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Synthesis of fluorinated polycarbonate-based polyurethane acrylate for UV-curable coatings

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Abstract

Fluorinated polycarbonate-based UV-curable polyurethane acrylate (F-PCUA) was synthesized by incorporating 1H, 1H, 2H, 2H-Perfluoro-1-octanol to the end of polycarbonate-based PUA chains. The structure of F-PCUA was determined by 1H-NMR, 19F-NMR, and FTIR analyses. The physical, surface, and thermal properties of F-PCUA were also examined. The F-PCUA was used as a hydrophobic additive in PUA coatings, and the water and oil wettability of the UV-cured film was investigated by contact angle measurements. The results showed that the coating system had great hydrophobicity. Furthermore, X-ray photoelectron spectroscopy research confirmed that a hydrophobic fluorine-enriched surface was obtained in the coating system. Moreover, the mechanical and chemical properties of the hydrophobic coatings did not show deterioration with the introduction of elemental F.

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References

  1. Guan, J, Song, Y, Lin, Y, et al., “Progress in Study of Non-isocyanate Polyurethane.” Ind. Eng. Chem. Res., 50 (11) 6517–6527 (2011)

    Article  Google Scholar 

  2. Liu, N, Zhao, Y, Kang, M, et al., “The Effects of the Molecular Weight and Structure of Polycarbonatediols on the Properties of Waterborne Polyurethanes.” Prog. Org. Coat., 82 46–56 (2015)

    Article  Google Scholar 

  3. Nam, KH, Seo, K, Seo, J, et al., “Ultraviolet-Curable Polyurethane Acrylate Nanocomposite Coatings Based on Surface-Modified Calcium Carbonate.” Prog. Org. Coat., 85 22–30 (2015)

    Article  Google Scholar 

  4. Lucio, B, de la Fuente, JL, et al., “Rheological Cure Characterization of an Advanced Functional Polyurethane.” Thermochim. Acta, 596 6–13 (2014)

    Article  Google Scholar 

  5. Hwang, HD, Park, CH, Moon, JI, et al., “UV-Curing Behavior and Physical Properties of Waterborne UV-Curable Polycarbonate-Based Polyurethane Dispersion.” Prog. Org. Coat., 72 663–675 (2011)

    Article  Google Scholar 

  6. Liu, J, Liu, Q, Zheng, X, et al., “Synthesis of UV-Curable Polycarbonate Diols (PCDL)-Based Polyurethane Acrylate for Negative Photoresist.” Polym. Bull., 73 647–659 (2016)

    Article  Google Scholar 

  7. Ji, H, Côté, A, Koshel, D, et al., “Hydrophobic Fluorinated Carbon Coatings on Silicate Glaze and Aluminum.” Thin Solid Films., 405 (1) 104–108 (2002)

    Article  Google Scholar 

  8. Cortese, G, Martina, F, Vasapollo, G, et al., “Modification of Micro-channel Filling Flow by Poly (dimethylsiloxane) Surface Functionalization with Fluorine-Substituted Aminonaphthols.” J. Fluor. Chem., 131 (3) 357–363 (2010)

    Article  Google Scholar 

  9. Futamata, M, Gai, X, Itoh, H, “Improvement of Water-Repellency Homogeneity by Compound Fluorine–Carbon Sprayed Coating and Silane Treatment.” Vacuum., 73 (3) 519–525 (2004)

    Article  Google Scholar 

  10. Yan, Z, Liu, W, Gao, N, et al., “Synthesis and Characterization of a Novel Difunctional Fluorinated Acrylic Oligomer Used for UV-Cured Coatings.” J. Fluor. Chem., 147 49–55 (2013)

    Article  Google Scholar 

  11. Wang, H, Tang, L, Wu, X, et al., “Fabrication and Anti-frosting Performance of Super Hydrophobic Coating Based on Modified Nano-sized Calcium Carbonate and Ordinary Polyacrylate.” Appl. Surf. Sci., 253 (22) 8818–8824 (2007)

    Article  Google Scholar 

  12. Moon, IJ, Lee, YH, Kim, HJ, et al., “Investigation of the Peel Test for Measuring Self-Cleanable Characteristic of Fluorine-Modified Coatings.” Polym. Test., 31 (3) 433–438 (2012)

    Article  Google Scholar 

  13. Bongiovanni, R, Medici, A, Zompatori, A, et al., “Perfluoropolyether Polymers by UV Curing: Design, Synthesis and Characterization.” Polym. Int., 61 (1) 65–73 (2012)

    Article  Google Scholar 

  14. Miao, H, Cheng, L, Shi, W, “Fluorinated Hyperbranched Polyester Acrylate Used as an Additive for UV Curing Coatings.” Prog. Org. Coat., 65 (1) 71–76 (2009)

    Article  Google Scholar 

  15. Kwon, JY, Kim, HD, “Preparation and Properties of Acid-Treated Multiwalled Carbon Nanotube/Waterborne Polyurethane Nanocomposites.” J. Appl. Polym. Sci., 96 (2) 595–604 (2005)

    Article  Google Scholar 

  16. Verdejo, R, Jell, G, Safinia, L, et al., “Reactive Polyurethane Carbon Nanotube Foams and Their Interactions with Osteoblasts.” J. Biomed. Mater. Res. Part. A., 88 (1) 65–73 (2009)

    Article  Google Scholar 

  17. Cho, JW, Kim, JW, Jung, YC, et al., “Electroactive Shape-Memory Polyurethane Composites Incorporating Carbon Nanotubes.” Macromol. Rapid Commun., 26 (5) 412–416 (2005)

    Article  Google Scholar 

  18. Deka, H, Karak, N, Kalita, RD, et al., “Biocompatible Hyperbranched Polyurethane/Multi-Walled Carbon Nanotube Composites as Shape Memory Materials.” Carbon, 48 (7) 2013–2022 (2010)

    Article  Google Scholar 

  19. Meng, Q, Hu, J, “Self-organizing Alignment of Carbon Nanotube in Shape Memory Segmented Fiber Prepared by In Situ Polymerization and Melt Spinning.” Compos. Part. A Appl. S., 39 (2) 314–321 (2008)

    Article  Google Scholar 

  20. Sahoo, NG, Jung, YC, Yoo, HJ, et al., “Influence of Carbon Nanotubes and Polypyrrole on the Thermal, Mechanical and Electroactive Shape-Memory Properties of Polyurethane Nanocomposites.” J. Compos. Sci. Technol., 67 (9) 1920–1929 (2007)

    Article  Google Scholar 

  21. Ma, CCM, Huang, YL, Kuan, HC, et al., “Preparation and Electromagnetic Interference Shielding Characteristics of Novel Carbon-Nanotube/Siloxane/Poly-(urea urethane) Nanocomposites.” J. Polym. Sci. Part B Polym. Phys., 43 (4) 345–358 (2005)

    Article  Google Scholar 

  22. Kojio, K, Nonaka, Y, Masubuchi, T, et al., “Effect of the Composition Ratio of Copolymerized Poly (carbonate) Glycol on the Microphase-Separated Structures and Mechanical Properties of Polyurethane Elastomers.” J. Polym. Sci. Part B Polym. Phys., 42 (24) 4448–4458 (2004)

    Article  Google Scholar 

  23. Špírková, M, Pavličević, J, Strachota, A, et al., “Novel Polycarbonate-Based Polyurethane Elastomers: Composition-Property Relationship.” Eur. Polym. J., 47 (5) 959–972 (2011)

    Article  Google Scholar 

  24. Feng, YX, Yin, N, Li, QF, et al., “Environmentally Benign Route for the Synthesis of Polycarbonate Diols (PCDLs)-Calcined MgAl Hydrotalcites as Heterogeneous Catalysts.” Ind. Eng. Chem. Res., 47 (7) 2140–2145 (2008)

    Article  Google Scholar 

  25. Hwang, HD, Kim, HJ, “UV-Curable Low Surface Energy Fluorinated Polycarbonate-Based Polyurethane Dispersion.” J. Colloid Interface Sci., 362 (2) 274–284 (2011)

    Article  Google Scholar 

  26. Hwang, HD, Kim, HJ, “Enhanced Thermal and Surface Properties of Waterborne UV-Curable Polycarbonate-Based Polyurethane (meth) Acrylate Dispersion by Incorporation of Polydimethylsiloxane.” J. React. Funct. Polym., 71 (6) 655–665 (2011)

    Article  Google Scholar 

  27. Hwang, HD, Park, CH, Moon, JI, et al., “UV-Curing Behavior and Physical Properties of Waterborne UV-Curable Polycarbonate-Based Polyurethane Dispersion.” Prog. Org. Coat., 72 (4) 663–675 (2011)

    Article  Google Scholar 

  28. Wu, S, “Calculation of Interfacial Tension in Polymer Systems.” J. Polym. Sci. Part C., 34 (1) 19–30 (1971)

    Article  Google Scholar 

  29. Asif, A, Shi, W, “UV Curable Waterborne Polyurethane Acrylate Dispersions Based on Hyperbranched Aliphatic Polyester: Effect of Molecular Structure on Physical and Thermal Properties.” Adv. Technol., 15 (11) 669–675 (2004)

    Article  Google Scholar 

  30. Yang, J, Wang, Z, Zeng, Z, et al., “Chain-Extended Polyurethane-Acrylate Ionomer for UV-Curable Waterborne Coatings.” J. Appl. Polym. Sci., 84 (10) 1818–1831 (2002)

    Article  Google Scholar 

  31. Lin, Y, Liao, K, Chou, N, et al., “UV-Curable Low-Surface-Energy Fluorinated Poly (Urethane-Acrylate)s for Biomedical Applications.” Eur. Polym. J., 44 (9) 2927–2937 (2008)

    Article  Google Scholar 

  32. Levine, F, La Scala, J, Kosik, W, “Properties of Clear Polyurethane Films Modified with a Fluoropolymer Emulsion.” Prog. Org. Coat., 69 (1) 63–72 (2010)

    Article  Google Scholar 

  33. Fabbri, P, Messori, M, Montecchi, M, et al., “Perfluoropolyether-Based Organic–Inorganic Hybrid Coatings.” Polymer, 47 (4) 1055–1062 (2006)

    Article  Google Scholar 

Download references

Acknowledgments

We acknowledge the financial support from the National Science Foundation of China (No. 51403082), the National Nature Science Foundation of Jiangsu Province (No. BK20130153), and the Fundamental Research Funds for the Central Universities (JUSRP11514).

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Correspondence to Yan Yuan.

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Liu, J., Wang, B., Yuan, Y. et al. Synthesis of fluorinated polycarbonate-based polyurethane acrylate for UV-curable coatings. J Coat Technol Res 14, 233–241 (2017). https://doi.org/10.1007/s11998-016-9847-8

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  • DOI: https://doi.org/10.1007/s11998-016-9847-8

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