% to 10% by weight, always better from 3% to 8% by weight, relative to the total weight of composition C.

[0030] Preferably, the total content of amino silicone(s) of formula (IV) ranges from 0.01% to 25% by weight, more preferably from 0.1% to 20% by weight, more preferably still from 0.5% to 20% by weight, better from 1% to 15% by weight, even better from 2% to 10% by weight, always better from 3% to 8% by weight, relative to the total weight of composition C.

[0031] Preferably, the total content of amino silicone of INCI name Bis-Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer, when present in the composition according to the invention, ranges from 0.01% to 25% by weight, more preferably from 0.1% to 20% by weight, more preferably still from 0.5% to 20% by weight, better still from 1% to 15% by weight, even better from 2% to 10% by weight, still better from 3% to 8% by weight, relative to the total weight of composition C. Coloring agent

[0032] Said composition C comprises at least one coloring agent.

[0033] Preferably, the coloring agent(s) are chosen from pigments, direct dyes, and their mixtures.

[0034] Said composition C may comprise one or more pigments.

[0035] By "pigment" is meant all pigments that impart color to materials keratin-based. Their solubility in water at 25 °C and atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01%.

[0036] The pigments that can be used are chosen in particular from among the organic and / or mineral pigments known in the art, in particular those described in Kirk-Othmer's Encyclopedia of Chemical Technology and in Ullmann's Encyclopedia of Industrial Chemistry.

[0037] They may be natural, of natural origin, or not.

[0038] These pigments may be in the form of powder or pigment paste. They may be coated or uncoated.

[0039] Pigments can, for example, be chosen from mineral pigments, organic pigments, lacquers, special effect pigments such as mother-of-pearl or glitter, and mixtures thereof.

[0040] The pigment may be a mineral pigment. By mineral pigment, we mean any pigment that meets the definition in the Ullmann Encyclopedia in the chapter on inorganic pigments. Examples of mineral pigments useful in the present invention include iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue, and titanium dioxide.

[0041] The pigment may be an organic pigment. By "organic pigment" is meant any pigment that meets the definition in the Ullmann encyclopedia in the chapter on organic pigment.

[0042] The organic pigment may in particular be chosen from the following compounds: nitroso, nitro, azo, xanthene, pyrene, quinoline, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane, quinophthalone.

[0043] In particular, the white or colored organic pigments may be selected from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments coded in the Color Index under references Cl 42090, 69800, 69825, 74100, 74160, the yellow pigments coded in the Color Index under references Cl 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments coded in the Color Index under references Cl 61565, 61570, 74260, the orange pigments coded in the Color Index under reference CI 11725, 45370, 71105, the red pigments coded in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, pigments obtained by oxidative polymerization of indole, phenolic derivatives as described in patent FR 2 679 771.

[0044] The organic pigment can also be a lacquer. By lacquer, we mean colorants adsorbed onto insoluble particles, the whole thus obtained remaining insoluble during use.

[0045] The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.

[0046] Among the colorants, we can mention carminic acid. We can also mention the colorants known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985), D & C Green (CI 61 570), D & C Yellow 1 O (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 (CI 42 090).

[0047] The pigment can also be a special effects pigment. Special effects pigments are defined as pigments that generally create a colored appearance (characterized by a certain shade, vibrancy, and clarity) that is non-uniform and changes depending on the viewing conditions (light, temperature, viewing angles, etc.). They are thus distinct from colored pigments that provide a uniform opaque, semi-transparent, or conventionally transparent tint.

[0048] The variety of pigments that can be used in the present invention makes it possible to obtain a rich palette of colors, as well as particular optical effects such as metallic, interference effects.

[0049] The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 µm, preferably between 20 nm and 80 µm, and more preferably between 30 nm and 50 µm.

[0050] Said composition C may comprise one or more direct colorant(s).

[0051] By "direct dye," we mean natural and / or synthetic dyes, different from oxidation dyes. These are dyes that diffuse superficially onto the fiber. They can be ionic, for example cationic or anionic, or non-ionic.

[0052] Examples of suitable direct dyes that can be mentioned include 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 mixtures.

[0053] Direct dyes can be selected from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly called "acid" direct dyes because of their affinity for alkali substances. Anionic direct dyes are understood to mean any direct dye having in its structure at least one CO2R or SO3R substituent, where R designates a hydrogen atom or a cation from a metal or an amine, or an ammonium ion. Anionic dyes can be selected from acidic nitro direct dyes, acidic azo dyes, acidic azinic dyes, acidic triarylmethanic dyes, acidic indoamine dyes, acidic anthraquinone dyes, indigoids, and acidic natural dyes.

[0054] A titre d’exemple de colorants acides on peut citer : Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3; Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2 ; Food yellow 3 ou sunset yellow; Acid Red 111, Acid Red 134, Acid yellow 38 ;

[0055] A titre d’exemple de colorants azo anioniques pyrazolones on peut citer : Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76Acid Yellow 17 ; As an example of anthraquinone dyes, we can cite: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT violet No. 2;: Acid Black 48;

[0057] Examples of nitro dyes include: Acid Brown 13; Acid Orange 3; examples of dyes of formula (XXII') include: Acid Yellow 1, Sodium salt of 2,4-dinitro-1-naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2(4'-N,N(2'-hydroxyethyl)amino-2'-nitro)aniline ethanesulfonic acid, 4-[3-hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C yellow 7;

[0058] Examples of triarylmethane dyes include: Acid Blue 1; Acid Blue 3; Acid Blue 7, Acid Blue 9; Acid Violet 49; Acid green 3; Acid green 5; Acid Green 50.

[0059] Examples of xanthenic dyes include: Acid Yellow 73; Acid Red 51; Acid Red 52, Acid Red 87; Acid Red 92; Acid Red 95; Acid Violet 9.

[0060] As an example of indole dyes, we can cite: Acid Blue 74;

[0061] Examples of quinoline dyes include: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.

[0062] Among the natural direct dyes that can be used according to the invention are lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine, and orceins. Extracts or decoctions containing these natural dyes, and in particular henna-based poultices or extracts, can also be used.

[0063] More preferably, the coloring agent(s) are chosen from among the pigments.

[0064] Preferably, the coloring agent(s) are present in a total quantity ranging from 0.001% to 20% by weight, preferably 0.005% to 15% by weight, relative to the total weight of composition C.

[0065] More preferably, the pigment(s) are present in a total quantity ranging from 0.001% to 20% by weight, preferably from 0.005% to 15% by weight, relative to the total weight of the composition C. Water

[0066] Preferably, said composition C further comprises water.

[0067] More preferably, the total water content present in composition C ranges from 5% to 90% by weight, more preferably from 10% to 80% by weight, more preferably still from 15% to 70% by weight, better still from 20% to 65% by weight, and even better still from 25% to 60% by weight, relative to the total weight of composition C. Organic solvents

[0068] Preferably, said composition C further comprises at least one organic solvent.

[0069] Examples of organic solvents include Ci-C4 alkanols such as ethanol and isopropanol; polyols and polyol ethers such as glycerol, 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0070] More preferably, the organic solvent(s) are chosen from ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, benzyl alcohol, and mixtures thereof.

[0071] More preferably, the organic solvent(s) are chosen from ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, and mixtures thereof.

[0072] In a particularly preferred manner, composition C comprises ethanol.

[0073] Preferably, the total content of organic solvent(s), when present in the composition, ranges from 1% to 70% by weight, more preferably from 2% to 60% by weight, more preferably still from 5% to 55% by weight, better from 10% to 55% by weight, even better from 15% to 50% by weight, relative to the total weight of composition C.

[0074] Preferably, the total ethanol content, when present in the composition, ranges from 1% to 70% by weight, more preferably from 2% to 60% by weight, more preferably from 5% to 55% by weight, better from 10% to 55% by weight, and even better from 15% to 50% by weight, relative to the total weight of composition C. Non-ionic surfactants

[0075] Preferably, said composition C further comprises at least one non-ionic surfactant.

[0076] The non-ionic surfactant(s) usable in the composition of the present invention are described in particular, for example, in "Handbook of Surfactants" by MR PORTER, Blackie & Son (Glasgow and London), 1991, pp 116-178.

[0077] By way of examples of nonionic surfactants, these may optionally be chosen from among oxyalkyl(C8-C24)phenols, oxyalkylated or glycerolated C8-C40 alcohols, oxyalkylated C8-C30 fatty acid amides, esters of C8-C30 acids and polyethylene glycols, esters of C8-C30 acids and sorbitol, esters of fatty acids and sucrose, alkyl(C8-C30)(poly)glucosides, alkenyl(C8-C30)(poly)glucosides, esters of alkyl(C8-C30)(poly)glucosides, oxyethylenated vegetable oils, condensates of ethylene oxide and / or propylene oxide, derivatives of A-alkyl(C8-C30)glucamine and A-acyl(C8-C30)-methylglucamine, amine oxides, and mixtures thereof.

[0078] More specifically, the following compounds may be cited, alone or in mixtures: - alkyl(C8-C24)oxyalkylened phenols; - alcohols in the C8 to C40 range, saturated or unsaturated, linear or branched, oxyalkylated or glycerolated, they preferably have one or two fatty chains; distinct from the fatty alcohols described previously; - C8 to C30 fatty acid amides, saturated or unsaturated, linear or branched, oxyalkylated; - esters of C8 to C30 acids, saturated or unsaturated, linear or branched, and of polyethylene glycols; - esters of C8 to C30 acids, saturated or unsaturated, linear or branched, and of sorbitol, preferably oxygenated; - fatty acid and sucrose esters, - alkyl(C8-C30)(poly)glucosides, alkenyl(C8-C30)(poly)glucosides, possibly oxyalkylated (0 to 10 oxyalkylated motifs) and comprising 1 to 15 glucose motifs, alkyl (C8-C30)(poly)glucoside esters, - oxyethylenated vegetable oils, saturated or unsaturated; - ethylene oxide and / or propylene oxide condensates; - A-alkyl(C8-C30)glucamine and A-acyl(C8-C30)-methylglucamine derivatives; - amine oxides.

[0079] They are chosen, in particular, from fatty alcohols, alpha-diols, alkyl(Ci-C2o)phenols, these compounds being ethoxylated, propoxylated or glycerolated, and having at least one fatty chain comprising, for example, from 8 to 40 carbon atoms, the number of ethylene oxide or propylene oxide groups being able to range in particular from 1 to 200 and the number of glycerol groups being able to range in particular from 1 to 30. Advantageously, the non-ionic surfactants are in particular C8-C30 fatty alcohols, preferably C8-C24, oxyalkylated, preferably ethoxylated comprising from 1 to 200 moles of ethylene oxide.

[0080] We can also mention ethylene oxide and propylene oxide condensates on fatty alcohols; ethoxylated fatty amides preferably having 1 to 30 ethylene oxide motifs, polyglycerol fatty amides having on average 1 to 5 glycerol groups and in particular 1.5 to 4, ethoxylated sorbitan fatty acid esters having 1 to 30 ethylene oxide motifs, sucrose fatty acid esters, polyethylene glycol fatty acid esters, (C6-C24 alkyl) polyglycosides, oxyethylenated vegetable oils, N-(C6-C24 alkyl)glucamine derivatives, amine oxides such as (C10-C14 alkyl)amine oxides or N-(C10-C14 acyl)aminopropylmorpholine oxides.

[0081] The esters (in particular mono, di, tri esters) of C8-C30 fatty acids, preferably C12-C22, and of sorbitan may be selected from: Sorbitan Caprylate; Sorbitan Cocoate; Sorbitan Isostearate; Sorbitan Laurate; Sorbitan Oleate; Sorbitan Palmitate; Sorbitan Stearate; Sorbitan Diisostearate; Sorbitan Dioleate; Sorbitan Distearate; Sorbitan Sesquicaprylate; Sorbitan Sesquiisostearate; Sorbitan Sesquioleate; Sorbitan Sesquistearate; Sorbitan Triisostearate; Sorbitan Trioleate; Sorbitan Tristearate.

[0082] Polyoxyethylenated C8-C30 fatty acid (preferably Ci2-Ci8) and sorbitan esters (in particular mono-, di-, and tri-esters) containing 2 to 20 moles of ethylene oxide may be selected from Ci2-Ci8 fatty acid esters, in particular lauric, myristic, cetyl, stearic, sorbitan (poly)oxyethylenated acid having in particular 1 to 30 moles of ethylene oxide, preferably 2 to 30 moles of ethylene oxide.

[0083] Non-ionic surfactants can also be chosen from alkyl(poly)glycoside (or APG) type non-ionic surfactants, also called alkyl(poly)glycoside non-ionic surfactants.

[0084] By "alky(poly)glycoside" is meant an alkylpolyglycoside or an alkylmonoglycoside, also called alkylglycoside in this application, the alkyl group of which comprises between 6 and 30 carbon atoms, preferably between 6 and 24 carbon atoms, and which may optionally be alkoxylated by one or more alkylene oxide groups, preferably at C2 to C4.

[0085] The non-ionic alkyl(poly)glycoside surfactant(s) are preferably chosen from the following compounds of formula (III) and their mixtures: R1O-(R2O)t(G)v (III) formula (I), wherein: - Ri represents a saturated or unsaturated, linear or branched alkyl group, comprising from 6 to 24 carbon atoms, an alkylphenyl group whose linear or branched alkyl group comprises from 6 to 24 carbon atoms, - R2 represents an alkylene group with approximately 2 to 4 carbon atoms, - G represents a saccharidic motif with 5 to 6 carbon atoms, -1 designates a value from 0 to 10, preferably 0 to 4, and -v designates a value from 1 to 15.

[0086] Preferably, the non-ionic alkyl(poly)glycoside surfactant(s) are chosen, alone or in mixture, from compounds of formula (III) in which: - Ri designates a saturated or unsaturated, linear or branched alkyl group comprising 8 to 18 carbon atoms, - G designates glucose, fructose or galactose, and preferably glucose, -1 denotes a value ranging from 0 to 3, and is preferably equal to 0, and - R2 and v are as defined previously.

[0087] The degree of polymerization of the non-ionic alkyl(poly)glycoside surfactant(s), as represented for example by the index v in formula (III) above, varies on average from 1 to 15, and preferably from 1 to 4. This degree of polymerization varies more particularly from 1 to 2, and even better from 1.1 to 1.5, on average.

[0088] The glycosidic bonds between the saccharidic motifs are in 1,6 or in 1,4; and preferably in 1,4.

[0089] The non-ionic alkyl(poly)glycosides surfactants that may be used in the present invention are preferably alkyl(poly)glucosides, in particular represented by the products sold by the company COGNIS under the names PLANTAREN ® (600 CS / U, 1200 and 2000) or PLANTACARE® (818, 1200 and 2000). The products sold by the company SEPPIC under the names TRITON CG 110 (or ORAMIX CG 110) and TRITON CG 312 (or ORAMIX® NS 10), the products sold by the company BASF under the name LUTENSOL GD 70, or those sold by the company CHEM Y under the name AGIO LK, or the products sold by the company EVONIK GOLDSCHMIDT under the trade names TEGO CARE CG 90 or TEGO CARE CG 90 MB, can also be used.

[0090] The nonionic alkyl(poly)glycoside surfactant(s) present in the composition of the invention are preferably selected from caprylyl / capryl glucoside, decyl glucoside, coco glucoside, lauryl glucoside, myristyl glucoside, cetearyl glucoside, arachidyl glucoside, and mixtures thereof. More preferably, the nonionic alkyl(poly)glycoside surfactant(s) are selected from caprylyl / capryl glucoside, decyl glucoside, coco glucoside, lauryl glucoside, and mixtures thereof. Even more preferably, the nonionic alkyl(poly)glycoside surfactant is coco glucoside.

[0091] Non-ionic surfactants can also be chosen from oxygenated vegetable oils.

[0092] The non-ionic surfactant(s) are preferably selected from: a) oxyethylated fatty alcohols, comprising at least one C8 to C40 alkyl chain including 1 to 100 moles of ethylene oxide, b) ethoxylated C8-C30 fatty acid and sorbitan esters having 1 to 30 moles of ethylene oxide, c) (C6-C24 alkyl) polyglycosides, and d) mixtures thereof.

[0093] More preferably, the non-ionic surfactant(s) are chosen from among the oxyethylated fatty alcohols, comprising at least one alkyl chain in C8 to C40, in particular in C8-C2o, even better in Ci0-Ci8, saturated or unsaturated, linear or branched, and comprising from 1 to 100 moles of ethylene oxide, preferably from 2 to 50 moles, more particularly from 2 to 40 moles, or even from 3 to 20 moles of ethylene oxide.

[0094] Preferably, the total content of non-ionic surfactant(s), when present in composition C, is in the range of 0.01% to 20% by weight; more preferably from 0.05% to 10% by weight; better from 0.1% to 5% by weight, relative to the total weight of composition C.

[0095] Preferably, when present in composition C, the total content of nonionic surfactant(s) selected from among oxyethylenated fatty alcohols having at least one alkyl chain at C8 to C40 and from 1 to 100 moles of ethylene oxide, is in the range of 0.01% to 20% by weight; more preferably of 0.05% to 10% by weight; better goes from 0.1% to 5% by weight, relative to the total weight of composition C. Film-forming polymers

[0096] Preferably, said composition C further comprises at least one film-forming polymer.

[0097] By "film-forming" polymer, we mean a polymer capable of forming, on its own or in the presence of an auxiliary film-forming agent, a macroscopically continuous film on a support, in particular on keratinous materials, and preferably a cohesive film.

[0098] By way of example, the film-forming polymer may be chosen from the group comprising: - film-forming polymers soluble in an organic solvent medium, in particular liposoluble polymers; this means that the polymer is soluble or miscible in the organic medium and will form a single homogeneous phase when incorporated into the medium. - Film-forming polymers dispersible in an organic solvent medium; this means that the polymer forms an insoluble phase in the organic medium, the polymer remaining stable and / or compatible once incorporated into this medium. In particular, such polymers can be in the form of non-aqueous dispersions of polymer particles, preferably dispersions in silicone or hydrocarbon oils; in one embodiment, the non-aqueous polymer dispersions comprise polymer particles stabilized on their surface by at least one stabilizing agent; these non-aqueous dispersions are often called "NADs (non-aqueous dispersions)". - Film-forming polymers in the form of aqueous dispersions of polymer particles mean that the polymer forms a water-insoluble phase. The polymer remains stable and / or compatible once incorporated into water, and the polymer particles can be stabilized on their surface by at least one stabilizing agent. These polymer particles are often called "latex"; in this case, the composition must include an aqueous phase. - film-forming (co)polymers of vinylpyrrolidone, - film-forming (co)polymers of vinyl alcohol, - vinyl acetate film-forming polymers, - carboxyvinyl film-forming (co)polymers, - film-forming (co)polymers of the acrylic acid type, - film-forming (co)polymers of the methacrylic acid type, - natural film-forming gums, - film-forming polysaccharides, - film-forming (co)polymers acrylamides, and - their mixtures.

[0099] The film-forming polymer(s) according to the invention may, for example, be selected from acrylic acid (co)polymers, methacrylic acid (co)polymers, acrylic acid ester homopolymers and copolymers, methacrylic acid ester homopolymers and copolymers, acrylic acid amide homopolymers and copolymers, methacrylic acid amide homopolymers and copolymers, olefin homopolymers and copolymers, styrene homopolymers and copolymers, ether homopolymers and copolymers, vinyl ester or amide homopolymers and copolymers, and (meth)acrylic acid ester or amide homopolymers and copolymers containing an alkyl group. Ci-C20, linear, branched or cyclic, a C6-Ci0 aryl group or a C2-C6 hydroxyalkyl group, polyurethanes, polyesters, polyamides, homopolymers or copolymers of N-vinylpyrrolidone,vinyl alcohol (co)polymers, vinyl acetate polymers, carboxyvinyl (co)polymers, vinyl caprolactam homopolymers or copolymers, vinyl N-alkyl(Ci-C6) pyrroles homopolymers or copolymers, vinyl oxazoles homopolymers or copolymers, vinyl thiazoles homopolymers or copolymers, vinyl pyrimidine homopolymers or copolymers, vinylimidazole homopolymers or copolymers, natural gums, polysaccharides, acrylamide (co)polymers, styrene / vinylpyrrolidone copolymers, vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / DMAPA acrylates copolymers, vinyl pyrrolidone / vinyl caprolactam / DMAPA acrylates copolymers, and mixtures thereof.

[0100] Examples include: - the ethylene / sodium acrylate copolymer marketed under the trade name ECOSMOOTH SATIN® by the company Dow; - copolymers whose CTFA designation (4th Ed., 1991) is Octylacrylamide / acrylates / butylaminoethyl-methacrylate copolymer, such as the products sold under the name AMPHOMER® or LOVOCRYL® 47 by the company NATIONAL STARCH, as well as copolymers whose CTFA designation is Acrylates / octylacrylamide copolymer, such as the products sold under the name DERMACRYL® LT or DERMACRYL® 79 by the company NATIONAL STARCH; - The copolymers are marketed by the company ROHM AND HAAS under the name Aculyn®33; - Copolymers of unsaturated ethylenic acid esters and alkoxylated fatty alcohols such as: Aculyn®28 (Acrylates / Beheneth-25 Methacrylate Copolymer), Structure 2001® (Acrylates / Steareth-20 Itaconate Copolymer), Structure 3001® (Copolymer Acrylates / Ceteth-20 Itaconate), Structure Plus® (Acrylates / Aminoacrylates copolymer C10-30 Alkyl PEG-20 Itaconate), Carbopol® 1342, 1382, Ultrez 20, Ultrez 21 (Acrylates / CiO-3oAlkyl acrylate crosspolymer), Synthalen W2000® (Acrylates / Palmeth-25 Acrylate copolymer) or SOLTEX OPT (acrylates / Ci2-22 alkyl methacrylate copolymer) marketed by ROHM AND HAAS; - vinylpyrrolidone (PVP) homopolymers marketed under the name Luviskol® K by BASF SE, in particular Luviskol® K 90 or Luviskol® K 85 by BASF SE; - vinylpyrrolidone / vinyl ester copolymers marketed under the name Luviskol® by BASF SE, in particular the non-ionic polymers Luviskol® VA64 and Luviskol® VA73 (vinylpyrrolidone / vinyl acetate copolymers); - Vinylpyrrolidone / vinyl caprolactam / DMAPA acrylates copolymers marketed by Ashland Inc. under the trade name Aquaflex® SF-40; - vinylpyrrolidone / DMAPA acrylates copolymers marketed by Ashland Inc. under the trade name Styleze CC-10.

[0101] By way of example, one may cite the film-forming polymer(s) selected from cationic acrylic copolymers, preferably insoluble in water, with the following motifs: a) Methacryloyloxyethyltrimethylammonium salt, b) Butyl methacrylate and c) Ethoxyethyl methacrylate.

[0102] Such copolymers are described, for example, in document JP5745266. Preferably, the polymer contains the three preceding monomers in the following proportions relative to the total number of monomer units, by weight in the resulting copolymer, without taking into account their salts: a) In a proportion of 0.5 to 20%, preferably between 1 and 5%; b) In a proportion of 20 to 98%, preferably between 40 and 97% and c) In a proportion of 1.5 to 95%, preferably between 2 and 55%.

[0103] Preferably, the copolymer is not amphoteric, that is to say, it does not have motifs carrying an anionic charge.

[0104] Preferably, the motifs of the copolymer are all methacrylate derivatives.

[0105] More specifically, the copolymer corresponds to the copolymer of INCI name Polyquaternium-99, such as for example the polymer marketed by the company GOO-CHEMICAL under the name Plascize L-514.

[0106] This is the butyl methacrylate / ethoxyethyl methacrylate / methacryloyloxyethyltrimethylammonium chloride copolymer, at 30% in ethanol: CH. CH,S CH, -4^4—Jt+chU—44"CHr4—4" 40 in 4° 0 9 I ca 9 A 9 A OEt H,;C-~AcH3 ^ci

[0107] In particular, the film-forming polymer(s) can also be chosen from polyurethanes, possibly from aqueous dispersions of polyurethane particles.

[0108] The polyurethanes usable according to the present invention may optionally further comprise compounds that are respectively located at the ends of the chains and terminate said chains (chain terminators). Such compounds are described in particular in US patents 7,445,770 and / or US patents 7,452,770.

[0109] By way of non-limiting example of polyurethanes, one can cite those sold under the name Baycusan® by Bayer such as, for example, Baycusan® C1000 or C1001 (INCI name: polyurethane-34), Baycusan® C1003 (INCI name: polyurethane-32), Baycusan® C1004 (INCI name: polyurethane-35) and Baycusan® C1008 (INCI name: polyurethane-48).

[0110] More preferably, the film-forming polymer(s) are selected from polyurethanes, cationic acrylic copolymers, vinylpyrrolidone (PVP) homopolymers, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / styrene copolymers, vinylpyrrolidone / ethylene copolymers, vinylpyrrolidone / propylene copolymers, vinylpyrrolidone / vinyl caprolactam copolymers, vinylpyrrolidone / vinylformamide copolymers, vinylpyrrolidone / vinyl alcohol copolymers, acrylamide copolymers, acrylic acid ester homopolymers or copolymers, acrylic acid homopolymers or copolymers, methacrylic acid homopolymers or copolymers, ethylene homopolymers or copolymers, and their mixtures.

[0111] More preferably still, the film-forming polymer(s) are chosen from polyurethanes, acrylic cationic copolymers, and their mixtures.

[0112] According to a particular embodiment of the invention, the film-forming polymer(s) are selected from Polyquatemium-99, Polyurethane-34, Polyurethane-32, Polyurethane-35, Polyurethane-48, and mixtures thereof.

[0113] Preferably, the total content of film-forming polymer(s) in the composition ranges from 0.1% to 30% by weight, more preferably from 1% to 25% by weight, more preferably still from 2% to 20% by weight, better still from 5% to 15% by weight, even better from 6% to 12% by weight, always better from 8% to 12% by weight, relative to the total weight of the composition.

[0114] Preferably, the total content of cationic acrylic copolymer(s) and polyurethane(s), when present in the composition, ranges from 0.1% to 30% by weight, more preferably from 1% to 25% by weight, more preferably from 2% to 20% by weight, better from 5% to 15% by weight, even better from 6% to 12% by weight, always better from 8% to 12% by weight, relative to the total weight of the composition.

[0115] Preferably, the pH of composition C is between 3 and 9, more preferably between 4 and 8, more preferably still between 5 and 8.

[0116] The pH of the composition according to the invention can be adjusted to the desired value by means of alkalizing agents (such as monoethanolamine) and / or acidifying agents (such as citric acid).

[0117] Said composition C may optionally also contain one or more additives used in cosmetics, such as, for example, thickeners, additional solvents (other than those previously disclosed), silicones different from those previously described, anionic surfactants, cationic surfactants, amphoteric surfactants, polymers.

[0118] These additives may be present in composition C in an amount ranging from 0 to 20% by weight relative to the total weight of composition C.

[0119] A person skilled in the art will take care to choose any such additives and their quantities so that they do not impair the properties of the compositions of the present invention.

[0120] According to a preferred embodiment of the invention, said composition C comprises: - at least one amino silicone of formula (I) as described above; - water; - at least one non-ionic surfactant; and - possibly at least one organic solvent chosen from among the alcohols, including ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, benzyl alcohol, and mixtures thereof.

[0121] Preferably according to this embodiment, the amino silicone is a silicone of formula (IV) as described above, more preferably the amino silicone of INCI name Bis-Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer.

[0122] According to another preferred embodiment of the invention, said composition C comprises: - at least one film-forming polymer chosen from Polyquatemium-99, Polyurethane-34, Polyurethane-32, Polyurethane-35, Polyurethane-48, and their mixtures; - at least one amino silicone of formula (I), preferably at least one amino silicone of formula (IV), as described above; more preferably the amino silicone with INCI name Bis-Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer; - water; - at least one non-ionic surfactant selected from among the oxyethylenated fatty alcohols, comprising at least one alkyl chain in the C8 to C40 range, particularly in the C8-C2O range, even better in the C10-C18 range, saturated or unsaturated, linear or branched, and comprising from 1 to 100 moles of ethylene oxide, preferably from 2 to 50 moles, more particularly from 2 to 40 moles, or even from 3 to 20 moles of ethylene oxide; and - possibly at least one organic solvent chosen from among the alcohols, preferably ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, benzyl alcohol, and mixtures thereof; more preferably ethanol;

[0123] Preferably, said composition C is free of cationic surfactant.

[0124] Preferably, said composition C is free of (poly)carbodiimide compound. The term "(poly)carbodiimide compound" means a compound comprising one or more carbodiimide group(s), preferably at least two carbodiimide groups, more preferably at least three carbodiimide groups, in particular the number of carbodiimide groups not exceeding 200, preferably 150, more preferably 100. The term “carbodiimide group” means a divalent linear triatomic fraction of general formula - (N=C=N) -.

[0125] The invention also relates to a hair coloring process comprising a step of applying to said hair a composition C of residual hair coloring as described above.

[0126] Preferably, said composition C is applied to dry or damp hair.

[0127] According to one embodiment, the hair is not rinsed, in particular with water, or washed, especially with shampoo, after the application of composition C containing formula silicone (I), or at least within 2 hours, preferably within 3 hours, more preferably within 4 hours, better within 6 hours, even better within 12 hours, or even within 24 hours, after the application step of composition C.

[0128] The following examples serve to illustrate the invention without, however, being intended to be limiting. Examples

[0129] Example 1: Process for synthesizing amino silicone of formula (I) In an aqueous emulsion comprising trideceth-10 and containing 35% amodimethicone bearing 3-(2-aminoethylamino)propyl functional groups, 1.1 stoichiometric equivalents of diethyl L-tartrate are added. The resulting mixture is homogenized at room temperature, yielding a smooth, white, low-viscosity silicone emulsion.

[0130] Example 2: Reference compositions A2.1 and A2.2, comparative compositions B2.1 and B2.2, as well as compositions C2.1 and C2.2 according to the invention, were prepared from the ingredients indicated in Tables 1 and 2 below, the quantities of which are expressed as % by weight of active material (ma).

[0131] [Tables 1] A2.1 (Reference) B2.1 (Comparative) C2.1 (Invention) Aminated silicone of formula (I)(1) - - 4.6 mA Amodimethicone (2) - 4.6 mA - Water Qsp 100 Qsp 100 Qsp 100

[0132] (1) synthesized according to the synthesis process described in Example 1

[0133] (2) sold by the company WACKER under the name BELSIL ADM LOG 1 (to (15% active ingredient)

[0134] [Tables2] A2.2 (Reference) B2.2 (Comparative) C2.2 (Invention) Formula silicone amino acid (I)(1) - - 2 mA Amodimethicone (2) - 2 mA - Water Qsp 100 Qsp 100 Qsp 100

[0135] (1) synthesized according to the synthesis process described in Example 1

[0136] (2) sold by the company WACKER under the name BELSIL ADM LOG 1 (to (15% active ingredient)

[0137] Application protocol for sensory evaluation:

[0138] The above compositions are applied with a finger to a 2.7g wick of Natural hair with a bath ratio of 0.8g per gram of hair. Each The strand is dried with a hairdryer while being combed with a comb, first with the large teeth and then the smaller ones. The experiment ends when the strand is dry.

[0139] Sensory evaluation protocol and results obtained:

[0140] In general, the application of amino silicone to the hair improves detangling, but has the disadvantage of sticking the hair together to form clumps of hair, unlike natural untreated hair which is individualized.

[0141] After the above treatment, the hair strands were evaluated by a panel of 5 people selected and trained for the sensory evaluation of hair strands.

[0142] The evaluation was carried out on the individualization of the hair.

[0143] The scores correspond to the criteria below: 0 = very bad, clumps of hair to the touch 5 = hairs very well individualized

[0144] The results are as follows:

[0145] [Tables3] Individualization A2.1 Reference B2.1 Comparison C2.1 Invention Panelist 1 4 1 1.5 Panelist 2 4 0.5 1.5 Panelist 3 5 0 2 Panelist 4 5 0.5 2 Panelist 5 5 0.5 2 Average 4.6 0.5 1.8

[0146] [Tables4] Individualization A2.2 Reference B2.2 Comparison C2.2 Invention Panelist 1 4 1.5 2.5 Panelist 2 4 1 2.5 Panelist 3 5 0 3 Panelist 4 5 1 2.5 Panelist 5 5 1.5 3.5 Average 4.6 1 2.8

[0147] These results show an improvement in hair individualization after treatment with the amino silicone of formula (I). The use of this silicone allows for better hair individualization and a reduction in the clumping effect, compared to the use of a conventional amino silicone, i.e., amodimethicone.

[0148] Example 3: Comparative compositions A3.1, A3.2, B3.1 and B3.2, as well as compositions C3.1 and C3.2 according to the invention, were prepared from the ingredients indicated in Tables 5 and 6 below, the quantities of which are expressed as % by weight of active material (ma).

[0149] The film-forming polymer is used to give texture to hair, particularly useful for fine hair.

[0150] [Tables5] A3.1 (Comparative) B3.1 (Comparative) C3.1 (Invention) Polyquaterium-99 9.6 mA 9.6 mA 9.6 mA Formula silicone amino (I)(1) - - 4.6 mA Amodimethicone (2) - 4.6 mA - Ethanol / Water mixture 50 / 50 Qsp 100 Qsp 100 Qsp 100

[0151] (1) synthesized according to the synthesis process described in Example 1

[0152] (2) sold by the company WACKER under the name BELSIL ADM LOG 1 (to (15% active ingredient)

[0153] [Tableauxô] A3.2 (Comparative) B3.2 (Comparative) C3.2 (Invention) Polyurethane-34 9.6 mA 9.6 mA 9.6 mA Formula Aminated Silicone (I)(1) - - 4.6 mA Amodimethicone (2) - 4.6 mA - Water Qsp 100 Qsp 100 Qsp 100

[0154] (1) synthesized according to the synthesis process described in Example 1

[0155] (2) sold by the company WACKER under the name BELSIL ADM LOG 1 (to (15% active ingredient) Sensory evaluation of hair#:

[0156] For this evaluation, 2.7g strands of HT4 natural hair were used.

[0157] Each of the compositions is applied to a strand of dry hair at a bath ratio of 0.8g of composition / gram of hair.

[0158] Each wick is then dried and stored at 22°C for 24 hours before evaluation.

[0159] A sensory evaluation of the smoothness to the touch (smooth feel) and of the suppleness is then carried out for each of the strands by 5 experts.

[0160] Each cosmetic attribute is evaluated by a score between 0 and 5: 0 / 5 corresponding to a strand of hair with a rough and non-cosmetic feel, 5 / 5 corresponding to a strand of hair with a very satisfactory cosmetic feel.

[0161]

[0162] The results are grouped in Tables 7 to 10 below. [Tables 7] Smooth to the touch A3.1 (Comparative) B3.1 (Comparative) C3.1 (Invention) Expert #1 5 5 5 Expert #2 3 2 5 Expert #3 3 1.5 4 Expert #4 3 2 5 Expert #5 3 4 5 Average 3.4 2.9 4.8

[0163] [Tables8] Smooth to the touch A3.2 (Comparative) B3.2 (Comparative) C3.2 (Invention) Expert #1 0 1 2 Expert #2 0 2 2 Expert #3 0 1 4 Expert #4 0 2 4 Expert #5 0 1 3 Average 0 1.4 3

[0164] [Tables9] Flexibility A3.1 (Comparative) B3.1 (Comparative) C3.1 (Invention) Expert #1 4 3 5 Expert #2 3 2 5 Expert #3 3 1.5 3 Expert #4 1 3 5 Expert #5 1 2 4 Average 2.4 2.3 4.4

[0165] [TableauxlO] Flexibility A3.2 (Comparative) B3.2 (Comparative) C3.2 (Invention) Expert #1 1 2 3.5 Expert #2 1 3 4 Expert #3 1 2 4 Expert #4 0 3 5 Expert #5 1 3 4 Average 0.8 2.6 4.1

[0166] In the A3.1 and A3.2 comparisons, it can be noted that the feel obtained when using a film-forming polymer is unsatisfactory. With such compositions, hair texture is indeed improved, but at the expense of the feel, which is rough and unacceptable to the user of the composition. Compositions B3.1 and B3.2 show that the addition of aminosilicone improves the cosmetic appearance, but without providing a satisfactory result for the user; the hair remains rough to the touch.

[0167] For compositions C3.1 and C3.2 according to the invention containing the amino silicone of formula (I), a clear improvement in touch is noted, which then becomes acceptable for the user.

[0168] Hair strands treated with one of the compositions C3.1 or C3.2 according to the invention exhibit a higher level of conditioning than hair strands treated with one of the comparative compositions A3.1, A3.2, B3.1 or B3.2, particularly in terms of smooth feel and hair suppleness.

Claims

1. Demands Use of at least one amino silicone of the following formula (I): (I) in which: - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms; - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, and L is an amine group, possibly quaternized, chosen from the following groups: -N(R3)2; -N+(R3)3 A; -NR3-YN(R3)2 and -NR-Y-N+(R3)3 A, in which R3, identical or different, represents a hydrogen atom, a phenyl group, a benzyl group, or a monovalent saturated hydrocarbon radical, for example a Ci-C20 alkyl group; Y denotes a group of formula CrH2r, linear or branched, r being an integer from 2 to 6, preferably from 2 to 4; and A represents a cosmetically acceptable anion, in particular a halide such as fluoride, chloride, bromide or iodide; - X represents a radical corresponding to the following formula (II):

2. - A independently represents an alkylene group having from 1 to 10 linear or branched carbon atoms, which may be interrupted by at least one heteroatom chosen from O, S, NH or a carbonyl group (CO), preferably NH, and - Q represents an alkylene group having from 1 to 20 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer from 0 to 500 with n+m+o varying from 250 to 500, in a permanent hair coloring composition C comprising at least one coloring agent, to improve hair conditioning. Use according to the preceding claim, characterized in that the amino silicone(s) of formula (I) are such that: - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, and L is an amine group, possibly quaternized, chosen from the following groups: -N(R3)2 ; - N(R3)-CH2-CH2-N(R3)2 ; in which R3, identical or different, represents a hydrogen atom, a phenyl group, a benzyl group, or a monovalent saturated hydrocarbon radical, for example a Ci-C20 alkyl group; - X represents a radical corresponding to the following formula (II) (II) OQ

3. - A independently represents an alkylene group having from 1 to 6 linear or branched carbon atoms, being interrupted by at least one heteroatom chosen from O, S, NH or a carbonyl group (CO), preferably NH, and - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer from 0 to 500 with n+m+o varying from 250 to 500. Use according to any one of the preceding claims, characterized in that the amino silicone(s) of formula (I) are such that: - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms; - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number from 2 to 8, and L is an amine group of the following formula: - N(R3)-CH2-CH2-N(R3)2; in which R3 represents a hydrogen atom, - X represents a radical corresponding to the following formula (III): ô G (HD in which: - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and, - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer from 0 to 500 with n+m+o varying from 250 to 500.

4. Use according to any one of the preceding claims, characterized in that the amino silicone(s) of formula (I) are of the following formula (IV):

5. (IV) in which: - RI independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms; - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group possibly being substituted by at least one alkoxy group having from 1 to 10 carbon atoms, a hydroxy group or an aminoalkyl group having from 1 to 20 carbon atoms, and, - n denotes an integer from 0 to 500, m denotes an integer from 1 to 500 and o denotes an integer from 0 to 500 with n+m+o varying from 250 to 500. Use according to any one of the preceding claims, characterized in that the total content of amino silicone(s) of formula (I) ranges from 0.01% to 25% by weight, preferably from 0.1% to 20% by weight, more preferably from 0.5% to 20% by weight, more preferably from 1% to 15% by weight, better from 2% to 10% by weight, even better from 3% to 8% by weight, relative to the total weight of composition C.

6. Use according to any one of the preceding claims, characterized in that composition C further comprises water.

7. Use according to the preceding claim, characterized in that the total water content ranges from 5% to 90% by weight, preferably from 10% to 80% by weight, more preferably from 15% to 70% by weight, more preferably still from 20% to 65% by weight, better from 25% to 60% by weight, relative to the total weight of composition C.

8. Use according to any one of the preceding claims, characterized in that composition C further comprises at least one organic solvent; preferably selected from CrC4 alkanols, polyols, polyol ethers, aromatic alcohols, and mixtures thereof; more preferably from ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, benzyl alcohol, and mixtures thereof; even better ethanol.

9. Use according to the preceding claim, characterized in that the total content of organic solvent(s) ranges from 1% to 70% by weight, preferably from 2% to 60% by weight, more preferably from 5% to 55% by weight, more preferably still from 10% to 55% by weight, better from 15% to 50% by weight, relative to the total weight of composition C.

10. Use according to any one of the preceding claims, characterized in that composition C further comprises at least one non-ionic surfactant; preferably selected from oxyethylated fatty alcohols, having at least one C8 to C4o alkyl chain, in particular C8-C2o, even better Ci0-Ci8, saturated or unsaturated, linear or branched, and comprising from 1 to 100 moles of ethylene oxide, preferably from 2 to 50 moles, more particularly from 2 to 40 moles, or even from 3 to 20 moles of ethylene oxide.

11. Use according to the preceding claim, characterized in that the total content of non-ionic surfactant(s) ranges from 0.01% to 20% by weight; more preferably from 0.05% to 10% by weight; better goes from 0.1% to 5% by weight, relative to the total weight of composition C.

12. Use according to any one of the preceding claims, characterized in that composition C further comprises at least one film-forming polymer; preferably selected from acrylic cationic copolymers, polyurethanes, and mixtures thereof.

13. A hair coloring process comprising a step of applying to said hair a composition C as defined in any one of claims 1 to 12.