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WO2012080286A2 - Composition colorante comprenant une base d'oxydation hétérocyclique et un agent de couplage 3,5-diaminopyridine cationique - Google Patents

Composition colorante comprenant une base d'oxydation hétérocyclique et un agent de couplage 3,5-diaminopyridine cationique Download PDF

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WO2012080286A2
WO2012080286A2 PCT/EP2011/072669 EP2011072669W WO2012080286A2 WO 2012080286 A2 WO2012080286 A2 WO 2012080286A2 EP 2011072669 W EP2011072669 W EP 2011072669W WO 2012080286 A2 WO2012080286 A2 WO 2012080286A2
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radical
amino
alkyl
chosen
radicals
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WO2012080286A3 (fr
WO2012080286A9 (fr
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Anne-Marie Couroux
Aziz Fadli
Valérie NICOU
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LOreal SA
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LOreal SA
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Priority claimed from FR1060759A external-priority patent/FR2968967B1/fr
Priority claimed from FR1060757A external-priority patent/FR2968965B1/fr
Priority claimed from FR1060756A external-priority patent/FR2968964B1/fr
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Publication of WO2012080286A2 publication Critical patent/WO2012080286A2/fr
Publication of WO2012080286A3 publication Critical patent/WO2012080286A3/fr
Publication of WO2012080286A9 publication Critical patent/WO2012080286A9/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A61K8/4906—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
    • A61K8/49—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
    • 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
    • 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
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • 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
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits

Definitions

  • the subject of the invention is a dyeing composition
  • a dyeing composition comprising at least one particular heterocyclic oxidation base and at least one suitably selected cationic 3,5-diaminopyridine coupler, and also the dyeing process using this composition.
  • oxidation bases such as ortho- or para- phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds via a process of oxidative condensation.
  • couplers or coloration modifiers the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta- diphenols and certain heterocyclic compounds such as indole compounds.
  • the "permanent" coloration obtained by means of these oxidation dyes must, moreover, meet a certain number of requirements. Thus, it must have no toxicological drawbacks, it must allow shades to be obtained in the desired intensity and it must show good persistence with respect to external agents such as light, bad weather, washing, permanent-waving, perspiration and rubbing.
  • the dyes must also allow grey hair to be covered, and they must, finally, be as unselective as possible, i.e. they must produce the smallest possible coloration differences along the same keratin fibre, which is generally differently sensitized (i.e. damaged) between its end and its root.
  • the aim of the present invention is to obtain a composition for dyeing the hair which has improved dyeing properties in terms of strength and/or chromaticity and/or selectivity and/or resistance to external agents.
  • composition for dyeing keratin fibres comprising, in a suitable dyeing medium:
  • R 2 , R3, R 4 , R5 and R 6 which may be identical or different, represent a hydrogen atom; a C C 6 alkyl radical which is unsubstituted or substituted with at least one substituent chosen from OR, NHR, NRR', SR, SOR, S02R, COR, COOH, CONH2, CONHR, CONRR', PO(OH) 2 , SH, S0 3 X, a noncationic heterocycle, CI, Br or I, X denoting a hydrogen atom, Na, K or NH 4 , and R and R', which may be identical or different, representing a C C 4 alkyl or alkenyl; a C 2 -C 4 hydroxyalkyl radical; a C 2 -C 4 aminoalkyl radical; a phenyl radical; a phenyl radical substituted with a halogen atom or a C C 4 alkyl, C C 4 alkoxy, nitro, trifluoromethyl
  • n are integers, which may be identical or different, between 0 and 3 inclusive
  • X represents an oxygen atom or else the N H group
  • Y represents a hydrogen atom or else a C C 4 alkyl radical
  • Z represents a methyl radical when n is equal to 0, or Z represents a C C 4 alkyl radical, or an OR or NR"R"' group when n is greater than or equal to 1 , R" and R'", which may be identical or different, denoting a hydrogen atom or a C C 4 alkyl radical; or R 5 forms, with the nitrogen atom of the NR 3 R 4 group in position 5, a heterocycle comprising at least 4 ring members;
  • R 2 , R3 and R 4 radicals represents a hydrogen atom; ⁇ aminopyrazolopyridine oxidation bases of formula (II) and also their addition salts, their solvates :
  • Ri , R2, R3, R 4 and R 5 which may be identical or different, represent a hydrogen or halogen atom; an -NHSO 3 H radical; a hydroxyl radical; a (C C 4 )alkyl radical; a (Ci-C 4 )alkoxy radical; a (C C 4 )alkylthio radical; mono(CrC 4 )alkylamino; a di(Ci-C 4 )alkylamino radical in which the two alkyl groups can, together with the nitrogen atom to which they are bonded, form a ring which can be interrupted with one or more nitrogen, oxygen or sulphur atoms; a heterocycle; a nitro radical; a phenyl radical; a carbonyl radical; a (C C 4 )alkoxycarbonyl radical; a carboxamido radical; a cyano radical; an amino radical; a sulphonyl radical; a -C0 2 H radical, an -NH
  • Zi can also represent a divalent radical -S-, -SO- or -S0 2 - when R is a methyl radical;
  • R and R' 2 independently represent:
  • ring a substituted or unsubstituted, saturated, unsaturated or aromatic, 5- to 8-membered ring, optionally containing one or more heteroatoms or groups chosen from N, O, S, S0 2 and -CO-, it being possible for the ring to be cationic and/or substituted with a cationic radical;
  • R 17 R 18 Ri 9 group R 17 , R 18 and R 19 being linear or branched C1-C5 alkyls optionally substituted with one or more hydroxyl groups;
  • R when Zi , respectively Z 2 , represents a covalent bond, then R , respectively R' 2 , can also represent:
  • R and R' independently represent a hydrogen atom or an optionally substituted C C 6 alkyl radical
  • R' 3 , R' 4 and R' 5 which may be identical or different, represent:
  • R' 3 , R' 4 and R' 5 can form, in pairs, an optionally partially saturated ring
  • X represents an ion or group of ions for ensuring the electronegativity of the derivative of formula (III);
  • RL R 2 , R3 and R 4 which may be identical or different, represent:
  • a linear or branched C C 6 alkyl radical optionally substituted with one or more radicals chosen from the group consisting of an OR 5 radical, an N R 6 R 7 radical, a carboxy radical, a sulphonic radical, a carboxamido radical CON R 6 R 7 , a sulphonamido radical S0 2 N R 6 R 7 , a heteroaryl, or an aryl optionally substituted with one or more (C C 4 )alkyl, hydroxyl, C C 2 alkoxy, amino or di(C C 2 )alkylamino groups;
  • R 3 and R 4 can also represent a hydrogen atom
  • R 5 , R 6 and R 7 which may be identical or different, represent:
  • C C 4 alkyl radical optionally substituted with one or more radicals chosen from hydroxyl, C C 2 alkoxy, carboxamido CONR 8 Rg, sulphonyl S0 2 R 8 , aryl optionally substituted with a (C C 4 )alkyl, hydroxyl, C C 2 alkoxy, amino or di(Ci-C 2 )alkylamino; an aryl radical optionally substituted with a (C C 4 )alkyl, hydroxyl, C C 2 alkoxy, amino or di(C C 2 )alkylamino;
  • R 6 and R 7 which may be identical or different, can also represent a carboxamido radical CONR 8 R 9 ; or a sulphonyl radical S0 2 R 8 ;
  • R 8 and R 9 which may be identical or different, represent a hydrogen atom; or a linear or branched C C 4 alkyl radical optionally substituted with one or more hydroxyl or C C 2 alkoxy; and R 2 , on the one hand, and R 3 and R 4 , on the other hand, can form, with the nitrogen atom(s) to which they are attached, a saturated or unsaturated heterocycle comprising 5 to 7 ring members, which is optionally substituted with one or more radicals chosen from the group consisting of halogen atoms, amino, di(Ci-C 4 )-alkylamino, hydroxyl, carboxy, carboxamido and (C C 2 )alkoxy radicals, and Ci-C 4 alkyl radicals optionally substituted with one or more hydroxyl, amino, (di)alkylamino, alkoxy, carboxy or sulphonyl radicals;
  • R 3 and R 4 can also form, together with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle of which the carbon atoms can be replaced with an oxygen or nitrogen atom, which is optionally substituted;
  • Zi is an oxygen atom or an NR' 2 group
  • R' 2 is a hydrogen atom or a linear or branched C C 4 alkyl radical, a benzyl radical or an acetyl radical;
  • R is a linear or branched, saturated C 1 -C 10 alkyl radical which is substituted or interrupted with a cationic radical, which is optionally interrupted with one or more oxygen atoms and/or with one or more NR' 2 groups, which is optionally substituted with one or more radicals chosen from C C 4 hydroxyalkyi and alkoxy and hydroxyl radicals, or R is a saturated, unsaturated or aromatic cationic heterocycle comprising from 5 to 8 ring members, which is optionally substituted with one or more radicals chosen from C C 4 alkyl, hydroxyl, C C 4 alkoxy, amino, (C C 4 )alkyl- amino, di(C C 4 )alkylamino, thio, (C C 4 )alkylthio, carboxy, (C C 4 )alkylcarbonyl, sulphonyl, amido and C C 4 hydroxyalkyi radicals;
  • ⁇ R' and R' 2 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic heterocycle comprising from 5 to 8 ring members, which is optionally substituted with one or more radicals chosen from C C 10 alkyl radicals, and hydroxyl, C C 4 alkoxy, amino, (C C 4 )alkylamino, di(C C 4 )alkylamino, thio, (C C 4 )alkylthio, carboxy, (C C 4 )alkylcarbonyl, sulphonyl, amido and C C 4 hydroxyalkyi radicals, it being possible for this heterocycle to contain one or more heteroatoms chosen from N or O, preferably N, or
  • ⁇ R and R' 2 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated noncationic heterocycle comprising from 5 to 8 ring members, which is substituted with a cationic radical and optionally substituted with one or more radicals chosen from C 1 -C 10 alkyl radicals, and hydroxyl, C C 4 alkoxy, amino, (C C 4 )alkylamino, di(C C 4 )alkylamino, thio, (C C 4 )alkylthio, carboxy, (Ci-C 4 )alkylcarbonyl, sulphonyl, amido and C C 4 hydroxyalkyi radicals;
  • R' 3 is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine or bromine, and linear or branched C C 4 alkyl, carboxyl (-COOH) and (C C 4 )- alkoxycarbonyl radicals;
  • An- represents an anion or a mixture of anions; with the exception of the following compounds:
  • compositions 1 to 3 resulting from mixing each of the compositions 1 to 3 with an equal weight of 20-volume aqueous hydrogen peroxide solution (6% by weight).
  • the subject of the present invention is also a composition for dyeing keratin fibres comprising, in a suitable dyeing medium:
  • Z'i is an oxygen atom or an NR" 2 group
  • R" 2 is a hydrogen atom or a linear or branched C C 4 alkyl radical, a benzyl radical or an acetyl radical;
  • R"i is a linear or branched, saturated C1-C1 0 alkyl radical which is substituted or interrupted with a cationic radical, which is optionally interrupted with one or more oxygen atoms and/or with one or more NR" 2 groups, which is optionally substituted with one or more radicals chosen from C C 4 hydroxyalkyi and alkoxy and hydroxyl radicals, or R' is a saturated, unsaturated or aromatic cationic heterocycle comprising from 5 to 8 ring members, which is optionally substituted with one or more radicals chosen from C C 4 alkyl, hydroxyl, C C 4 alkoxy, amino, (C C 4 )- alkylamino, di(C C 4 )alkylamino, thio, (C C 4 )alkylthio, carboxy, (C C 4 )alkylcarbonyl, sulphonyl, amido and C C 4 hydroxyalkyi radicals;
  • R"i and R" 2 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic heterocycle comprising from 5 to 8 ring members, which is optionally substituted with one or more radicals chosen from C1-C1 0 alkyl radicals, and hydroxyl, C C 4 alkoxy, amino, (C C 4 )alkylamino, di(Ci-C 4 )alkylamino, thio, (C C 4 )alkylthio, carboxy, (C C 4 )alkylcarbonyl, sulphonyl, amido and C C 4 hydroxylalkyl radicals, it being possible for this heterocycle to contain one or more heteroatoms chosen from N or O, preferably N, or
  • R"i and R" 2 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated noncationic heterocycle comprising from 5 to 8 ring members, which is substituted with a cationic radical and optionally substituted with one or more radicals chosen from C1-C1 0 alkyl radicals, and hydroxyl, C C 4 alkoxy, amino, (C C 4 )alkylamino, di(C C 4 )alkylamino, thio, (C C 4 )alkylthio, carboxy, (Ci-C 4 )alkylcarbonyl, sulphonyl, amido and C C 4 hydroxylalkyl radicals;
  • R" 3 is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine or bromine, and linear or branched C C 4 alkyl, carboxyl (-COOH) and (C C 4 )alkoxy- carbonyl radicals;
  • An- represents an anion or a mixture of anions
  • the benzene coupler(s) is (are) chosen from meta-diphenols, meta-phenylenediamines and meta-aminophenols. Even more preferentially, the benzene coupler(s) is (are) chosen from the compounds of formula (VII) below and their addition salts, their solvat their salts:
  • R"'i represents a hydrogen atom or a C C 4 hydroxyalkyl radical
  • R'" 2 represents an amino radical or a hydroxyl radical
  • R'" 3 represents a hydrogen atom, a C C 4 alkyl radical, a C C 4 hydroxyalkyl radical or a Ci-C 4 hydroxyalkoxy radical;
  • R'" 4 represents a hydrogen atom or a halogen atom, for example a fluorine, chlorine, bromine or iodine atom.
  • R'" 2 is a hydroxyl radical.
  • the subject of the invention is also a dyeing process using this composition.
  • Another subject of the invention is the use of the composition of the present invention for dyeing keratin fibres, and in particular human keratin fibres such as the hair.
  • the invention also relates to multicompartment devices comprising compositions using at least one oxidation base chosen from the compounds of formulae (I), (II), (III) and (IV), their addition salts, their solvates and the solvates of their salts, and at least one coupler chosen from the compounds of formula (V) or (VI), and also their addition salts, their solvates and the solvates of their salts.
  • composition of the present invention makes it possible in particular to obtain a composition for dyeing keratin fibres which is suitable for use in oxidation dyeing and makes it possible to obtain a colouring with varied, intense or chromatic, powerful, attractive and sparingly selective shades which are highly resistant to the various attacks that the hair may be subjected to, such as shampooing, sweat, permanent reshaping operations and light.
  • the composition in accordance with the invention produces particularly chromatic shades.
  • the expression “at least one” is equivalent to the expression “one or more”.
  • the present invention also covers the mesomeric forms and the stereoisomers of the various oxidation dyes of the invention.
  • alkyl used for alkyl radicals and also for groups comprising an alkyl component, means a linear or branched carbon-based chain containing from 1 to 4 carbon atoms, which is unsubstituted or substituted with one or more heterocycles, or with one or more phenyl groups or with one or more groups chosen from halogen atoms such as chlorine, bromine, iodine and fluorine; and hydroxyl, alkoxy, amino, carbonyl, carboxamido, sulphonyl, -C0 2 H, -S0 3 H, -P0 3 H 2 , -P0 4 H 2 , - NHSO 3 H, sulphonamide, mono(CrC 4 )alkylamino and tri(Ci-C 4 )alkylammonium radicals, or alternatively with a di(C C 4 )alkylamino radical in which the two alkyl groups can
  • alkoxy used for the alkoxy radicals and also for groups comprising an alkoxy component, means a linear or branched O-carbon-based chain containing from 1 to 4 carbon atoms, which is unsubstituted or substituted with one or more groups chosen from heterocycles; halogen atoms such as chlorine, bromine, iodine and fluorine; and hydroxyl, amino, carbonyl, carboxamido, sulphonyl, -C0 2 H, -SO 3 H, -P0 3 H 2 , -P0 4 H 2 , -NHSO 3 H, sulphonamide, mono(CrC 4 )alkylamino and tri(Ci-C 4 )alkylammonium radicals, or alternatively with a di(C C 4 )alkylamino radical in which the two alkyl groups can form, together with the nitrogen atom of said di(C C 4 )alkylamino
  • heterocycle is intended to mean an aromatic or nonaromatic ring containing 5, 6, 7 or 8 ring members, and from 1 to 3 heteroatoms chosen from nitrogen, sulphur and oxygen atoms. These heterocycles can be condensed with other heterocycles or with a phenyl group.
  • halogen atom a (C C 4 )alkyl radical; a (C C 4 )alkoxy radical; a hydroxyl radical; an amino radical; a (C C 4 )alkylamino radical; or di(C C 4 )alkylamino in which the two alkyl groups can, together with the nitrogen atom to which they are bonded, form a ring which can be interrupted with one or more nitrogen, oxygen or sulphur atoms.
  • These heterocycles can also be quaternized with a (CrC 4 )alkyl radical.
  • thiadiazole triazole, isoxazole, oxazole, azaphosphole, thiazole, isothiazole, imidazole, pyrazole, triazine, thiazine, pyrazine, pyridazine, pyrimidine, pyridine, diazepine, oxazepine, benzotriazole, benzoxazole, benzimidazole, benzothiazole, morpholine, piperidine, piperazine, azetidine, pyrrolidine, aziridine, 3-(2-hydroxyethyl)benzothiazol-3-ium and 1-(2- hydroxyethyl)pyridinium.
  • phenyl is intended to mean a phenyl radical which is unsubstituted or substituted with one or more cyano, carbonyl, carboxamido, sulphonyl, -C0 2 H, -S0 3 H, -P0 3 H 2 , -P0 4 H 2 , hydroxyl, amino or mono(CrC 4 )alkylamino radicals, or di(C C 4 )alkylamino radicals in which the two alkyl groups can form, together with the nitrogen atom of said di(C C 4 )alkylamino group to which they are bonded, a ring which can be interrupted with one or more nitrogen, oxygen or sulphur atoms.
  • acetamide dimethylurea
  • O-methylcarbamate methylcarbonate
  • N-dimethyl- carbamate groups mention may in particular be made of acetamide, dimethylurea, O-methylcarbamate, methylcarbonate and N-dimethyl- carbamate groups and the esters.
  • the coupler or base compounds described above can be in the form of addition salts, in particular chosen from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates.
  • a base such as the sodium, potassium, ammonium or alkanolamine salts.
  • solvates for example a hydrate, or a solvate of a linear or branched alcohol such as ethanol or isopropanol.
  • the diaminopyrazole of formula (I) is such that R 6 is hydrogen.
  • R 2 , R 3 and R 4 represent a hydrogen atom or a C C 4 alkyl radical
  • R 5 is an alkyl, hydroxyalkyl or alkoxyalkyl radical.
  • RL R 2 and R 3 which may be identical or different, represent a hydrogen or halogen atom; a hydroxyl radical; a (C C 4 )alkyl radical; a (C C 4 )alkylthio radical; a (Ci-C 4 )alkoxy radical; an -NHSO 3 H radical; an amino radical; a (C C 4 )alkylamino radical; a di(C C 4 )alkylamino radical in which the two alkyl groups can, together with the nitrogen atom to which they are bonded, form a ring which can be interrupted with one or more nitrogen, oxygen or sulphur atoms; a heterocycle as defined above; a sulphonamide radical, a carbonyl radical, a (C C 4 )alkoxycarbonyl radical, a carboxamido radical, or a group of formula: R'" represents an oxygen or nitrogen atom, Q represents an oxygen atom or an NH or NH(C C 4 )alky
  • cationic heterocycle or ring is intended to mean a ring containing one or more quaternary ammonium groups.
  • radicals of the -N + R 17 R 18 Rig type mention may be made of trimethylammonium, triethylammonium, dimethylethylammonium, diethylmethylammonium, diisopropylmethylammonium, diethylpropylammonium, beta-hydroxyethyldiethylammonium, di(beta-hydroxyethyl)methylammonium and tri(beta-hydroxyethyl)ammonium radicals.
  • a cationic heterocycle By way of example of a cationic heterocycle, mention may be made of imidazolium, pyridinium, piperazinium, pyrrolidinium, morpholinium, pyrimidinium, thiazolium, benzimidazolium, benzothiazolium, oxazolium, benzotriazolium, pyrazolium, triazolium and benzoxazolium heterocycles.
  • a cationic heterocycle By way of example of a cationic heterocycle, mention may be made of imidazoliums, pyridiniums, piperaziniums, pyrrolidiniums, morpholiniums, pyrimidiniums, thiazoliums, benzimidazoliums, benzothiazoliums, oxazoliums, benzotriazoliums, pyrazoliums, triazoliums and benzoxazoliums.
  • Zi and/or Z 2 represent(s) a covalent bond, an -NR'6(CH 2 )q- radical or an -0(CH 2 ) p - radical and R and/or R' 2 is (are) a cationic radical.
  • R or R' 2 denotes a heterocycle
  • this heterocycle is preferably a cationic heterocycle or a heterocyle substituted with a cationic radical.
  • imidazoles substituted with a quaternary ammonium radical or imidazoliums piperazines substituted with a quaternary ammonium radical or piperaziniums, pyrrolidines substituted with a quaternary ammonium radical or pyrrolidiniums, and diazepanes substituted with a quaternary ammonium radical or diazepaniums.
  • R or R' 2 represents an -N + R 17 R 18 Ri 9 group, R 18 and R 19 being linear or branched C C 5 alkyls optionally substituted with one or more hydroxyl groups, such as trialkylammonium, tri(hydroxyalkyl)ammonium, hydroxyalkyldialkylammonium or di(hydroxy- alkyl)alkylammonium.
  • R' 3 , R' 4 and R' 5 radicals independently may be a hydrogen atom, or a C C 4 alkyl radical which can be substituted.
  • R' 3 , R' 4 and R' 5 independently represent a hydrogen or a C C 4 alkyl radical.
  • R' 4 and R' 5 together form a partially saturated or unsaturated 5- or 8-membered ring, in particular a
  • Zi represents a covalent bond, an -NR'6(CH 2 )q- radical or an -0(CH 2 ) p - radical and R is a cationic radical.
  • Ci-C 6 preferably C C 4 , alkyl radical, optionally substituted with a hydroxyl, a (CrC 2 )alkoxy, an amino or a (di)(CrC 2 )alkylamino;
  • the R ⁇ and R 2 radicals which may be identical or different, are chosen from a methyl, ethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2- hydroxypropyl or phenyl radical.
  • the R ⁇ and R 2 radicals form, together with the nitrogen atoms to which they are attached, a saturated or unsaturated, optionally substituted, 5- or 6-membered ring.
  • the R ⁇ and R 2 radicals form, together with the nitrogen atoms to which they are attached, a pyrazolidine ring or a pyridazolidine ring, which is optionally substituted with one or more C C 4 alkyl, hydroxyl,
  • R ⁇ and R 2 radicals form, together with the nitrogen atoms to which they are attached, a pyrazolidine ring or a pyridazolidine ring.
  • R 3 and R 4 radicals which may be identical or different, are more particularly chosen from a hydrogen atom; a linear or branched C C 6 , preferably C C 4 , alkyl radical optionally substituted with one or more hydroxyl, (C
  • the R 3 and R 4 radicals which may be identical or different, are chosen from a hydrogen atom, and a methyl, ethyl, isopropyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl and 2-carboxyethyl radical.
  • the R 3 and R 4 radicals represent a hydrogen atom.
  • the R 3 and R 4 radicals form, together with the nitrogen atom to which they are attached, a 5- or 7- membered ring chosen from pyrrolidine, piperidine, homopiperidine, piperazine and homopiperazine heterocycles; it being possible for said rings to be substituted with one or more of the following radicals: hydroxyl, amino, (di)(CrC 2 )alkylamino, carboxy, carboxamido, C C 4 alkyl which is optionally substituted with one or more hydroxyl, amino or (di)(CrC 2 )alkylamino radicals.
  • the R 3 and R 4 radicals form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, 2,5-dimethylpyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxy- pyrrolidine-2-carboxylic acid, 4-hydroxypyrrolidine-2-carboxylic acid, 2,4-dicarboxy- pyrrolidine, 3-hydroxy-2-hydroxymethylpyrrolidine, 2-carboxamidopyrrolidine, 3- hydroxy-2-carboxamidopyrrolidine, 2-(diethylcarboxamido)pyrrolidine, 2-hydroxy- methylpyrrolidine, 3,4-dihydroxy-2-hydroxymethylpyrrolidine, 3-hydroxypyrrolidine, 3,4-dihydroxypyrrolidine, 3-aminopyrrolidine, 3-methylaminopyrrolidine, 3-dimethyl- aminopyrrolidine, 4-amino-3-hydroxypyrrolidine, 3-hydroxy-4-(2-hydroxy- ethyl)amino
  • the R 3 and R 4 radicals form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine, 3-dimethylaminopyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, piperidine, hydroxypiperidine, homopiperidine, diazepane, N-methylhomopiperazine and ⁇ - ⁇ - hydroxyethylhomopiperazine.
  • a 5- or 7-membered ring chosen from pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine, 3-dimethylaminopyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, piperidine, hydroxypiperidine, homopiperidine, diazepane, N-methylhomopiperazine and ⁇ - ⁇ - hydroxyethylhomopiperazine.
  • the R 3 and R 4 radicals form, together with the nitrogen atom to which they attached, a 5-membered ring such as pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine or
  • diamino-N,N-dihydropyrazolone derivatives of formula (IV) or their addition salts, their solvates and the solvates of their salts which are particularly preferred are:
  • composition of the invention contains an oxidation base chosen from:
  • the cationic aminopyridines of formula (III) are chosen from the ollowing compounds:
  • the composition comprises a benzene coupler, preferably of formula (VII).
  • R" represents a hydrogen atom.
  • R'" 2 represents a hydroxyl radical.
  • R'" 3 represents a C C 4 alkyl radical.
  • R'" 3 represents a methyl radical.
  • R'" 4 represents a halogen atom.
  • R'" 4 represents a chlorine atom.
  • the composition in accordance with the invention comprises at least one benzene coupler chosen from 2-methyl-5- aminophenol, 5-N- ⁇ -hydroxyethyl)amino-2-methylphenol and 2-chloro-6-methyl-3- aminophenol.
  • the bases and the couplers used in the present invention are generally each present in an amount of between 0.001 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
  • the dyeing composition of the invention can optionally comprise one or more additional oxidation bases conventionally used for dyeing keratin fibres, which are different from the oxidation bases described above.
  • these additional oxidation bases are chosen from para- phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, bis-para- aminophenols, ortho-aminophenols, heterocyclic bases, and their addition salts, their solvates and the solvates of their salts.
  • para-phenylenediamines mention may be made, by way of example, of para-phenylenediamine, para-toluenediamine, 2-chloro-para- phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phen- ylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylene- diamine, ⁇ , ⁇ -dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylene- diamine, ⁇ , ⁇ -dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methyl- aniline, N,N-bis ⁇ -hydroxyethyl)-para-phenylenediamine, 4-N,N-bis -hydroxy- ethyl)amino-2-methylaniline, 4-N,N-bis ⁇
  • para-phenylenediamines mentioned above, para-phenylene- diamine, para-toluenediamine, 2-isopropyl-para-phenylenediamine, 2 ⁇ -hydroxy- ethyl-para-phenylenediamine, 2 ⁇ -hydroxyethyloxy-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, 2 ⁇ -acetylaminoethyloxy-para-phenylenediamine, their addition salts with an acid, their solvates and the solvates of their salts are particularly preferred.
  • N,N'-bis(4-methylaminophenyl)tetramethylenediamine N,N'-bis(ethyl)-N,N'-bis(4'- amino-3'-methylphenyl)ethylenediamine, 1 ,8-bis(2,5-diaminophenoxy)-3,6- dioxaoctane, their addition salts with an acid, their solvates and the solvates of their salts.
  • para-aminophenol examples include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3- hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- - hydroxyethylaminomethyl)phenol, 4-amino-2-fluorophenol, 1-hydroxy-4- methylaminobenzene, 2,2'-methylenebis-4-aminophenol, their addition salts with an acid, their solvates and the solvates of their salts.
  • ortho-aminophenols mention may be made, by way of example, of 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido- 2-aminophenol, their addition salts with an acid, their solvates and the solvates of their salts.
  • heterocyclic bases mention may be made, by way of example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino- 6-methoxypyridine, 2- ⁇ -methoxyethyl)amino-3-amino-6-methoxypyridine, 3,4- diaminopyridine, their addition salts with an acid, their solvates and the solvates of their salts.
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2359399; JP 88-169571 ; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2,4,5,6- tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-tri- aminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2750048 and among which mention may be made of pyrazolo[1 ,5- a]pyrimidine-3,7-diamine; 2,5-dimethylpyrazolo[1 ,5-a]pyrimidine-3,7-diamine; pyrazolo[1 ,5-a]pyrimidine-3,5-diamine; 2,7-
  • the additional oxidation base(s) is (are) generally each present in an amount of between 0.001 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
  • a coupler By way of example of a coupler, mention may be made of sesamol, 1- ⁇ - hydroxyethylamino-3,4-methylenedioxybenzene, oc-naphthol, 2-methyl-1-naphthol, 1 ,5-dihydroxynaphthalene, 2,7-naphthalenediol, 1-acetoxy-2-methylnaphthalene, 6- hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 3,5-diamino-2,6- dimethoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 3-amino-2-methylamino-6- methoxypyridine, 1-N- ⁇ -hydroxyethyl)amino-3,4-methylenedioxybenzene, 3- methyl-1-phenyl-5-pyrazolone, their addition salts with an acid, their solvates and the solvates of their salts.
  • the additional coupler(s) is (are) generally each present in an amount of between 0.001 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
  • the addition salts of the additional oxidation bases and of the additional couplers that can be used in the context of the invention are in particular chosen from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates, and the addition salts with a base, such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
  • the dyeing composition in accordance with the invention can also contain one or more direct dyes which can in particular be chosen from nitrobenzene dyes, azo direct dyes, and methine direct dyes. These direct dyes may be nonionic, anionic or cationic in nature. They may be synthetic or of natural origin.
  • the medium suitable for dyeing also called dyeing support, generally comprises water or a mixture of water and one or more organic solvents, for instance C C 4 lower alkanols, such as ethanol and isopropanol, polyols, for instance propylene glycol, dipropylene glycol or glycerol, and polyol ethers, for instance dipropylene glycol monomethyl ether.
  • organic solvents for instance C C 4 lower alkanols, such as ethanol and isopropanol
  • polyols for instance propylene glycol, dipropylene glycol or glycerol
  • polyol ethers for instance dipropylene glycol monomethyl ether.
  • the solvent(s) is (are) generally present in proportions which can be between
  • the dyeing composition in accordance with the invention can also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestrants, fragrances, buffers, dispersants, conditioning agents such as, for example, volatile or non-volatile, modified or unmodified silicones, film-forming agents, ceramides, preservatives and opacifiers.
  • adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic,
  • the above adjuvants are generally present in an amount, for each of them, of between 0.01 and 20% by weight, relative to the total weight of the composition.
  • the pH of the dyeing composition in accordance with 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 normally used in the dyeing of keratin fibres, or else by means of conventional buffer systems.
  • inorganic or organic acids such as hydrochloric acid, (ortho)phosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
  • basifying agents mention may be made, by way of example, of aqueous ammonia, alkali metal carbonates, sodium metasilicate, sodium silicate, alkanolamines such as mono-, di- and triethanolamines, and also derivatives thereof, for example monoethanolamine, aminomethylpropanol, triethanolamine, sodium hydroxide or potassium hydroxide, for example sodium hydroxide solution, sodium pyrrolidine carboxylate, and the compounds of formula (A) below:
  • W is a propylene residue optionally substituted with a hydroxyl group or a C1-C4 alkyl radical
  • R a , R b , R c and R d which may be identical or different, represent a hydrogen atom or a C C 4 alkyl or C C 4 hydroxyalkyl radical.
  • composition according to the invention may comprise one or more oxidizing agents.
  • the oxidizing agents are those conventionally used for the oxidation dyeing of keratin fibres and are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, peracids and oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases, and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
  • composition with or without oxidizing agent according to the invention can be in various forms, such as in the form of liquids, creams or gels, or in any form suitable for dyeing keratin fibres, and in particular human hair.
  • compositions one comprising at least one oxidation base chosen from the compounds of formulae (I), (II), (III) and (IV) and their addition salts, their solvates and the solvates of their salts, and at least one coupler chosen from the compounds of the formula (V) or (VI), and also their addition salts, their solvates and the solvates of their salts, and another composition comprising at least one oxidizing agent as described above.
  • composition of the invention is therefore applied to the hair for dyeing keratin fibres either as it is or in the presence of at least one oxidizing agent, for dyeing keratin fibres.
  • the process of the present invention is a process in which the composition without oxidant according to the present invention as defined above is applied to the fibres in the presence of an oxidizing agent for a period of time sufficient to develop the desired colouring.
  • the colour can be revealed at acidic, neutral or alkaline pH and the oxidizing agent can be added to the composition of the invention just at the time of use or it can be used on the basis of an oxidizing composition containing it, applied simultaneously with or sequentially to the composition of the invention.
  • the composition without oxidizing agent according to the present invention is mixed, preferably at the time of use, with a composition containing, in a medium suitable for dyeing, at least one oxidizing agent.
  • the mixture obtained is then applied to the keratin fibres. After a leave-in time of from 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, the keratin fibres are rinsed, optionally washed with shampoo, rinsed again, and then dried.
  • the oxidizing agents are those described above.
  • the oxidizing composition can also contain various adjuvants conventionally used in hair dyeing compositions and as defined above.
  • the pH of the oxidizing composition containing the oxidizing agent is such that, after mixing with the dyeing composition, the pH of the resulting composition applied to the keratin fibres preferably ranges between 3 and 12 approximately, and even more preferentially between 5 and 1 1. It can be adjusted to the desired value by means of acidifying or basifying agents normally used in the dyeing of keratin fibres and as defined above.
  • the subject of the invention is also a dyeing kit or multicompartment device in which a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above, comprising at least one oxidation base chosen from the compounds of formula (I), (II), (III) or (IV), their addition salts, their solvates and the solvates of their salts, and at least one coupler chosen from the compounds of formula (V) or (VI), and also their addition salts, their solvates and the solvates of their salts, and a second compartment contains at least one oxidizing agent.
  • a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above, comprising at least one oxidation base chosen from the compounds of formula (I), (II), (III) or (IV), their addition salts, their solvates and the solvates of their salts, and at least one coupler chosen from the compounds of formula (V) or (VI), and also their addition salts, their solvates and the solvates of their salts,
  • a second device consists of a first compartment containing a composition comprising at least one oxidation base chosen from the compounds of formula (I), (II), (III) or (IV), their addition salts, their solvates and the solvates of their salts, and a second compartment containing a composition comprising at least one coupler chosen from the compounds of formula (V) or (VI), and also their addition salts, their solvates and the solvates of their salts.
  • a third device can optionally comprise the two compartments of the second device plus a third compartment containing a composition comprising at least one oxidizing agent.
  • These devices can be fitted with a means for delivering the desired mixture onto the hair, such as the devices described in patent FR-2 586 913 in the name of the applicant.
  • the compounds of formula (IV) are synthesized according to a procedure such as those which are described in document EP 0 550 656.
  • the cationic aminopyridines of formula (I I I) as defined above can be prepared according to various synthesis routes.
  • R" 3 is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine or bromine, and linear or branched C C 4 alkyl, carboxyl (-COOH), and (Ci-C 4 )alkoxycarbonyl radicals, and x represents 0, 1 or 2.
  • cationic aminopyridines of formula (III) can be prepared from a compound of
  • Y represents a halogen or an S0 2 R" 4 group with R" 4 chosen from C C 4 alkyls, preferably methyl, a phenyl radical or a methylphenyl radical;
  • R" 3 is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine or bromine, and linear or branched C C 4 alkyl, carboxyl (-COOH) and (Ci-C 4 )alkoxycarbonyl radicals;
  • A represents a linear or branched alkyl chain optionally interrupted with a heteroatom of O, N or S type.
  • the substitution reaction is carried out in a dipole solvent such as acetonitrile or THF or in DMF or NMP or in an alcohol such as ethanol, in the presence of a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, and one or more ⁇ ⁇ for 1 to 24 hours at a temperature of from 20°C to the reflux temperature of the solvent.
  • a dipole solvent such as acetonitrile or THF or in DMF or NMP or in an alcohol such as ethanol
  • a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, and one or more ⁇ ⁇ for 1 to 24 hours at a temperature of from 20°C to the reflux temperature of the solvent.
  • hydroxyl function thus introduced is then substituted with a halide (mesyl or tosyl halide, for example) in a solvent such as acetonitrile or THF or in an alcohol such as ethanol, for example, in the presence of a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, for 1 to 24 hours at a temperature of from 20°C to the reflux temperature of the solvent.
  • a halide mesyl or tosyl halide, for example
  • a solvent such as acetonitrile or THF or in an alcohol such as ethanol
  • a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, for 1 to 24 hours at a temperature of from 20°C to the reflux temperature of the solvent.
  • substitution of the leaving group introduced in the preceding step is carried out either by reaction with an aromatic tertiary amine such as methylimidazole, so as to directly produce the cationic compounds, or by reaction with a particular primary or secondary amine, for instance ⁇ , ⁇ -dimethylethylenediamine or 2-piperidin-1- ylethanamine, so as to produce compounds which are alkylated with at least one equivalent of alkyl halide or methyl sulphate in a solvent such as THF or acetonitrile or dioxane or ethyl acetate for 15 minutes to 24 hours at a temperature ranging from 15°C to the reflux temperature of the solvent, so as to produce the cationic nitrous compounds.
  • an aromatic tertiary amine such as methylimidazole
  • a particular primary or secondary amine for instance ⁇ , ⁇ -dimethylethylenediamine or 2-piperidin-1- ylethanamine
  • a solvent such as THF or acetonit
  • the reduction of the nitro groups of these compounds is carried out under conventional conditions, for example by performing a hydrogenation reaction by heterogeneous catalysis in the presence of Pd/C, Pd(ll)/C, Ni/Ra, etc., or else by performing a reduction reaction with a metal, for example with zinc, iron, tin, etc. (see Advanced Organic Chemistry, 3 rd Edition, J. March, 1985, Wiley Interscience and Reduction in Organic Chemistry, M. Hudlicky, 1983, Ellis Horwood Series Chemical Science).
  • Step 1 Synthesis of N'-(3,5-dinitropyridin-2-yl)-N,N-dimethylethane-1 ,2-diamine
  • reaction medium After cooling of the reaction medium, the latter is poured onto a mixture of ice and water with stirring.
  • the yellow solid formed is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of desiccant until the weight is constant. 10.5 g (yield of 82.5%) of expected compound are obtained in the form of a yellow solid.
  • reaction medium After cooling under argon, the reaction medium is filtered under a stream of argon, on a sinter funnel packed with celite and over a vacuum flask containing 200 ml of 6.0 N hydrochloric 2-propanol at 0°C.
  • the expected compound crystallizes in the vacuum flask with stirring.
  • the solid is filtered off, dried quickly by suction on a sinter funnel under argon, rinsed with a minimum amount of cold iPrOH and then with 3 x 100 ml of iPr 2 0.
  • the compound is dried under vacuum at 50°C in the presence of desiccant until the weight is constant. 17.5 g (yield 87.4%) of expected compound are obtained in the form of a beige solid.
  • the yellow solid formed is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of desiccant until the weight is constant. 10.7 g (yield of 62%) of yellow solid, corresponding to the expected compound, are thus isolated.
  • the mass spectrometry analysis confirms the expected compound: the quasi- molecular ions [M+H] + and [M+Na] + of the expected molecule are mainly detected,
  • Step 3 2-[(3,5-dinitropyridin-2-yl)(methyl)amino]-N, N, N-trimethylethanammonium me
  • the mass spectrometry analysis confirms the expected compound.
  • Step 3 Synthesis of 2-[(3,5-diaminopyridin-2-yl)(methyl)amino]-N, N, N-trimethyl- ethanammonium chloride dihydrochloride
  • the medium is brought to 50°C, 5 g of palladium-on-carbon are introduced in small fractions, and the whole mixture is brought to reflux for 2 hours.
  • reaction medium After cooling under argon, the reaction medium is filtered, under a stream of argon, on a sinter funnel packed with celite and over a vacuum flask containing 250 ml of 6.0 N hydrochloric 2-propanol at 0°C.
  • the expected compound which crystallizes in the flask with stirring is filtered off, dried quickly by suction on a sinter funnel under argon, and rinsed with a minimum amount of cold iPrOH and then with 3 x 100 ml of iPr 2 0.
  • the compound is dried under vacuum at 50°C in the presence of desiccant until the weight is constant. 12.1 g (yield 81 %) of expected compound are thus isolated in the form of a beige solid.
  • Step 1 Synthesis of 1-(3,5-dinitropyridin-2-yl)-4-methylpiperazine
  • a yellow solid crystallizes from the medium; it is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of desiccant until the weight is constant. 5.7 g (yield of 88%) of expected compound are thus isolated in the form of a yellow solid.
  • the mass spectrometry analysis confirms the structure of the expected compound.
  • the quasi-molecular ions [M+H] + and [M+Na] + of the expected molecule are mainly detected, C10H13N5O4.
  • Step 2 Synthesis of 4-(3,5-dinitropyridin-2-yl)-1 , 1-dimethylpiperazin-1-ium methyl sulphate
  • the yellow solid formed is filtered off on a sinter funnel, dried by suction, washed with THF and then subsequently dried under vacuum at 50°C in the presence of desiccant until the weight is constant. 7.4 g (yield 94%) of expected compound are thus isolated in the form of a yellow solid.
  • the mass spectrometry analysis confirms the structure of the expected compound.
  • the expected cation is mainly detected.
  • Step 3 Synthesis of 4-(3,5-diaminopyridin-2-yl)-1 , 1-dimethylpiperazin-1-ium chlo
  • the medium is brought to 50°C and 3.5 g of palladium-on-carbon are introduced in small fractions and then the whole mixture is brought to reflux for 24 hours.
  • reaction medium is filtered on a sinter funnel packed with celite and over a vacuum flask containing 250 ml of 6.0 N hydrochloride 2-propanol at 0°C.
  • the expected compound crystallizes in the flask; it is filtered off on a sinter funnel, dried quickly by suction under argon, and rinsed with a minimum amount of cold iPrOH and then with 3 x 100 ml of iPr 2 0. The solid is then dried under vacuum at 50°C in the presence of desiccant until the weight is constant. 4.6 g (yield 88%) of expected compound are thus isolated in the form of a beige solid.
  • the expected cation [Cn H 2 oN 5 ] + is mainly detected.
  • the medium which has become heterogeneous, is then poured onto 500 g of ice.
  • a yellow solid precipitates more abundantly; it is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of desiccant until the weight is constant. 1 1.5 g (yield 78%) of expected compound are thus isolated in the form of a yellow solid.
  • the mass spectrometry analysis confirms the structure of the expected compound: the quasi-molecular ions [M+H] + and [M+Na] + of the expected molecule Ci 2 H 17 N 5 0 4 are mainly detected.
  • Step 2 Synthesis of 1- ⁇ 2-[(3,5-dinitropyridin-2-yl)amino]ethyl ⁇ -1-methylpiperidinium m
  • the yellow solid formed is filtered off on a sinter funnel, dried by suction, washed with ethyl acetate and then subsequently dried under vacuum at 50°C in the presence of desiccant until the weight is constant. 7.6 g (yield 90%) of expected compound are thus isolated in the form of a yellow solid.
  • the mass spectrometry analysis confirms the structure of the expected compound.
  • the expected cation [Ci 3 H 2 oN 5 0 4 ] + is mainly detected.
  • Step 3 Synthesis of 1- ⁇ 2-[(3,5-diaminopyridin-2-yl)amino]ethyl ⁇ -1-methyl- piperidinium chloride dihydrochloride
  • the expected cation [Ci 3 H 2 4N 5 ] + is mainly detected.
  • Example 4 The process is performed in an identical manner to that of Example 4, with substitution using 3-aminopropylimidazole and cationization using chloroethanol, followed by a catalytic reduction in an autoclave.
  • the expected cation [Ci 3 H 2 i N 5 0] + is mainly detected.
  • compositions 1 C1 , 1 C2 and C3 were prepared
  • Oleoyl amine comprising 2 EO, sold under
  • composition was diluted extemporaneously with 1 times its weight of 20- volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried. Results
  • the hair colouring was evaluated visually.
  • the colourings obtained are particularly strong and chromatic.
  • compositions 1 C1 , 1 C2 and 1 C3 were prepared.
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually.
  • the colourings obtained are particularly strong and chromatic.
  • compositions 1 C4, 1 C5 and 1 C6 were prepared
  • Oleoyl amine comprising 2 EO, sold under
  • carboxylic acid monoethanolamide (2 EO) 10 g A.M. 10 g A.M. 10 g A.M.
  • composition was diluted extemporaneously with 1 times its weight of 20- volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried. Results
  • the hair colouring was evaluated visually.
  • the colourings obtained are particularly strong and chromatic.
  • compositions 1 C7, 1 C8 and 1 C9 were pre pared.
  • Oleoyl amine comprising 2 EO, sold under
  • carboxylic acid monoethanolamide (2 EO) 10 g A.M. 10 g A.M. 10 g A.M.
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually.
  • compositions 2C1 and 2C1 were prepared.
  • Oleoyl amine comprising 2 EO, sold under the name
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually.
  • the colourings obtained are particularly chromatic.
  • composition 2C2 was prepared.
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried. Results
  • the hair colouring was evaluated visually.
  • the colouring obtained is particularly chromatic.
  • composition 2C3 was prepared.
  • Polyglycerolated oleoyl alcohol comprising 2 mol of glycerol 4 g A.M.
  • Polyglycerolated oleoyl alcohol comprising 4 mol of glycerol (78% 6 g A.M.
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually.
  • composition 3C1 was prepared.
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried. Results
  • the hair colouring was evaluated visually.
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually.
  • the colouring obtained is particularly strong and chromatic.
  • composition 3C3 was prepared.
  • composition was diluted extemporaneously with 1 times its weight of 20-volumes aqueous hydrogen peroxide solution.
  • the mixture was applied to grey hair containing 90% of white hairs, in a proportion of 10 g of mixture for 1 g of hair. After a leave-on time of 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually.
  • the colouring obtained is particularly strong and chromatic.

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Abstract

L'objet de la présente invention est une composition pour colorer des fibres kératiniques comprenant, dans un milieu approprié pour colorer des fibres kératiniques : - au moins une base d'oxydation choisie parmi les bases hétérocycliques 4,5-diaminopyrazole, pyrazolopyridine et diamino-N,N- dihydropyrazolone ; et - au moins un agent de couplage de type 3,5-diaminoyridine cationique. La composition selon l'invention permet, en particulier, d'obtenir une coloration ayant diverses nuances, qui sont fortes, chromatiques, puissantes, séduisantes, modérément sélectives et qui résistent aux diverses attaques auxquelles les cheveux peuvent être soumis.
PCT/EP2011/072669 2010-12-17 2011-12-14 Composition colorante comprenant une base d'oxydation hétérocyclique et un agent de couplage 3,5-diaminopyridine cationique Ceased WO2012080286A2 (fr)

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
FR1060759A FR2968967B1 (fr) 2010-12-17 2010-12-17 Composition tinctoriale comprenant une base d'oxydation pyrazolopyridine secondaire et un coupleur 3,5-diamino pyridine cationique
FR1060757A FR2968965B1 (fr) 2010-12-17 2010-12-17 Composition tinctoriale comprenant une base d'oxydation diamino-pyrazole et un coupleur 3,5-diamino pyridine cationique
FR1060756 2010-12-17
FR1060757 2010-12-17
FR1060756A FR2968964B1 (fr) 2010-12-17 2010-12-17 Composition tinctoriale comprenant une base d'oxydation diamino-n,n-dihydro-pyrazolone et un coupleur 3,5-diamino pyridine cationique
FR1060759 2010-12-17
US201161432296P 2011-01-13 2011-01-13
US201161432304P 2011-01-13 2011-01-13
US201161432300P 2011-01-13 2011-01-13
US61/432,304 2011-01-13
US61/432,300 2011-01-13
US61/432,296 2011-01-13

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Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1026978A (en) 1962-03-30 1966-04-20 Schwarzkopf Verwaltung G M B H Method of dyeing hair
GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
DE2359399A1 (de) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Haarfaerbemittel
FR2586913A1 (fr) 1985-09-10 1987-03-13 Oreal Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede
JPS63169571A (ja) 1987-01-06 1988-07-13 Nec Corp ト−ン検出装置
DE3843892A1 (de) 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
EP0550656A1 (fr) 1990-09-28 1993-07-14 Procter & Gamble Compositions de shampooing ameliorees.
WO1994008969A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Procede de production de derives de 4,5-diaminopyrazole, leur utilisation pour la teinture des cheveux, et nouveaux derives de pyrazole
WO1994008970A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Colorants d'oxydation pour cheveux, renfermant des derives du 4,5-diaminopyrazole, nouveaux derives du 4,5-diaminopyrazole et leur procede de fabrication
US5457200A (en) 1989-12-21 1995-10-10 Boehringer Mannheim 3-aminopyrazolo heterocyclic derivatives, and use for colorimetric determinations
WO1996015765A1 (fr) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation
EP0728464A1 (fr) 1995-02-27 1996-08-28 L'oreal Composition de teinture d'oxydation des fibres kératiniques comprenant un dérivé de diaminopyrazole et un coupleur hétérocyclique et procédé de teinture
FR2733749A1 (fr) 1995-05-05 1996-11-08 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
EP0770375A1 (fr) 1995-10-21 1997-05-02 GOLDWELL GmbH Composition pour la teinture des cheveux
DE19543988A1 (de) 1995-11-25 1997-05-28 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate
FR2750048A1 (fr) 1996-06-21 1997-12-26 Oreal Compositions de teinture des fibres keratiniques contenant des derives pyrazolo-(1, 5-a)-pyrimidine, procede de teinture, nouveaux derives pyrazolo-(1, 5-a)-pyrimidine et leur procede de preparation
EP1550656A1 (fr) 2003-12-01 2005-07-06 L'oreal Dérivés de 4-5-diamino-N,N-dihydro-pyrazol-3-one utilisés pour la teinture des fibres keratiniques
EP1792903A1 (fr) 2005-11-09 2007-06-06 L'oreal Composition pour la teinture des fibres kératiniques comprenant au moins un dérivé 3-amino pyrazolopyridine cationique
EP1792606A1 (fr) 2005-11-09 2007-06-06 L'Oréal Composition pour la teinture des fibres keratiniques comprenant au moins un dérive 3-amino pyrazolopyridine

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3071931B2 (ja) * 1992-03-05 2000-07-31 花王株式会社 ２−（アリール置換アルコキシ）−３，５−ジアミノピリジン誘導体及びこれを使用する角質繊維染色組成物
FR2822692B1 (fr) * 2001-03-27 2005-01-28 Oreal Composition pour la teinture d'oxydation contenant au moins une base d'oxydation 3-amino pyrazolo-[1,5-a]-pyridine et au moins un coupleur aminophenol particulier
FR2822691B1 (fr) * 2001-03-27 2005-02-25 Oreal Composition pour la teinture d'oxydation contenant au moins une base d'oxydation 3-amino pyrazolo-[1,5-a]-pyridine et au moins un coupleur pyridinique particulier
FR2852240B1 (fr) * 2003-03-13 2007-10-05 Oreal Nouveaux coupleurs du type 2,3,5-triaminopyridine et utilisation de ces coupleurs pour la teinture des fibres keratiniques
FR2874821B1 (fr) * 2004-09-08 2006-10-20 Oreal Nouveaux colorants directs noirs di-noyaux heteroaromatiques
FR2915886B1 (fr) * 2007-05-09 2014-05-09 Oreal Composition tinctoriale comprenant une base d'oxydation aminopyrazolopyridine particuliere, un coupleur et un tensioactif particulier
FR2927078B1 (fr) * 2008-02-06 2010-02-26 Oreal Composition pour la teinture des fibres keratiniques comprenant au moins un derive de diamino-n,n-dihydro-pyrazolone cationique
FR2953517B1 (fr) * 2009-12-07 2012-04-27 Oreal Nouvelles amino-pyridines cationiques, composition tinctoriale comprenant une amino-pyridine cationique, procedes et utilisations

Patent Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1026978A (en) 1962-03-30 1966-04-20 Schwarzkopf Verwaltung G M B H Method of dyeing hair
GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
DE2359399A1 (de) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Haarfaerbemittel
FR2586913A1 (fr) 1985-09-10 1987-03-13 Oreal Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede
JPS63169571A (ja) 1987-01-06 1988-07-13 Nec Corp ト−ン検出装置
DE3843892A1 (de) 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
US5457200A (en) 1989-12-21 1995-10-10 Boehringer Mannheim 3-aminopyrazolo heterocyclic derivatives, and use for colorimetric determinations
EP0550656A1 (fr) 1990-09-28 1993-07-14 Procter & Gamble Compositions de shampooing ameliorees.
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
WO1994008970A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Colorants d'oxydation pour cheveux, renfermant des derives du 4,5-diaminopyrazole, nouveaux derives du 4,5-diaminopyrazole et leur procede de fabrication
WO1994008969A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Procede de production de derives de 4,5-diaminopyrazole, leur utilisation pour la teinture des cheveux, et nouveaux derives de pyrazole
WO1996015765A1 (fr) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation
EP0728464A1 (fr) 1995-02-27 1996-08-28 L'oreal Composition de teinture d'oxydation des fibres kératiniques comprenant un dérivé de diaminopyrazole et un coupleur hétérocyclique et procédé de teinture
FR2733749A1 (fr) 1995-05-05 1996-11-08 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
EP0770375A1 (fr) 1995-10-21 1997-05-02 GOLDWELL GmbH Composition pour la teinture des cheveux
DE19543988A1 (de) 1995-11-25 1997-05-28 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate
FR2750048A1 (fr) 1996-06-21 1997-12-26 Oreal Compositions de teinture des fibres keratiniques contenant des derives pyrazolo-(1, 5-a)-pyrimidine, procede de teinture, nouveaux derives pyrazolo-(1, 5-a)-pyrimidine et leur procede de preparation
EP1550656A1 (fr) 2003-12-01 2005-07-06 L'oreal Dérivés de 4-5-diamino-N,N-dihydro-pyrazol-3-one utilisés pour la teinture des fibres keratiniques
EP1792903A1 (fr) 2005-11-09 2007-06-06 L'oreal Composition pour la teinture des fibres kératiniques comprenant au moins un dérivé 3-amino pyrazolopyridine cationique
EP1792606A1 (fr) 2005-11-09 2007-06-06 L'Oréal Composition pour la teinture des fibres keratiniques comprenant au moins un dérive 3-amino pyrazolopyridine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. MARCH: "Advanced Organic Chemistry", 1985, WILEY INTERSCIENCE
M. HUDLICKY: "Reduction in Organic Chemistry", 1983, ELLIS HORWOOD SERIES CHEMICAL SCIENCE

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