Patent GB-591454-A (GB)
Title: Process for chroming chromable dyestuffs containing sulphonic acid groups and the resulting dyestuffs
IPC: C09B45/01
Filed: 1944-06-03
Abstract: Chromium complex compounds are prepared from salicylic acid and its homologues and substitution products, e.g., 3-, 4-, or 5-methyl-, 5-chloro-, 5-p-toluenesulphamino- or 5-phenoxy-2-hydroxybenzoic acid, or 2-hydroxybenzoic-5-sulphonic acid or its derivatives such as its N-ethylanilide or phenyl or o-tolyl ester.  In examples: (1) ammonium chromium salicylate is obtained by neutralizing a mixture of 1 mol of a chromium salt, e.g., chromium fluoride, and 2 mols of salicylic acid with ammonia at a raised temperature; (5) a hot solution of sodium 2-hydroxy-5-sulphoethylanilide benzoate and chromium fluoride is neutralized with sodium carbonate; (29) a chromium hydroxide paste is boiled with salicylic acid and the resulting chromium salicylate is dissolved with aqueous ammonia.ALSO:Dyestuffs containing sulphonic acid groups are chromed in substance by using, as chroming agents, chromium complex compounds of salicylic acid or its homologues or substitution products.  In examples, the following dyes are chromed with ammonium chromium salicylate (made by neutralizing a mixture of 1 mol. of a chromic salt, e.g. chromium fluoride, and 2 mols. of salicylic acid with ammonia): 4-chloro-5-nitro - 2 - aminophenol --> 1 : 8 - naphtholsulphonic acid-3-sulphomethylanilide, 4-chloro-2-aminophenol --> 1 : 8-naphtholsulphonic acid-3-sulphoethylanilide, 4 - chloro- or 5 - nitro - 2 - aminophenol --> 1 : 8-naphtholsulphonic acid-3 - sulphanilide, 1 - aminonaphthalene - 4- or 5 - sulphonic acid --> salicylic acid, 4-nitro-2-aminophenol-6-sulphonic acid --> 4-isobutyl-2-methylphenol, aniline-3-sulphonic acid --> 2-hydroxytoluene-3-carboxylic acid, aniline-3-or 4-sulphonic acid --> salicylic acid, 5-nitro-2-aminophenol --> 1 : 8-naphtholsulphonic acid - 3 - sulphonic acid - 41 - methoxyanilide, 2 - aminobenzoic acid or 5-nitro-, 6- or 5-nitro-4-methyl- or 4-chloro-5-nitro-2-aminophenol --> 1 : 8 - naphtholsulphonic acid - 3 - sulphoethyl - anilide, 6 - nitro - 4 - chloro - 2 - aminophenol --> 1-naphthol-5-sulphonic acid-ethyl-(31-sulphonic acid phenyl) - amide, 5 - nitro - 2 - aminophenol --> 1 : 8 - naphtholsulphonic acid - 3 - sulphonic acid-ethyl - (31-nitrophenyl)-amide, 5 - nitro- or 5 - nitro - 4 - methyl - 2 - aminophenol --> 1 : 8 - naphtholsulphonic acid-3-sulphonic acid-ethyl-(21-methylphenyl)-amide, 5-nitro-4-methyl- or 5 - nitro - 2 - aminophenol --> 1 : 8 - naphthol - sulphonic acid - 3 - sulphomethylanilide, 5 nitro - 4-chloro- or 5-nitro-2-aminophenol --> 1 : 8-naphtholsulphonic acid - 5 - sulphomethylanilide, 5 - nitro - 4 - methyl- or 5 - nitro - 2 - aminophenol --> 1 : 8 - naphtholsulphonic acid - 3 - sulphonic acid-41-methylphenyl-ester, 6-nitro-4-amyl-2-aminophenol --> 31-sulphophenyl-3-methyl-5-pyrazalone and 2-(21-hydroxy-51-chloro-31-sulphophenyl) - 4 : 5 : 111 : 211 - naphthotriazol - 311-carboxylic acid.  The ammonium chromium salicylate used with the last-named dye is made by boiling a chromium hydroxide paste with salicylic acid and dissolving the chromium salicylate with aqueous ammonia. In a further example, the dyestuff 4 : 6-dinitro-2-aminophenol --> 1-naphthol-5-sulphonic acid is chromed with a complex obtained by neutralizing with sodium carbonate a hot solution of sodium 2 - hydroxy - 5 - sulphoethylanilide benzoate and chromium fluoride. Other specified salicylic acid derivatives, the chromium complex compounds of which may be used in the process of the invention, are 3-, 4- or 5-methyl-, 5-chloro-, 5-sulpho-, 5-p-toluenesulphamino- or 5-phenoxy-2-hydroxybenzoic acid and the phenyl or o-tolyl esters of 5-sulpho-2-hydroxybenzoic acid.  The products dye wool from weak mineral acid (e.g. 1 per cent sulphuric acid) baths or from organic acid (e.g. 2-4 per cent formic acid) baths, and are thus suitable for dyeing half wool or loose wool. They may also be applied to natural silk, to artificial fibres such as those of casein or nylon, and to leather.  1 : 8-Naphtholsulphonic acid-3-sulphonic acid-41-methoxyanilide is obtained by condensing 1 : 8 - naphthosultone - 3 - sulphochloride with 4-methoxyaniline and saponifying the product.  1 - Naphthol - 5 - sulphonic acid - ethyl - (31 - sulphonic acid-phenyl)-amide is obtained by condensing 1-carbomethoxy-hydroxy-naphthalene-5-sulphochloride with 1-ethylamino-benzene-3-sulphonic acid and saponifying the product.  1 : 8-Naphtholsulphonic acid-3-sulphonic acidethyl - (31 - nitrophenyl) - amide is obtained by condensing 1 : 8 - naphthosultone - 3 - sulpho - chloride with 1-ethylamino-3-nitrobenzene and saponifying the product.  1 : 8-Naphtholsulphonic-5-sulphomethylanilide is obtained by condensing 1 : 8-naphthosultone-5-sulphochloride (obtained from the sulphonic acid and phosphorus pentachloride with methylaniline and saponifying the product.  1 : 8-Naphtholsulphonic acid-3-sulphonic acid-41-methylphenyl ester is obtained by condensing 1 : 8-naphthosultone-3-sulphochloride with 4-methylphenol and saponifying the product.