Issue 21, 2022

Facile construction of functional poly(monothiocarbonate) copolymers under mild operating conditions

Abstract

The installation of both oxazolidone and thiocarbonate linkages within a single polymer backbone remains elusive by simple procedures under mild conditions. In this work, we report the construction of copolymers containing these two linkages by the one-pot terpolymerization of diamines, dithiols and a CO2-sourced activated dicyclic carbonate of the α-alkylidene type. This process is facile and efficient with many commercially available diamine and dithiol comonomers, and occurs at room temperature under catalyst-free conditions. In contrast to polyoxazolidones that are insoluble in many organic solvents, the copolymers are highly soluble, facilitating their processing as adhesives. The polymers present an unusual thermal behavior with the presence of two glass transition temperatures. Importantly, they can undergo facile and quantitative dehydration by a simple thermal treatment at moderate temperature (110–160 °C) without using any catalyst or dehydrating agent, thereby furnishing novel polymers presenting both thiocarbonate and α-alkylidene oxazolidone linkages. The pendant double bonds are exploited for the facile thiol–ene functionalization with a scope of commercially available thiols under mild conditions. This work gives access to functional poly(monothiocarbonate)-based copolymers under mild operating conditions without requiring specific equipment.

Graphical abstract: Facile construction of functional poly(monothiocarbonate) copolymers under mild operating conditions

Supplementary files

Article information

Article type
Paper
Submitted
11 မတ် 2022
Accepted
07 မေ 2022
First published
09 မေ 2022

Polym. Chem., 2022,13, 3076-3090

Facile construction of functional poly(monothiocarbonate) copolymers under mild operating conditions

T. Habets, F. Siragusa, A. J. Müller, Q. Grossman, D. Ruffoni, B. Grignard and C. Detrembleur, Polym. Chem., 2022, 13, 3076 DOI: 10.1039/D2PY00307D

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