Synthesis and characterization of new optically active segmented poly(amide imide urethane)s based on different diacids via an isocyanate route

Abstract

A new class of optically active poly(amide imide urethane)s (PAIUs) was synthesized via a two-step diisocyanate route. In the first step, 4,4′-methylenebis(phenyl isocyanate) (MDI) was reacted with different diacids to produce an isocyanate-terminated oligo(amide imide). The chain extension of the previous hard segment with poly (ethylene glycol) diols with a molecular weight of 400 was the second step for furnishing a series of new PAIUs. N-Trimellitylimido-L-leucine was used as a diacid monomer for polycondensation reactions. Polymerization reactions were performed without any catalysts or with pyridine or dibutyltin dilaurate as a catalyst. The optimized reaction conditions were used for the reaction of N-trimellitylimido-L- isoleucine, N-trimellitylimido-L-methionine, N-trimellitylimido-s-valine, and N-trimellitylimido-L-phenylalamne as diacid monomers with MDI. The resulting multiblock copolymers had inherent viscosities of 0.25-0.78 dL/g. These multiblock copolymers were optically active, thermally stable, and soluble in amide-type solvents. All these polymers were fully characterized with Fourier transform infrared spectroscopy,1H-NMR and ultraviolet-visible spectroscopy, specific rotation measurements, and thermal analyses. Some structural characteristics and physical properties of these new optically active PAIUs were examined. © 2008 Wiley Periodicals, Inc.