Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-10-26
2001-11-06
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S423000, C008S568000, C008S571000, C008S102000, C008S431000, C008S548000, C548S366100
Reexamination Certificate
active
06312478
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to nonoxidative hair colorants based on certain anionic polymethine dyes and to a method for temporary hair coloration whereby the coloration can be removed at any time.
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 fades with every hair washing. Thus, depending on the product used and the type of hair, such colorations 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, because the products used for this purpose are usually very aggressive causing hair damage.
2. Prior Art
In the literature are described many attempts to restore the color of fibers. For example, German Patent DE 38 42 74 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 based on the use of oxidative or reductive decoloration 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 a maximum 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 foregoing 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 shading that requires 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 exists for nonoxidative colorants that can be removed at any time without causing major hair damage.
Some of the polymethine dyes and their suitability for the coloring of fibers have been known for a long time. A review of these dyes can be found, for example, in Houben-Weyl 5/1d, 4th edition (1954) page 227 ff. Some of these polymethine dyes are also commercially available. Although in some cases good to satisfactory coloring results are obtained, a complete removal of such dyes is usually very difficult. Thus pentamethine isooxazolone dyes produce a coloration, but the removal of this coloration is possible only to an insufficient degree.
SUMMARY OF THE INVENTION
Surprisingly, we have now found that colorants based on certain anionic polymethine dyes (in the following referred to as “oxonol dyes”), particularly the pyrazolone and pyridone compounds of formulas (II) to (IV), produce excellent hair coloration which can again be removed within a short time in simple and gentle manner. The decoloration can be achieved with either reducing or oxidizing agents, the use of reducing decolorizing agents being preferred.
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 highlights, particularly in the bright-red to blue 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 coloration into fashion and to provide an expression of personality.
Hence, the object of the present application is a hair colorant characterized in that it contains at least one oxonol dye of the tautomeric formula (Ia)/(Ib) or a physiologically tolerated salt thereof,
wherein in the general formula (Ia)/(Ib) X and Y independently of each other and always together with the two carbon atoms of the ring system indicated in formula (Ia)/(Ib) represent elements required for the formation of a five-membered or six-membered heterocyclic ring, and L denotes a bridging group of general formula
wherein R denotes a hydrogen atom, a phenyl, methyl or carboxamido group or a halogen atom, and the indices m and n each equal 0, 1 or 2, the sum of m and n not exceeding 2.
In general formula (Ia)/(Ib), it is possible to use as the five-membered or six-membered heterocyclic ring a pyrazolone, pyridone, dioxothiazoline, rhodanine, dioxoimidazoline or barbituric acid group, the ring systems in general formula (Ia)/(Ib) being either equal or different. Preferably, these two ring systems are equal keeping in mind that they are tautomeric forms, and L stands for a monomethine unit, trimethine unit or pentamethine unit.
Physiologically tolerated salts of the compounds of formula (Ia)/(Ib) are, in particular, the alkali metal and ammonium salts, for example the ammonium, sodium, potassium, N-methylmorpholinium, monoethanolammonium, diethanolammonium and triethanolammonium salts, among which the sodium, potassium and particularly ammonium salts are preferred.
When represented in their acid form, the dyes of the present invention preferably have the structures of general formulas (II) to (IV), shown in one of their possible tautomeric forms
wherein R1, R1′ and R6 denote hydrogen, a straight-chain or branched C1 to C8 alkyl, hydroxyethyl, dihydroxypropyl, methoxyethyl, carboxyethyl or C1 to C4 sulfoalkyl group, or a phenyl group possibly substituted with one or more halogen atoms, one or two sulfonic acid groups, one or two carboxyl groups, one or more unbranched or branched C1 to C8 alkyl groups or C1 to C8 alkoxy groups, or a benzyl group possibly substituted with one or more halogen atoms, a C1 to C4 alkyl, hydroxyl, methoxy, carboxyl, nitro or amino group or a five-membered or six-membered saturated or unsaturated heterocyclic ring, R1 and R1′ being equal or different, and
R2, R2′ and R7 denote hydrogen, a branched or unbranched C1 to C6 alkyl, phenyl or amino group which can also be acylated or sulfonylated, an acetyl, methoxy or carboxyl group possibly esterified with a straight-chain or branched C1 to C8 alcohol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, a carboxamido, carboxanilido, 2-amino-2-oxyethyl or nitrilo group, R2 and R2′ being equal or different, and
R3, R3′ and R8 denote hydrogen, a straight-chain or branched C1 to C11 alkyl group, a straight-chain or branched C1 to C11 monohydroxyalkyl group, a straight-chain or branched C1 to C11 dihydroxyalkyl group, a straight-chain or branched C1 to C11 alkoxyalkyl group, a straight-chain or branched C1 to C11 monoalkylamino group, a straight-chain or branched amino group of formula (CH
2
)
x
—NR11R12 (where x is an integer from 0 to 3 and R11 and R12 independently of each other denote a C1 to C3 alkyl group), a C2 to C4 sulfoalkyl or group, carboxyalkyl group or a phenyl group possibly substituted with one or more halogen atoms, one or two sulfonic acid groups, one or two carboxyl groups, one or more unbranched or branched C1 to C8 alkyl gr
Goettel Otto
Pirrello Aline
Einsmann Margaret
Striker Michael J.
Wella Aktiengesellschaft
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