Skip to main content
SpringerLink
Log in

Urethane methacrylate reactive diluents for UV-curable polyester powder coatings

  • Published:
Journal of Coatings Technology and Research Aims and scope Submit manuscript

Abstract

Three urethane methacrylates, one monofunctional derivative and two di-functional derivatives with different chain lengths were used as reactive diluents in UV-curable polyester powder coatings. Each reactive diluent was formulated with a methacrylated polyester oligomer using conventional melt extrusion techniques. The effect of these compounds on zero-shear melt viscosity was investigated. Incorporation of 10 wt% reactive diluent effectively reduced the viscosity by an order of magnitude. After UV-curing, the viscoelastic, thermal, and mechanical properties of the films were characterized using dynamic mechanical analysis, differential scanning calorimetry, thermogravimetric analysis, and tensile tests. The type and concentration of reactive diluent that was used directly influenced the glass transition temperature, modulus, % elongation-at-break, and crosslink density. Of the two di-functional reactive diluents that were used, the derivative that contained a shorter methylene spacer group resulted in more heterogeneous crosslinked networks.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Sharmin, E, Zafar, F, Akram, D, Alam, M, Ahmad, S, “Recent Advances in Vegetable Oils Based Environment Friendly Coatings: A Review.” Ind. Crops Prod., 76 215–229 (2015)

    Article  CAS  Google Scholar 

  2. Noordover, BAJ, Van Staalduinen, VG, Duchateau, R, Koning, CE, Van Benthem, RATM, Mak, M, Heise, A, Frissen, AE, Van Haveren, J, “Co- and Terpolyesters Based on Isosorbide and Succinic Acid for Coating Applications: Synthesis and Characterization.” Biomacromolecules, 7 3406–3416 (2006)

    Article  CAS  Google Scholar 

  3. Noordover, BAJ, Heise, A, Malanowski, P, Senatore, D, Mak, M, Molhoek, L, Duchateau, R, Koning, CE, Van Benthem, RATM, “Biobased Step-Growth Polymers in Powder Coating Applications.” Prog. Org. Coat., 65 187–196 (2009)

    Article  CAS  Google Scholar 

  4. Gioia, C, Minesso, A, Cavalieri, R, Marchese, P, Celli, A, Colonna, M, “Powder Coatings for Indoor Applications from Renewable Resources and Recycled Polymers.” J. Coat. Technol. Res., 12 555–562 (2015)

    Article  CAS  Google Scholar 

  5. Tiwari, A, Galanis, A, Soucek, MD, Biobased and Environmental Benign Coatings. Wiley, Hoboken (2016)

    Book  Google Scholar 

  6. Wicks, Z, Jones, F, Pappas, P, Wicks, D, “Powder Coatings.” In: Organic Coatings: Science and Technology, pp. 548–573. Wiley, Hoboken (2007).

  7. Gilles de Lange, P, Powder Coatings: Chemistry and Technology. Vincentz Network (2004).

  8. Mafi, R, Mirabedini, SM, Attar, MM, Moradian, S, “Cure Characterization of Epoxy and Polyester Clear Powder Coatings Using Differential Scanning Calorimetry (DSC) and Dynamic Mechanical Thermal Analysis (DMTA).” Prog. Org. Coat., 54 164–169 (2005)

    Article  CAS  Google Scholar 

  9. McGinniss, V, “Ultraviolet Curable Epoxy Polyester Powder Paints.” US Patent 4129488A (1976).

  10. Castell, P, Wouters, M, Fischer, H, De With, G, “Kinetic Studies of a UV-Curable Powder Coating Using Photo-DSC, Real-Time FTIR and Rheology.” J. Coat. Technol. Res., 4 411–423 (2007)

    Article  CAS  Google Scholar 

  11. Udding-louwrier, S, Baijards, RA, Jong, ES, “New Developments in Radiation-Curable Powder Coatings.” J. Coat. Technol., 72 71–75 (2000)

    Article  CAS  Google Scholar 

  12. Li, Y, Liu, L, Gu, Y, Xie, J, Zhang, J, Qu, J, “Improve Surface Levelling of Powder Coating with Semi-Crystalline Polyester Resin.” Prog. Org. Coat., 99 191–196 (2016)

    Article  CAS  Google Scholar 

  13. Johansson, M, Malmstrom, E, Jansson, A, Hult, A, “Novel Concept for Low Temperature Curing Powder Coatings Based on Hyperbranched Polyesters.” J. Coat. Technol., 72 49–54 (2000)

    Article  CAS  Google Scholar 

  14. Claesson, H, Malmstrom, E, Johansson, M, Hult, A, Doyle, M, Manson, JAE, “Rheological Behaviour During UV-Curing of a Star-Branched Polyester.” Prog. Org. Coat., 44 63–67 (2002)

    Article  CAS  Google Scholar 

  15. Claesson, H, Malmstrom, E, Johansson, M, Hult, A, “Synthesis and Characterisation of Star Branched Polyesters with Dendritic Cores and the Effect of Structural Variations on Zero Shear Rate Viscosity.” Polymer, 43 3511–3518 (2002)

    Article  CAS  Google Scholar 

  16. Chang, Y, “Thermosetting Powder Coating Compositions.” World Patent 1994002552 A1, (1992)

  17. Muthiah, J, Daly, AT, Haley, RP, Kozlowski, JJ, “Dual Thermal and Ultraviolet Curable Powder Coatings.” US Patent 5922473A, (1996)

  18. Twigt, F, Van der Linde, R, “Radiation Curable Binder Composition for Powder Paint Formulations.” US Patent 5703198A, (1993)

  19. Wouters, M, De Ruiter, B, “Contact-Angle Development of Polymer Melts.” Prog. Org. Coat., 48 207–213 (2003)

    Article  CAS  Google Scholar 

  20. Wang, X, Soucek, MD, “Investigation of Non-isocyanate Urethane Dimethacrylate Reactive Diluents for UV-Curable Polyurethane Coatings.” Prog. Org. Coat., 76 1057–1067 (2013)

    Article  CAS  Google Scholar 

  21. Wu, S, Sears, MT, Soucek, MD, Simonsick, WJ, “Synthesis of Reactive Diluents for Cationic Cycloaliphatic Epoxide UV Coatings.” Polymer, 40 5675–5686 (1999)

    Article  CAS  Google Scholar 

  22. Nalawade, PP, Mehta, B, Pugh, C, Soucek, MD, “Modified Soybean Oil as a Reactive Diluent: Synthesis and Characterization.” J. Polym. Sci. Part A Polym. Chem., 52 3045–3059 (2014)

    Article  CAS  Google Scholar 

  23. Speckhard, TA, Hwang, KKS, Lin, SB, Tsay, SY, “Properties of UV-Curable Polyurethane Acrylates: Effect of Reactive Diluent.” J. Appl. Polym. Sci., 30 647–666 (1985)

    Article  CAS  Google Scholar 

  24. Maurin, V, Croutxé-Barghorn, C, Allonas, X, “Photopolymerization Process of UV Powders. Characterization of Coating Properties.” Prog. Org. Coat., 73 250–256 (2012)

    Article  CAS  Google Scholar 

  25. Johansson, M, Falkén, H, Irestedt, A, Hult, A, “On the Synthesis and Characterization of New Low Temperature Curing Powder Coatings Cured with Radiation.” J. Coat. Technol., 70 57–62 (1998)

    Article  CAS  Google Scholar 

  26. Assumption, HJ, Mathias, LJ, “Photopolymerization of Urethane Dimethacrylates Synthesized Via a Non-isocyanate Route.” Polymer, 44 5131–5136 (2003)

    Article  CAS  Google Scholar 

  27. Rokicki, G, Piotrowska, A, “A New Route to Polyurethanes from Ethylene Carbonate, Diamines and Diols.” Polymer, 43 2927–2935 (2002)

    Article  CAS  Google Scholar 

  28. Khalyavina, A, Häußler, L, Lederer, A, “Effect of the Degree of Branching on the Glass Transition Temperature of Polyesters.” Polymer, 53 1049–1053 (2012)

    Article  CAS  Google Scholar 

  29. Brinke, G, Karasz, F, Thomas, E, “Depression of Glass Transition Temperatures of Polymer.” Macromolecules, 16 244–249 (1983)

    Article  Google Scholar 

  30. Simon, J, Barla, F, Kelemen-Haller, A, Farkas, F, Kraxner, M, “Thermal Stability of Polyurethanes.” Chromatographia, 25 99–106 (1988)

    Article  CAS  Google Scholar 

  31. Hentschel, T, Munstedt, H, “Kinetics of Molar Mass Decrease in Polyurethane Melt: A Rheological Study.” Polymer, 42 3195–3203 (2001)

    Article  CAS  Google Scholar 

  32. Safranski, DL, Gall, K, “Effect of Chemical Structure and Crosslinking Density on the Thermo-Mechanical Properties and Toughness of (Meth) Acrylate Shape Memory Polymer Networks.” Polymer, 49 4446–4455 (2008)

    Article  CAS  Google Scholar 

  33. Elliott, JE, Bowman, CN, “Monomer Functionality and Polymer Network Formation.” Macromolecules, 34 4642–4649 (2001)

    Article  CAS  Google Scholar 

  34. Young, JS, Kannurpatti, AR, Bowman, CN, “Effect of Comonomer Concentration and Functionality on Photopolymerization Rates, Mechanical Properties and Heterogeneity of the Polymer.” Macromol. Chem. Phys., 199 1043–1049 (1998)

    Article  CAS  Google Scholar 

  35. Kannurpatti, AR, Anseth, JW, Bowman, CN, “A Study of the Evolution of Mechanical Properties and Structural Heterogeneity of Polymer Networks Formed by Photopolymerizations of Multifunctional (Meth)Acrylates.” Polymer, 39 2507–2513 (1998)

    Article  CAS  Google Scholar 

  36. Khonakdar, HA, Morshedian, J, Wagenknecht, U, Jafari, SH, “An Investigation of Chemical Crosslinking Effect on Properties of High-Density Polyethylene.” Polymer, 44 4301–4309 (2003)

    Article  CAS  Google Scholar 

  37. Sahagun, CM, Morgan, SE, “Thermal Control of Nanostructure and Molecular Network Development in Epoxy-Amine Thermosets.” ACS Appl. Mater. Interfaces, 4 564–572 (2012)

    Article  CAS  Google Scholar 

  38. Young, JS, Bowman, CN, “Effect of Polymerization Temperature and Cross-Linker Concentration on Reaction Diffusion Controlled Termination.” Macromolecules, 32 6073–6081 (1999)

    Article  CAS  Google Scholar 

  39. Daly, AT, Muthiah, J, Haley, RP, Decker, OH, Reinheimer, EP, Snyder, MB, “Non-hazing UV Curable Powder Coatings Containing Crystalline Resins.” US Patent 6011080A (1998)

  40. The Powder Coating Institute, Frequently asked questions. https://www.powdercoating.org/page/FAQ#PA3. Accessed 15 Feb 2020

  41. Nebioglu, A, Soucek, MD, “Microgel Formation and Thermo-Mechanical Properties of UV-Curing Unsaturated Polyester Acrylates.” J. Appl. Polym. Sci., 107 2364–2374 (2007)

    Article  Google Scholar 

  42. Nebioglu, A, Soucek, MD, “Reaction Kinetics and Microgel Particle Size Characterization of Ultraviolet-Curing Unsaturated Polyester Acrylates.” J. Polym. Sci. Part A Polym. Chem., 44 6544–6557 (2006)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Polymer Engineering, University of Akron, Akron, OH, 44325, USA

    Theodore J. Hammer, Hamideh M. Shokouhi Mehr & Mark D. Soucek

  2. Department of Polymer Science, University of Akron, Akron, OH, 44325, USA

    Theodore J. Hammer & Coleen Pugh

  3. Department of Chemistry, Wichita State University, Wichita, KS, 67260, USA

    Coleen Pugh

Authors
  1. Theodore J. Hammer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hamideh M. Shokouhi Mehr
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Coleen Pugh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mark D. Soucek
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mark D. Soucek.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 386 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hammer, T.J., Mehr, H.M.S., Pugh, C. et al. Urethane methacrylate reactive diluents for UV-curable polyester powder coatings. J Coat Technol Res 18, 333–348 (2021). https://doi.org/10.1007/s11998-020-00391-8

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-020-00391-8

Keywords

Search

Navigation