GB473615A - Manufacture of arylides of hydroxy-ortho-carboxy-benzoacridones and of azo-dyestuffs therefrom - Google Patents

Abstract

Arylides of o-hydroxycarboxy-benzoacridones are made by condensing a o-hydroxycarboxybenzoacridone with a primary arylamine which is free from groups lending solubility, such as SO3H or COOH. In examples: (1) and (2) 4<1>-hydroxy-5<1>-carboxy-1 : 2-benzoacridone is condensed with aniline in presence of phosphorus trichloride or phosphorus pentoxide, or (3) and (4) with o- or p-anisidine in presence of phosphorus trichloride in chlorbenzene, or (5) with 1-amino-2-methyl-4-methoxybenzene in presence of o-nitroanisole and phosphorus trichloride; (6) and (7) 4<1>-hydroxy p - 5<1> - carboxy - 3 : 4 - benzoacridone is condensed with aniline and p-anisidine as above; (8) and (9) 4<1>-hydroxy-5<1>-carboxy-1 : 2-benzoacridone is condensed with a - or b -naphthylamine as above. o-Hydroxycarboxybenzoacridones are made by heating an o-carboxyphenylamino-2-naphthol-3-carboxylic acid with concentrated sulphuric acid, e.g. 4<1>-hydroxy-5<1>-carboxy-1 : 2-benzoacridone from 6-(2<1>-carboxyphenylamino)-2-naphthol-3-carboxylic acid and 4<1>-hydroxy-5<1>-carboxy - 3 : 4 - benzoacridone from 8 - (2<1>-carboxyphenylamino)-2-naphthol-3-carboxylic acid. Azo dyes are made in substance on the fibre or on a substratum by coupling an arylide of an o-hydroxycarboxybenzoacridone as above defined with any diazo compound, the components containing no solubilizing groups. Olive green, grey and brown shades are obtained. In examples: (11) cotton is grounded with a solution of the anilide of 4<1>-hydroxy-5<1>-carboxy-1 : 2-benzoacridone in alcohol, caustic soda, water, sulphite cellulose waste liquor and oleylmethyltaurine and developed with diazotized p-nitroaniline; (12) the dyestuff of (12) is made in substance. Additional diazo components specified in a table are: 4- or 5-chlor-2-methoxy-1-aniline, 2-nitro-4-methyl-1-aniline, 4-chlor-2-nitroaniline, 4 - nitro - 2 - methoxy - 1 - aniline, 2 : 5-dichloraniline, 5-nitro-2-methoxy-1 - aniline, 2- or 3 - chloraniline, 2 - nitro - 4-methoxy - 1 - aniline, 4<1> - methoxy - 4 - aminodiphenylamine, 2<1> : 3 - dimethyl - 4 - aminoazobenzene, 4-nitro-2-methyl-1-aniline, 4-chlor-2-methyl-1-aniline, 2-chlor-5-methoxy-4-benzoylamino-1-aniline, 3-nitroaniline, 4<1>-nitro-3 : 6-dimethoxy-4-aminoazobenzene, 1-aminoanthraquinone, 4 : 6 - dimethyl - 3 - benzoylamino - 1 - aniline.