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Cationic dimeric dyes

IP.com Disclosure Number: IPCOM000031281D
Publication Date: 2004-Sep-21

Publishing Venue

The IP.com Prior Art Database

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Eva Veenstra: CONTACT

Abstract

The present invention relates to novel cationic dyes. Further, the present invention relates to compositions thereof, especially comprising other dyes, to processes for the preparation thereof and to the use thereof in the dyeing of organic material, such as keratin, wool, leather, silk, paper, cellulose or polyamides, and preferably human hair.

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Cationic dimeric dyes

The present invention relates to novel cationic dyes, compositions thereof, to processes for their preparation and to their use in the dyeing of organic material, such as keratin fibers, wool, leather, silk, paper, cellulose or polyamides, especially keratin-containing fibers, cotton or nylon, and preferably hair, more preferably human hair.

It is known, for example, from WO 95/01772, WO 95/15144, EP 714 954 and EP 318 294 that cationic dyes can be used to dye organic material, for example keratin, silk, cellulose or cellulose derivatives, and also synthetic fibers, for example polyamides. Cationic dyes exhibit very brilliant shades. A disadvantage is their unsatisfactory fastness to hydrolysis and to light, their frequently inadequate stability under reducing or oxidizing conditions, and their frequently unsatisfactory storage stability (see: John F. Corbett:"The Chemistry of Hair-Care Products", JSCD August 1976, page 290).

The actual technical problem of the present invention was to provide brilliant dyes that are distinguished by deep dyeing having good fastness properties with respect to washing, light, shampooing and rubbing, for the dyeing of organic material.

Accordingly, the cationic dyes of formula (1) or (1a)

 (1)     (1a)

have been discovered,

wherein

A is an organic radical of formula (2) or (3)
(2)

 (3)

wherein

R1 and R2 are each independently of the other unsubstituted or substituted C1-C14alkyl or an aryl radical,

R3 is hydrogen, unsubstituted or substituted C1-C14alkyl, unsubstituted or substituted

C1-C14alkoxy, cyan or halogenid,

R4 is hydrogen, unsubstituted or substituted C1-C14alkyl or an aryl radical,

and

X- is an anion.

Preferred is a cationic dye of formula (1) and/or (1a), wherein

R1 and R2 are each independently of the other unsubstituted or substituted C1-C6alkyl or unsubstituted or substituted benzyl,

R3 is hydrogen, unsubstituted or substituted C1-C6alkyl, unsubstituted or substituted C1-C6alkoxy, cyan or chlorid,

R4 is hydrogen, unsubstituted or substituted C1-C6alkyl or unsubstituted or substituted benzyl,

and

X- is an anion.

More preference is given to a cationic dye of formula (1) and/or (1a), wherein

R1 and R2 are each independently of the other unsubstituted or substituted C1-C6alkyl or unsubstituted or substituted benzyl,

R3 is hydrogen,

R4 is hydrogen, unsubstituted or substituted C1-C6alkyl or unsubstituted or substituted benzyl,

and

X- is an anion.

In the present invention, substituents of C1-C14alkyl, C1-C6alkyl, aryl or benzyl are, for example hydroxyl, NR5R6, wherein

R5 and R6 are each independently of the other hydrogen, unsubstituted or substituted aryl radical or C1-C6alkyl; or C1-C8alkyl, C1-Calkoxy, cyanide and/or halide.

C1-C14alkyl is, for example, C1-C8alkyl, C1-C6alkyl and preferably C1-C4alkyl, and may be straight-chain, branched, substituted or unsubstituted, or, from C5alkyl upwards, monocyclic or polycyclic, and may be uninterrupted or interrupted by hetero a...