Polyimide (PI) derived from 3,3',4,4'-biphenyltetracarboxylic dianhydride (s-BPDA) with trans-1,4-cyclohexanediamine (CHDA), i.e., s-BPDA/CHDA was investigated from the viewpoint of ordered structure and intermolecular interaction. Thermodynamic parameters of the model compounds for melting behavior suggested significantly restricted conformational changes in the trans-1,4-cyclohexylene unit and the presence of strong BPDI—BPDI interaction in s-BPDA/CHDA. The effect of diamine structure on the fluorescence yield also supported the presence of the BPDI—BPDI interaction or the BPDI dimer in s-BPDA-based semi-cycloaliphatic PIs. The results of the fluorescence depolarization measurements can be rationalized by a proposed mechanism assuming the presence of the BPDI dimer sites, where the fluorescence of s-BPDA/CHDA occurs by excitation of the lower energy trap sites consisting of the BPDI dimer via excitation energy migration or direct excitation of the dimer. The structure-sensitive infrared band around 550 cm-1 gradually shifted toward higher frequency with simultaneous narrowing with increasing cure temperature, suggesting gradual ordered structure formation in s-BPDA/CHDA. Thermal imidization at 400 °C caused splitting of the C—H stretching band around 2940 cm-1, corresponding to the disappearance of distinct glass transition for the s-BPDA/CHDA system.
Mittal, K.L. (ed.) (1984). Polyimides: Synthesis, Characterization and Application, Plenum, New York.
2.
Bessonov, M.I.,Koton, M.M., Kudryavtsev, V.V. and Laius, L.A. (eds) (1987). Polyimide: Thermally Stable Polymers, Plenum, New York.
3.
Feger, C.,Khojasteh, M.M. and McGrath, J.E. (eds) (1989). Polyimides: Materials, Chemistry and Characterization , Elsevier, Amsterdam.
4.
Feger, C.,Khojasteh, M.M. and Htoo, M.S. (eds) (1993). Advances in Polyimide Science and Technology, Technomic, Lancaster.
5.
Bessonov, M.I., Zubkov, VA. (eds) (1993). Polyamic acid and Polyimides: Synthesis, Transformation and Structure, CRC Press, Boca Ranton, FL.
6.
Ghosh, M.K. and Mittal, K.L. (eds) (1996). Polyimides: Fundamentals and Applications, Marcel Dekker, New York.
7.
Feger, C.,Khojasteh, M.M. and Molis, S.E. (eds) (1996). Polyimides: Trends in Materials and Applications , Society of Plastic Engineers, New York.
8.
Sachdev, H.S., Khojasteh, M.M. and Feger, C. (eds) (1999). Advances in Polyimides and Low Dielectric Polymers, Society of Plastic Engineers, New York.
9.
Mittal, K.L. (ed) (2001 ). Polyimides and Other High Temperature Polymers: Synthesis, Characterization and Applications, vol. 1, VSP, Zeist, The Netherland.
10.
Imai, Y. and Yokota, R. (eds) (2002). The Latest Polyimides: Fundamentals and Applications, NTS, Tokyo (in Japanese).
11.
Hasegawa, M. (2001). Semi-aromatic Polyimides with Low Dielectric Constant and Low CTE, High Perform. Polym. , 13: S93-S106.
12.
Hasegawa, M. and Koyanaka, M. (2003). Polyimides Containing Trans-1,4-cyclohexane Unit: Polymerizability of their Precursors and Low-CTE and Low-K and High-Tg Properties, High Perform. Polym., 15: 47-64.
13.
Hasegawa, M., Horiuchi, M. and Wada, Y. (2007). Polyimides containing trans-1,4-cyclohexane unit (II). Low-K and Low-CTE Semi- and Wholly Cycloaliphatic Polyimides, High Perform. Polym. , 19: 175-193.
14.
Ogura, T. and Ueda, M. (2007). Facile Synthesis of Semiaromatic Poly(amic acid)s from trans-1,4-Cyclohexanediamine and Aromatic Tetracarboxylic Dianhydrides, Macromolecules, 40: 3527-3529.
15.
Ford, W.E. and Kamat, P.V. (1987). Photochemistry of 3,4,9,10-perylenetetracarboxylic dianhydride dyes. 3. Singlet and triplet excited-state properties of the bis(2,5-di-tert-butylphenyl)imide derivative , J. Phys. Chem., 91: 6373-6380.
16.
Hasegawa, M. and Horii, S. (2007). Low-CTE Polyimides derived from 2,3,6,7-Naphthalenetetracarboxylic Dianhydride, Polym. J., 39: 610-621.
17.
Hasegawa, M., Sensui, N., Shindo , Y. and Yokota, R. (1999). Improvement of Thermoplasticity for s-BPDA/PDA by Copolymerization and Blend with Novel Asymmetric BPDA-based Polyimides, J. Polym. Sci. Part B, 37: 2499-2511.
18.
Hasegawa, M., Matano, T., Shindo , Y. and Sugimura, T. (1996). Spontaneous Molecular Orientation of Polyimides induced by Thermal Imidization (2). In-plane Orientation, Macromolecules, 29: 7897-7909.
19.
Shi, Z., Hasegawa, M., Shindo , Y., Yokota, R., He , F., Yamaguchi, H. and Ozawa, H. (2000). Thermo-processable Polyimides with High Thermo-oxidative Stability as Derived from Oxydiphthalic Anhydride (ODPA) and Bisphenol A type Dianhydride, High Perform. Polym. , 12: 377-393.
20.
Hasegawa, M., Sensui, N., Shindo , Y. and Yokota, R. (1999). Structure and Properties of Novel Asymmetric Biphenyl Type Polyimides. Homo- and Copolymers and Blends, Macromolecules, 32: 387-396.
21.
Baklagina, Yu.G. and Milevskaya, I.S. (1993). Supermolecular Structure of Polyamic Acids and Polyimides, In: Bessonov, M.I. and Zubkov V.A. (eds), Polyamic Acids and Polyimides: Synthesis, Transformation, and Structure, CRC Press, Boca Ranton , 197-280.
22.
Hasegawa, M. and Horie, K. (2001). Photophysics, Photochemistry, and Optical Properties of Polyimides, Progress Polym. Sci. , 26: 259-335.
23.
Hasegawa, M., Kobayashi, J. and Vladimirov, L. (2004). Solution-processable Low-CTE Polybenzoxazoles, J. Photopolym. Sci. Technol., 17: 253-258.
24.
Miyazaki, T. and Hasegawa, M. (2007). Highly Tough and Highly Transparent Soluble Polybenzoxazoles, High Perform. Polym. , 19: 243-269.
25.
Miyazaki, T. and Hasegawa, M.Highly Tough and Highly Transparent Soluble Polybenzoxazoles (II). Effect of Sulfone Group, High Perform. Polym., [in press].
26.
Hemker, D.J. , Frank, C.W. and Thomas, J.W. (1988). Photophysical Studies of Amorphous Orientation in Poly(ethylene terephthalate) films, Polymer, 29: 437-447.
27.
Frank, C.W. and Gashgari, M.A. (1979). Excimer Fluorescence as a Molecular Probe of Polymer Blend Compatibility. 1. Blends of Poly(2-vinylnaphthalene) with Poly(alkyl methacrylates), Macromolecules, 12: 163-165.
28.
Hasegawa, M. , Shindo, Y., Sugimura, T., Ohshima, S., Horie, K., Kochi, M., Yokota, R. and Mita, I. (1993). Photophysical Processes in Aromatic Polyimides. Studies with Model Compounds, J. Polym. Sci., Part B, 31: 1617-1625.
29.
Hasegawa, M. , Shi, Z.Yokota, R., He, F. and Ozawa, H. (2001). Thermo-processable Polyimides with High Tg and High Thermo-oxidative Stability as Derived from 2,3,3',4'-Biphenyltetracarboxylic Dianhydride, High Perform. Polym., 13: 355-364.
30.
Tong, Y., Huang, W., Luo, J. and Ding, M. (1999). Synthesis and Properties of Aromatic Polyimides derived from 2, 2',3, 3'-Biphenyltetracarboxylic Dianhydride, J. Polym. Sci., Part A, 37: 1425-1433.
31.
Rozhanskii, I., Okuyama, K. and Goto, K. (2000). Synthesis and Properties of Polyimides derived from Isomeric Biphenyltetracarboxylic Dianhydrides, Polymer, 41: 7057-7065.
32.
Chen, C., Yokota, R., Hasegawa, M., Kochi, M., Horie, K. and Hergenrother, P.M. , (2005). Isomeric Biphenyl Polyimides (I). Chemical Structure-Property Relationships, High Perform. Polym., 17: 317-333.
33.
Hasegawa, M., Kochi, M., Mita , I. and Yokota, R. (1989). Molecular Aggregation and Fluorescence Spectra of Aromatic Polyimides, Eur. Polym. J., 25: 349-354.
34.
Hashimoto, H., Hasegawa, M., Horie , K., Yamashita, T., Ushiki, H. and Mita, I. (1993). Fluorescence Study of Thermotropic Liquid-Crystalline Polyesters, J. Polym. Sci., Part B, 31: 1187-1196.
35.
Eiselt, P. , Denzinger, S. and Schmidt, H.-W. (1995). Liquid Crystalline Model Compounds based on 3,3',4,4'-Biphenyltetracarboxylic Dianhydride (BPDA) , Liquid Crystals, 18: 257-262.
36.
Coburn, J.C. and Pottiger, M.T. (1996). Thermal Curing in Polyimide Films and Coatings , In: Ghosh, M.K. and Mittal, K.L. (eds) Polyimides: Fundamentals and Applications, Marcel Dekker, New York, 207-247.
37.
Vladimirov, L., Hasegawa, M. and Yokota, R. (1998). FT-IR Studies of Molecular Ordering in Biphenyl-type Polyimide, Network Polymers, 19: 18-33 (in Japanese).
38.
Vladimirov, L. , Hasegawa, M., Yokota , R. and Kochi, M. (1999). FTIR Studies of Molecular Ordering in Biphenyl-type Polyimide, In: Sachdev, H.S., Khojasteh, M.M. and Feger, C. (eds), Advances in Polyimides and Low Dielectric Polymers, Society of Plastic Engineers, New York, 185-189.
