Patent GB-520199-A (GB)
Title: Process for the manufacture of phthalocyanine sulphonamides
IPC: C09B47/04
Filed: 1938-10-14
Abstract: 520,199. Dyes and lakes; cellulose derivative compositions. I.G. FARBENINDUSTRIE AKT.-GES. Oct. 14, 1938, Nos. 29849 and 29850. Convention dates, Oct. 14, 1937, and Sept. 24, 1938. [Classes 2 (ii), 2 (iii) and 15 (ii)] Phthalocyanine sulphonamides are manufactured by reacting phthalocyanine sulphochlorides, obtainable by the process of Specification 515,637, with ammonia or amines, e.g. aniline, dodecylamine, stearylamine, cyclohexylamine, perhydrocarbazole, butyloxyethylamine or diethanolamine, or polyamines such as benzidine or ethylenediamine, or substituted amines such as 5-amino-2-hydroxybenzoic acid. Those of the products which still contain replaceable hydrogen atoms linked to the nitrogen may be converted into lakes by treatment with metal salts, e.g. alkaline-earth metal salts, whilst those containing a salicylic acid residue yield lakes with chromium salts. The products obtained from aliphatic or hydroaromatic amines are soluble in fats or organic solvents such as alcohol, acetone, chloroform, benzene or pyridine and compatible with polystyrene and cellulose triacetate, and are thus suitable for use in varnish lacquers. In some cases the sulphochloride residues are only partly converted into amides, the remainder being saponified. In examples : (1) copper phthalocyanine sulphochloride '(obtainable by the action of chlorsulphonic acid on copper phthalocyanine at an elevated temperature) is stirred with monoisohexylamine ; (2) copper phthalocyanine sulphochloride is heated with dodecylamine ; (3) copper phthalocyanine sulphochloride is reacted with excess of an equimolecular mixture of butylamine, butanolamine, monoisohexylamine and hexahydroaniline ; (4) tetraphenyl copper phthalocyanine sulphochloride (obtainable by the action of chlorsulphonic acid on tetraphenyl copper phthalocyanine) is stirred with hexahydroaniline; (5) diphenyl copper phthalocyanine sulphochloride (obtainable by the action of chlorsulphonic acid on diphenyl copper phthalocyanine) is stirred with butylamine ; (6) copper phthalocyanine sulphochloride is stirred with ammonia solution ; (7) copper phthalocyanine sulphochloride is stirred with an aqueous suspension of aniline in the presence of sodium carbonate ; (8) copper phthalocyanine sulphochloride is stirred with 5-amino-2-hydroxybenzoic acid ; the product may be converted on the fibre into a chromium complex compound ; (9) copper phthalocyanine sulphochloride (obtainable by the action of chlorsulphonic acid on the copper phthalocyanine tetrasulphonic acid obtained from phthalic acid-4-sulphonic acid) is stirred with butylamine ; (10) the copper phthalocyanine sulphochloride of (9) is stirred with ammonia solution; (11) metal-free phthalocyanine sulphochloride (obtainable by the action of chlorsulphonic acid on metal-free phthalocyanine) is stirred with aniline, water and sodium carbonate ; (12) metal-free phthalocyanine sulphochloride is stirred with ammonia solution; (13) cobalt phthalocyanine sulphochloride is stirred with butylamine ; (14) copper phthalocyanine sulphochloride is heated with monomethylaniline ; (15) copper phthalocyanine sulphochloride (obtained by heating copper phthalocyanine with chlorosulphonic acid and phosphorus pentachloride) is stirred with aniline in nitrobenzene.