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

Parijat Ray, Timothy Hughes, Craig Smith, George Philip Simon, Kei Saito

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)2040-2048
Number of pages9
JournalACS Omega
Volume3
Issue number2
DOIs
Publication statusPublished - 28 Feb 2018

Cite this

@article{7430ec4ad5c4421290a5bd48d8618891,
title = "Synthesis of Bioacrylic Polymers from Dihydro-5-hydroxyl furan-2-one (2H-HBO) by Free and Controlled Radical Polymerization",
abstract = "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.",
author = "Parijat Ray and Timothy Hughes and Craig Smith and Simon, {George Philip} and Kei Saito",
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language = "English",
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journal = "ACS Omega",
issn = "2470-1343",
publisher = "American Chemical Society (ACS)",
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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 Philip; Saito, Kei.

In: ACS Omega, Vol. 3, No. 2, 28.02.2018, p. 2040-2048.

Research output: Contribution to journalArticleResearchpeer-review

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AB - 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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