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

Binks, Fiona C., Cavalli, Gabriel, Henningsen, Michael, Howlin, Brendan J. and Hamerton, Ian (2019) Examining the Influence of Anion Nucleophilicity on the Polymerisation Initiation Mechanism of Phenyl Glycidyl Ether Polymers, 11 (4).

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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.

Item Type: Article
Divisions : Faculty of Engineering and Physical Sciences > Chemistry
Authors :
NameEmailORCID
Binks, Fiona C.
Cavalli, GabrielG.Cavalli@surrey.ac.uk
Henningsen, Michael
Howlin, Brendan J.B.Howlin@surrey.ac.uk
Hamerton, IanI.Hamerton@surrey.ac.uk
Date : 10 April 2019
DOI : 10.3390/polym11040657
Copyright Disclaimer : © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Uncontrolled Keywords : Epoxy resins; Phenyl glycidyl ether; Ionic liquids; Initiators; Latent cure
Depositing User : Clive Harris
Date Deposited : 26 Apr 2019 13:51
Last Modified : 26 Apr 2019 13:51
URI: http://epubs.surrey.ac.uk/id/eprint/851702

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