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01-10-2015 | Original Paper | Issue 10/2015

Polymer Bulletin 10/2015

Synthesis and characterization of α-(cyclic carbonate), ω-hydroxyl/itaconic acid asymmetric telechelic poly(ε-caprolactone)

Journal:
Polymer Bulletin > Issue 10/2015
Authors:
Ravindra Mahadev Patil, Han Hong, Christina L. L. Chai, Anil A. Ghanwat, Satyanarayana Ganugapati, Rudhramyna Gnaneshwar
Important notes

Electronic supplementary material

The online version of this article (doi:10.​1007/​s00289-015-1413-5) contains supplementary material, which is available to authorized users.

Abstract

Well-defined α-(cyclic carbonate), ω-hydroxyl asymmetric telechelic poly(ε-caprolactone)s (PCLs) were prepared with good end-group fidelity by ring-opening polymerization (ROP) of ε-CL catalyzed by Sn(Oct)2 in conjunction with a renewable, functional bio-based initiator namely glycerol 1,2-carbonate (GC) in bulk at 110 °C. The end group’s structure derived from the alcohol initiator was confirmed by NMR, FTIR and MALDI TOF MS. The living character of ROP of ε-CL using GC/Sn(Oct)2 was demonstrated by the linear correlation of molecular weight versus monomer conversion. End-capping reaction of α-(cyclic carbonate), ω-hydroxyl asymmetric telechelic PCL with itaconic anhydride to yield α-(cyclic carbonate), ω-(itaconic acid) asymmetric telechelic PCL was presented. Five-membered cyclic carbonate end group reaction with 2-phenylethylamine enabled the hydroxyurethane end functional PCL without the use of the relatively more hazardous isocyanates and without any by-product.

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