Skip to main content
Log in

Polyimides prepared without the use of toxic amidic solvents

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

Abstract

Polyimides and their modified forms (e.g., poly(imide-siloxanes)) are an important class of unique polymers. Their typical two-step preparation includes the preparation of a solution of the polyimide precursor in an amidic solvent (e.g., N-methyl-2-pyrrolidone, N,N-dimethylacetamide). Currently, these solvents are classified as toxic, and there is a strong demand to limit their use. Therefore, this study addresses the preparation of polyimides by nontoxic γ-butyrolactone as a solvent and the synthesis of polyimides and poly(imide-siloxanes) in the presence of an enzyme without the use of a solvent. The ability of these products to form self-standing films (membranes) and their thermal and mechanical properties have been found, at least partly, to be comparable to those of the products prepared by using traditional amidic solvents.

Chemoenzymatic Preparation of Poly(imide-siloxane) without Use any Solvent.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Liaw D-J, Wang K-L, Huang Y-C, Lee K-R, Lai J-Y, Ha C-S (2012) Advanced polyimide materials: syntheses, physical properties and applications. Prog Polym Sci 37:907–947

    Article  CAS  Google Scholar 

  2. Al R, Rybak A, Kaszuwara W, Awietjan S, Molak R, Sysel P, Grzywna ZJ (2017) The magnetic inorganic-organic hybrid membranes based on polyimide matrices for gas separation. Composites Part B-Engineering 110:161–170

    Article  Google Scholar 

  3. Zhai Y, Huang Y, Zhu R, Gu Y (2010) Phase separation of poly(amic-co-imide) solution. Chem Eng Comm 197:289–304

    Article  CAS  Google Scholar 

  4. Zhang Y, Tan Y-Y, Liu J-G, Zhi X-X, Huangfu M-G, Jiang G-L, Wu X, Zhang X (2019) Molecular design, synthesis and characterization of intrinsically black polyimide films with high thermal stability and good electrical properties. J Polym Res 26: Article no. 171

  5. Figoli A, Marino T, Simone S, Di Nicolo E, Li X-M, He T, Tornaghi S, Drioli E (2014) Towards non-toxic solvents for membrane preparation. Green Chem 16:4034–4059

    Article  CAS  Google Scholar 

  6. Duereh A, Sato Y, Smith Jr RL, Inomata H (2015) Replacement of hazardous chemicals used in engineering plastics with safe and renewable hydrogen-bond donor and acceptor solvent-pair mixtures. ACS Sustain Chem Eng 3:1881–1889

    Article  CAS  Google Scholar 

  7. Johnson EL (1971) The effect of reaction temperature and hydrolysis on polyamic acids and polyimides. J Appl Polym Sci 15:2825–2839

    Article  CAS  Google Scholar 

  8. Kreuz JA (1990) Hydrolyses of polyamic-acid solutions. J Polym Sci: Part A: Polym Chem 28:3787–3793

    Article  CAS  Google Scholar 

  9. Sysel P, Sindelar V, Chanova E, Wallin B (2002) Preparation of polyimides by using mixtrures of tetrahydrofuran and methanol and their properties. Polym J 34:54–56

    Article  CAS  Google Scholar 

  10. Brandes BT, Smith DK (2016) Calorimetric study of the exothermic decomposition of dimethyl sulfoxide. Process Saf Prog 35:374–391

    Article  CAS  Google Scholar 

  11. Mosurkal R, Samuelson LA, Parmar VS, Kumar J, Watterson AC (2007) Biocatalytic synthesis of organosiloxane copolyimide. Macromolecules 40:7742–7744

    Article  CAS  Google Scholar 

  12. Lanc M, Sysel P, Soltys M, Stepanek F, Fonod K, Klepic M, Vopicka O, Lhotka M, Ulbrich P, Friess K (2018) Synthesis, properties and characterization of novel hyperbranched 6FDA-TTM based polyimide membranes for CO2separation. Effect of embedded mesoporous silica particles and siloxane linkages. Polymer 144:33–42

    Article  CAS  Google Scholar 

  13. Henderson RK, Jimenez-Gonzales C, Constable DJC, Alston SR, Inglis GGA, Fisher G, Sherwood J, Binks SP, Curzons AD (2011) Expanding GSK’s solvent selection guide-embedding sustainability into solvent selection starting at medicinal chemistry. Green Chem 13:854–862

    Article  CAS  Google Scholar 

  14. Brekner M-J, Feger C (1987) Curing studies of a polyimide precursor. II. Polyamic acid. J Polym Sci: Part A: Polym Chem 25:2479–2491

    Article  CAS  Google Scholar 

  15. Goodwin AK, Brown PR, Jansen EEW, Jakobs C, Gibson KM, Weerts EM (2009) Behavioral effects and pharmacokinetics of gamma-hydroxybutyrate (GHB) precursors gamma-butyrolactone (GBL) and 1,4-butanediol (1,4-BD) in baboons. Psychopharmacology 204:465–476

    Article  CAS  Google Scholar 

  16. Ghosh A, Sen SK, Banerjee S, Voit B (2012) Solubility improvements in aromatic polyimides by molecular engineering. RSC Adv 2:5900–5926

    Article  CAS  Google Scholar 

  17. Li R, Lu Z, Liu Y, Zeng K, Hu J, Yang G (2019) The retarding effects and structural evolution of a bio-based high-performance polyimide during thermal imidization. J Appl Polym Sci 136:46953 (12 pp)

    Article  Google Scholar 

  18. Kumar A, Khan A, Malhotra S, Mosurkal R, Dhawan A, Pandey MK, Singh BK, Kumar R, Prasad AK, Sharma SK, Samuelson LA, Cholli AL, Len C, Richards GJ, Kumar J, Haag R, Watterson AC, Parmar VS (2016) Synthesis of macromolecular systems via lipase catalyzed biocatalytic reactions: applications and future petrspectives. Chem Soc Rev 45:6855–6887

    Article  CAS  Google Scholar 

  19. Frampton MB, Zelisko PM (2013) Synthesis of lipase catalyzed silicone-polyesters and silicone-polyamides at elevated temperatures. Chem Commun 49:9269–9271

    Article  CAS  Google Scholar 

  20. Miletic N, Nastasovic A, Loos K (2012) Immobilization of biocatalysts for enzymatic polymerizations: possibilities, advantages, applications. Bio/Technology 115:126–135

    CAS  Google Scholar 

  21. Kurinchyselvan S, Hariharan A, Prabunathan P, Gomathipriya P, Alagar M (2019) Fluorinated polyimide nanocomposites for low K dielectric applications. J Polym Res 26: Article no. 207

  22. Patel DC, Woods RM, Breitbach ZS, Berthod A, Armstrong DW (2017) Thermal racemization of biaryl atropisomers. Tetrahedron Asymmetry 28:1557–1561

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Grant Agency of the Czech Republic (17-00089S). We acknowledge the Dr. Karel Friess research group (Department of Physical Chemistry, University of Chemistry and Technology, Prague, Czech Republic) for the determination of gas transport properties of the selected polymers.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Petr Sysel.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Highlights

Polyimides Prepared without Amidic Solvents

Non-toxic Preparations of (Modified) Polyimides

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sysel, P., Kulhánková, H. & Weinertová, K. Polyimides prepared without the use of toxic amidic solvents. J Polym Res 27, 227 (2020). https://doi.org/10.1007/s10965-020-02177-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-020-02177-3

Keywords

Navigation