Issue 47, 2022

Diverse chemically recyclable polymers obtained by cationic vinyl and ring-opening polymerizations of the cyclic ketene acetal ester “dehydroaspirin”

Abstract

In the quest for sustainable polymers, preparing two different types of recyclable polymer from only one monomer is efficient and interesting. Herein, we report the polymerizations of 2-methylene-4H-benzo[d][1,3]dioxin-4-one (MBDO or dehydroaspirin) to afford degradable polymers by two reaction modes, vinyl polymerization (VP) and ring-opening polymerization (ROP). The radical polymerization proceeded in VP selectively, and the monomer reactivity was evaluated as Q = 0.13 and e = −1.14, by copolymerization with methyl methacrylate. The product of VP was found to be degradable by acid and base hydrolysis to afford acetic acid and salicylic acid, that is, the raw materials of MBDO. The e value suggested that MBDO is cationically polymerizable. In fact, cationic polymerization resulted in both VP and ROP; in particular, polymerization in the presence of EtAlCl2 below 0 °C proceeded in selective ROP to afford a polyester composed of a β-ketoester unit that exhibited degradability by basic hydrolysis to the raw materials of MBDO. Therefore, MBDO is a chemically recyclable monomer to afford diverse sustainable polymers by VP and ROP.

Graphical abstract: Diverse chemically recyclable polymers obtained by cationic vinyl and ring-opening polymerizations of the cyclic ketene acetal ester “dehydroaspirin”

Supplementary files

Article information

Article type
Paper
Submitted
14 Sept. 2022
Accepted
14 Okt. 2022
First published
17 Okt. 2022

Polym. Chem., 2022,13, 6484-6491

Diverse chemically recyclable polymers obtained by cationic vinyl and ring-opening polymerizations of the cyclic ketene acetal ester “dehydroaspirin”

A. Kazama and Y. Kohsaka, Polym. Chem., 2022, 13, 6484 DOI: 10.1039/D2PY01181F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements