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Synthesis and optical properties of semi-fluorinated poly(ether imide)s derived from non-fluorinated 1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride (HQDPA) and trifluoromethyl-substituted diamines

Published online by Cambridge University Press:  21 January 2019

Yong Xu*
Affiliation:
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
Linshuang Li
Affiliation:
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
Jianfei Che
Affiliation:
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
Zhifeng Ye
Affiliation:
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
*
a)Address all correspondence to this author. e-mail: [email protected]
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Abstract

A series of optically transparent and colorless semi-fluorinated poly(ether imide)s (PEIs) (III) were prepared from non-fluorinated 1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride (HQDPA) with various trifluoromethyl-substituted diamines. The III series showed more colorless and higher optical transparency with a cutoff absorption wavelength (λ0) below 370 nm than the IV series based on the corresponding non-fluorinated analogues and V series derived from CF3-free pyromellitic dianhydride (PMDA). Compared with the fluorinated VI series based on fluorinated 4,4′-hexafluoroisopropylidenediphthalic anhydride (6FDA), the semi-fluorinated III series not only exhibited much better optical transparency, but also had better mechanical and thermal properties. The III series had a tensile strength of 79.8–109.5 MPa, modulus of elasticity of 3.0–7.7 GPa and elongation at break of 14.2–26.7%, together with glass-transition temperatures (Tg) ranging from 214.3 to 265.1 °C and temperatures of 5% weight loss (T5%) beyond 530 °C. Meanwhile, the novel semi-fluorinated PEI IIIb was optically transparent and colorless with a λ0 of 367 nm coupled with dielectric constants below 3.2 and contact angles against water over 112°. In particular, the optically transparent IIIa exhibited the best tensile strength of 109.5 MPa when compared with already reported counterparts.

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Copyright © Materials Research Society 2019 

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References

Spechler, J.A., Koh, T.W., Herb, J.T., Rand, B.P., and Arnold, C.B.: A transparent, smooth, thermally robust, conductive polyimide for flexible electronics. Adv. Funct. Mater. 25, 7428 (2015).CrossRefGoogle Scholar
Kim, J., Kwon, J., Kim, M., Do, J., Lee, D., and Han, H.: Low-dielectric-constant polyimide aerogel composite films with low water uptake. Polym. J. 134, 48 (2016).Google Scholar
Zha, J.W., Fan, B.H., Dang, Z.M., and Li, S.T.: Microstructure and electrical properties in three-component (Al2O3–TiO2)/polyimide nanocomposite films. J. Mater. Res. 25, 2384 (2010).CrossRefGoogle Scholar
Lin, C.Y., Kuo, D.H., Sie, F.R., Cheng, J.Y., and Liou, G.S.: Preparation and characterization of organosoluble polyimide/BaTiO3 composite films with mechanical-and chemical-treated ceramic fillers. Polym. J. 44, 1131 (2012).CrossRefGoogle Scholar
Li, L.S., Xu, Y., Che, J.F., Su, X., Song, C.R., and Ma, X.P.: Transparent fluorinated poly(imide siloxane) copolymers with good adhesivity. Macromol. Res. 25, 1076 (2017).CrossRefGoogle Scholar
Ni, H.J., Liu, J.G., Wang, Z.H., and Yang, S.Y.: A review on colorless and optically transparent polyimide films: Chemistry, process and engineering applications. J. Ind. Eng. Chem. 28, 16 (2015).CrossRefGoogle Scholar
Ando, S., Matsuura, T., and Sasaki, S.: Coloration of aromatic polyimides and electronic properties of their source materials. Polym. J. 29, 69 (1997).CrossRefGoogle Scholar
Hasegawa, M., Hirano, D., Fujii, M., Haga, M., Takezawa, E., Yamaguchi, S., Ishikawa, A., and Kagayama, T.: Solution-processable colorless polyimides derived from hydrogenated pyromellitic dianhydride with controlled steric structure. J. Polym. Sci., Part A: Polym. Chem. 51, 575 (2013).CrossRefGoogle Scholar
Ke, F.Y., Song, N.H., Liang, D.H., and Xu, H.Y.: A method to break charge transfer complex of polyimide: A study on solution behavior. J. Appl. Polym. Sci. 127, 797 (2013).CrossRefGoogle Scholar
Liu, Y.W., Zhang, Y., Lan, Q., Liu, S.W., Qin, Z.X., Chen, L.H., Zhao, C.Y., Chi, Z.G., Xu, J.R., and Economy, J.: High-performance functional polyimides containing rigid nonplanar conjugated triphenylethylene moieties. Chem. Mater. 24, 1212 (2012).CrossRefGoogle Scholar
Mathews, A.S., Kim, I., and Ha, C.S.: Synthesis, characterization, and properties of fully aliphatic polyimides and their derivatives for microelectronics and optoelectronics applications. Macromol. Res. 15, 114 (2007).CrossRefGoogle Scholar
Hou, Y.G., Chen, G.F., Pei, X.L., and Fang, X.Z.: Synthesis and characterization of novel optically transparent and organosoluble polyimides based on diamines containing cyclohexane moiety. J. Polym. Res. 19, 9955 (2012).CrossRefGoogle Scholar
Liu, H.S. and Jeng, S.C.: Liquid crystal alignment by polyhedral oligomeric silsesquioxane (POSS)-polyimide nanocomposites. Opt. Mater. 35, 1418 (2013).CrossRefGoogle Scholar
Bong, S., Yeo, H., Goh, M., Ku, B.C., Kim, Y.Y., Bong, P.H., Park, B., and You, N.H.: Synthesis and characterization of colorless polyimides derived from 4-(4-aminophenoxy)-2,6-dimethylaniline. Macromol. Res. 12, 1091 (2016).CrossRefGoogle Scholar
Yi, L., Li, C.Y., Huang, W., and Yan, D.Y.: Soluble and transparent polyimides with high T g from a new diamine containing tert-butyl and fluorene units. J. Polym. Sci., Part A: Polym. Chem. 54, 976 (2016).CrossRefGoogle Scholar
Chen, G.F., Zhou, Y., Ma, K., Wang, W., and Fang, X.Z.: Synthesis and properties of transparent polyimides derived from 1,4-cyclohexylene bis(trimellitate anhydride). High Perform. Polym. 29, 627 (2017).CrossRefGoogle Scholar
Jarzabek, B., Schab-Balcerzak, E., Chamenko, T., Sek, D., Cisowski, J., and Volozhin, A.: Optical properties of new aliphatic–aromatic co-polyimides. J. Non-Cryst. Solids 299, 1057 (2002).CrossRefGoogle Scholar
Mathews, A.S., Kim, I., and Ha, C.S.: Fully aliphatic polyimides from adamantane-based diamines for enhanced thermal stability, solubility, transparency, and low dielectric constant. J. Appl. Polym. Sci. 102, 3316 (2006).CrossRefGoogle Scholar
Guo, Y., Shen, D., Ni, H., Liu, J., and Yang, S.: Organosoluble semi-alicyclic polyimides derived from 3,4-dicarboxy-1,2,3,4-tetrahydro-6-tert-butyl-1-naphthalene succinic dianhydride and aromatic diamines: Synthesis, characterization and thermal degradation investigation. Prog. Org. Coat. 76, 768 (2013).CrossRefGoogle Scholar
Kim, S.D., Kim, S.Y., and Chung, I.S.: Soluble and transparent polyimides from unsymmetrical diamine containing two trifluoromethyl groups. J. Polym. Sci., Part A: Polym. Chem. 51, 4413 (2013).CrossRefGoogle Scholar
Choi, I.H., Sohn, B., and Chang, J.H.: Synthesis and characterization of transparent copolyimide films containing CF3 groups: Comparison with copolyimide nanocomposites. Appl. Clay Sci. 48, 117 (2010).CrossRefGoogle Scholar
Damaceanu, M.D., Constantin, C.P., Nicolescu, A., Bruma, M., Belomonia, N., and Begunov, R.S.: Highly transparent and hydrophobic fluorinated polyimide films with ortho-kink structure. Eur. Polym. J. 50, 200 (2014).CrossRefGoogle Scholar
Chen, Y.C. and Hsiao, S.H.: Optically transparent and organosoluble poly(ether imide)s based on a bis(ether anhydride) with bulky 3,3′,5,5′-tetramethylbiphenyl moiety and various fluorinated bis(ether amine)s. High Perform. Polym. 30, 47 (2018).CrossRefGoogle Scholar
Tapaswi, P.K., Choi, M.C., Nagappan, S., and Ha, C.S.: Synthesis and characterization of highly transparent and hydrophobic fluorinated polyimides derived from perfluorodecylthio substituted diamines monomers. J. Polym. Sci., Part A: Polym. Chem. 53, 479 (2015).CrossRefGoogle Scholar
Ghaemy, M., Berenjestanaki, F.R., and Bazzar, M.: Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains. Des. Monomers Polym. 17, 101 (2014).CrossRefGoogle Scholar
Chung, C.L., Yang, C.P., and Hsiao, S.H.: Organosoluble and colorless fluorinated poly(ether imide)s from 1,2-bis(3,4-dicarboxyphenoxy)benzene dianhydride and trifluoromethyl-substituted aromatic bis(ether amine)s. J. Polym. Sci., Part A: Polym. Chem. 44, 3092 (2006).CrossRefGoogle Scholar
Jang, W.B., Shin, D., Choi, S., Park, S., and Han, H.: Effects of internal linkage groups of fluorinated diamine on the optical and dielectric properties of polyimide thin films. Polymer 48, 2130 (2007).CrossRefGoogle Scholar
Chen, Y.C., Hsiao, S.H., and Su, Y.Y.: Organosoluble and colorless fluorinated poly(ether imide)s derived from a highly contorted biphenyl-2,2′-diol bis(ether anhydride) and aromatic bis(ether amine)s with trifluoromethyl substituents. J. Polym. Res. 24, 87 (2017).CrossRefGoogle Scholar
Yang, C.P., Su, Y.Y., and Chen, Y.Y.: Colorless poly(ether-imide)s deriving from 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride(BPADA) and aromatic bis(ether amine)s bearing pendent trifluoromethyl groups. Eur. Polym. J. 42, 721 (2006).CrossRefGoogle Scholar
Zhou, Y., Chen, G.F., Wang, W., Song, L.P., and Fang, X.Z.: Comparative study of transparent polyimides derived from bis(ether anhydride)s and bis(ester anhydride)s using 2,2′-bis(trifluoromethyl)biphenyl-4,4′-diamine. High Perform. Polym. 29, 218 (2017).CrossRefGoogle Scholar
Yang, C.P., Su, Y.Y., Wen, S.J., and Hsiao, S.H.: Highly optically transparent/low color polyimide films prepared from hydroquinone- or resorcinol-based bis(ether anhydride) and trifluoromethyl-containing bis(ether amine)s. Polymer 47, 7021 (2006).CrossRefGoogle Scholar
Choi, I.H. and Chang, J.H.: Colorless polyimide nanocomposite films containing hexafluoroisopropylidene group. Polym. Adv. Technol. 22, 682 (2011).CrossRefGoogle Scholar
Liu, Y., Xing, Y., Zhang, Y.H., Guan, S.W., Zhang, H.B., Wang, Y., Wang, Y.P., and Jiang, Z.H.: Novel soluble fluorinated poly(ether imide)s with different pendant groups: Synthesis, thermal, dielectric, and optical properties. J. Polym. Sci., Part A: Polym. Chem. 48, 3281 (2010).CrossRefGoogle Scholar
Xiao, T.C., Fang, X., and Fan, D.S.: High thermal conductivity and low absorptivity/emissivity properties of transparent fluorinated polyimide films. Polym. Bull. 74, 4561 (2017).CrossRefGoogle Scholar
Ge, Z.Y., Fan, L., and Yang, S.Y.: Synthesis and characterization of novel fluorinated polyimides derived from 1,1′-bis(4-aminophenyl)-1-(3-trifluoromethylphenyl)-2,2,2-trifluoroethane and aromatic dianhydrides. Eur. Polym. J. 44, 1252 (2008).CrossRefGoogle Scholar
Behniafar, H. and Sefid-girandehi, N.: Optical and thermal behavior of novel fluorinated polyimides capable of preparing colorless, transparent and flexible films. J. Fluorine Chem. 132, 878 (2011).CrossRefGoogle Scholar
Li, B.M., Wu, Z.Y., and Lin, L.: Structure, thermal stability, electrochemical behaviors, and mechanical properties of organosoluble polyimide with pyrimidine ring in the main chain. J. Appl. Polym. Sci. 133, 43680 (2016).CrossRefGoogle Scholar
Seyed, M.A., Soheila, E., Mehdi, T., and Zahed, S.: Fabrication and characterization of novel high-performance fluorinated polyimides with xanthene pendent architecture: Study of thermal, photophysical, antibacterial and heavy metal ion adsorption behavior. J. Fluorine Chem. 192, 48 (2016).Google Scholar
Wang, C.Y., Cao, S.J., Chen, W.T., Xu, C., Zhao, X.Y., Li, J., and Ren, Q.: Synthesis and properties of fluorinated polyimides with multi-bulky pendant groups. RSC Adv. 7, 26420 (2017).CrossRefGoogle Scholar
Meador, M.A.B., McMillon, E., Sandberg, A., Barrios, E., Wilmoth, N.G., Mueller, C.H., and Miranda, F.A.: Dielectric and other properties of polyimide aerogels containing fluorinated blocks. ACS Appl. Mater. Interfaces 6, 6062 (2014).CrossRefGoogle ScholarPubMed
Wu, T.T., Dong, J., Gan, F., Fang, Y.T., Zhao, X., and Zhang, Q.H.: Low dielectric constant and moisture-resistant polyimide aerogels containing trifluoromethyl pendent groups. Appl. Surf. Sci. 440, 595 (2018).CrossRefGoogle Scholar
Wozniak, A.I., Yegorov, A.S., Ivanov, V.S., Igumnov, S.M., and Tcarkova, K.V.: Recent progress in synthesis of fluorine containing monomers for polyimides. J. Fluorine Chem. 180, 45 (2015).CrossRefGoogle Scholar