WO2017134132A1 - Utilisation de composés de polyamine comportant une séquence de liaison aliphatique en présence d'agents oxydants pour le traitement des fibres kératiniques - Google Patents

Utilisation de composés de polyamine comportant une séquence de liaison aliphatique en présence d'agents oxydants pour le traitement des fibres kératiniques Download PDF

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Publication number
WO2017134132A1
WO2017134132A1 PCT/EP2017/052200 EP2017052200W WO2017134132A1 WO 2017134132 A1 WO2017134132 A1 WO 2017134132A1 EP 2017052200 W EP2017052200 W EP 2017052200W WO 2017134132 A1 WO2017134132 A1 WO 2017134132A1
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formula
chosen
crc
iii
keratin fibres
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PCT/EP2017/052200
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English (en)
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Stéphane SABELLE
Leila Hercouet
Alain Lagrange
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L'oreal
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the invention relates to the use of polyamine compounds having an aliphatic linker L comprising from 2 to 5 carbon atoms in the presence of chemical oxidizing agents for treating keratin fibres, in particular as a replacement for aqueous ammonia and/or monoethanolamine (MEA), to a process for treating keratin fibres using said particular polyamine compounds in the presence of chemical oxidizing agents, and to a multicompartment device comprising same.
  • chemical oxidizing agents for treating keratin fibres
  • MEA monoethanolamine
  • oxidation dyeing or permanent dyeing. More particularly, this dyeing method uses one or more oxidation dyes, usually one or more oxidation bases optionally combined with one or more couplers.
  • oxidation bases are chosen from ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds. These oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, afford access to coloured species.
  • the shades obtained with these oxidation bases are often varied by combining them with one or more couplers, these couplers being chosen in particular from aromatic meta- diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds.
  • direct dyes which are coloured and colouring molecules that have affinity for fibres.
  • the direct dyes generally used are chosen from nitrobenzene, anthraquinone, nitropyridine, azo, methine, azomethine, xanthene, acridine, azine and triarylmethane direct dyes. The presence of such compounds enables the colouring obtained to be further enriched with glints or enables the chromaticity of the colouring obtained to be increased.
  • Oxidation dyeing processes thus consist in using with these dye compositions a composition comprising at least one oxidizing agent, generally hydrogen peroxide, under alkaline pH conditions in the vast majority of cases.
  • the role of this oxidizing agent is, inter alia, to reveal the colouring, via an oxidative condensation reaction between the oxidation dyes.
  • Oxidation dyeing must moreover satisfy a certain number of requirements. Thus, it must be free of toxicological drawbacks, it must enable shades to be obtained in the desired intensity and it must show a good wear property in the face of external attacking factors such as light, bad weather, washing, permanent waving, perspiration and rubbing.
  • the dyes must also be able to cover white hair and, finally, they must be as unselective as possible, i.e. they must produce the smallest possible colour differences along the same keratin fibre, which generally comprises areas that are differently sensitized (i.e. damaged) from its end to its root.
  • compositions obtained must also have good mixing and application properties, and in particular good rheological properties so as not to run down the face, onto the scalp or beyond the areas that it is proposed to dye, when they are applied.
  • aqueous compositions comprising at least one oxidizing agent, under alkaline pH conditions in the vast majority of cases.
  • This oxidizing agent is to degrade the melanin of the hair, which, depending on the nature of the oxidizing agent present, leads to varying degrees of lightening of the fibres.
  • aqueous ammonia As alkaline agent. This agent has the drawback of having a very strong odour. It has occasionally been replaced with monoethanolamine (MEA), which has a much fainter odour but does not always have the same performance qualities, especially in terms of bleaching and dyeing, as aqueous ammonia.
  • MEA monoethanolamine
  • US 2012/325256 describes a hair treatment composition.
  • Said document describes a composition comprising a polyamine polymer compound (polyethyleneimine PEI- 35) and MEA. Nevertheless, this type of combination is not always satisfactory, especially in terms of lightening performance.
  • one aim is to find a replacement for aqueous ammonia and/or MEA that has a good level of performance in terms of bleaching or dyeing, while at the same time maintaining the integrity of the fibre or even improving the cosmeticity of the fibre relative to aqueous ammonia or MEA.
  • R 1 , R 2 , R 3 and R 4 which may be identical or different, represent: a) a hydrogen atom or b) a (CrC 6 )alkyl group optionally substituted with one or more groups chosen from i) hydroxyl, ii) (di)(CrC 6 )(alkyl)amino, iii) (CrC 6 )alkoxy, iv) -C(X)X'H such as carboxyl, v) heterocycle, and vi) sulfonate -S0 3 H;
  • L represents a linear or branched, saturated or unsaturated, preferably saturated, divalent hydrocarbon-based chain which comprises from 2 to 5 carbon atoms, said chain being optionally substituted with one or more groups chosen from i) hydroxyl, ii) (di)(CrC 6 )(alkyl)amino, iii) (CrC 6 )alkoxy, iv) carboxyl, v) heterocycle and vi) sulfonate; and
  • X and X' which may be identical or different, represent an oxygen or sulfur atom or a group N(R 5 ) with R 5 denoting a hydrogen atom or a (d-C 6 )alkyl group; in particular, X and X' represent an oxygen atom;
  • ingredients i) and ii) as defined previously, for the dyeing and/or lightening of keratin fibres.
  • Another subject of the invention is a multi-compartment kit or device comprising ingredients i) and ii) as defined previously.
  • the compounds of formula (I) according to the invention combined with the ingredient(s) ii) make it possible to obtain a good level of performance especially in terms of lightening of keratin fibres, while at the same time maintaining integrity of the keratin fibres that is comparable to or even greater than that obtained with aqueous ammonia or monoethanolamine (MEA).
  • MEA monoethanolamine
  • alkyf radicals are saturated, linear or branched, C C 6 hydrocarbon-based radicals, preferably C C 4 alkyl radicals, such as methyl, ethyl, propyl or butyl;
  • alkoxy radicals are alkyl-oxy radicals with alkyl as defined previously, preferably CrC 4 alkyl, such as methoxy, ethoxy, propoxy and butoxy;
  • hydrocarbon-based chain means a chain formed from carbon and hydrogen atoms, which may be saturated or unsaturated, and linear or branched, and which comprises from 1 to 12 carbon atoms, particularly from 2 to 10 carbon atoms; more particularly, it is (C 2 -C 8 )alkylene or (C 2 -C 8 )alkenylene; preferentially, the hydrocarbon- based chain is saturated and linear;
  • alkylene means a saturated, divalent, linear or branched, preferably linear, hydrocarbon-based chain -(CH 2 ) m - with m representing an integer between 2 and 4, in particular between 2 and 3 such as 2;
  • alkenylene means a divalent, linear or branched hydrocarbon-based chain, comprising from 1 to 3 conjugated or non-conjugated double bonds
  • heterocycle means a radical comprising, in at least one ring, one or more heteroatoms chosen in particular from O, N and S, preferably O or N, optionally substituted especially with one or more alkyl, alkoxy, carboxyl, hydroxyl, amine or ketone groups. These rings may contain one or more oxo groups on the carbon atoms of the heterocycle; among the heterocyclic radicals that may be used, mention may be made especially of furyl, morpholino, piperazino, piperidino, pyranyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl and thienyl groups;
  • organic or mineral acid salt means cosmetically acceptable salts, more particularly salts chosen from a salt derived i) from mineral acids and from halogenated acids such as the salts of hydrochloric acid HCI, hydrobromic acid HBr, sulfuric acid H 2 S0 4 , ii) from (d-C 6 )alkylsulfonic acids: Alk-S(0) 2 OH such as methanesulfonic acid and ethanesulfonic acid; iii) from arylsulfonic acids: Ar-S(0) 2 OH such as benzenesulfonic acid and toluenesulfonic acid; iv) from (poly)(hydroxy)(CrC 6 )alkylcarboxylic acids such as the salts of citric acid; of succinic acid; of tartaric acid; of lactic acid, x) from (C C 6 )alkoxysulfinic acids: Alk-0-S(0)OH such as methoxys
  • organic acid salts used in the invention are not derived from (di)carboxylic acids comprising a (C 2 -C 6 )alkenylene or (C 2 -C 6 )alkenyl group such as maleic acid;
  • the keratin fibres treated via the process according to the invention are in particular human and preferably the hair.
  • ingredients i) and ii) are used together for lightening keratin fibres.
  • ingredients i) and ii) are used for lightening keratin fibres.
  • ingredients i) and ii) are used together for simultaneously lightening and dyeing keratin fibres.
  • Polyamines of formula (I) The polyamine compounds of formula (I) of the invention are used in combination with one or more chemical oxidizing agents for treating keratin fibres.
  • the polyamine compound(s) of formula (I) of the invention are such that L represents an optionally substituted, preferably unsubstituted, (C 2 -C 5 )alkylene (preferentially (C 2 -C 4 )alkylene) chain.
  • L represents an ethylene or propylene, preferably ethylene chain.
  • the compounds of formula (I) are such that R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent: a) a hydrogen atom or b) a (CrC 6 )alkyl group; preferably, R 1 , R 2 , R 3 and R 4 represent a hydrogen atom.
  • the polyamine compounds of the invention are chosen from diamine compounds 1 and 2 below and also the organic or mineral acid salts thereof and the solvates thereof such as hydrates:
  • Chemical oxidizing agent means an oxidizing agent other than atmospheric oxygen.
  • alkali metal or quaternary ammonium persalts such as perborates, persulfates, percarbonates, peroxodiphosphates or Oxone®;
  • the oxidizing agent is chosen in particular from sodium perborate, sodium persulfate, potassium persulfate, ammonium persulfate, sodium percarbonate and potassium percarbonate;
  • aliphatic C C 6 and aromatic C 6 -C 20 organic peracids such as performic acid, peracetic acid, perbenzoic acid derivatives, trifluoroacetic acid, peroxyphthalic acid, peroxymaleic acid, peroxypropionic acid; the oxidizing agent is particularly peracetic acid;
  • organic peroxides such as dioxirane, C C 6 alkyl peroxides, benzoyl peroxide, peroxo(CrC 6 )alkyl carboxylates, bis(tri)(CrC 6 )alkylsilyl peroxides such as bis(trimethylsilyl) peroxide, C C 6 alkyl peroxydicarbonates, and sodium nonanoyloxybenzene sulfonate as described in patents WO 1995/000625 and US 4
  • oxidizing anions such as nitrites, nitrates, hypochlorites, hypobromites, hypoiodites, chlorites, bromites, iodites, chlorates, bromates, iodates or periodates;
  • the oxidizing agent is chosen in particular from alkali metal hypochlorite or periodate, such as sodium hypochlorite or sodium periodate;
  • N-oxy (NO ) radicals such as the 2,2,6,6-tetra(CrC 6 )alkylpiperidinooxy or 2,2,6,6-tetra(C 1 -C 6 )alkylmorpholinooxy radical, nitrosodisulfonate Fremy salts and morpholine N-oxide;
  • the oxidizing agent is particularly chosen from the 2,2,6,6- tetramethylpiperidyloxy radical;
  • hypervalent iodine derivatives such as iodotriacetate, iodosobenzene, iodobenzenetriacetate, iodoperbenzoic acid derivatives, periodinanes, and alkyl and benzoyl hypoiodites.
  • the oxidizing agent is chosen from iodotriacetate, iodosobenzene, iodobenzenetriacetate, iodoperbenzoic acid and Dess-Martin periodinane;
  • the optional supports for these oxidizing agents a1 ) to a8) may be chosen from silica, alumina, charcoal and charged or neutral polymers;
  • a9-2) polymeric complexes that can release hydrogen peroxide such as polyvinylpyrrolidone/H 2 0 2 in particular in the form of powders, and the other polymeric complexes described in US 5 008 093; US 3 376 1 10; US 5 183 901 ; a9-3) oxidases which produce hydrogen peroxide in the presence of a suitable substrate (for example glucose in the case of glucose oxidase or uric acid with uricase);
  • a suitable substrate for example glucose in the case of glucose oxidase or uric acid with uricase
  • metal peroxides which generate hydrogen peroxide in water, such as calcium peroxide or magnesium peroxide;
  • the chemical oxidizing agent(s) are chosen from a9) hydrogen peroxide or hydrogen peroxide-generating systems, more particularly H 2 0 2 .
  • the process uses one or more systems that generate hydrogen peroxide chosen from a9-1 ) urea peroxide, a9-2) polymeric complexes that can release hydrogen peroxide chosen from polyvinylpyrrolidone/H 2 0 2 ; a9-3) oxidases; a9-5) perborates and a9-6) percarbonates.
  • composition comprising the chemical oxidizing agent(s), in particular a) the hydrogen peroxide or the hydrogen peroxide generator(s), may also include various adjuvants conventionally used in hair dyeing compositions and as defined hereinbelow at the point entitled "cosmetic composition” .
  • the chemical oxidizing agent(s), in particular the hydrogen peroxide or the hydrogen peroxide-generating system(s) used preferably represent from 0.1 % to 50% by weight, preferably from 0.5% to 20% by weight, and even more preferentially from 1 % to 15% by weight, relative to the weight of the composition expressed as hydrogen peroxide, relative to the total weight of the composition containing them.
  • one or more persalts are used, preferably chosen from alkali metal or alkaline-earth metal persulfates, perborates and percarbonates.
  • the persalts are chosen from persulfate(s) such as sodium persulfate, potassium persulfate or ammonium persulfate, and mixtures thereof.
  • the persalt content may range from 0.01 % to 20% by weight, preferably from 0.1 % to 5% by weight, relative to the total weight of the composition used in the invention.
  • the compound(s) of formula (I) are used in the presence ii) of a chemical oxidizing agent which is in a cosmetic composition also comprising iii) one or more fatty substances.
  • fatty substance means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1 % and even more preferentially less than 0.1 %). They bear in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups.
  • the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, ethanol, benzene, liquid petroleum jelly or decamethylcyclopentasiloxane.
  • o/T means a "fatty substance” that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg or 1 .013 ⁇ 10 5 Pa).
  • non-silicone oif means an oil not containing any silicon (Si) atoms and the term “silicone oif means an oil containing at least one silicon atom.
  • the fatty substances are chosen from C 6 -C 16 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils of animal origin, triglycerides of plant or synthetic origin, fluoro oils, fatty alcohols, non-salified fatty acids, esters of fatty acid and/or of fatty alcohol other than triglycerides, non-silicone waxes other than solid fatty alcohols and than solid synthetic esters, and silicones, and mixtures thereof.
  • fatty alcohols, esters and acids more particularly bear at least one linear or branched, saturated or unsaturated hydrocarbon- based group comprising 6 to 30 carbon atoms, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • the linear or branched hydrocarbons of mineral or synthetic origin containing more than 16 carbon atoms are preferably chosen from liquid paraffins, liquid petroleum jelly, polydecenes and hydrogenated polyisobutene such as Parleam®, and mixtures thereof.
  • C 6 -Ci 6 lower alkanes they are linear or branched, or possibly cyclic.
  • Examples that may be mentioned include hexane, cyclohexane, undecane, dodecane, tridecane or isoparaffins, such as isohexadecane, isodecane or isododecane, and mixtures thereof.
  • a hydrocarbon-based oil of animal origin that may be mentioned is perhydrosqualene.
  • the triglycerides of plant or synthetic origin are preferably chosen from liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, more particularly from those present in plant oils, for instance sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, jojoba oil, shea butter oil or synthetic caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel, and mixtures thereof.
  • the fluoro oils may be chosen from perfluoromethylcyclopentane and perfluoro-1 ,3- dimethylcyclohexane, sold under the names Flutec® PC1 and Flutec® PC3 by the company BNFL Fluorochemicals; perfluoro-1 , 2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050® and PF 5060® by the company 3M, or alternatively bromoperfluorooctyl sold under the name Foralkyl® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethyl perfluoromorpholine sold under the name PF 5052® by the company 3M.
  • the fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols comprising from 8 to 30 carbon atoms.
  • Examples that may be mentioned include cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2- undecylpentadecanol, oleyl alcohol, linolenyl alcohol, ricinoleyl alcohol, undecylenyl alcohol and linoleyl alcohol, and mixtures thereof.
  • the fatty acids that may be used in the context of the invention are more particularly chosen from saturated or unsaturated carboxylic acids containing from 6 to 30 carbon atoms and in particular from 9 to 30 carbon atoms. They are advantageously chosen from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid. These fatty acids are, in the composition of the invention, not salified with organic or mineral bases, so as not to give rise to soaps.
  • esters of fatty acids and/or of fatty alcohols other than the triglycerides mentioned above and plant waxes mention may be made in particular of esters of saturated or unsaturated, linear C C ⁇ e or branched C 3 -C 26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear Ci-C 26 or branched C 3 -C 2 6 aliphatic monoalcohols or polyalcohols, the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; C 12 -C 15 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methylacetyl ricinoleate; myristyl stearate;
  • esters of C 4 -C 22 dicarboxylic or tricarboxylic acids and of C C- 22 alcohols and esters of mono-, di- or tricarboxylic acids and of C 2 -C 26 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • esters mentioned above it is preferred to use ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate and cetyl octanoate, and mixtures thereof.
  • alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobuty
  • composition may also comprise, as fatty ester, sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sugar esters oxygen-bearing hydrocarbon-based compounds bearing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • sucrose or saccharose
  • glucose or galactose
  • ribose or fucose
  • maltose fructose
  • mannose mannose
  • arabinose xylose
  • lactose and derivatives thereof, in particular alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen in particular from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 3 o and preferably Ci 2 -C 22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • the esters according to this variant may also be chosen from mono-, di-, tri- and tetraesters, polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters.
  • monoesters and diesters and especially sucrose, glucose or methylglucose monooleate or dioleate, stearate, behenate, oleopalmitate, linoleate, linolenate or oleostearate.
  • esters or mixtures of esters of sugar and of fatty acid examples include:
  • sucrose palmitostearates formed from 73% monoester and 27% diester and triester, from 61 % monoester and 39% diester, triester and tetraester, from 52% monoester and 48% diester, triester and tetraester, from 45% monoester and 55% diester, triester and tetraester, from 39% monoester and 61 % diester, triester and tetraester, and sucrose monolaurate;
  • Ryoto Sugar Esters for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% di-triester- polyester;
  • sucrose mono-dipalmito-stearate sold by the company Goldschmidt under the name Tegosofl® PSE.
  • non-silicone wax(es) other than solid fatty alcohols and solid synthetic esters are chosen especially from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, plant waxes, such as olive tree wax, rice wax, hydrogenated jojoba wax or absolute flower waxes, such as the blackcurrant blossom essential wax sold by the company Bertin (France), or animal waxes, such as beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy raw materials that may be used according to the invention are in particular marine waxes, such as the wax sold by the company Sophim under the reference M82, polyethylene waxes or polyolefin waxes in general.
  • the silicones that may be used in the cosmetic compositions of the present invention are volatile or non-volatile, cyclic, linear or branched silicones, which are unmodified or modified with organic groups, having a viscosity of 5x 10 ⁇ 6 to 2.5 m 2 /s at 25°C, and preferably 1 x 1 0 "5 to 1 m 2 /s.
  • the silicones that may be used in accordance with the invention may be in the form of oils, waxes, resins or gums.
  • the silicone is chosen from polydialkylsiloxanes, especially polydimethylsiloxanes (PDMSs), and organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • PDMSs polydimethylsiloxanes
  • organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • Organopolysiloxanes are defined in greater detail in Walter Noll's Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • the silicones are more particularly chosen from those with a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone ® 7207 by Union Carbide or Silbione ® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone ® 7158 by Union Carbide, and Silbione ® 70045 V5 by Rhodia, and mixtures thereof.
  • Non-volatile polydialkylsiloxanes are preferably used.
  • silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes bearing trimethylsilyl end groups.
  • the viscosity of the silicones is measured at 25°C according to ASTM Standard 445 Appendix C.
  • oils of the 200 series from the company Dow Corning such as DC200 with a viscosity of 60 000 mm 2 /s;
  • the silicone gums that may be used in accordance with the invention are especially polydialkylsiloxanes and preferably polydimethylsiloxanes with high number-average molecular weights of between 200 000 and 1 000 000, used alone or as a mixture in a solvent.
  • This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.
  • Products that may be used more particularly in accordance with the invention are mixtures such as:
  • CTFA such as the product Q2 1401 sold by Dow Corning
  • the product SF 1236 is a mixture of a gum SE 30 defined above, with a viscosity of 20 m 2 /s and of an oil SF 96 with a viscosity of 5x 10 ⁇ 6 m 2 /s.
  • This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96.
  • organopolysiloxane resins that may be used in accordance with the invention are crosslinked siloxane systems containing the following units:
  • R represents an alkyl containing 1 to 16 carbon atoms.
  • R denotes a C C 4 lower alkyl group, more particularly methyl.
  • organomodified silicones that may be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
  • the organomodified silicones may be polydiarylsiloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized by the organofunctional groups mentioned previously.
  • the polyalkylarylsiloxanes are particularly chosen from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity ranging from 1 10 "5 to 5 ⁇ 10 "2 m 2 /s at 25°C.
  • silicones of the PK series from Bayer such as the product PK20;
  • silicones of the PN and PH series from Bayer such as the products PN1000 and PH1000;
  • oils of the SF series from General Electric such as SF 1023, SF 1 154, SF 1250 and SF 1265.
  • organomodified silicones mention may be made of polyorganosiloxanes comprising:
  • C 6 - polyethyleneoxy and/or polypropyleneoxy groups optionally including C 6 -C 2 4 alkyl groups, such as the products known as dimethicone copolyol sold by the company Dow Corning under the name DC 1248 or the oils Silwet® L 722, L 7500, L 77 and L 71 1 by the company Union Carbide, and the (C 12 )alkylmethicone copolyol sold by the company Dow Corning under the name Q2 5200;
  • substituted or unsubstituted amino groups such as the products sold under the names GP 4 Silicone Fluid and GP 7100 by the company Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning.
  • the substituted amino groups are, in particular, CrC 4 aminoalkyl groups;
  • the fatty substance(s) do not comprise any C 2 -C 3 oxyalkylene units. Preferably, they do not contain any glycerol units. More particularly, the fatty substances are other than fatty acids.
  • the fatty substances are chosen from compounds that are liquid or pasty at room temperature and at atmospheric pressure.
  • the fatty substance is a compound that is liquid at a temperature of 25°C and at atmospheric pressure, or oil.
  • the fatty substances are not silicone-based.
  • the fatty substances are preferably chosen from C 6 -C 16 hydrocarbons, hydrocarbons comprising more than 16 carbon atoms, non-silicone oils of animal origin, triglycerides of plant or synthetic origin, fatty alcohols, fatty acid and/or fatty alcohol esters, or mixtures thereof.
  • the fatty substance is chosen from liquid petroleum jelly, liquid paraffin, polydecenes, fatty acid and/or fatty alcohol esters that are liquid at room temperature and at atmospheric pressure, fatty alcohols that are liquid at room temperature and at atmospheric pressure and fatty acids that are liquid at room temperature and at atmospheric pressure, or mixtures thereof.
  • composition which comprises ingredients i) and ii) as defined previously also preferably comprises iii) one or more fatty substances, preferably one or more oils in a content of between 0.1 % and 80% by weight, in particular between 1 % and 60% by weight, preferably between 5% and 40% by weight and more particularly between 10% and 30% by weight relative to the total weight of the composition comprising i), ii) and iii).
  • the composition of the process according to the invention comprises iv) at least one surfactant, which is preferably nonionic.
  • the nonionic surfactants according to the invention are preferably chosen from fatty alcohols, a-diols and alkylphenols, these three types of compound being polyethoxylated, polypropoxylated and/or polyglycerolated and containing a fatty chain comprising, for example, 8 to 22 carbon atoms, the number of ethylene oxide or propylene oxide groups possibly ranging especially from 2 to 50 and the number of glycerol groups possibly ranging especially from 2 to 30.
  • polyethoxylated fatty amides preferably having from 2 to 30 ethylene oxide units, polyglycerolated fatty amides containing on average 1 to 5, and in particular 1 .5
  • the nonionic surfactant(s) are chosen from:
  • fatty chain means a linear or branched, saturated or unsaturated hydrocarbon- based chain comprising from 6 to 30 carbon atoms and preferably from 8 to 24 carbon atoms.
  • alkylpolyglycosides these compounds are well known and may be represented more particularly by the following general formula:
  • R 2 represents an alkylene radical comprising from about 2 to 4 carbon atoms
  • G represents a sugar unit comprising from 5 to 6 carbon atoms
  • t denotes an integer between 0 and 10 inclusive, preferably between 0 and 4;
  • Alkylpolyglycosides that are preferred according to the present invention are compounds of formula (II) in which ⁇ denotes more particularly a linear or branched, saturated or unsaturated alkyl radical comprising from 8 to 18 carbon atoms, t denotes a value ranging from 0 to 3 even more particularly equal to 0, and G can denote glucose, fructose or galactose, preferably glucose.
  • the degree of polymerization i.e. the value of v in formula (II), may range from 1 to 15 and preferably from 1 to 4.
  • the average degree of polymerization is more particularly between 1 and 2 and even more preferentially from 1 .1 to 1 .5.
  • glycoside bonds between the sugar units are of 1 -6 or 1 -4 type and preferably of 1 -4 type.
  • Compounds of formula (II) are especially 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). It is also possible to use the products sold by the company SEPPIC under the names Triton CG 1 10 or Oramix CG 1 10 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 AG10 LK.
  • the mono- or polyglycerolated surfactants preferably comprise on average from 1 to 30 glycerol groups, more particularly from 1 to 10 and in particular from 1 .5 to 5 glycerol groups.
  • the monoglycerolated or polyglycerolated surfactants are preferably chosen from the compounds of the following formulae:
  • R represents a linear or branched, saturated or unsaturated, hydrocarbon-based radical comprising from 8 to 40 carbon atoms and preferably from 10 to 30 carbon atoms; and m is a number between 1 and 30, preferably between 1 and 10, more particularly from 1 .5 to 6.
  • R may optionally comprise heteroatoms, for instance oxygen and nitrogen.
  • R may optionally comprise one or more hydroxyl and/or ether and/or amide groups.
  • R preferably denotes optionally mono- or polyhydroxylated C 10 -C 20 alkyl and/or alkenyl radicals.
  • Use may be made, for example, of the polyglycerolated (3.5 mol) hydroxylauryl ether sold under the name Chimexane® NF from Chimex.
  • the (poly)ethoxylated fatty alcohols which are suitable for implementing the invention are selected more particularly from alcohols containing from 8 to 30 carbon atoms, and preferably from 12 to 22 carbon atoms.
  • the (poly)ethoxylated fatty alcohols more particularly contain one or more linear or branched, saturated or unsaturated hydrocarbon-based groups, comprising 8 to 30 carbon atoms, which are optionally substituted, in particular with one or more (in particular 1 to 4) hydroxyl groups. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • the (poly)ethoxylated fatty alcohol(s) preferably have the following formula:
  • - n representing an integer between 1 and 200 inclusive, preferentially between 2 and 50 and more particularly between 2 and 30 inclusive, such as 20.
  • the (poly)ethoxylated fatty alcohols are more particularly fatty alcohols comprising from 8 to 22 carbon atoms and oxyethylenated with 1 to 30 mol of ethylene oxide (1 to 30 EO).
  • fatty alcohols comprising from 8 to 22 carbon atoms and oxyethylenated with 1 to 30 mol of ethylene oxide (1 to 30 EO).
  • nonionic surfactants use is preferably made of C 6 -C 2 4 alkyl polyglucosides and (poly)ethoxylated fatty alcohols, and C 8 -C 16 alkyl polyglucosides are more particularly used.
  • the amount of nonionic surfactants preferably ranges from 0.5% to 25% by weight, in particular from 1 % to 20% by weight and more particularly from 2% to 10% by weight relative to the total weight of the composition of the invention.
  • the surfactant(s) iii) are chosen from oxyethylenated nonionic surfactants in particular comprising a number of EO units ranging from 1 to 9; they are preferentially chosen from the following categories:
  • esters of saturated or unsaturated, linear or branched, C 8 -C 30 acids and of polyethylene glycols are examples of esters of saturated or unsaturated, linear or branched, C 8 -C 30 acids and of polyethylene glycols,
  • oxyethylenated nonionic surfactant comprising from 1 to 9 EO units
  • Emulgin 05 (Cognis) [oleocetyl alcohol 5 EO].
  • the content of oxyethylenated nonionic surfactant(s) comprising from 1 to 9 EO units in the composition according to the invention may range from 0.1 % to 10% by weight, preferably from 0.2% to 5% by weight and better still from 0.25% to 1 % by weight relative to the total weight of the composition.
  • the oxyethylenated nonionic surfactants comprising at least 10 EO units used in the invention may especially have a number of oxyethylene groups ranging from 10 to 50, preferably from 15 to 30.
  • the oxyethylenated nonionic surfactants comprising at least 10 EO units used in the invention comprise at least 15 oxyethylene groups.
  • oxyethylenated nonionic surfactants comprising at least 10 EO units
  • ethylene oxide with oleyl alcohol especially those comprising from 10 to 20 oxyethylene groups, for instance the products sold under the references Brij 96V (Oleth-10) and Brij 98V (Oleth-20) by the company Croda.
  • the content of oxyethylenated nonionic surfactants comprising at least 10 oxyalkylene groups in the composition according to the invention may range from 0.1 % to 20% by weight, preferably from 0.5% to 15% by weight and better still from 1% to 10% by weight relative to the total weight of the composition.
  • the total amount of oxyethylenated nonionic surfactants in the composition is preferably less than or equal to 10% by weight relative to the total weight of the composition. It may range from 0.1 % to 10% by weight, preferably from 1% to 7% by weight and even better still from 2% to 6% by weight.
  • additional basifying agents The process according to the invention may also use one or more basifying agents other than the polyamine compounds of formula (I) as defined previously.
  • the basifying agent may be mineral or organic or hybrid.
  • the mineral basifying agent(s) are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, sodium hydroxide and potassium hydroxide, and mixtures thereof.
  • the organic basifying agent(s) are preferably chosen from organic amines with a pKb at 25°C of less than 12, preferably less than 10 and even more advantageously less than 6. It should be noted that it is the pKb corresponding to the function of highest basicity.
  • the additional alkaline agent(s) are chosen from i) (bi)carbonates, ii) aqueous ammonia, iii) alkanolamines such as monoethanolamine, diethanolamine, triethanolamine and derivatives thereof, iv) optionally oxyalkylenated fatty amines, v) mineral or organic hydroxides, vi) alkali metal silicates such as sodium metasilicates, vii) amino acids, preferably basic amino acids such as arginine, lysine, ornithine, citrulline and histidine, and viii) the compounds of formula (III) other than the polyamine compounds of formula (I), below:
  • W is a divalent (CrC 8 )alkylene radical optionally substituted with at least one hydroxyl group or at least one (CrC 4 )alkyl radical and/or optionally interrupted with at least one heteroatom, such as oxygen or sulfur, or with an -N(R e )- group;
  • R a , Rb, R c , Rd and R e which may be identical or different, represent a hydrogen atom or a (CrC 4 )alkyl or hydroxy(CrC 4 )alkyl radical; preferably, W represents a propylene radical.
  • the process according to the invention may optionally comprise one or more dyes chosen from a) oxidation dyes and b) direct dyes, or mixtures of a) and b) that will be detailed hereinbelow.
  • the composition comprises one or more dyes and preferably a) at least one oxidation dye.
  • the oxidation dyes are generally chosen from one or more oxidation bases optionally combined with one or more couplers.
  • the oxidation bases are chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and the corresponding addition salts.
  • para-phenylenediamines that may be mentioned are, for example, para- phenylenediamine, para-toluenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl- para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para- phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para- phenylenediamine, ⁇ , ⁇ -diethyl-para-phenylenediamine, N,N-dipropyl-para- phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(p-hydroxyethyl)-para- phenylenediamine, 4-N,N-bis(p-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(3-
  • para-phenylenediamine para- toluenediamine, 2-isopropyl-para-phenylenediamine, 2-p-hydroxyethyl-para- phenylenediamine, 2-p-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para- phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis(p-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine and 2- ⁇ - acetylaminoethyloxy-para-phenylenediamine, and the corresponding addition salts with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines that may be mentioned, for example, are ⁇ , ⁇ '- bis(p-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1 ,3-diaminopropanol, N,N'-bis(p-hydroxyethyl)- N,N'-bis(4'-aminophenyl)ethylenediamine, N,N'-bis(4-aminophenyl)tetramethylenediamine, N,N'-bis(p-hydroxyethyl)-N,N'-bis(4-aminophenyl)tetramethylenediamine, N,N'-bis(4- methylaminophenyl)tetramethylenediamine, N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'- methylphenyl)ethylenediamine and 1 ,8-bis(2,5-dia
  • para-aminophenols that are mentioned are, for example, para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3- hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2- methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(p-hydroxyethyl- aminomethyl)phenol and 4-amino-2-fluorophenol, and the corresponding addition salts with an acid.
  • para-aminophenol 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3- hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2- methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(p-hydroxyeth
  • ortho-aminophenols that may be mentioned, for example, are 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the corresponding addition salts.
  • heterocyclic bases that may be mentioned, for example, are pyridine, pyrimidine and pyrazole derivatives.
  • pyridine derivatives that may be mentioned are the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, for example 2,5-diaminopyridine, 2-(4- methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the corresponding addition salts.
  • pyridine oxidation bases that are useful in the present invention are the 3- aminopyrazolo[1 ,5-a]pyridine oxidation bases or the corresponding addition salts described, for example, in patent application FR 2 801 308.
  • Examples that may be mentioned include pyrazolo[1 ,5-a]pyrid-3-ylamine, 2-acetylaminopyrazolo[1 ,5-a]pyrid-3-ylamine, 2-(morpholin-4- yl)pyrazolo[1 ,5-a]pyrid-3-ylamine, 3-aminopyrazolo[1 ,5-a]pyridine-2-carboxylic acid, 2- methoxypyrazolo[1 ,5-a]pyrid-3-ylamine, (3-aminopyrazolo[1 ,5-a]pyrid-7-yl)methanol, 2-(3- aminopyrazolo[1 ,5-a]pyrid-5-yl)ethanol, 2-
  • the oxidation bases that are useful in the present invention are chosen from 3-aminopyrazolo[1 ,5-a]pyridines and are preferably substituted on carbon atom 2 with: a) a (di)(CrC 6 )(alkyl)amino group, said alkyl group possibly being substituted with at least one hydroxyl, amino or imidazolium group;
  • an optionally cationic 5- to 7-membered heterocycloalkyl group comprising from 1 to 3 heteroatoms, optionally substituted with one or more (CrC 6 )alkyl groups such as a di(d- C 4 )alkylpiperazinium group; or
  • pyrimidine derivatives that may be mentioned are the compounds described, for example, in patents DE 2359399; JP 88-169571 ; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6- triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists.
  • pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, for instance 4,5-diamino-1 -methylpyrazole, 4,5- diamino-1 -(p-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1 -(4'- chlorobenzyl)pyrazole, 4,5-diamino-1 ,3-dimethylpyrazole, 4,5-diamino-3-methyl-1 - phenylpyrazole, 4,5-diamino-1 -methyl-3-phenylpyrazole, 4-amino-1 ,3-dimethyl-5- hydrazinopyrazole, 1 -benzyl-4,5-diamino-3-methylpyrazole,
  • a 4,5-diaminopyrazole will preferably be used and even more preferentially 4,5-diamino- 1 -(p-hydroxyethyl)pyrazole and/or a corresponding salt.
  • pyrazole derivatives that may also be mentioned include diamino-N,N- dihydropyrazolopyrazolones and in particular those described in patent application FR-A-2 886 136, such as the following compounds and the corresponding addition salts: 2,3- diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-ethylamino-6,7-dihydro- 1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-isopropylamino-6,7-dihydro-1 H,5H- pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-(pyrrolidin-1 -yl)-6,7-dihydro-1 H,5H-pyrazolo[1 ,2- a]pyrazol-1 -one, 4,5-dia
  • Use will preferably be made of 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 - one and/or a corresponding salt.
  • Heterocyclic bases that will preferably be used include 4,5-diamino-1 -(p- hydroxyethyl)pyrazole and/or 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one and/or a corresponding salt.
  • composition according to the invention may optionally comprise one or more coupling agents advantageously chosen from those conventionally used in the dyeing of keratin fibres.
  • these coupling agents mention may be made in particular of meta- phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based coupling agents and heterocyclic coupling agents, and also the corresponding addition salts.
  • 6-methylpyrazolo[1 ,5-a]benzimidazole 2-methyl-5-aminophenol, 5-N-(B-hydroxyethyl)amino- 2-methylphenol, 3-aminophenol and 3-amino-2-chloro-6-methylphenol, the corresponding addition salts with an acid and the corresponding mixtures.
  • addition salts of oxidation bases and couplers that may be used in the context of the invention are chosen in particular from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the oxidation base(s) each advantageously represent from 0.001 % to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight relative to the total weight of the composition and of the ready-to-use composition.
  • composition according to the invention may optionally comprise b) one or more synthetic or natural direct dyes chosen from cationic, anionic and nonionic species, preferably cationic or nonionic species, either as sole dyes or in addition to the oxidation dye(s).
  • Suitable direct dyes include azo direct dyes; (poly)methine dyes such as cyanins, hemicyanins and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanin dyes and natural direct dyes, alone or in the form of mixtures.
  • the direct dyes are preferably cationic direct dyes. Mention may be made of the hydrazono cationic dyes of formulae (Ilia) and (lll'a), the azo cationic dyes (IVa) and (IV'a) and the diazo cationic dyes (Va) below:
  • Het + represents a cationic heteroaryl radical, preferably bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, optionally substituted preferably with one or more (CrC 8 )alkyl groups such as methyl;
  • Ar + represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferably ammonium, particularly tri(C 1 -C 8 )alkylammonium such as trimethylammonium;
  • Ar represents an aryl group, in particular phenyl, which is optionally substituted, preferably with one or more electron-donating groups such as i) optionally substituted (CrC 8 )alkyl, ii) optionally substituted (CrC 8 )alkoxy, iii) (di)(CrC 8 )(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, iv) aryl(C C 8 )alkylamino, v) optionally substituted N-(C 1 -C 8 )alkyl-N-aryl(C 1 -C 8 )alkylamino or, as a variant, Ar represents a julolidine group;
  • Ar' represents an optionally substituted divalent (hetero)arylene group such as phenylene, particularly para-phenylene, or naphthalene, which are optionally substituted, preferably with one or more groups (CrC 8 )alkyl, hydroxyl or (C C 8 )alkoxy;
  • Ar represents an optionally substituted (hetero)aryl group such as phenyl or pyrazolyl, which are optionally substituted, preferably with one or more (C C 8 )alkyl, hydroxyl, (di)(C C 8 )(alkyl)amino, (Ci-C 8 )alkoxy or phenyl groups;
  • R a and R b which may be identical or different, represent a hydrogen atom or a (CrC 8 )alkyl group, which is optionally substituted, preferably with a hydroxyl group; or, as a variant, the substituent R a with a substituent of Het + and/or R b with a substituent of Ar and/or R a with R b form, together with the atoms that bear them, a (hetero)cycloalkyl; particularly, R a and R b represent a hydrogen atom or a (CrC 4 )alkyl group, which is optionally substituted with a hydroxyl group;
  • An " represents an anionic counterion, such as mesylate or halide.
  • the cationic part is derived from the following derivatives:
  • - R 1 represents a (CrC 4 )alkyl group such as methyl
  • - R 2 and R 3 which may be identical or different, represent a hydrogen atom or a (d- C 4 )alkyl group, such as methyl
  • R 4 represent a hydrogen atom or an electron-donating group such as an optionally substituted (CrC 8 )alkyl group, an optionally substituted (CrC 8 )alkoxy group, or a (di)(Ci- C 8 )(alkyl)amino group optionally substituted on the alkyl group(s) with a hydroxyl group; in particular, R 4 represents a hydrogen atom,
  • - Z represents a CH group or a nitrogen atom, preferably CH
  • An " represents an anionic counterion, such as mesylate or halide.
  • the dye of formulae (llla-1) and (IVa-1 ) is chosen from Basic Red 51 , Basic Yellow 87 and Basic Orange 31 or corresponding derivatives:
  • hennotannic acid juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orcein. Extracts or decoctions containing these natural dyes and in particular henna-based poultices or extracts may also be used.
  • the direct dye(s) more particularly represent from 0.001 % to 10% by weight and preferably from 0.005% to 5% by weight relative to the total weight of the composition.
  • the process is a dyeing process and the composition contains at least one dye and preferably at least one oxidation dye as defined previously.
  • the process is solely a lightening process, which does not use any dye (the composition does not contain any dye).
  • the cosmetic composition :
  • composition(s) used in the process of the invention are cosmetic, i.e. cosmetically acceptable, in other words they generally comprise vii) water or a mixture of water and of viii) one or more organic solvents or a mixture of organic solvents.
  • organic solvent means an organic substance that is capable of dissolving or dispersing another substance without chemically modifying it.
  • organic solvents examples include C C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2- butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, hexylene glycol, and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol.
  • C C 4 lower alkanols such as ethanol and isopropanol
  • polyols and polyol ethers such as 2- butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, hexylene glycol
  • aromatic alcohols such as benzyl alcohol or phenoxyethanol.
  • the organic solvents are present in proportions preferably of between 1 % and 40% by weight approximately and more preferably still between 5% and 30% by weight approximately, relative to the total weight of the dyeing composition.
  • the pH of the cosmetic composition comprising ingredients i) and ii) is basic or alkaline, i.e. it has a pH of greater than 7, preferably between 8 and 12 and more particularly inclusively between 8 and 1 1 .
  • the pH of the composition(s) may be adjusted to the desired value by means of basifying agents as defined previously or by using acidifying agents usually used in the dyeing of keratin fibres, or alternatively by means of standard buffer systems.
  • acidifying agents for the compositions used in the invention mention may be made of the acids mentioned previously in the definition of the "salts of organic or mineral acids"; by way of example, mention may be made particularly of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids as defined previously, for instance acetic acid, tartaric acid, citric acid or lactic acid, or sulfonic acids.
  • Adjuvants Adjuvants:
  • composition(s) of the dyeing and/or lightening process in accordance with the invention may also contain various adjuvants conventionally used in hair dye compositions, such as cationic, anionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, film-forming agents, ceramides, preserving agents and opacifiers.
  • adjuvants conventionally used in hair dye compositions, such as cationic, anionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, mineral or organic thickeners, and in particular ani
  • Said adjuvants are preferably chosen from surfactants such as cationic, anionic or zwitterionic surfactants or mixtures thereof and mineral or organic thickeners.
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 40% by weight relative to the weight of the composition, and preferably between 0.1 % and 20% by weight relative to the weight of the composition i) or ii) which contains them.
  • the cosmetic composition(s) of the invention may be in various presentation forms, such as a powder, a lotion, a foam, a cream or a gel, or in any other form that is suitable for dyeing keratin fibres. They may also be packaged in a propellant-free pump-action bottle or under pressure in an aerosol container in the presence of a propellant and form a foam.
  • the process for dyeing and/or lightening keratin fibres, especially human keratin fibres such as the hair, of the invention is performed by applying to said fibres a cosmetic composition comprising ingredients i) and ii) as defined previously, and optionally ingredients iii) to x) as defined previously and ii) one or more chemical oxidizing agents as defined previously.
  • composition according to the invention as previously defined is applied to dry or wet keratin fibres. It is left in place on the fibres for a time generally ranging from 1 minute to 1 hour and preferably from 5 minutes to 30 minutes.
  • the temperature during the dyeing process conventionally ranges from room temperature (between 15°C and 25°C) to 80°C, preferably from room temperature to 50°C.
  • the human keratin fibres are optionally rinsed with water, optionally washed with a shampoo and then rinsed with water, before being dried or left to dry.
  • composition according to the invention may be prepared by mixing at least two compositions.
  • composition of the process according to the invention results from the mixing of two compositions:
  • composition (A) comprising i) one or more polyamine compound(s) of formula (I) as defined previously;
  • composition (B) comprising ii) one or more chemical oxidizing agents such as hydrogen peroxide, and
  • compositions (A) and (B) also comprises at least one of the ingredients iii) to x) as defined previously.
  • the process of the invention is performed in the absence of alkaline agent other than the polyamine compound(s) of formula (I) as defined previously.
  • the process of the invention is performed in the absence of crosslinking agent such as maleic acid.
  • a subject of the invention is the use of ingredients i) and ii) as defined previously, and optionally iii) to x) as defined previously, for dyeing and/or lightening keratin fibres, especially human keratin fibres such as the hair.
  • the use i) of the polyamine compound(s) of formula (I) as defined previously with ii) the chemical oxidizing agent(s) as defined previously, and optionally the ingredient(s) iii) to x) as defined previously, is performed in the absence of crosslinking agent, in particular of maleic acid.
  • the use i) of the polyamine compound(s) of formula (I) as defined previously with ii) the chemical oxidizing agent(s) as defined previously, and optionally the ingredient(s) iii) to x) as defined previously, is performed in the absence of aqueous ammonia and/or monoethanolamine.
  • the use i) of the polyamine compound(s) of formula (I) as defined previously with ii) the chemical oxidizing agent(s) as defined previously, and optionally the ingredient(s) iii), iv) and vi) to x) as defined previously, is performed in the absence of alkaline agents other than said polyamine compounds of formula (I).
  • Multi-compartment kit or device Another subject of the invention is a kit or device containing several separate compartments comprising ingredients i) and ii) as defined previously.
  • the kit comprises at least two compartments in which the ingredient(s) i) as defined previously are in one compartment and the ingredient(s) ii) as defined previously are in another compartment, and optionally ingredients iii) to x) as defined previously are together with i) and/or ii).
  • the kit comprises at least two compartments in which the ingredient(s) i) as defined previously are in one compartment and the ingredient(s) ii) as defined previously are in another compartment, and ingredients iii) to x) as defined previously are separate from i) or ii).
  • compositions were prepared (amount in grams per 100 g (% g)).
  • compositions 1 to 3 At the time of use, compositions 1 to 3 were prepared according to the mixtures in the following table:
  • compositions 1 to 3 Use of compositions 1 to 3:
  • L * , a * and b * represent the values measured on locks of TD4 hair after treatment and L 0 * , a 0 * and b 0 * represent the values measured on TD4 locks before treatment.
  • ⁇ * the more observable the colour variation or the lightening.
  • compositions 4 and 5 and the oxidizing formulation were prepared from the ingredients whose contents are indicated, as mass percentage of active material, in the tables below.
  • compositions 4 and 5 are Compositions 4 and 5:
  • composition 4 or 5 1 g of composition 4 or 5 is mixed with 1 .5 g of the oxidizing composition. The mixture is then applied to 250 mg locks of natural hair with a tone depth of 4. After a leave-on time of 30 minutes at 27°C, the locks are washed with a standard shampoo, rinsed and dried.
  • the colorimetric data for each of the locks are then measured with a Minolta CM- 361 Od spectrophotometer.
  • composition 4 according to the invention makes it possible to obtain much better lightening than comparative composition 5.

Abstract

L'invention concerne l'utilisation de composés de polyamine comportant une séquence de liaison aliphatique comprenant de 2 à 5 atomes de carbone en présence d'agents oxydants chimiques, pour le traitement des fibres kératiniques, en particulier en remplacement de l'ammoniaque et/ou de la monoéthanolamine (MEA), un procédé pour le traitement des fibres kératiniques utilisant lesdits composés de polyamine particuliers en présence d'agents oxydants chimiques, et un dispositif à plusieurs compartiments en contenant. Les composés de formule (I) selon l'invention associés à un ou plusieurs ingrédients ii) permettent d'obtenir un bon niveau de performance, notamment en termes d'éclaircissement des fibres kératiniques, tout en préservant parallèlement l'intégrité des fibres kératiniques de façon comparable, ou même supérieure, à la MEA. De plus, aucune odeur désagréable associée aux composés de formule (I) en présence d'un agent oxydant n'est observée.
PCT/EP2017/052200 2016-02-04 2017-02-02 Utilisation de composés de polyamine comportant une séquence de liaison aliphatique en présence d'agents oxydants pour le traitement des fibres kératiniques WO2017134132A1 (fr)

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FR1650894 2016-02-04
FR1650894A FR3047413B1 (fr) 2016-02-04 2016-02-04 Utilisation de composes polyamines a linker aliphatique en presence d’oxydants pour traiter les fibres keratiniques

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