Citation: Li-nan Li, Cheng-dong Xiong, Dong-liang Chen. Novel Terpolymers of Poly(p-dioxanone-co-trimethylene carbonate-co-L-phenylalanine): Synthesis, Characterization, Thermal Properties and Copolymerization Mechanism[J]. Chinese Journal of Polymer Science, ;2016, 34(5): 594-605. doi: 10.1007/s10118-016-1777-5 shu

Novel Terpolymers of Poly(p-dioxanone-co-trimethylene carbonate-co-L-phenylalanine): Synthesis, Characterization, Thermal Properties and Copolymerization Mechanism

a.
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Dong-liang Chen, 1633cdl@cioc.ac.cn
Received Date: 11 November 2015
Revised Date: 26 December 2015
Accepted Date: 26 December 2015

In order to exploit the biological functions of materials, a series of new random terpolymers were synthesized by the ring-opening polymerization of p-dioxanone, trimethylene carbonate, and L-phenylalanine N-carboxyanhydride (L-Phe-NCA) in the presence of stannous octoate. The terpolymers were characterized by ¹H-NMR, ¹³C-NMR, FTIR, and gel permeation chromatography. The effects of the reactant ratio, catalyst dosage, reaction temperature and time on the copolymerization were investigated, and were found to regulate the composition of the terpolymer. Increases in the reaction temperature, polymerization time, L-Phe-NCA monomer amount, and catalyst content generated a product with a slightly decreased molecular weight. The crystallinity of the terpolymer was investigated by differential scanning calorimetry and polarized optical microscopy. A reasonable mechanism for the polymerization was proposed based on the obtained results.
- Terpolymers,
- p-Dioxanone,
- Trimethylene carbonate,
- L-Phenylalanine,
- Mechanism
1. [1]
  Wang, X.L., Huang, Y., Zhu, J., Pan, Y.B., He, R. and Wang, Y.Z., Carbohyd. Res., 2009, 344: 801 doi: 10.1016/j.carres.2009.02.009
2. [2]
  Yang, K.K., Wang, X.L., Wang, Y.Z. and Huang, H.X., J. Appl. Polym. Sci., 2006, 100: 2331 doi: 10.1002/(ISSN)1097-4628
3. [3]
  Vert, M., Biomacromolecules, 2005, 6: 538 doi: 10.1021/bm0494702
4. [4]
  Huang, W., Wang, M.J., Liu, C.L., You, J., Chen, S.C., Wang, Y.Z. and Liu, Y., J. Mater. Chem. A., 2014, 2: 8416 doi: 10.1039/c4ta00417e
5. [5]
  Niu, Y., Zhang, P., Zhang, J.J., Xiao, L.P., Yang, K.K. and Wang, Y.Z., Polym. Chem., 2012, 3: 2508 doi: 10.1039/c2py20311a
6. [6]
  Weigel, T., Mohr, R. and Lendlein, A., Smart Mater. Struct., 2009, 18: 1282
7. [7]
  Schüller-Ravoo, S., Teixeira, S.M., Feijen, J., Grijpma, D.W. and Poot, A.A., Macromol. Biosci., 2013, 13: 1711 doi: 10.1002/mabi.201300399
8. [8]
  Dong, J.T., Liao, L., Ma, Y., Shi, L., Wang, G.X., Fan, Z.Y., Li, S.M. and Lu, Z.Q., Polym. Degrad. Stab., 2014, 103: 26 doi: 10.1016/j.polymdegradstab.2014.03.004
9. [9]
  Huang, J., Yu, J.F., Yu, H.J., Sun, W.L. and Shen, Z.Q., Chinese J. Polym. Sci., 2011, 29(3): 390 doi: 10.1007/s10118-011-1044-8
10. [10]
  Kramer, J.R. and Deming, T.J., Polym. Chem., 2013, 5: 671
11. [11]
  Hyungjin, K., Takami, A. and Mitsuru, A., Macromol. Biosci., 2009, 9: 842 doi: 10.1002/mabi.v9:9
12. [12]
  Deng, M.X., Wu, J., Reinhart-King, C.A. and Chu, C.C., Biomacromolecules, 2009, 10: 3037 doi: 10.1021/bm9006437
13. [13]
  Li, Z.B. and Zhao, G.S., Chinese Journal of Hypertension, 1999, 7: 163
14. [14]
  Gao, P.J., Zhu, D.L., Zhan, Y.M., Olivier, S., Pierre, M. and Zhao, G.S., Acta Physiologica Sinica, 1998, 50: 401
15. [15]
  Wang, B., Dong, J., Li, Q.J., Xiong, Z.C., Xiong, C.D. and Chen, D.L., J. Biomed. Mater. Res. A, 2014, 102: 4062 doi: 10.1002/jbm.a.v102.11
16. [16]
  Kostyuk, P.G., Martynyuk, A.E. and Pogorelaya, N.C., Brain Res., 1991, 550: 11 doi: 10.1016/0006-8993(91)90399-G
17. [17]
  Doddi, N., Versfelt, C.C. and Wasserman, D., 1977, U.S. Pat., 4052988
18. [18]
  Deming, T.J., Adv. Mater., 1997, 9: 299 doi: 10.1002/(ISSN)1521-4095
19. [19]
  Ilya, Y. and Deming, T.J., J. Am. Chem. Soc., 2015, 137: 4078 doi: 10.1021/jacs.5b01543
20. [20]
  Yang, W.X., Wang, L.L., Zhu, H., Xu, R.W. and Wu, Y.X., Chinese J. Polym. Sci., 2013, 31(12): 1706 doi: 10.1007/s10118-013-1363-z
21. [21]
  Daly, W.H. and Poché, D., Tetrahedron Lett., 1988, 29: 5859 doi: 10.1016/S0040-4039(00)82209-1
22. [22]
  Vyner, M.C., Li, A. and Amsden, B.G., Biomaterials, 2014, 35: 9041 doi: 10.1016/j.biomaterials.2014.07.023
23. [23]
  Zeng, Q., Yang, K.K., Chen, S.C., Wang, X.L., Zeng, J.B. and Wang, Y.Z., Eur. Polym. J., 2008, 44: 465 doi: 10.1016/j.eurpolymj.2007.11.008
24. [24]
  Kricheldorf, H.R., Lossow, C.V., Lomadze, N. and Schwarz, G., J. Polym. Sci., Part A: Polym. Chem., 2008, 46: 4012 doi: 10.1002/(ISSN)1099-0518
25. [25]
  Yang, K.K., Wang, X.L. and Wang, Y.Z., J. Macromol. Sci-Pol. R., 2002, 42: 373 doi: 10.1081/MC-120006453
26. [26]
  Deming, T.J., Adv. Drug Delivery Rev., 2002, 54: 1145 doi: 10.1016/S0169-409X(02)00062-5
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1.
沈阳化工大学材料科学与工程学院沈阳 110142