Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Original Article
  • Published:

Immobilization of β-cyclodextrin onto polypropylene nonwoven fabric based on photooxidative surface modification

Polymer Journal volume 55, pages 599–605 (2023)Cite this article

Subjects

Abstract

We developed β-cyclodextrin (CD)/polypropylene (PP) composite nonwoven fabrics (NWFs) via surface modification of PP using the photoactivated chlorine dioxide radical (ClO2•) oxidation method. The hydrophilicity and dyeability of the PP NWFs were improved owing to the immobilization of β-CD. In addition, the prepared β-CD/PP composite NWFs showed sustained drug release for over 12 h in phosphate buffer, indicating that the β-CD supported on PP fibers functioned successfully.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on SpringerLink
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Nava-Ortíz CAB, Alvarez-Lorenzo C, Bucio E, Concheiro A, Burillo G. Cyclodextrin-functionalized polyethylene and polypropylene as biocompatible materials for diclofenac delivery. Int J Pharm. 2009;382:183–91.

    Article  PubMed  Google Scholar 

  2. Lee JH, Park SH, Kim SH. Fabrication of bio-based polyurethane nanofibers incorporated with a triclosan/cyclodextrin complex for antibacterial applications. RSC Adv. 2020;10:3450–8.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Canbolat MF, Celebioglu A, Uyar T. Drug delivery system based on cyclodextrin-naproxen inclusion complex incorporated in electrospun polycaprolactone nanofibers. Colloids Surf B. 2014;115:15–21.

    Article  CAS  Google Scholar 

  4. Haji A, Mehrizi MK, Sarani M. Surface modification of polypropylene Nonwoven by plasma and β-Cyclodextrin: optimization and cationic dye removal studies. Surf Interfaces. 2021;25:101278.

    Article  CAS  Google Scholar 

  5. Thuaut PL, Martel B, Crini G, Maschke U, Coqueret X, Morcellet M. Grafting of cyclodextrins onto polypropylene nonwoven fabrics for the manufacture of reactive filters. I. Synthesis parameters. J Appl Polym Sci. 2000;77:2118–25.

    Article  Google Scholar 

  6. Martel B, Thuaut PL, Crini G, Morcellet M, Naggi AM, Maschke U, et al. Grafting of cyclodextrins onto polypropylene nonwoven fabrics for the manufacture of reactive filters. II. Characterization J Appl Polym Sci. 2000;78:2166–73.

    Article  CAS  Google Scholar 

  7. Martel B, Thuaut PL, Bertini S, Crini G, Bacquet M, Torri G, et al. Grafting of cyclodextrins onto polypropylene nonwoven fabrics for the manufacture of reactive filters. III Study of the sorption properties. J Appl Polym Sci. 2002;85:1771–8.

    Article  CAS  Google Scholar 

  8. Gawish SM, Matthews SR, Wafa DM, Breidt F, Bourham MA. Atmospheric plasma-aided biocidal finishes for nonwoven polypropylene fabrics. I. Synthesis and characterization. J Appl Polym Sci. 2007;103:1900–10.

    Article  CAS  Google Scholar 

  9. Wafa DM, Breidt F, Gawish SM, Matthews SR, Donohue KV, Roe RM, et al. Atmospheric plasma-aided biocidal finishes for nonwoven polypropylene fabrics. II Functionality of synthesized fabrics. J Appl Polym Sci. 2007;103:1911–7.

    Article  CAS  Google Scholar 

  10. Ghoul YE, Martel B, Achari AE, Campagne C, Razafimahefa L, Vroman I. Improved dyeability of polypropylene fabrics finished with β-cyclodextrin–citric acid polymer. Polym J. 2010;42:804–11.

    Article  Google Scholar 

  11. Ohkubo K, Hirose K. Light-driven C–H oxygenation of methane into methanol and formic acid by molecular oxygen using a perfluorinated solvent. Angew Chem Int Ed. 2018;57:2126–9.

    Article  CAS  Google Scholar 

  12. Ohkubo K, Asahara H, Inoue T. Photochemical C–H oxygenation of side-chain methyl groups in polypropylene with chlorine dioxide. Chem Commun. 2019;55:4723–6.

    Article  CAS  Google Scholar 

  13. Jia Y, Chen J, Asahara H, Asoh T, Uyama H. Polymer surface oxidation by light-activated chlorine dioxide radical for metal–plastics adhesion. ACS Appl Polym Mater. 2019;1:3452–8.

    Article  CAS  Google Scholar 

  14. Jia Y, Chen J, Asahara H, Hsu Y, Asoh T, Uyama H. Photooxidation of the ABS resin surface for electroless metal plating. Polymer. 2020;200:122592.

    Article  CAS  Google Scholar 

  15. Ghalei S, Li J, Douglass M, Garren M, Handa H. Synergistic approach to develop antibacterial electrospun scaffolds using honey and S-nitroso-N-acetyl penicillamine. ACS Biomater Sci Eng. 2021;7:517–26.

    Article  CAS  PubMed  Google Scholar 

  16. Sano S, Kato K, Ikada Y. Introduction of functional groups onto the surface of polyethylene for protein immobilization. Biomaterials. 1993;14:817–22.

    Article  CAS  PubMed  Google Scholar 

  17. Carrazana J, Reija B, Cabrer P, Soufi W, Novo M, Tato J. Complexation of methyl orange with ß-cyclodextrin: detailed analysis and application to quantification of polymer-bound cyclodextrin. Supramol Chem. 2004;16:549–59.

    Article  CAS  Google Scholar 

  18. Mehta SK, Bhasin KK, Dham S. Energetically favorable interactions between diclofenac sodium and cyclodextrin molecules in aqueous media. J Colloid Interface Sci. 2008;326:374–81.

    Article  CAS  PubMed  Google Scholar 

  19. Zemljič LF, Plohl O, Vesel A, Luxbacher T, Potrč S. Physicochemical characterization of packaging foils coated by chitosan and polyphenols colloidal formulations. Int J Mol Sci. 2020;21:495.

    Article  PubMed  PubMed Central  Google Scholar 

  20. It is generally known that when the pH of surrounding solution increases, the positive charge on the PEI coated samples was shielded by OH−. The zeta potential of Ox-80-PEI decreases above pH 8.5, which indicates that cationic PEI is coated. Selected examples of zeta potential measurement for PEI coated material, see;

  21. Wei X, Bao X, Wu J, Li C, Shi Y, Chen J, et al. Typical pharmaceutical molecule removal behavior from water by positively and negatively charged composite hollow fiber nanofiltration membranes. RSC Adv. 2018;8:10396–408.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Barick P, Saha BP, Mitra R, Joshi SV. Effect of concentration and molecular weight of polyethylenimine on zeta potential, isoelectric point of nanocrystalline silicon carbide in aqueous and ethanol medium. Ceram Int. 2015;41:4289–93.

    Article  CAS  Google Scholar 

  23. Ding L, Zhang X, Wang Y. Study on the behavior of BOPP film treated by corona discharge. Coatings. 2020;10:1195.

    Article  CAS  Google Scholar 

  24. Strobel M, Jones V, Lyons CS, Ulsh M, Kushner MJ, Dorai R, et al. A comparison of corona-treated and flame-treated polypropylene films. Plasma Process Polym. 2003;8:61–95.

    Article  CAS  Google Scholar 

  25. Szewczyk PK, Ura DP, Metwally S, Knapczyk-Korczak J, Gajek M, Marzec MM, et al. Roughness and fiber fraction dominated wetting of electrospun fiber-based porous meshes. Polymers. 2019;11:34.

    Article  Google Scholar 

  26. Cohen-Arazi N, Domb AJ, Katzhendler J. New biocompatible polyesters derived from α-amino acids: hydrolytic degradation behavior. Polymers. 2010;2:418–39.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by JSPS KAKENHI Grant JP20K05606 to HA, NEDO (New Energy and Industrial Technology Development Organization) grant 17101509-0 to HA, and JST OPERA (Open Innovation with Enterprises, Research Institute, and Academia) grant JPMJOP1861 to TI.

Author information

Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka, 565-0871, Japan

    Keita Yamamoto, Haruyasu Asahara, Maiko Moriguchi & Tsuyoshi Inoue

  2. Institute for Open and Transdisciplinary Research Initiatives, Osaka University, 1-6 Yamadaoka, Suita, Osaka, 565-0871, Japan

    Haruyasu Asahara & Tsuyoshi Inoue

Authors
  1. Keita Yamamoto
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Haruyasu Asahara
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Maiko Moriguchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tsuyoshi Inoue
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Haruyasu Asahara.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

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

Supplementary information

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yamamoto, K., Asahara, H., Moriguchi, M. et al. Immobilization of β-cyclodextrin onto polypropylene nonwoven fabric based on photooxidative surface modification. Polym J 55, 599–605 (2023). https://doi.org/10.1038/s41428-022-00751-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41428-022-00751-8

Search

Advanced search

Quick links