GB374548A - Manufacture of hydroxycarboxylic acid arylides - Google Patents

Abstract

2 : 3-Hydroxynaphthoyl derivatives are made by condensing 2 : 3-oxynaphthoic acid or a substitution product thereof with 4-aminodiphenyl or a substitution product thereof which does not contain a further amino group in the diphenyl nucleus. The substitution products of 4-aminodiphenyl include compounds containing a bridge in the 2 : 2<1>-position of the diphenyl nucleus, e.g. 2-aminofluorene, 2-aminofluorenone, 2-aminocarbazole or 2-aminodiphenyleneoxide. In examples (1) 2 : 3-oxynaphthoic acid is condensed with 4-aminodiphenyl in presence of toluene and phosphorus trichloride; the 4<1>-nitro, 4<1>-chloro, 3-methoxy, 2 : 5-dimethoxy, 2 : 5 : 4<1>-trimethoxy, and 2<1>-methoxy derivatives of 4-aminodiphenyl are also specified as starting materials; the 6-bromo-2 : 3-oxynaphthoyl derivatives of 4-aminodiphenyl and 4-amino-2 : 5-dimethoxydiphenyl and the 7-methoxy-2 : 3-oxynaphthoyl derivative of 4-aminodiphenyl may be similarly prepared, (2) 2 : 3-oxynaphthoic acid is condensed with 2-aminofluorene by means of phosphorus trichloride in chlorobenzene, (3) 2-acetoxy-3-naphthoyl chloride is condensed with 2-aminofluorenone in presence of pyridine using benzene as solvent and the product hydrolysed, (4) 2 : 3-oxynaphthoic acid and 2-aminocarbazole are condensed by means of phosphorus trichloride in xylene. Specification 23732/13, [Class 2(iii), Dyes &c.], is referred to. Azo dyes, forming on the material. The above arylides which have a high substantivity are used for producing azo dyes on the fibre. In examples (5) cotton impregnated with 2<1> : 3<1>-oxynaphthoyl-4-aminodiphenyl is developed with diazotized 4-chloro-2-nitraniline; the residual grounding liquor may be used for a further impregnation, (6) cotton grounded with 2<1> : 3<1>-oxynaphthoyl-4-amino-2 : 5-dimethoxy-diphenyl is developed with diazotized 1-amino-2-methyl-5-chlorobenzene (blueish red fast to light), (7) cotton impregnated with 2<1> : 3<1>-oxynaphthoyl-2-aminofluorene is developed with diazotized 4-chloro-2-nitraniline, (8) cotton grounded with 2<1> : 3<1>-oxynaphthoyl-2-amino-fluorenone is developed with diazotized 4-nitro-2-toluidine. A table showing the shades obtained by using various components is given. Specification 228,913, [Class 2 (iii), Dyes &c.], is referred to.