Patent GB-446584-A (GB)
Title: Manufacture of azo-dyestuffs
IPC: C09B45/16
Filed: 1934-11-03
Abstract: Azo dyestuffs are manufactured by coupling the diazo-compound of a sulphoanthranilic acid derivative not containing a hydroxyl group in a-position to the diazotizable amino-group and having the constitution <FORM:0446584/IV/1> where R represents OH, O-alkyl, O-aryl, O-aralkyl or <FORM:0446584/IV/2> where X and Y are hydrogen or alkyl, aryl, aralkyl or hydroaromatic radicles, and R<1> and R<11> represent hydrogen or alkyl, aryl, aralkyl or hydroaromatic radicles free from sulphonic acid groups, with an aminonaphtholsulphonic acid or a derivative of a 1-aryl-5-pyrazolone containing at least one solubilizing group.  The products are suitable for dyeing animal fibres, the dyeings in some cases being capable of being after-chromed.  Examples describe the preparation of the following dyestuffs: (1) 1 - aminobenzene - 2 - carboxylic acid - diethylamide - 5 - sulphonic acid - diethylamide --> 2 - amino - 8 - naphthol - 6 - sulphonic acid; the product dyes wool in an acid bath bluish red tints and also dyes unloaded or loaded silk; (2) the same diazo-component --> 1-(2<1>-hydroxy - 3<1> - carboxy - 5<1> - sulpho) - phenyl-3-methyl-5-pyrazolone; the product dyes wool clear yellow tints; (3) the same diazo-component --> 1-(2<1>-chloro-5<1>-sulpho)-phenyl-3-methyl-5-pyrazolone (somewhat greener shades than in (2)); (4) 1-aminobenzene-2-carboxylic acid-dimethylamide-5-sulphonic acid-dimethylamide --> 2-amino-8-naphthol-6-sulphonic acid (tints similar to those of (1)); (5) 1-aminobenzene - 2 - carboxylic acid - methyl - ester - 5-sulphonic acid-diethylamide --> 2-amino-8-naphthol-6-sulphonic acid (bluer tints than those of (1)); (6) the diazo-component of (5) --> 1-acetylamino-8-naphthol-3 : 6-disulphonic acid (yellowish red tints); (7) the diazo-component of (5) --> 1-(2<1>-hydroxy-3<1>-carboxy-5<1>-sulpho)-phenyl - 3 - methyl - 5 - pyrazolone (reddish yellow dyeings which may be after-chromed); (8) the diazo-component of (5) --> 1-(2<1>-chloro5<1> - sulpho) - phenyl - 3 - methyl - 5 - pyrazolone (greenish yellow tints); (9) 1-aminobenzene-2-carboxylic acid-5-sulphonic acid-diethylamide --> 1-(2<1>-chloro-5<1>-sulpho)-phenyl-3-methyl-5-pyrazolone (greenish yellow dyeings becoming more reddish on after-chroming). A table gives the properties of further dyestuffs, the following additional components being specified: diazo - components: 1 - aminobenzene - 2 - carboxylic acid-5-sulphonic acid-amide, -phenylamide and N - ethylphenylamide, 1 - aminobenzene - 5 - carboxylic acid - amide - 5 - sulphonic acid - amide, 1 - aminobenzene - 2 - carboxylic acid - methylamide - 5 - sulphonic acidmethylamide, 1 - aminobenzene - 2 - carboxylic acid - ethylamide-5-sulphonic acid-ethylamide and 1-aminobenzene-2-carboxylic acid-N-ethylphenylamide-5-sulphonic acid-N-ethylphenylamide; coupling components: 2-phenylamino-8-naphthol-6-sulphonic acid and 1-(4<1>-sulphophenyl) - 3 - methyl - 5 - pyrazolone. Specifications 302,965, [Class 2 (iii)], and 413,588 are referred to.  Sulphoanthranilic acid derivatives of the general formula given above are obtainable by condensing an acid chloride of one of the following formul  <FORM:0446584/IV/3> with the appropriate amine and reducing the nitro-group.  For the production of compounds having different substituents in the sulphonic acid and carboxylic acid groups, the compound <FORM:0446584/IV/4> (prepared as described above, or by treating 2-nitrotoluene or a derivative thereof not substituted in the 4-position with chlorsulphonic acid, condensing the sulphochloride with the appropriate amine and oxidizing the methyl group, e.g. with permanganate) is transformed into the carboxylic acid chloride, which is condensed with a second amine or converted into the ester.