Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-01-04
2002-03-26
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S407000, C008S423000, C008S568000, C008S571000, C008S573000, C008S638000, C008S639000, C008S643000, C008S644000
Reexamination Certificate
active
06361571
ABSTRACT:
The present invention relates to nonoxidative colorants for keratin fibers, for example hair or wool, based on a combination of natural or synthetic nonoxidative dyes (known as “direct dyes”) and polymethine dyes, as well as to a method for coloring keratin fibers.
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 results in very durable tints. 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, as a rule and depending on the product used and the type of hair, such colorants do not last more than a maximum of 10 hair washings.
Hence, a need exists for nonoxidative colorants which besides good coloring properties have improved color stability, particularly in terms of wash-out resistance.
Surprisingly, we have now found that colorants based on a combination of natural or synthetic nonoxidative dyes and polymethine dyes (in the following also referred to as “oxonol dyes”) produce an outstanding and, in particular, very long-lasting coloring of keratin fibers.
Oxonol dyes have been known for a long time, and a wide range of substitution patterns can be found in the literature. A review of these dyes can be found, for example, in Houben-Weyl 5/1d, 4th edition (1954), page 227 ff. Some of these oxonol dyes are also available commercially.
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 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 color into fashion and to provide an expression of personality.
The object of the present application is therefore a colorant for keratin fibers, for example furs, feathers, wool and hair, particularly human hair, characterized in that it contains a combination of (a) at least one natural or synthetic nonoxidative dye and (b) at least one polymethine dye having the tautomeric formula (Ia)(Ib) or a physiologically tolerated salt thereof
wherein in general formula (Ia)(Ib) X and Y independently of each other and together with the two carbon atoms of the ring system indicated in formula (Ia)(Ib) represent the elements needed for the formation of a five-membered or six-membered heterocyclic ring, and L stands for a linking group of general formula
wherein R denotes a hydrogen atom, a phenyl, methyl or carboxamido group or a halogen atom, and indices m and n are equal to 0, 1 or 2, the sum of m and not exceeding 2.
For example, the five-membered or six-membered heterocyclic ring in general formula (Ia)(Ib) can be a pyrazolone, pyridone, isoxazolone, dioxothiazoline, rhodanine, dioxoimidazolidine, barbituric acid or thiobarbituric acid group, the two ring systems present in general formula (Ia)(Ib) being equal or different. Preferably, taking into account their tautomeric forms, these two ring systems are identical, and L stands for a monomethine, trimethine or pentamethine unit.
Suitable physiologically tolerated salts of the compounds of formula (Ia)(Ib) are, in particular, the 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 the ammonium salts are preferred.
Written in their acid form, the dyes of formula (I) used in the colorant of the invention contain polymethine dyes of general formulas (II) to (IV), presented in 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, 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 or 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, a 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;
R2, R2′ and R7 denote hydrogen, a branched or unbranched C1 to C6 alkyl group, a phenyl radical, an amino group which can also be acylated or sulfonylated, an acetyl or methoxy or 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 or nitrile 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 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, an amino group having formula (CH2)
x
—NR11R12 (wherein x stands for 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 carboxyalkyl group, a phenyl group or a phenyl group substituted with one or more halogen atoms, or a phenyl group substituted with one or two sulfonic acid groups, or with one or two carboxyl groups, or with one or more unbranched or branched C1 to C8 alkyl groups or with C1 to C8 alkoxy groups, or a benzyl group or a benzyl group substituted with one or more halogen atoms, or with a C1 to C4 alkyl, hydroxyl, methoxy, nitro or amino group, or a phenylethyl group, a five-membered or six-membered aromatic or nonaromatic heterocyclic ring which can be linked directly through a methylene group, a pyrolidino, morpholino, piperazino, piperidino or pyridino (C2 or C3) alkyl group or a trialkylammonium group of formula R13—N(R14)
3
+
(wherein R13 denotes a C1 to C6 alkylene group and R14 denotes a methyl or ethyl group, the total number of carbon atoms in the molecule being 5 to 9), R3 and R3′ being equal or different, and
R4, R4′ and R9 denote hydrogen, a nitrile, carboxylate ester, carboxamido, sulfonic acid, sulfomethyl or methanesulfonyl group or a pyridinium or imidazolium radical, R4 and R4′ being equal or different, and
R5, R5′ and R10 denote hydrogen or a C1 to C4 alkyl group or a C5-C6 cycloalkyl, phenylethyl, methoxyphenyl, benzyl, phenyl or carboxyl group, R5 and R5′ being equal or different, and
Z denotes oxygen or a radical of formula C(CN)
2
, C(CN)COOQ or C(COOQ)
2
wherein Q denotes a C1 to C8 alkyl group or an ethylene glycol mono-(C3 to C7)-alkyl ether, and L denotes a linking 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 equal 0, 1 or 2, the sum of m and n not exceeding 2.
Particularly preferred are dyes of general formulas (II) to (IV) and the salts thereof wherein
R1 and R1′ are equal and denote hydrogen, a straight-chain or branched C1 to C4 alkyl group, a hydroxyethyl, dihydroxypropyl, methoxye
Goettel Otto
Pirrello Aline
Einsmann Margaret
Striker Michael J.
Wella Aktiengesellschaft
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