EP1909913A1 - Procede pour dissimuler rapidement des racines capillaires resultant de la pousse de cheveux colores - Google Patents

Procede pour dissimuler rapidement des racines capillaires resultant de la pousse de cheveux colores

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Publication number
EP1909913A1
EP1909913A1 EP06762630A EP06762630A EP1909913A1 EP 1909913 A1 EP1909913 A1 EP 1909913A1 EP 06762630 A EP06762630 A EP 06762630A EP 06762630 A EP06762630 A EP 06762630A EP 1909913 A1 EP1909913 A1 EP 1909913A1
Authority
EP
European Patent Office
Prior art keywords
amino
hydroxy
formyl
phenylenediamine
diamino
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.)
Ceased
Application number
EP06762630A
Other languages
German (de)
English (en)
Inventor
Sabine Babiel
Horst Höffkes
Oliver Kuhnert
Detlef Hollenberg
Manuela Ehlert
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1909913A1 publication Critical patent/EP1909913A1/fr
Ceased legal-status Critical Current

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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits

Definitions

  • the present invention relates to a process for rapid lamination of the regrown hairline in dyed hair in which a hairline dye of a defined viscosity is left on the hairline for a defined period of time and rinsed off again. Furthermore, the use of the Haaransatzfärbeschs for selective coloring of the hairline, as well as a packaging unit (kit), containing the Haaransatzfärbesch, as well as application aids and optionally a mixing bowl, the invention.
  • Human hair is today treated in a variety of ways with hair cosmetic preparations. These include, for example, the cleansing of hair with shampoos, the care and regeneration with rinses and cures and the bleaching, dyeing and shaping of the hair with dyes, tinting agents, waving agents and styling preparations. In this case, means for changing or nuancing the color of the head hair play a prominent role. Apart from the bleaching agents that cause an oxidative lightening of the hair by degradation of the natural hair dyes, so in the field of hair coloring essentially four types of hair dyes of importance:
  • oxidation colorants For permanent, intensive colorations with corresponding fastness properties, so-called oxidation colorants are used.
  • hairline colorants usually contain oxidation dye precursors, so-called
  • the developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or with coupling with one or more coupler components.
  • the oxidation dyes are characterized by excellent, long-lasting dyeing results. For naturally acting dyeings but usually a mixture of a larger number of Oxidation dye precursors are used; In many cases, direct dyes are still used for shading.
  • developer components are usually primary aromatic amines with a further, located in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used ,
  • Specific examples are, for example, p-phenylenediamine, p-toluenediamine, 2,4,6,6-tetra-aminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-) Diaminophenyl) ethanol, 2- (2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolone-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2 -Hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine and 1,3-N, N'-bis (2-hydroxyethyl) -N, N'-bis (4-aminophenyl) -diaminopropan-2-ol
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used.
  • Suitable coupler substances are, in particular, 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomonomethyl ether, m-phenylenediamine, 1 -Phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6 -methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol
  • dyeing or tinting agents which contain so-called direct drawers as a coloring component. These are dye molecules that grow directly on the hair and do not require an oxidative process to form the color. These dyes include, for example, the henna already known from antiquity for coloring body and hair. These dyeings are generally much more sensitive to shampooing than the oxidative dyeings, so that a much more undesirable nuance shift or even a visible "discoloration" occurs much more quickly. Finally, another dyeing process has received much attention. In this method, precursors of the natural hair dye melanin are applied to the hair; These then form naturally-analogous dyes in the course of oxidative processes in the hair. Such
  • One way to stain keratinous fibers is to use stains that contain a combination of component
  • component B compounds selected from (a) CH-acidic compounds and (b) compounds having primary or secondary amino group or hydroxy group selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds
  • the corresponding dyeing method (referred to below as oxo dyeing) is described, for example, in the publications WO-A1-99 / 18916, WO-A1 -00 / 38638, WO-A1-0 01/34106 and WO-A 1-01 / 47483.
  • the resulting dyeings have partially color fastness on the keratin-containing fiber, which are comparable to those of the oxidation dyeing.
  • the Nuancenspektrum achievable with the gentle oxo staining is very broad and the color obtained often has an acceptable brilliance and color depth.
  • the aforementioned components A and B hereinafter referred to as Oxofarbstoffvor area, are generally not themselves dyes, and are therefore each alone taken not for coloring keratin-containing fibers. In combination, they form dyes in a non-oxidative process.
  • corresponding compounds of component B may also contain corresponding oxidation dye precursors of the developer and / or coupler type with or without Use of an oxidizing agent find use.
  • the oxo staining method can be readily combined with the oxidative staining system.
  • the hair dyeing with permanent or semi-permanent colorants has the disadvantage that after some time the hair coloring outgrows. This results in the hairline a zone of undyed hair, which is usually eliminated by over-dyeing the entire hair.
  • the already dyed hair is again treated with the hairline dye. The dyed before the treatment and thus strained hair lengths are unnecessarily repeatedly strained by overdyeing.
  • the coloring of the hairline with a tinting agent based solely on direct dyes offers no permanent solution for the lamination of the hairline due to the temporary color thus achievable.
  • EP-B1-624 362 it is proposed, to protect the already more heavily used hair lengths in a two-stage dyeing process to dye the hairline with an alkaline and the entire hair length with an acidic oxidation dye.
  • this procedure means for the already damaged hair length, that it again comes in contact with the oxidizing agent in each dyeing process.
  • W0-A1 -01 / 26616 a two-stage hair dyeing process is described in which the undyed hairline is first dyed with a conventional oxidative hair dye and the hair lengths are dyed with a hairline dye based on, for example, oxo dye precursors.
  • the exposure time of the oxidative hair dye to the hairline is, if an effective color is to be achieved, over 20 minutes.
  • the known methods offer a time-consuming possibility to re-color the hairline.
  • the object of the present invention is therefore to provide a fast To provide a method for lamination of the regrown hairline, which provides an effective and uniform staining result with short application time, without the already dyed hair lengths are subjected to a new staining.
  • a first subject of the invention is therefore a process for the selective dyeing of the undyed hairline of hair which has a hair coloring in the hair lengths, wherein in the first step
  • the entire fibers are subsequently treated with a hair conditioning agent wherein the hairline has a viscosity of 2000 to a maximum of 27000 mPa s, in particular from 4000 to a maximum 27000 mPa s (Brookfield rotary viscometer, type RTV, spindle 5, 2 rpm) at 2O 0 C. and the exposure time Z1 does not exceed a duration of 20 minutes.
  • keratin-containing fibers are understood to mean furs, wool, feathers and, in particular, human hair.
  • the keratin-containing fibers to be treated according to the method of the invention have a partial hair coloring and have two zones. Examples of corresponding keratin-containing fibers are found in the case of an outgrown hair coloring.
  • the undyed hairline (zone 1) consists of freshly regrown, almost unstretched hair.
  • the dyed hair lengths (zone 2) were dyed with a, preferably permanent or semipermanent, hair color.
  • the dyed hair lengths are treated neither with the Haaransatzstärbesch still with any other hair dye. Only the undyed hairline is specifically post-dyed with said hairline dye.
  • the Haaransatzstärbesch must be applied from the hairline to the transition to the dyed hair length. It can be difficult to avoid that minimal areas of previously colored hair also come into contact with the Haaransatzstärbesch.
  • These minimum ranges should preferably be less than 20% of the dyed hair length, but preferably not more than 1 cm.
  • An aerosol can, a pump container, a brush or a brush, particularly preferably a brush, is preferably used as an application aid in the method according to the invention.
  • Corresponding brushes which can be used for the batch application are described, for example, in US Pat. No. 6,092,535 or in the hairdressing textbook "Chemistry in Modern Hairdressing Practice” by H. Möller et al., Handcraft and Technology, 2nd revised edition, 1971, p. 106, to which each expressly and fully incorporated by reference.
  • the hairline colorant has a viscosity of 2000 to at most 10000 mPa s, in particular from 4000 to at most 10000 mPa s (Brookfield rotary viscometer, type RTV, spindle 5, 2 rpm) at 20 ° C.
  • the container may, in the context of this embodiment, have a plurality of chambers from which different compositions emerge from each other and mix before being discharged from the container to the hair preparation colorant.
  • the spray head of the aerosol or pump container is kept extremely close during the application process, preferably with a distance of not more than 2 cm, to the hairline to be treated, and sprayed or sprayed onto the hairline dye.
  • an applicator in the form of a brush or a brush can also be attached to the spray head, whereby, when the hairline colorant leaves the said container, the hairline colorant passes directly to the applicator and is thus ready for application.
  • the hair is combed smooth before application of the Haaransatzfärbeschs. Then the hair is parted with a comb. The hairline dye is then applied to the unstained hairline from the scalp to the transition to dyed hair length along the crown by brush. After the application, the hair is parted again and proceed in the application process analogous to the above procedure. It should be noted that the Haaransatzstärbesch already in the hair is not combed into the hair lengths. According to this method, the entire uncolored hairline is post-dyed.
  • the hairline colorant is preferably added to a dish for better dosage before application or, if mixed from two components before use, mixed in this dish.
  • the bristles of the brush (about 2/3 of the bristle length) are then soaked with the Haaransatzfärbesch and the agent, preferably as described above, applied to the hairline.
  • the hair dye heats up from ambient temperature to body temperature. This heating is often accompanied by a change in viscosity or decrease.
  • such Haaransatzstärbesch be used in the process according to the invention, which are viscosity stable when heated from 2O 0 C to 45 ° C, so that the predetermined viscosity parameters are maintained even at the application temperature. It has been shown that the rapid batch dyeing takes place in the viscosity interval according to the invention.
  • the hairline can be selectively colored in this interval. The Haaransatzstärbesch does not run and thus remains in the area of the undyed Hairline. In this way, a re-staining of large parts of the already dyed hair lengths is prevented.
  • the process of the invention has a viscosity of 2000 to at most 27000 mPa s, in particular from 4000 to a maximum 27000 mPa s, (Brookfield rotary viscometer, type RTV, spindle 5, 2 rpm) in a temperature range of 20 0 C to 45 0 C, in particular from 2O 0 C to 40 0 C, has.
  • the 2-component colorants disclosed therein consist of a composition containing the coloring components and a further oxidizing agent-containing composition which additionally comprises at least one branched (C 6 to C 30 ) fatty acid and / or at least one branched or unbranched (C 8 to C 30 ) dicarboxylic acid.
  • the publication does not contain information about the viscosity of the colorants.
  • the contact time Z1 of the hairline colorant according to the method according to the invention is preferably at most 15 minutes, particularly preferably at most 10 minutes.
  • the process of the invention is an oxidative Haaransatzfetzsch, it contains as a coloring component at least one developer component and optionally additionally at least one coupler component.
  • Preferred developer components are primary aromatic amines having a further, in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof ,
  • p-phenylenediamine derivatives of the formula (E1) in which
  • G 1 is a hydrogen atom, a C 1 - to C 4 -alkyl radical, a C r to C 4 -
  • Monohydroxyalkyl radical a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) -
  • G 2 is a hydrogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -
  • Monohydroxyalkyl radical a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) -
  • G 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or
  • Fluorine atom a C 1 to C 4 alkyl radical, a C 1 to C 4 monohydroxyalkyl radical, a
  • G 4 represents a hydrogen atom, a halogen atom or a C 1 - to C 4 -alkyl radical or, when G 3 and G 4 are ortho to each other, they may together form a bridging ⁇ , ⁇ -alkylenedioxy group, such as, for example, an ethylenedioxy group ,
  • C 1 - to C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals.
  • C 1 -C 4 -alkoxy radicals which are preferred according to the invention are, for example, a methoxy or an ethoxy group.
  • a C 1 to C 4 hydroxyalkyl group there may be mentioned a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred.
  • a particularly preferred C 2 to C 4 polyhydroxyalkyl group is 1, 2 Dihydroxyethyl.
  • halogen atoms are according to the invention F, Cl or Br atoms, Cl atoms are very particularly preferred.
  • the other terms used are derived according to the invention from the definitions given here.
  • nitrogen-containing groups of the formula (E1) are especially the amino groups, C r -C 4 monoalkylamino, C 1 - to C 4 dialkylamino, C 1 - to C 4 - trialkylammonium groups, C 1 - to C 4 -Monohydroxyalkylamino phenomenon, imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (E1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2 , 6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4 -Amino-3-methyl- (N, N-diethyl) -aniline, N, N-bis- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino-2- methylaniline, 4-N,
  • Very particularly preferred p-phenylenediamine derivatives of the formula (E1) according to the invention are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p-phenylenediamine and N, N bis (.beta.-hydroxyethyl) -p-phenylenediamine.
  • developer component compounds which contain at least two aromatic nuclei which are substituted by amino and / or hydroxyl groups.
  • binuclear developer components which can be used in the hairline colorants according to the invention, one can especially use the Name compounds corresponding to the following formula (E2) and their physiologically acceptable salts:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 -ReSt, which is optionally substituted by a C 1 - to C 4 -alkyl radical, by a C 1 - to C 4 -
  • the bridge Y is an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, of one or more nitrogen-containing groups and / or one or more
  • Heteroatoms such as oxygen, sulfur or nitrogen atoms may be interrupted or terminated and possibly by one or more hydroxyl or C 1 -
  • C ⁇ -alkoxy may be substituted, or a direct bond
  • G 5 and G 6 independently of one another represent a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -
  • Polyhydroxyalkyl radical a C 1 - to C 4 -aminoalkyl radical or a direct compound for bridging Y,
  • G 7 , G 8 , G 9 , G 10 , G 11 and G 12 are each independently
  • Hydrogen atom a direct bond to the bridging Y or a C 1 - to C 4 -
  • the compounds of formula (E2) contain only one bridge Y per molecule and the compounds of formula (E2) contain at least one amino group which carries at least one hydrogen atom.
  • the substituents used in formula (E2) are defined according to the invention analogously to the above statements.
  • Preferred binuclear developer components of the formula (E2) are in particular: N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis - ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N 1 N'-diethyl-N, N ' bis (4'-amino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminophenyl) methane, 1,
  • Very particularly preferred binuclear developer components of the formula (E2) are N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, Bis (2-hydroxy-5-aminophenyl) methane, 1, 3-bis (2,5-diaminophenoxy) -propan-2-ol, N, N'-bis (4'-aminophenyl) -1, 4-diazacycloheptane and 1, 10-bis- (2 ', 5'-diaminophenyl) -1, 4, 7, 10-tetraoxadecane or one of their physiologically acceptable salts.
  • the hairline colorant of the inventive method is free of binuclear developer components.
  • p-aminophenol derivatives of the formula (E3) it may be preferred according to the invention to use as the developer component a p-aminophenol derivative or one of its physiologically tolerable salts. Particular preference is given to p-aminophenol derivatives of the formula (E3)
  • G 13 is hydrogen atom for a halogen atom, a d- to C 4 alkyl, C 1 - to C 4 monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4 J- AIkOXy- (C 1 - to C 4 ) -alkyl radical, a C 1 - to C 4 -Aminoalkylrest, a hydroxy (C r to C 4 ) -alkylamino, a C 1 - to C 4 -hydroxyalkoxy, a C 1 - aminoalkyl -C 4 hydroxyalkyl (C r to C 4), or (di-C 1 - to C 4 -alkylamino) - alkyl group, and - (C 4 to C 1)
  • G 14 is a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) - Alkoxy- (C 1 - to C 4 ) -alkyl radical, a C 1 - to C 4 -aminoalkyl radical or a C 1 - to C 4 -cyanoalkyl radical,
  • G 15 is hydrogen, C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
  • G 16 is hydrogen or a halogen atom.
  • Preferred p-aminophenols of the formula (E3) are, in particular, p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 -Amino-3-hydroxymethylphenol, 4-amino-2- (D-hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino 2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2 chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethylaminomethyl) phenol and their physiologically acceptable salts.
  • Very particularly preferred compounds of the formula (E3) are p-aminophenol, A-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol and 4-amino 2- (diethylaminomethyl) -phenol.
  • the developer component may be selected from o-aminophenol and its derivatives such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component may be selected from heterocyclic developer components such as the pyridine, pyrimidine, pyrazole, pyrazole pyrimidine derivatives and their physiologically acceptable salts.
  • Preferred pyridine derivatives are, in particular, the compounds described in the patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) amino-3-amino-pyridine, 2,3-diamino-6-methoxy-pyridine, 2- ( ⁇ -
  • Methoxyethyl amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are, in particular, the compounds described in German Patent DE 2 359 399, Japanese Laid-Open Patent Publication JP 02019576 A2 or in the published patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy- 2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6- triaminopyrimidine.
  • Preferred pyrazole derivatives are, in particular, the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740 931 and DE 195 43 988, such as 4,5 Diamino-1-methylpyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4.5- Diamino-1, 3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-Benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1
  • Preferred pyrazolopyrimidine derivatives are, in particular, the derivatives of the pyrazolo [1,5-a] pyrimidine of the following formula (E4) and their tautomeric forms, if a tautomeric equilibrium exists:
  • G 17 , G 18 , G 19 and G 20 independently of one another represent a hydrogen atom, a C 1 - to C 4 -alkyl radical, an aryl radical, a C 1 - to C 4 -hydroxyalkyl radical, a C ⁇ - to C 4
  • Polyhydroxyalkyl radical is a (C 1 to C 4 ) -alkoxy- (C 1 to C 4 ) -alkyl radical, a C 1 to C 4 -aminoalkyl radical which may optionally be protected by an acetyl-ureide or a sulfonyl radical, a C 1 - to C 4) alkylamino (Cr to C 4) - alkyl group, a DK (C 1 - to C 4) alkyl] - (C r to C 4) aminoalkyl, wherein the dialkyl residues optionally a Carbon cycle or a heterocycle having 5 or 6 chain members, a C 1 - to C 4
  • pyrazolo [1, 5-a] pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.
  • indoles and indolines which have at least one hydroxy or amino group, preferably as a substituent on the six-membered ring.
  • These groups may carry further substituents, e.g. Example in the form of etherification or esterification of the hydroxy group or alkylation of the amino group.
  • These indoles or indolines can be used as a developer component in the hairline colorant.
  • Particularly suitable precursors of natural-analogous hair dyes are derivatives of 5,6-dihydroxyindoline of the formula (Ia),
  • R 1 represents hydrogen, hydroxy-alkyl group, a -C 4 alkyl group or a C r C 4,
  • R 2 is hydrogen or a -COOH group, where the -COOH group may also be present as a salt with a physiologically compatible cation
  • R 3 is hydrogen or a C 1 -C 4 -alkyl group
  • R 4 is hydrogen, a C 1 -C 4 -alkyl group or a group -CO-R 6 , in which R 6 is a C 1 -C 6 -alkyl group, and R 5 is one of the groups mentioned under R 4 , as well as physiologically tolerated salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6 dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid and 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially 5, 6-Dihydroxyindolin.
  • R 1 is hydrogen, a C 1 -C 4 -alkyl group or a C 1 -C 4 -hydroxyalkyl group
  • R 2 is hydrogen or a -COOH group, wherein the -COOH group may also be present as a salt with a physiologically compatible cation,
  • R 3 is hydrogen or a C 1 -C 4 -alkyl group
  • R 4 is hydrogen, a C r C 4 -alkyl group or a group -CO-R 6 , in which R 6 is a C 1 -C 4 -alkyl group, and
  • R 5 is one of the groups mentioned under R 4 , as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5, 6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and A-aminoindole.
  • N-methyl-5,6-dihydroxyindole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, and especially the 5,6 -Dihydroxyindol.
  • the indoline and indole derivatives can be used both as free bases and in the form of their physiologically acceptable salts with inorganic or organic acids, eg. As the hydrochlorides, sulfates and hydrobromides are used.
  • the indole or indoline derivatives are contained therein usually in amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-%.
  • the indoline or indole derivative in combination with at least one amino acid or an oligopeptide in the hairline colorants.
  • the amino acid is advantageously an ⁇ -amino acid; Very particularly preferred ⁇ -amino acids are arginine, ornithine, lysine, serine and histidine, in particular arginine.
  • the Haaransatzfärbesch the process of the invention additionally contain at least one coupler component.
  • m-phenylenediamine derivatives naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives and heterocyclic compounds are generally used.
  • Preferred coupler components according to the invention are m-aminophenol and its derivatives, such as, for example, 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2 6-dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2'- Hydroxyethyl) amino-2-methylphenol, 3- (diethylamino) phenol, N-cyclopentyl-3-aminophenol, 1,3-dihydroxy-5- (methylamino) benzene, 3-ethylamino-4-methylphenol and 2,4- Dichloro-3-aminophenol, o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as 2,
  • Di- or trihydroxybenzene derivatives such as resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1,2,4-trihydroxybenzene, pyridine derivatives such as 2,6-dihydroxypyridine , 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dihydroxy 4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine, naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2- Hydr
  • Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
  • Quinoxaline derivatives such as 6-methyl-1,2,3,4-tetrahydroquinoxaline, pyrazole derivatives such as 1-phenyl-3-methylpyrazol-5-one, indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole, pyrimidine derivatives, such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyrimidine, 2-amino-4 hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine, or
  • Methylenedioxybenzene derivatives such as, for example, 1-hydroxy-3,4-methylenedioxybenzene, 1-amino-3,4-methylenedioxybenzene and 1- (2'-methylenedioxybenzene)
  • coupler components according to the invention are 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, m-phenylenediamine, 1-phenyl-3 methyl pyrazol-5-one, 2,4-dichloro-3-aminophenol, 1,3-bis- (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chloro-resorcinol, 2-chloro 6-methyl-3-aminophenol, 3-amino-2-methylamino-6-methoxypyridine, 2-amino-3-hydroxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2- Methylresorcin, 5-methylresorcinol, 2-methyl-4-chloro-5-aminophenol and the physiologically acceptable salts
  • the hairline colorants of the method according to the invention contain both the developer components and the coupler components preferably in an amount of 0.005 to 10 wt .-%, preferably from 0.1 to 5 wt .-%, each based on the entire Haaransatzfärbesch.
  • developer components and coupler components are generally used in approximately molar amounts to each other. Although the molar use has proved to be useful, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1 : 2, may be included.
  • the hairline colorant of the process according to the invention contains as colorant component i at least one compound containing a reactive carbonyl group, in combination with component ii of at least one compound selected from (a) CH-acidic compounds and (b) compounds with primary or secondary amino group or hydroxy group selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds.
  • Component i and component ii are preferably formulated in separate cosmetic compositions 1 and 2, and the actual hairline colorant from these two compositions is mixed only shortly before use.
  • At least one of the compositions 1 and 2 of this embodiment may additionally contain at least one branched (C 6 to C 30 ) fatty acid and / or at least one branched or unbranched (C 8 to C 30 ) dicarboxylic acid for viscosity stabilization.
  • the fatty acids used are preferably saturated.
  • branched (C 6 to C 30 ) fatty acids are 2-ethylhexanoic acid, isotridecanoic acid, isopalmitic acid, isostearic acid, 2-hexyldecanoic acid and 2-octyldodecanoic acid.
  • the isostearic which are sold for example under the names Emersol ® 871 and Emersol ® 875 are especially preferred, and the isopalmitic, such as the commercial product Edenor ® IP 95.
  • the isostearic is a particularly preferred C 6 - to C 30 fatty acid.
  • the dicarboxylic acid (mixture) has been found, which is formed by reaction of linoleic acid with acrylic acid. It is a mixture of 8- (2'-carboxy-4'-hexyl-cyclohex-5'-ene) -1-octanoic acid and 8- (2'-carboxy-4'-hexyl-cyclohex-5 ' -en) -1-octanoic acid.
  • Such compounds are commercially available under the designations Westvaco Diacid 1550 Westvaco Diacid ® ® 1595 (manufacturer: Westvaco).
  • Compounds according to the invention having a reactive carbonyl group have at least one carbonyl group as reactive group which reacts with the compounds of component ii to form a chemical bond linking both components. Furthermore, according to the invention, those compounds are also included as component i in which the reactive carbonyl group is derivatized or masked such that the reactivity of the carbon atom of the derivatized or masked carbonyl group with respect to component ii is always present.
  • These derivatives are preferably condensation compounds of reactive carbonyl compounds with a) amines and their derivatives to form imines or oximes as a condensation compound b) alcohols to form acetals or ketals as a condensation compound c) water to form hydrates as a condensation compound of aldehydes.
  • Component i is preferably selected from the group formed from acetophenone, propiophenone, 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, 2-hydroxypropiophenone, 3-hydroxypropiophenone, 4-hydroxypropiophenone, 2-hydroxybutyrophenone, 3-hydroxybutyrophenone, 4-hydroxybutyrophenone, 2,4-dihydroxyacetophenone, 2,5-dihydroxyacetophenone, 2,6-dihydroxyacetophenone, 2,3,4-trihydroxyacetophenone, 3,4,5-trihydroxyacetophenone, 2,4,6-trihydroxyacetophenone non, 2,4,6-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone diethyl ketal, 4-hydroxy-3-methoxy-acetophenone, 3,5-dimethoxy-4- hydroxyacetophenone, 4-aminoacetophenone, 4-dimethylaminoacetophenone, A
  • Ethoxybenzaldehyde 4-hydroxy-2,3-dimethoxybenzaldehyde, 4-hydroxy-2,5-dimethoxybenzaldehyde, 4-hydroxy-2,6-dimethoxybenzaldehyde, 4-hydroxy-2-methylbenzaldehyde, 4- Hydroxy-3-methylbenzaldehyde, 4-hydroxy-2,3-dimethylbenzaldehyde, 4-hydroxy-2,5-dimethylbenzaldehyde, 4-hydroxy-2,6-dimethylbenzaldehyde, 4-hydroxy-3, 5-dimethoxybenzaldehyde, 4-hydroxy-3,5-dimethylbenzaldehyde, 3,5-diethoxy-4-hydroxybenzaldehyde, 2,6-diethoxy-4-hydroxybenzaldehyde, 3-hydroxy-4-methoxy- benzaldehyde, 2-hydroxy-4-methoxy-benzaldehyde, 2-ethoxy-4-hydroxy-benzaldehyde, 3-ethoxy-4-hydroxy-benzaldeh
  • Formylmethylene-1, 3,3-trimethylindoline Fischer's aldehyde or tribasic aldehyde
  • 2-indolaldehyde, 3-indolaldehyde 1-methylindole-3-aldehyde, 2-methylindole-3-aldehyde, 1-acetylindole-3-aldehyde, 3 Acetylindole, 1-methyl-3-acetylindole, 2- (1 ', 3', 3'-trimethyl-2-indolinylidene) acetaldehyde, 1-methylpyrrole-2-aldehyde, 1-methyl-2-acetylpyrrole, 4-pyridinealdehyde, 2-pyridinaldehyde, 3-pyridinaldehyde, 4-acetylpyridine, 2-acetylpyridine, 3-acetylpyridine, pyridoxal, quinoline-3-aldehyde, quinoline-4-aldehyde
  • Benzylideneacetone 4-hydroxybenzylideneacetone, 2-hydroxybenzylideneacetone, 4-methoxybenzylideneacetone, 4-hydroxy-3-methoxybenzylideneacetone, 4-dimethylaminobenzylidene acetone, 3,4-methylenedioxybenzylideneacetone, 4-pyrrolidinobenzylideneacetone, 4-piperidinobenzylideneacetone, 4-morpholinobenzylideneacetone, A-
  • CH-acidic compounds are generally considered to carry a hydrogen atom bound to an aliphatic carbon atom, wherein due to electron-withdrawing substituents activation of the corresponding carbon-hydrogen bond is effected.
  • CH-acidic compounds also include enamines which are formed by alkaline treatment of quaternized N-heterocycles with a CH-acidic alkyl group in conjugation with the quaternary nitrogen.
  • the CH-acidic compounds of component ii are preferably selected from the group consisting of 1, 2,3,3-tetramethyl-3H-indolium iodide, 1, 2,3,3-tetramethyl-3H-indolium p-toluenesulfonate, 1, 2,3,3-tetramethyl-3H-indolium methanesulfonate, 1,3,3-trimethyl-2-methylenindoline (Fischer's base), 2,3-dimethylbenzothiazolium iodide, 2,3-dimethylbenzothiazolium-p- toluenesulfonate, 2,3-dimethyl-naphtho [1,2-d] thiazolium p-toluenesulfonate, 3-ethyl-2-methyl-naphtho [1,2-d] thiazolium p-toluenesulfonate, rhodanine, rhodanine-3
  • Trimethylquinoxalinium iodide 3-ethyl-2-methyl-benzoxazolium-p-toluenesulfonate, 3-ethyl-2-methyl-benzothiazolium-p-toluenesulfonate, 1-ethyl-4-methyl-quinolinium-p-toluenesulfonate, 1-ethyl-2- methylquinolinium p-toluenesulfonate, 1,2,3-trimethylquinoxaluminum p-toluenesulfonate, 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium chloride, 1,2-dihydro-1, 3,4,6-tetramethyl-2-oxopyrimidinium hydrogensulfate, 1, 2-dihydro-1, 3,4-trimethyl-2-oxopyrimidinium chloride, 1, 2-dihydro-4,6-dimethyl- 1, 3-dipropyl-2
  • anionic counterions of the abovementioned cationic CH-acidic compounds can be replaced arbitrarily by halide (in particular chloride, bromide), benzenesulfonate, p-toluenesulfonate, C 1 -C 4 -alkanesulfonate, trifluoromethanesulfonate, perchlorate, hemisulfate, hydrogensulfate, tetrafluoroborate, hexafluorophosphate or tetrachlorozincate.
  • Preferred primary or secondary aromatic amines of component ii are selected from N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N- (2-hydroxyethyl) -N-ethyl-p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, N- (2-methoxyethyl) -p-phenylenediamine, 2,3-dichloro-p-phenylenediamine, 2,4-dichloro-p-phenylenediamine, 2.5- Dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl 4-aminophenol, o-phenylenediamine,
  • R 7 represents a hydroxy or an amino group represented by C 1-4 -alkyl, C 1-4 -hydroxyalkyl, Ci. 4 -alkoxy or Ci. 4- alkoxy-C 1-4 -alkyl groups may be substituted,
  • R 8, R 9, R 10, R 11 and R 12 independently represent a hydrogen atom, a hydroxy or an amino group represented by C r C 4 alkyl, dC 4 hydroxyalkyl, C 1 -C 4 - alkoxy, -, C r C 4 -Aminoalkyl- or C 1 -C 4 alkoxy-C 1 -C 4 alkyl groups may be substituted, and
  • P is a direct bond, a saturated or unsaturated, optionally substituted by hydroxyl groups carbon chain having 1 to 4 carbon atoms, a carbonyl, sulfoxy, sulfonyl or imino group, an oxygen or sulfur atom, or a group having the formula III
  • Q signifies a direct bond, a CH 2 or CHOH group
  • Q 'and Q independently represent an oxygen atom, an NR 13 group, wherein R 13 is a hydrogen atom, a C 1-4 alkyl or a hydroxy C 1-4 alkyl group, both of which groups together with the remainder of the molecule may form a 5-, 6- or 7-membered ring means the group O- (CH 2 ) P -NH or NH- (CH 2 ) P -O, wherein p and p 'are 2 or 3 , stand and
  • O is a number from 1 to 4,
  • 4,4'-diaminostilbene and its hydrochloride 4,4'-diaminostilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochloride, 4, 4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfide, 4,4'-diaminodiphenylsulfoxide, 4,4'-diaminodiphenylamine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, 4,4 ' Diaminodiphenyl ether, 3,3 ', 4,4'-tetraaminodiphenyl, 3,3', 4,4'-tetraaminobenzophenone, 1,3-bis- (2,4-diaminophenoxy) -propane, 1, 8 - bis
  • the abovementioned compounds can be used both in free form and in the form of their physiologically acceptable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are, for. B. 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-amino-3-hydroxy-pyridine, 2,6-diamino-pyridine, 2,5-diamino-pyridine, 2- (aminoethylamino) -5-aminopyridine, 2,3-diamino-pyridine, 2-dimethylamino-5-amino-pyridine, 2-methylamino-3-amino-6-methoxy-pyridine, 2,3-diamino-6-methoxy-pyridine, 2,6- Dimethoxy-3,5-diamino-pyridine, 2,4,5-triamino-pyridine, 2,6-dihydroxy-3,4-dimethylpyridine, N- [2- (2,4-diaminophenyl) aminoethyl] -N - (5-amino-2-pyridyl) -amine, N- [2- (4-
  • heterocyclic compounds the hydroxypyrimidines disclosed in DE-U 1-299 08 573 can be used according to the invention.
  • the aforementioned compounds can be used both in free form and in the form of their physiologically acceptable salts, for. B. as salts of inorganic acids, such as hydrochloric or sulfuric acid, are used.
  • Suitable aromatic hydroxy compounds are, for. 2-methylresorcinol, 4-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 3 Dimethylaminophenol, 2- (2-hydroxyethyl) phenol, 3,4-methylenedioxyphenol, 2,4-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 2,4-dihydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid, gallic acid, 2 , 4,6-trihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, 2-chlororesorcinol, 4-chlororesorcinol, 1-naphthol, 1, 5-dihydroxynaphthalene, 2,3-d
  • the compounds of component i and the compounds of component ii are preferably used in the hair-setting colorants according to the invention in each case in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the entire hair-setting dye.
  • the molar ratio of component i and the compound of component ii may range from 0.5 to 2.0, preferably using equimolar amounts.
  • the actual Haaransatzstärbesch is prepared with separate storage of components i and ii immediately before use by mixing.
  • the hairline colorants may additionally contain at least one conventional substantive dye for shading, such as nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those having the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds as well as 1 , 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis ( ⁇ -hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- ( ⁇ -hydroxyethyl) -aminophenol, 2 - (2'-hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxyethyl) amino
  • Ureidoethyl) amino-4-nitrobenzene 4-amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, 2-hydroxy-1,4-naphthoquinone, picramic acid and its salts, 2-Amino-6-chloro-4-nitrophenol, 4-ethylamino-3-nitrobenzoic acid and 2-chloro-6-ethylamino-1-hydroxy-4-nitrobenzene.
  • Particularly preferred substantive dyes are cationic dyes, such as
  • Preferred cationic substantive dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic substantive dyes of group (c).
  • the cationic direct dyes which are sold under the trademark Arianor ® are, according to the invention also very particularly preferred cationic direct dyes.
  • the hairline colorants may contain the substantive dyes in an amount of from 0.1% to 5% by weight, based on the total hairline colorant.
  • the process of the invention may also naturally occurring dyes such as red henna, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included ,
  • oxidation dye precursors or the direct dyes it is not necessary for the oxidation dye precursors or the direct dyes to be in each case homogeneous compounds. Rather, in the Haaransatzfärbeschn invention, due to the production process for the individual dyes, in minor amounts, other components may be included, as far as they do not adversely affect the dyeing result or for other reasons, e.g. toxicological, must be excluded.
  • Oxidative staining of the hairline can be carried out in the presence of atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent is used, especially if, in addition to the coloring, a whitening effect of the natural pigments of the human hair is desired. This lightening effect may be desired regardless of the staining method.
  • the presence of oxidation dye precursors is not a mandatory requirement for the use of oxidizing agents in the Haaransatzfärbeschn the process of the invention.
  • the oxidizing agent is in particular hydrogen peroxide or its addition products of urea, melamine and sodium borate in Question.
  • the hair preparation colorant is mixed before application from a composition containing at least one coloring component in a cosmetic carrier and a further composition containing at least one oxidizing agent in a cosmetic carrier.
  • the oxidizing agent-containing composition of this embodiment may additionally contain at least one branched (C 6 to C 30 ) fatty acid and / or at least one branched or unbranched (C 8 to C 30 ) dicarboxylic acid for viscosity stabilization.
  • the fatty acids used are preferably saturated.
  • Especially preferred branched (C 6 to C 30 ) fatty acids according to the invention are 2-ethylhexanoic acid, isotridecanoic acid, isopalmitic acid, isostearic acid, 2-hexyldecanoic acid and 2-octyldodecanoic acid.
  • isostearic acids for example, among the isostearic acids.
  • Isopalmitic acids such as the commercial product Edenor ® IP 95.
  • Isostearic acid is a particularly preferred C 6 - to C 30 fatty acid.
  • the dicarboxylic acid (mixture) has been found, which is formed by reaction of linoleic acid with acrylic acid. It is a mixture of 8- (2'-carboxy-4'-hexyl-cyclohex-5'-ene) -1-octanoic acid and 8- (2'-carboxy-4'-hexyl-cyclohex-5 ' -en) -1-octanoic acid.
  • Such compounds are commercially available under the designations Westvaco Diacid 1550 Westvaco Diacid ® ® 1595 (manufacturer: Westvaco).
  • the Haaransatzfärbesch can also be applied together with a catalyst on the hair, which activates the oxidation of the dye precursors, for example by atmospheric oxygen.
  • catalysts are, for example, metal ions, iodides, quinones or certain enzymes.
  • the catalysts can also be used in the presence of an oxidizing agent.
  • Suitable metal ions are, for example, Zn 2+ , Cu 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al 3+ .
  • Particularly suitable are Zn 2+ , Cu 2+ and Mn 2+ .
  • the metal ions can in principle be used in the form of any physiologically acceptable salt or in the form of a complex compound.
  • Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
  • Suitable enzymes are e.g. Peroxidases that can significantly increase the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as, for example, the laccases, or generate small amounts of hydrogen peroxide in situ and thus biocatalytically activate the oxidation of the dye precursors.
  • Particularly suitable catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the specific substrates, e.g. Pyranose oxidase and e.g. D-glucose or galactose,
  • Alcohol oxidase and alcohol (MeOH, EtOH), lactate oxidase and lactic acid and their salts, tyrosinase oxidase and tyrosine,
  • Uricase and uric acid or their salts choline oxidase and choline, amino acid oxidase and amino acids.
  • the actual Haaransatzfetzbesch is conveniently prepared immediately prior to use by mixing the preparation of the oxidizing agent with the preparation containing the coloring components.
  • the resulting ready-to-use hair dye preparation should be preferred have a pH in the range of 6 to 12. Particularly preferred is the application of the Haaransatzfetzbesch in a weakly alkaline medium.
  • the washing with a shampoo is omitted if a strong surfactant-containing carrier, e.g. a dyeing shampoo was used.
  • a strong surfactant-containing carrier e.g. a dyeing shampoo was used.
  • the Haaransatzfärbesch the process of the invention preferably contain the ingredients of the invention in a cosmetic carrier.
  • a cosmetic carrier Suitable examples are aqueous, alcoholic or aqueous-alcoholic cosmetic carrier.
  • Such carriers are for example creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • a solvent such as e.g. Water gives an application mixture with the features according to the invention as Haaransatzstärbesch.
  • Aqueous cosmetic vehicles contain at least 50% by weight of water
  • aqueous-alcoholic cosmetic carrier of the present invention are aqueous carrier containing understand 3 to 70 wt .-% of a C r C 4 -alcohol, in particular ethanol or isopropanol in a sense.
  • the compositions of the invention may additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1, 2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • the Haaransatzfärbesch the process of the invention may further contain all known for such preparations active ingredients, additives and excipients.
  • the Haaransatzstärbesch contain at least one surfactant, wherein in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, however, it has proved to be advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such. Example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 10 to 22 carbon atoms.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium and the mono-, di- and Trialkanolammoniumsalze with 2 or 3 C atoms in the alkanol group, linear fatty acids having 10 to 22 carbon atoms (soaps )
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 C atoms in the alkyl group and up to 12 glycol ether groups. in the molecule and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Nonionic surfactants contain as hydrophilic group z.
  • a polyol group for example, a polyalkylene glycol ether or a combination of polyol and Polyglykolether- group.
  • Such compounds are, for example
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula R 1 O- (Z) x . These connections are identified by the following parameters.
  • the alkyl radical R 1 contains 6 to 22 carbon atoms and may be both linear and branched. Preference is given to primary linear and methyl-branched in the 2-position aliphatic radicals.
  • Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. Particularly preferred are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl.
  • oxo-alcohols compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • the alkyl polyglycosides which can be used according to the invention can contain, for example, only one particular alkyl radical R 1 .
  • these compounds are prepared starting from natural fats and oils or mineral oils.
  • the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the particular work-up of these compounds.
  • R 1 consists essentially of C 8 and C 10 -alkyl groups, essentially of C 2 - and C 14 alkyl groups, essentially of C 8 - to C 16 -alkyl groups or consists essentially of C 12 - to C 6 alkyl groups is.
  • sugar building block Z it is possible to use any desired mono- or oligosaccharides.
  • sugars with 5 or 6 carbon atoms and the corresponding oligosaccharides are used.
  • Such sugars are, for example, glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, altrose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar building blocks are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain on average from 1.1 to 5 sugar units. Alkyl polyglycosides having x values of 1.1 to 1.6 are preferred. Very particular preference is given to alkyl glycosides in which x is 1: 1 to 1, 4.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • this substance class as a further constituent of the preparations according to the invention in the event that an effect of the perfume oil on the hair which exceeds the duration of the hair treatment is desired.
  • alkoxylated homologs of said alkyl polyglycosides can also be used according to the invention. These homologs may contain on average up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • zwitterionic surfactants can be used, in particular as cosurfactants.
  • Zwitterionic surfactants are surface-active compounds which carry at least one quaternary ammonium group and at least one -COO H or -SO 3 H group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinates, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example the cocoacylaminopropyldimethylammoniumglycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines having in each case 8 to 18 C atoms in the alkyl or acyl group and the cocoacylaminoethyl hydroxyethylcarboxymethylglycinat.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
  • ampholytic surfactants are also particularly suitable as co-surfactants.
  • am- pholytica surfactants are surface-active compounds which, apart from a C 8 -C 8 alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO 3 H group and to form internal Salts are capable.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12-18 acylsarcosine.
  • the cationic surfactants used are, in particular, those of the quaternary ammonium compound type, the esterquats and the amidoamines.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names Quatemium-27 and Quaternium-83.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred esterquats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are marketed under the trade names Stepantex® ®, ® and Dehyquart® Armocare® ®.
  • the alkylamidoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group of substances that available under the name Tegoamid ® S 18 commercially stearamidopropyldimethylamine is dimethylamine.
  • cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • cationic silicone oils such as the commercially available products Q2-7224 (manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicones), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® - Quat 3270 and 3272 (manufacturer: Th Goldschmidt; diquaternary polydimethylsiloxanes, quaternium-80.).
  • Q2-7224 manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone
  • Dow Corning 929 emulsion containing a hydroxylamino-modified silicone, also referred to as amodimethicones
  • SM-2059 manufactured by General Electric
  • SLM-55067 manufactured by Wacker
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to INCI nomenclature a "lauryl methyl GIu- Ceth-10 hydroxypropyl dimonium chloride".
  • the compounds used as surfactant with alkyl groups may each be uniform substances. However, it is generally preferred to use native vegetable or animal raw materials in the production of these substances, so that substance mixtures having different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrow homolog distribution can be used.
  • "normal” homolog distribution are thereby Mixtures of homologs obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts.
  • Narrowed homolog distributions are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts.
  • the use of products with narrow homolog distribution may be preferred.
  • Active ingredients and additives such as nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes,
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, diethyl sulfate-quaternized dimethylaminoethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methylmethacrylate / tert-butylaminoethylmethacrylamide-hydroxypropyl methacrylate copolymers,
  • anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert-butyl acrylamide terpolymers
  • Structural agents such as maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins,
  • Protein hydrolysates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, their condensation products with fatty acids and quaternized protein hydrolysates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, fibrous structure-improving active substances, in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fructose and lactose,
  • quaternized amines such as methyl-1-alkylamidoethyl-2-alkylimidazolinium methosulfate defoamers such as silicones,
  • Antidandruff active ingredients such as Piroctone Olamine, Zinc Omadine and Climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines,
  • Substances for adjusting the pH such as, for example, customary acids, in particular edible acids and bases,
  • Active ingredients such as allantoin, pyrrolidonecarboxylic acids and their salts, and bisabolol,
  • Vitamins, provitamins and vitamin precursors in particular those of groups A,
  • Plant extracts such as extracts of green tea, oak bark, stinging nettle,
  • Melissa, hominy, coltsfoot, marshmallow, meristem, ginseng and ginger root Melissa, hominy, coltsfoot, marshmallow, meristem, ginseng and ginger root ,.
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as spermaceti, beeswax, montan wax and paraffins,
  • - swelling and penetrating substances such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate,
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air,
  • Suitable conditioners are all conditioners known to the person skilled in the art, in the form of leave-on or rinse-off conditioners.
  • a second object of the present application is a sales unit (kit) of a hairline colorant comprising
  • a container C1 comprising a composition which contains at least one coloring component in a cosmetic carrier
  • a container C2 containing a composition which comprises in a cosmetic carrier at least one branched (C 6 to C 30 ) fatty acid and / or at least one branched or unbranched (C 8 to C 30 ) dicarboxylic acid and / or at least one oxidizing agent contains and
  • the hairline colorant is the composition of container C1 or the mixture of the compositions of containers C1 and C2,
  • the hairline colorant contains as a coloring component
  • At least one developer component optionally in combination with at least one coupler component and / or
  • component i of at least one reactive carbonyl compound with component ii of at least one compound selected from the group consisting of (a) CH-acidic compounds and (b) compounds with primary or secondary amino group or hydroxy group selected from primary or secondary aromatic amines, nitrogen-containing eterocyclic compounds and aromatic hydroxy compounds.
  • the preferred embodiments of the first subject of the invention can be analogously transferred to the kit of the second subject of the invention.
  • the kit preferably additionally contains a shell which is suitable in particular for mixing the hair preparation colorant and as a container for storing the hair preparation colorant during the performance of the method according to the invention.
  • a shell according to the invention is understood to mean an open vessel which has a base surface and a wall on this base surface, preferably along the edge of the base surface.
  • the base may be, for example, triangular, quadrangular, pentagonal, hexagonal, heptagonal, octagonal, circular or oval.
  • the wall may be straight or curved along its extension, which is not in the plane of the base.
  • the wall is preferably at an angle of 45 ° to 135 ° on the base. An angle of 75 ° to 105 °, in particular of 90 °, is particularly preferred.
  • the shell may be opaque or transparent.
  • the shell may also be a component of the package, e.g. a so-called tray with a reservoir.
  • container C1 contains the cosmetic carrier which contains as color-providing component at least one developer component, optionally in combination with at least one coupler component.
  • container C2 an oxidant-containing composition is stored.
  • the latter additionally preferably contains in its cosmetic vehicle at least one branched (C 6 to C 30 ) fatty acid and / or at least one branched or unbranched (C 8 to C 30 ) dicarboxylic acid. Preferred representatives of these acids are those of the first subject of the invention.
  • either the compounds of component i in container C2 and the compounds of component ii in container C1 or the compounds of component i in container C1 and the compounds of component ii are stored separately in container C2.
  • the container C2 contains no oxidizing agent.
  • the containers C1 and C2 can be different chambers within a two- or multi-chamber container, for example a multi-chamber tube, a multi-chamber aerosol can or a multi-chamber bottle. Such containers are known to those skilled in the art. When the contents are taken from a multi-chamber container, the content of the individual chambers is mixed with the ready-to-use hair preparation colorant before the contents emerge.
  • the kit of the invention may additionally comprise a container C3 containing a conditioning agent.
  • the kit may additionally include a use instruction which prescribes the use of the kit according to the method of the first subject of the invention.
  • a third object of the invention is the use of the kit according to the second aspect of the invention in a method of the first subject of the invention.

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Abstract

L'invention concerne un procédé pour colorer sélectivement la racine non colorée de cheveux qui ont subi une coloration sur leur longueur. Ce procédé comporte plusieurs étapes qui consistent : A) au cours d'une première étape, à appliquer un agent de coloration de racine capillaire sur la racine de cheveux non colorée, cet agent de coloration contenant au moins un composant colorant dans un support cosmétique, puis à rincer ledit agent de coloration après un temps d'action (Z1), et éventuellement ; B) au cours d'une étape supplémentaire, à traiter l'ensemble des fibres à l'aide d'un agent de conditionnement capillaire. Selon l'invention, l'agent de coloration de racine capillaire présente une viscosité pouvant aller de 2000 à maximum 27000 mPa s (viscosimètre Brookfield, type RTV, broche 5, 2 UpM) à 20 °C, et le temps d'action (Z1) ne dépasse pas une durée de 20 minutes. Le procédé selon l'invention permet de colorer ultérieurement, de manière rapide et sélective, une racine capillaire non colorée qui résulte de la pousse des cheveux. Ledit procédé peut être effectué de manière autonome par l'utilisateur sans l'aide d'une autre personne.
EP06762630A 2005-08-05 2006-07-17 Procede pour dissimuler rapidement des racines capillaires resultant de la pousse de cheveux colores Ceased EP1909913A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510037681 DE102005037681A1 (de) 2005-08-05 2005-08-05 Verfahren zu schnellen Kaschierung des nachgewachsenen Haaransatzes bei gefärbtem Haar
PCT/EP2006/006990 WO2007017048A1 (fr) 2005-08-05 2006-07-17 Procede pour dissimuler rapidement des racines capillaires resultant de la pousse de cheveux colores

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EP (1) EP1909913A1 (fr)
AU (1) AU2006278923A1 (fr)
DE (1) DE102005037681A1 (fr)
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WO (1) WO2007017048A1 (fr)

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EP2272489A1 (fr) * 2009-07-09 2011-01-12 KPSS-Kao Professional Salon Services GmbH Procédé de nivellement de couleur de cheveux

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DE10138094A1 (de) * 2001-08-03 2003-02-13 Henkel Kgaa Selektive Farbveränderung

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DE19815341C1 (de) * 1998-04-06 1999-08-26 Goldwell Gmbh Verfahren zur Herstellung von stabilen wäßrigen Haarfärbeemulsionen und wäßrige Haarfärbeemulsion
DE19815338C1 (de) * 1998-04-06 1999-09-09 Goldwell Gmbh Verfahren zur Herstellung von stabilen wäßrigen Haarfärbeemulsionen
US7056351B2 (en) * 2000-12-13 2006-06-06 The Procter & Gamble Company Oxidative hair dye composition containing polyakyleneglyco(n)alkylamine and a solid fatty compound
DE10101946A1 (de) * 2001-01-17 2002-08-01 Goldwell Gmbh Haarfärbemittel

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Publication number Priority date Publication date Assignee Title
DE10138094A1 (de) * 2001-08-03 2003-02-13 Henkel Kgaa Selektive Farbveränderung

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Title
See also references of WO2007017048A1 *

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