Diacetylene-containing polymers. XV. Synthesis and characterization of poly(dipropargyloxybenzoates) containing Disperse Red 1

In order to obtain novel polymers having a very high chromophore density, dipropargyloxy benzoic acids converted to benzoates containing an azo dye, Disperse Red 1, were synthesized and characterized. 2,6-Dipropargyloxy benzoic acid could not be obtained. The bisacetylenic monomers were then polymerized by oxidative coupling reaction. Amorphous polymers with an inherent viscosity of around 0.3 in N-methylpyrrolidone (NMP) were obtained. The polymers were soluble in polar solvents such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone. The solutions in DMF caused precipitation due to the agglomeration of the dye groups on standing for a few days, but the precipitated polymers became soluble again in NMP. The UV irradiation on the spin-coated films at 80 °C cross-linked the films to convert them to thermoset resin films.