Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property

Rosin is an important forestry resource with a specific three-membered phenanthrene ring structure, which can improve the mechanical resistance of polymer coatings. In this paper, a high purity rosin monomer, tri-allyl maleopimarate containing three allyl groups has been synthesized. The yield of th...

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Autores principales: Lu, Yanju, Zhao, Zhendong, Bi, Liangwu, Chen, Yuxiang, Wang, Jing, Xu, Shichao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5799196/
https://www.ncbi.nlm.nih.gov/pubmed/29403028
http://dx.doi.org/10.1038/s41598-018-20695-5
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author Lu, Yanju
Zhao, Zhendong
Bi, Liangwu
Chen, Yuxiang
Wang, Jing
Xu, Shichao
author_facet Lu, Yanju
Zhao, Zhendong
Bi, Liangwu
Chen, Yuxiang
Wang, Jing
Xu, Shichao
author_sort Lu, Yanju
collection PubMed
description Rosin is an important forestry resource with a specific three-membered phenanthrene ring structure, which can improve the mechanical resistance of polymer coatings. In this paper, a high purity rosin monomer, tri-allyl maleopimarate containing three allyl groups has been synthesized. The yield of the monomer product was 93.2% with the purity of 96.1%. The structure of the synthesized monomer was characterized through gas chromatography (GC), mass spectrometry (MS), hydrogen nuclear magnetic resonance spectroscopy ((1)H NMR), carbon nuclear magnetic resonance spectroscopy ((13)C NMR) and elemental analysis. Additionally, we present new experimental results regarding the polymerization reaction under ultraviolet (UV) irradiation. The cured film of tri-allyl maleopimarate exhibited good mechanical properties. The films were also characterized through thermogravimetric (TG) and differential scanning calorimetry (DSC) analyses and a mechanism for polymerization was proposed. Overall, a facile catalytic process for the valorization of rosin in the field of UV polymerization is reported.
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spelling pubmed-57991962018-02-14 Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property Lu, Yanju Zhao, Zhendong Bi, Liangwu Chen, Yuxiang Wang, Jing Xu, Shichao Sci Rep Article Rosin is an important forestry resource with a specific three-membered phenanthrene ring structure, which can improve the mechanical resistance of polymer coatings. In this paper, a high purity rosin monomer, tri-allyl maleopimarate containing three allyl groups has been synthesized. The yield of the monomer product was 93.2% with the purity of 96.1%. The structure of the synthesized monomer was characterized through gas chromatography (GC), mass spectrometry (MS), hydrogen nuclear magnetic resonance spectroscopy ((1)H NMR), carbon nuclear magnetic resonance spectroscopy ((13)C NMR) and elemental analysis. Additionally, we present new experimental results regarding the polymerization reaction under ultraviolet (UV) irradiation. The cured film of tri-allyl maleopimarate exhibited good mechanical properties. The films were also characterized through thermogravimetric (TG) and differential scanning calorimetry (DSC) analyses and a mechanism for polymerization was proposed. Overall, a facile catalytic process for the valorization of rosin in the field of UV polymerization is reported. Nature Publishing Group UK 2018-02-05 /pmc/articles/PMC5799196/ /pubmed/29403028 http://dx.doi.org/10.1038/s41598-018-20695-5 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Lu, Yanju
Zhao, Zhendong
Bi, Liangwu
Chen, Yuxiang
Wang, Jing
Xu, Shichao
Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property
title Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property
title_full Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property
title_fullStr Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property
title_full_unstemmed Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property
title_short Synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and UV-curing property
title_sort synthesis of a multifunctional hard monomer from rosin: the relationship of allyl structure in maleopimarate and uv-curing property
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5799196/
https://www.ncbi.nlm.nih.gov/pubmed/29403028
http://dx.doi.org/10.1038/s41598-018-20695-5
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