Skip to main content
Log in

Effects of different dicarboxylic acid on the UV-curable urethane resins made from palm fatty acid distillate

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

Abstract

A series of four polyol macromers with similar hydroxyl number was prepared by reacting palm fatty acid distillate with neopentaglycol, pentaerythritol, and separate equimolar amounts of isophthalic acid (IPA), terephthalic acid (TPA), phthalic anhydride (PA), and adipic acid (AA). Each macromer was then copolymerized with 2-hydroxylethyl acrylate (2-HEA) and toluene diisocyanate to produce the UV curable resins labeled as UA–IPA, UA–TPA, UA–PA, and UA–AA, respectively. The glass transition temperature (Tg), pendulum hardness, and adhesion properties of the cured films were studied. In general, all the resins produced coatings with high gloss and good adhesion. When accelerated weathering tests were carried out, films of UA–TPA could withstand UVA exposure up to 1500 h. When subjected to methyl ethyl ketone double rub test, cured films of UA–IPA and UA–TPA could withstand the highest double rubs at 90 times, followed by UA–PA and UA–AA at 45 and 15 times, respectively. Under salt spray corrosion test for 720 h, cured films showed good corrosion resistance with no observable blistering, except for UA–AA that showed slight blistering. Excellent water resistance was achieved by all cured films with good adhesion and minimal gloss reduction.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4
Scheme 2
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. Hermas, AA, “XPS Analysis of the Passive Film Formed on Austenitic Stainless Steel Coated with Conductive Polymer.” Corros. Sci., 50 2498–2505 (2008)

    CAS  Google Scholar 

  2. Okamoto, G, Shibata, T, The Electrochemical Society Monograph Series, Chapter 6. Pennington Publish, New Jersey (1978)

    Google Scholar 

  3. Schultze, JW, Lohrengel, MM, “Stability, Reactivity and Breakdown of Passive Films: Problems of Recent and Future Research.” Electrochim. Acta, 45 2499–2513 (2000)

    CAS  Google Scholar 

  4. Molenaar, F, Buijsen, P, Smit, CN, “Adhesion of Electron Beam Curable Coatings on Metal Substrates.” Prog. Org. Coat., 22 393–399 (1993)

    CAS  Google Scholar 

  5. Roose, P, Fallais, I, Vamdermiers, C, Olivier, MG, Oieknab, M, “Radiation Curing Technology: An Attractive Technology for Metal Coating.” Prog. Org. Coat., 64 163–170 (2009)

    CAS  Google Scholar 

  6. Hoyle, CE, Kingstle, JF, (Eds.), Radiation Curing of Polymeric Materials. Advances Chemistry Series, American Chemical Society, No. 417, 1990.

  7. Decker, C, “The Use of UV Irradiation in Polymerization.” Polym. Int., 45 133 (1998)

    CAS  Google Scholar 

  8. Decker, C, Moussa, K, “Recent Advances in UV-Curing Chemistry.” J. Coat. Technol, 65 (819) 49 (1993)

    CAS  Google Scholar 

  9. Wang, XF, Zhan, J, Xing, W, Wang, X, Song, L, Qian, X, Yu, B, Hu, Y, “Flame Retardancy and Thermal Properties of Novel UV-Curable Epoxy Acrylate Coatings Modified by a Silicon-Bearing Hyperbranched Polyphosphonate Acrylate.” Ind. Eng. Chem., 52 (16) 5548–5555 (2013)

    CAS  Google Scholar 

  10. Kulkarni, RD, Chaudhari, ME, Mishra, S, “UV Cure Acrylate Monomers: Synthesis, Analysis and Storage.” Pigm. Resin. Technol., 42 53–67 (2013)

    CAS  Google Scholar 

  11. Wang, X, Wang, B, Xing, W, Tang, G, Zhan, J, Yang, W, Song, L, Hu, Y, “Flame Retardancy and Thermal Property of Novel UV-Curable Epoxy Acrylate Coatings Modified by Melamine-Based Hyperbranched Polyphosphonate Acrylate.” Prog. Org. Coat., 77 (1) 94–100 (2014)

    CAS  Google Scholar 

  12. Mohtadizadeh, F, Zohutiaan-Mehr, MJ, “Highly Accelerated Synthesis of Epoxy-Acrylate Resin.” J. Polym Mater., 30 (4) 461–469 (2013)

    CAS  Google Scholar 

  13. Dzunuzovic, E, Tasic, S, Bozic, B, Babic, D, Dunjic, B, “UV-Curable Hyperbranched Urethane Acrylate Oligomers Containing Soybean Fatty Acids.” Prog. Org. Coat., 52 (2) 136–143 (2005)

    CAS  Google Scholar 

  14. Schwalm, R, Haubling, L, Reich, W, Beck, E, Enenkel, P, Menzel, K, “Tuning the Mechanical Properties of UV Coatings Towards Hard and Flexible Systems.” Prog. Org. Coat., 32 (1–4) 191–196 (1997)

    CAS  Google Scholar 

  15. Dai, J, Ma, S, Wu, Y, Zhu, J, Liu, X, “High Bio-Based Content Waterborne UV-Curable Coatings with Excellent Adhesion and Flexibility.” Prog. Org. Coat., 87 197–203 (2015)

    CAS  Google Scholar 

  16. Chittavanich, P, Miller, K, Soucek, MD, “A Photo Curing Study of a Pigmented UV Curable Alkyd.” Prog. Org. Coat., 73 392–400 (2012)

    CAS  Google Scholar 

  17. Ping, BTY, Yusof, M, “Characteristics and Properties of Fatty Acid Distillates from Palm Oil.” Oil Palm Bull., 59 5–11 (2009)

    CAS  Google Scholar 

  18. Nang, HLL, Wafti, NSA, May, CY, MPOB TT No. 430 (2009)

  19. Teo, KT, Gan, SN, “Effects of Composition Variations and Curing Conditions on the Gloss of Water Reducible Clear Coatings Prepared from Palm Stearin Alkyds.” Jocca-Surf. Coat. Int., 82 (1) 31–36 (1999)

    Google Scholar 

  20. Teo, KT, Gan, SN, “Curing and Film Properties of Palm Stearin Alkyds.” Pigment Resin Technol., 28 283–292 (1999)

    Google Scholar 

  21. Patton, TC, Alkyd Resin Technology. Interscience, New York and London (1962)

    Google Scholar 

  22. Teo, KT, Hassan, A, Gan, SN, “UV-Curable Urethane Acrylate Resin from Palm Fatty Acid Distillate.” Polymers, 10 1374 (2018)

    Google Scholar 

  23. Kunwong, D, Summanochitraporn, N, Kaewpirom, S, “Curing Behaviour of a UV-Curable Coating Based on Urethane Acrylate Oligomer: The Influence of Reactive Monomers.” Songklanakarin J. Sci. Technol., 33 (2) 201–207 (2011)

    CAS  Google Scholar 

  24. Ke, X, Liang, H, Xiong, L, Huang, S, Zhu, M, “Synthesis, Curing Process and Thermal Reversible Mechanism of UV Curable Polyurethane Based on Diels-Alder Structure.” Prog. Org. Coat., 100 63–69 (2016)

    CAS  Google Scholar 

  25. Hua, FJ, Hu, CP, “Interpenetrating Polymer Networks of Epoxy Resin and Urethane Acrylate Resin: 1: Kinetics of Network Formation.” Eur. Polym. J., 35 103–112 (1999)

    CAS  Google Scholar 

  26. Kozyro, AA, Maksimuk, YV, Kabo, GY, “Thermodynamics of Vaporization of Phthalic Acids and Additivity of Enthalpies and Entropies of Sublimation of Benzenecarboxylic Acids.” Russ. J. Appl. Chem., 73 (2) 208–212 (2000)

    Google Scholar 

  27. Kimyonok, ABE, Ulutürk, M, “Determination of the Thermal Decomposition Products of Terephthalic Acid by Using Curie-Point Pyrolyzer.” J. Energ. Mater., 34 (2) 113–122 (2016)

    Google Scholar 

  28. Umare, SS, Chandure, AS, Pandey, RA, “Synthesis, Characterization and Biodegradable Studies of 1,3-Propanediol Based Polyesters.” Polym. Degrad. Stabil., 92 464–479 (2007)

    CAS  Google Scholar 

  29. Pavia, DL, Lampan, GM, Kriz, GS, Introduction to Spectroscopy: A Guide for Students of Organic Chemistry, 2nd ed. Saunders College, Washington (1996), (Appendix 1)

    Google Scholar 

  30. Zhang, J, Hu, CP, “Synthesis, Characterization and Mechanical Properties of Polyester-Based Aliphatic Polyurethane Elastomers Containing Hyperbranched Polyester Segments.” Eur. Polym. J., 44 3708–3714 (2008)

    CAS  Google Scholar 

  31. Stoye, D, Freitag, W, Beuschel, D (eds.), Resins for Coatings: Chemistry, Properties and Applications, Vol. 47. Hanser Gardner Publications, Cincinnati, Ohio, USA (1996)

    Google Scholar 

  32. Deligny, P, “Polyester Resins.” In: Oldring, PKT (ed.) Alkyds & Polyesters 2nd, Vol. 141. John Wiley and Sons Ltd. in Association with SITA Technology Ltd., Exeter (2000)

  33. Johansson, K, Johansson, M, “Tile Effect of Fatty Acid Methyl Esters on the Curing Performance and Final Properties of Thermally Cured Solvent-Borne Coil Coatings.” Prog. Org. Coat., 59 146–151 (2007)

    CAS  Google Scholar 

  34. McKee, MG, Unal, S, Wilkes, GL, Long, TE, “Branched Polyesters: Recent Advances in Synthesis and Performance.” Prog. Polym. Sci., 30 507–539 (2005)

    CAS  Google Scholar 

  35. Hwanga, H-D, Parka, C-H, Moona, J-I, Kima, H-J, Masubuchi, T, “UV-Curing Behavior and Physical Properties of Waterborne UV-Curable Polycarbonate-Based Polyurethane Dispersion.” Prog. Org. Coat., 72 (4) 663–675 (2011)

    Google Scholar 

  36. Massingill, JL, Sheih, PS, Whiteside, RC, Benton, DE, Morisse Arnold, DK, “Fundamental Studies of Epoxy Resins for Can and Coil Coatings: II: Flexibility and Adhesion of Epoxy Resins.” JCT J. Coat. Technol., 61 (781) 31–39 (1990)

    Google Scholar 

  37. Kojima, S, Watanabe, Y, “Flexibility of Epoxy Coatings. Part 2: The Relationship with the Degree of Cure.” Polym. Eng. Sci., 36 (2) 224–228 (1996)

    CAS  Google Scholar 

  38. Danick, C, “Improving Flexibility and Impact Resistance.” International Waterborne, High-Solids, and Powder Coatings Symposium, February 2–4, 2005. New Orleans, LA, USA

  39. Perou, AL, Vergnaud, JM, “Correlation Between the State of Cure of a Coil Coating and Its Resistance to Liquids.” Polym. Test., 16 19–31 (1997)

    CAS  Google Scholar 

  40. Marsh, SJ, Honeycutt, AH, “Coating Compositions Containing Acrylic and Aliphatic Polyester Blends.” Eastman Chemical (2010)

  41. Kadkin, O, Osajda, K, Kaszynski, P, Barber, TA, “Polyester Polyols: Synthesis and Characterization of Diethylene Glycol Terephthalate Oligomers.” J. Polym. Sci., 41 (8) 1114–1123 (2003)

    CAS  Google Scholar 

  42. Pospisil, J, Nespurek, S, “Photo-Stabilization of Coatings: Mechanisms and Performance.” Prog. Polym. Sci., 25 1261–1335 (2000)

    CAS  Google Scholar 

  43. Singh, B, Sharma, N, “Mechanistic Implications of Plastic Degradation.” Polym. Degrad. Stabil., 93 561–584 (2008)

    CAS  Google Scholar 

  44. Malanowski, P, “Weathering of Aromatic Polyester Coatings.” PhD thesis, Technical University Eindhoven (2009)

  45. Shanti, K, “Degradation of Polymers.” Int. J. Math. Sci. Technol. Hum., 82 937–940 (2003)

    Google Scholar 

  46. Maetens, D, “Weathering Degradation Mechanism in Polyester Powder Coatings.” Prog. Org. Coat., 58 (2–3) 172–179 (2007)

    CAS  Google Scholar 

  47. Turpin, ET, “Hydrolysis of Water Dispersible Resins.” J. Paint Technol., 47 (602) 40–46 (1975)

    CAS  Google Scholar 

  48. Aklonis, JJ, MacKnight, WJ, Shen, M, Introduction to Polymer Viscoelasticity, pp. 60–87. Wiley-Interscience, New York (1972)

    Google Scholar 

Download references

Acknowledgments

The authors would like to acknowledge the financial support from the University Malaya, under Grant PG013-2014A.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Seng Neon Gan.

Ethics declarations

Conflict of interest

The authors declare no conflicts of interest.

Additional information

Publisher's Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Teo, K.T., Hassan, A. & Gan, S.N. Effects of different dicarboxylic acid on the UV-curable urethane resins made from palm fatty acid distillate. J Coat Technol Res 17, 1571–1585 (2020). https://doi.org/10.1007/s11998-020-00379-4

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-020-00379-4

Keywords

Navigation