Skip to main content
SpringerLink
Log in

Crosslinking of Brominated Poly(1-trimethylsilyl-1-propyne) Using Polyethylenimine as a Crosslinking Agent

  • Published:
Membranes and Membrane Technologies Aims and scope Submit manuscript

Abstract

Сrosslinked polymer memranes are obtained by the heat treatment of films prepared from a solution of a mixture of bromine-containing poly(1-trimethylsilyl-1-propyne) (PTMSP) and polyfunctional amine polyethyleneimine (PEI) as a crosslinking agent. Crosslinked products are identified from IR spectra, elemental analysis data, and stability of reaction products to a solvent (CCl4), in which the original brominated PTMSP is soluble. According to the IR spectra, the crosslinking reaction occurs via reactive C–Br bond in bromine-containing PTMSP with the participation of PEI amino groups at a temperature above 90°С. The crosslinking of bromine-containing PTMSP makes it resistant to organic solvents. An increase in the content of PEI in the mixture correlates with the proportion of bromine atoms involved in the reaction. For brominated PTMSP films crosslinked by PEI transport parameters for individual gases and in the mixture n-butane/methane (98.4 mol % methane and 1.6 mol % n-butane) are studied. In the sequence PTMSP–brominated PTMSP-Br–PTMSP-Br/PEI (before crosslinking)–PTMSP-Br/PEI (after crosslinking) permeability for individual gases decreases. Crosslinked PTMSP in the mixture methane/n-butane demonstrates high permeability coefficients of n-butane (\({{P}_{{n{\text{-}}{{{\text{C}}}_{{\text{4}}}}{{{\text{H}}}_{{10}}}}}}\) = 12 000 Barrer) and selectivity for n-butane separation from a mixture with methane (\({{\alpha }_{{n{\text{-}}{{{\text{C}}}_{{\text{4}}}}{{{\text{H}}}_{{10}}}{\text{/C}}{{{\text{H}}}_{4}}}}}\) = 13).

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.

REFERENCES

  1. M. Galizia, W. S. Chi, Z. P. Smith, T. C. Merkel, R. W. Baker, and B. D. Freeman, Macromolecules 50, 7809 (2017).

    Article  CAS  Google Scholar 

  2. Y. K. Ong, G. M. Shi, N. L. Le, Y. P. Tang, J. Zuo, S. P. Nunes, and T. S Chung, Prog. Polym. Sci. 57, 1 (2016).

    Article  CAS  Google Scholar 

  3. A. Car, C. Stropnik, W. Yave, and K. V. Peinemann, Adv. Funct. Mater. 18, 2815 (2018).

    Article  Google Scholar 

  4. I. Pinnau and L. G. Toy, J. Membr. Sci. 116, 199 (1996).

    Article  CAS  Google Scholar 

  5. N. A. Plate, A. K. Bokarev, N. E. Kaliuzhnyi, E. G. Litvinova, V. S. Khotimskii, V. V. Volkov, and Yu. P. Yampolskii, J. Membr. Sci. 60, 13 (1991).

    Article  CAS  Google Scholar 

  6. A. V. Yakovlev, M. G. Shalygin, S. M. Matson, V. S. Khotimskiy, and V. V. Teplyakov, J. Membr. Sci. 434, 99 (2013).

    Article  CAS  Google Scholar 

  7. A. Trusov, S. Legkov, L. J. P. Broeke, E. Goetheer, V. Khotimsky, and A. Volkov, J. Membr. Sci. 383, 241 (2011).

    Article  CAS  Google Scholar 

  8. G. Consolati, I. Genco, M. Pegoraro, and L. Zande-righi, J. Polym. Sci., Part B: Polym. Phis. 34, 357 (1996).

    Article  CAS  Google Scholar 

  9. M. Langsam and L. M. Robeson, Polym. Eng. Sci. 29, 44 (1989).

    Article  CAS  Google Scholar 

  10. H. Hachisuka, H. Kito, Y. Tsujita, A. Takizawa, and T. Kinoshita, J. Appl. Polym. Sci. 35, 1333 (1988).

    Article  CAS  Google Scholar 

  11. A. Tanaka, K. Nitta, R. Maekawa, T. Masuda, and T. Higashimura, Polym. J. 24, 1173 (1992).

    Article  CAS  Google Scholar 

  12. K. Nagai, A. Higuchi, and T. Nakagawa, J. Polym. Sci. B: Polym. Phys. 33, 289 (1995).

    Article  CAS  Google Scholar 

  13. J. D. Wind, C. Staudt-Bickel, D. R. Paul, and W. J. Koros, Macromolecules 36, 1882 (2003).

    Article  CAS  Google Scholar 

  14. A. M. W. Hillock and W. J. Koros, Macromolecules 40, 583 (2007).

    Article  CAS  Google Scholar 

  15. B. Kraftschik and W. J. Koros, Macromolecules 46, 6908 (2013).

    Article  CAS  Google Scholar 

  16. H. Eguchi, D. J. Kim, and W. J. Koros, Polymer 58, 121 (2015).

    Article  CAS  Google Scholar 

  17. T. Masuda, E. Isobe, and T. Higashimura, Macromolecules 18, 841 (1985).

    Article  CAS  Google Scholar 

  18. R. W. Baker, Membrane Technology and Applications (John Wiley & Sons, 2012).

    Book  Google Scholar 

  19. S. Kim and Y. M. Lee, Prog. Polym. Sci. 43, 1 (2015).

    Article  CAS  Google Scholar 

  20. Q. Song, C. Shuai, R. H. Pritchard, B. Ghalei, S. A. Al-Muhtaseb, E. M. Terentjev, A. K. Cheetham, and E. Sivaniah, Nat. Commun. 5, 4813 (2014).

    Article  PubMed  Google Scholar 

  21. M. Calle, H. J. Jo, C. M. Doherty, A. J. Hill, and Y. M. Lee, Macromolecules 48, 2603 (2015).

    Article  CAS  Google Scholar 

  22. J. J. Krol, M. Boerrigter, and G. H. Koops, J. Membr. Sci. 184, 275 (2001).

    Article  CAS  Google Scholar 

  23. A. F. Ismail and W. Lorna, Sep. Purif. Technol. 27, 173 (2002).

    Article  CAS  Google Scholar 

  24. T. S. Chung, J. Ren, R. Wang, D. F. Li, Y. Liu, K. P. Pramoda, C. Cao, and W. W. Loh, J. Membr. Sci. 214, 5769 (2003).

    Article  Google Scholar 

  25. C. N. Dudley, B. Shoeberl, G. K. Sturgill, H. W. Beckham, and M. E. Rezac, J. Membr. Sci. 191, 1 (2001).

    Article  CAS  Google Scholar 

  26. M. M. Khan, G. Bengston, S. Shishatskiy, B. N. Gacal, Md. M. Rahman, S. Neumann, V. Filiz, and V. Abetz, Eur. Polym. J. 49, 4157 (2013).

    Article  CAS  Google Scholar 

  27. M. S. McCaig and D. R. Paul, Polymer 40, 7209 (1999).

    Article  CAS  Google Scholar 

  28. J. Jia and G. L. Baker, J. Polym. Sci. Part B: Polym. Phys. 36, 959 (998).

  29. S. D. Kelman, S. Matteucci, C. W. Bielawski, and B. D. Freeman, Polymer 48, 6881 (2007).

    Article  CAS  Google Scholar 

  30. K. Nagai, T. Masuda, T. Nakagawa, and B. D. Freeman, Prog. Polym. Sci. 26, 721 (2001).

    Article  CAS  Google Scholar 

  31. B. T. Low, Y. Xiao, T. S. Chung, and Y. Liu, Macromolecules 41, 1297 (2008).

    Article  CAS  Google Scholar 

  32. K. Vanherck, A. Cano-Odena, G. Koeckelberghs, T. Dedroog, and I. Vankelecom, J. Membr. Sci. 353, 135 (2010).

    Article  CAS  Google Scholar 

  33. A. M. W. Hillock and W. J. Koros, Macromolecules 40, 583 (2007).

    Article  CAS  Google Scholar 

  34. J. D. Wind, D. R. Paul, and W. J. Koros, J. Membr. Sci. 228, 227 (2004).

    Article  CAS  Google Scholar 

  35. J. D. Wind, C. Staudt-Bickel, D. R. Paul, and W. J. Koros, Macromolecules 36, 1882 (2003).

    Article  CAS  Google Scholar 

  36. W. S. Hung, C. H. Tsou, and M. De Guzman, Q. F. An, Y. L. Liu, Y. M. Zhang, C. C. Hu, K. R. Lee, and J. Y. Lai, Chem. Mater. 26, 2983 (2014).

    Article  CAS  Google Scholar 

  37. Z. Jia, Y. Wang, W. Shi, and J. Wang, J. Membr. Sci. 520, 139 (2016).

    Article  CAS  Google Scholar 

  38. F. Aziz and A. F. Ismail, Sep. Purif. Technol. 73, 421 (2010).

    Article  CAS  Google Scholar 

  39. P. S. Tin, T. S. Chung, Y. Liu, R. Wang, S. L. Liu, and K. P. Pramoda, J. Membr. Sci. 225, 77 (2003).

    Article  CAS  Google Scholar 

  40. Y. Liu, R. Wang, and T. S. Chung, J. Membr. Sci. 189, 231 (2001).

    Article  CAS  Google Scholar 

  41. S. Zhang, C. Li, X. Xie, and F. Zhang, Int. J. Hydrog. Energy 39, 13718 (2014).

    Article  CAS  Google Scholar 

  42. L. Shao, L. Liu, S. X. Cheng, Y. D. Huang, and J. Ma, J. Membr. Sci. 312, 174 (2008).

    Article  CAS  Google Scholar 

  43. X. Y. Qiao and T. S. Chung, AIChE J. 52, 3462 (2006).

    Article  CAS  Google Scholar 

  44. L. Shao, T. S. Chung, S. H. Goh, and K. P. Pramoda, J. Membr. Sci. 267, 78 (2005).

    Article  CAS  Google Scholar 

  45. L. Shao, C. H. Lau, and T. S. Chung, Int. J. Hydrog. Energy 34, 8716 (2009).

    Article  CAS  Google Scholar 

  46. D. W. Mangindaan, G. M. Shi, and T. S. Chung, J. Membr. Sci. 458, 76 (2014).

    Article  CAS  Google Scholar 

  47. T.-S. Chung, L. Shao, and P. S. Tin, Int. J. Hydrog. Energy 27, 998 (2006).

    CAS  Google Scholar 

  48. M. Omidvar, C. M. Stafford, and H. Lin, J. Membr. Sci. 575, 118 (2019).

    Article  CAS  Google Scholar 

  49. NasirN. A. Abdul, J. H. Ling, M. U. M. Junaidi, N. A. Hashim, H. F. Hizzaddin, M. F. Rabuni, M. I. I. Z. Abidin, and R. Rohani, Asia-Pac. J. Chem. Eng. 15, e2411 (2020).

    Google Scholar 

  50. H. Li, N. Yu, F. Gellrich, A. K. Reumert, M. R. Kraglund, J. Dong, D. Aili, and J. Yang, J. Membr. Sci. 633, 119418 (2021).

    Article  CAS  Google Scholar 

  51. S. Xu, L. Liu, and Y. Wang, Sep. Purif. Technol. 185, 215 (2017).

    Article  CAS  Google Scholar 

  52. J. Gao, S. P. Sun, W. P. Zhu, and T. S. Chung, J. Membr. Sci. 452, 300 (2014).

    Article  CAS  Google Scholar 

  53. L. Shao, T. S. Chung, S. H. Goh, and K. P. Pramoda, J. Membr. Sci. 238, 153 (2004).

    Article  CAS  Google Scholar 

  54. Y. Xiao, T. S. Chung, and M. L. Chung, Langmuir 20, 8230 (2004).

    Article  CAS  PubMed  Google Scholar 

  55. K. Vanherck, P. Vandezande, S. O. Aldea, and I. F. J. Vankelecom, J. Membr. Sci. 320, 468 (2008).

    Article  CAS  Google Scholar 

  56. Y. H. See-Toh, M. Silva, and A. Livingston, J. Membr. Sci. 324, 220 (2008).

    Article  CAS  Google Scholar 

  57. K. Vanherck, G. Koeckelberghs, and I. F. Vankelecom, Prog. Polym. Sci. 38, 874 (2013).

    Article  CAS  Google Scholar 

  58. A. A. Tashvigh, L. Luo, T. S. Chung, M. Weber, and C. Maletzko, J. Membr. Sci. 545, 221 (2018).

    Article  Google Scholar 

  59. M. H. D. A. Farahani, D. Hua, and T. S. Chung, J. Membr. Sci. 548, 319 (2018).

    Article  Google Scholar 

  60. Q. Ge, X. Liang, L. Ding, J. Hou, J. Miao, B. Wu, Z. Yang, and T. Xu, J. Membr. Sci. 573, 595 (2019).

    Article  CAS  Google Scholar 

  61. S. M. Matson, E. G. Litvinova, V. K. Chernikov, G. N. Bondarenko, and V. S. Khotimskiy, Polymer 236, 124308 (2021).

    Article  CAS  Google Scholar 

  62. C. Ba, J. Langer, and J. Economy, J. Membr. Sci. 327, 49 (2009).

    Article  CAS  Google Scholar 

  63. V. S. Khotimsky, M. V. Tchirkova, E. G. Litvinova, A. I. Rebrov, and G. N. Bondarenko, J. Polym. Sci. A: Polym. Chem. 41, 2133 (2003).

    Article  CAS  Google Scholar 

  64. V. G. Polevaya, G. N. Bondarenko, G. A. Shandryuk, V. D. Dolzhikova, and V. S. Khotimskiy, Russ. Chem. Bull. 65, 1067 (2016).

    Article  CAS  Google Scholar 

  65. V. P. Makrushin, V. K. Chernikov, I. S. Levin, A. A. Kossov, and S. M. Matson, Membr. Membr. Technol. 5, 148 (2023).

    Article  CAS  Google Scholar 

  66. W. Yave, K. V. Peinemann, S. Shishatskiy, V. Khotimskiy, M. Chirkova, S. Matson, E. Litvinova, and N. Lecerf, Macromolecules 40, 8991 (2007).

    Article  CAS  Google Scholar 

Download references

Funding

This work was carried out within the framework of State Assignment for the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991, Moscow, Russia

    V. P. Makrushin, A. A. Kossov, E. G. Litvinova, G. N. Bondarenko & S. M. Matson

Authors
  1. V. P. Makrushin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Kossov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. G. Litvinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. N. Bondarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. M. Matson
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. M. Matson.

Ethics declarations

The authors of this work declare that they have no conflicts of interest.

Additional information

Translated by T. Soboleva

Publisher’s Note.

Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makrushin, V.P., Kossov, A.A., Litvinova, E.G. et al. Crosslinking of Brominated Poly(1-trimethylsilyl-1-propyne) Using Polyethylenimine as a Crosslinking Agent. Membr. Membr. Technol. 6, 84–91 (2024). https://doi.org/10.1134/S2517751624020057

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2517751624020057

Keywords:

Search

Navigation