Skip to main content
SpringerLink
Log in

A facile antibacterial coating based on UV-curable acrylated imidazoliums

  • Published:
Journal of Coatings Technology and Research Aims and scope Submit manuscript

Abstract

Using ultraviolet (UV)-curable 3-(2-(methacryloyloxy)ethyl)-1-alkyl imidazoliums with different alkyl substituents as the bactericidal monomers and trimethylolpropane triacrylate as the crosslinker, highly efficient antibacterial coatings were designed and facilely prepared by a one-step UV-curing method. The differential photocalorimetry experiment showed these monomers polymerized within 120 s under UV irradiation, indicating a very good curable property. The excellent antibacterial activity of these coatings, which reached up to 99.8% ratio against Escherichia Coli, was demonstrated by a shake flask test method.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Engler, AC, Wiradharma, N, Ong, ZY, Coady, DJ, Hedrick, JL, Yang, Y-Y, “Emerging Trends in Macromolecular Antimicrobials to Fight Multi-drug-Resistant Infections.” Nano Today, 7 (3) 201–222 (2012)

    Article  Google Scholar 

  2. Exley, SE, Paslay, LC, Sahukhal, GS, Abel, BA, Brown, TD, McCormick, CL, Heinhorst, S, Koul, V, Choudhary, V, Elasri, MO, Morgan, SE, “Antimicrobial Peptide Mimicking Primary Amine and Guanidine Containing Methacrylamide Copolymers Prepared by Raft Polymerization.” Biomacromolecules, 16 (12) 3845–3852 (2015)

    Article  Google Scholar 

  3. Uppu, DS, Samaddar, S, Ghosh, C, Paramanandham, K, Shome, BR, Haldar, J, “Amide Side Chain Amphiphilic Polymers Disrupt Surface Established Bacterial Bio-films and Protect Mice from Chronic Acinetobacter baumannii Infection.” Biomaterials, 74 131–143 (2016)

    Article  Google Scholar 

  4. Charnley, M, Textor, M, Acikgoz, C, “Designed Polymer Structures with Antifouling–Antimicrobial Properties.” React. Funct. Polym., 71 (3) 329–334 (2011)

    Article  Google Scholar 

  5. Tashiro, T, “Antibacterial and Bacterium Adsorbing Macromolecules.” Macromol. Mater. Eng., 286 (2) 63–87 (2001)

    Article  Google Scholar 

  6. El-R, K, Worley, SD, Broughton, R, “The Chemistry and Applications of Antimicrobial Polymers: A State-of-the-Art Review.” Biomacromolecules, 8 (5) 1359–1384 (2007)

    Article  Google Scholar 

  7. Majumdar, P, He, J, Lee, E, Kallam, A, Gubbins, N, Stafslien, SJ, Daniels, J, Chisholm, BJ, “Antimicrobial Activity of Polysiloxane Coatings Containing Quaternary Ammonium-Functionalized Polyhedral Oligomeric Silsesquioxane.” J. Coat. Technol. Res., 7 (4) 455–467 (2009)

    Article  Google Scholar 

  8. Salwiczek, M, Qu, Y, Gardiner, J, Strugnell, RA, Lithgow, T, McLean, KM, Thissen, H, “Emerging Rules for Effective Antimicrobial Coatings.” Trends Biotechnol., 32 (2) 82–90 (2014)

    Article  Google Scholar 

  9. Degli Esposti, M, Pilati, F, Bondi, M, de Niederhäusern, S, Iseppi, R, Toselli, M, “Preparation, Characterization, and Antibacterial Activity of Photocured Thymol-doped Acrylic Resins.” J. Coat. Technol. Res., 10 (3) 371–379 (2012)

    Article  Google Scholar 

  10. Docherty, KM, Kulpa, JCF, “Toxicity and Antimicrobial Activity of Imidazolium and Pyridinium Ionic Liquids.” Green Chem., 7 (4) 185 (2005)

    Article  Google Scholar 

  11. Iwai, N, Nakayama, K, Kitazume, T, “Antibacterial Activities of Imidazolium, Pyrrolidinium and Piperidinium Salts.” Bioorg. Med. Chem. Lett., 21 (6) 1728–1730 (2011)

    Article  Google Scholar 

  12. Khabnadideh, S, Rezaei, Z, Khalafi-Nezhad, A, Bahrinajafi, R, Mohamadi, R, Farrokhroz, AA, “Synthesis of N-Alkylated Derivatives of Imidazole as Antibacterial Agents.” Bioorg. Med. Chem. Lett., 13 (17) 2863–2865 (2003)

    Article  Google Scholar 

  13. Łuczak, J, Jungnickel, C, Łącka, I, Stolte, S, Hupka, J, “Antimicrobial and Surface Activity of 1-Alkyl-3-Methylimidazolium Derivatives.” Green Chem., 12 (4) 593 (2010)

    Article  Google Scholar 

  14. Venkata Nancharaiah, Y, Reddy, GK, Lalithamanasa, P, Venugopalan, VP, “The Ionic Liquid 1-Alkyl-3-Methylimidazolium Demonstrates Comparable Antimicrobial and Antibiofilm Behavior to a Cationic Surfactant.” Biofouling, 28 (10) 1141–1149 (2012)

    Article  Google Scholar 

  15. Gilbert, P, Moore, LE, “Cationic Antiseptics: Diversity of Action Under a Common Epithet.” J. Appl. Microbiol., 99 (4) 703–715 (2005)

    Article  Google Scholar 

  16. Hodyna, D, Kovalishyn, V, Rogalsky, S, Blagodatnyi, V, Petko, K, Metelytsia, L, “Antibacterial Activity of Imidazolium-Based Ionic Liquids Investigated by QSAR Modeling and Experimental Studies.” Chem. Biol. Drug Des., 88 (3) 422–433 (2016)

    Article  Google Scholar 

  17. Cornellas, A, Perez, L, Comelles, F, Ribosa, I, Manresa, A, Garcia, MT, “Self-Aggregation and Antimicrobial Activity of Imidazolium and Pyridinium Based Ionic Liquids in Aqueous Solution.” J. Colloid Interface Sci., 355 (1) 164 (2011)

    Article  Google Scholar 

  18. Pernak, J, Sobaszkiewicz, K, Mirska, I, “Anti-Microbial Activities of Ionic Liquids.” Green Chem., 5 (1) 52–56 (2003)

    Article  Google Scholar 

  19. Zheng, Z, Xu, Q, Guo, J, Qin, J, Mao, H, Wang, B, Yan, F, “Structure-Antibacterial Activity Relationships of Imidazolium-Type Ionic Liquid Monomers, Poly(ionic liquids) and Poly(ionic liquid) Membranes: Effect of Alkyl Chain Length and Cations.” ACS Appl. Mater. Interfaces, 8 (20) 12684–12692 (2016)

    Article  Google Scholar 

  20. Patachia, S, Damian, N, “Cryogels Based on Poly(Vinyl Alcohol)/Ionic Liquids: From Obtaining to Antimicrobial Activity.” Soft Mater., 12 (4) 371–379 (2014)

    Article  Google Scholar 

  21. Guo, J, Xu, Q, Zheng, Z, Zhou, S, Mao, H, Wang, B, Yan, F, “Intrinsically Antibacterial Poly(Ionic Liquid) Membranes: The Synergistic Effect of Anions.” ACS Macro Lett., 4 (10) 1094–1098 (2015)

    Article  Google Scholar 

  22. Zhou, C, Li, Y-H, Jiang, Z-H, Ahn, K-D, Hu, T-J, Wang, Q-H, Wang, C-H, “Poly[(mercaptopropyl)methylsiloxane] (PMMS)-Based Antibacterial Polymer Coatings Prepared by a Two-Step Sequential Thiol–Ene Click Chemistry.” Chin. Chem. Lett., 27 (5) 685–688 (2016)

    Article  Google Scholar 

  23. Zhou, C, Li, Y-H, Jiang, Z-H, Ahn, K-D, Hu, T-J, Wang, Q-H, Wang, C-H, “Facile Preparation of Antibacterial Polymer Coatings Via Thiol-yne Click Photopolymerization.” Chin. Chem. Lett., 27 (5) 681–684 (2016)

    Article  Google Scholar 

  24. Yin, L-H, Ran, B, Hu, T-J, Yang, C, Fei, J-J, Li, Y-H, “Preparation of Highly Efficient Antibacterial Polymeric Films Via the Modulation of Charge Density and Hydrophobicity.” RSC Adv., 7 (10) 6006–6012 (2017)

    Article  Google Scholar 

  25. Zhang, Z, Li, YH, Xiao, H, Tu, CZ, Wang, CH, “Synthesis of Functional Ionic Liquids by Thermal Heating and Ultrasonic-Assisted Methods.” Adv. Mater. Res., 581–582 326–329 (2012)

    Google Scholar 

  26. Kim, KS, Anthony, BF, “Importance of Bacterial Growth Phase in Determining Minimal Bactericidal Concentrations of Penicillin and Methicillin.” Antimicrob. Agents Chemother., 19 (6) 1075–1077 (1981)

    Article  Google Scholar 

  27. Pridmore, A, Burch, D, Lees, P, “Determination of Minimum Inhibitory and Minimum Bactericidal Concentrations of Tiamulin Against Field Isolates of Actinobacillus Pleuropneumoniae.” Vet. Microbiol., 151 (3–4) 409–412 (2011)

    Article  Google Scholar 

  28. Seyidoglu, T, Yilmazer, U, “Modification and Characterization of Bentonite with Quaternary Ammonium and Phosphonium Salts and Its Use in Polypropylene Nanocomposites.” J. Thermoplast. Compos. Mater., 28 (1) 86–110 (2013)

    Article  Google Scholar 

  29. Chen, K, Zhou, X, Wang, X, “Synthesis and Application of a Hyperbranched Polyester Quaternary Ammonium Surfactant.” J. Surfactants Deterg., 17 (6) 1081–1088 (2014)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Science, National University of Defense Technology, Changsha, 410073, China

    Bin Ran, Tianjiao Hu, Zhenhua Jiang, Qinghua Wang & Yihe Li

  2. State Key Laboratory of NBC Protection for Civilian, Beijing, 102205, China

    Zhe Zhang & Yihe Li

  3. College of Chemistry, Xiangtan University, Xiangtan, 411100, China

    Lihua Yin

Authors
  1. Bin Ran
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhe Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lihua Yin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tianjiao Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhenhua Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Qinghua Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yihe Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yihe Li.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ran, B., Zhang, Z., Yin, L. et al. A facile antibacterial coating based on UV-curable acrylated imidazoliums. J Coat Technol Res 15, 345–349 (2018). https://doi.org/10.1007/s11998-017-9990-x

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-017-9990-x

Keywords

Search

Navigation