Skip to main content
SpringerLink
Log in

A Novel Strategy for Poly(β-alanine-b-lactone)s: Sequentially HTP and AROP

  • Article
  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

A series of poly(β-alanine-b-lactone)s were prepared by combination of hydrogen-transfer polymerization (HTP) of acrylamide and anionic ring-opening polymerization (AROP) of β-propiolactone, α-methyl propiolactone, β-butyrolactone, and δ-valerolactone. Poly-β-alanine (PBA) having a living anionic end-group for a further extension was obtained via HTP of acrylamide. Then, the anionic end-group on PBA chains was used as initiation sites for AROP of the lactones. By varying acrylamide feeds, a series of copolymers was obtained with a hard segment (β-alanine) content between 6.86 and 36.82 mol%. Elemental analyses and spectral data (MALDI-MS, 1H-NMR, and FT-IR) for all new products were consistent with the proposed structures.

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

Similar content being viewed by others

References

  1. H. Feng, X. Lu, W. Wang, N. G. Kang and J. W. Mays, Polymers (Basel), 9, 494 (2017).

    Article  CAS  Google Scholar 

  2. S. D. Fitzpatrick, L. E. Fitzpatrick, A. Thakur, M. A. J. Mazumder, and H. Sheardown, Expert Rev. Med. Devices, 9, 339 (2012).

    Article  CAS  PubMed  Google Scholar 

  3. M. Ponjavic, M. S. Nikolic, J. Nikodinovic-Runic, T. Ilic-Tomic, and J. Djonlagic, Int. J. Polym. Mater. Polym. Biomater., 68, 308 (2019).

    Article  CAS  Google Scholar 

  4. G. J. Galo, E. L. Crepaldi, D. Grosso, and C. Sanchez, Curr. Opin. Colloid Interface Sci., 8, 109 (2003).

    Article  CAS  Google Scholar 

  5. M. Li and C. K. Ober, Mater. Today, 9, 30 (2006).

    Article  CAS  Google Scholar 

  6. A. Sandeau, S. Mazières, and M. Destarac, Polymer (Guildf), 53, 5601 (2012).

    Article  CAS  Google Scholar 

  7. K. Matyjaszewski and J. Spanswick, Mater. Today, 8, 26 (2005).

    Article  CAS  Google Scholar 

  8. M. H. Acar and K. Matyjaszewski, Macromol. Chem. Phys., 200, 1094 (1999).

    Article  CAS  Google Scholar 

  9. D. Le, T. N. T. Phan, L. Autissier, L. Charles, and D. Gigmes, Polym. Chem., 7, 1659 (2016).

    Article  CAS  Google Scholar 

  10. E. Tinajero-Díaz, A. Martínez-de Ilarduya, S. Muñoz-Guerra, M. V. dePaz, and E. Galbis, Eur. Polym. J., 108, 380 (2018).

    Article  CAS  Google Scholar 

  11. D. S. Breslow, G. E. Hulse, and A. S. Matlack, J. Am. Chem. Soc., 79, 3760 (1957).

    Article  CAS  Google Scholar 

  12. B. A. Rozenberg, Des. Monomers Polym., 7, 135 (2004).

    Article  CAS  Google Scholar 

  13. B. A. Rozenberg, Macromol. Symp., 199, 443 (2003).

    Article  CAS  Google Scholar 

  14. T. Iwamura, I. Tomita, M. Suzuki, and T. Endo, J. Polym. Sci. Part A Polym. Chem., 37, 465 (1999).

    Article  CAS  Google Scholar 

  15. L. L. Gur’eva, A. I. Tkachuk, E. A. Dzhavadyan, G. A. Estrina, N. F. Surkov, I. V. Sulimenkov, and B. A. Rozenberg, Polym. Sci. Ser. A, 49, 987 (2007).

    Article  Google Scholar 

  16. L. Trossarelli, M. Guaita, and G. Camino, J. Polym. Sci. Part C Polym. Symp., 22, 721 (1969).

    Article  Google Scholar 

  17. K. Kumar, P. Adhikary, K. Tungala, V. Azmeera, and S. Krishnamoorthi, J. Appl. Polym. Sci., 132, 1 (2015).

    Google Scholar 

  18. K. Roos, M. Planes, C. Bakkali-Hassani, J. Mehats, A. Vax, and S. Carlotti, Macromolecules, 49, 2039 (2016).

    Article  CAS  Google Scholar 

  19. J. Masamoto, K. Sasaguri, C. Ohizumi, K. Yamaguchi, and H. Kobayashi, J. Appl. Polym. Sci., 14, 667 (1970).

    Article  CAS  Google Scholar 

  20. M. R. Lee, S. S. Stahl, S. H. Gellman, and K. S. Masters, J. Am. Chem. Soc., 131, 16779 (2009).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. M. T. Dohm, B. P. Mowery, A. M. Czyzewski, S. S. Stahl, S. H. Gellman, and A. E. Barron, J. Am. Chem. Soc., 132, 7957 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. R. Liu, K. Z. Vang, P. K. Kreeger, S. H. Gellman, and K. S. Masters, J. Biomed. Mater. Res. Part A, 100A, 2750 (2012).

    Article  CAS  Google Scholar 

  23. S. Chakraborty, R. Liu, J. J. Lemke, Z. Hayouka, R. A. Welch, B. Weisblum, K. S. Masters, and S. H. Gellman, ACS Macro Lett., 2, 753 (2013).

    Article  CAS  Google Scholar 

  24. R. Liu, K. S. Masters, and S. H. Gellman, Biomacromolecules, 13, 1100 (2012).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. E. Çatiker, E. Konuk, T. Gültan, and M. Gümüşderelioğlu, Int. J. Polym. Mater. Polym. Biomater., 68, 338 (2019).

    Article  CAS  Google Scholar 

  26. Z. Jedlinński, J. Heterocycl. Chem., 38, 1249 (2001).

    Article  Google Scholar 

  27. A. C. Albertsson and I. K. Varma, Biomacromolecules, 4, 1466 (2003).

    Article  CAS  PubMed  Google Scholar 

  28. S. A. Mirmohammadi, M. Imani, H. Uyama, and M. Atai, Int. J. Polym. Mater. Polym. Biomater., 63, 624 (2014).

    Article  CAS  Google Scholar 

  29. Q. Song, C. Pascouau, J. Zhao, G. Zhang, F. Peruch, and S. Carlotti, Prog. Polym. Sci., 110, 101309 (2020).

    Article  CAS  Google Scholar 

  30. M. Winnacker and B. Rieger, Polym. Chem., 7, 7039 (2016).

    Article  CAS  Google Scholar 

  31. P. Garg, H. Keul, D. Klee, and M. Möller, Des. Monomers Polym., 12, 405 (2009).

    Article  CAS  Google Scholar 

  32. A. C. Fonseca, M. H. Gil, and P. N. Simöes, Prog. Polym. Sci., 39, 1291 (2014).

    Article  CAS  Google Scholar 

  33. P. Karimi, A. S. Rizkalla, and K. Mequanint, Materials (Basel), 3, 2346 (2010).

    Article  CAS  PubMed Central  Google Scholar 

  34. A. Rodriguez-Galan, L. Franco, and J. Puiggali, Polymers (Basel), 3, 65 (2011).

    Article  CAS  Google Scholar 

  35. S. Lin, X. Yu, Y. Tu, H. Xu, S. Z. D. Cheng, and L. Jia, Chem. Commun., 46, 4273 (2010).

    Article  CAS  Google Scholar 

  36. E. Çatiker, E. Meyvaci, M. Atakay, B. Salih, and T. Öztürk, Polym. Bull., 76, 2113 (2019).

    Article  CAS  Google Scholar 

  37. A. Uzunlar and E. Çatiker, Hacettepe J. Biol. Chem., 3, 435 (2018).

    Article  Google Scholar 

  38. S. Penczek and A. Duda, Makromol. Chemie. Macromol. Symp., 67, 15 (1993).

    Article  CAS  Google Scholar 

  39. S. Penczek, M. Cypryk, A. Duda, P. Kubisa, and S. Słomkowski, Prog. Polym. Sci., 32, 247 (2007).

    Article  CAS  Google Scholar 

  40. A. Duda and A. Kowalski, in Handbook of Ring-Opening Polymerization, P. Dubois, O. Coulembier, and J.-M. Requez, Eds., WILEY-VCH Verlay GmbH & Co. KGaA, Weinheim, 2009, pp 1–51.

  41. A. Rodríguez-Galán, L. Franco, and J. Puiggalí, in Handbook of Biodegradable Polymers, A. Lendlein and A. Sisson, Eds., Wiley-VCH Verlag & Co. KGaA, Weinheim, 2011, Chap. 6, pp 133–154.

  42. H. G. Chae, S. H. Park, B. C. Kim, and D. K. Kim, J. Polym. Sci. Part B Polym. Phys., 42, 1759 (2004).

    Article  CAS  Google Scholar 

  43. E. Çatiker, T. Öztürk, M. Atakay, and B. Salih, J. Macromol. Sci. Part A Pure Appl. Chem., 57, 600 (2020).

    Article  CAS  Google Scholar 

  44. J. Hong, D. Cho, T. Chang, W. S. Shim, and D. S. Lee, Macromol. Res., 11, 341 (2003).

    Article  CAS  Google Scholar 

  45. M. Girod, M. Mazarin, T. N. T. Phan, D. Gigmes, and L. Charles, J. Polym. Sci. Part A Polym. Chem., 47, 3380 (2009).

    Article  CAS  Google Scholar 

  46. M. Chausson, A. S. Fluchère, E. Landreau, Y. Aguni, Y. Chevalier, T. Hamaide, N. Abdul-Malak, and I. Bonnet, Int. J. Pharm., 362, 153 (2008).

    Article  CAS  PubMed  Google Scholar 

  47. B. Savaş, E. Çatiker, T. Öztürk, and E. Meyvaci, J. Polym. Res., 28, 1 (2021).

    Article  CAS  Google Scholar 

  48. M. Pitsikalis, Ionic Polymerization, in Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier, 2013.

  49. A. Hirao, R. Goseki, and T. Ishizone, Macromolecules, 47, 1883 (2014).

    Article  CAS  Google Scholar 

  50. T. Ishizone and R. Goseki, Eds. S. Kobayashi and K. Müllen, Berlin, Heidelberg, Springer Berlin Heidelberg, 2021, pp 1–18.

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Art&Science, Ordu University, Ordu, 52200, Turkey

    Efkan Çatıker & Ayçanur Hamzaçebi

Authors
  1. Efkan Çatıker
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ayçanur Hamzaçebi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Efkan Çatıker.

Additional information

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

Acknowledgment: The study has been supported by the Scientific and Technological Research Council of Turkey (TUBITAK) with project number 116Z542.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Çatıker, E., Hamzaçebi, A. A Novel Strategy for Poly(β-alanine-b-lactone)s: Sequentially HTP and AROP. Macromol. Res. 30, 305–313 (2022). https://doi.org/10.1007/s13233-022-0034-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-022-0034-8

Keywords

Search

Navigation