Synthesis and properties of biodegradable network poly(ether-urethane)s from L-lysine triisocyanate and poly(alkylene glycol)s

Authors

  • Minoru Nagata,

    Corresponding author
    1. Division of Applied Life Sciences, Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Shimogamo, Sakyoku, Kyoto 606-8522, Japan
    • Division of Applied Life Sciences, Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Shimogamo, Sakyoku, Kyoto 606-8522, Japan
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  • Akito Oi,

    1. Department of Macromolecular Science and Engineering, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyoku, Kyoto 606-8585, Japan
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  • Wataru Sakai,

    1. Department of Macromolecular Science and Engineering, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyoku, Kyoto 606-8585, Japan
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  • Naoto Tsutsumi

    Corresponding author
    1. Department of Macromolecular Science and Engineering, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyoku, Kyoto 606-8585, Japan
    • Department of Macromolecular Science and Engineering, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyoku, Kyoto 606-8585, Japan
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Abstract

Biodegradable network poly(ether-urethane) films with different hydrophilicity were prepared from L-lysine triisocyanate (LTI) and poly(ethylene glycol) (PEG), poly(1,4-tetramethylene glycol) (PTMG) or poly (propyrene glycol) (PPG) with the molecular weights of 250–2000 g mol−1. Prepolymers prepared by a melt-polycondensation were cast from tetrahydrofuran solution and heated at 65–80°C for 9 h, then postpolymerized at 150–180°C for 10–20 min to form a network. The resultant films were transparent to opaque and insoluble in water and organic solvents. These network films were fully characterized by FTIR, density measurement, wide-angle X-ray scattering (WAXS), differential scanning calorimetry, dynamic mechanical analysis, and tensile tests. WAXS intensity curves of LTI/PEG-1000 and LTI/PEG-2000 exhibited crystalline peaks due to PEG segments, while those of all other network films did amorphous halos. The molecular weights (Mw) between cross-links increased, while the cross-linking density decreased with increasing the Mws of the poly(alkylene glycol)s. Mechanical properties were strongly affected by the type and molecular weights of poly(alkylene glycol)s used. The weight losses of the LTI/PEG series network films that were degraded in a phosphate buffer solution (pH 7.2) at 37°C and the equilibrium water content in distilled water at 20°C were much larger than those of LTI/PTMG and LTI/PPG series ones. In contrast, LTI/PTMG-1000 and LTI/PPG-1000 network films absorbed 150–216% of organic solvents such as benzene and toluene under equilibrium state at 20°C. The use of poly(alkylene glycol)s with different types and the MWs allowed the preparation of novel network poly(ether-urethane) films with a broad range of properties. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012

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