Patent GB-320030-A (GB)
Title: Process for the manufacture of polyazo dyestuffs
IPC: C09B31/16
Filed: 1928-05-01
Abstract: 320,030. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). May 1, 1928. Samples furnished. Azo dyes are obtained by diazotizing an aminomono- or disazo compound (obtained from any diazo or diazo azo compound and an aromatic aminoether or aminothioether which couples para to the amino group) and coupling with an N- aminobenzoylaminobenzoylaminobenzoyl - periaminonaphthol or an N-aminobenzoylaminobenzoyl-peri-aminonaphthol, in which one or more of the -CO-NH-linkages may be replaced by -NHCO-NH-, then diazotizing again and coupling with a pyrazolone, acetoacetic arylide, methol ketol, sulphazone, 1 : 3-dihydroxyquinoline, salicylic acid or derivatives thereof. The final coupling may be made on the fibre. Green shades are obtained. The following dyestuffs are specified, (1) H acid # 3-amino-4-cresolethylether # N-4<11>-aminobenzoyl-4<1>-aminobenzoyl-H acid # m-carboxylphenyl-3-methyl-5-pyrazolone, (2) 1 : 8-aminonaphthol-5 : 7-disulphonic acid # (4<1>-methyl- 2<1>-aminophenoxy)-#-propionic acid # urea from H acid and 4-methoxy-3-aminobenzoyl-p-phenylenediamine # (5<1>-chlor-2<1>-carboxy-phenyl-3- methyl-5-pyrazolone, (3) H acid # 1-naphthylamine-7-sulphonic acid # 3-amino-4-cresol hydroxyethylether # N - 4<11> - aminobenzoyl -4<1>- aminobenzoyl-4-aminobenzoyl H acid # (5<1>- carboxy-4<1>-hydroxy-3<1>-methoxy,1-phenyl-3-methyl- 5-pyrazolone, (4) 1 : 8-aminonaphthol-4 : 7-disulphonic acid # 3-amino-4-cresolethylether # -N-4<11>-aminobenzoyl-4<1>-aminobenzoyl H acid # (on the fibre) 3-methyl-1-phenyl-5-pyrazolone, (4a) 4: 5-dichloraniline-2-sulphonic acid # 1-amino-2-naphtholethylether-6-sulphonic acid # N-4<11>-aminobenzoyl-4<1>-aminobenzoyl-H acid # (on the fibre) 1-phenyl-3-methyl-5-pyrazolone; the first component mav be replaced by aniline- 2-sulphonic acid, 3-chloro-2-aminotoluene-5-sul phonic acid, 1 :3-dimethyl-4-aminobenzene-5- sulphonic acid, 2-naphthylamine-8-sulphonic acid, 1-naphthylamine-2-sulphonic acid or 2-naphthylamine-8-sulphonic acid # 3-toluidine; the second component by the below mentioned aminonaphtholethers and the third by a thrice benzoylated compound or by N-3<11>-amino-4<11>-methoxybenzoyl- 4<1>-aminobenzoyl H acid. (5) 4-amino-2-sulphooxanilic acid # 1-naphthylamine-2-methylthioether # N-4<11>-aminobenzoyl-3<1>-amino-4<1>- metboxybenzoyl H acid # (on the fibre) 3- methyl-1-phenyl-5-pyrazolone. Other aminoethers of the benzene series referred to as middle components are 3-amino-4-cresolmethylether and the sulphuric acid ester of 3-amino-4-cresolhydroxyethyl ether (c.f Specification 266,940) and of the naphthalene series, 1-amino-2-naphtholethylether, (1-amino-2-naphthoxy) -#- propionic acid, the sulphuric acid ester of 1-amino-2-naphtholhydroxyethylether and the 6-(or 7-)-sulphonic acids of these naphthol ethers, 1-amino-7-naphtholmethylether and 1 - aminonaphthalene - 2 - methylthioether-6-sulphonic acid. (4<1>-Methyl-2<1>-aminophenoxy)-#-propionic acid is obtained by treating 3-nitro-3-cresol with #- chloropropionic acid and reducing the nitro compound formed. 1-Amino-6-(or 7)-sulpho-2-naphthoxy-#-propionic is obtained from 2-naphthol-6- (or 7)- sulphonic acid and #-chloropropionic acid, nitrating and reducing. 1-Amino-2-naphtholoxyethylether-sulphuric acid ester-6- (or 7). sulphonic acid is prepared from 2- naphthol-6- (or 7)- sulphonic acid and glycolchlorhydrin, esterifying the w-hydroxy group with sulphuric acid (c.f. Specification 266,940) nitrating and reducing. 1-Aminonaphthalene - 2 - methylthioether - 6 - sulphonic acid is obtained by diazotizing 2 naphthylamine-6-sulphonic acid, converting into the mercapto compound by Sandmeyers's reaction, methylating with methylbromide, nitrating and reducing. 1-Aminonaphthalene-2-methylthioether is made by introducing the methyl group into #-naphthylmercaptan, nitrating and reducing. Aminobenzoyl-peri-aminonaphthols are made by treating the naphthol with the appropriate nitrobenzoylchloride or derivative thereof, reducing and repeating the nitrobenzoylation process once or twice as required. To introduce the -NH-CONH-group with the chain the nitrobenzoyl compound is replaced by the appropriate nitrophenylisocyanate. (5<1>-Carboxy-4<1>-hydroxy-3<1>-methoxy)-1-phenyl-3- methyl-5-pyrazolone is made from 5-hydrazine- 3-methoxy-2-hydroxybenzoic acid and aceto-acetic ester. 5-Hydrazine-3-methoxy-2-hydroxybenzoic acid is made by nitrating 3-methoxy-2-hydroxybenzoic acid, reducing, diazotizing and reducing the diazo compound with stannous chloride.