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Original Articles

Organosoluble, low dielectric constant and highly transparent fluorinated pyridine-containing poly(ether imide)s derived from new diamine: 4-(4-trifluoromethyl)phenyl-2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]pyridine

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Pages 234-244 | Received 16 Jun 2018, Accepted 08 Nov 2018, Published online: 25 Jan 2019

References

  • Sroog, C. E. Polyimides. Prog. Polym. Sci. 1991, 16, 561–694. DOI:10.1016/0079-6700(91)90010-I.
  • Ghosh, M. K.; Mittal, K. L. Polyimides: Fundamentals and Applications. Marcel Dekker: New York, 1996.
  • Mittal, K. L. Polyimides and Other High-temperature Polymers. VSP/Brill: Leiden, 2009.
  • Liaw, D. J.; Wang, K. L.; Huang, Y. C.; Lee, K. R.; Lai, J. Y.; Ha, C. S. Advanced Polyimide Materials: Syntheses, physical Properties and Applications. Prog. Polym. Sci. 2012, 37, 907–974. DOI:10.1016/j.progpolymsci.2012.02.005.
  • Tsai, C.-L.; Yen, H.-J.; Liou, G.-S. Highly Transparent Ployimide Hybrids for Optoelectronic Applications. React. Funct. Polym. 2016, 108,2–30.
  • Chao, M.; Kou, K. C.; Wu, G. L.; Zhang, D. N. Synthesis and Characterization of Novel Sulfone-containing Polyimides Molding Powder Derived from 2, 2-Bis[4-(4-aminophenoxy) phenyl] Sulfone and Aromatic Dianhydrides. J. Macromol. Sci. A 2012, 49, 578–585. DOI:10.1080/10601325.2012.687967.
  • Lin, C. H.; Chang, S. L.; Cheng, P. W. Dietheramine from an Alkaline-stable Phosphinated Bisphenol for Soluble Polyetherimides. Polymer 2011, 52, 1249–1255. DOI:10.1016/j.polymer.2011.01.035.
  • Liu, J. T.; Chen, G. F.; Fang, X. Z. Preparation, characterization, and Properties of Poly(thioether Imide)s from Isomeric Bis(chlorophthalimide)s and Bisthiophenols. High Perform. Polym. 2016, 28, 64–74. DOI:10.1177/0954008315570400.
  • Ghaemy, M.; Sharifi, S.; Nasab, S. M. A.; Taghavi, M. Synthesis and Characterization of Organosoluble Poly(imide-ether)s with Bulky 2,3-Diaryl Imidazole Moiety: Study Physical, Thermal and Optical Properties. J. Macromol. Sci. A 2013, 50, 487–497. DOI:10.1080/10601325.2013.780948.
  • Hsiao, S. H.; Kung, Y. R. Synthesis and Properties of New Aromatic Polyimides Containing Redox-active Anthraquinone Moieties. Polym. Int. 2013, 62, 573–580. DOI:10.1002/pi.4312.
  • Yi, L.; Li, C. Y.; Huang, W.; Yan, D. Y. Soluble Polyimides from 4,4′-diaminodiphenyl ether with one or two tert-butyl pedant groups. Polymer 2015, 80, 67–75. DOI:10.1016/j.polymer.2015.10.045.
  • Wen, P. S.; He, R.; Li, X.-D.; Lee, M.-H. Syntheses and Characterizations of High Refractive Index and Low Birefringence Polyimides Containing Spirobifluorene in the Side Chain. Polymer 2017, 117, 76–83.
  • Cai, W. A.; Cai, J. W.; Niu, H. J.; Xiao, T. D.; Bai, X. D.; Wang, C.; Zhang, Y. H.; Wang, W. Synthesis and Electrochromic Properties of Polyimides with Pendent Benzimidazole and Triphenylamine Units. Chin. J. Polym. Sci. 2016, 34, 1091–1102. DOI:10.1007/s10118-016-1833-1.
  • Tan, J. H.; Wang, Q.; Liu, Y. W.; Zeng, Y.; Ding, Q.; Wu, R. M.; Liu, Y. J.; Xiang, X. W. Synthesis, gas Barrier and Thermal Properties of Polyimide Containing Rigid Planar Fluorene Moieties. J. Macromol. Sci. A 2018, 55, 75–84. DOI:10.1080/10601325.2017.1387492.
  • Sheng, S.-R.; Zhang, W.; Lu, C.; Wan, J.; Liu, X.-L.; Song, C.-S. Synthesis and Characterization of New Cardo Poly(ether Imide)s Derived from 9,9-bis [4-(4-aminophenoxy)phenyl]Xanthene. J. Appl. Polym. Sci. 2012, 126, 297–303.
  • Yang, F. C.; Li, Y. F.; Ma, T.; Bu, Q. Q.; Zhang, S. Synthesis and Characterization of Fluorinated Polyimides Derived from Novel Unsymmetrical Diamines. J. J. Fluorine Chem. 2010, 131, 767–775. DOI:10.1016/j.jfluchem.2010.03.014.
  • Wu, Z. L.; Han, B. C.; Zhang, C. H.; Zhu, D. Y.; Gao, L. X.; Ding, M. X.; Yang, Z. H. Novel Soluble and Optically Active Polyimides Containing Axially Asymmetric 9,9′-spirobifluorene units: Synthesis, thermal, optical and chiral properties. Polymer 2012, 53, 5706–5716. DOI:10.1016/j.polymer.2012.10.024.
  • Reddy, D. S.; Shu, C. F.; Wu, F. I. Synthesis and Characterization of Soluble Polyimides Derived from 2,2′-bis(3,4-dicarboxyphenoxy)-9,9′-spirobifluorene dianhydride. J. Polym. Sci. Part A: Polym. Chem. 2002, 40,262–268.
  • Liu, Y. W.; Zhang, Y.; Lan, Q.; Qin, Z. X.; Liu, S. W.; Zhao, C. Y.; Chi, Z. G.; Xu, J. R. Synthesis and Properties of High-performance Functional Polyimides Containing Rigid Nonplanar Conjugated Tetraphenylethylene Moieties. J. Polym. Sci. A Polym. Chem. 2013, 51, 1302–1314. DOI:10.1002/pola.26498.
  • Liaw, D. J.; Wang, K. L.; Chang, F. C.; Lee, K. R.; Lai, J. Y. Novel Poly(pyridine Imide) with Pendent Naphthalene Groups: Synthesis and Thermal, optical, electrochemical, electrochromic, and Protonation Characterization. J. Polym. Sci. A Polym. Chem. 2007, 45, 2367–2374. DOI:10.1002/pola.21997.
  • Fekri, S.; Mansoori, Y. Novel Organosoluble and Thermally Stable Polyetherimides Based on a New Dianhydride Monomer 2,6-bis-(Isobenzofuran-1,3-dione-5-yl)pyridine (BIDP). J. Macromol. Sci. A 2018, 55, 116–123. DOI:10.1080/10601325.2017.1387497.
  • Vaganova, T. A.; Shundrina, I. K.; Kusov, S. Z.; Rodionov, V. I.; Malykhin, E. V. Synthesis and Characterization of Novel Fluorinated Pyridine-based Polyimides. J. Fluorine Chem. 2013, 149, 57–64. DOI:10.1016/j.jfluchem.2013.01.037.
  • Guan, Y.; Wang, C. B.; Wang, D. M.; Dang, G. D.; Chen, C. H.; Zhou, H. W.; Zhao, X. G. High Transparent Polyimides Containing Pyridine and Biphenyl Units: Synthesis, thermal, mechanical, crystal and Optical Properties. Polymer 2015, 62, 1–10. DOI:10.1016/j.polymer.2015.02.009.
  • Wu, G. L.; Liu, J. G.; Li, Z. B.; Ge, Z. Y.; Fan, L.; Yang, S. Y. Synthesis and Characterization of Organo-soluble Fluorinated Polyimides from 4,4′-Bis(3-amino-5-trifluorotrimethylphenoxy)-biphenyl and Various Aromatic Dianhydrides. Chinese J. Polym. Sci. 2005, 23, 55–61. DOI:10.1142/S0256767905000114.
  • Tao, L. M.; Yang, H. X.; Liu, J. G.; Fan, L.; Yang, S. Y. Synthesis and Characterization of Highly Optical Transparent and Low Dielectric Constant Fluorinated Polyimides. Polymer 2009, 50, 6009–6018. DOI:10.1016/j.polymer.2009.10.022.
  • Sheng, S. R.; Li, D. P.; Liu, X. L.; Lai, T. Q.; Song, C. S. Organosoluble, low-dielectric-constant Fluorinated Polyimides Based on 9,9-bis[4-(4-amino-2-trifluoromethyl- phenoxy)phenyl] Xanthene. Polym. Int. 2011, 60, 1185–1193.
  • Chen, Y.-C.; Hsiao, S.-H.; Wu, C.-H. Thermally Stable and Organosoluble Poly(amide-imide)s Based on the Imide Ring-preformed Dicarboxylic Acids Derived from 3,4′-oxydianiline with trimellitic anhydride and 6FDA. J. Macromol. Sci. A 2017, 54, 582–588. DOI:10.1080/10601325.2017.1309252.
  • Kim, S. D.; Lee, S.; Heo, J.; Kim, S. Y.; Chung, I. S. Soluble Polyimides with Trifluoromethyl Pendent Groups. Polymer 2013, 54, 5648–5654. DOI:10.1016/j.polymer.2013.08.057.
  • Wozniak, A. I.; Yegorov, A. S.; Ivanov, V. S.; Igumnov, S. M.; Tcarkova, K. V. Recent Progress in Synthesis of Fluorine Containing Monomers for Polyimides. J. Fluorine Chem. 2015, 180, 45–54. DOI:10.1016/j.jfluchem.2015.08.021.
  • Weiss, M. Acetic Acid—Ammonium Acetate Reactions. An Improved Chichibabin Pyridine Synthesis 1. J. Am. Chem. Soc. 1952, 74, 200–202. DOI:10.1021/ja01121a051.
  • Banerjee, S.; Madhra, M. K.; Kute, V. Polyimides 6: Synthesis, characterization, and Comparison of Properties of Novel Fluorinated Poly(ether Imides). J. Appl. Polym. Sci. 2004, 93, 821–832. DOI:10.1002/app.20532.

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