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Synthesis and Characterization of Soluble Polyimides Derived from the Polycondensation of 2,6-bis(4-amino-2-trifluoromethylphenoxy-4'-benzoyl)pyridine with Some Aromatic Dianhydrides

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Institute of Biochemical Engineering & Environmqental Technology, Lanzhou University, Lanzhou 730000, China

Yan-Feng Li

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Institute of Biochemical Engineering & Environmqental Technology, Lanzhou University, Lanzhou 730000, China, liyf{at}lzu.edu.cn

Xiao-Long Wang

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Institute of Biochemical Engineering & Environmqental Technology, Lanzhou University, Lanzhou 730000, China

Xyn Zhao

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Institute of Biochemical Engineering & Environmqental Technology, Lanzhou University, Lanzhou 730000, China

Yu Shao

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Institute of Biochemical Engineering & Environmqental Technology, Lanzhou University, Lanzhou 730000, China

Tao Ma

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Institute of Biochemical Engineering & Environmqental Technology, Lanzhou University, Lanzhou 730000, China

A new aromatic diamine monomer containing both pyridine and fluorine, 2,6-bis(4-amino-2-trifluoromethylphenoxy-4 ^'-benzoyl)pyridine (BAFP), was successively synthesized by the nucleophilic substitution reaction of 2,6-bis(4,4^'-dihydroxybenzoyl)pyridine with 2-chloro-5-nitro-trifluoromethylbenzene in the presence of k₂CO ₃ in N,N-dimethylacetamide, and followed by reduction with SnCl₂ and HCl in ethanol. The polycondensation of BAFP with four aromatic dianhydrides afforded a series of novel aromatic polyimides containing both pyridine and fluorine. The reaction was conducted by the one-step thermal imidization method. The resulting polyimides were characterized for inherent viscosity, solubility, and thermo-oxidative stability. The polyimides exhibited excellent solubility in various solvents such as N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO) and chloroform. The glass-transition temperatures (T_g) were in the range of 206—227^°C. The polyimides displayed good thermal stability, e.g. the temperatures at the 5% weight loss range were at 487—543^°C in nitrogen and 463—521^°C in air, respectively. Wide-angle X-ray diffraction measurements revealed that the polyimides were predominantly amorphous.

Key Words: Pyridine-containing diamine • polyimides • synthesis • polycondensation

References

• Wilson, D., Stenzenberger, H.D. and Hergenrother, P.M. (1990). Polyimides, Chapman and Hall, New York.
• Ghost, M.K. and Mittal, K.L. (1996). Polyimides Fundamentals and Applications, Marcel Decke, New York.
• Hergenrother, P.M. (2000). Development of Composites, Adhesives and Sealants for High-speed Commercial Airplanes, SAMPE J., 36: 30—41.
• Hu, A.J., He, T. and Yang, S.Y. (1999). Synthesis and Characterization of High-Temperature Fluorine-Containing PMR Polyimides, Macromolecules, 32: 8046-8051.[CrossRef][Web of Science]
• Qiu, Z.M. and Zhang, S.B. (2005). Synthesis and Properties of Organosoluble Polyimides based on 2,2'diphenoxy-4,4',5,5'-biphenyltetracarboxylic dianhydride, Polymer, 46: 1693—1700.[CrossRef][Web of Science]
• Yin, D.X., Li, Y.F., Yang, H'.X. and Yang, S.Y. (2005). 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: 3119—3127.[CrossRef][Web of Science]
• Yang, S.Y., Ge, Z.Y., Yin, D.X., Liu, J.G., Li, Y.F. and Fan, L. (2004). 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: 4143—4152.[CrossRef]
• Hsiao, S.H., Yang, C.P. and Huang, S.C. (2004). Polyimides from 1,5-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and Aromatic Tetracarboxylic Dianhydrides, Eur. Polym.r J., 40: 1063—1074.[CrossRef]
• Butt, M.S., Akhtar, Z., Zaman, M.Z. and Munir, A. (2005). Synthesis and Characterization of some Novel Aromatic Polyimides, Eur. Polym. J., 41: 1638—1646.[CrossRef]
• Shahram, M.A., Yaghoub, S. and Hatami, M. (2004). Novel Thermally Stable Polyimides based on Flexible Diamine: Synthesis, Characterization, and Properties, Eur. Polym. J., 40: 2009—2015.[CrossRef]
• Wang, X.L., Li, Y.F., Zhang, S.J., Yin, D.X., Liu, J.G. and Yang, S.Y. (2005). Polymers containing Pyridine Moieties in Main Chain, Hua Xue Tong Bao (Chem. Bull.) 68: 329—337 (in Chinese).
• Butuc, E. and Gherasim, G.M. (1984). Ordered Heterocyclic Copolymers Polyamide-imides with S-triazine Rings, J. Polym. Sci. Polym. Chem. Ed., 22: 503—507.[CrossRef]
• Kurita, K. and Williams, R.L. (1974). Heat-resisant Polymers containing Bipyridyl units. III. Polyimides having o-, m-, p-phenylenedioxy Linkage, J. Polym. Sci. Polym. Chem. Ed., 12: 1809—1902.[CrossRef]
• Shahram, M.A. and Ahmad, A. (2005). Novel Thermally Stable Poly(ether imide ester)s from 2,6-bis (4-aminophenoxy) pyridine, J. Appl. Polym. Sci., 96: 570—576.[CrossRef]
• Liu, J.G., Wang, L.F., Yang, H.X., Li, Y.F. and Yang, S.Y. (2004). Synthesis and Characterization of New Polybenzimidazopyrrolones derived from Pyridine-bridged Aromatic Tetraamines and Dianhydrides. J. Polym. Sci., Part A: Polym. Chem. 42: 1845—1856.[CrossRef]
• Shahram, M., Mehdipour-Ataei and Hani, H. (2004). Preparation of Novel Pyridine-based, Thermally Stable Poly(ether imide), J. Appl. Polym. Sci., 91: 22—26.[CrossRef]
• Tamami, B. and Yeganeh, H. (2001). Preparation and Properties of Novel Polyimides derived from 4-aryl-2,6 bis(4-amino phenyl)pyridine, J. Polym. Sci., Part A: Polym. Chem., 39: 3826—3831.[CrossRef]
• Banerjee, S., Madhra, M.K., Salunke, A.K. and Jaiswal, D.K. (2003). Synthesis and Properties of Fluorinated Polyimides. 3. Derived from novel 1,3-bis[3'-trifluoromethyl -4'(4''-amino benzoxy) benzyl] benzene and 4,4-bis[3'-trifluoromethyl-4'(4-amino benzoxy) benzyl] biphenyl, Polymer, 44: 613—622.[CrossRef][Web of Science]
• Hariharan, R., Bhuvana, S., Anitha, M.M. and Sarojadevi, M. (2004). Synthesis and Characterization of Polyimides containing Pyridine Moiety, J. Appl. Polym. Sci., 93:1846—1853.[CrossRef]
• Shahram, M.A., Rezvaneh, M.M. and Majid, N. (2005). Synthesis and Characterization of Heat-resistant, Pyridine-based Polyimides with Preformed Ether and Ester Groups, Eur. Polym. J. 41: 1024—1029.[CrossRef]
• Zhang, S.J., Li, Y.F., Yin, D.X., Wang, X.L., Zhao, X. and Shao, Y. (2005). Study on Synthesis and Characterization of Novel Polyimides derived from 2,6-Bis(3-aminobenzoyl) pyridine, Eur. Polym. J., 41: 1097—1107.[CrossRef]
• Zhang, S.J., Li, Y.F., Wang, X.L., Zhao, X., Shao, Y., Yin, D.X. and Yang, S.Y. (2005). Synthesis and Properties of Novel Polyimides derived from 2,6-bis(4-aminophenoxy-4'-benzoyl)pyridine with some of Dianhydride Monomers, Polymer, 46: 11986—11993.[CrossRef][Web of Science]
• Ratta, V., Ayamben, A., McGrath, J.E. and Wilkes, G.L. (2001). Crystallization and Multiple Melting Behavior of a new Semicrystalline Polyimide-based on 1,3-bis(4-aminophenoxy) benzene (TPER) and 3,3',4,4'-biphenonetetracarboxylic Dianhydride (BTDA), Polymer, 42: 6173—6186.[CrossRef][Web of Science]
• Liu, X.Q., Yamanaka, K., Mitsutoshi, J.K. and Kakimoto, M. (2000). Semicrystalline Polyimides Starting from AB-Type Monomers, Chem. Mater., 12: 3885—3891.[CrossRef][Web of Science]

This version was published on August 1, 2007

High Performance Polymers, Vol. 19, No. 4, 462-476 (2007)
DOI: 10.1177/0954008307078514


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This Article Abstract Free Full Text (Free PDF) Free Alert me when this article is cited Alert me if a correction is posted Services Email this article to a friend Similar articles in this journal Similar articles in Web of Science Alert me to new issues of the journal Add to Saved Citations Download to citation manager Request Permissions Request Reprints Add to My Marked Citations Citing Articles Citing Articles via Google Scholar Citing Articles via Scopus Google Scholar Articles by Zhang, S.-J. Articles by Ma, T. Search for Related Content Social Bookmarking                         What's this?