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Ethylene Glycol Dicyclopentenyl (Meth)Acrylate Homo and Block Copolymers via Nitroxide Mediated Polymerization

Department of Chemical Engineering, Centre québécois sur les matériaux fonctionnels/Quebec Centre for Advanced Materials (CQMF/QCAM), Centre de recherche sur les systèmes polymères et composites à haute performance (CREPEC), McGill Institute of Advanced Materials (MIAM), McGill University, Montreal, QC H3A 0C5, Canada
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Materials 2019, 12(9), 1547; https://doi.org/10.3390/ma12091547
Received: 22 March 2019 / Revised: 5 May 2019 / Accepted: 8 May 2019 / Published: 11 May 2019
(This article belongs to the Special Issue Novel Materials and Applications by Controlled Radical Polymerization)
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Abstract

Nitroxide-mediated polymerization (NMP), (homo and block copolymerization with styrene (S) and butyl methacrylate/S) of ethylene glycol dicyclopentenyl ether (meth)acrylates (EGDEA and EGDEMA) was studied using BlocBuilder alkoxyamines. EGDEA homopolymerization was not well-controlled, independent of temperature (90–120 °C), or additional free nitroxide (0–10 mol%) used. Number average molecular weights (Mn) achieved for poly(EGDEA) were 4.0–9.5 kg mol−1 and were accompanied by high dispersity (Ð = Mw/Mn = 1.62–2.09). Re-initiation and chain extension of the poly(EGDEA) chains with styrene (S) indicated some block copolymer formation, but a high fraction of chains were terminated irreversibly. EGDEA-stat-S statistical copolymerizations with a low mol fraction S in initial feed, fS,0 = 0.05, were slightly better controlled compared to poly(EGDEA) homopolymerizations (Ð was reduced to 1.44 compared to 1.62 at similar conditions). EGDEMA, in contrast, was successfully polymerized using a small fraction of S (fS,0 ~ 10 mol%) to high conversion (72%) to form well-defined EGDEMA-rich random copolymer (molar composition = FEGDEMA = 0.87) of Mn = 14.3 kg mol−1 and Ð = 1.38. EGDEMA-rich compositions were also polymerized with the unimolecular succinimidyl ester form of BlocBuilder initiator, NHS-BlocBuilder with similar results, although Ðs were higher ~1.6. Chain extensions resulted in monomodal shifts to higher molecular weights, indicating good chain end fidelity. View Full-Text
Keywords: nitroxide mediated polymerization; copolymerization; block copolymers nitroxide mediated polymerization; copolymerization; block copolymers
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Maupu, A.; Kanawati, Y.; Métafiot, A.; Maric, M. Ethylene Glycol Dicyclopentenyl (Meth)Acrylate Homo and Block Copolymers via Nitroxide Mediated Polymerization. Materials 2019, 12, 1547.

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