Composition for the dyeing of human hair Number:7,056,352 from the United States Patent and Trademark Office (PTO) owispatent Hair dyeing composition on the basis of an oxidation dyestuff precursor reacting with peroxide, comprising at least one developing and/or coupling substance selected from the group a) 3-chloro-p-aminophenol and b) 2-methyl-5-.gamma.-hydroxypropyl aminophenol, 2-methyl-5-methyl aminophenol, 2-methyl-5-ethyl aminophenol, 2-methoxy-5-aminophenol, 2-methyl-4-methoxy-5-aminophenol and/or 2-methyl-4-methoxy-5-hydroxyethyl aminophenol and c) 1-methoxy-2,4-diaminobenzene, 1-.beta.-hydroxyethyloxy-2,4-diaminobenzene, 1-(1,2-dihydroxypropyloxy)-2,4-diaminobenzene, 1-methoxy-2-amino-4-.beta.-hydroxyethyl aminobenzene, 1,3-bis-(2,4-diaminophenoxy)-propane, 2,4-diamino-5-methyl-phenetol and/or 1-.beta.-hydroxyethyloxy-5-methyl-2,4-diaminobenzene.<H Composition, dyeing, Composition, for, 7056352.html, Patent, pto, 7056352

Title: Composition for the dyeing of human hair

Abstract: Hair dyeing composition on the basis of an oxidation dyestuff precursor reacting with peroxide, comprising at least one developing and/or coupling substance selected from the group a) 3-chloro-p-aminophenol and b) 2-methyl-5-.gamma.-hydroxypropyl aminophenol, 2-methyl-5-methyl aminophenol, 2-methyl-5-ethyl aminophenol, 2-methoxy-5-aminophenol, 2-methyl-4-methoxy-5-aminophenol and/or 2-methyl-4-methoxy-5-hydroxyethyl aminophenol and c) 1-methoxy-2,4-diaminobenzene, 1-.beta.-hydroxyethyloxy-2,4-diaminobenzene, 1-(1,2-dihydroxypropyloxy)-2,4-diaminobenzene, 1-methoxy-2-amino-4-.beta.-hydroxyethyl aminobenzene, 1,3-bis-(2,4-diaminophenoxy)-propane, 2,4-diamino-5-methyl-phenetol and/or 1-.beta.-hydroxyethyloxy-5-methyl-2,4-diaminobenzene.

Patent Number: 7,056,352 Issued on 06/06/2006 to Lorenz, et al.

Inventors: Lorenz; Heribert (Gross-Bieberau, DE); Kaffenberger; Klaus (Alsbach-Haehnlein, DE); Noecker; Bernd (Ober-Ramstadt, DE); Wilz; Ruediger (Pfungstadt, DE)
Assignee: KPSS-Kao Professional Salon Services GmbH (Darmstadt, DE)

Appl. No.: 465255

Filed: June 19, 2003

Foreign Application Priority Data


Jul 11, 2002 [DE]			102 31 260

Current U.S. Class: 8/405 ; 8/406; 8/408; 8/410; 8/411; 8/421

Field of Search: 8/405,406,408,410,411,421

References Cited [Referenced By]

U.S. Patent Documents


4865619	September 1989	Junino et al.
5514188	May 1996	Cotteret et al.
5578087	November 1996	Audousset et al.
5672759	September 1997	Junino et al.
5863300	January 1999	Audousset et al.

Foreign Patent Documents


38 18 139	Dec., 1988	DE
693 09 638	Jul., 1997	DE
198 34 567	Feb., 2000	DE
200 17 642	Jan., 2001	DE
100 51 034	Apr., 2002	DE
101 18 892	Oct., 2002	DE

Primary Examiner: Elhilo; Eisa
Attorney, Agent or Firm: Norris McLaughlin & Marcus PA

Claims

The invention claimed is:

1. Hair dyeing composition on the basis of an oxidation dyestuff precursor reacting with peroxide, which contains developing and coupling substance(s) comprising a) 3-chloro-p-aminophenol; b) at least one compound selected from the group consisting of: 2-methyl-5-.gamma.-hydroxypropyl aminophenol, 2-methyl-5-methyl aminophenol, 2-methyl-5-ethyl aminophenol, 2-methoxy-5-aminophenal, 2-methyl-4-methoxy-5-aminophenol and 2-methyl-4-methoxy-5-hydroxyethyl aminophenol; and c) at least one compound selected from the group consisting of 1-methoxy-2,4-diaminobenzene, 1-.beta.-hydroxyethyloxy-2,4-diaminobenzene, 1-(1,2-dihydroxypropyloxy)-2,4-diaminobenzene, 1-methoxy-2-amino-4-.beta.-hy-droxyethyl aminobenzene, 1,3-bis-(2,4-diaminophenoxy)-propane, 2,4-diamino-5-methyl-phenol and/or 1-.beta.-hydroxyethyloxy-5-methyl-2,4-diaminobenzene wherein said developing and/or coupling substance(s) includes salt forms thereof and said hair dyeing composition produces hair colorations in the range of red.

2. The hair dyeing composition of claim 1 wherein the total concentration of the developing substance is from 0.05% to 5% by weight, calculated from the total weight of the hair dyeing composition excluding the oxidation agent.

3. The hair dyeing composition of claim 1 which further comprises of a shading agent in an amount of from about 0.05% to about 2.5% by weight based on the total weight of the hair dyeing composition (excluding the oxidizing agent).

4. The hair dyeing composition of claim 3 wherein the shading agent is a nitro dyestuff.

Description

The present invention concerns a composition for the dyeing of human hair on the basis of an oxidation dyestuff precursor system reacting with peroxide which provides long-lasting, intensive colors either used as such, or which can be used to obtain further shades in combination with additional developing and/or coupling agents and which does not damage the hair even upon repeated application within short intervals.

The developing substances still most frequently used in hair dyeing compositions are 1,4-diaminobenzene (p-phenylenediamine) and 1-methyl-2,5-diaminobenzene (p-toluylenediamine). Although incorporation of these substances largely fulfills the user's color wishes, there are still shades that cannot be completely achieved by the use thereof.

Proposals have also been made to close this gap by the use of alternative developing substances. To a limited degree this is possible with the use of tetraaminopyrimidine or 2-(2,5-diaminophenyl)ethanol (see and EP-B 400 330); however, it is then necessary to accept reduced color intensity in other shades. A further satisfactory solution of this problem is disclosed in EP-A 615 743, with the use of 2-(2'-hydroxyethyl amino)-5-aminotoluene or the water-soluble salts thereof, as a component of oxidation hair dye compositions.

However, to the present it has not been possible to achieve strong colorations in the range of red by this means.

The invention starts from the task of counteracting this deficiency and providing an oxidation dyestuff composition which achieves intensive, glossy colorations, especially in the range of red, and which leaves the hair without damage even upon repeated application within short periods of time.

This task is solved when such a hair dyeing composition comprises an oxidation dyestuff system reacting with peroxide which is selected from a) 3-chloro-p-aminophenol and b) 2-methyl-5-.gamma.-hydroxypropyl aminophenol, 2-methyl-5-methyl aminophenol, 2-methyl-5-ethyl aminophenol, 2-methoxy-5 aminophenol, 2-methyl-4-methoxy-5-aminophenol and/or 2-methyl-4-methoxy-5-hydroxyethyl amino-phenol and c) 1-methoxy-2,4-diaminobenzene, 1-.beta.-hydroxyethyloxy-2,4-diamino-benzene, 1-(1,2-dihydroxypropyloxy)-2,4-diaminobenzene, 1-methoxy-2-amino-4-.beta.-hydroxyethyl aminobenzene, 1,3-bis-(2,4-diaminophenoxy)-propane, 2,4-diamino-5-methyl-phenol and/or 1-.beta.-hydroxyethyloxy-5-methyl-2,4-diaminobenzene.

After oxidation with peroxide, use of these compositions on the basis of a customary carrier provides very expressive, intensive, long-lasting hair colorations, especially in the range of red, which can be varied to achieve further shades by the addition of the respective further developing and coupling substances.

In addition to the named developing and coupling substances it is also possible to incorporate further substances of this type. Further suitable coupling substances are, for example, 1-methoxy-2-amino-4-(.beta.-hydroxyethyl amino)benzene, 2-amino-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, resorcinol, 2-methyl resorcinol, 4-chlororesorcinol, 1,3-diamino benzene, 1,6-dihydroxynaphthaline, 1,7-dihydroxy-naphthaline, p-phenylenediamine, p-toluylenediamine, 2,6-dimethyl-p-phenylenediamine, 2-hydroxymethyl-p-phenylenediamine, 2-hydroxyethyl-p-phenylenediamine, 2-n-propyl-p-phenylenediamine, N,N-bis(.beta.-hydroxyethyl)-p-phenylenediamine, N-methoxyethyl-p-phenylenediamine and/or 5-chloro-2-hydroxyethyl-p-phenylenediamine or the water-soluble salts thereof.

The total concentration of the developing substances is customarily from 0.05% to 5%, preferably 0.1% to 4%, in particular 0.5% to 3% by weight, calculated to the total hair dyeing composition (excluding the oxidation agent), whereby these figures are always related to the proportion of free base. The preferred weight proportion of the developing substances to the additional developing and coupling substances range between about 1:8 to 8:1, preferably about 1:5 to 5:1, in particular 1:2 to 2:1.

In the hair dyeing compositions according to the invention, the coupling substance(s) as reaction partners of the developing substance(s) are present in approximately the same molecular proportions as the developing substances, i.e. in amounts from 0.05% to 5.0%, preferably 0.1% to 4%, in particular 0.5% to 3% by weight, calculated to the total composition (excluding the oxidizing agent), whereby these figures are always related to the proportion of free base.

If desired, the compositions according to the invention can also contain so-called shading agents for precise adjustment of the desired shade, in particular direct-acting dyestuffs.

Such shading agents are, for example, nitro dyestuffs such as 2-amino-4,6-dinitrophenol, 2-amino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, etc., preferably in amounts from about 0.05% to 2.5%, in particular 0.1% to 1% by weight of the dyestuff composition (excluding the oxidizing agent).

The hair dyeing compositions according to the invention can comprise the basic substances and additives customarily found in such compositions, conditioning agents, etc., known as state of the art and described, for example, in the monography of K. Schrader, "Grundlagen und Rezepturen der Kosmetika", 2nd Ed. (Huthig Buch Verlag, Heidelberg, 1989), pp. 782 to 815. They can be prepared as solutions, creams, gels or also in the form of aerosol products; suitable carrier material compositions are known as state of the art.

For application, the oxidation dyestuff precursor is mixed with an oxidizing agent. The preferred oxidizing agent is hydrogen peroxide, for example in a concentration of 2% to 6% by weight.

However, the use of other peroxides such as urea peroxide and melamine peroxide is also possible.

The pH-value of the ready-to-use hair dyeing composition, i.e. after mixing with peroxide, can be in a slightly acidic range, i.e. from 5.5 to 6.9, as well as in the neutral or alkaline range, i.e. between pH 7.1 and 10.

In the following, various Examples are used to illustrate the invention.

TABLE-US-00001 Carrier Stearyl alcohol 8.0 (% by wt.) Coco fatty acid monoethanolamide 4.5 1,2-Propanediol mono/distearate 1.3 Coco fatty alcohol polyglycol ether 4.0 Sodium lauryl sulfate 1.0 Oleic acid 2.0 1,2-Propanediol 1.5 Na-EDTA 0.5 Sodium sulfite 1.0 Protein hydrolyzate 0.5 Ascorbic acid 0.2 Perfume 0.4 Ammonia, 25% 1.0 Ammonium chloride 0.5 Panthenol 0.8 Water ad 100.00

The oxidation dyestuff combinations according to the invention were incorporated into this carrier, whereby the water content was reduced accordingly.

The colorations were carried out on wool patches and strands of bleached human hair by application of a 1:1 mixture of a dyestuff precursor and a 6% hydrogen peroxide solution (pH-value of the mixture: 9.8) with twenty minutes processing at room temperature, subsequent rinsing and drying.

The following colorations were achieved:

TABLE-US-00002 Example 1: 0.21 (% by wt.) 3-Chloro-p-aminophenol HCl 0.14 2-Methyl-5-.gamma.-hydroxypropyl aminophenol 0.27 1-.beta.-Hydroxyethyloxy-2,4-diaminobenzene HCl 0.20 1-Phenyl-3-methyl-5-pyrazolone Coloration: Brilliant beige-red. Example 2: 0.41 (% by wt.) 3-Chloro-p-aminophenol HCl 0.14 2-Methyl-5-.gamma.-hydroxypropyl aminophenol 0.31 1-Methoxy-2-amino-4-.beta.-hydroxyethyl aminobenzene H.sub.2SO.sub.4 Coloration: Brilliant carmine red. Example 3: 0.41 (% by wt.) 3-Chloro-p-aminophenol HCl 0.145 2-Methyl-5-.gamma.-hydroxypropyl aminophenol 0.49 1,3-Bis-(2,4-diaminophenoxy)-propane 4HCl Coloration Brilliant mahogany-red. Example 4: 0.41 (% by wt.) 3-Chloro-p-aminophenol HCl 0.09 2-Methyl-5-.gamma.-hydroxypropyl aminophenol 0.21 1-Methoxy-2-amino-4.beta.-hydroxyethyl amino benzene 0.33 H.sub.2SO.sub.4 1,3-Bis-(2,4-diaminophenoxy)-propane 4HCl Coloration: Brilliant mahogany-violet. Example 5: 0.41 (% by wt.) 3-Chloro-p-aminophenol HCl 0.19 2-Methyl-5-.gamma.-hydroxypropyl aminophenol 0.27 1-.beta.-Hydroxyethyloxy-2,4-diaminobenzene HCl Coloration: Brilliant beige- red-orange. Example 6: 0.41 (% by wt.) 3-Chloro-p-aminophenol HCl 0.14 2-Methyl-5-.gamma.-hydroxypropyl aminophenol 0.27 1-.beta.-Hydroxyethyloxy-2,4-diaminobenzene HCl Coloration: Brilliant beige- red-orange.

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