Skip to main content
SpringerLink
Log in

Novel Polyetherimides Based on 5-Methyl-1,3-phenylene-bis-4-oxyphthalic Acid Dianhydride: Synthesis and Physicochemical Properties

  • SYNTHESIS
  • Published:
Polymer Science, Series B Aims and scope Submit manuscript

Abstract—

A novel monomer for the synthesis of polyimides, 5-methyl-1,3-phenylene-bis-4-oxyphthalic acid dianhydride was developed. The synthesis was carried out in three stages: the reaction of nucleophilic nitro substitution of 4-nitrophthalonitrile with 5‑methylresorcinol (orcinol) potassium salt and subsequent hydrolysis of the nitrile groups have afforded 5‑methyl-1,3-phenylene-bis-4-oxyphthalic acid, dehydration of which has given the corresponding dianhydride. A series of new thermoplastic high molecular weight polyetherimides based on 5-methyl-1,3-phenylene-bis-4-oxyphthalic acid dianhydride and several aromatic diamines of various structures were synthesized by the method of one-stage catalytic polycondensation in a benzoic acid melt. Inherent viscosity and weight-average molecular mass of the polyetherimides have been of 0.28‒1.20 dL/g and (33‒114) × 103, respectively. The polyetherimides have been soluble in chloroform, THF, DMF, DMAA, N-methylpyrrolidone, and DMSO and have revealed film-forming properties. According to the DSC and wide-angle X-ray scattering data, the polyetherimides have been found completely amorphous, the glass transition temperature being in the 185–307°C 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

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.

Similar content being viewed by others

REFERENCES

  1. J. De Abajo and J. G. De la Campa, Prog. Rolyimide Chem. I, 23 (1999).

    Article  Google Scholar 

  2. M. I. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A. Laius, Polyimides: Thermally Stable Polymers (Springer, New York, 1987).

    Book  Google Scholar 

  3. Advanced Polyimide Materials: Synthesis, Characterization, and Applications, Ed. by S. Y. Yang (Elsevier, Amsterdam, 2018).

    Google Scholar 

  4. D. J. Liaw, K.-L. Wang, Y.-C. Huang, K.-R. Lee, J.‑Y. Lai, and C.-S. Ha, Prog. Polym. Sci. 37 (7), 907 (2012).

    Article  CAS  Google Scholar 

  5. H. Sanaeepur, A. E. Amooghin, S. Bandehali, A. Moghadassi, T. Matsuura, and B. Van der Bruggen, Prog. Polym. Sci. 91, 80 (2019).

    Article  CAS  Google Scholar 

  6. Zhen Xu, Zacary L. Croft, Dong Guo, Ke Cao, and Guoliang Liu, J. Polym. Sci. 59 (11), 943 (2021). https://doi.org/10.1002/pol.20210001

    Article  CAS  Google Scholar 

  7. Y.-H. Xiao, Chin. Chem. Lett 27 (3), 454 (2016).

    Article  CAS  Google Scholar 

  8. Y. Hwan-Chul, J. Macromol. Sci., A 54, 97 (2017).

  9. T. Takekoshi, J. G. Wirth, D. R. Heath, J. E. Kochanowski, J. S. Manello, and M. J. J. Webber, J. Polym. Sci., Polym. Chem. Ed. 18 (10), 3069 (1980).

    Article  CAS  Google Scholar 

  10. US Patent No. 3983093 (1976).

  11. S. H. Hsiao and L. R. Dai, J. Polym. Sci., Part A: Polym. Chem. 37 (5), 665 (1999).

    Article  CAS  Google Scholar 

  12. C. P. Yang, Y. Y. Su, S. J. Wen, and S. H. Hsiao, Polymer 47 (20), 7021 (2006).

    Article  CAS  Google Scholar 

  13. T. Takekoshi, J. Polym. Sci., Polym. Symp. 74 (1), 93 (1986).

  14. G. C. Eastmond and J. Paprotny, Macromolecules 28 (7), 2140 (1995).

    Article  CAS  Google Scholar 

  15. M. D. Damaceanu, C. P. Constantin, M. Bruma, and R. S. Begunov, Polymer 151, 34 (2018).

    Article  CAS  Google Scholar 

  16. V. M. Svetlichnyi, T. I. Zhukova, V. V. Kudriavtsev, G. N. Gubanova, V. E. Yudin, and A. M. Leksovskii, Polym. Eng. Sci. 35 (16), 1321 (1995).

    Article  Google Scholar 

  17. V. E. Yudin, V. M. Svetlichnyi, G. N. Gubanova, A. I. Grigor’ev, T. E. Sukhanova, I. V. Gofman, A. L. Didenko, E. N. Popova, G. N. Fedorova, and V. V. Kudryavtsev, Polym. Sci., Ser. A 44 (2), 148 (2002).

    Google Scholar 

  18. V. E. Yudin, V. M. Svetlichnyi, G. N. Gubanova, A. L. Didenko, T. E. Sukhanova, V. V. Kudryavtsev, S. Ratner, and G. Marom, J. Appl. Rolym. Sci 83 (13), 2873 (2002).

    CAS  Google Scholar 

  19. V. V. Plakhtinskii, P. S. Kaninskii, G. S. Mironov, I. G. Abramov, and O. A. Yasinskii, SU Patent No. 1509352 (1989).

  20. A. A. Kuznetsov, High Perform. Polym. 12 (3), 445 (2000).

    Article  CAS  Google Scholar 

  21. B. V. Tawade, A. D. Kulkarni, and P. P. Wadgaonkar, Polym. Int. 64 (12), 1770 (2015).

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

Registration of the IR and NMR spectra and thermal studies was made using the equipment of the Collaborative Access Center “Center for Polymer Research” of ISPM RAS.

Funding

This study was partially financial supported by the Russian Foundation for Basic Research (project code 19-03-00820) and performed in the scope of the State Task no. 0086-2019-0007. Registration of the IR and NMR spectra and thermal studies were supported by the Ministry of Science and Higher Education of Russian Federation.

Author information

Authors and Affiliations

  1. Enikolopov Institute of Synthetic Polymeric Materials, Russian Academy of Sciences, 117393, Moscow, Russia

    A. M. Orlova, A. Yu. Tsegelskaya, T. I. Kolesnikov & A. A. Kuznetsov

  2. Yaroslavl State Technical University, 150023, Yaroslavl, Russia

    I. G. Abramov

Authors
  1. A. M. Orlova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Yu. Tsegelskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. I. Kolesnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. G. Abramov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Kuznetsov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. M. Orlova.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Translated by E. Karpushkin

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Orlova, A.M., Tsegelskaya, A.Y., Kolesnikov, T.I. et al. Novel Polyetherimides Based on 5-Methyl-1,3-phenylene-bis-4-oxyphthalic Acid Dianhydride: Synthesis and Physicochemical Properties. Polym. Sci. Ser. B 64, 17–25 (2022). https://doi.org/10.1134/S1560090422010031

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1560090422010031

Search

Navigation