Patent GB-423256-A (GB)
Title: Manufacture of dyestuffs
IPC: D01H1/00
Filed: 1933-09-20
Abstract: 423,256. Dyes. SOC. OF CHEMICAL INDUSTRY IN BASLE, Basle, Switzerland. Sept. 20, 1933, Nos. 25978 and 25979. Convention dates, Sept. 20, 1932 and April 8, 1933. [Classes 2 (iii) and 15 (ii)] Dyes of the general formula (the groups -NHx and -NHy being the sole nuclear substituents in the anthraquinone nucleus) wherein x stands for an oxyalkyl residue and y for a residue of the benzene series containing an NH2-group or an OH-group in p-position to the -NH-group are prepared (a) by causing a primary oxyalkylamine to react with a compound of the general formula wherein y is as above and z stands for a negative substituent such as OH, OR (R being alkyl or phenyl), nitro or halogen ; (b) by causiag a primary amine of the benzene series containing in p-position the primary amino group a further NH2-group or an OH-group to react with a compound of the formula wherein x and z are as above ; (c) by treating a 1 - amino - 4 - (4<1> - oxy) - phenylaminoanthraquinone with ethylene oxide or a homologue or analogue thereof, such as propylene oxide or glycide ; (d) by condensing the leuco body of a 1À4 - di - (4<1> - oxy or 4<1> - amino) - phenylamino - anthraquinone with an oxyalkylamine with simultaneous or subsequent oxidation ; (e) by condensing the leuco body of a 1À4-di-(oxyalkylamino)anthraquinone with a primary amine of the benzene series containing in p-position to the amino group a further NH2-group or an OH-group, with simultaneous or subsequent oxidation ; (f) by reacting a leuco-1À4-diaminoanthraquinone with an oxyalkylamine and a primary amine of the benzene series containing in p-position to the amino group a further NH2-group or an OH-group, with simultaneous or subsequent oxidation. The products have good affinity for acetate artificial silk and dye in blue to green shades. They may be sulphonated to give acid wool dyes. In examples : (1) 1 - # - oxyethylamino - 4 - methoxy (or 4- bromo-) anthraquinone is condensed with p-phenylenediamine in presence of dimethylaniline ; (2) 1-amino-p-oxyphenylaminoanthraquinone is condensed with ethyleneoxide in glacial acetic acid ; (3) leuco-1À4-di-(#-oxyethylamino)-anthraquinone is condensed with pphenylene diamine hydrochloride in alcohol, and the product oxidized; (4) leuco-1À4-di- (p - oxyphenylamino) - anthraquinone is condensed with #-oxyethylamine in pyridine, entry of air being permitted towards the end of the operation ; (5) leuco-1À4-diaminoanthraquinone is condensed with p-aminophenol and #-oxyethylamine in alcohol and glacial acetic acid ; (6) the product of (1) is sulphonated with monohydrate ; it dyes wool green shades. Specifications 26336/10, 289,807, [both in Class 2 (iii)], and 385,202, are referred to. The Specification as open to inspection under Sect. 91 comprises the manufacture of the foregoing and similar dyes by condensing the leuco - body of a 1 - oxy - 4 - arylamino - anthraquinone with an oxyalkylamine or by condensing a 1-oxy-4-oxyalkylaminoanthraquinone with an aromatic amine, in either case with simultaneous or subsequent oxidation. Also the above processes are directed to the manufacture of dyes of the first general formula wherein y stands for an aryl residue. An additional example is given wherein leuco-1-oxy- 4-(4<1>-aminophenylamino)-anthraquinone is condensed with #-oxyethylamine in presence of sodium chlorate and boric acid. Details illustrating the application of the products to the dyeing of acetate artificial silk are also furnished. This subject-matter does not appear in the Specification as accepted.