Isatin derivatives for coloring keratin-containing fibers

Details Isatin derivatives for coloring keratin-containing fibers Isatin derivatives for coloring keratin-containing fibers

1995-10-30

1997-03-18

Lieberman, Paul

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

8409, 8423, 8574, A61K 713

Patent

active

056118171

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to the use of certain isatin derivatives containing sulfo groups or carboxyl groups 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.


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.


DESCRIPTION OF THE INVENTION

It has now surprisingly been found that certain isatin derivatives containing sulfo groups or carboxyl groups are eminently suitable for coloring keratin-containing fibers.
Examples of keratin-containing fibers are wool, furs, skins and human hair. In principle, however, the isatin derivatives containing sulfo or carboxyl groups 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.
The present invention relates to the use of isatin derivatives corresponding to formula I: ##STR2## in which R.sup.1 is hydrogen, a C.sub.1-4 alkyl, C.sub.2-4 hydroxyalkyl, C.sub.2-20 acyl, benzyl or phenyl group, R.sup.2 is hydrogen, a C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, halogen or nitro group, X is a sulfo group --SO.sub.3 H or a carboxyl group --COOH and n is an integer of 0 to 3, and water-soluble salts thereof for coloring keratin-containing fibers.
Examples of water-soluble salts are inter alia the alkali metal or ammonium salts.
Isatin derivatives corresponding to formula I, in which R.sup.1 and R.sup.2 are hydrogens and in which N=0, i.e. isatin derivatives corresponding to formula I in which the sulfo group or the carboxyl group is directly attached to the aromatic ring, are preferably used for coloring keratin-containing fibers. Isatin-5-sulfonic acid, isatin-4-carboxylic acid and isatin-5-carboxylic acid are most particularly suitable.
The isatin derivatives corresponding to formula I give yellow color tones

REFERENCES:
patent: 4750908 (1988-06-01), Rosenbaum et al.
patent: 4921503 (1990-05-01), Anderson et al.
patent: 5190564 (1993-03-01), Lang et al.
patent: 5261926 (1993-11-01), Lang et al.
patent: 5279616 (1994-01-01), Lang et al.
patent: 5340366 (1994-08-01), Lang et al.
"High Pressure Liquid Chromatographic Determination of Intermediates and Subsidiary Colors in FD&C Blue No., 2", J.E. Bailey, J. Assoc. Off. Anal. Chem., 1980, Abstract only.

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