Abstract
A new aromatic diamine bearing ether and pendant 9(10H)-anthrone groups, 10,10-bis[4-(4-aminophenoxy)phenyl]-9(10H)-anthrone was reacted with various aromatic dianhydrides to yield the corresponding cardo polyimides via the poly(amic acid) (PAA) precursors and thermal or chemical imidization. The PAAs were produced with moderate to high inherent viscosities of 0.91–1.53 dL/g. All the PAAs could be cast from DMAc solution and thermally converted into transparent, flexible and tough polyimide films with tensile strength of 79.6–115.2 MPa, tensile modulus of 1.97–2.48 GPa, and elongation at break of 10.8–21.7%. These polyimides were predominantly amorphous, and displayed excellent thermal stability with glass-transition temperature of 290–359 °C, 10% weight loss temperature of 522–566 °C, and the residue of 59–65% at 800 °C in nitrogen. Most of the polyimides obtained by chemical cyclodehydration procedure were found to be soluble in NMP, DMF and mcresol at room temperature.
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References
Sroog CE (1991) Polyimides. Prog Polym Sci 16:561–694
Hasegawa M, Horie K (2001) Photophysics, photochemistry, and optical properties of polyimides. Prog Polym Sci 26:259–335
Ding MX (2007) Isomeric polyimides. Prog Polym Sci 32:623–668
Liaw D-J, Wang K-L, Huang Y-C, Lee K-R, Lai J-Y, Ha C-S (2012) Advanced polyimide materials: syntheses, physical properties and applications. Prog Polym Sci 37:907–974
Huang XH, Mei M, Liu CJ, Pei XL, Wei C (2015) Synthesis and characterization of novel highly soluble and optical transparent polyimides containing tert-butyl and morpholinyl moieties. J Polym Res 22:169
Li CY, Yi L, Xu ST, Wu XM, Huang W, Yan DY (2017) Synthesis and characterization of polyimides from 4, 4′-(3-(tert-butyl)-4-aminophenoxy)diphenyl ether. J Polym Res 24:7
Wu F, Zhou X, Yu X (2017) Synthesis and characterization of novel star-branched polyimides derived from 2,2-bis[4-(2,4-diaminophenoxy)phenyl]hexafluoropropane. RSC Adv 7:35786–35794
Hsiao SH, Liao YC (2018) Synthesis and properties of novel organosoluble and light-colored poly(ester-amide)s and poly(ester-imide)s with triptycene moiety. J Polym Res 25:52
Yi L, Huang W, Yan DY (2017) Polyimides with side groups: synthesis and effects of side groups on their properties. J Polym Sci Part A Polym Chem 55:533–559
Liu JT, Chen GF, Fang XZ (2016) Preparation, characterization, and properties of poly(thioether imide)s from isomeric bis(chlorophthalimide)s and bisthiophenols. High Perform Polym 28:64–74
Li Z, Wen Y, Wang Y, Zhu SM (2017) Highly transparent and organosoluble polyimides derived from 2,2′-bis[4-(5-amino-2-pyridinoxy)phenyl]propane. High Perform Polym 29:161–169
Kaya I, Kamaci M (2018) Synthesis, optical, and thermal properties of polyimides containing flexible ether linkage. J Appl Polym Sci 135:46573
Mirsamiei A (2018) Synthesis and properties of polyimides derived from bis-(aminophenoxy) containing naphthalene, [phenyl]propane and [methyl]cyclohexane segment and 4, 4′-carbonyldiphthalic anhydride. J Macromol Sci A 55:519–525
Zhou Y-T, Liu X-L, Wei M-H, Song C, Huang Z-Z, Sheng S-R (2019) New fluorinated copoly(pyridine ether imide)s derived from 4,4′-oxydianiline, pyromellitic dianhydride and 4-(4-trifluoromethyl)phenyl-2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]pyridine. Polym Bulletin 76:4139–4155
Zhang L, Wu X, Liu SY, Peng JW, Liu BJ (2019) Low-Tg polyimides containing multiple ether linkages and cyano pendants. High Perform Polym 31:369–379
Yang C-P, Lin J-H (1993) Syntheses and properties of aromatic polyamides and polyimides derived from 9,9-bis[4-(p-aminophenoxy )phenyl]fluorene. J Polym Sci Part A Polym Chem 31:2153–2163
Yang YH, Xia JC, Ding ZJ, Zheng YX, Ding SJ, Shen YZ (2018) Synthesis and resistive switching characteristics of polyimides derived from 2,7-aryl substituents tetraphenyl fluorene diamines. Eur Polym J 108:85–97
Yang C-P, Lin J-H (1994) Preparation and properties of aromatic polyamides and polyimides derived from 3,3-bis[4-(4-aminophenoxy)phenyl]phthalide. J Polym Sci Part A Polym Chem 32:423–433
Tang YM, Li L, Ma K, Chen GF, Wang W, Fang XZ (2018) Transparent and organosoluble cardo polyimides with different trans/cis ratios of 1,4-diaminocyclohexane via aromatic nucleophilic substitution polymerization. Polym Int 67:598–605
Liaw D-J, Liaw B-Y (1999) Synthesis and properties of new polyimides derived from 1,1-bis[4-(4-aminophenoxy)phenyl]cyclododecane. Polymer 40:3183–3189
Chen Y-Y, Yang C-P, Hsiao S-H (2006) Novel organosoluble and colorless poly(ether imide)s based on 1,1-bis[4-(3,4-dicarboxyphenoxy)phenyl]cyclohexane dianhydride and trifluoromethyl-substituted aromatic bis(ether amine)s. Eur Polym J 42:1705–1717
Yao JA, Wang CB, Zhao XG, Zhou HW, Chen CH, Wang DM (2018) Highly transparent and soluble polyimides with synergistic effects of pyridine and cyclohexane. High Perform Polym 30:418–426
Korshak VV, Vinogradova SV, Vygodski YS (1974) Cardo polymers. J Macromol Sci Rev Macromol Chem C11:45–142
Sheng S-R, Zhang W, Lu C, Wan J, Liu X-L, Song C-S (2012) Synthesis and characterization of new cardo polyimides derived from 9,9-bis[4-(4-aminophenoxy)phenyl]xanthene. J Appl Polym Sci 126:297–303
Sheng S-R, Li D-P, Liu X-L, Lai T-Q, Song C-S (2011) Organosoluble, low dielectric constant fluorinated polyimides based on 9,9-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]xanthene. Polym Int 60:1185–1193
Acknowledgments
The financial support for this work provided by the National Natural Science Foundation of China (No. 21564005, 51663011), the Research Program of Jiangxi Science and Technology Department (No. 20192BBE50049), the Ground Project for Science and Technology of Jiangxi Universities (No. KJLD14022) and the Research Program of Jiangxi Province Department of Education (No. GJJ14236) is gratefully acknowledged.
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Li, J., Mao, XC., Huang, ZZ. et al. Synthesis and properties of novel polyimides based on 10,10-bis[4-(4-aminophenoxy)phenyl]-9(10H)-anthrone. J Polym Res 27, 214 (2020). https://doi.org/10.1007/s10965-020-02190-6
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DOI: https://doi.org/10.1007/s10965-020-02190-6