Stilbene 구조를 지닌 바이오 기반 에폭시 열경화성 수지의 높은 Tg 및 난연성

Guangming Lu; Xuezhen Wang; Na Teng; Jingyuan Hu; Liyue Zhang; Jinyue Dai; Yongjia Xu; Sakil Mahmud; Xiaoqing Liu

Polymer(Korea), Vol.45, No.4, 581-591, July, 2021

DOI10.7317/pk.2021.45.4.581 Export Citation

Stilbene 구조를 지닌 바이오 기반 에폭시 열경화성 수지의 높은 Tg 및 난연성

Bio-based Epoxy Thermoset Containing Stilbene Structure with Ultrahigh Tg and Excellent Flame Retardancy

Guangming Lu^{1, 2}, Xuezhen Wang², Na Teng², Jingyuan Hu², Liyue Zhang², Jinyue Dai^{2, 3, †}, Yongjia Xu^{1, †}, Sakil Mahmud², and Xiaoqing Liu²

¹School of Marine Sciences, Ningbo University, Ningbo 315820, PR China
²Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China
³University of Chinese Academy of Sciences, Beijing 100049, China

E-mail:,

Bio-based epoxy resins with an ultrahigh glass transition temperature (Tg) and excellent flame retardancy are critical for developing sustainable polymers. Herein, a novel trifunctional epoxy monomer triglycidyl ether of resveratrol (TGER) was synthesized from renewable resveratrol. The chemical structure of TGER was confirmed by Fourier transform infrared (FTIR), 1H, and 13C nuclear magnetic resonance (NMR) spectroscopy which was then reacted with 4,4'-diaminodiphenylmethane (DDM) to form resin. The obtained resin was evaluated in terms of flame retardance and thermal properties. The resultant TGER-DDM 240 resin shows excellent flame-retardant properties, presenting a residual char of 42.5% at 800 °C, limiting oxygen index (LOI) of 31.2%, and flammability rating of V-0 in UL94 test. Moreover, the resin possesses an ultrahigh Tg at 294 °C. This work provides a facile method for preparing high-performance flame-retardant epoxy resin from a renewable resource.

Keywords:bio-based;stilbene structure;flame retardancy;epoxy resin

[References]

Ye J, Ma S, Wang B, Chen Q, Huang K, Xu X, Li Q, et al., Green Chem., 23, 1772 (2021)
Nabipour H, Wang X, Song L, Hu YA, Green Chem., 23, 501 (2021)
Qi Y, Wang J, Kou Y, Pang H, Zhang S, Li N, Liu C, Weng Z, Jian X, Nat. Commun., 10, 2107 (2019)
Wang X, Guo W, Song L, Hu Y, Composites Part B, 179, 107487 (2019)
Zhang D, Liang E, Li T, Chen S, Zhang J, Cheng X, Zhou J, Zhang A, RSC Adv., 3, 3095 (2013)
Qi Y, Weng Z, Kou Y, Song L, Li J, Wang J, Zhang S, Liu C, Jian X, Chem. Eng. J., 406, 126881 (2021)
Qi Y, Weng Z, Zhang K, Wang J, Zhang S, Liu C, Jian X, Chem. Eng. J., 387, 124115 (2020)
Ma S, Liu X, Jiang Y, Tang Z, Zhang C, Zhu J, Green Chem., 15, 245 (2013)
Tao Y, Fang L, Dai M, Wang C, Sun J, Fang Q, Polym. Chem., 11, 4500 (2020)
Savonnet E, Grau E, Grelier S, Defoort B, Cramail H, ACS Sustain. Chem. Eng., 6, 11008 (2018)
Chi Z, Guo Z, Xu Z, Zhang M, Li M, Shang L, Ao Y, Polym. Degrad. Stabil., 176, 109151 (2020)
Liu J, Dai J, Wang S, Peng Y, Cao L, Liu X, Composites Part B, 190, 107926 (2020)
Xie W, Huang S, Tang D, Liu S, Zhao J, RSC Adv., 10, 1956 (2020)
Menard R, Negrell C, Fache M, Ferry L, Sonnier R, David G, RSC Adv., 5, 70856 (2015)
Gao L, Zheng G, Nie X, Wang Y, J. Ther. Anal. Calorim., 127, 1419 (2017)
Deng LL, Shen MM, Yu J, Wu K, Ha CY, Ind. Eng. Chem. Res., 51(24), 8178 (2012)
Wan JT, Gan B, Li C, Molina-Aldareguia J, Kalali EN, Wang X, Wang DY, Chem. Eng. J., 284, 1080 (2016)
Wu JN, Chen L, Fu T, Zhao HB, Guo DM, Wang XL, Wang YZ, Chem. Eng. J., 336, 622 (2018)
Xie W, Huang S, Tang D, Liu S, Zhao J, Chem. Eng. J., 394, 123667 (2020)
Dai J, Teng N, Liu J, Feng J, Zhu J, Liu X, Composites Part B, 179, 107523 (2019)
Dai J, Peng Y, Teng N, Liu Y, Liu C, Shen X, Mahmud S, Zhu J, Liu X, ACS Sustain Chem. Eng., 6, 7589 (2018)
Yang D, Dong L, Hou X, Zheng W, Xiao J, Xu J, Ma H, Polym. Advan. Technol., 31, 135 (2020)
Huang G, Fang L, Wang C, Dai M, Sun J, Fang Q, Polym. Chem., 12, 402 (2021)
Hou J, Chen X, Sun J, Fang Q, Polymer, 200, 122570 (2020)
Guo Z, Zhang M, Zhang Y, Liu L, Li M, Shang L, Ao Y, J. Appl. Polym. Sci., 137, 49122 (2020)
Tian Y, Ke M, Wang X, Wu G, Zhang J, Cheng JA, Eur. Polym. J., 147, 110282 (2021)
Tian Y, Wang Q, Shen L, Cui Z, Kou L, Cheng J, Zhang J, Chem. Eng. J., 383, 123124 (2020)
Meng J, Zeng Y, Zhu G, Zhang J, Chen P, Cheng Y, Fang Z, Guo K, Polym. Chem., 2370 2019.
Bai YW, Wang XD, Wu DZ, Ind. Eng. Chem. Res., 51(46), 15064 (2012)
Ma S, Liu X, Fan L, Jiang Y, Cao L, Tang Z, Zhu J, ChemSusChem, 7, 555 (2014)
Li T, Liu X, Jiang Y, Ma S, Zhu J, Iran. Polym. J., 25, 957 (2016)
Dai J, Ma S, Wu Y, Han L, Zhang L, Zhu J, Liu X, Green Chem., 17, 238/3 (2015)
John MJ, Green composites for automotive applications, pp.43, 2019.
Li C, Dai J, Liu X, Jiang Y, Ma S, Zhu J, Macromol. Chem. Phys., 217, 1439 (2016)

[1] Ye J, Ma S, Wang B, Chen Q, Huang K, Xu X, Li Q, et al., Green Chem., 23, 1772 (2021)

[2] Nabipour H, Wang X, Song L, Hu YA, Green Chem., 23, 501 (2021)

[3] Qi Y, Wang J, Kou Y, Pang H, Zhang S, Li N, Liu C, Weng Z, Jian X, Nat. Commun., 10, 2107 (2019)

[4] Wang X, Guo W, Song L, Hu Y, Composites Part B, 179, 107487 (2019)

[5] Zhang D, Liang E, Li T, Chen S, Zhang J, Cheng X, Zhou J, Zhang A, RSC Adv., 3, 3095 (2013)

[6] Qi Y, Weng Z, Kou Y, Song L, Li J, Wang J, Zhang S, Liu C, Jian X, Chem. Eng. J., 406, 126881 (2021)

[7] Qi Y, Weng Z, Zhang K, Wang J, Zhang S, Liu C, Jian X, Chem. Eng. J., 387, 124115 (2020)

[8] Ma S, Liu X, Jiang Y, Tang Z, Zhang C, Zhu J, Green Chem., 15, 245 (2013)

[9] Tao Y, Fang L, Dai M, Wang C, Sun J, Fang Q, Polym. Chem., 11, 4500 (2020)

[10] Savonnet E, Grau E, Grelier S, Defoort B, Cramail H, ACS Sustain. Chem. Eng., 6, 11008 (2018)

[11] Chi Z, Guo Z, Xu Z, Zhang M, Li M, Shang L, Ao Y, Polym. Degrad. Stabil., 176, 109151 (2020)

[12] Liu J, Dai J, Wang S, Peng Y, Cao L, Liu X, Composites Part B, 190, 107926 (2020)

[13] Xie W, Huang S, Tang D, Liu S, Zhao J, RSC Adv., 10, 1956 (2020)

[14] Menard R, Negrell C, Fache M, Ferry L, Sonnier R, David G, RSC Adv., 5, 70856 (2015)

[15] Gao L, Zheng G, Nie X, Wang Y, J. Ther. Anal. Calorim., 127, 1419 (2017)

[16] Deng LL, Shen MM, Yu J, Wu K, Ha CY, Ind. Eng. Chem. Res., 51(24), 8178 (2012)

[17] Wan JT, Gan B, Li C, Molina-Aldareguia J, Kalali EN, Wang X, Wang DY, Chem. Eng. J., 284, 1080 (2016)

[18] Wu JN, Chen L, Fu T, Zhao HB, Guo DM, Wang XL, Wang YZ, Chem. Eng. J., 336, 622 (2018)

[19] Xie W, Huang S, Tang D, Liu S, Zhao J, Chem. Eng. J., 394, 123667 (2020)

[20] Dai J, Teng N, Liu J, Feng J, Zhu J, Liu X, Composites Part B, 179, 107523 (2019)

[21] Dai J, Peng Y, Teng N, Liu Y, Liu C, Shen X, Mahmud S, Zhu J, Liu X, ACS Sustain Chem. Eng., 6, 7589 (2018)

[22] Yang D, Dong L, Hou X, Zheng W, Xiao J, Xu J, Ma H, Polym. Advan. Technol., 31, 135 (2020)

[23] Huang G, Fang L, Wang C, Dai M, Sun J, Fang Q, Polym. Chem., 12, 402 (2021)

[24] Hou J, Chen X, Sun J, Fang Q, Polymer, 200, 122570 (2020)

[25] Guo Z, Zhang M, Zhang Y, Liu L, Li M, Shang L, Ao Y, J. Appl. Polym. Sci., 137, 49122 (2020)

[26] Tian Y, Ke M, Wang X, Wu G, Zhang J, Cheng JA, Eur. Polym. J., 147, 110282 (2021)

[27] Tian Y, Wang Q, Shen L, Cui Z, Kou L, Cheng J, Zhang J, Chem. Eng. J., 383, 123124 (2020)

[28] Meng J, Zeng Y, Zhu G, Zhang J, Chen P, Cheng Y, Fang Z, Guo K, Polym. Chem., 2370 2019.

[29] Bai YW, Wang XD, Wu DZ, Ind. Eng. Chem. Res., 51(46), 15064 (2012)

[30] Ma S, Liu X, Fan L, Jiang Y, Cao L, Tang Z, Zhu J, ChemSusChem, 7, 555 (2014)

[31] Li T, Liu X, Jiang Y, Ma S, Zhu J, Iran. Polym. J., 25, 957 (2016)

[32] Dai J, Ma S, Wu Y, Han L, Zhang L, Zhu J, Liu X, Green Chem., 17, 238/3 (2015)

[33] John MJ, Green composites for automotive applications, pp.43, 2019.

[34] Li C, Dai J, Liu X, Jiang Y, Ma S, Zhu J, Macromol. Chem. Phys., 217, 1439 (2016)