Synthesis and characterization of carbamoylphosphonate monomer and its copolymer with styrene. II

Authors

  • Shi Lin,

    1. Polymer Research Institute, Faculty of Chemistry, State University of New York–ESF, Syracuse, New York 13210
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  • Israel Cabasso

    Corresponding author
    1. Polymer Research Institute, Faculty of Chemistry, State University of New York–ESF, Syracuse, New York 13210
    • Polymer Research Institute, Faculty of Chemistry, State University of New York–ESF, Syracuse, New York 13210
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Abstract

A monomer, diethyl α,α-dimethyl-m-isopropenylbenzyl carbamoylphosphonate, has been prepared by the base-catalyzed reaction of the isocyanate m-TMI (α,α-dimethyl-m-isopropenylbenzylisocyanate) with diethyl phosphite. The structure of the carbamoylphosphonate monomer and its styrene copolymer was confirmed spectroscopically, and the nature of the hydrogen bondings in the [BOND]NHC([DOUBLE BOND]O)P([DOUBLE BOND]O)(OR)2 unit in the monomer and copolymer is discussed in detail. A bulk polymerization of the carbamoylphosphonate is very slow and tends to yield a crosslinked product, but a solution polymerization produced the soluble copolymers. The Tg(midpoint) of the homo-polymer is low, 67°C, and its capacity to complex UO2(NO3)2 is very high, 28 wt % (19 mol %). © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 889–899, 1997

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