US3578386A - Dyeing human hair with benzothiazole azo compounds - Google Patents

Dyeing human hair with benzothiazole azo compounds Download PDF

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Publication number
US3578386A
US3578386A US705925A US3578386DA US3578386A US 3578386 A US3578386 A US 3578386A US 705925 A US705925 A US 705925A US 3578386D A US3578386D A US 3578386DA US 3578386 A US3578386 A US 3578386A
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Prior art keywords
hair
dyeing
lower alkyl
human hair
composition
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US705925A
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English (en)
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Gregoire Kalopissis
Andree Bugaut
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LOreal SA
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LOreal SA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3691—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and sulfur as heteroatom

Definitions

  • R, R and R may be lower alkyl radicals, but in some of the formulae they may be H or acyl radicals instead, as set forth in detail in the specification.
  • R and R are combined with an adjacent N- to form a heterocyclic radical falling within the group consisting of morpholino, piperidino and pyrrolidino radicals.
  • the object of the present invention is to provide a new dyeing composition for keratinic fibers and more particularly for human hair, essentially characterized by the fact that it contains in solution at least one compound taken from the group consisting of:
  • R, R and n have the significances indicated above, and R represents a lower alkyl radical having from 1 to 4 carbon atoms or an acyl radical but cannot be a lower alkyl radical when R represents a hydrogen atom; R and R may be included with the nitrogen in heterocyclic ring falling within the group consisting of morpholino, piperidino and pyrrolidino radicals, R represents a lower alkyl radical and X a halogen atom or a SO,CH radical, it being undestood that in the latter case R may represent only a methyl group:
  • the dyeing compositions according to the invention may be used in a relatively wide pH range, but that the pH of these compositions should preferably be between 5 and 8.
  • the length of time that the dyeing compositions according to the invention should be in contact with the hair may vary greatly, but should preferably fall between 5 and 30 minutes.
  • the application temperature of these dyeing compositions may also vary, but in most cases, they should preferably be used at room temperature.
  • concentrations of dyes responding to Formulas I, II and III may vary significantly in the dyeing compositions according to the invention, but this concentration is preferably between 0.01% and 3%.
  • the dyes according to the invention may be mixed with each other or with other dyes normally used in dyeing hair, such as benzene, anthraquinone or azo dyes.
  • the dyeing compositions according to the invention may contain ingredients normally used in cosmetics, such as dispersing or wetting agents, thickeners, detergents, emollients or perfumes.
  • Another object of the present invention is to provide a process for dyeing keratinic fibers and particularly human hair essentially characterized by the fact that the hair is impregnated with a dyeing composition according to the invention, such as those described above, and that the composition is allowed to act for 5 to 30 minutes after which the hair is shampooed, rinsed and then dried.
  • Another object of the present invention is toprovide the new articles of manufacture consisting of those new chemical compounds having the Formulas I, II and III which are not described in the French Pat. No. 1,443,251, that is to say the new compositions consisting of those chemical compounds having the general Formula I, II or III, in which the radicals R and R form with the adjacent nitrogen atom a heterocyclic ring belonging to the group consisting of piperidino, morpholino and pyrrolidino radicals.
  • the new compounds described above may be prepared by condensing a diazonium salt obtained by diazotation of Z-aminobenzothiazole on an N,N-disubstituted aniline having the general formula:
  • R and n have the significances hereinbefore indicated; R and R form with the adjacent nitrogen atom a heterocyclic ring belonging to the group consisting of morpholino, piperidino and pyrrolidino radicals; the final mono or bis-quaternization being carried out with methyl sulfate or a halide of a lower alkyl with or without an appropriate solvent.
  • 0.2 mole (46.4 g.) of (N-ethyl- N-fi-piperidinoethyl)-ani1ine in solution is 50 cm. of acetic acid and 50 cm. of Water.
  • the reaction mixture is left for two hours at 0 C. and overnight at the ambient temperature.
  • the mixture is partially neutralized to a pH of 4 to 5 by means of a 3 N sodium hydroxide solution, and cooled overnight at 0 'C., after which drying yields the azo compound in the form of a salt.
  • the precipitate is suspended in one liter of Water at 80 C.; rendered alkaline by means of a N sodium hydroxide solution; and cooled; after which drying yields 55 g. of the desired azo compound, which, after recrystallization in alcohol melts at 130 C.
  • EXAMPLE 2' hydrate are obtained which, after recrystallization in alcohol at melts with decomposition at between 250 and 255 C.
  • This composition is applied to brown hair and left thereon for 15 minutes. The hair is then rinsed and shampooed.
  • This composition is applied to chestnut hair and left thereon for 15 minutes. The hair is then rinsed and shampooed.
  • This composition is applied to chestnut hair and left thereon for 15 minutes. The hair is then rinsed and sham- This composition is applied to White hair and left for 15 minutes, after which the hair is rinsed and shampooed.
  • This composition is applied to 90% white hair and left thereon for 15 minutes. The hair is then rinsed and shampooed.
  • a composition for dyeing human hair which comprises an aqueous solution of a compound selected from the group consisting of (a) a compound having the formula wherein R represents lower alkyl having 1-4 carbon atoms; n is a number between 2-6 inclusive; and R and R form, in combination with the nitrogen atom to which they are attached, piperidino;
  • peridino said compound being present in amounts from 0.01-3 weight percent of the total composition.
  • composition of claim 1 having a pH between 5-8 inclusive.
  • a method for dyeing human hair comprising impregnating said hair with a composition comprising an aqueous solution of a compound selected from the group consisting of (a) a compound having the formula wherein R represents lower alkyl having from 1 to 4 carbon atoms; n is a number between 2 and 6 inclusive, R represents a member selected from the group consisting of hydrogen and lower alkyl having from 1 to 4 carbon atoms, R is selected from the group consisting of hydrogen, lower alkyl having 1 to 4 carbon atoms and formyl, and R and R may form, in combination with the nitrogen, piperidino;
  • R represents a member selected from the group consisting of lower alkyl having 1 to 4 carbon atoms and formyl, with the proviso that R is not lower alkyl when R is hydrogen, and R and R may form, in combination with the nitrogen atom to which they are attached, piperidino;
  • R represents lower alkyl and
  • X represents a member selected from the group consisting of halogen and CH SO with the proviso that when X is CH SO R is methyl; and (c) a compound having the formula:
  • R, R X and n have the meanings given above;
  • R and R each independently represent lower alkyl having 1 to 4 carbon atoms and may form, in combination with the nitrogen atom to which they are attached, piperidino, said compounds being present in amounts from 0.01 to 3 weight percent of said composition, said composition being applied to the hair in amounts to effectively dye said hair, leaving said composition in contact with the hair for 5 to 30 minutes, and then washing, rinsing and drying said hair.
US705925A 1967-02-22 1968-02-16 Dyeing human hair with benzothiazole azo compounds Expired - Lifetime US3578386A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU53050A LU53050A1 (zh) 1967-02-22 1967-02-22

Publications (1)

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US3578386A true US3578386A (en) 1971-05-11

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US705925A Expired - Lifetime US3578386A (en) 1967-02-22 1968-02-16 Dyeing human hair with benzothiazole azo compounds

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US (1) US3578386A (zh)
DE (2) DE1794404C3 (zh)
FR (1) FR1560664A (zh)
GB (2) GB1211802A (zh)
LU (1) LU53050A1 (zh)

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3933787A (en) * 1973-01-12 1976-01-20 Sandoz Ltd., (Sandoz Ag) Substituted 4-(2-benzothiazolyl)phenylazo dyes having a quaternary ammonium, hydrazinium or optionally substituted amino substituent
US3988311A (en) * 1966-05-23 1976-10-26 Ciba-Geigy Ag Basic azo dyestuffs containing a heterocyclic diazo component and a para-N-tertiary or quaternary heterocyclic amine alkylene amino benzene coupling component
US4051084A (en) * 1974-01-11 1977-09-27 Bayer Aktiengesellschaft Cationic dyestuffs
US4714606A (en) * 1984-05-15 1987-12-22 Cytocolor Incorporated Method of staining and identifying cells and compositions thereof
US5879412A (en) * 1996-12-23 1999-03-09 L'oreal Compositions and processes for dyeing keratin fibers with an oxidation base, a coupler, a cationic direct dye, and an oxidizing agent
US5919273A (en) * 1996-12-23 1999-07-06 L'oreal Compositions and processes for dyeing keratin fibers with an oxidation base, a coupler, a cationic direct dye, and an oxidizing agent
US5993490A (en) * 1996-12-23 1999-11-30 L'oreal Composition for the oxidation dyeing of keratin fibers containing a cationic direct dye and dyeing process using this composition
US6001135A (en) * 1996-12-23 1999-12-14 L'oreal Compositions and processes for dyeing keratin fibers with cationic direct dyes, oxidation bases, and oxidizing agents
US6371994B2 (en) * 1998-05-28 2002-04-16 L'oreal S.A. Dye composition for keratin fibers, with a cationic direct dye and a polyol or polyol ether
US6436153B2 (en) * 1998-05-28 2002-08-20 L'ORéAL S.A. Composition for the direct dyeing of keratin fibres with a cationic direct dye and a polyol and/or a polyol ether
FR2822698A1 (fr) * 2001-04-03 2002-10-04 Oreal Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant monoazoique dicationique
FR2825623A1 (fr) * 2001-06-12 2002-12-13 Oreal Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques
FR2825624A1 (fr) * 2001-06-12 2002-12-13 Oreal Composition de teinture des fibres keratiniques humaines avec des colorants directs et des composes dicationiques
FR2825625A1 (fr) * 2001-06-12 2002-12-13 Oreal Utilisation de composes dicationiques en teinture des fibres keratiniques humaines et compositions les contenant
US6712861B2 (en) * 1997-10-22 2004-03-30 L'oreal S.A. Composition for dyeing keratin fibers and dyeing method using same
US20050183211A1 (en) * 2003-06-16 2005-08-25 Henri Samain Lightening dye composition comprising at least one cationic direct dye containing mixed chromophores
US20050204483A1 (en) * 2003-06-16 2005-09-22 Henri Samain Dye composition comprising at least one direct dye containing mixed chromophores
US20050241074A1 (en) * 2004-02-27 2005-11-03 Andrew Greaves Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero)arylmethane type, dyeing process and mixed dyes
FR2872035A1 (fr) * 2004-06-23 2005-12-30 Oreal Utilisation de composes polycationiques en teinture des fibres keratiniques
US20060037151A1 (en) * 2004-06-23 2006-02-23 L'oreal Use of polycationic compounds in the dyeing of keratinous fibres
US20060080791A1 (en) * 2004-10-14 2006-04-20 Nicolas Daubresse Dyeing composition comprising at least one disulphide dye and method of dyeing human keratin fibers using this dye
US20070125261A1 (en) * 2005-08-26 2007-06-07 Nicolas Daubresse Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing
EP1820536A1 (en) * 2006-02-18 2007-08-22 Wella Aktiengesellschaft Coloring agents for keratin fibers
EP1820537A1 (en) * 2006-02-18 2007-08-22 Wella Aktiengesellschaft Agents for coloring keratin fibers
US20090313769A1 (en) * 2006-03-24 2009-12-24 Nicolas Daubresse Method of dyeing and lightening keratin materials in the presence of a reducing agent comprising a fluorescent disulphide dye
US20100287714A1 (en) * 2006-03-24 2010-11-18 L'oréal Dye composition containing a thiol/disulphide fluorescent dye comprising amino groups and comprising an internal cationic charge, process for lightening keratin materials using this dye
FR2955860A1 (fr) * 2010-02-03 2011-08-05 Oreal Colorants directs azoiques fonctionnalises par une aniline secondaire n-alkylaminee, procede de coloration capillaire a partir de ces colorants
US9044412B2 (en) 2011-07-05 2015-06-02 L'oreal Dye composition using a long-chain ether of an alkoxylated fatty alcohol and a cationic polymer, processes and devices using the same
US9060944B2 (en) 2011-07-05 2015-06-23 L'oreal Cosmetic composition rich in fatty substances comprising a polyoxyalkylenated fatty alcohol ether and a direct dye and/or an oxidation dye, the dyeing method and the device
US9066890B2 (en) 2011-07-05 2015-06-30 L'oreal Dye composition comprising an alkoxylated fatty alcohol ether and a fatty alcohol
US9265705B2 (en) 2011-02-25 2016-02-23 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a nonionic surfactant, an amphoteric surfactant, an ethoxylated fatty alcohol, an alkaline agent and a reducing agent
US9271915B2 (en) 2011-02-25 2016-03-01 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a non-cellulose-based thickening polymer, an alkaline agent and a reducing agent
US9345652B2 (en) 2011-02-25 2016-05-24 L'oreal Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a sparingly or non-ethoxylated fatty alcohol, a cationic surfactant, an alkaline agent and a reducing agent
US9522106B2 (en) 2011-02-25 2016-12-20 L'oreal Composition for dyeing keratinous fibres comprising a direct dye having a disulphide/thiol functional group, a thickening polymer, an ethoxylated fatty alcohol and/or a nonionic surfactant, an alkaline agent and a reducing agent
US9827185B2 (en) 2012-08-02 2017-11-28 L'oreal Dyeing composition comprising at least one fatty substance, at least one oxidizing agent and at least one non-ionic, anionic and amphoteric surfactant
US10117811B2 (en) 2013-12-23 2018-11-06 L'oreal Packaging article comprising an envelope and an anhydrous dye composition comprising an oxidation dye, use of the same and process for dyeing keratin fibres
US10130829B2 (en) 2013-12-23 2018-11-20 L'oreal Packaging article comprising an envelope and an anhydrous dye composition comprising a direct dye, use of the same and process for dyeing keratin fibres
US10137063B2 (en) 2012-08-02 2018-11-27 L'oreal Dye composition comprising nonionic guar gum or a nonionic derivative thereof, process and device for the same
US10201483B2 (en) 2012-08-02 2019-02-12 L'oreal Dye composition in cream form comprising at least one oil and little or no solid fatty alcohol, dyeing process and suitable device
US10226411B2 (en) 2012-08-02 2019-03-12 L'oreal Dyeing composition comprising a fatty substance, a non-ionic guar gum, an amphoteric surfactant and a non-ionic or anionic surfactant, and an oxidizing agent, dyeing process and suitable device
US11096880B2 (en) 2017-06-16 2021-08-24 L'oreal Process for dyeing keratin fibres using at least one direct dye and at least one disulfide, thiol or protected-thiol fluorescent dye
US11278482B2 (en) 2017-06-16 2022-03-22 L'oreal Process for dyeing keratin materials using at least one blue, purple or green dye and at least one disulfide, thiol or protected thiol fluorescent dye
US11672747B2 (en) 2018-12-21 2023-06-13 L'oreal Process for dyeing keratin materials using a direct dye and an aliphatic ammonium salt, and composition comprising same
US11911636B2 (en) 2013-12-23 2024-02-27 L'oreal Process for treating keratin fibers using a packaging article comprising an envelope and an anhydrous composition comprising an oxidizing agent

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FR2766178B1 (fr) 1997-07-16 2000-03-17 Oreal Nouvelles bases d'oxydation cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture
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FR3136976A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition
FR3136966A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition
FR3136967A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition
FR3136968A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition
FR3136972A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition

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US4051084A (en) * 1974-01-11 1977-09-27 Bayer Aktiengesellschaft Cationic dyestuffs
US4714606A (en) * 1984-05-15 1987-12-22 Cytocolor Incorporated Method of staining and identifying cells and compositions thereof
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US5993490A (en) * 1996-12-23 1999-11-30 L'oreal Composition for the oxidation dyeing of keratin fibers containing a cationic direct dye and dyeing process using this composition
US6001135A (en) * 1996-12-23 1999-12-14 L'oreal Compositions and processes for dyeing keratin fibers with cationic direct dyes, oxidation bases, and oxidizing agents
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US6371994B2 (en) * 1998-05-28 2002-04-16 L'oreal S.A. Dye composition for keratin fibers, with a cationic direct dye and a polyol or polyol ether
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FR2822698A1 (fr) * 2001-04-03 2002-10-04 Oreal Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant monoazoique dicationique
WO2002080869A3 (fr) * 2001-04-03 2004-02-19 Oreal Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant monoazoique dicationique particulier
US7060110B2 (en) 2001-04-03 2006-06-13 L'oreal Dyeing composition for dyeing keratinous fibres comprising a particular dicationic monoazo dye
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WO2002080869A2 (fr) * 2001-04-03 2002-10-17 L'oreal Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant monoazoique dicationique particulier
US7172631B2 (en) 2001-06-12 2007-02-06 L'oreal S.A. Dyeing composition for human keratinous fibers with oxidation dyes and dicationic compounds
US7189266B2 (en) 2001-06-12 2007-03-13 L'oreal, S.A. Dyeing composition for human keratinous fibres with direct dyes and dicationic compounds
WO2002100366A2 (fr) * 2001-06-12 2002-12-19 L'oreal Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques
WO2002100366A3 (fr) * 2001-06-12 2004-02-19 Oreal Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques
WO2002100367A1 (fr) * 2001-06-12 2002-12-19 L'oreal Composition de teinture des fibres keratiniques humaines avec des colorants directs et des composes dicationiques
FR2825625A1 (fr) * 2001-06-12 2002-12-13 Oreal Utilisation de composes dicationiques en teinture des fibres keratiniques humaines et compositions les contenant
US20040237213A1 (en) * 2001-06-12 2004-12-02 Gregory Plos Dyeing composition for human keratinous fibres with direct dyes and dicationic compounds
US20040244124A1 (en) * 2001-06-12 2004-12-09 Gregory Plos Dyeing composition for human keratinous fibres with oxidation dyes and dicationic compounds
US20050039268A1 (en) * 2001-06-12 2005-02-24 Gregory Plos Use of dicatonic compounds for dyeing human keratinous fibres and compositions containing the same
US7261743B2 (en) 2001-06-12 2007-08-28 L'oreal Dicationic compounds for dyeing human keratin fibers, and compositions comprising them
WO2002100365A1 (fr) * 2001-06-12 2002-12-19 L'oreal Utilisation de composes dicationiques en teinture des fibres keratiniques humaines et compositions les contenant
FR2825623A1 (fr) * 2001-06-12 2002-12-13 Oreal Composition de teinture des fibres keratiniques humaines avec des colorants d'oxydation et des composes dicationiques
FR2825624A1 (fr) * 2001-06-12 2002-12-13 Oreal Composition de teinture des fibres keratiniques humaines avec des colorants directs et des composes dicationiques
US20050204483A1 (en) * 2003-06-16 2005-09-22 Henri Samain Dye composition comprising at least one direct dye containing mixed chromophores
US20050183211A1 (en) * 2003-06-16 2005-08-25 Henri Samain Lightening dye composition comprising at least one cationic direct dye containing mixed chromophores
US7201779B2 (en) 2003-06-16 2007-04-10 L'oreal S.A. Dye composition comprising at least one direct dye containing mixed chromophores
US7172633B2 (en) 2003-06-16 2007-02-06 L'ORéAL S.A. Lightening dye composition comprising at least one cationic direct dye containing mixed chromophores
US7300471B2 (en) 2004-02-27 2007-11-27 L'oreal S.A. Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero) arylmethane type, dyeing process and mixed dyes.
US20050241074A1 (en) * 2004-02-27 2005-11-03 Andrew Greaves Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero)arylmethane type, dyeing process and mixed dyes
FR2872035A1 (fr) * 2004-06-23 2005-12-30 Oreal Utilisation de composes polycationiques en teinture des fibres keratiniques
EP1618865A1 (fr) * 2004-06-23 2006-01-25 L'oreal Utilisation de composés polycationiques en teinture des fibres kératiniques
US20060037151A1 (en) * 2004-06-23 2006-02-23 L'oreal Use of polycationic compounds in the dyeing of keratinous fibres
US7326259B2 (en) 2004-06-23 2008-02-05 L'oreal S.A. Use of polycationic compounds in the dyeing of keratinous fibres
US20060080791A1 (en) * 2004-10-14 2006-04-20 Nicolas Daubresse Dyeing composition comprising at least one disulphide dye and method of dyeing human keratin fibers using this dye
US7488354B2 (en) 2004-10-14 2009-02-10 L'oreal S.A. Dyeing composition comprising at least one disulphide dye and method of dyeing human keratin fibers using this dye
US20070125261A1 (en) * 2005-08-26 2007-06-07 Nicolas Daubresse Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing
US7582122B2 (en) 2005-08-26 2009-09-01 L'oreal S.A. Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing
EP1820537A1 (en) * 2006-02-18 2007-08-22 Wella Aktiengesellschaft Agents for coloring keratin fibers
CN101384302B (zh) * 2006-02-18 2013-04-03 宝洁公司 用于着色角蛋白纤维的试剂
US20070199160A1 (en) * 2006-02-18 2007-08-30 The Procter & Gamble Company Agents for coloring keratin fibers
US20070199161A1 (en) * 2006-02-18 2007-08-30 Cecile Pasquier Coloring agents for keratin fibers
WO2007093943A1 (en) * 2006-02-18 2007-08-23 The Procter & Gamble Company Coloring agents for keratin fibers
US7513917B2 (en) 2006-02-18 2009-04-07 The Procter & Gamble Company Coloring agents for keratin fibers
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US20090158532A1 (en) * 2006-02-18 2009-06-25 Cecile Pasquier Coloring Agents for Keratin Fibers
US20090165221A1 (en) * 2006-02-18 2009-07-02 Cecile Pasquier Agents for Coloring Keratin Fibers
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WO2007097930A1 (en) * 2006-02-18 2007-08-30 The Procter & Gamble Company Agents for coloring keratin fibers
US7658770B2 (en) 2006-02-18 2010-02-09 The Procter & Gamble Company Agents for coloring keratin fibers
US7658771B2 (en) 2006-02-18 2010-02-09 The Procter & Gable Company Coloring agents for keratin fibers
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US8038731B2 (en) 2006-03-24 2011-10-18 L'oreal S.A. Method of dyeing and lightening keratin materials in the presence of a reducing agent comprising a fluorescent disulphide dye
US20100287714A1 (en) * 2006-03-24 2010-11-18 L'oréal Dye composition containing a thiol/disulphide fluorescent dye comprising amino groups and comprising an internal cationic charge, process for lightening keratin materials using this dye
US8562693B2 (en) 2006-03-24 2013-10-22 L'oreal Method of dyeing and lightening keratin materials in the presence of a reducing agent comprising a fluorescent deisulphide dye
US20090313769A1 (en) * 2006-03-24 2009-12-24 Nicolas Daubresse Method of dyeing and lightening keratin materials in the presence of a reducing agent comprising a fluorescent disulphide dye
FR2955860A1 (fr) * 2010-02-03 2011-08-05 Oreal Colorants directs azoiques fonctionnalises par une aniline secondaire n-alkylaminee, procede de coloration capillaire a partir de ces colorants
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US11096880B2 (en) 2017-06-16 2021-08-24 L'oreal Process for dyeing keratin fibres using at least one direct dye and at least one disulfide, thiol or protected-thiol fluorescent dye
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US11672747B2 (en) 2018-12-21 2023-06-13 L'oreal Process for dyeing keratin materials using a direct dye and an aliphatic ammonium salt, and composition comprising same

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DE1794404C3 (de) 1978-04-06
DE1719377B2 (de) 1977-08-04
DE1794404A1 (de) 1975-11-27
DE1794404B2 (de) 1977-08-11
DE1719377C3 (de) 1978-03-30
GB1211802A (en) 1970-11-11
LU53050A1 (zh) 1968-08-27
FR1560664A (zh) 1969-03-21
GB1211801A (en) 1970-11-11
DE1719377A1 (de) 1971-10-21

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