Issue 47, 2023

Branched polyesters from radical ring-opening polymerization of cyclic ketene acetals: synthesis, chemical hydrolysis and biodegradation

Abstract

Herein, we report a new synthetic route to the cyclic ketene acetal, 2-methylene-4-methyl-1,3-dioxepane (Me-MDO) as a way to expand the tool box of synthesis procedures for cyclic ketene acetals and actualize them as realistic alternatives for synthesizing biodegradable polymers. In this work, 2-methylene-1,3-dioxepane (MDO) and Me-MDO were polymerized by radical ring-opening polymerization to synthesize degradable polyesters. NMR and SEC were used to monitor the polymerization while DSC was used to study the thermal properties. Poly(2-methylene-1,3-dioxepane) (PMDO) showed increased degree of branching with higher conversion, subsequently decreasing crystallinity. The effect of branching and the introduction of side-groups on the chemical hydrolysis rate and biodegradability of the polyesters was assessed using a chemical hydrolysis test and the OECD 301D ready biodegradability screening test, respectively. A significant reduction in the chemical hydrolysis rate and biodegradability was observed upon the introduction of a side group in the poly(2-methylene-4-methyl-1,3-dioxepane) (PMe-MDO) polyester. Less obvious effects on the hydrolysis rate and biodegradability were observed as a result of the polyester branching.

Graphical abstract: Branched polyesters from radical ring-opening polymerization of cyclic ketene acetals: synthesis, chemical hydrolysis and biodegradation

Supplementary files

Article information

Article type
Paper
Submitted
03 6月 2023
Accepted
11 10月 2023
First published
18 10月 2023
This article is Open Access
Creative Commons BY license

Polym. Chem., 2023,14, 5154-5165

Branched polyesters from radical ring-opening polymerization of cyclic ketene acetals: synthesis, chemical hydrolysis and biodegradation

M. Mousa, M. Jonsson, O. Wilson, R. Geerts, H. Bergenudd, C. Bengtsson, A. Larsson Kron and E. Malmström, Polym. Chem., 2023, 14, 5154 DOI: 10.1039/D3PY00630A

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