Issue 30, 2023, Issue in Progress

Polythioethers bearing side groups for efficient degradation by E1cB reaction: reaction design for polymerization and main-chain scission

Abstract

We have previously reported the polycondensation by the tandem reactions of dithiols and α-(bromomethyl)acrylates, consisting of conjugate substitution (SN2′ reaction) and conjugate addition (Michael addition) reactions. The resulting polythioethers underwent a main-chain scission (MCS) by E1cB reaction, which is the reverse reaction of conjugate addition, although it was not quantitative due to the equilibrium. Herein, the modification of the structures of polythioethers led to irreversible MCS, whereby the β-positions of ester moieties were substituted with a phenyl group. This slight modification in the polymer structure influenced the monomer structures and polymerization mechanisms. The understanding of reaction mechanisms by model reactions was required to obtain high molecular weights of polythioethers. It was clarified that the consequent additions of 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and PBu3 were effective to achieve high molecular weight. The resulting polythioethers decomposed by irreversible MCS via E1cB reaction with DBU.

Graphical abstract: Polythioethers bearing side groups for efficient degradation by E1cB reaction: reaction design for polymerization and main-chain scission

Supplementary files

Article information

Article type
Paper
Submitted
05 Jun 2023
Accepted
23 Jun 2023
First published
10 Jul 2023
This article is Open Access
Creative Commons BY license

RSC Adv., 2023,13, 20782-20786

Polythioethers bearing side groups for efficient degradation by E1cB reaction: reaction design for polymerization and main-chain scission

R. Kawatani, K. Hagiwara, A. Tanaka and Y. Kohsaka, RSC Adv., 2023, 13, 20782 DOI: 10.1039/D3RA03751G

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