WO2001066071A1 - Compositions de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition - Google Patents
Compositions de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition Download PDFInfo
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- WO2001066071A1 WO2001066071A1 PCT/FR2001/000660 FR0100660W WO0166071A1 WO 2001066071 A1 WO2001066071 A1 WO 2001066071A1 FR 0100660 W FR0100660 W FR 0100660W WO 0166071 A1 WO0166071 A1 WO 0166071A1
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- amino
- methyl
- paraphenylenediamine
- radical
- bis
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- 0 CC1(C=C(*(*)C(*)CO2)C2=CC=C1)N Chemical compound CC1(C=C(*(*)C(*)CO2)C2=CC=C1)N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- 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
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- 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
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- 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
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
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- 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
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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, at least one oxidation base chosen from certain derivatives. substituted paraphenylenediamine and their addition salts with an acid and at least one selected coupler, as well as the dyeing process using this composition.
- oxidation bases it is known to dye keratin fibers and in particular human hair with dye compositions containing oxidation dye precursors, in particular ortho or paraphenylenediamines, ortho or paraaminophenols, heterocyclic bases, generally called oxidation bases.
- oxidation dye precursors in particular ortho or paraphenylenediamines, ortho or paraaminophenols, heterocyclic bases, generally called oxidation bases.
- 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 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 differently sensitized effect (ie damaged) between its tip and its root.
- compositions for the oxidation dyeing of keratin fibers containing, as oxidation dye precursors, certain substituted derivatives of phenylenediamine.
- the colorings obtained by using these compositions are not always powerful enough, chromatic or resistant to the various aggressions that the hair can undergo.
- 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: at least one oxidation base chosen from the substituted paraphenylenediamine derivatives of formula (I) below, and their addition salts with an acid:
- Ri and R 2 can take one of the following meanings i) to v)
- Ri and R 2 simultaneously represent a radical - (CH 2 ) 2CHOHCH 2 OH; or ii) Ri represents a radical -CH 2 (CHOH) 4 CH 2 OH and R 2 represents a hydrogen atom, an alkyl, aryl radical or a heterocycle; or iii) R ⁇ represents an alkyl or aryl radical or a heterocycle and R 2 represents an alkylene radical - (CH 2 ) m - in which m is an integer equal to 2 or 3, said alkylene radical forming a ring together with nitrogen atom, the carbon atom of the benzene ring carrying the nitrogen atom and one of the two carbon atoms of the benzene ring which are adjacent to it, it being understood that when R 1 is an alkyl or aryl radical, then either Ri or said alkylene radical is substituted by a radical containing at least one nitrogen, oxygen or sulfur atom; iv) R- ⁇ represents a radical - (CH 2 CH 2 O)
- said alkyl radicals having from 1 to 25 carbon atoms and which may be linear, branched or cyclic and be substituted by one or more radicals and then represent a mono or polyhydroxyalkyl, alkoxyalkyl, aminoalkyl radical optionally substituted on the nitrogen atom, carboxyalkyl , alkylcarboxyalkyle, thioalkyle, alkylthioalkyle, cyanoalkyle, trifluoroalkyle, sulfoalkyle, phosphoalkyle, or haloalkyle; said alkoxy radicals having from 1 to 25 carbon atoms and which may be linear, branched or cyclic; said aryl radicals containing from 6 to 26 carbon atoms and which can be substituted by one or more radicals chosen from alkyl, substituted alkyl or alkoxy radicals; the heterocycles being mono or polycyclic, each cycle comprising 3, 4, 5 or 6 members and possibly containing one or more heteroatoms, it being understood
- - n is an integer between 0 and 4; it being understood that when n is greater than 1, then the radicals R 3 may be identical or different and form between them a saturated or unsaturated ring with 3, 4, 5, or 6 links;
- At least one coupler chosen from heterocyclic couplers, substituted metadiphenols, substituted metaphenylenediamines, naphthols and acylated naphthols, and the metaaminophenols of the following formula (II), and their addition salts with an acid:
- R 5 represents a hydrogen atom, an alkyl radical in C- ⁇ -C 4 , monohydroxyalkyl in CrC, or polyhydroxyalkyl in C 2 -C,
- R 6 represents a hydrogen atom, an alkyl radical in dC 4 , alkoxy in C ⁇ -C, or a halogen atom chosen from chlorine, bromine or fluorine,
- - R represents a hydrogen atom, an alkyl radical C ⁇ -C4 alkoxy, C ⁇ -C 4 monohydroxyalkyl -C 4 polyhydroxyalkyl, C 2 -C monohydroxyalkoxy C ⁇ -C 4, or polyhydroxyalkoxy C 2 -C 4 ;
- R 7 denotes a methyl radical, and that R 6 denotes a hydrogen atom, then R 5 does not denote a hydrogen atom.
- the dye composition in accordance with the invention leads to coloring in various shades, chromatic, powerful, aesthetic, having a low selectivity and excellent resistance properties both with respect to atmospheric agents such as light and bad weather. and with regard to perspiration and the various treatments that the hair can undergo.
- the oxidation base is chosen from the substituted paraphenylenediamine derivatives of formula (I) below, and their addition salts with an acid: in which :
- Ri and R 2 simultaneously represent a radical - (CH 2 ) 2 CHOHCH 2 OH; or ii) Ri represents a radical -CH 2 (CHOH) CH 2 OH and R 2 represents a hydrogen atom, an alkyl radical; or iv) R ⁇ represents a radical in which p is an integer between 2 and 8 inclusive, l ⁇ and R 2 , identical or different, represent a hydrogen atom, an alkyl radical; v) Ri and R 2 form, together with the nitrogen atom to which they are attached, a saturated 5, 6 or 7-membered heterocycle, said heterocycle being substituted by at least one radical containing at least one carbon atom, or nitrogen, or oxygen, not located in the meta position relative to the nitrogen atom of the heterocycle; - R 3 represents a halogen atom, an alkyl or aryl radical, a heterocycle, - n is an integer equal to 0, 1 or 2;
- the groups R1 and R2 form a heterocycle comprising a single heteroatom, nitrogen, for example a pyrolidinic heterocycle.
- the oxidation base is chosen from 1-N, N-bis- (3 ', 4'- dihydroxybutyl) paraphenylenediamine, 1-N, N-bis- (3', 4'-dihydroxybutyl) - 3- methyl paraphenylenediamine, 1-N, N-bis- (3 ', 4'-dihydroxybutyl) -3-ethyl paraphenylenediamine, 1-N, N-bis- (3', 4'-dihydroxybutyl) -3- propyl paraphenylenediamine, 1-N- (2 ', 3', 4 ', 5', 6'-pentahydroxyhexyl) paraphenylenediamine, 1-N- (2 ', 3', 4 ', 5', 6'-pentahydroxyhexyl ) -3-methyl paraphenylenediamine, 1-N- (2 ', 3', 4 ', 5', 6'-pentahydroxyhexyl) -3-methyl parapheny
- the oxidation base is chosen from 1- (4'-amino-3'-methylphenyl) -3-hydroxyethyloxy pyrrolidine, 1- (4'-amino-3'-methylphenyl) -4-hydroxy- 2-methyl pyrrolidine, 1- (4'-amino-3'-methylphenyl) -3- methylsulfonamido pyrrolidine, 1- (4'-amino-3'-phenoxyphenyl) -3- methylsulfonamido pyrrolidine, 1- (4 '-aminophenyl) -2- (4 "-aminophenoxymethyl) piperidine, 1- (4'-aminophenyl) -2- (hydroxyethyl) piperidine, 1- (4'-amino-3'- isopropylphenyl) -2-hydroxymethyl piperidine, 1- (4'-aminophenyl) -4-methyl piperidine, 1- (4'-aminophenyl) -2,7-dimethyl aza
- the paraphenylenediamine derivative (s) of formula (I) used as oxidation base in the dye composition in accordance with the invention preferably represent from 0.0001 to 20% by weight approximately, more preferably from 0.001 to 15% weight and even more preferably from 0.01 to 10% by weight relative to the total weight of the composition.
- meta-aminophenols of formula (II) 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-chloro 2-methyl phenol, 5-amino 2,4-dimethoxy phenol, 5- ( ⁇ -hydroxypropylamino) 2-methyl phenol, and their addition salts with an acid.
- substituted meta-diphenols which can be used as couplers in the dye composition according to the invention, use will preferably be made of the compounds of formula (III) below, and their addition salts with an acid:
- R ⁇ and R 9 identical or different, represent a hydrogen atom, a C ⁇ -C 4 alkyl radical, or a halogen atom chosen from chlorine, bromine or fluorine;
- radicals R 8 and Rg are different from a hydrogen atom.
- substituted meta-diphenols of formula (III) mention may more particularly be made of 2-methyl 1,3-dihydroxy benzene, 4-chloro 1, 3-dihydroxy benzene, 2-chloro 1,3- dihydroxybenzene, and their addition salts with an acid.
- - Rio represents a hydrogen atom, a C ⁇ -C alkyl, C ⁇ -C 4 monohydroxyalkyl, or C 2 -C 4 polyhydroxyalkyl radical;
- Rn and R ⁇ 2 identical or different, represent a hydrogen atom, a C ⁇ -C 4 alkyl radical, C ⁇ -C monohydroxyalkoxy, or C 2 -C polyhydroxyalkoxy;
- R ⁇ 3 represents a hydrogen atom, a C ⁇ -C alkoxy, CrC aminoalkoxy, C ⁇ -C 4 monohydroxyalkoxy, C 2 -C polyhydroxyalkoxy, or a 2,4-diaminophenoxyalkoxy radical; it being understood that at least one of the radicals Rio to R ⁇ 3 is different from a hydrogen atom.
- heterocyclic couplers which can be used in the dye composition in accordance with the invention, mention may especially be made of indole derivatives, indole derivatives, benzimidazole derivatives, benzomorpholine derivatives, sesamol derivatives, pyrazolo-azole derivatives , the pyrroloazole derivatives, imidazolo-azole derivatives, pyrazolo- pyrimidine derivatives, pyrazolin-3,5-diones derivatives, pyrrolo- [3,2-d] - oxazole derivatives, pyrazolo- [3,4 derivatives -d] -thiazoliques, S-oxide-thiazolo-azoliques derivatives, S, S-dioxide-thiazolo-azoliques derivatives, and their addition salts with an acid.
- - Ru represents a hydrogen atom, a C ⁇ -C 4 alkyl radical, C ⁇ -C monohydroxyalkyl, C 2 -C 4 polyhydroxyalkyl, or CrC 4 aminoalkyl, the amine of which is mono or disubstituted by an alkyl group in C ⁇ -C;
- R ⁇ 5 represents a hydrogen atom or an alkyl radical in CrC
- R ⁇ 6 represents a hydrogen atom, a C ⁇ -C alkyl or hydroxyl radical
- - X represents a hydroxyl radical or NHR ⁇ in which R ⁇ 7 represents a hydrogen atom, an alkyl radical in CrC, or hydroxyalkyl in dC.
- indole derivatives of formula (V) above there may be more particularly mentioned 4-hydroxy indole, 6-hydroxy indole, 7-amino indole, 6-amino indole, 7-hydroxy indole, 7 -ethyl 6- ( ⁇ -hydroxyethyl) amino indole, 4-amino indole, 6-hydroxy 1-methyl indole, 5,6-dihydroxy indole, 4-hydroxy 1-N-methyl indole, 4-hydroxy 2-methyl indole, 4-hydroxy 5-methyl indole, 4-hydroxy lN- ( ⁇ -hydroxyethyl) indole, 4-hydroxy lN- ( ⁇ -hydroxypropyl) indole, 1-N- ( ⁇ , ⁇ - dihydroxypropyl) 4-hydroxy indole, 4-hydroxy lN- ( ⁇ -hydroxyethyl) 5-methyl indole, lN- ( ⁇ -dimethylaminopropyl) 4-hydroxy indole, and their addition salt
- indoline derivatives which can be used as heterocyclic couplers in the dye composition in accordance with the invention, mention may be made of 4-hydroxy indoline, 6-hydroxy indoline, 6-amino indoline, 5,6-dihydroxy indoline, and their addition salts with an acid.
- - Rie represents a hydrogen atom or a C ⁇ -C 4 alkyl radical
- - Ri represents a hydrogen atom, a C ⁇ -C alkyl radical, or phenyl
- R 2 o represents a hydroxyl, amino or methoxy radical
- R 2 ⁇ represents a hydrogen atom, a hydroxyl, methoxy or C ⁇ -C 4 alkyl radical; provided that: - when R 20 denotes an amino radical, then it occupies position 4,
- benzimidazole derivatives of formula (VI) above there may be mentioned more particularly 4-hydroxy benzimidazole, 4-amino benzimidazole, 4-hydroxy 7-methyl benzimidazole, 4-hydroxy 2-methyl benzimidazole, 1-butyl 4-hydroxy benzimidazole, 4-amino 2-methyl benzimidazole, 5,6-dihydroxy benzimidazole, 5-hydroxy 6-methoxy benzimidazole, 4,7-dihydroxy benzimidazole, 4,7-dihydroxy 1- methyl benzimidazole, le, 7-dimethoxy benzimidazole, 5,6-dihydroxy 1-methyl benzimidazole, le 5,6-dihydroxy 2-methyl benzimidazole, 5,6-dimethoxy benzimidazole, and their addition salts with an acid.
- R 22 and R 23 which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical
- Z represents a hydroxyl or amino radical.
- benzomorpholine derivatives of formula (VII) above there may be mentioned more particularly 6-hydroxy 1,4-benzomorpholine, N-methyl 6-hydroxy 1,4-benzomorpholine, 6-amino 1,4- benzomorpholine, and their addition salts with an acid.
- R 2 denotes a hydroxyl, amino, alkyl (CrC) amino, monohydroxyalkyl (CrC) amino or polyhydroxyalkyl (C 2 -C 4 ) amino radical
- R 25 denotes a hydrogen or halogen atom or a C ⁇ - alkoxy radical C 4 .
- sesamol derivatives of formula (VIII) above there may be mentioned more particularly 2-bromo 4,5-methylenedioxy phenol, 2-methoxy 4,5-methylenedioxy aniline, 2- ( ⁇ -hydroxyethyl) amino 4,5-methylenedioxy benzene, and their addition salts with an acid.
- pyrazolo-azole derivatives which can be used as heterocyclic couplers in the dye composition in accordance with the invention, mention may be made more particularly of the compounds described in the following patent applications and patents: FR-A-2,075,583, EP-A -0 119 860, EP-A-0 285 274, EP-A-0 244 160, EP-A-0 578 248, GB 1 458 377, US 3 227 554, US 3 419 391, US 3 061 432, US 4,500,630, US 3,725,067, US 3,926,631, US 5,457,210, JP 84/99437, JP 83/42045, JP 84/162548, JP 84/171956, JP 85/33552, JP 85/43659, JP 85/172982, and JP 85/190779, as well as in the following publications: Chem.
- imidazolo-azolic derivatives there may be mentioned in particular:
- acylated naphthols and naphthols which can be used as couplers in the dye composition according to the invention, use will preferably be made of the compounds of formula (IX) below, and their addition salts with an acid:
- - R 26 represents a hydrogen atom or a group -CO-R in which R represents a CC alkyl radical; - R 27 represents a hydrogen atom, a hydroxyl radical, C ⁇ -C alkyl, or a group -SO 3 H;
- R 28 represents a hydrogen atom, or a hydroxyl radical; it being understood that at least one of the radicals R 26 to R 2 ⁇ is different from a hydrogen atom.
- acylated naphthols and naphthols of formula (IX) which can be used as couplers in the dye composition according to the invention, mention may be made in particular of 1,7-dihydroxy naphthalene, 2,7-dihydroxy naphthalene, 2, 5-dihydroxy naphthalene, 2,3-dihydroxy naphthalene, 1-acetoxy 2-methyl naphthalene, 1-hydroxy 2-methyl naphthalene, 1-hydroxy 4-naphthalene sulfonic acid, and their addition salts with a acid.
- the coupler (s) as defined above according to the invention preferably represent from 0.0001 to 10% by weight approximately of the total weight of the composition, and even more preferably from 0.005 to 5% by weight approximately of this weight.
- the dye composition according to the invention may, in addition to the coupler (s) defined above, contain one or more additional couplers.
- Additional couplers are more particularly chosen from 2-methyl 5-amino phenol, 1, 3-dihydroxybenzene, or 1, 3-diaminobenzene.
- the additional coupler (s) preferably represent from 0.0001 to 8% by weight relative to the total weight of the composition.
- the dye composition in accordance with the invention may, in addition, contain one or more additional oxidation bases different from the substituted paraphenylenediamine derivatives of formula (I) and / or one or more direct dyes.
- paraphenylenediamines different from those of formula (I), such as for example the paraphenylenediamine, paratoluylenediamine, 2-hydroxyethyl paraphenylenediamine, 1-N, N ⁇ bis- ⁇ -hydroxyethyl paraphenylenediamine, paraaminophenols such as, for example, 3-methyl-4-aminophenol and 4-aminophenol, orthophenylaminophenols, orthophenylaminophenols , double bases, heterocyclic bases such as pyrimidines such as for example 2,4,5,6-tetraaminopyrimidine or such as pyrazoles such as for example 1- (2-hydroxyethyl) -4,5-diamino pyrazole.
- the additional oxidation base (s) represent from 0.0001 and 15% by weight relative to the total weight of the dye composition.
- 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, 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.
- organic solvent mention may for example be made of lower C ⁇ -C aicanols, 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, analogues and their mixtures.
- 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. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers.
- the acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid, lactic acid, sulfonic acids.
- the basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, aicanolamines such as mono-, di- and triethanolamines as well as their derivatives, hydroxyalkylamines and ethylene diamines oxyethylenated and / or oxypropylenes , sodium or potassium hydroxides and the compounds of formula (X) below:
- R 33 is a propylene residue optionally substituted by a hydroxyl group or a dC 4 alkyl radical
- R 2g, R 3 o, R 3 and R 32 identical or different, represent a hydrogen atom, an alkyl radical -C 4 hydroxyalkyl dC 4.
- 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, non-ionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, reducing or antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such that for example silicones, film-forming agents, preservatives, opacifying agents, silicone or non-silicone UV filters, vitamins or provitamins.
- adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, anionic polymers, cationic, non-ionic, amphoteric, zwitterionic or their mixtures, mineral or organic thickening agents, reducing or
- the reducing or antioxidant agents can be chosen in particular from sodium sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite, dehydroascorbic acid, hydroquinone, 2-methyl-hydroquinone, ter- butyl-hydroquinone and homogentisic acid, and they are then generally present in amounts which can vary between 0.05 and 1.5% by weight approximately relative to the total weight of the composition.
- the dye composition in accordance with the invention contains at least one nonionic surfactant in a proportion preferably varying between 0.1 and 20% by weight approximately relative to the total weight of the composition, and at least a cationic or amphoteric substantive polymer in a proportion preferably varying between 0.05 and 10% by weight relative to the total weight of the composition.
- the dye composition in accordance with the invention contains at least one thickening polymer comprising at least one hydrophilic unit and at least one fatty chain in a proportion preferably varying between 0.05 and 10% by weight relative to the total weight of the composition.
- the dye composition in accordance with the invention may 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 or which is present in an oxidizing composition applied simultaneously or sequentially separately.
- the dye composition as defined above is 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.
- 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 bramates, persalts such as as perborates and persulfates, peracids and oxidative enzymes such as peroxidases, laccases, tyrosynases and oxidoreductases among which may be mentioned in particular pyranose oxidases, glucose oxidases, glycerol oxidases, lactates oxidases, pyruvate oxidases, and uricases, said enzymes possibly being associated with their respective donors.
- 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 even 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. .
- Another subject of the invention is a device with several compartments or "kit” for dyeing with several compartments or any other packaging system with several compartments in which a first compartment contains the dye composition as defined above and a second compartment contains the oxidizing composition 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 mixtures thus produced were applied for 30 minutes to locks of permanent natural gray hair containing 90% white hairs.
- the locks were then rinsed, washed with a standard shampoo, rinsed again and then dried.
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Abstract
Description
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Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0202009A HUP0202009A2 (hu) | 2000-03-06 | 2001-03-06 | Keratintartalmú rostok oxidációs festésére való készítmény és festési eljárás a készítmény alkalmazásával |
JP2001564724A JP2003525888A (ja) | 2000-03-06 | 2001-03-06 | ケラチン繊維の酸化染色用組成物及びそれを用いた染色方法 |
KR1020017014181A KR20010113914A (ko) | 2000-03-06 | 2001-03-06 | 케라틴 섬유용 산화 염색 조성물 및 그를 이용한 염색방법 |
AU42544/01A AU4254401A (en) | 2000-03-06 | 2001-03-06 | Oxidation dyeing composition for keratinous fibres and dyeing method using same |
US09/959,704 US6890362B2 (en) | 2000-03-06 | 2001-03-06 | Oxidation dyeing composition for keratinous fibers and dyeing method using same |
CA002373097A CA2373097A1 (fr) | 2000-03-06 | 2001-03-06 | Compositions de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
BR0105562-3A BR0105562A (pt) | 2000-03-06 | 2001-03-06 | Composição de tintura de oxidação das fibras queratìnicas compreendendo derivados substituìdos de para-fenilenodiamina, processo de tintura de oxidação das mesmas e, dispositivo com vários compartimentos, ou "kit" de tintura com vários compartimentos |
EP01915449A EP1181005A1 (fr) | 2000-03-06 | 2001-03-06 | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR00/02857 | 2000-03-06 | ||
FR0002857A FR2805737B1 (fr) | 2000-03-06 | 2000-03-06 | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001066071A1 true WO2001066071A1 (fr) | 2001-09-13 |
Family
ID=8847769
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2001/000660 WO2001066071A1 (fr) | 2000-03-06 | 2001-03-06 | Compositions de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
Country Status (14)
Country | Link |
---|---|
US (1) | US6890362B2 (fr) |
EP (1) | EP1181005A1 (fr) |
JP (1) | JP2003525888A (fr) |
KR (1) | KR20010113914A (fr) |
CN (1) | CN1372458A (fr) |
AU (1) | AU4254401A (fr) |
BR (1) | BR0105562A (fr) |
CA (1) | CA2373097A1 (fr) |
CZ (1) | CZ20013944A3 (fr) |
FR (1) | FR2805737B1 (fr) |
HU (1) | HUP0202009A2 (fr) |
PL (1) | PL352384A1 (fr) |
WO (1) | WO2001066071A1 (fr) |
ZA (1) | ZA200109069B (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002074269A2 (fr) * | 2001-03-21 | 2002-09-26 | L'oreal | Compositions pour la teinture des fibres keretiniques contenant des derives de paraphenvienediamine a groupement pyrrolidinyle |
WO2002074259A2 (fr) * | 2001-03-21 | 2002-09-26 | L'oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement pyrrolidinyle |
EP1512684A1 (fr) * | 2003-09-04 | 2005-03-09 | L'oreal | Utilisation, pour la teinture des fibres kératiniques, d'un dérivés de para-phénylènediamine substituée par un noyau homopiperidine |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2831054B1 (fr) * | 2001-10-24 | 2004-05-28 | Oreal | Composition tinctoriale comprenant une paraphenylenediamine, le 1-n-(b-hydroxy indole et un metaaminophenol ; procedes de teinture |
FR2831055B1 (fr) * | 2001-10-24 | 2004-05-28 | Oreal | Composition tinctoriale comprenant au moins une base heterocyclique et le 1-n-(b-hydroxyethyl) 4-hydroxy indole a titre de coupleur ; procedes de teinture |
FR2831057B1 (fr) * | 2001-10-24 | 2004-05-28 | Oreal | Composition tintoriale comprenant une paraphenylenediamine, une paraaminophenol, le 1-n(b-hydroxyethyl) 4-hydroxy indole et un metaaminophenol ; procedes de teinture |
FR2864957A1 (fr) * | 2004-01-09 | 2005-07-15 | Oreal | Composition pour la teinture des fibres keratiniques comprenant au moins un derive de para-phenylenediamine substitue par un noyau heptamethylenediamine |
WO2005068431A1 (fr) * | 2004-01-09 | 2005-07-28 | L'oreal | Composition pour colorer des fibres de keratine comprenant au moins un derive de para-phenylenediamine |
US7591860B2 (en) * | 2004-02-27 | 2009-09-22 | L'oreal, S.A. | N-alkylpolyhydroxylated secondary para-phenylenediamines, dye compositions comprising them, processes, and uses thereof |
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2000
- 2000-03-06 FR FR0002857A patent/FR2805737B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-06 WO PCT/FR2001/000660 patent/WO2001066071A1/fr not_active Application Discontinuation
- 2001-03-06 AU AU42544/01A patent/AU4254401A/en not_active Abandoned
- 2001-03-06 BR BR0105562-3A patent/BR0105562A/pt not_active IP Right Cessation
- 2001-03-06 HU HU0202009A patent/HUP0202009A2/hu unknown
- 2001-03-06 PL PL01352384A patent/PL352384A1/xx unknown
- 2001-03-06 CN CN01801179A patent/CN1372458A/zh active Pending
- 2001-03-06 CA CA002373097A patent/CA2373097A1/fr not_active Abandoned
- 2001-03-06 CZ CZ20013944A patent/CZ20013944A3/cs unknown
- 2001-03-06 US US09/959,704 patent/US6890362B2/en not_active Expired - Fee Related
- 2001-03-06 EP EP01915449A patent/EP1181005A1/fr not_active Withdrawn
- 2001-03-06 JP JP2001564724A patent/JP2003525888A/ja active Pending
- 2001-03-06 KR KR1020017014181A patent/KR20010113914A/ko not_active Application Discontinuation
- 2001-11-02 ZA ZA200109069A patent/ZA200109069B/xx unknown
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002074269A2 (fr) * | 2001-03-21 | 2002-09-26 | L'oreal | Compositions pour la teinture des fibres keretiniques contenant des derives de paraphenvienediamine a groupement pyrrolidinyle |
WO2002074259A2 (fr) * | 2001-03-21 | 2002-09-26 | L'oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement pyrrolidinyle |
FR2822374A1 (fr) * | 2001-03-21 | 2002-09-27 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement pyrrolidinyle |
FR2822373A1 (fr) * | 2001-03-21 | 2002-09-27 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement pyrrolidinyle |
WO2002074269A3 (fr) * | 2001-03-21 | 2004-02-19 | Oreal | Compositions pour la teinture des fibres keretiniques contenant des derives de paraphenvienediamine a groupement pyrrolidinyle |
WO2002074259A3 (fr) * | 2001-03-21 | 2004-07-29 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement pyrrolidinyle |
EP1512684A1 (fr) * | 2003-09-04 | 2005-03-09 | L'oreal | Utilisation, pour la teinture des fibres kératiniques, d'un dérivés de para-phénylènediamine substituée par un noyau homopiperidine |
FR2859472A1 (fr) * | 2003-09-04 | 2005-03-11 | Oreal | Utilisation, pour la teinture des fibres keratiniques, d'un derive de para-phenylenediamine substituee par un noyau homopiperidine |
Also Published As
Publication number | Publication date |
---|---|
AU4254401A (en) | 2001-09-17 |
EP1181005A1 (fr) | 2002-02-27 |
CN1372458A (zh) | 2002-10-02 |
FR2805737A1 (fr) | 2001-09-07 |
US20030009835A1 (en) | 2003-01-16 |
BR0105562A (pt) | 2002-03-19 |
FR2805737B1 (fr) | 2003-01-03 |
CZ20013944A3 (cs) | 2002-05-15 |
CA2373097A1 (fr) | 2001-09-13 |
ZA200109069B (en) | 2002-08-28 |
US6890362B2 (en) | 2005-05-10 |
PL352384A1 (en) | 2003-08-25 |
JP2003525888A (ja) | 2003-09-02 |
HUP0202009A2 (hu) | 2002-12-28 |
KR20010113914A (ko) | 2001-12-28 |
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