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Diblock and triblock copolymers catalyzed by benzo-12-crown-4 bridged N-heterocyclic carbene: synthesis, characterization and degradation behavior

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Abstract

The sequential ring-opening polymerizations (ROP) of ε-caprolactone (ε-CL) and L-lactide (LLA) with benzo-12-crown-4-imidazole carbene (B-12-C-4imY) as the catalyst have been performed. Using either benzyl alcohol or ethylene glycol as an initiator, the corresponding poly(ε-caprolactone)-poly(L-lactide) (PCL-b-PLLA) diblock or poly(L-lactide)-poly(ε-caprolactone)-poly(L-lactide) (PLLA-PCL-PLLA) triblock copolymers were easily prepared. The results indicated that B-12-C-4imY was quite effective for the copolymerization. The diblock copolymerization of ε-CL with LLA could only be achieved when ε-CL was first polymerized followed by LLA. Feeding the two monomers simultaneously, however, only resulted in the formation of LLA homopolymers. Thermogravimetric analysis (TGA) measurements demonstrated that block copolymers exhibited the decomposition temperature lower than the PCL homopolymer. The copolymers were characterized by 1H NMR and 13C NMR, FT-IR, GPC, and DSC analyses. 20 × 10 mm2 rectangular specimens made of the triblock copolymer were allowed to degrade in a pH = 7.4 phosphate buffer at 37 °C. Degradation was monitored by various analytical techniques such as GPC, IR, and ESEM.

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Acknowledgements

This work was supported by Basic Research Project of Shanxi Province of China (No.2015011029), Undergraduate Innovative Experiment Program of Shanxi Normal University (No.SD2014CXXM-36) and Shanxi Province Education Innovation Project for Postgraduate (No.2015BY38).

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  1. Institute of Material Chemistry, Shanxi Normal University, Linfen, 041004, People’s Republic of China

    Yan Wang, Ni Wu, Junhua Bai, Qianru Li & Lifang Zhang

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  1. Yan Wang
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Correspondence to Lifang Zhang.

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Wang, Y., Wu, N., Bai, J. et al. Diblock and triblock copolymers catalyzed by benzo-12-crown-4 bridged N-heterocyclic carbene: synthesis, characterization and degradation behavior. J Polym Res 25, 254 (2018). https://doi.org/10.1007/s10965-018-1639-7

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