EP1730149A1 - Nouveaux derives de naphtaline et produits colorants contenant ces composes, destines a des fibres de keratine - Google Patents

Nouveaux derives de naphtaline et produits colorants contenant ces composes, destines a des fibres de keratine

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Publication number
EP1730149A1
EP1730149A1 EP04790662A EP04790662A EP1730149A1 EP 1730149 A1 EP1730149 A1 EP 1730149A1 EP 04790662 A EP04790662 A EP 04790662A EP 04790662 A EP04790662 A EP 04790662A EP 1730149 A1 EP1730149 A1 EP 1730149A1
Authority
EP
European Patent Office
Prior art keywords
group
methyl
amino
ethyl
hydroxyethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04790662A
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German (de)
English (en)
Inventor
Markus Speckbacher
Hans-Jürgen BRAUN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Deutschland GmbH
Original Assignee
Wella GmbH
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Filing date
Publication date
Application filed by Wella GmbH filed Critical Wella GmbH
Publication of EP1730149A1 publication Critical patent/EP1730149A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/06—Peri-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • 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
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems

Definitions

  • the present invention relates to novel, uncharged and cationic naphthalene derivatives and colorants containing these compounds for keratin fibers, such as human hair.
  • oxidation dyes which are formed by oxidative coupling of one or more developer components with one or more coupler components
  • direct dyes are generally used.
  • oxidation-stable, direct dyes can be added to the oxidative system in order to achieve special color effects.
  • Direct dyes are incorporated into suitable substrates to be applied to the fiber. This method, commonly known as tinting, is easy to use and is characterized by little damage to the keratin fiber, since it is possible to work without the addition of ammonia or peroxide. However, the dyes used have to meet some requirements.
  • the object of the present invention is therefore to provide direct dyes for dyeing keratin fibers, in particular human hair, which meet these requirements.
  • the present invention therefore relates to asymmetrically substituted naphthalene derivatives of the general formula (I)
  • Ai and A 2 are different and, independently of one another, represent partial structures of the formulas (II), (purple), (Illb) (IV), (V) or (VI), of which formulas (II), (purple), ( Illb), (IV) and (V) are preferred;
  • E represents an oxygen or a sulfur atom
  • Y is a nitrogen atom or (preferably) a quaternary one
  • Nitrogen atom which is branched or linear Ci-C ⁇ -alkyl groups, branched or linear C 2 -C -hydroxyalkyl groups or branched or linear C -C 6 -polyhydroxyalkyl groups;
  • Ri is a hydrogen atom, an aromatic or heterocyclic radical of the general formula (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV) or (XVI )
  • Ria has the same meaning as Ri with the exception of hydrogen;
  • R 2 and R 3 can be the same or different and are hydrogen, an amino group, a C 1 -C 6 -alkylamino group, a C 1 -C 6 -N, N-dialkyl- amino group, a C ⁇ -C 6 -N, N- (dihydroxyalkyl) amino group, fluorine, chlorine, bromine, iodine, a cyano group, a C-rC ⁇ -alkylcyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a CrCe- Alkyl group, a -CC 6 alkyloxy group, a CrCe-hydroxyalkyl group,
  • Alkylcarboxylic acid group a Ci-C ⁇ -alkylcarboxylic acid ester group, a -C-C 6 alkyl - carboxylic acid amide group, represents a C ⁇ -C 6 -Alkylsulfonklarerios, a CrC 6 -Alkylsulfonklareester michleskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyinskyin
  • R 4 and R 5 may be the same or different and are hydrogen, a C 6 -C 6 -alkylamino group, a CiC- ⁇ -N ⁇ -dialkylamino group, a C 1 -C 6 -alkylcyano group, a methoxymethyl group, a tert-butyl group, an isopropyl group, a C ⁇ -C6 alkyl group, a C 6 alkyl oxy group, a -C 6 hydroxyalkyl group, a C ⁇ -C group 6 -Alkylcarbonklare-, a C ⁇ -C 6 -Alkylcarbonklareesteromia, a CrC 6 -Alkylcarbon- acid amide group, a C ⁇ -C 6 -Alkylsulfonklairerios, a C-rC sulfonic 6 alkyl, a C ⁇ -C 6 -Alkylsulfonklamidoli, a phenyl
  • an aromatic heterocyclic quaternary ammonium compound - preferably a quaternary compound of N-methylimidazole, N-allylimidazole, 2-ethylimidazole, 1, 2-dimethylimidazole, pyridine, 4-dimethylaminopyridine, pyrimidine, pyrazole, N-methylpyrazole Chinolins-; a non-aromatic heterocyclic quaternary ammonium compound-especially a quaternary compound of N-methyl-morpholine, N-ethylmorpholine or 1-methylpiperidine; a quaternary alkylammonium compound or arylammonium compound of the formula NR a RbR c , where R a , Rt > , and R c independently of one another are a benzyl radical, a phenyl radical or a Ci-to C ⁇ -alkyl radical - in particular a methyl radical, an ethyl radical,
  • the general formula (I) also includes all possible E and Z isomers.
  • Suitable neutral or cationic naphthalene derivatives of the general formula (I) are: 1- (2-tert-butylphenyl) -6- (2-hydroxyethyl) -1 H-indolo [5,4,3-def] isoquinoline- 2,5,7 (6H) - trione, 1- (2-tert-butylphenyl) -6- [2-hydroxy-1- (hydroxymethyl) ethyl] -1H-indoIo [5,4,3-def] isoquinoline- 2,5,7 (6H) -trione, 3- ⁇ 2- [2- (2,5-dioxo-5,6-dihydroisoindolo [6,7,1-cde] indole-1 (2H) -yI) - 5-methoxy-anilino] ethyl ⁇ -1-methyl-1 H-imidazol-3-ium bromide, 3- ⁇ 2- [4- (2,5-dioxo-5,6-d
  • Preferred compounds of the general formula (I) are 1- (2-tert-butylphenyl) -6- (2-hydroxyethyl) -1 H-indolo [5,4,3-def] isoquinoline-2,5,7 (6H) - trione, 1 - (2-tert-butylphenyl) -6- [2-hydroxy-1 - (hydroxymethyl) ethyl] -1 H -indolo [5,4,3-def] isoquinoline-2,5,7 (6H ) -t on, 3- ⁇ 2- [2- (2,5-dioxo-5,6-dihydroisoindolo [6,7,1-cde] indole-1 (2H) -yI) -5-methoxyanilino] ethyl ⁇ -1-methyl-1 H-imidazol-3-ium bromide, 3- ⁇ 2- [4- (2,5-dioxo-5,6-dihydroisoindol
  • naphthalene derivatives according to the invention of the general formula (!) are accessible by known synthetic processes from commercially available or easily manufactured components.
  • Naphthalene-1,8 4,5-tetracarboxylic acid bisanhydride (XVII) and 6-bromo-naphthostyril-5-carboxylic acid (XVIII).
  • Condensation reactions at elevated temperatures in suitable solvents can be used, according to scheme 1, to extract naphthalene-1, 8: 4,5-tetracarboxylic acid bisanhydride (XVII) with primary aliphatic, aromatic or heterocyclic amines and hydrazones ( A1 / A2) produce the corresponding asymmetrically substituted imides, amidines or isoamidines.
  • suitable solvents such as glacial acetic acid, DMF or molten imidazole
  • Lactams (XX) can be according to H. Langhals et. al. (Angew. Chem. 1995, 107, 2436-2439; Angew. Chem., Int. Ed. Engl. 1995, 34, 2234-2236) and EP 0 769 532 A1 by a ring narrowing reaction in a DMSO / methanol mixture under strong represent alkaline conditions from any bisimide derivative (XIX) (Scheme 2).
  • Bislactams (XXI) can be obtained via Ullmann condensation of aromatic or heterocyclic amines or p-phenylenediamine derivatives (A) with 6-bromonaphthostyril-5-carboxylic acid (XVIll) according to S. S. Daivi et. al. (Indian Journal of Chemistry, Vol. 24B, April 1985, 377-382) preparatively accessible (Scheme 3).
  • cationic representatives can be prepared in a simple manner either by introducing a cationic group (Scheme 4) or by quaternization of heterocyclic nitrogen atoms (Scheme 5).
  • the new naphthalene derivatives of the general formula (I) enable uniform, intensive and brilliant dyeing of fibers, in particular keratin fibers, such as human hair, but also wool or furs, under gentle and skin-friendly conditions, the dyeings being extraordinarily good against light , Sweat and shampooing. Furthermore, with particular excitation, for example by UV light, a pronounced solid-state fluorescence of the colored fiber z: u can be observed in certain cases.
  • the present invention therefore further provides (a) an agent for dyeing keratin fibers, in particular human hair, and (b) an oxidizing agent for simultaneously lightening and dyeing keratin fibers, in particular human hair, which are characterized in that they have at least one Contain naphthalene derivative of the general formula (I).
  • the naphthalene derivatives of the general formula (I) are preferably present in the colorant according to the invention in an amount of 0.01 to 10 percent by weight, in particular 0.1 to 8 percent by weight.
  • the colorant (a) according to the invention can also comprise further known direct-dyeing dyes from the group consisting of nitro dyes, azo dyes, athraquinone dyes and triphenylmethane dyes, alone or in a mixture with one another, such as, for example, 1, 4- Bis [(2-hydroxyethyl) amino] -2-nitrobenzene, 1- (2-hydroxyethyl) amino-2-nitro-4- [di (2-hydroxyethyl) amino] benzene, (HC Blue No. 2), 1 -Amino-3-methyl-4 - [(2-hydroxyethyl) amino] -6-nitrobenzene, (HC Violet No.
  • direct-dyeing dyes from the group consisting of nitro dyes, azo dyes, athraquinone dyes and triphenylmethane dyes, alone or in a mixture with one another, such as, for example, 1, 4- Bis [(2-hydroxyethyl) amino] -2-nitrobenz
  • 1,4-diamino-9,10-anthraquinone (CI61100, Disperse Violet No. 1), 1-amino-4- (methylamino ) -9,10-anthraquinone (CI61105, Disperse Violet No. 4, Solvent Violet No. 12), N- (6 - ((3-Chloro-4- (methylamino) phenyl) - imino) -4-methyl-3 -oxo-1,4-cyclohexadien-1-yl) urea (HC Red No.
  • the above-mentioned additional direct dyes can be present in the agent according to the invention in a total amount of about 0.01 to 4 percent by weight, the total amount of dyes in the dye according to the invention preferably being about 0.01 to 10 percent by weight, in particular 0.1 to 5 percent by weight, is.
  • the colorant according to the invention can furthermore all known and customary additives for such preparations, for example perfume oils, complexing agents, waxes, preservatives, thickeners, alginates, guar gum, hair-care substances, such as, for example, cationic polymers or lanolin derivatives, or anionic, nonionic, amphoteric or cationic surface-active agents Contain substances.
  • perfume oils for example perfume oils, complexing agents, waxes, preservatives, thickeners, alginates, guar gum, hair-care substances, such as, for example, cationic polymers or lanolin derivatives, or anionic, nonionic, amphoteric or cationic surface-active agents Contain substances.
  • Amphoteric or nonionic are preferred surface-active substances, for example betaine surfactants, propoinates and glycinates, such as, for example, cocoamphoglycinate or cocoamphdiglacinate, ethoxylated surfactants with 1 to 1000 ethylene oxide units, preferably with 1 to 300 ethylene oxide units, such as, for example, glyceride alkoxylates, for example ethoxylated castor oil with 25 ethylene oxide units, Polyglycolamides, ethoxylated alcohols and ethoxylated fatty alcohols (fatty alcohol alkoxylates) and ethoxylated fatty acid sugar esters, in particular ethoxylated sorbitan fatty acid esters, are used.
  • betaine surfactants propoinates and glycinates
  • ethoxylated surfactants with 1 to 1000 ethylene oxide units, preferably with 1 to 300 ethylene oxide units, such as, for example, glyceride alkoxylates, for
  • the abovementioned constituents are used in the amounts customary for such purposes, for example the surface-active substances in a concentration of 0.1 to 30 percent by weight, and the care substances in an amount of 0.1 to 5 percent by weight.
  • the colorant according to the invention in particular if it is a hair colorant, can be in the form of an aqueous or aqueous-alcoholic solution, a cream, a gel, an emulsion or an aerosol foam, the hair colorant being both in the form of a one-component preparation and in the form of a multicomponent preparation, for example in the form of a two-component preparation in which the respective dye derivative of the general formula (I) is packaged separately from the other constituents and the ready-to-use hair dye is only prepared immediately before use by mixing the two components.
  • the coloring agent can also be made up in the form of a two-component preparation, in which one component contains the oxidizing agent and the other component contains the other constituents of the agent, the oxidizing agent possibly also can consist of several components (eg 1st hydrogen peroxide and 2nd persulfate).
  • the colorant according to the invention has a pH of about 2 to 10, preferably about 5 to 10, and in particular a neutral to basic pH of about 7 to 10. Both organic and inorganic acids or bases are suitable for adjusting the pH value according to the invention.
  • Suitable acids include, in particular, ⁇ -hydroxycarboxylic acids, such as, for example, glycolic acid, lactic acid, tartaric acid, citric acid or malic acid, ascorbic acid, gluconic acid lactone, acetic acid, hydrochloric acid or phosphoric acid, and mixtures of these acids.
  • Suitable bases include sodium carbonate, sodium hydrogen carbonate, alkanolamines, for example monoethanolamine or triethanolamine, ammonia, aminomethylpropanol and sodium hydroxide.
  • the dye according to the invention is normally used by applying a sufficient amount of the dye, usually about 30 to 120 grams, of the dye (optionally with the addition of a suitable oxidizing agent) to the fiber, the dye at about 15 to 45 degrees Celsius about 1 to 60 minutes, preferably 5 to 30 minutes, then the fiber is rinsed thoroughly with water, optionally washed with a shampoo and finally dried.
  • the coloring agent described above can furthermore contain natural or synthetic polymers or modified polymers of natural origin, which are customary for cosmetic agents, whereby hair is at the same time achieved with the coloring.
  • Such agents are generally referred to as tinting or color strengthening agents.
  • polyvinylpyrrolidone polyvinyl acetate
  • polyvinyl alcohol or polyacrylic compounds such as polyacrylic acid or polymethacrylic acid
  • basic polymers of esters of polyacrylic acid polymethylacrylic acid and amino alcohols, for example their salts or quaternizing products, polyacrylonitrile, and copolymers of such vinyl acetate
  • natural polymers or modified natural polymers for example chitosan (deacetylated chitin) or chitosan derivatives, can be mentioned.
  • the abovementioned polymers can be present in the colorant according to the invention in the amounts customary for such agents, in particular in an amount of about 1 to 5 percent by weight.
  • the pH value of the tinting or color fixing agent according to the invention is preferably about 6 to 9.
  • the dye with additional setting is used in a known and customary manner by moistening the hair with the setting agent, setting (inserting) the hair for the hairstyle and subsequent drying.
  • the colorant according to the invention enables excellent, uniform, intensive and extremely long-lasting coloring of keratin fibers (for example human hair, wool or furs) without significant staining of the skin or scalp, which lasts five or more washes without noticeable fading of the hair color.
  • keratin fibers for example human hair, wool or furs
  • the following examples are intended to explain the subject matter of the invention in more detail without restricting it thereto.
  • Stage 1 Preparation of 2- (2-tert-butylphenylV7- (2-hvdroxyethyl) - benzo ⁇ mnH3.81phenanthroline-1, 3.6.8 (2H, 7H) -tetron 3.0 g (11, 19 mmol) naphthalene 1, 8: 4,5-tetracarboxylic acid bisanhydride are mixed with 8 g of imidazole and stirred at 150 ° C. 2.0 g (13.24 mmol) of 2-tert-butylaniline are slowly added to this mixture, alternately using an injection needle and 0.82 g (13.43 mmol) of ethanolamine are added dropwise. After 2.5 hours, the mixture is poured into 2N hydrochloric acid and stirred overnight. The precipitate is filtered off and dried. The crude product thus obtained is passed directly to stage 2 without further purification used.
  • Step 2 Preparation of 1 - (2-tert-butylphenyl) -6- (2-hvdroxyethyl) -1 H -indolof5,4,3-def1isoquinoline-2,5,7 (6H) -trione 1,7 g (3rd , 84 mmol) 2- (2-tert-butylphenyl) -7- (2-hydroxyethyl) benzo [lmn] - [3,8] - phenanthroline-1, 3,6,8 (2H, 7H) -tetron from step 1 are dissolved in a mixture of 40 ml DMSO and 20 ml methanol.
  • Step 1 Preparation of 1 - (2-tert-butylphenyl 6- (2-bromoethyl) -1 H -indolor5,4,3-deflisoquinoline-2,5,7 (6H) -trione 0.92 g (2.22 mmol) 1- (2-tert-butylphenyl) -6- (2-hydroxyethyl) -1 H-indolo [5,4,3-defjisoquinoline-2,5,7 (6H) -trione are dissolved in 60 ml chloroform and 15 ml (15.54 mmol) of phosphorus tribromide are added dropwise over the course of 20 minutes, the solution is refluxed for 2 hours, the reaction mixture is poured onto ice and the aqueous phase is extracted with chloroform and the combined organic phases are transferred Magnesium sulfate was dried and purified by column chromatography on silica gel using toluene as the eluent.
  • Step 2 Preparation of 3- ⁇ 2- [1 - (2-tert-butylphenvn-2,5,7-trioxo-1,2,5,7-tetrahvdro-6H-indolor5,4,3-def1-isoquinoline-6- vn-ethyl ⁇ - 1-methyl-1 H-imidazol-3-ium bromide 0.40 g (0.84 mmol) 1- (2-tert-butylphenyl) -6- (2-bromoethyl) -1 H- indolo [5,4,3-defjisoquinoline-2,5,7 (6H) -trione from stage 1 are dissolved in 40 ml of acetonitrile.
  • UV / Vis (DMSO): ⁇ max 361, 382, 433, 534 nm.
  • Example 8 Hair dye (without oxidizing agent)
  • naphthalene derivative of the general formula (I) 2.5 mmol of naphthalene derivative of the general formula (I) 5.0 g of ethanol 4.0 g of decyl polyglucose 0.2 g of ethylenediaminotetraacetic acid disodium salt hydrate ad 100.0 g of water, fully desalinated
  • the coloring solution is adjusted to a pH of 7 to 10 by adding ammonia.
  • the hair is colored by applying a sufficient amount of the colorant to the hair, rinsing the hair with lukewarm water after 30 minutes at 40 ° C. and then drying.
  • the dyeing results are summarized in Table 1 below.
  • Example 9 Hair dye (without oxidizing agent)
  • naphthalene derivative of the general formula (I) 2.5 mmol of naphthalene derivative of the general formula (I) 1.3 g of citric acid, anhydrous 25.0 g of ethanol 10.0 g of 1,2-propanediol 9.0 g of benzyl alcohol 4.0 g of hydroxyethyl cellulose ad 100.0 g of water, fully desalinated
  • the hair is colored by applying a sufficient amount of the colorant to the hair, rinsing the hair with lukewarm water after 30 minutes at 40 ° C. and then drying.
  • the dyeing results are summarized in Table 1 below.
  • Example 10 Hair dye (with oxidizing agent)
  • naphthalene derivative of the general formula (I) 1,000 g potassium persulfate 1,500 g ammonium persulfate 1,200 g sodium silicate 0.625 g magnesium oxide 0.250 g hydroxyethyl cellulose 0.300 g soap pearls 0.100 g disperse silica 0.025 g disodium EDTA 10,000 g hydrogen peroxide (12% in water )
  • the specified components are mixed to a homogeneous mass so that no dye particles can be seen.
  • a sufficient amount of the aforementioned coloring material for hair coloring is applied to the hair. After an exposure time of 45 minutes at 40 ° C, the hair is rinsed with lukewarm water and treated with an acidic conditioner, rinsed out again and dried.
  • Example 11 Hair dye (with oxidizing agent and other direct dye)
  • the specified components are mixed to a homogeneous mass, so that no dye particles can be recognized. Then a sufficient amount of the aforementioned coloring material for hair coloring is applied to the hair. After an exposure time of 45 minutes at 40 ° C, the hair is rinsed with lukewarm water and dried. A turquoise color is obtained.
  • Example 12 Hair dye (with oxidizing agent and other direct dye)
  • the specified components are mixed to a homogeneous mass, so that no dye particles can be recognized. Then a sufficient amount of the aforementioned coloring material for hair coloring is applied to the hair. After an exposure time of 45 minutes at 40 ° C, the hair is rinsed with lukewarm water and dried. A light red color is obtained.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des dérivés de naphtaline asymétriques de formule (I) et des produits contenant ces composés, destinés à colorer des fibres de kératine ou des produits à la fois pour colorer et éclaircir des fibres de kératine, A 1 et A2 étant différents et représentant indépendamment l'un de l'autre des structures partielles de formules (II), (IIIa), (IIIb), (IV), (V) ou (VI).
EP04790662A 2004-02-07 2004-10-20 Nouveaux derives de naphtaline et produits colorants contenant ces composes, destines a des fibres de keratine Withdrawn EP1730149A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004006143A DE102004006143A1 (de) 2004-02-07 2004-02-07 Neue Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern
PCT/EP2004/011853 WO2005075481A1 (fr) 2004-02-07 2004-10-20 Nouveaux derives de naphtaline et produits colorants contenant ces composes, destines a des fibres de keratine

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Publication Number Publication Date
EP1730149A1 true EP1730149A1 (fr) 2006-12-13

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Country Link
US (1) US7452385B2 (fr)
EP (1) EP1730149A1 (fr)
JP (1) JP2007523070A (fr)
BR (1) BRPI0418509A (fr)
DE (1) DE102004006143A1 (fr)
WO (1) WO2005075481A1 (fr)

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FR2958155B1 (fr) * 2010-04-02 2012-04-20 Oreal Composition de decoloration comprenant un sel peroxygene dans une base fortement riche en corps gras
US9812645B2 (en) 2015-02-13 2017-11-07 Flexterra, Inc. Perylene-based semiconductors
JPWO2022050286A1 (fr) * 2020-09-02 2022-03-10

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BRPI0418509A (pt) 2007-05-15
US7452385B2 (en) 2008-11-18
JP2007523070A (ja) 2007-08-16
DE102004006143A1 (de) 2005-08-25
WO2005075481A1 (fr) 2005-08-18
US20070157398A1 (en) 2007-07-12

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