EP1727514A1 - Agents pour colorer des fibres de keratine - Google Patents

Agents pour colorer des fibres de keratine

Info

Publication number
EP1727514A1
EP1727514A1 EP04821679A EP04821679A EP1727514A1 EP 1727514 A1 EP1727514 A1 EP 1727514A1 EP 04821679 A EP04821679 A EP 04821679A EP 04821679 A EP04821679 A EP 04821679A EP 1727514 A1 EP1727514 A1 EP 1727514A1
Authority
EP
European Patent Office
Prior art keywords
amino
azo
phenylmethyl
methyl
phenyl
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Withdrawn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
EP04821679A
Other languages
German (de)
English (en)
Inventor
Cécile Pasquier
Caroline Kiener
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
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 GmbH filed Critical Wella GmbH
Publication of EP1727514A1 publication Critical patent/EP1727514A1/fr
Withdrawn legal-status Critical Current

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
    • A61K8/49—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

Definitions

  • the present invention relates to agents for dyeing keratin fibers, such as wool, furs and in particular human hair, containing thiazolium azo dyes.
  • Two dyeing processes are generally used for the color-changing treatment of keratin fibers.
  • the coloring is produced with so-called oxidative or permanent coloring agents, using a mixture of different developer substances and coupler substances and an oxidizing agent.
  • so-called direct (non-oxidative) dyes can be added in this process to round off the coloring result or to produce special color effects.
  • the second method uses only direct dyes that are applied to the fibers in a suitable carrier. This process is easy to use, extremely gentle and is characterized by low damage to the keratin fiber. A large number of requirements are imposed on the direct dyes used here.
  • the present invention therefore relates to an agent for dyeing keratin fibers, in particular human hair, which is characterized in that it contains at least one thiazolium azo dye of the general formula (I),
  • R1 is a saturated or unsaturated (-CC 2 ) -alkyl group, one with a
  • R2 and R3 can be the same or different and independently of one another hydrogen, a halogen atom (F, Cl, Br, J), a saturated or unsaturated (C- ⁇ -C ⁇ 2 ) alkyl group, a (-CC-C ⁇ 2 ) alkoxy group, a nitro group, an amino group, a (C ⁇ -C ⁇ 2) alkylamino group, a di (Cr Ci2) -alkylamino group, a (CrC- ⁇ 2) -Hydroxyalkylamino distr, a di (C ⁇ -Ci2) -hydroxyalkylamino distr represent a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heteroaryl group;
  • R4 is hydrogen, a saturated or unsaturated (C 1 -C 12 ) alkyl group, a substituted with a halogen atom (F, Cl, Br, J) (-C-C ⁇ 2 ) alkyl group, a hydroxy- (C- ⁇ -C ⁇ 2 ) alkyl group, an amino (-C 1 -C 2 ) alkyl group or a benzyl group;
  • R5 and R6 can be the same or different and independently of one another hydrogen, a halogen atom (F, Cl, Br, J), a saturated or unsaturated (-C-C-
  • a " is an anion of an organic
  • Preferred compounds of the formula (I) are those in which R1 is a saturated or unsaturated (C 1 -C 12) alkyl group, compounds in the formula (I) in which R1 is a saturated or unsaturated (C ⁇ - C ⁇ 2 ) alkyl group and R4 is a saturated or unsaturated (C ⁇ -C-
  • a " is preferably the same as chloride, bromide, iodide, hydrogen sulfate, sulfate, toluenesulfonate, benzenesulfonate, monomethyl sulfate, hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate, tetraphenylborate, formate, acetate or propionate, the chloride ion, the bromide ion, the monomethyl sulfate ion and the acetate being particularly preferred.
  • Particularly preferred compounds of the formula (I) are 3-methyl-2 - [[4- [methyl (phenylmethyl) amino] phenyl] azo] thiazolium chloride, 3-methyl-2- [[4- [methyl (phenylmethyl) amino] phenyl] azo] thiazolium bromide, 3-methyl-2 - [[4- [methyl (phenylmethyl) amino] phenyl] azo] thiazolium monomethyl sulfate, 3-methyl-2 - [[4- [ methyl (phenylmethyl) amino] phenyl] -azo] thiazolium acetate, 3,4-dimethyl-2 - [[4- [methyl (phenylmethyl) amino] -phenyl] azo] thiazolium chloride, 3,4-dimethyl -2 - [[4- [methyl (phenylmethyl) amino] phenyl] azo] thiazolium bromide, 3,4-dimethyl-2 - [[4- [
  • the compounds of the 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 according to the invention can additionally include other known direct-coloring dyes from the group consisting of nitro-dyes, azo-dyes, anthraquinone dyes and triphenylmethane dyes and natural direct-coloring dyes (for example henna or indigo), alone or as a mixture with one another, contain, 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.
  • the abovementioned direct dyes can be present in a total amount of about 0.01 to 4 percent by weight, the total amount of dyes in the colorant according to the invention preferably being about 0.01 to 10 percent by weight, in particular 0.1 to 8 percent by weight.
  • oxidation dye precursors developer substances and coupler substances
  • suitable oxidizing agents can also be added to the colorant according to the invention.
  • the preparation form of the colorant according to the invention can, for example, be a solution, in particular an aqueous or aqueous-alcoholic solution, a cream, a gel, a surfactant-containing foaming solution (shampoo, aerosol), an emulsion or another water-containing solution which is more suitable for use on the hair Be carrier.
  • the colorant according to the invention is in the form of pellets, granules or powders, which are dissolved in an aqueous preparation, for example in water or an aqueous oxidizing agent preparation, before use.
  • the composition of these agents is a mixture of the dye component with the additives customary for such preparations.
  • Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic monohydric or polyhydric alcohols, their esters and ethers, for example alkanols, in particular with 1 to 4C atoms, for example ethanol, propanol or isopropanol, butanol, isobutanol , dihydric and trihydric alcohols, especially those having 2 to 6 carbon atoms, for example ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1,6-hexanediol, 1, 2 , 6-hexanetriol, glycerin, diethylene glycol, dipropylene glycol, polyalkylene glycols, such as triethylene glycol, polyethylene glycol, tripropylene glycol, polypropylene glycol, lower alkyl ethers of polyhydric alcohols
  • wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric, nonionic or zwitterionic surface-active substances such as, for example, fatty alcohol sulfates, oxyethylated fatty alcohol sulfates, alkyl sulfonates, alkyl benzene sulfonates, ⁇ -olefin sulfonates, alkyl trimethylammonium saltsium, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanolamides, ethoxylated fatty acid esters, fatty alcohol polyglycol ether sulfates, alkyl polyglucosides, thickening agents such as higher fatty alcohols, starch, cellulose derivatives, petroleum jelly, paraffin oil, fatty acids, and other fat components in emulsified form, natural solvents, solvent-based solvents, water-based solvents, Xanthan
  • a water-soluble organic solvent or a mixture of such solvents and a water / solvent mixture can also be used.
  • the components mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.1 to 30 percent by weight, the thickeners in an amount of about 0.1 to 30 percent by weight and the care substances in a concentration of about 0.1 to 5 percent by weight.
  • the colorant according to the invention has a pH of about 3 to 11, preferably about 3 to 10.
  • Both organic and inorganic acids or bases are suitable for adjusting the pH value according to the invention.
  • the following acids are particularly suitable as acids: ⁇ -hydroxycarboxylic acids, such as, for example, glycolic acid, lactic acid, tartaric acid, citric acid or malic acid; Ascorbic acid; gluconolactone; Acetic acid; Hydrochloric acid or phosphoric acid, as well as mixtures of these acids.
  • Suitable bases are in particular sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, sodium phosphate, borax (Na 2 B 0 7 x 10H 2 O), disodium hydrogen phosphate, sodium hydroxide, potassium hydroxide, ammonia and other organic amines such as monoethanolamine, diethanonolamine, triethanolamine, N -Methyl-N-ethanolamine, N-methyl-N, I -diethanolamine, 2- (2-hydroxyethoxy) ethanolamine, di-2- (2-hydroxyethoxy) ethanolamine and tri-2- (2-hydroxyethoxy) ethanolamine , to call.
  • Alkaline pH values are preferably set with ammonia and / or monoethanolamine.
  • the coloring agent according to the invention is generally applied by applying an amount sufficient for hair coloring, depending on the length of the hair about 30 to 120 grams, of the hair coloring agent to the hair, the hair dye at about 15 to 50 degrees Celsius, preferably 30 to 40 degrees Celsius , about 1 to 60 minutes, preferably 5 to 30 minutes, Allows to act, then rinse the hair thoroughly with water, if necessary, wash with a shampoo and finally dry.
  • the colorant described above can furthermore contain natural or synthetic polymers or modified polymers of natural origin which are customary for cosmetic products, as a result of which hair is set at the same time as 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 quaternization products
  • Polymerizate from such compounds such as polyvinyl pyrrolidone vinyl acetate mentioned; while, for example, chitosan (deacetylated chitin) or chitosan derivatives can be used as natural polymers or modified natural polymers.
  • the abovementioned polymers can be present in the agent 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 4 to 10.
  • the application of the hair dye with additional strengthening takes place in a known and customary manner by moistening the hair with the Fixing, setting (inserting) the hair for hairstyle and subsequent drying.
  • the compounds of the formula (I) according to the invention enable an excellent, uniform, intense, brilliant and extremely permanent blue to violet coloration of keratin fibers, in particular human hair, under gentle and skin-compatible conditions, with excellent stability against light, and exceptional stability against sweat.
  • the dyes are known per se.
  • the dyes of the formula (I) can be prepared analogously to known production processes, for example via azo coupling of 2-aminothiazole derivatives with N-benzylaminophenyl derivatives and subsequent quaternization, or via oxidative condensation of thiazolone hydrazone with N-benzylaminophenyl - Derivatives are made.
  • the coloring solution is optionally adjusted to the desired pH values by adding ammonia or citric acid.
  • the hair is colored by applying a sufficient amount of the dye to the hair and spreading it evenly with a brush. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
  • the coloring solution is optionally adjusted to the desired pH values by adding ammonia or citric acid.
  • the hair is colored by applying a sufficient amount of the dye to the hair and spreading it evenly with a brush. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
  • the coloring solution is optionally adjusted to the desired pH values by adding ammonia or citric acid.
  • the hair is colored by applying a sufficient amount of the dye to the hair and spread evenly with a brush. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
  • the coloring solution is optionally adjusted to the desired pH values by adding ammonia or citric acid.
  • the hair is colored by applying a sufficient amount of the dye to the hair and spreading it evenly with a brush. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with lukewarm water, washed with a shampoo, rinsed with lukewarm water and then dried.
  • the L * a * b * color measurement values given in the present examples were determined using a color measuring device from Minolta, type Chromameter II.
  • the L-value stands for the brightness (that is, the lower the L-value, the greater the color intensity)
  • the a-value is a measure of the red component (that is, the larger the a-value, the greater the red component is larger).
  • the b-value is a measure of the blue component of the color, whereby the more negative the b-value, the greater the blue component.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des agents conçus pour colorer des fibres de kératine, qui sont caractérisés en ce qu'ils contiennent au moins un colorant thiazoliumazo de formule générale (I).
EP04821679A 2004-02-21 2004-11-16 Agents pour colorer des fibres de keratine Withdrawn EP1727514A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004008603A DE102004008603A1 (de) 2004-02-21 2004-02-21 Mittel zur Färbung von Keratinfasern
PCT/EP2004/012983 WO2005079733A1 (fr) 2004-02-21 2004-11-16 Agents pour colorer des fibres de keratine

Publications (1)

Publication Number Publication Date
EP1727514A1 true EP1727514A1 (fr) 2006-12-06

Family

ID=34832913

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04821679A Withdrawn EP1727514A1 (fr) 2004-02-21 2004-11-16 Agents pour colorer des fibres de keratine

Country Status (6)

Country Link
US (1) US7537620B2 (fr)
EP (1) EP1727514A1 (fr)
JP (1) JP2007523101A (fr)
BR (1) BRPI0418387A (fr)
DE (1) DE102004008603A1 (fr)
WO (1) WO2005079733A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005003821A1 (de) * 2005-01-27 2006-08-10 Wella Ag Mittel zur Färbung von Keratinfasern

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2433229C3 (de) * 1974-07-11 1979-06-07 Hoechst Ag, 6000 Frankfurt Verfahren zur Herstellung von Tbiazolazoverbindungen
DE2822912A1 (de) 1978-05-26 1979-11-29 Hoechst Ag Verfahren zur verbesserung des weissgrades von polymeren und mischpolymeren des acrylnitrils, insbesondere beim verspinnen aus der spinnmasse
DE2840121C2 (de) * 1978-09-15 1982-10-28 Hoechst Ag, 6000 Frankfurt Verfahren zur Herstellung von Chlorzinksalzen von Thiazoliumazofarbstoffen
DE3602587A1 (de) 1986-01-29 1987-07-30 Hoechst Ag Verfahren zur herstellung von hochkonzentrierten farbstoffloesungen kationischer farbstoffe
DE10118271A1 (de) 2001-04-12 2002-03-14 Henkel Kgaa Diazothiazol-Farbstoffe

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005079733A1 *

Also Published As

Publication number Publication date
US20070258928A1 (en) 2007-11-08
WO2005079733A1 (fr) 2005-09-01
US7537620B2 (en) 2009-05-26
BRPI0418387A (pt) 2007-05-22
JP2007523101A (ja) 2007-08-16
DE102004008603A1 (de) 2005-09-08

Similar Documents

Publication Publication Date Title
DE19822198C2 (de) Oxonolfarbstoffe enthaltende Mittel und Verfahren zur Erzeugung von semipermanenten Färbungen auf Haaren
DE19856342A1 (de) Mittel zur Färbung von Fasern
DE102004006142A1 (de) Neutrale und kationische Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern
JP4759001B2 (ja) カチオン性アザシアニン染料を含む着色剤
DE102005003821A1 (de) Mittel zur Färbung von Keratinfasern
EP1143923B1 (fr) Agent et procede pour la coloration de fibres
EP1002516B1 (fr) Compositions tinctoriales pour cheveux renfermant des dérivés d'indane
EP1805266B1 (fr) Colorants azoaziniques cationiques, et agents de coloration contenant ces composes
EP1716209B1 (fr) Utilisation d'une composition contenant des colorants azoïques d'indolylthiazolium pour colorer les fibres kératiniques
DE19737987C1 (de) Mittel zur Entfernung von Färbungen und dessen Verwendung
WO1998023247A1 (fr) Agent pour colorer et decolorer des fibres
WO2005079733A1 (fr) Agents pour colorer des fibres de keratine
DE102005003363A1 (de) Verwendung kationischer Azacyanin-Farbstoffe zur Färbung von Keratinfasern
DE102004051071A1 (de) Kationische Azacyanin-Farbstoffe und diese enthaltende Färbemittel
DE602005001848T2 (de) System zum reduktiven Färben von Keratinfasern
EP1771517A1 (fr) Colorants pyrazolone cationiques, leurs procedes de production et agents colorants pour fibres keratiniques, contenant ces composes
DE102004006143A1 (de) Neue Naphthalinderivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern
DE19905652A1 (de) Naphthochinonderivate enthaltende Färbemittel
DE102004051072A1 (de) Kationische Heteroarylpyrazolonazofarbstoffe und diese Verbindung enthaltende Färbemittel für Keratinfasern
DE202004019358U1 (de) Mittel zur Färbung von keratinischen Fasern
DE19933313A1 (de) Mittel und Verfahren zur Färbung von Fasern

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20060526

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LU MC NL PL PT RO SE SI SK TR

17Q First examination report despatched

Effective date: 20070322

DAX Request for extension of the european patent (deleted)
GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20080304