Abstract
The properties of a series of imide oligomers were characterized according to their molecular weights, solubility, and thermal and rheological properties. This series of imide oligomers was synthesized via a two-step method using 2,2′,3,3′-biphenyltetracarboxylic dianhydride(3,3′-BPDA) and aromatic diamines as the monomers, and 4-phenylethynyl phthalic anhydride(PEPA) as the end-capping agent. The imide oligomers based on 3,3′-BPDA showed excellent solubility in low boiling point solvents and low melt viscosity, which were attributed to their unique bent architectures. High-performance thermosetting polyimides were produced from these oligomers via thermal crosslinking of the phenylethynyl groups. The mechanical and thermal properties of the thermosets were studied using tensile testing, dynamic mechanical thermal analysis(DMTA), and thermogravimetric analysis(TGA). The 3,3′-BPDA-based thermosets exhibited excellent thermal properties, with glass transition temperatures of up to 455 °C, and 5% mass loss temperatures of up to 569 °C in air. The thermosets based on 3,3′-BPDA showed superior thermal properties compared to those derived from TriA-X series oligomers.
Similar content being viewed by others
References
Sroog C. E., Prog. Polym. Sci., 1991, 16(4), 561
Hasegawa M., Matano T., Shindo Y., Macromolecules, 1996, 29(24), 7897
Meador M. A., Annu. Rev. Mater. Sci., 1998, 28(1), 599
Hergenrother P. M., Watson K. A., Smith J. G., Connell J. W., Yokota R., Polymer, 2002, 43(19), 5077
Hergenrother P. M., Watson K. A., Smith J. G., Connell J. W., Yokota R., Polymer, 2004, 45(16), 5441
Liu Y. W., Huang J., Tan J. H., Zeng Y., Ding Q., Zhang H. L., Liu Y. J., Xiang X. W., Polym. Int., 2017, 66(8), 1214
Khalid N., Park O. O., Akhter T., Siddiqi H. M., J. Appl. Polym. Sci., 2017, 134(9), 1
Song G. L., Wang D. M., Zhao X. G., Dang G. D., Zhou H. W., Chen C. H., High Perform. Polym., 2013, 25(3), 354
Li T. Y., Huang H. H., Wang L., Chen Y. M., RSC Adv., 2017, 7(65), 40996
Ma X. Y., Kang C. Q., Chen W. H., Jin R. Z., Guo H. Q., Qiu X. P., Gao L. X., J. Polym. Sci. Pol. Chem., 2016, 54(4), 570
Yan S. Y., Chen W. Q., Yang X. J., Chen C. A., Huang M. F., Xu Z. S., Yeung K. W. K., Yi C. F., Polym. Bull., 2011, 66(9), 1191
Serafini T. T., Delvigs P., Lightsey G. R., J. Appl. Polym. Sci., 1972, 16(4), 905
Vannucci R. D., SAMPE J., 1987, 19(1), 31
Scola D. A., Wai M., J. Appl. Polym. Sci., 1994, 52(3), 421
Chuang K. C., Bowman C. L., Tsotsis T. K., Arendt C. P., High Perform. Polym., 2003, 15(4), 459
Hao J. Y., Hu A. J., Yang S. Y., High Perform. Polym., 2002, 14(4), 325
Wilson D., British Polym. J., 1988, 20(5), 405
Pater R. H., SAMPE J., 1994, 30(5), 29
Hergenrother P. M., Connell J. W., Smith J. G., Polymer, 2000, 41(13), 5073
Yokota R., Yamamoto S., Yano S., Sawaguchi T., Hasegawa M., Yamaguchi H., Ozawa H., Sato R., High Perform. Polym., 2001, 13(2), S61
Hergenrother P. M., High Perform. Polym., 2003, 15(1), 3
Liu Y. F., Wang Z., Li G., Ding M. X., High Perform. Polym., 2010, 20(1), 95
Meng X. S., Yan J. L., Fan W. F., Liu J. F., Wang Z., Li G. D., RSC Adv., 2014, 4(71), 37458
Smith J. G., Connell J. W., Hergenrother P. M., Ford L. A., Criss J. M., Macromol. Symp., 2003, 199(1), 401
Connell J. W., Smith J. G., Hergenrother P. M., High Perform. Polym., 2003, 15(4), 375
Connell J. W., Smith J. G., Hergenrother P. M., 49th Int. SAMPE Symp., Covina: Soc Advancement Material & Process Engineering, Long Beach, CA, 2004
Smith J. G., Connell J. W., Hergenrother P. M., Criss J. M., J. Compos. Mater., 2002, 36(19), 2255
Hergenrother P. M., Connell J. W., Smith J. G., Polymer, 2000, 41(3), 5073
Ishida Y., Ogasawara T., Yokota R., High Perform. Polym., 2006, 18(5), 727
Hergenrother P. M., Smith J. G., Polymer, 1994, 35(22), 4857
Smith J. G., Connell J. W., Hergenrother P. M., J. Compos. Mater., 2000, 34(7), 614
Miyauchi M., Ishida Y., Ogasawara T., Yokota R., Polym. J., 2012, 44(9), 959
Miyauchi M., Ishida Y., Ogasawara T., Yokota R., React. Funct. Polym., 2013, 73(2), 340
Fan W. F., Liu X. J., Yan J. L., Meng X. S., Liu J. F., Wang Z., Chem. J. Chinese Universities, 2016, 37(10), 1926
Tong Y. J., Huang W. X., Luo J., Ding M. X., J. Polym. Sci. Polym. Chem., 1999, 37(10), 1425
Rozhanskii I., Okuyama K., Goto K., Polymer, 2000, 41(19), 7057
Zhou H. W., Chen C. H., Kanbara R., Sasaki T., Yokota R., High Perform. Polym., 2005, 17(2), 193
Ding M. X., Wang X. Q., Yang Z. H., Process for the Preparation of 3,3′,4,4′-Biphenyltetracarboxylic Acid and Its Derivatives, US 5081281, 1992
Wang Z., Gao L. X., Ding M. X., Preparation of 4-Phenylethynyl Phthalic Anhydride, CN ZL200310115829.8, 2003
Author information
Authors and Affiliations
Corresponding author
Additional information
Supported by the Technology Innovation Fund of Chinese Academy of Sciences(No.CXJJ-17-M159) and the National Natural Science Foundation of China(No.51473157).
Rights and permissions
About this article
Cite this article
Meng, X., Lu, G., Liu, X. et al. Highly Soluble Phenylethynyl-terminated Imide Oligomers and Thermosetting Polyimides Based on 2,2′,3,3′-Biphenyltetracarboxylic Dianhydride. Chem. Res. Chin. Univ. 35, 530–536 (2019). https://doi.org/10.1007/s40242-019-8334-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-019-8334-z