Skip to main content

Advertisement

SpringerLink
Log in

Bio-based polyester itaconates as binder resins for UV-curing offset printing inks

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

Abstract

UV-curing inks have several economic and environmental advantages compared with standard printing inks, such as high printing velocities, low VOC emissions and good adhesion to nonabsorbing substrates. However, there are also some drawbacks, such as residual monomers, pungent odor and allergic potential of monomers and prepolymers derived from acrylic acid. In addition, only few examples of UV-curing inks derived from renewable resources are known. Herein, acrylate-free UV-curing polyester itaconates with a renewable content up to 100% and their application as binder resins in UV-curing offset ink formulations are presented. In order to obtain a high renewable content in the polyester resins, Zn(OAc)2 had to be used as polycondensation catalyst, as standard Brønsted acid catalyst led to undesired side reactions. The resins obtained with this synthetic protocol were tested on their reactivity, which was slightly lower than a commercial polyester acrylate. Printing inks formulated from these polyester itaconates showed interesting properties despite the fact that no acrylic acid was incorporated in the resins.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Ulber, R, Muffler, K, Tippkötter, N, Hirth, T, Sell, D, “Introduction to Renewable Resources in the Chemical Industry.” In: Ulber, R, Sell, D, Hirth, T (eds.) Renewable Raw Materials, pp. 1–5. Wiley-VCH (2011)

  2. Corma, A, Iborra, S, Velty, A, “Chemical Routes for the Transformation of Biomass into Chemicals.” Chem. Rev., 107 2411–2502 (2007)

    Article  Google Scholar 

  3. Schneiderman, DK, Hillmyer, MA, “50th Anniversary Perspective: There Is a Great Future in Sustainable Polymers.” Macromolecules, 50 3733–3749 (2017)

    Article  Google Scholar 

  4. Belgacem, MN, Gandini, A, Monomer, Polymers and Composites from Renewable Resources. Elsevier, Amsterdam (2008)

    Google Scholar 

  5. Gandini, A, Lacerda, TM, “From Monomers to Polymers from Renewable Resources: Recent Advances.” Prog. Polym. Sci., 48 1–39 (2015)

    Article  Google Scholar 

  6. Zhu, Y, Romain, C, Williams, CK, “Sustainable Polymers from Renewable Resources.” Nature, 540 354 (2016)

    Article  Google Scholar 

  7. Hillmyer, MA, “The Promise of Plastics from Plants.” Science, 358 868–870 (2017)

    Article  Google Scholar 

  8. Werpy, T, Petersen, G, Aden, A, Bozell, J, Holladay, J, White, J, Manheim, A, Eliot, D, Lasure, L, Jones, S, Top Value Added Chemicals From Biomass, Volume 1—Results of Screening for Potential Candidates from Sugars and Synthesis Gas. U.S. Department of Energy, Oak Ridge, TN (2004). http://www.dtic.mil/dtic/tr/fulltext/u2/a436528.pdf

  9. Bozell, JJ, Petersen, GR, “Technology Development for the Production of Biobased Products from Biorefinery Carbohydrates—The US Department of Energy’s “Top 10” Revisited.” Green Chem., 12 539 (2010)

    Article  Google Scholar 

  10. Delidovich, I, Hausoul, PJC, Deng, L, Pfützenreuter, R, Rose, M, Palkovits, R, “Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production.” Chem. Rev., 116 1540–1599 (2016)

    Article  Google Scholar 

  11. Leach, R, The Printing Ink Manual, 5th ed. Springer, Heidelberg (1993)

    Book  Google Scholar 

  12. Board, N, The Complete Technology Book on Printing Inks. Asia Pacific Business Press, Dehli (2007)

    Google Scholar 

  13. Robert, T, “‘Green Ink in All Colors’—Printing Ink from Renewable Resources.” Prog. Org. Coat., 78 287–292 (2015)

    Article  Google Scholar 

  14. Balmer, RP, Hazell, MP, Mawby, TR, “Energy-Curable Ink Composition Useful for Printing on Cold-Set Lithographic Press.” In: Balmer, RP, Hazell, MP, Mawby, TR (eds.) Comprises Acrylate-Functional Derivative of Soybean Oil and At Least One Further Acrylate-Functional Material. Flint Ink Corp, Flint Group Inc, Luxembourg (2006)

    Google Scholar 

  15. Rengasamy, S, Mannari, V, “Development of Soy-Based UV-Curable Acrylate Oligomers and Study of Their Film Properties.” Prog. Org. Coat., 76 78–85 (2013)

    Article  Google Scholar 

  16. Kela, L, Jokiaho, K, Ilmonen, A, Harlin, A, “Growing Inks from Trees.” Eur. Coat. J., leaflet 5–8 (2012)

  17. Ilmonen, A, Kela, L, Jokiaho, K, Method of Printing. Teknologian Tutkimuskeskus VTT, Espoo (2013)

    Google Scholar 

  18. Fertier, L, Koleilat, H, Stemmelen, M, Giani, O, Joly-Duhamel, C, Lapinte, V, Robin, J-J, “The Use of Renewable Feedstock in UV-Curable Materials—A New Age for Polymers and Green Chemistry.” Prog. Polym. Sci., 38 932–962 (2013)

    Article  Google Scholar 

  19. Fertier, L, Ibert, M, Buffe, C, Saint-Loup, R, Joly-Duhamel, C, Robin, JJ, Giani, O, “New Biosourced UV Curable Coatings Based on Isosorbide.” Prog. Org. Coat., 99 393–399 (2016)

    Article  Google Scholar 

  20. Chakraborty, S, Ju, L, Galuska, AA, Moore, RB, Turner, SR, “Suspension Polymerization of Itaconic Acid Diesters.” J. Appl. Polym. Sci., 135 46417 (2018)

    Article  Google Scholar 

  21. Satoh, K, “Controlled/Living Polymerization of Renewable Vinyl Monomers Into Bio-Based Polymers.” Polym. J., 47 527–536 (2015)

    Article  Google Scholar 

  22. Farmer, T, Castle, R, Clark, J, Macquarrie, D, “Synthesis of Unsaturated Polyester Resins from Various Bio-Derived Platform Molecules.” Int. J. Mol. Sci., 16 14912 (2015)

    Article  Google Scholar 

  23. Tang, T, Takasu, A, “Facile Synthesis of Unsaturated Polyester-Based Double-Network Gels Via Chemoselective Cross-Linking Using Michael Addition and Subsequent UV-Initiated Radical Polymerization.” RSC Adv., 5 819–829 (2015)

    Article  Google Scholar 

  24. Robert, T, Friebel, S, “Itaconic Acid—A Versatile Building Block for Renewable Polyesters with Enhanced Functionality.” Green Chem., 18 2922–2934 (2016)

    Article  Google Scholar 

  25. Panic, VV, Seslija, SI, Popovic, IG, Spasojevic, VD, Popovic, AR, Nikolic, VB, Spasojevic, PM, “Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid.” Biomacromolecules, 18 3881–3891 (2017)

    Article  Google Scholar 

  26. Hu, X, Kang, H, Li, Y, Geng, Y, Wang, R, Zhang, L, “Preparation, Morphology and Superior Performances of Biobased Thermoplastic Elastomer by In Situ Dynamical Vulcanization for 3D-Printed Materials.” Polymer, 108 11–20 (2017)

    Article  Google Scholar 

  27. Patil, DM, Phalak, GA, Mhaske, ST, “Design and Synthesis of Bio-Based UV Curable PU Acrylate Resin from Itaconic Acid for Coating Applications.” Des. Monomers Polym., 20 269–282 (2017)

    Article  Google Scholar 

  28. Mehtiö, T, Anghelescu-Hakala, A, Hartman, J, Kunnari, V, Harlin, A, “Crosslinkable Poly(Lactic Acid)-Based Materials: Biomass-Derived Solution for Barrier Coatings.” J. Appl. Polym. Sci., 134 1–8 (2017)

    Article  Google Scholar 

  29. Brännström, S, Malmström, E, Johansson, M, “Biobased UV-Curable Coatings Based on Itaconic Acid.” J. Coat. Technol. Res., 14 851–861 (2017)

    Article  Google Scholar 

  30. Dai, J, Liu, X, Ma, S, Wang, J, Shen, X, You, S, Zhu, J, “Soybean Oil-Based UV-Curable Coatings Strengthened by Crosslink Agent Derived from Itaconic Acid Together with 2-Hydroxyethyl Methacrylate Phosphate.” Prog. Org. Coat., 97 210–215 (2016)

    Article  Google Scholar 

  31. Dai, J, Ma, S, Liu, X, Han, L, Wu, Y, Dai, X, Zhu, J, “Synthesis of Bio-Based Unsaturated Polyester Resins and Their Application in Waterborne UV-Curable Coatings.” Prog. Org. Coat., 78 49–54 (2015)

    Article  Google Scholar 

  32. Han, L, Dai, J, Zhang, L, Ma, S, Deng, J, Zhang, R, 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 49471–49477 (2014)

    Article  Google Scholar 

  33. Friebel, S, Biemans, T, “Synthesis of Wood Coatings with Binder Resins Derived from Itaconic Acid.” In: Funded by the German Federal Ministry of Food and Agriculture Through the Fachagentur für nachwachsende Rohstoffe e.V., FKZ: 22020408, 2013

  34. Kilambi, H, Stansbury, JW, Bowman, CN, “Deconvoluting the Impact of Intermolecular and Intramolecular Interactions on the Polymerization Kinetics of Ultrarapid Mono(meth)acrylates.” Macromolecules, 40 47–54 (2007)

    Article  Google Scholar 

  35. Schoon, I, Kluge, M, Eschig, S, Robert, T, “Catalyst Influence on Undesired Side Reactions in the Polycondensation of Fully Bio-Based Polyester Itaconates.” Polymers, 9 693 (2017)

    Article  Google Scholar 

Download references

Acknowledgments

This project was funded by the Fachagentur Nachwachsende Rohstoffe e.V. (FKZ: 22015614) and the Federal Ministry of Food and Agriculture of Germany. The financial support is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Fraunhofer Institute for Wood Research – Wilhelm-Klauditz-Institut WKI, Bienroder Weg 54E, 38108, Braunschweig, Germany

    Tobias Robert & Steven Eschig

  2. Worlée Chemie GmbH, Worléestraße 16, 21481, Lauenburg, Germany

    Toine Biemans

  3. Jänecke+Schneemann Druckfarben GmbH, Hannoversche Straße 33, 31319, Sehnde, Germany

    Frank Scheifler

Authors
  1. Tobias Robert
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Steven Eschig
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Toine Biemans
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Frank Scheifler
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tobias Robert.

Ethics declarations

Conflict of interest

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Robert, T., Eschig, S., Biemans, T. et al. Bio-based polyester itaconates as binder resins for UV-curing offset printing inks. J Coat Technol Res 16, 689–697 (2019). https://doi.org/10.1007/s11998-018-0146-4

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-018-0146-4

Keywords

Search

Navigation