POLY[(4-N-ETHYLENE-N-ETHYLAMINO)-ALPHA-CYANOCINNAMATE] - A NONLINEAR OPTICAL POLYMER WITH A CHROMOPHORIC MAINCHAIN .1. SYNTHESIS AND SPECTRAL CHARACTERIZATION

Poly[(4-N-ethylene-N-ethylamino)-alpha-cyanocinnamate] was prepared by solution esterification of (4-N-ethyl-N-(2-hydroxyethyl)amino)-alpha-cyanocinnamic acid and by melt transesterification of ethyl (4-N-ethyl-N-(2-hydroxyethyl)amino)-alpha-cyanocinnamate. The melt transesterification generally yielded polymer with a number-average molecular weight of about 10,200 by gel permeation chromatography (GPC) versus polystyrene standards. The polymer was found to be amorphous with a glass transition temperature of about 103-degrees-C by differential scanning calorimetry (DSC). The solution esterification generally gave a polymer with a number-average molecular weight of about 2200 by GPC versus polystyrene standards. This polymer was found to have a glass transition temperature varying between 60 and 90-degrees-C by DSC. The infrared (IR) spectrum of the polymer made from both methods were analyzed in detail. The H-1- and C-13-NMR spectra of the melt-synthesized ethyl cinnamate derivative polymer are consistent with the reported structure.