Agent for coloring keratin containing fibers

Details Agent for coloring keratin containing fibers Agent for coloring keratin containing fibers

2002-04-18

2004-09-14

Mruk, Brian P. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S407000, C008S574000, C008S575000, C008S576000, C008S587000, C008S592000, C008S607000, C008S608000

Reexamination Certificate

active

06790239

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a composition for coloring keratin-containing fibers, more particularly human hair, which contains a combination of aromatic aldehydes or ketones and CH-active compounds, 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-tetraamino-pyrimidine 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-phenylene-diamine 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, 5amino-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-amino-phenol, 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-6methoxy-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. Zvlak, The Science of Hair Care, Chapter 7 (pages 248-250; Substantive Dyes) and Chapter 8 (pages 264-267; Oxidation Dyes) and to the “Europäische Inventar der Kosmetik-Rohstoffe” published by the European Commission and available on floppy disk from the Bundesver-band 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 aromatic aldehydes or ketones and CH-active compounds described hereinafter 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 aromatic aldehydes or ketones represented in formula I and CH-active compounds corresponding to formulae II and/or III 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 aromatic aldehydes or ketones corresponding to formula I:
in which
R
1
is a hydrogen atom, a C
1-4
alkyl or an aryl group,
R
2
, R
3
and R
4
independently of one another represent a hydrogen atom, a C
1-4
alkyl group, a halogen atom, a hydroxy, C
1-4
alkoxy or nitro group or two of these groups together may form a fused aromatic ring,
R
5
represents a hydrogen atom, a C
1-4
alkyl, C
2-4
hydroxyalkyl, C
1-4
alkenyl or aryl group or, together with R
2
, R
3
or R
4
, forms a fused five- to seven-membered heterocyclic ring or, together with the oxygen atom, forms an olate group of which the negative charge is compensated by an alkali metal or ammonium ion,
n=0, 1 or 2,
and CH-active compounds corresponding to formulae II and/or III:
 in which
R
6
is a C
1-10
alkyl, C
2-4
alkenyl, C
2-4
hydroxyalkyl, C
2-4
carboxyalkyl, C
2-4
sulfoalkyl or aralkyl group,
R
7
and R
8
independently of one another represent a hydrogen atom, a C
1-4
alkyl group, a halogen atom, a hydroxy, C
1-4
alkoxy or nitro group or together form a fused aromatic ring,
R
9
represents a hydrogen atom, a C
1-4
alkyl or an aryl group,
X is an oxygen or sulfur atom, the group —CH═CH— or >N—R
12
, where R
12
is a C
1-4
alkyl, C
2-4
carboxyalkyl, C
2-4
sulfoalkyl, C
2-4
sulfoxyalkyl, C
2-4
hydroxyalkyl or aralkyl group, and
Y
−
is an anion selected from halide, C
1-4
alkyl sulfate, C
1-4
alkane sulfonate, arene sulfonate, C
1-4
perfluoroalkanesulfonate, tetrafluoroborate, perhalogenate, sulfate, hydrogen sulfate or carboxylate,
 in which
R
10
is a C
1-4
acyl group, aroyl, C
1-4
alkylsulfonyl, C
1-4
alkylsulfinyl, C
1-4
alkylamino, di-C
1-4
-alkylamino, vinylcarbonyl, methineimino, nitrile, ester or carboxylic acid amide group which may optionally be substituted by C
1-4
alkyl, C
2-4
hydroxyalkyl or aryl groups and
R
11
is a C
1-4
acyl, C
1-4
alkoxy, C
1-4
alkylamino, C
1-4
acylamino or di-C
1-4
-alkylamino group,
the substituents R
10
and R
11
together with the rest of the molecule forming a 5-, 6- or 7-membered heterocycle from the series of thiazolidine-2,5-diones, thiazolidine-2-thione-5-ones, perhydropyrimidine-2,4,6-triones, perhydropyrimidine-2-thione-4,6-diones, cyclopentane-1,3-diones, cyclo-hexane-1,3-diones, indane-1,3-diones, 2-pyrazoline-5-ones, 1,2-dihydro6-hydroxy-2-hydroxypyridines, benzothiazine-3-ones or enol esters thereof, and
Z represents oxygen, sulfur or the dicyanomethylene group,
and/or reaction products of the compounds corresponding to formulae I and II and/or III.


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The Science of Hair Care, Chapter 7,

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