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Alternating copolymerization of 5-oxazolones with electrophilic monomers via zwitterion intermediates

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Summary

5-Oxazolone (1a) and 4-methyl-5-oxazolone (1b) were found to serve as a nucleophilic monomer (MN) toward electrophilic monomers (ME) like acrylamide (AM) and 2-hydroxyethyl acrylate (HEA). Copolymerizations between these MN and ME monomers took place without added initiator at room temperature and at110 °C to give solid polymers having alternating structures of 3 and 4. The molecular weight of these alternating copolymers is not high. The copolymerization mechanism is explained in terms of zwitterionic intermediates involving a proton-transfer step.

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References

  1. S. Kobayashi, L. L. Bryant, Jr., Y. Tsukamoto and T. Saegusa, Macromolecules in press.

  2. A recent review on alternating copolymerizations via zwitterion intermediates, see S. Kobayashi and T. Saegusa, in “Alternating Copolymers”, Ed. by J. M. G. Cowie, Plenum Publishing Co. New York and London, pp 189–238 (1985).

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Authors and Affiliations

  1. Department of Chemistry, University of Tennessee, 37996, Knoxville, TN, USA

    Lonnie L. Bryant Jr.

  2. Polaroid Corp., 750 Main Street-2W, 02139, Cambridge, MA, USA

    James F. Kinstle

  3. Department of Synthetic Chemistry, Kyoto University, 606, Kyoto, Japan

    Takeo Saegusa & Shiro Kobayashi

Authors
  1. Lonnie L. Bryant Jr.
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  2. James F. Kinstle
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  3. Takeo Saegusa
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  4. Shiro Kobayashi
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Bryant, L.L., Kinstle, J.F., Saegusa, T. et al. Alternating copolymerization of 5-oxazolones with electrophilic monomers via zwitterion intermediates. Polymer Bulletin 15, 227–231 (1986). https://doi.org/10.1007/BF00255067

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  • DOI: https://doi.org/10.1007/BF00255067

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