Hair dyeing process using a specific aminosilicone

Abstract

The present invention relates to a process for dyeing hair, comprising the application of a specific aminosilicone for conditioning the hair, and more particularly for the separation into individual strands of the hair in order to maintain lightness in the hair mass.

Description

[0001] HAIR DYEING PROCESS USING A SPECIFIC AMINOSILICONE

[0002] The present invention relates to a process for dyeing hair, comprising the application of a specific aminosilicone for conditioning the hair, and more particularly for the separation into individual strands of the hair (hair individualization) in order to maintain lightness in the hair mass.

[0003] Hair may be embrittled or damaged by the action of external atmospheric agents such as light and bad weather, or by mechanical or chemical treatments, such as brushing, combing, dyeing, bleaching, permanent-waving and / or relaxing. To overcome these drawbacks, it is common practice to make use of hair treatments that are able to condition the hair. These hair care compositions may be conditioning shampoos or hair conditioners, which may be in the form of gels, hair lotions or creams of varying thickness.

[0004] To improve the cosmetic properties of these compositions, it is known practice to introduce therein conditioning agents intended primarily to repair or limit the harmful or undesirable effects brought about by the various treatments or attacking factors to which hair fibres are repeatedly subjected to a varying degree.

[0005] However, there is still scope for improving haircare performance, particularly in terms of providing strength, while at the same time retaining a certain lightness (toned and tangle-free hair), and also in terms of cosmetic properties such as disentangling and smooth feel; both immediately, at the time of application of the composition to the hair (at To), but also more permanently, i.e. after multiple shampoo washes.

[0006] There is accordingly a real need to develop a hair dyeing process capable of improving the strength imparted to hair (denser, more rigid hair) and in particular to hair embrittled or damaged by hair dyeing, while at the same time retaining lightness; both immediately, at the time of application of the composition to the hair (at To), but also permanently, i.e. after multiple shampoo washes, for example permanently after at least 5 shampoo washes.

[0007] It is also advantageous for the dye compositions applied to hair to have good use properties, in particular for them to be easy to apply to keratin fibres.

[0008] These aims are achieved with the present invention, which provides in particular a process for dyeing hair comprising a step of applying to said hair a composition C, preferably cosmetic, for permanent hair dyeing comprising: - at least one dyeing agent, and

[0009] - at least one amino silicone of formula (I) below: in which:

[0010] - R1 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 which q is a number ranging from 2 to 8 and L is an optionally quaternized amine group selected from the following groups:

[0012] -N(R3)2; -N+(R3)3A’; -NR3-Y-N(R3)2and -NR-Y-N+(R3)3A; in which R3, which may be identical or different, represents a hydrogen atom, a phenyl group, a benzyl group or a saturated monovalent hydrocarbon radical, for example a Ci-C2o alkyl group; Y denotes a linear or branched group of formula CrH2r, r being an integer ranging from 2 to 6, preferably from 2 to 4; and A" represents a cosmetically acceptable anion, especially a halide such as fluoride, chloride, bromide or iodide;

[0013] - X represents a radical corresponding to formula (II) below:

[0014] (ID in which:

[0015] - A independently represents a linear or branched alkylene group having from 1 to 10 carbon atoms, which may be interrupted by at least one heteroatom selected from O, S, NH or a carbonyl group (CO), preferably NH, and

[0016] - Q represents an alkylene group having from 1 to 20 carbon atoms, said alkylene group being optionally substituted with 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

[0017] - n denotes an integer ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to 500.

[0018] It has been found that the silicone of formula (I) provides excellent conditioning / care for hair. Hair thus treated, and more particularly hair that is embrittled or damaged from hair dyeings, shows good separation of the individual strands, giving it a soft, smooth feel and making it easy to disentangle. The improvement in the conditioning of the hair is particularly significant when the silicone of formula (I) is applied to the hair by means of a permanent hair dyeing composition.

[0019] It has also been found that the treated hair, and in particular hair embrittled or damaged by hair dyeings, is strengthened, with more body and less breakage on combing.

[0020] Other subjects, features, aspects and advantages of the invention will become more apparent on reading the description and the example that follows.

[0021] In the present description, and unless otherwise stated:

[0022] - The expression “at least one” is equivalent to the expression “one or more” and can be substituted therewith.

[0023] - The expression “between... and...” is equivalent to the expression “ranging from... to...” and can be substituted therewith, and implies that the limits are included.

[0024] - The expression “greater than” and the expression “less than” are understood for the purposes of the invention as meaning an open-ended range that is respectively strictly greater or strictly less and thus non-inclusive of the limits.

[0025] - "Permanent dyeing of the hair” is understood according to the present patent application as meaning a long-lasting dyeing of the hair that withstands preferably at least 4 shampoo washes, more preferably at least 5 shampoo washes, better still at least 10 shampoo washes. In other words, the treated hair has not reverted to its natural colour (i.e. without artificial dyeing), even after preferably at least 4 shampoo washes, more preferably 5 shampoo washes and better still 10 shampoo washes.

[0026] - “Keratin fibres” are understood according to the present patent application as meaning in particular human keratin fibres such as head hair, eyelashes, eyebrows, and body hair, preferably head hair, eyebrows and eyelashes, even more preferably head hair.

[0027] - For the purposes of the present invention, “hair” is understood as meaning head hair. This term does not correspond to body hair, eyebrows or eyelashes.

[0028] - “Fatty acid” is understood according to the present patent application as meaning an organic acid comprising in its structure a linear or branched, saturated or unsaturated hydrocarbon chain comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, more preferably from 10 to 22 carbon atoms.

[0029] - “Fatty alcohol” is understood according to the present patent application as meaning an alcohol comprising in its structure a linear or branched, saturated or unsaturated hydrocarbon chain comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, more preferably from 10 to 22 carbon atoms.

[0030] Aminosilicones of formula (I)

[0031] According to the invention, at least one aminosilicone of formula (I) below is used in a composition C for permanent dyeing of the hair comprising at least one dyeing agent, in order to improve the conditioning of the hair:

[0032] (I) in which:

[0033] - R1 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 ranging from 2 to 8 and L is an optionally quatemized amine group selected from the following groups:

[0034] -N(R3)2; -N+(R3)3A’; -NR3-Y-N(R3)2and -NR-Y-N+(R3)3A; in which R3, which may be identical or different, represents a hydrogen atom, a phenyl group, a benzyl group or a saturated monovalent hydrocarbon radical, for example a Ci-C2o alkyl group; Y denotes a linear or branched group of formula CrH2r, r being an integer ranging from 2 to 6, preferably from 2 to 4; and A" represents a cosmetically acceptable anion, especially a halide such as fluoride, chloride, bromide or iodide;

[0035] - X represents a radical corresponding to formula (II) below:

[0036] (ID in which:

[0037] - A independently represents a linear or branched alkylene group having from 1 to 10 carbon atoms, which may be interrupted by at least one heteroatom selected from O, S, NH or a carbonyl group (CO), preferably NH; and

[0038] - Q represents an alkylene group having from 1 to 20 carbon atoms, said alkylene group being optionally substituted with 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

[0039] - n denotes an integer ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to 500.

[0040] Most particularly, at least one aminosilicone of formula (I) is used in a composition C for permanent dyeing of the hair comprising at least one dyeing agent, in order to improve the separation into individual strands of the hair and thus maintain lightness in the hair mass.

[0041] An “aminosilicone” refers to any silicone containing at least one primary, secondary or tertiary amine or a quaternary ammonium group. The weight- average molecular masses of these aminosilicones can be measured by gel-permeation chromatography (GPC) at room temperature (25 °C), as polystyrene equivalent. The columns used are p Styragel columns. The eluent is THF and the flow rate is 1 ml / min. 200 pl of a 0.5% by weight solution of silicone in THF is injected. Detection is by refractometry and UV spectrometry.

[0042] According to a preferred embodiment, the aminosilicone(s) of formula (I) is / are such that:

[0043] - R1 independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms;

[0044] - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number ranging from 2 to 8 and L is an optionally quaternized amine group selected from the following groups:

[0045] -N(R3)2;

[0046] -N(R3)-CH2-CH2-N(R3)2in which R3, which may be identical or different, represents a hydrogen atom, a phenyl group, a benzyl group or a saturated monovalent hydrocarbon radical, for example a Ci-C2o alkyl group;

[0047] - X represents a radical corresponding to formula (II) below: in which:

[0048] - A independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms that is interrupted by at least one heteroatom selected from O, S, NH or a carbonyl group (CO), preferably NH; and

[0049] - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group being optionally substituted with 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

[0050] - n denotes an integer ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to According to a more preferred embodiment, the aminosilicone(s) of formula (I) is / are such that:

[0051] - R1 independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms;

[0052] - R2 independently represents a monovalent radical of formula -CqH2qL in which q is a number ranging from 2 to 8 and L is an amine group having the following formula: -N(R3)-CH2-CH2-N(R3)2in which R3 represents a hydrogen atom,

[0053] - X represents a radical corresponding to formula (III) below: in which:

[0054] - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group being optionally substituted with 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

[0055] - n denotes an integer ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to 500.

[0056] According to a more preferred embodiment, the aminosilicone used in the composition C is of formula (IV) below:

[0057]

[0058] (IV) in which:

[0059] - R1 independently represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms;

[0060] - Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group being optionally substituted with 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

[0061] - n denotes an integer ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to

[0062] 500. According to a particular embodiment, the aminosilicone(s) of formula (I) is / are present in the composition C in the form of an emulsion or microemulsion with one or more surfactants, preferably nonionic surfactants such as Trideceth-10.

[0063] The aminosilicones of formula (I) employable in the composition C include the aminosilicone having the INCI name Bis-Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer. They also include the commercial product Belsil® DADM 3240 E sold by Wacker, of the formula below: in which the radicals R represent, independently of one another and are preferably identical, a methyl group -CH3, hydroxyl -OH, or -OCH3 group.

[0064] Preferably, the total content of aminosilicone(s) of formula (I) ranges from 0.01% to 25% by weight, more preferably from 0.1% to 20% by weight, even more preferably from 0.5% to 20% by weight, better still from 1% to 15% by weight, even better still from 2% to 10% by weight, even better still again from 3% to 8% by weight, relative to the total weight of the composition C.

[0065] Preferably, the total content of aminosilicone(s) of formula (IV) ranges from 0.01% to 25% by weight, more preferably from 0.1% to 20% by weight, even more preferably from 0.5% to 20% by weight, better still from 1% to 15% by weight, even better still from 2% to 10% by weight, even better still again from 3% to 8% by weight, relative to the total weight of the composition C.

[0066] Preferably, the total content of aminosilicone having the INCI name Bis- Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer, if 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, even more preferably from 0.5% to 20% by weight, better still from 1% to 15% by weight, even better still from 2% to 10% by weight, even better still again from 3% to 8% by weight, relative to the total weight of the composition C.

[0067] Dyeing agent

[0068] Said composition C comprises at least one dyeing agent.

[0069] Preferably, the dyeing agent(s) is / are selected from pigments, direct dyes and mixtures thereof.

[0070] Said composition C may comprise one or more pigments.

[0071] A “pigment” refers to any pigment that imparts colour to keratin materials. Their solubility in water at 25 °C and at atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01%.

[0072] The pigments that may be used are selected in particular from the organic and / or mineral pigments known in the art, especially those described in the Kirk- Othmer Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry.

[0073] They may be natural, of natural origin, or non-natural.

[0074] These pigments may be in the form of a pigment paste or powder. They may be coated or uncoated.

[0075] The pigments may be selected for example from mineral pigments, organic pigments, lakes, special-effect pigments such as nacres or glitter flakes, and mixtures thereof.

[0076] The pigment may be a mineral pigment. A “mineral pigment” is understood as meaning any pigment that meets the definition in Ullmann’s Encyclopedia in the chapter on inorganic pigments. Mineral pigments that are useful in the present invention include iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide. The pigment may be an organic pigment. An “organic pigment” is understood as meaning any pigment that meets the definition in Ullmann's Encyclopedia in the chapter on organic pigments.

[0077] The organic pigment may especially be selected from nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluoran, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine and quinophthalone compounds.

[0078] In particular, the white or coloured organic pigments may be selected from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references Cl 42090, 69800, 69825, 74100 and 74160, the yellow pigments codified in the Color Index under the references Cl 11680, 11710, 19140, 20040, 21100, 21108, 47000 and 47005, the green pigments codified in the Color Index under the references CI 61565, 61570 and 74260, the orange pigments codified in the Color Index under the references CI 11725, 45370 and 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 and 75470, and the pigments obtained by oxidative polymerization of indole or phenol derivatives as described in patent FR 2 679 771.

[0079] The organic pigment may also be a lake. A “lake” is understood as meaning dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.

[0080] The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.

[0081] Dyes include carminic acid. They also include 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 42 053), D&C Blue 1 (CI 42 090).

[0082] The pigment may also be a special-effect pigment. Special-effect pigments are understood as meaning pigments that generally create a coloured appearance (characterized by a certain shade, a certain vibrancy and a certain level of luminance) that is nonuniform and changes according to the conditions of observation (light, temperature, angles of observation, etc.). They thereby differ from coloured pigments that afford a standard uniform opaque, semi-transparent or transparent tint.

[0083] The variety of pigments that may be used in the present invention makes it possible to obtain a wide range of colours, as well as particular optical effects such as metallic effects or interference effects.

[0084] 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 preferably between 30 nm and 50 pm.

[0085] Said composition C may comprise one or more direct dyes.

[0086] A “direct dye” is understood as meaning natural and / or synthetic dyes other than oxidation dyes. These are dyes that will spread superficially on the fibre. They may be ionic, for example cationic or anionic, or nonionic.

[0087] Examples of suitable direct dyes 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 the form of mixtures.

[0088] The direct dyes may be selected from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly referred to as “acid” direct dyes on account of their affinity for alkaline substances. Anionic direct dyes are understood as meaning any direct dye containing in its structure at least one CO2R or SO3R substituent where R denotes a hydrogen atom or a cation originating from a metal or an amine, or an ammonium ion. The anionic dyes may be selected 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.

[0089] Acid dyes include: 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, Acid 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 or Sunset Yellow; Acid Red 111, Acid Red 134 and Acid Yellow 38. Examples of anionic pyrazolone azo dyes include: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76 and Acid Yellow 17.

[0090] Examples of anthraquinone dyes include: 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 and Acid Black 48.

[0091] Examples of nitro dyes include: Acid Brown 13 and Acid Orange 3; examples of dyes of formula (XXII’) include: Acid Yellow 1, the sodium salt of 2,4-dinitro-l- naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2-(4'-N,N-(2"- hydroxyethyl)amino-2'-nitro)anilineethanesulfonic acid, 4-P-hydroxyethylamino-3- nitrobenzenesulfonic acid; EXT D&C Yellow 7.

[0092] 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 and Acid Green 50.

[0093] Examples of xanthene dyes include: Acid Yellow 73; Acid and Acid Violet 9.

[0094] Examples of indole dyes include: Acid Blue 74.

[0095] Examples of quinoline dyes include: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.

[0096] Natural direct dyes employable according to the invention include lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechualdehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orceins. It is also possible to use extracts or decoctions containing these natural dyes and especially henna-based poultices or extracts.

[0097] More preferably, the dyeing agent(s) is / are selected from pigments.

[0098] Preferably, the dyeing agent(s) is / are present in a total amount 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.

[0099] More preferably, the pigment(s) is / are present in a total amount 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.

[0100] Water

[0101] Preferably, said composition C also comprises water. More preferably, the total content of water present in the composition C ranges from 5% to 90% by weight, more preferably from 10% to 80% by weight, even more preferably from 15% to 70% by weight, better still from 20% to 65% by weight, even better still from 25% to 60% by weight, relative to the total weight of the composition C.

[0102] Organic solvents

[0103] Preferably, said composition C also comprises at least one organic solvent.

[0104] Examples of organic solvents include C1-C4 alkanols, for example ethanol and isopropanol, polyols and polyol ethers, such as glycerol, 2-butoxy ethanol, propylene glycol, propylene glycol monomethyl ether, and diethylene glycol monoethyl ether or monomethyl ether, and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0105] More preferably, the organic solvent(s) is / are selected from ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, benzyl alcohol, and mixtures thereof.

[0106] Even more preferably, the organic solvent(s) is / are selected from ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, and mixtures thereof.

[0107] Most particularly preferably, the composition C comprises ethanol.

[0108] Preferably, the total content of organic solvent(s), if present in the composition, ranges from 1% to 70% by weight, more preferably from 2% to 60% by weight, even more preferably from 5% to 55% by weight, better still from 10% to 55% by weight, even better still from 15% to 50% by weight, relative to the total weight of the composition C.

[0109] Preferably, the total content of ethanol, if present in the composition, ranges from 1% to 70% by weight, more preferably from 2% to 60% by weight, even more preferably from 5% to 55% by weight, better still from 10% to 55% by weight, even better still from 15% to 50% by weight, relative to the total weight of the composition C. Nonionic surfactants

[0110] Preferably, said composition C also comprises at least one nonionic surfactant.

[0111] The nonionic surfactant(s) employable in the composition of the present invention are in particular described, for example, in “Handbook of Surfactants” by M.R. Porter, published by Blackie & Son (Glasgow and London), 1991, pp. 116-178.

[0112] Nonionic surfactants may optionally be selected for example from oxyalky lenated (Cs-C24)alkylphenols, oxy alky lenated or glycerolated Cs to C40 alcohols, oxy alky lenated Cs to C30 fatty acid amides, esters of Cs to C30 acids and polyethylene glycols, esters of Cs to C30 acids and sorbitol, esters of fatty acids and sucrose, (Cs-C3o)alkyl(poly)glucosides, (Cs-C3o)alkenyl(poly)glucosides, (Cs- C3o)alkyl(poly)glucoside esters, oxyethylenated plant oils, ethylene oxide and / or propylene oxide condensates, N-(Cs-C3o)alkylglucamine and N-(Cs- C3o)acylmethylglucamine derivatives, amine oxides, and mixtures thereof.

[0113] More particularly, these include the following compounds, alone or as a mixture:

[0114] - oxy alky lenated (Cs-C24)alkylphenols;

[0115] - oxyalkylenated or glycerolated, linear or branched, saturated or unsaturated Cs to C40 alcohols, preferably containing one or two fatty chains; different from the fatty alcohols described previously;

[0116] - oxyalkylenated, linear or branched, saturated or unsaturated Cs to C30 fatty acid amides;

[0117] - esters of linear or branched, saturated or unsaturated Cs to C30 acids and polyethylene glycols;

[0118] - esters of linear or branched, saturated or unsaturated Cs to C30 acids and sorbitol, preferably oxyethylenated;

[0119] - fatty acid esters of sucrose;

[0120] - (Cs-C3o)alkyl(poly)glucosides, (Cs-C3o)alkenyl(poly)glucosides, optionally oxyalkylenated (0 to 10 oxyalkylene units) and comprising from 1 to 15 glucose units, (Cs-C3o)alkyl(poly)glucoside esters;

[0121] - oxyethylenated, saturated or unsaturated plant oils;

[0122] - ethylene oxide and / or propylene oxide condensates;

[0123] - / V-(Cs-C3o)alkylglucamine and A^-(Cs-C3o)acylmethylglucamine derivatives;

[0124] - amine oxides. They are especially selected from fatty alcohols, a-diols and (Ci- C2o)alkylphenols, these compounds being ethoxylated, propoxylated or glycerolated and having at least one fatty chain containing, for example, from 8 to 40 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range in particular from 1 to 200 and for the number of glycerol groups to range in particular from 1 to 30. The nonionic surfactants are advantageously especially oxyalkylenated, preferably ethoxylated, Cs-Cao, preferably C8-C24, fatty alcohols comprising from 1 to 200 mol of ethylene oxide.

[0125] They also include condensates of ethylene oxide and propylene oxide with fatty alcohols, ethoxylated fatty amides having preferably from 1 to 30 ethylene oxide units, poly glycerolated fatty amides containing on average from 1 to 5, and in particular from 1.5 to 4, glycerol groups, ethoxylated fatty acid esters of sorbitan having from 1 to 30 ethylene oxide units, fatty acid esters of sucrose, fatty acid esters of polyethylene glycol, (C6-C24 alkyl)polyglycosides, oxyethylenated plant oils, N-(Ce- C24 alkyl)glucamine derivatives, amine oxides such as (C10-C14 alkyl)amine oxides or N-(Cio-Ci4 acyl)aminopropylmorpholine oxides.

[0126] The C8-C30, preferably C12-C22, fatty acid esters (especially monoesters, diesters and triesters) 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, and sorbitan tristearate.

[0127] The polyoxyethylenated C8-C30 (preferably C12-C18) fatty acid esters (especially monoesters, diesters and triesters) of sorbitan having especially from 2 to 20 mol of ethylene oxide may be selected from (poly)oxyethylenated esters of C12-C18 fatty acids, in particular lauric, myristic, palmitic or stearic acid, and sorbitan having especially from 1 to 30 mol of ethylene oxide, preferably from 2 to 30 mol of ethylene oxide.

[0128] The nonionic surfactants may also be selected from nonionic surfactants of alkyl(poly)glycoside (APG) type, also known as alkyl(poly)glycoside nonionic surfactants.

[0129] An “alkyl(poly)glycoside” refers to an alkylpolyglycoside or an alkylmonoglycoside, also termed an alkylglycoside in the present patent application, the alkyl group of which comprises between 6 and 30 carbon atoms, preferably between 6 and 24 carbon atoms, and may optionally be alkoxylated with one or more preferably C2 to C4 alkylene oxide groups.

[0130] The nonionic surfactant(s) of alkyl(poly)glycoside type is / are preferably selected from the compounds of formula (III) below and mixtures thereof:

[0131] RiO-(R2O)t(G)v(III) in which:

[0132] - Ri represents a linear or branched, saturated or unsaturated alkyl group containing from 6 to 24 carbon atoms, or an alkylphenyl group in which the linear or branched alkyl group contains from 6 to 24 carbon atoms,

[0133] - R2 represents an alkylene group containing about from 2 to 4 carbon atoms,

[0134] - G represents a saccharide unit containing 5 or 6 carbon atoms,

[0135] - 1 denotes a value ranging from 0 to 10 and preferably 0 to 4, and

[0136] - v denotes a value ranging from 1 to 15.

[0137] Preferably, the nonionic surfactant(s) of alkyl(poly)glycoside type is / are selected, alone or as a mixture, from the compounds of formula (III) in which:

[0138] - Ri denotes a linear or branched, saturated or unsaturated alkyl group containing from 8 to 18 carbon atoms,

[0139] - G denotes glucose, fructose or galactose, preferably glucose,

[0140] - 1 denotes a value ranging from 0 to 3, and is preferably equal to 0, and

[0141] - R2and v are as defined previously.

[0142] The degree of polymerization of the alkyl(poly)glycoside nonionic surfactant(s), as represented for example by the index v in formula (III), ranges on average from 1 to 15 and preferably from 1 to 4. This degree of polymerization more particularly ranges from 1 to 2 and better still from 1.1 to 1.5, on average.

[0143] The glycoside bonds between the saccharide units are 1,6- or 1,4-bonds, preferably 1,4-bonds.

[0144] The alkyl(poly)glycoside nonionic surfactants that may be used in the present invention are preferably alkyl(poly)glycosides represented in particular by the products sold by Cognis under the names Plantaren® (600 CS / U, 1200 and 2000) or Plantacare® (818, 1200 and 2000). It is also possible to use the products sold by Seppic under the names Triton CG 110 (or Oramix CG 110) and Triton CG 312 (or Oramix® NS 10), the products sold by BASF under the name Lutensol GD 70 or else the products sold by Chem Y under the name AGIO LK, or the products sold by Evonik Goldschmidt under the trade names Tego Care CG 90 or Tego Care CG 90 MB. The nonionic surfactant(s) of alkyl(poly)glycoside type present in the composition of the invention is / 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 surfactant(s) of alkyl(poly)glycoside type is / are selected from caprylyl / capryl glucoside, decyl glucoside, coco glucoside, lauryl glucoside and mixtures thereof. Even more preferably, the nonionic surfactant of alkyl(poly)glycoside type is coco glucoside.

[0145] The nonionic surfactants may also be selected from oxyethylenated plant oils.

[0146] The nonionic surfactant(s) is / are preferably selected from: a) oxyethylenated fatty alcohols containing at least one Cs to C40 alkyl chain containing from 1 to 100 mol of ethylene oxide, b) ethoxylated esters of C8-C30 fatty acids and sorbitan containing from 1 to 30 mol of ethylene oxide, c) (C6-C24 alkyl)polyglycosides, and d) mixtures thereof.

[0147] Even more preferably, the nonionic surfactant(s) is / are selected from oxyethylenated fatty alcohols containing at least one linear or branched, saturated or unsaturated Cs to C40, especially C8-C20, better still Cio-Cis, alkyl chain and containing from 1 to 100 mol of ethylene oxide, preferably from 2 to 50 mol, more particularly from 2 to 40 mol, or even from 3 to 20 mol of ethylene oxide.

[0148] Preferably, the total content of nonionic surfactant(s), if present in the composition C, is within the range from 0.01% to 20% by weight, more preferably from 0.05% to 10% by weight, better still from 0.1% to 5% by weight, relative to the total weight of the composition C.

[0149] Preferably, if present in the composition C, the total content of nonionic surfactant(s) selected from oxyethylenated fatty alcohols containing at least one Cs to C40 alkyl chain and from 1 to 100 mol of ethylene oxide is within the range from 0.01% to 20% by weight, more preferably from 0.05% to 10% by weight, better still from 0.1% to 5% by weight, relative to the total weight of the composition C.

[0150] Film-forming polymers

[0151] Preferably, said composition C further comprises at least one film-forming polymer. A ''Ji'lni-Jorming ' polymer is understood as meaning a polymer capable of forming, by itself or in the presence of an auxiliary film-forming agent, a macroscopically continuous film on a support, especially on keratin materials, and preferably a cohesive film.

[0152] The film-forming polymer may for example be selected from the group comprising:

[0153] - film-forming polymers that are soluble in an organic solvent medium, in particular liposoluble polymers; this means that the polymer is soluble or miscible in the organic medium and leads to the formation of a single homogeneous phase when it is incorporated into the medium;

[0154] - film-forming polymers that are dispersible in an organic solvent medium, which 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 may be in the form of non-aqueous dispersions of polymer particles, preferably dispersions in silicone oils or hydrocarbon oils; in one embodiment, the non-aqueous polymer dispersions comprise polymer particles stabilized on their surface with at least one stabilizer; these non-aqueous dispersions are often referred to as NADs.

[0155] - film-forming polymers in the form of aqueous dispersions of polymer particles; this means that the polymer forms an insoluble phase in water, the polymer remaining stable and / or compatible once incorporated into the water; the polymer particles may be stabilized on their surface with at least one stabilizer. These polymer particles are often termed “latex”, in which case the composition must comprise an aqueous phase.

[0156] - film-forming vinylpyrrolidone (co)polymers,

[0157] - film- forming vinyl alcohol (co)polymers,

[0158] - film- forming vinyl acetate polymers,

[0159] - film- forming carboxy vinyl (co)polymers,

[0160] - film-forming (co)polymers of acrylic acid type,

[0161] - film-forming (co)polymers of methacrylic acid type,

[0162] - film-forming natural gums,

[0163] - film-forming polysaccharides,

[0164] - film-forming acrylamide (co)polymers, and

[0165] - mixtures thereof. The film-forming polymer(s) according to the invention may for example be selected from acrylic acid (co)polymers, methacrylic acid (co)polymers, homopolymers and copolymers of acrylic esters, homopolymers and copolymers of methacrylic esters, homopolymers and copolymers of acrylic amides, homopolymers and copolymers of methacrylic amides, homopolymers and copolymers of olefins, homopolymers and copolymers of styrene, homopolymers and copolymers of ethers, homopolymers and copolymers of vinyl esters or amides, homopolymers and copolymers of (meth)acrylic esters or amides containing a linear, branched or cyclic C1-C20 alkyl group, a Ce-Cio aryl group or a C2-C6 hydroxyalkyl group, polyurethanes, polyesters, polyamides, N- vinylpyrrolidone homopolymers or copolymers, vinyl alcohol (co)polymers, vinyl acetate polymers, carboxyvinyl (co)polymers, vinylcaprolactam homopolymers or copolymers, homopolymers or copolymers of vinyl N-alkyl(Ci-C6)pyrroles, homopolymers or copolymers of vinyloxazoles, homopolymers or copolymers of vinylthiazoles, vinylpyrimidine homopolymers or copolymers, vinylimidazole homopolymers or copolymers, natural gums, polysaccharides, acrylamide (co)polymers, styrene / vinylpyrrolidone copolymers, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / DMAPA acrylate copolymers, vinylpyrrolidone / vinylcaprolactam / DMAPA acrylate copolymers, and mixtures thereof.

[0166] They also include, for example:

[0167] - the ethylene / sodium acrylate copolymer marketed under the trade name Eco smooth Satin® by Dow;

[0168] - the copolymers for which the CTFA (4th Ed., 1991) name is Octylacrylamide / Acrylates / Butylaminoethyl Methacrylate Copolymer, such as the products sold under the name Amphomer® or Lovocryl® 47 by National Starch, and also the copolymers having the CTFA name Acrylates / Octylacrylamide Copolymer, such as the products sold under the name Dermacryl® LT or Dermacryl® 79 by National Starch;

[0169] - the copolymers marketed by Rohm & Haas under the name Aculyn® 33;

[0170] - the copolymers of esters of an ethylenically unsaturated acid and alkoxylated fatty alcohols, such as: Aculyn® 28 (Acrylates / Beheneth-25 Methacrylate Copolymer), Structure 2001® (Acrylates / Steareth-20 Itaconate Copolymer), Structure 3001® (Acrylates / Ceteth-20 Itaconate Copolymer), Structure Plus® (Acrylates / Aminoacrylates C 10-30 Alkyl PEG-20 Itaconate Copolymer), Carbopol® 1342, 1382, Ultrez 20, Ultrez 21 (Acrylates / Cio-30 Alkyl Acrylate Crosspolymer), Synthalen W2000® (Acrylates / Palmeth-25 Acrylate Copolymer) or Soltex OPT (Acrylates / Ci2-22 Alkyl Methacrylate Copolymer) marketed by Rohm and Haas;

[0171] - the vinylpyrrolidone (PVP) homopolymers marketed under the name Luviskol® K by BASF SE, in particular Luviskol® K 90 or Luviskol® K 85 by BASF SE;

[0172] - the vinylpyrrolidone / vinyl ester copolymers marketed under the name Luviskol® by BASF SE, in particular the nonionic polymers Luviskol® VA64 and Luviskol® VA73 (vinylpyrrolidone / vinyl acetate copolymers);

[0173] - the vinylpyrrolidone / vinylcaprolactam / DMAPA acrylates copolymers marketed by Ashland Inc. under the trade name Aquaflex® SF-40;

[0174] - the vinylpyrrolidone / DMAPA acrylates copolymers marketed by Ashland Inc. under the trade name Styleze CC-10.

[0175] They also include, for example, film-forming polymer(s) selected from cationic acrylic copolymers, preferably insoluble in water, and containing the following structural units: a) methacryloyloxyethyltrimethylammonium salt, b) butyl methacrylate, and c) ethoxyethyl methacrylate.

[0176] Such copolymers are described for example in JP5745266. Preferably, the polymer contains the above three monomers in the following proportions relative to the sum total of monomer units by weight in the formed 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%.

[0177] Preferably, the copolymer is not amphoteric, i.e. it does not contain any units bearing an anionic charge.

[0178] Preferably, the structural units of the copolymer are all methacrylate derivatives.

[0179] Even more particularly, the copolymer corresponds to the copolymer having the INCI name Polyquatemium-99, for example the polymer marketed by GOO- Chemical under the name Plascize L-514. This is the butyl methacrylate / ethoxyethyl methacrylate / methacryloyloxyethyltrimethylammonium chloride copolymer, 30% in ethanol:

[0180] In particular, the film-forming polymer(s) may also be selected from polyurethanes, optionally from aqueous dispersions of polyurethane particles.

[0181] The polyurethanes employable according to the present invention may optionally also comprise compounds that are situated at the chain ends and terminate said chains (chain terminators). Such compounds are in particular described in patents US 7 445 770 and / or US 7 452 770.

[0182] Non-limiting examples of polyurethanes include those sold under the name Baycusan® by Bayer, 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) .

[0183] More preferably, the film-forming polymer(s) is / are selected from polyurethanes, cationic acrylic copolymers, vinylpyrrolidone homopolymers (PVP), 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, homopolymers or copolymers of acrylic esters, acrylic acid homopolymers or copolymers, methacrylic acid homopolymers or copolymers, ethylene homopolymers or copolymers, and mixtures thereof.

[0184] Even more preferably, the film-forming polymer(s) is / are selected from polyurethanes, cationic acrylic copolymers, and mixtures thereof.

[0185] According to a particular embodiment of the invention, the film-forming polymer(s) is / are selected from Polyquatemium-99, Polyurethane-34, Polyurethane- 32, Polyurethane-35 and Polyurethane-48, and mixtures thereof. 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, even more preferably from 2% to 20% by weight, better still from 5% to 15% by weight, even better still from 6% to 12% by weight, even better still again from 8% to 12% by weight, relative to the total weight of the composition.

[0186] Preferably, the total content of cationic acrylic copolymer(s) and polyurethane(s), if present in the composition, ranges from 0.1% to 30% by weight, more preferably from 1% to 25% by weight, even more preferably from 2% to 20% by weight, better still from 5% to 15% by weight, even better still from 6% to 12% by weight, even better still again from 8% to 12% by weight, relative to the total weight of the composition.

[0187] Preferably, the pH of the composition C is between 3 and 9, more preferably between 4 and 8 and even more preferably between 5 and 8.

[0188] The pH of the composition according to the invention may be adjusted to the desired value with the aid of alkalinizing agents (such as monoethanolamine) and / or acidifying agents (such as citric acid).

[0189] Said composition C may optionally also contain one or more additives used in cosmetics, for example thickeners, additional solvents (other than those disclosed above), silicones other than those described above, anionic surfactants, cationic surfactants, amphoteric surfactants and polymers.

[0190] These additives may be present in the composition C in an amount ranging from 0% to 20% by weight relative to the total weight of the composition C.

[0191] A person skilled in the art will take care to select these optional additives and the amounts thereof such that they do not adversely affect the properties of the compositions of the present invention.

[0192] According to a preferred embodiment of the invention, said composition C comprises:

[0193] - at least one dyeing agent;

[0194] - at least one aminosilicone of formula (I) as described above;

[0195] - water;

[0196] - at least one nonionic surfactant; and - optionally at least one organic solvent selected from alcohols, especially ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, benzyl alcohol, and mixtures thereof.

[0197] According to this embodiment, the aminosilicone is preferably a silicone of formula (IV) as described above, more preferably the aminosilicone having the INCI name Bis-Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer.

[0198] According to another preferred embodiment of the invention, said composition C comprises:

[0199] - at least one dyeing agent;

[0200] - at least one film-forming polymer selected from Polyquaternium-99, Polyurethane-34, Polyurethane-32, Polyurethane-35 and Polyurethane-48, and mixtures thereof;

[0201] - at least one aminosilicone of formula (I), preferably at least one aminosilicone of formula (IV) as described above, more preferably the aminosilicone having the INCI name Bis-Hydroxy / Methoxy / Methyl Amodimethicone Crosspolymer;

[0202] - water;

[0203] - at least one nonionic surfactant selected from oxyethylenated fatty alcohols containing at least one linear or branched, saturated or unsaturated Cs to C40, especially C8-C20, better still Cio-Cis, alkyl chain and containing from 1 to 100 mol of ethylene oxide, preferably from 2 to 50 mol, more particularly from 2 to 40 mol, or even from 3 to 20 mol of ethylene oxide; and

[0204] - optionally at least one organic solvent selected from alcohols, preferably ethanol, isopropanol, glycerol, 2-butoxyethanol, propylene glycol, hexylene glycol, ethylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, benzyl alcohol, and mixtures thereof, more preferably ethanol.

[0205] Preferably, said composition C is free of cationic surfactant.

[0206] Preferably, said composition C is free of (poly)carbodiimide compound.

[0207] A ^(poly)carbodiimide compound" is understood as meaning a compound comprising one or more carbodiimide groups, preferably at least two carbodiimide groups, more preferably at least three carbodiimide groups; in particular, the number of carbodiimide groups does not exceed 200, preferably 150, more preferably 100.

[0208] A “carbodiimide group” is understood as meaning a divalent linear triatomic moiety of general formula -(N=C=N)-.

[0209] Preferably, said composition C is applied to dry or damp hair.

[0210] According to one embodiment, the hair is not rinsed, especially not rinsed with water, or washed, especially not given a shampoo wash, after application of the composition C containing the silicone of formula (I), or at least not rinsed / washed within 2 hours, preferably within 3 hours, more preferably within 4 hours, better still within 6 hours, even better still within 12 hours, or even within 24 hours, after the step of applying the composition C.

[0211] The examples that follow serve to illustrate the invention, but without being limiting in nature.

[0212] Examples

[0213] Example 1: Method of synthesis of the aminosilicone of formula (I

[0214] 1.1 stoichiometric equivalents of diethyl L-tartrate are added to an aqueous emulsion comprising Trideceth-10 and containing 35% of amodimethicone bearing 3- (2-aminoethylamino)propyl functional groups. The mixture obtained is homogenized at room temperature, giving a white, smooth, low-viscosity silicone emulsion.

[0215] Example 2:

[0216] Reference compositions A2.1 and A2.2, comparative compositions B2.1 and B2.2 and inventive compositions C2.1 and C2.2 were prepared from the ingredients indicated in Tables 1 and 2 below, the amounts of which are expressed in % by weight of active material (a.m.).

[0217] [Table 1]

[0218] (1) synthesized according to the method of synthesis described in example 1

[0219] (2) sold by Wacker under the name Belsil ADM LOG 1 (containing 15% active material).

[0220] [Table 2]

[0221] (1) synthesized according to the method of synthesis described in example 1

[0222] (2) sold by Wacker under the name Belsil ADM LOG 1 (containing 15% active material).

[0223] Application protocol for the sensory evaluation:

[0224] The above compositions are applied by finger to a lock of 2.7 g of natural hair with a bath ratio of 0.8 g per gram of hair. Each lock is dried with a hairdryer and at the same time combed, using first the large teeth of the comb and then the smaller ones. The experiment ends when the lock is dry. Sensory evaluation protocol and results obtained:

[0225] The application of aminosilicone to the hair generally makes it possible to improve disentangling, with the drawback of the hairs sticking together to form clumps of hair, unlike untreated natural hair which is separated into individual strands.

[0226] After the above treatment, the locks of hair were evaluated by a panel of five selected individuals trained in the sensory evaluation of locks of hair.

[0227] The evaluation examined the separation into individual locks of the hair.

[0228] The scores correspond to the criteria below:

[0229] 0 = very poor, clumps of hair to the touch

[0230] 5 = hair very well separated into individual locks

[0231] The results are as follows:

[0232] [Table 3]

[0233] [Table 4]

[0234] These results demonstrate an improvement in the separation into individual strands of the hair after treatment with the aminosilicone of formula (I). The use of this silicone permits better separation into individual strands of the hair and a reduction in clumping (hair individualization), by comparison with the use of a standard aminosilicone, i.e. amodimethicone.

[0235] Furthermore, it has been observed that adding a dyeing agent to the compositions A2.1, A2.2, B2.1, B2.2, C2.1 and C2.2 would achieve the same results as above, in terms of cosmeticity.

[0236] Example 3:

[0237] Comparative compositions A3.1, A3.2, B3.1 and B3.2 and inventive compositions C3.1 and C3.2 were prepared from the ingredients stated in Tables 5 and 6 below, the amounts of which are expressed in % by weight of active material (a.m.).

[0238] The film-forming polymer is used to give the hair texture, which is particularly useful for fine hair.

[0239] [Table 5]

[0240] (1) synthesized according to the method of synthesis described in example 1

[0241] (2) sold by Wacker under the name Belsil ADM LOG 1 (containing 15% active material).

[0242] [Table 6]

[0243] (1) synthesized according to the method of synthesis described in example 1

[0244] (2) sold by Wacker under the name Belsil ADM LOG 1 (containing 15% active material). Sensory evaluation of the hair:

[0245] Locks of 2.7 g of natural HT4 hair were used for this evaluation.

[0246] Each composition is applied to a lock of dry hair in a bath ratio of 0.8 g of composition / gram of hair.

[0247] Each lock is then dried and then stored at 22°C for 24 hours prior to evaluation.

[0248] A sensory evaluation of the smoothness to the touch (smooth feel) and suppleness is then carried out for each of the locks by five experts. Each cosmetic attribute is evaluated by means of a score between 0 and 5:

[0249] 0 / 5 corresponds to a lock of hair that has a rough and non-cosmetic feel. 5 / 5 corresponds to a lock of hair having a very satisfactory cosmetic feel.

[0250] The results are collated in Tables 7 to 10 below. [Table 7]

[0251] [Table 8] [Table 9]

[0252] [Table 10] In the comparative A3.1 and A3.2, it can be noted that the feel obtained when using a film-forming polymer is unsatisfactory. With such compositions, although the texture of the locks of hair is improved, this is at the expense of the feel, which is rough and unacceptable for the user of the composition. Compositions B3.1 and B3.2 demonstrate that addition of the aminosilicone improves the cosmetic quality, but without this being satisfactory for the user, the hair still having a coarse feel.

[0253] In the case of inventive compositions C3.1 and C3.2 containing the aminosilicone of formula (I), a clear improvement in feel is noted, which then becomes acceptable for the user.

[0254] The locks of hair treated with one of the inventive compositions C3.1 or C3.2 display a higher level of conditioning than the locks of hair treated with one of the comparative compositions A3.1, A3.2, B3.1 or B3.2, especially in terms of smooth feel and suppleness of the hair. Furthermore, it has been observed that adding a dyeing agent to the compositions A3.1, A3.2, B3.1, B3.2, C3.1 and C3.2 would achieve the same results as above, in terms of cosmeticity.

[0255] Example 4:

[0256] Reference composition A4, comparative compositions B4 and C4, and compositions D4 according to the invention were prepared from the ingredients indicated in Table 11 below, the amounts of which are expressed in % by weight of active material (a.m.).

[0257] [Table 11]

[0258] (1) synthesized according to the method of synthesis described in example 1

[0259] 4.1 Chromaticity evaluation:

[0260] Locks of 2.7 g of natural HT4 hair were used for this evaluation.

[0261] Each composition is applied to a lock of dry hair in a bath ratio of 0.8 g of composition / gram of hair.

[0262] Each lock is then dried and then stored at 22°C for 24 hours prior to evaluation.

[0263] The colorimetric data for each of the locks are then measured with a Minolta CM-3610d spectrophotometer. In this L* a* b* system, L* represents the lightness, a* indicates the green / red color axis and b* indicates the blue / yellow color axis. The higher the value of L, the lighter or less intense the color. Conversely, the lower the value of L, the darker or more intense the color. The higher the value of a*, the redder the shade, and the higher the value of b*, the yellower the shade. The chromaticity is calculated according to the following formula:

[0264] The higher the chromaticity value C*, the more chromatic the color of the treated keratin fibers.

[0265] The results are collated in Table 12 below.

[0266] [Table 12]

[0267] It is observed that the dyeing of the hair treated with the composition D4 according to the invention presents a better chromaticity than the dyeings obtained with the reference composition A4 or the comparative compositions B4 and C4.

[0268] 4.2 Hair individualization evaluation:

[0269] Locks of 2.7 g of natural HT4 hair were used for this evaluation.

[0270] Each of the compositions B4, C4 and D4 is applied to a lock of dry hair in a bath ratio of 0.8 g of composition / gram of hair.

[0271] Each lock is then is blow-dried while combing, first with the large teeth, then with the smaller ones. The experiment stops when the lock is dry.

[0272] Generally, applying amino silicone to hair improves detangling, but has the disadvantage of sticking hair together to form clumps, unlike untreated natural hair, which is individualized.

[0273] After the above treatment, the individualization of hair for each hair locks were evaluated by a panel of five experts, trained in the sensory evaluation of hair locks. The hair individualization is evaluated by means of a score between 0 and 5 (in 0.5 steps):

[0274] 0 / 5 corresponds to a lock of hair with a very bad individualization, presence of clumps of hair to the touch;

[0275] 5 / 5 corresponds to a lock of hair with a very good individualization. No clumps of hair to the touch, well separated into individual strands.

[0276] The results are collated in Table 13 below.

[0277] [Table 13]

[0278] It is observed that the hair individualization of the hair treated with the composition D4 according to the invention is superior to that of hair treated with the comparative compositions B4 or C4.

Claims

CLAIMS1. Process for dyeing hair comprising a step of applying to said hair a composition C for permanent hair dyeing comprising:- at least one dyeing agent, and- at least one amino silicone of formula (I) below:in which:- R1 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 ranging from 2 to 8 and L is an optionally quaternized amine group selected from the following groups:-N(R3)2; -N+(R3)3A’; -NR3-Y-N(R3)2and -NR-Y-N+(R3)3A', in which R3, which may be identical or different, represents a hydrogen atom, a phenyl group, a benzyl group or a saturated monovalent hydrocarbon radical, for example a Ci-C2o alkyl group; Y denotes a linear or branched group of formula CrH2r, r being an integer ranging from 2 to 6, preferably from 2 to 4; and A" represents a cosmetically acceptable anion, especially a halide such as fluoride, chloride, bromide or iodide;- X represents a radical corresponding to formula (II) below:in which:- A independently represents a linear or branched alkylene group having from 1 to 10 carbon atoms, which may be interrupted by at least one heteroatom selected 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 being optionally substituted with 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 ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to 500.

2. Process according to the preceding claim, characterized in that the aminosilicone(s) of formula (I) are such that:- R1 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 ranging from 2 to 8 and L is an optionally quaternized amine group selected from the following groups:-N(R3)2;-N(R3)-CH2-CH2-N(R3)2in which R3, which may be identical or different, represents a hydrogen atom, a phenyl group, a benzyl group or a saturated monovalent hydrocarbon radical, for example a Ci-C2o alkyl group;- X represents a radical corresponding to formula (II) below:in which:- A independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms, that is interrupted by at least one heteroatom selected 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 being optionally substituted with 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 ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to 500.

3. Process according to any one of the preceding claims, characterized in that the aminosilicone(s) of formula (I) are such that:- R1 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 ranging from 2 to 8 and L is an amine group having the following formula: -N(R3)-CH2-CH2-N(R3)2in which R3 represents a hydrogen atom,- X represents a radical corresponding to formula (III) below:(HD in which:- Q represents an alkylene group having from 1 to 10 carbon atoms, said alkylene group being optionally substituted with 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 ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to 500.

4. Process according to any one of the preceding claims, characterized in that the aminosilicone(s) of formula (I) are of formula (IV) below:in which:- R1 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 being optionally substituted with 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 ranging from 0 to 500, m denotes an integer ranging from 1 to 500 and o denotes an integer ranging from 0 to 500, where n+m+o ranges from 250 to500.

5. Process according to any one of the preceding claims, characterized in that the total content of aminosilicone(s) of formula (I) ranges from 0.01% to 25% byweight, preferably from 0.1% to 20% by weight, more preferably from 0.5% to 20% by weight, even more preferably from 1% to 15% by weight, better still from 2% to 10% by weight, even better still from 3% to 8% by weight, relative to the total weight of the composition C.

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

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

8. Process according to any one of the preceding claims, characterized in that the composition C further comprises at least one organic solvent; preferably selected from C1-C4 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 and monomethyl ether, benzyl alcohol, and mixtures thereof; better still ethanol.

9. Process 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, even more preferably from 10% to 55% by weight, better still from 15% to 50% by weight, relative to the total weight of the composition C.

10. Process according to any one of the preceding claims, characterized in that the composition C further comprises at least one nonionic surfactant; preferably selected from oxyethylenated fatty alcohols containing at least one linear or branched, saturated or unsaturated Cs to C40, especially C8-C20, better still Cio-Cis, alkyl chain and containing from 1 to 100 mol of ethylene oxide, preferably from 2 to 50 mol, more particularly from 2 to 40 mol, or even from 3 to 20 mol of ethylene oxide.

11. Process according to the preceding claim, characterized in that the total content of nonionic surfactant(s) ranges from 0.01% to 20% by weight, more preferably from 0.05% to 10% by weight, better still from 0.1% to 5% by weight, relative to the total weight of the composition C.

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

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