Synthesis of novel poly(aryl ether sulfone)s bearing bulky pendants for gas separation membranes

Zhuang Liu; Baijun Liu; Long Li; Yinan Zhang; Zhenhua Jiang

Macromolecular Research, Vol.21, No.6, 608-613, June, 2013

DOI10.1007/s13233-013-1056-z Export Citation

Synthesis of novel poly(aryl ether sulfone)s bearing bulky pendants for gas separation membranes

Zhuang Liu, Baijun Liu, Long Li, Yinan Zhang, and Zhenhua Jiang^†

Alan G. MacDiarmid Institute, Jilin University, 2699 Qianjin Street, Changchun, 130012, P. R. China

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A hydroxylated poly(aryl ether sulfone) (PES-OH) was synthesized by a demethylation reaction of a methoxy-functionalized PES (PES-OCH3) using the HCl/pyridine system. Derived from this hydroxylated PES precursor, bulky (2-trifluoromethyl-4-nitro) phenyl (TFN) and benzophenone (BZP) were introduced to the PES backbones as side groups via aromatic nucleophilic substitution reactions. A direct property comparison of PES-OH, PES-OCH3, PES-TFN and PES-BZP has been made, and these analogues exhibited different solubility, thermal properties and gas permeability. PES grafted with the trifluoromethyl side group (PES-TFN) demonstrated more attractive permeabilities and permselectivities for O2/N2 separation compared to the others, and it exhibited the best P(O2)/P(N2) value of 8.44.

Keywords:poly(aryl ether sulfone)s;gas separation;selectivity;grafting reactions

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[1] Gatham KV, Turner S, Polymer, 15, 665 (1974)

[2] Rao VL, J. Macromol. Sci.-Polym. Rev, 39, 655 (1999)

[3] Kim JP, Kang JW, Kim JJ, Lee JS, Polymer, 44(15), 4189 (2003)

[4] Fox DW, in Kirk-Othmer Encyclopedia of Chemical Technology, Kroschwitz J, Ed., Wiley, New York, 1985, Vol. 18, p 479.

[5] Sauers ME, Mckenna LA, Merria CN, in High Performance Polymers, Elsevier Science, New York, 1986, p 159.

[6] Pandey P, Chauhan RS, Prog. Polym. Sci, 26, 853 (2001)

[7] McHattie JS, Koros WJ, Paul DR, Polymer, 32, 2618 (1991)

[8] Dai Y, Guiver MD, Robertson GP, Kang YS, Lee KJ, Macromolecules, 36(18), 6807 (2003)

[9] Robeson LM, J. Membr. Sci., 62, 165 (1991)

[10] Freeman BD, Macromolecules, 32(2), 375 (1999)

[11] Jung CH, Lee YM, Macromol. Res., 16(6), 555 (2008)

[12] Peter MB, Neil BM, Polym. Chem., 1, 63 (2010)

[13] Gao H, Wang D, Jiang W, Guan SW, Jiang ZH, J. Appl. Polym. Sci., 109(4), 2341 (2008)

[14] Dai Y, Guiver MD, Robertson GP, Bilodeau F, Kang YS, Lee KJ, Jho JY, Won J, Polymer, 43(20), 5369 (2002)

[15] Dai Y, Guiver MD, Robertson GP, Kang YS, Macromolecules, 38(23), 9670 (2005)

[16] Chen WH, Liu BJ, Yang YH, Yue XG, Jing LW, Guo MM, Sun XH, Gao LX, Jiang ZH, Chem. J. Chin. Univ., 30, 2534 (2009)

[17] Yue XG, Zhang HB, Chen WH, Wang YS, Zhang SL, Wang GB, Jiang ZH, Polymer, 48(16), 4715 (2007)

[18] Lee WM, Polym. Eng. Sci., 20, 65 (1980)

[19] Bondi A, J. Phys. Chem., 68, 441 (1964)

[20] van Krevelen DW, Properties of Polymers: Their Correlation with Chemical Structure; Their Numerical Estimation and Prediction from Additive Group Contributions, Elsevier, Amsterdam, 1990.

[21] Chern RT, Sheu FR, Jia L, Stannett VT, Hopfenberg HB, J. Membr. Sci., 35, 103 (1987)

[22] Park JY, Paul DR, J. Membr. Sci., 125(1), 23 (1997)

[23] Robeson LM, J. Membr. Sci., 320(1-2), 390 (2008)