WO2017108696A1 - Utilisation de composés polyamine particuliers en présence d'agents oxydants pour le traitement de fibres kératiniques - Google Patents

Utilisation de composés polyamine particuliers en présence d'agents oxydants pour le traitement de fibres kératiniques Download PDF

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WO2017108696A1
WO2017108696A1 PCT/EP2016/081754 EP2016081754W WO2017108696A1 WO 2017108696 A1 WO2017108696 A1 WO 2017108696A1 EP 2016081754 W EP2016081754 W EP 2016081754W WO 2017108696 A1 WO2017108696 A1 WO 2017108696A1
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process according
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PCT/EP2016/081754
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Stéphane SABELLE
Leila Hercouet
Alain Lagrange
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L'oreal
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients

Definitions

  • the invention relates to the use of particular polyamine compounds bearing an interrupted aliphatic chain in the presence of chemical oxidizing agents for treating keratin fibres, in particular as a replacement for aqueous ammonia and/or monoethanolamine (MEA), to a process for treating keratin fibres using said particular polyamine compounds in the presence of chemical oxidizing agents, and to a multi-compartment device comprising same.
  • chemical oxidizing agents for treating keratin fibres
  • MEA monoethanolamine
  • oxidation dyeing or permanent dyeing. More particularly, this dyeing method uses one or more oxidation dyes, usually one or more oxidation bases optionally combined with one or more couplers.
  • oxidation bases are chosen from ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds. These oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, afford access to coloured species.
  • direct dyes which are coloured and colouring molecules that have affinity for fibres.
  • the direct dyes generally used are chosen from nitrobenzene, anthraquinone, nitropyridine, azo, methine, azomethine, xanthene, acridine, azine and triarylmethane direct dyes. The presence of such compounds enables the colouring obtained to be further enriched with glints or enables the chromaticity of the colouring obtained to be increased.
  • Oxidation dyeing must moreover satisfy a certain number of requirements. Thus, it must be free of toxicological drawbacks, it must enable shades to be obtained in the desired intensity and it must show a good wear property in the face of external attacking factors such as light, bad weather, washing, permanent waving, perspiration and rubbing.
  • the dyes must also be able to cover white hair and, finally, they must be as unselective as possible, i.e. they must produce the smallest possible colour differences along the same keratin fibre, which generally comprises areas that are differently sensitized (i.e. damaged) from its end to its root.
  • compositions obtained must also have good mixing and application properties, and in particular good rheological properties so as not to run down the face, onto the scalp or beyond the areas that it is proposed to dye, when they are applied.
  • aqueous compositions comprising at least one oxidizing agent, under alkaline pH conditions in the vast majority of cases.
  • This oxidizing agent is to degrade the melanin of the hair, which, depending on the nature of the oxidizing agent present, leads to varying degrees of lightening of the fibres.
  • aqueous ammonia As alkaline agent. This agent has the drawback of having a very strong odour. It has occasionally been replaced with monoethanolamine (MEA), which has a much fainter odour but does not always have the same performance qualities, especially in terms of bleaching and dyeing, as aqueous ammonia.
  • MEA monoethanolamine
  • one aim is to find a replacement for aqueous ammonia and/or MEA that has a good level of performance in terms of bleaching or dyeing, while at the same time maintaining the integrity of the fibre or even improving the cosmeticity of the fibre relative to aqueous ammonia or MEA.
  • R 1 , R 2 , R 3 and R 4 which may be identical or different, represent: a) a hydrogen atom or b) a (CrC 6 )alkyl group optionally substituted with one or more groups chosen from i) hydroxyl, ii) (di)(Ci-C 6 )(alkyl)amino, iii) (CrC 6 )alkoxy, iv) carboxyl -C(0)OH, v) heterocycle, and vi) sulfonate -S0 3 H;
  • L represents a linear or branched, saturated or unsaturated, preferably saturated, divalent hydrocarbon-based chain which comprises from 2 to 12 carbon atoms, said chain being interrupted and/or terminated with a) one or more non-contiguous heteroatoms chosen from oxygen, sulfur, N(R 5 ) and C(X), and also b) combinations between the group C(X) and said heteroatoms such as -N(R 5 )-C(X)-, -C(X)-N(R 5 )- , -N(R 5 )-C(X)-N(R 5 )-, -O-C(X)- and -C(X)-0-, said chain being optionally substituted with one or more groups chosen from i) hydroxyl, ii) (di)(Ci-C 6 )(alkyl)amino, iii) (Cr C 6 )alkoxy, iv) carboxyl, v) heterocycle and vi) sulfon
  • X represents an oxygen or sulfur atom or a group N(R 6 ) with R 6 denoting a hydrogen atom or a (CrC 6 )alkyl group; in particular, X represents an oxygen or sulfur atom, preferably an oxygen atom;
  • Another subject of the invention is the use of ingredients i) and ii) as defined previously, for the dyeing and/or lightening of keratin fibres.
  • Another subject of the invention is a multi-compartment kit or device comprising ingredients i) and ii) as defined previously.
  • the compounds of formula (I) according to the invention combined with the ingredient(s) ii) make it possible to obtain a good level of performance especially in terms of lightening of keratin fibres, while at the same time maintaining integrity of the keratin fibres that is comparable to or even greater than that obtained with aqueous ammonia or MEA.
  • no unpleasant odour associated with the compounds of formula (I) in the presence of oxidizing agent is observed.
  • alkyr radicals are saturated, linear or branched, Ci-C 6 hydrocarbon-based radicals, preferably Ci-C 4 alkyl radicals, such as methyl, ethyl, propyl or butyl;
  • alkoxy radicals are alkyl-oxy radicals with alkyl as defined previously, preferably C C 4 alkyl, such as methoxy, ethoxy, propoxy and butoxy;
  • hydrocarbon-based chain means a chain formed from carbon and hydrogen atoms, which may be saturated or unsaturated, and linear or branched, and which comprises from 1 to 12 carbon atoms, particularly from 2 to 10 carbon atoms; more particularly, it is (C 2 -C 8 )alkylene or (C 2 -C 8 )alkenylene; preferentially, the hydrocarbon- based chain is saturated and linear;
  • alkenylene means a divalent, linear or branched hydrocarbon-based chain, comprising from 1 to 3 conjugated or non-conjugated double bonds
  • heterocycle means a radical comprising, in at least one ring, one or more heteroatoms chosen in particular from O, N and S, preferably O or N, optionally substituted especially with one or more alkyl, alkoxy, carboxyl, hydroxyl, amine or ketone groups. These rings may contain one or more oxo groups on the carbon atoms of the heterocycle; among the heterocyclic radicals that may be used, mention may be made especially of furyl, morpholino, piperazino, piperidino, pyranyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl and thienyl groups;
  • the keratin fibres treated via the process according to the invention are in particular human and preferably the hair.
  • the polyamine compound(s) of formula (I) of the invention are such that L represents a (C 2 -Ci 2 )alkylene (preferentially (C 2 -C 8 )alkylene) chain, interrupted and/or terminated with from 1 to 3 groups chosen from -N(R 5 )-C(X)- and -C(X)-N(R 5 )- with R 5 and X as defined previously; preferably, X represents an oxygen atom and R5 represents a hydrogen atom or a (CrC 4 )alkyl group.
  • L represents a (C 2 -Ci 2 )alkylene (preferentially (C 2 -C 8 )alkylene) chain, interrupted and/or terminated with from 1 to 3 groups chosen from -N(R 5 )-C(X)- and -C(X)-N(R 5 )- with R 5 and X as defined previously; preferably, X represents an oxygen atom and R5 represents a hydrogen atom or
  • the compounds of formula (I) are such that R 1 , R 2 , R 3 and R 4 , which may be identical or different, represent: a) a hydrogen atom or b) a (CrC 6 )alkyl group; preferably, R 1 , R 2 , R 3 and R 4 represent a hydrogen atom.
  • one or more the polyamine compounds of the invention are chosen from 2-(2-Aminoethoxy)ethylamine1.
  • content of polyamine according to invention is lower than 0.5 * 10 "2 % by weight, relative to the total weight of the composition which contains the polyamines with oxidizing agent (after mixture). More particularly range from 0.5 * 10 "4 % et 4.5 * 10 "3 % by weight relative to the total weight of the composition used in the invention, such as 4.1 * 10 "3 % by weight relative to the total weight of the composition which contains the polyamines with oxidizing agent. / ) Chemical oxidizing agent:
  • chemical oxidizing agent means an oxidizing agent other than atmospheric oxygen.
  • alkali metal or quaternary ammonium persalts such as perborates, persulfates, percarbonates, peroxodiphosphates or Oxone®;
  • the oxidizing agent is chosen in particular from sodium perborate, sodium persulfate, potassium persulfate, ammonium persulfate, sodium percarbonate and potassium percarbonate;
  • Ci-C 6 and aromatic C 6 -C 2 o organic peracids a3) aliphatic Ci-C 6 and aromatic C 6 -C 2 o organic peracids, and the percarboxylate forms thereof, such as performic acid, peracetic acid, perbenzoic acid derivatives, trifluoroacetic acid, peroxyphthalic acid, peroxymaleic acid, peroxypropionic acid; the oxidizing agent is particularly peracetic acid;
  • organic peroxides such as dioxirane, Ci-C 6 alkyl peroxides, benzoyl peroxide, peroxo(CrC 6 )alkyl carboxylates, bis(tri)(CrC 6 )alkylsilyl peroxides such as bis(trimethylsilyl) peroxide, Ci-C 6 alkyl peroxydicarbonates, and sodium nonanoyloxybenzene sulfonate as described in patents WO 1995/000625 and US 4 412 934;
  • organic peroxides such as dioxirane, Ci-C 6 alkyl peroxides, benzoyl peroxide, peroxo(CrC 6 )alkyl carboxylates, bis(tri)(CrC 6 )alkylsilyl peroxides such as bis(trimethylsilyl) peroxide, Ci-C 6 alkyl peroxydicarbonates, and sodium nonanoyloxybenzene sulfonate
  • the oxidizing agent is particularly chosen from the 2,2,6,6- tetramethylpiperidyloxy radical;
  • the oxidizing agent is chosen from iodotriacetate, iodosobenzene, iodobenzenetriacetate, iodoperbenzoic acid and Dess-Martin periodinane; a8) the following organic compounds: N-halosuccinimides, trichloroisocyanuric acid, N- hydroxyphthalimide, alkyl nitrites.
  • the optional supports for these oxidizing agents a1 ) to a8) may be chosen from silica, alumina, charcoal and charged or neutral polymers;
  • a9-2) polymeric complexes that can release hydrogen peroxide such as polyvinylpyrrolidone/H 2 02 in particular in the form of powders, and the other polymeric complexes described in US 5 008 093; US 3 376 1 10; US 5 183 901 ; a9-3) oxidases which produce hydrogen peroxide in the presence of a suitable substrate (for example glucose in the case of glucose oxidase or uric acid with uricase);
  • a suitable substrate for example glucose in the case of glucose oxidase or uric acid with uricase
  • the chemical oxidizing agent(s) are chosen from a9) hydrogen peroxide or hydrogen peroxide-generating systems, more particularly H 2 0 2 .
  • composition comprising the chemical oxidizing agent(s), in particular a) the hydrogen peroxide or the hydrogen peroxide generator(s), may also include various adjuvants conventionally used in hair dyeing compositions and as defined hereinbelow at the point entitled "cosmetic composition".
  • the chemical oxidizing agent(s), in particular the hydrogen peroxide or the hydrogen peroxide-generating system(s) used preferably represent from 0.1 % to 50% by weight, preferably from 0.5% to 20% by weight, and even more preferentially from 1 % to 15% by weight, relative to the weight of the composition expressed as hydrogen peroxide, relative to the total weight of the composition containing them.
  • one or more persalts are used, preferably chosen from alkali metal or alkaline-earth metal persulfates, perborates and percarbonates.
  • the persalts are chosen from persulfate(s) such as sodium persulfate, potassium persulfate or ammonium persulfate, and mixtures thereof.
  • the persalt content may range from 0.01 % to 20% by weight, preferably from 0.1 % to 5% by weight, relative to the total weight of the composition used in the invention. / ' //) Fatty substances
  • fatty substance means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1 % and even more preferentially less than 0.1 %). They bear in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups.
  • the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, ethanol, benzene, liquid petroleum jelly or decamethylcyclopentasiloxane.
  • o/T means a "fatty substance” that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg or 1 .013x10 5 Pa).
  • non-silicone o/T means an oil not containing any silicon (Si) atoms and the term "silicone o/T means an oil containing at least one silicon atom.
  • the fatty substances are chosen from C 6 -Ci 6 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils of animal origin, triglycerides of plant or synthetic origin, fluoro oils, fatty alcohols, non-salified fatty acids, esters of fatty acid and/or of fatty alcohol other than triglycerides, non-silicone waxes other than solid fatty alcohols and than solid synthetic esters, and silicones, and mixtures thereof.
  • the linear or branched hydrocarbons of mineral or synthetic origin containing more than 16 carbon atoms are preferably chosen from liquid paraffins, liquid petroleum jelly, polydecenes and hydrogenated polyisobutene such as Parleam®, and mixtures thereof.
  • a hydrocarbon-based oil of animal origin that may be mentioned is perhydrosqualene.
  • the triglycerides of plant or synthetic origin are preferably chosen from liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, more particularly from those present in plant oils, for instance sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, jojoba oil, shea butter oil or synthetic caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel, and mixtures thereof.
  • the fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols comprising from 8 to 30 carbon atoms.
  • Examples that may be mentioned include cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2- undecylpentadecanol, oleyl alcohol, linolenyl alcohol, ricinoleyl alcohol, undecylenyl alcohol and linoleyl alcohol, and mixtures thereof.
  • the fatty acids that may be used in the context of the invention are more particularly chosen from saturated or unsaturated carboxylic acids containing from 6 to 30 carbon atoms and in particular from 9 to 30 carbon atoms. They are advantageously chosen from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid. These fatty acids are, in the composition of the invention, not salified with organic or mineral bases, so as not to give rise to soaps.
  • esters of fatty acids and/or of fatty alcohols other than the triglycerides mentioned above and plant waxes mention may be made in particular of esters of saturated or unsaturated, linear Ci-C 2 6 or branched C 3 -C 2 6 aliphatic monoacids or polyacids and of saturated or unsaturated, linear Ci-C 2 6 or branched C 3 -C 2 6 aliphatic monoalcohols or polyalcohols, the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; Ci 2 -Ci 5 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methylacetyl ricinoleate; myristyl stearate
  • esters of C 4 -C 22 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C 2 -C 2 6 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • esters mentioned above it is preferred to use ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate and cetyl octanoate, and mixtures thereof.
  • alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobuty
  • composition may also comprise, as fatty ester, sugar esters and diesters of C 6 -C 3 o and preferably C12-C22 fatty acids.
  • sugar esters and diesters of C 6 -C 3 o and preferably C12-C22 fatty acids.
  • sugar esters means oxygen-bearing hydrocarbon-based compounds bearing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • the sugar esters of fatty acids may be chosen in particular from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 3 o and preferably 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 or mixtures of esters of sugar and of fatty acid that may also be mentioned include:
  • sucrose palmitostearates formed from 73% monoester and 27% diester and triester, from 61 % monoester and 39% diester, triester and tetraester, from 52% monoester and 48% diester, triester and tetraester, from 45% monoester and 55% diester, triester and tetraester, from 39% monoester and 61 % diester, triester and tetraester, and sucrose monolaurate;
  • Ryoto Sugar Esters for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% di-triester- polyester;
  • sucrose mono-dipalmito-stearate sold by the company Goldschmidt under the name Tegosoft® PSE.
  • the silicones that may be used in the cosmetic compositions of the present invention are volatile or non-volatile, cyclic, linear or branched silicones, which are unmodified or modified with organic groups, having a viscosity of 5x 10 "6 to 2.5 m 2 /s at 25°C, and preferably 1 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 comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone ® 7207 by Union Carbide or Silbione ® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone ® 7158 by Union Carbide, and Silbione ® 70045 V5 by Rhodia, and mixtures thereof.
  • Non-volatile polydialkylsiloxanes are preferably used.
  • the composition of the process according to the invention comprises iv) at least one surfactant, which is preferably nonionic.
  • the nonionic surfactants according to the invention are preferably chosen from fatty alcohols, a-diols and alkylphenols, these three types of compound being polyethoxylated, polypropoxylated and/or polyglycerolated and containing a fatty chain comprising, for example, 8 to 22 carbon atoms, the number of ethylene oxide or propylene oxide groups possibly ranging especially from 2 to 50 and the number of glycerol groups possibly ranging especially from 2 to 30.
  • ⁇ Ri represents a linear or branched alkyl and/or alkenyl radical comprising from about
  • R 2 represents an alkylene radical comprising from about 2 to 4 carbon atoms
  • G represents a sugar unit comprising from 5 to 6 carbon atoms
  • Alkylpolyglycosides that are preferred according to the present invention are compounds of formula (II) in which Ri denotes more particularly a linear or branched, saturated or unsaturated alkyl radical comprising from 8 to 18 carbon atoms, t denotes a value ranging from 0 to 3 even more particularly equal to 0, and G can denote glucose, fructose or galactose, preferably glucose.
  • the degree of polymerization i.e. the value of v in formula (II), may range from 1 to 15 and preferably from 1 to 4.
  • the average degree of polymerization is more particularly between 1 and 2 and even more preferentially from 1.1 to 1 .5.
  • Compounds of formula (II) are especially represented by the products sold by the company Cognis under the names Plantaren® (600 CS/U, 1200 and 2000) or Plantacare® (818, 1200 and 2000). It is also possible to use the products sold by the company SEPPIC under the names Triton CG 1 10 or Oramix CG 1 10 and Triton CG 312 or Oramix® NS 10, the products sold by the company BASF under the name Lutensol GD 70 or those sold by the company Chem Y under the name AG10 LK.
  • the mono- or polyglycerolated surfactants preferably comprise on average from 1 to 30 glycerol groups, more particularly from 1 to 10 and in particular from 1 .5 to 5 glycerol groups.
  • the monoglycerolated or polyglycerolated surfactants are preferably chosen from the compounds of the following formulae:
  • Use may be made, for example, of the polyglycerolated (3.5 mol) hydroxylauryl ether sold under the name Chimexane® NF from Chimex.
  • - R a representing a linear or branched Ci-C 40 alkyl or linear or branched C 2 -C 3 o alkenyl (preferentially C 8 -C 3 o alkyl) group and - n representing an integer between 1 and 200 inclusive, preferentially between 2 and 50 and more particularly between 2 and 30 inclusive, such as 20.
  • nonionic surfactants use is preferably made of C 6 -C 2 4 alkyl polyglucosides and (poly)ethoxylated fatty alcohols, and C 8 -Ci 6 alkyl polyglucosides are more particularly used.
  • the amount of nonionic surfactants preferably ranges from 0.5% to 25% by weight, in particular from 1 % to 20% by weight and more particularly from 2% to 10% by weight relative to the total weight of the composition of the invention.
  • the surfactant(s) iii) are chosen from oxyethylenated nonionic surfactants in particular comprising a number of EO units ranging from 1 to 9; they are preferentially chosen from the following categories:
  • esters of saturated or unsaturated, linear or branched, C 8 -C 3 o acids and of polyethylene glycols are examples of esters of saturated or unsaturated, linear or branched, C 8 -C 3 o acids and of polyethylene glycols,
  • oxyethylenated nonionic surfactant comprising from 1 to 9 EO units
  • CTFA name: laureth-2 the products of addition of ethylene oxide and decyl alcohol
  • decyl alcohol 3 EO CTFA name: deceth-3
  • decyl alcohol 5 EO CFA name: deceth-5
  • Emulgin 05 (Cognis) [oleocetyl alcohol 5 EO].
  • the content of oxyethylenated nonionic surfactant(s) comprising from 1 to 9 EO units in the composition according to the invention may range from 0.1 % to 10% by weight, preferably from 0.2% to 5% by weight and better still from 0.25% to 1 % by weight relative to the total weight of the composition.
  • oxyethylenated nonionic surfactants comprising at least 10 EO units
  • the content of oxyethylenated nonionic surfactants comprising at least 10 oxyalkylene groups in the composition according to the invention may range from 0.1 % to 20% by weight, preferably from 0.5% to 15% by weight and better still from 1 % to 10% by weight relative to the total weight of the composition.
  • the total amount of oxyethylenated nonionic surfactants in the composition is preferably less than or equal to 10% by weight relative to the total weight of the composition. It may range from 0.1 % to 10% by weight, preferably from 1 % to 7% by weight and even better still from 2% to 6% by weight. v) additional basifying agents
  • the process according to the invention may also use one or more basifying agents other than the polyamine compounds of formula (I) as defined previously.
  • the basifying agent may be mineral or organic or hybrid.
  • the mineral basifying agent(s) are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, sodium hydroxide and potassium hydroxide, and mixtures thereof.
  • the organic basifying agent(s) are preferably chosen from organic amines with a pKb at 25°C of less than 12, preferably less than 10 and even more advantageously less than 6. It should be noted that it is the pKb corresponding to the function of highest basicity.
  • the additional alkaline agent(s) are chosen from i) (bi)carbonates, ii) aqueous ammonia, iii) alkanolamines such as monoethanolamine, diethanolamine, triethanolamine and derivatives thereof, iv) optionally oxyalkylenated fatty amines, v) mineral or organic hydroxides, vi) alkali metal silicates such as sodium metasilicates, vii) amino acids, preferably basic amino acids such as arginine, lysine, ornithine, citrulline and histidine, and viii) the compounds of formula (III) other than the polyamine compounds of formula (I), below:
  • W is a divalent (CrC 8 )alkylene radical optionally substituted with at least one hydroxyl group or at least one (CrC 4 )alkyl radical and/or optionally interrupted with at least one heteroatom, such as oxygen or sulfur, or with an -N(R e )- group;
  • R a , Rb, R c , Rd and R e which may be identical or different, represent a hydrogen atom or a (CrC 4 )alkyl or hydroxy(Ci-C 4 )alkyl radical; preferably, W represents a propylene radical.
  • the process according to the invention may optionally comprise one or more dyes chosen from a) oxidation dyes and b) direct dyes, or mixtures of a) and b) that will be detailed hereinbelow.
  • the composition comprises one or more dyes and preferably a) at least one oxidation dye.
  • the oxidation dyes are generally chosen from one or more oxidation bases optionally combined with one or more couplers.
  • para-phenylenediamines that may be mentioned are, for example, para- phenylenediamine, para-toluenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl- para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para- phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para- phenylenediamine, ⁇ , ⁇ -diethyl-para-phenylenediamine, N,N-dipropyl-para- phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(p-hydroxyethyl)-para- phenylenediamine, 4-N,N-bis(p-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(3-
  • para-phenylenediamine para- toluenediamine, 2-isopropyl-para-phenylenediamine, 2-p-hydroxyethyl-para- phenylenediamine, 2-p-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para- phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis(p-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine and 2- ⁇ - acetylaminoethyloxy-para-phenylenediamine, and the corresponding addition salts with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines that may be mentioned, for example, are ⁇ , ⁇ '- bis(p-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1 ,3-diaminopropanol, N,N'-bis(p-hydroxyethyl)- N,N'-bis(4'-aminophenyl)ethylenediamine, N,N'-bis(4-aminophenyl)tetramethylenediamine, N,N'-bis(p-hydroxyethyl)-N,N'-bis(4-aminophenyl)tetramethylenediamine, N,N'-bis(4- methylaminophenyl)tetramethylenediamine, N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'- methylphenyl)ethylenediamine and 1 ,8-bis(2,5-dia
  • para-aminophenols that are mentioned are, for example, para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3- hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2- methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(p-hydroxyethyl- aminomethyl)phenol and 4-amino-2-fluorophenol, and the corresponding addition salts with an acid.
  • para-aminophenol 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3- hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2- methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(p-hydroxyeth
  • ortho-aminophenols that may be mentioned, for example, are 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the corresponding addition salts.
  • heterocyclic bases for example, are pyridine, pyrimidine and pyrazole derivatives.
  • pyridine derivatives that may be mentioned are the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, for example 2,5-diaminopyridine, 2-(4- methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the corresponding addition salts.
  • pyridine oxidation bases that are useful in the present invention are the 3- aminopyrazolo[1 ,5-a]pyridine oxidation bases or the corresponding addition salts described, for example, in patent application FR 2 801 308.
  • Examples that may be mentioned include pyrazolo[1 ,5-a]pyrid-3-ylamine, 2-acetylaminopyrazolo[1 ,5-a]pyrid-3-ylamine, 2-(morpholin-4- yl)pyrazolo[1 ,5-a]pyrid-3-ylamine, 3-aminopyrazolo[1 ,5-a]pyridine-2-carboxylic acid, 2- methoxypyrazolo[1 ,5-a]pyrid-3-ylamine, (3-aminopyrazolo[1 ,5-a]pyrid-7-yl)methanol, 2-(3- aminopyrazolo[1 ,5-a]pyrid-5-yl)ethanol, 2-
  • the oxidation bases that are useful in the present invention are chosen from 3-aminopyrazolo[1 ,5-a]pyridines and are preferably substituted on carbon atom 2 with: a) a (di)(Ci-C 6 )(alkyl)amino group, said alkyl group possibly being substituted with at least one hydroxyl, amino or imidazolium group;
  • an optionally cationic 5- to 7-membered heterocycloalkyl group comprising from 1 to 3 heteroatoms, optionally substituted with one or more (CrC 6 )alkyl groups such as a di(Cr C 4 )alkylpiperazinium group; or
  • pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, for instance 4,5-diamino-1 -methylpyrazole, 4,5- diamino-1 -(p-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1 -(4 - chlorobenzyl)pyrazole, 4,5-diamino-1 ,3-dimethylpyrazole, 4,5-diamino-3-methyl-1 - phenylpyrazole, 4,5-diamino-1 -methyl-3-phenylpyrazole, 4-amino-1 ,3-dimethyl-5- hydrazinopyrazole, 1 -benzyl-4,5-diamino-3-methylpyrazole,
  • a 4,5-diaminopyrazole will preferably be used and even more preferentially 4,5-diamino- 1-(P-hydroxyethyl)pyrazole and/or a corresponding salt.
  • Use will preferably be made of 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 - one and/or a corresponding salt.
  • Heterocyclic bases that will preferably be used include 4,5-diamino-1 -(p- hydroxyethyl)pyrazole and/or 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one and/or a corresponding salt.
  • composition according to the invention may optionally comprise one or more coupling agents advantageously chosen from those conventionally used in the dyeing of keratin fibres.
  • addition salts of oxidation bases and couplers that may be used in the context of the invention are chosen in particular from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the oxidation base(s) each advantageously represent from 0.001 % to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight relative to the total weight of the composition and of the ready-to-use composition.
  • composition according to the invention may optionally comprise b) one or more synthetic or natural direct dyes chosen from cationic, anionic and nonionic species, preferably cationic or nonionic species, either as sole dyes or in addition to the oxidation dye(s).
  • Suitable direct dyes include azo direct dyes; (poly)methine dyes such as cyanins, hemicyanins and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanin dyes and natural direct dyes, alone or in the form of mixtures.
  • the direct dyes are preferably cationic direct dyes. Mention may be made of the hydrazono cationic dyes of formulae (Ilia) and (lll'a), the azo cationic dyes (IVa) and (IV'a) and the diazo cationic dyes (Va) below:
  • Ar + represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferably ammonium, particularly tri(Ci-C 8 )alkylammonium such as trimethylammonium;
  • Ar represents an aryl group, in particular phenyl, which is optionally substituted, preferably with one or more electron-donating groups such as i) optionally substituted (CrC 8 )alkyl, ii) optionally substituted (CrC 8 )alkoxy, iii) (di)(Ci-C 8 )(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, iv) aryl(Ci-
  • Ar' represents an optionally substituted divalent (hetero)arylene group such as phenylene, particularly para-phenylene, or naphthalene, which are optionally substituted, preferably with one or more groups (Ci-C 8 )alkyl, hydroxyl or (d-
  • Ar represents an optionally substituted (hetero)aryl group such as phenyl or pyrazolyl, which are optionally substituted, preferably with one or more (CrC 8 )alkyl, hydroxyl, (di)(Ci-C 8 )(alkyl)amino, (Ci-C 8 )alkoxy or phenyl groups;
  • R a and R b which may be identical or different, represent a hydrogen atom or a (C C 8 )alkyl group, which is optionally substituted, preferably with a hydroxyl group;
  • R a with a substituent of Het + and/or R b with a substituent of Ar and/or R a with R b form, together with the atoms that bear them, a (hetero)cycloalkyl; particularly, R a and R b represent a hydrogen atom or a (CrC 4 )alkyl group, which is optionally substituted with a hydroxyl group;
  • An " represents an anionic counterion, such as mesylate or halide.
  • the cationic part is derived from the following derivatives:
  • R 1 represents a (Ci-C 4 )alkyl group such as methyl
  • R 2 and R 3 which may be identical or different, represent a hydrogen atom or a (C C 4 )alkyl group, such as methyl;
  • R 4 represent a hydrogen atom or an electron-donating group such as an optionally substituted (Ci-C 8 )alkyl group, an optionally substituted (Ci-C 8 )alkoxy group, or a (di)(Ci- C 8 )(alkyl)amino group optionally substituted on the alkyl group(s) with a hydroxyl group; in particular, R 4 represents a hydrogen atom,
  • - Z represents a CH group or a nitrogen atom, preferably CH, -
  • An " represents an anionic counterion, such as mesylate or halide.
  • the dye of formulae (llla-1 ) and (IVa-1 ) is chosen from Basic Red 51 , Basic Yellow 87 and Basic Orange 31 or corresponding derivatives:
  • Basic Red 51 Basic Orange 31 Basic Yellow 87 Among the natural direct dyes that may be used according to the invention, mention may be made of hennotannic acid, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orcein. Extracts or decoctions containing these natural dyes and in particular henna-based poultices or extracts may also be used.
  • the lightening is evaluated visually in a CMB2028 light box and colorimetrically with a Minolta CM2600D spectrocolori meter.
  • the colorimetric data are comparable even better between the invention and the comparative one .
  • compositions 5 to 7 were prepared (amount in grams per 100 g (% g)). Table 4: Compositions 5 to 7
  • the lightening obtained with the diamine compounds of the invention is greater than that obtained with MEA.
  • the latter is confirmed with spectrocolorimetric evaluation: see table 5.
  • polyamines 1 and 2 according to invention are significantly superior in terms of AEab and lightening AL related to the MEA (comparative) even at very low concentration of polyamine according to the invention (4.1 .10 "3 mol of polyamine 100 g after mixture with oxidizing agent).
  • compositions were prepared from ingredients wherein the amount is given, in weight percentage of active mater in table 6.
  • the locks are rinsed and then shampooed.
  • the lightening is evaluated colorimetrically with a Minolta CM3610D spectrocolorimeter.
  • the lightening obtained with the diamine compounds is greater than that obtained with MEA.
  • the colorimetric data are comparable between the prior art and the invention.
  • the polyamine compounds according to the invention make it possible to obtain lightening greater than that obtained with the mixture of MEA and PEI (comparative composition).

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Abstract

L'invention concerne l'utilisation de composés polyamine particuliers portant une chaîne aliphatique interrompue en présence d'agents oxydants chimiques, pour le traitement de fibres kératiniques, en particulier en remplacement de l'ammoniaque et/ou de la monoéthanolamine (MEA), un procédé pour le traitement de fibres kératiniques utilisant lesdits composés polyamine particuliers en présence d'agents oxydants chimiques, et un dispositif à plusieurs compartiments comprenant ceux-ci. Les composés de formule (I) selon l'invention associés à un ou plusieurs ingrédients (ii) permettent d'obtenir un bon niveau de performances, notamment en termes d'éclaircissement des fibres kératiniques, tout en maintenant parallèlement l'intégrité des fibres kératiniques qui est comparable, ou même supérieure, à celle obtenue avec de l'ammoniaque ou de la MEA. De plus, aucune odeur désagréable associée aux composés de formule (I) en présence d'un agent oxydant n'est observée.
PCT/EP2016/081754 2015-12-21 2016-12-19 Utilisation de composés polyamine particuliers en présence d'agents oxydants pour le traitement de fibres kératiniques WO2017108696A1 (fr)

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FR1562907 2015-12-21
FR1562907A FR3045344B1 (fr) 2015-12-21 2015-12-21 Utilisation de composes polyamines particuliers en presence d'oxydants pour traiter les fibres keratiniques

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2412209A (en) * 1943-04-22 1946-12-10 Eastman Kodak Co Preparation of aliphatic amines
EP1196525A1 (fr) * 1999-07-16 2002-04-17 The Procter & Gamble Company Composition de lessives comportant des polyamines et des tensio-actifs ramifies en milieu de chaine
EP1403246A1 (fr) * 2002-09-26 2004-03-31 Bayer Polymers LLC Résines polyaspartate à flexibilité améliorée
US20120325256A1 (en) * 2011-06-24 2012-12-27 L'ORéAL S.A. Compositions containing a polyamine, a nonionic surfactant, and a carboxylate compound for lifting color and/or imparting shine onto keratinous substrates

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2412209A (en) * 1943-04-22 1946-12-10 Eastman Kodak Co Preparation of aliphatic amines
EP1196525A1 (fr) * 1999-07-16 2002-04-17 The Procter & Gamble Company Composition de lessives comportant des polyamines et des tensio-actifs ramifies en milieu de chaine
EP1403246A1 (fr) * 2002-09-26 2004-03-31 Bayer Polymers LLC Résines polyaspartate à flexibilité améliorée
US20120325256A1 (en) * 2011-06-24 2012-12-27 L'ORéAL S.A. Compositions containing a polyamine, a nonionic surfactant, and a carboxylate compound for lifting color and/or imparting shine onto keratinous substrates

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