Skip to main content
SpringerLink
Log in

Synthesis and characterization of novel organosoluble and thermally stable polyamides bearing triptycene in their backbones

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

Abstract

New triptycene-containing polyamides were prepared from 1,4-bis(4-carboxyphenoxy)triptycene with aromatic diamines or from 1,4-bis(4-aminophenoxy)triptycene with aromatic dicarboxylic acids via the phosphorylation polyamidation reaction. These polyamides were essentially amorphous and showed a significantly increased solubility as compared with their analogs without the triptycene units. All the polyamides could be solution-cast into flexible and tough films. They also showed good thermal stability with glass transition temperatures of 252–295 °C and 10 % weight loss temperatures higher than 540 °C. These polyamides are considered to be promising processable high-temperature polymeric materials.

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
Fig. 9

Similar content being viewed by others

References

  1. Yang HH (1989) Aromatic high-strength fibers. Wiley, New York, pp 66–289

    Google Scholar 

  2. Yang HH (1993) Kevlar aramid fiber. Wiley, New York

    Google Scholar 

  3. Hsiao SH, Huang TL (2002) J Polym Sci Part A Polym Chem 40:947–957

    Article  CAS  Google Scholar 

  4. Liaw DJ, Hsu PN, Chen WH, Lin SL (2002) Macromolecules 35:4669–4676

    Article  CAS  Google Scholar 

  5. Hsiao SH, Chang YM (2004) J Polym Sci Part A Polym Chem 42:4056–4062

    Article  CAS  Google Scholar 

  6. Hsiao SH, Lin KH (2004) Polymer 45:7877–7885

    Article  CAS  Google Scholar 

  7. Liaw DJ, Chang FC, Leung MK, Chou MY, Muellen K (2005) Macromolecules 38:4024–4029

    Article  CAS  Google Scholar 

  8. Liaw DJ (2005) J Polym Sci Part A Polym Chem 43:4559–4569

    Article  CAS  Google Scholar 

  9. Liou GS, Fang YK, Yen HJ (2007) J Polym Res 14:147–155

    Article  CAS  Google Scholar 

  10. Behniafar H, Khosravi-Borna S (2009) Polym Int 58:1299–1307

    Article  CAS  Google Scholar 

  11. Ghaemy M, Amini Nasab SM (2010) React Funct Polym 70:306–313

    Article  CAS  Google Scholar 

  12. Espeso JK, Lozano AE, de la Campa JG, Garcia-Yoldi I, de Abajo J (2010) J Polym Sci Part A Polym Chem 48:1743–1751

    Article  CAS  Google Scholar 

  13. Garcia JM, Garcia FC, Serna F, de la Pena JL (2010) Prog Polym Sci 35:623–686

    Article  CAS  Google Scholar 

  14. Damaceanu MD, Rusu RD, Nicolescu A, Bruma M, Rusanov AL (2011) Polym Int 60:1248–1258

    Article  CAS  Google Scholar 

  15. Patil VB, Sayyed MM, Mahanwar PA, Wadgaonkar PP, Maldar NN (2011) J Polym Res 18:549–557

    Article  CAS  Google Scholar 

  16. Chen JC, Rajendran K, Huang SW, Chang HW (2011) J Polym Res 18:1693–1703

    Article  CAS  Google Scholar 

  17. Nechifor M (2011) J Polym Res 18:2477–2485

    Article  CAS  Google Scholar 

  18. Yang JS, Yan JL (2008) Chem Commun 1501–1512

  19. Bartlett PD, Ryan MJ, Cohen SG (1942) 64:2649–2653

  20. Wittig G, Ludwig R (1956) Angew Chem 68:40

    Article  CAS  Google Scholar 

  21. Wittig G (1959) Org Synth 39:75

    CAS  Google Scholar 

  22. Skvarchenko VR, Shalaev VK, Klabunovskii EI (1974) Russ Chem Rev (Engl Transl) 43:951–966

    Article  Google Scholar 

  23. Klanderman BH, Faber JWH (1968) J Polym Sci Part A-1 6:2955–2965

    Article  CAS  Google Scholar 

  24. Hoffmeister E, Kropp JE, McDowell TL, Michel RH, Rippie WL (1969) J Polym Sci Part A-1 7:55–72

    Article  CAS  Google Scholar 

  25. Yang JS, Swager TM (1998) J Am Chem Soc 120:11864–11873

    Article  CAS  Google Scholar 

  26. Long TM, Swager TM (2003) J Am Chem Soc 125:14113–14119

    Article  CAS  Google Scholar 

  27. Tsui NT, Paraskos AJ, Torun L, Swager TM, Thomas EL (2006) Macromolecules 39:3350–3358

    Article  CAS  Google Scholar 

  28. Tsui NT, Torun L, Pate BD, Paraskos AJ, Swager TM, Thomas EL (2007) Adv Funct Mater 17:1595–1602

    Article  CAS  Google Scholar 

  29. Chen Z, Swager TM (2008) Macromolecules 41:6880–6885

    Article  CAS  Google Scholar 

  30. Tsui NT, Yang Y, Mulliken AD, Torun L, Boyce MC, Swager TM, Thomas EL (2008) Polymer 49:4703–4712

    Article  CAS  Google Scholar 

  31. Swager TM (2008) Acc Chem Res 41:1181–1189

    Article  CAS  Google Scholar 

  32. Cho YJ, Park HB (2011) Macromol Rapid Commun 32:579–586

    Article  CAS  Google Scholar 

  33. Hsiao SH, Wang HM, Chen WJ, Lee TM, Leu CM (2011) J Polym Sci Part A Polym Chem 49:3109–3312

    Article  CAS  Google Scholar 

  34. Hsiao SH, Chang CF (1996) Macromol Chem Phys 197:1255–1272

    Article  CAS  Google Scholar 

  35. Yamazaki N, Matsumoto M, Higashi F (1975) J Polym Sci Polym Chem Ed 13:1373–1380

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei, Taiwan

    Sheng-Huei Hsiao, Hui-Min Wang, Ji-Shian Chou, Wenjen Guo & Teh-Hua Tsai

Authors
  1. Sheng-Huei Hsiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hui-Min Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ji-Shian Chou
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wenjen Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Teh-Hua Tsai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sheng-Huei Hsiao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hsiao, SH., Wang, HM., Chou, JS. et al. Synthesis and characterization of novel organosoluble and thermally stable polyamides bearing triptycene in their backbones. J Polym Res 19, 9902 (2012). https://doi.org/10.1007/s10965-012-9902-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-012-9902-9

Keywords

Search

Navigation