Dyeing agent for keratinous fibers

Details Dyeing agent for keratinous fibers Dyeing agent for keratinous fibers

2002-05-21

2004-06-29

Mruk, Brian P. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S406000, C008S414000, C008S415000, C008S570000, C008S571000, C008S572000, C008S574000, C008S581000, C008S607000, C008S608000, C548S100000, C548S122000, C548S215000

Reexamination Certificate

active

06755872

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a composition for coloring keratin fibers, more particularly human hair, which contains a combination of heteroaromatic aldehydes and ketones and aromatic or heteroaromatic nitroamines, to the use of this combination as a coloring component in hair colorants and to a process for coloring keratin-containing fibers, more particularly human hair.
In general, keratin-containing fibers, for example hair, wool or pelts, are dyed either with substantive dyes or with oxidation dyes which are formed by oxidative coupling of one or more primary intermediates with one another or with one or more secondary intermediates. Primary and secondary intermediates are also known as oxidation dye precursors.
The primary intermediates normally used are primary aromatic amines containing another free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof.
Special representatives are, for example, p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)-ethanol, 2-(2,5-diaminophenoxy)-ethanol, 1-phenyl-3-carboxyamido-4-amino-5-pyrazolone, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
The secondary intermediates used are generally m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives. Particularly suitable secondary intermediates are &agr;-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol, 2-amino-4-(2-hydroxyethylamino)-anisole (Lehmann's blue), 1-phenyl-3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)-propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methyl resorcinol, 5-methyl resorcinol, 3-amino-6-methoxy-2-methylaminopyridine and 3,5-diamino-2,6-dimethoxypyridine.
With regard to other typical dye components, reference is specifically made to the series entitled “Dermatology” (Editors: Ch. Culnan and H. Maibach), Marcel Dekker Inc., New York/Basel, 1986, Vol. 7, Ch. Zviak, The Science of Hair Care, Chapter 7 (pages 248-250; Substantive Dyes) and Chapter 8 (pages 264-267; Oxidation Dye Precursors) and to the “Europäische Inventar der Kosmetik-Rohstoffe” published by the European Commission and available on floppy disk from the Bundesverband Deutscher Industrie- und Handelsunternehmen für Arzneimittel, Reformwaren und Körperpflegemittel e.V., Mannheim, Germany.
Although intensive colors with good fastness properties can be obtained with oxidation dyes, the color is generally developed under the influence of oxidizing agents, such as H
2
O
2
for example, which in some cases can result in damage to the fibers. In addition, some oxidation dye precursors or certain mixtures of oxidation dye precursors can occasionally have a sensitizing effect in people with sensitive skin. Although substantive dyes are applied under more moderate conditions, their disadvantage is that, in many cases, the colors obtained often have inadequate fastness properties.
The use of the combination of heteroaromatic aldehydes and aromatic or heteroaromatic nitroamines for coloring keratin-containing fibers has not hitherto been known.
The problem addressed by the present invention was to provide colorants for keratin fibers, more especially human hair, which would be at least equivalent in quality to conventional oxidation hair dyes in regard to depth of color, grey coverage and fastness properties, but which would not necessarily have to contain oxidizing agents, such as H
2
O
2
for example. In addition, the colorants according to the invention would have very little, if any, sensitizing potential.
It has surprisingly been found that the combination of the heteroaromatic aldehydes and ketones represented in formula I and aromatic or heteroaromatic nitroamines corresponding to formula II is eminently suitable for coloring keratin-containing fibers, even in the absence of oxidizing agents. They give colors with excellent brilliance and depth of color and lead to a wide variety of shades. In principle, however, oxidizing agents may be present.
SUMMARY OF THE INVENTION
The present invention relates to a composition for coloring keratin-containing fibers, more particularly human hair, containing a combination of heteroaromatic aldehydes corresponding to formula I:
in which
R
1
is a hydrogen atom, a C
1-4
alkyl group, an aryl or heteroaryl group,
R
2
is a C
1-4
alkyl group, an aryl, aralkyl or heteroaryl group,
R
3
, R
4
, R
5
and R
6
represent a hydrogen or halogen atom, a C
1-4
alkyl, C
1-4
alkoxy or C
1-4
hydroxyalkoxy group, a hydroxy, nitro or amino group, which may be substituted by C
1-4
alkyl groups, or a C
1-4
acyl group; two of the substituents together may also form a fused aromatic ring or one of the substituents together with R
1
or with R
2
may form a fused 5-, 6- or 7-membered ring which may also carry a fused aromatic ring,
X is a direct bond, an optionally substituted vinylene, phenylene or vinylenephenylene group,
Y is a sulfur atom, an oxygen atom, the group CR
7
R
8
, where R
7
and R
8
represent a C
1-4
alkyl group, the group NR
10
, where R
10
is a C
1-4
alkyl group, or an optionally substituted vinylene group and
Z
−
is halide, C
1-4
alkyl sulfate, arene sulfate, C
1-4
alkanesulfonate, C
1-4
perfluoroalkane sulfonate, perhalogenate, sulfate, hydrogen sulfate, tetrafluoroborate, hexafluorophosphate or tetrachlorozincate,
and aromatic or heteroaromatic nitroamines corresponding to formula II:
in which
AR represents benzene, naphthalene, pyridine, quinoline, isoquinoline, pyrimidine, indole, benzimidazole, benzothiazole, indazole, benzoxazole, quinoxaline, quinazoline, cinnoline, acenaphthene, fluorene, biphenyl, diphenylmethane, benzophenone, azobenzene, azonaphthalene, 1-arylazonaphthalene, 2-arylazonaphthalene, diphenylamine, stilbene, benzylidene aminobenzene and
R
11
, R
12
, R
13
and R
14
represent a hydrogen atom, a halogen atom, a C
1-4
alkyl, C
1-4
alkoxy, C
1-4
aminoalkyl, C
1-4
hydroxyalkoxy, hydroxy, nitro, carboxy, C
1-4
alkoxycarbonyl, sulfo, sulfamoyl, arylazo or amino group which may be substituted by C
1-4
alkyl or C
1-4
hydroxyalkyl groups,
and/or a reaction product of the compounds corresponding to formulae I and II.
DETAILED DESCRIPTION OF THE INVENTION
In the context of the invention, keratin-containing fibers are understood to include wool, pelts, feathers and, in particular, human hair. In principle, however, the colorants according to the invention may also be used to color other natural fibers such as, for example, cotton, jute, sisal, linen or silk, modified natural fibers such as, for example, regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as, for example, polyamide, polyacrylonitrile, polyurethane and polyester fibers.
Preferred compounds corresponding to formula I are the 4-formyl-1-methylpyridinium, 2-formyl-1-methylpyridinium, 4-formyl-1-ethylpyridinium, 2-formyl-1-ethylpyridinium, 4-formyl-1-benzylpyridinium, 2-formyl-1-benzylpyridinium, 4-formyl-1,2-dimethylpyridinium, 4-formyl-1,3-dimethylpyridinium, 4-formyl-1-methylquinolinium, 2-formyl-1-methylquinolinium, 5-formyl-1-methylquinolinium, 6-formyl-1-methylquinolinium, 7-formyl-1-methylquinolinium, 8-formyl-1-methylquinolinium, 4-acetyl-1-methylpyridinium, 2-acetyl-1-methylpyridinium, 4-acetyl-1-methylquinolinium, 5-acetyl-1-methylquinolinium, 6-acetyl-1-methylquinolinium, 7-acetyl-1-methylquinolinium, 8-acetyl-1-methylquinolinium, 9-formyl-10-methylacridinium, 4-(2-formylvinyl)-1-methylpyridinium, 1,3-dimethyl-

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