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Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers
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 Menschutki...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5456198/ https://www.ncbi.nlm.nih.gov/pubmed/28788147 http://dx.doi.org/10.3390/ma7085581 |
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author | Kim, Moon Suk Lee, Sang Bong |
author_facet | Kim, Moon Suk Lee, Sang Bong |
author_sort | Kim, Moon Suk |
collection | PubMed |
description | 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 (SbF(6)). 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. |
format | Online Article Text |
id | pubmed-5456198 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-54561982017-07-28 Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers Kim, Moon Suk Lee, Sang Bong Materials (Basel) Article 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 (SbF(6)). 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. MDPI 2014-07-31 /pmc/articles/PMC5456198/ /pubmed/28788147 http://dx.doi.org/10.3390/ma7085581 Text en © 2014 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 license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Kim, Moon Suk Lee, Sang Bong Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers |
title | Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers |
title_full | Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers |
title_fullStr | Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers |
title_full_unstemmed | Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers |
title_short | Benzylpyrazinium Salts as Photo-Initiators in the Polymerization of Epoxide Monomers |
title_sort | benzylpyrazinium salts as photo-initiators in the polymerization of epoxide monomers |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5456198/ https://www.ncbi.nlm.nih.gov/pubmed/28788147 http://dx.doi.org/10.3390/ma7085581 |
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