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

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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-cap** 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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Acknowledgments

Ravindra Mahadev Patil would like to thank Syngene International Ltd, Bangalore, India for financial assistance for his doctoral research.

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Authors and Affiliations

  1. Syngene International Ltd, Biocon Park, Plot No. 2 & 3, Bommasandra Industrial Estate, Phase-IV Bommasandra-Jigani Link Road, Bangalore, 560 099, India

    Ravindra Mahadev Patil, Satyanarayana Ganugapati & Rudhramyna Gnaneshwar

  2. Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research (A*STAR), 1 Pesek Road, Jurong Island, Singapore, 627833, Singapore

    Han Hong

  3. Institute of Chemical and Engineering Sciences, Organic Chemistry @ Neuros, Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, # 07-01, Neuros, Singapore, 138665, Singapore

    Christina L. L. Chai

  4. School of Chemical Sciences, Solarpur University, Solapur, 413 255, India

    Ravindra Mahadev Patil & Anil A. Ghanwat

Authors
  1. Ravindra Mahadev Patil
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  2. Han Hong
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  3. Christina L. L. Chai
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  4. Anil A. Ghanwat
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  5. Satyanarayana Ganugapati
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  6. Rudhramyna Gnaneshwar
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Correspondence to Rudhramyna Gnaneshwar.

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Patil, R.M., Hong, H., Chai, C.L.L. et al. Synthesis and characterization of α-(cyclic carbonate), ω-hydroxyl/itaconic acid asymmetric telechelic poly(ε-caprolactone). Polym. Bull. 72, 2489–2501 (2015). https://doi.org/10.1007/s00289-015-1413-5

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