Patent GB-860278-A (GB)
Title: New tetrazo-dyestuffs
IPC: C09B43/38
Filed: 1957-10-21
Abstract: Dyes, free from groups imparting solubility in water, of formula <FORM:0860278/IV (a)/1> where R1 is a benzene or naphthalene residue free from carboxylic ester groups, R2 is a benzene or naphthalene residue free from carboxylic ester groups, to which the azo links are bound in the 1,4-position relatively to one another, R2 being different from R1, R3 is a naphthalene residue the azo link, the OH group and CONHAr group being in the 1,2,3-positions and Ar is the residue of an aromatic diamine, are used to colour synthetic resins, e.g. polyvinyl chloride foils, polyvinyl chloride or polyvinyl acetate emulsion printing inks and polystyrene, polyethylene or polyacrylate lacquers.  Specified aryl diamines include 4-methyl - 1,3 - diaminobenzene, 3,31 - dichloro-diaminodiphenyl, 4,41 - diaminodiphenyl ether, diaminopyrene, 2,8 - diaminochrysene, 4,11-diaminofluoranthene and 2,6-diaminonaphthalene.  Representative of compounds specified for R1 and R2 are aniline, p-nitraniline, toluidine, 3-trifluoromethylaniline, p-aminodiphenyl, 4-chloro-2,5-dimethoxy-aniline and 1-amino-8-chloronaphthalene. R3 may contain further substituents such as halogen, alkyl and alkoxy groups.  Advantageously Ar contains, at most, four carbocyclic rings. In examples, polyvinyl chloride foils, plasticized with dioctylphthalate are coloured in red or blue shades by rolling in dyes of the above formula.  Specification 730,384 is referred to.ALSO:The invention comprises dyes, free from groups imparting solubility in water, of formula : <FORM:0860278/IV(c)/1> where R1 is a benzene or napthalene residue free from carboxylic acid ester groups, R2 is a benzene or naphthalene residue free from carboxylic acid ester groups, to which the azo links are bound in the 1, 4-position relatively to one another, R2 being different from R1, R3 is a napthalene residue the azo link, the OH and CONH Ar groups being in the 1, 2, p  3-positions and Ar is the residue of an aromatic-diamine.  They may be made by treating appropriate aryl diamines with the requisite disazo dyes containing acid halide groups. Representative of specified aryl diamines are 1, 4-diaminobenzene, 4-methyl-1, 3-diaminobenzene, 3, 31-dichloro-diamino-diphenyl, 4, 41-diamino-diphenyl ether, diamino-pyrene, 2, 8-diamino chrysene, 4, 11-diaminofluoranthene and 2, 6-diaminonaphthalenes. Representative of compounds specified from which R1 is derived are aniline, m-chloroaniline, p-nitraniline, #s-methoxyaniline, toluidine, 3-trifluoromethylaniline, p-aminodiphenyl 3-cyanoaniline, 2-methyl-5-chloroaniline and 4-chloro-2, 5-dimethoxyaniline.  Representative of compounds specified from which R2 is derived are 1-naphthylamine, 1-amino-8-chloronaphthalene, aniline, -2-chloro, -ethoxy and -methyl-anilines and 2-chloro-5-methyl-aniline.  Indicated as further substituents for R3 are halogen, alkyl and alkoxy groups. Advantageously Ar contains, at the most, four carbocyclic rings.  The dyes are used for colouring polyvinyl compounds, in pigment printing, in a dispersed form for colouring artificial silk, viscose, cellulose ethers or esters or super-polyamides or urethanes and for colouring such products as lacquers or lacquerformers, natural and synthetic resins, rubber, coloured pencils, cosmetic preparations and laminated sheets.  Examples are provided of the preparation of the dyes and their use in colouring polyvinyl chloride in red and blue shades. Specification 730,384 is referred to.