Combining Cationic Ring-Opening Polymerization and Click Chemistry for the Design of Functionalized Polyurethanes

A straightforward strategy for the synthesis and functionalization of polyurethanes (PUs) via the use of alkyne-functionalized polytetrahydrofuran (PTHF) diols is described. The alkyne groups have been introduced into the PTHF chains by the cationic ring-opening copolymerization of tetrahydrofuran and glycidyl propargyl ether. These PTHF prepolymers were combined with 1,4-butanediol and hexamethylene diisocyanate for the synthesis of linear PUs with latent functionalization sites. The polyether segments of the PUs have then been coupled with several types of functionalized azides by the copper-catalyzed azide-alkyne click'' chemistry, for example with phosphonium containing azides for their antibacterial properties. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 1597-1604, 2011