Alternating copolymerization of vinylphosphonic acid monoethyl ester with cyclic phosphonites involving proton-transfer

Jun Ichi Kadokawa, I. Fang Yen, Shin Ichiro Shoda, Hiroshi Uyama, Shiro Kobayashi

Research output: Contribution to journalArticlepeer-review

Abstract

This paper describes the alternating copolymerization of vinylphosphonic acid monoethyl ester 1 with five-, six-, and seven-membered cyclic phosphonites (2a, 2b, and 2c). The copolymerization took place without any catalyst. Reaction of the 1:1 monomer feed ratio gave alternating copolymers having the phosphonite-phosphonate unit. During the copolymerization the proton-transfer in monomer 1 took place and the oxidation-reduction process is involved. The copolymerization is reasonably explained by a mechanism which involves zwitterion intermediates. The apparent monomer reactivity ratios determined in benzonitrile at 150°C are r1=0.00 and r2b=0.16. A kinetic study of the Michael-type addition in the initiation stage showed that 2b was more reactive than 2a or 2c.

Original languageEnglish
Pages (from-to)1205-1214
Number of pages10
JournalPolymer Journal
Volume24
Issue number11
DOIs
Publication statusPublished - 1992 Nov

Keywords

  • Alternating copolymerization
  • Cyclic phosphonite
  • Proton-transfer
  • Vinylphosphonic acid monoethyl ester
  • Zwitterion mechanism

ASJC Scopus subject areas

  • Polymers and Plastics
  • Materials Chemistry

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