NO802391L - Hair Dye. - Google Patents

Description

The object of the invention is a means for oxidative dyeing of hair based on 3-amino-2-methylphenol as coupling component.

For hair dyeing, the so-called oxidation colors which arise from oxidative coupling of a developing r •• component with a coupling component play a preferred role on

due to its intense colors and very good authenticity properties. Nitrogen bases, such as p-phenylenediamine derivatives, diaminopyridines, 4-amino-pyrazolone derivatives, heterocyclic hydrazones, are usually used as developer substances. Phenols, naphthols, resorcin derivatives and pyrazolones are mentioned as so-called coupling components.

Good oxidation hair dye components must i

First of all, fulfill the following conditions:

They must by the oxidative connection with the possible developers or coupling compound, form the desired color shades in sufficient intensity. They must also have a sufficient to very good pulling power on human hair, and they must also be harmless from a toxicological and dermatological point of view. Furthermore, it is important that on the hair to be dyed, as strong as possible and strongly corresponding to the natural hair color shades are obtained. Furthermore, the general stability of the dye formed,

as well as their light fastness, wash fastness and thermostability of very special importance, in order to avoid color shifts from the original color shade, or even color conversion to other shades.

Therefore, when searching for usable oxidation hair dyes, the task is to find suitable components that fulfill the above-mentioned prerequisites in an optimal way.

It has now been found that hair dyes based on oxidation hair dyes with a content of 3-amino-2-methyl-phenol as a coupling agent and common developer components in oxidation hair dyes to a high degree satisfy the requirements.

When used as coupling components, the compound according to the invention with the so-called f rein r substance usually used for oxidation hair dyes gives very intense and light-fast color shades that range from brown to dark blue, and thus forms a significant enrichment of the oxidative hair dyeing possibilities . Especially with the frenkaller component p-toluylenediamine, a surprisingly light-stable, interesting reddish-brown hair color appears. But also the dark blue color shades obtainable with different developer components have increased interest in the production of a natural brown tone. In addition, 3-amino-2-methylphenol is characterized by good solubility in water, good storage stability, and toxicological and dermatological harmlessness.

The invention as a coupling component usable 3-amino-2-methylphenol is a known compound whose preparation is discussed by Noelting in Berichten der Deutschen Chemischen Gesellschaft 37 (1904), page 1020/21.

Examples of developer components that can be used in the hair dyes according to the invention include primary aromatic amines with an additional functional group in the p-position, such as p-phenylenediamine, p-toluylenediamine, monochloro-p-phenylenediamine, p- dimethylaminoaniline, p-aminophenol, p-aminoanilsol, resp. other compounds of known types, as well as one or more functional groups such as OH groups, NE^f-r groups, NHR groups, NR^ groups, where R means a alkyl or hydroxyalkyl residue with 1 more in carbon atoms, further diaminopyridine derivatives, heterocyclic hydrazone derivatives, 4-arainopyrazolone derivatives" such as 4.-amino-1-phenylcarbamoylpyrazolone-5.

As additional developer components which can advantageously be combined with 3-amino-2-methylphenol, tetraamino-pyrimidines with the general formula in which R^- R^ means hydrogen, an alkyl residue with 1-4 carbon atoms, the remainder - (Ch^^-X where n=1 - 4 and X means a hydroxyl group, a halogen atom, a -N^-, -NHR1 - and -NR'R" group, R' and R" can mean alkyl residue with 1 - 4-carbon atoms, or with the nitrogen atom, can be joined to a heterocyclic ring which can contain a further nitrogen atom or oxygen atom, R and R0, respectively RQ and R,, respectively.

R^ and R^ can form with any nitrogen atom a heterocyclic 5- or 6-membered ring with one or two nitrogen atoms or a nitrogen atom or an oxygen atom, as well as their inorganic or organic salts.

The tetra-amnopyrimidines usable as developing components can either be used as such, or in the form of their salts with • inorganic or organic acids, such as, for example chlorides, sulphates, phosphates, acetates, propionates, lactates, citrates.

For combination with the 3-amino-2-phenol used as a coupling component according to the invention, suitable developing agents are, for example

2.4- . 5, 6-tetraamino-,

Out 5-diamino-2,6-bimethylamino -,

2, 5-dimaino-4.” 6-bismethylamino-,

1.5-diamino-6-butylamino-2-dimethylamino -,

2, 5-diamino -4.-diethylamino - 6-methylamino -,

Ut5-diamino-6-diethylamino-2-dimethylamino-,

Ut5-diamino-2-diethylamino-6-methylamino-,

Ut5-diamino-2-dimethylamino-6-ethylamino-,

1, 5-diamino-2-dimethylamino-6-isopropylamino-, Ut5-diamino-2-dimethylamino-6-methylamino-, 4.'' 5-diamino-6-dimethylamino-2-methylamino-,

i,5 -diamino-2-dimethylamino-6-propylamino-,

2,4-, 5-triamino-6-dimethylamino-,

Out 51 6-triamino-2-dimethylamino-,

2, Ut 5-triamino-6-methylamino-,

Out 51 6-triamino-2-methylamino-,

Out 5-diamino-2-dimethylamino-6-piperidino-,

Out 5-diamino-6-methylamino-2-piperidino-,

2,4,5 - triamino-6-piperidino-,

2, 4, 5-triamino-6-anilino-,

2.4. » 5-tr i amino-6-benzyl amino-,

2,4» 5-triamino-6-benzylideneamino-,

4,5,6-triamino-2-piperidino-,

2,4»6-trismethylamino-5-amino-,

2,4» 5-triamino-6-di-n-propylamino-,

2.4.5- triamino-6-morpholino-,

2.5.6-triamino-4-dimethylamino

4,5,6-triamino-2-morpholino-,

2,4,5-triamino-6-3-hydroxyethylamino-,

4.5, 6-triamino-2-6-amino-ethylamino-,

2, 5, 6-triamino-4-3-methylamino-ethylamino-,

2, 5-diamino-4,6-bis-y-diethylamino-propylamino-, 4,5-diamino-2-methylamino-6-3-hydroxy-ethylamino-, 5-amino-2,4» 6-triethylamino- ,

2,4-bis-3-hydroxyethylamino-6-anilino-5-amino-pyrimidine.

In the hair dyes according to the invention, the coupling components are usually used in approximately molar amounts, with reference to the developers used. When the molar application also turns out to be disastrous, it is however not unfortunate when the coupler components are used in a certain surplus or deficit. Furthermore, it is not necessary that the developer components and the coupling substance form uniform products, but the developer components can form mixtures of the developer compounds that can be used according to the invention. In addition, the hair dyes according to the invention may optionally contain common direct dyes in the mixture, if this is necessary to achieve certain color shades.

The oxidative coupling, i.e. development of the coloring can in principle also take place as with other oxidation hair dyes, with the help of atmospheric oxygen. However, chemical oxidizing agents are used appropriately. As such, hydrogen peroxide or its addition products to urea, ineramine and sodium borate, as well as mixtures of such hydrogen peroxide addition products, come into particular consideration.

compounds with potassium peroxide disulfate.

The hair dyes according to the invention, in-

is prepared for use in corresponding cosmetic preparations such as creams, emulsions, gels or also simple solutions, and mixed immediately before application to the hair with one of the aforementioned oxidizing agents. The concentration of such color preparations of coupler-developer combinations amounts to 0.2 to 5% by weight, preferably 1 to 3

weight$. For the production of creams, emulsions or gels, the dye components are mixed with the additional ::constituents usual for such preparations. Examples of such additional ingredients include wetting or emulsifying agents of the non-ionic or non-ionic type, such as alkylbenzene sulphonates, fatty alcohol sulphates, alkyl sulphonates, fatty acid alkanolamides, addition products of ethylene oxides to fatty alcohols, thickeners such as methyl cellulose, starch , higher'fatty alcohols, paraffin oil, fatty acids, visceral acids, further perfume oil and hair care agents such as pantothenic acid and cholesterol.

The aforementioned additives are thereby used in the usual amounts for these purposes, such as, for example, wetting and emulsifying agents in concentrations from 0.5 to 30% by weight, and thickeners in concentrations from 0.1 to 25% by weight, each time referred to the total preparation.

The use of the hair dye original according to the invention can, regardless of whether it is a solution,

an emulsion, a cream or a gel. take place in slightly acidic,

neutral or particularly alkaline environment at a pH value from 8 to 10. The application temperatures therefore move in the range from 15 to £0oC. After an impact time of

approx. 30 minutes, the hair coloring agent is removed from the hair to be dyed, by rinsing. The hair is then washed with a mild shampoo and dried.

The following examples will further explain the object of the invention.

Examples

The 3-amino-2-methylphenol used as a coupling component in the following examples was prepared according to the corresponding indication in Noelting in Berichte der Deutchen Chemiscfeen Gesellschaft 37 (1904), page 1020/21.

The following compounds were used as developer components in the following examples:

E 1 p-toluy^Lendiamine

E 2 : p-phenylenediamine

E 3 : p-diaminoanisole sulfate

E 4 : N,N-dimethyl-p-phenylenediamine

E 5 : p-aminophenol

E 6 : 2-chloro-p-phenylenediamine

E 7 : 1-phenyl-3-carbamoyl-4-amino-pyrazolone-5

E 8 : N-methyl-pyrrolidone-2-hydrazone

E 9 : N-butyl-N-sulfobutyl-p-phenylenediamine

E 10 : N-methyl-p-phenylenediamine

E 11 : N^, N^-diethyl-2-methyl-p-phenylenediamine

E 12 : N-ethyl-N-hydroxyethyl-p-phenylenediamine-

E 13 : 2,4,5,6-tetraaminopyrimidine.

The hair coloring agent according to the invention is used

in the form of a cream emulsion. This resulted in an emulsion of 10 parts by weight of fatty alcohols of chain length<C>12"<C>18'

10 parts by weight fatty alcohol sulfate (sodium salt)

of chain length C^-C-ig,

75 parts by weight water

each time 0.01 mol of the developers listed in the following table and 3-amino-2-methylphenol are incorporated. The pH value of the emulsion was then set to 9.5 using ammonia, and the emulsion filled with water to 100 parts by volume. The oxidative coupling was carried out with a 1% hydrogen peroxide solution as oxidizing agent, with 10 parts by weight of hydrogen peroxide solution being added to 100 parts by weight of the mixture. The possible coloring cream with

additional oxidizer, was applied to up to 90% greyed, not specially pre-treated human hair, and left there for 30 minutes. After completion • of the dyeing process,. the hair was washed out with a normal hair detergent, and then dried. The colors thus formed are listed in the following table 1.

Claims (3)

1. Hair dye on the basis of oxidation dyes - substances, characterized by a content of 3-amino-2-methylphenol as a coupling agent, and the developer components common in oxidation dyes. 2. Hair coloring agent according to Kravl, characterized by an e-t content of p-toluyl-endiamine as a developing component. 3. Hair coloring agent according to claims 1 and 2, characterized by a content of developer-coupler combinations from 0.2 to 5% by weight, preferably 1 to 3% by weight, referred to the total agent.