Abstract
Highly refractive and transparent polyimides (PIs) have been developed. The PIs were prepared from a para-substituted sulfonyl-bridged dianhydride, 4,4′-[p-sulfonylbis(phenylenesulfanyl)]diphthalic anhydride (p-DPSDA) and various sulfur-containing aromatic diamines including 4,4′-thiobis[(p-phenylenesulfanyl)aniline] (3SDA), 4,4′-sulfonylbis[(p-phenylene-sulfanyl)aniline] (BADPS), and 2,7-bis(p-aminophenylenesulfanyl)thianthrene (APTT) by employing a two-step polycondensation procedure. The PIs showed excellent thermal stabilities with 5% weight loss temperatures (Td5) exceeding 470 °C in nitrogen and the glass transition temperatures (Tgs) higher than 208 °C. The PI films exhibited good optical transmittances exceeding 85% at 450 nm and high refractive indices of 1.7169–1.7420 at 632.8 nm that are almost same as those of the PIs derived from 4,4′-[m-sulfonylbis(phenylenesulfanyl)]diphthalic anhydride (mDPSDA). The para-substituted electron-withdrawing sulfonyl moiety improves the transparency but lowers the refractive index. In addition, very small birefringence (Δn) of 0.0065–0.0093 was obtained for the PIs.
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References
“Polyimides: Fundamentals and Applications,” M. K. Ghosh and K. L. Mittal, Ed. Marcel Decker, New York, 1996.
J. Nakai and T. Aoki, U. S. Patent 7087945 (2006).
C.-C. Chang and W.-C. Chen, J. Polym. Sci., Part A: Polym. Chem., 39, 3419 (2001).
C.-C. Chang and W.-C. Chen, Chem. Mater., 14, 4242 (2002).
C.-M. Chang, C.-L. Chang, and C.-C. Chang, Macromol. Mater. Eng., 291, 1521 (2006).
G. Liu, Y. Nakamura, Y. Shibasaki, S. Ando, and M. Ueda, Polym. J., 39, 543 (2007).
G. Liu, Y. Nakamura, Y. Shibasaki, S. Ando, and M. Ueda, J. Polym. Sci., Part A: Polym. Chem., 45, 5606 (2007).
G. Liu, Y. Nakamura, Y. Shibasaki, S. Ando, and M. Ueda, Macromol. Chem. Phys., in press.
G. Liu, Y. Nakamura, Y. Shibasaki, S. Ando, and M. Ueda, Macromolecules, 40, 4614 (2007).
S. Ando, T. Matsuura, and S. Sasaki, Polym. J., 29, 69 (1997).
G. Liu, Y. Nakamura, Y. Suzuki, Y. Shibasaki, S. Ando, and M. Ueda, Macromolecules, 40, 7902 (2007).
J. Yan, Z. Wang, L. Gao, and M. Ding, Polymer, 46, 7678 (2005).
J. M. Salley and C. W. Frank, “Polyimides Fundamentals and Applications” M. K. Ghosh and K. L. Mittal, Ed., Marcel Decker, New York, 1996, p 288.
Y. Ding and A. S. Hay, Macromolecules, 29, 6386 (1996).
S. Ando, T. Fujigaya, and M. Ueda, Jpn. J. Appl. Phys. 41, L105 (2002).
Y. Terui and S. Ando, J. Photopolym. Sci. Technol., 18, 337 (2005).
T. Sugioka and A. S. Hay, J. Polym. Sci., Part A: Polym. Chem., 39, 1040 (2001).
K. St. Clair, T. L. Clair, and W. P. Winfree, Proc. ACS Polym. Mater. Sci. Eng., 59, 28 (1988).
R. J. Nussbaumer, W. R. Caseri, O. Smith, and T. Tervoort, Macromol. Mater. Eng., 288, 44 (2003).
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Suzuki, Y., Liu, Jg., Nakamura, Y. et al. Synthesis of Highly Refractive and Transparent Polyimides Derived from 4,4′-[p-Sulfonylbis(phenylenesulfanyl)]diphthalic Anhydride and Various Sulfur-containing Aromatic Diamines. Polym J 40, 414–420 (2008). https://doi.org/10.1295/polymj.PJ2007233
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DOI: https://doi.org/10.1295/polymj.PJ2007233
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