Patent GB-580642-A (GB)
Title: Manufacture of vat dyestuffs
IPC: C09B5/28
Filed: 1943-05-14
Abstract: Vat dyes are obtained by linking together components of which at least two are vattable and of which at least one carries attached directly to carbon a grouping -SOnR, wherein n represents 1 or 2 and R represents an external organic residue. The linking may be of two anthraquinone residues to form an anthrimide, which may then be subjected to carbazolisation.  The products are applicable for dyeing or printing wool, silk, leather, cotton, linen and artificial silk or staple fibre of regenerated cellulose.  Examples relate to the condensation of (1) 1 - amino - 4 - (Bz3 - methylsulphone) benzoylamino-anthraquinone with 1-chloro-5-benzoylaminoanthraquinone by boiling in nitrobenzene containing a copper salt; the product is carbazolised by treatment successively with concentrated sulphuric acid and sodium bichromate or with chlorosulphonic acid and sodium perborate; (2) 1-amino-4-(Bz3-methylsulphone) benzoylamino-anthraquinone with 1-chloro-4-benzoylaminoanthraquinone; the product is carbazolised by treatment successively with concentrated sulphuric acid and sodium nitrite or sodium bichromate; (3) 1-amino-4-(Bz3-methylsulphone) benzoylamino-anthraquinone with 1-chloro-5-(Bz3-methylsulphone)benzoylamino-anthraquinone; the product is carbazolised by treatment successively with concentrated sulphuric acid and sodium bichromate or sodium nitrate; (4) 1-amino-4-benzoylaminoanthraquinone with 1 - chloro - 5 - (Bz3 - methylsulphone)benzoylamino - anthraquinone; the product is similarly carbazolised; (5) 1-amino - 4 - (Bz4 - phenylsulphone)benzoylaminoanthraquinone with 1-chloro-5-benzoylaminoanthraquinone or 1 - amino - 4 - benzoylaminoanthraquinone with 1 - chloro - 5 - (Bz4 - phenylsulphone)benzoylamino - anthraquinone or 1 - amino - 4 - (Bz4 - phenylsulphone)benzoylaminoanthraquinone with 1 - chloro - 5 - (Bz4 - phenylsulphone)benzoylamino - anthraquinone; the products are carbazolised by treatment successively with concentrated sulphuric acid and sodium nitrate or sodium bichromate; (6) 1-amino-4-(Bz4-phenylsulphone)benzoylaminoanthraquinone with 1-chloro-4-benzoylaminoanthraquinone; the product is similarly carbazolised; (7) 1-aminoanthraquinone with 1-chloro-5-(Bz4-phenylsulphone)benzoylaminoanthraquinone; the product is carbazolised by treatment with aluminium chloride in presence of dry sulphur dioxide and common salt, followed by oxidation by treatment first with sodium bichromate in acid solution and then with Javelle water; (8) amino-dibenzanthrone with 1-chloro-5-(Bz4-phenylsulphone-benzoylamino)anthraquinone in the presence of sodium carbonate, copper acetate and nitrobenzene; (9) two mols. of 1-amino-4-(Bz3-methylsulphone-benzoylamino)-anthraquinone, and one mol. of 1 : 5 - dichloranthraquinone in nitrobenzene followed by carbazolisation of the product with aluminium chloride in pyridine; (10) one mol. of dibromofluoranthrene and two mols. of 1-amino-4-(Bz3-methylsulphone-benzoylamino) anthraquinone and carbazolising the product with sulphuric acid; (11) fluoranthrene-dicarboxylic acid chloride and 1-amino-5-(Bz3-methylsulphone-benzoylamino) anthraquinone; (12) 2 : 7-dichloro-anthraquinone and 1-amino-5-(Bz4-phenylsulphone-benzoylamino) anthraquinone in the presence of sodium carbonate, copper acetate and nitrobenzene; (13) 1-amino-5-(Bz4-phenylsulphone-benzoylamino) anthraquinone and oxalyl chloride in nitrobenzene.  Iso-phthalic acid may be substituted for oxalyl chloride; (14) 1-amino-5-(Bz4-phenylsulphone-benzoylamino)-anthraquinone and 1-chloro-5-(Bz4 - phenylsulphone - benzoylamino) anthraquinone in nitrobenzene sodium carbonate and copper acetate followed by carbazolising the product with sulphuric acid; (15) 1-amino-4-(Bz3 - methylsulphone - benzoylamino) anthraquinone and cyanuric chloride in the presence of nitrobenzene diethylaniline and sodium carbonate; (16) the dyestuff obtained in example (1) is used to dye cotton from a hydrosulphite vat; (17) a printing preparation is made up from the dyestuff paste from the dye of example (1), potassium carbonate thickening, urea and sodium formaldehyde sulphoxylate, and a cotton fabric is printed and soaped to give a reddish brown print.  A sample has been filed of a dyestuff made by the condensation of 1-chloro-5-benzoylamino-anthraquinone and 1-amino-4-(Bz3-methylsulphoxide-benzoylamino)-anthraquinone followed by carbazolising the product with sulphuric acid and sodium nitrite. Specification 555,055 is referred to.