GB796350A - Improvements relating to metallisable monoazo dyestuffs, complex heavy metal compounds thereof, and their use - Google Patents

Abstract

The invention comprises dyestuffs of formula <FORM:0796350/IV (b)/1> where A is a benzene residue bound to -N = N- in o-position to OH and containing no water-solubilizing groups which dissociate acid in neutral water and complex metal compounds of formula (F-M1-F1)M2 where M1 is Cr or Co, M2 is an alkali metal cation, F is F1 or a coordinated o,o1-dihydroxy monazo dyestuff containing no water-solubilizing groups which dissociate acid in neutral water and F1 is a coordinated dyestuff of the above formula. The metal free dyestuffs are made by coupling o-aminophenols with 1-carbamylamino-7-naphthol advantageously in aqueous-alkaline solution and optionally in the presence of tert. nitrogen bases. The phenols may contain halogen, alkyl, nitro, acylamino, acyl, alkyl or aryl sulphone, cyano, carboxylic acid amide, or sulphonamide substituents the latter especially when derived from secondary aliphatic, araliphatic or heterocyclic amines and particularly carboxylic acid anilide groups. Specified diazo components are 4-, 5- and 6-nitro-, 4- and 5-chloro-, 4,5- and 4,6-dichloro-, 3,4,6-trichloro-, 4-methyl-, tert. and n-butyl-, tert. amyl-, acetyl-, benzoyl-, cyano-, phenyl-, p-toluylsulphonyl-, 4-methyl- and chloro-5-nitro-, 4-methyl-, tert. butyl-, tert. amyl acetylamino- and chloro-6-nitro-, 6-acetylamino- and chloro-4-nitro -, 6 - acetylamino - 4 - acetyl -, chloro-and butylsulphonyl - and 4,6 - dinitro - 2-aminophenols, 2 - aminophenol - 4 - sulphonic acid - dimethyl - and diethyl - amides, anilide, N-methyl - and ethyl - anilides, piperidide and morpholide. Metallization is effected in conventional fashion either in substance or on substrata. Mixed metal complexes are preferred where F1 is derived from a dyestuff which yields blue to green metal complexes and F is derived from a dyestuff having no SO3H groups and which produces yellow to orange metal complexes as obtainable, e.g. from diazotized o-amino-phenols or benzene carboxylic acids and acyl acetic acid arylamides and 5-pyrazolones. The resulting mixed metal complexes have brown to green or grey shades. The metal dyestuffs dye natural and synthetic polypeptide fibres such as wool, silk, polyamide and polyurethane fibres from weakly alkaline to weakly acid dyebaths. When dyeing textiles it is preferred that the complexes are used as their alkali metal salts. Examples and a Table are provided illustrating the preparation of the dyestuffs and their metal complexes and the use of the latter in dyeing wool, the components used are chosen from those listed above with the addition of 2-aminophenol-4-phenyl sulphone, for single dyestuffs the components used corresponding to F when not F1 are 2-aminophenol-4-ethyl sulphone and acetoacetic acid o-chloranilide and 1-(31-chlorophenyl)-3-methyl-5-pyrazolone. Reference has been directed by the Comptroller to Specification 637,404.