Abstract
A series of polyimide (PI) films were prepared through a two-step polycondensation process via chemical imidization using five commercial aromatic dianhydrides and a novel diamine containing an imidazole unit and trifluoromethyl groups, i.e., 4,4′-(((4,5-diphenyl-1H-imidazole-1,2-diyl)bis(4,1-phenylene))bis(oxy)) bis(3-(trifluoromethyl)aniline) (referred to as diamine 3). The number average molecular weights of the resulting PIs ranged from 1.57 × 104 to 3.17 × 104 g·mol−1 with polydispersity indices between 2.53 and 3.60, which were obtained through gel permeation chromatography measurements using a polystyrene standard. All the PIs prepared using diamine 3 were amorphous because of the large side group and kink structure of the diamine. They are soluble in common high-boiling point solvents, such as N-methyl pyrrolidone, dimethyl acetamide, and m-cresol, as well as several low-boiling point solvents, including chloroform and tetrahydrofuran. They exhibit the thermal stability with 10% weight loss temperatures in the range of 545 to 562 °C and 5% weight loss temperatures in the range of 500 to 541 °C in a nitrogen atmosphere. Their glass transition temperatures exceed 245 °C. All the resulting PI films show transmittances of over 74% in the visible light region ranging from 400 to 760 nm. The tensile strength of the PI films is in the range of 30.1 to 52.8 MPa, while the tensile modulus ranges from 1.0 to 1.7 GPa.
Article PDF
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
References
S. Bong, H. Yeo, B. C. Ku, M. Goh, and N. H. You, Macromol. Res., 26, 85 (2018).
W. M. Edwards and R. I. Robison, US Patent, 2710853 (1955).
D. J. Liaw, K. L. Wang, Y. C. Huang, K. R. Lee, J. Y. Lai, and C. S. Ha, Prog. Polym. Sci., 37, 907 (2012).
X. H. Huang, W. Huang, J. Liu, L. Meng, and D. Y. Yan, Polym. Int., 61, 1503 (2012).
Y. C. Xiao, B. T. Low, S. S. Hosseini, T. S. Chung, and D. R. Paul, Prog. Polym. Sci., 34, 561 (2009).
S. K. Yesodha, C. K. S. Pillai, and N. Tsutsumi, Prog. Polym. Sci., 29, 45 (2004).
P. K. Tapaswi and C. S. Ha, Macromol. Chem. Phys., 220, 1800313 (2019).
H. S. Jin, J. H. Chang, and J. C. Kim, Macromol. Res., 16, 503 (2008).
W. Huang, D. Y. Yan, and Q. H. Lu, Macromol. Rapid Commun., 22, 1481 (2001).
J. Weber, J. Schmidt, A. Thomas, and W. Bohlmann, Langmuir, 26, 15650 (2010).
K. V. Rao, R. Haldar, C. Kulkarni, T. K. Maji, and S. J. George, Chem. Mater., 24, 969 (2012).
A. S. Mathews, I. Kim, and C. S. Ha, Macromol. Res., 15, 114 (2007).
H. J. Ni, J. G. Liu, Z. H. Wang, and S. Y. Yang, J. Ind. Eng. Chem., 28, 16 (2015).
M. Hasegawa and K. Horie, Prog. Polym. Sci., 26, 259 (2001).
Y. Zhuang, J. G. Seong, and Y. M. Lee, Prog. Polym. Sci., 92, 35 (2019).
C. Y. Li, L. Yi, S. Xu, X. M. Wu, W. Huang, and D. Y. Yan, J. Polym. Res., 24, 7 (2017).
L. Yi, W. Huang, and D. Y. Yan, J. Polym. Sci., Part A Polym. Chem., 55, 533 (2017).
X. M. Wu, C. Shu, X. Q. He, S. Wang, X. Fan, Z. Yu, D. Y. Yan, and W. Huang, Macromol. Chem. Phys., 221, 1900506 (2020).
K. M. Jeong, P. K. Tapaswi, T. Kambara, R. Ishige, S. Ando, and C. S. Ha, High Perform. Polym., 32, 620 (2020).
C. Y. Wang, G. Li, X. Y. Zhao, and J. M. Jiang, J. Polym. Sci., Part A: Polym. Chem., 47, 3309 (2009).
K. Zeng, Q. Guo, S. Gao, D. Wu, H. Fan, and G. Yang, Macromol. Res., 20, 10 (2012).
G. S. Liou, Y. L. Yang, and Y. O. Su, J. Polym. Sci., Part A: Polym. Chem., 44, 2587 (2006).
C. Liu, M. Mei, L. Zang, H. Zhou, X. Huang, and C. Wei, Macromol. Res., 27, 232 (2019).
R. Revathi, P. Prabunathan, S. Devaraju, and M. Alagar, High Perform. Polym., 27, 247 (2015).
S. J. Zhang, Q. Q. Bu, Y. F. Li, C. L. Gong, X. Y. Xu, and H. Li, Mater. Chem. Phys., 128, 392 (2011).
Y. H. Kim, H. S. Kim, and S. K. Kwon, Macromolecules, 38, 7950 (2005).
C. Wang, W. Chen, Y. Chen, X. Zhao, J. Li, and Q. Ren, Mater. Chem. Phys., 144, 553 (2014).
S. D. Kim, S. Y. Kim, and I. S. Chung, J. Polym. Sci., Part A: Polym. Chem., 51, 4413 (2013).
M. Ghaemy and R. Alizadeh, Eur. Polym. J., 45, 1681 (2009).
L. Yi, W. Huang, and D. Y. Yan, J. Polym. Sci., Part A: Polym. Chem., 54, 976 (2016).
A. Ghosh, S. K. Sen, S. Banerjee, and B. Voit, RSC Adv., 2, 5900 (2012).
M. Ghaemy and F. R. Berenjestanaki, J. Fluorine Chem., 144, 86 (2012).
S. M. Amininasab, S. Esmaili, M. Taghavi, and Z. Shami, J. Fluorine Chem., 192, 48 (2016).
S. M. A. Nasab and M. Ghaemy, J. Polym. Res., 18, 1575 (2011).
W. Jang, H. S. Lee, S. Lee, S. Choi, D. Shin, and H. Han, Mater. Chem. Phys., 104, 342 (2007).
M. Ghaemy and R. Alizadeh, Eur. Polym. J., 45, 1681 (2009).
D. Yin, Y. Li, H. Yang, S. Yang, L. Fan, and J. Liu, Polymer, 46, 3119 (2005).
K. M. Jeong, Y. Li, D. G. Yoo, N. K. Lee, H. G. Lee, S. Ando, and C. S. Ha, Polym, Int., 67, 588 (2018).
L. Yi, C. Y. Li, W. Huang, and D. Y. Yan, Polymer, 80, 67 (2015).
M. Hasegawa, M. Fujii, J. Ishii, S. Yamaguchi, E. Takezawa, and T. Kagayama, Polymer, 55, 4693 (2014).
M. Hasegawa, K. Kasamatsu, and K. Koseki, Eur. Polym. J., 48, 483 (2012).
P. K. Tapaswi, M. C. Choi, S. Nagappan, and C. S. Ha, J. Polym. Sci., Part A: Polym. Chem., 53, 479 (2015).
M. Zhang, W. Liu, X. Gao, P. Cui, T. Zou, G. Hu, L. Tao, and L. Zhai, Polymers, 12, 1532 (2020).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Acknowledgments: The work was financially supported by the Korea Institute for Advancement of Technology funded by the Ministry of Trade, Industry and Energy (P0017531) and the National Research Foundation of Korea (NRF) Grant funded by the Ministry of Science and ICT, Korea (NRF-2017R1A2B3012961 and Brain Korea 21 Plus Program (4199990414196)).
Rights and permissions
About this article
Cite this article
He, X., Tapaswi, P.K., Ha, CS. et al. Soluble Polyimides Derived from a Novel Aromatic Diamine Containing an Imidazole Unit and Trifluoromethyl Groups. Macromol. Res. 29, 365–375 (2021). https://doi.org/10.1007/s13233-021-9045-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13233-021-9045-0