Patent GB-1092451-A (GB)
Title: Benzonaphthindolizinedione-carboxyarylamide colouring matters and their production
Inventor: INMAN ERIC RICHARD
IPC: C07D471/04
Filed: 1964-11-07
Abstract: The invention comprises benzo-[g]-naphth-[2,3 - b-] - indolizine - 8,13 - dione - 14 - carboxyarylamides of the formula <FORM:1092451/C4-C5/1> wherein A is an arylene residue unsubstituted or substituted with one or more halogen atoms or C1-C5 alkyl or alkoxy, aryloxy or halogen-substituted aryloxy groups; B is a phenyl or an a - or b -naphthyl group unsubstituted or substituted with one or more halogen atoms or C1-C5 alkyl or alkoxy, CF3, CN, C1-C5 alkanoyl, aroyl, NO2, N-(C1-C5) alkyl-substituted-carbamoyl or -sulphamoyl, C1-C5 alkyl sulphone, aryl sulphone, C1-C5 alkyl-substituted-carbonylamino or -sulphonylamino or C1 - C5 alkoxy -substituted carbonylamino groups.  They may be obtained by (i) reacting a benzo - [g] - naphth - [2,3 - b-] - indolizine-8,13 -dione-14-carboxylic acid halide of the formula <FORM:1092451/C4-C5/2> with a substituted or unsubstituted mono-N-benzoylarylene diamine or mono-N(1- or 2-naphthoyl)-arylene diamine of the formula H2N.A.NH.CO.B (ii) condensing a benzo-[g]-naphth-[2,3-b-]-indolizine-8,13-dione-14-carboxylic acid of the formula <FORM:1092451/C4-C5/3> with a substituted or unsubstituted mono-N-benzoyl-arylene diamine of the formula H2N.A.NH.CO.B e.g. by using PCl3 as a condensing agent; or (iii) reacting an acetoacetylaminobenzanilide or acetoacetylamino - N - (1- or 2 - naphthanilide) of the formula CH3CO.CH2CO.NH.A.NHCO.B with an appropriate 1:4-naphthoquinone and with isoquinoline.  Examples are given for the production of the dyes.  They are suitable for pigmenting paints, lacquers, printing inks, rubber, artificial polymeric materials, paper and textile materials.ALSO:Polyvinyl chloride polymers and other polyolefin polymers, and lacquers, are pigmented with pigments of the formula <FORM:1092451/C3/1> wherein A is an arylene residue unsubstituted or substituted with one or more halogen atoms or lower alkyl, lower alkoxy, aryloxy or halogen-substituted aryloxy groups; and B is a phenyl or an a - or b -naphthyl group unsubstituted or substituted with one or more halogen atoms or lower alkyl, lower alkoxy, CF3, CN, lower alkanoyl, aroyl, NO2, N-lower alkyl-substituted carbamoyl, N-lower alkyl-substituted sulphamoyl, lower alkyl sulphone, aryl sulphone, lower alkyl-substituted carbonylamino, lower alkyl-substituted sulphonylamino or lower alkoxy-substituted carbonylamino groups, wherein lower indicates a group containing not more than 5 carbon atoms.  Particular pigments are specified in the examples for colouring, a polyvinyl chloride composition also containing dialphenyl phthalate, barium-cadmium and epoxy stabilizers and titanium dioxide, and an example is given in which a lacquer derived from a carbamide resin, an alkyd resin and a melamine formaldehyde resin is coloured.ALSO:Benzo - [G] - naphth - [2,3 - b-] - indolizine-8,13-dione-14-carboxylic acid is obtained by hydrolysis of the corresponding alkyl esters, which may themselves be obtained by condensation of a 2,3-dihalo-1,4-naphthoquinone, an alkyl acetoacetate and isoquinoline.  This carboxylic acid may be converted to the corresponding acid chloride by treatment with thionyl chloride.