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A self-crosslinking monomer, α-pinene methacrylate: understanding and exploiting hydrogen abstraction

Monaghan, Olivia R.; Skowron, Stephen T.; Moore, Jonathan C.; Pin-Nó, María; Kortsen, Kristoffer; Atkinson, Rachel L.; Krumins, Eduards; Lentz, Joachim C.; Machado, Fabricio; Onat, Zeynep; Brookfield, Adam; Collison, David; Khlobystov, Andrei N.; De Focatiis, Davide; Irvine, Derek J.; Taresco, Vincenzo; Stockman, Robert A.; Howdle, Steven M.


Olivia R. Monaghan

Stephen T. Skowron

María Pin-Nó

Kristoffer Kortsen

Rachel L. Atkinson

Eduards Krumins

Joachim C. Lentz

Fabricio Machado

Zeynep Onat

Adam Brookfield

David Collison

Professor of Materials Chemistry


Crosslinking is a valuable route to creating new polymeric materials and normally involves introduction of a cross linker or some form of secondary processing. Here we report the discovery and analysis of a self-crosslinking sustainable terpene derived monomer, α-pinene methacrylate (αPMA). This monomer undergoes crosslinking during free radical homopolymerisation and with comonomers e.g. methyl methacrylate (MMA). αPMA does not appear to contain any obvious functionality that would induce crosslinking such as vinyl bonds, but we postulate that it may undergo a fortuitous abstraction of a hydrogen atom from the pendant group. A combined computational (DFT) and experimental approach has been applied to investigate this. Further, we used DFT analysis to predict the behaviour of a related monomer, beta-pinene methacrylate (βPMA). To the best of our knowledge this is the first-time that self-crosslinking has been observed in free radical polymerisation of methacrylates via chain transfer through hydrogen abstraction from a pendant group. We have exploited this crosslinking to generate new, renewable poly high internal phase emulsions (polyHIPEs) that could rival those derived from fossil-based styrene- polyHIPEs and we have done this in a process which does not require any additional cross-linking agent.


Monaghan, O. R., Skowron, S. T., Moore, J. C., Pin-Nó, M., Kortsen, K., Atkinson, R. L., …Howdle, S. M. (2022). A self-crosslinking monomer, α-pinene methacrylate: understanding and exploiting hydrogen abstraction. Polymer Chemistry, 13(39), 5557-5567.

Journal Article Type Article
Acceptance Date Aug 30, 2022
Online Publication Date Sep 1, 2022
Publication Date Oct 21, 2022
Deposit Date Sep 26, 2022
Publicly Available Date Sep 27, 2022
Journal Polymer Chemistry
Print ISSN 1759-9954
Electronic ISSN 1759-9962
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 13
Issue 39
Pages 5557-5567
Keywords Organic Chemistry; Polymers and Plastics; Biochemistry; Bioengineering
Public URL
Publisher URL


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