Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers
Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)—NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)—have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida...
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ftdoajarticles:oai:doaj.org/article:d1175464b26f4ccea39134ece8bdabfa 2023-05-15T14:03:28+02:00 Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers Florian Diot-Néant Loïs Migeot Louis Hollande Felix A. Reano Sandra Domenek Florent Allais 2017-12-01T00:00:00Z https://doi.org/10.3389/fchem.2017.00126 https://doaj.org/article/d1175464b26f4ccea39134ece8bdabfa EN eng Frontiers Media S.A. http://journal.frontiersin.org/article/10.3389/fchem.2017.00126/full https://doaj.org/toc/2296-2646 2296-2646 doi:10.3389/fchem.2017.00126 https://doaj.org/article/d1175464b26f4ccea39134ece8bdabfa Frontiers in Chemistry, Vol 5 (2017) antioxidants ROMP lipase CAL-B norbornene ferulic acid Chemistry QD1-999 article 2017 ftdoajarticles https://doi.org/10.3389/fchem.2017.00126 2022-12-31T04:32:54Z Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)—NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)—have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida antarctica Lipase B (Cal-B). The ring opening metathesis polymerization (ROMP) of these monomers was investigated according to ruthenium catalyst type (GI) vs. (HGII) and monomer to catalyst molar ratio ([M]/[C]). The co-polymerization of antioxidant functionalized monomer (NDF or NDS) and non-active norbornene (N) has also been performed in order to adjust the number of SHP groups present per weight unit and tune the antioxidant activity of the copolymers. The polydispersity of the resulting copolymers was readily improved by a simple acetone wash to provide antioxidant polymers with well-defined structures. After hydrogenation with p-toluenesulfonylhydrazine (p-TSH), the radical scavenging ability of the resulting saturated polymers was evaluated using α,α-diphenyl-β-picrylhydrazyl (DPPH) analysis. Results demonstrated that polymers bearing sinapic acid SHP exhibited higher antiradical activity than the polymer bearing ferulic acid SHP. In addition it was also shown that only a small SHP content was needed in the copolymers to exhibit a potent antioxidant activity. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Frontiers in Chemistry 5 |
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Open Polar |
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Directory of Open Access Journals: DOAJ Articles |
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ftdoajarticles |
language |
English |
topic |
antioxidants ROMP lipase CAL-B norbornene ferulic acid Chemistry QD1-999 |
spellingShingle |
antioxidants ROMP lipase CAL-B norbornene ferulic acid Chemistry QD1-999 Florian Diot-Néant Loïs Migeot Louis Hollande Felix A. Reano Sandra Domenek Florent Allais Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers |
topic_facet |
antioxidants ROMP lipase CAL-B norbornene ferulic acid Chemistry QD1-999 |
description |
Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)—NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)—have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida antarctica Lipase B (Cal-B). The ring opening metathesis polymerization (ROMP) of these monomers was investigated according to ruthenium catalyst type (GI) vs. (HGII) and monomer to catalyst molar ratio ([M]/[C]). The co-polymerization of antioxidant functionalized monomer (NDF or NDS) and non-active norbornene (N) has also been performed in order to adjust the number of SHP groups present per weight unit and tune the antioxidant activity of the copolymers. The polydispersity of the resulting copolymers was readily improved by a simple acetone wash to provide antioxidant polymers with well-defined structures. After hydrogenation with p-toluenesulfonylhydrazine (p-TSH), the radical scavenging ability of the resulting saturated polymers was evaluated using α,α-diphenyl-β-picrylhydrazyl (DPPH) analysis. Results demonstrated that polymers bearing sinapic acid SHP exhibited higher antiradical activity than the polymer bearing ferulic acid SHP. In addition it was also shown that only a small SHP content was needed in the copolymers to exhibit a potent antioxidant activity. |
format |
Article in Journal/Newspaper |
author |
Florian Diot-Néant Loïs Migeot Louis Hollande Felix A. Reano Sandra Domenek Florent Allais |
author_facet |
Florian Diot-Néant Loïs Migeot Louis Hollande Felix A. Reano Sandra Domenek Florent Allais |
author_sort |
Florian Diot-Néant |
title |
Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers |
title_short |
Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers |
title_full |
Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers |
title_fullStr |
Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers |
title_full_unstemmed |
Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers |
title_sort |
biocatalytic synthesis and polymerization via romp of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
publisher |
Frontiers Media S.A. |
publishDate |
2017 |
url |
https://doi.org/10.3389/fchem.2017.00126 https://doaj.org/article/d1175464b26f4ccea39134ece8bdabfa |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Frontiers in Chemistry, Vol 5 (2017) |
op_relation |
http://journal.frontiersin.org/article/10.3389/fchem.2017.00126/full https://doaj.org/toc/2296-2646 2296-2646 doi:10.3389/fchem.2017.00126 https://doaj.org/article/d1175464b26f4ccea39134ece8bdabfa |
op_doi |
https://doi.org/10.3389/fchem.2017.00126 |
container_title |
Frontiers in Chemistry |
container_volume |
5 |
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1766274152891678720 |