Patent GB-844794-A (GB)
Title: New acid amide disazo-pigment-dyestuffs and process for their manufacture
IPC: C09B33/147
Filed: 1957-10-11
Abstract: Dyes, free from water-solubilising groups, and of formula: <FORM:0844794/IV(a)/1> where R1 is a benzene residue containing a carboxylic ester group in m-or p-position to the azo group, R2 is a naphthalene residue in which N2, OH and CONH are in the 1, 2, 3 positions and which may contain halogen, alkyl and alkoxy groups and R3 is an aryl radical are used to colour polyvinyl chloride, e.g. by rolling into foils.  Preferably the ester group is in the m-position to the azo group, R1 contains a chlorine atom p to the ester group, R2 is unsubstituted and R3 contains, at most, 4 carbocyclic rings. Indicated as diamines from which R3 may be derived are 1, 4-diaminobenzene, 4, 41-diaminodiphenyl, 4, 41-diaminodiphenyl ether, 2, 6-and 1, 5-diaminonaphthalene, 2, 8-diaminochrysene and 4, 11-diaminofluoranthene.  Indicated ester groups include phenyl esters although preferred are esters with alcohols containing up to 6 carbon atoms in the molecule. Examples are provided red shades being obtained.  In one example the polyvinyl chloride is plasticized with dioctyl phthalate. Specification 730,384 is referred to.ALSO:The invention comprises dyes, free from water-solubilising-groups, and of formula:  <FORM:0844794/IV (c)/1> where R1 is a benzene residue containing a carboxylic ester group in m- or p-position to the azo-group, R2 is a naphthalene residue in which N2, OH and CONH are in the 1, 2, 3 positions and which may contain halogen, alkyl and alkoxy groups and R3 is an aryl radical.  They are made by condensing about one mol of a diamine, corresponding to R3, with two mols of the same, or with one mol each of two different, appropriate carboxylic acid halides.  Preferably the ester group is in the m-position to the azo group.  Preferably R1 contains a chlorine atom p to the ester group, R2 is unsubstituted and R3 contains, at most, 4 carbocyclic rings. Examples of indicated diamines (R3) are 1, 4 diaminobenzene which may contain nitro, halogen, alkoxy and alkyl groups in the 2, 5-positions, 4, 41-diaminodiphenyl and its 3, 31-dichloro, -dimethyl- and -dialkoxyderivatives, 3, 5, 31, 51-tetrachloro-4, 41-diaminodiphenyl, 4, 41-diamino-diphenyl ether, 2, 8-diamino-chrysene, 4, 11-diaminofluoranthene and 2, 6- and 1, 5-diamino-naphthalene. Indicated ester groups include phenyl esters which may be substituted with alkyl, alkoxy, or halogen groups, preferred being esters with alcohols containing up to 6 carbon atoms in the molecule such as methanol, isopropanols, butanols and hexanols. Amongst specified ester groups are the methyl ester of aniline 3- and -4- carboxylic acids, the ethyl ester of 2-nitraniline -4- carboxylic acid, the methyl ester of 4-nitraniline -5- carboxylic acid, the ethyl ester of 2-methoxy-or-phenoxy-aniline-5-carboxylic acid and the methyl ester of 2-chloro-aniline-5-carboxylic acid.  The acid chlorides of the monoazo dyes are made in conventional fashion the preferred halogenating agent being thioriyl chloride.  The dyes are pigments and are used to colour polyvinyl chloride foils and in the pigment printing of textiles, paper, and glass fabrics. They are also used in spinning compositions for colouring artificial silk, viscose, cellulose esters and ethers and superpoly-amides and urethanes, and to colour lacquers, lacquer formers, natural and synthetic resins, rubber, coloured pencils, and cosmetic preparations.  Examples are provided of the preparation of the pigments and their use in colouring polyvinyl chloride foils in red, brown and orange shades.  Specification 730,384 is referred to.