화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.26, No.3, 246-253, March, 2018
DOI10.1007/s13233-018-6038-8  Export Citation
Thermally Stable Bio-Based Aliphatic Polycarbonates with Quadra-Cyclic Diol from Renewable Sources
Jeong Eon Park, Wook Kyeom Kim, Da Young Hwang, Gwang Ho Choi, and Dong Hack Suh†
  • Department of Chemical Engineering, College of Engineering, Hanyang University, Seoul 04763, Korea
E-mail:
CM diol (i.e., 2,4:3,5-di-O-camphor-D-mannitol) is bio-based monomer derived from D-mannitol and camphor. CM diol consists of complex hexagonal rings that are linked as the form of spiro, fused and bridged ring and the structure of CM diol influence the rigidity and thermal properties. Primary alcohol at the ends of CM diol is more reactive than secondary alcohol in isosorbide which is applied for the field of polycarbonate. A series of copolycarbonates based on CM diol was synthesized and a homo-polycarbonate except bisphenol A (BPA) diol had a high Tg value of 164 °C, which is higher than Tg (138 °C) of polycarbonates based on BPA (BPAPC). In addition, the polycarbonates containing CM diol showed enhanced susceptibility to hydrolysis at acidic solution and decomposed better than BPA-PC.
Keywords:biopolymers;polycarbonates;degradable;BPA free
  1. Zhai WT, Yu J, Ma WM, He JS, Macromolecules, 40(1), 73 (2007)
  2. Gross SM, Roberts GW, Kiserov DJ, DeSimone JM, Macromolecules, 34(12), 3916 (2001)
  3. Watson MD, Wagener KB, Macromolecules, 33(24), 8963 (2000)
  4. Garcia-Martin MG, Perez RR, Hernandez EB, Espartero JL, Munoz-Guerra S, Galbis JA, Macromolecules, 38(21), 8664 (2005)
  5. Hoekstra EJ, Simoneau C, Crit. Rev. Food Sci. Nutr., 53, 386 (2013)
  6. Zhu W, Zhou W, Li C, Xiao Y, Zhang D, Guan G, Wang D, J. Macromol. Sci., Phys. Part A, 48, 583 (2011)
  7. Hagenaars AC, Pesce JJ, Bailly C, Wolf BA, Polymer, 42(18), 7653 (2001)
  8. vom Saal FS, Akingbemi BT, Belcher SM, Birnbaum LS, Crain DA, Eriksen M, Farabollini F, Guillette LJ, et al., Regul. Toxicol., 24, 131 (2007)
  9. Chatti S, Schwarz G, Kricheldorf HR, Macromolecules, 39(26), 9064 (2006)
  10. Fenouillot F, Rousseau A, Colomines G, Saint-Loup R, Pascault JP, Prog. Polym. Sci, 35, 578 (2010)
  11. Noordover BAJ, Haveman D, Duchateau R, van Benthem RATM, Koning CE, J. Appl. Polym. Sci., 121(3), 1450 (2011)
  12. Feng J, Zhuo RX, Zhang XZ, Prog. Polym. Sci, 37, 211 (2012)
  13. Lee CH, Takagi H, Okamoto H, Kato M, J. Appl. Polym. Sci., 127(1), 530 (2013)
  14. Wu J, Eduard P, Jasinska-Walc L, Rozanski A, Noordover BAJ, van Es DS, Koning CE, Macromolecules, 46(2), 384 (2013)
  15. Yoon WJ, Hwang SY, Koo JM, Lee YJ, Lee SU, Im SS, Macromolecules, 46, 7219 (2013)
  16. Wu J, Eduard P, Thiyagarajan S, Noordover BA, van Es DS, Koning CE, ChemSusChem, 8, 67 (2015)
  17. Li Q, Zhu WX, Li CC, Guan GH, Zhang D, Xiao YN, Zheng LC, J. Polym. Sci. A: Polym. Chem., 51(6), 1387 (2013)
  18. Feng L, Zhu W, Li C, Guan G, Zhang D, Xiao Y, Zheng L, Polym. Chem., 6, 633 (2015)
  19. Lavilla C, de Ilarduya AM, Alla A, Garcia-Martin MG, Galbis JA, Munoz-Guerra S, Macromolecules, 45(20), 8257 (2012)
  20. Lavilla C, Alla A, de Ilarduya AM, Munoz-Guerra S, Biomacromolecules, 14(3), 781 (2013)
  21. Japu C, de Ilarduya AM, Alla A, Garcia-Martin MG, Galbis JA, Munoz-Guerra S, Macromol. Chem. Phys., 215, 2048 (2014)
  22. Yokoe M, Aoi K, Okada M, J. Polym. Sci. A: Polym. Chem., 43(17), 3909 (2005)
  23. Gubbels E, Lavilla C, de Ilarduya AM, Noordover BAJ, Koning CE, Munoz-Guerra S, J. Polym. Sci. A: Polym. Chem., 52(2), 164 (2014)
  24. Hauenstein O, Reiter M, Agarwal S, Rieger B, Greiner A, Green Chem., 18, 760 (2016)
  25. Hashimoto T, Takagi H, Hasegawa Y, Matsui H, Urushisaki M, Sakaguchi T, J. Polym. Sci. A: Polym. Chem., 48(4), 952 (2010)
  26. Smith JA, Brzezinska KR, Valenti DJ, Wagener KB, Macromolecules, 33(10), 3781 (2000)
  27. Dobrzynski P, Kasperczyk J, J. Polym. Sci. A: Polym. Chem., 44(10), 3184 (2006)
  28. Bajaj P, Khanna DN, Eur. Polym. J., 17, 275 (1981)
  29. Kim YW, Park JT, Koh JH, Min BR, Kim JH, Polym. Adv. Technol., 19, 944 (2008)
  30. Fox TG, Flory PJ, J. Polym. Sci., 14, 315 (1954)
  31. Lee HJ, Kodaira T, Urushisaki M, Hashimoto T, Polymer, 54, 7505 (2004)
  32. Lee HJ, Nakai H, Kodaira T, Urushisaki M, Hashimoto T, Eur. Polym. J., 41, 1225 (2005)
  33. Kwan EE, J. Chem. Educ., 82, 1026 (2005)
  34. Binauld S, Stenzel MH, Chem. Commun., 49, 2082 (2013)
  35. Akiyama Y, Harada A, Nagasaki Y, Kataoka K, Macromolecules, 33(16), 5841 (2000)
  36. Seyednejad H, Ji W, Schuurman W, Dhert WJ, Malda J, Yang F, Jansen JA, van Nostrum C, Vermonden T, Hennink WE, Macromol. Biosci., 11, 1684 (2011)
  37. Zheng M, Yang C, Meng F, Peng R, Zhong Z, Macromol. Res., 20(3), 327 (2012)
  38. Jin B, Shen J, Peng R, Shu Y, Chu S, Dong H, Macromol. Res., 22(2), 117 (2014)