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Thermal yellowing and photobleaching of automotive topcoats

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Abstract

Thermal yellowing and photobleaching are common problems that are seen to some extent in all automotive topcoat systems today. These effects can cause difficulties in the matching of light colors in the assembly plant and then later upon delivery to the customer. Current literature offers no clear mechanism for the thermal yellowing and photobleaching. Based on observed formulation dependencies, a mechanism is proposed based on oxidation of amine compounds. We constructed a model in vitro system using a hydroperoxide to thermally oxidize amines in solution. In this system, a series of amines were tested and both yellowing and photobleaching were reproduced. Loss of basicity confirmed that amine oxidation occurred under these conditions. Both the location of the UV absorption peak and strong amine structure dependence indicate nitrone formation as the yellow chromophore.

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References

  1. Garland, RM, Elrod, MJ, Jimenez, JL, Tolbert, MA, “Acid-Catalyzed Reactions of Hexanal on Sulfuric Acid Particles: Identification of Reaction Products.” Atmos. Environ., 40 6863–6878 (2006)

    Article  Google Scholar 

  2. Scheirs, J, Long, TE, Modern Polyesters: Chemistry and Technology of Polyesters and Copolyesters, p. 62. John Wiley and Sons, West Sussex, UK

  3. Templeman, C, “Yellowing in Automotive Clearcoats.” SAE World Congress 2016

  4. Florio, M, Handbook of Coatings Additives, pp. 25–26. CRC Press, Boca Raton (2004)

    Google Scholar 

  5. Borland, JE, Chen, YDM, Sauer, JD, Smith, KR, Smith, RF, “Bleaching of Colored Amine Oxides.” US Patent 5,068,430

  6. Sun, M, Hong, C, Pan, C, “A Unique Aliphatic Tertiary Amine Chromophore: Fluorescence, Polymer Structure, and Application in Cell Imaging.” J. Am. Chem. Soc. Commun., 134 20581–20584 (2012)

    Article  Google Scholar 

  7. Jai, D, Cao, L, Wang, D, Guo, X, Liang, H, Zao, F, Gu, Y, Wang, D, “Uncovering a Broad Class of Fluorescent amine-containing Compounds by Heat Treatment.” Chem. Commun., 50 11488 (2014)

    Article  Google Scholar 

  8. Chu, C, Imae, T, “Fluorescence Investigations of Oxygen-Doped Simple Amine Compared with Fluorescent PAMAM Dendrimer.” Macromol. Rapid Commun., 30 89–93 (2009)

    Article  Google Scholar 

  9. Riazy, M, Lougheed, M, Adomat, H, Tomlinson Guns, E, Eigendorf, G, Duronio, V, Steinbrecher, U, “Fluorescent Adducts Formed by Reaction of Oxidized Unsaturated Fatty Acids with Amines Increase Macrophage Viability.” Free Radic. Biol. Med., 51 1926–1936 (2011)

    Article  Google Scholar 

  10. Kochany, J, Lipczynska-Kochany, E, “Photochemistry of Some Alpha-(2-naphthyl) Nitrones.” J. Photochem. Photobiol. A Chem., 45 65–79 (1988)

    Article  Google Scholar 

  11. Kada, T, Obara, A, Wantanbe, T, Miyata, S, “Fabrication of Refractive Index Distributions in Polymer Using a Photochemical Reaction.” J. Appl. Phys., 87 (2) 638–642 (2000)

    Article  Google Scholar 

  12. Mielewski, DF, Bauer, DR, Gerlock, JL, “Determination of Hydroperoxide Concentrations in Crosslinked Polymer Coatings Containing Hindered Amine Light Stabilizers.” Polym. Degrad. Stab., 41 323–331 (1993)

    Article  Google Scholar 

  13. Gerlock, JL, Smith, CA, Cooper, VA, Dusbiber, TG, Weber, WH, “On the Use of Fourier Transform Infrared Spectroscopy to Assess the Weathering Performance of Isolated Clearcoats from Different Chemical Families.” Polym. Degrad. Stab., 62 225–234 (1998)

    Article  Google Scholar 

  14. Reproduced from J. Appl. Phys., 87(2) 638–642 (2000), with the permission of AIP Publishing

  15. Cope, AC, Ciganek, E, “Methylenecyclohexane and N, N-Dimethylhydroxylamine Hydrochloride.” Org. Synth., 4 612 (1963)

    Google Scholar 

  16. Laughlin, RG, “Reversible Cycloelimination and Disproportionation Reactions in Aliphatic Amine Oxide-N, N,-Dimethylhydroxylamine-Olefin Systems.” J. Am. Chem. Soc., 95 (10) 3295–3299 (1973)

    Article  Google Scholar 

  17. Schnabel, W, “Thermolysis of Poly(Chloroethyl Methacrylates) and Poly(Chloroethyl Acrylates).” In: Clough, JR, et al. (eds.) Advances in Chemistry, Polymer Durability, pp. 33–45. American Chemical Society, Washington DC (1996)

    Chapter  Google Scholar 

  18. Bogner, G, Brunner, H, Hoehn, K, “Epoxy Resin Systems, which are Resistant to Aging, Moulding Materials, Components Produced Therefrom and the Use Thereof.” US Patent 7,183, 661, 2007

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Authors and Affiliations

  1. BASF Corporation, Automotive Coatings, 26701 Telegraph Rd., Southfield, MI, 48033, USA

    Donald H. Campbell, Colin Wade, Kevin M. Turley & Paragkumar Thanki

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  1. Donald H. Campbell
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  2. Colin Wade
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  3. Kevin M. Turley
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  4. Paragkumar Thanki
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Correspondence to Donald H. Campbell.

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Campbell, D.H., Wade, C., Turley, K.M. et al. Thermal yellowing and photobleaching of automotive topcoats. J Coat Technol Res 15, 131–139 (2018). https://doi.org/10.1007/s11998-017-9957-y

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  • DOI: https://doi.org/10.1007/s11998-017-9957-y

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