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Sulfide Hair dyes Disclosure Number: IPCOM000130141D
Publication Date: 2005-Oct-13

Publishing Venue

The Prior Art Database


Disclosed sulfide dyes and dyeing compositions comprising sulfide dyes. The sulfide dyes are selcted from anionic, cationic, neutral, amphoter and zwitterionic dyes., and are preferably derived from anthraquinone, acridine dye, azo, azomethine, hydrazo¬methine, benzodifuranone, cou¬marine, diketopyrrolopyrrol, dio¬xaxine, diphenylmethane, formazane, indigoid, indophenol, naphtalimide, naphtha¬quinone, nitroaryl, merocyanine, methine, oxazine, perinone, perylene, pyrenequinone, phtalocyanine, phena¬zine, quinoneimine, quinacridone, quinophtalone, styryl, triphenylmethane, xanthene, thia¬zine dye and thioxanthene dyes. The dyes which can be used as single components or as mixtures of 2 or more than 2 components of the same or different dye classes are useful for the dyeing of organic materials, such as keratin fibers, preferably human hair.

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Sulfide dyes

The present disclosure relates to sulfide dyes, mixtures of these dyes, compositions thereof, and to their use for the dyeing of organic materials, 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 that cationic dyes can be used for thedyeing of 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 washing.

The technical problem is to provide dyes that are distinguished by deep dying having good fastness properties with respect to washing, light, shampooing and rubbing.

Accordingly, the present disclosure relates to sulfoide dyes of formula
(1) S Y1


1 A1 ,

A1 is hydrogen; a radical of formula (1a) S Y2 (Z2)r D2

* ; or a thio ester group of


, wherein

E1 is O; S; or N-Ra;

B1 is -ORb; -NRbRc; or -SRb;

Ra, Rb and Rc, independently from each other are hydrogen; C1-C12alkyl; C6-C12aryl; or C6-


D1 and D2 independently from each other is a residue of an organic dye;

Y1 and Y2 independently from each other are unsubstituted or substituted, straight-chain or branched, interrupted for example by N, O or S or uninterrupted C1-C30alkylene; C5- C30cycloalkylene; C5-C40arylene; or-C5-C40arylene-(C1-C30alkylene);

Z1 and Z2 independently from each other are *-(CH2)p1-C(O)-**; *-((CH2)p1O)p2-**;

*-(CH2)p1-C(O)O-**; *-(CH2)p1-OCO-**; *-(CH2)p1-N(R60)-**; N+



formula (1b) *




* ;

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*-(CH2)p1-CON(R60)-**; *-(CH2)p1-(R60)NC(O)-**; -O-; -S-; -S(O)-; -S(O)2-; or a cationic biradical of a substituted or unsubstituted aromatic or heteroaromatic compound of the

formula (1a) G1

    N+ *



An -


An -


       N+ * **


; (1b)


; (1c)




* R62










; or (1e) N+

     G1 **



; wherein

An -

An -

G1 is N; -O-; -S-; or a radical of CR64; the asterix * indicatesthe linkage to D1 and/or D2; the asterix ** indicatesthe linkage to Y1 and/or Y2 ;

R60, R61, R62, R63 and R64 independently from each other are hydrogen; C1-C30alkyl; C2-

C30alkenyl; C6-C40aryl; C6-C40aryl-(C1-C30alkyl) ; or -C1-C30alkyl(C5-C40aryl).

C1-C30alkyl 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, nonyl, decyl,.undecyl, dodecyl, eicosyl or triacontyl.

C1-C30alkylene is for example methylene, ethylene, propylene, isopropylene, n-butylene, sec- butylene, tert-butylene, n-pentylene, 2-pentylene, 3-pentylene or 2,2'-dimethylpropylene, n- hexylene, n-octylene, 1,1',3,3'-tetramethylbutylene, 2-ethylhexylene, nonylene, dec...