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Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization

In order to discuss the polymerization effect from the substituted position and methoxy group of Type I photinitiators, a series of naphthalene-based oxime esters was designed and synthesized. Compared to the 2-naphthalene-substituted compound, the UV absorption region of the 1-naphthalene-based com...

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Autores principales: Lee, Zhong-Han, Yen, Shih-Chieh, Hammoud, Fatima, Hijazi, Akram, Graff, Bernadette, Lalevée, Jacques, Chen, Yung-Chung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9735988/
https://www.ncbi.nlm.nih.gov/pubmed/36501655
http://dx.doi.org/10.3390/polym14235261
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author Lee, Zhong-Han
Yen, Shih-Chieh
Hammoud, Fatima
Hijazi, Akram
Graff, Bernadette
Lalevée, Jacques
Chen, Yung-Chung
author_facet Lee, Zhong-Han
Yen, Shih-Chieh
Hammoud, Fatima
Hijazi, Akram
Graff, Bernadette
Lalevée, Jacques
Chen, Yung-Chung
author_sort Lee, Zhong-Han
collection PubMed
description In order to discuss the polymerization effect from the substituted position and methoxy group of Type I photinitiators, a series of naphthalene-based oxime esters was designed and synthesized. Compared to the 2-naphthalene-substituted compound, the UV absorption region of the 1-naphthalene-based compound was greatly improved. In addition, the methoxy substitution exhibited longer absorption characteristics than did the methoxy-free one. The photochemical reaction behavior of these novel compounds was also studied by photolysis, cyclic voltammetry (CV), and electron spin resonance (ESR) experiments. Finally, the initiation abilities of naphthalene-based oxime esters toward trimethylolpropane triacrylate (TMPTA) monomer were conducted through the photo-DSC instrument under UV and a 405@nm LED lamp. Remarkedly, the naphthalene-based oxime ester (NA-3) that contains 1-naphthalene with o-methoxy substituent showed the rather red-shifted absorption region with the highest final conversion efficiency under UV (46%) and 405@nm LED (41%) lamp irradiation.
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spelling pubmed-97359882022-12-11 Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization Lee, Zhong-Han Yen, Shih-Chieh Hammoud, Fatima Hijazi, Akram Graff, Bernadette Lalevée, Jacques Chen, Yung-Chung Polymers (Basel) Article In order to discuss the polymerization effect from the substituted position and methoxy group of Type I photinitiators, a series of naphthalene-based oxime esters was designed and synthesized. Compared to the 2-naphthalene-substituted compound, the UV absorption region of the 1-naphthalene-based compound was greatly improved. In addition, the methoxy substitution exhibited longer absorption characteristics than did the methoxy-free one. The photochemical reaction behavior of these novel compounds was also studied by photolysis, cyclic voltammetry (CV), and electron spin resonance (ESR) experiments. Finally, the initiation abilities of naphthalene-based oxime esters toward trimethylolpropane triacrylate (TMPTA) monomer were conducted through the photo-DSC instrument under UV and a 405@nm LED lamp. Remarkedly, the naphthalene-based oxime ester (NA-3) that contains 1-naphthalene with o-methoxy substituent showed the rather red-shifted absorption region with the highest final conversion efficiency under UV (46%) and 405@nm LED (41%) lamp irradiation. MDPI 2022-12-02 /pmc/articles/PMC9735988/ /pubmed/36501655 http://dx.doi.org/10.3390/polym14235261 Text en © 2022 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
Lee, Zhong-Han
Yen, Shih-Chieh
Hammoud, Fatima
Hijazi, Akram
Graff, Bernadette
Lalevée, Jacques
Chen, Yung-Chung
Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization
title Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization
title_full Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization
title_fullStr Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization
title_full_unstemmed Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization
title_short Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization
title_sort naphthalene-based oxime esters as type i photoinitiators for free radical photopolymerization
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9735988/
https://www.ncbi.nlm.nih.gov/pubmed/36501655
http://dx.doi.org/10.3390/polym14235261
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