Patent GB-730692-A (GB)
Title: Improvements in and relating to the colouration of plastic materials
IPC: C08K5/3465
Filed: 1953-04-28
Abstract: "Perinones," i.e. substances containing the ring <FORM:0730692/IV (c)/1> in which the two free linkages are connected directly to two carbon atoms are used for dyeing synthetic resins.  The substances are obtained by condensing 1 : 8-naphthylene-diamine or its derivatives with ortho- or peri-dicarboxylic acids, ortho- or peri-tetracarboxylic acids, aliphatic 1 : 2- or 1 : 3-dicarboxylic acids or their substitution derivatives, anhydrides, esters, or imides.  The condensations may be effected by heating the components in the dry state, or an organic solvent, or in an autoclave in the presence of water.  If desired, the C-perimidylcarboxylic acid intermediates may be isolated. Specified perinones 11- and 14-, 12- and 13-chlorophthaloperinones, 11 : 12 : 13 : 14 - tetrachlorophthaloperinone, 13- and 14-bromonaphthaloperinones, 12- and 15-, 13- and 14-nitronaphthaloperinones, 12- and 15-oxynaphthaloperinones, 12- and 15-acetyloxynaphthaloperinones, 12- and 15-methoxynaphthaloperinones, 13- and 14-acetyl- or 14-benzoylnaphthaloperinones, 13- and 14-(o-carboxybenzoyl) - naphthaloperinones, 12- and 15-, 13- and 14-acetylamino-naphthaloperinones, 11 : 12- and 13 : 14-phthaloyl-phthalo-perinones, 12 : 13-phthaloyl-phthaloperinone, 12 : 13- and 14 : 15-phthaloyl-naphthaloperinones, bz-12-acetyloxy-14 : 15- and bz-15-acetyloxy-12 : 13-phthaloylnaphthaloperinones, bz-12-methoxy-14 : 15- and bz - 15 - methoxy - 12 : 13 - phthaloyl - naphthaloperinones, cyclization products of 13- and 14-benzoylnaphthaloperinones, a mixture of the two isomeric diperinones of benzene-1 : 2 : 4 : 5-carboxylic acid and of naphthalene-1 : 4 : 5 : 8-tetracarboxylic acid, naphthaloperinone-13 : 14-dicarboxylic acid, 13-bromo- and 13-nitro-12-oxy- and 14-bromo- and 14-nitro-15-oxynaphthaloperinones, 11 : 12-, 13 : 14-, 12 : 13- and 11 : 14-dichloro-phthaloperinones, and 13 : 14- and 12 : 15-dinitronaphthaloperinones.  Perinones may also be made by condensing 1 : 8-naphthylene diamine with maleic, phthalic, tetrachlorophthalic, 3- or 4-nitronaphthalic, naphthalic, 4 : 5- or 3 : 6-dinitronaphthalic, 3 : 4- or 4 : 5- or 3 : 6-dichlorophthalic, 3- or 4-chlorophthalic, 4-bromophthalic, bz-3-oxy- or bz - 3 - acetyloxy - 1 : 2 - benzanthraquinone - peridicarboxylic, naphthoylene - 4 : 5 - phenylimide-1 : 8 - dicarboxylic, naphthoylene - 4 : 5 - (o1-oxy) phenyl - imide - 1 : 8 - dicarboxylic, 4 - acetylaminonaphthalic, 4 - nitro - 3 - oxynaphthalic, 3 - oxynaphthalic, or 4 - bromo - 3-oxynaphthalic acids.ALSO:Coloured synthetic resin compositions are obtained by incorporating in the resin, e.g. as a melt, at least one perinone or derivative thereof, i.e. a substance containing the structure <FORM:0730692/IV (a)/1> The compositions may also contain other dyestuffs, plasticizers, e.g. tricresyl phosphate, fillers, e.g. cellulose, and accelerators.  The synthetic resin may be phenol-, urea-, thiourea-, melamine - formaldehyde, superpolyamides, superpolyesters, polymers of an ethylene glycol ester of terephthalic acid, polystyrene, polyethylene, polyacrylics or copolymers of vinyl and vinylidene chlorides.  The Specification contains an extensive list of perinones (see Group IV (c)).  The compositions may be used as moulding powders or made into fibres or sheets.