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Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization

[Image: see text] In this work, dihydro-5-hydroxyl furan-2-one (2H-HBO), a renewable-sourced chemical containing the hydroxyl functionality, is converted into its acrylic counterpart for the first time through a green chemical procedure using methacrylic anhydride. This newly synthesized acrylic mon...

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Autores principales: Ray, Parijat, Hughes, Timothy, Smith, Craig, Simon, George P., Saito, Kei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641244/
https://www.ncbi.nlm.nih.gov/pubmed/31458513
http://dx.doi.org/10.1021/acsomega.7b01929
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author Ray, Parijat
Hughes, Timothy
Smith, Craig
Simon, George P.
Saito, Kei
author_facet Ray, Parijat
Hughes, Timothy
Smith, Craig
Simon, George P.
Saito, Kei
author_sort Ray, Parijat
collection PubMed
description [Image: see text] In this work, dihydro-5-hydroxyl furan-2-one (2H-HBO), a renewable-sourced chemical containing the hydroxyl functionality, is converted into its acrylic counterpart for the first time through a green chemical procedure using methacrylic anhydride. This newly synthesized acrylic monomer is able to be polymerized using different techniques such as bulk, solution, and emulsion polymerization. The ability of this monomer to copolymerize with other commercially available acrylates is studied using emulsion polymerization techniques. The pendent lactone ring remains unopened during polymerization and the new monomer is able to copolymerize with other acrylates such as methyl methacrylate and styrene. Reversible addition-fragmentation chain transfer reaction emulsion polymerization is also studied with the same monomer, leading to a steady conversion (∼60%) with a low polydispersity of 1.06. The homopolymer produced from such an emulsion polymerization shows a higher molecular weight than that produced from other methods, with a glass transition temperature of around 105 °C. This demonstrates the potential of this monomer as an interesting, green replacement for methyl methacrylate in certain fields of application.
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spelling pubmed-66412442019-08-27 Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization Ray, Parijat Hughes, Timothy Smith, Craig Simon, George P. Saito, Kei ACS Omega [Image: see text] In this work, dihydro-5-hydroxyl furan-2-one (2H-HBO), a renewable-sourced chemical containing the hydroxyl functionality, is converted into its acrylic counterpart for the first time through a green chemical procedure using methacrylic anhydride. This newly synthesized acrylic monomer is able to be polymerized using different techniques such as bulk, solution, and emulsion polymerization. The ability of this monomer to copolymerize with other commercially available acrylates is studied using emulsion polymerization techniques. The pendent lactone ring remains unopened during polymerization and the new monomer is able to copolymerize with other acrylates such as methyl methacrylate and styrene. Reversible addition-fragmentation chain transfer reaction emulsion polymerization is also studied with the same monomer, leading to a steady conversion (∼60%) with a low polydispersity of 1.06. The homopolymer produced from such an emulsion polymerization shows a higher molecular weight than that produced from other methods, with a glass transition temperature of around 105 °C. This demonstrates the potential of this monomer as an interesting, green replacement for methyl methacrylate in certain fields of application. American Chemical Society 2018-02-20 /pmc/articles/PMC6641244/ /pubmed/31458513 http://dx.doi.org/10.1021/acsomega.7b01929 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Ray, Parijat
Hughes, Timothy
Smith, Craig
Simon, George P.
Saito, Kei
Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization
title Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization
title_full Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization
title_fullStr Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization
title_full_unstemmed Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization
title_short Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization
title_sort synthesis of bioacrylic polymers from dihydro-5-hydroxyl furan-2-one (2h-hbo) by free and controlled radical polymerization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641244/
https://www.ncbi.nlm.nih.gov/pubmed/31458513
http://dx.doi.org/10.1021/acsomega.7b01929
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