WO2014191354A1 - Colorants directs de quinone portant un groupe aniline encombré, composition de colorant comprenant au moins un tel colorant, procédé de mise en œuvre associé et leur utilisation - Google Patents

Colorants directs de quinone portant un groupe aniline encombré, composition de colorant comprenant au moins un tel colorant, procédé de mise en œuvre associé et leur utilisation Download PDF

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Publication number
WO2014191354A1
WO2014191354A1 PCT/EP2014/060836 EP2014060836W WO2014191354A1 WO 2014191354 A1 WO2014191354 A1 WO 2014191354A1 EP 2014060836 W EP2014060836 W EP 2014060836W WO 2014191354 A1 WO2014191354 A1 WO 2014191354A1
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formula
fibres
compounds
keratin fibres
composition
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PCT/EP2014/060836
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English (en)
Inventor
Stéphane SABELLE
Madeleine Leduc
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L'oreal
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Publication of WO2014191354A1 publication Critical patent/WO2014191354A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B53/00—Quinone imides
    • C09B53/02—Indamines; Indophenols

Definitions

  • the present invention relates to quinone direct dyes bearing a hindered aniline group of formula (I) and the leuco forms thereof of formula (II), and also to the use thereof for dyeing keratin fibres, in particular human keratin fibres such as the hair.
  • direct dyeing It is known practice to dye keratin fibres, and in particular the hair, with dye compositions containing one or more direct dyes, according to a "direct dyeing" process.
  • the process conventionally used in direct dyeing consists in applying to keratin fibres one or more direct dyes, or colouring molecules, which have affinity for the said fibres, leaving them to stand on the fibres, and then rinsing the fibres.
  • the direct dyes used hitherto are generally nitrobenzene dyes, anthraquinone dyes, nitropyridine dyes, dyes of azo, xanthene, acridine or azine type or triarylmethane-based dyes.
  • the colorations resulting therefrom are temporary or semi-permanent since the nature of the interactions that bind the direct dyes to the keratin fibre and their desorption from the surface and/or the core of the fibre are responsible for their weak dyeing power and their poor persistence with respect to washing, inclement weather or perspiration.
  • Y represents i) a hydroxyl group or ii) an amino group -NR2R 3 with R 2 and R 3 , which may be identical or different, representing:
  • Ci-C 6 alkyl radical substituted with one or more hydroxyl or linear or branched C1-C4 alkoxy radicals.
  • Another subject of the present invention concerns the use of one or more quinone direct dyes of formula (I) as defined previously for dyeing keratin fibres, in particular human keratin fibres such as the hair.
  • the present invention also relates to a composition for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising, in a suitable dyeing medium, one or more quinone direct dyes of formula (I) as defined previously.
  • the invention also relates to the use of the said dye composition for dyeing keratin fibres, especially human keratin fibres such as the hair.
  • the invention also relates to a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, in which the said dye composition according to the invention is applied to the said fibres for a time that is sufficient to obtain the desired coloration, after which the fibres are rinsed, optionally washed with shampoo, rinsed again and the resulting fibres dried or left to dry.
  • the invention relates more particularly to a process for dyeing and lightening keratin fibres, in particular human keratin fibres such as the hair, in which (i) the said dye composition, free of oxidizing agent, and (ii) a cosmetic composition comprising one or more oxidizing agents are applied to the said fibres; compositions (i) and (ii) being applied to the said keratin fibres sequentially or simultaneously for a time that is sufficient to obtain the desired lightening, after which the fibres are rinsed, optionally washed with shampoo and rinsed again, and the resulting fibres are dried or left to dry.
  • the quinone direct dyes of formula (I) according to the invention can thus give colorations that are resistant to the various attacking factors to which keratin fibres may be subjected, such as inclement weather, light, washing and perspiration.
  • the direct dyes according to the invention can satisfactorily dye keratin fibres, especially producing powerful, chromatic and sparingly selective colorations.
  • the direct dyes according to the invention have the advantage of being light-stable and can be used in the presence of an oxidizing agent, which facilitates their use in lightening direct dyeing compositions based on oxidizing agents.
  • the direct dyes according to the present invention lead to persistent colorations and are compatible with dye compositions intended for lightening keratin fibres.
  • a subject of the invention is colourless or weakly coloured compounds of leuco type, which are the reduced form of the quinone direct dyes according to the invention of formula (II) below, organic or mineral acid or base salts thereof, tautomeric forms, optical isomers or geometrical isomers thereof, and/or solvates thereof:
  • the compounds of leuco type according to the invention lead, in the presence of one or more oxidizing agents, to the quinone direct dyes of formula (I).
  • the invention also relates to the use of one or more compounds of leuco type of formula (II) as precursors of the direct dyes of formula (I).
  • the invention relates to the use of one or more compounds of leuco type of formula (II) in the presence of one or more oxidizing agents, for dyeing keratin fibres, in particular human keratin fibres such as the hair.
  • the invention also relates to a multi-compartment device or "kit” containing a first compartment comprising one or more compounds of leuco type of formula (II) as defined previously, and a second compartment comprising one or more oxidizing agents.
  • the compounds of leuco type of formula (II) used under oxidizing conditions thus have the advantage of giving colorations that are resistant to the various attacking factors to which keratin fibres may be subjected, such as inclement weather, washing, light and perspiration.
  • the dyeing process using colourless or weakly coloured compounds of formula (II) followed by a step of revealing the colour in the presence of a chemical oxidizing agent makes it possible to produce a clean coloration, i.e. a coloration that does not stain or only very sparingly stains the clothing or linen used during the hair dyeing operation, such as towels.
  • quinone direct dyes according to the invention are such that, taken together or separately:
  • Ci-C 3 alkyl radical substituted with a hydroxyl radical
  • n an integer equal to 1 ;
  • Y represents:
  • R 2 and R 3 an amino radical -NR2R 3 with R 2 and R 3 , which may be identical or different, representing a hydrogen atom or a linear or branched C1-C3 alkyl radical optionally substituted with a hydroxyl radical;
  • An " denotes a cosmetically acceptable anionic counterion or mixture of anionic counterions, for instance halides, such as chloride, methosulfates, nitrates; alkylsulfonates: Alk-S(0) 2 0 " such as methanesulfonate or mesylate and ethanesulfonate; arylsulfonates: Ar-S(0) 2 0 " such as benzenesulfonate and toluenesulfonate or tosylate; citrate; succinate; tartrate; lactate; alkyl sulfates: Alk-O- S(0)0 " such as methyl sulfate; aryl sulfates such as benzene sulfate and toluene sulfate; phosphate; acetate; triflate; and borates such as tetrafluoroborate.
  • halides such as chloride, methosulfates, nit
  • An " is an anionic counterion chosen from bromide, chloride, methyl sulfate and toluenesulfonate ions or a mixture of these ions.
  • n represents 2 or 3 and more particularly n is equal to 2
  • Ri represents a linear C1-C3 alkyl radical.
  • quinone direct dyes according to the invention of formula (I) are such that Z represents an amino radical -NR2R 3 with R 2 and R 3 as defined previously and more particularly Z represents -NH 2 .
  • the compounds of formula (I) may be used directly for dyeing the hair.
  • the quinone direct dyes of formula (I) according to the invention are chosen from the following compounds and the geometrical or optical isomer forms thereof, the tautomers thereof, the organic or mineral acid or base salts thereof or the solvates thereof such as hydrates:
  • the direct dyes of formula (I) according to the present invention are of formula
  • the quinone direct dyes of formula (I) may be obtained according to the procedure described below:
  • the compounds corresponding to formula (I) are generally obtained by reacting the derivatives 1 a with the morpholine derivatives 2 in basic medium in the presence of an oxidizing agent.
  • the base used is preferentially an aqueous solution of ammonia or of sodium hydroxide and the oxidizing agent is preferentially chosen from aqueous hydrogen peroxide solution, potassium ferricyanide, air, ammonium persulfate and manganese oxide.
  • the quinone direct dyes of formula (I) may also be obtained according to the procedure as described below:
  • the compounds corresponding to formula (I) are generally obtained by reacting the derivatives 1 a or 1 d with the meta- hydroxyethylaminophenols 3 in basic medium in the presence of an oxidizing agent.
  • the base used is preferentially an aqueous solution of ammonia or of sodium hydroxide and the oxidizing agent is preferentially chosen from aqueous hydrogen peroxide solution, potassium ferricyanide, air, ammonium persulfate and manganese oxide.
  • the invention also relates to the use of one or more quinone direct dyes of formula (I) as described previously for dyeing keratin fibres, in particular human keratin fibres such as the hair.
  • the present invention also relates to a composition for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising, in a suitable dyeing medium, one or more direct dyes of formula (I) as defined previously.
  • the dye composition comprises one or more quinone direct dyes of formula (I) chosen from compounds (1 ) to (4) as defined previously, and mixtures thereof.
  • the dye composition comprises one or more quinone direct dyes of formula (I) chosen from the compounds of formula (1 ).
  • the direct dye(s) as defined previously may be present in the dye composition according to the invention in a content ranging from 0.001 % to 10% by weight and preferably in a content ranging from 0.005% to 6% by weight, relative to the total weight of the dye composition.
  • the dye composition of the invention may also comprise one or more oxidation dyes.
  • the oxidation dyes are generally chosen from oxidation bases optionally combined with one or more couplers.
  • the oxidation bases are chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and the addition salts thereof.
  • para-phenylenediamines examples that may be mentioned include para- phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl- para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para- phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para- phenylenediamine, ⁇ , ⁇ -diethyl-para-phenylenediamine, N,N-dipropyl-para- phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(p-hydroxyethyl)-para- phenylenediamine, 4-N,N-bis(p-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(p- hydroxye
  • para-phenylenediamine para-phenylenediamine, para- tolylenediamine, 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-p-acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines examples that may be mentioned include N,N'-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, 1 ,8-bis(2,5-diaminophenoxy)-3
  • para-aminophenols examples that may be mentioned include para- aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2- hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(p-hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • ortho-aminophenols examples that may be mentioned include 2- aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2- aminophenol and the addition salts thereof.
  • heterocyclic bases examples that may be mentioned include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives examples that may be mentioned include the compounds described 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-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,
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2359399, JP 88-169571 , JP 05-63124 and EP 0 770 375 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 addition salts thereof, and tautomeric forms thereof, when a tautomeric equilibrium exists.
  • a 4,5-diaminopyrazole will preferably be used, and even more preferentially 4,5- diamino-1 -(p-hydroxyethyl)pyrazole and/or a salt thereof.
  • Pyrazole derivatives that may also be mentioned include diamino-N,N- dihydropyrazolopyrazolones and especially those described in patent application FR-A-2 886 136, such as the following compounds and the addition salts thereof: 2,3-diamino- 6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-ethylamino-6,7-dihydro- 1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-isopropylamino-6,7-dihydro-1 H,5H- pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-(pyrrolidin-1 -yl)-6,7-dihydro-1 H,5H-pyrazolo[1 ,2- a]pyrazol-1 -one, 4,5-diamin
  • Use will preferably be made of 2,3-diamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol- 1 -one and/or one of its salts.
  • Heterocyclic bases that will preferentially 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 salt thereof.
  • the dye composition may optionally comprise one or more couplers advantageously chosen from those conventionally used for the dyeing of keratin fibres.
  • couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof.
  • Examples that may be mentioned include 1 ,3-dihydroxybenzene, 1 ,3-dihydroxy-2- methylbenzene, 4-chloro-1 ,3-dihydroxybenzene, 2,4-diamino-1 -(3- hydroxyethyloxy)benzene, 2-amino-4-(3-hydroxyethylamino)-1 -methoxybenzene, 1 ,3- diaminobenzene, 1 ,3-bis(2,4-diaminophenoxy)propane, 3-ureidoaniline, 3-ureido-1 - dimethylaminobenzene, sesamol, 1 -3-hydroxyethylamino-3,4-methylenedioxybenzene, a- naphthol, 2-methyl-1 -naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N- methylindole, 2-amino-3-hydroxypyridine, 6-hydroxybenzomorpholine,
  • addition salts of the oxidation bases and couplers that may be used in the context of the invention are especially chosen 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 and preferably from 0.005% to 6% by weight relative to the total weight of the composition.
  • the dye composition according to the invention may also comprise one or more additional direct dyes other than the quinone direct dyes according to the present invention.
  • the additional direct dye(s) according to the invention are chosen from neutral, acidic or cationic nitrobenzene dyes, neutral, acidic or cationic azo direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes other than those of the present invention, azine direct dyes, triarylmethane direct dyes, azomethine direct dyes and natural direct dyes.
  • benzene-based direct dyes that may be used according to the invention, mention may be made, in a non-limiting manner, of the following compounds: ,4-diamino-2-nitrobenzene
  • azo direct dyes that may be used according to the invention, mention may be made of the cationic azo dyes described in patent applications WO 95/15144, WO- 95/01772 and EP-714954, the content of which forms an integral part of the invention.
  • azo direct dyes that may also be mentioned are the following dyes, described in the Colour Index International, 3rd edition: Disperse Red 17, Acid Yellow 9, Acid Black 1 , Basic Red 22, Basic Red 76, Basic Red 51 , Basic Yellow 57, Basic Brown
  • Acid Yellow 36 Acid Yellow 7
  • Acid Red 33 Acid Red 35
  • Basic Brown 17 Acid Yellow 23
  • Acid Orange 24 Disperse Black 9.
  • quinone direct dyes mention may be made of the following dyes: Disperse Red 15, Solvent Violet 13, Acid Violet 43, Disperse Violet 1 , Disperse Violet 4, Disperse Blue 1 , Disperse Violet 8, Disperse Blue 3, Disperse Red 1 1 , Acid Blue 62, Disperse Blue 7, Basic Blue 22, Disperse Violet 15, Basic Blue 99, and also the following compounds:
  • triarylmethane dyes that may be used according to the invention, 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.
  • azomethine dyes that may be used according to the invention, mention may be made of the following compounds:
  • the additional direct dye(s) may be present in the dye composition in a content ranging from 0.001 % to 10% by weight and preferably in a content ranging from 0.005% to 6% by weight, relative to the total weight of the composition.
  • the dye composition comprises one or more quinone direct dyes of formula (I) and one or more azomethine direct dyes.
  • the medium that is suitable for dyeing is a cosmetic medium generally formed from water or a mixture of water and of at least one organic solvent.
  • organic solvents include Ci-C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers, for instance 2- butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the solvents are present in proportions preferably of between 1 % and 99% by weight approximately and even more preferentially between 5% and 95% by weight approximately relative to the total weight of the dye composition.
  • the dye composition may also contain various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic or amphoteric surfactants or mixtures thereof, anionic, cationic, nonionic or amphoteric polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, solubilizers, conditioning agents, for instance volatile or non-volatile, modified or unmodified silicones such as amino silicones, film-forming agents, ceramides, preserving agents and opacifiers.
  • adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic or amphoteric surfactants or mixtures thereof, anionic, cationic, nonionic or amphoteric polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic
  • the above adjuvants are generally present in an amount, for each of them, of between 0.01 % and 20% by weight relative to the weight of the composition.
  • the pH of the dye composition in accordance with the invention is generally between 3 and 12 approximately, preferably between 5 and 1 1 approximately and even more particularly from 6 to 9. It may be adjusted to the desired value by means of acidifying or basifying agents commonly used in the dyeing of keratin fibres, or alternatively using standard buffer systems.
  • acidifying agents examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • mineral or organic acids for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • basifying agents examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines such as monoethanolamine, diethanolamine and triethanolamine, and also derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (III) below:
  • R a R b N-W-NR c R d in which W is a linear or branched (CrC 6 )alkylene group, which is optionally substituted, especially with one or more hydroxyl or amino groups, and preferably W propylene optionally substituted with a hydroxyl group or a Ci-C 4 alkyl radical;
  • R a , Rb, R c and R d which may be identical or different, represent a hydrogen atom or a C C 4 alkyl or d-C 4 hydroxyalkyl radical.
  • the dye composition according to the invention may be in various forms, such as in the form of liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibres, and especially human hair.
  • the invention also relates to the use of the dye composition as defined previously for dyeing keratin fibres, in particular human keratin fibres such as the hair.
  • the dyeing process according to the present invention consists in applying to wet or dry keratin fibres a dye composition as defined previously, comprising at least one compound of formula (I) or (II), preferably (I), for a time that is sufficient to obtain the desired coloration, and the fibres are then rinsed, optionally washed with shampoo and rinsed again, and the resulting fibres are dried or left to dry.
  • the leave-on time for the dye composition is between 1 and 60 minutes, preferably between 5 and 40 minutes and even more preferably between 10 and 30 minutes.
  • the dye composition is generally applied to the keratin fibres at room temperature, preferably between 25 and 55°C.
  • the dye composition according to the invention is applied to the keratin fibres in the presence of one or more chemical oxidizing agents for a time that is sufficient to obtain the desired lightening.
  • the chemical oxidizing agent may be present in the dye composition or may be used separately in a cosmetic composition.
  • the chemical oxidizing agent is used separately in a cosmetic composition.
  • the present invention also relates to a process for lightening keratin fibres, in particular human keratin fibres such as the hair, in which (i) the dye composition as defined previously, free of chemical oxidizing agent, and (ii) a cosmetic composition comprising one or more chemical oxidizing agents are applied to the said fibres; compositions (i) and (ii) being applied to the said keratin fibres sequentially or simultaneously for a time that is sufficient to obtain the desired lightening, and the fibres are then rinsed, optionally washed with shampoo and rinsed again, and the resulting fibres are dried or left to dry.
  • the term "sequentially” means that the oxidizing composition is applied before or after the dye composition, i.e. as a pretreatment or a post-treatment, preferably as a post-treatment.
  • the chemical oxidizing agents used are chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids, and oxidase enzymes (with the possible cofactors thereof), among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases, and 4-electron oxygenases, for instance laccases.
  • the chemical oxidizing agent is preferably hydrogen peroxide.
  • the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined previously.
  • the pH of the oxidizing composition containing the chemical oxidizing agent is such that, after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibres preferably ranges between 3 and 12 approximately, even more preferentially between 5 and 1 1 and even more particularly between 6 and 8.5. It may be adjusted to the desired value by means of acidifying or basifying agents usually used in the dyeing of keratin fibres and as defined previously.
  • the present invention also relates to compounds of leuco type of formula (II) below, organic or mineral acid or base salts thereof, tautomeric forms, optical isomers or ge of:
  • n, Y and Ri in formula (II) of the compounds of leuco type correspond to those indicated in formula (I) of the direct dyes.
  • the compounds of leuco type corresponding to formula (II) are generally obtained by reacting the compounds of quinone type of formula (I) with a reducing agent according to the reaction scheme below:
  • the compounds of leuco type of formula (II) are used as precursors of the direct dyes of formula (I).
  • the compounds of leuco type of formula (II) are chosen from the compounds corresponding to the reduced form of the quinone direct dyes (1 ) to (5) as defined previously, and also mixtures thereof.
  • the dye composition comprises one or more quinone direct dyes of formula (II) corresponding to the reduced form of those chosen from the compounds of formula (1 ) mentioned previously.
  • the invention relates to a cosmetic composition
  • a cosmetic composition comprising one or more compounds of leuco type of formula (II) as defined previously.
  • the present invention also relates to a dyeing process in which a cosmetic composition comprising one or more compounds of leuco type of the abovementioned formula (II) is applied to keratin fibres in the presence of one or more oxidizing agents for a time that is sufficient to develop the desired coloration, after which the fibres are rinsed, optionally washed with shampoo and rinsed again, and the resulting fibres are dried or left to dry.
  • a cosmetic composition comprising one or more compounds of leuco type of the abovementioned formula (II) is applied to keratin fibres in the presence of one or more oxidizing agents for a time that is sufficient to develop the desired coloration, after which the fibres are rinsed, optionally washed with shampoo and rinsed again, and the resulting fibres are dried or left to dry.
  • the dyeing operation using the leuco compounds of formula (II) is performed with atmospheric oxygen.
  • Simple exposure to air of the keratin fibres treated with the composition comprising the compound(s) of leuco type makes it possible to generate the colouring species and, consequently, to colour the fibres.
  • the oxidizing agent(s) may be applied simultaneously or sequentially to the cosmetic composition comprising the compounds of leuco type.
  • the dyeing process is a sequential process which consists, in a first stage, in applying to the keratin fibres, especially human keratin fibres such as the hair, one or more leuco compounds of formula (II), and then in revealing the colour by applying an oxidizing composition comprising one or more chemical oxidizing agents.
  • This process especially makes it possible to perform clean colorations, i.e. colorations that do not stain or stain only very sparingly linen and clothing, since the first composition uses compounds of formula (II) that are uncoloured or very sparingly coloured, and the colour is then revealed once the said colourless compounds (II) have been applied to the hair, so that the staining of fabrics is avoided during the process.
  • the cosmetic composition comprising the chemical oxidizing agent(s) may be applied to the keratin fibres before, simultaneously with or after the cosmetic composition comprising the compounds of leuco type of formula (II) according to the invention.
  • a ready-to-use composition which results from the mixing of a cosmetic composition comprising one or more compounds of leuco type of the abovementioned formula (II) and of a cosmetic composition comprising one or more chemical oxidizing agents is applied to the keratin fibres.
  • the invention relates to a composition, in particular for dyeing keratin fibres such as the hair, comprising one or more compounds of formula (II) as defined previously and optionally comprising one or more chemical oxidizing agents.
  • the ready-to-use composition that is thus applied to the keratin fibres may be in various forms, such as in the form of liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibres, and in particular human hair.
  • the leave-on time for the composition(s) ranges from 1 to 60 minutes, preferably from 5 to 40 minutes and even more preferentially from 10 to 30 minutes.
  • the cosmetic composition comprising such compounds of leuco type is generally applied to the keratin fibres at room temperature, preferably between 25 and 55°C.
  • the present invention also relates to a multi-compartment device or "kit” comprising a first compartment containing a cosmetic composition comprising one or more dyes of formula (I) as defined previously or containing one or more compounds of leuco type of formula (II) as defined previously, and optionally a second compartment comprising one or more chemical oxidizing agents.
  • the invention relates to a multi-compartment dyeing device or "kit” comprising a first compartment containing a cosmetic composition comprising one or more direct dyes of formula (I) as defined previously or containing one or more compounds of leuco type of formula (II) as defined previously, and a second compartment comprising one or more chemical oxidizing agents.
  • the invention relates to a multi-compartment dyeing device or "kit” comprising a first compartment containing a cosmetic composition comprising one or more direct dyes of formula (I) as defined previously, free of chemical oxidizing agent, and a second compartment containing a cosmetic composition comprising one or more chemical oxidizing agents.
  • the invention also relates to a multi-compartment dyeing device or "kit” comprising a first compartment containing a cosmetic composition comprising one or more compounds of leuco type of the abovementioned formula (II), and a second compartment containing a cosmetic composition comprising one or more chemical oxidizing agents.
  • the device may comprise at least one compartment comprising a cosmetic composition comprising one or more compounds of leuco type of the abovementioned formula (II).
  • composition comprising the compound(s) of leuco type as defined above is applied to the keratin fibres, which become coloured due to their exposure to air.
  • the devices mentioned above are suitable for dyeing keratin fibres.
  • the evaluation of the coloration can be done visually or read on a spectrocolorimeter (such as Minolta CM3600d, illuminant D65, angle 10°, SCI values) for the L * , a * , b * colorimetric measurements.
  • L * represents the intensity of the color
  • a * indicates the green/red color axis
  • b * indicates the blue/yellow color axis.
  • the lower the value of L the darker or more intense the color.
  • the higher the value of a * the redder the shade; the higher the value of b * , the yellower the shade.
  • ⁇ * J( L * - L o 7 + ( a * - a 0 7 + ( b * - b 0 7
  • L * , a * and b * represent the values measured after dyeing the natural hair comprising 90% of white hairs and L 0 * , a 0 * and b 0 * represent the values measured for the untreated natural hair comprising 90% of white hairs.
  • L * , a * and b * represent the values measured after dyeing the natural hair comprising 90% of white hairs and L 0 * , a 0 * and b 0 * represent the values measured after dyeing the permed or sensibilised hair.
  • the lowest ⁇ * the best homogeneity of the hair color.
  • ⁇ * is also calculated for the L 0 * , a 0 * , b 0 * and L * , a * , b * measured of the locks before and after exposure to the light, respectively.
  • 1 .25 g of the resulting mixture are applied to a lock of 0.25 g of grey hair containing 90% white hairs. After a leave-on time of 30 minutes at room temperature, the lock is rinsed, washed with a standard shampoo, rinsed again and then dried.
  • the colour obtained with the lock thus treated is a very aesthetic golden brown. Furthermore, it appears that the colour is uniform along the fibre.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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Abstract

La présente invention concerne des colorants directs de quinone portant un groupe aniline encombré de formule (I) et leurs formes leuco de formule (II), ainsi que leur utilisation pour la coloration de fibres de kératine, en particulier des fibres de kératine humaines telles que les cheveux, dans la formule (I) ou (II) n, R1 et Y sont tels que définis dans la description. Les composés de formule (I) selon l'invention peuvent ainsi donner des colorations puissantes, chromatiques et modérément sélectives qui sont résistantes aux divers facteurs d'attaque auxquels les fibres de kératine peuvent être soumises, tels que le climat peu clément, la lumière, le lavage et la transpiration.
PCT/EP2014/060836 2013-05-29 2014-05-26 Colorants directs de quinone portant un groupe aniline encombré, composition de colorant comprenant au moins un tel colorant, procédé de mise en œuvre associé et leur utilisation WO2014191354A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1354862A FR3006179B1 (fr) 2013-05-29 2013-05-29 Colorants directs quinoniques a groupe aniline encombre, composition tinctoriale comprenant au moins un tel colorant, procede de mise en œuvre et utilisation
FR1354862 2013-05-29

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WO2014191354A1 true WO2014191354A1 (fr) 2014-12-04

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* Cited by examiner, † Cited by third party
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GB1026978A (en) 1962-03-30 1966-04-20 Schwarzkopf Verwaltung G M B H Method of dyeing hair
GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
FR2047932A1 (fr) 1969-06-25 1971-03-19 Oreal
FR2056799A5 (fr) 1969-08-11 1971-05-14 Oreal
FR2106661A5 (fr) 1970-09-18 1972-05-05 Oreal
FR2121101A5 (fr) 1970-12-30 1972-08-18 Oreal
FR2165965A1 (fr) 1971-07-14 1973-08-10 Oreal
FR2189380A1 (fr) 1972-06-21 1974-01-25 Oreal
FR2234277A1 (fr) 1973-06-22 1975-01-17 Oreal
DE2359399A1 (de) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Haarfaerbemittel
FR2262023A1 (fr) 1974-02-22 1975-09-19 Oreal
US4023926A (en) * 1972-06-21 1977-05-17 Societe Anonyme Dite: L'oreal Diaminobenzoquinones in hair dye compositions
FR2359182A1 (fr) * 1976-07-21 1978-02-17 Oreal Compositions liquides de colorants destinees a la teinture des cheveux
GB1565105A (en) * 1976-07-21 1980-04-16 Oreal Liquid dyestuff compositions intended for dyeing hair
JPS63169571A (ja) 1987-01-06 1988-07-13 Nec Corp ト−ン検出装置
DE3843892A1 (de) 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
WO1994008969A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Procede de production de derives de 4,5-diaminopyrazole, leur utilisation pour la teinture des cheveux, et nouveaux derives de pyrazole
WO1994008970A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Colorants d'oxydation pour cheveux, renfermant des derives du 4,5-diaminopyrazole, nouveaux derives du 4,5-diaminopyrazole et leur procede de fabrication
WO1995001772A1 (fr) 1993-07-05 1995-01-19 Ciba-Geigy Ag Procede de teinture de fibres keratiniques
WO1995015144A1 (fr) 1993-11-30 1995-06-08 Ciba-Geigy Ag Colorants cationiques pour fibres keratiniques
WO1996015765A1 (fr) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation
EP0714954A2 (fr) 1994-11-03 1996-06-05 Ciba-Geigy Ag Colorants cationiques glyoxalin azoiques
FR2733749A1 (fr) 1995-05-05 1996-11-08 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
EP0770375A1 (fr) 1995-10-21 1997-05-02 GOLDWELL GmbH Composition pour la teinture des cheveux
DE19543988A1 (de) 1995-11-25 1997-05-28 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate
FR2801308A1 (fr) 1999-11-19 2001-05-25 Oreal COMPOSITIONS DE TEINTURE DE FIBRES KERATINIQUES CONTENANT DE DES 3-AMINO PYRAZOLO-[1,(-a]-PYRIDINES, PROCEDE DE TEINTURE, NOUVELLES 3-AMINO PYRAZOLO-[1,5-a]-PYRIDINES
FR2886136A1 (fr) 2005-05-31 2006-12-01 Oreal Composition pour la teinture des fibres keratiniques comprenant au moins un derive de diamino-n,n-dihydro- pyrazolone et un colorant d'oxydation cationique

Patent Citations (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1026978A (en) 1962-03-30 1966-04-20 Schwarzkopf Verwaltung G M B H Method of dyeing hair
GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
FR2047932A1 (fr) 1969-06-25 1971-03-19 Oreal
FR2056799A5 (fr) 1969-08-11 1971-05-14 Oreal
FR2106661A5 (fr) 1970-09-18 1972-05-05 Oreal
FR2121101A5 (fr) 1970-12-30 1972-08-18 Oreal
FR2165965A1 (fr) 1971-07-14 1973-08-10 Oreal
FR2189380A1 (fr) 1972-06-21 1974-01-25 Oreal
US4023926A (en) * 1972-06-21 1977-05-17 Societe Anonyme Dite: L'oreal Diaminobenzoquinones in hair dye compositions
FR2234277A1 (fr) 1973-06-22 1975-01-17 Oreal
DE2359399A1 (de) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Haarfaerbemittel
FR2262023A1 (fr) 1974-02-22 1975-09-19 Oreal
FR2359182A1 (fr) * 1976-07-21 1978-02-17 Oreal Compositions liquides de colorants destinees a la teinture des cheveux
GB1565105A (en) * 1976-07-21 1980-04-16 Oreal Liquid dyestuff compositions intended for dyeing hair
JPS63169571A (ja) 1987-01-06 1988-07-13 Nec Corp ト−ン検出装置
DE3843892A1 (de) 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
WO1994008969A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Procede de production de derives de 4,5-diaminopyrazole, leur utilisation pour la teinture des cheveux, et nouveaux derives de pyrazole
WO1994008970A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Colorants d'oxydation pour cheveux, renfermant des derives du 4,5-diaminopyrazole, nouveaux derives du 4,5-diaminopyrazole et leur procede de fabrication
WO1995001772A1 (fr) 1993-07-05 1995-01-19 Ciba-Geigy Ag Procede de teinture de fibres keratiniques
WO1995015144A1 (fr) 1993-11-30 1995-06-08 Ciba-Geigy Ag Colorants cationiques pour fibres keratiniques
EP0714954A2 (fr) 1994-11-03 1996-06-05 Ciba-Geigy Ag Colorants cationiques glyoxalin azoiques
WO1996015765A1 (fr) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation
FR2733749A1 (fr) 1995-05-05 1996-11-08 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
EP0770375A1 (fr) 1995-10-21 1997-05-02 GOLDWELL GmbH Composition pour la teinture des cheveux
DE19543988A1 (de) 1995-11-25 1997-05-28 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate
FR2801308A1 (fr) 1999-11-19 2001-05-25 Oreal COMPOSITIONS DE TEINTURE DE FIBRES KERATINIQUES CONTENANT DE DES 3-AMINO PYRAZOLO-[1,(-a]-PYRIDINES, PROCEDE DE TEINTURE, NOUVELLES 3-AMINO PYRAZOLO-[1,5-a]-PYRIDINES
FR2886136A1 (fr) 2005-05-31 2006-12-01 Oreal Composition pour la teinture des fibres keratiniques comprenant au moins un derive de diamino-n,n-dihydro- pyrazolone et un colorant d'oxydation cationique

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