Patent GB-523035-A (GB)
Title: The manufacture of new azo dyestuffs
IPC: C09B35/28
Filed: 1938-12-22
Abstract: 523,035. Dyes KNIGHT, A. H., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Dec. 22, 1938, No. 37341. [Class 2 (iii)] Disazo dyes for dyeing animal fibres such as wool or silk are obtained by tetrazotising a diamine of the general formula H 2 N.C 6 H 4 . NR.CO.CO-NR.C 6 H 4 .NH 2  or H 2 N.C 6 H 4 .NR. CO.CnH 2 n.CO.NR.C 6 H 4 .NH 2 , wherein n represents one of the whole numbers 2 to 10, R represents an alkyl radicle with not more than 5 carbon atoms or benzyl, the amino groups are in the same relative positions in the two phenylene residues, and these residues may be substituted, e.g., by halogen, methyl, or alkoxy, in the same positions in each, and coupling with two molecular proportions of a sulphoarylpyrazolone, a naphtholsulphonic acid, an aminonaphtholsulphonic acid or an N-phenyl, N-acyl or N-alkyl derivative of an aminonaphtholsulphonic acid. In examples the manufacture of the following dyestuffs is described : (1), (2), (3) and (7) the di-(4-amino- N-ethylanilide) of sebacic acid<SP>#</SP> (1) 1-(2<SP>1</SP>:5<SP>1</SP>- dichloro-4<SP>1</SP>-sulpho) phenyl-3-methyl-5-pyrazolone, (2) N-acetyl-1:8:3:6-aminonaphtholdisulphonic acid, (3) 2:8:6-aminonaphtholsulphonic acid, (7) 1:5-naphtholsulphonic acid (2 mols.), which dye wool (1) greenish yellow, fast to milling, washing and light, from a bath containing ammonium acetate, (2) red, similarly fast, from a bath containing sulphuric acid and Glauber salt, (3) red, fast to milling and washing, from an acid bath, (7) red, fast to milling, washing, perspiration, sulphur stoving and light, from a bath containing ammonium acetate, (4) the di-(4-amino-N-ethylanilide) of oxalic acid## 1- (4<SP>1</SP>-sulpho) phenyl-3-methyl - 5 - pyrazolone (2 mols.), which dyes wool reddish yellow, fast to milling, washing, perspiration, sulphur stoving and light, from an acid bath, (5) the di-(4-amino- N-ethylanilide) of succinic acid## 1:4-naphtholsulphonic acid (2 mols.), which dyes wool scarlet, similarly fast, from an acid bath, (6) the di-(4-amino-N-ethyl- or N-methyl-anilide) of azelaic acid##1:4-naphtholsulphonic acid (2 mols.), which dye wool scarlet, fast to milling, washing, perspiration and light, from an acid bath, (7) the di-(4-amino-2-N-benzyltoluidide) of adipic acid## 1-(4<SP>1</SP>-sulpho) phenyl-3-methyl- 5-pyrazolone or its 2<SP>1</SP>:5<SP>1</SP>-dichloro derivative (2 mols.), which dye wool reddish yellow or greenish yellow respectively, fast to milling, washing, sulphur stoving and light, from an acid or ammonium acetate bath, (18) the di-(4- amino-N-ethyl- or N-nbutyl-anilide) of adipic acid## 1-(2<SP>1</SP>:5<SP>1</SP>-dichloro-4<SP>1</SP>-sulpho) phenyl-3- methyl-5-pyrazolone (2 mols.), which dye wool greenish yellow, fast to milling, washing, perspiration, sulphur stoving and light, from an acid bath, (19) the di-(4- or 3-amino-N-benzylanilide) of adipic acid## 2:6:8-naphtholdisulphonic acid (2 mols.), which dye wool bright orange or yellowish orange respectively, fast to milling, washing, perspiration and light, from an acid bath, (20) the di- (4-amino-2-N-benzylanisidide) of adipic acid## N-acetyl-2:5:7- aminonaphtholsulphonic acid (2 mols), which dyes wool red, fast to washing and sulphur stoving, from an acid bath. Tables are also given (Examples 8 to 16 and 21 to 42) showing the shades obtainable on wool with the dyestuffs from various combinations of components, additional tetrazo components being the di- (4-amino-2-N-benzyltoluidide) of oxalic or of sebacic acid, the di-(4-amino-N-ethylanilide) of α:α-dimethylsuccinic acid, and the di-(5-amino- 2-N-benzylanisidide), di-2-amino-N-ethylanilide), and di-(4-amino-2-N-p-chlorobenzyltoluidide) of adipic acid and additional coupling components being 2:8-naphtholsulphonic acid, 1:3:6-naphtholdisulphonic acid, N-benzoyl-N-#-hydroxyethyl-2:8:6-aminonaphtholsulphonic acid (cf. Specification 462,176), 1-(4<SP>1</SP>-sulpho)-phenyl-5- pyrazolone-3-carboxylic acid, 1-(3<SP>1</SP>-sulpho) phenyl-3-methyl-5-pyrazolone, 1-(21-chloro-51- sulpho or 4<SP>1</SP>-chloro-2<SP>1</SP>-sulpho) phenyl-3-methyl- 5-pyrazolone, N-p-toluenesulphonyl-1:8:3:6- or 1:8:4:6-aminonaphtholdisulphonic acid, N-acetyl-1:8:6-aminonaphtholsulphonc acid, N-phenyl-2:8:6-aminonaphtholsulphonic acid and its 41-methoxy derivative. Diamines of the above general formulae are obtained by condensing a halide (1 mol.) of the corresponding dicarboxylic acid with the nitrophenyl-alkyl- or benzyl-amine (2 mols.) and reducing the nitro groups. N-acetyl-1:8:6- aminonaphthol sulphonic acid is obtained by acetylating the 1:8:6-acid with acetic anhydride.