Abstract
It is of great significance to design epoxy coatings with superior antibacterial properties and high adhesive properties, as well as excellent processing, superior durability, and high transparency. However, it is still a challenge because of the common complex design and synthesis. Herein, the bio-based monomer protocatechuic acid (PCA) was used as raw material, the catechol structure with high bonding and antibacterial properties was introduced into the flexible alkane segment of ethylene glycol diglycidyl ether (EGDE) through an efficient, and green method, and it was cured with isophorone diamine (IPDA) to prepare corresponding thermosets. The cured resins exhibited excellent all-around qualities, particularly in bonding and antibacterial. When 30% PCA was added to pure epoxy resin, the adhesion between substrate and coating increased from 4.40 MPa to 13.60 MPa and the antibacterial rate of coating against E. coli and S. aureus could approach 100%. All of this is due to the fact that the catechol structure present in PCA has the ability to interact with various substrates and alter the permeability of bacterial cell membranes. The architecture of this method offers a fresh approach to dealing with the issues of challenging raw material selection and complex synthesis techniques.
References
Dai, J.; Peng, Y.; Teng, N.; Liu, Y.; Liu, C.; Shen, X.; Mahmud, S.; Zhu, J.; Liu, X. High-performing and fire-resistant biobased epoxy resin from renewable sources. ACS Sustainable Chem. Eng. 2018, 6, 7589–7599.
Shundo, A.; Yamamoto, S.; Tanaka, K. Network formation and physical properties of epoxy resins for future practical applications. JACS Au 2022, 2, 1522–1542.
Chen, P.; Wang, G.; Li, J.; Zhang, M.; Qiao, X. Preparation of textured epoxy resin coatings for excellent hydrophobicity and corrosion resistance. Prog. Org. Coat. 2023, 175.
Wang, H.; Wang, M.; Xu, X.; Gao, P.; Xu, Z.; Zhang, Q.; Li, H.; Yan, A.; Kao, R. Y.; Sun, H. Multi-target mode of action of silver against Staphylococcus aureus endows it with capability to combat antibiotic resistance. Nat. Commun. 2021, 12, 3331.
Wang, Y.; Wang, Y.; Li, X.; Li, J.; Su, L.; Zhang, X.; Du, X. Dendritic silica particles with well-dispersed ag nanoparticles for robust antireflective and antibacterial nanocoatings on polymeric glass. ACS Sustainable Chem. Eng. 2018, 6, 14071–14081.
Xia, L.; Wang, X.; Liu, H.; Luo, Q.; Guo, C.; Miao, Z.; Dai, J.; Li, D.; Xu, Y.; Yuan, C.; Zeng, B.; Dai, L. Cu2O based on core-shell nanostructure for enhancing the fire-resistance, antibacterial properties and mechanical properties of epoxy resin. Compos. Commun. 2023, 37, 101445.
Guerrero Correa, M.; Martinez, F. B.; Vidal, C. P.; Streitt, C.; Escrig, J.; de Dicastillo, C. L. Antimicrobial metal-based nanoparticles: a review on their synthesis, types and antimicrobial action. Beilstein J. Nanotechnol. 2020, 11, 1450–1469.
Yang, X.; Yu, Q.; Gao, W.; Tang, X.; Yi, H.; Tang, X. The mechanism of metal-based antibacterial materials and the progress of food packaging applications: a review. Ceram. Int. 2022, 48, 34148–34168.
Marín-Caba, L.; Bodelón, G.; Negrín-Montecelo, Y.; Correa-Duarte, M. A. Sunlight-sensitive plasmonic nanostructured composites as photocatalytic coating with antibacterial properties. Adv. Funct. Mater. 2021, 31.
Bhattacharyya, S.; Ali, S. R.; Venkateswarulu, M.; Howlader, P.; Zangrando, E.; De, M.; Mukherjee, P. S. Self-assembled Pd(12) coordination cage as photoregulated oxidase-like nanozyme. J. Am. Chem. Soc. 2020, 142, 18981–18989.
Li, P.; Li, J.; Feng, X.; Li, J.; Hao, Y.; Zhang, J.; Wang, H.; Yin, A.; Zhou, J.; Ma, X.; Wang, B. Metal-organic frameworks with photocatalytic bactericidal activity for integrated air cleaning. Nat. Commun. 2019, 10, 2177.
Xu, X.; Wang, Y.; Zhang, D. A novel strategy of hydrothermal in situ grown bismuth based film on epoxy resin as recyclable photocatalyst for photodegrading antibiotics and sterilizing microorganism. Sep. Purif. Technol. 2022, 290, 120842.
Li, R.; Yang, G.; Wang, Y.; Liu, L.; Wang, Q.; Wang, G.; Ouyang, X. Synthesis of antibacterial polyether biguanide curing agent and its cured antibacterial epoxy resin. Des. Monomers Polym. 2021, 24, 63–72.
Chen, Q.; Zhang, L.; Zhang, J.; Habib, S.; Lu, G.; Dai, J.; Liu, X. Bio-based polybenzoxazines coatings for efficient marine antifouling. Prog. Org. Coat. 2023, 174, 107298.
Hao, L.; Jiang, R.; Fan, Y.; Xu, J.-n.; Tian, L.; Zhao, J.; Ming, W.; Ren, L. Formation and antibacterial performance of metal-organic framework films via dopamine-mediated fast assembly under visible light. ACS Sustainable Chem. Eng. 2020, 8, 15834–15842.
Ou, X.; Xue, Bin.; Yanee, W.; Tian, R.; Zou, A.; Yang, L.; Wang, W.; Cao, Y.; Li, J. Structure and sequence features of mussel adhesive protein lead to its salt-tolerant adhesion ability. Sci. Adv. 2020, 6, eabb7620.
Hemmatpour, H.; De Luca, O.; Crestani, D.; Stuart, M. C. A.; Lasorsa, A.; van der Wel, P. C. A.; Loos, K.; Giousis, T.; Haddadi-Asl, V.; Rudolf, P. New insights in polydopamine formation via surface adsorption. Nat. Commun. 2023, 14, 664.
Saiz-Poseu, J.; Mancebo-Aracil, J.; Nador, F.; Busque, F.; Ruiz-Molina, D. The chemistry behind catechol-based adhesion. Angew. Chem. Int. Ed. Engl. 2019, 58, 696–714.
Fang, Z.; Nikafshar, S.; Hegg, E. L.; Nejad, M. Biobased divanillin as a precursor for formulating biobased epoxy resin. ACS Sustainable Chem. Eng. 2020, 8, 9095–9103.
Alsuwait, R. B.; Souiyah, M.; Momohjimoh, I.; Ganiyu, S. A.; Bakare, A. O. Recent development in the processing, properties, and applications of epoxy-based natural fiber polymer biocomposites. Polymers 2022, 15, 145.
Fang, X.; Guo, X.; Tang, W.; Gu, Q.; Wu, Y.; Sun, H.; Gao, J. Efficient toughening of DGEBA with a bio-based protocatechuic acid derivative. ACS Omega 2023, 8, 9962–9968.
Miklasinska-Majdanik, M.; Kepa, M.; Kulczak, M.; Ochwat, M.; Wasik, T. J. The array of antibacterial action of protocatechuic acid ethyl ester and erythromycin on staphylococcal strains. Antibiotics 2022, 11, 848.
Shi, J.; Zhang, F.; Wu, S.; Guo, Z.; Huang, X.; Hu, X.; Holmes, M.; Zou, X. Noise-free microbial colony counting method based on hyperspectral features of agar plates. Food Chem. 2019, 274, 925–932.
Liu, W.; Yan, M.; Zhao, W. Antibacterial-renew dual-function anti-biofouling strategy: self-assembled Schiff-base metal complex coatings built from natural products. J. Colloid Interface Sci. 2023, 629 (Pt A), 496–507.
Paschalidou, K.; Salta, K.; Koulougliotis, D. Exploring the connections between systems thinking and green chemistry in the context of chemistry education: a scoping review. Sustain. Chem. Pharm. 2022, 29, 100788.
Liu, J.; Dai, J.; Wang, S.; Peng, Y.; Cao, L.; Liu, X. Facile synthesis of bio-based reactive flame retardant from vanillin and guaiacol for epoxy resin. Compos. Part B: Eng. 2020, 190, 107926.
Dell’Anno, G.; Partridge, I.; Cartié, D.; Hamlyn, A.; Chehura, E.; James, S.; Tatam, R. Automated manufacture of 3D reinforced aerospace composite structures. Int. J. of Struct. Integr. 2012, 3, 22–40.
Zhao, S.; Abu-Omar, M. M. Biobased epoxy nanocomposites derived from lignin-based monomers. Biomacromolecules 2015, 16, 2025–2031.
Filippidi, E.; Cristiani, T. R.; Eisenbach, C. D.; Waite, J. H.; Israelachvili, J. N.; Ahn, B. K.; Valentine, M. T. Toughening elastomers using mussel-inspired iron-catechol complexes. Science 2017, 358, 502–505.
Wei, H.; Xia, J.; Zhou, W.; Zhou, L.; Hussain, G.; Li, Q.; Ostrikov, K. Adhesion and cohesion of epoxy-based industrial composite coatings. Compos. Part B: Eng. 2020, 193, 108035.
Xie, Y.; Qian, Y.; Li, Z.; Liang, Z.; Liu, W.; Yang, D.; Qiu, X. Near-infrared-activated efficient bacteria-killing by lignin-based copper sulfide nanocomposites with an enhanced photothermal effect and peroxidase-like activity. ACS Sustainable Chem. Eng. 2021, 9, 6479–6488.
Giannakas, A.; Vlacha, M.; Salmas, C.; Leontiou, A.; Katapodis, P.; Stamatis, H.; Barkoula, N. M.; Ladavos, A. Preparation, characterization, mechanical, barrier and antimicrobial properties of chitosan/PVOH/clay nanocomposites. Carbohydr. Polym. 2016, 140, 408–15.
Kim, Y. S.; Kim, K. S.; Han, I.; Kim, M. H.; Jung, M. H.; Park, H. K. Quantitative and qualitative analysis of the antifungal activity of allicin alone and in combination with antifungal drugs. PLoS One 2012, 7, e38242.
Kang, B.; Lan, D.; Yao, C.; Liu, P.; Chen, X.; Qi, S. Evaluation of antibacterial property and biocompatibility of Cu doped TiO2 coated implant prepared by micro-arc oxidation. Front. Bioeng. Biotech. 2022, 10, 941109.
Demir, C.; Ceren Süer, N.; Yapaöz, M. A.; Kébir, N.; Okullu, S. Ö.; Kocagöz, T.; Eren, T. Biocidal activity of ROMP-polymer coatings containing quaternary phosphonium groups. Prog. Org. Coat. 2019, 135, 299–305.
Polinarski, M. A.; Beal, A. L. B.; Silva, F. E. B.; Bernardi-Wenzel, J.; Burin, G. R. M.; Muniz, G. I. B.; Alves, H. J. New perspectives of using chitosan, silver, and chitosan-silver nanoparticles against multidrug-resistant bacteria. Part. Part. Syst. Char. 2021, 38, 2100009.
Deng, Y.; Xia, L.; Song, G.-L.; Zhao, Y.; Zhang, Y.; Xu, Y.; Zheng, D. Development of a curcumin-based antifouling and anticorrosion sustainable polybenzoxazine resin composite coating. Compos. Part B: Eng. 2021, 225, 109263.
Torrisi, C.; Malfa, G. A.; Acquaviva, R.; Castelli, F.; Sarpietro, M. G. Effect of protocatechuic acid ethyl ester on biomembrane models: multilamellar vesicles and monolayers. Membranes 2022, 12, 283.
Cheng, H.; Wang, F.; Ou, J.; Li, W.; Xue, R. Solar reflective coatings with luminescence and self-cleaning function. Surf. Interfaces 2021, 26, 101325.
Guo, H.; Liu, M.; Xie, C.; Zhu, Y.; Sui, X.; Wen, C.; Li, Q.; Zhao, W.; Yang, J.; Zhang, L. A sunlight-responsive and robust anti-icing/deicing coating based on the amphiphilic materials. Chem. Eng. J. 2020, 40, 126161.
Wang, Z.; Liu, B.; Zeng, F.; Lin, X.; Zhang, J.; Wang, X.; Wang, Y.; Zhao, H. Fully recyclable multifunctional adhesive with high durability, transparency, flame retardancy, and harsh-environment resistance. Sci. Adv. 2022, 8, eadd8527.
Zhang, J.; Long, C.; Zhang, X.; Liu, Z.; Zhang, X.; Liu, T.; Li, J.; Gao, Q. An easy-coating, versatile, and strong soy flour adhesive via a biomineralized structure combined with a biomimetic brush-like polymer. Chem. Eng. J. 2022, 450, 138387.
Chen, J.; He, Z.; Liu, J.; Wang, Y.; Hodgson, M.; Gao, W. Antibacterial anodic aluminium oxide-copper coatings on aluminium alloys: preparation and long-term antibacterial performance. Chem. Eng. J. 2023, 461, 141873.
Cao, Y.; Yang, Z.; Ou, J.; Jiang, L.; Chu, G.; Wang, Y.; Chen, S. Ultratransparent, hard and antibacterial coating with pendent quaternary pyridine salt. Prog. Org. Coat. 2023, 175, 107369.
Nguyen, Q. X.; Nguyen, T. T.; Pham, N. M.; Khong, T. T.; Cao, T. M.; Pham, V. V. A fabrication of CNTs/TiO2/polyurethane films toward antibacterial and protective coatings. Prog. Org. Coat. 2022, 167, 106838.
Acknowledgments
This work was financially supported by the National Natural Science Foundation of China (Nos. U1909220 and 52003283), Science and Technology Innovation 2025 Major Project of Ningbo (Nos. 2021Z092, 2022Z111 and 2022Z160), Defense Industrial Technology Development Program (No. JCKY2021513B001) and the Research Project of Technology Application for Public Welfare of Ningbo City (No. 202002N3122).
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The Role of Renewable Protocatechol Acid in Epoxy Coating Modification: Significantly Improved Antibacterial and Adhesive Properties
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Chen, MX., Dai, JY., Zhang, LY. et al. The Role of Renewable Protocatechol Acid in Epoxy Coating Modification: Significantly Improved Antibacterial and Adhesive Properties. Chin J Polym Sci 42, 63–72 (2024). https://doi.org/10.1007/s10118-023-3029-9
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DOI: https://doi.org/10.1007/s10118-023-3029-9