Table of Contents
Journal of Polymers
Volume 2014, Article ID 830137, 7 pages
http://dx.doi.org/10.1155/2014/830137
Research Article

Cyclic Oligolactic Acid in Direct Polycondensation PLLA and Its Extraction with Organic Solvent

1Department of Biobased Materials Science, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
2Rajamangala University of Technology Thanyaburi, Rangsit-Nakhon Nayok, Pathum Thani 12110, Thailand

Received 22 August 2014; Revised 17 October 2014; Accepted 18 October 2014; Published 25 November 2014

Academic Editor: Iliya Rashkov

Copyright © 2014 Keiichiro Nomura et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. W. Leenslag and A. J. Pennings, “Synthesis of high-molecular-weight poly(L-lactide) initiated with tin 2-ethylhexanoate,” Die Makromolekulare Chemie, vol. 188, no. 8, pp. 1809–1814, 1987. View at Publisher · View at Google Scholar
  2. S. I. Moon, C. W. Lee, M. Miyamoto, Y. Kimura, and J. Polym, “Melt polycondensation of L-lactic acid with Sn(II) catalysts activated by various proton acids: a direct manufacturing route to high molecular weight Poly(L-lactic acid),” Journal of Polymer Science Part A: Polymer Chemistry, vol. 38, no. 9, pp. 1673–1679, 2000. View at Publisher · View at Google Scholar
  3. J. Weil, R. T. Mathers, and Y. D. Y. L. Getzler, “Lactide cyclopolymerization by an alumatrane-inspired catalyst,” Macromolecules, vol. 45, no. 2, pp. 1118–1121, 2012. View at Publisher · View at Google Scholar · View at Scopus
  4. E. J. Shin, A. E. Jones, and R. M. Waymouth, “Stereocomplexation in cyclic and linear polylactide blends,” Macromolecules, vol. 45, no. 1, pp. 595–598, 2012. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Masuda and K. Nishimura, “Absolute configurations of quercus lactones, (3s,4r)- and (3s,4s)-3-methyl-4-octanolide, from oak wood and chiroptical properties of mono-cyclic γ-lactones,” Chemistry Letters, vol. 10, pp. 1333–1336, 1981. View at Google Scholar
  6. A. Fürstner and K. Langemann, “Macrocycles by ring-closing metathesis,” Synthesis, no. 7, pp. 792–803, 1997. View at Google Scholar · View at Scopus
  7. J. Bolard, “How do the polyene macrolide antibiotics affect the cellular membrane properties?” Biochimica et Biophysica Acta, vol. 864, no. 3-4, pp. 257–304, 1986. View at Publisher · View at Google Scholar · View at Scopus
  8. J. M. Hamilton-Miller, “Chemistry and biology of the polyene macrolide antibiotics,” Bacteriological Reviews, vol. 37, no. 2, pp. 166–196, 1973. View at Google Scholar · View at Scopus
  9. J. Retsema, A. Girard, W. Schelkly et al., “Spectrum and mode of action of azithromycin (CP-62,993), a new 15-membered-ring macrolide with improved potency against gram-negative organisms,” Antimicrobial Agents and Chemotherapy, vol. 31, no. 12, pp. 1939–1947, 1987. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Takada, Y. Nagato, and M. Yamamura, “Effect of cyclic polylactates on tumor cells and tumor bearing mice,” Biochemistry and Molecular Biology International, vol. 43, no. 1, pp. 9–17, 1997. View at Google Scholar
  11. S. Aizawa, N. Shimizu, H. Handa et al., “Effects of cyclic polylactate (CPL) on the growth of cloned leukemic cells in vitro,” Hematological Oncology, vol. 18, no. 2, pp. 51–60, 2000. View at Publisher · View at Google Scholar · View at Scopus
  12. S. Sawa, T. Kawamoto, Y. Horibe, and H. Ohara, Japan patent JPA1995-138253, 1995.
  13. J. L. Espartero, I. Rashkov, S. M. Li, N. Manolova, and M. Vert, “NMR analysis of low molecular weight poly(lactic acid)s,” Macromolecules, vol. 29, no. 10, pp. 3535–3539, 1996. View at Publisher · View at Google Scholar · View at Scopus
  14. M. M. Conn and J. Rebek Jr., “Self-assembling capsules,” Chemical Reviews, vol. 97, no. 5, pp. 1647–1668, 1997. View at Publisher · View at Google Scholar · View at Scopus
  15. C. J. Pedersen, “The discovery of crown Ethers (Noble Lecture),” Angewandte Chemie International Edition, vol. 27, no. 8, pp. 1021–1027, 1988. View at Google Scholar
  16. C. Seel and F. Vögtle, “Molecules with large cavities in supramolecular chemistry,” Angewandte Chemie—International Edition, vol. 31, no. 5, pp. 528–549, 1992. View at Publisher · View at Google Scholar
  17. S. Dai, Y. H. Ju, and C. E. Barnes, “Solvent extraction of strontium nitrate by a crown ether using room-temperature ionic liquids,” Journal of the Chemical Society, Dalton Transactions, no. 8, pp. 1201–1202, 1999. View at Google Scholar
  18. S. Shirakawa, L. Wang, A. Kasai, and K. Maruoka, “New neutral reaction system with crown ether-KCl complexes in aqueous solution,” Chemistry—A European Journal, vol. 18, no. 28, pp. 8588–8590, 2012. View at Publisher · View at Google Scholar · View at Scopus
  19. D. W. van Krevelen, Properties of Polymers, Elsevier, Amsterdam, The Netherlands, 3rd edition, 1990.
  20. D. Zhang, M. A. Hillmyer, and W. B. Tolman, “A new synthetic route to poly[3-hydroxypropionic acid] (P[3-HP]): ring-opening polymerization of 3-HP macrocyclic esters,” Macromolecules, vol. 37, no. 22, pp. 8198–8200, 2004. View at Publisher · View at Google Scholar · View at Scopus
  21. J. H. Gross, Mass Spectrometry, Springer, Heidelberg, Germany, 2004.