Classifications

• • 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
  • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
  • A61K8/66—Enzymes
• • 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

• the subject of the invention is a dye composition
• a dye composition comprising an oxidation base of the diaminopyrazole type and an oxidizing agent of enzymatic nature of the oxidoreductase type.
• Another subject of the invention is the use of this composition for dyeing keratin fibers as well as the dyeing process using this composition.
• oxidation bases such as ortho or paraphenylenediamines, ortho or paraaminophenols and heterocyclic compounds.
• oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, through an oxidative condensation process, to colored compounds.
• couplers or color modifiers the latter being chosen in particular from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds such as as indole compounds.
• dyes must also make it possible to cover white hair, and finally be the least selective possible, that is to say allow to obtain the smallest possible color differences throughout the same keratin fiber, which is in general differently sensitized (ie damaged) between its tip and its root.
• Dye compositions are already known comprising, as the oxidation base, diaminopyrazole derivatives.
• patent application DE 3843892 describes dye compositions for dyeing keratinous fibers comprising 4,5-diaminopyrazole derivatives which can be substituted in position 2 by alkyl or hydroxyalkyl radicals.
• Patent application EP 692245 describes dye compositions comprising 4,5-diaminopyrazole derivatives associated with particular metaphenylenediamines.
• Patent application DE 19643059 describes dye compositions combining 4,5-diaminopyrazole derivatives with metaaminophenol and metaphenylenediamine couplers.
• Patent application DE 19646609 describes dye compositions combining 4,5-diaminopyrazole derivatives with benzoxazine couplers.
• the oxidation dyeing of keratin fibers is generally carried out in an alkaline medium, in the presence of an oxidizing agent, in general hydrogen peroxide.
• an oxidizing agent in general hydrogen peroxide.
• the use of alkaline media in the presence of hydrogen peroxide leads to a significant degradation of the fibers as well as a significant discoloration of the keratin fibers which is not always desirable.
• the aim of the present invention is to provide new dye compositions for dyeing keratin fibers which do not degrade keratin fibers, while being capable of generating intense colorings in varied shades, not very selective and particularly resistant.
• R 1 is an alkyl radical in substituted by one or more OR radicals, R being a C 6 -C 6 alkyl radical, and
• an enzymatic oxidizing agent chosen from (a) an enzymatic system comprising an oxidoreductase with 2 electrons and a donor for this oxidoreductase or (b) an oxidoreductase with 4 electrons.
• the invention also relates to a dyeing process using this composition.
• composition of the present invention for dyeing keratin fibers, in particular human keratin fibers such as the hair.
• composition of the present invention makes it possible in particular to obtain a coloration of chromatic keratin fibers, very powerful, not very selective and tenacious while avoiding the degradation of these fibers.
• alkyl means linear or branched radicals, for example methyl, ethyl, n-propyl, iso-propyl, butyl, etc.
• the 4,5-diaminopyrazole oxidation base of formula (I) is such that R1 represents an alkyl radical in CC ,, preferably C2-C4 substituted by an OR radical, R being a C r C 4 alkyl radical, preferably C1-C2.
• the oxidation base of formula (I) is 4,5-diamino-1- (2'-methoxyethyl) -pyrazole.
• the 2-electron oxidoreductase is chosen from pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases, uricases, choline oxidases, sarcosine oxidases, bilirubin oxidases and amino acid oxidases.
• the 2-electron oxidoreductase is preferably chosen from uricases of animal, microbiological or biotechnological origin. By way of example, mention may in particular be made of uricase extracted from boar liver, the uricase of Arthrobacter globiformis, as well as the uricase of Aspergillus flavus.
• the 2-electron oxidoreductase (s) can be used in pure crystalline form or in a diluted form in an inert diluent for said 2-electron oxidoreductase.
• the term “donor” is understood to mean the various substrates necessary for the functioning of the 2-electron redoxases.
• the nature of the donor for said enzyme varies depending on the nature of the 2-electron redoxase which is used.
• a donor for pyranose oxidases mention may be made of D-glucose, L-sorbose and D-xylose
• a donor for glucose oxidases mention may be made of D-glucose
• a donor for the glycerol oxidases mention may be made of glycerol and dihydroxyacetone
• lactate oxidase donors there may be mentioned lactic acid and its salts
• the donor for pyruvate oxidases mention may be made of pyruvic acid and its salts
• uricase donors mention may be made of uric acid and its salts
• a donor for the choline oxidases mention may be made of choline and its addition salts with an acid such as choline hydrochloride, and betaine aldehyde; as a donor for sarc
• the 2-electron oxidoreductase generally represents from 0.01 to 20%, preferably from 0.1 to 5% by weight of the total weight of the dye composition and the donor generally represents from 0.01 to 20%, preferably 0.1 to 5% by weight of the total weight of the dye composition.
• the amount of enzyme according to its activity.
• the enzymatic activity of the 2-electron oxidoreductases useful in the present invention can be defined from the oxidation of the donor under aerobic conditions.
• One unit U corresponds to the quantity of enzyme leading to the generation of one ⁇ mole of H 2 O 2 per minute at a pH of 8.5 and at a temperature of 25 ° C.
• the amount of 2-electron oxidoreductase according to the invention is between 10 and 10 ⁇ units U approximately per 100 g of dye composition.
• the 4-electron oxidoreductase (s) useful in the dye composition of the invention can in particular be chosen from laccases, tyrosinases, catechol oxidases and polyphenol oxidases.
• the oxidoreductase (s) with 4 electrons are chosen from laccases.
• laccases can in particular be chosen from laccases of plant origin, of animal origin, of fungal origin (yeasts, molds, fungi) or of bacterial origin, the organisms of origin being able to be mono- or multicellular. Laccases can also be obtained by biotechnology.
• laccases of vegetable origin mention may be made of laccases produced by plants carrying out chlorophyll synthesis, such as those indicated in patent application FR-A-2694018. Mention may in particular be made of the laccases present in the extracts of Anacardiaceae such as for example the extracts of Magnifera indica, of Schinus molle or of Pleiogynium timoriense; in extracts from Podocarpaceae; of Rosmarinus off. ; Solanum tuberosum; Iris sp. ; from Coffea sp. ; Daucus carrota; of Vinca minor; Persea americana; Catharenthus roseus; from Musa sp.
• laccases of fungal origin possibly obtained by biotechnology, mention may be made of the laccase (s) derived from Polyporus versicolor, from Rhizoctonia practitionola and Rhus vernicifera as described for example in patent applications FR-A-2 112 549 and EP-A-504005; the laccases described in patent applications WO95 / 07988, WO95 / 33836, WO95 / 33837, WO96 / 00290, WO97 / 19998 and WO97 / 19999, such as for example the laccase (s) from Scytalidium, Polyporus pinsitus, Myceliophtora thermophila , Rhizoctonia solani, Pyricularia orizae, and their variants.
• laccase originating from Trametes versicolor, Fomes fomentarius, Chaetomium thermophile, Neurospora crassa, Colorius versicol, Botrytis cinerea, Rigidoporus lignosus, Phellinus noxius, Pleurotus ostreatus, Aspergillus nidulans, Podospora anserina, Agaricus bisporus, Ganoderma lucidum, Glomerella cingulata, Lactarius piperatus, Russula delica, Heterobasidion annosum, Thelephora terrestris, Cladosporium cladosporioides, Cerrena unicolor, Coholus hirsutus Coprinus cinereus, Panaeolus papilionaceus, Panaeolus sphinctrinus, Schizophyllum commune, Dichomitius squalens
• laccases of fungal origin possibly obtained by biotechnology, will be chosen.
• the enzymatic activity of laccases can be defined from the oxidation of syringaldazine under aerobic conditions.
• the Lacu unit corresponds to the quantity of enzyme catalyzing the conversion of 1 mmol of syringaldazine per minute at a pH of 5.5 and at a temperature of 30 ° C.
• the unit U corresponds to the quantity of enzyme producing an absorbance delta of 0.001 per minute, at a wavelength of 530 nm, using syringaldazine as substrate, at 30 ° C. and at a pH of 6, 5.
• the enzymatic activity of the laccases used according to the invention can also be defined from the oxidation of paraphenylenediamine.
• the ulac unit corresponds to the quantity of enzyme producing an absorbance delta of 0.001 per minute, at a wavelength of 496.5 nm, using paraphenylenediamine as substrate (64 mM), at 30 ° C and at a pH of 5.
• the oxidoreductase (s) with 4 electrons represent from 0.01 to 20% by weight approximately of the total weight of the dye composition, and preferably from 0.1 to 5% by weight approximately of this weight.
• the amount of laccase (s) present in the dye composition according to the invention varies according to the nature of the laccase (s) used.
• the amount of laccase (s) is between 0.5 and 2000 Lacu approximately (either between 10000 and 40.10 6 units U approximately or between 20 and 20.10 6 units ulac) per 100 g of dye composition.
• composition of the present invention may also comprise one or more additional oxidation bases conventionally used in oxidation dyeing other than those described above.
• additional oxidation bases are chosen from paraphenylenediamines, bisphenylalkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases other than those described above and their addition salts.
• paraphenylenediamines there may be mentioned by way of example, paraphenylenediamine, paratoluylenediamine, 2-chloro paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine, 2,5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N, N- bis- ( ⁇ - hydroxyethyl) paraphenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline, 2- ⁇ -hydroxyethyl paraphenyl
• paraphenylenediamine paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2- ⁇ -hydroxyethyloxy paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, NN-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 2-chloro paraphenylenediamine, 2- ⁇ -acetylaminoethyloxy paraphenylenediamine, and their addition salts with an acid are particularly preferred.
• 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-methyl-aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N, N ' -bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1, 8-bis- (2,5
• para-aminophenol there may be mentioned by way of example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4- amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
• para-aminophenol 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4- amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
• ortho-aminophenols there may be mentioned by way of example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their addition salts with an acid.
• heterocyclic bases for example, 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-diamino pyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine, 2,3-diamino 6-methoxy pyridine, 2- ( ⁇ -methoxyethyl) amino 3-amino 6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.
• pyridine oxidation bases useful in the present invention are the 3-amino pyrazolo- [1,5-a] -pyridine oxidation bases or their addition salts described for example in patent application FR 2801308.
• pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2359399; JP 88-169571; JP 05-63124; EP 0770375 or patent application WO 96/15765 such as 2,4,5,6-tetra-aminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2 , 4-dihydroxy 5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2750048 and among which mention may be made of pyrazolo- [1, 5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] - pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3,5-diamine;
• the oxidation base or bases present in the composition of the invention are generally each present in an amount of between 0.001 to 10% by weight approximately of the total weight of the dye composition, preferably between 0.005 and 6%.
• the composition according to the invention may contain one or more couplers conventionally used for dyeing keratin fibers. Among these couplers, mention may especially be made of metaphenylenediamines, meta-aminophenols, metadiphenols, naphthalene couplers, heterocyclic couplers and their addition salts.
• the coupler or couplers are each generally present in an amount of between 0.001 and 10% by weight approximately of the total weight of the dye composition, preferably between 0.005 and 6%.
• addition salts of the oxidation bases and of the couplers which can be used in the context of the invention are in particular chosen from addition salts with an acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates and addition salts with a base such as soda, potash, ammonia, amines or alkanolamines.
• an acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates
• a base such as soda, potash, ammonia, amines or alkanolamines.
• the dye composition in accordance with the invention may also contain one or more direct dyes which can in particular be chosen from nitro dyes from the benzenic series, azo direct dyes and methine direct dyes. These direct dyes can be of nonionic, anionic or cationic nature.
• the medium suitable for dyeing also called dye support, generally consists of water or of a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
• organic solvent mention may, for example, be made of lower C r C 4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
• the solvents are preferably present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
• 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 surfactants, amphoteric, zwitteric or mixtures thereof, anionic, cationic, nonionic polymers, amphoteric, zwitterionic or mixtures thereof, inorganic or organic thickeners, and in particular associative thickeners, anionic, cationic, nonionic and amphoteric polymers antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, agents preservatives, clouding agents.
• 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 according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers or even using conventional buffer systems.
• acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
• mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
• basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula (II) below:
• RF cd (ll) in which W is a propylene residue optionally substituted by a hydroxyl group or a C r C 4 alkyl radical;
• R a , R b , R c and R d identical or different, represent a hydrogen atom, an alkyl radical in C, ⁇ or hydroxyalkyl in 0, -0 4 .
• the dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair.
• the oxidation bases and the oxidoreductase (s) with 2 electrons or with 4 electrons are present within the same composition, and therefore the composition if it is stored before use must be free of gaseous oxygen, so as to avoid premature oxidation of the oxidation dye (s).
• the invention also relates to a process for dyeing keratin fibers and in particular human keratin fibers such as the hair, using the dye composition as defined above.
• the dye composition as defined above is applied to the fibers, for a time sufficient to develop the desired coloration.
• the fibers are then rinsed, optionally washed with shampoo, then dried.
• the application temperature is preferably between room temperature and 60 ° C and even more preferably between 35 ° C and 50 ° C.
• the time sufficient to develop the coloration on the keratin fibers is generally between 1 and 60 minutes and preferably between 5 and 30 minutes.
• Another object of the invention is a device with several compartments in which a first compartment contains a dye composition comprising an oxidation base of formula (I) and a second compartment contains an enzymatic oxidizing agent as defined above.
• These devices can be equipped with a means enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant.
• the compounds useful in the composition of the present invention are known compounds which can be obtained from general preparation methods known to those skilled in the art.
• the synthetic approach shown below is described in the literature up to intermediary (2) (JHP Juffermanns, C. L; Habraken; J. Org. Chem., 1986, 51, 4656; Klebe and al.; Synthesis, 1973, 294; R. H ⁇ ttel, F. B ⁇ chele; Chem. Ber.; 1955, 88, 1586.).
• the passage from compound 3 to compound 2 is carried out by means of a NI-yEtOH mixture.
• U unit (amount of uricase which oxidizes one ⁇ mol of uric acid per minute at 25 ° C and at pH 8.5 in a borate buffer)
• the mixture is applied to gray hair containing 90% white hairs, whether permanent or not, at a rate of 10 g per 1 g of hair. After 30 min. the hair is then rinsed, washed with a standard shampoo, rinsed again and dried.
• Hair color is assessed visually.
• the reflection on the wick is an intense coppery red.

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