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Characterization of the anionic polymerization of 2-(ethoxy)ethyl methacrylate by t-C4H9MgBr in toluene

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Abstract

Anionic polymerizations of 2-(ethoxy)ethyl methacrylate (EOEMA) were carried out under several conditions that allowed for living polymerization of methyl methacrylate (MMA). It was found that the polymerization rate of EOEMA by t-C4H9MgBr in toluene was much lower than that of MMA under these conditions. However, the polymerization rate of EOEMA by t-C4H9MgBr in tetrahydrofuran was not much lower than the polymerization of MMA. Interactions between the counter cation (magnesium) and the ether oxygen of the ester moiety in the EOEMA unit are considered important to delay the polymerization. Random and block copolymerizations of EOEMA and MMA by t-C4H9MgBr in toluene were also carried out and the results support the interaction of ether oxygen. 4-(Ethoxy)butyl methacrylate (EOBMA) was successfully prepared from 4-ethoxy-1-butanol and methacryloyl chloride and purified. Polymerization of EOBMA with t-C4H9MgBr in toluene provides a polymer with good yield, suggesting that the number of carbon atoms between the ester group and the ether oxygen is important to the interactions with the ether oxygen. Some of the thermal properties of the polymers and copolymers, including their glass transition temperature and thermal stability, were also evaluated.

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Acknowledgments

The authors would like to thank Ms. Chizuka Hirokawa and Mr. Dai Ogura from the Tokyo National College of Technology for their help with the NMR and thermal analysis experiments.

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Authors and Affiliations

  1. Department of Chemical Science and Engineering, Tokyo National College of Technology, Hachioji, Tokyo, 193-0997, Japan

    Osamu Nakagawa, Hitoshi Saito & Kie Shinomiya

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  1. Osamu Nakagawa
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  2. Hitoshi Saito
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  3. Kie Shinomiya
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Correspondence to Osamu Nakagawa.

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Nakagawa, O., Saito, H. & Shinomiya, K. Characterization of the anionic polymerization of 2-(ethoxy)ethyl methacrylate by t-C4H9MgBr in toluene. Polym. Bull. 71, 1645–1660 (2014). https://doi.org/10.1007/s00289-014-1146-x

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  • DOI: https://doi.org/10.1007/s00289-014-1146-x

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