WO2000052100A1 - Agent pour colorer des fibres - Google Patents

Agent pour colorer des fibres Download PDF

Info

Publication number
WO2000052100A1
WO2000052100A1 PCT/EP2000/001024 EP0001024W WO0052100A1 WO 2000052100 A1 WO2000052100 A1 WO 2000052100A1 EP 0001024 W EP0001024 W EP 0001024W WO 0052100 A1 WO0052100 A1 WO 0052100A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
thioxo
dye
dihydro
dione
Prior art date
Application number
PCT/EP2000/001024
Other languages
German (de)
English (en)
Inventor
Thomas Kripp
Thomas Czigler
Pascal André SEMADENI
Original Assignee
Wella Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Wella Aktiengesellschaft filed Critical Wella Aktiengesellschaft
Publication of WO2000052100A1 publication Critical patent/WO2000052100A1/fr

Links

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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • 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
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups

Definitions

  • the present application relates to new dyes obtainable by reacting thiobarbituric acid with one or more carbonyl compounds, a process for the preparation of these dyes and an agent for dyeing fibers, in particular hair, and a method for dyeing and later decoloring fibers using this agent.
  • dyestuffs For the dyeing of keratin-containing fibers, such as hair, wool or furs, either direct synthetic or vegetable dyes or oxidation dyes, which result from the oxidative coupling of so-called developer substances with so-called coupler substances, are generally used. Although a large number of dyestuffs are known, only a few dyestuffs are suitable for use in dyes for keratin fibers, since these have to meet a multitude of conditions which in other areas of dyeing (dyeing synthetic fibers or foodstuffs) only have to be partially fulfilled .
  • a dye for keratin fibers must be able to dye the hair, be toxicologically harmless, enable coloring under mild conditions (low temperatures etc.), cause as little skin staining as possible, be water-soluble, largely sweat-resistant and washable, apply evenly to the fiber ( particularly important for dye mixtures), evenly (ie without changing the color) washed out, have the highest possible coverage, damage the fiber as little as possible and do not interfere with other hair treatment methods (e.g. permanent wave treatment)
  • the present invention therefore relates to the reaction of (a) thiobarbituric acid and / or its derivatives, for example the alkali metal or alkaline earth metal salts of thiobarbituric acid, with (b) one or more carbonyl compounds from the group consisting of saturated dialdehydes, saturated diketones, saturated ketoaldehydes , unsaturated dialdehydes, unsaturated diketones, unsaturated ketoaldehydes, monoaldehydes with one or more chromophoric groups, monoketones with one or more chromophoric groups and quinones, available non-oxidative dyes and a process for the preparation of these dyes.
  • dialdehydes for example glutacodialdehyde or glutacondialdehyde monoenolate, gemsteinedialdehyde,
  • keto aldehydes mono aldehydes with one or more chromophoric groups or monoketones with one or several chromophoric groups, for example 2,3,4-trihydroxybenzaldehyde, 3-oxobutyraldehyde, acrolein, acetaldehyde, benzaldehyde and its derivatives (for example p-dimethylaminobenzaldehyde), dimethylamino-phenylpentadienal, ethylvanillin, glyceraldehyde, isovanillin, methylfurfural , o-vanillin, stilbenaldehyde, vanillin, cinnamaldehyde and its derivatives (for example p-dimethylamino-cinnamaldehyde, p-nitro-cinnamaldehyde or o-nitro-cinnamaldehyde), benzo
  • the new dyes can be prepared in a simple manner by heating an aqueous solution containing one or more suitable carbonyl compounds and a 1 to 2-fold molar excess (based on the number of aldehyde, ketone or quinone groups in the carbonyl compound) on thiobarbituric acid or its derivatives with a pH value of less than / equal to 3 to at least 50 ° C, the reaction mixture being preferably stirred.
  • the desired pH is adjusted by adding a suitable organic or inorganic acid, with the use of hydrochloric acid being particularly preferred. With less reactive carbonyl compounds, higher temperatures (approx. 80 ° C) and / or longer reaction times (1-2 hours) are required.
  • the reaction mixture is then cooled and the precipitated dye is filtered off.
  • the dye thus obtained can be cleaned again.
  • 1 g of the dye is fine in a grater pulverized, the powder obtained is then heated in 200 ml of 0.6 N hydrochloric acid for 40 minutes, then cooled to 60 ° C and filtered through a glass frit with a slight vacuum.
  • the powder obtained is washed again with 100 ml of 0.6 N hydrochloric acid, then with 25 ml of cold water, 25 ml of ethanol and finally with 100 ml of diethyl ether. It is then dried in vacuo at 60 ° C. to constant weight.
  • the second thiobarbituric acid group can also be replaced by a corresponding chromophoric system for monovalent carbonyl compounds (example: benzaldehyde ⁇ vanillin ⁇ p-dimethylaminobenzaldehyde).
  • a broadband absorption behavior with high extinction coefficients can generally be observed.
  • the dyes have a high dyeing capacity and very good sweat and wash fastness without containing azo groups or metal salts and have a number of advantages over conventional non-oxidative dyes (so-called direct draws) (see Table 7).
  • the present invention therefore further relates to an agent for dyeing or tinting fibers containing at least one of the dyes according to the invention described above.
  • the fibers in particular are keratin fibers, for example wool, silk, furs or hair (in particular human hair), but also non-keratin fibers, for example cotton, linen, hemp textiles, Breness fibers, viscose, acetyl cellulose, cellulose triacetate or polyamide fibers.
  • the agent for dyeing fibers according to the invention can be present, for example, in the form of a solution, in particular as an aqueous alcohol solution, a cream, a gel or an emulsion.
  • a solution in particular as an aqueous alcohol solution, a cream, a gel or an emulsion.
  • lower aliphatic monohydric or polyhydric alcohols, their esters and ethers, or else mixtures of these solvents with one another or with water can be used as solvents.
  • the maximum boiling point of the abovementioned suitable solvents is approximately 400 ° C., a boiling point of 20 ° C. to 250 ° C. being preferred. It is also possible to remove the agent according to the invention with the aid of an atomizer or other suitable pump devices or spray devices or in a mixture with conventional propellants liquefied under pressure as an aerosol spray or as an aerosol foam from a pressure container.
  • the dye is contained in the colorant according to the invention in an amount of 0.001 to 10 percent by weight, preferably 0.01 to 3 percent by weight.
  • the pH of the colorant according to the invention can vary from 0 to 14, depending on the fiber to be colored, over the entire pH range.
  • the pH is preferably about 2 to 10, with an acidic pH of 2 to 7 being particularly preferred, particularly when coloring human hair.
  • An alkaline pH is preferably adjusted with ammonia or sodium hydroxide solution, but it is also possible to use organic amines, such as monoethanolamine or triethanolamine, instead of ammonia.
  • an organic or inorganic acid such as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, citric acid, tartaric acid, glycolic acid or lactic acid, can be used to set an acidic pH.
  • the colorant according to the invention can additionally contain other additives customary for such colorants, such as care agents, thickeners, plasticizers, preservatives, wetting agents or emulsifiers, for example from the classes of anionic, amphoteric, nonionic or zwitterionic surface-active substances such as fatty alcohol sulfates, alkane sulfonates, Alkylbenzenesulfonates, alkylcarnitines, acyl-carnitines, alkylbetaines, ⁇ -olefinsulfonates, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid aeanolamines, ethoxylated fatty acid esters, fatty alcohol polyglycol ether sulfates, alkyl polyglucosides, thickeners such as higher fatty alcohol cellulose, paraffin oil, benton oil, benton derivatives, starch Fatty acids, water-soluble polymeric thickeners
  • the colorant according to the invention can furthermore contain natural or synthetic polymers or modified polymers of natural origin, whereby a strengthening of the keratin fiber is achieved simultaneously with the coloring.
  • synthetic polymers known for this purpose in cosmetics, for example polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol or polyacrylic compounds such as polyacrylic acid or polymethacrylic acid, polyacrylonitrile, polyvinyl acetates and copolymers of such compounds, such as polyvinylpyrrolidone-vinyl acetate, are mentioned; while, for example, chitosan (deacetylated chitin) or chitosan derivatives can be used as natural polymers or modified natural polymers.
  • the ingredients mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, the thickeners in an amount of about 0.1 to 25 percent by weight and the care substances in an amount of about 0.1 to 5 weight percent.
  • the abovementioned polymers can be used in the amount customary for such agents, in particular in an amount of about 1 to 5 percent by weight.
  • the agent according to the invention for dyeing fibers can additionally have coloring herbal components, for example henna leaves, indigo, chamomile flowers, curcuma roots, rot tree bark, olive leaves, Canadian blood root, turmeric root, yellow wood, red wood, red sandalwood, blue wood, madder root, in order to achieve special shades.
  • the substantive dyes mentioned can be contained in an amount of about 0.01 to 4 percent by weight.
  • the colorant according to the invention enables uniform, wash-stable dyeings of fibers, in particular keratin fibers, such as human hair, which do not show any significant difference from the original color even after 20 washes with a shampoo, with virtually any color tone being obtainable by varying the dyes used. Furthermore, there is little, if any, hair coloring on the scalp.
  • the agent according to the invention can also be used to add a multitude of different fashionable or natural shades, for example purple-violet to black, red, orange, yellow, blue, violet, without the addition of other dyes or brown shades can be achieved (see Table 8).
  • Table 8 Dyes obtained by reacting thiobarbituric acid with various carbonyl compounds, sorted by color
  • the dyeing with the colorant according to the invention is carried out by applying an amount sufficient for dyeing the hair, generally about 50 to 150 grams, to the hair after an exposure time sufficient for hair dyeing, which is usually about 3 to at 20 to 50 ° C. 60 minutes, preferably 5 to 30 minutes, the hair is rinsed with water, optionally washed with a shampoo and / or rinsed and dried with an aqueous solution of a weak organic acid, such as citric acid or tartaric acid.
  • a weak organic acid such as citric acid or tartaric acid.
  • the intensity of the dyes can also be adjusted by weakening the concentration of the dyes, which can be achieved step by step by repeated use of the method (due to the particularly gentle method of dyeing, this is possible without restrictions) Add final color. This is the first time that a discreet, step-by-step approach to a target hair color is possible, for example from white or gray hair to dark hair.
  • the colorants according to the invention are also particularly suitable for dyeing near the eyes.
  • one of the blue dyes can be used in a shampoo for gray hair in very low concentrations ( «0.1%) to compensate for the frequently occurring yellow tinge. After the first dye treatment, the hair appears light gray or gray-brown and the color is completely resistant to abrasion.
  • the color tone can be intensified in the manner described above by repeated application of the colorant to the desired color.
  • the hair dyed with the colorant according to the invention has a coloration which is extremely stable to the effects of sweat and air, it can be preferably at any desired time at an acidic or alkaline pH with a suitable reducing agent, such as, for example, sulfites, pyrosulfites or hydrogen sulfites Alkali sulfites (e.g. sodium sulfite), alkali hydrogen sulfites (e.g. sodium hydrogen sulfite) or alkali pyrosulfites (e.g.
  • a suitable reducing agent such as, for example, sulfites, pyrosulfites or hydrogen sulfites
  • Alkali sulfites e.g. sodium sulfite
  • alkali hydrogen sulfites e.g. sodium hydrogen sulfite
  • alkali pyrosulfites e.g.
  • the bleaching agents generally have a content of 5 to 50 percent by weight, preferably 15 to 30 percent by weight, of ammonium persulfate and / or alkali persulfates.
  • the decolorization is preferably carried out reductively in an alkaline medium using the aforementioned decolorizing agents (in particular with ammonium sulfite or ammonium hydrogen sulfite), the use of the aforementioned sulfites, hydrogen sulfites and pyrosulfites in combination with other reducing agents, such as reductones and / or thiols, being particularly preferred.
  • the aforementioned decolorizing agents in particular with ammonium sulfite or ammonium hydrogen sulfite
  • the use of the aforementioned sulfites, hydrogen sulfites and pyrosulfites in combination with other reducing agents, such as reductones and / or thiols being particularly preferred.
  • the exposure time of the decolorizer is 5 to 45 minutes, in particular 5 to 30 minutes, depending on the color to be decolorized, depending on the pH of the decolorization agent and the temperature (about 20 to 50 degrees Celsius), the decolorization process being accelerated by the application of heat.
  • the hair is rinsed with water, optionally washed with a shampoo and / or treated with a neutral or weakly acidic rinse and then dried, where both the shampoo and the rinse can contain a reductone, for example ascorbic acid .
  • a further, particularly hair-friendly variant of the decolorization consists in the use of alkaline, low-percentage sulfite solution, as described in DE OS 19737987.
  • the coloring agent according to the invention and the corresponding decolorizing agent can expediently also be packed together in a two-component kit.
  • any permanent wave treatment that may be required must always be carried out before the dyeing treatment, since normal (reductive) permanent wave treatment destroys the dyes.
  • the colorants according to the invention have a very good shelf life and do not cause any additional damage to the hair, they are particularly suitable for coloring hair after the permanent wave treatment, although the coloring may only be carried out after the permanent wave treatment. It is particularly advantageous here that if the perm has to be renewed, it is also necessary to supplement the dyeing, this dyeing then taking place automatically on a hair material which has been decolourized evenly by the permanent wave treatment.
  • Precipitation arises. It is then cooled to about 5 ° C. The precipitated dye is filtered off and washed with a 0.5 N HCl solution and dried at 60 ° C. under reduced pressure (vacuum drying cabinet). A violet-blue solid is obtained.
  • UV (DMSO): ⁇ max ( ⁇ ) 566 nm (36874).
  • the precipitated dye is filtered off and washed with a 0.5 N HCl solution and dried at 60 ° C. under reduced pressure (vacuum drying cabinet). A black solid is obtained.
  • a customary cosmetic preparation for example a shampoo, an emulsion, a cream, a lotion, a gel, a foam, a spray or a
  • Example 9 Hair dye
  • the coloring is carried out in the manner described in Example 7.
  • the hair gets a pink color.
  • 50 g of the above oxidation hair dye are mixed with 50 g of hydrogen peroxide solution (6% strength aqueous solution) immediately before use and applied to bleached hair. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with water and shampooed.
  • hydrogen peroxide solution 6% strength aqueous solution
  • the dyed hair is then "re-shaded” (ie changed in color) by using a 0.6% 5- [3- (6-hydroxy-4-oxo-2-thioxo-1, 2,3,4-tetrahydro-pyrimidine -5-yl) -allylidene] -2-thioxodihydro-pyrimidine-4,6-dione, the hair dye composition according to the invention is applied to this hair and after an exposure time of 30 minutes, the hair is rinsed with water, shampooed and dried.
  • the hair is given a dark brown color due to the refinement.
  • 50 g of the above oxidation hair dye are mixed with 50 g of hydrogen peroxide solution (6% strength aqueous solution) immediately before use and applied to bleached hair. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with water and shampooed.
  • hydrogen peroxide solution 6% strength aqueous solution
  • the dyed hair is then "re-shaded” (ie changed in color) by using a 0.6% 5- [5- (6-hydroxy-4-oxo-2-thioxo-1, 2,3,4-tetrahydro-pyrimidine -5-yl) -penta-2,4-dienylidene] -2-thioxo-dihydro-pyrimidine-4,6-dione, the hair dye composition according to the invention which is applied to this hair and, after an exposure time of 30 minutes, the hair is rinsed with water, shampooed and dries. The hair is given a black-blue-violet color through the refinement.
  • Example 13 Hair dye with direct dyes
  • the coloring is carried out in the manner described in Example 7.
  • the hair gets a brown color.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des matières colorantes non-oxydantes obtenues par réaction d'un ou plusieurs composés de carbonyle avec de l'acide thiobarbiturique ou ses dérivés. Elle concerne également un procédé de production desdites matières colorantes, des colorants les contenant ainsi qu'un procédé de coloration et de décoloration ultérieure de cheveux au moyen de ce colorant.
PCT/EP2000/001024 1999-02-27 2000-02-09 Agent pour colorer des fibres WO2000052100A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19908654 1999-02-27
DE19908654.0 1999-02-27

Publications (1)

Publication Number Publication Date
WO2000052100A1 true WO2000052100A1 (fr) 2000-09-08

Family

ID=7899159

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/001024 WO2000052100A1 (fr) 1999-02-27 2000-02-09 Agent pour colorer des fibres

Country Status (1)

Country Link
WO (1) WO2000052100A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1166753A2 (fr) * 2000-06-27 2002-01-02 Kao Corporation Composition de coloration capillaire
WO2003019289A1 (fr) * 2001-08-27 2003-03-06 Axiom Biotechnologies, Inc. Colorants fluorescents
WO2008028861A1 (fr) * 2006-09-05 2008-03-13 Henkel Ag & Co. Kgaa Agents servant à colorer des fibres kératiniques

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739147A (en) * 1951-11-14 1956-03-20 Eastman Kodak Co Monomethine dyes containing a thiobarbituric acid nucleus
US5126222A (en) * 1989-06-12 1992-06-30 Canon Kabushiki Kaisha Electrophotographic photosensitive member containing a barbituric acid or thiobarbituric acid derivative
EP0873745A2 (fr) * 1997-04-24 1998-10-28 Henkel Kommanditgesellschaft auf Aktien Agent de teinture de fibres kératiniques
DE19717224A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Verwendung von ungesättigten Aldehyden zum Färben von keratinhaltigen Fasern
DE19820894A1 (de) * 1998-05-09 1999-11-11 Wella Ag Mittel und Verfahren zum Färben von Fasern

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739147A (en) * 1951-11-14 1956-03-20 Eastman Kodak Co Monomethine dyes containing a thiobarbituric acid nucleus
US5126222A (en) * 1989-06-12 1992-06-30 Canon Kabushiki Kaisha Electrophotographic photosensitive member containing a barbituric acid or thiobarbituric acid derivative
EP0873745A2 (fr) * 1997-04-24 1998-10-28 Henkel Kommanditgesellschaft auf Aktien Agent de teinture de fibres kératiniques
DE19717224A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Verwendung von ungesättigten Aldehyden zum Färben von keratinhaltigen Fasern
DE19820894A1 (de) * 1998-05-09 1999-11-11 Wella Ag Mittel und Verfahren zum Färben von Fasern

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1166753A2 (fr) * 2000-06-27 2002-01-02 Kao Corporation Composition de coloration capillaire
EP1166753A3 (fr) * 2000-06-27 2004-02-18 Kao Corporation Composition de coloration capillaire
WO2003019289A1 (fr) * 2001-08-27 2003-03-06 Axiom Biotechnologies, Inc. Colorants fluorescents
WO2008028861A1 (fr) * 2006-09-05 2008-03-13 Henkel Ag & Co. Kgaa Agents servant à colorer des fibres kératiniques

Similar Documents

Publication Publication Date Title
EP1098627B1 (fr) Colorant pour colorer des fibres keratiniques
DE19822199C2 (de) Mono- oder Polymethinfarbstoffe enthaltende nicht-oxidative Haarfärbemittel und Verfahren zur temporären Haarfärbung
DE3132885C2 (fr)
DE19820894A1 (de) Mittel und Verfahren zum Färben von Fasern
WO2001015662A2 (fr) Procede pour la coloration des cheveux
WO1983001771A1 (fr) Derives du 2-hydroxy-4-amino-benzene, leur preparation et colorant de cheveux contenant de tels derives
EP0376047B1 (fr) Dérivés du 2-amino-6-chloro-4-nitrophénol, procédé pour leur préparation et composition pour la teinture des cheveux contenant ces composés
DE3131409A1 (de) Neue nitrofarbstoffe, verfahren und zwischenverbindungen zu deren herstellung, mittel, welche diese farbstoffe enthalten und anwendungsverfahren zur faerbung keratinischer fasern
WO2001002492A1 (fr) Nouvelles teintures et nouveaux colorants
EP0132568B1 (fr) Dérivés de 1,4-diamino-5-chloro-2-nitrobenzène, procédé de leur production et agents pour la teinture des cheveux
DE10118271A1 (de) Diazothiazol-Farbstoffe
DE19712649C1 (de) Mittel und Verfahren zur Färbung keratinischer Fasern
WO2000052100A1 (fr) Agent pour colorer des fibres
DE3131348C2 (fr)
EP0601302B1 (fr) Composition pour la teinture des cheveux contenant des colorants de type pyridinazoiques et nouveaux colorants de type pyridinazoiques
EP0600045B1 (fr) Colorant capillaire
DE3442128A1 (de) Neue 3-amino-5-hydroxypyridinderivate und diese verbindungen enthaltende haarfaerbemittel
DE2913821A1 (de) Neue para-phenylendiamine, verfahren zu deren herstellung und diese enthaltende mittel
DE4227403A1 (de) Haarfärbemittel
WO1992006670A1 (fr) Colorant des cheveux contenant 1,4-bis-[(dihydroxyalkyl)amino]-anthraquinone et nouvelles 1,4-bis-[(dihydroxyalkyl)amino]-anthraquinones
DE3325790C2 (fr)
DE19649243C1 (de) Mittel und dessen Verwendung zur Entfernung von Tönungen aus dem Haar
DE4018335A1 (de) Mittel zum faerben von haaren mit einem gehalt an 2-amino-4-halogen-6-nitrophenolen sowie 2-amino-4-fluor-6-nitrophenol
DE3616720C2 (de) 1-(2',3'-Dihydroxypropyl)amino -4-(N-ethyl,N-2'-hydroxyethyl)amino-2-nitro-benzol und Mittel zum Färben von Haaren
EP0226973B1 (fr) 4-Bis(2'-hydroxyéthyl)amino-1-(3'-hydroxypropyl)amino-2-nitro-benzène, son procédé de préparation et moyen pour la teinture de cheveux

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 2000910655

Country of ref document: EP

AK Designated states

Kind code of ref document: A1

Designated state(s): BR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

WWE Wipo information: entry into national phase

Ref document number: 09647203

Country of ref document: US

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWW Wipo information: withdrawn in national office

Ref document number: 2000910655

Country of ref document: EP