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Maleimide Glycidyl Ether: A Bifunctional Monomer for Orthogonal Cationic and Radical Polymerizations
Author(s) -
Klein Rebecca,
Übel Fabian,
Frey Holger
Publication year - 2015
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201500400
Subject(s) - maleimide , cationic polymerization , copolymer , polymer chemistry , bifunctional , moiety , monomer , polymerization , chemistry , radical polymerization , ring opening polymerization , materials science , polymer , organic chemistry , catalysis
A novel bifunctional monomer, namely maleimide glycidyl ether (MalGE), prepared in a four‐step reaction sequence is introduced. This monomer allows for selective (co)polymerization of the epoxide group via cationic ring‐opening polymerization, preserving the maleimide functionality. On the other hand, the maleimide functionality can be copolymerized via radical techniques, preserving the epoxide moiety. Cationic ring‐opening multibranching copolymerization of MalGE with glycidol was performed, and a MalGE content of up to 24 mol% could be incorporated into the hyperbranched polymer backbone ( M n = 1000–3000 g mol −1 ). Preservation of the maleimide functionality during cationic copolymerization was verified via NMR spectroscopy. Subsequently, the maleimide moiety was radically crosslinked to generate hydrogels and additionally employed to perform Diels‐Alder (DA) “click” reactions with (functional) dienes after the polymerization process. Radical copolymerization of MalGE with styrene ( M n = 5000–9000 g mol −1 ) enabled the synthesis of a styrene copolymer with epoxide functionalities that are useful for versatile crosslinking and grafting reactions.