Skip to main content

Advertisement

SpringerLink
Log in

New fluorinated copoly(pyridine ether imide)s derived from 4,4′-oxydianiline, pyromellitic dianhydride and 4-(4-trifluoromethylphenyl)-2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]pyridine

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

A new aromatic diamine, 4-(4-trifluoromethylphenyl)-2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]pyridine (9FPBAPP), was prepared from 4-(4-trifluoromethylphenyl)-2,6-bis(4-hydroxyphenyl)pyridine with 2-chloro-5-nitrotrifluoromethylbenzene by substitution and reduction reactions successively. A series of fluorinated copoly(pyridine ether imide)s were prepared from 4,4′-oxydianiline (ODA), pyromellitic dianhydride and 9FPBAPP by thermal imidization procedure with various mole ratios of ODA and 9FPBAPP. All polymers were amorphous and soluble in organic solvents such as N,N-dimethylacetamide and N-methyl-2-pyrrolidone, and had Tgs of 285.8–310.0 °C, 5% weight loss temperature of 545.5–565.7 °C in nitrogen atmosphere. Tough and flexible polymer films also exhibited excellent mechanical properties with tensile strengths of 76.3–96.5 MPa, tensile moduli of 1.3–1.8 GPa, elongations at break of 15.6–25.1%, low dielectric constants of 3.04–3.51 (1 MHz) and water uptake of 0.44–0.65%, as well as high optical transparency with an ultraviolet–visible absorption cutoff wavelength in the 382–412 nm range.

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

Similar content being viewed by others

References

  1. Ghosh MK, Mittal KL (1996) Polyimides: fundamentals and applications. Marcel Dekker, New York

    Google Scholar 

  2. Mittal KL (2009) Polyimides and other high temperature polymers. VSP/Brill, Leiden

    Google Scholar 

  3. Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS (2012) Advanced polyimide materials: syntheses, physical properties and applications. Prog Polym Sci 37:907–974

    Article  CAS  Google Scholar 

  4. Sroog CE (1991) Polyimides. Prog Polym Sci 16:561–694

    Article  CAS  Google Scholar 

  5. Boise AI (1986) Optimizing polyimide cure using infrared spectroscopy and a factorial design. J Appl Polym Sci 32:4043–4048

    Article  Google Scholar 

  6. Dine-Hart RA, Wright WW (1971) A study of some properties of aromatic imides. Macromol Chem 143:189–206

    Article  CAS  Google Scholar 

  7. Hasegawa M, Horie K (2001) Photophysics, photochemistry, and optical properties of polyimides. Prog Polym Sci 26:259–335

    Article  CAS  Google Scholar 

  8. Maktouf LB, Ghorbel I, Afli A, Abid S, Gandini A (2011) Polyimides based on furanic diamines and aromatic dianhydrides: synthesis, characterization and properties. Polym Bull 67:1111–1122

    Article  CAS  Google Scholar 

  9. Liu JT, Chen GF, Fang XZ (2016) Preparation, characterization, and properties of poly(thioether imide)s from isomeric bis(chlorophthalimide)s and bisthiophenols. High Perform Polym 28:64–74

    Article  CAS  Google Scholar 

  10. Nabeshima S, Morikawa A (2015) Synthesis and properties of polyimides having a hexaphenylbenzene unit. High Perform Polym 27:772–781

    Article  CAS  Google Scholar 

  11. Hariharan A, Kumar S, Alagar M, Dinakaran K, Subramanian K (2018) Synthesis, photophysical and electrochemical properties of polyimides of tetraaryl imidazole. Polym Bull 75:93–107

    Article  CAS  Google Scholar 

  12. Rafiee Z, Khalili S (2013) Synthesis and characterization of highly soluble and thermally stable new polyimides based on 3,5-diamino benzoyl amino phenyl-14H-dibenzoxanthene. Polym Bull 70:2423–2435

    Article  CAS  Google Scholar 

  13. Wen PS, He R, Li X-D, Lee M-H (2017) Syntheses and characterizations of high refractive index and low birefringence polyimides containing spirobi.uorene in the side chain. Polymer 117:76–83

    Article  CAS  Google Scholar 

  14. Hsiao S-H, Lee C-T, Chern Y-T (1999) Synthesis and properties of new adamantane-based poly(ether imide)s. J Polym Sci, Part A: Polym Chem 37:1619–1628

    Article  CAS  Google Scholar 

  15. Yi L, Li CY, Huang W, Yan DY (2016) Soluble and transparent polyimides with high T g from a new diamine containing tert-butyl and fluorene units. J Polym Sci Part A: Polym Chem 54:976–984

    Article  CAS  Google Scholar 

  16. Ghaemy M, Alizadeh R (2009) Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2,4,5-triaryl imidazole pendent group. Eur Polym J 45:1681–1685

    Article  CAS  Google Scholar 

  17. Wu ZL, Han BC, Zhang CH, Zhu DY, Gao LX, Ding MX, Yang ZH (2012) Novel soluble and optically active polyimides containing axially asymmetric 9,9′-spirobifluorene units: synthesis, thermal, optical and chiral properties. Polymer 53:5706–5716

    Article  CAS  Google Scholar 

  18. Reddy DS, Shu CF, Wu FI (2002) Synthesis and characterization of soluble polyimides derived from 2,2′-bis(3,4-dicarboxyphenoxy)-9,9′-spirobifluorene dianhydride. J Polym Sci, Part A: Polym Chem 40:262–268

    Article  CAS  Google Scholar 

  19. Liu YW, Zhang Y, Lan Q, Qin ZX, Liu SW, Zhao CY, Chi ZG, Xu JR (2013) Synthesis and properties of high-performance functional polyimides containing rigid nonplanar conjugated tetraphenylethylene moieties. J Polym Sci, Part A: Polym Chem 51:1302–1314

    Article  CAS  Google Scholar 

  20. Wang XL, Li YF, Gong CL, Zhang SJ, Ma T (2007) Synthesis and characterization of novel soluble pyridine-containing polyimides based on 4-phenyl-2,6-bis[4-(4-aminophenoxy)phenyl]pyridine and various aromatic dianhydrides. J Appl Polym Sci 104:212–219

    Article  CAS  Google Scholar 

  21. Amutha N, Tharakan SA, Sarojadevi M (2015) Synthesis and characterization of new soluble polyimides based on pyridine unit with flexible linkages. High Perform Polym 27:979–989

    Article  CAS  Google Scholar 

  22. Yang FC, Wang J, Chen L, Wang X, Chen X-Y, Zhang X (2015) Soluble and degradable polyimides with phenyl-2-pyridyl ether structure: synthesis and characterization. Chin J Polym Sci 33:481–489

    Article  CAS  Google Scholar 

  23. Wu GL, Liu JG, Li ZB, Ge Z-Y, Fan L, Yang S-Y (2005) Synthesis and characterization of organo-soluble fluorinated polyimides from 4,4′-bis(3-amino-5-trifluoromethylphenoxy)-biphenyl and various aromatic dianhydrides. Chin J Polym Sci 23:55–61

    Article  CAS  Google Scholar 

  24. Kim SD, Lee S, Heo J, Kim SY, Chung IS (2013) Soluble polyimides with trifluoromethyl pendent groups. Polymer 54:5648–5654

    Article  CAS  Google Scholar 

  25. Yeo H, Goh M, Ku B-C, You N-H (2015) Synthesis and characterization of highly-fluorinated colorless polyimides derived from 4,4′-((perfluoro-[1,10-biphenyl]-4,4′-diyl)bis(oxy))bis(2,6-dimethylaniline) and aromatic dianhydrides. Polymer 76:280–286

    Article  CAS  Google Scholar 

  26. Tsai CL, Yen HJ, Liou GS (2016) Highly transparent polyimide hybrids for optoelectronic applications. React Funct Polym 108:2–30

    Article  CAS  Google Scholar 

  27. Li X, Liu X-L, Cheng L-J, Jiang J-W, Sheng S-R (2014) Synthesis and properties of poly(aryl ether ketone)s with 2,6-diphenylpyridyl moieties and 4-trifluoromethylphenyl side groups. J Fluorine Chem 157:30–34

    Article  CAS  Google Scholar 

  28. Gerber AH (1973) Thermally stable polymers derived from 2,3,5,6-tetraaminopyridine. J Polym Sci Part A: Polym Chem 11:1703–1719

    Article  CAS  Google Scholar 

  29. Niu HQ, Huang MJ, Qi SL, Han EL, Tian GF, Wang XD, Wu DZ (2013) High-performance copolyimide fibers containing quinazolinone moiety: preparation, structure and properties. Polymer 54:1700–1708

    Article  CAS  Google Scholar 

  30. Fang C, Zhou YM, He M, Bu XH, Yin K, Weng JJ, Zhang ZW (2013) Synthesis and characterization of ternary-copolymer of soluble fluorinated polyimides based on 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene. J Appl Polym Sci 128:80–88

    Article  CAS  Google Scholar 

  31. McCulloch I, Yoon H (1995) Fluorinated NLO polymers with improved optical transparency in the near infrared. J Polym Sci, Part A: Polym Chem 33:1177–1183

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The financial support for this research provided by the National Natural Science Foundation of China (Nos. 21464007, 21564005, 51763012), the Training Program for Science and Technology Leaders in Major Subjects of Jiangxi Province of China (No. 20113BCB22012), the Ground Project for Science and Technology of Jiangxi Universities (No. KJLD14022) and the Research Program of Jiangxi Province Department of Education (No. GJJ14236) is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Key Laboratory of Functional Small Organic Molecule of Ministry of Education, Jiangxi Normal University, Nanchang, 330022, China

    Yu-Ting Zhou, Xiao-Ling Liu, Mei-Hong Wei, Cheng Song, Zhen-Zhong Huang & Shou-Ri Sheng

  2. College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, China

    Yu-Ting Zhou, Xiao-Ling Liu, Mei-Hong Wei, Cheng Song, Zhen-Zhong Huang & Shou-Ri Sheng

Authors
  1. Yu-Ting Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiao-Ling Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mei-Hong Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Cheng Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhen-Zhong Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Shou-Ri Sheng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Xiao-Ling Liu or Shou-Ri Sheng.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhou, YT., Liu, XL., Wei, MH. et al. New fluorinated copoly(pyridine ether imide)s derived from 4,4′-oxydianiline, pyromellitic dianhydride and 4-(4-trifluoromethylphenyl)-2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]pyridine. Polym. Bull. 76, 4139–4155 (2019). https://doi.org/10.1007/s00289-018-2585-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-018-2585-6

Keywords

Search

Navigation