GB869031A - Improvements in or relating to heterocyclic monoazo dyestuffs and their chromium andcobalt complex compounds - Google Patents

Abstract

The invention comprises dyestuffs of formula: <FORM:0869031/IV(c)/1> where B is the residue of an azo component of the naphthalene series coupling in the orthoposition to a hydroxy group or to a primary or secondary amino group, or for the residue of an azo component of the pyrazolone or acylacetylamino series coupling in ortho-position to an enolic hydroxy group, Y for a substituent capable of metallization, Z for a phenolic or enolic hydroxy group or a primary or secondary amino group in ortho-position to the -N=N-group, n for 1 or 2 and p for 3 or 4 and where A and B may contain further substituents and the heterocyclic group may be a substituent in either A or B, or in both A and B but excludes those dyes where p is 3 and the heterocyclic group is in A. The invention also includes chromium and -cobalt complexes of the above-claimed dyestuffs, the 1, 2-complexes being preferred. The dyestuffs may be made by coupling appropriate diazo compounds containing nucleus A with the required component B and metallizing if desired. Conventional processes are used for the preparations, coupling with hydroxy or enolic compounds being effected preferably in weakly acid to strongly alkaline media and with amines in a weakly acid, preferably acetic acid, medium. Metallization may be effected in substance on the fibre. Substituent Y is preferably OH, COOH or MeO. Indicated as substituents for A are halogen atoms, nitro, acetyl-, benzoyl-, carbomethoxy- and carboethoxy-amino, carboxy, methyl, ethyl, tert. buty, methoxy, sulphonic acid, sulphonamide, N-methyl-, -dimethyl-, -(21-hydroxyethyl)-, -di-(21-hydroxyethyl)-, -(31-hydroxypropyl)- and -(31-methoxy-propyl)-, -(phenyl)- and -(21-carboxyphenyl)-amide and methylsulphonyl groups and the above heterocyclic group. Indicated coupling components are hydroxy-napthalenes, amino-, alkylamino-, cycloalkylamino-, aralkylamino and arylaminonaphthalenes, 1-aryl-3-methyl-5-pyrazolones and acylacetylamino-alkanes, -benzenes and -naphthalenes which may carry the same substituents as the diazo components the heterocyclic substituents being preferred. The dyestuffs dye wool, silk, leather and polyamide fibres by afterchroming and one bath chroming processes in red, yellow, green, blue, violet, grey and brown shades. The metal dyes dye the same materials from neutral or weakly acid dye baths in similar shades. Dyestuffs soluble in organic solvents may be used in spun filaments, plastics and lacquer media. In examples which illustrate the preparation of the dyestuffs and their use in dyeing processes the diazo cpmponents used are 2-amino-4-nitro-phenol and 2-aminophenol-4-sulphonamide and -sulphonmethylamide and the coupling components are 1-acetylamino-7-naphthol, 1-Y (where Y is the heterocyclic group with p=4)-7-naphthol and 2-(31-X-phenyl-amino)-naphthalene. A Table is also provided of a great number of dyestuffs obtained by the above processes and the results of their use in dyeing wool or spun dyed fibres the components used being selected from those indicated above with cyano and various N-substituted sulphonamido groups as additional substituents. Reference has been directed by the Comptroller to Specification 753,987.