Cargando…
Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators
Three novel visible-light absorbing benzophenone-based hydrogen acceptors (BPD-D, BPDM-D and BPDP-D) were designed on the basis of a donor–benzophenone–donor structural backbone. Mono or diketone units and double diphenylamine electron-donating groups in para-or meta-positions were introduced to com...
Autores principales: | , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199044/ https://www.ncbi.nlm.nih.gov/pubmed/34072579 http://dx.doi.org/10.3390/polym13111801 |
_version_ | 1783707283303170048 |
---|---|
author | Huang, Tung-Liang Chen, Yung-Chung |
author_facet | Huang, Tung-Liang Chen, Yung-Chung |
author_sort | Huang, Tung-Liang |
collection | PubMed |
description | Three novel visible-light absorbing benzophenone-based hydrogen acceptors (BPD-D, BPDM-D and BPDP-D) were designed on the basis of a donor–benzophenone–donor structural backbone. Mono or diketone units and double diphenylamine electron-donating groups in para-or meta-positions were introduced to comprehend the electronic and structural effects on free radical photopolymerization (FRPP). Such a structural change leads not only to a red-shift of the absorption maxima but strongly enhances their molar extinction coefficients compared to the commercial phototinitiators such as benzophenone (BP) and 4,4′-bis(diethylamino) benzophenone (EMK). In addition, excellent melting points and thermal decomposition temperatures were achieved for those novel compounds. Further, the photochemical reaction behavior was studied by cyclic voltammograms (CV), photolysis and electron spin resonance (ESR) spectroscopy. Finally, benzophenone derivatives in combination with an amine (TEA, triethylamine) as a co-initiator were prepared and initiated the FRPP of trimethylolpropane trimethacrylate (TMPTMA) using a UV lamp as a light source. When used in stoichiometric amounts, the BPDP-D/TEA had the best double bond conversion efficiency among all the compounds studied, and were even superior to the reference compounds of BP/TEA and EMK/TEA. The results and conclusions could provide the fundamental rules applicable for the structural design of benzophenone derivative-based photoinitiators. |
format | Online Article Text |
id | pubmed-8199044 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-81990442021-06-14 Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators Huang, Tung-Liang Chen, Yung-Chung Polymers (Basel) Article Three novel visible-light absorbing benzophenone-based hydrogen acceptors (BPD-D, BPDM-D and BPDP-D) were designed on the basis of a donor–benzophenone–donor structural backbone. Mono or diketone units and double diphenylamine electron-donating groups in para-or meta-positions were introduced to comprehend the electronic and structural effects on free radical photopolymerization (FRPP). Such a structural change leads not only to a red-shift of the absorption maxima but strongly enhances their molar extinction coefficients compared to the commercial phototinitiators such as benzophenone (BP) and 4,4′-bis(diethylamino) benzophenone (EMK). In addition, excellent melting points and thermal decomposition temperatures were achieved for those novel compounds. Further, the photochemical reaction behavior was studied by cyclic voltammograms (CV), photolysis and electron spin resonance (ESR) spectroscopy. Finally, benzophenone derivatives in combination with an amine (TEA, triethylamine) as a co-initiator were prepared and initiated the FRPP of trimethylolpropane trimethacrylate (TMPTMA) using a UV lamp as a light source. When used in stoichiometric amounts, the BPDP-D/TEA had the best double bond conversion efficiency among all the compounds studied, and were even superior to the reference compounds of BP/TEA and EMK/TEA. The results and conclusions could provide the fundamental rules applicable for the structural design of benzophenone derivative-based photoinitiators. MDPI 2021-05-29 /pmc/articles/PMC8199044/ /pubmed/34072579 http://dx.doi.org/10.3390/polym13111801 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Huang, Tung-Liang Chen, Yung-Chung Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators |
title | Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators |
title_full | Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators |
title_fullStr | Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators |
title_full_unstemmed | Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators |
title_short | Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators |
title_sort | ketone number and substitution effect of benzophenone derivatives on the free radical photopolymerization of visible-light type-ii photoinitiators |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199044/ https://www.ncbi.nlm.nih.gov/pubmed/34072579 http://dx.doi.org/10.3390/polym13111801 |
work_keys_str_mv | AT huangtungliang ketonenumberandsubstitutioneffectofbenzophenonederivativesonthefreeradicalphotopolymerizationofvisiblelighttypeiiphotoinitiators AT chenyungchung ketonenumberandsubstitutioneffectofbenzophenonederivativesonthefreeradicalphotopolymerizationofvisiblelighttypeiiphotoinitiators |