Polybenzoxazine/organosilicon composites with low dielectric constant and dielectric loss

doi:10.1016/j.cjche.2023.06.024

中国化学工程学报 ›› 2023, Vol. 64 ›› Issue (12): 241-249.DOI: 10.1016/j.cjche.2023.06.024

• Full Length Article • 上一篇下一篇

Polybenzoxazine/organosilicon composites with low dielectric constant and dielectric loss

Manlin Yuan, Xin Lu, Xiaoyun Ma, Hao Lin, Angui Lu, Liyan Shao, Zhong Xin

State Key Laboratory of Chemical Engineering, School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China

收稿日期:2023-03-16 修回日期:2023-06-06 出版日期:2023-12-28 发布日期:2024-02-05
通讯作者: Zhong Xin,E-mail:xzh@ecust.edu.cn
基金资助:
This work was supported by the Innovation Program of the Shanghai Municipal Education Commission (2019-01-07-00-02-E00061) and the Shanghai Municipal Science and Technology Commission (21520761100).

Polybenzoxazine/organosilicon composites with low dielectric constant and dielectric loss

Manlin Yuan, Xin Lu, Xiaoyun Ma, Hao Lin, Angui Lu, Liyan Shao, Zhong Xin

State Key Laboratory of Chemical Engineering, School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China

Received:2023-03-16 Revised:2023-06-06 Online:2023-12-28 Published:2024-02-05
Contact: Zhong Xin,E-mail:xzh@ecust.edu.cn
Supported by:
This work was supported by the Innovation Program of the Shanghai Municipal Education Commission (2019-01-07-00-02-E00061) and the Shanghai Municipal Science and Technology Commission (21520761100).

摘要/Abstract

摘要： The evolution of electronic communication technology raises higher requirements for low dielectric constant (low-k) materials. For this, a benzoxazine functional organosilicon (HP-aptes) with dense Si—O—Si crosslinking networks and large sterically hindered tert-butyl groups was prepared by the sol–gel method. Then, a series of polybenzoxazine composites (PPHP) were prepared from intrinsically low dielectric constant bis-functional benzoxazine monomer (P-aptmds) and HP-aptes. The double crosslinking networks of polybenzoxazine and organosilicon further increased the crosslinking density and decreased the dipole density of composites, which endowed the composites with enhanced low-k properties. When the content of HP-aptes is 30% (mass), the crosslinking density was 2.05×10^-3 mol·cm^-3, while that of PP-aptmds was 3.31×10^-3 mol·cm^-3. In addition, the dielectric constant and dielectric loss of PPHP composite at 1 MHz could reach 2.61 and 0.0056, respectively.

关键词: Polybenzoxazine, Organosilicon, Composite, Dielectric constant

Abstract: The evolution of electronic communication technology raises higher requirements for low dielectric constant (low-k) materials. For this, a benzoxazine functional organosilicon (HP-aptes) with dense Si—O—Si crosslinking networks and large sterically hindered tert-butyl groups was prepared by the sol–gel method. Then, a series of polybenzoxazine composites (PPHP) were prepared from intrinsically low dielectric constant bis-functional benzoxazine monomer (P-aptmds) and HP-aptes. The double crosslinking networks of polybenzoxazine and organosilicon further increased the crosslinking density and decreased the dipole density of composites, which endowed the composites with enhanced low-k properties. When the content of HP-aptes is 30% (mass), the crosslinking density was 2.05×10^-3 mol·cm^-3, while that of PP-aptmds was 3.31×10^-3 mol·cm^-3. In addition, the dielectric constant and dielectric loss of PPHP composite at 1 MHz could reach 2.61 and 0.0056, respectively.

Key words: Polybenzoxazine, Organosilicon, Composite, Dielectric constant

Manlin Yuan, Xin Lu, Xiaoyun Ma, Hao Lin, Angui Lu, Liyan Shao, Zhong Xin. Polybenzoxazine/organosilicon composites with low dielectric constant and dielectric loss[J]. 中国化学工程学报, 2023, 64(12): 241-249.

Manlin Yuan, Xin Lu, Xiaoyun Ma, Hao Lin, Angui Lu, Liyan Shao, Zhong Xin. Polybenzoxazine/organosilicon composites with low dielectric constant and dielectric loss[J]. Chinese Journal of Chemical Engineering, 2023, 64(12): 241-249.

参考文献

[1] L.X. Fang, J.F. Zhou, C.Q. He, Y.Q. Tao, C.Y. Wang, M.L. Dai, H.Y. Wang, J. Sun, Q.A. Fang, Understanding how intrinsic micro-pores affect the dielectric properties of polymers: An approach to synthesize ultra-low dielectric polymers with bulky tetrahedral units as cores, Polym. Chem. 11 (15) (2020) 2674–2680.
[2] S.H. Han, Y.N. Li, F.Y. Hao, H. Zhou, S.L. Qi, G.F. Tian, D.Z. Wu, Ultra-low dielectric constant polyimides: Combined efforts of fluorination and micro-branched crosslink structure, Eur. Polym. J. 143 (2021) 110206.
[3] Y. Yuan, S. Diao, C.D. Zhao, S.H. Ge, X. Wang, B.R. Duan, Preparation of hollow glass microsphere/organic silicone resin composite material with low dielectric constant by In-situ polymerization, Silicon 12 (6) (2020) 1417–1423.
[4] Z.L. Wang, X.R. Zhang, L. Weng, L.Z. Liu, Low dielectric constant and high toughness epoxy resin based on hyperbranched polyester grafted by flexible chain modified, J. Mater. Sci. 30 (6) (2019) 5936–5946.
[5] Y.Y. Ma, L. Xu, Z.A. He, J.W. Xie, L. Shi, M.Y. Zhang, W.L. Zhang, W.W. Cui, Tunable dielectric and other properties in high-performance sandwich-type polyimide films achieved by adjusting the porous structure, J. Mater. Chem. C 7 (24) (2019) 7360–7370.
[6] J.Q. Ren, P. Yang, Z.J. Peng, X.L. Fu, Novel Al₂Mo₃O₁₂-PTFE composites for microwave dielectric substrates, Ceram. Int. 47 (15) (2021) 20867–20874.
[7] H.B. Zhu, W.H. Hu, Y.D. Xu, B.H. Wang, D. Zheng, Y.Z. Fu, C.Y. Zhang, G.Z. Zhao, Z. Wang, Gradient structure based dual-robust superhydrophobic surfaces with high-adhesive force, Appl. Surf. Sci. 463 (2019) 427–434.
[8] J.A. Liu, X. Lu, Z. Xin, C.L. Zhou, Synthesis and surface properties of low surface free energy silane-functional polybenzoxazine films, Langmuir 29 (1) (2013) 411–416.
[9] K. Zeng, H. Li, H.X. Shi, J.Y. Wu, J.L. Xu, Y.T. Li, C.X. Zhao, Synthesis and thermal properties of silicon-containing benzoxazine, High Perform. Polym. 32 (1) (2020) 59–64.
[10] R. Yang, K. Zhang, Strategies for improving the performance of diallyl bisphenol A-based benzoxazine resin: Chemical modification via acetylene and physical blending with bismaleimide, React. Funct. Polym. 165 (2021) 104958.
[11] Z.J. Feng, M. Zeng, D.W. Meng, J.B. Chen, W.L. Zhu, Q.Y. Xu, J.X. Wang, A novel bio-based benzoxazine resin with outstanding thermal and superhigh-frequency dielectric properties, J. Mater. Sci. 31 (5) (2020) 4364–4376.
[12] K. Zhang, B.R. Hao, H. Ishida, Synthesis of a smart bisbenzoxazine with combined advantages of bismaleimide and benzoxazine resins and its unexpected formation of very high performance cross-linked polybenzoxazole, Polymer 223 (2021) 123703.
[13] J.L. Xu, H. Li, K. Zeng, G.X. Li, X.H. Zhao, C.X. Zhao, Curing kinetics and thermal stability of novel siloxane-containing benzoxazines, Thermochim. Acta 671 (2019) 119–126.
[14] A. Ábrahám, L. Kócs, E. Albert, B. Tegze, B. Szolnoki, N. Nagy, G. Sáfrán, P. Basa, Z. Hórvölgyi, Durability of microporous hybrid silica coatings: Optical and wetting properties, Thin Solid Films 699 (2020) 137914.
[15] Y.D. Zhao, M.L. Yuan, L.T. Wang, X. Lu, Z. Xin, Preparation of bio-based polybenzoxazine/pyrogallol/polyhedral oligomeric silsesquioxane nanocomposites: Low dielectric constant and low curing temperature, Macromol. Mater. Eng. 307 (3) (2022) 2100747.
[16] S.P. Asrafali, T. Periyasamy, R. Haldhar, S. Madhappan, S.C. Kim, Fabrication of SiO₂-reinforced polybenzoxazine composites and their thermal and dielectric properties, J. Polym. Res. 29 (5) (2022) 1–11.
[17] S. Kumar, A. Hariharan, M. Alagar, K. Dinakaran, Low-k and UV shielding polybenzoxazine nanocomposites synthesised from quinoline amine and bio-silica, Compos. Interfaces 28 (9) (2021) 905–923.
[18] A. Forchetti Casarino, S.A. Bortolato, N. Casis, D.A. Estenoz, M.E. Spontón, Novel polybenzoxazine and polybenzoxazine/epoxy thermosetting copolymers containing polysilsesquioxane nanostructures for high-performance thermal protection systems, Eur. Polym. J. 182 (2023) 111722.
[19] M.L. Yuan, X. Lu, Y.D. Zhao, S.W. Kuo, Z. Xin, Study of two novel siloxane-containing polybenzoxazines with intrinsic low dielectric constant, Polymer 245 (2022) 124572.
[20] C.L. Zhou, X. Lu, Z. Xin, J. Liu, Corrosion resistance of novel silane-functional polybenzoxazine coating on steel, Corros. Sci. 70 (2013) 145–151.
[21] R. Joseph, S.M. Zhang, W.T. Ford, Structure and dynamics of a colloidal silica–poly(methyl methacrylate) composite by 13C and 29Si MAS NMR spectroscopy, Macromolecules 29 (4) (1996) 1305–1312.
[22] Y.Y. Ma, Z.A. He, Z.W. Liao, J.W. Xie, H.Y. Yue, X. Gao, Facile strategy for low dielectric constant polyimide/silsesquioxane composite films: Structural design inspired from nature, J. Mater. Sci. 56 (12) (2021) 7397–7408.
[23] C.L. Zhou, M. Tao, J. Liu, Z. Xin, Thermal curing behavior of benzoxazine functional polysilsesquioxane nanospheres, Thermochim. Acta 678 (2019) 178295.
[24] L.E. Nielsen, Cross-linking–effect on physical properties of polymers, J. Macromol. Sci. C 3 (1) (1969) 69–103.
[25] H. Yee Low, H. Ishida, Structural effects of phenols on the thermal and thermo-oxidative degradation of polybenzoxazines, Polymer 40 (15) (1999) 4365–4376.
[26] S.W. King, D. Jacob, D. Vanleuven, B. Colvin, J. Kelly, M. French, J. Bielefeld, D. Dutta, M. Liu, D. Gidley, Film property requirements for hermetic low-k a-SiOxCyNz: H dielectric barriers, ECS J. Solid State Sci. Technol. 1 (6) (2012) N115–N122.
[27] V. Selvaraj, T.R. Raghavarshini, M. Alagar, Low temperature cure siloxane based hybrid renewable cardanol benzoxazine composites for coating applications, J. Polym. Environ. 27 (12) (2019) 2682–2696.
[28] Li, X.; Feng, J.; Zhang, S.; Tang, Y.; Hu, X.; Liu, X.; Liu, X. Epoxy/benzoxazinyl POSS nanocomposite resin with low dielectric constant and excellent thermal stability. J. Appl. Polym. Sci. 2020 138 49887-49895.
[29] X.D. Li, J.C. Feng, S.A. Zhang, Y. Tang, X.Y. Hu, X.P. Liu, X.Q. Liu, Epoxy/benzoxazinylPOSS nanocomposite resin with low dielectric constant and excellent thermal stability, J. Appl. Polym. Sci. 138 (8) (2021) 49887.

Polybenzoxazine/organosilicon composites with low dielectric constant and dielectric loss

Polybenzoxazine/organosilicon composites with low dielectric constant and dielectric loss

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