Synthesis and characterization of novel fluorinated polyimides derived from 1,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides

European Polymer Journal

Volumn 46, Issue 9, 2010, Pages 1878-1890

  Hsiao, Sheng Huei ^a   Guo, Wenjeng ^a   Chung, Cheng Lin ^b   Chen, Wen Tung ^c  

^a NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

^b TATUNG UNIVERSITY   (Taiwan)

^c TAIWAN TEXTILE RESEARCH INSTITUTE   (Taiwan)

Author keywords

1,3 Catenated naphthalene; Fluorinated polyimides; Low dielectric constants; Optical transparency; Solubility

Indexed keywords

1,3-CATENATED NAPHTHALENE; AIR ATMOSPHERE; AROMATIC DIANHYDRIDES; CHEMICAL IMIDIZATION; CUTOFF WAVELENGTHS; DIAMINE MONOMERS; DIANHYDRIDES; DIHYDROXYNAPHTHALENES; ETHER LINKAGES; FLUORINATED POLYIMIDES; GLASS TRANSITION TEMPERATURE; LOW DIELECTRIC CONSTANTS; MOISTURE ABSORPTION; NEW SERIES; OPTICAL TRANSPARENCY; SOFTENING TEMPERATURE; SOLUTION CASTING; SYNTHESIS AND CHARACTERIZATIONS; THERMO-MECHANICAL ANALYSIS; TRIFLUOROMETHYL; TWO-STAGE PROCESS;

AROMATIC COMPOUNDS; ETHERS; GLASS TRANSITION; ORGANIC SOLVENTS; PERMITTIVITY; POLYIMIDES; SOLUBILITY; TRANSPARENCY;

NAPHTHALENE;

EID: 77956181763     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2010.06.010     Document Type: Article

References (52)

1. D. Wilson, H.D. Stenzenberger, P.M. Hergenrother, Polyimides 1990 Blackie Glasgow and London
2. C.E. Sroog Polyimides Prog Polym Sci 16 1991 561 694
3. M.M. Ghosh, K.L. Mittal, Polyimides: fundamentals and applications 1996 Marcel Dekker New York
4. J. De Abajo, and J.G. de la Campa Processable aromatic polyimides Adv Polym Sci 140 1999 23 59
5. T. Takekoshi, J.E. Kochanowski, J.S. Manello, and M.J. Webber Polyetherimides. II. High-temperature solution polymerization J Polym Sci: Polym Symp 74 1986 93 108
6. S. Tamai, A. Yamaguchi, and M. Ohta Melt processible polyimides and their chemical structures Polymer 37 1996 3683 3692
7. S.H. Hsiao, and P.C. Huang Synthesis and characterization of polyimides based on isopropylidene-containing bis(ether anhydride)s J Polym Res 4 1997 183 190
8. S.H. Hsiao, and C.H. Yu Aromatic poly(ether imide)s bearing isopropylidene or hexafluoroisopropylidene links in the main chain Polym J 29 1997 944 948
9. S.H. Hsiao, and W.T. Chen Syntheses and properties of aromatic polyimides based on 1,1-bis[4-(4-aminophenoxy)phenyl]-1-phenyl-2,2,2-trifluoroethane and 1,1-bis[4-(4-aminophenoxy)phenyl]-1-phenylethane J Polym Res 10 2003 95 103
10. Y. Shao, Y.F. Li, X. Zhao, T. Ma, C.L. Gong, and F.C. Yang Synthesis and characterization of soluble polyimides derived from a novel unsymmetrical diamine monomer: 1,4-(2′,4″-diaminodiphenoxy)benzene Eur Polym J 43 2007 4389 4397
11. Y. Imai Synthesis of novel organic-soluble high-temperature aromatic polymers High Perform Polym 7 1995 337 345
12. Y. Imai Recent advances in synthesis of high-temperature aromatic polymers React Funct Polym 30 1996 3 15
13. G.C. Eastmond, and J. Paprotny Pendant adamantyl poly(ether imide)s: synthesis and a preliminary study of properties Eur Polym J 35 1999 2097 2106
14. J. Xu, C. He, and T.S. Chung Synthesis and characterization of soluble polyimides derived from [1,1′;4′,1″]terphenyl-2′, 5′-diol and biphenyl-2,5-diol J Polym Sci Part A: Polym Chem 39 2001 2998 3007
15. D.S. Reddy, C.H. Chou, C.F. Shu, and G.H. Lee Synthesis and characterization of soluble poly(ether imide)s based on 2,2′-bis(4- aminophenoxy)-9,9′-spirobifluorene Polymer 44 2003 557 563
16. B.Y. Myung, J.S. Kim, J.J. Kim, and T.H. Yoon Synthesis and characterization of novel polyimides with 2,2-bis[4(4-aminophenoxy)phenyl] phthalein-3′,5′-bis(trifluoromethyl)anilide J Polym Sci Part A: Polym Chem 41 2003 3361 3374
17. S.H. Hsiao, and T.L. Huang Synthesis and characterization of new polyimides based on 3,6-bis(4-aminophenoxy)benzonorbornane J Polym Res 11 2004 9 21
18. S.H. Hsiao, C.L. Chung, and M.L. Lee Synthesis and characterization of soluble polyimides derived from 2′,5′-bis(3,4-dicarboxyphenoxy)-p- terphenyl dianhydride J Polym Sci Part A: Polym Chem 42 2004 1008 1017
19. S.M. Kwak, J.H. Yeon, and T.H. Yoon Synthesis and characterization of polyimides from bis(3-aminophenyl)-4-(1-adamantyl)phenoxyphenyl phosphine oxide J Polym Sci Part A: Polym Chem 44 2006 2567 2578
20. Q.Y. Zhang, H.S. Li, W.M. Li, and S.B. Zhang Synthesis and properties of novel organosoluble polyimides derived from 1,4-bis[4-(3,4-dicarboxylphenoxy)] triptycene dianhydride and various aromatic diamines Polymer 48 2007 6246 6253
21. C.H. Lin, and C.H. Lin Synthesis and properties of polyimides derived from 1,4-bis(4-aminophenoxy)-2-(6-oxido-6H-dibenz[c,e] [1,2]oxaphosphorin-6-yl) phenylene J Polym Sci Part A: Polym Chem 45 2007 2897 2912
22. g polyimides J Polym Sci Part A: Polym Chem 47 2009 2486 2499
23. P.M. Hergenrother, K.A. Watson, J.G. Smith Jr., J.W. Connell, and R. Yokota Polyimides from 2,3,3′,4′-biphenyltetracarboxylic dianhydride and aromatic diamines Polymer 43 2002 5077 5093
24. X.Z. Fang, Z. Wang, Z.H. Yang, L.X. Gao, Q.G. Li, and M.X. Ding Novel polyimides derived from 2,3,3′,4′-benzophenonetetracarboxylic dianhydride Polymer 44 2003 2641 2646
25. Q.X. Li, X.Z. Fang, Z. Wang, L.X. Gao, and M.X. Ding Polyimides from isomeric oxydiphthalic anhydrides J Polym Sci Part A: Polym Chem 41 2003 3249 3260
26. S.H. Hsiao, and K.H. Lin Polyimides derived from novel asymmetric ether diamine J Polym Sci Part A: Polym Chem 43 2005 331 341
27. Z.X. Li, L.Q. Lin, W.M. Zhang, T. Wu, and J.L. Pu Synthesis and characterization of polyimides derived from (3-amino-2,4,6-trimethylphenyl)- (3′-aminophenyl)methanone and aromatic dianhydrides J Polym Sci Part A: Polym Chem 44 2006 1291 1298
28. W.M. Li, G. Chen, S.B. Zhang, H. Wang, and D.H. Yan Synthesis and properties of novel regioirregular polyimides from easily synthesized asymmetrical dichlorophthalimide monomers J Polym Sci Part A: Polym Chem 45 2007 3550 3561
29. M.X. Ding Isomeric polyimides Prog Polym Sci 32 2007 623 668
30. Y.T. Chern, and J.Y. Tsai Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1,4-bis(4-aminophenoxy)-2,6-di-tert-butylbenzene Macromolecules 41 2008 9556 9564
31. Y.T. Chern, and M.H. Ju Conformation of polyimide backbone structures for determination of the pretilt angle of liquid crystals Macromolecules 42 2009 169 179
32. g and high organosolubility of novel polyimides containing twisted structures derived from 4-(4-amino-2-chlorophenyl)-1-(4-aminophenoxy)-2,6-di-tert-butylbenzene Eur Polym J 45 2009 1127 1138
33. Cheng KL, Chen WT. Preparation of 1,3-bis(4-aminophenoxy)naphthalene and corresponding polyamide and polyimides. TW Pat 400,339, 2000.
34. Cheng KL, Chen WT. Formulation for the production of 1,3-bis(4- aminophenoxy)naphthalene and its polymer. US Pat 6197,920, 2001.
35. C.P. Yang, S.H. Hsiao, and M.F. Hsu Organosoluble and light-colored fluorinated polyimides from 4,4′-bis(4-amino-2-trifluoromethylphenoxy) biphenyl and aromatic dianhydrides J Polym Sci Part A: Polym Chem 40 2002 524 534
36. M.K. Madhra, A.K. Salunke, S. Banerjee, and S. Prabha Synthesis and properties of fluorinated polyimides, 2. Derived from novel 2,6-bis(3′- trifluoromethyl-p-aminobiphenyl ether)pyridine and 2,5-bis(3′- trifluoromethyl-p-aminobiphenyl ether)thiophene Macromol Chem Phys 203 2002 1238 1248
37. C.P. Yang, S.H. Hsiao, and K.L. Wu Organosoluble and light-colored fluorinated polyimides derived from 2,3-bis(4-amino-2-trifluoromethylphenoxy) naphthalene and aromatic dianhydrides Polymer 44 2003 7067 7078
38. S.H. Hsiao, C.P. Yang, and C.L. Chung Synthesis and characterization of novel fluorinated polyimides based on 2,7-bis(4-amino-2-trifluoromethylphenoxy) naphthalene J Polym Sci Part A: Polym Chem 41 2003 2001 2018
39. K. Xie, J.G. Liu, H.W. Zhou, S.Y. Zhang, M.H. He, and S.Y. Yang Soluble fluoro-polyimides derived from 1,3-bis(4-amino-2-trifluoromethylphenoxy)benzene and dianhydrides Polymer 42 2001 7267 7274
40. B.Y. Myung, J.J. Kim, and T.H. Yoon Synthesis and characterization of novel 3,6-di[3′,5′-bis(trifluoromethyl)phenyl]pyromellitic dianhydride for polyimide synthesis J Polym Sci Part A: Polym Chem 40 2002 4217 4227
41. S.Y. Yang, Z.Y. Ge, D.X. Yin, J.G. Liu, Y.F. Li, and L. Fan Synthesis and characterization of novel fluorinated polyimides derived from 4,4′-[2,2,2-trifluoro-1-(3-trifluoromethylphenyl)ethylidene]diphthalic anhydride and aromatic diamines J Polym Sci Part A: Polym Chem 42 2004 4143 4152
42. C.P. Yang, S.H. Hsiao, and C.L. Chung Organosoluble, low-dielectric- constant fluorinated polyimides based on 2,6-bis(4-amino-2- trifluoromethylphenoxy)naphthalene Polym Int 54 2005 716 724
43. D.X. Yin, Y.F. Li, H.X. Yang, S.Y. Yang, L. Fan, and J.G. Liu Synthesis and characterization of novel polyimides derived from 1,1-bis[4-(4′- aminophenoxy)phenyl]-1-[3″,5″-bis(trifluoromethyl)phenyl]-2,2,2- trifluoroethane Polymer 46 2005 3119 3127
44. B.J. Liu, W. Hu, T. Matsumoto, Z.H. Jiang, and S. Ando Synthesis and characterization of organosoluble ditrifluoromethylated aromatic polyimides J Polym Sci Part A: Polym Chem 43 2005 3018 3029
45. Y. Shao, Y.F. Li, X. Zhao, X.L. Wang, T. Ma, and F.C. Yang Synthesis and properties of fluorinated polyimides from a new unsymmetrical diamine: 1,4-(2′-trifluoromethyl-4′,4′-diaminodiphenoxy)benzene J Polym Sci Part A: Polym Chem 44 2006 6836 6846
46. C.L. Chung, C.P. Yang, and S.H. Hsiao 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 2006 3092 3102
47. D.J. Liaw, C.C. Huang, and W.H. Chen Optical transparency and light color of novel highly organosoluble alicyclic polyimides with 4-tert-butylcyclohexyl group Macromol Chem Phys 207 2006 434 443
48. C.L. Chung, and S.H. Hsiao Novel organosoluble fluorinated polyimides derived from 1,6-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides Polymer 49 2008 2476 2485
49. C.L. Chung, W.F. Lee, C.H. Lin, and S.H. Hsiao Highly soluble fluorinated polyimides based on an asymmetric bis(ether amine): 1,7-bis(4-amino-2- trifluoromethylphenoxy)naphthalene J Polym Sci Part A: Polym Chem 47 2009 1756 1770
50. F.C. Yang, J.J. Zhao, Y.F. Li, S.J. Zhang, Y. Shao, and H. Shao Synthesis and properties of novel organosoluble polyimides derived from bis[3-(4-amino-2-trifluoromethylphenoxy)phenyl] ether Eur Polym J 45 2009 2053 2059
51. S.H. Hsiao, C.P. Yang, and S.C. Huang Preparation and properties of new polyimides and polyamides based on 1,4-bis(4-amino-2-trifluoromethylphenoxy) naphthalene J Polym Sci Part A: Polym Chem 42 2004 2377 2394
52. S.H. Hsiao, C.P. Yang, and S.C. Huang Polyimides from 1,5-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic tetracarboxylic dianhydrides Eur Polym J 40 2004 1063 1074