Highly soluble polyimide based on asymmetric diamines containing trifluoromethyl group for high performance dielectric material

Sehwa Bong; Hyeonuk Yeo; Bon-Cheol Ku; Munju Goh; Nam-Ho You

Macromolecular Research, Vol.26, No.1, 85-91, January, 2018

DOI10.1007/s13233-018-6010-7 Export Citation

Highly soluble polyimide based on asymmetric diamines containing trifluoromethyl group for high performance dielectric material

Sehwa Bong, Hyeonuk Yeo¹, Bon-Cheol Ku, Munju Goh, and Nam-Ho You^†

Carbon Composite Materials Research Center, Institute of Advanced Composites Materials, Korea Institute of Science and Technology, Eunha-ri san 101, Bondong-eup, Wanju-gun, Jeonbuk 55324, Korea
¹Department of Chemistry Education, Kyungpook National University, Chemistry Building, 80, Daehak-ro, Buk-gu, Daegu 41566, Korea

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In this study, we report the newly synthesized asymmetric diamine monomers and polyimides (PIs). The new diamines containing a trifluoromethyl group, 4- (4-amino-3-(trifluoromethyl)phenoxy)-2,6-dimethylaniline (ARFPA) and 4-(4-amino-2-(trifluoromethyl)phenoxy)-2,6-dimethylaniline (ALFPA) were synthesized by the nucleophilic aromatic substitution reaction, followed by reduction of nitro groups. The new PIs were synthesized by the conventional polycondensation from the newly synthesized diamines and 6FDA (4,4′-(hexafluoroisopropylidene)diphthalic anhydride). The all PI films showed the improved thermal stability (a temperature of 5% loss in weight) in the range of 523-562 °C and high glass transition temperature (T g >307 °C). The all PIs also exhibited good solubility in several solvents including chloroform, dimethyl sulfoxide, ethyl acetate, and acetone. Additionally, the PIs showed a low refractive index (1.5470-1.5475 at 637 nm) as well as a low dielectric constant.

Keywords:polyimide;trifluoromethyl groups;polymer optics;refractive index;dielectric constant

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Lim J, Yeo H, Kim SG, Park OK, Yu J, Hwang JY, Goh M, Ku BC, Lee HS, You NH, Compos. Part B: Eng., 114, 280 (2017)
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[Referenced By]

[1] Ganeshkumar A, Bera D, Mistri EA, Banerjee S, Eur. Polym. J., 60, 235 (2014)

[2] Hsiao SH, Peng SC, Kung YR, Leu CM, Lee TM, Eur. Polym. J., 73, 50 (2015)

[3] Zhai L, Yang SY, Fan L, Polymer, 53(16), 3529 (2012)

[4] Inoue Y, Mori H, US Patent, 20170044321 (2017).

[5] Lim J, Yeo H, Kim SG, Park OK, Yu J, Hwang JY, Goh M, Ku BC, Lee HS, You NH, Compos. Part B: Eng., 114, 280 (2017)

[6] Lim J, Yeo H, Goh M, Ku BC, Kim SG, Lee HS, Park B, You NH, Chem. Mater., 27, 2040 (2015)

[7] Yeo H, Lee J, Goh M, Ku BC, Sohn H, Ueda M, You NH, J. Polym. Sci. A: Polym. Chem., 53(7), 944 (2015)

[8] Nam KH, Kim H, Choi HK, Yeo H, Goh M, Yu J, Hahn JR, Han H, Ku BC, You NH, Polymer, 108, 502 (2017)

[9] Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS, Prog. Polym. Sci, 37, 907 (2012)

[10] Dhara MG, Banerjee S, Prog. Polym. Sci, 35, 1022 (2010)

[11] Vaganova TA, Plekhanov AI, Simanchuk AE, Mikerin SL, Spesivtsev EV, Karpova EV, Frolova TS, Malykhin EV, J. Fluor. Chem., 195, 70 (2017)

[12] Stoakley DM, Stclair AK, Croall CI, J. Appl. Polym. Sci., 51(8), 1479 (1994)

[13] Kim J, Kwon J, Kim M, Do J, Lee D, Han H, Polym. J., 48, 829 (2016)

[14] Lin T, Jianqing Z, Fang Z, Shumei L, Petrochem. Technol., 37, 744 (2008)

[15] Lv P, Dong Z, Dai X, Zhao Y, Qiu X, RSC Adv., 7, 4848 (2017)

[16] Liu Y, Zhou Z, Qu L, Zou B, Chen Z, Zhang Y, Liu S, Chi Z, Chen X, Xu J, Mater. Chem. Frontiers, 1, 326 (2017)

[17] Li Q, Wang YY, Zhang SL, Pang L, Tong H, Li J, Xu ZS, J. Mater. Sci., 52(9), 5283 (2017)

[18] Dong J, Yang C, Cheng Y, Wu T, Zhao X, Zhang Q, J. Mater. Chem., 5, 2818 (2017)

[19] Chisca S, Musteata VE, Sava I, Bruma M, Eur. Polym. J., 47, 1186 (2011)

[20] Feng L, Iroh JO, Eur. Polym. J., 49, 1811 (2013)

[21] Hsiao SH, Guo W, Chung CL, Chen WT, Eur. Polym. J., 46, 1878 (2010)

[22] Yeo H, Goh M, Ku BC, You NH, Polymer, 76, 280 (2015)

[23] Xiao TC, Fan X, Fan DS, Li Q, Polym. Bull., 74(11), 4561 (2017)

[24] Amininasab SM, Esmaili S, Taghavi M, Shami Z, J. Fluor. Chem., 192, 48 (2016)

[25] Wang J, Jin K, He F, Sun J, Fang Q, RSC Adv., 4, 40782 (2014)

[26] Choi H, Chung IS, Hong K, Park CE, Kim SY, Polymer, 49(11), 2644 (2008)

[27] Kim MK, Kim SY, Macromolecules, 35(12), 4553 (2002)

[28] Walsh CJ, Mandal BK, Chem. Mater., 13, 2472 (2001)

[29] Liaw DJ, Chang FC, Leung MK, Chou MY, Muellen K, Macromolecules, 38(9), 4024 (2005)

[30] Wang CS, Leu TS, Polymer, 41(10), 3581 (2000)

[31] Dal Kim S, Kim SY, Chung IS, J. Polym. Sci. A: Polym. Chem., 51(20), 4413 (2013)

[32] Dannhauser W, Bahe LW, J. Chem. Phys., 40, 3058 (1964)