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RESEARCH PRODUCT
Maleimide Glycidyl Ether: A Bifunctional Monomer for Orthogonal Cationic and Radical Polymerizations.
Fabian ÜBelRebecca KleinHolger Freysubject
Polymers and PlasticsFree RadicalsChemistryPolymersPropanolsOrganic ChemistryRadical polymerizationCationic polymerizationChain transferPolymerizationMaleimideschemistry.chemical_compoundPolymerizationCationsMaterials ChemistryCopolymerOrganic chemistryEpoxy CompoundsReversible addition−fragmentation chain-transfer polymerizationIonic polymerizationMaleimideEthersdescription
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 (Mn = 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 (Mn = 5000-9000 g mol(-1)) enabled the synthesis of a styrene copolymer with epoxide functionalities that are useful for versatile crosslinking and grafting reactions.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-07-11 | Macromolecular rapid communications |