Skip to main content
SpringerLink
Log in

Tentative identification of BADGE derivatives in epoxy type coatings in a model sample: a beverage can

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

Abstract

Organic coatings have been applied to the inside surfaces of cans intended to come into contact with food and beverages. In general, polymeric coatings are complex formulations that may contain different components such as resins, crosslinking agents, catalysts, wetting agents, etc. The most widely used type of polymeric coating is epoxy, which is obtained by the condensation of epichlorohydrin and bisphenol A, which yields bisphenol A diglycidyl ether (BADGE). The resulting finished material may have starting substances such as monomers and additives, and also non-intentionally added substances that can potentially migrate from the food contact material into the food. In the present study, a beverage can, as a model sample, was evaluated. First, the internal surface was identified as epoxy-based coating using an infrared spectrometer with attenuated total reflectance. In the second part of the work, an acetonitrile extract of the can sample was obtained in order to tentatively identify potential BADGE derivatives using a non-targeted screening by liquid chromatography coupled to tandem mass spectrometry in positive and negative atmospheric pressure chemical ionization mode. Several BADGE derivatives could be tentatively identified comparing their characteristic m/z with a homemade database developed taking into account possible starting substances used in epoxy 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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

References

  1. European Commission. “Commission Regulation (EC) No. 1895/2005 of 18 November 2005 on the Restriction of Use of Certain Epoxy Derivatives in Materials and Articles Intended to Come into Contact with Food.” J. Eur. Union, L302, 28–32 (2005)

    Google Scholar 

  2. European Commission. “Commission Regulation (EU) No. 2018/213, on 12 February 2018 on the Use of Bisphenol A in Varnishes and Coatings Intended to Come into Contact with Food.” Off. J. Eur. Union, L41, 6–12 (2018)

    Google Scholar 

  3. Paseiro-Cerrato, R, DeVries, J, Begley, TH, “Evaluation of Short-term and Long-term Migration Testing from Can Coatings into Food Simulants: Epoxy and Acrylic–Phenolic Coatings.” J. Agric. Food Chem., 65(12), 2594–2602 (2017)

    Article  CAS  Google Scholar 

  4. Paseiro-Cerrato, R, Noonan, GO, Begley, TH, “Evaluation of Long-term Migration Testing from Can Coatings into Food Simulants: Polyester Coatings.” J. Agric. Food Chem., 64(11), 2377–2385 (2016)

    Article  CAS  Google Scholar 

  5. Berger, U, Oehme, M, “Identification of Derivatives of Bisphenol A Diglycidyl Ether and Novolac Glycidyl Ether in Can Coatings by Liquid Chromatography/ion Trap Mass Spectrometry.” J. AOAC Int., 83(6), 1367–1376 (2000)

    Article  CAS  Google Scholar 

  6. EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF), “Recent Developments in the Risk Assessment of Chemicals in Food and Their Potential Impact on the Safety Assessment of Substances Used in Food Contact Materials.” EFSA J., 14(1), 4357 (2016)

    Article  Google Scholar 

  7. Toxtree v3.1.0. Available online: http://toxtree.sourceforge.net/cramer.html

  8. Lestido-Cardama, A, Sendón, R, Bustos, J, Santillana, MI, Paseiro Losada, P, Bernaldo, R, de Quirós, A, “Multi-analyte Method for the Quantification of Bisphenol Related Compounds in Canned Food Samples and Exposure Assessment of the Spanish Adult Population.” Food Packag. Shelf Life, 28, 100671 (2021)

    Article  CAS  Google Scholar 

  9. Poovarodom, N, Jinkarn, T, Tangmongkollert, P, Chaloeijitkul, W, Charubhum, S, “Survey of Food Can Coatings in Thailand-Their Use, Extractable Residues and Migrations.” Packag. Technol. Sci., 30(7), 317–329 (2017)

    Article  CAS  Google Scholar 

  10. Munguia-Lopez, EM, Soto-Valdez, H, “Effect of Heat Processing and Storage Time on Migration of Bisphenol A (BPA) and Bisphenol A−Diglycidyl Ether (BADGE) to Aqueous Food Simulant from Mexican Can Coatings.” J. Agric. Food Chem., 49(8), 3666–3671 (2001)

    Article  CAS  Google Scholar 

  11. Summerfield, W, Goodson, A, Cooper, I, “Survey of Bisphenol A Diglycidyl Ether (BADGE) in Canned Foods.” Food Addit. Contam., 15(7), 818–830 (1998)

    Article  CAS  Google Scholar 

  12. Lestido-Cardama, A, Vázquez Loureiro, P, Sendón, R, Paseiro Losada, P, Bernaldo, R, de Quirós, A, “Application of Chromatographic Analysis for Detecting Components from Polymeric Can Coatings and Further Determination in Beverage Samples.” J. Chromatogr. A, 1638, 461886 (2021)

    Article  CAS  Google Scholar 

  13. Driffield, M., Bradley, E. L., Castle, L., Zweigenbaum, J. “Identification of Unknown Reaction By-Products and Contaminants in Epoxyphenolic-Based Food Can Coatings by LC-TOF-MS.” Application Note. Available online: https://www.gimitec.com/file/5989-5898EN.pdf

  14. Theobald, A, Simoneau, C, Roncari, A, Anklam, E, “Identification of Epoxy Containing Migrants from Can Coatings in Edible Oil: A Model Study on Reaction Products of Bisphenol-A-diglycidyl-ether (BADGE) with Solvents for Coating Production.” Dtsch. Lebensm.-Rundsch., 98(7), 249–256 (2002)

    CAS  Google Scholar 

  15. Schaefer, A, Simat, TJ, “Migration from Can Coatings: Part 3. Synthesis, Identification and Quantification of Migrating Epoxy-based Substances Below 1000 Da.” Food Addit. Contam., 21(4), 390–405 (2004)

    Article  CAS  Google Scholar 

  16. Bradley, EL, Driffield, M, Harmer, N, Oldring, PKT, Castle, L, “Identification of Potential Migrants in Epoxy Phenolic Can Coatings.” Int. J. Polym. Anal. Charact., 13(3), 200–223 (2008)

    Article  CAS  Google Scholar 

  17. Vázquez-Loureiro, P, Lestido-Cardama, A, Sendón, R, López-Hernández, J, Paseiro-Losada, P, Rodríguez-Bernaldo de Quirós, A, “Identification of Volatile and Semi-Volatile Compounds in Polymeric Coatings Used in Metal Cans by GC-MS and SPME.” Materials, 14(13), 3704 (2021)

    Article  Google Scholar 

  18. Beszterda, M, Kasperkowiak, M, Frańska, M, Jęziołowska, S, Frański, R, “Ethoxylated Butoxyethanol-BADGE Adducts—New Potential Migrants from Epoxy Resin Can Coating Material.” Materials, 14 (13) 3682 (2021)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Antía Lestido is grateful for her grant “Programa de axudas á etapa predoutoral” da Xunta de Galicia (Consellería de Cultura, Educación e Ordenación Universitaria).

Funding

The study was financially supported by the Ministerio de Ciencia, Innovación y Universidades, by Fondo Europeo de Desarrollo Regional (FEDER), and by Agencia Estatal de Investigación Ref. No. PGC2018-094518-B-I00 “MIGRACOATING” (MICIU/FEDER, UE).

Author information

Authors and Affiliations

  1. Department of Analytical Chemistry, Nutrition and Food Science, Faculty of Pharmacy, University of Santiago de Compostela, Campus Vida, 15782, Santiago de Compostela, Spain

    Antía Lestido-Cardama, Raquel Sendón & Ana Rodríguez Bernaldo de Quirós

Authors
  1. Antía Lestido-Cardama
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Raquel Sendón
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ana Rodríguez Bernaldo de Quirós
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Conceptualization: RS and ARBdQ; methodology: RS and ARBdQ; investigation: ALC; writing—original draft preparation: ALC; writing—review and editing: RS and ARBdQ; supervision: RS and ARBdQ; project administration: RS and ARBdQ; funding acquisition: ARBdQ.

Corresponding author

Correspondence to Antía Lestido-Cardama.

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

Lestido-Cardama, A., Sendón, R. & Rodríguez Bernaldo de Quirós, A. Tentative identification of BADGE derivatives in epoxy type coatings in a model sample: a beverage can. J Coat Technol Res 19, 1893–1900 (2022). https://doi.org/10.1007/s11998-022-00662-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-022-00662-6

Keywords

Search

Navigation