Eco-friendly biodegradable polyurethane based coating for antibacterial and antifouling performance

doi:10.1016/j.cjche.2022.09.004

中国化学工程学报 ›› 2023, Vol. 54 ›› Issue (2): 80-88.DOI: 10.1016/j.cjche.2022.09.004

• Full Length Article • 上一篇下一篇

Eco-friendly biodegradable polyurethane based coating for antibacterial and antifouling performance

Abid Ali¹, Bilal Ul Amin¹, Wenwu Yu², Taijiang Gui³, Weiwei Cong³, Kai Zhang³, Zheming Tong¹, Jiankun Hu¹, Xiaoli Zhan^1,4, Qinghua Zhang^1,4

1. College of Chemical and Biological Engineering, Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, Zhejiang University, Hangzhou 310027, China;
2. Institute of Mold Technology, Changzhou Vocational Institute of Mechatronic Technology, Changzhou 213164, China;
3. State Key Laboratory of Marine Coatings, Marine Chemical Research Institute Co. Ltd, Qingdao 266072, China;
4. Quzhou Research Institute, Zhejiang University, Quzhou 324000, China

收稿日期:2021-12-31 修回日期:2022-09-20 出版日期:2023-02-28 发布日期:2023-05-11
通讯作者: Xiaoli Zhan,E-mail:xlzhan@zju.edu.cn;Qinghua Zhang,E-mail:qhzhang@zju.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (21878267).

Eco-friendly biodegradable polyurethane based coating for antibacterial and antifouling performance

Abid Ali¹, Bilal Ul Amin¹, Wenwu Yu², Taijiang Gui³, Weiwei Cong³, Kai Zhang³, Zheming Tong¹, Jiankun Hu¹, Xiaoli Zhan^1,4, Qinghua Zhang^1,4

1. College of Chemical and Biological Engineering, Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, Zhejiang University, Hangzhou 310027, China;
2. Institute of Mold Technology, Changzhou Vocational Institute of Mechatronic Technology, Changzhou 213164, China;
3. State Key Laboratory of Marine Coatings, Marine Chemical Research Institute Co. Ltd, Qingdao 266072, China;
4. Quzhou Research Institute, Zhejiang University, Quzhou 324000, China

Received:2021-12-31 Revised:2022-09-20 Online:2023-02-28 Published:2023-05-11
Contact: Xiaoli Zhan,E-mail:xlzhan@zju.edu.cn;Qinghua Zhang,E-mail:qhzhang@zju.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (21878267).

摘要/Abstract

摘要： Biofouling, which comprises the absorption of proteins and the adhesion of bacteria to the surface of living entities, is a severe concern for the maritime sector since it ultimately leads to hydrodynamic drag, resulting in a higher increase in fuel consumption. As a result, polymer resins are crucial in the marine sector for anti-biofouling coatings. In this work, the poly(caprolactone-ethylene glycol-caprolactone)-polyurethane (PECL-PU) are prepared through ε-caprolactone (CL), poly(ethylene glycol) (PEG), 4,4'-methylene bis(cyclohexyl isocyanate) and 1,4 butanediol. Our study demonstrate that the PECL-PU copolymer degraded in artificial seawater (5.21%), enzymatic solution (12.63%), and seawater (13.75%) due to the presence of PEG segments in the laboratory-based test under static condition. Because the addition of PEG segments are increased the polymer's amorphous area and decreased the crystallization of the polycaprolactone (PCL) in the copolymer, as demonstrated by differential scanning calorimetry, X-ray diffraction, and water contact angle studies. Therefore, the hydrolysis rates of PECL-PU were higher than the caprolactone-co-polyurethane (CL-PU). The antifouling test showed that PECL-PU3 copolymer had about 90.29% protein resistance, 85.2% Escherichia coli (E. coli) reduction and 94.61% marine diatom Navicula incerta reduction comparison to the control. We have developed an eco-friendly and inexpensive promising degradable polyurethane for reduction of bacterial biofilm, which can preserve the formation of biofouling on marine coating under practical sea conditions.

关键词: Caprolactone, PEG segments, Biodegradable polyurethane, Biofouling, Hydrolytic degradation

Abstract: Biofouling, which comprises the absorption of proteins and the adhesion of bacteria to the surface of living entities, is a severe concern for the maritime sector since it ultimately leads to hydrodynamic drag, resulting in a higher increase in fuel consumption. As a result, polymer resins are crucial in the marine sector for anti-biofouling coatings. In this work, the poly(caprolactone-ethylene glycol-caprolactone)-polyurethane (PECL-PU) are prepared through ε-caprolactone (CL), poly(ethylene glycol) (PEG), 4,4'-methylene bis(cyclohexyl isocyanate) and 1,4 butanediol. Our study demonstrate that the PECL-PU copolymer degraded in artificial seawater (5.21%), enzymatic solution (12.63%), and seawater (13.75%) due to the presence of PEG segments in the laboratory-based test under static condition. Because the addition of PEG segments are increased the polymer's amorphous area and decreased the crystallization of the polycaprolactone (PCL) in the copolymer, as demonstrated by differential scanning calorimetry, X-ray diffraction, and water contact angle studies. Therefore, the hydrolysis rates of PECL-PU were higher than the caprolactone-co-polyurethane (CL-PU). The antifouling test showed that PECL-PU3 copolymer had about 90.29% protein resistance, 85.2% Escherichia coli (E. coli) reduction and 94.61% marine diatom Navicula incerta reduction comparison to the control. We have developed an eco-friendly and inexpensive promising degradable polyurethane for reduction of bacterial biofilm, which can preserve the formation of biofouling on marine coating under practical sea conditions.

Key words: Caprolactone, PEG segments, Biodegradable polyurethane, Biofouling, Hydrolytic degradation

Abid Ali, Bilal Ul Amin, Wenwu Yu, Taijiang Gui, Weiwei Cong, Kai Zhang, Zheming Tong, Jiankun Hu, Xiaoli Zhan, Qinghua Zhang. Eco-friendly biodegradable polyurethane based coating for antibacterial and antifouling performance[J]. 中国化学工程学报, 2023, 54(2): 80-88.

参考文献

[1] H. Yan, Q.S. Wu, C.M. Yu, T.Y. Zhao, M.J. Liu, Recent progress of biomimetic antifouling surfaces in marine, Adv. Mater. Interf. 7 (20) (2020) 2000966.
[2] X.Y. Hu, J.H. Tian, C. Li, H. Su, R.R. Qin, Y.F. Wang, X. Cao, P. Yang, Amyloid-like protein aggregates: A new class of bioinspired materials merging an interfacial anchor with antifouling, Adv. Mater. 32 (23) (2020) 2000128.
[3] A. Vena, S. Kolle, S. Stafslien, J. Aizenberg, P. Kim, Self-stratifying porous silicones with enhanced liquid infusion and protective skin layer for biofouling prevention, Adv. Mater. Interf. 8 (2) (2021) 2000359.
[4] M.S. Selim, S.A. El-Safty, M.A. Shenashen, S.A. Higazy, A. Elmarakbi, Progress in biomimetic leverages for marine antifouling using nanocomposite coatings, J. Mater. Chem. B 8 (17) (2020) 3701–3732.
[5] S. Kinkley, J. Helmuth, J.K. Polansky, I. Dunkel, G. Gasparoni, S. Fröhler, W. Chen, J. Walter, A. Hamann, H.R. Chung, reChIP-seq reveals widespread bivalency of H3K4me3 and H3K27me3 in CD4⁺ memory T cells, Nat. Commun. 7 (2016) 12514.
[6] M.S. Selim, M.A. Shenashen, S.A. El-Safty, S.A. Higazy, M.M. Selim, H. Isago, A. Elmarakbi, Recent progress in marine foul-release polymeric nanocomposite coatings, Prog. Mater. Sci. 87 (2017) 1–32.
[7] M. Lejars, A. Margaillan, C. Bressy, Fouling release coatings: A nontoxic alternative to biocidal antifouling coatings, Chem. Rev. 112 (8) (2012) 4347–4390.
[8] R. Ciriminna, V. Pandarus, G. Gingras, F. Béland, M. Pagliaro, Closing the organosilicon synthetic cycle: Efficient heterogeneous hydrosilylation of alkenes over SiliaCatPt(0), ACS Sustain. Chem. Eng. 1 (2) (2013) 249–253.
[9] X. Su, D.Z. Hao, Z.N. Li, X.L. Guo, L. Jiang, Design of hierarchical comb hydrophilic polymer brush (HCHPB) surfaces inspired by fish mucus for anti-biofouling, J. Mater. Chem. B 7 (8) (2019) 1322–1332.
[10] H. Okoro, O. Fatoki, F.A. Adekola, B.J. Ximba, R. Snyman, Sources, environmental levels and toxicity of organotin in marine environment: A review, Asain J. Chem. 23 (2) (2011) 473–482.
[11] K.V. Thomas, S. Brooks, The environmental fate and effects of antifouling paint biocides, Biofouling 26 (1) (2010) 73–88.
[12] R. Deng, T. Shen, H.L. Chen, J.X. Lu, H.C. Yang, W.H. Li, Slippery liquid-infused porous surfaces (SLIPSs): A perfect solution to both marine fouling and corrosion? J. Mater. Chem. A 8 (16) (2020) 7536–7547.
[13] C.Q. Wei, G.F. Zhang, Q.H. Zhang, X.L. Zhan, F.Q. Chen, Silicone oil-infused slippery surfaces based on sol–gel process-induced nanocomposite coatings: A facile approach to highly stable bioinspired surface for biofouling resistance, ACS Appl. Mater. Interf. 8 (50) (2016) 34810–34819.
[14] Q.Y. Xie, H.H. Zeng, Q.M. Peng, C. Bressy, C.F. Ma, G.Z. Zhang, Self-stratifying silicone coating with nonleaching antifoulant for marine anti-biofouling, Adv. Mater. Interf. 6 (13) (2019) 1900535.
[15] P. Hu, Q.Y. Xie, C.F. Ma, G.Z. Zhang, Silicone-based fouling-release coatings for marine antifouling, Langmuir 36 (9) (2020) 2170–2183.
[16] X.L. Zhan, G.F. Zhang, Q.H. Zhang, F.Q. Chen, Preparation, surface wetting properties, and protein adsorption resistance of well-defined amphiphilic fluorinated diblock copolymers, J. Appl. Polym. Sci. 131 (23) (2014), https://doi.org/10.1002/app.41167.
[17] F. Gao, G.F. Zhang, Q.H. Zhang, X.L. Zhan, F.Q. Chen, Improved antifouling properties of poly(ether sulfone) membrane by incorporating the amphiphilic comb copolymer with mixed poly(ethylene glycol) and poly(dimethylsiloxane) brushes, Ind. Eng. Chem. Res. 54 (35) (2015) 8789–8800.
[18] X. Chen, G.F. Zhang, Q.H. Zhang, X.L. Zhan, F.Q. Chen, Preparation and performance of amphiphilic polyurethane copolymers with capsaicin-mimic and PEG moieties for protein resistance and antibacteria, Ind. Eng. Chem. Res. 54 (15) (2015) 3813–3820.
[19] G.X. Dai, Q.Y. Xie, X.Q. Ai, C.F. Ma, G.Z. Zhang, Self-generating and self-renewing zwitterionic polymer surfaces for marine anti-biofouling, ACS Appl. Mater. Interf. 11 (44) (2019) 41750–41757.
[20] A. Ali, Y. Xiao, L.N. Song, J.K. Hu, Q.Q. Rao, M. Shoaib, B.U. Amin, X.L. Zhan, Q.H. Zhang, Biodegradable polyurethane based clay composite and their anti-biofouling properties, Colloids Surf. A Physicochem. Eng. Aspects 625 (2021) 126946.
[21] Y.K. Demirel, M. Khorasanchi, O. Turan, A. Incecik, On the importance of antifouling coatings regarding ship resistance and powering, in: 3rd International Conference on Technologies, Operations, Logistics and Modelling for Low Carbon Shipping, 2013.
[22] I.M. Organization , I.M.O.M.E.P. Committee, Anti-fouling systems: International Convention on the Control of Harmful Anti-fouling Systems on Ships, 2001 (AFS 2001) and Guidelines for Survey and Certification of Anti-fouling Systems on Ships (resolution MEPC. 102 (48)), Guidelines for Brief Sampling of Anti-fouling Systems on Ships (resolution MEPC. 104 (49)), and Guidelines for Inspection of Anti-fouling Systems on Ships (resolution , MEPC , 105 , IMO Publishing , 2005.
[23] A. Ali, M.I. Jamil, J.X. Jiang, M. Shoaib, B.U. Amin, S.Z. Luo, X.L. Zhan, F.Q. Chen, Q.H. Zhang, An overview of controlled-biocide-release coating based on polymer resin for marine antifouling applications, J. Polym. Res. 27 (4) (2020) 1–17.
[24] Q.Y. Xie, J.S. Pan, C.F. Ma, G.Z. Zhang, Dynamic surface antifouling: Mechanism and systems, Soft Matter 15 (6) (2019) 1087–1107.
[25] S.S. Chen, C.F. Ma, G.Z. Zhang, Biodegradable polymers for marine antibiofouling: Poly(ε-caprolactone)/poly(butylene succinate) blend as controlled release system of organic antifoulant, Polymer 90 (2016) 215–221.
[26] J.L. Ma, C.F. Ma, G.Z. Zhang, Degradable polymer with protein resistance in a marine environment, Langmuir 31 (23) (2015) 6471–6478.
[27] Q.Y. Xie, Q.N. Xie, J.S. Pan, C.F. Ma, G.Z. Zhang, Biodegradable polymer with hydrolysis-induced zwitterions for antibiofouling, ACS Appl. Mater. Interf. 10 (13) (2018) 11213–11220.
[28] Y.F. Wang, Q.F. Hong, Y.J. Chen, X.X. Lian, Y.F. Xiong, Surface properties of polyurethanes modified by bioactive polysaccharide-based polyelectrolyte multilayers, Colloids Surf. B Biointerf. 100 (2012) 77–83.
[29] R. Konradi, B. Pidhatika, A. Mühlebach, M. Textor, Poly-2-methyl-2-oxazoline: A peptide-like polymer for protein-repellent surfaces, Langmuir 24 (3) (2008) 613–616.
[30] G. Emilsson, R.L. Schoch, L. Feuz, F. Höök, R.Y.H. Lim, A.B. Dahlin, Strongly stretched protein resistant poly(ethylene glycol) brushes prepared by grafting-to, ACS Appl. Mater. Interf. 7 (14) (2015) 7505–7515.
[31] S.Y. Jiang, Z.Q. Cao, Ultralow-fouling, functionalizable, and hydrolyzable zwitterionic materials and their derivatives for biological applications, Adv. Mater. 22 (9) (2010) 920–932.
[32] J. Wu, C. Zhao, R.D. Hu, W.F. Lin, Q.M. Wang, J. Zhao, S.M. Bilinovich, T.C. Leeper, L.Y. Li, H.M. Cheung, S.F. Chen, J. Zheng, Probing the weak interaction of proteins with neutral and zwitterionic antifouling polymers, Acta Biomater. 10 (2) (2014) 751–760.
[33] W. Yandi, S. Mieszkin, A. di Fino, P. Martin-Tanchereau, M.E. Callow, J.A. Callow, L. Tyson, A.S. Clare, T. Ederth, Charged hydrophilic polymer brushes and their relevance for understanding marine biofouling, Biofouling 32 (6) (2016) 609–625.
[34] J. Koc, T. Simovich, E. Schönemann, A. Chilkoti, H. Gardner, G.W. Swain, K. Hunsucker, A. Laschewsky, A. Rosenhahn, Sediment challenge to promising ultra-low fouling hydrophilic surfaces in the marine environment, Biofouling 35 (4) (2019) 454–462.
[35] C.F. Ma, H.J. Yang, X. Zhou, B. Wu, G.Z. Zhang, Polymeric material for anti-biofouling, Colloids Surf. B Biointerf. 100 (2012) 31–35.
[36] C.H. Tsou, H.T. Lee, H.A. Tsai, H.J. Cheng, M.C. Suen, Synthesis and properties of biodegradable polycaprolactone/polyurethanes by using 2,6-pyridinedimethanol as a chain extender, Polym. Degrad. Stab. 98 (2) (2013) 643–650.
[37] C.H. Tsou, H.T. Lee, W.S. Hung, C.C. Wang, C.C. Shu, M.C. Suen, M. de Guzman, Synthesis and properties of antibacterial polyurethane with novel bis(3-pyridinemethanol) silver chain extender, Polymer 85 (2016) 96–105.
[38] G.R. da Silva, A. da Silva-Cunha Jr, F. Behar-Cohen, E. Ayres, R.L. Oréfice, Biodegradation of polyurethanes and nanocomposites to non-cytotoxic degradation products, Polym. Degrad. Stab. 95 (4) (2010) 491–499.
[39] M.H. Xiao, N. Zhang, J. Zhuang, Y.C. Sun, F. Ren, W.W. Zhang, Z.S. Hou, Degradable poly(ether-ester-urethane)s based on well-defined aliphatic diurethane diisocyanate with excellent shape recovery properties at body temperature for biomedical application, Polymers 11 (6) (2019) 1002.
[40] S.Z. Fu, L.L. Yang, J. Fan, Q.L. Wen, S. Lin, B.Q. Wang, L.L. Chen, X.H. Meng, Y. Chen, J.B. Wu, In vitro mineralization of hydroxyapatite on electrospun poly(ε-caprolactone)-poly(ethylene glycol)-poly(ε-caprolactone) fibrous scaffolds for tissue engineering application, Colloids Surf. B Biointerfaces 107 (2013) 167–173.
[41] Y. Li, H.M. Chen, D. Liu, W.X. Wang, Y. Liu, S.B. Zhou, pH-responsive shape memory poly(ethylene glycol)–poly(ε-caprolactone)-based polyurethane/cellulose nanocrystals nanocomposite, ACS Appl. Mater. Interf. 7 (23) (2015) 12988–12999.
[42] H.P. Wang, D.J. Tong, L. Wang, L. Chen, N. Yu, Z.X. Li, A facile strategy for fabricating PCL/PEG block copolymer with excellent enzymatic degradation, Polym. Degrad. Stab. 140 (2017) 64–73.
[43] L.D. Zhu, K.M. Bratlie, Supramolecular assemblies of alkane functionalized polyethylene glycol copolymers for drug delivery, Mater. Sci. Eng. C 81 (2017) 432–442.
[44] Q.N. Xie, X. Zhou, C.F. Ma, G.Z. Zhang, Self-cross-linking degradable polymers for antifouling coatings, Ind. Eng. Chem. Res. 56 (18) (2017) 5318–5324.
[45] American Society for Testing and Materials, Standard practice for the preparation of substitute ocean water, ASTM International, 2013.
[46] A. Güney, C. Gardiner, A. McCormack, J. Malda, D.W. Grijpma, Thermoplastic PCL-b-PEG-b-PCL and HDI polyurethanes for extrusion-based 3D-printing of tough hydrogels, Bioengineering 5 (4) (2018) 99.
[47] A. Ali, L.N. Song, J.K. Hu, J.X. Jiang, Q.Q. Rao, M. Shoaib, S. Fahad, Y.J. Cai, X.L. Zhan, F.Q. Chen, Q.H. Zhang, Synthesis and characterization of caprolactone based polyurethane with degradable and antifouling performance, Chin. J. Chem. Eng. 34 (2021) 299–306.
[48] J.L. Ma, C.F. Ma, Y. Yang, W.T. Xu, G.Z. Zhang, Biodegradable polyurethane carrying antifoulants for inhibition of marine biofouling, Ind. Eng. Chem. Res. 53 (32) (2014) 12753–12759.
[49] C.F. Ma, L.G. Xu, W.T. Xu, G.Z. Zhang, Degradable polyurethane for marine anti-biofouling, J. Mater. Chem. B 1 (24) (2013) 3099–3106.
[50] F. Faÿ, I. Linossier, J.J. Peron, V. Langlois, K. Vallée-Rehel, Antifouling activity of marine paints: Study of erosion, Prog. Org. Coat. 60 (3) (2007) 194–206.
[51] E. Guégain, J.P. Michel, T. Boissenot, J. Nicolas, Tunable degradation of copolymers prepared by nitroxide-mediated radical ring-opening polymerization and point-by-point comparison with traditional polyesters, Macromolecules 51 (3) (2018) 724–736.
[52] C.F. Ma, W.T. Xu, J.S. Pan, Q.Y. Xie, G.Z. Zhang, Degradable polymers for marine antibiofouling: Optimizing structure to improve performance, Ind. Eng. Chem. Res. 55 (44) (2016) 11495–11501.
[53] J. Pan, Q. Xie, H. Chiang, Q. Peng, P.Y. Qian, C. Ma, G. Zhang, “From the nature for the nature”: An eco-friendly antifouling coating consisting of poly(lactic acid)-based polyurethane and natural antifoulant, ACS Sustain. Chem. Eng. 8 (3) (2019) 1671-1678.
[54] S.S. Chen, C.F. Ma, G.Z. Zhang, Biodegradable polymer as controlled release system of organic antifoulant to prevent marine biofouling, Prog. Org. Coat. 104 (2017) 58–63.
[55] B.L. Ou, M.L. Chen, Y.J. Guo, Y.H. Kang, Y. Guo, S.G. Zhang, J.H. Yan, Q.Q. Liu, D.X. Li, Preparation of novel marine antifouling polyurethane coating materials, Polym. Bull. 75 (11) (2018) 5143–5162.
[56] C.F. Ma, W.P. Zhang, G.Z. Zhang, P.Y. Qian, Environmentally friendly antifouling coatings based on biodegradable polymer and natural antifoulant, ACS Sustain. Chem. Eng. 5 (7) (2017) 6304–6309.
[57] M.L. Chen, B.L. Ou, Y.J. Guo, Y. Guo, Y.H. Kang, H.Y. Liu, J.H. Yan, L. Tian, Preparation of an environmentally friendly antifouling degradable polyurethane coating material based on medium-length fluorinated diols, J. Macromol. Sci. A 55 (6) (2018) 483–488.
[58] T. Ekblad, G. Bergström, T. Ederth, S.L. Conlan, R. Mutton, A.S. Clare, S. Wang, Y.L. Liu, Q. Zhao, F. D’Souza, G.T. Donnelly, P.R. Willemsen, M.E. Pettitt, M.E. Callow, J.A. Callow, B. Liedberg, Poly(ethylene glycol)-containing hydrogel surfaces for antifouling applications in marine and freshwater environments, Biomacromolecules 9 (10) (2008) 2775–2783.
[59] M. Ulbricht, H. Yang, Porous polypropylene membranes with different carboxyl polymer brush layers for reversible protein binding via surface-initiated graft copolymerization, Chem. Mater. 17 (10) (2005) 2622–2631.
[60] G. Cheng, H. Xue, Z. Zhang, S.F. Chen, S.Y. Jiang, A switchable biocompatible polymer surface with self-sterilizing and nonfouling capabilities, Angew. Chem. Int. Ed. 47 (46) (2008) 8831–8834.
[61] T. McPherson, A. Kidane, I. Szleifer, K. Park, Prevention of protein adsorption by tethered poly(ethylene oxide) layers: Experiments and single-chain mean-field analysis, Langmuir 14 (1) (1998) 176–186.
[62] J.H. Yao, Z.W. Dai, J. Yi, H.L. Yu, B. Wu, L.Y. Dai, Degradable polyurethane based on triblock polyols composed of polypropyleneglycol and ε-caprolactone for marine antifouling applications, J. Coat. Technol. Res. 17 (4) (2020) 865–874.

Eco-friendly biodegradable polyurethane based coating for antibacterial and antifouling performance

Eco-friendly biodegradable polyurethane based coating for antibacterial and antifouling performance

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