Efficient Synthesis of Zwitterionic Sulfobetaine Group Functional Polyurethanes via Click Reaction

A novel polyurethane material containing zwitterionic sulfobetaine groups has been synthesized using the copper-catalyzed 1,3-dipolar cycloaddition (azide-alkyne click chemistry). A standard two-step polyaddition method was used to produce the well-defined polyurethane based on polycarbonatediol (PCDL) with alkyne groups. These polyurethanes containing alkyne units were then efficiently clicked using 3-((2-azidoethyl) dimethylammonio) propane-1-sulfonate (DMPS-N-3). The novel PU material was characterized by H-1 NMR, Fourier transform infrared (FTIR) spectrometer, gel permeation chromatography (GPC), elemental analysis, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and dynamic mechanical analysis (DMA). This facile click reaction provides a useful tool for the development of novel functional polyurethanes for biomedical applications. (C) 2011 Wiley Periodicals, Inc. J Appl Polym Sci 122: 1251-1257, 2011