Patent GB-308617-A (GB)
Title: Manufacture of vat dyestuffs
IPC: C09B3/50
Filed: 1929-03-23
Abstract: 308,617. I. G. Farbenindustrie Akt.- Ges. March 23, 1928. [Convention date]. Anthraquinone vat dycs.-Vat dyes of the dibenzpyrenequinone series are made by treating a halogendibenzpyrenequinone with a nitrogen compound containing at least one reactive Hydrogen atom linked to the nitrogen atom, in the presence of a solvent, such as nitrobenzene or ocresol, an acid-binding agent, such as sodium carbonate or sodium acetate, and a copper catalyst, such as copper powder, or a copper salt, e.g. copper acetate. The tints and fastness properties of the products may be changed by treating them with acid condensing agents, such as aluminium chloride, sulphuric acid, or chlorsulphonic acid, in the presence of a flux, such as sodium chloride, if required. According to examples, (1) monobrom-4 : 5 : 8 : 9-dibenzpyrene- 3: 10-quinone (Specification 287,050) is heated with a-aminoanthraquinone, sodium acetate, copper acetate and nitrobenzene: the product, which dyes cotton from an orange-red vat in dull red tints, may be converted into a dyestuff dyeing cotton in reddish-brown tints fast to chlorine and washing by fusing it with sodium-aluminium chloride, (2) monobrom-4- : 5 : 8 : 9-dibenzpyrene- 3 : 10-quinone is heated with anthranilic acid, anhydrous sodium carbonate, copper acetate and o-cresol; the product dyes claret-red tints, and is converted into a dyestuff dyeing in brownishorange tints by heating with concentrated sulphuric acid, (3) dibrom-4: 5 : 8 : 9-dibenzpyrene- 3:10-quinone, made according to example 2 of Specification 287,845, is heated with a-aminoanthraquinone, sodium acetate, copper acetate, and nitrobenzene; the product dyes cotton in a red vat intense violet tints, (4) monochlor- 3:4:8: 9-dibenzpyrene-5 : 10-quinone, made by condensing benzoyl chloride with 5-chlorbenzanthrone in the presence of aluminium chloride according to the process described in Specification 205,502, is heated with phthalimide sodium acetate, copper powder, and nitrobenzene, and the phthalimidobenzpyrenequinone obtained is saponified by heating with concentrated sulphuric acid: the resulting monoaminodibenzpyrenequinone dyes cotton from a red vat in violet tints, (5) tetrachlor-3 : 4 : 8 : 9-dibenzpyrene-5 : 10 - quinone is heated in nitrobenzene with #-aminoanthraquinone, sodium acetate and copper acetate; the product dyes brownish-black tints, (6) the corresponding product from alpha-aminoanthraquinone dyes bluish-black tints, (7) tetrachlor-3 : 4 : 8 : 9- dibenzpyrene-5 : 10-quinone is condensed with anthranilic acid, the product gives pure green dyeings; by treating the product with a dehydrating agent, such as sodium-aluminium chloride or chlorsulphonic acid, it is converted into another dyestuff which dyes in intense brown tints, and (8) dibrom-4 : 5: 8 : 9-dibeiazpyrene-3 : 10-quinone (Specification 287,845) is heated with benzamide, anhydrous sodium carbonate and copper acetate in nitrobenzene; the product dyes violet tints, while the corresponding monobenzoylamino derivative obtained from the monochlordibenzpyrenequinone dyes cotton in clear fast scarlet tints. Specification 318,180 also is referred to. The Specification as open to inspection under Sect. 91 (3) (a) mentions naphthalene and quinoline as solvents, and copper oxide and copper chloride as catalysts, and includes the following additional examples :-(9) dibrom-3 : 4 : 8 : 9-di. benzpyrene-5 70-quinone is heated with naphthalene, sodium carbonate, copper oxide and aaminoanthraquinone, the product dyes cotton in intense clear currant tints fast to washing, chlorine, bucking and light; the corresponding dyestuffs from 1: 5-diaminoanthraquinone and 1 : 5-aminobenzoylaminoanthraquinone have similar properties, (10) the dyestuffs made according to examples 6 and 9 are fused with aluminium chloride or sodium-aluminium chloride; the products dye cotton in brownish tints, (11) dibrom-3 : 4 : 8 : 9-dibenzpyrene-5 : 10 - quinone is heated with 1-aminoanthraquinone-2-carboxylic acid, sodium acetate, copper acetate and nitrobenzene; the product dyes in olive-brown tints, (12) the corresponding product from 1-aminoanthraquinone - 2 - aldehyde dves reddish-brown tints, (13) dibrom-3 : 4 8 : 9-dibenzpyrene-5 : 10- quinone is heated with 1-amino-4-benzoylaminoanthraquinone, sodium carbonate, sodium acetate, end copper chloride in naphthalene; the product dyes cotton in bluish-grey tints, and (14) dibrom- 4:5:8: 9-dibenzpyrene-3 : 10-quinone is heated with 1 - amino - 5 - benzoylaminoanthraquinone, sodium acetate, copper acetate and naphthalene; the product dyes cotton in grey tints. This subject-matter does not appear in the Specification as accepted.