Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/153601
Title: Synthesis of degradable and chemically recyclable polymers using 4,4-disubstituted five-membered cyclic ketene hemiacetal ester (CKHE) monomers
Authors: Oh, Xin Yi
Ge, Yicen
Goto, Atsushi
Keywords: Science::Chemistry::Organic chemistry::Polymers
Issue Date: 2021
Source: Oh, X. Y., Ge, Y. & Goto, A. (2021). Synthesis of degradable and chemically recyclable polymers using 4,4-disubstituted five-membered cyclic ketene hemiacetal ester (CKHE) monomers. Chemical Science, 12(40), 13546-13556. https://dx.doi.org/10.1039/D1SC03560F
Project: NRF-NRFI05-2019-0001
A1786a0029
Journal: Chemical Science
Abstract: Novel degradable and chemically recyclable polymers were synthesized using five-membered cyclic ketene hemiacetal ester (CKHE) monomers. The studied monomers were 4,4-dimethyl-2-methylene-1,3-dioxolan-5-one (DMDL) and 5-methyl-2-methylene-5-phenyl-1,3-dioxolan-4-one (PhDL). The two monomers were synthesized in high yields (80-90%), which is an attractive feature. DMDL afforded its homopolymer with a relatively high molecular weight (Mn > 100,000, where Mn is the number-average molecular weight). DMDL and PhDL were copolymerized with various families of vinyl monomers, i.e., methacrylates, acrylates, styrene, acrylonitrile, vinyl pyrrolidinone, and acrylamide, and various functional methacrylates and acrylate. Such a wide scope of the accessible polymers is highly useful for material design. The obtained homopolymers and random copolymers of DMDL degraded in basic conditions (in the presence of a hydroxide or an amine) at relatively mild temperatures (room temperature to 65 °C). The degradation of the DMDL homopolymer generated 2-hydroxyisobutyric acid (HIBA). The generated HIBA was recovered and used as an ingredient to re-synthesize DMDL monomer, and this monomer was further used to re-synthesize the DMDL polymer, demonstrating the chemical recycling of the DMDL polymer. Such degradability and chemical recyclability of the DMDL polymer may contribute to circular materials economy.
URI: https://hdl.handle.net/10356/153601
ISSN: 2041-6520
DOI: 10.1039/D1SC03560F
Rights: © 2021 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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