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Cationic substituted hydrazone dyes

IP.com Disclosure Number: IPCOM000030555D
Publication Date: 2004-Aug-17

Publishing Venue

The IP.com Prior Art Database

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Eva Veenstra: CONTACT

Abstract

The present invention relates to novel cationic hydrazone 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 fibers, especially hair; or wool, leather, silk, cellulose or polyamides, and preferably human hair.

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HP/5-22838

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Cationic substituted hydrazone 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 fibres, 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 fibres, 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 oxidising 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 oxidising dyeing conditions, for the dyeing of organic material.

Accordingly, the cationic dyes of formula (1), (2) or (3)

R3

R3

R4

R4

+

R1

N

N N

N

N N

+

X-

R2

R1

X-

R2

(1),

(2) and

R1 R3

X-

+

N

R4

N N

R2

(3)

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have been discovered, wherein
R1 and R2 are each independently of the other a C1-C8alkyl radical or an unsubstituted or substituted benzyl radical, R3 is hydrogen, C1-C8alkyl, C1-C8alkoxy, cyanide or halide, preferably hydrogen, and R4 is a C1-C8alkyl radical or an unsubstituted or substituted aryl radical, and X- is an anion.

In the present invention, substituents of aryl, especially benzyl, or heterocyclic organic radical are, for example C1-C8alkyl, C1-C8alkoxy, cyanide and/or halide.

The alkyl radical is, for example, C1-C8alkyl, 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 atoms, such as O, S, N, NH.

C1-C8alkyl is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2'-dimethylpropyl, cyclopentyl, cyclohexyl, n-hexyl, n-octyl, 1,1',3,3'-tetramethylbutyl or 2-ethylhexyl.

C1-C4alkyl is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

C1-C8alkoxy is O-C1-C8alkyl, preferably O-C1-C4alkyl.

Aryl radical is, for example, a phenyl-, benzyl-, tolyl radical or a substituted or unsubstituted heterocyclic organic radical.

Heterocyclic organic radical is, for example, a five-membered nitrogen-containing heterocyclic radical such as imidazolyl, pyrazolyl, triazolyl, pyrrolyl, pyrrol...