Synthesis, characterization and application of methyl 3,5-disulfo-benzoate dipotassium dihydrate as nucleating agent for poly( L-lactide)

Abstract

A newly synthesized aromatic sulfonate compound, complex 2 with formula of K₂[H₃COOC-C₆H₃(SO₃)₂]·2H₂O(methyl 3,5-disulfo-benzoate dipotassium dihydrate) was synthesized and characterized by elemental analysis, infrared(IR) spectrometry, nuclear magnetic resonance(NMR) and crystal structure measurement. Single-crystal X-ray diffraction(XRD) revealed that complex 2 crystallized in the triclinic system with space group $P_{\bar 1}$. Complex 2 was used as nucleating agent for poly(L-lactide)(PLLA). The crystallization of PLLA with powder of complex 2 was investigated by means of differential scanning calorimetry(DSC) and polarized optical microscopy (POM). The results prove that complex 2 was effective as nucleating agent for PLLA. It could accelerate crystallization by reducing the induction time and increasing the density of nuclei in the crystallization process. The half-time of crystallization(t _0.5) for pure PLLA was about 8 times longer than that of PLLA sample with 1.0%(mass fraction) of complex 2.

Keywords

Nucleating agent / Crystal structure / Poly( L-lactide) / Isothermal crystallization

References

[1] Athanasiou K A, Niederauer G G, Agrawal C M. Biomaterials, 1996, 17: 93.

[2] Lim L T, Auras R, Rubino M. Prog. Polym. Sci., 2008, 33: 820.

[3] Lin Y M, Boccaccini A R, Polak J M, Bishop A E, Maquet V. J. Biomater. Appl., 2006, 21: 109.

[4] Madhavan N K, Nair N R, John R P. Bioresour. Technol., 2010, 101: 8493.

[5] Yan J, Gao Y, Wang Q, Cui X J, Zhong S L, Wang P, Wang H Y. Chem. J. Chinese Universities, 2012, 33(2): 389.

[6] Luo B H, Li J H, Yang J, Xu C, Tian J H, Zhou C R. Chem. J. Chinese Universities, 2012, 33(6): 1360.

[7] Tian H Y, Tang Z H, Zhuang X L, Chen X S, Jing X B. Prog. Polym. Sci., 2012, 37: 237.

[8] Drumright R E, Gruber P R, Henton D E. Adv. Mater., 2000, 12: 1841.

[9] Dorgan J R, Lehermeier H, Mang M. J. Polym. Environ., 2000, 8: 1.

[10] Tokiwa Y, Jarerat A. Macromol. Symp., 2003, 201: 283.

[11] Sawyer D J. Macromol. Symp., 2003, 201: 271.

[12] John R P, Nampoothiri K M, Pandey A. Process Biochem., 2006, 41: 759.

[13] Liu Q, Cai C, Dong C M. J. Biomed. Mater. Res. A, 2009, 88A: 990.

[14] Pang X, Zhuang X L, Tang Z H, Chen X S. Biotechnol. J., 2010, 5: 1125.

[15] Bai H W, Zhang W Y, Deng H, Zhang Q, Fu Q. Macromolecules, 2011, 44: 1233.

[16] Zhang Y, Xu J, Guo B H. Acta. Polym. Sin., 2012, 1: 83.

[17] Zhang N W, Zeng C, Wang L, Ren J. Polym. Environ., 2013, 21: 286.

[18] Kristiansen M, Tervoort T, Smith P, Goossens H. Macromolecules, 2005, 38: 10461.

[19] Jiang N, Zhao L F, Gan Z H. Polym. Degrad. Stab., 2010, 95: 1045.

[20] Luo F, Geng C Z, Wang K, Deng H, Chen F, Fu Q, Na B. Macromolecules, 2009, 42: 9325.

[21] Li H B, Huneault M A. Polymer, 2007, 48: 6855.

[22] Wei J C, Ma L L, Dai Y F, Chen Y, Zhang P, Cui Y, Chen X S. Chem. J. Chinese Universities, 2011, 32(11): 2674.

[23] Wang S G, Wan Y Q, Cai Q, He B, Chen W N. Chem. Res. Chinese Universities, 2004, 20(2): 191.

[24] Pluta M, Jeszka J K, Boiteux G. Eur. Polym. J, 2007, 43: 2819.

[25] Sarazin P, Li G, Orts W J, Favis B D. Polymer, 2008, 49: 599.

[26] Yokohara T, Yamaguchi M. Eur. Polym. J., 2008, 44: 677.

[27] Kolstad J J. J. Appl. Polym. Sci., 1996, 62: 1079.

[28] Ogato N, Jimenez G, Kawai H, Ogihara T. J. Polym. Sci. B, 1997, 35: 389.

[29] Li Y L, Wang Y, Liu L, Han L, Xiang F M, Zhou Z W. J. Polym. Sci. B, 2009, 47: 326.

[30] Angela M H, Ellen C L. J. Appl. Polym. Sci., 2008, 107: 2246.

[31] Schmidt S C, Hillmyer M A. J. Polym. Sci. B, 2001, 39: 300.

[32] Tsuji H. Macromol. Biosci., 2005, 5: 569.

[33] Fujita M, Sawayanagi T, Abe H, Muller D A, Wiesner U. Macromolecules, 2008, 41: 852.

[34] Sun J, Yu H, Zhuang X, Chen X S, Jing X B. J. Phys. Chem. B, 2011, 115: 2864.

[35] Hao Q, Li F, Li Q, Li Y, Jia L, Yang J. Biomacromolecules, 2005, 6: 2236.

[36] Nakajima H, Takahashi M, Kimura Y. Macromol. Mater. Eng., 2010, 295: 460.

[37] Sheldrick G M. Acta. Crystallogr., 2008, A64: 112.

[38] Fischer E W, Sterzel H J, Wegner G. Colloid Polym. Sci., 1973, 251: 980.

[39] Qu X H, Wu Q, Liang J, Zou B, Chen G Q. Biomaterials, 2006, 27: 2944.