Synthesis and characterization of poly(N-arylenebenzimidazole ketone ketone)s

Yewei Xu; Jie Tang; Guanjun Chang; Fanghua Zhu; Xuan Luo; Lin Zhang

Macromolecular Research, Vol.21, No.6, 681-686, June, 2013

DOI10.1007/s13233-013-1059-9 Export Citation

Synthesis and characterization of poly(N-arylenebenzimidazole ketone ketone)s

Yewei Xu, Jie Tang¹, Guanjun Chang, Fanghua Zhu, Xuan Luo, and Lin Zhang^†

Research Center of Laser Fusion, China Academy of Engineering Physics, Mianyang, 621900, P. R. China
¹School of Chemistry and Chemical Engineering, Mianyang Normal University, Mianyang, 621000, P. R. China, Korea

E-mail:

Poly(N-arylenebenzimidazole ketone ketone)s (PNABIKKs) consisting of m- and p-phenylene linkages have been synthesized by nucleophilic aromatic substitution from bis(benzimidazolyl) derivatives containing sulfonyl, carbonyl, and ether groups with activated aromatic difluorides in sulfolane at 210 °C in the presence of anhydrous potassium carbonate. The structures of the polymers were characterized by means of Fourier tramsfom infrared (FTIR), proton nuclear magnetic resonance (1H NMR) spectroscopy, and elemental analysis, and the results were largely consistent with the proposed structure. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TG) measurements demonstrated that polymers had high glass transition temperatures (T g >220 °C) and good thermal stability with high decomposition temperatures (T D >480 °C). These novel polymers also showed good solubility.

Keywords:polybenzimidazole;poly(N-arylenebenzimidazole ketone ketone)s;thermal properties;solubility

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[2] Critchle JP, Knight GJ, Wright WW, Heat-Resistant Polymers, Plenum Press, New York, 1993.

[3] Asensio JA, Sanchez EM, Gomez-Romero P, Chem. Soc. Rev., 39, 3210 (2010)

[4] Laberty-Robert C, Valle K, Pereira F, Sancheza C, Chem. Soc. Rev., 40, 961 (2011)

[5] Hergenrother PM, Smith JG, Connell JW, Polymer, 34, 856 (1993)

[6] Twieg R, Matray T, Hedrick JL, Macromolecules, 29(23), 7335 (1996)

[7] Guan Y, Pu H, Wan D, Polym. Chem., 2, 1287 (2011)

[8] Lakshmi Narayan TV, Marvel CS, J. Polym. Sci. A: Polym. Chem., 5, 1113 (1967)

[9] Bhavsar RS, Nahire SB, Kale MS, Patil SG, Aher PP, Bhavsar RA, Kharul UK, J. Appl. Polym. Sci., 120(2), 1090 (2011)

[10] Chung IS, Park CE, Ree M, Kim SY, Chem. Mater., 13, 2801 (2001)

[11] Berrada M, Carriere F, Abboud Y, Abourriche A, Benamara A, Lajrhed N, Kabbaj M, Berrada M, J. Mater. Chem., 12, 3551 (2002)

[12] Choi H, Chung IS, Hong K, Park CE, Kim SY, Polymer, 49(11), 2644 (2008)

[13] Kim SK, Kim TH, Jung JW, Lee JC, Polymer, 50(15), 3495 (2009)

[14] Banihashemi A, Atabaki F, Eur. Polym. J., 38, 2119 (2002)

[15] Toiserkani H, Sheibani H, Saidi K, Eur. Polym. J., 46, 185 (2010)

[16] Johnson FE, Cabasso I, Macromolecules, 43(8), 3634 (2010)

[17] Yamaguchi I, Osakada K, Yamamoto T, Macromolecules, 30(15), 4288 (1997)

[18] Klaehn JR, Luther TA, Orme CJ, Jones MG, Wertsching AK, Peterson ES, Macromolecules, 40(21), 7487 (2007)

[19] Kumbharkar SC, Kharul UK, Eur. Polym. J., 45, 3363 (2009)

[20] Hua M, Chen H, Tsai R, Leu Y, Liu Y, Lai J, J. Mater. Chem., 21, 7254 (2011)

[21] Li ZX, Liu JH, Yang SY, Huang SH, Lu JD, Pu JL, J. Polym. Sci. A: Polym. Chem., 44(19), 5729 (2006)

[22] Xu HJ, Chen KC, Guo XX, Fang JH, Yin J, J. Polym. Sci. A: Polym. Chem., 45(6), 1150 (2007)

[23] Kulkarni M, Potrekar R, Kulkarni RA, Vernekar SP, J. Polym. Sci. A: Polym. Chem., 46(17), 5776 (2008)

[24] Xu N, Guo XX, Fang JH, Xu HJ, Yin J, J. Polym. Sci. A: Polym. Chem., 47(24), 6992 (2009)

[25] Li Q, Jensen JO, Savinell RF, Bjerrum NJ, Prog. Polym. Sci, 34, 449 (2009)

[26] Smith JG, Connell JW, Hergenrother PM, J. Polym. Sci. A: Polym. Chem., 31, 3099 (1993)

[27] Hlil AR, Matsumura S, Hay AS, Macromolecules, 41(6), 1912 (2008)

[28] Qi YH, Gao Y, Tian SH, Hlil AR, Gaudet J, Guay D, Hay AS, J. Polym. Sci. A: Polym. Chem., 47(7), 1920 (2009)

[29] Sannigrahi A, Arunbabu D, Sankar RM, Jana T, J. Phys. Chem. B, 111(42), 12124 (2007)

[30] Musto P, Karasz FE, Macknight WJ, Polymer, 34, 2934 (1993)

[31] Kim TH, Kim SK, Lim TW, Lee JC, J. Membr. Sci., 323(2), 362 (2008)