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Preparation of novel marine antifouling polyurethane coating materials

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Abstract

Polyurethane coating materials with different compositions of low surface energy polydimethylsiloxane and degradable poly(l-lactic acid) were synthesized by three major steps. Initially, the hydroxylation-terminated poly(l-lactide)-functionalized graphene (G-g-PLLA) was prepared by ring-opening polymerization of l-lactic acid using the phenol-functionalized graphene (G-f-OH), which was prepared by 1,3-dipolar cycloaddition reaction of graphene and 3,4-dihydroxybenzaldehyde when N-methylglycine and tin octoate were used as initiator and catalyst, respectively. Subsequently, isocyanate-terminated polyurethane prepolymer with polydimethylsiloxane was obtained by condensation polymerization of polydimethylsiloxane and isocyanate-terminated polyurethane prepolymer that was obtained by the condensation polymerization of 4,4′-diphenylmethane diisocyanate and 1,4-butane diol. Finally, the novel polyurethane coating materials were prepared by the condensation polymerization of G-g-PLLA and isocyanate-terminated polyurethane prepolymer with polydimethylsiloxane. These synthesized materials were carefully analyzed with Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance spectra (1H NMR), field-emission scanning electron microscopy (SEM), and high-resolution transmission (TEM). In addition, the water contact angles were measured. It was found that the surface free energy of the polyurethane coating materials decreased from 52.19 to 11.74 N/m2 with the increase of polydimethylsiloxane content from 0 to 20% and the water contact angle of the polyurethane coating materials increased from 71° to 108°. Moreover, the mechanical property was investigated. The studies also demonstrated that functionalized polyurethane was able to hydrolyze in seawater and the hydrolysis rate decreased as the PDMS content increased. At the same time, simulative ocean hanging plate experiment confirmed that the novel polyurethane coating materials exhibited a good antifouling performance, which indicated that the functionalized polyurethane has a potentiality in marine antifouling coating application.

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Acknowledgements

This work was financially supported by National Natural Science Foundation of China (Grant nos. 51775183, 51275167, 51475161), Hunan Provincial Natural Science Foundation of China (Grant no. 2018JJ2125), Scientific Research Fund of Hunan Provincial Education Department (Grant nos. 15K041, 15A059), Research Innovation Project of Hunan Provincial Graduate Student (Grant no. CX2017B643), Open Research Fund of State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, and the Tribology Science Fund of State Key Laboratory of Tribology, Tsinghua University (Grant no. SKLTKF17B14). So, the affiliation of State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022 China, and State Key Laboratory of Tribology, Tsinghua University, Beijing, 100084 China.

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Authors and Affiliations

  1. School of Materials Science and Engineering, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, Hunan Provincial Key Defense Laboratory of High Temperature Wear-resisting Materials and Preparation Technology, Key Laboratory of Theoretical Organic Chemistry and Function Molecule, Ministry of Education, Hunan University of Science and Technology, Xiangtan, 411201, China

    Baoli Ou, Meilong Chen, Yuanjun Guo, Yonghai Kang, Yan Guo, Shanggao Zhang, Jianhui Yan & Qingquan Liu

  2. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China

    Baoli Ou

  3. State Key Laboratory of Tribology, Tsinghua University, Beijing, 100084, China

    Baoli Ou

  4. State Key Laboratory of Powder Metallurgy, Central South University, Changsha, 410083, China

    Duxin Li

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  1. Baoli Ou
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  2. Meilong Chen
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  3. Yuanjun Guo
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  4. Yonghai Kang
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  5. Yan Guo
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  6. Shanggao Zhang
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  8. Qingquan Liu
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Correspondence to Baoli Ou or Yuanjun Guo.

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Ou, B., Chen, M., Guo, Y. et al. Preparation of novel marine antifouling polyurethane coating materials. Polym. Bull. 75, 5143–5162 (2018). https://doi.org/10.1007/s00289-018-2302-5

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  • DOI: https://doi.org/10.1007/s00289-018-2302-5

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