EP1274392A1 - Oxidationsfärbemittel für keratinische fasern und färbungsverfahren mit diesem mittel - Google Patents

Oxidationsfärbemittel für keratinische fasern und färbungsverfahren mit diesem mittel

Info

Publication number
EP1274392A1
EP1274392A1 EP01923795A EP01923795A EP1274392A1 EP 1274392 A1 EP1274392 A1 EP 1274392A1 EP 01923795 A EP01923795 A EP 01923795A EP 01923795 A EP01923795 A EP 01923795A EP 1274392 A1 EP1274392 A1 EP 1274392A1
Authority
EP
European Patent Office
Prior art keywords
phenylenediamine
para
acid
composition according
addition salts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP01923795A
Other languages
English (en)
French (fr)
Inventor
Marie-Pascale Audousset
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1274392A1 publication Critical patent/EP1274392A1/de
Pending legal-status Critical Current

Links

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
    • A61K8/4906—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
    • 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
    • A61Q5/10—Preparations for permanently dyeing the hair

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 first coupler at least one derivative of 3,5-diaminopyridine chosen appropriately;
  • the subject of the invention is also the dyeing process using this composition.
  • oxidation dye precursors in particular ortho or para-phenylenediamines, ortho or para-aminophenols, heterocyclic bases, generally called bases oxidation.
  • the precursors of oxidation dyes, or oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, through an oxidative condensation process, to colored and coloring compounds.
  • couplers or color modifiers the latter being chosen in particular from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds.
  • 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 3,5-d ⁇ am ⁇ no py ⁇ dine derivative corresponding to the following general formula (I)
  • R T and R 2 identical or different, represent a C ⁇ -C 4 alkyl radical, monohydroxyalkyle in or C 2 -C 4 polyhydroxyalkyl,
  • R 3 represents a hydrogen atom, a CC alkyl, monohydroxyalkyl CC 4 or polyhydroxyalkyl C 2 -C radical and / or one of its addition salts with an acid; - And as a second coupler, a meta-phenylenediamine and / or one of its addition salts with an acid;
  • At least one oxidation base of the para-phenylenediamine type and / or one of its addition salts with an acid At least one oxidation base of the para-phenylenediamine type 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.
  • 3,5-diamino pyridine derivatives of formula (I) in accordance with the invention, mention may be made of 2,6-dimethoxy-3,5-diaminopyridine, 2,6-diethoxy-3,5-diaminopyridine, 2,6-di- ( ⁇ -hydroxyethyloxy) -3,5-diaminopyridine and their addition salts with an acid.
  • the dye composition preferably contains 2,6-dimethoxy-3,5-diaminopyridine, and / or at least one of its addition salts with an acid.
  • the 3,5-diaminopyhdin 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.
  • meta-phenylenediamines which can be used as second coupler in the dye compositions in accordance with the invention, mention may in particular be made of the compounds of formula (II) below and their addition salts with an acid: in which
  • - R represents a hydrogen atom, an alkyl radical in CrC 4 , monohydroxyalkyle in CC or polyhydroxyalkyle in C 2 -C,
  • R 5 and R 6 identical or different, represent a hydrogen atom, an alkyl radical in CC 4 OR hydroxyalkoxy in Cr ⁇ ,
  • R 7 represents a hydrogen atom, an alkoxy radical in CC, aminoalkoxy in C -, - C, monohydroxyalkoxy in C! -C 4 , polyhydroxyalkoxy in C 2 -C or a radical 2,4-d ⁇ am ⁇ nophénoxyalkoxy
  • meta-phenylenediamines of formula (II) above mention may more particularly be made of meta-phenylenediamine, 2,4-d ⁇ am ⁇ no phenoxyethanol, 2,4-d ⁇ am ⁇ no 1-ethoxybenzene, 2-am ⁇ no 4-N- ( ⁇ -hydroxyethyl) am ⁇ no anisole, 3,5-d ⁇ am ⁇ no 1-ethyl 2-methoxybenzene, 3,5-d ⁇ am ⁇ no 2-methoxy 1-methyl benzene, 1, 3-b ⁇ s- (2,4-d ⁇ am ⁇ nophenoxy) propane, b ⁇ s- (2,4-d ⁇ am ⁇ nophenoxy) methane, 1- ( ⁇ - aminoethyloxy) 2,4-d ⁇ am ⁇ no benzene, 2-am ⁇ no l- ( ⁇ -hydroxyethyloxy) 4-methylam ⁇ no benzene, 2,4-d ⁇ am ⁇ no 1 -ethoxy 5-methyl benzene, 2,4-d
  • the meta-phenylenediamine (s) in accordance with 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
  • R 8 represents a hydrogen atom, an alkyl radical in C ⁇ -C 4 , monohydroxyalkyle in CC 4 , polyhydroxyalkyle in C 2 -C 4 , alkoxy (C ⁇ -C 4 ) alkyl (CC 4 ), substituted alkyl in CVC 4 by a nitrogen, phenyl or 4'-aminophenyl group;
  • R 9 represents a hydrogen atom, an alkyl radical in C ⁇ -C 4 , monohydroxyalkyle in CC 4 , polyhydroxyalkyle in C 2 -C 4 , alkoxy (CrC) alkyl (CC 4 ) or alkyl in CC 4 substituted by a group nitrogen;
  • R 10 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C ⁇ -C 4 alkyl radical, C ⁇ C A monohydroxyalkyl, hydroxyalkoxy in CrC 4 , acetylaminoalkoxy in CrC, mesylaminoalkoxy in C ⁇ -C or carbamoylaminoalkoxy in C ⁇ -C 4 ,
  • - Ru represents a hydrogen or halogen atom or a C ⁇ C ⁇ alkyl radical
  • nitrogen groups of formula (III) above there may be mentioned in particular the amino, monoalky C-j-C amino, dialkyl (C C) amino, trialkyl (C ⁇ -C) amino, monohydroxyalkyl (C C) amino, imidazolinium and ammonium radicals.
  • 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 are para-phenylenediamine, paratoluylenediamine, 2-isopropyl para-phenylenediamine, 2- ⁇ -hydroxyethyl para-phenylenediamine, 2,6-dimethyl para-phenylenediamine, 2,6-diethyl para-phenylenediamine, 2,3-dimethyl para-phenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, and 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 or compounds of formula (I) above and of or meta-phenylenediamines, one or more additional couplers which can be chosen from the couplers conventionally used in oxidation dye and among which mention may be made of meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives other than those of the invention and pyrazolones, and their addition salts with an acid.
  • additional couplers which can be chosen from the couplers conventionally used in oxidation dye and among which mention may be made of meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives other than those of the invention and pyrazolones, and their addition salts with an acid.
  • couplers are more particularly chosen from 2-methyl 5-amino phenol, 5-N- ( ⁇ -hydroxyethyl) amino 2-methyl phenol, 3-amino phenol, 1, 3-dihydroxy benzene, 1, 3 -dihydroxy 2-methyl benzene, 4-chloro 1, 3-dihydroxy benzene, 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-pyridinium and their addition salts with an acid.
  • these additional couplers 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 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 heterocyclic bases.
  • the bis-phenylalkylenediamines there may be more particularly mentioned by way of example, 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-(2-
  • 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 addition salts with an acid.
  • 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-triaminopyhmidine, 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-methyl pyrazole, 4,5-diamino 3-tert-butyl 1-methyl pyrazole, 4,5-diamino 1- tert-
  • 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.
  • 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 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.
  • a solvent organic for example, lower CC 4 alkanols, such as ethanol and isopropanol, may be mentioned; 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.
  • 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 1 1 approximately. It can be adjusted to the desired value by means of acidifying or basifying 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.
  • 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 (IV) below:
  • R i2 , R 13 , R M and R 15 which may be identical or different, represent a hydrogen atom, a CC 6 alkyl or C -, - C 6 hydroxyalkyl radical.
  • 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, zwittenonic surfactants or mixtures thereof, anionic polymers, cationic, non-ionic, amphoteric, zwittenonic or mixtures thereof, 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, modified or unmodified cones, 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 subject 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 described above is preferably mixed, at the time of use, 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
  • 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 leave on 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 basifying 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 mixture is applied to gray hair containing 90% white, permanent hair, 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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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
EP01923795A 2000-04-12 2001-04-11 Oxidationsfärbemittel für keratinische fasern und färbungsverfahren mit diesem mittel Pending EP1274392A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0004719A FR2807648B1 (fr) 2000-04-12 2000-04-12 Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
FR0004719 2000-04-12
PCT/FR2001/001109 WO2001078667A1 (fr) 2000-04-12 2001-04-11 Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition

Publications (1)

Publication Number Publication Date
EP1274392A1 true EP1274392A1 (de) 2003-01-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP01923795A Pending EP1274392A1 (de) 2000-04-12 2001-04-11 Oxidationsfärbemittel für keratinische fasern und färbungsverfahren mit diesem mittel

Country Status (6)

Country Link
US (1) US7141079B2 (de)
EP (1) EP1274392A1 (de)
JP (1) JP2003530416A (de)
AU (1) AU2001250483A1 (de)
FR (1) FR2807648B1 (de)
WO (1) WO2001078667A1 (de)

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US7141079B2 (en) 2006-11-28
AU2001250483A1 (en) 2001-10-30
FR2807648B1 (fr) 2005-06-10
JP2003530416A (ja) 2003-10-14
WO2001078667A1 (fr) 2001-10-25
US20040010862A1 (en) 2004-01-22
FR2807648A1 (fr) 2001-10-19

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