Novel processable and heat resistant poly(phenylthiourea azomethine imide)s: Synthesis and characterization

N-(4-chloro-3-aminobenzal)N'(4-aminophenyl)thiourea having phenylthiourea and azomethine groups was synthesized and exploited as starting material for the fabrication of new polymers. Novel diamine was condensed with pyromellitic dianhydride, 3,3',4,4'-benzophenone-tetrcarboxylic dianhydride and 4,4'-(hexafluoroisopropylidene) diphthalic dianhydride to obtain poly(phenylthiourea azomethine imide)s. The structural explication of monomers and poly(phenylthiourea azomethine imide)s were carried out by FTIR, H-1 and C-13 NMR techniques along with crystallinity, organosolubility, inherent viscosity and molecular weight measurements. Accordingly, polymers bearing C=S and -C=N- moieties in the backbone demonstrated an amorphous nature and were readily soluble in amide solvents such as DMAc, DMF, and DMSO. Poly(phenylthiourea azomethine imide)s encompassed eta(inh) of 1.40-1.55 dL/g and were obtained in quantitative yields. In addition, GPC measurements of polymers revealed M-w around 60,291-67,665. Thermal stability of these polymers was ascertained via 10% weight loss temperatures around 514-533 degrees C in an inert atmosphere. Besides, glass transition temperatures of polyimides were found to be 272-276 degrees C. (C) 2010 Elsevier Ltd. All rights reserved.