WO1995017878A1 - Diaminotoluenes for use as couplers in dyes - Google Patents

Diaminotoluenes for use as couplers in dyes Download PDF

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Publication number
WO1995017878A1
WO1995017878A1 PCT/EP1994/004171 EP9404171W WO9517878A1 WO 1995017878 A1 WO1995017878 A1 WO 1995017878A1 EP 9404171 W EP9404171 W EP 9404171W WO 9517878 A1 WO9517878 A1 WO 9517878A1
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WIPO (PCT)
Prior art keywords
hair
components
developer
oxidation
hydrogen
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Application number
PCT/EP1994/004171
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German (de)
French (fr)
Inventor
Georg KNÜBEL
Horst Höffkes
Bernd Meinigke
Günther KONRAD
Edgar Lieske
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1995017878A1 publication Critical patent/WO1995017878A1/en

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Classifications

    • 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
    • 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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus

Definitions

  • the invention relates to oxidation colorants for dyeing human hair, which contain conventional developer components and diaminotoluenes which are certain as coupler components.
  • oxidation hair dyeing agents play a preferred role for dyeing hair because of their intense colors and good fastness properties.
  • Such hair colorants contain oxidation dye precursors in a cosmetic carrier.
  • Developer components and coupler components 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.
  • a certain developer component can also 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 component. In practice, therefore, a combination of different developer components and coupler components is usually required in order to obtain a single, naturally acting hair dye. There is therefore a constant need for new, improved coupler / developer combinations.
  • Good oxidation dye precursors primarily have to meet the following requirements: they have to develop the desired color shades with sufficient intensity and fastness in the oxidative coupling. They must also have a good ability to draw on human hair, with no noticeable differences between stressed and freshly regrown hair (leveling ability). 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 in toxicological and dermatological terms.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, furthermore diaminopyridine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives are usually used as developer components. -Phenylenediamine derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler components.
  • German patent DE 213581 only discloses the use of 2,3-diaminotoluene as the sole component for dyeing furs and hair pretreated with metal salts. The colorations obtained range from yellow-brown to dark brown.
  • the invention relates to oxidation colorants for dyeing human hair containing coupler components and developer components in a water-containing carrier, at least one conventional developer component in an amount of 0.05 to 20 mmol and as a coupler component at least one diolotoluene of the formula I ,
  • X represents hydrogen, a methyl group or a fluorine, chlorine, bromine or iodine atom
  • R * to R ⁇ independently of one another are hydrogen, C 1 -C 4 -alkyl groups, phenyl (C 1 -C 4) alkyl groups, C2 ⁇ C4 -Hydroxyalkyl phenomenon or C2 ⁇ C4- (-C-C4-alkoxy) -alkyl groups mean, in an amount of 0.05 to 20 mmol, each per 100 g of the oxidation dye is contained.
  • R * to R ⁇ are preferably hydrogen and hydrogen or a methyl group.
  • the substances which have already been described in more detail above can be considered as customary developer components.
  • the developer and coupler components can be used both as free bases and in the form of their inorganic or organic salts, e.g. the hydrochloride or hydrobromide.
  • the colorants according to the invention provide a broad spectrum of oxidation colors of interest in terms of application technology in the range from yellow to purple shades of high brilliance, good leveling ability and good fastness properties.
  • Preferred colorants provide shades in the red range; Such nuances can be achieved with the oxidation hair colorants according to the invention in particular when the developer components are selected from the group of p-aminophenols and p-phenylenediamines. P-Aminophenol and 2,5-diaminotoluene are particularly preferred.
  • the hair colorants according to the invention contain, in addition to the coupler components of the formula I and the developer components, customary direct dyes, e.g. from the group of nitrophenylenediae, nitroa inophenols, anthraquinones or indophenols, in an amount of 0.05 to 20 mmol, per 100 g of the oxidation hair dye.
  • coupler components of the formula I it is not necessary that the coupler components of the formula I, the developer components or the optional substantive dyes each represent uniform compounds. Rather you can Mixtures of various coupler components of the formula I, developer components and substantive dyes are also used in the hair colorants according to the invention.
  • other customary coupler components for. B. from the group of m-phenylenediamine derivatives, naphthols, resorcinols and pyrazolones.
  • 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 hair colorants according to the invention are preferably based on "unheated", ie. H. hair not pretreated with metal salts.
  • the oxidation dye precursors are incorporated in a suitable water-containing carrier.
  • suitable water-containing carrier are e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions, e.g. Shampoos, foam aerosols or other preparations that 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 with fatty alcohols, with fatty acids, with alkyl phenols acid, with sorb 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 with fatty alcohols, with fatty acids, with alkyl phenols acid, with sorb partial glycerides and
  • 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 i, guar gum, locust bean gum, linseed; biosynthetic gums, for example xanthan gums and dextrans; synthetic gums, e.g. B. agar and algin, starch fractions and derivatives such as amylose, amylopectin and dextrins; modified cellulose molecules, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxy ethyl cellulose; Clays such as B.
  • hair care additives such as. B. water-soluble cationic polymers, anionic polymers, nonionic 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, e.g. B. ascorbic acid; finally, dyes for coloring the cosmetic preparations can also be present.
  • locust bean gum and guar gum are ideal thickeners for non-swellable woods, e.g. B. sandalwood, containing natural hair dyes known. Accordingly, these thickeners are to be used if the oxidation hair colorants according to the invention additionally contain non-swellable woods.
  • constituents of the water-containing carrier are used in the amounts customary for this purpose for the preparation of the hair colorants according to the invention; e.g. 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 coloring can in principle take place with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially when, in addition to the coloring, a lightening effect on the hair is desired.
  • 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 dyeing the hair.
  • 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 range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is rinsed out of the hair to be colored away. Washing with a shampoo is not necessary if a carrier with a high tenside content, eg a coloring shampoo, has been used.
  • Hair colorants according to the invention were produced in the form of a hair color cream emulsion in the following composition:
  • Coupler component (K1-K2) 7.5 mmol
  • 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 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 approx. 5 cm long strands of standardized, 90% gray but not specially pretreated human hair and left there for 30 minutes at 27 ° C. After the dyeing process was completed, the hair was rinsed, washed with a conventional shampoo and then dried.

Abstract

The invention concerns oxidative hair dyes containing as couplers 2,3-diaminotoluenes together with the customary developers.

Description

"Diaminotoluole als Kuppler in Färbemitteln" "Diaminotoluenes as Couplers in Colorants"
Die Erfindung betrifft Oxidationsfärbemittel zum Färben von menschlichen Haaren, die übliche Entwicklerkomponenten und als Kupplerkomponenten be¬ stimmte Diaminotoluole enthalten.The invention relates to oxidation colorants for dyeing human hair, which contain conventional developer components and diaminotoluenes which are certain as coupler components.
Für das Färben von Haaren spielen die sogenannten Oxidationshaarfärbemit¬ tel wegen ihrer intensiven Farben und guten Echtheitseigenschaften eine bevorzugte Rolle. Solche Haarfärbemittel enthalten OxidationsfarbstoffVor¬ produkte in einem kosmetischen Träger. Als Oxidationsfarbstoffvorprodukte werden Entwicklerkomponenten und Kupplerkomponenten eingesetzt. Die Ent¬ wicklerkomponenten bilden unter dem Einfluß von Oxidationsmitteln oder von Luftsauerstoff untereinander oder unter Kupplung mit einer oder mehreren Kupplerkomponenten die eigentlichen Farbstoffe aus.So-called oxidation hair dyeing agents play a preferred role for dyeing hair because of their intense colors and good fastness properties. Such hair colorants contain oxidation dye precursors in a cosmetic carrier. Developer components and coupler components 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.
Eine bestimmte Entwicklerkomponente kann durch Kombination mit unter¬ schiedlichen Kupplern auch sehr unterschiedliche Farbnuancen bilden. Trotzdem gelingt es oft nicht, mit Hilfe einer einzigen Entwicklerkompo¬ nente zu der Vielzahl natürlicher Haarfarbnuancen zu kommen. In der Praxis ist daher meist eine Kombination verschiedener Entwicklerkomponenten und Kupplerkomponenten erforderlich, um eine einzige, natürlich wirkende Haar¬ färbung zu erhalten. Es besteht daher ständig Bedarf an neuen, verbesser¬ ten Kupp1er/Entwick1er-Kombinationen.A certain developer component can also 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 component. In practice, therefore, a combination of different developer components and coupler components is usually required in order to obtain a single, naturally acting hair dye. There is therefore a constant need for new, improved coupler / developer combinations.
Gute Oxidationsfarbstoffvorprodukte müssen in erster Linie folgende Vor¬ aussetzungen erfüllen: Sie müssen bei der oxidativen Kupplung die ge¬ wünschten Farbnuancen in ausreichender Intensität und Echtheit ausbilden. Sie müssen ferner ein gutes Aufziehvermögen auf menschlichem Haar besit¬ zen, wobei keine merklichen Unterschiede zwischen strapaziertem und frisch nachgewachsenem Haar bestehen dürfen (Egalisiervermögen). Sie sollen be¬ ständig sein gegen Licht, Wärme und dem Einfluß chemischer Reduktionsmit¬ tel, z. B. gegen Dauerwellflüssigkeiten. Schließlich sollen sie die Kopf¬ haut nicht zu sehr anfärben, und vor allem sollen sie in toxikologischer und dermatologischer Hinsicht unbedenklich sein. Als Entwicklerkomponenten werden üblicherweise primäre aromatische Amine mit einer weiteren in Para- oder Orthoposition befindlichen freien oder substituierten Hydroxy- oder Aminogruppe, ferner Diaminopyridinderivate, heterocycTische Hydrazonderivate oder 4-Aminopyrazolonderivate eingesetzt. Als sogenannte Kupplerkomponenten werden -Phenylendiaminderivate, Naph- thole, Resorcinderivate und Pyrazolone verwendet.Good oxidation dye precursors primarily have to meet the following requirements: they have to develop the desired color shades with sufficient intensity and fastness in the oxidative coupling. They must also have a good ability to draw on human hair, with no noticeable differences between stressed and freshly regrown hair (leveling ability). 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 in toxicological and dermatological terms. Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, furthermore diaminopyridine derivatives, heterocyclic hydrazone derivatives or 4-aminopyrazolone derivatives are usually used as developer components. -Phenylenediamine derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler components.
Die Verwendung von 2,3-Diaminotoluolen als Kupplerkomponenten gemeinsam mit üblichen Entwicklerkomponenten zum oxidativen Färben menschlicher Haare ist bisher noch nicht beschrieben worden. Die deutsche Patentschrift DE 213581 offenbart lediglich die Verwendung von 2,3-Diaminotoluol als alleiniger Komponente zum Färben von mit Metallsalzen vorbehandelten Pel¬ zen und Haaren. Die damit erhaltenen Färbungen reichen von gelbbraun bis dunkelbraun.The use of 2,3-diaminotoluenes as coupler components together with conventional developer components for the oxidative dyeing of human hair has not yet been described. German patent DE 213581 only discloses the use of 2,3-diaminotoluene as the sole component for dyeing furs and hair pretreated with metal salts. The colorations obtained range from yellow-brown to dark brown.
Überraschenderweise wurde nun gefunden, daß sich 2,3-Diaminotoluole her¬ vorragend als Kupplerkomponenten in Kombination mit üblichen Entwickler¬ komponenten zum Färben von menschlichen Haaren eignen.Surprisingly, it has now been found that 2,3-diaminotoluenes are outstandingly suitable as coupler components in combination with conventional developer components for dyeing human hair.
Gegenstand der Erfindung sind Oxidationsfärbemittel zum Färben von mensch¬ lichen Haaren enthaltend Kupplerkomponenten und Entwicklerkomponenten in einem wasserhaltigen Träger, wobei mindestens eine übliche Entwicklerkom¬ ponente in einer Menge von 0,05 bis 20 mMol und als Kupplerkomponente min¬ destens ein Dia inotoluol der Formel I,The invention relates to oxidation colorants for dyeing human hair containing coupler components and developer components in a water-containing carrier, at least one conventional developer component in an amount of 0.05 to 20 mmol and as a coupler component at least one diolotoluene of the formula I ,
Figure imgf000004_0001
worin X für Wasserstoff, eine Methylgruppe oder ein Fluor-, Chlor-, Brom¬ oder Jodatom steht, und R* bis R^ unabhängig voneinander Wasserstoffe, Cι-C4-Alkylgruppen, Phenyl-(Cι-C4)-alkylgruppen, C2~C4-Hydroxyalkylgruppen oder C2~C4-(Cι-C4-Alkoxy)-alkylgruppen bedeuten, in einer Menge von 0,05 bis 20 mMol, jeweils pro 100 g des Oxidationsfärbe ittels, enthalten ist.
Figure imgf000004_0001
where X represents hydrogen, a methyl group or a fluorine, chlorine, bromine or iodine atom, and R * to R ^ independently of one another are hydrogen, C 1 -C 4 -alkyl groups, phenyl (C 1 -C 4) alkyl groups, C2 ~ C4 -Hydroxyalkylgruppen or C2 ~ C4- (-C-C4-alkoxy) -alkyl groups mean, in an amount of 0.05 to 20 mmol, each per 100 g of the oxidation dye is contained.
Vorzugsweise stehen R* bis R^ für Wasserstoffe und für Wasserstoff oder eine Methylgruppe.R * to R ^ are preferably hydrogen and hydrogen or a methyl group.
Als übliche Entwicklerkomponenten kommen die bereits oben näher beschrie¬ benen Substanzen in Frage. Die Entwickler- und Kupplerkomponenten können dabei sowohl als freie Basen als auch in Form ihrer anorganischen oder organischen Salze, z.B. der Hydrochloride oder Hydrobromide, eingesetzt werden.The substances which have already been described in more detail above can be considered as customary developer components. The developer and coupler components can be used both as free bases and in the form of their inorganic or organic salts, e.g. the hydrochloride or hydrobromide.
Die erfindungsgemäßen Färbemittel liefern ein breites Spektrum an¬ wendungstechnisch interessanter Oxidationsfarben im Bereich gelber bis purpurner Nuancen von hoher Brillanz, gutem Egalisiervermögen und guten Echtheitseigenschaften.The colorants according to the invention provide a broad spectrum of oxidation colors of interest in terms of application technology in the range from yellow to purple shades of high brilliance, good leveling ability and good fastness properties.
Bevorzugte Färbemittel liefern Nuancen im Rot-Bereich; solche Nuancen lassen sich mit den erfindungsgemäßen Oxidationshaarfärbemitteln insbe¬ sondere dann erzielen, wenn die Entwicklerkomponenten ausgewählt sind aus der Gruppe der p-Aminophenole und der p-Phenylendiamine. Besonders bevorzugt sind dabei p-Aminophenol und 2,5-Diaminotoluol.Preferred colorants provide shades in the red range; Such nuances can be achieved with the oxidation hair colorants according to the invention in particular when the developer components are selected from the group of p-aminophenols and p-phenylenediamines. P-Aminophenol and 2,5-diaminotoluene are particularly preferred.
In einer bevorzugten Ausführungsform enthalten die erfindungsgemäßen Haar¬ färbemittel zur weiteren Modifizierung der Farbnuancen neben den Kuppler¬ komponenten der Formel I und den Entwicklerkomponenten zusätzlich übliche direktziehende Farbstoffe, z.B. aus der Gruppe der Nitrophenylendia ine, Nitroa inophenole, Anthrachinone oder Indophenole, in einer Menge von 0,05 bis 20 mMol, pro 100 g des Oxidationshaarfärbemittels.In a preferred embodiment, the hair colorants according to the invention contain, in addition to the coupler components of the formula I and the developer components, customary direct dyes, e.g. from the group of nitrophenylenediae, nitroa inophenols, anthraquinones or indophenols, in an amount of 0.05 to 20 mmol, per 100 g of the oxidation hair dye.
Es ist nicht erforderlich, daß die Kupplerkomponenten der Formel I, die Entwicklerkomponenten oder die fakultativ enthaltenen direktziehenden Farbstoffe jeweils einheitliche Verbindungen darstellen. Vielmehr können in den erfindungsgemäßen Haarfärbemitteln auch Gemische verschiedener Kupplerkomponenten der Formel I, Entwicklerkomponenten und direktziehender Farbstoffe verwendet werden. Insbesondere können neben den Kupplerkompo¬ nenten der Formel I weitere übliche Kupplerkomponenten, z. B. aus der Gruppe der m-Phenylendiaminderivate, der Naphthole, der Resorcine und der Pyrazolone enthalten sein.It is not necessary that the coupler components of the formula I, the developer components or the optional substantive dyes each represent uniform compounds. Rather you can Mixtures of various coupler components of the formula I, developer components and substantive dyes are also used in the hair colorants according to the invention. In particular, in addition to the coupler components of the formula I, other customary coupler components, for. B. from the group of m-phenylenediamine derivatives, naphthols, resorcinols and pyrazolones.
In den erfindungsgemäßen Haarfärbemitteln werden Entwicklerkomponenten und Kupplerkomponenten im allgemeinen in etwa molaren Mengen zueinander einge¬ setzt. Wenn sich auch der molare Einsatz als zweckmäßig erwiesen hat, so ist ein gewisser Überschuß einzelner Oxidationsfarbstoffvorprodukte nicht nachteilig, so daß Entwicklerkomponenten und Kupplerkomponenten in einem Mol-Verhältnis von 1 : 0,5 bis 1 : 2 enthalten sein können.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.
Die erfindungsgemäßen Haarfärbemittel werden vorzugsweise auf "ungeheiz¬ tes", d. h. nicht mit Metallsalzen vorbehandeltes Haar, aufgetragen. Zur Herstellung der erfindungsgemäßen Färbemittel werden die Oxidationsfarb¬ stoffvorprodukte 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 Zubereitun¬ gen, die für die Anwendung auf dem Haar geeignet sind.The hair colorants according to the invention are preferably based on "unheated", ie. H. hair not pretreated with metal salts. To produce the colorants according to the invention, the oxidation dye precursors are incorporated in a suitable water-containing carrier. Such carriers are e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions, e.g. Shampoos, foam aerosols or other preparations that are suitable for use on the hair.
Der wasserhaltige Träger enthält üblicherweise Netz- und Emulgiermittel wie anionische, nichtionische oder ampholytische Tenside, z.B. Fettalko¬ holsulfate, Alkansulfonate, α-Olefinsulfonate, Fettalkoholpolyglykolether- sulfate, Alkylglycoside, Ethylenoxidanlagerungsprodukte an Fettalkohole, an Fettsäuren, an Alkylphenole, an Sorbitanfettsäureester, an Fettsäure¬ partialglyceride und Fettsäurealkanolamide; Verdickungsmittel, z. B. Fett¬ alkohole, Fettsäuren, Paraffinöle, Fettsäureester und andere Fettkomponen¬ ten in emulgierter Form; wasserlösliche polymere Verdickungsmittel wie natürliche Gummen, z. B. Gummi arabicum, Karaya-Gum i, Guar-Gummi, Johan¬ nisbrotkernmehl, Leinsa engummen; biosynthetische Gummen, z.B. Xanthan- Gumrni und Dextrane; synthetische Gummen, z. B. Agar-Agar und Algin, Stär¬ ke-Fraktionen und Derivate wie Amylose, Amylopektin und Dextrine; modifi¬ zierte Cellulosemoleküle, z. B. Methylcellulose, Hydroxyalkylcellulose und Carboxy ethylcellulose; Tone wie z. B. Bentonit oder vollsynthetische Hydrokolloide, z.B. Polyvinylalkohol oder Polyvinylpyrrolidon; haarpfle¬ gende Zusätze, wie z. B. wasserlösliche kationische Polymere, anionische Polymere, nichtionische Polymere, amphotere oder zwitterionische Polymere, Pantothensäure, Vitamine, Pflanzenextrakte oder Cholesterin; pH-Stellmit¬ tel, Komplexb ldner und Parfumöle sowie Reduktionsmittel zur Stabilisie¬ rung der Inhaltsstoffe, z. B. Ascorbinsäure; schließlich können auch Farb¬ stoffe zum Einfärben der kosmetischen Zubereitungen enthalten sein. Insbe¬ sondere Johannisbrotkernmehl und Guarkernmehl sind als ideale Verdickungs¬ mittel für nicht-quellfähige Hölzer, z. B. Sandelholz, enthaltende Natur¬ haarfarbstoffe bekannt. Dementsprechend sind diese Verdickungsmittel be¬ vorzugt zu verwenden, wenn die erfindungsgemäßen Oxidationshaarfärbemittel zusätzlich nicht-quellfähige Hölzer enthalten.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 with fatty alcohols, with fatty acids, with alkyl phenols acid, with sorb 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 i, guar gum, locust bean gum, linseed; biosynthetic gums, for example xanthan gums and dextrans; synthetic gums, e.g. B. agar and algin, starch fractions and derivatives such as amylose, amylopectin and dextrins; modified cellulose molecules, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxy ethyl cellulose; Clays such as B. bentonite or fully synthetic Hydrocolloids, for example polyvinyl alcohol or polyvinyl pyrrolidone; hair care additives, such as. B. water-soluble cationic polymers, anionic polymers, nonionic 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, e.g. B. ascorbic acid; finally, dyes for coloring the cosmetic preparations can also be present. In particular locust bean gum and guar gum are ideal thickeners for non-swellable woods, e.g. B. sandalwood, containing natural hair dyes known. Accordingly, these thickeners are to be used if the oxidation hair colorants according to the invention additionally contain non-swellable woods.
Die Bestandteile des wasserhaltigen Trägers werden zur Herstellung der erfindungsgemäßen Haarfärbemittel in für diesen Zweck üblichen Mengen ein¬ gesetzt; 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.The constituents of the water-containing carrier are used in the amounts customary for this purpose for the preparation of the hair colorants according to the invention; e.g. 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.
Die oxidative Entwicklung der Färbung kann grundsätzlich mit Luftsauer¬ stoff erfolgen. Bevorzugt wird jedoch ein chemisches Oxidationsmittel ein¬ gesetzt, 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 oxidative development of the coloring can in principle take place with atmospheric oxygen. However, a chemical oxidizing agent is preferably used, especially when, in addition to the coloring, a lightening effect on the hair is desired. 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 unmittelbar vor dem Haarefärben mit der Zubereitung aus den Oxidationsfarbstoffvor- produkten vermischt. Das dabei entstehende gebrauchsfertige Haarfärbeprä¬ parat sollte bevorzugt einen pH-Wert im Bereich von 6 bis 10 aufweisen. Besonders bevorzugt ist die Anwendung der Haarfärbemittel in einem schwach alkalischen Milieu. Die Anwendungstemperaturen können in einem Bereich zwischen 15 und 40 °C liegen. Nach einer Einwirkungszeit von ca. 30 Minu¬ ten wird das Haarfärbemittel durch Ausspülen von dem zu färbenden Haar entfernt. Das Nachwaschen mit einem Shampoo entfällt, wenn ein stark ten- sidhaltiger Träger, z.B. ein Färbeshampoo, verwendet wurde.The preparation of the oxidizing agent is expediently mixed with the preparation from the oxidation dye precursors immediately before dyeing the hair. 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 range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is rinsed out of the hair to be colored away. Washing with a shampoo is not necessary if a carrier with a high tenside content, eg a coloring shampoo, has been used.
Die nachfolgenden Beispiele sollen den Erfindungsgegenstand näher erläu¬ tern, 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.
BeispieleExamples
Herstellunosbeispiele (und Literaturhinweise) zu den Kupplerkomponenten der Formel IManufacturing examples (and references) to the coupler components of formula I.
2,3-Diaminotoluol: E. Lellmann, Liebigs Annalen, 228, 2432,3-diaminotoluene: E. Lellmann, Liebigs Annalen, 228, 243
3,4-Diamino-o-xyld: Dellweg, Biochem. Z., 327 (1956) 422 3,4-diamino-o-xyld: Dellweg, Biochem. Z., 327 (1956) 422
AnwendunosbeiSDie1e:Applications at Die1e:
Es wurden erfindungsgemäße Haarfärbemittel in Form einer Haarfärbecreme- emulsion in der folgenden Zusammensetzung hergestellt:Hair colorants according to the invention were produced in the form of a hair color cream emulsion in the following composition:
Fettalkohol C12 bis Ciβ 10 g, Fettalkohol C12 bis C14 + 2 EO-Sulfat,Fatty alcohol C12 to Ciβ 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 (E1-E8) 7,5 mMol,Developer component (E1-E8) 7.5 mmol,
Kupplerkomponente (K1-K2) 7,5 mMol,Coupler component (K1-K2) 7.5 mmol,
Na2S03 (Inhibitor) 1,0 g, konzentrierte Ammoniaklösung bis pH = 9,5,Na2S03 (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 de pH-Wert der Emulsion auf 9,5 einge¬ stellt, 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 then made up to 100 g with water.
Die oxidative Entwicklung der Färbung wurde mit 3 %iger Wasserstoffper¬ oxidlösung als Oxidationslösung durchgeführt. Hierzu wurden 100 g der Emulsion mit 50 g Wasserstoffperoxidlösung (3 %ig) versetzt und vermischt.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.
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 Haarwaschmittel gewaschen und anschließend getrocknet.The coloring cream was applied to approx. 5 cm long strands of standardized, 90% gray but not specially pretreated human hair and left there for 30 minutes at 27 ° C. After the dyeing process was completed, the hair was rinsed, washed with a conventional shampoo and then dried.
Als Kupplerkomponenten Kl und K2 wurden 2,3-Diaminotoluol (Kl) und l,2-Diamino-3,4-dimethylbenzol (K2) eingesetzt. Als Entwicklerkomponenten El bis E8 wurden die in Tabelle 1 aufgeführten Verbindungen eingesetzt; die erzielten Ausfärbungen sind Tabelle 1 zu entnehmen: 2,3-Diaminotoluene (Kl) and 1,2-diamino-3,4-dimethylbenzene (K2) were used as coupler components K1 and K2. The compounds listed in Table 1 were used as developer components E1 to E8; the colorations achieved are shown in Table 1:
Tabelle 1Table 1
Entwicklerkomponenten E1-E8 erzielte Ausfärbungen erzielte Ausfärbungen mit Kl mit K2Developer components E1-E8 achieved colorations achieved colorations with Kl with K2
El 3-Methyl-p-aminophenol elfenbeinEl 3-methyl-p-aminophenol ivory
E2 p-Aminophenol Hydrochlorid hennarot kaneelbraunE2 p-aminophenol hydrochloride henna red panel brown
E3 2,5-Diaminotoluolsulfat dunkelrubin totenkopfE3 2,5-diaminotoluenesulfate dark ruby skull
E4 2-(2,5-Diaminophenyl)ethanol rotviolettE4 2- (2,5-diaminophenyl) ethanol red violet
E5 l,10-Bis-(2,5-Diaminophenyl)-E5 l, 10-bis (2,5-diaminophenyl) -
1,4,7,10-tetraoxadecan Hydrochlorid violett/magenta1,4,7,10-tetraoxadecane hydrochloride violet / magenta
E6 Tetraaminopyrimidinsulfat bernsteingelb sonnenblumengelbE6 Tetraaminopyrimidine sulfate amber yellow sunflower yellow
E7 2,4,5-Triamino-6-hydroxypyrimidιn- sulfat champagnergelbE7 2,4,5-triamino-6-hydroxypyrimidine sulfate champagne yellow
E8 5,6-Diamino-2,4-dihydroxypyrimidin sulfat hellgelb E8 5,6-diamino-2,4-dihydroxypyrimidine sulfate light yellow

Claims

Patentansprüche claims
1. Oxidationsfärbemittel zum Färben von menschlichen Haaren enthaltend Kupplerkomponenten und Entwicklerkomponenten in einem wasserhaltigen Träger, dadurch gekennzeichnet, daß mindestens eine übliche Entwick¬ lerkomponente in einer Menge von 0,05 bis 20 mMol, und als Kupplerkomponente mindestens ein Diaminotoluol der Formel I,1. oxidation dye for dyeing human hair containing coupler components and developer components in a water-containing carrier, characterized in that at least one conventional developer component in an amount of 0.05 to 20 mmol, and as coupler component at least one diaminotoluene of the formula I,
Figure imgf000013_0001
Figure imgf000013_0001
worin X für Wasserstoff, eine Methylgruppe oder ein Fluor-, Chlor-, Brom- oder Jodatom steht, und R*** bis R4 unabhängig voneinander Wasser¬ stoffe, Cι-C4-Alkylgruppen, Phenyl-(Cι-C4)-alkylgruppen, C2-C4-Hydroxyalkylgruppen oder C2-C4-(Cι-C4-Alkoxy)-alkylgruppen be¬ deuten, in einer Menge von 0,05 bis 20 mMol, jeweils pro 100 g des Oxidationsfärbemittels, enthalten ist.wherein X represents hydrogen, a methyl group or a fluorine, chlorine, bromine or iodine atom, and R *** to R 4 independently of one another hydrogen, C 1 -C 4 -alkyl groups, phenyl (C 1 -C 4) alkyl groups , C2-C4-hydroxyalkyl groups or C2-C4- (-C-C4-alkoxy) alkyl groups mean in an amount of 0.05 to 20 mmol, in each case per 100 g of the oxidation colorant.
2. Mittel nach Anspruch 1, dadurch gekennzeichnet, daß im Diaminotoluol der Formel I R**- bis R4 für Wassserstoffe stehen und X Wasserstoff oder eine Methylgruppe ist.2. Composition according to claim 1, characterized in that in diaminotoluene of the formula IR ** - to R 4 are hydrogen and X is hydrogen or a methyl group.
3. Mittel nach Anspruch 1, dadurch gekennzeichnet, daß die Entwicklerkom¬ ponenten ausgewählt sind aus der Gruppe der p-Aminophenole und der p- Phenylendiamine.3. Composition according to claim 1, characterized in that the developer components are selected from the group of p-aminophenols and p-phenylenediamines.
4. Mittel nach Anspruch 3, dadurch gekennzeichnet, daß die Entwicklerkom¬ ponenten ausgewählt sind aus p-Aminophenol und 2,5-Diaminotoluol. 4. Composition according to claim 3, characterized in that the developer components are selected from p-aminophenol and 2,5-diaminotoluene.
5. Mittel nach Anspruch 1 bis 4, dadurch gekennzeichnet, daß zusätzlich übliche direktziehende Farbstoffe in einer Menge von 0,05 bis 20 mMol, pro 100 g des Oxidationshaarfärbemittels, enthalten sind. 5. Composition according to claim 1 to 4, characterized in that in addition conventional direct dyes are contained in an amount of 0.05 to 20 mmol, per 100 g of the oxidation hair dye.
PCT/EP1994/004171 1993-12-24 1994-12-15 Diaminotoluenes for use as couplers in dyes WO1995017878A1 (en)

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DE213581C (en) *
DE4028661A1 (en) * 1990-09-10 1992-03-12 Wella Ag AGENT FOR THE OXIDATIVE COLORING OF HAIR AND NEW 5-HALOGEN-2,4-DIAMINOALKYLBENZOLE
DE4132615A1 (en) * 1991-10-01 1993-04-15 Schwarzkopf Gmbh Hans NEW SUBSTITUTED 2,6-DIAMINOTOLUOLES, METHOD FOR THE PRODUCTION THEREOF, AND COLORING AGENTS FOR CERATINAL FIBERS CONTAINING THEM

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DE213581C (en) *
DE4028661A1 (en) * 1990-09-10 1992-03-12 Wella Ag AGENT FOR THE OXIDATIVE COLORING OF HAIR AND NEW 5-HALOGEN-2,4-DIAMINOALKYLBENZOLE
DE4132615A1 (en) * 1991-10-01 1993-04-15 Schwarzkopf Gmbh Hans NEW SUBSTITUTED 2,6-DIAMINOTOLUOLES, METHOD FOR THE PRODUCTION THEREOF, AND COLORING AGENTS FOR CERATINAL FIBERS CONTAINING THEM

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