Patent GB-292660-A (GB)
Title: The manufacture of new copper compounds of substantive azo dyestuffs
IPC: C09B45/01
Filed: 1927-03-18
Abstract: 292,660. Carpmael, W., (I. G. Farbenindustrie Akt.-Ges.). March 18, 1927. Azo dyes, copper compounds of.-Copper compounds of substantive azo dyes derived from a diazo or diazoazo compound corresponding to a monoamine containing at least one substituted or unsubstituted alkyloxy-, aralkyloxy, or aryloxy group in o-position to the amino group, are obtained by treating the dyestuffs with a compound yielding copper. Dyestuffs containing an o-alkoxyazo group as well as an o-oxyazo or ocarboxyazo group derived from the diazo components are excepted. The products dye cotton in various shades fast to alkali, ironing and light. The following dyestuffs are specified :-(1) primary disazo dyes, two molecules of 2-aminoanisol, 2 : 6-dimethaxyaniline, or 4-chlor-2-aminoanisol or one molecule of 2-aminoanisol and one molecule of 4-chlor-2-aminoanisol # one molecule of 5 : 5<1>-dioxy (or 5-oxy-5<1>-methoxy) -2 : 2<1>-dinaphthylamine-7 : 7<1>-disluphonic acid; two molecules of 4-nitro-2-aminoanisol, or one molecule of 4- nitro-2-aminoanisol and one molecule of 2-chloraniline, 3-nitraniline, 4-aminobenzamide, 3- aminobenzoic acid, 3-aminobenzaldehyde, 4- amino-3-methoxy - 4<1>-oxyazobenzene-3<1>-carboxylic acid, or 2-aminonaphthalene-6-carboxylic acid # 5: 5<1>-dioxy-2 : 2<1>-dinaphthylamine-7 : 7<1>-disulphonic acid; (2) monoazo dyes 5-nitro-2-aminoanisol-4-sulphonic acid # 2-phenylamino-5- naphthol-7-sulphonic acid; 5-nitro-2.aminoanisol- 3-sulphonic acid # 4<1>-tolyl-2-amino-5-naphthol-7-sulphonic acid; (3) a disazo dye, one molecule of di-(2<1>-amino-1<1>-methoxybenzene-4<1>-sulphon)-1 : 4-phenylenediamide # two molecules of 4<1>-tolyl-2-amino-5-naphthol-7-sulphonic acid ; (4) primary disazo dyes, two molecules of 2- aminophenolbenzylether, its 4-carboxylic or 4-sulphonic acid, 2-aminophenol-4<1>-oxy-3<1>-carboxybenzylether-4-sulphonic acid, or 2-aminophenolcyclohexylether # one molecule of 5 : 5<1>-dioxy 2 : 2<1>- dinaphthylurea-7 : 7<1>-disulphonic acid, 5: 5<1>-dioxy-2 : 2<1>-dinaphthylamine-7 : 7<1>-disulphonic acid, 3<1>-aminophenyl-1 : 2-naphthimidazol-5-oxy-7 - sulphonic acid, or 5<1> : 5<11>-dioxy-7<1> : 7<11>-disulpho- 2<1> : 2" - dinaphthyl - 1 : 4-phenylenediamine; (5) primary disazo dyes, two molecules of 2-aminophenetol, 2-amino-1-ethoxybenzene-4-sulphamide, or 2-amino-1-isobutyloxybenzene-4-sulphomonomethylamide, or one molecule of 2-aminoanisol and one molecule of 2-amino-1-ethoxybenzene-4- sulphanilide # one molecule of 5 : 5<1>-dioxy-2: 2<1>-dinaphthylamine-7 : 7<1>-disulphonic acid; one molecule of 2-aminoanisol, 2-aminophenetol, 2- aminophenetol-4-sulphomethylanilide, or 3-amino- 4-ethoxy-benzoic acid, and one molecule of aniline-2-sulphonic acid or a substitution product thereof# one molecule of 5 : 5<1>-dioxy-2 : 2<1>-dinaphthyl-urea-7 : 7<1>-disulphonic acid, the bisimidazol or 5 : 5<1>-dioxy-2 : 2<1>-dinaphthylamine-7 : 7<1>-disulphonic acid; one molecule of 2-aminoanisol, and one molecule of 2-aminobenzaldehyde # one molecule of 5: 5<1>-dioxy-2 : 2<1>-dinaphthylamine-7 : 71-disulphonic acid, followed by treatment with hydroxylamine as described in Specification 245,128; two molecules of 3-amino-4-nbutyloxy-benz-n-butylamide # one molecule of 5 : 5<1>-dioxy-2 : 2<1>-dinaphthylamine - 7 : 7<1>- disulphonic acid; (6) primary disazo dyes, two molecules of 2-aminophenoxyacetic acid, or #-(2- aminophenoxy)propionic acid # one molecule of 5 : 5<1>-dioxy-2 : 2<1>-dinaphthylamine (or dinaphthylurea) -7: 7<1>-disulphonic acid; (7) primary disazo dyes, two molecules of 2-aminophenolglycolether, 2-aminophenolglycerinether, 4-nitro (chloro-, or sulpho-) -2-aminophenolglycolether, or 4-nitro (or chloro-, or sulpho-) -2aminophenolglycerinether # one molecule 5 : 5<1>-dioxy-2 : 2<1>-dinaphthylamine (or dinaphthylurea) .7: 7<1>-disulphonic acid; (8) the monoazo dye, the sulphuric acid ester of 2-amino-4-cresol-oxyethylether (described in Specification 266,940) # 4<1>-aminobenzoyl-2-amino-5-naphthol-7- sulphonic acid may be diazotized on the fibre and developed, e.g. with #-naphthol; (9) a secondary disazo dye aniline -2 : 5-disulphonic acid # aminohydroquinonedimethylether # 2-phenylamino-5-naphthol-7-sulphonic acid. Dyes containing a hydroxy group with a free o-position may be coupled on the fibre, e.g. with p-nitraniline. 5-Oxy-5<1>-methoxy-2 : 2<1>-dinaphthylamine-7 : 7<1>- disulphonic acid is obtained by partial methylation of 5 : 5<1>-dioxy-2 : 2<1>-dinaphthylamine-7 : 7'- disulphonic acid. 5-nitro-2-aminoanisol-3-sulphonic acid is obtained by sulphonating 5-nitro-2-aminoanisol, e.g. in an organic solvent. Di- (2<1>-amino-1<1>-methoxybenzene-4<1>-sulphon)- 1 : 4-phenylenediamide is obtained by reduction of the nitro groups of the compound which is produced when 2-nitro-1-chlorobenzene-4-sulphonic chloride (2 mols.) is treated with 1 : 4-phenylene diamine (1 mol.) and the product is boiled with methyl alcohol in presence of an acid-binding agent. 2-Aminophenolbenzylether and its 4-carboxylic and 4-sulphonic acids are obtained by reduction of the nitro group of the products of interaction of 2-nitrophenol and of its 4-carboxylic end 4-sulphonic acids with benzyl chloride in presence of an acid-binding agent. 2-Aminophenol-4<1>-oxy-3<1>-carboxybenzylether-4- sulphonic acid is obtained by reduction of the nitro group of the product of interaction of 2- nitro-1-chlorobenzene-4-sulphonic acid with 5-oxymethylsalicylic acid. 2-Aminophenolcyclohexylether is obtained by reduction of the nitro group of the product of interaction of cyclohexanol and 2-chloro (or bromo) benzene. 2-Amino-1-isobutyloxybenzene-4-sulphomonomethylamide is obtained by reduction of the nitro group of the product obtained when 2-nitrochlorobenzene-4-sulphonic chloride reacts with methylamine and the resulting sulphomethylamide is treated with isobutyl alcohol in presence of an acid-binding agent. 3 - Amino - - 4-n-butyloxy-benz-n-butylamide is obtained by reduction of the nitro group of the product of condensation of 3-nitro-4-n-butyloxybenzoyl chloride with n-butylamine. 3-Nitro-4-n-butyloxy-benzoyl chloride is obtained by treating with thionyl chloride the 3-nitro-4- n-butyloxy-benzoic acid resulting from the interaction of 3-nitro-4-oxybenzoic acid with n-butyl chloride (or bromide) in presence of an acidbinding agent. #-(2-Aminophenoxy)-propionic acid is obtained by reduction of the product of interaction of #- chloropropionic acid with 2-nitrophenol in aqueous solution in presence of sodium carbonate. 4-Nitro-2-aminophenolglycol (or glycerin) ether is obtained by reduction of 2 : 4-dinitrophenoxy. ethanol (or the corresponding propane diol) with alkali sulphides or polysulphides.