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WO2019063611A1 - Oxidation dyeing process using a coupler and a peroxygenated salt as oxidizing agent - Google Patents

Oxidation dyeing process using a coupler and a peroxygenated salt as oxidizing agent Download PDF

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Publication number
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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Prior art keywords
amino
composition
chosen
process according
weight
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French (fr)
Inventor
Mickaël AGACH
Ambre SOUVIROU
Simon DONCK
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LOreal SA
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LOreal SA
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23Sulfur; Selenium; Tellurium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31Hydrocarbons
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/411Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88Two- or multipart kits
    • A61K2800/882Mixing prior to application
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88Two- or multipart kits
    • A61K2800/884Sequential 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

The subject of the present invention 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: of at least one composition (A) comprising at least one coupler and of at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts; it being understood that the dyeing process does not use any oxidation base, and it being understood that compositions (A) and (B) may be applied simultaneously or separately.

Description

Oxidation dyeing process using a coupler and a peroxygenated salt as
oxidizing agent 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.
Many people have sought for a long time to modify the colour of their hair and in particular to mask their grey hair.
It is known practice to obtain "permanent" or oxidation dyeing with dyeing compositions containing oxidation dye precursors, which are generally known as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds. These 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.
It is also known that the shades obtained with these 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. The variety of molecules used as oxidation bases and couplers allows a wide range of colours to be obtained.
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. 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.
However, the use of hydrogen peroxide, in particular in high amounts, can cause damage to keratin fibres.
It is therefore sought to use compounds which are friendlier to keratin fibres or else to increase the efficiency of the reaction of the oxidation dyes used during this process in order to improve their build-up on keratin fibres. Indeed, such an improvement would make it possible in particular to decrease the contents of the oxidation dyes present in dyeing compositions, to reduce the leave-on time on keratin fibres and/or to use other dye families which have a weak dyeing capacity but which are capable of exhibiting a good toxicological profile, of providing new shades or of producing colourations which are resistant with respect to external agents such as light or shampoos.
In this regard, it has been proposed to dispense with the presence of oxidation bases by using only couplers, optionally boosted by metal catalysts, but processes of this type are not entirely satisfactory from a dyeing property point of view. In addition, the use of metal compounds is not always desired.
There is therefore a real need to provide a process for dyeing keratin fibres which is carried out in the presence of an oxidizing agent and which does not have the drawbacks of the existing processes, i.e. which is capable of resulting in a satisfactory intensity and chromaticity of the oxidation dyes on the keratin fibres while at the same time resulting in relatively non-selective colourations, allowing good coverage of grey hair, and which is friendly to the integrity of keratin fibres.
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:
a) of at least one composition (A) comprising at least one coupler and
b) of at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts;
characterized in that it does not use hydrogen peroxide, it being understood that the dyeing process does not use any oxidation base and it being understood that the compositions (A) and (B) can be applied simultaneously or separately.
The compositions (A) and (B) are distinct compositions.
Preferably, the dyeing process does not use a chemical oxidizing agent other than the peroxygenated salt(s). In other words, 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. Moreover, 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.
Other characteristics and advantages of the invention will emerge more clearly on reading the description and the examples that follow.
In that which follows and unless otherwise indicated, the limits of a range of values are included in this range.
The expression "at least one" is equivalent to the expression "one or more".
Composition (A) Oxidation couplers:
The composition (A) comprises one or more couplers that are conventionally used for dyeing keratin fibres.
Preferably, 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, onaphthol, 2-methyl-1 -naphthol, 6- hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 5-methoxy-6-hydroxyindole, 2- amino-3-hydroxypyridine, 6-hydroxybenzomorpholine, 2-amino-4- hydroxyethylaminoanisole, 3-amino-6-methoxy-2-methylaminopyridine, 3,5-diamino-2,6- dimethoxypyridine, 1 -N-(3-hydroxyethyl)amino-3,4-methylenedioxybenzene, 2,6-bis(3- hydroxyethylamino)toluene, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 2-chloro- 3,5-diaminopyridine, 2-chloro-3,5-diamino-6-methoxypyridine, 2-chloro-3,5-diamino-6- methylpyridine, 1 -H-3-methylpyrazol-5-one, 1 -phenyl-3-methylpyrazol-5-one, 4-(3,5- diaminopyridin-2-yl)-1 -(2-hydroxyethyl)-1 -methylpiperazin-1 -ium chloride, 2,6- dimethylpyrazolo[1 ,5-b]-1 ,2,4-triazole, 2,4,6-trimethoxyaniline hydrochlorate, 2,6- dimethyl[3,2-c]-1 ,2,4-triazole and 6-methylpyrazolo[1 ,5-a]benzimidazole, 2,6- diaminopyrazine, the addition salts thereof and/or the solvates thereof, and mixtures thereof.
Preferably, 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 -(β- 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. Even more preferentially, 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. In general, 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).
The process according to the invention does not use oxidation bases. Such bases are for example para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, and the addition salts and/or solvates thereof. Among the 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- hydroxyethyl)amino-2-chloroaniline, 2-p-hydroxyethyl-para-phenylenediamine, 2-fluoro- para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(p-hydroxypropyl)-para- phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl- para-phenylenediamine, N-ethyl-N-(p-hydroxyethyl)-para-phenylenediamine, Ν-(β,γ- dihydroxypropyl)-para-phenylenediamine, N-(4'-aminophenyl)-para-phenylenediamine, N- phenyl-para-phenylenediamine, 2-p-hydroxyethyloxy-para-phenylenediamine, 2-β- acetylaminoethyloxy-para-phenylenediamine, N-(p-methoxyethyl)-para- phenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl-para-phenylenediamine, 2-β- hydroxyethylamino-5-aminotoluene, 3-hydroxy-1-(4'-aminophenyl)pyrrolidine, and the addition salts thereof with an acid.
Among the bis(phenyl)alkylenediamines that may be mentioned, for example, are Ν,Ν'- 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-diaminophenoxy)-3,6-dioxaoctane, and the addition salts thereof.
Among the 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.
Among the 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. Among the heterocyclic bases, mention may be made of those comprising at least two nitrogen atoms, in particular pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
Among the 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.
Other 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-(3-aminopyrazolo[1 ,5-a]pyrid- 7-yl)ethanol; (3-aminopyrazolo[1 ,5-a]pyrid-2-yl)methanol; 3,6-diaminopyrazolo[1 ,5- a]pyridine; 3,4-diaminopyrazolo[1 ,5-a]pyridine; pyrazolo[1 ,5-a]pyridine-3,7-diamine; 7- (morpholin-4-yl)pyrazolo[1 ,5-a]pyrid-3-ylamine; pyrazolo[1 ,5-a]pyridine-3,5-diamine; 5- (morpholin-4-yl)pyrazolo[1 ,5-a]pyrid-3-ylamine; 2-[(3-aminopyrazolo[1 ,5-a]pyrid-5-yl)(2- hydroxyethyl)amino]ethanol; 2-[(3-aminopyrazolo[1 ,5-a]pyrid-7-yl)(2- hydroxyethyl)amino]ethanol; 3-aminopyrazolo[1 ,5-a]pyridin-5-ol; 3-aminopyrazolo[1 ,5- a]pyridin-4-ol; 3-aminopyrazolo[1 ,5-a]pyridin-6-ol; 3-aminopyrazolo[1 ,5-a]pyridin-7-ol; 2- (2-hydroxyethoxy)-3-aminopyrazolo[1 ,5-a]pyridine and 2-(4-methylpiperazinium-1 -yl)-3- aminopyrazolo[1 ,5-a]pyridine; and the addition salts thereof.
Among the 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.
Among the 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-methylpyrazole, 4,5-diamino-3-tert-butyl-1 - methylpyrazole, 4,5-diamino-1 -tert-butyl-3-methylpyrazole, 4,5-diamino-1 -(β- hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1 -ethyl-3-methylpyrazole, 4,5-diamino-1 - ethyl-3-(4'-methoxyphenyl)-pyrazole, 4,5-diamino-1 -ethyl-3-hydroxymethylpyrazole, 4,5- diamino-3-hydroxymethyl-1 -methylpyrazole, 4,5-diamino-3-hydroxymethyl-1 - isopropylpyrazole, 4,5-diamino-3-methyl-1 -isopropylpyrazole, 4-amino-5-(2'- aminoethyl)amino-1 ,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1 -methyl-3,4,5- triaminopyrazole, 3,5-diamino-1 -methyl-4-methylaminopyrazole and 3,5-diamino-4-(p- hydroxyethyl)amino-1 -methylpyrazole, and the addition salts thereof. Mention may also be made of 4,5-diamino-1 -(p-methoxyethyl)pyrazole.
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-diamino-1 ,2-dimethyl-1 ,2-dihydropyrazol-3-one, 4,5-diamino-1 ,2- diethyl-1 ,2-dihydropyrazol-3-one, 4,5-diamino-1 ,2-di(2-hydroxyethyl)-1 ,2-dihydropyrazol- 3-one, 2-amino-3-(2-hydroxyethyl)amino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-dimethylamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one, 2,3-diamino- 5,6,7,8-tetrahydro-1 H,6H-pyridazino[1 ,2-a]pyrazol-1 -one, 4-amino-1 ,2-diethyl-5- (pyrrolidin-1 -yl)-1 ,2-dihydropyrazol-3-one, 4-amino-5-(3-dimethylaminopyrrolidin-1 -yl)-1 ,2- diethyl-1 ,2-dihydropyrazol-3-one, 2,3-diamino-6-hydroxy-6,7-dihydro-1 H,5H-pyrazolo[1 ,2- a]pyrazol-1 -one.
Alkaline agents:
Preferably, 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. In addition, the organic amines do not comprise any alkyl or alkenyl fatty chain comprising more than ten carbon atoms.
The organic alkaline agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (III) below:
Figure imgf000009_0001
in which formula (III) 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 NRU, and Rx, Ry, Rz, Rt and Ru, 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.
The term "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.
Among the compounds of this type, mention may be made of monoethanolamine (MEA), 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.
More particularly, the 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.
As amino acids that may be used in the present invention, mention may be made in particular of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N- phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine. Advantageously, 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:
Figure imgf000010_0001
in which formula IV) R represents a group chosen from:
Figure imgf000010_0002
-(CH2)2NH2; -(CH2)2NHCONH2; and
-(CH2)2NH C— NH2
NH
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. As 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. As 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. Preferably, 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). Even more preferentially, the alkaline agent(s) are chosen from aqueous ammonia, sodium hydroxide and alkanolamines, most particularly monoethanolamine (MEA), and mixtures thereof. Fatty substances
According to one embodiment, the composition A of the process according to the invention comprises one or more fatty substances.
The term "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. In addition, 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.
According to the invention, the fatty substances are chosen from compounds that are liquid or pasty at ambient temperature and at atmospheric pressure.
More particularly, 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.
It is recalled that, for the purposes of the invention, 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.
As 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;
- triglyceride 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;
- linear or branched hydrocarbons of mineral or synthetic origin, containing more than 16 carbon atoms, such as volatile or non-volatile liquid paraffins, and derivatives thereof, petroleum jelly, liquid petroleum jelly, polydecenes, and hydrogenated polyisobutenes such as Parleam®; preferably liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes and hydrogenated polyisobutenes such as Parleam®;
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.
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.
Among the monoesters, mention may be made of 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; octyl isononanoate; 2- ethylhexyl isononanoate; octyl palmitate; octyl pelargonate; octyl stearate; octyldodecyl erucate; oleyl erucate; ethyl and isopropyl palmitates, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl, 2-octyldodecyl, myristyl or stearyl myristate, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2- hexyldecyl laurate.
Still within the context of this variant, 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.
Mention may be made especially of: diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; propylene glycol dicaprylate; propylene glycol dicaprate; tridecyl erucate; triisopropyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; propylene glycol dioctanoate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate; and polyethylene glycol distearates.
Among the 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.
The composition may also comprise, as fatty ester, sugar esters and diesters of C6- C30 fatty acids and preferably C12-C22 fatty acids. It is recalled that the term "sugar" 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. These sugars may be monosaccharides, oligosaccharides or polysaccharides.
Examples of suitable sugars that may be mentioned 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.
The esters according to this variant may also be chosen from mono-, di-, tri- and tetraesters, polyesters, and mixtures thereof.
These 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.
More particularly, use is made of monoesters and diesters and especially sucrose, glucose or methylglucose monooleate or dioleate, stearate, behenate, oleopalmitate, linoleate, linolenate or oleostearate.
An example that may be mentioned is the product sold under the name Glucate® DO by Amerchol, which is a methylglucose dioleate.
Examples of esters or mixtures of esters of sugar and of fatty acid that may also be mentioned include:
- the products sold under the names F160, F140, F1 10, F90, F70 and SL40 by the company Crodesta, respectively denoting 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;
- the products sold under the name Ryoto Sugar Esters, for example referenced B370 and corresponding to sucrose behenate formed of 20% monoester and 80% diester, triester and polyester;
- the 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 m2/s at 25°C, and preferably 1 x10"5 to 1 m2/s.
The silicones that may be used in accordance with the invention may be in the form of oils, waxes, resins or gums.
Preferably, 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.
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.
When they are 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:
(i) 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.
Mention may also be made of cyclocopolymers of the dimethylsiloxane/methylalkylsiloxane type, such as Volatile Silicone® FZ 3109 sold by Union Carbide, having the formula:
D" - D' D" - D'—
CH3 ' ' CH3
with D" : — Si - O— with D' : - Si - O—
CH3 C8H17
Mention may also be made of mixtures of cyclic polydialkylsiloxanes with organosilicon compounds, such as the mixture of octamethylcyclotetrasiloxane and tetra(trimethylsilyl)pentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1 ,1 '-bis(2,2,2',2',3,3'-hexatrimethylsilyloxy)neopentane; (ii) linear volatile polydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity of less than or equal to 5x 10"6 m2/s at 25°C. An example thereof is decamethyltetrasiloxane sold especially under the name SH 200 by Toray Silicone. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91 , Jan. 76, pp. 27-32, Todd & Byers, "Volatile Silicone Fluids for Cosmetics".
Non-volatile polydialkylsiloxanes, polydialkylsiloxane gums and resins, polyorganosiloxanes modified with the above organofunctional groups, and mixtures thereof, are preferably used.
These 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.
Among these polydialkylsiloxanes, mention may be made, in a non-limiting manner, of the following commercial products:
- the Silbione® oils of the 47 and 70 047 series or the Mirasil® oils sold by Rhodia, for instance the oil 70 047 V 500 000;
- the oils of the Mirasil® series sold by the company Rhodia;
- the oils of the 200 series from the company Dow Corning, such as DC200 with a viscosity of 60 000 mm2/s;
- the Viscasil® oils from General Electric and certain oils of the SF series (SF 96, SF 18) from General Electric.
Mention may also be made of polydimethylsiloxanes bearing dimethylsilanol end groups, known under the name dimethiconol (CTFA), such as the oils of the 48 series from the company Rhodia.
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. Products that may be used more particularly in accordance with the invention are mixtures such as:
- mixtures formed from a polydimethylsiloxane with a hydroxy-terminated chain, or dimethiconol (CTFA), and from a cyclic polydimethylsiloxane, also known as cyclomethicone (CTFA), such as the product Q2 1401 sold by the company Dow Corning;
- mixtures of a polydimethylsiloxane gum and a cyclic silicone, such as the product SF 1214 Silicone Fluid from the company General Electric; this product is an SF 30 gum corresponding to a dimethicone, having a number-average molecular weight of 500 000, dissolved in the oil SF 1202 Silicone Fluid corresponding to decamethylcyclopentasiloxane;
- mixtures of two PDMSs with different viscosities, and more particularly of a PDMS gum and a PDMS oil, such as the product SF 1236 from General Electric. The product SF 1236 is the mixture of a gum SE 30 defined above with a viscosity of 20 m2/s and of an oil SF 96 with a viscosity of 5x106 m2/s. This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96.
The organopolysiloxane resins that may be used in accordance with the invention are crosslinked siloxane systems containing the following units:
R2S1O2/2, R3S1O1/2, RS1O3/2 and S1O4/2,
in which R represents an alkyl containing 1 to 16 carbon atoms. Among these products, the ones that are particularly preferred are those in which R denotes a C1-C4 lower alkyl group, more particularly methyl.
Among these resins, mention may be made of the product sold under the name Dow Corning 593 or those sold under the names Silicone Fluid SS 4230 and SS 4267 by the company General Electric, which are silicones of dimethyl/trimethylsiloxane structure.
Mention may also be made of the trimethyl siloxysilicate-type resins sold especially under the names X22-4914, X21 -5034 and X21 -5037 by the company Shin-Etsu.
The 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.
Besides the silicones described above, 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 χ 10"5 to 5* 10"2 m2/s at 25°C. Among these polyalkylarylsiloxanes, examples that may be mentioned include the products sold under the following names:
. the Silbione® oils of the 70 641 series from Rhodia;
. the oils of the Rhodorsil® 70 633 and 763 series from Rhodia;
. the oil Dow Corning 556 Cosmetic Grade Fluid from Dow Corning;
. the silicones of the PK series from Bayer, such as the product PK20;
. the silicones of the PN and PH series from Bayer, such as the products PN1000 and
PH1000;
. certain oils of the SF series from General Electric, such as SF 1023, SF 1 154, SF 1250 and SF 1265.
Among the organomodified silicones, mention may be made of polyorganosiloxanes including:
- polyethyleneoxy and/or polypropyleneoxy groups optionally 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;
- alkoxylated groups such as the product sold under the name Silicone Copolymer F-755 by SWS Silicones, and Abil Wax® 2428, 2434 and 2440 by the company Goldschmidt.
Preferably, the fatty substance(s) do not comprise any C2-C3 oxyalkylene units or any glycerolated units.
More particularly, the fatty substances are chosen from compounds that are liquid or pasty at ambient temperature and at atmospheric pressure.
Preferably, 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.
Preferably, 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.
According to one embodiment, 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.
Composition B
Chemical oxidizing agents:
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.
Preferably, 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. The 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).
The 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.
Additional ingredients or adjuvants:
According to one particular embodiment, the compositions (A) and/or (B) comprise one or more non-ionic, preferably oxyalkylenated, surfactants.
In accordance with a preferred embodiment of the invention, 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.
Preferably, 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.
The 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.
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.
The compositions (A) and/or (B) are preferably aqueous compositions.
The term "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.
Even more preferentially, 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.
The compositions (A) and/or (B) may optionally comprise one or more organic solvents. Examples of organic solvents that may be mentioned 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 pH of the compositions (A) and/or (B), if they are aqueous, ranges from 2 to 13. For 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.
Dyeing processes: The process according to the invention comprises the application to keratin fibres:
a) of at least one composition (A) comprising at least one coupler and
b) of at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts;
and is characterized in that it does not use hydrogen peroxide,
it being understood that the process does not use any oxidation base and it being understood that compositions (A) and (B) may be applied simultaneously or separately.
According to one embodiment of the process of the invention, 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.
According to another embodiment of the process of the invention, 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. According to another embodiment of the process of the invention, 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. In this embodiment, the compositions (A) and (B) are extemporaneously mixed at the time of use.
In one preferred variant of the process of the invention, 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. According to one particular embodiment of the invention, the dyeing process carries out a step a') of rinsing the keratin fibres, preferably with water, between steps a) and b).
According to one particularly advantageous embodiment of the invention, the dyeing process carries out the steps successively a), then a'), then b).
More particularly, the process for the oxidation dyeing of keratin fibres comprises
a) the application to the keratin fibres of at least one composition (A) comprising at least one coupler, then
a') optionally a washing, rinsing, drying and/or wringing out step, then
b) the application of at least one oxidizing composition (B) comprising a chemical oxidizing agent chosen from peroxygenated salts;
it being understood that the dyeing process does not use any oxidation base and does not use hydrogen peroxide.
When the compositions (A) and (B) are applied separately, 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.
In particular, the 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.
According to one preferred embodiment, 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.
After the treatment, i.e. after the application of the composition (B) as previously defined, 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.
According to one preferred embodiment, 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.
The metal salts may be mineral or organic salts. Device:
Finally, 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.
The examples that follow serve to illustrate the invention without, however, being limiting in nature. EXAMPLE 1 The following compositions were prepared. Unless otherwise mentioned, the amounts indicated are expressed in g%.
Compositions A1 to A3
Figure imgf000024_0001
Oxidizing compositions B1 and B2
Composition B1 with peroxygenated salt
Sodium persulfate 1
Lactic acid qs pH 2.2
Water qs 100 Composition B2 with hydrogen peroxide
Figure imgf000025_0001
*AM = active material The following processes are carried out:
P1 : 1 part by weight of formula A1 (leave-on-time 10 min) is applied, rinsing is performed and then 1 part by weight of formula B1 is applied (leave-on time 30 min), and rinsing, shampooing and drying are performed [invention]
P2: 1 part by weight of formula A1 (leave-on-time 10 min) is applied, rinsing is performed and then 1 part by weight of formula B2 is applied (leave-on time 30 min), and rinsing, shampooing and drying are performed [comparative]
P3: 1 part by weight of formula A2 (leave-on-time 10 min) is applied, rinsing is performed and then 1 part by weight of formula B1 is applied (leave-on time 30 min), and rinsing, shampooing and drying are performed [invention]
- P4: 1 part by weight of formula A3 (leave-on-time 10 min) is applied, rinsing is performed and then 1 part by weight of formula B1 is applied is applied (leave-on time 30 min), and rinsing, shampooing and drying are performed [comparative] Each of the processes is carried out on locks of hair containing 90% natural grey (NG) hair in a proportion of 10 g of composition per 1 g of hair.
After the final leave-on time, 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.
In this L*a*b* system, L* represents the intensity of the colour, a* indicates the green/red colour axis and b* the blue/yellow colour axis.
The lower the value of L*, the darker or more intense the colour.
Results:
Figure imgf000026_0001
As shown in the table above, the use of the coupler in the absence of oxidation base in combination with a peroxygenated oxidizing agent (process P1 or P3) 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).
Moreover, 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%.
Figure imgf000027_0001
100 100 100 100 100
Oxidizing composition B3
Figure imgf000028_0001
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.
For each mixture, an intense chromatic colour is obtained, with good integrity of the hair.
Example 3
The following compositions were prepared. Unless otherwise mentioned, the amounts indicated are expressed in g%.
A1 A2 A3 A4 A5 A6 AT A8
6- HYDROXY 10
- - - - - - BENZOMORPHOLINE mmol
M ET H YL-2- H YD ROXY-4- B ETA-
10
HYDROXYETHYLAMINO- - - - - - - mmol
BENZENE
10
2-AMINO-3-HYDROXYPYRIDINE - - - - - - mmol
10
5-AMINO-6-CHLORO-0-CRESOL - - - - - - mmol
SULFATE DE 2-AMINO-4- 10
- - - - - - HIDROXYETHYLAMINOANISOLE mmol 3-AM 1 N 0-6-M ETH OXY-2-
10
METHYLAMINO PYRIDINE - - - - - - mmol
DIHYDROCHLORIDE - A130
4-hydroxyindole - - - - - - 10 mmol -
2,4-DIAMINOPHENOXYETHANOL 10
- - - - - - HCI mmol
Alkyl (C8/C10/C12/C14
34/24/29/10) polyglucoside (1 ,4) as
2 am 2 am 2 am 2 am 2 am 2 am 2 am 2 am an aqueous solution at 53%, nonprotected (pH 1 1 .5 using NaOH)
Ceteth-2 1 1 1 1 1 1 1 1
0.075 0.075 0.075 0.075 0.075 0.075 0.075 0.075
Hexadimethrine chloride
am am am am am am am am
0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1
Poyquaterinum-6
am am am am am am am am
SMD l/polyethylene glycol polymer
bearing decyl end groups, as a 1 am 1 am 1 am 1 am 1 am 1 am 1 am 1 am water-glycol solution
Polyquaternium-67 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2
Liquid petroleum jelly 63.5 63.5 63.5 63.5 63.5 63.5 63.5 63.5
Sodium metabisulfite 0.22 0.22 0.22 0.22 0.22 0.22 0.22 0.22
Sodium hydroxide Qs
Qs Qs Qs Qs Qs Qs pH Qs pH
pH 10 pH 10 pH 10 pH 10 pH 10 10 pH 10 10
Water Qs Qs Qs Qs Qs Qs Qs 100 Qs
100 100 100 100 100 100 100 Oxidizing composition
Figure imgf000030_0001
Protocole
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.
Coloration data
The color is measured by using a spectrocolorimeter Konica Minolta CM 3600d (D65, 10°, specular components included) in the L*a*b* system..
According to this system, L indicates the lightness. The lowest is the value of L, the most intense is the color of the hair.
L*
Process 1 Process 2
(comparative) (invention)
Ai 62,61 39,23
A2 68,31 55,58
A3 65,95 62,18
A4 64,54 59,48
Figure imgf000031_0001
Process 2 according to the invention provides lower L* values, thus a more intense color on hair compared to comparative process 1 , whatever the coupler used.

Claims

1 . Process for the oxidation dyeing of keratin fibres, in particular human keratin fibres such as the hair, comprising the application to the keratin fibres:
a) of at least one composition (A) comprising at least one coupler and b) of at least one oxidizing composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts,
characterized in that it does not use hydrogen peroxide,
it being understood that the dyeing process does not use any oxidation base, it being understood that compositions (A) and (B) may be applied simultaneously or separately.
2. Process according to either one of the preceding claims, characterized in that the peroxygenated salt(s) is (are) the only chemical oxidizing agent(s) used in said process.
3. Process according to any one of the preceding claims, in which the coupler is 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.
4. Process according to any one of the preceding claims, in which the coupler is chosen from 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, a-naphthol, 2-methyl-1 -naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 5-methoxy-6- hydroxyindole, 2-amino-3-hydroxypyridine, 6-hydroxybenzomorpholine, 2-amino-4- hydroxyethylaminoanisole, 3-amino-6-methoxy-2-methylaminopyridine, 3,5-diamino-2,6- dimethoxypyridine, 1 -N-(3-hydroxyethyl)amino-3,4-methylenedioxybenzene, 2,6-bis(3- hydroxyethylamino)toluene, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 2- chloro-3,5-diaminopyridine, 2-chloro-3,5-diamino-6-methoxypyridine, 2-chloro-3,5- diamino-6-methylpyridine, 1 -H-3-methylpyrazol-5-one, 1 -phenyl-3-methylpyrazol-5-one, 4-(3,5-diaminopyridin-2-yl)-1 -(2-hydroxyethyl)-1 -methylpiperazin-1 -ium chloride, 2,6- dimethylpyrazolo[1 ,5-b]-1 ,2,4-triazole, 2,4,6-trimethoxyaniline hydrochlorate, 2,6- dimethyl[3,2-c]-1 ,2,4-triazole, 6-methylpyrazolo[1 ,5-a]benzimidazole, 2,6- diaminopyrazine, the addition salts thereof and/or the solvates thereof, and mixtures thereof, preferably 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-(3-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, better still from 3-amino-6-methoxy-2- methylaminopyridine, 6-hydroxybenzomorpholine, 2,4-diamino-1 -(β- 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.
5. Process according to one of the preceding claims, characterized in that the content of coupler(s) ranges from 0.001 % to 10% by weight, preferably from 0.005% to 5% by weight, relative to the total weight of the composition (A).
6. Process according to one of the preceding claims, characterized in that the composition (A) comprises at least one fatty substance, preferably chosen from compounds that are liquid at a temperature of 25°C and at atmospheric pressure, or oil(s).
7. Process according to any one of the preceding claims, characterized in that the fatty substances are chosen from C6-C16 hydrocarbons, hydrocarbons comprising more than 16 carbon atoms, non-silicone oils of animal origin, triglycerides of plant or synthetic origin, fatty alcohols, and fatty acid and/or fatty alcohol esters, or mixtures thereof.
8. Process according to any one of the preceding claims, in which the fatty substance is chosen from linear or branched hydrocarbons, of mineral or synthetic origin, containing more than 16 carbon atoms, preferably liquid petroleum jelly.
9. Process according to any one of the preceding claims, in which the composition A 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.
1 0. Process according to any one of the preceding claims, in which the composition (A) comprises one or more organic or mineral alkaline agents, preferably chosen from aqueous ammonia, sodium hydroxide, alkanolamines, and mixtures thereof.
1 1 . Process according to any one of the preceding claims, characterized in that the peroxygenated salt(s) are chosen from persulfates, perborates, peracids and/or salts thereof, percarbonates, in particular of alkali or alkaline-earth metals, and mixtures thereof.
12. Process according to any one of the preceding claims, characterized in that the peroxygenated salt(s) are chosen from persulfates and salts thereof, preferably from sodium persulfate, potassium persulfate, ammonium persulfate, and mixtures thereof, more preferably sodium persulfate.
13. Process according to any one of the preceding claims, characterized in that the concentration of peroxygenated salt(s) ranges from 0.05% to 20% by weight, and more preferentially from 0.1 % to 15% by weight, better still from 0.5% to 10% by weight relative to the composition (B).
14. Process according to any one of the preceding claims, characterized in that 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, characterized in that it does not use any hydrogen peroxide, it being understood that the dyeing process does not use any oxidation base.
15. Process according to any one of the preceding claims, characterized in that it comprises a step a') of rinsing the keratin fibres, preferably with water, between steps a) and b).
16. Process according to the preceding claim, characterized in that it carries out the successive steps a), then a') and then b).
17. Multicompartment device comprising a first compartment containing a composition (A), as defined in any one of Claims 1 to 16, and a second compartment containing a composition (B) comprising at least one chemical oxidizing agent chosen from peroxygenated salts, preferably as defined in any one of Claims 1 to 16, characterized in that it does not use any hydrogen peroxide, said composition not comprising any oxidation bases.
PCT/EP2018/076127 2017-09-28 2018-09-26 Oxidation dyeing process using a coupler and a peroxygenated salt as oxidizing agent Ceased WO2019063611A1 (en)

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