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Non-isocyanate synthesis and application of telechelic polyurethanes via polycondensation of diurethanes obtained from ethylene carbonate and diamines

Authors

  • Bungo Ochiai,

    Corresponding author
    1. Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata, 992-8510, Japan
    • Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata, 992-8510, Japan
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  • Tomohisa Utsuno

    1. Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata, 992-8510, Japan
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Abstract

Aliphatic polyurethanes could be obtained in high yield via a non-isocyanate method based on the self-polycondensation of dihydroxyurethanes obtained by the reaction of diamines and ethylene carbonate. The polycondensation under a N2 atmosphere yielded [6,2]polyurethane with a Mn value of 5300 in 87% yield. Two-step polycondensation, consisting of the polycondensation under a N2 atmosphere followed by that under reduced pressure, was effective to improve the yield and the molecular weight up to 90% and 10,000, respectively. Although the second polycondensation step at 180 °C was accompanied by formation of urea groups, this side reaction was relatively suppressed at 150 °C. The resulting polyurethane having hydroxyl groups at both of the end groups was converted to polyurethane methacrylate via a reaction with glycidyl methacrylate, and the polyurethane methacrylate served as a crosslinker for radical polymerization of methyl acrylate. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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