Skip to main content
SpringerLink
Log in

Low dielectric constant and organosolubility of polyimides derived from unsymmetric phthalic-thioether-naphthalic dianhydrides

  • Published:
Journal of Materials Science Aims and scope Submit manuscript

Abstract

A series of polyimides (PIs) with low dielectric constant were synthesized via a polycondensation from two new unsymmetric phthalic-thioether-naphthalic dianhydride isomers which were synthesized from 3- or 4-chlorophthalic anhydride by a four-step procedure. The introduction of the unsymmetric phthalic-thioether-naphthalic dianhydride into polymer backbone is regarded as an effective way to increase the free volume and decrease the intermolecular force and packing ability of the resulting polymers. Thus, the novel PIs exhibit low dielectric constant, low moisture absorption good solubility, high modulus, and high glass transition temperature. The polyimides show good solubility in phenol, dipolar aprotic solvents, and other common organic solvents. In addition, the isomeric effect of 3- and 4-thioether-linked phthalic anhydride on the properties of PIs was discussed.

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

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

Similar content being viewed by others

References

  1. Sroog CE (1991) Prog Polym Sci 16(4):561

    Article  CAS  Google Scholar 

  2. Hasegawa M, Horie K (2001) Prog Polym Sci 26(2):259

    Article  CAS  Google Scholar 

  3. Eastmond GC, Paprotny J (1995) Macromolecules 28(7):2140

    Article  CAS  Google Scholar 

  4. Inoue T, Kakimoto M-a, Imai Y, Watanabe J (1995) Macromolecules 28(18):6368

    Article  CAS  Google Scholar 

  5. Tamai S, Yamaguchi A, Ohta M (1996) Polymer 37(16):3683

    Article  CAS  Google Scholar 

  6. Yang CP, Su YY, Wen SJ, Hsiao SH (2006) Polymer 47(20):7021

    Article  CAS  Google Scholar 

  7. Chern YT, Shiue HC (1997) Macromolecules 30(16):4646

    Article  CAS  Google Scholar 

  8. Chern YT, Shiue HC (1997) Macromolecules 30(19):5766

    Article  CAS  Google Scholar 

  9. Eastmond GC, Gibas M, Paprotny J (1999) Eur Polym J 35(12):2097

    Article  CAS  Google Scholar 

  10. Hsiao SH, Li CT (1998) Macromolecules 31(21):7213

    Article  CAS  Google Scholar 

  11. Hsiao SH, Chung CL, Lee ML (2004) J Polym Sci Part A Polym Chem 42(4):1008

    Article  CAS  Google Scholar 

  12. Yang CP, Su YY (2006) J Polym Sci Part A Polym Chem 44(9):3140

    Article  CAS  Google Scholar 

  13. Yang CP, Su YY, Hsiao SH (2006) J Polym Sci Part A Polym Chem 44(20):5909

    Article  CAS  Google Scholar 

  14. Wang CY, Li G, Zhao XY, Jiang JM (2009) J Polym Sci Part A Polym Chem 47(13):3309

    Article  CAS  Google Scholar 

  15. Al-Masri M, Kricheldorf HR, Fritsch D (1999) Macromolecules 32(23):7853

    Article  CAS  Google Scholar 

  16. Hsiao SH, Yang CY, Yang CY (1997) J Polym Sci Part A Polym Chem 35(8):1487

    Article  CAS  Google Scholar 

  17. Chou CH, Reddy DS, Shu CF (2002) J Polym Sci Part A Polym Chem 40(21):3615

    Article  CAS  Google Scholar 

  18. Fang XZ, Yang ZH, Zhang SB, Gao LX, Ding MX (2002) Macromolecules 35(23):8708

    Article  CAS  Google Scholar 

  19. Lin SH, Li F, Cheng SZD, Harris FW (1998) Macromolecules 31(7):2080

    Article  CAS  Google Scholar 

  20. Li QX, Fang XZ, Wang Z, Gao LX, Ding MX (2003) J Polym Sci Part A Polym Chem 41(21):3249

    Article  CAS  Google Scholar 

  21. Evans TL, Williams FJ, Donahue PE, Grade MM (1984) Polym Prepr (Am Chem Soc Div Polym Chem) 25:268

    CAS  Google Scholar 

  22. Ding MX, Li HY, Yang ZH, Li YS, Zhang J, Wang XQ (1996) J Appl Polym Sci 59(6):923

    Article  CAS  Google Scholar 

  23. Bell VL, Stump BL, Gager H (1976) J Polym Sci Polym Chem Ed 14(9):2275

    Article  CAS  Google Scholar 

  24. Havens SJ, Hergenrother PM (1992) J Polym Sci Part A Polym Chem 30(6):1209

    Article  CAS  Google Scholar 

  25. Ding MX (2007) Prog Poly Sci 32(6):623

    Article  CAS  Google Scholar 

  26. Dingemans TJ, Mendes E, Hinkley JJ, Weiser ES, StClair TL (2008) Macromolecules 41(7):2474

    Article  CAS  Google Scholar 

  27. Chern YT, Tsai JY (2008) Macromolecules 41(24):9556

    Article  CAS  Google Scholar 

  28. Eastmond GC, Paprotny J, Pethrick RA, Santamaria-Mendia FA (2006) Macromolecules 39(22):7534

    Article  CAS  Google Scholar 

  29. Chung IS, Kim SY (2000) Macromolecules 33(9):3190

    Article  CAS  Google Scholar 

  30. Wang JY, Liao GX, Liu C, Jian XG (2004) J Polym Sci Part A Polym Chem 42(23):6089

    Article  CAS  Google Scholar 

  31. Choi H, Chung IS, Hong K, Park CE, Kim SY (2008) Polymer 49(11):2644

    Article  CAS  Google Scholar 

  32. Wang CY, Li G, Jiang JM (2009) Polymer 50(7):1709

    Article  CAS  Google Scholar 

  33. Sek D, Wanic A, Schab-Balcerzak E (1997) J Polym Sci Part A Polym Chem 35(3):539

    Article  CAS  Google Scholar 

  34. Gao JP, Wang ZY (1995) J Polym Sci Part A Polym Chem 33(10):1627

    Article  CAS  Google Scholar 

  35. Rusanov AL (1994) Adv Polym Sci 111:115

    Article  CAS  Google Scholar 

  36. Sek D, Wanic A, Schab-Balcerzak E (1993) Polymer 34:2440

    Article  CAS  Google Scholar 

  37. Sek D, Wanic A, Schab-Balcerzak E (1995) J Polym Sci Part A Polym Chem 33(3):547

    Article  CAS  Google Scholar 

  38. Shao Y, Li YF, Zhao X, Wang XL, Ma T, Yang FC (2006) J Polym Sci Part A Polym Chem 44(23):6836

    Article  CAS  Google Scholar 

  39. Niu Y, Zhu X, Liu L, Zhang Y, Wang G, Jiang Z (2006) React Funct Polym 66(5):559

    Article  CAS  Google Scholar 

  40. Chen BK, Du JU, Hou CW (2008) IEEE Trans Dielectr Electr Insul 15(1):127

    Article  Google Scholar 

  41. Chern YT, Tsai JY, Wang J (2009) J Polym Sci Part A Polym Chem 47(9):2443

    Article  CAS  Google Scholar 

  42. Hougham G, Tesoro G, Viehbeck A, Chapple-Sokol JD (1994) Macromolecules 21(27):5964

    Article  Google Scholar 

  43. Hougham G, Tesoro G, Viehbeck A (1996) Macromolecules 29(10):3453

    Article  CAS  Google Scholar 

  44. Zheng HB, Wang ZY (2000) Macromolecules 33(12):4310

    Article  CAS  Google Scholar 

  45. Williams FJ, Donahue PE (1977) J Org Chem 42(21):3414

    Article  CAS  Google Scholar 

  46. Ding Y, Hay AS (1996) Macromolecules 29(20):6386

    Article  CAS  Google Scholar 

  47. Sek D, Pijet P, Wanic A (1992) Polymer 33(1):190

    Article  CAS  Google Scholar 

  48. Sek D, Wanic A, Janeczek H, Abadie MJM (1999) J Polym Sci Part A Polym Chem 37(17):3523

    Article  CAS  Google Scholar 

  49. Zhang M, Wang Z, Gao LX, Ding MX (2006) J Polym Sci Part A Polym Chem 44(2):959

    Article  CAS  Google Scholar 

  50. Long TM, Swager TM (2003) J Am Chem Soc 125(46):14113

    Article  CAS  Google Scholar 

  51. Genies C, Mercier R, Sillion B, Petiaud R, Cornet N, Gebel G, Pineri M (2001) Polymer 42(12):5097

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors acknowledge Mr. Jinghua Wu and Mr. Changrong He for dielectric constant measurement. The authors are also grateful to Mr. Shoudong Mao for moisture absorption measurements. We thank the Natural Science Foundation of Ningbo City (2009A610055) and International Science and Technology Cooperation Program of Ningbo City (2009D10017), China.

Author information

Authors and Affiliations

  1. Ningbo Key Laboratory of Polymer Materials, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo, Zhejiang, 315201, People’s Republic of China

    Benlin Hu, Haibing Wei, Ying Han, Guanghui Zhu, Xueliang Pei, Jin Zhu & Xingzhong Fang

Authors
  1. Benlin Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Haibing Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ying Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Guanghui Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xueliang Pei
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jin Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Xingzhong Fang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xingzhong Fang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hu, B., Wei, H., Han, Y. et al. Low dielectric constant and organosolubility of polyimides derived from unsymmetric phthalic-thioether-naphthalic dianhydrides. J Mater Sci 46, 1512–1522 (2011). https://doi.org/10.1007/s10853-010-4956-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10853-010-4956-8

Keywords

Search

Navigation