Issue 14, 2024

Azlactone-based copolymers by redox-initiated MADIX polymerization at room temperature in ethanol

Abstract

Macromolecular design via the interchange of xanthate (MADIX) polymerization of 2-vinyl-4,4-dimethylazlactone (VDM) used as comonomer is reported. Rhodixan® A1 was employed as chain transfer agent and ethanol was used as solvent. An efficient control of the MADIX polymerization with complete monomer conversion was reached after 6 h using either a thermal initiation at 70 °C or a redox initiating system at 25 °C. In contrast with thermal-initiated MADIX polymerization at 70 °C, redox-initiated MADIX polymerization allows the reaction to be carried out at 25 °C and avoids solvolysis of the azlactone ring after 6 h. The resulting azlactone-based copolymers were used as a “clickable” platform for chemical post-polymerization modification (PPM) as demonstrated using allylamine as a model of primary amine. PPM with allylamine performed in ethanol at 25 °C was quantitative and selective in 2 h.

Graphical abstract: Azlactone-based copolymers by redox-initiated MADIX polymerization at room temperature in ethanol

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2024
Accepted
06 Mar 2024
First published
08 Mar 2024

Polym. Chem., 2024,15, 1453-1459

Azlactone-based copolymers by redox-initiated MADIX polymerization at room temperature in ethanol

F. François, G. Gody, J. Wilson, L. Fontaine and S. Pascual, Polym. Chem., 2024, 15, 1453 DOI: 10.1039/D4PY00070F

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