Skip to main content

Advertisement

SpringerLink
Log in

Dielectric properties of polyethersulfone copolymers containing bisphenol S and six fluorine hexafluorobisphenolA (6AF) segments

  • Original Paper
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

In this study, a series of fluorinated polyethersulfone (PES-6AF) copolymers with intrinsic low-dielectric-constants are prepared by the introduction of fluorine-containing group, which are derived from the polycondensation reaction of 4,4′-dichlorophenyl sulfone (DCS), bisphenol S (BPS) and six fluorine hexafluorobisphenolA (6AF) compounds by nucleophilic aromatic substitution. Different proportions of PES-6AF copolymers show high glass transition temperatures (Tg) ranging from 206 °C to 230 °C, and the thermal decomposition temperatures of PES-6AF copolymers are up to 500 °C under N2 atmospheres. The PES-6AF copolymers display outstanding tensile strength (62–69 MPa). Added different proportions of 6AF into the PES-6AF copolymers could improve dielectric property and decrease dielectric constant (k) from 3.6 to 2.5 at 1 kHz. In addition, the dielectric properties were found to be relatively stable until the Tg, it is because that the 6AF units were existed in the molecular backbone. Furthermore, the PES-6AF copolymers were soluble in many common solvents and could be made the molten films using DMF as solvent.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Farrell R, Goshal T, Cvelbar U, Petkov N, Morris AM (2011) Advances in ultralow dielectric constant ordered porous materials. Soc Interface 20:39–46

    CAS  Google Scholar 

  2. Grill A, Gates S, Ryan T, Nguyen S, Priyadarshini D (2014) Progress in the development and understanding of advanced low k and ultralow k dielectrics for very large-scale integrated interconnects—state of the art. Appl Phys Rev 1:011306

    Article  Google Scholar 

  3. Yl Q, Yin XD, Zhu TY, Li H, Tang CB (2018) Dielectric polymers with novel chemistry, compositions and architectures. Prog Polym Sci 80:153–162

    Article  Google Scholar 

  4. Kim CB, Woo DH, Lee HC (2012) Design of a readout circuit for improving the SNR of satellite infrared time delay and integration arrays. IEICE Trans Electron E95:1406–1414

    Article  Google Scholar 

  5. Quan B, Shi WH, Ong SJH, Lu XC, Wang PLY, Ji GB, Guo YF, Zheng LR, Xu ZCJ (2019) Defect engineering in two common types of dielectric materials for electromagnetic absorption applications. Adv Funct Mater 29:1901236

  6. Cheng YL, Hung WJ, Chen GS, Fang JS, Lee CY (2018) Comparison of various low dielectric constant materials. Thin Solid Films 660:871–878

    Article  CAS  Google Scholar 

  7. Zhan YQ, Zhang JM, Zhao SM, He SJ (2019) Thermally stable and dielectric nanocomposite based on poly (arylene ether nitrile) and BaTiO3 functionalized by modified mussel-inspired route. J Polym Res 26:77

    Article  Google Scholar 

  8. Volksen W, Miller R, Dubois G (2010) Low dielectric constant materials. Chem Rev 110:56–110

    Article  CAS  Google Scholar 

  9. Wang JJ, Zhou JF, Wang L, Jin KK, Sun J, Fang Q (2017) A new fluorinated polysiloxane with good optical properties and low dielectric constant at high frequency based on easily available tetraethoxysilane (TEOS). Macromolecules 50:9394–9402

    Article  CAS  Google Scholar 

  10. Wei JJ, Ju TX, Huang W, Song JL, Yan N, Wang FY, Shen AQ, Li ZP, Zhu L (2019) High dielectric constant dipolar glass polymer based on sulfonylated poly (ether ether ketone). Polymer 178:121688

    Article  Google Scholar 

  11. Zhuang YB, Seong JG, Wang G, Lee MJ, Lee YM, Guiver MD, Jo HJ (2014) Effect of isomerism on molecular packing and gas transport properties of poly (benzoxazole-co-imide)s. Macromolecules 47:7947–7957

    Article  CAS  Google Scholar 

  12. Zhao YT, Wang X, Ren YW, Pei DS (2018) Mesh-embedded polysulfone/sulfonated polysulfone supported thin film composite membranes for forward osmosis. ACS Appl Mater Interfaces 10:2918–2928

    Article  CAS  Google Scholar 

  13. Li S, Pang JH, Chen Z, Liu D, Han YT, Wang KQ, Jiang ZH, Huang S (2019) A high-performance anion exchange membrane based on poly (arylene ether sulfone) with a high concentration of quaternization units. J Membrane Sci 589:117266

    Article  Google Scholar 

  14. Tashvigh A, Luo L, Chung T, Weber M, Maletzko C (2018) A novel ionically cross-linked sulfonated polyphenylsulfone (sPPSU) membrane for organic solvent nanofiltration (OSN). J Membrane Sci 545:221–228

    Article  Google Scholar 

  15. You Y, Liu S, Tu L, Wang YJ, Zhan CH, Du XY, Wei RB, Liu XB (2019) Controllable fabrication of poly (arylene ether nitrile) dielectrics for thermal-resistant film capacitors. Macromolecules 52:5850–5859

    Article  CAS  Google Scholar 

  16. Shukla D, Negi YS, Uppadhyaya JS, Kumar V (2012) Synthesis and modification of poly (ether ether ketone) and their properties: a review. Polym Rev 52:189–228

    Article  CAS  Google Scholar 

  17. Huang YW, Liu LL, Zhang SB, Yu HT, Yang JX (2018) Polycarbosilane-modified styrene-based polymers with ultra-low dielectric constant, greatly enhanced mechanical strength and thermal stability. Eur Polym J 98:347–353

    Article  CAS  Google Scholar 

  18. Wang B, Shang YR, Ma Z, Pan L, Li YS (2017) Non-porous ultralow dielectric constant materials based on novel silicon-containing cycloolefin copolymers with tunable performance. Polymer 116:105–112

    Article  CAS  Google Scholar 

  19. Zhang S, Yan YH, Li XD, Fan HJ, Ran QC, Fu Q, Gu Y (2018) A novel ultralow-k nanocomposites of benzoxazinyl modified polyhedral oligomeric silsesquioxane and cyanate ester. Eur Polym J 103:124–132

    Article  CAS  Google Scholar 

  20. Tkachenko IM, Kononevich YN, Kobzar YL, Purikova O, Yakovlev Y, Shevchenko VV, Khalakhan I, Yakovlev Y (2018) Low dielectric constant silica-containing cross-linked organic-inorganic materials based on fluorinated poly (arylene ether)s. Polymer 157:131–138

    Article  CAS  Google Scholar 

  21. Bucholz TL, Li SP, Loo YL (2008) Ultralow-k materials derived from poly(d,l-lactide-b-pentafluorostyrene) diblock copolymers. J Mater Chem 18:530–536

    Article  CAS  Google Scholar 

  22. Lv PX, Dong ZX, Dai XM, Wang HF, Qiu XP (2018) Synthesis and properties of ultralow dielectric porous polyimide films containing adamantane. Polym Chem 56:549–559

    Article  CAS  Google Scholar 

  23. Zhang PP, Zhao JP, Zhang K, Wu YY, Li Y (2018) Effect of co-solvent on the structure and dielectric properties of porous polyimide membranes. J Phys D-Appl Phys 51:215305

    Article  Google Scholar 

  24. Wang GL, Zhao GQ, Dong GW, Song LB, Park CB (2018) Lightweight, thermally insulating, and low dielectric microcellular high-impact polystyrene (HIPS) foams fabricated by high-pressure foam injection molding with mold opening. J Mater Chem 6:12294–12305

    CAS  Google Scholar 

  25. Krause B, Koops GH, Wessling M, Wubbenhorst M, Turnhout VJ, Nico FA, Vegt VD (2002) Ultralow-k dielectrics made by supercritical foaming of thin polymer films. Adv Mater 14:1041–1046

    Article  CAS  Google Scholar 

  26. Asghar H, Ilyas A, Tahir Z, Li X, Khan A (2018) Fluorinated and sulfonated poly (ether ether ketone) and Matrimid blend membranes for CO2 separation. Sep Purif Technol 203:233–241

    Article  CAS  Google Scholar 

  27. Yin XD, Feng YY, Zhao Q, Li Y, Li SW, Feng W, Hu WP, Dong HL (2018) Highly transparent, strong, and flexible fluorographene/fluorinated polyimide nanocomposite films with low dielectric constant. J Mater Chem 6:6378–6384

    CAS  Google Scholar 

  28. Hu ZX, Lu Y, Zhang XL, Yan XB, Li N, Chen SW (2018) Fluorinated poly (ether sulfone) ionomers with disulfonated naphthyl pendants for proton exchange membrane applications. Front Mater Sci 12:156–167

    Article  Google Scholar 

  29. Gao Q, Pan XT, Buregeya PI, Lu Y, Zhang XL, Yan XB, Hu ZX, Chen SW (2018) Stable anion exchange membranes derived from fluorinated poly (aryl ethers) with quaternized fluorene units for fuel cell applications. J Appl Polym Sci 135:46301

    Article  Google Scholar 

  30. Tsuchiya K, Ishii H, Shibasaki YJ, Ando SJ, Ueda M (2004) Synthesis of a novel poly (binaphthylene ether) with a low dielectric constant. Macromolecules 37:4794–4797

    Article  CAS  Google Scholar 

  31. Jia MC, Zhou MT, Li YJ, Lu GL, Huang XY (2018) Construction of semi-fluorinated polyimides with perfluorocyclobutyl aryl ether-based side chains. Polym Chem 9:920–930

    Article  CAS  Google Scholar 

  32. Luo YJ, Jin KK, He CQ, Wang JJ, Sun J, He FK, Zhou JF, Wang YQ, Fang Q (2016) An intrinsically microporous network polymer with good dielectric properties at high frequency. Macromolecules 49:7314–7321

    Article  CAS  Google Scholar 

  33. Zheng XY, Pu ZJ, Hu LQ, Tian YH, Xia JL, Cheng J, Zhong JC (2019) Synthesis and properties of high performance polysulfone resin with low dielectric constant and dielectric loss. J Mater Sci-Mater Electron 30:18168–18176

    Article  CAS  Google Scholar 

  34. Lee CG, Khalifehzadeh R, Ratner BD, Boydston AJ (2018) Facile synthesis of fluorine-substituted polylactides and their amphiphilic block copolymers. Macromolecules 51:1280–1289

    Article  CAS  Google Scholar 

  35. Kang JW, Kim J, Lee WY, Lee J, Kim JJ (2001) Low-loss fluorinated poly (arylene ether sulfide) waveguides with high thermal stability. J Lightwave Technol 19:872–875

    Article  CAS  Google Scholar 

  36. Zou XQ, Yang XL, Xu MZ, Jia K, Liu XB (2015) Curing behaviors and properties of allyl- and benzoxazine-functional phthalonitrile with improved processability. J Polym Res 23:2

    Article  Google Scholar 

  37. Pu ZJ, Hu LQ, Tian YH, Zheng XY, Zhong JC, Liu XB (2018) Synthesis and properties of novel organosoluble copoly (arylene ether nitriles) containing thioether moiety. J Polym Res 25:100

    Article  Google Scholar 

  38. Hu WB, You Y, Tong LF, Wang YJ, Wei RB, Liu XB (2019) Preparation and physical properties of polyarylene ether nitrile and polyarylene ether sulfone random copolymers. High Perform Polym 31:686–693

    Article  CAS  Google Scholar 

  39. Tong LF, Lei XT, Yang GY, Liu XB (2019) Self-toughening and self-enhancement poly (arylene ether nitrile) with low dielectric constant by solid crosslinking reaction. Polymers 11:1403

    Article  Google Scholar 

  40. Pu ZJ, Zheng XY, Xia JL, Zhong JC (2020) Novel low-dielectric-constant fluorine-functionalized polysulfone with outstanding comprehensive properties. Polym Int 69:604–610

    Article  CAS  Google Scholar 

  41. Wei RB, Wang JL, Zhang HX, Han WH, Liu XB (2017) Crosslinked polyarylene ether nitrile interpenetrating with zinc ion bridged graphene sheet and carbon nanotube network. Polymers 9(8):342

    Article  Google Scholar 

Download references

Acknowledgements

The authors wish to thank for the Opening Project of Key Laboratories of Fine Chemicals and Surfactants in Sichuan Provincial Universities (2018JXY04), Opening Project of Material Corrosion and Protection Key Laboratory of Sichuan province (2019CL04) and Major Project of Education Department in Sichuan (18ZA0346), Key science and technology planning project of Zigong (2019YYJC04).

Author information

Authors and Affiliations

  1. College of Materials Science and Engineering, Material Corrosion and Protection Key Laboratory of Sichuan province, Key Laboratories of Fine Chemicals and Surfactants, Sichuan Provincial Universities, Sichuan University of Science & Engineering, Zigong, 643000, China

    Jialing Xia, Zejun Pu, Xiaoyi Zheng, Linqing Hu & Xianguang Zeng

Authors
  1. Jialing Xia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zejun Pu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiaoyi Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Linqing Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xianguang Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jiachun Zhong
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Jialing Xia and Zejun Pu contributed equally to this work, and they are the co-first author. Besides, all the authors approved the final version of the manuscript.

Corresponding author

Correspondence to Zejun Pu.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xia, J., Pu, Z., Zheng, X. et al. Dielectric properties of polyethersulfone copolymers containing bisphenol S and six fluorine hexafluorobisphenolA (6AF) segments. J Polym Res 27, 289 (2020). https://doi.org/10.1007/s10965-020-02267-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-020-02267-2

Keywords

Search

Navigation