Skip to main content
SpringerLink
Log in

Synthesis and characterization of branched phenylethynyl-terminated polyimides

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

Abstract

A series of PEPA-TAP-ODA-6FDA branched phenylethynyl-terminated polyimides (BPIs) are successfully synthesized by incorporation of branching units into the linear PI. The molecular structures, thermal and rheological properties of the BPIs are investigated and characterized by FTIR, 1H NMR, elemental analysis, TGA and rheological test. All the BPIs exhibit high transparent in visible region, high solubility, excellent thermal stabilities and melting processability. All the BPIs have excellent thermal stabilities, and the corresponding T5 and heat resistance index values of the BPIs are all higher than 470 and 265 °C, respectively. All the BPIs have a relatively lower melt viscosity values. Compared to that of neat PI, the minimum melt viscosity values of the BPIs are all decreased obviously. Herein, BPIs-b exhibits the minimum melt viscosity (210 Pa•s), far below than that of neat PI (1260 Pa•s).

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

Similar content being viewed by others

References

  1. Liaw DJ, Chang FC, Leung MK, Chou MY, Müllen K (2005) High thermal stability and rigid rod of novel organosoluble polyimides and polyamides based on bulky and noncoplanar naphthalene-biphenyldiamine[J]. Macromolecules 38(9):4024–4029

    Article  CAS  Google Scholar 

  2. Luong ND, Hippi U, Korhonen JT, Soininen AJ, Ruokolainen J, Johansson LS (2011) Enhanced mechanical and electrical properties of polyimide film by graphene sheets via in situ polymerization[J]. Polymer 52(23):5237–5242

    Article  Google Scholar 

  3. Wang KL, Liou WT, Liaw DJ, Huang ST (2008) High glass transition and thermal stability of new pyridine-containing polyimides: effect of protonation on fluorescence[J]. Polymer 49(6):1538–1546

    Article  Google Scholar 

  4. Koohmareh GA, Mohammadifard N (2011) Synthesis and characterization of some new thermally stable polyimides and copolyimides bearing bipyridine side-chain groups[J]. J Polym Res 18(5):983–991

    Article  CAS  Google Scholar 

  5. Tamai S, Kuroki T, Shibuya A, Yamaguchi A (2001) Synthesis and characterization of thermally stable semicrystalline polyimide based on 3, 4′-oxydianiline and 3, 3′, 4, 4′-biphenyltetracarboxylic dianhydride[J]. Polymer 42(6):2373–2378

    Article  CAS  Google Scholar 

  6. Seiler M (2006) Hyperbranched polymers: phase behavior and new applications in the field of chemical engineering[J]. Fluid Phase Equilib 241(1):155–174

    Article  CAS  Google Scholar 

  7. Ree M (2006) High performance polyimides for applications in microelectronics and flat panel displays[J]. Macromol Res 14(1):1–33

    Article  CAS  Google Scholar 

  8. Mathews AS, Kim I, Ha CS (2007) Synthesis, characterization, and properties of fully aliphatic polyimides and their derivatives for microelectronics and optoelectronics applications[J]. Macromol Res 15(2):114–128

    Article  CAS  Google Scholar 

  9. Hu YC, Chen CJ, Yen HJ, Lin KY, Yeh JM, Chen WC, Liou GS (2012) Novel triphenylamine-containing ambipolar polyimides with pendant anthraquinone moiety for polymeric memory device, electrochromic and gas separation applications[J]. J Mater Chem 22(38):20394–20402

    Article  CAS  Google Scholar 

  10. Powell CE, Qiao GG (2006) Polymeric CO2/N2 gas separation membranes for the capture of carbon dioxide from power plant flue gases[J]. J Membr Sci 279(1–2):1–49

    Article  CAS  Google Scholar 

  11. Kuroki T, Shibuya A, Toriida M, Tamai S (2004) Melt‐processable thermosetting polyimide: synthesis, characterization, fusibility, and property[J]. J Polym Sci A Polym Chem 42(10):2395–2404

    Article  CAS  Google Scholar 

  12. Nasab SMA, Ghaemy M (2011) Synthesis and characterization of new polyamides and polyimides containing dioxypyrimidine moiety in the main chain with bulky imidazole pendent group: solubility, thermal and photophysical properties[J]. J Polym Res 18(6):1575–1586

    Article  CAS  Google Scholar 

  13. MehdipourAtaei S, AkbarianFeizi L (2011) Soluble polyimides from a semi-aliphatic diamine containing ester, amide and ether groups[J]. Chin J Polym Sci 29(1):93–100

    Article  CAS  Google Scholar 

  14. Shao Y, Li Y, Zhao X, Ma T, Gong C, Yang F (2007) Synthesis and characterization of soluble polyimides derived from a novel unsymmetrical diamine monomer: 1, 4-(2′, 4″-diaminodiphenoxy) benzene[J]. Eur Polym J 43(10):4389–4397

    Article  CAS  Google Scholar 

  15. Chung CL, Lee WF, Lin CH, Hsiao SH (2009) Highly soluble fluorinated polyimides based on an asymmetric bis (ether amine): 1, 7-bis (4-amino-2-trifluoromethylphenoxy) naphthalene[J]. J Polym Sci A Polym Chem 47(7):1756–1770

    Article  CAS  Google Scholar 

  16. Sydlik SA, Chen Z, Swager TM (2011) Triptycene polyimides: soluble polymers with high thermal stability and low refractive indices[J]. Macromolecules 44(4):976–980

    Article  CAS  Google Scholar 

  17. Ghaemy M, Alizadeh R (2009) Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2, 4, 5-triaryl imidazole pendent group[J]. Eur Polym J 45(6):1681–1688

    Article  CAS  Google Scholar 

  18. Ghaemy M, Porazizollahy R, Bazzar M (2011) Novel thermal stable organosoluble polyamides and polyimides based on quinoxalin bulky pendent group[J]. Macromol Res 19(6):528–536

    Article  CAS  Google Scholar 

  19. Rao X, Zhou H, Dang G, Chen C, Wu Z (2006) New kinds of phenylethynyl-terminated polyimide oligomers with low viscosity and good hydrolytic stability[J]. Polymer 47(17):6091–6098

    Article  CAS  Google Scholar 

  20. Cho D, Lee S, Yang G, Fukushima H, Drzal LT (2005) Dynamic mechanical and thermal properties of phenylethynyl‐terminated polyimide composites reinforced with expanded graphite nanoplatelets[J]. Macromol Mater Eng 290(3):179–187

    Article  CAS  Google Scholar 

  21. Rao X, Dang G, Zhou H, Yang W, Cui G, Chen C, Yokota R (2007) Design and synthesis of a tribranched phenylethynyl‐terminated aryl ether compound and its use as a reactive diluent for PETI-5[J]. J Polym Sci A Polym Chem 45(21):4844–4854

    Article  CAS  Google Scholar 

  22. Smith J, Connell J, Hergenrother P (2000) The effect of phenylethynyl terminated imide oligomer molecular weight on the properties of composites[J]. J Compos Mater 34(7):614–628

    Article  CAS  Google Scholar 

  23. Yao P, Gu JW, Lei XF, Sun WL, Chen Y, Zhang QY (2015) Highly soluble and thermally stable copolyimidesmodified with trifluoromethyl and siloxane[J]. J Appl Polym Sci. doi:10.1002/app.41713

    Google Scholar 

  24. Yan D, Gao C, Frey H (2011) Hyperbranched polymers: synthesis, properties and applications[M]. Vol. 8. Wiley

  25. Han J, Li S, Tang A, Gao C (2012) Water-soluble and clickable segmented hyperbranched polymers for multifunctionalization and novel architecture construction[J]. Macromolecules 45(12):4966–4977

    Article  CAS  Google Scholar 

  26. Gupta U, Agashe HB, Asthana A, Jain N (2006) Dendrimers: novel polymeric nanoarchitectures for solubility enhancement[J]. Biomacromolecules 7(3):649–658

    Article  CAS  Google Scholar 

  27. Chen Y, Zhang QY, Sun WL, Lei XF, Yao P (2014) Synthesis and gas permeation properties of hyperbranched polyimides membranes from a novel (A2+ B2B′+ B2)-type method[J]. J Membr Sci 450:138–146

    Article  CAS  Google Scholar 

  28. Dhara MG, Banerjee S (2010) Fluorinated high-performance polymers: poly (arylene ether) s and aromatic polyimides containing trifluoromethyl groups[J]. Prog Polym Sci 35(8):1022–1077

    Article  CAS  Google Scholar 

  29. Calle M, Lozano AE, de Abajo J, José G, Álvarez C (2010) Design of gas separation membranes derived of rigid aromatic polyimides. 1. Polymers from diamines containing di-tert-butyl side groups[J]. J Membr Sci 365(1–2):145–153

    Article  CAS  Google Scholar 

  30. Chung CL, Hsiao SH (2008) Novel organosoluble fluorinated polyimides derived from 1, 6-bis (4-amino-2-trifluoromethylphenoxy) naphthalene and aromatic dianhydrides[J]. Polymer 49(10):2476–2485

    Article  CAS  Google Scholar 

  31. Behniafar H, Sefid-girandehi N (2011) Optical and thermal behavior of novel fluorinated polyimides capable of preparing colorless, transparent and flexible films[J]. J Fluor Chem 132(11):878–884

    Article  CAS  Google Scholar 

  32. Yang CP, Su YY (2005) Colorless and high organosoluble polyimides from 2, 5-bis (3, 4-dicarboxyphenoxy)-t-butylbenzene dianhydride and aromatic bis (ether amine) s bearing pendent trifluoromethyl groups[J]. Polymer 46(15):5778–5788

    Article  CAS  Google Scholar 

  33. Gu JW, Zhang QY, Dang J, Yin CJ, Chen SJ (2012) Preparation and properties of polystyrene/SiCw/SiCp thermal conductivity composites. J Appl Polym Sci 124(1):132–137

    Article  CAS  Google Scholar 

  34. Yokota R, Yamamoto S, Yano S, Sawaguchi T, Hasegawa M, Yamaguchi H, Ozawa H, Sato R (2001) Molecular design of heat resistant polyimides having excellent processability and high glass transition temperature[J]. High Perform Polym 13(2):S61–S72

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful for the financial support provided by the National Natural Science Foundation of China (51403175, 81400765 and 51173146); National High Technology Research and Development Program of China (2012AA02A404); Shanxi National Science Foundation (2014JQ6203); Space Supporting Fund from China Aerospace Science and Industry Corporation (2014-HT-XGD) and the Fundamental Research Funds for the Central Universities (3102015ZY066).

Author information

Authors and Affiliations

  1. Key Laboratory of Space Applied Physics and Chemistry, Ministry of Education, Department of Applied Chemistry, School of Science, Northwestern Polytechnical University, Xi’an, 710072, People’s Republic of China

    Wanlu Sun, Junwei Gu, Lidong Tian, Pan Yao & Qiuyu Zhang

Authors
  1. Wanlu Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Junwei Gu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lidong Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pan Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qiuyu Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Junwei Gu or Qiuyu Zhang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sun, W., Gu, J., Tian, L. et al. Synthesis and characterization of branched phenylethynyl-terminated polyimides. J Polym Res 22, 85 (2015). https://doi.org/10.1007/s10965-015-0735-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-015-0735-1

Keywords

Search

Navigation