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Cationic dyes

IP.com Disclosure Number: IPCOM000030740D
Publication Date: 2004-Aug-25

Publishing Venue

The IP.com Prior Art Database

Related People

Eva Veenstra: CONTACT

Abstract

The present invention relates to novel cationic azo 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, cellulose or polyamides, and preferably human hair.

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Page 1 of 102

Case HP/5-22839

- 1 -

Cationic 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, 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 dying having good fastness properties with respect to washing, light, shampooing and rubbing, and that preferably exhibit satisfactory stability under reducing or oxidizing dyeing conditions, for the dyeing of organic material.

Accordingly, the cationic dye of formula (1)

N

N

CH3

-CH3

+ N

H R1

R2 R7

N N

(1),

has been discovered, wherein R1 and R7 are each independently of the other hydrogen, hydroxyl; unsubstituted or substituted C1-C6alkyl, aryl radical or C1-C6alkoxy; or -NR3R4, wherein

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Page 2 of 102

- 2 -

R3 and R4 are each independently of the other hydrogen, unsubstituted or substituted aryl radical or C1-C6alkyl, and
R2 is hydrogen, hydroxyl, unsubstituted or substituted C1-C6alkyl, aryl radical or

C1-C6alkoxy, -NR3R4, or an organic radical of formula (2)

C

H3

N

NR5 N N

+

N

C

H3 X (2)

wherein

R5 is hydrogen, unsubstituted or substituted aryl radical or C1-C6alkyl, and X- is an anion.

Preferred is a cationic dye of formula (1), wherein R1 and R7 are each independently of the other hydrogen, unsubstituted C1-C6alkyl, -(C1- C6alkylen)-OH, -(C1-C6alkylen)-NR3R4 or -NR3R4, wherein R3 and R4 are each independently of the other hydrogen, unsubstituted C1-C6alkyl, and R2 is hydrogen, hydroxyl, unsubstituted C1-C6alkyl, -(C1-C6alkylen)-OH, -(C1-C6alkylen)- NR3R4; or -NR3R4, or an organic radical of formula (2).

Further, preference is given to a cationic dye of formula (1), wherein R1, R2 and R7 are the same substituents, such as hydrogen, unsubstituted C1-C6alkyl, -(C1-C6alkylen)-OH, or -(C1- C6alkylen)-NR3R4.

More preferred is a cationic dye of formula (1), wherein R1 and R7 are hydrogen.

In the present invention, substituents of C1-C6alkyl, aryl or benzyl are, for example hydroxyl, NR3R4, wherein
R3 and R4 are each independently of the other hydrogen, unsubstituted or substituted aryl radical or C1-C6alkyl; or
C...