WO1995007068A1 - Oxidation dyes containing 2-hydroxy-4-aminobenzene derivatives as couplers and hydroxytriaminopyrimidines or dihydroxydiaminopyrimidines as developers - Google Patents
Oxidation dyes containing 2-hydroxy-4-aminobenzene derivatives as couplers and hydroxytriaminopyrimidines or dihydroxydiaminopyrimidines as developers Download PDFInfo
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- WO1995007068A1 WO1995007068A1 PCT/EP1994/002929 EP9402929W WO9507068A1 WO 1995007068 A1 WO1995007068 A1 WO 1995007068A1 EP 9402929 W EP9402929 W EP 9402929W WO 9507068 A1 WO9507068 A1 WO 9507068A1
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- hydroxy
- dihydroxy
- diaminopyrimidine
- triaminopyrimidine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- 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
Definitions
- OXIDATION PAINT CONTAINING 2-HYDR0XY-4-AMIN0-BENZ0L DERIVATIVES AS COUPLING SUBSTANCES AND HYDROXYTRIAMINOPYRIMIDINE OR DIHYDROXYDIAMINO-PYRIMIDINE AS DEVELOPING SUBSTANCES.
- compositions for dyeing keratin-containing fibers, in particular human hair which contain a specially substituted aminophenol as developer component and a hydroxytriaminopyrimidine and / or dihydroxydiaminopyrirnidine as coupler component.
- oxidation hair colorants play a preferred role for dyeing hair because of their intense colors and good fastness properties.
- hair dyes contain oxidation dye precursors in a cosmetic carrier.
- Developer substances and coupler substances are used as oxidation dye precursors.
- the developer components form the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
- Good oxidation dye precursors must first of all meet the following requirements: They must have the desired color shades in sufficient intensity and fastness in the oxidative coupling form. They must also have a good ability to draw on human hair, with no noticeable differences between damaged and freshly regrown hair. They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against perm fluids. After all, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view.
- a certain developer substance can form very different shades of color when combined with different couplers. Nevertheless, it is often not possible to achieve the multitude of natural hair color shades with the help of a single developer substance. In practice, therefore, a combination of different developer components and coupler components is usually required in order to obtain a single, natural-looking hair color. There is therefore a constant need for new, improved coupler / developer combinations.
- Primary aromatic amines with a further free or substituted hydroxy or amino group in para or ortho position, tetraaminopyrimidines, hydroxytriaminopyrimidines, dihydroxydiaminopyrimidines, diaminopyridine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives are usually used as developer components.
- M-Phenylenediamine derivatives, m-aminophenol derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler components.
- German patent application DE 34 21 694 AI describes hair colorants which contain substituted 3,4-dihydroxyilines as coupler components.
- German published patent application DE 31 45 811 A1 discloses hair dye compositions which also contain substituted 3,4-dihydroxyanilines, for example 1- (2'-hydroxyethoxy) -2-hydroxy-4-aminobenzene, in combination with tetraaminopyrimidine as the developer component.
- coupler components as disclosed in DE 31 45 811 AI can be combined in an ideal manner with hydroxytriaminopyrimidines and dihydroxydiaminopyrimidines and thus provide oxidation hair colorants which have the properties disclosed in DE 31 45 811 AI in terms of dyeing-relevant properties, e.g. Wash fastness, light fastness, rubbing fastness, color winding, leveling behavior are superior.
- the invention relates to compositions for dyeing keratin-containing fibers
- R * and R ⁇ independently of one another are hydrogen, C1-C4-alkyl or C2 ⁇ C4-hydroxyalkyl groups,
- At least one developer component selected from the group 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 5-hydroxy-2,4,6-triaminopyrimidine, 2,4-dihydroxy -5,6-di-aminopyrimidine, 2,5-dihydroxy-4,6-diaminopyrimidine, 4,5-dihy- droxy-2,6-diaminopyrimidine and 4,6-dihydroxy-2,5-diaminopyrimidine,
- Keratin-containing fibers are hair, furs, wool or feathers.
- the coupler and developer components can be used both as free bases and in the form of their inorganic or organic salts, e.g. the hydrochloride or hydrobromide.
- Preferred colorants are those in which the developer component is selected from 4-hydroxy-2,5,6-triaminopyrimidine and 2,4-dihydroxy-5,6-diaminopyrimidine or in those in the coupler component of the formula IR * and R ⁇ represent hydrogens.
- the colorants according to the invention provide a broad spectrum of oxidation colors which are of interest in terms of application technology, in the range from red to ruby shades, which are suitable for dyeing human hair, owing to their brilliance, good leveling ability and good fastness properties.
- a further subject of the invention is therefore hair dyes
- At least one coupler component of the formula I in an amount of 0.05 to 20 mmol, preferably 1 to 10 mmol,
- At least one developer component selected from the group 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 5-hydroxy-2,4,6-triaminopyrimidine, 2,4-dihydroxy -5,6-di-aminopyrimidine, 2,5-dihydroxy-4,6-diaminopyrimidine, 4,5-dihy- droxy-2,6-diaminopyrimidine and 4,6-dihydroxy-2,5-diaminopyrimidine, in an amount of 0.05 to 20 mmol, preferably 1 to 10 mmol, in each case based on 100 g of the total hair dye,
- the hair dye according to the invention can in addition to the above.
- Developer components optionally other customary developer components e.g. from the group of primary aromatic amines with a further free or substituted hydroxy or amino group in the p or o position, diaminopyridine derivatives, tetraaminopyrimidine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives.
- coupler components of formula I they can also contain other conventional coupler components, e.g. from the group of m-phenylenediamine derivatives, naphthols, resorcinols and pyrazolones.
- direct dyes e.g. from the group of nitrophenylene diamines, nitroa inophenols, anthraquinones or indophenols.
- developer components and coupler components are generally used in approximately molar amounts to one another. If the molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components can be present in a molar ratio of 1: 0.5 to 1: 2 .
- the oxidation dye precursors are incorporated in a suitable water-containing carrier.
- suitable water-containing carrier are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions, for example shampoos, aerosols or other preparations which are suitable for use on the hair.
- the water-containing carrier usually contains wetting and emulsifying agents, such as anionic, nonionic or ampholytic surfactants, for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on sorbitan fatty acids, on alkylphenols, on Fatty acid partial glycerides and fatty acid alkanolamides; Thickeners, e.g. B.
- anionic, nonionic or ampholytic surfactants for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on sorbitan fatty acids, on alky
- fatty alcohols fatty acids, paraffin oils, fatty acid esters and other fat components in emulsified form
- water-soluble polymeric thickeners such as natural gums, e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin, biosynthetic gums, for example xanthan gum i and dextrans, synthetic gums, e.g. B. agar-agar and algin, starch fractions and derivatives such as amylose, amylopectin and dextrins, modified cellulose molecules, eg. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, clays such as. B.
- natural gums e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin
- biosynthetic gums for example xanthan gum i
- the constituents of the water-containing carrier are used for the production of the hair colorants according to the invention in amounts customary for this purpose;
- emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
- the oxidative development of the color can in principle be carried out with atmospheric oxygen.
- a chemical oxidizing agent is preferably used, especially when a lightening effect on the hair is desired in addition to the coloring.
- Particularly suitable oxidizing agents are hydrogen peroxide or its adducts with urea, melamine or sodium borate and mixtures of such hydrogen peroxide adducts with potassium peroxide disulfate.
- the preparation of the oxidizing agent is expediently mixed with the preparation from the oxidation dye precursors immediately before hair coloring.
- the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
- the application temperatures can be in a range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is removed from the hair to be colored by rinsing. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a color shesha poo was used.
- Hair dyes according to the invention were produced in the form of a hair dye emulsion with the following composition:
- the ingredients were mixed together in order. After the oxidation dye precursors and the inhibitor had been added, the pH of the emulsion was first adjusted to 9.5 with concentrated ammonia solution, and the mixture was then made up to 100 g with water.
- the oxidative development of the color was carried out with 3% hydrogen peroxide solution as the oxidation solution.
- 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
- the coloring cream was applied to strands approx. 5 cm long, 90% gray but not specially pretreated, and left there for 30 minutes at 27 ° C. After the dyeing process had ended, the hair was rinsed, washed with a conventional shampoo and then dried.
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Abstract
Description
OXIDATIONSFARBEMITTEL, ENTHALTEND 2-HYDR0XY-4-AMIN0-BENZ0L-DERIVATE ALS KUPPLERSUBSTANZEN UND HYDROXYTRIAMINOPYRIMIDINE ODER DIHYDROXYDIAMINO- PYRIMIDINE ALS ENTWICKLERSUBSTANZEN.OXIDATION PAINT, CONTAINING 2-HYDR0XY-4-AMIN0-BENZ0L DERIVATIVES AS COUPLING SUBSTANCES AND HYDROXYTRIAMINOPYRIMIDINE OR DIHYDROXYDIAMINO-PYRIMIDINE AS DEVELOPING SUBSTANCES.
Die Erfindung betrifft Mittel zum Färben von keratinhaltigen Fasern, insbesondere menschlichen Haaren, die als Entwicklerkomponente ein speziell substituiertes Aminophenol und als Kupplerkomponente ein Hydroxytriaminopyrimidin und/oder Dihydroxydiaminopyrirnidin enthal¬ ten.The invention relates to compositions for dyeing keratin-containing fibers, in particular human hair, which contain a specially substituted aminophenol as developer component and a hydroxytriaminopyrimidine and / or dihydroxydiaminopyrirnidine as coupler component.
Für das Färben von Haaren spielen die sogenannten Oxidationshaar- färbemittel wegen ihrer intensiven Farben und guten Echtheitseigen¬ schaften eine bevorzugte Rolle. Solche Haarfärbemittel enthalten Oxidationsfarbstoffvorprodukte in einem kosmetischen Träger. Als OxidationsfarbstoffVorprodukte werden Entwicklersubstanzen und Kupp¬ lersubstanzen eingesetzt. Die Entwicklerkomponenten bilden unter dem Einfluß von Oxidationsmitteln oder von Luftsauerstoff untereinander oder unter Kupplung mit einer oder mehreren Kupplerkomponenten die eigentlichen Farbstoffe aus.The so-called oxidation hair colorants play a preferred role for dyeing hair because of their intense colors and good fastness properties. Such hair dyes contain oxidation dye precursors in a cosmetic carrier. Developer substances and coupler substances are used as oxidation dye precursors. The developer components form the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
Gute Oxidationsfarbstoffvorprodukte müssen in erster Linie folgende Voraussetzungen erfüllen: Sie müssen bei der oxidativen Kupplung die gewünschten Farbnuancen in ausreichender Intensität und Echtheit ausbilden. Sie müssen ferner ein gutes Aufziehvermögen auf mensch¬ lichem Haar besitzen, wobei keine merklichen Unterschiede zwischen strapaziertem und frisch nachgewachsenem Haar bestehen dürfen. Sie sollen beständig sein gegen Licht, Wärme und dem Einfluß chemischer Reduktionsmittel, z. B. gegen Dauerwellflüssigkeiten. Schließlich sollen sie die Kopfhaut nicht zu sehr anfärben, und vor allem sollen sie in toxikologischer und dermatologischer Hinsicht unbedenklich sein.Good oxidation dye precursors must first of all meet the following requirements: They must have the desired color shades in sufficient intensity and fastness in the oxidative coupling form. They must also have a good ability to draw on human hair, with no noticeable differences between damaged and freshly regrown hair. They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against perm fluids. After all, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view.
Eine bestimmte Entwicklersubstanz kann durch Kombination mit unter¬ schiedlichen Kupplern sehr unterschiedliche Farbnuancen bilden. Trotzdem gelingt es oft nicht, mit Hilfe einer einzigen Entwickler¬ substanz zu der Vielzahl natürlicher Haarfarbnuancen zu kommen. In der Praxis ist daher meist eine Kombination verschiedener Entwick¬ lerkomponenten und Kupplerkomponenten erforderlich, um eine einzige, natürlich wirkende Haarfärbung zu erhalten. Es besteht daher ständig Bedarf an neuen, verbesserten Kuppler/Entwickler-Kombinationen.A certain developer substance can form very different shades of color when combined with different couplers. Nevertheless, it is often not possible to achieve the multitude of natural hair color shades with the help of a single developer substance. In practice, therefore, a combination of different developer components and coupler components is usually required in order to obtain a single, natural-looking hair color. There is therefore a constant need for new, improved coupler / developer combinations.
Als Entwicklerkomponenten werden üblicherweise primäre aromatische Amine mit einer weiteren in Para- oder Orthoposition befindlichen freien oder substituierten Hydroxy- oder Aminogruppe, Tetraaminopy- rimidine, Hydroxytriaminopyrimidine, Dihydroxydiaminopyrimidine, Di- a inopyridinderivate, heterocyclische Hydrazonderivate oder 4-Ami- nopyrazolonderivate eingesetzt. Als sogenannte Kupplerkomponenten werden m-Phenylendiaminderivate, m-Aminophenolderivate, Naphthole, Resorcinderivate und Pyrazolone verwendet.Primary aromatic amines with a further free or substituted hydroxy or amino group in para or ortho position, tetraaminopyrimidines, hydroxytriaminopyrimidines, dihydroxydiaminopyrimidines, diaminopyridine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives are usually used as developer components. M-Phenylenediamine derivatives, m-aminophenol derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler components.
Die deutsche Offenlegungsschrift DE 34 21 694 AI beschreibt Haar¬ färbemittel, die als Kupplerkomponenten substituierte 3,4-Dihydro- xyaniline enthalten. Die deutsche Offenlegungsschrift DE 31 45 811 AI offenbart Haarfär¬ bemittel, die ebensolche substituierten 3,4-Dihydroxyaniline, z.B. l-(2'-Hydroxyethoxy)-2-hydroxy-4-aminobenzol , in Kombination mit Te- traaminopyrimidin als Entwicklerkomponente enthalten.The German patent application DE 34 21 694 AI describes hair colorants which contain substituted 3,4-dihydroxyilines as coupler components. German published patent application DE 31 45 811 A1 discloses hair dye compositions which also contain substituted 3,4-dihydroxyanilines, for example 1- (2'-hydroxyethoxy) -2-hydroxy-4-aminobenzene, in combination with tetraaminopyrimidine as the developer component.
Überraschenderweise wurde nun gefunden, daß sich Kupplerkomponenten wie sie in DE 31 45 811 AI offenbart sind, in idealer Weise mit Hy- droxytriaminopyrimidinen und Dihydroxydiaminopyrimidinen kombinieren lassen und so Oxidationshaarfärbemittel liefern, die den in DE 31 45 811 AI offenbarten in färbetechnisch relevanten Eigenschaften wie z.B. Waschechtheit, Lichtechtheit, Reibecht, Farbaufzug, Egalisier¬ verhalten überlegen sind.Surprisingly, it has now been found that coupler components as disclosed in DE 31 45 811 AI can be combined in an ideal manner with hydroxytriaminopyrimidines and dihydroxydiaminopyrimidines and thus provide oxidation hair colorants which have the properties disclosed in DE 31 45 811 AI in terms of dyeing-relevant properties, e.g. Wash fastness, light fastness, rubbing fastness, color winding, leveling behavior are superior.
Gegenstand der Erfindung sind Mittel zum Färben von keratinhaltigen Fasern enthaltendThe invention relates to compositions for dyeing keratin-containing fibers
mindestens ein Aminophenol der Formel I als Kupplerkomponenteat least one aminophenol of the formula I as a coupler component
0-CH2CH20R20-CH 2 CH 2 0R2
wobei R* und R^ unabhängig voneinander Wasserstoffe, C1-C4-AI- kyl- oder C2~C4-Hydroxyalkylgruppen bedeuten,where R * and R ^ independently of one another are hydrogen, C1-C4-alkyl or C2 ~ C4-hydroxyalkyl groups,
mindestens eine Entwicklerkomponente ausgewählt aus der Gruppe 2-Hydroxy-4,5,6-triaminopyrimidin, 4-Hydroxy-2,5,6-triaminopyri- midin, 5-Hydroxy-2,4,6-triaminopyrimidin, 2,4-Dihydroxy-5,6-di- aminopyrimidin, 2,5-Dihydroxy-4,6-diaminopyrimidin, 4,5-Dihy- droxy-2,6-diaminopyrimidin und 4,6-Dihydroxy-2,5-diaminopyrimi- din,at least one developer component selected from the group 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 5-hydroxy-2,4,6-triaminopyrimidine, 2,4-dihydroxy -5,6-di-aminopyrimidine, 2,5-dihydroxy-4,6-diaminopyrimidine, 4,5-dihy- droxy-2,6-diaminopyrimidine and 4,6-dihydroxy-2,5-diaminopyrimidine,
und einen wasserhaltigen Träger.and a water-based carrier.
Unter keratinhaltigen Fasern sind Haare, Pelze, Wolle oder Federn zu verstehen.Keratin-containing fibers are hair, furs, wool or feathers.
Die Kuppler- und Entwicklerkomponenten können sowohl als freie Basen als auch in Form ihrer anorganischen oder organischen Salze, z.B. der Hydrochloride oder Hydrobromide, verwendet werden.The coupler and developer components can be used both as free bases and in the form of their inorganic or organic salts, e.g. the hydrochloride or hydrobromide.
Bevorzugte Färbemittel die diejenigen, in denen die Entwicklerkompo¬ nente ausgewählt ist aus 4-Hydroxy-2,5,6-triaminopyrimidin und 2,4- Dihydroxy-5,6-diaminopyrimidin bzw. in denen in der Kupplerkomponen¬ te der Formel I R* und R^ Wasserstoffe darstellen.Preferred colorants are those in which the developer component is selected from 4-hydroxy-2,5,6-triaminopyrimidine and 2,4-dihydroxy-5,6-diaminopyrimidine or in those in the coupler component of the formula IR * and R ^ represent hydrogens.
Die erfindungsgemäßen Färbemittel liefern ein breites Spektrum an¬ wendungstechnisch interessanter Oxidationsfarben im Bereich roter bis rubiner Nuancen, die sich wegen ihrer Brillanz, des guten Egali¬ siervermögens und der guten Echtheitseigenschaften, insbesondere zum Färben von menschlichen Haaren eignen.The colorants according to the invention provide a broad spectrum of oxidation colors which are of interest in terms of application technology, in the range from red to ruby shades, which are suitable for dyeing human hair, owing to their brilliance, good leveling ability and good fastness properties.
Ein weiterer Erfindungsgegenstand sind deshalb Haarfärbemittel ent¬ haltendA further subject of the invention is therefore hair dyes
mindestens eine Kupplerkomponente der Formel I in einer Menge von 0,05 bis 20 mMol, vorzugsweise 1 bis 10 mMol,at least one coupler component of the formula I in an amount of 0.05 to 20 mmol, preferably 1 to 10 mmol,
mindestens eine Entwicklerkomponente ausgewählt aus der Gruppe 2-Hydroxy-4,5,6-triaminopyrimidin, 4-Hydroxy-2,5,6-triaminopyri- midin, 5-Hydroxy-2,4,6-triaminopyrimidin, 2,4-Dihydroxy-5,6-di- aminopyrimidin, 2.5-Dihydroxy-4,6-diaminopyrimidin, 4,5-Dihy- droxy-2,6-diaminopyrimidin und 4,6-Dihydroxy-2,5-diaminopyrimi- din, in einer Menge von 0,05 bis 20 mMol, vorzugsweise 1 bis 10 mMol, jeweils bezogen auf 100 g des gesamten Haarfärbemittels,at least one developer component selected from the group 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 5-hydroxy-2,4,6-triaminopyrimidine, 2,4-dihydroxy -5,6-di-aminopyrimidine, 2,5-dihydroxy-4,6-diaminopyrimidine, 4,5-dihy- droxy-2,6-diaminopyrimidine and 4,6-dihydroxy-2,5-diaminopyrimidine, in an amount of 0.05 to 20 mmol, preferably 1 to 10 mmol, in each case based on 100 g of the total hair dye,
und einen wasserhaltigen Träger.and a water-based carrier.
Die erfindungsgemäßen Haarfärbemittel können neben den o.g. Entwick¬ lerkomponenten fakultativ weitere übliche Entwicklerkomponenten z.B. aus der Gruppe der primären aromatischen Amine mit einer weiteren in p- oder o-Position befindlichen freien oder substituierten Hydroxy- oder Aminogruppe, Diaminopyridinderivate, Tetraaminopyrimidinderi- vate, heterocycTische Hydrazonderivate oder 4-Aminopyrazolonderivate enthalten. Außerdem können sie neben den Kupplerkomponenten der For¬ mel I weitere übliche Kupplerko ponten z.B. aus der Gruppe der m-Phenylendiaminderivate, Naphthole, Resorcine und Pyrazolone ent¬ halten. Gegebenenfalls können zur weiteren Modifizierung der Farb¬ nuancen auch direktziehende Farbstoffe, z.B. aus der Gruppe der Ni- trophenylendiamine, Nitroa inophenole, Anthrachinone oder Indophe- nole enthalten sein.The hair dye according to the invention can in addition to the above. Developer components optionally other customary developer components e.g. from the group of primary aromatic amines with a further free or substituted hydroxy or amino group in the p or o position, diaminopyridine derivatives, tetraaminopyrimidine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives. In addition to the coupler components of formula I, they can also contain other conventional coupler components, e.g. from the group of m-phenylenediamine derivatives, naphthols, resorcinols and pyrazolones. If necessary, direct dyes, e.g. from the group of nitrophenylene diamines, nitroa inophenols, anthraquinones or indophenols.
In den erfindungsgemäßen Haarfärbemitteln werden Entwicklerkompo¬ nenten und Kupplerkomponenten im allgemeinen in etwa molaren Mengen zueinander eingesetzt. Wenn sich auch der molare Einsatz als zweck¬ mäßig erwiesen hat, so ist ein gewisser Überschuß einzelner Oxida¬ tionsfarbstoffvorprodukte nicht nachteilig, so daß Entwicklerkom¬ ponenten und Kupplerkomponenten in einem Mol-Verhältnis von 1 : 0,5 bis 1 : 2 enthalten sein können. Zur Herstellung der erfindungsge¬ mäßen Färbemittel werden die Oxidationsfarbstoffvorprodukte in einem geeigneten wasserhaltigen Träger eingearbeitet. Solche Träger sind z.B. Cremes, Emulsionen, Gele oder auch tensidhaltige schäumende Lösungen, z.B. Shampoos, Schaumaerosole oder andere Zubereitungen, die für die Anwendung auf dem Haar geeignet sind. Der wasserhaltige Träger enthält üblicherweise Netz- und Emulgier¬ mittel wie anionische, nichtionische oder ampholytische Tenside, z.B. Fettalkoholsulfate, Alkansulfonate, α-Olefinsulfonate, Fett- alkoholpolyglykolethersulfate, Alkylglycoside, Ethylenoxidanla- gerungsprodukte an Fettalkohole, an Fettsäuren, an Alkylphenole, an Sorbitanfettsäureester, an Fettsäurepartialglyceride und Fettsäure- alkanolamide; Verdickungsmittel, z. B. Fettalkohole, Fettsäuren, Paraffinöle, Fettsäureester und andere Fettkomponenten in emulgier- ter Form; wasserlösliche polymere Verdickungsmittel wie natürliche Gummen, z. B. Gummi arabicum, Karaya-Gummi , Guar-Gummi , Johannis¬ brotkernmehl, Leinsamengummen und Pektin, biosynthetische Gummen, z.B. Xanthan-Gum i und Dextrane, synthetische Gummen, z. B. Agar- Agar und Algin, Stärke-Fraktionen und Derivate wie Amylose, Amylo- pektin und Dextrine, modifizierte Cellulosemoleküle, z. B. Methyl- cellulose, Hydroxyalkylcellulose und Carboxymethylcellulose, Tone wie z. B. Bentonit oder vollsynthetische Hydrokolloide, z.B. Poly- vinylalkohol oder Polyvinylpyrrolidon, haarpflegende Zusätze, wie z. B. wasserlösliche kationische Polymere, anionische Polymere, nicht¬ ionische Polymere, amphotere oder zwitterionische Polymere, Panto- thensäure, Vitamine, Pflanzenextrakte oder Cholesterin, pH-Stell¬ mittel, Komplexbildner und Parfumöle sowie Reduktionsmittel zur Stabilisierung der Inhaltsstoffe, z. B. Ascorbinsäure, schließlich können auch Farbstoffe zum Einfärben der kosmetischen Zubereitungen enthalten sein.In the hair colorants according to the invention, developer components and coupler components are generally used in approximately molar amounts to one another. If the molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components can be present in a molar ratio of 1: 0.5 to 1: 2 . To produce the colorants according to the invention, the oxidation dye precursors are incorporated in a suitable water-containing carrier. Such carriers are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions, for example shampoos, aerosols or other preparations which are suitable for use on the hair. The water-containing carrier usually contains wetting and emulsifying agents, such as anionic, nonionic or ampholytic surfactants, for example fatty alcohol sulfates, alkane sulfonates, α-olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on sorbitan fatty acids, on alkylphenols, on Fatty acid partial glycerides and fatty acid alkanolamides; Thickeners, e.g. B. fatty alcohols, fatty acids, paraffin oils, fatty acid esters and other fat components in emulsified form; water-soluble polymeric thickeners such as natural gums, e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin, biosynthetic gums, for example xanthan gum i and dextrans, synthetic gums, e.g. B. agar-agar and algin, starch fractions and derivatives such as amylose, amylopectin and dextrins, modified cellulose molecules, eg. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, clays such as. B. bentonite or fully synthetic hydrocolloids, such as polyvinyl alcohol or polyvinylpyrrolidone, hair care additives such. B. water-soluble cationic polymers, anionic polymers, non-ionic polymers, amphoteric or zwitterionic polymers, pantothenic acid, vitamins, plant extracts or cholesterol, pH-adjusting agents, complexing agents and perfume oils and reducing agents for stabilizing the ingredients, eg. As ascorbic acid, finally, dyes for coloring the cosmetic preparations can also be included.
Die Bestandteile des wasserhaltigen Trägers werden zur Herstellung der erfindungsgemäßen Haarfärbemittel in für diesen Zweck üblichen Mengen eingesetzt; z.B. werden Emulgiermittel in Konzentrationen von 0,5 bis 30 Gew.-% und Verdickungsmittel in Konzentrationen von 0,1 bis 25 Gew.-% des gesamten Färbemittels eingesetzt. Die oxidative Entwicklung der Färbung kann grundsätzlich mit Luft¬ sauerstoff erfolgen. Bevorzugt wird jedoch ein chemisches Oxidati¬ onsmittel eingesetzt, besonders dann, wenn neben der Färbung ein Aufhelleffekt am Haar gewünscht ist. Als Oxidationsmittel kommen insbesondere Wasserstoffperoxid oder dessen Anlagerungsprodukte an Harnstoff, Melamin oder Natriumborat sowie Gemische aus derartigen Wasserstoffperoxidanlagerungsprodukten mit Kaliumperoxiddisulfat in Betracht.The constituents of the water-containing carrier are used for the production of the hair colorants according to the invention in amounts customary for this purpose; For example, emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant. The oxidative development of the color can in principle be carried out with atmospheric oxygen. However, a chemical oxidizing agent is preferably used, especially when a lightening effect on the hair is desired in addition to the coloring. Particularly suitable oxidizing agents are hydrogen peroxide or its adducts with urea, melamine or sodium borate and mixtures of such hydrogen peroxide adducts with potassium peroxide disulfate.
Zweckmäßigerweise wird die Zubereitung des Oxidationsmittels unmit¬ telbar vor dem Haarefärben mit der Zubereitung aus den Oxidations- farbstoffVorprodukten vermischt. Das dabei entstehende gebrauchsfer¬ tige Haarfärbepräparat sollte bevorzugt einen pH-Wert im Bereich von 6 bis 10 aufweisen. Besonders bevorzugt ist die Anwendung der Haar¬ färbemittel in einem schwach alkalischen Milieu. Die Anwendungstem¬ peraturen können in einem Bereich zwischen 15 und 40 °C liegen. Nach einer Einwirkungszeit von ca. 30 Minuten wird das Haarfärbemittel durch Ausspülen von dem zu färbenden Haar entfernt. Das Nachwaschen mit einem Shampoo entfällt, wenn ein stark tensidhaltiger Träger, z.B. ein Färbesha poo verwendet wurde.The preparation of the oxidizing agent is expediently mixed with the preparation from the oxidation dye precursors immediately before hair coloring. The resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment. The application temperatures can be in a range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is removed from the hair to be colored by rinsing. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a color shesha poo was used.
Die nachfolgenden Beispiele sollen den Erfindungsgegenstand näher erläutern, ohne ihn jedoch hierauf zu beschränken. The following examples are intended to explain the subject of the invention in more detail, but without restricting it thereto.
B e i s p i e l eB e i s p i e l e
Anwendunqsbeispiele:Application examples:
Es wurden erfindungsgemäße Haarfärbemittel in Form einer Haarfär- becremeemulsion in der folgenden Zusammensetzung hergestellt:Hair dyes according to the invention were produced in the form of a hair dye emulsion with the following composition:
Fettalkohol C1 bis Ci8 10 g, Fettalkohol C12 bis C14 + 2 EO-Sulfat,Fatty alcohol C1 to Ci8 10 g, fatty alcohol C12 to C14 + 2 EO sulfate,
Natriumsalz 28 %ig 25 g,Sodium salt 28% 25 g,
Wasser 60 g,Water 60 g,
Entwicklerkomponente E 7,5 mMol, l-(2'-Hydroxyethoxy)-2-hydroxy-4- aminobenzol (Kupplerkomponente) 7,5 mMol,Developer component E 7.5 mmol, l- (2'-hydroxyethoxy) -2-hydroxy-4-aminobenzene (coupler component) 7.5 mmol,
Na2Sθ3 (Inhibitor) 1,0 g, konzentrierte Ammoniaklösung bis pH = 9,5,Na2Sθ3 (inhibitor) 1.0 g, concentrated ammonia solution up to pH = 9.5,
Wasser ad 100 g.Water ad 100 g.
Die Bestandteile wurden der Reihe nach miteinander vermischt. Nach Zugabe der Oxidationsfarbstoffvorprodukte und des Inhibitors wurde zunächst mit konzentrierter Ammoniaklösung der pH-Wert der Emulsion auf 9,5 eingestellt, dann wurde mit Wasser auf 100 g aufgefüllt.The ingredients were mixed together in order. After the oxidation dye precursors and the inhibitor had been added, the pH of the emulsion was first adjusted to 9.5 with concentrated ammonia solution, and the mixture was then made up to 100 g with water.
Die oxidative Entwicklung der Färbung wurde mit 3 %iger Wasserstoff¬ peroxidlösung als Oxidationslösung durchgeführt. Hierzu wurden 100 g der Emulsion mit 50 g Wasserstoffperoxidlösung (3 %ig) versetzt und vermischt. Die Färbecreme wurde auf ca. 5 cm lange Strähnen standardisierten, zu 90 % ergrauten aber nicht besonders vorbehandelten Menschenhaars aufgetragen und dort 30 Minuten bei 27 °C belassen. Nach Beendigung des Färbeprozesses wurde das Haar gespült, mit einem üblichen Haar¬ waschmittel gewaschen und anschließend getrocknet.The oxidative development of the color was carried out with 3% hydrogen peroxide solution as the oxidation solution. For this purpose, 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed. The coloring cream was applied to strands approx. 5 cm long, 90% gray but not specially pretreated, and left there for 30 minutes at 27 ° C. After the dyeing process had ended, the hair was rinsed, washed with a conventional shampoo and then dried.
Als Entwicklerkomponenten E wurden folgende Verbindungen eingesetzt:The following compounds were used as developer components E.
El 4-Hydroxy-2,5,6-triaminopyrimidin E2 2,4-Dihydroxy-5,6-diaminopyrimidin.El 4-hydroxy-2,5,6-triaminopyrimidine E2 2,4-dihydroxy-5,6-diaminopyrimidine.
Erzielte Ausfärbungen:Color achievements:
Entwickler NuanceDeveloper nuance
El Dunkelrubin E2 Rubin El Dark Ruby E2 Ruby
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19934330711 DE4330711A1 (en) | 1993-09-10 | 1993-09-10 | An oxidation |
| DEP4330711.6 | 1993-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1995007068A1 true WO1995007068A1 (en) | 1995-03-16 |
Family
ID=6497371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1994/002929 Ceased WO1995007068A1 (en) | 1993-09-10 | 1994-09-02 | Oxidation dyes containing 2-hydroxy-4-aminobenzene derivatives as couplers and hydroxytriaminopyrimidines or dihydroxydiaminopyrimidines as developers |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE4330711A1 (en) |
| WO (1) | WO1995007068A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004029797A1 (en) * | 2004-06-19 | 2006-06-08 | Henkel Kgaa | Agent for dyeing keratinous fibers |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2282858A1 (en) * | 1973-11-29 | 1976-03-26 | Henkel & Cie Gmbh | HAIR DYES CONTAINING TETRAAMINOPYRIMIDINES |
| DE3145811A1 (en) * | 1981-11-19 | 1983-05-26 | Wella Ag, 6100 Darmstadt | NEW 2-HYDROXY-4-AMINOBENZOLS, METHOD FOR THE PRODUCTION THEREOF AND HAIR COLORING AGENTS CONTAINING THESE COMPOUNDS |
| EP0467026A1 (en) * | 1990-07-17 | 1992-01-22 | Goldwell Aktiengesellschaft | Hair dyeing composition and its use |
| WO1992019220A1 (en) * | 1991-05-08 | 1992-11-12 | Henkel Kommanditgesellschaft Auf Aktien | Hair colouring agent |
-
1993
- 1993-09-10 DE DE19934330711 patent/DE4330711A1/en not_active Withdrawn
-
1994
- 1994-09-02 WO PCT/EP1994/002929 patent/WO1995007068A1/en not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2282858A1 (en) * | 1973-11-29 | 1976-03-26 | Henkel & Cie Gmbh | HAIR DYES CONTAINING TETRAAMINOPYRIMIDINES |
| DE3145811A1 (en) * | 1981-11-19 | 1983-05-26 | Wella Ag, 6100 Darmstadt | NEW 2-HYDROXY-4-AMINOBENZOLS, METHOD FOR THE PRODUCTION THEREOF AND HAIR COLORING AGENTS CONTAINING THESE COMPOUNDS |
| EP0467026A1 (en) * | 1990-07-17 | 1992-01-22 | Goldwell Aktiengesellschaft | Hair dyeing composition and its use |
| WO1992019220A1 (en) * | 1991-05-08 | 1992-11-12 | Henkel Kommanditgesellschaft Auf Aktien | Hair colouring agent |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4330711A1 (en) | 1995-03-16 |
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