Patent GB-768999-A (GB)
Title: New disazo-dyestuffs and process for making them
IPC: C09B35/033
Filed: 1953-09-11
Abstract: Vinyl polymers, e.g. polyvinyl chloride, are coloured with pigment dyestuffs of formula R2-N=N-R1-N=N-R2, where R1 is an anthraquinone residue free of sulphonic and carboxylic acid groups and in which the two carbon atoms to which the azo linkages are bound are separated from one another by at least three carbon atoms of the anthraquinone nucleus and R2 is a residue of an azo component free of sulphonic and carboxylic acid groups and bound to the azo linkage in a position vicinal to a hydroxyl group.  The preparation of the dyestuffs and lists of components from which they are obtained is in Group IV (c). Yellow, red, brown and blue shades are obtained.  In examples, polyvinyl chloride is coloured by rolling in pigments made from 1,5-diaminoanthraquinone and (1) 1-acetoacetylamino-2-chloro- and -methoxy-, -2-chloro-5-trifluoromethyl, -4-methyl-, -2,5-dichloro-, 2,4-dimethyl-5-chloro-, -2-chloro-4-acetylamino-5-methoxy-, -2,5-dimethoxy-4-chloro-, -3-sulphonamido- and -2-methoxy-5-methyl-benzenes, 2-acetoacetylamino-6-ethoxybenzthiazole, acetoacetylaminobenzene, 1 - benzoylacetylamino - 2 - methoxy - 5 - methylbenzene and 1-phenyl- and -(21-chlorophenyl)-3-methyl-5-pyrazolone; (2) 1-(21-oxy-31 - naphthoylamino) - benzene and -2-methoxybenzene and (4) 2 - oxycarbazole - 3 - carboxylic acid -(41-chlor)-anilide and 2-oxydiphenylene oxide -3-carboxylic acid -(21,51-dimethoxy)-anilide from 2,6-diaminoanthraquinone and (3) 1 - acetoacetylamino - 2 - chloro- and -methoxy-, -2,5-dichloro-, -4-methyl- and 2,5-dimethoxy-4-chloro - benzenes, 1 - acetoacetylamino - benzene, 1-(21-chlorophenyl)-3-methyl-5-pyrazolone and 21 - oxy - 31 - naphthoylamino - benzene and -2-methoxybenzene, from 2,5- and 2,6-diaminoanthraquinones and (5) 5,8-dichloro-1-naphthol and from 2,6-diamino-3,7-dibrom-, 1,5-dichloro-and -1,3,5,7-tetrabrom-anthraquinones and (6) 1-acetoacetylamino-2-chlorobenzene.ALSO:The invention comprises dyestuffs of formula R2-N=N-R1-N=N-R2 where R1 is an anthraquinone residue free of sulphonic and carboxylic acid groups and in which the two carbon atoms to which the azo linkages are bound are separated from one another by at least three carbon atoms of the antraquinone nucleus and R2 is a residue of an azo component free of sulphonic and carboxylic acid groups and bound to the azo linkage in a position vicinal to a hydroxyl group.  They are made by coupling appropriate tetrazotized diamino anthraquinones with coupling components. Advantageously the diamine is tetrazotized in concentrated sulphuric acid and the tetrazo compound isolated before coupling.  Coupling is advantageously effected in a weakly acid medium in the presence of a wetting or dispersing agent.  Specified diaminoanthraquinones are: 1, 5-, 1, 6-, 1, 7-, 2, 6-, and 2, 7-diamino-, 4, 8-dichlor-, 2, 4, 6, 8-tetrachlor-, 2, 6-dibromo- and 2, 4, 6, 8-tetrabromo-1, 5-diamino-, 1, 5-dichloro-, 1, 5- and 3, 7-dibromo- and 1, 3, 5, 7-tetrabromo-2, 6-diamino- and 3, 6-dibromo-2, 7-diamino-anthraquinone.  Azo components specified are 4-methyl- and 5, 8-dichloro-1-naphthol, 2-naphthol, 6-bromo-2-naphthol, 2-naphthol-3-carboxylic acid naphthyl-(1)-amide, -phenylamide and -21-methoxyphenylamide. 2-oxycarbazole-3-carboxylic acid anilide and -41-chloranilide, 2-oxydiphenylene oxide-3-carboxylic acid anilide or -21, 51dimethoxy-anilide, 1-benzoylacetylamino-2-methoxy-5-methylbenzene and acetylamino compounds derived from the following amines: aniline, 1-amino-2-chloro, -methyl- and -methoxy-, -4-methyl, -2, - 5-dichloro-, -2, - 4-dimethyl-5-chloro-, 2-chloro-4-acetylamino-5-methoxy-2-chloro-5-trifluoromethyl-, -2, - 5-dimethoxy-4-chloro-, -2-methoxy-5-methyl- and -2, 6-dimethylbenzene and 1-aminobenzene-3-sulphonic acid amide and 2-acetoacetylamino-6-methoxybenzthiazole, barbuturic acid, 1-naphthyl-(2)-, -phenyl-, ,-(21-chlorophenyl)- and (21methoxy-51 methylphenyl)-3-methyl-5-pyrazoline. The products are used in the dyeing or printing of a wide variety of materials and especially in pigment printing.  The following materials may be dyed, paper, glass fibres, artificial silks, rubber, lacquers, natural and synthetic resins, coloured pencils, cosmetic preparations and laminated plates, yellow, red, brown and blue shades are obtained.  Examples and tables specified components an additional of dyestuffs from certain of the above are provided illustrating the preparation coupling component being 2-acetoacetylamino-6-ethoxy-benzthiazole.ALSO:Pigment dyestuffs of formula R2 - N = N - R1 - N = N - R2 where R1 is an anthraquinone residue free of sulphuric and carboxylic acid groups and in which the two carbon atoms to which the azo linkages are bound are separated from one another by at least three carbon atoms of the anthraquinone nucleus and R2 is a residue of an azo component free of sulphuric and carboxylic acid groups and bound to the azo linkage in a position vicinal to a hydroxyl group are used for colouring rubber.  The preparation of the dyestuffs and lists of components used therein is in Group IV(c).  The pigments are in yellow, red, brown, and blue shades.