Skip to main content

Advertisement

SpringerLink
Log in

Highly soluble phenylethynyl terminated oligoimides derived from 5(6)-amino-1-(4-aminophenyl)-1,3,3-trimethylindane, 4,4′-oxydianiline and mixed thioetherdiphthalic anhydride isomers

  • ORIGINAL PAPER
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Novel highly soluble phenylethynyl-endcapped oligoimides derived from mixed thioetherdiphthalic anhydride isomers (m-TDPA) and 5(6)-amino-1-(4-aminophenyl)-1,3,3-trimethylindane (DAPI), 4,4′-oxydianiline (4,4’-ODA) with 4-phenylethynylphthalic anhydride (PEPA) as a reactive endcapping agent were synthesized. The calculated molecular weights of all the oligoimides were 2500 g·mol−1.The effect of the mole ratio of DAPI/4,4’-ODA on solubility and melt viscosity of oligoimides as well as the thermal and mechanical properties of cured polyimide films was investigated. Experimental results indicated that DAPI greatly improved the solubility (>30 wt.%) of the oligoimides in low boiling points solvents when the content of DAPI was more than 10 mol% per total diamine. All the oligoimides exhibited very good processability with minimum melt viscosity lower than 60 Pa·s at about 330 °C. Tough and brown films were obtained after thermally cured at 370 °C for 1 h and dynamic mechanical analysis (DMA) showed that glass transition temperatures of the cured films increased up to 340 °C with the increasing content of DAPI. However, the thermal stability and mechanical properties decreased with the increase of DAPI content. The temperature of 5% weight loss was higher than 470 °C in both air and N2 atmosphere obtained by thermogravimetric analysis (TGA). And the tensile strengths of the cured films were about 60 MPa.

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
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Serafini TT, Delvigs P, Lightsey GR (1972) Thermally stable polyimides from solutions of monomeric reactants. J Appl Polym Sci 16:905–915

    Article  CAS  Google Scholar 

  2. Daniel AS, Martin W (1994) The thermo-oxidative stability of fluorinated polyimides and polyimide/graphite composites at 371°c. J Appl Polym Sci 52:421–429

    Article  Google Scholar 

  3. Criss JM, Arendt CP, Connell JW, Smith JG, Hergenrother PM (2000) Resin transfer molding and resin infusion fabrication of high-temperature composites. SAMPE J 36(3):32–41

    CAS  Google Scholar 

  4. Smith JG, Connell JW, Hergenrother PM, Ford LA, Criss JM (2003) Transfer molding imide resins based on 2,3,3′,4′-biphenyltetracarboxylic dianhydride. Macromol Symp 199(1):401–418

    Article  CAS  Google Scholar 

  5. Connell JW, Smith JG, Hergenrother PM, Criss JM (2003) High temperature transfer molding resins: status of PETI-298 and PETI-330. High Perform Polym 15(4):375–394

    Article  CAS  Google Scholar 

  6. Smith JG, Connell JW, Li CJ, Wu W, Criss JM (2006) Microwave synthesis of phenylethynyl imide oligomers: neat resin and composite properties of PETI-298. High Perform Polym 18(3):341–354

    Article  CAS  Google Scholar 

  7. Hinkley JA, Jensen BJ (1996) Crosslinking in phenylethynyl terminated polyimides. High Perform Polym 8(4):599–605

    Article  CAS  Google Scholar 

  8. Zhou HW, Chen CH, Kanbara R et al (2005) Isomeric dianhydrides based modified phenylethynyl-terminated addition-type imide oligomers. High Perform Polym 17(2):193–212

    Article  CAS  Google Scholar 

  9. Rao XH, Zhou HW, Dang GD et al (2006) New kinds of phenylethynyl-terminated polyimide oligomers with low viscosity and good hydrolytic stability. Polymer 47(17):6091–6098

    Article  CAS  Google Scholar 

  10. Jensen BJ, Bryant RG, Smith JG, Hergenrother PM (1995) Adhesive properties of cured phenylethynyl-terminated imide oligomers. J Adhes 54(1):57–66

    Article  CAS  Google Scholar 

  11. Hou TH, Jensen BJ, Hergenrother PM (1996) Processing and properties of IM7/PETI composites. J CompMater 30(1):109–122

    CAS  Google Scholar 

  12. Hergenrother PM, Smith JG (1994) Chemistry and properties of imide oligomers end-capped with phenylethynylphthalic anhydrides. Polymer 35(22):4857–4864

    Article  CAS  Google Scholar 

  13. Cano RJ, Jensen BJ (1997) Effect of molecular weight on processing and adhesive properties of the phenylethynyl-terminated polyimide LARC™-PETI-5. J Adhes 60(1–4):113–123

    Article  CAS  Google Scholar 

  14. Hergenrother PM, Connell JW, Smith JG (2000) Phenylethynyl containing imide oligomers. Polymer 41:5073–5081

    Article  CAS  Google Scholar 

  15. Ogasawara T, Ishikawa T, Yokota R et al (2003) Processing and properties of carbon fiber reinforced triple-A polyimide (Tri-A PI) matrix composites. Adv Compos Mater 11(3):277–286

    Article  CAS  Google Scholar 

  16. Tong YJ, Huang WX, Luo J et al (1999) Synthesis and properties of aromatic polyimides derived from 2,2′,3,3′-biphenyltetracarboxylic dianhydride. J Polym Sci Polym Chem 37(10):1425–1433

    Article  CAS  Google Scholar 

  17. Hergenrother PM, Watson KA, Smith JG et al (2002) Polyimides from 2, 3, 3′, 4′-biphenyltetracarboxylic dianhydride and aromatic diamines. Polymer 43(19):5077–5093

    Article  CAS  Google Scholar 

  18. Miyauchi M, Ishida Y, Ogasawara T, Yokota R (2013) Synthesis and characterization of soluble phenylethynyl-terminated imide oligomers derived from pyromellitic dianhydride and 2-phenyl-4,4′-diaminodiphenyl ether. React Funct Polym 73:340–345

    Article  CAS  Google Scholar 

  19. Ishida Y, Ogasawara T, Yokota R (2006) Development of highly soluble addition-type imide oligomers for matrix of carbon fiber composite (I): imide oligomers based on asymmetric biphenyltetracarboxylic dianhydride and 9,9-bis(4-aminophenyl)fluorine. High Perform Polym 18(5):727–737

    Article  CAS  Google Scholar 

  20. Sun WL, JW G, Tian LD, Yao P, Zhang QY (2015) Synthesis and characterization of branched phenylethynyl-terminated polyimides. J Polym Res 22(5):1–8

    Google Scholar 

  21. Miyauchi M, Ishida Y, Ogasawara T, Yokota R (2013) Highly soluble phenylethynyl-terminated imide oligomers based on KAPTON-type backbone structures for carbon fiber-reinforced composites with high heat resistance. Polym J 45:594–600

    Article  CAS  Google Scholar 

  22. Chen W, Jia M, Yang SY (2016) High thermal stable polyimide resins derived from phenylethynylendcapped fluorenyl oligoimides with low melt viscosities. Chinese J Polym Sci 34(8):933–948

    Article  CAS  Google Scholar 

  23. Meng XS, Yan JL, Fan WF, Liu JF, Wang Z, Li GD (2014) Thermosetting polyimides and composites based on highly soluble phenylethynyl-terminated isoimide oligomers. RSC Adv 4:37458–37469

    Article  CAS  Google Scholar 

  24. Bateman JH, Geresy WJ, Neiditch DS (1975) Soluble polyimides derived from phenylindane diamine: a new approach to heat resistant protective coatings. Am Chem Soc Div Org Chem Coat Plast Chem 35:77

    CAS  Google Scholar 

  25. Farr IV, Glass TE, Ji Q, McGrath JE (1997) Synthesis and characterization of diaminophenylindane based polyimides via ester-acid solution imidization. High Perform Polym 9:345–352

    Article  CAS  Google Scholar 

  26. Farr IV, Kratzner D, Glass TE, Dunson D, Ji Q, McGrath JE (2000) The synthesis and characterization of polyimide homopolymers based on 5(6)-Amino-1-(4-aminophenyl)-1,3,3-trimethylindane. J Polym Sci: Part A: Polym Chem 38:2840–2854

    Article  CAS  Google Scholar 

  27. Han Y, Fang XZ, Zuo XX (2010) Melt processable homo- and copolyimides with high thermo-oxidative stability as derived from mixed thioetherdiphthalic anhydride isomers. Express Polym Lett 4(11):712–722

    Article  CAS  Google Scholar 

  28. Han Y, Fang XZ, Zuo XX (2010) The influence of molecular weight on properties of melt-processable copolyimides derived from thioetherdiphthalic anhydride isomers. J Mater Sci 45(7):1921–1929

    Article  CAS  Google Scholar 

  29. Han Y, Fang XZ, Zuo XX (2010) Synthesis and properties of novel melt processable isomeric polythioetherimides. High Perform Polym 22(8):989–1003

    Article  CAS  Google Scholar 

  30. Pei XL, Chen GF, Fang XZ (2011) Preparation and characterization of poly(imide siloxane) block copolymers based on diphenylthioether dianhydride isomer mixtures. High Perform Polym 23(8):625–632

    Article  CAS  Google Scholar 

  31. Sun L, Wang W, LB X, Chen GF, Fang XZ (2016) Phenylethynyl-terminated imide oligomers derived from thioetherdiphthalic anhydride isomers with decreased melt viscosities. High Perform Polym 28(8):927–935

    Article  CAS  Google Scholar 

  32. Liu JT, Chen GF, Fang XZ (2014) Preparation, characterization, and properties of poly(thioether ether imide)s from isomeric bis(chlorophthalimide)s and 4,4′-thiobisbenzenethiol. Polym Adv Technol 25(3):329–337

    Article  CAS  Google Scholar 

  33. Wei HB, XS W, BL H et al (2011) Preparation, characterization, and properties of poly(thioether ether ketone imide)s from isomeric bis(chlorophthalimide)s. Polym Adv Technol 22(12):2488–2495

    Article  CAS  Google Scholar 

  34. Yi L, Li CY, Huang W, Yan DY (2014) Soluble aromatic polyimides with high glass transition temperature from benzidine containing tert-butyl groups. J Polym Res 21(11):572

    Article  Google Scholar 

  35. Chung CL, Tzu TW, Hsiao SH (2006) Organosoluble, low-colored fluorinated polyimides based on 1,1-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]-1-phenyl-2,2,2-trifluoroethane. J Polym Res 13:495–506

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the program of National Natural Science Foundation of China (Grant No. 51703231), Ningbo Municipal Science and Technology Innovative Research Team (Grant No. 2015B11002 and 2016B10005) and Science & Technology Planning Project of Guangdong Province (Grant No. 2016B090906004).

Author information

Authors and Affiliations

  1. School of Materials Science and Engineering, Shanghai University, Shanghai, 200444, People’s Republic of China

    Hanyuan Li & Yinfeng Liu

  2. Key Laboratory of Additive Manufacturing Materials of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo, Zhejiang, 315201, People’s Republic of China

    Hanyuan Li, Wei Wang, Guofei Chen & Xingzhong Fang

Authors
  1. Hanyuan Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Guofei Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yinfeng Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xingzhong Fang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Wei Wang or Xingzhong Fang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, H., Wang, W., Chen, G. et al. Highly soluble phenylethynyl terminated oligoimides derived from 5(6)-amino-1-(4-aminophenyl)-1,3,3-trimethylindane, 4,4′-oxydianiline and mixed thioetherdiphthalic anhydride isomers. J Polym Res 25, 32 (2018). https://doi.org/10.1007/s10965-017-1434-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-017-1434-x

Keywords

Search

Navigation