GB514353A - New azo compounds and dyestuffs derived therefrom - Google Patents

Abstract

514,353. Dyes. DU PONT DE NEMOURS & CO., E. I. Jan. 24, 1938, No. 2301. Void. Convention date, Jan. 23,1937. [Classes 2 (iii) and 15 (ii)] Disazo dyes are made by tetrazotizing an N : N<1>-di (aminoaroyl)-phenylene- or naphthylenediamine and coupling with two mols. of the same or different coupling components having at least one free amino group. The aryl nuclei may be substituted by sulphonic, alkyl, alkoxy, halogen, oxyacetic acid, or azo groups. Many of one products are direct dyes for cotton and regenerated cellulose, the shades obtained ranging from yellow to red. In examples, (1) N: N<1>-di-(p-aminobenzoyl)- m-phenylene diamine is tetrazotized and coupled with (a) J-acid (2 mols.), (b) 1-m-aminophenyl- 5-pyrazolone-3-carboxylic acid (2 mols.), and (2) N: N<1>-di (p-aminobenzoyl)-1: 3-diaminobenzene-4-sulphuric acid is tetrazotized and coupled with (a) 1-m-aminophenyl-3-methyl-5- pyrazolone (2 mols.), (b) 1-m-aminophenyl-5- pyrazolone-3-carboxylic acid (2 mols.), (c) p-aminobenzoyl-J-acid (2 mols.) and (d) maminobenzoyl-J-acid (2 mols.). A large number of other combinations is tabulated, the following additional components being specified : tetrazo components - N : N<1>-di-(p-aminobenzoyl)-pphenylenediamine, N: N<1>-di-(p-aminobenzoyl)- 1 : 4-naphthylenediamine, and N : N1-di- (p-aminobenzoyl)-1 : 4-phenylenediamine-5-sulphonic acid ; coupling components :-di-(paminobenzoyl)-3 : 5-diaminobenzoyl-J-acid, and m-toluidine. The disazo dyes from (1) N: N<1>- di-(p-aminobenzoyl)-1 : 3-phenylenediamine-4- sulphonic acid (1 mol.), 1-m-aminophenyl-5- pyrazolone-3-carboxylic acid (1 mol.) and p-aminobenzoyl-J-acid (1 mol.), and (2) N: N<1>- di-(p-aminobenzoyl)-m-phenylenediamine and 1-maminophenyl - 5 - pyrazolone - 3 -carboxylic acid (2 mols.), are tetrazotized and further coupled with 1-m-aminophenyl-5-pyrazolone- 3-carboxylic acid (2 mols.).