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Polymers 2017, 9(11), 608;

Allylthioketone Mediated Free Radical Polymerization of Methacrylates

CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China
Institute of Biophysics, Hebei University of Technology, Tianjin 300401, China
Authors to whom correspondence should be addressed.
Received: 17 October 2017 / Revised: 9 November 2017 / Accepted: 10 November 2017 / Published: 13 November 2017
(This article belongs to the Special Issue Living Polymerization)
PDF [2945 KB, uploaded 15 November 2017]


By combination of high trapping free radical efficiency of the thioketone and resonance of the allylic radical, a new type of mediating agent, 1,3,3-triphenylprop-2-ene-1-thione (TPPT) has been successfully synthesized, and then is used to study controlled free radical polymerization of methacrylates. Very stable TPPT radicals at the end of poly(methyl methacrylate) (PMMA) are detected in the polymerization of MMA using TPPT and AIBN as the control agent and initiator. The MALDI-TOF MS spectra are used to identify terminal groups of the resultant poly(glycidyl methacrylate) (PGMA), and major component of the obtained polymer has the structure, (CH3)2(CN)C-PGMA-C7H9O3. Chain extension reaction tests ascertain formation of the dead polymers during the polymer storage and purification process of the polymers. Owing to very slow fragmentation reaction of the TPPT-terminated polymethacrylate radical and addition reaction of this radical with a primary radical, the growing chain radicals are difficult to be regenerated, leading to an unobvious change of the molecular weight with monomer conversion. The molecular weights of polymers can be controlled by the ratios of monomer/initiator and TPPT/initiator. However, the first order kinetics of the polymerization and the polymers with narrow polydispersity are obtained, and these phenomena are discussed. This study provides useful information on how to design a better controlling agent. View Full-Text
Keywords: allylthioketone; controlled radical polymerization; livingness; electron paramagnetic resonance; MALDI-TOF MS allylthioketone; controlled radical polymerization; livingness; electron paramagnetic resonance; MALDI-TOF MS

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Zhong, F.; Qiu, L.; Hong, C.-Y.; Pan, C.-Y. Allylthioketone Mediated Free Radical Polymerization of Methacrylates. Polymers 2017, 9, 608.

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