Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-06-19
2002-04-16
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S406000, C008S407000, C008S408000, C008S409000
Reexamination Certificate
active
06371993
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to the use of onium aldehydes and ketones and derivatives thereof for coloring keratin-containing fibers, more particularly human hair, to a composition containing onium aldehydes and ketones for coloring keratin-containing fibers and to a process for coloring keratin-containing fibers.
BACKGROUND OF THE INVENTION
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-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine and 1,3-N,N′-bis-(2′-hydroxyethyl)-N,N′-bis-(4′-aminophenyl)-diaminopropan-2-ol.
The secondary intermediates used are generally m-phenylene-diamine derivatives, naphthols, resorcinol and resorcinol derivatives and m-aminophenol derivatives. Particularly suitable secondary intermediates are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 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-amino-3-hydroxy-pyridine, 2-methyl resorcinol, 5-methyl resorcinol and 2-methyl4-chloro-5-aminophenol.
With regard to the dyes suitable for use in the hair coloring and tinting formulations according to the invention, reference is also specifically made to Ch. Zviak's work The Science of Hair Care, Chapter 7 (pages 248-250; Substantive Dyes) and Chapter 8, pages 264-267; Oxidation Dye Precursors), published as Vol. 7 of the Series “Dermatology” (Editors: Ch. Culnan and H. Maibach), Marcel Dekker Inc., New York/Basel, 1986 and to the “Europäische Inventar der Kosmetik-Rohstoffe” published by the Europäische Gemeinschaft and available in diskette form from the Bundesverband Deutscher Industrie- und Handelsuntemehmen 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 have inadequate fastness properties.
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. Another problem addressed by the invention was to provide colorants with which a wide range of color tones could be obtained without any staining of the skin. In addition, the colorants according to the invention would have very little, if any, sensitizing potential.
It has now surprisingly been found that a combination of onium aldehydes and ketones as defined hereinafter and amines, hydroxy compounds and CH-active compounds are eminently suitable for coloring keratin-containing fibers. They give colors with excellent brilliance and depth of color and lead to a wide variety of color tones. The use of oxidizing agents is not necessary but, in principle, is not ruled out either.
Accordingly, the present invention relates to the use of onium aldehydes and ketones corresponding to formula I below or derivatives thereof:
BRIEF DESCRIPTION OF THE INVENTION
in which
R
1
is a hydrogen atom, a (C
1-4
) alkyl group, an aryl group or a heteroaryl group,
R
2
, R
3
and R
4
independently of one another represent a hydrogen atom, a halogen atom, a (C
1-4
) alkyl group, a (C
1-4
) alkoxy group hydroxy-(C
1-4
)-alkoxy group, hydroxy group, nitro group, aryl group, trifluoromethyl group, 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 benzene ring,
R
5
is a (C
1-4
) alkyl group, aryl group, aralkyl group or heteroaryl group,
X is a direct bond or a vinylene or phenylene group which may be substituted and
Y
−
is halide, benzenesulfonate, p-toluene sulfonate, methane sulfonate, trifluoromethane sulfonate, perchlorate, sulfate, hydrogen sulfate or tetrachlorozincate or the N-oxide of the heterocycle,
in combination with at least one compound containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, &agr;- to &ohgr;-amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound, for coloring keratin-containing fibers.
The present invention also relates to a composition for coloring keratin-containing fibers, more particularly human hair, characterized in that it contains
(A) one or more onium aldehydes or ketones corresponding to formula I or derivatives thereof and
(B) at least one compound containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen containing heterocyclic compounds, &agr;- to &ohgr;-amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound; the reaction product of components A and B may also be present.
DETAILED DESCRIPTION OF THE INVENTION
In the contexts 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.
The scope of the present invention also encompasses the use of substances which are reaction products of the individual components with one another.
Examples of derivatives of the compounds corresponding to formula I are oximes, acetals, ketals or hydrazones.
Suitable compounds corresponding to formula I which may be used as component A are the benzenesulfonates, p-toluene sulfonates, methane sulfonates, trifluoromethane sulfonates, perchlorates, sulfates, chlorides, bromides, iodides and/or tetrachlorozincates of 4-formyl-1-methyl pyridinium, 3-formyl-1-methyl pyridinium, 2-formyl-1-methyl pyridinium, 4-formyl-1-ethyl pyridinium, 2-formyl-1-ethyl pyridinium, 4-formyl-1-benzyl pyridinium, 2-formyl-1-benzyl pyridinium, 4-formyl-1,2-dimethyl pyridinium, 4-formyl-1,3-dimethyl pyridinium, 4-formyl-1-methyl quinolinium, 2-formyl-1-methyl quinolinium, 4-(2-formylvinyl)-1-methyl quinolinium, 4-acetyl-1-methyl pyridini
Hoeffkes Horst
Moeller Hinrich
Elhilo Eisa
Gupta Yogendra N.
Henkel Kommanditgesellschaft auf Aktien
Hild Kimberly R.
Jaeschke Wayne C.
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