Abstract
A new rigid tetracarboxylic dianhydride, 3,3''''',4,4'''''-p-sexiphenyltetracarboxylic dianhydride, was synthesized in seven steps starting from diethyl 4-bromophthalate. New aromatic polyimides containing a p-sexiphenyl unit were synthesized from this tetracarboxylic dianhydride and various aromatic diamines by the conventional two-step procedure of ring-opening polyaddition in a polar amide-type solvent and subsequent thermal cyclic dehydration. These polyimides had inherent viscosities of 1.20—1.69 dL g-1, and were insoluble in organic solvents. The polyimides were characterized by differential scanning calorimetry (DSC), thermogravimetry (TG), wide-angle X-Ray diffraction measurements, and dynamic mechanical analysis (DMA). Typical polyimides were noncrystalline and showed excellent thermal stability, and had glass transition temperatures (Tg) at about 250°C. Decrease in the modulus at the glass transition temperature was less than corresponding polyimides having no p-sexiphenyl unit due to the presence of the rigid p-sexiphenyl unit.
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References
P. E. Cassidy, “Thermally Stable Polymer”, Marcel Dekker, New York, N.Y., 1980, Chapter 4.
I. K. Spiliopoulos and J. A. Mikroyannidis, Macromolecules, 29, 5313 (1996).
I. K. Spiliopoulos and J. A. Mikroyannidis, Polymer, 38, 2733 (1997).
I. K. Spiliopoulos and J. A. Mikroyannidis, Macromolecules, 31, 1236 (1998).
I. K. Spiliopoulos and J. A. Mikroyannidis, Macromolecules, 31, 515 (1998).
Y. Imai, N. N. Maldar, and M. Kakimoto, J. Polym. Sci., Polym. Chem. Ed., 22, 2189 (1984).
H.-J. Jeong, A. Kobayashi, M. Kakimoto, and Y. Imai, Polym. J., 26, 373 (1994).
H.-J. Jeong, Y. Ohishi, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 29, 39 (1991).
H.-J. Jeong, M. Kakimoto, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 29, 1691 (1991).
Y. Oishi, M. Ishida, M. Kakimoto, Y. Imai, and T. Kurosaki, J. Polym. Sci., Polym. Chem. Ed., 30, 1027 (1992).
A. Morikawa and T. Hatakeyama, Polym. J., 31, 76 (1999).
A. Morikawa, Polym. J., 32, 275 (2000).
F. R. Bean and J. R. Johnson, J. Am. Chem. Soc., 54, 4415 (1932).
G. C. Coutts, H. R. Goldschmid, and O. C. Musgrave, J. Chem. Soc. Sect C, 488 (1970).
A. Morikawa, Macromolecules, 31, 5999 (1998).
T. Oh-e, N. Miyaura, and A. Suzuki, Synlett, 221 (1990).
W. C. Shieh and J. A. Carlson, J. Org. Chem., 57, 379 (1992).
M. M. Koton and Yu. N. Saganov, J. Therm. Anal. Calorim., 7, 165 (1975).
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Morikawa, A., Ono, K. Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3''''',4,4'''''-p-Sexiphenyltetracarboxylic Dianhydride. Polym J 32, 948–953 (2000). https://doi.org/10.1295/polymj.32.948
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DOI: https://doi.org/10.1295/polymj.32.948