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US 4,083,858 AGranted
Anthraquinone dyes
AssigneeImperial Chemical Industries PLC
InventorsJohn Stuart Manson, Denis Robert Annesley Ridyard
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Abstract
A process for the manufacture of water-soluble anthraquinone dyes having the general formula: ##STR1## wherein Z represents an optionally substituted hydrocarbon residue carrying at least one half sulphuric acid ester or sulphonic acid group which comprises reacting 1,8-dihydroxy-4-amino-5-nitroanthraquinone with a primary amine of the formula: Z-NH.sub.2 in the presence of boric acid or its anhydride or a derivative thereof and a secondary or tertiary organic base or a polar solvent.
Claims1
A process for the manufacture of a water-soluble anthraquinone dye having the formula:
- ##STR11## which comprises reacting 1,8-dihydroxy-4-amino-5-nitroanthraquinone with a primary amine of the formula
- Z - NH.sub.2
- wherein Z represents a radical of the formula ##STR12## wherein the aromatic ring may optionally carry one or more substituents selected from halogen, hydroxy, lower alkyl, lower alkoxy, nitro and acetylamino, or ##STR13## the reaction being carried out in the presence of boric acid present in amounts of 1-3 moles per mole of said 1,8-dihydroxy-4-amino-5-nitroanthraquinone and either an organic base selected from pyridine, piperidine, morpholine, triethylamine and N,N-dimethylaniline present in amounts of 0.1-10 moles per mole of said 1,8-dihydroxy-4-amino-5-nitroanthraquinone or a polar solvent selected from dimethylformamide and dimethylsulphoxide present in amounts of from 0.1 mole to a large excess per mole of said 1,8-dihydroxy-4-amino-5-nitroanthraquinone.
Dependencies are inferred from the claim text.