Examining the Influence of Anion Nucleophilicity on the Polymerisation Initiation Mechanism of Phenyl Glycidyl Ether

Fiona C. Binks, Gabriel Cavalli, Michael Henningsen, Brendan J. Howlin, Ian Hamerton*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

3 Citations (Scopus)
181 Downloads (Pure)

Abstract

The reaction of phenyl glycidyl ether (PGE) with 1-ethyl-3-methylimidazolium acetate and 1-ethyl-3-methylimidazolium thiocyanate to initiate the polyetherification reaction was examined using thermal and spectral analysis techniques. The influence of the nucleophilicity of the anions on the deprotonation of the 1-ethyl-3-methylimidazolium cation determined the reaction pathway. The thermal degradation of the ionic liquid liberated the acetate ion and led, subsequently, to the deprotonation of the acidic proton in the imidazole ring. Thus, polymerisation of PGE occurred via a carbene intermediate. The more nucleophilic thiocyanate anion was not sufficiently basic to deprotonate the 1-ethyl-3-methylimidazolium cation, and thus proceeded through direct reaction with the PGE, unless the temperature was elevated and a competing carbene mechanism ensued.

Original languageEnglish
Article number657
Number of pages18
JournalPolymers
Volume11
Issue number4
Early online date10 Apr 2019
DOIs
Publication statusPublished - 10 Apr 2019

Keywords

  • Epoxy resins
  • Initiators
  • Ionic liquids
  • Latent cure
  • Phenyl glycidyl ether

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