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Open AccessArticle

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
Author to whom correspondence should be addressed.
Materials 2019, 12(9), 1547;
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 Applicaitons by Controlled Radical Polymerization)
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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MDPI and ACS Style

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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