[en] Radical polymerization of exo-methylene cyclic monomers is a straightforward strategy for preparing polymers with pendant heterocycles used as protective groups for reactive functions. In spite of their availability and possible chemical transformations, so far, methylene oxazolidinones have been disregarded in the field of macromolecular synthesis. This work reports the radical (co)polymerization of 4,4-dimethyl-5-methyleneoxazolidin-2-one (DMOx) and the transformation of the pendant oxazolidinone groups into vicinal amino-alcohol functions. DMOx was produced through an optimized procedure of carboxylative cyclization of dimethylpropargylamine. In addition to the conventional radical (co)polymerization of DMOx, we considered its reversible deactivation radical copolymerization with VAc by organometallic-mediated radical polymerization (OMRP) and reversible addition fragmentation chain transfer (RAFT). The ability of these methods to produce well-defined copolymers was studied as well as their respective reactivity ratios. Finally, the poly(DMOx-co-VAc) were converted into vicinal amino-alcohol functional poly(vinyl alcohol)s presenting peculiar multi-responsive behavior, namely pH-, thermal- and metal-ion sensitivity.
Research center :
CERM - Center for Education and Research on Macromolecules CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Wang, Zhuoqun ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Debuigne, Antoine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Language :
English
Title :
Reversible deactivation radical (co)polymerization of dimethyl methylene oxazolidinone towards responsive vicinal aminoalcohol-containing copolymers
Publication date :
07 December 2020
Journal title :
Polymer Chemistry
ISSN :
1759-9954
eISSN :
1759-9962
Publisher :
Royal Society of Chemistry, United Kingdom
Volume :
11
Issue :
45
Pages :
7207-7220
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
Excellence of Science "EOS" program
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen [BE]