Azo dyes for thermotransfer printing

Abstract

Azo dyes useful for thermotransfer printing have the formula ##STR1##

We claim: 
     
       1. A process comprising printing a substrate by thermotransfer printing with a transfer dye which is an azo dye of the general formula I ##STR32## in which the substituents have the following meanings: R 1  is hydrogen; C 1  -C 15  -alkyl, C 1  -C 15  -alkyl substituted by phenyl or phenoxy; cyclohexyl, cyclohexyl substituted by C 1  -C 5  -alkyl, C 1  -C 5  -alkoxy or halogen;   phenyl, phenyl substituted by C 1  -C 5  -alkyl, C 1  -C 5  -alkoxy, sulfonamido or halogen;   thienyl, thienyl substituted by C 1  -C 5  -alkyl or halogen; furanyl or pyridyl;   a radical of the formula II   [--W--O].sub.n --R.sup.4                                   II     where     W is identical or different C 2  -C 6  -alkylene,   n is from 1 to 6 and   R 4  is C 1  -C 4  -alkyl, phenyl or benzyl; phenyl or benzyl substituted by C 1  -C 4  -alkyl or C 1  -C 4  -alkoxy;   R 2  and R 3  are each hydrogen; alkyl, alkoxy, alkoxyalkyl, alkanoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylalkyl, haloalkyl, hydroxyalkyl or cyanoalkyl, each containing up to 15 carbon atoms;   alkyl, alkoxyalkyl, alkanoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylalkyl, haloalkyl, hydroxyalkyl or cyanoalkyl, each containing up to 15 carbon atoms, substituted by phenyl, C 1  -C 4  -alkylphenyl, C 1  -C 4  -alkoxyphenyl, halophenyl, benxyloxy, C 1  -C 4  -alkylbenzyloxy, C 1  -C 4  -alkoxybenzyloxy, halogenzyloxy, halogen, hydroxyl or by cyano;   cyclohexyl, cyclohexyl substituted by C 1  -C 15  -alkyl, C 1  -C 15  -alkoxy or halogen;   phenyl, phenyl substituted by C 1  -C 15  -alkyl, C 1  -C 15  -alkoxy, benzyloxy or halogen;   a radical of the above-mentioned formula II; and     D is the radical of a diazo component III.   D--NH.sub.2                                                III     .Iadd.wherein D is the radical of a diazo component III of the aminothiophene, phenylazoaminothiophene, aminothiazole, phenylazoaminothiazole, aminoisothiazole, aminobenzisothiazole, aminothiadiazole, aminoisothiadiazole, aminooxazole, aminooxadiazole, aminodiazole, aminotriazole or aminopyrrole series..Iaddend.     
     
     
       2. A process comprising transferring an azo dye or dyes by diffusiton from a transfer to a plastic-coated substrate by means of a thermal printing head, wherein said azo dye or dyes is or are of the formula I ##STR33## in which the substituents have the following meanings: R 1  on is hydrogen; C 1  -C 15  -alkyl, C 1  -C 15  -alkyl substituted by phenyl or phenoxy; cyclohexyl, cyclohexyl substituted by C 1  -C 5  -alkyl, C 1  -C 5  -alkoxy or halogen;   phenyl, phenyl substituted by C 1  -C 5  -alkyl, C 1  -C 5  -alkoxy, sulfonamido or halogen;   thienyl, thienyl substituted by C 1  -C 5  -alkyl or halogen; furanyl or pyridyl;   a radical of the formula II   [--W--O].sub.n --R.sup.4                                   II      where   W is identical or different C 2  -C 6  -alkylene,   n is from 1 to 6 and   R 4  is C 1  -C 4  -alkyl, phenyl or benzyl; phenyl or benzyl substituted by C 1  -C 4  -alkyl or C 1  -C 4  -alkoxy;     R 2  and R 3  are each hydrogen; alkyl, alkoxy, alkoxyalkyl, alkanoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylalkyl, haloalkyl, hydroxyalkyl or cyanoalkyl, each containing up to 15 carbon atoms;   alkyl, alkoxy, alkoxyalkyl, alkanoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylalkyl, haloalkyl, hydroxyalkyl or cyanoalkyl, each containing up to 15 carbon atoms, substituted by phenyl, C 1  -C 4  -alkylphenyl, C 1  -C 4  -alkoxyphenyl, halophenyl, benzyloxy, C 1  -C 4  -alkylbenzyloxy, C 1  -C 4  -alkoxybenzyloxy, halogenzyloxy, halogen, hydroxyl or by cyano;   cyclohexyl, cyclohexyl substituted by C 1  -C 15  -alkyl, C 1  -C 15  -alkoxy or halogen;   phenyl, phenyl substituted by C 1  -C 5  -alkyl, C 1  -C 5  -alkoxy, C 1  -C 15  -alkoxy, benzyloxy or halogen;   a radical of the above-mentioned formula II; and     D is the radical of a diazo component III   D--NH.sub.2                                                III     .Iadd.wherein D is the radical of a diazo component III of the aminothiophene, phenylazominothiophene, aminothiazole, phenylazominothiazole, aminoisothiazole, aminobenzisothiazole, aminothiadiazole, aminoisothiadiazole, aminooxazole, aminooxadiazole, aminoidazole, aminotriazole or aminopyrrole series..Iaddend.     
     
     
       3. A process as claimed is claim 2, wherein the azo dye or dyes has the formula Ia ##STR34## where the substituents have the following meanings: R 1  is C 1  14 C 8  -alkyl, C 1  -C 8  -alkyl substituted by phenyl or phenoxy; cyclohexyl;   phenyl, phenyl substituted by C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy or chlorine;   thienyl;   a radical of the formula IIa ##STR35##  where p is 0 or 1, q is from 1 to 4, and   R 4'   is C 1  -C 4  -alkyl, phenyl or benzyl;   R 2'  and R 3'  are each C 1  -C 12  -alkyl, C 1  -C 10  -alkoxy or C 1  -C 10  -cyanoalklyl or a radical of the above-mentioned formula IIa; and   D' is the radical of a diazo component III of the .[.aniline, phenylazoaniline..]. aminothiophene, phenylazoaminothiophene, aminothiazole, phenylazoaminothiazole, aminoisothiazole, aminobenzisothiazole, aminothiadiazle, aminooxadiazole, aminodiazole, aminotriazole or aminopyrrole series.