WO2012069639A2 - Composition pour traiter des fibres de kératine comprenant un tensioactif cationique comprenant une chaîne hydroxylée - Google Patents

Composition pour traiter des fibres de kératine comprenant un tensioactif cationique comprenant une chaîne hydroxylée Download PDF

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WO2012069639A2
WO2012069639A2 PCT/EP2011/071046 EP2011071046W WO2012069639A2 WO 2012069639 A2 WO2012069639 A2 WO 2012069639A2 EP 2011071046 W EP2011071046 W EP 2011071046W WO 2012069639 A2 WO2012069639 A2 WO 2012069639A2
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radical
formula
composition
composition according
alkyl
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PCT/EP2011/071046
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WO2012069639A3 (fr
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Alain Lagrange
Bruno Laguitton
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L'oreal
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Priority claimed from FR1059741A external-priority patent/FR2967897B1/fr
Priority claimed from FR1059742A external-priority patent/FR2967898B1/fr
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Publication of WO2012069639A2 publication Critical patent/WO2012069639A2/fr
Publication of WO2012069639A3 publication Critical patent/WO2012069639A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • One subject of the present invention is a composition for treating keratin fibres, in particular dyeing processes using an oxidizing agent, and that contains a cationic surfactant comprising at least one hydroxylated chain.
  • oxidation dyeing or permanent dyeing.
  • This dyeing method uses one or more oxidation dye precursors, more particularly one or more oxidation bases optionally combined with one or more couplers which, in the presence of an alkaline agent and an oxidizing agent form, by a process of oxidative condensation, coloured species.
  • the mixing of the dye precursors and the oxidizing agent is carried out at the moment of use.
  • oxidation bases are especially selected from ortho- or para- phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds.
  • These oxidation bases are generally combined with one or more couplers, these couplers being chosen especially from aromatic mefa-diamines, mefa-aminophenols, mefa-diphenols and certain heterocyclic compounds, such as indole compounds.
  • couplers such as aromatic mefa-diamines, mefa-aminophenols, mefa-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 composition is of a more or less deep or more or less chromatic colour and does not always correspond perfectly to the final coloration of the hair, which may be misleading for the user.
  • the stronger the colour of the composition the greater are the risks of marking of the skin and the scalp.
  • the coloration of the composition also results in a drop in the effectiveness of the dyeing operation, the formation of the coloured species taking place in the bowl before application and not in the keratin fibre. Consequently, it is often necessary to use larger amounts of dye precursors than are needed for dyeing the hair in order to compensate for this loss of reagents, giving rise, amongst other things, to an increase in the cost of the composition.
  • an oxidizing agent generally hydrogen peroxide, optionally combined with persalts such as persulphates.
  • Organic amines also have a certain odour and may also cause scalp irritations. All these drawbacks have to a large extent been overcome by the use of particular formulations that especially comprise fatty-chain cationic surfactants. Such formulations are described, for example, in document FR 292371 1.
  • the objective of the present invention is therefore to propose compositions that are less ecotoxic and that limit the aforementioned drawbacks linked to the coloration of the composition before application to the hair, and to the unpleasant odour linked to the use of an alkaline agent such as aqueous ammonia or organic amines and without degrading the dyeing properties.
  • composition comprising:
  • F which may be identical or different, represent a hydrogen atom, a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical, optionally bearing at least one hydroxyl or alkoxy group, the alkyl part of which is a C C 4 alkyl;
  • R 2 which may be identical or different, represent a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical;
  • R 3 representing a linear or branched C 8 -C 32 hydrocarbon-based radical that is saturated or that comprises one or more conjugated or unconjugated unsaturated groups, optionally bearing at least one hydroxyl group
  • a radical -CH 2 0-R' 3 with R' 3 representing a linear or branched C 8 -C 32 hydrocarbon-based radical that is saturated or that comprises one or more conjugated or unconjugated unsaturated groups, optionally bearing at least one hydroxyl group;
  • n 2 or 3
  • p is equal to 0 or 1 and the sum of n and p is equal to 3;
  • R represents a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical, optionally bearing at least one hydroxyl or alkoxy group, the alkyl part of which is a
  • R' 2 represents a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical, optionally bearing at least one hydroxyl or alkoxy group, the alkyl part of which is a C1-C4 alkyl; a radical -CH r CH(OH)-[CH(OH)] n » H with n' representing an integer ranging from 1 to 4;
  • R' 3 representing a linear or branched C 8 -C 32 hydrocarbon-based radical that is saturated or that comprises one or more conjugated or unconjugated unsaturated groups, optionally bearing at least one hydroxyl group
  • n is an integer ranging from 1 to 3;
  • X " represents a counterion
  • a subject of the invention is also a method for treating human keratin fibres, in which the aforementioned composition is applied to the fibres.
  • the invention furthermore relates to a multicompartment device comprising a first compartment containing a composition comprising at least one dye chosen from oxidation dye precursors, direct dyes or mixtures thereof, or at least one alkaline agent, or mixtures thereof and a second compartment containing a composition comprising one or more oxidizing agents, at least one of the two compartments comprising at least one cationic surfactant of formula (I) or ( ⁇ ).
  • the invention finally relates to the use of cationic surfactant(s) of formula (I) or ( ⁇ ) for dyeing or bleaching human keratin fibres, especially the hair.
  • cationic surfactant(s) of formula (I) or ( ⁇ ) for dyeing or bleaching human keratin fibres, especially the hair.
  • the human keratin fibres treated according to the invention are preferably the hair.
  • the expression "at least one” is understood to mean “one or more”.
  • composition according to the invention comprises at least one cationic surfactant of formula (I) or ( ⁇ ) below.
  • RL which may be identical or different, represent a hydrogen atom, a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical, optionally bearing at least one hydroxyl or alkoxy group, the alkyl part of which is a C C 4 alkyl;
  • R 2 which may be identical or different, represent a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical;
  • R 3 representing a linear or branched C 8 -C 32 hydrocarbon-based radical that is saturated or that comprises one or more conjugated or unconjugated unsaturated groups (groups containing carbon-carbon double bonds), optionally bearing at least one hydroxyl group; a radical -CH 2 0-R' 3 with R' 3 representing a linear or branched C 8 -C 32 hydrocarbon-based radical that is saturated or that comprises one or more conjugated or unconjugated unsaturated groups (groups containing carbon-carbon double bonds), optionally bearing at least one hydroxyl group; n is equal to 2 or 3; p is equal to 0 or 1 and the sum of n and p is equal to 3;
  • X " represents a counterion.
  • the cationic surfactant(s) of formula (I) are such that R 3 represents a C 8 -C 32 , preferably Ci 0 -C 30 , alkyl radical or a radical -CH 2 0-R' 3 with R' 3 representing a C 8 -C 32 , preferably Ci 0 -C 30 , alkyl radical.
  • the radical represents a hydrogen atom.
  • R 2 which may be identical or different, more particularly represent a Ci-C 4 alkyl radical, preferably a methyl radical.
  • n is equal to 2 and p is equal to 1.
  • the electroneutrality of the cationic surfactants of formula (I) is ensured by the counterion X " which may be an organic or mineral anion or a mixture of organic or mineral anions.
  • X " represents, for example, a halide ion such as chloride, bromide, fluoride or iodide; a hydroxide ion; a sulphate ion; a hydrogensulphate ion; an alkylsulphate ion in which the linear or branched alkyl part is a C C 6 alkyl, such as the methylsulphate or ethylsulphate ion; carbonate and hydrogencarbonate ions; ions derived from carboxylic acids, such as formate, acetate, citrate, tartrate and oxalate ions; alkylsulphonate ions for which the linear or branched alkyl part is a C C 6 alkyl, such as the methylsulphonate ion; arylsulphonate ions for which the aryl part, preferably phenyl, is optionally substituted by one or more C C 4 alkyl radicals, such as, for example, 4-toly
  • cationic surfactants of formula (I) that are suitable for the implementation of the invention, mention may be made of the following compounds, taken alone or as a mixture:
  • X denotes a counterion as defined previously.
  • X " denotes a chloride ion.
  • composition according to the invention advantageously has a content of cationic surfactant(s) of formula (I) ranging from 0.01 % to 20%, more particularly from 0.1 % to 10%, and preferably from 0.5% to 5% by weight relative to the total weight of the composition.
  • R represents a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical, optionally bearing at least one hydroxyl or alkoxy group, the alkyl part of which is a C1-C4 alkyl;
  • R' 2 represents a linear C C 6 alkyl radical or a branched C 3 -C 6 alkyl radical, optionally bearing at least one hydroxyl or alkoxy group, the alkyl part of which is a C1-C4 alkyl; a radical -CH 2 -CH(OH)-[CH(OH)] n -H with n' representing an integer ranging from 1 to 4;
  • R' 3 representing a linear or branched C 8 -C 32 hydrocarbon-based radical that is saturated or that comprises one or more conjugated or unconjugated unsaturated groups (groups containing carbon-carbon double bonds), optionally bearing at least one hydroxyl group
  • n is an integer ranging from 1 to 3;
  • X " represents a counterion.
  • the cationic surfactant(s) of formula ( ⁇ ) are such that R' 3 represents a C 8 -C 32 , preferably Ci 0 -C 30 , alkyl radical, or a radical -CH(OH)-(CH 2 0)p-R" 3 with R" 3 representing a C 8 -C 32 , preferably Ci 0 -C 30 , alkyl radical, p being equal to 0 or 1.
  • n is equal
  • the radical R' ⁇ represents a C C 4 alkyl radical.
  • R' 2 more particularly represents a C C 4 alkyl radical or a radical -CH 2 - CH(OH)-[CH(OH)]n'-H with n' representing an integer ranging from 1 to 3.
  • n' is equal to 3. More advantageously still, R' 2 represents a C C 4 alkyl radical.
  • the electroneutrality of the cationic surfactants of formula ( ⁇ ) is ensured by the counterion X " which may be an organic or mineral anion or a mixture of organic or mineral anions.
  • X " represents, for example, a halide ion such as chloride, bromide, fluoride or iodide; a hydroxide ion; a sulphate ion; a hydrogensulphate ion; an alkylsulphate ion in which the linear or branched alkyl part is a C C 6 alkyl, such as the methylsulphate or ethylsulphate ion; carbonates and hydrogencarbonates; an ion derived from a carboxylic acid, such as formate, acetate, citrate, tartrate and oxalate ions; alkylsulphonate ions for which the linear or branched alkyl part is a C C 6 alkyl, such as the methylsulphonate ion; arylsulphonate ions for which the aryl part, preferably phenyl, is optionally substituted by one or more C C 4 alkyl radicals, such as, for example, the
  • cationic surfactants of formula ( ⁇ ) that are suitable for the implementation of the invention, mention may be made of the following compounds, taken alone or as a mixture:
  • X " denotes a chloride ion.
  • composition according to the invention advantageously has a content of cationic surfactant(s) of formula (I) or ( ⁇ ) ranging from 0.01 % to 20% by weight, more particularly from 0.1 % to 10% by weight, and preferably from 0.5% to 5% by weight relative to the total weight of the composition.
  • composition according to the invention comprises at least one oxidizing agent.
  • this oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulphates, perborates and percarbonates of alkali metals or alkaline-earth metals, such as sodium, potassium and magnesium.
  • the oxidizing agent is preferably hydrogen peroxide.
  • the composition according to the invention may comprise one or more oxidation dye precursors. These oxidation dye precursors are chosen from oxidation bases and couplers.
  • the oxidation bases may be chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, orf 70-aminophenols and heterocyclic bases, and the addition salts thereof.
  • para-phenylenediamines that may be mentioned, for example, are 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 -hydroxyethyl)-para- phenylenediamine, 4-N,N-bis ⁇ -hydroxyethyl)amino-2-methylaniline, 4-N,N-bis - hydroxyeth, 4-
  • para-phenylenediamine para-toluenediamine, 2-isopropyl-para-phenylenediamine, 2 ⁇ -hydroxyethyl-para- phenylenediamine, 2 ⁇ -hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para- phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para- phenylenediamine, N,N-bis ⁇ -hydroxyethyl)-para-phenylenediamine, 2-chloro-para- phenylenediamine and 2- ⁇ -acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines that may be mentioned, for example, are N,N'-bis( ⁇ -hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1 ,3-diaminopropanol, N,N'-bis( ⁇ - hydroxyethyl)-N,N'-bis(4'-aminophenyl)ethylenediamine, N,N'-bis(4-aminophenyl)- tetramethylenediamine, N,N'-bis ⁇ -hydroxyethyl)-N,N'-bis(4-amino- phenyl)tetramethylenediamine, N,N'-bis(4-methylaminophenyl)-tetramethylenediamine, N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'-methylphenyl)ethylenediamine, 1 ,8-bis(2,5- di
  • 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-( ⁇ -hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • o/f/70-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 that may be mentioned, for example, are 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 the 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-ylpyrazolo[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-a
  • pyrimidine derivatives that may be mentioned are the compounds described, for example, in the patents DE 2359399; JP 88-169571 ; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4- hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6- diaminopyrimidine, 2,5,6-triaminopyrimidine and their addition salts and their tautomeric forms, when a tautomeric equilibrium exists.
  • pyrazole derivatives that may be mentioned are the compounds described in the patents DE 3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, such as 4,5-diamino-1-methyl- pyrazole, 4,5-diamino-1- ⁇ -hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4'- chlorobenzyl)pyrazole, 4,5-diamino-1 ,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenyl- pyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1 ,3-dimethyl-5-hydrazino- pyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-d
  • Pyrazole derivatives that may also be mentioned include diamino-N,N- dihydropyrazolones and especially those described in patent application FR 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 ,
  • Heterocyclic bases that will preferentially be used include 4,5-diamino-1- - hydroxyethyl)pyrazole and/or 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]-pyrazol-1- one and the addition salts thereof.
  • couplers mention may be made of mefa-phenylenediamines, meta- aminophenols, mefa-diphenols, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof.
  • addition salts of the oxidation bases and couplers that may be used in the context of the invention are especially selected from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates.
  • the oxidation base(s) each represent, when they are present, from 0.0001 % 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.
  • the coupler(s) each represent, when they are present, from 0.0001 % 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.
  • the composition may also comprise one or more direct dyes. These direct dyes are chosen, for example, from neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, tetraazapentamethine dyes, neutral, acidic or cationic quinone and in particular anthraquinone dyes, azine direct dyes, triarylmethane direct dyes, indoamine direct dyes and natural direct dyes.
  • nitrobenzene direct dyes that may be mentioned, in a non-limiting manner, are the following compounds:
  • azo direct dyes mention may be made of the cationic azo dyes described in patent applications WO-95/15144, WO-95/01772 and EP-714 954, the content of which forms an integral part of the invention.
  • dyes 1 ,3-dimethyl-2-[[4-(dimethylamino)phenyl]azo]-1 H-imidazolium chloride, 1 ,3- dimethyl-2-[(4-aminophenyl)azo]-1 H-imidazolium chloride, 1-methyl-4-[(methylphenyl hydrazono)methyl]pyridinium methyl sulphate.
  • quinone direct dyes that may be mentioned are the following dyes:
  • azine dyes that may be mentioned are the following compounds:
  • triarylmethane dyes mention may be made of the following compounds: Basic Green 1 , Acid Blue 9, Basic Violet 3, Basic Violet 14, Basic Blue 7, Acid Violet 49, Basic Blue 26, Acid Blue 7.
  • indoamine dyes mention may be made of the following compounds: -2- ⁇ -hydroxyethlyamino-5-[bis( ⁇ -4'-hydroxyethyl)amino]anilino-1 ,4-benzoquinone;
  • the direct dye(s) more particularly represent from 0.0001 % to 10 % by weight and preferably from 0.005% to 5 % by weight of the total weight of the composition.
  • the composition may also comprise at least one alkaline agent. More particularly, the alkaline agent is chosen from mineral or organic or hybrid alkaline agents, or mixtures thereof.
  • the mineral alkaline agent(s) are preferably chosen from aqueous ammonia, alkali 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 pK 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 pK corresponding to the function of highest basicity.
  • Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid.
  • organic amines with a pK at 25°C of less than 12 are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (A) below:
  • W is a C C 6 alkylene residue optionally substituted with a hydroxyl group or a Ci-C 6 alkyl radical
  • Rx, Ry, Rz and Rt which may be identical or different, represent a hydrogen atom or a C C 6 alkyl, C C 6 hydroxyalkyl or C C 6 aminoalkyl radical.
  • Examples of such amines that may be mentioned include 1 ,3-diaminopropane, 1 ,3- diamino-2-propanol, spermine and spermidine.
  • alkanolamine means an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C C 8 alkyl groups bearing one or more hydroxyl radicals.
  • Alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising from one to three identical or different C C 4 hydroxyalkyl radicals are in particular suitable for performing the invention.
  • 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, sulphonic acid, phosphonic acid or phosphoric acid functions.
  • the amino acids may be in neutral or ionic form.
  • amino acids that may be used in the present invention, mention may be made especially 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.
  • 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
  • i e a group chosen from:
  • the compounds corresponding to formula (B) 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 be made in particular 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 baleine.
  • the organic amine is chosen from compounds comprising a guanidine function.
  • amines of this type that may be used in the present invention, besides arginine that 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-sulphonic acid.
  • composition of the invention preferably contains aqueous ammonia and/or an alkanolamine such as monoethanolamine.
  • the composition according to the invention has a content of alkaline agent(s), if it (they) is (are) present, ranging from 0.01 % to 30% by weight and preferably from 0.1 % to 20% by weight relative to the total weight of said composition.
  • the composition according to the invention may also comprise one or more fatty esters.
  • fatty esters within the meaning of the present invention, is understood more particularly to mean an ester of a carboxylic acid comprising in its structure a fatty chain with at least 10 carbon atoms, preferably having from 10 to 30 carbon atoms, preferably from 10 to 22 carbon atoms, and of an alcohol which is preferably a monoalcohol, especially CrC 30 , more particularly C C 2 2, or a sugar.
  • these compounds are chosen from:
  • these esters may be selected in particular from oleate, laurate, palmitate, myristate, behenate, cocoate, stearate, linoleate, linolenate, caprate, arachidonate, or mixtures thereof, in particular such as the oleopalmitates, oleostearates and palmitostearates of C C 30 monoalcohols.
  • these esters use is more particularly made of isopropyl palmitate, isopropyl myristate, octyldodecyl stearate and isononyl isononaoate.
  • esters of linear or branched C 3 -C 8 monoalcohols with bifunctional, linear or branched, saturated or unsaturated Ci 2 -C 30 fatty acids, that may be more particularly cited are the isopropyl diester of sebacic acid, also known as diisopropyl sebacate.
  • composition may also comprise, as fatty ester, sugar esters and diesters of Ci 0 - C 30 fatty acids.
  • sugar esters and diesters of Ci 0 - C 30 fatty acids.
  • sugar esters and diesters of Ci 0 - C 30 fatty acids.
  • sugar esters and diesters of Ci 0 - C 30 fatty acids.
  • sugar esters and diesters of Ci 0 - C 30 fatty acids.
  • sugar esters means compounds that have several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms. These sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose (or saccharose), 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 be selected especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C10-C22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • the esters may also be selected from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates of sugar(s), or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters of sugar(s).
  • monoesters and diesters and especially sucrose, glucose or methylglucose monooleates or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
  • esters or mixtures of esters of sugar and of fatty acid examples include:
  • sucrose palmitostearates formed from 73% monoester and 27% diester and triester, from 61 % monoester and 39% diester, triester and tetraester, from 52% monoester and 48% diester, triester and tetraester, from 45% monoester and 55% diester, triester and tetraester, from 39% monoester and 61 % diester, triester and tetraester, and sucrose monolaurate;
  • Ryoto Sugar Esters for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% diester, triester and polyester;
  • sucrose monodipalmitostearate sold by the company Goldschmidt under the name Tegosoft® PSE.
  • fatty ester of compounds chosen from esters of saturated, linear or branched C Ci 8 monoalcohols, with Ci 4 -Ci 8 monofunctional fatty acids, it being possible for the latter to be linear or branched, saturated or unsaturated.
  • the composition according to the invention has a content of fatty ester(s) ranging advantageously from 0.3% to 12.5% by weight, preferably from 0.5% to 10% by weight relative to the total weight of the composition.
  • the composition according to the invention may furthermore comprise one or more fatty alcohols.
  • said fatty alcohol is chosen from non-(poly)oxyalkylenated (the alkyl having 1 to 3 carbon atoms) and non-(poly)glycerolated alcohols, comprising one or more fatty chains having from 10 to 30 carbon atoms, more particularly from 14 to 22 carbon atoms and more advantageously still from 16 to 18 carbon atoms, which are saturated or unsaturated, the fatty chains optionally being substituted by one or two additional hydroxyl groups.
  • the fatty alcohol is a monoalcohol.
  • fatty alcohols mention may be made of lauryl, cetyl, stearyl, behenyl, myristyl, linoleyl, undecylenyl, palmitoleyl, linolenyl, arachidonyl, erucyl, isocetyl, isostearyl and isobehenyl alcohols, oleyl alcohol and mixtures thereof.
  • the composition comprises one or more non-(poly)oxyalkylenated and non-(poly)glycerolated fatty monoalcohols, comprising from 14 to 22 carbon atoms and more specifically from 16 to 18 carbon atoms, which are saturated.
  • the composition has a content of fatty alcohol(s) ranging from 1 % to 25% by weight, relative to the total weight of the composition, preferably from 3% to 20% by weight and in accordance with one even more preferred variant of the invention, from 5% to 18% by weight.
  • the composition according to the invention comprises water or a mixture of water and one or more organic solvents.
  • organic solvents examples include linear or branched C 2 -
  • C 4 alkanols such as ethanol and isopropanol; glycerol; glycols and glycol ethers, for instance 2-butoxyethanol, propylene glycol, dipropylene glycol, propylene glycol monomethyl ether and diethylene glycol monomethyl ether or monoethyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the solvent(s) may be present in proportions preferably ranging from 1 % to 90% by weight relative to the weight of the composition, and even more preferentially from 5% to
  • composition according to the invention may also optionally comprise one or more cationic or amphoteric substantive polymers.
  • the substantive character (i.e. the capacity for deposition on the hair) of the polymers is determined conventionally using the test described by Richard J. Crawford, Journal of the Society of Cosmetic Chemists, 1980, 31 - (5) - pages 273 to 278 (detection by Red 80 acid dye).
  • polymers selected from cationic cellulose derivatives homopolymers of dimethyldiallylammonium halide and copolymers of dimethyldiallylammonium halide and of (meth)acrylic acid; homopolymers and copolymers of methacryloyloxyethyltrimethylammonium halide; quaternary polyammonium polymers; vinylpyrrolidone polymers with cationic units; cationic polysiloxanes; and mixtures thereof.
  • the substantive polymers of the quaternary polyammonium type that can be used according to the invention are as follows:
  • CH, CH 3 in which p denotes an integer ranging from 1 to 6 approximately, D may be zero or may represent a group (CH 2 ) r -CO- in which r denotes a number equal to 4 or 7,
  • cationic polysiloxanes mention may especially be made of:
  • T is a hydrogen atom or a phenyl, hydroxyl (-OH) or Ci-Cs alkyl radical, and preferably methyl, or a C C 8 alkoxy, preferably methoxy,
  • a denotes the number 0 or an integer from 1 to 3, and preferably 0,
  • b denotes 0 or 1 , and in particular 1 ,
  • n and n are numbers such that the sum (n + m) can range especially from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and in particular from 49 to 149, and for m to denote a number from 1 to 2000 and in particular from 1 to 10;
  • R1 is a monovalent radical of formula -C q H 2q L in which q is a number from 2 to 8 and L is an optionally quaternized amino group chosen from the following groups:
  • R2 can denote a hydrogen atom, a phenyl, a benzyl or a saturated monovalent hydrocarbon-based radical, for example a CiC 20 alkyl radical
  • Q " represents a halide ion such as, for example, fluoride, chloride, bromide or iodide.
  • amino silicones corresponding to the definition of formula (5) are chosen from the compounds corresponding to the following formula:
  • R, R' and R which may be identical or different, denote a C C 4 alkyl radical, preferably CH 3 ; a C C 4 alkoxy radical, preferably methoxy; or OH; A represents a linear or branched, C 3 -C 8 and preferably C 3 -C 6 alkylene radical; m and n are integers dependent on the molecular weight and whose sum is between 1 and 2000.
  • R, R' and R" which may be identical or different, represent a C C 4 alkyl or hydroxyl radical
  • A represents a C 3 alkylene radical and m and n are such that the weight-average molecular weight of the compound is between 5000 and 500 000 approximately.
  • Compounds of this type are referred to in the CTFA dictionary as "amodimethicones”.
  • R, R' and R" which may be identical or different, represent a C C 4 alkoxy or hydroxyl radical, at least one of the radicals R or R" is an alkoxy radical and A represents a C 3 alkylene radical.
  • the hydroxy/alkoxy molar ratio is preferably between 0.2/1 and 0.4/1 and advantageously equal to 0.3/1.
  • m and n are such that the weight-average molecular weight of the compound is between 2000 and 10 6 . More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.
  • R and R" which are different, represent a C C 4 alkoxy or hydroxyl radical
  • at least one of the radicals R or R" is an alkoxy radical
  • R' represents a methyl radical
  • A represents a C 3 alkylene radical.
  • the hydroxy/alkoxy molar ratio is preferably between 1/0.8 and 1/1.1 and advantageously is equal to 1/0.95.
  • m and n are such that the weight-average molecular weight of the compound is between 2000 and 200 000. More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.
  • R and R" represent a hydroxyl radical
  • R' represents a methyl radical
  • A is a C 4 -C 8 and preferably C 4 alkylene radical.
  • m and n are such that the weight-average molecular weight of the compound is between 2000 and 10 6 . More particularly, n is between 0 and 1999 and m is between 1 and 2000, the sum of n and m being between 1 and 2000.
  • a product of this type is especially sold under the name DC 28299 by Dow Corning.
  • the molecular weight of these silicones is determined by gel permeation chromatography (room temperature, polystyrene standard; ⁇ styragem columns; THF eluent; flow rate of 1 mm/m; 200 ⁇ of a solution containing 0.5% by weight of silicone in THF are injected, and detection is performed by refractometry and using a UV-meter).
  • a product corresponding to the definition of formula (5) is in particular the polymer known in the CTFA dictionary as "trimethylsilylamodimethicone", corresponding to formula (6) below: (CH 3 ) 3 i(CH 3 ) 3
  • n and m have the meanings given above in accordance with formula (5).
  • R 3 represents a monovalent C Ci 8 hydrocarbon-based radical, and in particular a C Ci 8 alkyl or C 2 -Ci 8 alkenyl radical, for example methyl;
  • R 4 represents a divalent hydrocarbon-based radical, especially a C Ci 8 alkylene radical or a divalent C Ci 8 , and for example C C 8 , alkylenoxy radical;
  • Q " is a halide ion, especially chloride
  • r represents a mean statistical value from 2 to 20 and in particular from 2 to 8;
  • s represents a mean statistical value from 20 to 200 and in particular from 20 to 50.
  • a compound falling within this class is the product sold by the company Union Carbide under the name Ucar Silicone ALE 56.
  • R 7 which may be identical or different, represent a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a C Ci 8 alkyl radical, a C 2 -Ci 8 alkenyl radical or a ring comprising 5 or 6 carbon atoms, for example methyl;
  • R 6 represents a divalent hydrocarbon-based radical, especially a C Ci 8 alkylene radical or a divalent C Ci 8 , and for example C C 8 , alkylenoxy radical linked to the Si via an SiC bond;
  • R 8 which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon-based radical containing from 1 to 18 carbon atoms, and in particular a C
  • X " is an anion such as a halide ion, especially chloride, or an organic acid salt (acetate, etc.);
  • r represents a mean statistical value from 2 to 200 and in particular from 5 to 100;
  • R 2 , R3 and R 4 which may be identical or different, denote a C C 4 alkyl radical or a phenyl group,
  • R 5 denotes a C C 4 alkyl radical or a hydroxyl group
  • - n is an integer ranging from 1 to 5
  • - m is an integer ranging from 1 to 5
  • x is selected such that the amine number is between 0.01 and 1 meq/g.
  • the concentration of cationic or amphoteric substantive polymer may range from 0.01 % to 10% approximately relative to the total weight of the composition, and preferably from 0.1 % to 5% by weight relative to the weight of the composition.
  • the dyeing composition according to the invention may also comprise various additives conventionally used in the field of dyeing human keratin fibres.
  • the composition may thus comprise mineral or organic thickeners, and in particular fillers such as clays, optionally associative nonionic, anionic, cationic or amphoteric polymers; binders such as vinylpyrrolidone; lubricants such as polyol stearates or alkali metal or alkaline-earth metal stearates; hydrophilic or hydrophobic silicas; pigments; matting agents such as titanium oxides; anionic, nonionic, cationic, amphoteric or zwitterionic surfactants; penetrants, sequestrants, such as ethylenediaminetetraacetic acid or salts thereof; moisture absorbers such as amorphous silicas, buffers; dispersants; film-forming agents; preserving agents; opacifiers; vitamins; fragrances; ceramides; and volatile silicones.
  • fillers such as clays, optionally associative nonionic, anionic, cationic or amphoteric polymers
  • binders such as
  • the additives as defined above may be present in an amount, for each of them, of between 0.01 % and 40% by weight and preferably between 0.1 % and 30% by weight relative to the total weight of the composition.
  • the process according to the invention consists in applying the composition which has just been described in detail to human keratin fibres, it being possible for the latter to be wet or dry.
  • composition comprises at least one dye, it is a dyeing process.
  • the composition applied is obtained by prior extemporaneous mixing of the various ingredients, including the oxidizing agent.
  • this composition is obtained by mixing a composition that is free of oxidizing agent, with a composition comprising it (oxidizing composition).
  • the oxidizing composition and the composition comprising the dye(s) and/or the alkaline agent(s), may one and/or the other contain one or more cationic surfactants of formula (I) or ( ⁇ ).
  • This oxidizing composition advantageously comprises water and optionally one or more solvents such as are, for example, listed within the context of the description of the composition of the invention.
  • the oxidizing composition may take the form of a solution, an emulsion or a gel. It may optionally comprise one or more additives conventionally used in the field of dyeing human keratin fibres, as a function of the desired galenic form. Once again, reference may be made to the list of additives given above.
  • composition of the invention generally has a pH above 7 and preferably ranging from 8 to 12.
  • the pH of the composition that is free of oxidizing agent and that consequently comprises the dye(s) and/or the alkaline agent(s) is generally above 8, generally between 8 and 12, and preferably between 9 and 11.
  • the pH of the oxidizing composition is customarily below 7 and preferably between 3 and 6.
  • the pH of these compositions may be adjusted to the desired value by means of one or more acidifying agents or one or more alkaline agents customarily used in the field.
  • acidifying agents examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
  • mineral or organic acids for instance hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
  • alkalinizing agents reference will be made to the lists given above.
  • the cationic surfactant(s) of formula (I) or ( ⁇ ) are, without preference, in one and/or the other of the two compositions. Irrespective of the variant selected, the composition applied (resulting from extemporaneous mixing or from successive application) is left in place for a time generally from about 1 minute to 1 hour and preferably from 10 minutes to 30 minutes.
  • the temperature during the process conventionally ranges from room temperature (between 15°C and 25°C) to 80°C and preferably from room temperature to 60°C.
  • the human keratin fibres are optionally rinsed with water, washed with shampoo, rinsed again with water, and then dried or left to dry.
  • another subject of the invention is formed by a multicompartment device comprising a first compartment containing a composition comprising at least one dye chosen from oxidation dye precursors, direct dyes or mixtures thereof, or at least one alkaline agent, or mixtures thereof and a second compartment containing a composition comprising one or more oxidizing agents, at least one of the two compositions comprising at least one cationic surfactant of formula (I) or ( ⁇ ); the dye, the alkaline agent, the oxidizing agent and the cationic surfactant of formula (I) or ( ⁇ ) being as defined above.
  • compositions are prepared: C (comparative) and 11 to I4 in accordance with the invention, the ingredients of which are listed in Tables 1 and 2 below. These compositions differ due to the nature of the cationic surfactant used.
  • Surfactants 11 to I4' are more environmentally-friendly than surfactant C.
  • each composition is mixed with an equal weight of 20-volumes aqueous hydrogen peroxide solution (6% by weight). A final pH of 9.8 is obtained.
  • the locks are rinsed, washed with a standard shampoo, rinsed again and then dried.
  • compositions 11 ', I2', I3' and I4' which are acceptable from an ecotoxicity viewpoint unlike composition C, make it possible to obtain compositions as a mixture with aqueous hydrogen peroxide solution that are less coloured than the mixture resulting from composition C and which have a less noticeable odour of ammonia.
  • compositions The following compositions are prepared: C (comparative) and 11 to I4 in accordance with the invention, the ingredients of which are listed in Tables 1 and 2 below. These compositions differ due to the nature of the cationic surfactant used.
  • Cationic surfactants J1 to J4' are more environmentally-friendly than surfactant C.
  • the surfactants are first mixed with the fatty substances before being mixed with the other ingredients of the composition.
  • each composition is mixed with an equal weight of 20-volumes aqueous hydrogen peroxide solution (6% by weight). A final pH of 9.8 is obtained.
  • compositions J1', J2', J3' and J4' which are acceptable from an ecotoxicity viewpoint unlike composition D', make it possible to obtain compositions as a mixture with aqueous hydrogen peroxide solution that are less coloured than the mixture resulting from composition D and which have a less noticeable odour of ammonia.

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Abstract

La présente invention concerne une composition comprenant : (a) au moins un tensioactif cationique de formule (I) ou (I´) ci-dessous : où : R1 représente un hydrogène, un alkyle en C1-C6, comportant facultativement au moins un hydroxyle ou un alcoxy ; R2, qui peut être identique ou différent, représente un alkyle en C1-C6 ; R3 représentant un radical à base d'hydrocarbure en C8-C32, comportant facultativement au moins un hydroxyle ; -CH2O-R'3, R'3 représentant un radical à base d'hydrocarbure en C8-C32, comportant facultativement au moins un hydroxyle ; n est égal à 2 ou 3 ; p est égal à 0 ou 1 et la somme de n et p est égale à 3 ; R'1, représente un alkyle en C1-C6, comportant facultativement au moins un hydroxyle ou un alcoxy ; R'2 représente un alkyle en C1-C6, comportant facultativement au moins un hydroxyle ou un alcoxy ; un radical -CH2-CH(OH)-[CH(OH)]n'-H, n' représentant un entier dans la plage de 1 à 4 ; R'3 représentant un radical à base d'hydrocarbure en C8-C32, comportant facultativement au moins un hydroxyle ; un radical -CH(OH)-(CH2O)P-R"3, R"3 représentant un radical à base d'hydrocarbure en C8-C32, comportant facultativement au moins un hydroxyle, p étant égal à 0 ou 1 ; m est un entier dans la plage de 1 à 3 ; X" représente un contre-ion ; et (b) au moins un agent oxydant ; (c) au moins un colorant ou au moins un agent alcalin, ou des mélanges de ceux-ci. D'autres sujets de l'invention comprennent un procédé pour traiter des fibres de kératine, dans lequel cette composition est appliquée, et en outre un dispositif à compartiments multiples comprenant, dans un premier compartiment, une composition qui est dépourvue d'agent oxydant et, dans un autre compartiment, une composition comprenant cet agent oxydant, le(s) tensioactif(s) cationique(s) de formule (I) ou (I´) étant, sans préférence, dans l'un et/ou l'autre des compartiments. L'invention concerne finalement l'utilisation de ces tensioactifs cationiques de formule (I) ou (I´) pour colorer ou décolorer des fibres de kératine humaine, en particulier les cheveux.
PCT/EP2011/071046 2010-11-25 2011-11-25 Composition pour traiter des fibres de kératine comprenant un tensioactif cationique comprenant une chaîne hydroxylée WO2012069639A2 (fr)

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FR1059741 2010-11-25
FR1059741A FR2967897B1 (fr) 2010-11-25 2010-11-25 Composition pour traiter les fibres keratiniques comprenant un tensioactif cationique comprenant une chaine grasse hydroxylee
FR1059742 2010-11-25
FR1059742A FR2967898B1 (fr) 2010-11-25 2010-11-25 Composition pour traiter les fibres keratiniques comprenant un tensioactif cationique comprenant une chaine desoxyaminosucre
US41939010P 2010-12-03 2010-12-03
US41938210P 2010-12-03 2010-12-03
US61/419,382 2010-12-03
US61/419,390 2010-12-03

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DE2359399A1 (de) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Haarfaerbemittel
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US4719282A (en) 1986-04-22 1988-01-12 Miranol Inc. Polycationic block copolymer
JPS63169571A (ja) 1987-01-06 1988-07-13 Nec Corp ト−ン検出装置
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EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
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