ANTHRAQUINONE DYESTUFFS AND PROCESSES FOR THEIR PRODUCTION

The invention comprises anthraquinone dyestuffs of the formula wherein R1 represents a C1-C4 alkyl radical or a halogen atom, R2 represents a C1-C4 alkyl radical, R3 represents H or an alkyl radical; and Z represents a 5- or 6-membered heterocyclic ring which carries at least one labile substituent, or a group containing a 5- or 6-membered heterocyclic ring which carries at least one labile substituent, or an aliphatic, araliphatic or aromatic radical with at least one reactive substituent. They may be obtained either by condensing a sulphonamide of the formula with a sulphonic acid halide of the formula Hal-O2S-Z wherein Hal represents a halogen atom, or by condensing a sulphonic acid halide of the formula with a sulphonamide of the formula H2N-O2S-Z Some of the dyes may also be obtained by condensing 1 - amino - 4 - bromo - anthraquinone - 2 - sulphonic acid with an amine of the general formula:- Specified heterocyclic radicals Z are 2-chlorothiazol - 1,3 - yl - 4; 2 - chlorothiazol - 1,3 - yl - 5; 2,4 - dichloropyrimidin - 1,3 - yl - 5; 2- chlorobenzothiazol - 1,2 - yl - 5 and - yl - 6; 2-chlorobenzoxazol - 1,3 - yl - 5 and - yl - 6; 2,3 - dichloroquinoxalinyl - 6; 2,4 - dichloroquinazolinyl - 6 and - 7; 1,4 - dichlorophthalazinyl - 6 and 2 -, 3 - and 4 - (41,51-dichloropyridazon - 61 - yl - 11) - phenyl. Specified aromatic radicals Z are 4-fluoro- and 4 - chloro - 3 - nitrophenyl - 1. Specified aliphatic and araliphatic radicals Z are -CH2CH2Cl, -CH = CH2, -CH2CH2 OSO3H, -CH2CH2SO2CH3, -CH2CH2 OSO2CH3 and Examples are given for the production of dyestuffs where Z is the heterocyclic radical. They may be used for dyeing or printing cellulose-containing materials or materials containing amide groups. The sulphonic acid amides of the Formula II are obtained by sulphonating the appropriate anthraquinone compound analagous to those of Formula II but not containing a sulphonamide group, e.g. with ClSO3H, converting the sulphonic acid formed to the corresponding acid chloride, e.g. with thionyl chloride, and condensing the acid halide with NH3. An example is given for the preparation of 1-amino-4-(21,61 - dimethyl - 31 - sulphamido) - phenyl-amino - anthraquinone - 2 - sulphonic acid and the corresponding 41-sulphonamido compound.ALSO:Cellulose and amide group containing materials are dyed or printed with anthraquinone dyes of the formula: