DE29605174U1 - Hair dye - Google Patents

Description

Hair dye

The present invention relates to a hair dye based on a peroxide-reacting developer-coupler system, which provides expressive and permanent color tones that can either be used as such or, in combination with other developer and/or coupler substances, to achieve further color nuances.

The developer substances still most commonly used in hair dyes are 1,4-diaminobenzene (p-phenylenediamine) and l-methyl-2,5-diaminobenzene (p-toluenediamine). The use of these substances is not entirely problem-free, as they can lead to skin sensitization in extremely sensitive people in special cases (so-called "para-allergic" people).

Attempts have already been made to solve this problem by using alternative developing substances. This is possible to a limited extent by using tetraaminopyrimidine or 2-(2,5-diaminophenyl)ethanol (cf. EP-A 7537 and EP-B 400 330); however, this involves considerable reductions in the color intensity and the possibilities for varying the different color tones.

A largely optimal solution to the problem, namely the absence of skin sensitization on the one hand and a wide range of variation in the achievement of possible color nuances on the other hand, is achieved by the use of 2-(2'-hydroxyethylamino)-5-aminotoluene or its water-soluble salts as developer substances in hair dyes as described in EP-A 615 743.

Even so, there are still some color-related wishes that remain unfulfilled.

The invention is therefore based on the task of creating a hair dye which contains a non-sensitizing developer substance and is suitable for producing variable color tones.

This object is achieved by such a hair dye containing an oxidation dye precursor that reacts with peroxide and consists of 1,2,4-triaminobenzene or its water-soluble salts.

It was found that 1,2,4-triaminobenzene can not only be used in combination with conventional coupling substances, but also obviously performs a certain coupling function

In combination with other developing substances, surprising, expressive hair colors can also be achieved.

Even by using 1,2,4-triaminobenzene alone without the addition of other developers and couplers, a distinctive beige-brown hair color is achieved after mixing with peroxide oxidizing agents.

However, since the range of variations in the achievable color tones can of course be increased by combining with coupler substances, the use of triaminobenzene-coupler combinations is a preferred embodiment of the invention.

When these compositions are used on a conventional basis, very expressive basic colors are obtained after oxidation with peroxide, which can be varied to other color nuances by using mixtures of corresponding coupling substances.

Preferred coupler substances, which are used according to the invention in a molar ratio of developer substance to coupler substance between about 1:1 and about 2.5:1, are resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 2-amino-4-chlorophenol, 4-(N-methyl)aminophenol, 2-aminophenol, 3-aminophenol, 1-methyl-2-hydroxy-4-aminobenzene, 3-N,N-dimethylaminophenol, 4-amino-3-methylphenol, 5-amino-2-methylphenol, 6-amino-3-methylphenol, 3-amino-2-methylamino-6-methoxypyridine, 2-amino-3-hydroxypyridine, 4-aminodiphenylamine, 4,4'-diaminodiphenylamine,

2-Dimethylamino-5-aminopyridine _/ 2,6-diaminopyridine, 1,3-diaminobenzene, l-amino-3-(2'-hydroxyethylamino)benzene, l-amino-3· [bis(2'-hydroxyethyl)amino]benzene, 1,3-diaminotoluene, a-naphthol, l,4-diamino-2-chlorobenzene, 4,6-dichlororesorcinol, 4-hydroxy-l,2-methylenedioxybenzene, 1,5-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1-hydroxynaphthalene, 4-hydroxy-l,2-methylenedioxybenzene, 2,4-diamino-3-chlorophenol, and/or l-methoxy-2-amino-4-{2'-hydroxyethylamino)-benzene.

Preferred coupler substances are in particular resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 3-aminophenols, l-methyl-2-hydroxy-4-aminobenzene, 2-amino-4-ß-hydroxyethylaminoanisole or its water-soluble salts and α-naphthol.

A particularly preferred coupler substance is 2-amino-4-chlorophenol, which is particularly suitable for producing a grey-green base colour.

However, this does not mean that the addition of further coupling substances should be excluded .

The use of other known developer substances is also possible. In addition to those already mentioned, 4-aminophenol, 5-aminosalicylic acid and/or hydroxytriaminopyrimidines, as known from &Xgr;&Rgr;-&Xgr; 467 026, are also worth mentioning.

As such, in particular 2,4,5-triamino-6-hydroxypyrimidine and 4,5,6-triamino-2-hydroxypyrimidine, known from the aforementioned EP-B 467 026, are used, in particular also as sulfate salts.

The concentration of the developer substances is between about 0.05 and 5%, preferably 0.1 and 4%, in particular 0.25 to 0.5% and 2.5 to 3% by weight of the total composition of the hair dye (without oxidizing agent), whereby the information in each case refers to the proportion of free base.

The coupler substances as reaction partners of the developer substance(s) are present in the hair dyes according to the invention in approximately the same proportion as the developer substances, i.e. in amounts of 0.05 to 5.0%, preferably 0.1 to 4%, in particular 0.5 to 3% by weight of the total composition (without oxidizing agent), whereby the information in each case refers to the proportion of free base.

Here too, as already mentioned, it is possible and sometimes also expedient to use other known coupling substances if this is desired and necessary to achieve certain color nuances.

··· ·· A-5/95

The compositions according to the invention can, if desired, also contain so-called nuancers for fine-tuning the desired color tone, in particular direct dyes.

Such nuancers are, for example, nitro dyes such as 2-amino-4,6-dinitrophenol, 2-amino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, etc., preferably in amounts of about 0.05 to 2.5%, in particular 0.1 to 1% by weight of the color composition (without oxidizing agent).

1,2,4-Triaminobenzene is preferably used in the form of its water-soluble salts, for example as hydrochloride or sulfate.

The hair dyes according to the invention can contain the basic and additive substances, conditioning agents, etc. that are customary in such agents and that are known to the person skilled in the art and are described, for example, in the monograph by K. Schrader, "Grundlagen und Rezepturen der Kosmetika", 2nd edition (Hüthig Buch Verlag, Heidelberg, 1989), pp. 782 to 815. They can be in the form of solutions, creams, gels or in the form of aerosol preparations; suitable carrier material compositions are sufficiently known from the state of the art.

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For application, the oxidation dye precursor according to the invention is mixed with an oxidizing agent. The preferred oxidizing agent is hydrogen peroxide, for example in a 2 to 6 percent concentration.

However, other peroxides such as urea peroxide and melamine peroxide can also be used.

The pH value of the ready-to-use hair dye, i.e. after mixing with peroxide, can be either in the weakly acidic range, i.e. a range from 5.5 to 6.9, in the neutral range or in the alkaline range, i.e. between pH 7.1 and 9.5.

basis

Stearyl alcohol1 8.0 (wt.%) Coconut fatty acid monoethanolamide 4.5 1,2-Propanediol mono/distearate 1.3 Coconut oil alcohol polyglycol ether 4.0 Sodium lauryl sulfate 1.0 Oleic acid 2.0 1,2-Propanediol 1.5 Na-EDTA 0.5 Sodium sulphite 1.0 E iwhite hydroIysate 0.5 Ascorbic acid 0.2 Perfume 0.4 Ammonia, 25% 8.5 Ammonium chloride 0.5 Panthenol 0.8 Water @ 100,00

The developer-coupler combination according to the invention was incorporated into this base, with a corresponding reduction in the water content.

The dyeing was carried out on wool patches and strands of bleached human hair by applying a 1:1 mixture of dye precursor and 6% hydrogen peroxide solution and leaving it for 20 minutes at room temperature, followed by rinsing and drying.

The following colorations were achieved:

Example 1: 0.44 (weight • s) 1,2,4-triaminobenzene- dihydrochlorid 0.11 2-Araino-4-chloropheno1 0.08 3-Aminopheno1 0.08 Resorcin Coloring: Intensive Grey-green.

Further 1,2,4-triaminobenzene coupler combinations and the colors that can be achieved with them are listed below:

Example 2: 0.44 (wt.%) 1,2,4-triaminobenzene dihydrochloride

0.25 Resorcinol

Coloration: Strong beige brown.

Example 3 : O ₇ 44 (wt.%) 1,2,4-triamino-

benzene dihydrochloride

0.25 3-Aminopheno1

Coloration: Light olive green.

Example 4: 0.44 (wt.%) 1,2,4-triamino-

benzene dihydrochloride

0.32 a-naphthol

Coloration: Strong brown beige.

10

Example 5

Coloring:

0.44 (wt.%) 1,2,4-triamino-

benzoIdihydrochlor id

0.28 1-methyl-2-hydroxy-4-aminobenzene

Strong grey-blue.

Example 6

Coloring:

0.44 (wt%)

0.24 Light olive green, 1,2,4-triaminobenzene dihydrochloride

1,3-Diaminobenzene

Example 7

Coloring:

0.44 (wt%)

0.25

Brown beige.

1,2,4-Triaminobenzene dihydrochloride

2-amino-3-hydroxypyridine

Example 8 ;

Coloring:

0.44 (wt%)

0.25 Light yellow-green, 1,2,4-triaminobenzene dihydrochloride

2,6-Diaminopyridine

The following examples 9 to 11 show that excellent hair coloring can be achieved by combining 1,2,4-triaminobenzene with developing substances without the further addition of couplers.

11

Example 9: 0.44 (wt%) 1,2,4-Triamino- benzene dihydrochloride 0.50 p-Toluylenediamine sulf Coloring: Medium blonde. Example 10: 0.44 (wt%) 1,2,4-Triamino- benzene dihydrochloride 0.25 4-Aminopheno1 Coloring: Light brown. Example 11: 0.44 (wt%) 1,2,4-Triamino- benzene dihydrochloride 0.54 4-Hydroxy-2,5,6-tri-
aminopyrimidine sulfate Coloring: Beige yellow. Example 12: 0.88 (wt.%) 1,2,4-Triamino- benzene dihydrochloride Coloring: Beige brown.

Claims (5)

A-5/96^ 1. Hair dye based on an oxidation dye precursor system reacting with peroxide, characterized in that it contains 1,2,4-triaminobenzene or its water-soluble salts. 2. Hair dye according to claim 1, characterized in that it contains triaminobenzene or its water-soluble salts and at least one coupling substance. 3. Hair dye according to claim 2, characterized in that it contains at least one coupler substance selected from the group resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 2-amino-4-chlorophenol, 4-(N-methyl)aminophenol, 2-aminophenol, 3-aminophenol, l-methyl^-hydroxy^-aminobenzene, 3-N,N-dimethylaminophenol, 4-amino-3-methylphenol, 5-amino-2-methylphenol, 6-amino-3-methylphenol, 3-amino-2-methylamino-6-methoxypyridine, 2-amino-3-hydroxypyridine, 4-aminodiphenylamine, 4,4'-diaminodiphenylamine, 2-dimethylamino-5-aminopyridine, 2,6 -diaminopyridine, 1,3-diaminobenzene, l-amino-3-(2'-hydroxyethylamino)benzene, l-Amino-3-[bis(2'-hydroxyethyl)amino]benzene, 1,3-diaminotoluene, a-naphthol, 1,4-diami.no-2-chlorobenzene, 4,6-dichlororesorcinol, 4-hydroxy-l,2-methylenedioxybenzene, 1,5-dihydroxynaphthalene, 1,7-dihydroxy- naphthalene, 2,7-dihydroxynaphthalene, 1-hydroxynaphthalene, 4-hydroxy-1,2-methylenedioxybenzene, 2,4-diamino-3-chlorophenol and/or l-methoxy-2-amino-4-(2'-hydroxyethylamino)-benzene. 4. Hair dye according to claim 3, characterized in that it contains at least one additional coupling substance selected from the group resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 3-aminophenol, 2-amino-4-chlorophenol, l-methyl-2-hydroxy-4-aminobenzene, α-naphthol, ₃ -amino-2-methylamino-6-methoxypyridine and/or 2-amino-4-(β-hydroxyethylamino)anisole or its water-soluble salts. 5. Hair dye according to claim 4, characterized in that it contains 2-amino-4- _chlorophenol as a coupling substance.