Highly Thermally Stable, Organosoluble, and Hydrophobic Polyimides with Pyrrolidinylphenyl Pendant Groups and Pyridine Units

Chanjuan Liu; Mei Mei; Limin Zang; Huanfu Zhou; Xiaohua Huang; Chun Wei

Macromolecular Research, Vol.27, No.3, 232-237, March, 2019

DOI10.1007/s13233-019-7035-2 Export Citation

Highly Thermally Stable, Organosoluble, and Hydrophobic Polyimides with Pyrrolidinylphenyl Pendant Groups and Pyridine Units

Chanjuan Liu, Mei Mei, Limin Zang^†, Huanfu Zhou, Xiaohua Huang^†, and Chun Wei

Key Laboratory of New Processing Technology for Nonferrous Metal & Materials, Ministry of Education, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi, School of Materials Scien, Guilin University of Technology, Guilin, 541004, P. R. China

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A novel diamine monomer, 4-{4-(1-pyrrolidinyl)phenyl}-2,6-bis(4-aminophenyl) pyridine (PPAP), was synthesized using 4-(1-pyrrolidinyl)benzaldehyde as starting material, and a series of aromatic polyimides were prepared using PPAP and five aromatic dianhydrides by a two-step imidization method. The structure and properties of as-prepared polyimides were studied by Fourier transform infrared spectrometer (FTIR), nuclear magnetic resonance (NMR), thermogravimetric analysis (TG), differential scanning calorimetry (DSC), and wide angle X-ray diffraction (WAXD). The results indicated that these polymers had good solubility in highboiling organic solvents upon heating, such as N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and N-methyl-2-pyrrolidone (NMP). Furthermore, they had outstanding thermal properties with the glass transition temperature (Tg) exceeding 354°C, as well as T5% and T10% mass loss temperature under a nitrogen atmosphere in the range of 521~534 °C and 544~594 °C, respectively. Moreover, they exhibited excellent hydrophobic properties with the contact angles ranging from 82.7 to 90.5°. In addition, the results of WAXD showed that these polyimides exhibited the structure of amorphous polymers.

Keywords:polyimides;thermal stability;pyridine;organosoluble;hydrophobicity

[References]

Ding MX, Prog. Polym. Sci, 32, 623 (2007)
Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS, Prog. Polym. Sci, 37, 907 (2012)
Kim JG, Lee JM, Lee JE, Jo SI, Chang JY, Macromol. Res., 25(6), 629 (2017)
Yi L, Huang W, Yan DY, J. Polym. Sci. A: Polym. Chem., 55(4), 533 (2017)
Iredale RJ, Ward C, Hamerton I, Prog. Polym. Sci, 69, 1 (2017)
Li CY, Yi L, Xu ST, Wu XM, Huang W, Yan DY, J. Polym. Res., 24, 7 (2016)
Ghaemy M, Berenjestanaki FR, Bazzar M, Des. Monomers Polym., 17, 101 (2014)
Huang XH, Huang W, Zhou YF, Yan DY, Chinese J. Polym. Sci., 29, 506 (2011)
Zhao JJ, Gong CL, Zhang SJ, Shao Y, Li YF, Chin. Chem. Lett., 21, 277 (2010)
Mehdipour-Ataei S, Sarrafi Y, Hatami M, Eur. Polym. J., 40, 2009 (2004)
Gong SM, Liu M, Xia SL, Wang YH, J. Polym. Res., 21, 542 (2014)
Bong S, Yeo H, Goh M, Ku BC, Kim YY, Bong PH, Park B, You NH, Macromol. Res., 24(12), 1091 (2016)
Huang YC, Wang KL, Lee WY, Liao YA, Liaw DJ, Lee KR, Lai JY, J. Polym. Sci. A: Polym. Chem., 53(3), 405 (2015)
Serbezeanu D, Carja ID, Bruma M, Ronova IA, Struct. Chem., 27, 973 (2016)
Yi L, Li CY, Huang W, Yan DY, Polymer, 80, 67 (2015)
Yi L, Li CY, Huang W, Yan DY, J. Polym. Res., 21, 572 (2014)
Huang XH, Mei M, Liu CJ, Pei XL, Wei C, J. Polym. Res., 22, 169 (2015)
Huang XH, Pei XL, Wang LC, Mei M, Liu CJ, Wei C, J. Appl. Polym. Sci., 133, 43266 (2016)
Matsumoto T, Ozawa H, Ishiguro E, Komatsu S, J. Photopolym Sci. Technol., 29, 237 (2016)
Guo YZ, Shen D X, Ni HJ, Liu JG, S, Yang Y, Prog. Org. Coat., 76, 768 (2013)
Burdukovskii VF, Mognonov DM, Polym. Sci. Ser. B, 53, 341 (2011)
Wozniak AI, Yegorov AS, Ivanov VS, Igumnov SM, Tcarkova KV, J. Fluor. Chem., 180, 45 (2015)
Dhara MG, Banerjee S, Prog. Polym. Sci, 35, 1022 (2010)
Jung Y, Jeong B, Yang Y, Kim T, Kwon S, Macromol. Res., 25, 1 (2017)
Liu CJ, Pei XL. Mei M, Chou GO, Huang XH, Wei C, High Perform. Polym., 28, 1114 (2016)
Koohmareh GA, Des. Monomers Polym., 10, 517 (2007)
Mehdipour-Ataei S, Bahri-Laleh N, Iran. Polym. J., 17, 95 (2008)
Guan Y, Dong WB, Wang C, Shang DJ, Polym. Int., 66, 1044 (2017)
Guan Y, Wang CB, Wang DM, Dang GD, Chen CH, Zhou HW, Zhao XG, Polymer, 62, 1 (2015)
Dong WB, Guan Y, Shang DJ, RSC Adv., 6, 21662 (2016)
Zhuo L, Kou K, Yao P, Wu G, Wang Y, J. Therm. Anal. Calorim., 119, 2039 (2015)
Kenchappa R, Bodke YD, Chandrashekar A, Telkar S, Manjunatha KS, Sindhe MA, Arabian J. Chem., 10, 1336 (2017)
Huang Y, Xiu S, Niu HJ, Lian YF, Sci. Adv. Mater., 9, 249 (2017)
Khosa MK, Jamal MA, Iqbal R, Muneer M, Saif MJ, Zia KM, Hamid M, Polym-Plast. Technol., 56, 22 (2017)
Yao HY, Song NN, Shi KX, Feng SA, Zhu SY, Zhang YH, Guan SW, Polym. Chem., 7, 4728 (2016)
Chen JC, Wu JA, Chen KH, RSC Adv., 6, 33959 (2016)
Tapaswi PK, Choi MC, Nagappan S, Ha CS, J. Polym. Sci. A: Polym. Chem., 53(3), 479 (2015)

[Referenced By]

[1] Ding MX, Prog. Polym. Sci, 32, 623 (2007)

[2] Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS, Prog. Polym. Sci, 37, 907 (2012)

[3] Kim JG, Lee JM, Lee JE, Jo SI, Chang JY, Macromol. Res., 25(6), 629 (2017)

[4] Yi L, Huang W, Yan DY, J. Polym. Sci. A: Polym. Chem., 55(4), 533 (2017)

[5] Iredale RJ, Ward C, Hamerton I, Prog. Polym. Sci, 69, 1 (2017)

[6] Li CY, Yi L, Xu ST, Wu XM, Huang W, Yan DY, J. Polym. Res., 24, 7 (2016)

[7] Ghaemy M, Berenjestanaki FR, Bazzar M, Des. Monomers Polym., 17, 101 (2014)

[8] Huang XH, Huang W, Zhou YF, Yan DY, Chinese J. Polym. Sci., 29, 506 (2011)

[9] Zhao JJ, Gong CL, Zhang SJ, Shao Y, Li YF, Chin. Chem. Lett., 21, 277 (2010)

[10] Mehdipour-Ataei S, Sarrafi Y, Hatami M, Eur. Polym. J., 40, 2009 (2004)

[11] Gong SM, Liu M, Xia SL, Wang YH, J. Polym. Res., 21, 542 (2014)

[12] Bong S, Yeo H, Goh M, Ku BC, Kim YY, Bong PH, Park B, You NH, Macromol. Res., 24(12), 1091 (2016)

[13] Huang YC, Wang KL, Lee WY, Liao YA, Liaw DJ, Lee KR, Lai JY, J. Polym. Sci. A: Polym. Chem., 53(3), 405 (2015)

[14] Serbezeanu D, Carja ID, Bruma M, Ronova IA, Struct. Chem., 27, 973 (2016)

[15] Yi L, Li CY, Huang W, Yan DY, Polymer, 80, 67 (2015)

[16] Yi L, Li CY, Huang W, Yan DY, J. Polym. Res., 21, 572 (2014)

[17] Huang XH, Mei M, Liu CJ, Pei XL, Wei C, J. Polym. Res., 22, 169 (2015)

[18] Huang XH, Pei XL, Wang LC, Mei M, Liu CJ, Wei C, J. Appl. Polym. Sci., 133, 43266 (2016)

[19] Matsumoto T, Ozawa H, Ishiguro E, Komatsu S, J. Photopolym Sci. Technol., 29, 237 (2016)

[20] Guo YZ, Shen D X, Ni HJ, Liu JG, S, Yang Y, Prog. Org. Coat., 76, 768 (2013)

[21] Burdukovskii VF, Mognonov DM, Polym. Sci. Ser. B, 53, 341 (2011)

[22] Wozniak AI, Yegorov AS, Ivanov VS, Igumnov SM, Tcarkova KV, J. Fluor. Chem., 180, 45 (2015)

[23] Dhara MG, Banerjee S, Prog. Polym. Sci, 35, 1022 (2010)

[24] Jung Y, Jeong B, Yang Y, Kim T, Kwon S, Macromol. Res., 25, 1 (2017)

[25] Liu CJ, Pei XL. Mei M, Chou GO, Huang XH, Wei C, High Perform. Polym., 28, 1114 (2016)

[26] Koohmareh GA, Des. Monomers Polym., 10, 517 (2007)

[27] Mehdipour-Ataei S, Bahri-Laleh N, Iran. Polym. J., 17, 95 (2008)

[28] Guan Y, Dong WB, Wang C, Shang DJ, Polym. Int., 66, 1044 (2017)

[29] Guan Y, Wang CB, Wang DM, Dang GD, Chen CH, Zhou HW, Zhao XG, Polymer, 62, 1 (2015)

[30] Dong WB, Guan Y, Shang DJ, RSC Adv., 6, 21662 (2016)

[31] Zhuo L, Kou K, Yao P, Wu G, Wang Y, J. Therm. Anal. Calorim., 119, 2039 (2015)

[32] Kenchappa R, Bodke YD, Chandrashekar A, Telkar S, Manjunatha KS, Sindhe MA, Arabian J. Chem., 10, 1336 (2017)

[33] Huang Y, Xiu S, Niu HJ, Lian YF, Sci. Adv. Mater., 9, 249 (2017)

[34] Khosa MK, Jamal MA, Iqbal R, Muneer M, Saif MJ, Zia KM, Hamid M, Polym-Plast. Technol., 56, 22 (2017)

[35] Yao HY, Song NN, Shi KX, Feng SA, Zhu SY, Zhang YH, Guan SW, Polym. Chem., 7, 4728 (2016)

[36] Chen JC, Wu JA, Chen KH, RSC Adv., 6, 33959 (2016)

[37] Tapaswi PK, Choi MC, Nagappan S, Ha CS, J. Polym. Sci. A: Polym. Chem., 53(3), 479 (2015)