Citation: Shi-Yu Zhang, Teng Fu, Yue Gong, De-Ming Guo, Xiu-Li Wang, Yu-Zhong Wang. Design and synthesis of liquid crystal copolyesters with high-frequency low dielectric loss and inherent flame retardancy[J]. Chinese Chemical Letters, ;2023, 34(5): 107615. doi: 10.1016/j.cclet.2022.06.038 shu

Design and synthesis of liquid crystal copolyesters with high-frequency low dielectric loss and inherent flame retardancy

State Key Laboratory of Polymer Materials Engineering, The Collaborative Innovation Center for Eco-Friendly and Fire-Safety Polymeric Materials, National Engineering Laboratory of Eco-Friendly Polymeric Materials (Sichuan), College of Chemistry, Sichuan University, Chengdu 610064, China

futeng@scu.edu.cn

yzwang@scu.edu.cn

Received Date: 22 April 2022
Revised Date: 3 June 2022
Accepted Date: 14 June 2022
Available Online: 18 June 2022

Figures(4)

Ultra-low dielectric loss (Df) and low dielectric constant (Dk) materials are urgently required in high-speed and large-capacity transmission, in which the wholly aromatic liquid crystal polymer (LCP) has gained attention due to its excellent dielectric properties. However, the relationship between molecular structure and dielectric properties is still not clear. In this study, two copolyesters containing phenyl or naphthyl structures are synthesized, as well as the effects of benzene and naphthalene mesogens on dielectric properties are investigated. The synthesized copolyesters containing naphthalene structure have good comprehensive properties with high thermal stability (T_5% = 479 ℃ and T_g = 195–216 ℃), inherent flame retardance (LOI = 33.0–35.0 and UL-94 V-0 level at 0.8 mm), low Dk (2.9–3.0@10 GHz) and low Df (0.0027–0.0047@10 GHz). Naphthalene mesogen can reduce the dielectric loss more significantly than benzene at high frequency by reducing the density and mobility of polarizable groups, which leads to the effectively limited dipole polarization in copolyesters. Consequently, we proposed a new strategy for designing low Dk and low Df materials.
- Liquid crystal polymer,
- Low dielectric loss,
- Low dielectric constant,
- Naphthalene structure,
- Flame retardant
1. [1]
  I. Nishimura, S. Fujitomi, Y. Yamashita, N. Kawashima, N. Miyaki, IEEE Proc. Electron. Compon. Technol. Conf. (2020) 641–646. doi: 10.1109/ectc32862.2020.00106
2. [2]
  Y.H. Kim, Y.W. Lim, Y.H. Kim, B.S. Bae, ACS Appl. Mater. Interfaces 8 (2016) 8335–8340. doi: 10.1021/acsami.6b01497
3. [3]
  J. Chen, M. Zeng, Z. Feng, et al., ACS Appl. Polym. Mater. 1 (2019) 625–630. doi: 10.1021/acsapm.8b00083
4. [4]
  X. Li, T. Liu, Y. Jiao, et al., Chem. Eng. J. 359 (2019) 641–651. doi: 10.1016/j.cej.2018.11.175
5. [5]
  C.C. Kuo, Y.C. Lin, Y.C. Chen, et al., ACS Appl. Polym. Mater. 3 (2020) 362–371.
6. [6]
  J. Duan, C. Mei, W. Wu, et al., Macromolecules 54 (2021) 6947–6955. doi: 10.1021/acs.macromol.1c01002
7. [7]
  J. Guo, H. Wang, C. Zhang, Q. Zhang, H. Yang, Polymers 12 (2020) 1875. doi: 10.3390/polym12091875
8. [8]
  Y. Ji, Y. Bai, X.B. Liu, K. Jia, Adv. Ind. Eng. Polym. Res. 3 (2020) 160–174.
9. [9]
  V.K. Thakur, M.R. Kessler, Liquid Crystalline Polymers: Volume 1-Structure and Chemistry, Springer, Switzerland, 2016.
10. [10]
  H.N. Yoon, L.F. Charbonneau, G.W. Calundann, Adv. Mater. 4 (1992) 206–214. doi: 10.1002/adma.19920040311
11. [11]
  A. Buyle Padias, H.K. Hall Jr, Polymers 3 (2011) 833–845. doi: 10.3390/polym3020833
12. [12]
  A. Pirnia, C.S.P. Sung, Macromolecules 21 (1988) 2699–2706. doi: 10.1021/ma00187a009
13. [13]
  I. Ouchi, M. Hosoi, S. Shimotsuma, J. Appl. Polym. Sci. 21 (1977) 3445–3456. doi: 10.1002/app.1977.070211220
14. [14]
  B.X. Du, Z.Y. He, Q. Du, Y.G. Guo, IEEE Trans. Dielectr. Electr. Insul. 23 (2016) 134–141. doi: 10.1109/TDEI.2015.005203
15. [15]
  J.W. Long, X.H. Shi, B.W. Liu, et al., Acta Polym. Sin. 51 (2020) 681–686.
16. [16]
  P. Patel, T.R. Hull, C. Moffatt, Fire Mater. 36 (2012) 185–201. doi: 10.1002/fam.1100
17. [17]
  A. Sadezky, H. Muckenhuber, H. Grothe, R. Niessner, U. Pöschl, Carbon 43 (2005) 1731–1742. doi: 10.1016/j.carbon.2005.02.018
18. [18]
  B.W. Liu, H.B. Zhao, Y.Z. Wang, Adv. Mater. 34 (2021) 2107905.
19. [19]
  F. Kremer, A. Schönhals, Broadband Dielectric Spectroscopy, Springer Science & Business Media, Berlin, 2002.
20. [20]
  L. Zhu, Q. Wang, Macromolecules 45 (2012) 2937–2954. doi: 10.1021/ma2024057
21. [21]
  B. Wang, W. Huang, L. Chi, et al., Chem. Rev. 118 (2018) 5690–5754. doi: 10.1021/acs.chemrev.8b00045
22. [22]
  B. Wang, L. Liu, G. Liang, L. Yuan, A. Gu, J. Mater. Chem. A 3 (2015) 23162–23169. doi: 10.1039/C5TA07611K
23. [23]
  D.S. Kalika, D.Y. Yoon, Macromolecules 24 (1991) 3404–3412. doi: 10.1021/ma00011a057
24. [24]
  D.J. Wilson, C. Vonk, A. Windle, Polymer 34 (1993) 227–237. doi: 10.1177/088541229300700302
25. [25]
  C. Qian, R. Bei, T. Zhu, et al., Macromolecules 52 (2019) 4601–4609. doi: 10.1021/acs.macromol.9b00136
26. [26]
  Z. Ahmad, Polymer Dielectric Materials, IntechOpen, London, 2012.
27. [27]
  M.G. Saphiannikova, N.V. Lukasheva, A.A. Darinskii, Y.Y. Gotlib, J. Brickmann, Macromolecules 33 (2000) 606–612. doi: 10.1021/ma9819440
28. [28]
  T.T. Hsieh, C. Tiu, G.P. Simon, Polymer 41 (2000) 4737–4742. doi: 10.1016/S0032-3861(99)00833-2
1. [1]
  Li Yan , Jian Ping Liu , Nan Zheng , Yu Bin Zheng . Copolymerization of (10-oxo-10-hydro-9-oxa-10λ⁵-phosphaphenanthrene-10-yl)-methyl acrylate with styrene. Chinese Chemical Letters, 2009, 20(7): 881-884. doi: 10.1016/j.cclet.2009.01.036
2. [2]
  Siyi Xu , Yue Han , Cheng Zhou , Jianxi Li , Liguo Shen , Hongjun Lin . A biobased flame retardant towards improvement of flame retardancy and mechanical property of ethylene vinyl acetate. Chinese Chemical Letters, 2023, 34(1): 107202-1-107202-5. doi: 10.1016/j.cclet.2022.02.008
3. [3]
  Shang Ke , Liao Wang , Wang Yu-Zhong . Thermally stable and flame-retardant poly(vinyl alcohol)/montmorillonite aerogel via a facile heat treatment. Chinese Chemical Letters, 2018, 29(3): 433-436. doi: 10.1016/j.cclet.2017.08.017
4. [4]
  Chao Zhang , Hong Yao Xu , Xian Zhao . Structure and properties of low-dielectric-constant poly(acetoxystyrene-co-octavinyl-polyhedral oligomeric silsesquioxane)hybrid nanocomposite. Chinese Chemical Letters, 2010, 21(4): 488-491. doi: 10.1016/j.cclet.2009.11.038
5. [5]
  Xin LI , Yu Xiang OU , Yun Hong ZHANG , Dan Jun LIAN . Synthesis and Structure of A Novel Caged Bicyclic Phosphate Flame Retardant. Chinese Chemical Letters, 2000, 11(10): 887-890.
6. [6]
  Jie LU , Jie KE , Bu Xing HAN , Hai Ke YAN . Local Dielectric Constant of the Solvent Shell Surrounding Ethyl Acetoacetate in Cosolvent-Modified Supercritical Carbon Dioxide. Chinese Chemical Letters, 1997, 8(4): 327-330.
7. [7]
  Yu Zhi-Peng , Li Xue , He Chengliang , Wang Di , Qin Ran , Zhou Guanqing , Liu Zhi-Xi , Andersen Thomas Rieks , Zhu Haiming , Chen Hongzheng , Li Chang-Zhi . High-efficiency organic solar cells with low voltage-loss of 0.46 V. Chinese Chemical Letters, 2020, 31(7): 1991-1996. doi: 10.1016/j.cclet.2019.12.003
8. [8]
  ZHAO Xiong-Yan . Synthesis and Characterization of a Polyquinoline Derivative Thin Film with a Low Dielectric Constant. Acta Physico-Chimica Sinica, 2010, 26(04): 1164-1170. doi: 10.3866/PKU.WHXB20100425
9. [9]
  Xuejing Yang , Jianfeng Hu , Hao Zhang . LCPs勇闯5G人才招聘会. University Chemistry, 2022, 37(9): 2207136-0. doi: 10.3866/PKU.DXHX202207136
10. [10]
  Hui-Ting Wang , Li-Hui Kong , Ping-Ping Shi , Qiang Li , Qiong Ye , Da-Wei Fu . The structure and dielectric properties of ionic compounds with flexible ammonium moiety. Chinese Chemical Letters, 2015, 26(3): 382-386. doi: 10.1016/j.cclet.2014.10.025
11. [11]
  HUANG Deng-Deng , CHEN Li-Zhuang . A Novel Gd Coordination Polymer Based on 2-(pyridin-3-yl)-1H-imidazole-4,5-dicarboxylate: Synthesis, Structure and Dielectric Properties. Chinese Journal of Structural Chemistry, 2014, 33(3): 361-366.
12. [12]
  Li-Zhuang Chen , Deng-Deng Huang . Synthesis, structure and dielectric properties of a novel Gd coordination polymer based on 2-(pyridin-4-yl)-1H-imidazole-4, 5-dicarboxylate. Chinese Chemical Letters, 2014, 25(2): 279-282.
13. [13]
  Fang-Fang Wang , Cheng Chen , Yi Zhang , Da-Wei Fu . Crystal structure and dielectric property of supramolecular macrocyclic [(NDPA)·(18-crown-6)]²⁺·(DMA)⁺·3ClO₄^- assemblies. Chinese Chemical Letters, 2015, 26(1): 31-35. doi: 10.1016/j.cclet.2014.10.005
14. [14]
  Zhi Yong Wu , Wei Xu , Jin Kui Xia , Yao Chi Liu , Qian Xin Wu , Wei Jian Xu . Flame retardant polyamide 6 by in situ polymerization of ε-caprolactam in the presence of melamine derivatives. Chinese Chemical Letters, 2008, 19(2): 241-244. doi: 10.1016/j.cclet.2007.12.012
15. [15]
  Wang Wen-Hua , Wei Long , Zhang Tian-Bao , He Liu , Zhang Shu-Fan , Qi Zong-Neng . Phase Transition of Side Chain Liquid Crystal Polyacrylate Studied by Positron Annihilation Lifetime Spectra. Acta Physico-Chimica Sinica, 1996, 12(08): 688-692. doi: 10.3866/PKU.WHXB19960804
16. [16]
  Zhang Xian-Sheng , Xia Yan-Zhi , Shi Mei-Wu , Yan Xiong . The flame retardancy of alginate/flame retardant viscose fibers investigated by vertical burning test and cone calorimeter. Chinese Chemical Letters, 2018, 29(3): 489-492. doi: 10.1016/j.cclet.2017.07.023
17. [17]
  Hongfei Li , Liwei Wang , Yingke Zhu , Pingkai Jiang , Xingyi Huang . Tailoring the polarity of polymer shell on BaTiO₃ nanoparticle surface for improved energy storage performance of dielectric polymer nanocomposites. Chinese Chemical Letters, 2021, 32(7): 2229-2232. doi: 10.1016/j.cclet.2020.12.032

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(157)
HTML views(16)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142