Patent GB-747872-A (GB)
Title: Metallisable azo dyestuffs
Inventor: DAVIES ROBERT RONALD
IPC: F16F15/12
Filed: 1953-06-17
Abstract: Dyestuffs are made by diazotizing an o-amino-phenol sulphuric acid ester and coupling under alkaline conditions with a coupling component which contains at least one coupling position adjacent to a metallizable group, the coupling being effected at the said coupling position.  o-Aminophenol sulphuric acid esters specified are 2-amino-phenol sulphuric ester and the 4-methyl-and -methoxy derivatives thereof and 1-amino-2-naphthol and 2-amino-1-naphthol sulphuric esters.  Coupling components used in the preparation of monoazo dyestuffs are preferably free of carboxylic and sulphonic acid groups those specified being 6-methyl-2-(41-acetoacetaminophenyl) benzthiazole, 2-(21-hydroxy-31 -naphthoylamino) naphthalene, 6-(21-hydroxy -31- naphthoylamino) indazole and 21- hydroxy -31- naphthoylaminobenzene.  Disazo dyestuffs may be obtained by the use of coupling components containing two coupling positions adjacent to metallizable groups two molar proportions of sulphuric ester being used.  Coupling components specified for the preparation of disazo dyestuffs are 4, 41-bisacetoacetylamino-3, 31-dimethyl-and -dimethoxy-diphenyl, 4, 41-bisacetoacetylaminostilbene, 1, 5, 1, 4 and 2, 6-bisacetoacetylamino-naphthalene, 4, 41-bis (311-methylpyrazole-511-one-111-yl)-diphenyl and its 3, 31-dimethyl derivative 4, 4-1bis (611hydroxy - 211naphthoyl) - 3, 31-dimethoxy-diphenyl and 5, 6-dihydroxy-and -diamino-indazole. Coupling components may also be used which may themselves be diazotized so that the dyestuffs obtained by the use of such components may be diazotized and coupled with a second coupling or end component, which preferably is capable of metallization per se. Specified coupling components for this feature of the invention are 2-amino- and -(31-aminobenzoylamino) - 5 - naphthol - 7 - sulphonic acid and 2-amino-8-naphthol-6-sulphonic acid.  End components specified for use with diazotized aminomonoazo dyestuffs obtained as above are 8-hydroxyquinoline and its 7-chloro- and 6-methoxy derivatives, 4-hydroxy-acridine, -benzthiazole and -2- benzoyl- and -acetylaminobenzthiazole and 6-hydroxyndazole. The dyestuffs may be applied to cellulosic fibres e.g. cotton and cellulose acetate, particularly by the after coppering process the sulphonic acid ester group being displaced.  The dyeing of nylon and wool fibres is also mentioned.  Pink, yellow, orange, brown, red and blue shades are obtained according to the dyestuffs used.  Further metal compounds specified are those of nickel, chromium and cobalt.  In examples the sulphuric acid ester of o-amino-phenol is diazotized and coupled with (1) 2- or 6-(21-hydroxy-31-naphthoylamino) indazole or 1-(21hydroxy-31-naphthoylamino) naphthalene, (2) 4, 41-bisaceto-acetylamino-3, 31-dimethyldiphenyl or 1, 5-, 2, 7-, 2, 6-, 6- or 1, 4-disacetoacetylaminonaphthalene and the o-amino-phenol ester may be replaced by 4-methyl- or -methoxy-2-amino-phenol sulphuric acid ester, (3) 4, 41-bis-(311 methylpyrazol 511- one -111-yl) or -(311-methyl-511-aminopyrazole-111-yl) diphenyl, 4, 41-bis-acetoacetamino-diphenyl or bis (6-hydroxy-2-naphthoyl) dianisidine and the additional acid esters of (2) may be used and also 1-amino-2-naphthol sulphuric ester, (4) 5, 6-dihydroxy- or -diamino-indazole and the additional acid esters of (2) may be used, (5) resorcinol the monoazo dyestuff thus obtained being coupled with tetrazotized benzidine or anisidine and the additional acid esters of (2) may be used, (6) 2- amino -5- naphthol -7- and -8- naphthol -6- sulphonic acids the monoazo dyestuffs thus obtained being diazotized and coupled with 8-hydroxyquinoline, 4-methoxy -2-amino-phenol sulphuric acid also being used and (7) p-cresol or 1-(31-chlorophenyl)-3-methyl-5-pyrazolone.  b -Ethoxyethanol is present during some of the coupling reactions of the examples. Specification 282,107 [Class 2(iii)], is referred to.