Patent GB-747367-A (GB)
Title: Improvements in the production of water-soluble dyestuffs containing chromium
IPC: C09B45/48
Filed: 1954-01-06
Abstract: Water-soluble chromium-containing dyes are obtained by treating the 1.1-chromium complex of a monoazo or monoazomethine dye free from sulpho groups and containing one metallizable grouping in the molecule which is chelated with said chromium atom and further containing at least one sulphonamide, N-alkylated or arylated sulphonamide and/or one free or acylated amino group with a solution of a colourless aromatic chelating compound which can chelate with said chromium atom and which does not contain alkyl radicals of more than 3 carbon atoms, and acylating any free amino groups if present after the mixed chromium complex has been formed.  Acylamino groups specified are acetyl-, benzoyl-, propionyl-, hexahydrobenzoyl-, methylsulphonyl-, or benzenesulphonyl-amino, and urethane groups. Organic compounds specified are salicylic acid, pyrocateohol, o- and peri-dihydroxynaphthalenes, o- and peri-hydroxynapthoic acids, phthalic acid, naphthalic acid, o-nitrosophenols and naphthols, 8-hydroxyquinoline and the corresponding sulphonic acids and sulphonic acid amides.  The products dye wool, silk, leather casein, fibres and nylon.  In examples, the 1:1-chromium complexes of the following dyes are boiled in water, ethanol or methanol, sometimes with sodium acetate, and with 2-hydroxybenzoic acid-5-sulphophenylamide-; (1) 1-hydroxy - 2 - amino - 5 - nitrobenzene--> 2 - hydroxynaphthalene - 6 - sulphonamide, (2) 1 - hydroxy - 2 - aminobenzene - 4 - sulphonamide-->2 - hydroxynaphthalene or p - cresol, (3) 1 - hydroxy - 2 - amino - 4 - nitrobenzene - 6 - sulphonamide --> 1 phenyl - 3 - methyl - pyrazolone - (5), (4) 2 - aminobenzoic acid-->2 - hydroxynaphthalene - 6 - sulphonamide, (5) 1 - hydroxy2 - aminobenzene - 4 sulhonamide-->1 - amino - 1 - hydroxynapthalene, (6) 1 - hydroxy - 2 - amino - 5 - nitrobenzene--> 2 - benzenesulphonylamino - 7 - hydroxynaphthalene, (7) the azomethine dye from 2 - hydroxy - 5 - aminobenzaldehyde and 1 - hydroxy - 2 - amino - 4 - nitrobenzene, followed by acetylation with acetic anhydride, (8) 1 - hydroxy - 2 - aminobenzene - 4 - sulphonamide, -->1 - carbomethoxy - 7 - hydroxynaphthalene, (9) 4 - methyl - 1 - hydroxy - 2 - aminobenzene - 5 - sulphon - amide-->1 - phenyl - 3 - methyl - pyrazolone, (10) 4-chloro - 1 - hydroxy - 2 - aminobenzene or 1.4 - dihydroxy - 2 - aminoben - zene-->2 - hydroxynaphthalene - 4 - sulphonamide, (11) 4 - methoxy - 1 - hydroxy-2 - aminobenzene-->1 - hydroxynaphthalene. Also in examples, the following dyes are similarly reacted with salicylic acid: - (12) 1 - amino - 2 - methoxy - 5 - sulphonamide-->1 - hydroxynaphthalene - 5 - sulphonamide, (13) the azomethine dye from 1 - hydroxy - 2 - aminobenzene - 4 - sulphodiethylamide and 2 - hydroxy - 3.5 - dichlorbenzaldehyde, (14) 1 - methoxy - 2 - aminobenzene - 4 - sulphonamide or 1 - methoxy - 2 - amino - 5 - nitrobenzene--> 1 - benzenesulphonylamino - 7 - hydroxy - naphthalene, (15) 1 - hydroxy - 2 - amino - 5 - nitrobenzene-->1 - benzenesulphonyl - amino - 3 - hydroxybenzene.  Also in examples, the following dyes are similarly treated with 2 - hydroxybenzoic acid - 5 - sulpho - 41 - chlorphenylamide; - (16) 2 - aminobenzoic acid-->1 - (31 - benzenesulphonyl) - aminophenyl - 3 - methylpyrazolone, and (17) 1 - hydroxy - 2 - aminoben - zene - 4 - sulphonamide-->1 - (31 - chloro - phenyl - 3 - methylpyrazolone.  In further examples (18) the dye 1-amino-2.5 - dimethoxybenzene - 4 - sulphonamide -->2 - hydroxynaphthalene - 6 - sulpho - phenylamide is treated with 2 - hydroxy - benzoic acid - 5 - sulphonamide; (19) 1 - hydroxy - 2 aminobenzene - 4 - sulphodi - ethylamide or 1 - hydroxy - 2 - amino - 4 - chlorbenzene-->1 - hydroxynaphthalene - 8-sulphonamide is treated with 2 - hydroxy - benzoic acid - 5 - sulphoethylamide; (20) the dye 1 - hydroxy - 2 - aminobenzene - 4 - sulphonamide-->1 - hydroxy - 3 - (N - di - methyl) - aminobenzene is treated with 2 - hydroxybenzoic acid - 5 - sulpho - 21 - methoxyphenylamide; (21) the dye 1 - aminobenzene - 4 - sulphonamide --> 2 - hydrobenzoic acid is treated with 2 - hydroxybenzoic - 5 - sulpho - m - toly - amide.