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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ftinraparis:oai:prodinra.inra.fr:423110 2023-05-15T13:58:37+02:00 Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers Hollande, Louis Reano, Felix A. Domenek, Sandra Diot-Néant, Florian Migeot, Loïs Allais, Florent 2017 application/pdf http://prodinra.inra.fr/ft/D42CD072-2798-4C6D-975B-27A5FB67DB98 http://prodinra.inra.fr/record/423110 https://doi.org/10.3389/fchem.2017.00126 eng eng http://creativecommons.org/licenses/by-nd-nc/1.0/ CC-BY-ND-NC Frontiers in Chemistry (5), 1-10. (2017) Polymères Polymers antioxidants;ROMP;lipase;CAL-B;norbornene;ferulic acid;sinapic acid;DPPH ARTICLE 2017 ftinraparis https://doi.org/10.3389/fchem.2017.00126 2018-03-13T23:24:44Z 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 Institut National de la Recherche Agronomique: ProdINRA Frontiers in Chemistry 5 |
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Open Polar |
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Institut National de la Recherche Agronomique: ProdINRA |
op_collection_id |
ftinraparis |
language |
English |
topic |
Polymères Polymers antioxidants;ROMP;lipase;CAL-B;norbornene;ferulic acid;sinapic acid;DPPH |
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Polymères Polymers antioxidants;ROMP;lipase;CAL-B;norbornene;ferulic acid;sinapic acid;DPPH Hollande, Louis Reano, Felix A. Domenek, Sandra Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
topic_facet |
Polymères Polymers antioxidants;ROMP;lipase;CAL-B;norbornene;ferulic acid;sinapic acid;DPPH |
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. |
author2 |
Diot-Néant, Florian Migeot, Loïs Allais, Florent |
format |
Article in Journal/Newspaper |
author |
Hollande, Louis Reano, Felix A. Domenek, Sandra |
author_facet |
Hollande, Louis Reano, Felix A. Domenek, Sandra |
author_sort |
Hollande, Louis |
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 |
publishDate |
2017 |
url |
http://prodinra.inra.fr/ft/D42CD072-2798-4C6D-975B-27A5FB67DB98 http://prodinra.inra.fr/record/423110 https://doi.org/10.3389/fchem.2017.00126 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Frontiers in Chemistry (5), 1-10. (2017) |
op_rights |
http://creativecommons.org/licenses/by-nd-nc/1.0/ |
op_rightsnorm |
CC-BY-ND-NC |
op_doi |
https://doi.org/10.3389/fchem.2017.00126 |
container_title |
Frontiers in Chemistry |
container_volume |
5 |
_version_ |
1766266973783588864 |