Thiol-Ene Polymerizations Using Imide-Based Monomers

New diene and dithiol monomers, based on aromatic imides such as benzophenone-3,3,4,4-tetracarboxylic diimide were synthesized and used in thiol-ene polymerizations which yield poly(imide-co-thioether)s. These linear polymers exhibit limited solubility in various organic solvents. The molecular weights of the polymers were found to decrease with increasing imide content. The glass transition temperature (T-g) of these polymers is dependent on imide content, with T-g values ranging from -55 degrees C (with no imide) up to 13 degrees C (with 70% imide). These thermal property improvements are due to the H-bonding and rigidity of the aromatic imide moieties. Thermal degradation, as studied by thermogravimetric analysis, was not significantly different to the nonimide containing thiol-ene polymers made using trimethyloylpropane diallyl ether and 3,5-dioxa-1,8-dithiooctane. It is expected that such monomers may lead to increased glass transition temperatures in other thiol-ene polymer systems as these normally exhibit low glass transition temperatures. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4637-4642