Preparation and properties of thermally stable polyimides derived from asymmetric trifluoromethylated aromatic diamines and various dianhydrides

Polymer Degradation and Stability

Volumn 96, Issue 10, 2011, Pages 1911-1918

  Bu, Qianqian ^a   Zhang, Shujiang ^a   Li, Hui ^a   Li, Yanfeng ^a   Gong, Chenliang ^a   Yang, Fengchun ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

CF3 containing polyimide; Polymer films; Solubility; Unsymmetrical diamine monomer

Indexed keywords

APROTIC SOLVENTS; AROMATIC DIAMINE; CATALYTIC REDUCTION; CHEMICAL IMIDIZATION; DIAMINE MONOMERS; DIANHYDRIDES; DIELECTRIC CONSTANTS; INHERENT VISCOSITY; LOW DIELECTRIC CONSTANTS; MOISTURE ABSORPTION; NOVEL METHODS; NOVEL POLYIMIDES; NUCLEOPHILIC SUBSTITUTION REACTIONS; PHENONE; PI FILM; PREPARATION AND PROPERTIES; THERMALLY STABLE; TRIFLUOROMETHYL; TRIFLUOROMETHYL GROUP; WEIGHT LOSS;

ABSORPTION; AROMATIC COMPOUNDS; AROMATIZATION; FILM PREPARATION; GLASS TRANSITION; HYDROCHLORIC ACID; MOISTURE; POLYMER FILMS; POTASSIUM; SOLUBILITY; SUBSTITUTION REACTIONS; SURFACE PROPERTIES; THERMODYNAMIC STABILITY; VISCOSITY;

POLYIMIDES;

EID: 80052501519     PISSN: 01413910     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymdegradstab.2011.07.003     Document Type: Article

References (44)

1. D. Wilson, H.D. Stenzenberger, and P.M. Hergenrother Polyimides 1990 Chapman & Hall New York 1 352
2. M.K. Ghosh, and K.L. Mittal Polyimides: fundamentals and applications 1996 Marcel Dekker New York 1 48
3. G. Mousa, A. Raouf, and B. Hossein Synthesis of soluble and thermally stable polyimide from new diamine bearing N-[4-(9H-carbazol-9-yl)phenyl] formamide pendent group Eur Polym J 45 2009 3108 3115
4. C.P. Yang, Y.Y. Su, W.J. Guo, and S.H. Hsiao Synthesis and properties of novel fluorinated polynaphthalimides derived from 1,4,5,8- naphthalenetetracarboxylic dianhydride and trifluoromethyl-substituted aromatic bis(ether amine)s Eur Polym J 45 2009 721 729
5. X.W. Yun, G.M. Ming, H.Z. Guo, Y.L. Sheng, and K.C. Ming Synthesis of a new aromatic dianhydride monomer and related polyimide Chin Chem Lett 20 2009 229 230
6. K. Shingo, K. Hiroshi, I. Takashi, K. Toshinori, O. Tomohiro, and K. Syuji Synthesis of well-defined random and block copolymers of 2-(1-adamantyl)-1,3-butadiene with isoprene via anionic polymerization React Funct Polym 69 2009 409 415
7. D.J. Liaw, C.C. Huang, and W.H. Chen Color lightness and highly organosoluble fluorinated polyamides, polyimides and poly(amide-imide)s based on noncoplanar 2,2′-dimethyl-4,4′-biphenylene units Polymer 47 2006 2337 2348
8. W.T. Leu, and S.H. Hsiao Synthesis and properties of novel aromatic poly(ester-imide)s bearing 1,5-bis(benzoyloxy)naphthalene units Eur Polym J 42 2006 328 335
9. 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 (Pubitemid 43288560)
10. H.S. Li, J.G. Liu, K. Wang, K. Fan, and S.Y. Yang Synthesis and characterization of novel fluorinated polyimides derived from4,4′-[2,2,2- triuoro-1-(3,5-ditriuoromethylphenyl)ethylidene]diphthalic anhydride and aromatic diamines Polymer 47 2006 1443 1450 (Pubitemid 43199754)
11. H. Lai, L. Qin, X.Y. Liu, and Y. Gu Synthesis of novel polyimides with (tert-butyldimethylsiloxy)biphenyloxy groups and the effect of side-chains content on their properties Eur Polym J 44 2008 3724 3731
12. B.K. Chen, Y.J. Tsai, and S.Y. Tsay 2,6-Diamino-4-phenylphenol (DAPP) copolymerized polyimides: synthesis and characterization Polym Int 55 2006 93 100
13. Z.Q. Hu, S.J. Li, and C.H. Zhang Synthesis and characterization of novel chain-extended bismaleimides containing fluorenyl cardo structure J Appl Polym Sci 107 2008 1288 1293
14. H.S. Kim, Y.H. Kim, S.K. Ahn, and S.K. Kwon Synthesis and characterization of highly soluble and oxygen permeable new polyimides bearing a noncoplanar twisted biphenyl unit containing tert-butylphenyl or trimethylsilyl phenyl groups Macromolecules 36 2003 2327 2332
15. J.K. Choi, K.Y. Paek, and T.H. Yoon Adhesive and dielectric properties of novel polyimides with bis(3,3′-aminophenyl)-2,3,5,6-tetrauoro-4- triuoromethyl phenyl phosphine oxide (mDA7FPPO) Eur Polym J 45 2009 1652 1658
16. X.X. Guo, J.H. Fang, K. Tanaka, H. Kita, and K.I. Okamoto Synthesis and properties of novel sulfonated polyimides from 2,2′-bis(4-aminophenoxy) biphenyl-5,5′-disulfonic acid J Polym Sci, Part A: Polym Chem 42 2004 1432 1440 (Pubitemid 38311212)
17. F.C. Yang, Y.F. Li, Q.Q. Bu, S.J. Zhang, T. Ma, and J.J. Zhao Characterizations and thermal stability of soluble polyimide derived from novel unsymmetrical diamine monomers Polym Degrad Stab 95 2010 1950 1958
18. X.H. Yu, X.G. Zhao, C.W. Liu, Z.W. Bai, D.M. Wang, and G.D. Dang Synthesis and properties thermoplastic polyimides with ether ketone moieties J Polym Sci Part A Polym Chem 48 2010 2878 2884
19. G. Zhang, T.Z. Fu, J. Wu, X.F. Li, and H. Na Synthesis and characterization of a new type of sulfonated poly(ether ether ketone ketone)s for proton exchange membranes J Appl Polym Sci 116 2010 1515 1523
20. J.C. Chen, Y.T. Liu, C.M. Leu, H.Y. Liao, W.C. Lee, and T.M. Lee Synthesis and properties of organosoluble polyimides derived from 2,2′-dibromo- and 2,2′,6,6′-tetrabromo-4,4′- oxydianilines J App Polym Sci 117 2010 1144 1155
21. 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-trifluoromethyl phenoxy) phenyl] ether Eur Polym J 45 2009 2053 2059
22. S. Takeshi, M. Hiroyuki, Y. Shoichiro, and Yokotaa Rikio High thermal stable thermoplastic-thermosetting polyimide film by use of asymmetric dianhydride (a-BPDA) Polymer 46 2005 6968 6975
23. G. Mousa, and A. Raouf Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2,4,5-triaryl imidazole pendent group Eur Polym J 45 2009 1681 1688
24. C.L. Gao, X. Wu, G.H. Lv, M.X. Ding, and L.X. Gao Syntheses and properties of soluble biphenyl-based polyimides from asymmetric bis(chlorophthalimide)s Macromolecules 37 2004 2754 2761
25. C.P. Yang, and F.Z. Hsiao Synthesis and properties fluorinated polyimides based 1,4-bis(4-amino-2-trifluoromethylphenoxy)-2,5-di-tert-butylbenzene various aromatic dianhydrides J Polym Sci Part A Polym Chem 42 2004 2272 2284
26. B.Y. Myung, C.J. Ahn, and T.H. Yoon Synthesis and characterization of polyimides from novel 1-(3′,5′-bis(trifluoromethyl)benzene) pyromelliticdianhydride (6FPPMDA) Polymer 45 2004 185 193
27. K.U. Jeong, J.J. Kim, and T.H. Yoon Synthesis and characterization of novel polyimides containing fluorine and phosphine oxide moieties Polymer 42 2001 6091 6130
28. D.X. Yin, Y.F. Li, Y. Shao, X. Zhao, S.Y. Yang, and L. Fan Synthesis and characterization of soluble polyimides based on trifluoromethylated aromatic dianhydride and substitutional diaminetriphenylmethanes J Fluorine Chem 126 2005 819 823 (Pubitemid 40665450)
29. L. Zhuo, J.G. Liu, Z.Q. Gao, Z.H. Yin, L. Fan, and S.Y. Yang Organo-soluble and transparent polyimides containing phenylphosphine oxide and trifluoromethyl moiety: synthesis and characterization Eur Polym J 45 2009 1139 1148
30. S. Banerjee, M.K. Madhra, and V. Kute Polyimides 6: synthesis, characterization, and comparison of properties of novel fluorinated poly(ether imides) J Appl Polym Sci 93 2004 821 832 (Pubitemid 38710216)
31. T. Ma, S.J. Zhang, Y.F. Li, F.C. Yang, C.L. Gong, and J.J. Zhao Synthesis and characterization of novel polyimides derived from 4-phenyl-2, 6-bis [3-(4-aminophenoxy)-phenyl]-pyridine diamine and aromatic dianhydrides Polym Degra Stab 95 2010 1244 1250
32. 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 (Pubitemid 37326615)
33. J.K. Im, and J.C. Jung Synthesis and properties of polyimides derived from N-[4-(4-aminophenyloxy)phenyl]-4-aminophthalimide Polymer 41 2000 8709 8716
34. I.S. Chung, C.E. Park, M. Ree, and S.Y. Kim Soluble polyimides containing benzimidazole rings for interlevel dielectrics Chem Mater 13 2001 2801 2806 (Pubitemid 33121282)
35. 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
36. C.P. Yang, and Y.Y. Su Synthesis and properties of organosoluble polyimides based on 4,4′-bis(4-amino-2-trifluoromethylphenoxy)- benzophenone J Polym Sci: Part A: Polym Chem 42 2004 222 236
37. S.J. Zhang, Y.F. Li, D.X. Yin, X.L. Wang, X. Zhao, and Y. Shao Study on synthesis and characterization of novel polyimides derived from 2,6-bis(3-aminobenzoyl) pyridine Eur Polym J 41 2005 1097 1107 (Pubitemid 40305043)
38. Chen H, Yin J. Synthesis of autophotosensitive hyperbranched polyimides based on 3,3',4,4'-benzophenonetetracarboxylic dianhydride and 1,3,5-tris (4-aminophenoxy) benzene via end capping of the terminal anhydride groups by ortho-alkyl aniline. J Polym Sci Part A: Polym Chem 2003;41:2026-35. (Pubitemid 36789157)
39. S. Babanzadeh, A.R. Mahjoub, and S.M. Ataei Novel soluble thermally stable silane-containing aromatic polyimides with reduced dielectric constant Polym Degrad Stab 95 2010 2492 2498
40. D.M. Chao, J.F. Zhang, X.C. Liu, X.F. Lu, C. Wang, and W.J. Zhang Synthesis of novel poly(amic acid) and polyimide with oligoaniline in the main chain and their thermal, electrochemical, and dielectric properties Polymer 51 2010 4518 4524
41. J.K. Choi, K. Cho, and T.H. Yoon Synthesis and characterization of polyimides from triphenylamine-based diamine monomers with thiophene or trifluoromethyl side group Synth Met 160 2010 1938 1944
42. S.H. Hsiao, W.J. Guo, C.L. Chung, and W.T. Chen Synthesis and characterization of novel fluorinated polyimides derived from 1,3-bis(4-amino-2-triuoromethylphenoxy)naphthalene and aromatic dianhydrides Eur Polym J 46 2010 1878 1890
43. Nilakshi V. Sadavarte, C.V. Avadhani, V.N. Parimal, and P.W. Prakash Regularly alternating poly(amideimide)s containing pendent pentadecyl chains: synthesis and characterization Eur Polym J 46 2010 1307 1315
44. M.K. Madhra, A.K. Salunke, S. Banerjee, and S. Prabha Synthesis and properties of fluorinated polyimides 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