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Self-antibacterial UV-curable waterborne polyurethane with pendant amine and modified by guanidinoacetic acid

  • Biomaterials
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Abstract

Enhancing the dispersion stability and self-antibacterial properties of cationic waterborne polyurethane materials is of vital importance to its various applications. In this work, a novel UV-curable waterborne polyurethane with pendant amine (PWPU) from 4-NCO prepolymer and modified by guanidinoacetic acid (GAA) was prepared by a simple method. The 4-NCO prepolymer is originated from the progressively grafting of tridentate polycaprolactone. The GAA, which is rarely used in coating industry, plays a positive reinforced role in our self-antibacterial coatings. Taking fully advantage of the merits of pendant amine and GAA, PWPU without bactericides possesses excellent properties in gram-negative (92.05%) and gram-positive (94.77%) antibacterial tests. Compared with the linear amine waterborne polyurethane (LWPU), PWPU has significant superiority in stability, and the increase in antibacterial efficiency is about 50%. Moreover, antibacterial efficiency still maintained 87.94% after 12 times washing. AFM results display that GAA and pendant amine increase the hydrophilic groups of coating surface, which improves the antibacterial performance. The experiments of thermal, mechanical performance and chemical resistance proof the reliability of the coatings. Therefore, this work has large potential in the applications of antibacterial materials.

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References

  1. Fuchs AD, Tiller JC (2006) Contact-active antimicrobial coatings derived from aqueous suspensions. Angew Chem Int Ed 45:6759–6762

    Article  Google Scholar 

  2. Kumar M, Bala R, Gondil VS, Pandey SK, Chhibber S, Jain DVS, Sharma RK, Wangoo N (2017) Combating food pathogens using sodium benzoate functionalized silver nanoparticles: synthesis, characterization and antimicrobial evaluation. J Mater Sci. doi:10.1007/s10853-017-1072-z

    Google Scholar 

  3. Wynne JH, Fulmer PA, McCluskey DM, Mackey NM, Buchanan JP (2011) Synthesis and development of a multifunctional self-decontaminating polyurethane coating. ACS Appl Mater Interfaces 3:2005–2011

    Article  Google Scholar 

  4. Xu X, Zheng AN, Zhou XD, Guan Y, Pan YF, Xiao HN (2015) Antimicrobial polyethylene wax emulsion and its application on active paper-based packaging material. J Appl Polym Sci 132(27). doi:10.1002/app.42214

  5. Huang YH, Chen MHC, Lee BH, Hsieh KH, Tu YK, Lin JJ, Chang CH (2014) Evenly distributed thin-film Ag coating on stainless plate by tricomponent Ag/Silicate/PU with antimicrobial and biocompatible properties. ACS Appl Mater Interfaces 6:20324–20333

    Article  Google Scholar 

  6. Timofeeva L, Kleshcheva N (2011) Antimicrobial polymers: mechanism of action, factors of activity, and applications. Appl Microbiol Biotechnol 89:475–492

    Article  Google Scholar 

  7. Siedenbiedel F, Tiller JC (2012) Antimicrobial polymers in solution and on surfaces: overview and functional principles. Polymers 4:46–71

    Article  Google Scholar 

  8. Liu K, Su ZG, Miao SD, Ma GH, Zhang SP (2016) UV-curable enzymatic antibacterial waterborne polyurethane coating. Biochem Eng J 113:107–113

    Article  Google Scholar 

  9. Kugimoto Y, Wakabayashi A, Dobashi T, Ohnishi O, Doi TK, Kurokawa S (2016) Preparation and characterization of composite coatings containing a quaternary ammonium salt as an anti-static agent. Prog Org Coat 92:80–84

    Article  Google Scholar 

  10. Toker RD, Apohan NK, Kahraman MV (2013) UV-curable nano-silver containing polyurethane based organic–inorganic hybrid coatings. Prog Org Coat 76:1243–1250

    Article  Google Scholar 

  11. Li JH, Hong RY, Li MY, Li HZ, Zheng Y, Ding J (2009) Effects of ZnO nanoparticles on the mechanical and antibacterial properties of polyurethane coatings. Prog Org Coat 64:504–509

    Article  Google Scholar 

  12. Tiller JC, Liao CJ, Lewis K, Klibanov AM (2001) Designing surfaces that kill bacteria on contact. Proc Natl Acad Sci USA 98:5981–5985

    Article  Google Scholar 

  13. Garrison TF, Zhang ZY, Kim HJ, Mitra D, Xia Y, Pfister DP, Brehm-Stecher BF, Larock RC, Kessler MR (2014) Thermo-mechanical and antibacterial properties of soybean oil-based cationic polyurethane coatings: effects of amine ratio and degree of crosslinking. Macromol Mater Eng 299:1042–1051

    Google Scholar 

  14. Ho CH, Tobis J, Sprich C, Thomann R, Tiller JC (2004) Nanoseparated polymeric networks with multiple antimicrobial properties. Adv Mater 16:957–961

    Article  Google Scholar 

  15. Liu GF, Wu GM, Jin C, Kong ZW (2015) Preparation and antimicrobial activity of terpene-based polyurethane coatings with carbamate group-containing quaternary ammonium salts. Prog Org Coat 80:150–155

    Article  Google Scholar 

  16. Grapski JA, Cooper SL (2001) Synthesis and characterization of non-leaching biocidal polyurethanes. Biomaterials 22:2239–2246

    Article  Google Scholar 

  17. Wei DF, Ma QX, Guan Y, Hu FZ, Zheng A, Zhang X, Teng Z, Jiang H (2009) Structural characterization and antibacterial activity of oligoguanidine (polyhexamethylene guanidine hydrochloride). Mater Sci Eng C 29:1776–1780

    Article  Google Scholar 

  18. Wender PA, Galliher WC, Goun EA, Jones LR, Pillow TH (2008) The design of guanidinium-rich transporters and their internalization mechanisms. Adv Drug Deliv Rev 60:452–472

    Article  Google Scholar 

  19. Mattheis C, Wang H, Meister C, Agarwal S (2013) Effect of guanidinylation on the properties of poly (2-aminoethylmethacrylate)-based antibacterial materials. Macromol Biosci 13:242–255

    Article  Google Scholar 

  20. Michl TD, Locock KES, Stevens NE, Hayball JD, Vasilev K, Postma A, Qu Y, Traven A, Haeussler M, Meagherb L, Griesserd HJ (2014) RAFT-derived antimicrobial polymethacrylates: elucidating the impact of end-groups on activity and cytotoxicity. Polym Chem 5:5813–5822

    Article  Google Scholar 

  21. Fischer M, Vahdatzadeh M, Konradi RT, Friedrichs J, Maitz MF, Freudenberg U, Werner C (2015) Multilayer hydrogel coatings to combine hemocompatibility and antimicrobial activity. Biomaterials 56:198–205

    Article  Google Scholar 

  22. Qin LL, He Y, Liu BH, Jian Y, Li CG, Nie J (2013) Preparation and properties of polyurethane acrylates modified by saturated alcohols. Prog Org Coat 76:1594–1599

    Article  Google Scholar 

  23. Fang ZH, Duan HY, Zhang ZH, Wang J, Li DQ, Huang YX, Shang JJ, Liu ZY (2011) Novel heat-resistance UV curable waterborne polyurethane coatings modified by Melamine. Appl Surf Sci 257:4765–4768

    Article  Google Scholar 

  24. Pan XJ, Sun DC (2015) Novel cationic UV-curable cathodic electrophoretic coatings with pendant amine salt. J Chem Ind Eng 66:4696–4702

    Google Scholar 

  25. Dilger RN, Angeloni KB, Payne RL, Lemme A, Parsons CM (2013) Dietary guanidino acetic acid is an efficacious replacement for arginine for young chicks. Poult Sci 12:171–177

    Article  Google Scholar 

  26. Chaudhari AB, Tatiya PD, Hedaoo RK, Kulkarni RD, Gite VV (2013) Polyurethane prepared from neem oil polyesteramides for self-healing anticorrosive coatings. Ind Eng Chem Res 52:10189–10197

    Article  Google Scholar 

  27. Llorente O, Fernández-Berridi MJ, González A, Irusta L (2016) Study of the crosslinking process of waterborne UV curable polyurethane acrylates. Prog Org Coat 99:437–442

    Article  Google Scholar 

  28. Xu JC, Rong XS, Chi TY, Wang M, Wang YY, Yang DY, Qiu FX (2013) Preparation, characterization of UV-curable waterborne polyurethane acrylate and the application in metal iron surface protection. J Appl Polym Sci 130:3142–3152

    Article  Google Scholar 

  29. Madbouly SA, Otaigbe JU, Nanda AK, Wicks DA (2005) Rheological behavior of aqueous polyurethane dispersions: effects of solid content, degree of neutralization, chain extension, and temperature. Macromolecules 38:4014–4023

    Article  Google Scholar 

  30. Lu ZQ, Zhu YY, Lin JB, Jiang XK, Li ZT (2010) Hydrogen bonded foldamer-bridged biscoumarins: a UV-Vis absorption and fluorescent study of the solvent effect. Chin Sci Bull 55:2870–2878

    Article  Google Scholar 

  31. López-García JJ, Grosse C, Horno J (2009) On the use of the Stern-layer and the charged-layer formalisms for the interpretation of dielectric and electrokinetic properties of colloidal suspensions. J Colloid Interface Sci 329:384–389

    Article  Google Scholar 

  32. Liu K, Miao SD, Su ZG, Sun LJ, Ma GH, Zhang SP (2016) Castor oil-based waterborne polyurethanes with tunable properties and excellent biocompatibility. Eur J Lipid Sci Technol 118:1512–1520

    Article  Google Scholar 

  33. Zhang T, Wu WJ, Wang XJ, Mu YP (2010) Effect of average functionality on properties of UV-curable waterborne polyurethane-acrylate. Prog Org Coat 68:201–207

    Article  Google Scholar 

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Acknowledgements

The authors would like to thank the financial support from the Major Science and Technology Projects of Hunan Province, China (2015GK1004). Thanks to Prof. Shengpei Su of Hunan Normal University for his warm help and guidance.

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Correspondence to Yali Liu.

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Du, S., Wang, Y., Zhang, C. et al. Self-antibacterial UV-curable waterborne polyurethane with pendant amine and modified by guanidinoacetic acid. J Mater Sci 53, 215–229 (2018). https://doi.org/10.1007/s10853-017-1527-2

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  • DOI: https://doi.org/10.1007/s10853-017-1527-2

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