GB636914A - Improvements in dyes of the anthraquinone series and the dyeing of cellulose derivatives - Google Patents

Abstract

1-Nitro-5 or 8-sulpho-anthraquinone is obtained by nitrating 1-sulphoanthraquinone. 1-Nitro-5 or 8-chloro-anthraquinone is obtained by reacting the 5- or 8-sulpho body with sodium chlorate and hydrochloric acid.ALSO:Cellulose ester or ether (e.g. cellulose acetate) materials or superpolyamides are dyed with 1.4 - diamino - 2 - cyanoanthraquinones having halogen or amino groups in one or both of the 5- and 8-positions. The amino groups may contain alkyl, hydroxyalkyl, aralkyl, or hydroaryl substituents, e.g. methyl, ethyl, hydroxyethyl, propyl, butyl and hydroxybutyl, amyl, octyl, decyl, dodecyl, octodecyl, benzyl, phenyl, naphthyl, tolyl, cyclohexyl, b -phenylethyl, p-benzoylphenyl, hydroxy - methyl - phenyl, hydroxyphenyl, sulphonamidophenyl, alkoxyphenyl and naphthyl. The dyes are obtained by reacting with a cyanide, e.g. in aqueous solution a compound differing from the required compound in having a sulpho group instead of the cyano group, or by reacting with ammonia or an amine a compound differing from that required by having halogen instead of amino. The products may be applied as aqueous dispersions with the usual dispersing agents and may be used to colour lacquers and spinning solutions. In examples, an aqueous solution of potassium cyanide is reacted with (1) 1.4-diamino - 2 - sulpho - 5 - chloranthraquinone, (2) 1.4.5 - triamino - 2 - sulphoanthraquinone, (3) 1 - amino - 2 - sulpho - 4 - butylamino - 5 - chloranthraquinone, (4) 1-amino-2-sulpho-4-butylamino-5-aminoanthraquinone, (5) 1.4-diamino-2 - sulpho - 5 - methylaminoanthraquinone, (6) 1-amino-2-sulpho-4-butylamino-5- or 8-methylamino-anthraquinone. 1.4.5- or 1.4.8 - Triaminoanthraquinone - 2 - sulphonic acids are obtained from the corresponding 5- or 8-chlor bodies by reaction with amines or with an acid amide (see examples below), followed by hydrolysis. 1.4 - Diamino-5- or 8 - chloranthraquinone-2-sulphonic acids are obtained from the corresponding 4-brom bodies by reaction with amines corresponding to the substituents listed above, or by reaction with amides (e.g. p-toluene sulphonamide, p - toluene sulphomethylamide, benzamide, or phthalimide), followed by hydrolysis. 1 - Amino-8- or 9 - chloranthraquinone is obtained by reduction of the 1-nitro body, and may be sulphonated to give 1-amino-2-sulpho-5-or 8-chloroanthraquinone, which may then be brominated in 4-position.