Journal
POLYMER
Volume 154, Issue -, Pages 148-152Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.polymer.2018.09.004
Keywords
Stereoselective; Zwitterionic ring-opening polymerization; N-Heterocyclic carbene
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Funding
- Anhui Provincial Natural Science Foundation [1408085QB28]
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Stereoselective zwitterionic ring-opening polymerization (ZROP) poses a potentially great challenge in polymer chemistry because of its unique ion-pairing catalysis mechanism. Herein, a stereoselective ZROP of rac-lactide (rac-LA) was explored for synthesis of isotactic cyclic polylactides by using commercially available N-heterocyclic carbene (NHC) catalysts at low temperature in tetrahydrofuran. The epimerization of lactide during ZROP can be inhibited at low temperature. The best isoselectivity can reach to a high value of P-m = 0.91 associated with a high melting point (T-m) of 193 degrees C. The resulting polylactides exhibit narrow molecular weight distributions (M-w/M-n < 1.2) and inhibited transesterification as evidenced by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). The resulting polylactide is predominantly cyclic as evidenced by H-1 NMR and MALDI-TOF MS analyses.
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