Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Patent
1996-09-17
1998-04-28
McGinty, Douglas J.
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
8407, 8423, 8405, 8563, 8574, A61K 713
Patent
active
057439192
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to the use of certain N-substituted isatin derivatives for coloring keratin-containing fibers and to coloring formulations containing these isatin derivatives.
Keratin-containing fibers, for example hair, wool or furs, are generally colored 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. Although intensive colors with good fastness properties can be obtained with oxidation dyes, development of the color takes place under the effect of oxidizing agents, such as H.sub.2 O.sub.2 for example, which frequently results in damage to the fibers. Although substantive dyes are applied under more moderate conditions, their disadvantage is that the colors often have unsatisfactory fastness properties.
2. Discussion of Related Art
Coloring systems based on isatin or isatin derivatives offer an alternative solution. Isatin is described in DE-OS 36 35 147 A1 as a substantive dye for coloring keratin fibers either on its own or in conjunction with quinone dyes. Unfortunately, the range of variation of the color tones obtainable is limited. In most cases, a golden color is obtained.
Another isatin-containing coloring system is described in EP 359 465 A2. In this case, the color is obtained with a ketimine (Schiff's base) produced by the reaction of an isatin with an aniline derivative. The ketimine is either applied as such to keratin fibers where it develops color or, alternatively, a mixture consisting of an isatin and an aniline derivative is applied to the fibers and initially forms the ketimine in situ, after which the color develops on the fibers.
EP 497 697 A1 describes hair coloring formulations based on isatins and aminoindoles or indolines containing a primary amino group, Schiff's bases being formed in a condensation reaction.
EP 0 502 783 A1 describes hair coloring formulations containing isatins and aminopyridines or isatins and aminopyrimidines containing a primary amino group.
EP 0 502 784 A1 describes hair coloring formulations containing isatins and substituted diamines or aminophenols or isatins and (bisaryl) alkylenediamines.
Unfortunately, the hair colors obtainable with these isatins are not always satisfactory in regard to the brilliance and intensity of the color tones.
The problem addressed by the present invention was to provide hair coloring systems based on isatins which would give particularly intensive colors. It has now surprisingly been found that certain N-substituted isatin derivatives are outstanding in satisfying these requirements and are eminently suitable for coloring keratin fibers.
Examples of keratin-containing fibers are wool, furs, skins and human hair. In principle, however, the N-substituted isatin derivatives described in more detail hereinafter may also be used for coloring other natural fibers, for example cotton, jute, sisal, linen or silk, modified natural fibers, for example regenerated cellulose, nitrocellulose, alkyl or hydroxyalkylcellulose or acetyl cellulose and synthetic fibers, for example polyamide, polyacrylonitrile, polyurethane and polyester fibers.
DESCRIPTION OF THE INVENTION
The present invention relates to the use of isatin derivatives corresponding to formula I: ##STR3## in which R.sup.1 is a hydroxy group, an optionally C.sub.1-4 alkyl- or phenyl-substituted amino group, a C.sub.3-8 alkenyl, dihydroxy-(C.sub.3-6)-alkyl, trihydroxy-(C.sub.4-6)-alkyl, tetrahydroxy-(C.sub.5-6)-alkyl, pentahydroxy-C.sub.6 -alkyl, C.sub.2-4 -aminoalkyl, C.sub.1-4 -sulfoalkyl group, an optionally C.sub.1-4 -alkyl-substituted 2-furylmethyl, 2-thienylmethyl, 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl group or an aralkyl group corresponding to formula (II): ##STR4## in which R.sup.6 and R.sup.7 independently of one another represent hydrogens, halogen atoms, hydroxy groups, amino groups optionally substituted by C.sub.1-4 alkyl or phenyl, C.sub.1-4 alkyl g
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Hoeffkes Horst
Moeller Hinrich
Dvsheck Caroline L.
Grandmaison Real J.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
McGinty Douglas J.
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