Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers
AbstractIn 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
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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.
Kim MS, Lee SB. Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers. Materials. 2014; 7(8):5581-5590.Chicago/Turabian Style
Kim, Moon S.; Lee, Sang B. 2014. "Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers." Materials 7, no. 8: 5581-5590.