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Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers.

ABSTRACT: 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 ?,?-diphenyl-?-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.

SUBMITTER: Diot-Neant F

PROVIDER: S-EPMC5744638 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers.

Diot-Néant Florian F Migeot Loïs L Hollande Louis L Reano Felix A FA Domenek Sandra S Allais Florent F

Frontiers in chemistry 20171222

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 ...[more]

PMID: 29312930

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Project description:Advances in technology have led to the production of sustainable antioxidants and natural monomers for food packaging and targeted drug delivery applications. Of particular importance is the synthesis of lignin polymers, and graft polymers, dopamine, and polydopamine, inulin, quercetin, limonene, and vitamins, due to their free radical scavenging ability, chemical potency, ideal functional groups for polymerization, abundance in the natural environment, ease of production, and activation of biological mechanisms such as the inhibition of the cellular activation of various signaling pathways, including NF-κB and MAPK. The radical oxygen species are responsible for oxidative damage and increased susceptibility to cancer, cardiovascular, degenerative musculoskeletal, and neurodegenerative conditions and diabetes; such biological mechanisms are inhibited by both synthetic and naturally occurring antioxidants. The orientation of macromolecules in the presence of the plasticizing agent increases the suitability of quercetin in food packaging, while the commercial viability of terpenes in the replacement of existing non-renewable polymers is reinforced by the recyclability of the precursors (thyme, cannabis, and lemon, orange, mandarin) and marginal ecological effect and antioxidant properties. Emerging antioxidant nanoparticle polymers have a broad range of applications in tumor-targeted drug delivery, food fortification, biodegradation of synthetic polymers, and antimicrobial treatment and corrosion inhibition. The aim of the review is to present state-of-the-art polymers with intrinsic antioxidant properties, including synthesis scavenging activity, potential applications, and future directions. This review is distinct from other works given that it integrates different advances in antioxidant polymer synthesis and applications such as inulin, quercetin polymers, their conjugates, antioxidant-graft-polysaccharides, and polymerization vitamins and essential oils. One of the most comprehensive reviews of antioxidant polymers was published by Cirillo and Iemma in 2012. Since then, significant progress has been made in improving the synthesis, techniques, properties, and applications. The review builds upon existing research by presenting new findings that were excluded from previous reviews.

Dataset Information

Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers.

Publications

Biocatalytic Synthesis and Polymerization via ROMP of New Biobased Phenolic Monomers: A Greener Process toward Sustainable Antioxidant Polymers.

Similar Datasets

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