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Journal of Coatings Technology and Research

, Volume 16, Issue 2, pp 415–428 | Cite as

Castor oil-based waterborne hyperbranched polyurethane acrylate emulsion for UV-curable coatings with excellent chemical resistance and high hardness

  • Daidong Wei
  • Bing Liao
  • Qiwen Yong
  • Huiyi Wang
  • Tao Li
  • Jianheng Huang
  • Hao PangEmail author
Article
  • 212 Downloads

Abstract

Synthesis, characterization, and coating performance of castor oil (CO)-based waterborne hyperbranched polyurethane acrylate (WHPUA) emulsions are highlighted in this work. Herein, a second-generation CO-based hyperbranched polyester (C20) was synthesized by introducing the renewable CO as a B3 core and dimethylolpropionic acid as an AB2 monomer via a pseudo-one-pot condensation procedure. Three types of CO-based WHPUA emulsions were prepared through the addition of the hyperbranched C20 with maleic anhydride (MA) and the isocyanate-bearing semiadduct (IPDI-HEA) at different MA/IPDI-IH molar ratios without the addition of any emulsifiers. The prepared emulsions were further formulated into UV-curable coating formulations and exposed to a medium-pressure mercury lamp. Consequently, the obtained UV-cured coatings exhibited outstanding adhesion performance, excellent transparency, and an acceptable degree of final double bond conversion. Owing to a relatively low concentration of hydrophilic units and a large number of acrylate functionalities in the waterborne oligomer, the obtained films were endowed with high crosslinking density and low hydrophilic nature, thus producing enhanced tensile strength, pencil hardness, water resistance, and chemical resistance. Due to their combination of renewable materials, a waterborne system and a UV-curing technique, these CO-based WHPUA emulsions offer promising opportunities to be used as environmentally friendly coatings.

Keywords

Hyperbranched Waterborne polyurethane acrylate UV-curable coatings Castor oil Chemical resistance 

Notes

Acknowledgments

This research was supported by the Guangdong Academy of Sciences Project (Grant No. 2017GDASCX-0705).

Compliance with ethical standards

Conflict of interest

The authors declare there is no conflict of interest.

References

  1. 1.
    Zhang, QY, Huang, C, Wang, HX, Hu, MJ, Li, HB, Liu, XH, “UV-Curable Coating Crosslinked by a Novel Hyperbranched Polyurethane Acrylate with Excellent Mechanical Properties and Hardness.” RSC Adv., 6 (109) 107942–107950 (2016)CrossRefGoogle Scholar
  2. 2.
    Yu, B, Wang, X, Xing, WY, Yang, HY, Song, L, Hu, Y, “UV-Curable Functionalized Graphene Oxide/Polyurethane Acrylate Nanocomposite Coatings with Enhanced Thermal Stability and Mechanical Properties.” Ind. Eng. Chem. Res., 51 (45) 14629–14636 (2012)CrossRefGoogle Scholar
  3. 3.
    Guler, B, Onen, HA, Karahasanoglu, M, Serhatli, E, Canak, TC, “Preparation and Characterization of Chalcone Functional Urethane Acrylates for Coating Applications.” Prog. Org. Coat., 109 152–159 (2017)CrossRefGoogle Scholar
  4. 4.
    Fang, ZH, Duan, HY, Zhang, ZH, Wang, J, Li, DQ, Huang, YX, Shang, JJ, Liu, ZY, “Novel Heat-Resistance UV Curable Waterborne Polyurethane Coatings Modified by Melamine.” Appl. Surf. Sci., 257 (11) 4765–4768 (2011)CrossRefGoogle Scholar
  5. 5.
    Yuan, CD, Wang, MY, Li, HT, Wang, ZW, “Preparation and Properties of UV-Curable Waterborne Polyurethane-Acrylate Emulsion.” J. Appl. Polym. Sci., 134 (34) 45208 (2017)CrossRefGoogle Scholar
  6. 6.
    Zhang, T, Wu, W, Wang, X, Mu, Y, “Effect of Average Functionality on Properties of UV-Curable Waterborne Polyurethane-Acrylate.” Prog. Org. Coat., 68 (3) 201–207 (2010)CrossRefGoogle Scholar
  7. 7.
    Wang, J, Zhang, H, Miao, Y, Qiao, L, Wang, X, Wang, F, “UV-Curable Waterborne Polyurethane from CO2-Polyol with High Hydrolysis Resistance.” Polymer, 100 219–226 (2016)CrossRefGoogle Scholar
  8. 8.
    Shin, M, Lee, Y, Rahman, M, Kim, H, “Synthesis and Properties of Waterborne Fluorinated Polyurethane-Acrylate Using a Solvent-/Emulsifier-Free Method.” Polymer, 54 (18) 4873–4882 (2013)CrossRefGoogle Scholar
  9. 9.
    Xu, J, Rong, X, Chi, T, Wang, M, Wang, Y, Yang, D, Qiu, F, “Preparation, Characterization of UV-Curable Waterborne Polyurethane Acrylate and the Application in Metal Iron Surface Protection.” J. Appl. Polym. Sci., 130 (5) 3142–3152 (2013)CrossRefGoogle Scholar
  10. 10.
    Zhang, S, Chen, Z, Guo, M, Bai, H, Liu, X, “Synthesis and Characterization of Waterborne UV-Curable Polyurethane Modified with Side-Chain Triethoxysilane and Colloidal Silica.” Colloids Surf. A Physicochem. Eng. Asp., 468 1–9 (2015)CrossRefGoogle Scholar
  11. 11.
    Bai, CY, Zhang, XY, Dai, JB, Zhang, CY, “Water Resistance of the Membranes for UV Curable Waterborne Polyurethane Dispersions.” Prog. Org. Coat., 59 (4) 331–336 (2007)CrossRefGoogle Scholar
  12. 12.
    Asif, A, Shi, W, “UV Curable Waterborne Polyurethane Acrylate Dispersions Based on Hyperbranched Aliphatic Polyester: Effect of Molecular Structure on Physical and Thermal Properties.” Polym. Adv. Technol., 15 (11) 669–675 (2004)CrossRefGoogle Scholar
  13. 13.
    Voit, BI, Lederer, A, “Hyperbranched and Highly Branched Polymer Architecturess Synthetic Strategies and Major Characterization Aspects.” Chem. Rev., 109 (11) 5924–5973 (2009)CrossRefGoogle Scholar
  14. 14.
    Voit, B, “Hyperbranched Polymers-All Problems Solved After 15 years of Research?” J. Polym. Sci. Part A Polym. Chem., 43 (13) 2679–2699 (2005)CrossRefGoogle Scholar
  15. 15.
    Tasic, S, Bozic, B, Dunjic, B, “Synthesis of New Hyperbranched Urethane-Acrylates and Their Evaluation in UV-Curable Coatings.” Prog. Org. Coat., 51 (4) 321–328 (2004)CrossRefGoogle Scholar
  16. 16.
    Xiang, H, Wang, X, Xi, L, Dong, H, Hong, P, Su, J, Cui, Y, Liu, X, “Effect of Soft Chain Length and Generation Number on Properties of Flexible Hyperbranched Polyurethane Acrylate and Its UV-Cured Film.” Prog. Org. Coat., 114 216–222 (2018)CrossRefGoogle Scholar
  17. 17.
    Flory, PJ, “Molecular Size Distribution in Three Dimensional Polymers. VI. Branched Polymers Containing A-R-Bf−1 Type Units.” J. Am. Chem. Soc., 74 (11) 2718–2723 (1952)CrossRefGoogle Scholar
  18. 18.
    Asif, A, Hu, L, Shi, W, “Synthesis, Rheological, and Thermal Properties of Waterborne Hyperbranched Polyurethane Acrylate Dispersions for UV Curable Coatings.” Colloid Polym. Sci., 287 (9) 1041–1049 (2009)CrossRefGoogle Scholar
  19. 19.
    Asif, A, Huang, C, Shi, W, “Structure-Property Study of Waterborne, Polyurethane Acrylate Dispersions Based on Hyperbranched Aliphatic Polyester for UV-Curable Coatings.” Colloid Polym. Sci., 283 (2) 200–208 (2004)CrossRefGoogle Scholar
  20. 20.
    Asif, A, Huang, CY, Shi, WF, “Photopolymerization of Waterborne Polyurethane Acrylate Dispersions Based on Hyperbranched Aliphatic Polyester and Properties of The Cured Films.” Colloid Polym. Sci., 283 (7) 721–730 (2004)CrossRefGoogle Scholar
  21. 21.
    Asif, A, Shi, W, “Synthesis and Properties of UV Curable Waterborne Hyperbranched Aliphatic Polyester.” Eur. Polym. J., 39 (5) 933–938 (2003)CrossRefGoogle Scholar
  22. 22.
    Asif, A, Shi, W, Shen, X, Nie, K, “Physical and Thermal Properties of UV Curable Waterborne Polyurethane Dispersions Incorporating Hyperbranched Aliphatic Polyester of Varying Generation Number.” Polymer, 46 (24) 11066–11078 (2005)CrossRefGoogle Scholar
  23. 23.
    Zhang, J, Xu, H, Hu, L, Yang, Y, Li, H, Huang, C, Liu, X, “Novel Waterborne UV-Curable Hyperbranched Polyurethane Acrylate/Silica with Good Printability and Rheological Properties Applicable to Flexographic Ink.” ACS Omega, 2 (11) 7546–7558 (2017)CrossRefGoogle Scholar
  24. 24.
    Lin, X, Zhang, S, Qian, J, “Synthesis and Properties of a Novel UV-Curable Waterborne Hyperbranched Polyurethane.” J. Coat. Technol. Res., 11 (3) 319–328 (2013)CrossRefGoogle Scholar
  25. 25.
    Yin, W, Zeng, X, Li, H, Hou, Y, Gao, Q, “Synthesis, Photopolymerization Kinetics, and Thermal Properties of UV-Curable Waterborne Hyperbranched Polyurethane Acrylate Dispersions.” J. Coat. Technol. Res., 8 (5) 577–584 (2011)CrossRefGoogle Scholar
  26. 26.
    Yin, W, Zeng, X, Li, H, Lin, X, Ren, B, Tong, Z, “Steady Rheological Behaviors Of UV-Curable Waterborne Hyperbranched Polyurethane Acrylate Dispersions.” J. Coat. Technol. Res., 10 (1) 57–64 (2012)CrossRefGoogle Scholar
  27. 27.
    Li, GN, Jiang, SL, Gao, YJ, Liu, XK, Sun, F, “Synthesis and Property of Water-Soluble Hyperbranched Photosensitive Polysiloxane Urethane Acrylate.” Ind. Eng. Chem. Res., 52 (6) 2220–2227 (2013)CrossRefGoogle Scholar
  28. 28.
    Zagar, E, Zigon, M, “Characterization of a Commercial Hyperbranched Aliphatic Polyester Based on 2,2-Bis(methylol)propionic Acid.” Macromolecules, 35 (27) 9913–9925 (2002)CrossRefGoogle Scholar
  29. 29.
    Karak, N, Rana, S, Cho, JW, “Synthesis and Characterization of Castor-Oil-Modified Hyperbranched Polyurethanes.” J. Appl. Polym. Sci., 112 (2) 736–743 (2009)CrossRefGoogle Scholar
  30. 30.
    Eren, T, Çolak, S, Küsefoglu, SH, “Simultaneous Interpenetrating Polymer Networks Based on Bromoacrylated Castor Oil Polyurethane.” J. Appl. Polym. Sci., 100 (4) 2947–2955 (2006)CrossRefGoogle Scholar
  31. 31.
    Li, K, Shen, Y, Fei, G, Wang, H, Li, J, “Preparation and Properties of Castor Oil/Pentaerythritol Triacrylate-Based UV Curable Waterborne Polyurethane Acrylate.” Prog. Org. Coat., 78 146–154 (2015)CrossRefGoogle Scholar
  32. 32.
    Chen, G, Guan, X, Xu, R, Tian, J, He, M, Shen, W, Yang, J, “Synthesis and Characterization of UV-Curable Castor Oil-Based Polyfunctional Polyurethane Acrylate via Photo-Click Chemistry and Isocyanate Polyurethane Reaction.” Prog. Org. Coat., 93 11–16 (2016)CrossRefGoogle Scholar
  33. 33.
    Thakur, S, Karak, N, “Castor Oil-Based Hyperbranched Polyurethanes as Advanced Surface Coating Materials.” Prog. Org. Coat., 76 (1) 157–164 (2013)CrossRefGoogle Scholar
  34. 34.
    Malmstrom, E, Johansson, M, Hult, A, “Hyperbranched Aliphatic Polyesters.” Macromolecules, 28 (5) 1698–1703 (1995)CrossRefGoogle Scholar
  35. 35.
    Hu, H, Yuan, Y, Shi, W, “Preparation of Waterborne Hyperbranched Polyurethane Acrylate/LDH Nanocomposite.” Prog. Org. Coat., 75 (4) 474–479 (2012)CrossRefGoogle Scholar
  36. 36.
    Dzunuzovic, E, Tasic, S, Bozic, B, Jeremic, K, Dunjic, B, “Photoreactive Hyperbranched Urethane Acrylates Modified with a Branched Saturated Fatty Acid.” React. Funct. Polym., 66 (10) 1097–1105 (2006)CrossRefGoogle Scholar
  37. 37.
    Mao, HY, Qiang, SY, Xu, Y, Wang, CX, “Synthesis of Polymeric Dyes Based on UV Curable Multifunctional Waterborne Polyurethane for Textile Coating.” New J. Chem., 41 (2) 619–627 (2017)CrossRefGoogle Scholar
  38. 38.
    Malmstrom, E, Hult, A, “Kinetics of Formation of Hyperbranched Polyesters Based on 2,2-Bis(methylol)propionic acid.” Macromolecules, 29 (4) 1222–1228 (1996)CrossRefGoogle Scholar
  39. 39.
    Hanselmann, R, Holter, D, Frey, H, “Hyperbranched Polymers Prepared via the Core-Dilution_Slow Addition.” Macromolecules, 31 3790–3801 (1998)CrossRefGoogle Scholar
  40. 40.
    Bialas, N, Höcker, H, Marschner, M, Ritter, W, “13C NMR Studies on the Relative Reactivity of Isocyanate Groups of Isophorone Diisocyanate Isomers.” Macromol. Chem. Phys., 191 1843–1852 (1990)CrossRefGoogle Scholar
  41. 41.
    Rochery, M, Vroman, I, Lam, TM, “Kinetic Model for the Reaction of Ipdi and Macrodiols: Study on the Relative Reactivity of Isocyanate Groups.” J. Macromol. Sci. Part A, 37 (3) 259–275 (2000)CrossRefGoogle Scholar
  42. 42.
    Luo, S, Hu, X, Zhang, Y, Ling, C, Liu, X, Chen, S, “Synthesis of Thermoresponsive Unimolecular Polymeric Micelles with a Hydrophilic Hyperbranched Poly(glycidol) Core.” Polym. J., 43 (1) 41–50 (2010)CrossRefGoogle Scholar
  43. 43.
    Magnusson, H, Malmstrom, E, Hult, A, “Structure Buildup in Hyperbranched Polymers From 2,2-Bis(hydroxymethyl)propionic acid.” Macromolecules, 33 (8) 3099–3104 (2000)CrossRefGoogle Scholar
  44. 44.
    Hawker, CJ, Lee, R, Fréchet, JMJ, “One-Step Synthesis of Hyperbranched Dendritic Polyesters.” J. Am. Chem. Soc., 113 (12) 4583–4588 (1991)CrossRefGoogle Scholar
  45. 45.
    Zhang, S, Chen, J, Han, D, Feng, Y, Shen, C, Chang, C, Song, Z, Zhao, J, “Effect of Polyether Soft Segments on Structure and Properties of Waterborne UV-Curable Polyurethane Nanocomposites.” J. Coat. Technol. Res., 12 (3) 563–569 (2015)CrossRefGoogle Scholar
  46. 46.
    Jung, DH, Kim, EY, Kang, YS, Kim, BK, “High Solid and High Performance UV Cured Waterborne Polyurethanes.” Colloids Surf. A Physicochem. Eng. Asp., 370 (1–3) 58–63 (2010)CrossRefGoogle Scholar
  47. 47.
    Dzunuzovic, E, Tasic, S, Bozic, B, Babic, D, Dunjic, B, “Dynamical Mechanical Analysis of Photocrosslinked Hyperbranched Urethane Acrylates.” J. Serb. Chem. Soc., 69 (6) 441–453 (2004)CrossRefGoogle Scholar
  48. 48.
    Tan, J, Li, W, Wang, Z, “Preparation and Performance of Waterborne UV-Curable Polyurethane Containing Long Fluorinated Side Chains.” J. Appl. Polym. Sci., 134 (8) 44506 (2016)Google Scholar
  49. 49.
    Xu, H, Qiu, F, Wang, Y, Yang, D, Wu, W, Chen, Z, Zhu, J, “Preparation, Mechanical Properties of Waterborne Polyurethane and Crosslinked Polyurethane-Acrylate Composite.” J. Appl. Polym. Sci., 124 (2) 958–968 (2012)CrossRefGoogle Scholar
  50. 50.
    Xu, H, Qiu, F, Wang, Y, Wu, W, Yang, D, Guo, Q, “UV-Curable Waterborne Polyurethane-Acrylate: Preparation, Characterization and Properties.” Prog. Org. Coat., 73 (1) 47–53 (2012)CrossRefGoogle Scholar
  51. 51.
    Jiao, Z, Yang, Q, Wang, X, Wang, C, “UV-Curable Hyperbranched Urethane Acrylate Oligomers Modified with Different Fatty Acids.” Polym. Bull., 74 (12) 5049–5063 (2017)CrossRefGoogle Scholar
  52. 52.
    Han, LJ, Dai, JY, Zhang, LS, Ma, SQ, Deng, J, Zhang, RY, Zhu, J, “Diisocyanate Free and Melt Polycondensation Preparation of Bio-Based Unsaturated Poly(ester-urethane)s and Their Properties as UV Curable Coating Materials.” RSC Adv., 4 (90) 49471–49477 (2014)CrossRefGoogle Scholar
  53. 53.
    Mishra, V, Mohanty, I, Patel, MR, Patel, KI, “Development of Green Waterborne UV-Curable Castor Oil-Based Urethane Acrylate Coatings: Preparation and Property Analysis.” Int. J. Polym. Anal. Charact., 20 (6) 504–513 (2015)CrossRefGoogle Scholar
  54. 54.
    Džunuzović, ES, Tasić, SV, Božić, BR, Džunuzović, JV, Dunjić, BM, Jeremić, KB, “Mechanical and Thermal Properties of UV Cured Mixtures of Linear and Hyperbranched Urethane Acrylates.” Prog. Org. Coat., 74 (1) 158–164 (2012)CrossRefGoogle Scholar

Copyright information

© American Coatings Association 2018

Authors and Affiliations

  • Daidong Wei
    • 1
    • 2
  • Bing Liao
    • 3
  • Qiwen Yong
    • 1
    • 2
  • Huiyi Wang
    • 1
    • 2
  • Tao Li
    • 1
    • 2
  • Jianheng Huang
    • 1
  • Hao Pang
    • 1
    Email author
  1. 1.Key Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou Institute of ChemistryChinese Academy of SciencesGuangzhouChina
  2. 2.University of Chinese Academy of SciencesBeijingChina
  3. 3.Guangdong Academy of SciencesGuangzhouChina

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