Patent GB-1099041-A (GB)
Title: Improvements relating to isoindolinone diimine pigments for high molecular organic products and their use
IPC: C09B57/04
Filed: 1965-04-29
Abstract: The invention comprises pigments of the formula <FORM:1099041/C4-C5/1> wherein each X1, X2, X3 and X4 is Cl or Br and R is a phenyl group or a non-ionogenically substituted or condensed phenyl radical.  The pigments are prepared by condensing a compound of the formula <FORM:1099041/C4-C5/2> wherein Y1, Y2 and Y3 each represent a Cl, etherified hydroxy or tertiary amino group or Y1 and Y2 together are =N-R1 and Y3 is -NH-R1, where R1 is H or alkyl which may contain non-ionogenic substituents or a tautomer thereof with two equivalents of a non-ionogenically substituted or condensed primary phenylamine. Among the non-ionogenic substituents specified typical are Br, Cl, alkyl, alkoxy, -CF3, -CN, carboxylic and sulphonic acid amide and dicarboxylic acid imide groups. In Examples 117 and 118 pigments of the above formula are used in printing ink compositions containing (a) alumina hydrate, linseed oil, cobalt linoleate, (b) wax-free shellac, dibutyl phthalate, polyvinyl butyral, ethylene glycol monoethyl ether and ethanol.ALSO:Isoindolenine pigments are used to colour high molecular organic products the pigments being of formula <FORM:1099041/C3/1> in which each of X1-X4 is chlorine or bromine and R is an unsubstituted or non-ionogenically substituted or condensed phenyl radical.  In examples the following are specified. Example 119 urea resin lacquer, 120, alkyd resin, 121, alkyd resin modified with urea/formaldehyde, 122, polyester resin, 123, epoxide plus alkylphenol resins, 124, polyvinyl chloride, 125, polyvinyl chloride (emulsion powder), 126, polystyrene, 127, polyethylene, 128, rubber mixture, 130, polypropylene granulate, 131, formaldehyde/urea resin.ALSO:1,3,3 - Trimorpholino - 4,5,6,7 - tetrachloroisoindolenine is produced by reacting 1,3,3,4,5,6,7 - heptachloroisoindolenine with morpholine in benzene.  1,3,3 - trimethoxy - 4,5,6,7-tetrachloroisoindolenine is produced by reacting 1,3,3,4,5,6,7 - heptachloroisoindolenine with sodium methylate.ALSO:In Examples 118-123 and 125 coating compositions which contain a compound <FORM:1099041/B1-B2/1> in which X1-4 are chlorine or bromine and R is a non ionogenically substituted or condensed phenyl radical.  The compositions are applied to paper, cardboard, metal surfaces, aluminium, and cotton by flexographic printing, spraying and painting.  The coatings comprise as well as the above pigments, Ex. 118, wax-free shellac, dibutyl phthalate, polyvinyl butyral, ethanol and ethylene glycol monoethyl ether, Ex. 119, TiO2 colodium wool, phthalate resin, urea resin lacquer, butyl acetate, glycol monoethyl ether, toluene and alcohol, Ex. 120, TiO2 alkyd resin, melamine resin, xylene and butanol, Ex. 121, alkyd resin-urea/formaldehyde modified, xylene/butanol mixture, terpentine oil, Ex. 122, polyester resin, TiO2, monostyrene, cobalt drier, cumene hydrogen peroxide, ethyl acetate, butyl acetate, Ex. 123, epoxide resin, alkylphenol resin, xylene, diacetone alcohol, Ex. 125, polyvinyl chloride (emulsion polymer) dioctyl phthalate, dibutyl tin laurate, phosphate, chalk, mineral spirits.