Classifications

• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/347—Phenols
• • 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
  • 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
  • A61K8/415—Aminophenols
• • 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
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings

Definitions

• the subject of the invention is a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, comprising, in a medium suitable for dyeing,
• the third coupler at least one meta-aminophenol and / or one of its addition salts with an acid
• the subject of the invention is also the dyeing process using this composition.
• the subject of the invention is also the dyeing process using this composition.
• the 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 can be in differently sensitized effect (ie damaged) between its tip and its root
• the first object of the invention is therefore a composition for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair, characterized in that it comprises, in a medium suitable for dyeing - as first coupler, at least one derivative of 3,5-d ⁇ am ⁇ no pyndine corresponding to the following general formula (I)
• R T and R 2 identical or different, represent a C - * - C alkyl radical, monohydroxyalkyl in CC, or polyhydroxyalkyl in C 2 -C,
• R 3 represents a hydrogen atom, an alkyl radical in C * ⁇ -C l monohydroxyalkyle in C ⁇ -C 4 or polyhydroxyalkyle in C 2 -C 4 and / or one of its addition salts with an acid;
• the third coupler at least one meta-aminophenol and / or one of its addition salts with an acid
• the dye composition in accordance with the invention leads to powerful, very chromatic coloring, and having excellent resistance properties both with respect to atmospheric agents such as light and bad weather and with regard to perspiration and different treatments that the hair can undergo.
• the invention also relates to a process for the oxidation dyeing of keratin fibers using this dye composition.
• the dye composition preferably contains 2,6-dimethoxy-3,5-diaminopyhdin, and / or at least one of its addition salts with an acid.
• the 3,5-diaminopyridine derivative (s) of formula (I) which can be used as the first coupler in the dye composition according to the invention preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition , and even more preferably from 0.005 to 5% by weight approximately of this weight.
• the resorcinol which can be used as second coupler preferably represents from 0.0001 to 10% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 5% by weight approximately of this weight.
• - R 4 represents a hydrogen atom, an alkyl radical in C ⁇ -C, monohydroxyalkyle in C - * - C 4 or polyhydroxyalkyle in C 2 -C 4 ,
• R 5 represents a hydrogen atom, a C- ⁇ -C alkyl radical, C ⁇ -C alkoxy or a halogen atom chosen from chlorine, bromine or fluorine,
• R 6 represents a hydrogen atom, a C- ⁇ -C alkyl radical, C ⁇ -C alkoxy, C ** monohydroxyalkyl - C, C 2 -C 4 polyhydroxyalkyl, CC 4 monohydroxyalkoxy or C 4 polyhydroxyalkoxy 2 -C 4 .
• meta-aminophenols of formula (II) above there may be mentioned more particularly meta-aminophenol, 5-amino 2-methoxy phenol, 5-amino 2- ( ⁇ -hydroxyethyloxy) phenol, 5-amino 2-methyl phenol, 5-N- ( ⁇ -hydroxyethyl) amino 2-methyl phenol, 5-N- ( ⁇ -hydroxyethyl) amino 4-methoxy 2-methyl phenol, 5-amino 4-methoxy 2-methyl phenol, 5-amino 4-chloro 2-methyl phenol, 5-amino 2,4-dimethoxy phenol, 5- ( ⁇ -hydroxypropylamino) 2-methyl phenol, and their addition salts with an acid.
• the meta-aminophenol (s) which can be used as the third coupler preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 5% by weight approximately of this weight.
• para-phenylenediamines which can be used as oxidation base in the dye compositions in accordance with the invention, mention may in particular be made of the compounds of formula (III) below and their addition salts with an acid:
• R 7 represents a hydrogen atom, an alkyl radical in C * ⁇ -C 4 monohydroxyalkyl, C 1 -C 4 polyhydroxyalkyl, C 2 -C 4 alkoxy (C 1 -C 4) alkyl (C 1 - C 4 ), C ⁇ -C 4 alkyl substituted by a nitrogen group, phenyl or 4'-aminophenyl;
• - R 8 represents a hydrogen atom, an alkyl radical in CC, monohydroxyalkyle in C * ⁇ -C 4 , polyhydroxyalkyle in C 2 -C 4 , alkoxy (CC 4 ) alkyl (C ⁇ -C 4 ) or alkyl in CC 4 substituted by a nitrogen group;
• R 9 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, an alkyl radical in CC, monohydroxyalkyl in C- ⁇ -C 4 , hydroxyalkoxy in CC 4 , C 1 -C acetylaminoalkoxy, C ⁇ -C mesylaminoalkoxy or C- ⁇ -C 4 carbamoylaminoalkoxy,
• R 10 represents a hydrogen atom, a halogen atom or a C 1 -C 4 alkyl radical.
• nitrogen groups of formula (III) above mention may in particular be made of amino radicals, dialkyl (C 1 -C 4 ) amino, trialkyl (C 1 -C) amino, monohydroxyalky CrC-amino, imidazolinium and ammonium.
• para-phenylenediamines of formula (III) above there may be mentioned more particularly para-phenylenediamine, paratoluylenediamine, 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-methyl aniline, N, N-bis- ( ⁇ -hydroxyethyl) para-phenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline, 2-
• para-phenylenediamines of formula (III) above very particularly preferred is para-phenylenediamine, paratoluylenediamine, 2- ⁇ sopropyl para-phenylenediamine, 2- ⁇ -hydroxyethyl para-phenylenediamine, 2,6-dimethyl para-phenylenediamine, 2,6-methyl para-phenylenediamine, 2,3-dimethyl para-phenylenediamine, N, N-b ⁇ s- ( ⁇ -hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, and their addition salts with an acid
• the para-phenylenediamines preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition according to the invention, and even more preferably from 0.005 to 6% by weight approximately of this weight
• the dye composition in accordance with the invention may also contain, in addition to the compound (s) of formula (I) above, resorcinol and meta-aminophenols, one or more additional couplers which can be chosen from the couplers used conventionally in oxidation dyeing and among which there may be mentioned in particular substituted meta-diphenols, meta-phenylenediamines and heterocychic couplers such as for example the indo c derivatives, the indohnic derivatives, the py ⁇ dinic derivatives other than those of l invention and pyrazolones, and their acid addition salts
• couplers are more particularly chosen from 1, 3-d ⁇ hydroxy 2-methyl benzene, 4-chloro 1, 3-d ⁇ hydroxy benzene, 2,4-d ⁇ am ⁇ no l- ( ⁇ -hydroxyethyloxy) benzene, 2-am ⁇ no 4- ( ⁇ -hydroxyethylam ⁇ no) 1-methoxy benzene, 1, 3-d ⁇ am ⁇ no benzene, 1, 3-b ⁇ s- (2,4-d ⁇ am ⁇ nophenoxy) propane, sesamol, ⁇ -naphthol, 6-hydroxy indole, 4-hydroxy indole, 4-hydroxy N-methyl indole, 6-hydroxy indoline, 2,6-dihydroxy 4-methyl pyridine, 1-H 3-methyl pyrazole 5-one, 1-phenyl 3-methyl pyrazole 5-one, 3- (4-hydroxy-1-methyl-1 H-indol-5-ylmethyl) -1-methyl-pyr ⁇ d ⁇ n ⁇ um and their addition salts with an acid When they are present, these additional couplers
• the oxidation dye composition according to the invention may contain one or more additional oxidation bases which are preferably chosen from the oxidation bases conventionally used as an oxidation dye and among which mention may be made of bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocychic bases.
• para-aminophenol there may be mentioned more particularly 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.
• ortho-aminophenols mention may more particularly be made, by way of example, of 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 that may be mentioned more particularly by way of example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
• pyridine derivatives mention may more particularly 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 acid addition salts.
• pyrimidine derivatives mention may be made more particularly of the compounds described for example in German patents DE 2,359,399 or Japanese patents JP 88-169,571 and JP 91-10659 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.
• pyrazole derivatives mention may more particularly be made of the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 such as 4,5-diamino 1-methyl pyrazole, 3,4-diamino pyrazole, 4,5-diamino 1- (4'-chlorobenzyl) pyrazole, 4,5-diamino 1, 3-dimethyl pyrazole, 4,5-diamino 3-methyl 1-phenyl pyrazole, 4,5-diamino 1-methyl 3-phenyl pyrazole, 4-amino 1, 3-dimethyl 5-hydrazino pyrazole, 1-benzyl 4,5- diamino 3-méthy!
• pyrazole 4,5-diamino 3-tert-butyl 1-methyl pyrazole, 4,5-diamino 1- tert-butyl 3-methyl pyrazole, 4,5-diamino l- ( ⁇ -hydroxyethyl) 3-methyl pyrazole, 4,5-diamino 1-ethyl 3-methyl pyrazole, 4,5-diamino 1-ethyl 3- (4'-methoxyphenyl) pyrazole, 4,5-diamino 1-ethyl 3-hydroxymethyl pyrazole, 4,5-diamino 3-hydroxymethyl 1-methyl pyrazole, 4,5-diamino 3-hydroxymethyl 1-isopropyl pyrazole, 4,5-diamino 3-methyl 1-isopropyl pyrazole, 4-amino 5- (2 ' -aminoethyl) amino 1, 3-dimethyl pyrazole, 3,4,5-triamino pyrazole, 1-methyl 3,4,5-tri
• the additional oxidation base or bases preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
• the addition salts with an acid which can be used in the context of the dye compositions of the invention are in particular chosen from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates and acetates.
• the medium suitable for dyeing (or support) generally consists of water or 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 alkanols, C- ⁇ -C 4 , such as ethanol and isopropanol; glycerol; glycols and glycol 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, analogous products and mixtures thereof.
• lower alkanols such as ethanol and isopropanol
• glycerol glycols and glycol ethers
• glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether
• aromatic alcohols such as benzyl alcohol or phenoxyethanol, analogous products 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, and even more preferably between 5 and 30% by weight approximately.
• 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 alkalinizing agents usually used in dyeing keratin fibers.
• 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.
• alkalinizing agents that 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 (IV) below:
• the oxidation dye compositions in accordance with the invention may also contain at least one direct dye, in particular for modifying the shades or enriching them with reflections.
• 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, zwitterionic surfactants or their mixtures, anionic polymers, cationic, nonionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as by example of volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents.
• 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.
• Another object of the invention is a process for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair, using the dye composition as defined above.
• At least one dye composition as defined above is applied to the fibers, the color being revealed at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use. the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially.
• the dye composition described above is preferably mixed at the time of use. above with an oxidizing composition containing, in a medium suitable for dyeing, at least one oxidizing agent present in an amount sufficient to develop a coloration.
• the mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which it is rinsed, washed with shampoo, rinsed again and dried.
• the oxidizing agent can be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibers, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as as perborates and persulfates, and enzymes such as peroxidases, laccases, tyrosynases and oxidoreductases among which may be mentioned in particular pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases , and uricases.
• the pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12 approximately, and again more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or alkalinizing agents usually used in dyeing keratin fibers and as defined above.
• the oxidizing composition as defined above may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
• composition which is finally applied to the keratin fibers 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 invention finally relates to a device with several compartments or "kit” for dyeing or any other packaging system with several compartments, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition such 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 following examples are intended to illustrate the invention without limiting its scope
• the mixture is applied to gray hair containing 90% white hairs, permanent, at a rate of 28 g for 3 g of hair, for 30 min.
• the hair is then rinsed, washed with a standard shampoo and dried.
• the results are shown in the following table

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• 2000
  • 2000-04-12 FR FR0004718A patent/FR2807647B1/fr not_active Expired - Fee Related
• 2001
  • 2001-04-11 WO PCT/FR2001/001108 patent/WO2001078666A1/fr active Application Filing
  • 2001-04-11 EP EP01923794A patent/EP1274391A1/de not_active Ceased
  • 2001-04-11 AU AU2001250482A patent/AU2001250482A1/en not_active Abandoned
  • 2001-04-11 US US10/257,356 patent/US7141078B2/en not_active Expired - Fee Related
  • 2001-04-11 JP JP2001575968A patent/JP2003530415A/ja not_active Withdrawn

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