Patent GB-864896-A (GB)
Title: New metalliferous monoazo-dyestuff pigments and process for their manufacture
IPC: C09B45/14
Filed: 1957-04-26
Abstract: Polyvinyl chloride is coloured by a chromium, nickel, cobalt or copper 1, 1- or 1, 2- complex, which is free from groups imparting solubility in water, and derived from a dye of formula:- <FORM:0864896/IV (a)/1> where n is 1 or 2, R is a residue of an aromatic diazo component with -(CO)n-1-OH vicinal to N2, A is a coupling component residue with OH vicinal to N2 and B is an at least tricyclic aryl residue which may contain heterocyclic rings. Advantageously the diazo components are of the benzene or naphthalene series and may contain substituents such as nitro, halogen, alkyl, alkoxy and acylamino groups.  Preferred coupling components are those in which A is an at least bicyclic aryl residue or a pyrazolone or acetoacetic acid arylide residue.  In examples polyvinyl chloride e.g. in the form of foils, is coloured in orange, grey, red, blue and brown shades. Specifications 235,862, 540,743, 810,207 and 838,657 are referred to.ALSO:The invention comprises chromium, nickel, cobalt or copper complexes which are free from groups imparting solubility in water and derived from a dye of formula:-  <FORM:0864896/IV(c)/1> where n is 1 or 2, R is a residue of an aromatic diazo component with -(CO)n-1-OH vicinal to N2, A is a coupling component residue with OH vicinal to N2 and B is an at least tricyclic aryl residue which may contain heterocyclic rings.  They are made by metallizing appropriate metal-free dyes using conventional processes. 111- or 112-complexes may be obtained.  The metal-free dyes are made in the usual way although preferably the arylide is formed as a final step from the dye containing an appropriate carboxylic acid group.  Advantageously the diazo components are of the benzene or naphthalene series which may contain substituents such as nitro, halogen, alkyl, alkoxy and acylamino groups, representative of those specified being 2-naphthylamine-3-carboxylic acid, anthranilic acid, 4-methoxy-2-aminophenol, 3, 4, 6-trichlor-2-aminophenol, 6-nitro-4-acetylamino-2-aminophenol and 1-amino-2-naphthol. Corresponding alkoxy compounds e.g. 1, 4-dimethoxy-2-aminobenzene, may also be used.  Preferred coupling components are those in which A is an at least bicyclic aryl residue or a pyrazolone or acetoacetic acid arylide residue. Indicated coupling components are p-oxybenzene-, 2-oxycarbazole-3-, 3-oxydiphenylene oxide-2-, 5- pyrazolone-3-, 1-phenyl-3-methyl-5-pyrazolone-31-or -41- and preferably 2-naphthol-3-carboxylic acid arylides.  Specified amines from which arylides may be obtained are amino-carbazole, -phenanthrene, -anthracene, -anthraquinones and -pyrene, 2-amino-3-methoxy-diphenylene oxide and 3-aminochrysene.  The products are used in pigment printing processes, dyeing artificial silk, viscose, cellulose ethers or esters and superpolyamides and urethanes in the spinning mass, coloured lacquers and lacquer formers, solutions and products of acetyl-cellulose, nitro-cellulose and other synthetic or natural resins, coloured pencils, cosmetics and laminated plates.  Examples are provided of the preparation of the dyes and their use in colouring polyvinyl chloride materials in orange, grey, red, blue and brown shades.  Specifications 235,862, 540,743, 810,207 and 838,657 are referred to.