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Open AccessArticle

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

1
Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford GU2 7XH, UK
2
Intermediates Division, BASF AG, Carl-Bosch-Straße 38, 67056 Ludwigshafen, Germany
3
Bristol Composites Institute (ACCIS), Department of Aerospace Engineering, School of Civil, Aerospace, and Mechanical Engineering, Queen’s Building, University of Bristol, University Walk, Bristol BS8 1TR, UK
*
Author to whom correspondence should be addressed.
Present address: Hexcel Composites, Duxford, Cambridge CB22 4QD, UK.
Present address: School of Engineering and Materials Science, Queen Mary University of London, 327 Mile End Road, London E1 4NS, UK.
Polymers 2019, 11(4), 657; https://doi.org/10.3390/polym11040657
Received: 4 March 2019 / Revised: 28 March 2019 / Accepted: 2 April 2019 / Published: 10 April 2019
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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. View Full-Text
Keywords: epoxy resins; phenyl glycidyl ether; ionic liquids; initiators; latent cure epoxy resins; phenyl glycidyl ether; ionic liquids; initiators; latent cure
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Binks, F.C.; Cavalli, G.; Henningsen, M.; Howlin, B.J.; Hamerton, I. Examining the Influence of Anion Nucleophilicity on the Polymerisation Initiation Mechanism of Phenyl Glycidyl Ether. Polymers 2019, 11, 657.

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