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Synthesis and evaluation of tetra(2,7-octadienyl) titanate as a reactive diluent for air-drying alkyd paints

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Abstract

Environmental regulations are forcing the reformulation of many decorative and protective coatings systems. In particular, air-drying solventborne alkyd paints need to meet increasingly stringent emission limits and often must be reformulated with suitable exempt solvents or reactive diluents to achieve volatile organic compound (VOC) reduction. In the research summarized in this article, a new reactive diluent, tetra(2,7-octadienyl) titanate, was synthesized and evaluated in alkyd formulations for VOC reduction and property enhancement. A soy-based long-oil alkyd resin; a soy-based high-solids, long-oil alkyd resin; and a linseed-based, high-solids long-oil alkyd resin were evaluated in combination with the new reactive diluent at weight percentages ranging from 10% to 50%. Characterization included measuring viscosity, film dry times, and film performance of the reactive diluent formulations in comparison to neat alkyd resins used as control. The tetra(2,7-octadienyl) titanate formulations consistently exhibited reduced viscosities and dry times as a function of concentration. The resulting films were harder and more thoroughly cured than the control systems.

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References

  1. Zabel, KH, “Characteristics of Air-Drying High-Solid Alkyd Paints.” Polym. Paint Colour J., 178 526–529 (1988)

    CAS  Google Scholar 

  2. Proposal for a Council Directive on Limiting the Content of Volatile Organic Compounds in Decorative and Architectural Pints and in Cleaning Agents, Fillers, Primers, and Paints, Used in the Vehicle Refinishing Industry, CEPE, May 1996

  3. Proposal for a Council Directive on Limiting the Content of Volatile Organic Compounds Owing to the Use of Organic Solvents in Certain Industrial Activities, EC OJ, C99 26.3.1997, p. 32

  4. Lindeboom, J, “Air-Drying High Solids Alkyd Pants [Paints] for Decorative Coatings.” Prog. Org. Coat., 34 147–151 (1998)

    Article  CAS  Google Scholar 

  5. Holmberg, K, High Solid Alkyd Resins, p. 25. Marcel Dekker, New York (1987)

    Google Scholar 

  6. Zabel, KH, Klaasen, RP, Muizebelt, WJ, Gracey, BP, Hallett, C, Brooks, CD, “Design and Incorporation of Reactive Diluents for Air-Drying High Solids Alkyd Paints.” Prog. Org. Coat., 35 255–264 (1999)

    Article  CAS  Google Scholar 

  7. Muizebelt, WJ, Hubert, JC, Nielen, MWF, Klaasen, RP, Zabel, KH, “Crosslink Mechanisms of High-Solids Alkyd Resins in the Presence of Reactive Diluents.” Prog. Org. Coat., 40 121–130 (2000)

    Article  CAS  Google Scholar 

  8. Muturi, P, Wang, D, Dirlikov, S, “Epoxidized Vegetable Oils as Reactive Diluents, II, Comparison of Vernonia, Epoxidized Soybean, and Linseed Oils.” Prog. Org. Coat., 25 85–94 (1994)

    Article  CAS  Google Scholar 

  9. Stenberg, C, Swensson, M, Wallstrom, E, Johanssson, M, “Drying of Linseed Oil Wood Coatings Using Reactive Diluents.” Surf. Coat. Int. Part B: Coat. Trans., 88 119–126 (2005)

    Article  CAS  Google Scholar 

  10. Samuelsson, J, Sundell, PE, Johansson, M, “Synthesis and Polymerization of a Radiation Curable Hyperbranched Resin Based on Epoxy Functional Fatty Acids.” Prog. Org. Coat., 50 193–198 (2004)

    Article  CAS  Google Scholar 

  11. Dhein, R, Eimers, E, Renter, K, Ruf, G, “Forschungsbericht T85-005: Neue Oxidative Vernetzende Lacksystemen Mit Hohem Festkorpergehalt.” Bundes-ministerium fur Forschung und Technologie, January 1985.

  12. Toivonen, H, “Block Resistant Gloss Emulsion Paint Based on Air-Drying Amino Resin.” J. Oil Colour Chemists’ Assoc., 8 213–217 (1984)

    Google Scholar 

  13. Markey, KS, Fatty Acids. Part 2, p. 1399. Interscience Publishers Inc., New York (1961)

    Google Scholar 

  14. Jones, FN (ed.), “Alkyd Resins.” In: Ullman Encyclopedia of Industrial Chemistry, Vol. A1, p. 409. VCH Wiley, Verlag GmBH (1985)

  15. Frankel, EN, Lipid Oxidation. The Oily Press Ltd., Dundee, Scotland (1998)

    Google Scholar 

  16. Frankel, EN, Neff, WE, Rohwedder, WK, Khambay, BPS, Garwood, RF, Weedon, BCL, “Analysis of Autoxidized Fats by Gas Chromatography–Mass Spectrometry: III. Methyl Linolenate.” Lipids, 12 1055–1061 (1977)

    Article  CAS  Google Scholar 

  17. Muizebelt, WJ, Hubert, JC, Venderbosch, RAM, “Mechanistic Study of Drying of Alkyds Resins Using Ethyl Linoleate as a Model Substance.” Prog. Org. Coat., 24 263–279 (1994)

    Article  CAS  Google Scholar 

  18. Hartshorn, JH, “Time-Lapse Infrared Spectroscopic Investigation of Alkyd and Lindeed Oil Cure.” J. Coat. Technol., 54 53–61 (1982)

    CAS  Google Scholar 

  19. Salazar-Rojas, EM, Urban, MW, “Curing of Non-Pigmented Alkyd Coatings Detected by In Situ Photoacoustic Fourier Transform Infrared Spectroscopy (PAFT-IR).” Prog. Org. Coat., 16 371–386 (1989)

    Article  CAS  Google Scholar 

  20. Hubert, JC, Venderbosch, RAM, Muizebelt, WJ, Klassen, RP, Zabel, KH, “Mechanistic Study of Drying of Alkyd Resins using (Z,Z)- and (E,E)-3,6-Nonadiene as Mosel Substances.” Prog. Org. Coat., 31 331–340 (1997)

    Article  CAS  Google Scholar 

  21. Porter, NA, Weber, BA, Weenen, H, Khan, JA, “Autoxidation of Polyunsaturated Lipids. Factors Controlling the Stereochemistry of Product Hydroperoxides.” J. Am. Chem. Soc., 102 5597–5601 (1980)

    Article  CAS  Google Scholar 

  22. Porter, NA, Lehman, LS, Weber, BA, Smith, KJ, “Unified Mechanism for Polyunsaturated Fatty Acid Auxidation. Competition of Peroxy Radical Hydrogen Atom Abstraction, Beta-Scission, and Crystallization.” J. Am. Chem. Soc., 103 6447–6455 (1981)

    Article  CAS  Google Scholar 

  23. Porter, NA, Wujek, DG, “Autoxidation of Polyunsaturated Fatty Acids, an Expanded Mechanistic Study.” J. Am. Chem. Soc., 106 2626–2629 (1984)

    Article  CAS  Google Scholar 

  24. Muizebelt, WJ, Hubert, JC, Venderbosch, RAM, Lansbergen, AJH, Klaasen, RP, Zabel, KH, “Aluminum Compound as Additional Crosslinkers for Air-Drying High Solids Alkyd Paints.” J. Coat. Technol., 70 53–59 (1998)

    Article  CAS  Google Scholar 

  25. Enomoto, S, Nishida, HTS, Wada, H, Mukaida, Y, Yanaka, M, “Study of Reactive Diluent for Air-Drying Alkyd Paint.” J. Appl. Polym. Sci., 22 253–265 (1978)

    Article  CAS  Google Scholar 

  26. Milligan, CL, Ward, RJ, Martin, RA, “Hexadienol and Hexadienal Derivatives, Useful as Reactive Diluents in Drying Oil Coatings.” US Patent 3,529,389, 1970

  27. Johnson, NW, “Allyl Ether-Esters as Reactive Diluents for Coating Compositions.” GB Patent 2,190,672, 25, 1987

  28. Hofland, A, “Reactive Diluent for Paint Compositions.” EP Patent 0,357,128, A1, 1989

  29. Hoehlein, P, Meixner, J, Pedain, J, “Use of Octadienyl Ethers as Reactive Diluents.” EP Patent 0,546,417 A1, 1993

  30. Yamauchi, T, Sato, Y, Koizumi, K, “Alkyd Resin using Mono- and Dioctadienyl Esters of Good Hardness, Water and Alkali Resistance.” JP Patent 47045838, 1972

  31. The Powder Coating Institute, Powder Coating The Complete Finisher’s Handbook, 3rd edn., p. 425. Alexandria, VA (2004)

  32. Gracey, BP, Hatlett, C., “Reactive Diluents, Preparation and Use in Paints.” US Patent 20070004825 A1, 2007

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Acknowledgments

The authors gratefully acknowledge the support of Noetic Technologies, Inc. This study was also partially supported by the RET program of the National Science Foundation under Award Number EEC-0602032.

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Authors and Affiliations

  1. School of Polymers and High Performance Materials, The University of Southern Mississippi, 118 College Drive, Box 10076, Hattiesburg, MS, 39406-0001, USA

    Alp H. Alidedeoglu, Kevin Davis, Rhonda Robertson, Crystal Smith, James W. Rawlins & Sarah E. Morgan

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  1. Alp H. Alidedeoglu
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  2. Kevin Davis
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  3. Rhonda Robertson
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  4. Crystal Smith
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  5. James W. Rawlins
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  6. Sarah E. Morgan
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Corresponding author

Correspondence to Sarah E. Morgan.

Appendix

Appendix

See Figs. 7 and 8.

Fig. 7
figure 7

1H-NMR of tetra(2,7-octadienyl) titanate

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Fig. 8
figure 8

13C of tetra(2,7-octadienyl) titanate

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Alidedeoglu, A.H., Davis, K., Robertson, R. et al. Synthesis and evaluation of tetra(2,7-octadienyl) titanate as a reactive diluent for air-drying alkyd paints. J Coat Technol Res 8, 45–52 (2011). https://doi.org/10.1007/s11998-010-9276-z

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  • DOI: https://doi.org/10.1007/s11998-010-9276-z

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