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Copolymerization of succinic anhydride and epoxide with diethylene glycol side chain

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Abstract

To combine the properties of degradability and low critical solution temperature transition in a single macromolecule, a new thermoresponsive polyester with oligo (ethylene glycol) side chains was designed. This particular polymer P (ME2MO-alt-SA) was prepared by alternating ring-opening copolymerization of functionalized epoxide [2-((2-(2-methoxyethoxy)ethoxy)methyl) oxirane, ME2MO] and succinic anhydride (SA) in bulk using metallic alkoxide as initiator. The effects of various kinetics conditions on ME2MO–SA copolymerization, such as initiator, polymerization time, temperature, monomer/initiator ratio, and feed ratio, are discussed in detail. The formation of an alternative structure is demonstrated and the conditions for ME2MO–SA copolymerization are optimized: aluminum isopropoxide (AIP) as initiator; monomer/initiator molar ratio (M/I) at 150; the feed ratio of comonomers at 0.5; polymerization temperature at 120 °C more than 12 h. From the NMR spectra, the initiation end group is confirmed to be isopropanol ester that results from the initiation reaction of AIP with SA. However, the termination end group was variable and could be hydroxyl, carboxyl or their mixture, depending on the feed ratio of ME2MO/SA. Based on the above experimental results, the possible coordination–insertion mechanism was proposed for alternating ring-opening copolymerization of ME2MO and SA initiated by AIP, which suggested the two monomers are inserted into the O–Al and COO–Al active ends alternately.

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Acknowledgments

This work was supported by the National Natural Sciences Fund of China (No. 21204006), the Natural Science Foundation of Jiangsu Province (No. BK2012155) and the Science and Technology Development Project of Changzhou City (No. CE20125032).

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Authors and Affiliations

  1. Laboratory of Biomaterials, High-Tech Research Institute of Nanjing University (Changzhou), Changzhou, 213164, People’s Republic of China

    Lei Feng

  2. School of Microelectronics and Solid State Electronics, University of Electronic Science and Technology of China, Chengdu, 610054, People’s Republic of China

    Zhao Yang, Yu Liu & Jianyuan Hao

  3. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, People’s Republic of China

    Chengdong Xiong & Xianmo Deng

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  1. Lei Feng
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  2. Zhao Yang
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  3. Yu Liu
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  5. Chengdong Xiong
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  6. Xianmo Deng
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Correspondence to Lei Feng.

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Feng, L., Yang, Z., Liu, Y. et al. Copolymerization of succinic anhydride and epoxide with diethylene glycol side chain. Iran Polym J 23, 217–226 (2014). https://doi.org/10.1007/s13726-013-0217-4

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  • DOI: https://doi.org/10.1007/s13726-013-0217-4

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