Preparation of Low-dielectric Permittivity Polyimide Resins with High Surface Activity from Chemically Bonded Hyperbranched Polysiloxane

Xiu-Ting Li; Xiao-Meng Zhu; Jie Dong; Xin Zhao; Qing-Hua Zhang

doi:10.1007/s10118-021-2585-0

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Preparation of Low-dielectric Permittivity Polyimide Resins with High Surface Activity from Chemically Bonded Hyperbranched Polysiloxane

ARTICLE | Updated：2021-06-18

- Preparation of Low-dielectric Permittivity Polyimide Resins with High Surface Activity from Chemically Bonded Hyperbranched Polysiloxane
- Chinese Journal of Polymer Science Vol. 39, Issue 9, Pages: 1200-1210(2021)
- Affiliations：
  
  1.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China
- Author bio：
  
  qhzhang@dhu.edu.cn
- Funds：
- DOI：10.1007/s10118-021-2585-0
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Xiu-Ting Li, Xiao-Meng Zhu, Jie Dong, et al. Preparation of Low-dielectric Permittivity Polyimide Resins with High Surface Activity from Chemically Bonded Hyperbranched Polysiloxane. [J]. Chinese Journal of Polymer Science 39(9):1200-1210(2021)
DOI：

Xiu-Ting Li, Xiao-Meng Zhu, Jie Dong, et al. Preparation of Low-dielectric Permittivity Polyimide Resins with High Surface Activity from Chemically Bonded Hyperbranched Polysiloxane. [J]. Chinese Journal of Polymer Science 39(9):1200-1210(2021) DOI： 10.1007/s10118-021-2585-0.

摘要

Abstract

Thermosetting resin matrix is the key component of advanced wave-transparent composites, where low dielectric constant, excellent processability, high thermal stability, as well as good bonding ability are required for resins. Herein, we prepared a series of phenylethynyl terminated polyimide (PI) resins by grafting amine-functionalized hyperbranched polysiloxane (HBPSi) to PI chains during the ,in situ, polymerization. The effects of HBPSi on the processability of oligomers, molecular packing, thermal stability, dielectric property and bonding ability to reinforce Kevlar fibers of the cured PI/HBPSi composite resins have been examined in detail. The dielectric constants of the cured composite resins were greatly reduced from 3.29 to 2.19 without compromising its processability and thermal stability. Meanwhile, the 10 wt% HBPSi-containing PI resin demonstrated better bonding ability to reinforce fibers with the interfacial shear strength (IFSS) of 37.64 MPa, compared with that of neat PI-6 matrix (27.34 MPa), and better adhesion to metal with the lap shear strength of 10.48 MPa, 50% higher than that of neat resin PI-6 (6.98 MPa). These resultant PI/HBPSi composite resins exhibit excellent comprehensive properties, indicating their great potential as low-dielectric constant resin matrix in radar radome.

关键词

Keywords

Hyperbranched polysiloxanePolyimide resinLow dielectric constantProcessabilityBonding ability

references

Sun, Z.; Huang, P.; Gu, A.; Liang, G.; Li, Y.; Dai, S. . Novel high-performance wave-transparent aluminum phosphate/cyanate ester composites . J. Appl. Polym. Sci. , 2012 . 123 1576 -1583 . DOI:10.1002/app.34695http://doi.org/10.1002/app.34695 .

Gu, J.; Li, Y.; Liang, C.; Tang, Y.; Lin, T.; Zhang, Y.; Kong, J.; Liu, H.; Guo, Z. . Synchronously improved dielectric and mechanical properties of wave-transparent laminated composites combining with outstanding thermal stability by incorporating iysozyme/POSS functionalized PBO fibers . J. Mater. Chem. C , 2018 . 6 7652 -7660 . DOI:10.1039/C8TC02391Chttp://doi.org/10.1039/C8TC02391C .

Liu, Z.; Zhang, J.; Tang, L.; Zhou, Y.; Lin, Y.; Wang, R.; Kong, J.; Tang, Y.; Gu, J. . Improved wave-transparent performances and enhanced mechanical properties for fluoride-containing PBO precursor modified cyanate ester resins and their PBO fibers/cyanate ester composites . Compos. B Eng. , 2019 . 178 107466 -107475 . DOI:10.1016/j.compositesb.2019.107466http://doi.org/10.1016/j.compositesb.2019.107466 .

Tang, L.; Dang, J.; He, M.; Li, J.; Kong, J.; Tang, Y.; Gu, J. . Preparation and properties of cyanate-based wave-transparent laminated composites reinforced by dopamine/POSS functionalized Kevlar cloth . Compos. Sci. Technol. , 2019 . 169 120 -126 . DOI:10.1016/j.compscitech.2018.11.018http://doi.org/10.1016/j.compscitech.2018.11.018 .

Li, X.; Liu, T.; Jiao, Y.; Dong, J.; Gan, F.; Zhao, X.; Zhang, Q. . Novel high-performance poly(benzoxazole-co-imide) resins with low dielectric constants and superior thermal stabilities derived from thermal rearrangement of ortho-hydroxy polyimide oligomers . Chem. Eng. J. , 2019 . 359 641 -651 . DOI:10.1016/j.cej.2018.11.175http://doi.org/10.1016/j.cej.2018.11.175 .

Dong, J.; Yang, C.; Cheng, Y.; Wu, T.; Zhao, X.; Zhang, Q. . Facile method for fabricating low dielectric constant polyimide fibers with hyperbranched polysiloxane . J. Mater. Chem. C , 2017 . 5 2818 -2825 . DOI:10.1039/C7TC00196Ghttp://doi.org/10.1039/C7TC00196G .

Cano, R. J.; Jensen, B. J. . Effect of molecular weight on processing and adhesive properties of the phenylethynyl-terminated polyimide LARCTM-PETI-5 . J. Adhesion , 1997 . 60 113 -123 . DOI:10.1080/00218469708014413http://doi.org/10.1080/00218469708014413 .

Ogasawara, T.; Ishida, Y.; Yokota, R.; Watanabe, T.; Aoi, T.; Goto, J. . Processing and properties of carbon fiber/Triple-A polyimide composites fabricated from imide oligomer dry prepreg . Compos. Part A Appl. Sci. Manuf. , 2007 . 38 1296 -1303 . DOI:10.1016/j.compositesa.2006.11.007http://doi.org/10.1016/j.compositesa.2006.11.007 .

Lei, X.; Chen, Y.; Qiao, M.; Tian, L.; Zhang, Q. . Hyperbranched polysiloxane (HBPSi)-based polyimide films with ultralow dielectric permittivity, desirable mechanical and thermal properties . J. Mater. Chem. C , 2016 . 4 2134 -2146 . DOI:10.1039/C5TC03391Hhttp://doi.org/10.1039/C5TC03391H .

Min, C.; Wu, T.; Yang, W.; Chen, C. . Functionalized mesoporous silica/polyimide nanocomposite thin films with improved mechanical properties and low dielectric constant . Compos. Sci. Technol. , 2008 . 68 1570 -1578 . DOI:10.1016/j.compscitech.2007.09.021http://doi.org/10.1016/j.compscitech.2007.09.021 .

Wu, T.; Dong, J.; Xu, G.; Gan, F.; Zhao, X.; Zhang, Q. . Attapulgite-reinforced polyimide hybrid aerogels with high dimensional stability and excellent thermal insulation property . Polymer , 2019 . 176 196 -205 . DOI:10.1016/j.polymer.2019.05.007http://doi.org/10.1016/j.polymer.2019.05.007 .

Zhang, X.; Sheng, S.; Pan, Y.; Huang, Z.; Liu, X. . Organosoluble, low dielectric constant and highly transparent fluorinated pyridine-containing poly(ether imide)s derived from new diamine: 4-(4-trifluoromethyl)phenyl-2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]pyridine . J. Macromol. Sci. A , 2019 . 56 234 -244 . DOI:10.1080/10601325.2019.1565545http://doi.org/10.1080/10601325.2019.1565545 .

Liu, H.; Zhai, L.; Bai, L.; He, M.; Wang, C.; Mo, S.; Fan, L. . Synthesis and characterization of optically transparent semi-aromatic polyimide films with low fluorine content . Polymer , 2019 . 163 106 -114 . DOI:10.1016/j.polymer.2018.12.045http://doi.org/10.1016/j.polymer.2018.12.045 .

Li, F.; Liu, J.; Liu, X.; Wang, Y.; Gao, X.; Meng, X.; Tu, G. . High performance soluble polyimides from ladder-type fluorinated dianhydride with polymorphism . Polymers , 2018 . 10 546 -563 . DOI:10.3390/polym10050546http://doi.org/10.3390/polym10050546 .

Wu, T.; Dong, J.; Gan, F.; Fang, Y.; Zhao, X.; Zhang, Q. . Low dielectric constant and moisture-resistant polyimide aerogels containing trifluoromethyl pendent groups . Appl. Surf. Sci. , 2018 . 440 595 -605 . DOI:10.1016/j.apsusc.2018.01.132http://doi.org/10.1016/j.apsusc.2018.01.132 .

Liao, W. H.; Yang, S. Y.; Hsiao, S. T.; Wang, Y. S.; Li, S. M.; Ma, C. C.; Tien, H. W.; Zeng, S. J. . Effect of octa(aminophenyl) polyhedral oligomeric silsesquioxane functionalized graphene oxide on the mechanical and dielectric properties of polyimide composites . ACS Appl. Mater. Interfaces , 2014 . 6 15802 -15812 . DOI:10.1021/am504342jhttp://doi.org/10.1021/am504342j .

Lei, X. F.; Chen, Y.; Zhang, H. P.; Li, X. J.; Yao, P.; Zhang, Q. Y. . Space survivable polyimides with excellent optical transparency and self-healing properties derived from hyperbranched polysiloxane . ACS Appl. Mater. Interfaces , 2013 . 5 10207 -10220 . DOI:10.1021/am402957shttp://doi.org/10.1021/am402957s .

Yang, C.; Dong, J.; Fang, Y.; Ma, L.; Zhao, X.; Zhang, Q. . Preparation of novel low-κ polyimide fibers with simultaneously excellent mechanical properties, UV-resistance and surface activity using chemically bonded hyperbranched polysiloxane . J. Mater. Chem. C , 2018 . 6 1229 -1238 . DOI:10.1039/C7TC05153Khttp://doi.org/10.1039/C7TC05153K .

Hanselmann, R.; Hoelter, D.; Frey, H. . Hyperbranched polymers prepared via the core-dilution/slow addition technique: computer simulation of molecular weight distribution and degree of branching . Macromolecules , 1998 . 31 3790 -3801 . DOI:10.1021/ma971197rhttp://doi.org/10.1021/ma971197r .

Uppuluri, S.; Keinath, S. E.; Tomalia, D. A.; Dvornic, P. R. Rheology of dendrimers. I. . Rheology of dendrimers. I. Newtonian flow behavior of medium and highly concentrated solutions of polyamidoamine (PAMAM) dendrimers in ethylenediamine (EDA) solvent . Macromolecules , 1998 . 31 4498 -4510 . DOI:10.1021/ma971199bhttp://doi.org/10.1021/ma971199b .

Kräuter, G.; Schumacher, A.; Gösele, U. . Low temperature silicon direct bonding for application in micromechanics: bonding energies for different combinations of oxides . Sensor. Actuat. A-Phys. , 1998 . 70 271 -275 . DOI:10.1016/S0924-4247(98)00102-2http://doi.org/10.1016/S0924-4247(98)00102-2 .

Ni, Y.; Zheng, S.; Nie, K. . Morphology and thermal properties of inorganic-organic hybrids involving epoxy resin and polyhedral oligomeric silsesquioxanes . Polymer , 2004 . 45 5557 -5568 . DOI:10.1016/j.polymer.2004.06.008http://doi.org/10.1016/j.polymer.2004.06.008 .

Romo-Uribe, A.; Reyes-Mayer, A.; Paredes-Pérez, M.; Lichtenhan, J.; Yañez-Lino, M.; Sarmiento-Bustos, E. . POSS driven chain disentanglements, decreased the melt viscosity and reduced O2 transmission in polyethylene . Polymer , 2019 . 165 61 -71 . DOI:10.1016/j.polymer.2019.01.024http://doi.org/10.1016/j.polymer.2019.01.024 .

Oh, S. Y.; Kang, T. J. . Electrorheological response of inorganic-coated multi-wall carbon nanotubes with core-shell nanostructure . Soft Matter , 2014 . 10 3726 -3737 . DOI:10.1039/c3sm52962bhttp://doi.org/10.1039/c3sm52962b .

Harms, S.; Rätzke, K.; Faupel, F.; Schneider, G. J.; Willner, L.; Richter, D. . Free volume of interphases in model nanocomposites studied by positron annihilation lifetime spectroscopy . Macromolecules , 2010 . 43 10505 -10511 . DOI:10.1021/ma1022692http://doi.org/10.1021/ma1022692 .

Jia, M.; Li, Y.; He, C.; Huang, X. . Soluble perfluorocyclobutyl aryl ether-based polyimide for high-performance dielectric material . ACS Appl. Mater. Interfaces , 2016 . 8 26352 -26358 . DOI:10.1021/acsami.6b09383http://doi.org/10.1021/acsami.6b09383 .

Pandey, S.; Rath, S. K.; Samui, A. B. . Structure-thermomechanical property correlations of highly branched siloxane-urethane networks . Ind. Eng. Chem. Res. , 2012 . 51 3531 -3540 . DOI:10.1021/ie200629whttp://doi.org/10.1021/ie200629w .

Hao, J.; Wei, Y.; Li, X.; Mu, J. . Poly(arylene ether ketone)s with low dielectric constants derived from polyhedral oligomeric silsesquioxane and difluorinated aromatic ketones . J. Appl. Polym. Sci. , 2018 . 135 46084 DOI:10.1002/app.46084http://doi.org/10.1002/app.46084 .

Kim, Y. S.; Cho, H. J.; Lee, H.; Kim, W. Y.; Jung, Y. C.; Lee, S. Y. . Development of a multi-functional acrylic urethane coating with high hardness and low surface energy . Prog. Org. Coat. , 2020 . 147 105748 DOI:10.1016/j.porgcoat.2020.105748http://doi.org/10.1016/j.porgcoat.2020.105748 .

Chen, Z.; Zhou, Y.; Wu, Y.; Liu, S.; Huang, H.; Zhao, J. . Fluorinated polyimide with polyhedral oligomeric silsesquioxane aggregates: toward low dielectric constant and high toughness . Compos. Sci. Technol. , 2019 . 181 107700 DOI:10.1016/j.compscitech.2019.107700http://doi.org/10.1016/j.compscitech.2019.107700 .

Atawa, B.; Correia, N. T.; Couvrat, N.; Affouard, F.; Coquerel, G.; Dargent, E.; Saiter, A. . Molecular mobility of amorphous N-acetyl-α-methylbenzylamine and Debye relaxation evidenced by dielectric relaxation spectroscopy and molecular dynamics simulations . Phys. Chem. Chem. Phys. , 2019 . 21 702 -717 . DOI:10.1039/C8CP04880Khttp://doi.org/10.1039/C8CP04880K .

Dlubek, G.; Buchhold, R.; Hübner, Ch.; Nakladal, A. . Water in local free volumes of polyimides: a positron lifetime study . Macromolecules , 1999 . 32 2348 -2355 . DOI:10.1021/ma981381shttp://doi.org/10.1021/ma981381s .

Cao, J.; Wang, D.; An, P.; Zhang, J.; Feng, S. . Highly compression-tolerant and durably hydrophobic macroporous silicone sponges synthesized by a one-pot click reaction for rapid oil/water separation . J. Mater. Chem. A , 2018 . 6 18025 -18030 . DOI:10.1039/C8TA07327Ahttp://doi.org/10.1039/C8TA07327A .

Cheng, Z.; Zhang, L.; Jiang, C.; Dai, Y.; Meng, C.; Luo, L.; Liu, X. . Aramid fiber with excellent interfacial properties suitable for resin composite in a wide polarity range . Chem. Eng. J. , 2018 . 347 483 -492 . DOI:10.1016/j.cej.2018.04.149http://doi.org/10.1016/j.cej.2018.04.149 .

Choudhury, M. R.; Debnath, K. . Analysis of tensile failure load of single-lap green composite specimen welded by high-frequency ultrasonic vibration . Mater. Today: Proc. , 2020 . 28 739 -744 . DOI:10.1016/j.matpr.2019.12.290http://doi.org/10.1016/j.matpr.2019.12.290 .

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