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Materials 2014, 7(8), 5581-5590; doi:10.3390/ma7085581

Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers

1
Department of Molecular Science and Technology, Ajou University, Suwon 443-749, Korea
2
Division of Green Chemistry & Engineering Research, Research Institute of Chemical Technology, Daejeon 305-600, Korea
*
Author to whom correspondence should be addressed.
Received: 4 July 2014 / Revised: 23 July 2014 / Accepted: 24 July 2014 / Published: 31 July 2014
(This article belongs to the Special Issue Photocatalytic Materials)
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Abstract

In order to study the capability of pyrazinium salt derivatives to act as photo-initiators of epoxide monomers, benzyl pyrazinium hexafluoroantimonate (BPH), benzyl 3,5-dimethyl pyrazine hexafluoroantimonate (BDH) and benzyl quinoxalinium hexafluoroantimonate (BQH) were synthesized by the Menschutkin reaction of benzyl bromide with pyrazine, 2,6-dimethyl pyrazine, and quinoxaline, followed by exchanging with hexafluoroantimonate (SbF6). BPH, BDH, and BQH exhibited characteristic ultraviolet (UV) absorbance as well as exothermic peaks as a function of irradiation time in a differential photo-calorimeter (DPC). In the absence of photo-irradiation, cyclohexene oxide (CHO) underwent slow polymerization at 25 °C using BPH derivatives, but quantitative conversion was achieved even after a 5-min photo-irradiation. In addition, photo-irradiation was required for the photo-polymerization of CHO and styrene oxide (STO), which was characterized by a short induction period followed by a very rapid and exothermic polymerization. While glycidyl methyl ether (GME) required long induction periods, glycidyl phenyl ether (GPE) underwent rather slow and/or no photo-polymerization. The reactivity order of the monomers was CHO > STO >> GME >>> GPE, and the reactivity order for the photo-polymerization of CHO was BPH > BQH > BDH. It was found that BPH, BDH, and BQH could serve as photo-latent initiators for CHO, STO and GME, respectively. View Full-Text
Keywords: ultraviolet (UV) light irradiation; photo-initiators; latent; epoxide monomers; benzyl pyrazinium salt ultraviolet (UV) light irradiation; photo-initiators; latent; epoxide monomers; benzyl pyrazinium salt
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Kim, M.S.; Lee, S.B. Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers. Materials 2014, 7, 5581-5590.

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