We describe the synthesis, characterization, and select properties of a novel polyurethane (PU) prepared using a new polyisobutylene diol, HO-CH2CH2-S-PIB-S-CH2CH2-OH, soft segment and conventional hard segments. The diol is synthesized by terminal functionalization of ally-telechelic PIB followed by low-cost thiol-ene click chemistry. Properties of -S-containing PU (PIBS-PU) containing 72.5% PIB were investigated and compared to similar PUs made with HO-PIB-OH (PIBO-PU). Hydrolytic resistance was studied by contact with phosphate-buffered saline, oxidative resistance by immersing in concentrated HNO3, and metal ion oxidation resistance by exposure to CoCl2/H2O2. Hydrolytic and oxidative resistances of PIBS-PU and PIBO-PU are similar and superior to a commercial PDMS-based PU, Elast-Eon (TM) E(2)A. According to H-1 NMR spectroscopy the -S- in PIBS-PUs remained unchanged upon treatment with HNO3, however, oxidized mainly to -SO2- by CoCl2/H2O2. Static mechanical properties of PIBS-PU and PIBO-PU are similar, except creep resistance of PIBS-PU is surprisingly superior. The thermal stability of PIBS-PUs is similar to 15 degrees C higher than that of PIBO-PU. FTIR spectroscopy indicates H bonded S atoms (N-H center dot center dot center dot S) between soft and hard segments, which noticeably affect properties. DSC and XRD studies suggest random low-periodicity crystals dispersed within a soft matrix. Energy dispersive X-ray spectroscopy-scanning electron microscopy indicates homogeneous distribution of S atoms on PIBS-PU surfaces. (C) 2015 Wiley Periodicals, Inc.