Polyisobutylene-Based Segmented Polyureas. I. Synthesis of Hydrolytically and Oxidatively Stable Polyureas

Novel segmented polyurea elastomers containing soft polyisobutylene (PIB) segments were synthesized and characterized. The key ingredient, primary amine-telechelic PIB oligomers (NH2-PIB-NH2) with number average molecular weights of 2500 and 6200 g/mol were synthesized. PIB-based polyureas were prepared by using various aliphatic diisocyanates and diamine chain extenders with hard segment contents between 9.5 and 46.5% by weight. All copolymers displayed microphase morphologies as determined by dynamic mechanical analysis. Tensile strengths of nonchain-extended and chain-extended polyureas showed a linear dependence on the urea hard segment content. PIB-based polyureas prepared with NH2-PIB-NH2 of M-n = 2500 g/mol, 4,4'-methylendbis(cyclohexylisocyantate), and 1,6-diaminohexane containing 45% hard segment exhibited 19.5 MPa tensile strength which rose to 23 MPa upon annealing at 150 degrees C for 12 h. With increasing hard segment content, elongation at break decreased from similar to 450% to a plateau of 110%. The hydrolytic and oxidative stability of PIB-based polyureas were unprecedented. Although commercial oxidatively resistant thermoplastic polyurethanes degraded severely upon exposure to boiling water or concentrated nitric acid, the experimental polyureas survived without much degradation in properties. (c) 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 38-48, 2009