DE20115893U1 - Hair dyes containing aminopyridine oxidation dye precursors give more brilliant and intense shades when dihydroxy acetone, alloxan, methyl glyoxal or potassium iodide is present - Google Patents

Abstract

Hair dyes containing an aminopyridine (or water-soluble salt) as a water-based oxidation dye precursor also contain 0.0001-5 wt.% (based on total composition wt.) of dihydroxy acetone, alloxan, methyl glyoxal and/or potassium iodide.

Description

A-35/01-U

Hair dye

The present invention relates to a hair dye based on a peroxide-reacting oxidation dye system which provides permanent, intense shades which can either be used as such or, in combination with other developers and/or couplers, to achieve further color nuances.

The developer substances most commonly used in hair dyes are 1,4-diaminobenzene (p-phenylenediamine) and 1-methyl-2,5-diaminobenzene (p-toluenediamine). Although the use of these substances largely meets the color-technical wishes of the users, there are still color nuances that cannot be fully achieved or intensified.

Aminopyridines and their substitution products and salts have also been used as oxidation dye precursors.

However, this still leaves some color-technical wishes unfulfilled.

The invention is based on the task of creating a hair dye j:u,
which is suitable for producing a large number of colours and, above all,
creates a particularly intense, shiny color.

This object is achieved in that such a hair dye contains at least one oxidation dye precursor which reacts with peroxide and is selected from aminopyridines or their water-soluble salts, in an aqueous base, and contains 0.0001 to 5% by weight of dihydroxyacetone and/or alloxan and/or methylglyoxal and/or potassium iodide, calculated on the total composition of the agent.

Suitable aminopyridines are in particular 2,5-diaminopyridine, 2,3-diaminopyridine, 2,6-diaminopyridine, 3-amino-2-methylamino-6-methoxypyridine, 2-dimethyl-5-aminopyridine, 2-dimethylaminoethyl-3-hydroxypyridine, 2-Amino-4,6-dimethylpyridine, 2-amino-3-hydroxypyridine _;#>#

djn _t 3-A.min.o-2(ß-riyfiroxyetb.ylaminoi-6rmethoxypyridine,

α-35/01

-2-

E.g. e-dimethylamino-S-aminopyridine, 2-di(hydroxyethyl)amino-5-aminopyridine, 2-hydroxyethylamino-5-aminopyridine and/or their water-soluble salts. Preferably, the agent according to the invention contains at least one coupling substance which can be selected from resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 2-amino-4-chlorophenol, 5-amino-4-methoxy-2-methylphenol, 2-aminophenol, 3-aminophenol, 1-methyl-2-hydroxy-4-aminobenzene, 3-N,N-dimethylaminophenol, 2,6-dihydroxy-3,5-dimethoxypyridine, 5-amino-3-methylphenol, 6-amino-3-methylphenol, 1,3-diaminobenzene, 1-amino-3-(2'-hydroxyethylamino)benzene, 1-amino-3-[bis(2'-hydroxyethyl)amino]benzene, a-naphthol, 4,6-dichlororesorcinol, 1,3-diaminotoluene, 1-hydroxynaphthalene, 4-hydroxy-1,2-methylenedioxybenzene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1-hydroxy-2-methylnaphthalene, 4-hydroxy-1,2-methyldioxybenzene, 2,4-diamino-3-chlorophenol, 5-amino-2-methoxyphenol and/or 1-methoxy-2-amino-4-(2'-hydroxyethylamino)benzene or their water-soluble salts. However, this does not exclude the addition of other developers and couplers.

When these compositions are used on a conventional basis, very expressive, intense, permanent hair colors are obtained after oxidation with peroxide, which can be varied to other color nuances by adding appropriate additional developers and couplers. The additional use of other known developers is also possible. In particular, substituted p-phenylenediamines such as 2,5-diaminotoluene, 2-n-propyl- or 2-ethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2-(2,5-diaminophenyl)ethanol, 1-amino-4-bis-(2'-hydroxyethyl)aminobenzene, 2-(2-hydroxyethylamino)-5-aminotoluene, 4,4'-diaminodiphenylamine, 4-aminodiphenylamine, 2-amino-5-N,N-diethylaminotoluene, 4-amino-N-ethyl-N-isopropylaniline, 2-chloro-p-phenylenediamine, 1-ß-hydroxyethyl-2,5-diamino-4-chlorobenzene, 1-ß-hydroxyethyl-2,5-diamino-4-methylbenzene, 2-methoxy-p-phenylenediamine, N,N-Diethyl-p-phenylenediamine, 1-amino-4-ß-methoxyethyl-

-3-

aminobenzene, 1-dimethylamino-4-aminobenzene, 1-hydroxy^.ö-diiamino^-methylbenzene, i-hydroxymethyl^.ö-diaminobenzene, 1,3-dimethyl-2,5-diaminobenzene, 1,4-diaminoisopropylbenzene and/ or 1-amino-4-ß-hydroxypropylaminoben2:ol, pyrazole and its derivatives such as i-hydroxyethyM.ö-diaminopyrazole, 3,4-diamino-5-hydroxypyrazole, 3,5-diaminopyrazole, S.S-diaminopyrazole-i-carboxamide, 3-Amino-5-hydroxypyrazole, i-phenyl-2-methylpyrazole, i-phenyl-3-methylpyrazole-S-one, 3,5-dimethylpyrazole, 3,5-dimethylpyrazole-i-methanol, 3,5-diamino-1,2,4,-triazole, 2-aminophenol, 4-aminophenol and its derivatives such as 4-amino-3-methylphenol, 2-chloro-4-aminophenol, 2,6-dichloro-4- aminophenol, 2,4-diaminophenol, 2,6-dibromo-4-aminophenol, tetraaminopyrimidines, triaminohydroxypyrimidines, diaminomono- and dihydroxypyrimidines, aminotriazines, 5-aminosalicylic acid and/or 1,2,4-triaminobenzene or their water-soluble salts .

The total concentration of the developing substances is usually 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 preferred weight ratio of the developer substances mentioned to the other developer and coupler substances is between about 1:8 to 8:1, preferably about 1:5 to 5:1, in particular 1:2 to 2:1. The coupler substance(s) as reaction partner of the developer substance(s) are present in the hair dyes according to the invention in approximately the same molar proportion as the developer substances, i.e. in amounts of 0.01 to 5.0%, preferably 0.05 to 4%, in particular 0.1 to 3% by weight of the total composition (without oxidizing agent), whereby the information in each case refers to the proportion of free base.

The proportion of dihydroxyacetone and/or alloxan and/or methylglyoxal and/or potassium iodide is preferably about 0.0001 to 5, in particular about 0.001 to 1 wt.% of the colorant (without oxidizing agent composition).

If desired, the compositions according to the invention can also contain so-called shading agents 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).

The hair dyes according to the invention can contain the basic and additive ingredients, 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, "Fundamentals and formulations of cosmetics", 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 well known from the state of the art.

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 concentration of 2 to 12 percent.
However, other peroxides such as urea peroxide and melamine peroxide can also be used.

As an alternative to peroxide oxidation, air oxidation can also be carried out, for example by applying a composition containing an oxidation dye precursor to the hair as an aerosol foam and leaving it there for about 15 to 30 minutes.

The pH value of the ready-to-use hair dye, i.e. after mixing with peroxide, can be either in the weakly acidic range, e.g. a range of 15.5 to 6.9, in the neutral range or in the alkaline range, i.e. between pH 7.1 and 11.

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In the following, various embodiments are given to explain the invention.

basis 8.0 (wt.%) Stearyl alcohol 4.5 Coconut fatty acid monoethanolamide 1.3 1,2-Propanediol mono/distearate 4.0 Coconut fatty alcohol polyglycol ether 1.0 Sodium lauryl sulfate 2.0 Oleic acid 1.5 1,2-Propanediol 0.5 Na-EDTA 1.0 Sodium sulphite 0.5 Protein hydrolysate 0.2 Ascorbic acid 0.4 Perfume 1.0 Ammonia, 25% 0.5 Ammonium chloride 0.8 Panthenol 0.0001 to 0.50 Potassium iodide 0.50 to 5.0 Dihydroxyacetone and/or alloxan and/or methylglyoxal to 100.00 Water

The oxidation dye combinations according to the invention and dihydroxyacetone and/or alloxan and/or methylglyoxal and/or potassium iodide were 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 (pH value of the mixture: 9.8) and leaving it for 20 minutes at room temperature, followed by rinsing and drying.

The following colorations were achieved:

JL

Composition No. 1 2 3 4 5 6 7 3-Amino-2-(ß-hydroxyethylamino)-6-methoxypyridine
HCI 0.46 0.46 S-Amino^-methylamino-e-methoxypyridine 0.50 0.50 2-Dimethylamino-5-aminopyridine 0.47 2,5-Diaminopyridine 0.41 2-Dimethylaminoethyl-3-hydroxypyridine 0.34 2,3-Diaminopyridine 0.25 2-Amino-3-hydroxypyridine 0.25 2,6-Diaminopyridine 0.25 2-Amino-4,6-dimethylpyridine 0.27 4-Amino-2-hydroxytoluene 0.13 2-Amino-4-hydroxyethylaminoanisole sulfate 0.31 1-Naphthol 0.32 Resorcin 0.25 Dihydroxyacetone 0.50 0.20 0.20 Alloxane 0.50 0.30 0.50 Methylglyoxal 0.50 0.30 0.50 Potassium iodide 0.002 0.002 0.002

iisse: Without additional active ingredients With active ingredient combination 1 Grey blue Intense grey-blue 2 Turquoise Intense dark turquoise 3 Light brown-orange Intense red gold 4 Grey-green Intense dark grey green 5 Pale red Intense red 6 Pale yellow Intense beige yellow 7 Yellow grey Strong grey

• ■ ·

· t

2,

The following oxidation dye mixtures, each with and without active ingredient, were introduced into the described base and the pH value was adjusted so that when mixed with 2% aqueous H ₂ O ₂ solution in a weight ratio of 1:1, a pH value of the ready-to-use mixture of 6.8 was achieved.

The mixtures were then applied to wool patches and strands of bleached human hair, washed out and dried after 15 minutes of exposure, and the coloring was evaluated.
The following result was achieved:

No. 1 1a 2 2a 3-Amino-2-methylamino-6-methoxypyridine 0.50 0.50 0.75 0.75 2-Amino-3-hydroxypyridine 0.25 0.254 — 0.25 1-Naphthol — — 0.48 0.48 Alloxane 0.50 — — — Methylglyoxal — — 0.50 —

The inventive composition No. 1 achieved an intense brown-orange coloration, while with formulation No. 1a only a pale orange coloration was achieved.

The inventive composition No. 2 achieved an intense grey-brown colouring, while with formulation No. 2a only a weak grey-brown colouring was achieved.

Claims (5)

1. Agent for dyeing human hair, containing at least one oxidation dye precursor selected from aminopyridines and their water-soluble salts in an aqueous base, characterized by a content of 0.0001 to 5% by weight of dihydroxyacetone and/or alloxan and/or methylglyoxal and/or potassium iodide, calculated on the total composition of the agent. 2. Agent according to claim 1, containing as aminopyridine 2,5-diaminopyridine, 2,3-diaminopyridine, 2,6-diaminopyridine, 3-amino-2-methylamino-6-methoxypyridine, 2-dimethyl-5-aminopyridine, 2-dimethylaminoethyl-3-hydroxypyridine, 2-amino-4,6-dimethylpyridine, 2-amino-3-hydroxypyridine, 3-amino-2-(β-hydroxyethylamino)-6-methoxypyridine, 2,6-dimethylamino-5-aminopyridine, 2-di-(hydroxyethyl)amino-5-aminopyridine, 2-hydroxyethylamino-5-aminopyridine and/or its water-soluble salts. 3. Agent according to one or more of claims 1 and or 2, additionally containing a coupling substance. 4. Agent according to claim 3, containing at least one coupler substance selected from resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 2-amino-4-chlorophenol, 5-amino-4-methoxy-2-methylphenol, 2-aminophenol, 3-aminophenol, 1-methyl-2-hydroxy-4-aminobenzene, 3-N,N-dimethylaminophenol, 2,6-dihydroxy-3,5-dimethoxypyridine, 5-amino-3-methylphenol, 6-amino-3-methylphenol, 5-amino-2-methoxyphenol, 1,3-diaminobenzene, 1-amino-3-(2'-hydroxyethylamino)benzene, 1-amino-3-[bis(2'hydroxyethyl)amino]benzene, α-naphthol, 4,6-dichlororesorcinol, 1,3-diaminotoluene, 1-Hydroxynaphthalene, 4-hydroxy-1,2-methylenedioxybenzene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1-hydroxy-2-methylnaphthalene, 2,4-diamino-3-chlorophenol and/or 1-methoxy-2-amino-4-(2'-hydroxyethylamino)benzene or their water-soluble salts. 5. Agent according to one or more of claims 1 to 4, characterized by a content of 0.001 to 1 wt. % of dihydroxyacetone and/or alloxan and/or methylglyoxal and/or potassium iodide, calculated on the total composition.