Agent for dying keratin fibers

Details Agent for dying keratin fibers Agent for dying keratin fibers

2002-05-03

2004-08-03

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

06770102

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a composition for coloring keratin 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-tetraaminopyrimidine and derivatives thereof.
Special representatives are, for example, p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis-(2-hydroxyethylyp-phenylenediamine, 2-(2,5-diaminophenyl)-ethanol, 2-(2,5-diaminophenoxy)ethanol, 1-phenyl-3-carboxyamido4-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, 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; OxidaUon Dye Precursors) 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
and R
3
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
4
and R
5
represent a hydrogen atom, a C
1-4
alkyl, C
2-4
hydroxyalkyl, C
1-4
alkenyl or aryl group or, together with the nitrogen atom, form a five- to seven-membered heterocyclic ring or one of them forms a saturated or unsaturated 5-, 6- or 7-membered ring with one of the substituents R
2
or R
3
,
Q is a direct bond or a vinylene or vinylidene group which, together with one of the two substituents R
4
or R
5
, may form an indole ring or—where an exocyclic double bond is formed—an indoline ring and
n=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
2-10
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 >N—R
12
or —CH═CH—, 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 1,3-thiazolidine-2,5-diones, 1,3-thiazolidine-2-thione-5-ones, perhydropyrimidine-2,4,6-triones, perhydropydmidine-2-thione-4,6-diones, cyclopentane-1,3-diones, cyclo-hexane-1,3-diones, indolines, indan-1,3-diones, indan-1-ones, 2-pyrazoline-5ones, 1,2-dihydro-6-hydroxy-2-hydroxypyridines 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.
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, for example, 4-dimethylaminobenzaldehyde,

Affiliated with

Also associated with

Rating

Agent for dying keratin fibers does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Agent for dying keratin fibers, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Agent for dying keratin fibers will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3309740