WO2004043417A2 - Composition pour colorer des fibres de keratine contenant un precurseur de couleur et une enzyme ayant l'activite de la nitroreductase et procede d'utilisation de cette composition - Google Patents

Composition pour colorer des fibres de keratine contenant un precurseur de couleur et une enzyme ayant l'activite de la nitroreductase et procede d'utilisation de cette composition Download PDF

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Publication number
WO2004043417A2
WO2004043417A2 PCT/EP2003/015018 EP0315018W WO2004043417A2 WO 2004043417 A2 WO2004043417 A2 WO 2004043417A2 EP 0315018 W EP0315018 W EP 0315018W WO 2004043417 A2 WO2004043417 A2 WO 2004043417A2
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Prior art keywords
composition
composition according
amino
nitro
enzyme
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PCT/EP2003/015018
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English (en)
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WO2004043417A3 (fr
Inventor
Hervé Burgaud
Rui Pereira
Eric Metais
Andrew Greaves
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L'oreal
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Priority claimed from FR0214250A external-priority patent/FR2847161B1/fr
Application filed by L'oreal filed Critical L'oreal
Priority to AU2003300240A priority Critical patent/AU2003300240A1/en
Publication of WO2004043417A2 publication Critical patent/WO2004043417A2/fr
Publication of WO2004043417A3 publication Critical patent/WO2004043417A3/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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/606—Nucleosides; Nucleotides; Nucleic acids
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66—Enzymes

Definitions

  • the present invention relates to a composition for dyeing keratin fibres, containing at least one dye precursor, an enzyme with nitroreductase activity and an electron donor.
  • oxidation bases such as ortho- or para- phenylenediamines, ortho- or para-aminophenols and heterocyclic compositions.
  • oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds by a process of oxidative condensation.
  • oxidation bases may be varied by combining them with couplers or coloration modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenpls and certain heterocyclic compounds such as indole compounds.
  • couplers or coloration modifiers the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenpls and certain heterocyclic compounds such as indole compounds.
  • couplers or coloration modifiers the variety of molecules used as oxidation bases and couplers allows a wide range of colours to be obtained. It is often difficult, using conventional methods of reduction, to obtain these oxidation bases and aromatic amino couplers from the corresponding nitrated species.
  • the conventional methods of reduction use metals in the presence of acid or hydrogenation in the presence of a catalyst .
  • the aim of the present invention is to provide novel dye compositions based on dye precursors which make it possible to obtain oxidation bases and aromatic amino couplers at the moment of dyeing the keratin fibres, or to obtain, in the presence of carbonyl derivatives, coloured species for example of the azo or azomethine type .
  • This aim is achieved with the present invention, which relates to a dye composition comprising, in a carrier suitable for dyeing, at least one dye precursor chosen from aromatic compounds substituted with one or more nitro, nitroso or hydroxyamino radicals, and an enzyme with nitroreductase activity capable of reducing the nitro, nitroso or hydroxylamine radicals to an amino radical in the presence of an electron donor.
  • composition of the present invention makes it possible to form, at the moment of application to the keratin fibres, oxidation bases and/or amino couplers required for the formation of the coloured species.
  • compositions according to the present invention make it possible to simplify the methods for synthesizing the oxidation bases and the aromatic amino couplers conventionally used for dyeing keratin fibres.
  • a subject of the invention is also a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, a dyeing kit and device, and also the use of this composition in cosmetics, in particular for dyeing keratin fibres .
  • the enzyme with reductase activity is an enzyme which, when it is in the presence of an electron donor, has the ability to donate 2 to 6 electrons so as to reduce hydroxyamino, nitroso or nitro groups to an amino group.
  • the electron' donor is also known, in the art, as a cofactor.
  • the enzymes are then referred to as cofactor-dependent enzymes.
  • the enzymes with nitroreductase activity can be free or in a carrier. They can be chosen from the diaphorases of enzyme nomenclature (see Enzyme Nomenclature, Academic Press Inc.; 1992, IUBMB) . Specifically, such enzymes are known for their nitroreductase activity.
  • the enzymes with nitroreductase activity used in the dye composition according to the invention may be derived from an extract or from a fraction of extract chosen from extracts of plants, of animals or of microorganisms (bacterium, fungus, yeast, microalga) or viruses, or of differentiated or dedifferentiated cells, obtained in vivo or in vitro, modified or not modified genetically, or which are synthetic (obtained by chemical or biotechnological synthesis) .
  • the enzyme with nitroreductase activity can be obtained from the genera Actinomycetes , Agrobacterium, Archaeoglobus , Bacillus, Brucella, Campylobacter, Caulobacter, Ceratophyllum, Chara, Clostridium, Corynebacterium, Deinococcus, Desulfovibrio, Enterobacter, Escherichia, Fusobacterium, Haemophilus, Helicobacter, Lactobacillus, Leishmania, Methanobacterium, Methanopyrus , Methanosarcina, Moorella, Mycobacterium, Myriophyllum, Phytoplasma, Pseudomonas, Ralstonia, Rhodococcus, Staphylococcus , Streptomyces,
  • Thermoanaerobacter Vibrio, Xanthomonas, Yersinia, Typha, Sorghum, Zea, Glycine, Tamarix, Cyperus, Medicago, Brassica, Altemanthera , Populus, Lysopersicon, Dioscoria, Curcubita, Nicotiana, Spinacia, Salmonella.
  • the enzyme with nitroreductase activity obtained from E. coli is described in patent application EP 530 263.
  • Other enzymes with nitroreductase activity which are useful in the composition of the present invention are described in WO 00/047525, and also in the publications -Journal of Bacteriology, July 1995, p. 3837-3842, Vol. 177, No. 13; Applied and Environmental Microbiology, Jan. 1998, p. 246-252, Vol. 64, No. 1; The Journal of Biological Chemistry, p. 23922-23928, 1998, col. 273, No. 37; Journal of Bacteriology, Mar. 2001, p. 1780-1783, Vol. 183, No. 5.
  • the concentration of enzyme with nitroreductase activity which is useful in the dye composition is between 0.005% and 40% by weight relative to the total weight of said composition, and preferably between 0.05% and 10% by weight relative to the weight of this composition.
  • These enzymes with nitroreductase activity preferably use electron donors of the reduced nicotinamide adenine dinucleotide (NADH) and reduced nicotinamide adenine dinucleotide phosphate (NADPH) type. These enzymes can also use other electron donors, such as reduced pyridiniums, for example reduced nicotinamide or reduced 1-methylnicotinamide.
  • NADH reduced nicotinamide adenine dinucleotide
  • NADPH reduced nicotinamide adenine dinucleotide phosphate
  • the concentration of electron donor is generally between 0.005% and 40% by weight relative to the total weight of said composition, and preferably between 0.05% and 10% by weight relative to the total weight of the composition.
  • composition of the present invention may also contain a system for regenerating the electron donor which has been oxidized by the enzyme.
  • This regenerating system may be based on complementary enzyme systems, for example:
  • the amount of dye precursor is generally between 0.001 and 10% by weight relative to the total weight of the composition.
  • the dye precursor is a benzene or naphthalene precursor
  • it may be chosen from nitrobenzenes, hydroxyaminobenzene, nitrophenols, hydroxyaminophenols and nitrosoanilines .
  • benzene dye precursors mention may be made of ortho-nitroaniline, meta-nitroaniline, para-nitroaniline, 4-fluoronitrobenzene, 1, 4-dinitrobenzene, 2-amino- 5-nitrobenzene, 1, 3-dinitrobenzene, 2-amino- 3 -nitrobenzene, 2-amino-3, 5-dinitrobenzene, 2-amino- 3-nitro-6-alkoxybenzene, 2-amino-5-nitro- 6-alkoxybenzene, N,N-dimethyl-4-nitrosoaniline and 1- (hydroxyamino) -5-nitronaphthalene.
  • the dye precursor when it is a heteroaromatic precursor, it may be chosen from nitropyridines, nitropyrazoles, nitropyrimidines and their nitroso and hydroxyamino equivalents.
  • heteroaromatic dye precursors mention may be made of 3-nitropyridines such as 3, 5-dinitropyridin-4-amine, nitropyrimidines such as 4, 6-diamino-5-nitropyrimidine and 4-amino- 2, 6-dihydroxy-5-nitropyrimidine, nitropyrazoles such as l-ethyl-4-nitroso-lH-pyrazol-5-amine and 3-amino- 4-nitro-lH-pyrazole, 1, 3-dimethyl-4-nitro-lH-pyrazol- 5-amine, N- (3-methyl-4-nitro-l-phenyl-lH-pyrazol- 5-yl) ydroxylamine, 5-hydrazino-l, 3-dimethyl-4-nitro- lH-pyrazole, 3-methyl-4, 5-dinitro
  • R-NH 2 CcOoloured species may be of the para-phenylenedia ine, ortho-phenylenediamine, para-aminophenol, ortho- aminophenol, meta-diphenol, pyridine, pyrimidine, pyrazole, meta-aminophenol, meta-phenylenediamine, pyridine or indole type .
  • aromatic amines may be bases and couplers conventionally used for hair dyeing.
  • the oxidation bases and the couplers RNH 2 thus obtained form, in the presence of an oxidizing agent which may be oxygen from the air, by oxidative condensation, dyes which make it possible to permanently dye keratin fibres.
  • an oxidizing agent which may be oxygen from the air, by oxidative condensation, dyes which make it possible to permanently dye keratin fibres.
  • RNH 2 reacts with a carbonyl compound to give a coloured species of the azo or azomethine dye type.
  • carbonyl compounds useful for forming the coloured species mention may be made of those conventionally used in coloured reactions. In particular, mention may be made of those described in the following documents EP 502 784, FR 2763241, DE 10047480, WO 0197764,
  • carbonyl compounds may be mono- or polycarbonylated, they may be aromatic, heteroaromatic, ketone and/or aldehyde compounds.
  • the composition of the present invention may also contain oxidation bases and couplers which are conventional in dyeing.
  • the oxidation bases which may be added to the composition of the present invention are, for example, para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 2, 3-dimethyl-para-phenylenediamine, 2, 6-dimethyl-para- phenylenediamine, 2 , 6-diethyl-para-phenylenediamine, 2, 5-dimethyl-para-phenylenediamine, N,N-dimethyl-para- phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N- diethyl-3-methylaniline, N,N-bis ( ⁇ -hydroxyethyl) -para- phenylenediamine, 4-N,N-bis ( ⁇ -hydroxyethyl) amino- 2-methylaniline, 4-N,N-bis ( ⁇ -N-bis (
  • bisphenylalkylenediamines mention may be made, by way of example, of N,N'-bis( ⁇ - hydroxyethyl) -N,N' -bis (4' -aminophenyl) -1, 3-diamino- propanol, N,N' -bis ( ⁇ -hydroxyethyl) -N,N' -bis (4' - aminophenyl) ethylenediamine, N,N' -bis (4-aminophenyl) - tetramethylenediamine, N,N' -bis ( ⁇ -hydroxyethyl) -N,N' - bis (4-aminophenyl) tetramethylenediamine, N,N' -bis (4- methylaminophenyl) tetramethylenediamine, N,N'- bis (ethyl) -N,N' -bis (4' -amino-3' -methylphenyl) ethylene- di
  • para-aminophenol examples include para-aminophenol, 4-amino- 3-methylphenol, 4-amino-3-fluorophenol, -amino- 3- (hydroxymethyl) phenol, 4-amino-2-methylphenol, 4-amino-2- (hydroxymethyl) phenol, 4-amino-2- (methoxy- methyl) phenol, 4-amino-2- (aminomethyl) phenol, 4-amino- 2- ( ⁇ -hydroxyethylaminomethyl) phenol and 4-amino-
  • 2-fluorophenol and their addition salts with an acid.
  • ortho-aminophenols mention may be made, by way of example, of 2-aminophenol, 2-amino- 5-methylphenol, 2-amino-6-methylphenol and 5-acetamido- 2-aminophenol, and their addition salts with an acid.
  • heterocyclic bases mention may be made, by way of example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2 , 5-diaminopyridine, 2- (4-methoxyphenyl) amino- 3-aminopyridine and 3, -diaminopyridine, and their addition salts with an acid.
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2 359 399; JP 88-169 571; JP 05 163 124; EP 0 770 375 or patent application WO 96/15765, such as 2-hydroxy-4, 5, 6-triaminopyrimidine or 2, 4-dihydroxy- 5, 6-diaminopyrimidine, and the pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of pyrazolo [1, 5-a] pyrimidine-3, 7-diamine; 2, 5-dimethylpyrazolo [1, 5-a] pyrimidine-3 , 7-diamine; pyrazolo [1, 5-a] pyrimidine-3, 5-diamine; i
  • the dye composition in accordance with the invention may also contain one or more direct dyes which may in particular be chosen from dyes of the benzene series, cationic direct dyes, and azomethine, methine and azo direct dyes.
  • the medium suitable for dyeing also referred to. as dye carrier, generally consists of water or of a mixture of water and at least one organic solvent for solubilizing the compounds which would not be sufficiently soluble in water.
  • organic solvent mention may, for example, be made of C ⁇ -C 4 lower alcohols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and also aromatic alcohols such as benzyl alcohol or phenoxyethanol , and mixtures thereof.
  • the solvents may be present in proportions preferably of between 1 and 40% by weight approximately, relative to the total weight of the dye composition.
  • the dye composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, conditioning agents such as, for example, modified or unmodified, volatile or non-volatile silicones, film-forming agents, ceramides, preserving agents or opacifiers.
  • adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic,
  • the pH of the dye composition in accordance ' with the invention is generally between 3 and 12 approximately, and preferably between 6 and 10 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents conventionally used in the dyeing of keratin fibres, or else alternatively using conventional buffer systems.
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids .
  • basifying agents mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and also derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (III) below:
  • W is a propylene residue optionally substituted with a hydroxyl group or a C ⁇ -C 4 alkyl radical
  • Ra, Rb, Re and Rd which may be identical or different, represent a hydrogen atom, a C ! -C 4 alkyl radical or a C ⁇ -C 4 hydroxyalkyl radical.
  • the dye composition according to the invention may be in diverse forms, such as in the form of liquids, of creams or of gels, or in any other form suitable for dyeing keratin fibres and in particular human hair.
  • a subject of the invention is also a kit for dyeing keratin fibres, which comprises a first composition which comprises an enzyme with nitroreductase activity and an electron donor as defined above, a second composition which contains one or more dye precursors and, optionally, a third composition which contains an oxidizing agent.
  • a subject of the invention is also a process for dyeing keratin fibres, and in particular human keratin fibres such as the hair, such that at least one composition according to the invention is applied to these fibres for a period of time sufficient to develop the desired coloration.
  • the coloration of the keratin fibres can be obtained with oxygen from the air or using an oxidizing agent.
  • the oxidizing agents conventionally used for the oxidation dyeing of keratin fibres are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, peracids and oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
  • this process comprises a preliminary step which consists in mixing a first composition which contains an enzyme with nitroreductase activity in solution or in a carrier and an electron donor, a second composition which comprises the dye precursor as defined above and, optionally, a third composition which contains an oxidizing agent, and in applying this mixture to the keratin fibres.
  • the oxidizing agent is used from an oxidizing composition containing it applied simultaneously or sequentially to the composition of t e invention.
  • the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
  • the pH of the oxidizing composition containing the 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, and even more preferably between 5 and 11. It may be adjusted to the desired value by means of acidifying or basifying agents conventionally used in the dyeing of keratin fibres and as defined above.
  • composition which is finally applied to the keratin fibres may be in diverse forms, such as in the form of liquids, of creams or of gels or in any other form suitable for dyeing keratin fibres, and in particular human hair.
  • a subject of the present invention is a device comprising a first compartment comprising an enzyme with nitroreductase activity and an electron donor as defined above, a second compartment which comprises the dye precursor as defined above and, optionally, a third compartment which comprises an oxidizing agent.
  • This device may be equipped with a means for delivering the desired mixture onto the hair, such as the devices described in patent FR-2 586 913 in > the applicant's name.
  • This composition is applied to a lock of natural grey hair containing 90% white hair, heated to 35°C.
  • the lock of hair is impregnated with 4-nitroblue tetrazolium hydrochloride monohydrate (NBT) .
  • NBT 4-nitroblue tetrazolium hydrochloride monohydrate
  • This composition is applied to a lock of natural grey hair containing 90% white hair, heated to 35°C.
  • the lock of hair is impregnated with 4-nitroblue tetrazolium hydrochloride monohydrate (NBT) . After an application time of 30 min at 35°C, the hair is rinsed, washed with a standard shampoo and then dried. The lock of hair is then coloured mauve/brown.
  • NBT 4-nitroblue tetrazolium hydrochloride monohydrate
  • composition 25 mg/ml nitroreductase ⁇ E. coli) 0.5 ml
  • Diaphorase (10 mg protein/ml) 0.25 ml
  • composition A The following compositions are prepared Composition A
  • composition B 2 mM 2-hydroxy-3-nitropyridine 10 ml This composition A is incubated at ambient temperature until the nitro derivative is reduced to an amine. The insoluble portion is filtered off and 6.8 ml of the filtrate obtained are mixed with the composition B below.
  • Composition B
  • composition thus obtained is applied to a lock of natural grey hair containing 90% white hair. After an application time of 30 minutes, the hair is rinsed, washed with a standard shampoo and then dried. The lock of hair is then coloured chestnut brown.
  • Example 6 The following compositions are prepared
  • composition A 2 mM 1, 3-dinitrobenzene 10 ml
  • This composition A is incubated at ambient temperature until the nitro derivative is reduced to an amine.
  • the insoluble portion is filtered off and 6.8 ml of the filtrate obtained are mixed with the composition B below.
  • Composition B 10 mM 5-methylpyrazolo [1, 5-a]pyrimidine-3, 7-diamine dihydrochloride in a buffer containing 0.1 M triethanolamine, pH 8 2.3 ml
  • composition thus obtained is applied to a lock of natural grey hair containing 90% white hair. After an application time of 30 minutes, the hair is rinsed, washed with a standard shampoo and then dried. The lock of hair is then coloured iridescent brown.
  • composition A The following compositions are prepared Composition A
  • composition A is incubated at ambient temperature until the nitro derivative is reduced to an amine.
  • the insoluble portion is filtered off and 6.8 ml of the filtrate obtained are mixed with the composition B below.
  • Composition B 5-amino-2-methylphenol in a 0.1 M triethanolamine buffer, pH 8 2.3 ml
  • compositions are prepared Composition A Ground Sorghum bicolor root material 1 g NADH 20 mg
  • composition A is incubated at ambient temperature until the nitro derivative is reduced to an amine.
  • the insoluble portion is filtered off and 6.8 ml of the filtrate obtained are mixed with the composition B below.
  • Composition B 10 mM 5-methylpyrazol [1, 5-a]pyrimidine-3, 7-diamine dihydrochloride in a 0.1 M triethanolamine buffer, pH 8 2.3 ml
  • composition thus obtained is applied to a lock of natural grey hair containing 90% white hair. After an application time of 30 minutes, the hair is rinsed, washed with a standard shampoo and then dried. The lock of hair is then coloured purplish brown.
  • compositions are prepared Composition A Ground Sorghum bicolor root material 1 g NADH 20 mg
  • composition A is incubated at ambient temperature until the nitro derivative is reduced to an amine.
  • the insoluble portion is filtered off and 6.8 ml of the filtrate obtained are mixed with the composition B below.
  • Composition B 10 mM 6-hydroxyethyloxy-l, 3-diaminobenzene in a 0.1 M triethanolamine buffer, pH 8 2.3 ml H 2 0 2 at 20 vol 0.9 ml
  • composition thus obtained is applied to a lock of natural grey hair containing 90% white hair. After an application time of 30 minutes, the hair is rinsed, washed with a standard shampoo and then dried. The lock of hair is then coloured grey/black.

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Abstract

La présente invention porte sur une composition destinée à colorer des fibres de kératine et contenant au moins un précurseur de couleur, une enzyme ayant l'activité de la nitroréductase et un donneur d'électrons. L'invention porte également sur un procédé de coloration de fibres de kératine au moyen de cette composition.
PCT/EP2003/015018 2002-11-14 2003-11-13 Composition pour colorer des fibres de keratine contenant un precurseur de couleur et une enzyme ayant l'activite de la nitroreductase et procede d'utilisation de cette composition WO2004043417A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003300240A AU2003300240A1 (en) 2002-11-14 2003-11-13 Composition for dyeing keratin fibres containing a dye precursor and an enzyme with nitroreductase activity

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0214250A FR2847161B1 (fr) 2002-11-14 2002-11-14 Composition de teinture des fibres keratiniques contenant un precurseur de colorant et une enzyme a activite nitroreductase et procede mettant en oeuvre cette composition
FR0214250 2002-11-14
US43171102P 2002-12-09 2002-12-09
US60/431,711 2002-12-09

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WO2004043417A2 true WO2004043417A2 (fr) 2004-05-27
WO2004043417A3 WO2004043417A3 (fr) 2004-07-15

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1859782A1 (fr) * 2006-05-24 2007-11-28 Henkel Kommanditgesellschaft auf Aktien Compositions pour la coloration et l'éclairicsement des cheveux comprenant des tétrazoles
EP1875892A2 (fr) * 2006-07-05 2008-01-09 Henkel Kommanditgesellschaft Auf Aktien Matériau d'éclaircissement et/ou de coloration contenant de pyrazoles

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998054349A1 (fr) * 1997-05-29 1998-12-03 Battelle Memorial Institute Procede de reduction controlee de composes nitroaromatiques par une reaction enzymatique utilisant des enzymes sensibles a l'oxygene du type nitroreductase
WO1999020235A1 (fr) * 1997-10-22 1999-04-29 L'oreal Composition de teinture des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
WO2001057237A2 (fr) * 2000-02-02 2001-08-09 Amersham Biosciences Uk Limited Procede et reactif de detection par fluorescence

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998054349A1 (fr) * 1997-05-29 1998-12-03 Battelle Memorial Institute Procede de reduction controlee de composes nitroaromatiques par une reaction enzymatique utilisant des enzymes sensibles a l'oxygene du type nitroreductase
WO1999020235A1 (fr) * 1997-10-22 1999-04-29 L'oreal Composition de teinture des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
WO2001057237A2 (fr) * 2000-02-02 2001-08-09 Amersham Biosciences Uk Limited Procede et reactif de detection par fluorescence

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DATABASE BIOSIS [Online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; XP002251167 Database accession no. PREV199900247340 *
DATABASE CAPLUS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002251168 retrieved from STN Database accession no. 1995:798172 *
DATABASE CAPLUS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002251169 retrieved from STN Database accession no. 1988:201027 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1859782A1 (fr) * 2006-05-24 2007-11-28 Henkel Kommanditgesellschaft auf Aktien Compositions pour la coloration et l'éclairicsement des cheveux comprenant des tétrazoles
EP1875892A2 (fr) * 2006-07-05 2008-01-09 Henkel Kommanditgesellschaft Auf Aktien Matériau d'éclaircissement et/ou de coloration contenant de pyrazoles
EP1875892A3 (fr) * 2006-07-05 2012-01-11 Henkel AG & Co. KGaA Matériau d'éclaircissement et/ou de coloration contenant de pyrazoles

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