EP1412348A1 - Heteroaryl-substituierte diaminopyrazolderivate für die oxidative färbung von keratinfasern - Google Patents

Heteroaryl-substituierte diaminopyrazolderivate für die oxidative färbung von keratinfasern

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Publication number
EP1412348A1
EP1412348A1 EP02764953A EP02764953A EP1412348A1 EP 1412348 A1 EP1412348 A1 EP 1412348A1 EP 02764953 A EP02764953 A EP 02764953A EP 02764953 A EP02764953 A EP 02764953A EP 1412348 A1 EP1412348 A1 EP 1412348A1
Authority
EP
European Patent Office
Prior art keywords
diamine
pyrazole
pyridin
diamino
quinolin
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.)
Withdrawn
Application number
EP02764953A
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English (en)
French (fr)
Inventor
Thilo Fessmann
Eric Terranova
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
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Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1412348A1 publication Critical patent/EP1412348A1/de
Withdrawn legal-status Critical Current

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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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61K8/49—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
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
    • 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
    • A61K8/4966—Triazines or their condensed derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to new compounds derived from diaminopyrazole, to a composition for the oxidation dyeing of keratin fibers, and in particular of human keratin fibers such as the hair, comprising at least, as oxidation base, a compound diaminopyrazole derivative and the oxidation dyeing processes using it.
  • oxidation dye precursors in particular ortho- or paraphenylenediamines, ortho- or para-aminophenols, heterocyclic compounds such as derivatives diaminopyrazole, generally called oxidation bases.
  • 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, meta-aminophenols, metadiphenols and certain compounds. heterocyclic.
  • 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 fact differently sensitized (that is to say damaged) between its tip and its root. They must also have good chemical stability in the formulations. They must have a good toxicological profile.
  • DE 197 30 412 also discloses compounds of the azabispyrazole type which can be used as direct dyes in the field of reds.
  • the subject of the present invention is therefore a compound derived from diaminopyrazole of formula (I):
  • Ar is a 5 or 6-membered heteroaromatic radical which can be condensed with one or more aromatic or heteroaromatic rings each comprising 5 or 6 members.
  • the invention also relates to a compound of formula (I) characterized in that Ar is optionally substituted by at least one radical selected from alkyl to C 6 linear or branched alkoxy radicals, C 6 -C linear or branched, mono- or polyamino alkyl radicals to C 6 linear or branched, mono- or polyhydroxyalkyl radicals to C 6 linear or branched, amino, hydroxy, F, Cl, Br, I, trifluoromethyl , CHO, CO 2 H,
  • Ri being chosen from linear or branched C1 to Ce alkyl radicals, linear or branched C1 to Ce linear or polyaminoalkyl radicals, linear or branched mono- or polyhydroxyalkyl C1 to Ce radicals, trifluoromethyl, CHO, CO 2 Me, CO 2 Et, CONH 2 , SO 3 H, SO 2 NH 2 , SO 2 Me, and their physiologically acceptable salts.
  • Ri will be chosen from C 1 to C 4 alkyl derivatives.
  • 5 or 6-membered heteroaromatic within the meaning of the present application is meant an aromatic nucleus formed of 5 or 6 atoms of which at least one is a heteroatom chosen from the group formed by N, O, S.
  • it will be a radical chosen from the pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, imidazolyl, pyrazolyl, furanic, thiophenyl, triazolyl, triazinyl radicals, even more preferably, it will be a radical.
  • pyridinyl a radical chosen from the pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, imidazolyl, pyrazolyl, furanic, thiophenyl, triazolyl, triazinyl radicals, even more preferably, it will be a radical.
  • radical condensed with one or more aromatic or heteroaromatic rings each comprising 5 or 6 links within the meaning of the present application means a radical comprising 2 or 3 rings aromatic or heteroaromatic such that at least two carbon atoms of said radical are common to at least 2 of said aromatic or heterocyclic rings.
  • a radical chosen from the naphthyl, azanaphthyl, diazanaphthyl, triazanaphthyl, tetraazanaphthyl radicals such as the quinolinyl, isoquinolinyl, oxy-isoquinolinyl, quinoxalinyl, naphthyridinyl radicals; acridinyl, pyrazolo [3,4-b] pyridinyl, pyrazolo [3,4-c] pyridazinyl, thieno [3,2-c] pyridinyl radicals.
  • a subject of the invention is also the physiologically acceptable acid salts of the compounds of formula (I) such as hydrochlorides, hydrobromides, sulfates, tartrates, lactates or acetates.
  • a subject of the invention is also a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, characterized in that it contains, in a medium suitable for dyeing, as a base oxidation of at least one diaminopyrazole of formula (I) above, or its physiologically acceptable acid salts.
  • the colors obtained with the oxidation dye composition according to the invention are powerful, particularly bright and chromatic. They make it possible in particular to achieve red shades free or containing very little blue or yellow. They also have excellent resistance properties vis-à-vis the action of various external agents
  • the subject of the invention is also a process for the oxidation dyeing of keratin fibers using such a dye composition.
  • diaminopyrazoles of formula (I) As examples of diaminopyrazoles of formula (I) according to the invention, mention may be made of the compounds belonging to the following classes:
  • the diaminopyrazoles of formula (I) preferred according to the invention have the following structures:
  • the diaminopyrazoles of formula (I) which are more particularly preferred according to the invention are 2-Pyridin-2-yl-2H-pyrazole-3,4-diamine, 2-Pyridin-3-yl-2H- ⁇ yrazole-3,4- diamine, 2-Pyridin-4-yl-2H- pyrazole-3,4-diamine, 2-Pyrazin-2-yl-2H-pyrazole-3 5 4-diamine, 2'H- [1,3 '] Bipyrazolyl- 4,5-diamine, H- [1,4 '] Bipyrazolyl-4,5-diamine, 2- Pyrimidin-4-yl-2H-pyrazole-3, 4-diamine, 2-Pyrimidin-5-yl- 2H-pyrazole- 3,4-diamine, 2-Furan-2-yl-2H-pyrazole-3, 4-diamine, 3 (4,5-Diamino- pyrazol-1 -yl) -furane, 2-Thi
  • diaminopyrazoles of formula (I) according to the invention are prepared for example according to the following general method of preparation:
  • the operating conditions used will depend on the radical Ar of the reagent chosen.
  • the dye composition according to the invention contains in particular from 0.001 to 10% by weight, preferably from 0.05 to 6% by weight, and even more preferably from 0.1 to 3% by weight, of at least one diaminopyrazole of formula (I) or its salts.
  • the dye composition in accordance with the invention can also contain, in addition to (or) diaminopyrazole (s) defined above, at least one additional oxidation base which can be chosen from the oxidation bases conventionally used in oxidation dyeing and among which there may be mentioned in particular paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heretocyclic bases other than diaminopyrazole used in accordance with the invention.
  • at least one additional oxidation base which can be chosen from the oxidation bases conventionally used in oxidation dyeing and among which there may be mentioned in particular paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heretocyclic bases other than diaminopyrazole used in accordance with the invention.
  • paraphenylenediamines mention may more particularly be made, for example, of paraphenylenediamine, paratoluylenediamine, 2,6-dimethyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2-n- ⁇ ropyl paraphenylenediamine, 2-isopropyline , N- ( ⁇ - hydroxypropyl) paraphenylenediamine, N, N-bis- ( ⁇ -hydroxyéfhyl) paraphenylenediamine, 4-amino N- ( ⁇ -methoxyethyl) aniline, the paraphenylenediamines described in French patent application FR 2630438, and their addition salts.
  • the bis-phenylalkylenediamines there may be mentioned more particularly by way of example, N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1,3-diaminopropanol, N, N'-bis- ( ⁇ - hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylene diamine, the N, N'-bis- (4-amino phenyl) tetra-methylenediamine, N, N'-bis- ( ⁇ -hydroxyethyl), N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N ' -bis- (4-methylaminophenyl) tetramethylene diamine, N, N'-bis- (ethyl) N, N'- bis- (4'-amino, 3'-methylphenyl) ethylenediamine, and their addition salts
  • para-aminophenol mention may more particularly be made, for example, of para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxy-methyl 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 , and their addition salts.
  • para-aminophenol 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxy-methyl 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 , and their addition salts.
  • ortho-aminophenols that may be mentioned more particularly by way of example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methylphenoI, 5-acetamido 2-amino phenol, and their addition salts.
  • heterocyclic bases that may be mentioned more particularly by way of example, pyridine derivatives, pyrimidine derivatives, pyrazole derivatives other than the diamino pyrazoles of formula (I) used in accordance with the invention, and their addition salts.
  • these additional oxidation bases preferably represent from 0.0005 to 12% by weight of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight of this weight.
  • the oxidation dye compositions in accordance with the invention may also contain at least one coupler and / or at least one direct dye, in particular for modifying the nuances or enriching them with reflections.
  • the couplers which can be used in the oxidation dye compositions in accordance with the invention can be chosen from the couplers conventionally used in oxidation dyeing and among which there may be mentioned in particular metaphenylenediamines, meta-aminophenols, metadiphenols, mono or polyhydroxy derivatives of naphthalene and heterocyclic couplers such as, for example, indole or pyridine derivatives and their addition salts with an acid.
  • couplers are more particularly chosen from 2-methyl 5-aminophenol, 5-N- ( ⁇ -hydroxyethyl) amino 2-methyl phenol, 6-chloro-2-methyl-5-aminophenol, 3-amino phenol, 1,3-dihydroxy benzene, 1,3-dihydroxy 2-methyl benzene, 4-chloro 1,3-dihydroxy benzene, 2,4-diamino l- ( ⁇ -hydroxyethyloxy) benzene, 2-amino 4 - ( ⁇ - hydroxyethylamino) 1-methoxybenzene, 1,3-diamino benzene, 1,3- bis- (2,4-diaminophenoxy) propane, 3-ureido aniline, 3-ureido 1-dimethylamino benzene, sesamol, l- ⁇ -hydroxyethylamino-3,4-methylenedioxybenzene, -naphthol, 2 methyl-1-naphthol, 6-
  • these couplers represent in particular from 0.0001 to 10% of the total weight of the dye composition, preferably from 0.005 to 5% by weight, and even more preferably from 0.1 to 3% 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, tartrates, lactates and acetates.
  • the medium suitable for dyeing (or support) used according to the invention consists of water or of a mixture of water and at least one organic solvent chosen from lower alkanols in polyols and polyol ethers, aromatic alcohols, analogues and their mixtures.
  • the dye composition according to 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, cationic, nonionic, amphoteric, zwitterionic polymers or their mixtures, mineral or organic thickening agents, antioxidant agents, reducing agents, sun filters, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, silicones, film-forming agents, preserving agents, opacifying agents.
  • adjuvants conventionally used in compositions for dyeing the hair
  • adjuvants conventionally used in compositions for dyeing the hair such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, anionic, cationic, nonionic, amphoteric, zwitterionic polymers or their mixtures, mineral or organic thickening agents, antioxidant agents,
  • the pH of the dye composition according to the invention is between 3 and 12.
  • 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 subject of the invention is also a process for dyeing 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, for a time sufficient to develop the desired coloration, either in air or using an oxidizing agent.
  • the dye composition may optionally contain oxidation catalysts, in order to accelerate the oxidation process.
  • the coloring of the fibers can be carried out without the addition of an oxidizing agent, only in contact with the oxygen in the air.
  • At least one dye composition as defined above is applied to the fibers, the color being revealed at pH acid, neutral or alkaline using an oxidizing agent which is added just at the time of use to the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially separately.
  • the dye composition described above is preferably mixed with an oxidizing composition containing, in a medium suitable for dyeing, at the time of use, at least one oxidizing agent present in an amount sufficient to develop coloring.
  • the mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes, preferably 5 to 30 minutes, after which it is rinsed, washed with shampoo, rinsed again and dried.
  • the oxidizing agent present in the oxidizing composition as defined above 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, peroxide of urea, alkali metal bromates,. persalts such as perborates and persulfates. Hydrogen peroxide is particularly preferred.
  • 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, 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 object of the invention is 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. 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.
  • composition is prepared: - diaminopyrazole base of formula I 5 x 10 "3 mole
  • the base and the coupler are as defined below.
  • each weight-for-weight dye composition is mixed with a solution of hydrogen peroxide at 20 volumes (6% by weight), the pH of which has been adjusted to approximately 2.5 with orthophosphoric acid.
  • the mixture is applied to gray hair containing 90% white, natural hairs, at a rate of 5 g per 0.5 g of hair.
  • the hair is rinsed, washed with a standard shampoo, rinsed again and dried.
  • the color of the locks was evaluated in the L * a * b * system, on white and permanent hair, using a CM 2002 MINOLTA spectrophotometer.
  • the diaminopyrazoles according to the invention therefore make it possible to obtain intense and chromatic shades at alkaline pH.
  • the diaminopyrazoles according to the invention make it possible to obtain intense shades.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Cosmetics (AREA)
EP02764953A 2001-07-18 2002-07-09 Heteroaryl-substituierte diaminopyrazolderivate für die oxidative färbung von keratinfasern Withdrawn EP1412348A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0109622 2001-07-18
FR0109622A FR2827603B1 (fr) 2001-07-18 2001-07-18 Composes derives de diaminopyrazole substitues par un radical heteroaromatique et leur utilisation en teinture d'oxydation des fibres keratiniques
PCT/FR2002/002397 WO2003008405A1 (fr) 2001-07-18 2002-07-09 Composes derives de diaminopyrazole substitues par un radical heteroaromatique et leur utilisation en teinture d'oxydation des fibres keratiniques

Publications (1)

Publication Number Publication Date
EP1412348A1 true EP1412348A1 (de) 2004-04-28

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EP02764953A Withdrawn EP1412348A1 (de) 2001-07-18 2002-07-09 Heteroaryl-substituierte diaminopyrazolderivate für die oxidative färbung von keratinfasern

Country Status (4)

Country Link
US (1) US7056354B2 (de)
EP (1) EP1412348A1 (de)
FR (1) FR2827603B1 (de)
WO (1) WO2003008405A1 (de)

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Publication number Priority date Publication date Assignee Title
GB0218876D0 (en) * 2002-08-13 2002-09-25 Merck Sharp & Dohme Therapeutic agents
DE10254506A1 (de) * 2002-11-22 2004-06-03 Wella Ag N-Aryl-4,5-diaminopyrazole und diese Verbindungen enthaltende Färbemittel
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