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Radical Copolymerization of Thionoglycolide and Derivatives for Preparation of Degradable Vinyl Polymers

Authors :
Ivanchenko, Oleksandr
Mazières, Stéphane
Mallet-Ladeira, Sonia
Harrisson, Simon
Destarac, Mathias
Source :
Macromolecules; August 2024, Vol. 57 Issue: 16 p8059-8066, 8p
Publication Year :
2024

Abstract

This study explores the copolymerization behavior of thionated glycolide derivatives with a focus on thionoglycolide (TGD). It was found that TGD exhibits a nuanced reactivity profile, showing the highest compatibility with styrene and tert-butyl acrylate (tBA). Kinetic analysis of the TGD/tBA system conducted at 100 °C in bulk demonstrated comparable incorporation rates for both monomers. Furthermore, RAFT copolymerization mediated by a trithiocarbonate RAFT agent resulted in a well-defined copolymer with Mn= 13.4 kg mol–1and Đ= 1.2. 2D-NMR microstructural analysis revealed that TGD was exclusively incorporated in its ring-closed S,O-thioketal form, suggesting a selective 1,2-vinyl propagation mechanism. The degradability of the resulting copolymers was also investigated, with NaOCl, NaOMe, and benzoyl peroxide effectively cleaving S,O-thioketal linkages.

Details

Language :
English
ISSN :
00249297 and 15205835
Volume :
57
Issue :
16
Database :
Supplemental Index
Journal :
Macromolecules
Publication Type :
Periodical
Accession number :
ejs67185569
Full Text :
https://doi.org/10.1021/acs.macromol.4c01259