WO2019063611A1 - Procédé de teinture par oxydation utilisant un coupleur et un sel peroxygéné en tant qu'agent oxydant - Google Patents

Procédé de teinture par oxydation utilisant un coupleur et un sel peroxygéné en tant qu'agent oxydant Download PDF

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WO2019063611A1
WO2019063611A1 PCT/EP2018/076127 EP2018076127W WO2019063611A1 WO 2019063611 A1 WO2019063611 A1 WO 2019063611A1 EP 2018076127 W EP2018076127 W EP 2018076127W WO 2019063611 A1 WO2019063611 A1 WO 2019063611A1
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amino
composition
chosen
process according
weight
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PCT/EP2018/076127
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English (en)
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Mickaël AGACH
Ambre SOUVIROU
Simon DONCK
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L'oreal
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    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/882—Mixing prior to application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • Oxidation dyeing process using a coupler and a peroxygenated salt as
  • the present invention relates to a process for the oxidation dyeing of keratin fibres using one or more oxidation coupler(s) and an oxidizing composition comprising a peroxygenated salt, in the absence of oxidation base.
  • oxidation bases such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidation bases are initially colourless or weakly coloured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • oxidation bases may be varied by combining them with couplers or colour modifiers, the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
  • couplers or colour modifiers the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
  • the permanent dyeing process thus consists in applying, to the keratin fibres, bases or a mixture of bases and couplers with hydrogen peroxide (H2O2 or aqueous hydrogen peroxide solution), as oxidizing agent, in leaving them to diffuse, and in then rinsing the fibres.
  • H2O2 or aqueous hydrogen peroxide solution hydrogen peroxide
  • the role of this oxidizing agent is to degrade the melanin of the hair, which, depending on the nature of the oxidizing agent present, leads to more or less pronounced lightening of the fibres. It also has the role of activating the oxidation of the oxidation dye precursors and the formation of coloured species.
  • the oxidizing agent generally used is hydrogen peroxide.
  • the colourings resulting therefrom have the advantage of being permanent, strong and resistant to external agents, in particular to light, bad weather, washing, perspiration and rubbing.
  • This (these) aim(s) is (are) achieved by the present invention, one subject of which is a process for the oxidation dyeing of keratin fibres, in particular human keratin fibres such as the hair, comprising the application to the keratin fibres:
  • composition (A) comprising at least one coupler
  • At least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts;
  • compositions (A) and (B) can be applied simultaneously or separately.
  • compositions (A) and (B) are distinct compositions.
  • the dyeing process does not use a chemical oxidizing agent other than the peroxygenated salt(s).
  • the peroxygenated salt(s) is (are) the only chemical oxidizing agent(s) used in the process of the invention.
  • the expression "chemical oxidizing agent” is intended to mean any chemical oxidizing agent other than atmospheric oxygen.
  • the dyeing process according to the invention makes it possible to obtain very good dyeing properties of the colouration, in particular in terms of selectivity, that is to say colourations which are uniform along the keratin fibre, of chromaticity, of intensity (power) and of colour build-up, this being despite the absence of oxidation basis, while the same time being friendly to the integrity of the keratin fibres.
  • the dyeing process according to the invention makes it possible to improve the intensity of the colouration on the keratin fibres compared with a conventional dyeing process.
  • the present invention also relates to a multicompartment device comprising a first compartment containing a composition (A) as defined previously, and a second compartment containing a composition comprising at least one peroxygenated salt.
  • composition (A) comprises one or more couplers that are conventionally used for dyeing keratin fibres.
  • the couplers are chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof and/or the solvates thereof.
  • Examples that may be mentioned include 1 ,3-dihydroxybenzene, 1 ,3-dihydroxy-2- methylbenzene, 4-chloro-1 ,3-dihydroxybenzene, 1 -hydroxy-3-aminobenzene, 1 -methyl-2- hydroxy-4-3-hydroxyethylaminobenzene, 4-amino-2-hydroxytoluene, 5-amino-6-chloro-2- methylphenol, 2,4-diamino-1-(3-hydroxyethyloxy)benzene, 2-amino-4-(3- hydroxyethylamino)-1 -methoxybenzene, 1 ,3-diaminobenzene, 1 ,3-bis(2,4- diaminophenoxy)propane, 3-ureidoaniline, 3-ureido-1 -dimethylaminobenzene, sesamol, 1 - 3-hydroxyethylamino-3,4-methylenedioxybenzene, on
  • the coupler(s) used in the process of the invention are chosen from 1 ,3- dihydroxybenzene, 1 ,3-dihydroxy-2-methybenzene, 4-chloro-1 ,3-dihydroxybenzene, 1 - hydroxy-3-aminobenzene, 1 -methyl-2-hydroxy-4-3-hydroxyethylaminobenzene, 4-amino- 2-hydroxytoluene, 5-amino-6-chloro-2-methylphenol, 2,4-diamino-1 -( ⁇ - hydroxyethyloxy)benzene, a-naphthol, 6-hydroxyindole, 2-amino-3-hydroxypyridine, 6- hydroxybenzomorpholine, 3-amino-6-methoxy-2-methylaminopyridine, 2-amino-4- hydroxyethylaminoanisole, the addition salts thereof and/or the solvates thereof, and mixtures thereof.
  • the coupler(s) used in the process of the invention are chosen from 3-amino-6-methoxy-2-methylaminopyridine, 6- hydroxybenzomorpholine, 2,4-diamino-1-(3-hydroxyethyloxy)benzene, 2-amino-3- hydroxypyridine, 5-amino-6-chloro-2-methylphenol, 1 -methyl-2-hydroxy-4-3- hydroxyethylaminobenzene, 2-amino-4-hydroxyethylaminoanisole, the addition salts thereof and/or the solvates thereof, and mixtures thereof.
  • the addition salts of the couplers that may be used in the context of the invention are especially chosen from the addition salts with an acid, such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the content of coupler(s) can range from 0.001 % to 10% by weight and preferably from 0.005% to 5% by weight relative to the total weight of the composition (A).
  • oxidation bases are for example para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, and the addition salts and/or solvates thereof.
  • para-phenylenediamines examples that may be mentioned include para- phenylenediamine, para-tolylenediamine, 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, N,N-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(p- hydroxyeth
  • 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-diaminophen
  • para-aminophenols that may be mentioned, for example, are 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-hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • 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 addition salts thereof.
  • heterocyclic bases mention may be made of those comprising at least two nitrogen atoms, in particular pyridine derivatives, pyrimidine derivatives 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 instance 2,5-diaminopyridine, 2- (4-methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the addition salts thereof.
  • pyridine oxidation bases that are useful in the present invention are the 3- aminopyrazolo[1 ,5-a]pyridine oxidation bases or addition salts thereof 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-(
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2 359 399; JP 88-169571 ; JP 05-63124; EP 0770375 or patent application WO 96/15765, for instance 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6- triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6- diaminopyrimidine and 2,5,6-triaminopyrimidine, and the addition salts thereof and the tautomers thereof, when a tautomeric equilibrium exists.
  • pyrazole derivatives that may be mentioned are the compounds described in patents DE 3 843 892, DE 4 133 957 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-methylpyrazo
  • 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 addition salts thereof: 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-di
  • the composition (A) comprises one or more organic or mineral alkaline agents.
  • the alkaline agent(s) may be mineral or organic.
  • the mineral alkaline agent(s) is (are) preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium hydroxide or potassium hydroxide, or mixtures thereof.
  • the organic alkaline agent(s) are preferably chosen from organic amines with a pKb at 25°C of less than 12, preferably of less than 10 and even more advantageously of less than 6. It should be noted that it is the pKb corresponding to the function of highest basicity.
  • the organic amines do not comprise any alkyl or alkenyl fatty chain comprising more than ten carbon atoms.
  • organic alkaline agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (III) below:
  • W is a divalent C1-C6 alkylene radical optionally substituted with one or more hydroxyl groups or a C1-C6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as O, or NR U , and R x , R y , R z , Rt and R u , which may be identical or different, represent a hydrogen atom or a C1-C6 alkyl, C1-C6 hydroxyalkyl or C1-C6 aminoalkyl radical.
  • Examples of amines having formula (III) that may be mentioned include 1 ,3- diaminopropane, 1 ,3-diamino-2-propanol, spermine and spermidine.
  • alkanolamine is intended to mean an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C-i-Cs alkyl groups bearing one or more hydroxyl radicals.
  • Organic amines chosen from alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines, comprising one to three identical or different C1-C4 hydroxyalkyl radicals, are in particular suitable for implementing the invention.
  • MAA monoethanolamine
  • diethanolamine triethanolamine
  • monoisopropanolamine diisopropanolamine
  • N,N- dimethylethanolamine 2-amino-2-methyl-1 -propanol
  • triisopropanolamine 2-amino-2- methyl-1 ,3-propanediol
  • 3-amino-1 ,2-propanediol 3-dimethylamino-1 ,2-propanediol and tris(hydroxymethyl)aminomethane.
  • amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid and phosphoric acid functions.
  • the amino acids may be in neutral or ionic form.
  • the amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in a ureido function.
  • Such basic amino acids are preferably chosen from those corresponding to formula (IV) below, and also the salts thereof:
  • R represents a group chosen from:
  • the compounds corresponding to the formula (IV) are histidine, lysine, arginine, ornithine and citrulline.
  • the organic amine may also be chosen from organic amines of heterocyclic type. Besides histidine that has already been mentioned in the amino acids, mention may in particular be made of pyridine, piperidine, imidazole, triazole, tetrazole and benzimidazole.
  • the organic amine may also be chosen from amino acid dipeptides.
  • amino acid dipeptides that may be used in the present invention, mention may be made especially of carnosine, anserine and balenine.
  • the organic amine may also be chosen from compounds comprising a guanidine function.
  • amines of this type that may be used in the present invention, besides arginine, which has already been mentioned as an amino acid, mention may be made especially of creatine, creatinine, 1 ,1 -dimethylguanidine, 1 ,1 -diethylguanidine, glycocyamine, metformin, agmatine, N-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-1 -sulfonic acid.
  • Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid.
  • Guanidine carbonate or monoethanolamine hydrochloride may be used in particular.
  • the alkaline agent(s) present in the composition of the invention are chosen from aqueous ammonia, sodium hydroxide, alkanolamines, amino acids in neutral or ionic form, in particular basic amino acids, and preferably corresponding to those of formula (III).
  • the alkaline agent(s) are chosen from aqueous ammonia, sodium hydroxide and alkanolamines, most particularly monoethanolamine (MEA), and mixtures thereof.
  • MEA monoethanolamine
  • composition A of the process according to the invention comprises one or more fatty substances.
  • fatty substance is intended to mean 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 including 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.
  • the fatty substances are chosen from compounds that are liquid or pasty at ambient temperature and at atmospheric pressure.
  • the fatty substance(s) is (are) chosen from C6-C16 lower alkanes, non-silicone oils of animal, plant, mineral or synthetic origin, fatty alcohols, esters of a fatty acid and/or of a fatty alcohol, non-silicone waxes and silicones.
  • 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. As regards the C6-C16 lower alkanes, they are linear or branched, or possibly cyclic.
  • Examples that may be mentioned include hexane, undecane, dodecane, tridecane, and isoparaffins, for instance isohexadecane and isodecane.
  • oils of animal, vegetable, mineral or synthetic origin that may be used in the composition of the invention, examples that may be mentioned include: - hydrocarbon-based oils of animal origin, such as perhydrosqualene;
  • oils of plant or synthetic origin such as liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, 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, 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, jojoba oil and shea butter oil;
  • fluoro oils for instance 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 bromoperfluorooctyl sold under the name ForalkyI® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethylperfluoromorpholine 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. Mention may be made, for example, of cetyl alcohol, stearyl alcohol and a mixture thereof (cetearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2- undecylpentadecanol, oleyl alcohol or linoleyl alcohol.
  • esters By way of fatty acid and/or fatty alcohol esters, which are advantageously different from the triglycerides mentioned above, mention may be made in particular of esters of saturated or unsaturated, linear or branched C1-C26 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched C1-C26 aliphatic mono- or polyalcohols, the total carbon number of the esters being greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; C12-C15 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 isononate; isostearyl palmitate; methyl acetyl ricinoleate; myristyl stearate; o
  • esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C2-C26 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • esters mentioned above it is preferred to use ethyl, isopropyl, myristyl, cetyl or stearyl palmitates, 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 or cetyl octanoate.
  • alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stea
  • composition may also comprise, as fatty ester, sugar esters and diesters of C6- C30 fatty acids and preferably C12-C22 fatty acids.
  • sugar esters and diesters of C6- C30 fatty acids and preferably C12-C22 fatty acids.
  • sucrose is intended to mean oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and that comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may especially be chosen from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C6-C30, preferably C12-C22, fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • 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, in particular, 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 of 20% monoester and 80% diester, triester and polyester;
  • sucrose mono-dipalmito-stearate sold by the company Goldschmidt under the name Tegosoft® PSE.
  • the (non-silicone) wax(es) are chosen in particular from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, vegetable waxes, such as olive tree wax, rice wax, hydrogenated jojoba wax or absolute flower waxes, such as the blackcurrant flower essential wax sold by Bertin (France), or animal waxes, such as beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy raw materials which can be used according to the invention are in particular marine waxes, such as that sold by 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 5x10 "6 to 2.5 m 2 /s at 25°C, and preferably 1 x10 "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 containing from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes containing from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane, sold especially 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.
  • organosilicon compounds such as the mixture of octamethylcyclotetrasiloxane and tetra(trimethylsilyl)pentaerythritol (50/50) and the mixture of octamethylcyclot
  • 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;
  • CTFA dimethiconol
  • polydialkylsiloxanes In this category of polydialkylsiloxanes, mention may also be made of the products sold under the names Abil Wax® 9800 and 9801 by the company Goldschmidt, which are polydi(Ci-C2o)alkylsiloxanes.
  • 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.
  • PDMS polydimethylsiloxane
  • PPMS polyphenylmethylsiloxane
  • isoparaffins polyisobutylenes
  • methylene chloride pentane
  • dodecane and tridecane or mixtures thereof.
  • CTFA dimethiconol
  • CFA cyclic polydimethylsiloxane
  • the product SF 1236 is the 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 5x10 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 C1-C4 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.
  • examples that may be mentioned include the products sold under the following names:
  • 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
  • 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 including:
  • C6-C24 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 (Ci2)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, C1-C4 aminoalkyl groups;
  • the fatty substance(s) do not comprise any C2-C3 oxyalkylene units or any glycerolated units.
  • the fatty substances are chosen from compounds that are liquid or pasty at ambient temperature and at atmospheric pressure.
  • the fatty substance is a compound that is liquid at a temperature of 25°C and at atmospheric pressure.
  • the fatty substances are preferably chosen from C6-C16 lower alkanes, non-silicone oils of plant, mineral or synthetic origin, fatty alcohols, esters of a fatty acid and/or of a fatty alcohol, and silicones, or mixtures thereof.
  • the fatty substance is chosen from liquid petroleum jelly, polydecenes and liquid esters of a fatty acid and/or of a fatty alcohol, or mixtures thereof.
  • the composition A according to the invention more particularly has a fatty substance content ranging from 1 % to 80% by weight, even more preferentially from 5% to 75% and better still from 10% to 70% by weight, even better still from 20% to 65% relative to the weight of the composition.
  • the composition A according to the invention comprises at least 20% by weight of fatty substance, which is preferably liquid, preferably at least 25% by weight of fatty substance, which is preferably liquid, even better still at least 30% by weight of fatty substance, which is preferably liquid, more preferably at least 40% by weight of fatty substance, which is preferably liquid, relative to its total weight.
  • the cosmetic composition (B) according to the invention comprises at least one peroxygenated salt as oxidizing agent.
  • the peroxygenated salts are in particular chosen from persulfates, perborates, peracids and/or salts thereof, percarbonates, in particular of alkali or alkaline-earth metals, and mixtures thereof.
  • the peroxygenated salt(s) is (are) chosen from persulfates, preferably from sodium persulfates, potassium persulfates and ammonium persulfates, and mixtures thereof, more preferably sodium persulfate.
  • concentration of peroxygenated salt(s) may range more particularly from 0.05% to 20% by weight, even more preferentially from 0.1 % to 15% by weight and better still from 0.5% to 10% by weight relative to the composition (B).
  • composition B is preferably an aqueous composition; it can be prepared just before use by mixing the peroxygenated salt in powder form and an aqueous phase comprising water and optionally an organic solvent, as described below.
  • compositions (A) and/or (B) comprise one or more non-ionic, preferably oxyalkylenated, surfactants.
  • the surfactants are oxyalkylenated non-ionic surfactants and are chosen from oxyethylenated C8-C30 alcohols, and polyoxyethylenated esters of saturated or unsaturated, linear or branched C8-C30 acids and of sorbitol.
  • the cosmetic compositions (A) and/or (B) comprise one or more non-ionic surfactants.
  • the surfactant content in the compositions (A) and/or (B) represents more particularly from 0.1 % to 50% by weight and preferably from 0.5% to 30% by weight relative to the weight of the composition under consideration.
  • compositions (A) and/or (B) may also contain various adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, non-ionic, amphoteric or zwitterionic polymers or mixtures thereof; mineral thickeners, and in particular fillers such as clays or talc; organic thickeners/gelling agents with, in particular, anionic, cationic, non-ionic and amphoteric polymeric associative thickeners other than the polymers previously mentioned; antioxidants; penetrants; sequestrants; fragrances; dispersants; film-forming agents; ceramides; preservatives; opacifiers.
  • adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, non-ionic, amphoteric or zwitterionic polymers or mixtures thereof; mineral thickeners, and in particular fillers such as clays or talc; organic thickeners/gelling agents with, in particular, anionic, cationic, non-i
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 20% by weight relative to the weight of the composition under consideration.
  • compositions (A) and/or (B) are preferably aqueous compositions.
  • aqueous composition is intended to mean a composition comprising more than 5% by weight of water, preferably more than 10% by weight of water and even more advantageously more than 20% by weight of water.
  • the water concentration of the compositions (A) and (B) may range from 10% to 90% and better still from 20% to 80% of the total weight of the composition.
  • compositions (A) and/or (B) may optionally comprise one or more organic solvents.
  • organic solvents include linear or branched C2-C4 alkanols, such as ethanol and isopropanol; glycerol; polyols and polyol ethers, such as 2- butoxyethanol, propylene glycol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the organic solvent(s), if they are present, represent a content usually ranging from 1 % to 40% by weight and preferably ranging from 5% to 30% by weight relative to the weight of the composition containing them.
  • the composition (A) it preferably ranges from 6.5 to 12 and better still from 8 to 12.
  • the pH is adjusted using acidifying or alkaline agents.
  • the acidifying agents are chosen from organic or mineral acids, such as hydrochloric acid, phosphoric acid, lactic acid or citric acid.
  • the alkaline agents may be chosen from those described previously.
  • the pH of the composition (B) is preferably acidic, that is to say less than 7. More preferentially, the pH of the composition (B) ranges from 1 to 6, better still from 1 .5 to 5 and even better still from 2 to 4.
  • the process according to the invention comprises the application to keratin fibres:
  • composition (A) comprising at least one coupler
  • At least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts;
  • compositions (A) and (B) may be applied simultaneously or separately.
  • a) at least one composition (A) comprising at least one coupler is applied, then b) at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts is applied, it being understood that the dyeing process does not use any oxidation base and that it does not use hydrogen peroxide.
  • b) at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts is applied, then a) at least one composition (A) comprising at least one coupler is applied, it being understood that the dyeing process does not use any oxidation base and does not use hydrogen peroxide.
  • a) at least one composition (A) comprising at least one coupler and b) at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts are simultaneously applied, it being understood that the dyeing process does not use any oxidation base and does not use hydrogen peroxide.
  • the compositions (A) and (B) are extemporaneously mixed at the time of use.
  • a) at least one composition (A) comprising at least one coupler is applied, then b) at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts is applied, it being understood that the dyeing process does not use any oxidation base and does not use hydrogen peroxide.
  • the dyeing process carries out a step a') of rinsing the keratin fibres, preferably with water, between steps a) and b).
  • the dyeing process carries out the steps successively a), then a'), then b).
  • the process for the oxidation dyeing of keratin fibres comprises
  • At least one oxidizing composition (B) comprising a chemical oxidizing agent chosen from peroxygenated salts;
  • the dyeing process does not use any oxidation base and does not use hydrogen peroxide.
  • the time gap between the application of (A) and (B) may range from 5 seconds to 60 minutes, preferably from 2 minutes to 30 minutes.
  • the leave-on time of composition (A) on the keratin fibres may range from 1 to 60 minutes and is preferably from 2 to 30 minutes.
  • composition (A) is applied to the keratin fibres and is left on for 5 to 20 minutes at ambient temperature.
  • the oxidizing composition (B) may be left in place on the keratin fibres for a time generally of about from 1 to 60 minutes, preferably from 5 to 30 minutes and preferably for 20 minutes.
  • the temperature during the process conventionally ranges from ambient temperature (between 15 and 25°C) to 120°C if a straightening iron is used, preferably from ambient temperature to 40°C.
  • the composition (A) is applied to the dry or wet keratin fibres, then they are rinsed and wrung dry with a towel.
  • the composition (B) as defined previously is subsequently applied, and then said fibres are optionally washed, rinsed and/or dried.
  • the drying step may last from 5 to 20 minutes, preferably from 5 to 15 minutes, and in particular lasts 10 minutes.
  • the human keratin fibres are preferably rinsed with water, optionally washed with a shampoo and then rinsed with water, before being dried or left to dry.
  • the dyeing process according to the present invention does not use metal catalysts.
  • Metal catalysts are compounds which comprise in their structure one or more metals chosen from transition metals, rare earth metals and alloys thereof, in particular transition metals, such as manganese, iron, cobalt, copper, zinc, platinum, nickel, titanium, silver, zirconium, chromium, molybdenum, tungsten, platinum, gold or vanadium and, among these, most particularly manganese.
  • transition metals such as manganese, iron, cobalt, copper, zinc, platinum, nickel, titanium, silver, zirconium, chromium, molybdenum, tungsten, platinum, gold or vanadium and, among these, most particularly manganese.
  • the metal salts may be mineral or organic salts.
  • Device :
  • the invention relates to a multicompartment device comprising a first compartment containing a composition (A), as defined previously, and a second compartment containing a composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts, preferably as defined previously, said device not comprising any oxidation bases and does not use any hydrogen peroxide.
  • the device is suitable for implementing the dyeing process according to the present invention.
  • each lock is rinsed, washed with a standard shampoo and then left to dry at 60°C.
  • the colour of the locks was evaluated in the CIE L * a * b * system, using a Minolta CM-2600D spectrocolorimeter.
  • L * represents the intensity of the colour
  • a * indicates the green/red colour axis
  • b * the blue/yellow colour axis.
  • the use of the coupler in the absence of oxidation base in combination with a peroxygenated oxidizing agent makes it possible to obtain a colouring which is much more powerful than with a hydrogen peroxide-based oxidizing agent (P2) (L * much lower for the process according to the invention than the comparative process), without requiring the use of a metal catalyst (the colouring obtained with the process P3 is more powerful than that obtained with P1 which comprises a metal catalyst).
  • the process of the invention makes it possible to obtain a very good colouring, this being even in the absence of oxidation base, since the colouring obtained with the process P3 using a peroxygenated oxidizing agent with a coupler (without oxidation base) is more powerful than when using the coupler combined with an oxidation base (P4).
  • Example 2 The following compositions were prepared. Unless otherwise mentioned, the amounts indicated are expressed in g%.
  • each composition A4 to A10 1 part by weight of each composition A4 to A10 is applied to a lock of hair (leave-on-time 10 min), rinsing is performed, then 1 part by weight of composition B3 is applied (leave-on time 30 min), and rinsing, shampooing and drying are performed.
  • compositions were prepared. Unless otherwise mentioned, the amounts indicated are expressed in g%.
  • Process 1 1 part by weight of each composition A1 to A8 is applied to a locks of natural hair (leave-on-time 10 min), rinsing is performed, then 1 part by weight of composition B1 is applied (leave-on time 30 min), and rinsing, shampooing and drying at 60°C are performed.
  • Process 2 1 part by weight of each composition A1 to A8 is applied to a locks of natural hair (leave-on-time 10 min), rinsing is performed, then 1 part by weight of composition B2 is applied (leave-on time 30 min), and rinsing, shampooing and drying at 60°C are performed.
  • the color is measured by using a spectrocolorimeter Konica Minolta CM 3600d (D65, 10°, specular components included) in the L * a * b * system..
  • L indicates the lightness. The lowest is the value of L, the most intense is the color of the hair.
  • Process 2 provides lower L* values, thus a more intense color on hair compared to comparative process 1 , whatever the coupler used.

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Abstract

La présente invention a pour objet un procédé de teinture par oxydation des fibres kératiniques, en particulier de fibres kératiniques humaines telles que les cheveux, comprenant l'application aux fibres kératiniques : d'au moins une composition (A) comprenant au moins un coupleur et d'au moins une composition oxydante (B) comprenant au moins un agent oxydant chimique choisi parmi les sels peroxygénés ; étant entendu que le procédé de coloration n'utilise pas de base d'oxydation, et étant entendu que les compositions (A) et (B) peuvent être appliquées simultanément ou séparément.
PCT/EP2018/076127 2017-09-28 2018-09-26 Procédé de teinture par oxydation utilisant un coupleur et un sel peroxygéné en tant qu'agent oxydant WO2019063611A1 (fr)

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FR1759001A FR3071407B1 (fr) 2017-09-28 2017-09-28 Procede de coloration d’oxydation mettant en œuvre un coupleur et un sel peroxygene a titre d’agent oxydant
FR1759001 2017-09-28

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FR3124719B1 (fr) * 2021-06-30 2024-05-10 Oreal Composition comprenant au moins un coupleur particulier, au moins une base d’oxydation particulière, au moins un corps gras et au moins un polysaccharide anionique.

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JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
WO1994008969A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Procede de production de derives de 4,5-diaminopyrazole, leur utilisation pour la teinture des cheveux, et nouveaux derives de pyrazole
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WO1996015765A1 (fr) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation
FR2733749A1 (fr) 1995-05-05 1996-11-08 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
EP0770375A1 (fr) 1995-10-21 1997-05-02 GOLDWELL GmbH Composition pour la teinture des cheveux
DE19543988A1 (de) 1995-11-25 1997-05-28 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate
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GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
FR2233982A1 (fr) * 1973-06-22 1975-01-17 Oreal
DE2359399A1 (de) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Haarfaerbemittel
DE3843892A1 (de) 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
WO1994008969A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Procede de production de derives de 4,5-diaminopyrazole, leur utilisation pour la teinture des cheveux, et nouveaux derives de pyrazole
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EP0795313A2 (fr) * 1996-03-16 1997-09-17 Wella Aktiengesellschaft Agent et procédé de coloration par oxydation des fibres kératiniques
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FR2886136A1 (fr) 2005-05-31 2006-12-01 Oreal Composition pour la teinture des fibres keratiniques comprenant au moins un derive de diamino-n,n-dihydro- pyrazolone et un colorant d'oxydation cationique
JP2013169571A (ja) 2012-02-21 2013-09-02 Nippon Steel & Sumitomo Metal Corp 鍛鋼ロールの製造方法
US20160136069A1 (en) * 2013-06-21 2016-05-19 L'oreal Oxidation dyeing process using a composition rich in fatty substances which comprises metal catalysts and couplers

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