On the mechanism of acylphosphine oxide promoted cationic polymerization

Y. Yagci, J. Borbely, W. Schnabel

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51 Citations (Scopus)

Abstract

The light-induced initiation of the cationic polymerization of the diepoxide (3,4-epoxycyclohexylmethyl)-3′,4′-epoxy-cyclohexane carboxylate (EEC) and of n-butylvinyl ether in the presence of Ph2I+PF6- and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (TMDPO) or 2,6-dimethoxybenzoyldimethoxy-phosphine oxide (DMPME) was investigated. It turned out that 2,4,6-trimethylbenzoyl radicals and diphenylphosphonyl radicals do not react with Ph2I+ ions but abstract hydrogens from appropriate donors such as tetrahydrofuran. The resulting carbon-centered radicals are converted into carbocations by reaction with Ph2I+ ions. These carbocations initiate the polymerization of EEC. Radicals formed in the photolysis of DMPME seem to react with Ph2I+ ions. The species generated in these reactions were capable of initiating the polymerization of EEC. n-Butylvinyl ether was readily polymerized in the presence of TMDPO and Ph2I+ ions. Phosphorus was incorporated into the polymer as evidenced by P-31 NMR measurements. The proposed initiation mechanism assumes the addition of the Ph2 P ̇O radical to CH2CH(OR). The radical resulting from this addition is capable of reacting with Ph2I+.

Original languageEnglish
Pages (from-to)129-131
Number of pages3
JournalEuropean Polymer Journal
Volume25
Issue number2
DOIs
Publication statusPublished - 1989

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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