Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-12-09
2002-12-17
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S431000, C008S102000, C008S659000, C008S670000, C008S423000, C008S110000, C008S111000
Reexamination Certificate
active
06494923
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to nonoxidative colorants for keratin fibers, for example hair or wool, based on polymethine dyes and to a method for temporarily coloring keratin fibers, especially hair, whereby the color can be removed at any point in time.
2. Related Art
The coloring of hair is currently subject to the most varied trends. Whereas in the past hair was colored primarily to cover gray areas, today there is an increasing demand for integrating the hair color into current fashion as an expression of personality.
Now as before, two established methods of hair coloring are available. One of these is the oxidative hair coloring which a priori is unsuitable for temporary coloring, because it produces a very durable coloring result. The other method consists of the possibility of coloring hair with colorants containing nonoxidative, direct dyes (often referred to as toners). Although the dyes used for this purpose are optimized for dyeing performance as well as for remaining on the hair as long as possible, the color shade gradually weakens with every hair washing. Thus, depending on the product used and the type of hair, such colorants as a rule do not last more than a maximum of 10 hair washings. If the user of such nonoxidative colorants would like to restore her original hair color at an earlier time, no satisfactory means are currently available for rapidly restoring the original color shade, because the products used for this purpose are usually very aggressive and cause hair damage.
In the literature are described many attempts to restore the color of fibers. For example, German Patent DE 38 42 774 and U.S. Pat. No. 4,681,471 describe the decoloration of triarylmethane dyes with reducing agents. U.S. Pat. No. 5,474,578 uses the same approach whereby the dyes are decolorized by an oxidative or reducing treatment or a combination of these two treatments. A general problem underlying these methods is, in particular, that in most cases only partial decoloration is attained. Thus the method of U.S. Pat. No. 5,474,578 in the most favorable case produces at the most a degree of decoloration of 90 to 93%, and this degree of decoloration can be achieved only by applying a reductive treatment after an oxidative one. Such double treatment, however, causes extraordinary hair damage. Normally, such a method produces only partial (often <50%) hair decoloration.
The above-said patents also have in common that they deal with the decoloration of dye classes that have been used in hair cosmetics for a long time. The colorants are based on direct dyes with different chemical and physical properties and with different coloring and bleaching characteristics. Hence, at least for color shades requiring dye mixtures, it is very difficult to produce uniform decoloration, because the result is determined by the properties of the least active component.
Hence, a need existed for nonoxidative colorants that can be removed at any time without causing major damage to keratin fibers.
SUMMARY OF THE INVENTION
Surprisingly, it has now been found that colorants based on anionic or neutral mono- or polymethine dyes permit outstanding coloring of keratin fibers and that the resulting colorations can again be removed in a simple manner within a short time. Both reducing agents and oxidants are suitable for such decoloration.
Dyes of this type have been known for a long time, and a wide range of substitution patterns can be found in the literature. An overview of these dyes and of their methods of preparation can be found, for example, in Japanese Unexamined Patent Application JP 03-204640. Moreover, many dyes are commercially available.
By means of the colorants of the invention, it is possible to achieve color shades of a modified natural tone, but particularly those in the fashionable range. Moreover, besides the said color shades, it is possible to obtain a number of vivid color highlights, particularly in the yellow to red-violet range. As a result of the high tinting power of the dyes and their high substantivity, the original fiber color can be covered very effectively. As a result, it is possible to satisfy the aforementioned desire to integrate the hair color into fashion and to provide an expression of personality.
Hence, the object of the present application is a colorant for keratin fibers, for example furs, feathers, wool or hair, particularly human hair, characterized in that it contains at least one polymethine dye of formula (I) or a physiologically tolerated salt thereof:
wherein in general formula (I)
X and the two carbon atoms of the ring system shown in formula (I) together represent the elements needed to form a five-membered or six-membered heterocyclic ring system;
Y denotes an unsubstituted or substituted carbocyclic or heterocyclic aromatic ring containing no hydroxyl group in the &agr;-position to the polymethine group, or a group of general formula (II):
wherein E1 and E2 denote the radicals of a component with an active methylene group (—CH
2
—), or a group of general formula (III):
wherein E1 and E2 denote the radicals of a component with an active methylene group (—CH
2
—) and together form a nonaromatic ring, and n equals 0, 1 or 2.
For example, the five-membered or six-membered heterocyclic ring in general formula (I) can be a pyrazolone, pyridone, isoxazolone, dioxothiaxoline, rhodanine, dioxoimidazolidine, barbituric acid or thiobarbituric acid group.
In cases where in the general formula (I) substituent Y has general structure (II) or (III), the remaining hydrogen of the aforesaid active methylene component can form tautomers according to the following scheme:
The physiologically tolerated salts of the compounds of formula (I) are, in particular, the pyridinium, tetraalkylphosphonium, tetraarylphosphonium, alkali metal, and ammonium salts, for example the ammonium, triethylammonium, sodium, potassium, N-methylmorpholinium, monoethanolammonium, diethanolammonium and triethanolammonium salts among which the sodium, potassium and particularly ammonium salts are preferred.
Preferred among the compounds of formula (I) are the pyrazolone dyes of general structure (IV):
wherein
R1 denotes hydrogen, a straight-chain or branched C1 to C8 alkyl, hydroxyethyl, dihydroxypropyl, methoxyethyl, carboxyethyl or C1 to C4 sulfoalkyl group, a phenyl radical, a phenyl radical substituted with one or more halogen atoms, a phenyl radical substituted with one or two sulfonic acid groups, a phenyl radical substituted with one or two carboxylic acid groups, a phenyl radical substituted with one or more unbranched or branched C1 to C8 alkyl groups, a phenyl radical substituted with one or more unbranched or branched C1 to C8 alkoxy groups, a benzyl radical, a benzyl radical substituted with one or more halogen atoms, a benzyl radical substituted with a C1 to C4 alkyl group, a benzyl radical substituted with a hydroxyl group, a benzyl radical substituted with a methoxy group, a benzyl radical substituted with a carboxyl group, a benzyl radical substituted with a nitro group, a benzyl radical substituted with an amino group or a five-membered or six-membered saturated or unsaturated heterocyclic ring;
R2 denotes hydrogen, a branched or unbranched C1 to C6 alkyl group, a phenyl radical, an amino group, an acylated or sulfonylated amino group, an acetyl, methoxy or carboxylic acid group, a carboxylic acid group esterified with a straight-chain or branched C1 to C8 alcohol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, or a carboxamido, carboxanilido or 2-amino-2-oxyethyl group;
Y denotes an aromatic five-membered or six-membered carbocyclic or heterocyclic ring or a benzoanellated aromatic five-membered or six-membered carbocyclic or heterocyclic ring, or Y denotes a radical of general formula (II) or (III), wherein E1 and E2 independently of each other denote a nitrile, alkylsulfonyl, acyl, carboxylic ester or carboxamido group; and n is equal to 0, 1 or 2.
Particularly preferred are pyrazolone dyes of gener
Goettel Otto
Mettler Sandra
Pirrello Aline
Einsmann Margaret
Striker Michael J.
Wella Aktiengesellschaft
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