946
Views
16
CrossRef citations to date
0
Altmetric
Articles

Linear and cyclic oligomers in PET, glycol-modified PET and Tritan™ used for food contact materials

ORCID Icon, & ORCID Icon
Pages 160-179 | Received 12 Jul 2020, Accepted 17 Sep 2020, Published online: 17 Nov 2020

References

  • Barnes KA, Damant AP, Startin JR, Castle L. 1995. Qualitative liquid chromatographic-atmospheric-pressure chemical-ionisation mass spectrometric analysis of polyethylene terephthalate oligomers. J Chromatogr A. 712:191–199. doi:10.1016/0021967395005688
  • Besnoin J-M, Choi KY. 1989. Identification and characterization of reaction byproducts in the polymerization of polyethylene terephthalate. J Macromol Sci Part C Polym Rev. 29:55–81. doi:10.1080/07366578908055164
  • Brenz F, Linke S, Simat T. 2017. Qualitative and quantitative analysis of monomers in polyesters for food contact materials. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 34:307–319. doi:10.1080/19440049.2016.1265672
  • Brenz F, Linke S, Simat T. 2018. Linear and cyclic oligomers in polybutylene terephthalate for food contact materials. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 35:583–598. doi:10.1080/19440049.2017.1414958
  • Cramer GM, Ford RA, Hall RL. 1976. Estimation of toxic hazard—A decision tree approach. Food Cosmet Toxicol. 16:255–276. doi:10.1016/S0015-626476805226
  • Dulio V, Po R, Borrelli R, Guarini A, Santini C. 1995. Characterization of low-molecular-weight oligomers in recycled poly(ethylene terephthalate). Angew Makromol Chemie. 225:109–122. doi:10.1002/apmc.1995.052250110
  • Eckardt M, Hetzel L, Brenz F, Simat TJ. 2020. Release and migration of cyclic polyester oligomers from bisphenol A non-intent polyester-phenol-coatings into food simulants and infant food - a comprehensive study. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 37:681–703. doi:10.1080/19440049.2019.1616831
  • Eckardt M, Schneider J, Simat TJ. 2019. In vitro intestinal digestibility of cyclic aromatic polyester oligomers from polyethylene terephthalate (PET) and polybutylene terephthalate (PBT). Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 36:1882–1894. doi:10.1080/19440049.2019.1658903
  • [EFSA Scientific Committee] European Food Safety Authority Scientific Committee. 2012. Scientific opinion on exploring options for providing advice about possible human health risks based on the concept of threshold of toxicological concern (TTC). Efsa J. 10:2750. doi:10.2903/j.efsa.2012.2750
  • [EFSA CEF Panel] European Food Safety Authority Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids. 2014a. Scientific Opinion on the safety assessment of the substance, 2,4,8,10-tetraoxaspiroundecane-3, 9-diethanol, β3,β3,β9,β9-tetramethyl-, CAS No 1455-42-1, for use in food contact materials. EFS2. 12:3863. doi:10.2903/j.efsa.2014.3863
  • [EFSA CEF Panel] European Food Safety Authority Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids. 2014b. Scientific Opinion on the safety assessment of the substance, furan‐2, 5‐dicarboxylic acid, CAS No 3238‐40‐2, for use in food contact materials. EFS2. 12. doi: 10.2903/j.efsa.2014.3866.
  • [EFSA, WHO] European Food Safety Authority, World Health Organization. 2016. Review of the Threshold of Toxicological Concern (TTC) approach and development of new TTC decision tree. EFSA Supporting Publ. 13. doi: 10.2903/sp.efsa.2016.EN-1006.
  • [EFSA Scientific Committee] European Food Safety Authority Scientific Committee. 2019. Guidance on the use of the threshold of toxicological concern approach in food safety assessment. EFS2. 17:293. doi:10.2903/j.efsa.2019.5708
  • European Commission. 2011. Commission regulation (EU) No 10/2011 of 14 January 2011 on plastic materials and articles intended to come into contact with food. Official Journal of the European Commission. L 12: 1. 15.01.2011. Last amended by Commission Regulation (EU) 2019/1338 of 8 August 2019. Off J Eur Commission. 12:1–89.
  • Freire MT, Damant AP, Castle L, Reyes FGR. 1999. Thermal stability of polyethylene terephthalate (PET): oligomer distribution and formation of volatiles. Packag Technol Sci. 12:29–36.
  • Goodman I, Nesbitt BF. 1960. The structures and reversible polymerization of cyclic oligomers from poly(ethylene terephthalate). J Polym Sci. 48:423–433. doi:10.1002/pol.1960.1204815042
  • Holland BJ, Hay JN. 2002. Analysis of comonomer content and cyclic oligomers of poly(ethylene terephthalate). Polymer. 43:1797–1804. doi:10.1016/S0032-38610100773
  • Hoppe M, Fornari R, Voogt PD, Franz R. 2017. Migration of oligomers from PET: determination of diffusion coefficients and comparison of experimental versus modelled migration. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 34:1251–1260. doi:10.1080/19440049.2017.1322222
  • Hoppe M, Voogt PD, Franz R. 2016. Identification and quantification of oligomers as potential migrants in plastics food contact materials with a focus in polycondensates – A review. Trends Food Sci Technol. 50:118–130. doi:10.1016/j.tifs.2016.01.018
  • Hovenkamp SG, Munting JP. 1970. Formation of diethylene glycol as a side reaction during production of polyethylene terephthalate. J Polym Sci A-1 Polym Chem. 8:679–682. doi:10.1002/pol.1970.150080310
  • [ILSI Europe] International Life Sciences Institute Europe. 2015. Guidance on best practices on the risk assessment of non-intentional added substances (NIAS) in food contact materials and articles. In: Koster S, Bani-Estivals MH, Bonuomo M, Bradley E, Chagnon MC, Garcia ML, Godts F, Gude T, Helling R, Paseiro-Losada P, et al, editors. ILSI Europe Report Series. Brussels (Belgium): ILSI Europe; p. 70.
  • Jang S, Ji K. 2015. Effect of chronic exposure to two components of Tritan copolyester on Daphnia magna, Moina macrocopa, and Oryzias latipes, and potential mechanisms of endocrine disruption using H295R cells. Ecotoxicology. 24:1906–1914. doi:10.1007/s10646-015-1526-5
  • Kim D-J, Lee KT. 2012a. Analysis of specific migration of monomers and oligomers from polyethylene terephthalate bottles and trays according to the testing methods as prescribed in the legislation of the EU and Asian countries. Polym Test. 31:1001–1007. doi:10.1016/j.polymertesting.2012.07.012
  • Kim D-J, Lee K-T. 2012b. Determination of monomers and oligomers in polyethylene terephthalate trays and bottles for food use by using high performance liquid chromatography-electrospray ionization-mass spectrometry. Polym Test. 31:490–499. doi:10.1016/j.polymertesting.2012.02.001
  • Komolprasert V, McNeal TP, Agrawal A, Adhikari C, Thayer DW. 2001. Volatile and non-volatile compounds in irradiated semi-rigid crystalline poly(ethylene terephthalate) polymers. Food Addit Contam. 18:89–101. doi:10.1080/02652030010006096
  • Lim B-H, Kwon S-H, Kang E-C, Park H, Lee H-W, Kim W-G. 2003. Isolation and identification of cyclic oligomers of the poly(ethylene terephthalate)-poly(ethylene isophthalate) copolymer. J Polym Sci A Polym Chem. 41:881–889. doi:10.1002/pola.10637
  • López-Cervantes J, Sánchez-Machado DI, Simal-Lozano J, Paseiro-Losada P. 2003. Migration of ethylene terephthalate oligomers from roasting bags into olive oil. Chromatographia. 58:321–326. doi:10.1365/s10337-003-0034-6
  • Munro IC, Ford RA, Kennepohl E, Sprenger JG. 1996. Correlation of structural class with no-observed-effect levels: A proposal for establishing a threshold of concern. Food Chem Toxicol. 34:829–867. doi:10.1016/S0278-69159600049
  • Nasser ALM, Lopes LMX, Eberlin MN, Monteiro M. 2005. Identification of oligomers in polyethyleneterephthalate bottles for mineral water and fruit juice. Development and validation of a high-performance liquid chromatographic method for the determination of first series cyclic trimer. J Chromatogr A. 1097:130–137. doi:10.1016/j.chroma.2005.08.023
  • Osimitz TG, Eldridge ML, Sloter E, Welsh W, Ai N, Sayler GS, Menn F, Toole C. 2012. Lack of androgenicity and estrogenicity of the three monomers used in Eastman’s Tritan™ copolyesters. Food Chem Toxicol. 50:2196–2205. doi:10.1016/j.fct.2012.02.010
  • Patlewicz G, Jeliazkova N, Safford RJ, Worth AP, Aleksiev B. 2008. An evaluation of the implementation of the Cramer classification scheme in the Toxtree software. SAR QSAR Environ Res. 19:495–524. doi:10.1080/10629360802083871
  • Peebles LH, Huffman MW, Ablett CT. 1969. Isolation and identification of the linear and cyclic oligomers of poly(ethylene terephthalate) and the mechanism of cyclic oligomer formation. J Polym Sci A-1 Polym Chem. 7:479–496. doi:10.1002/pol.1969.150070207
  • Schaefer A, Ohm VA, Simat TJ. 2004. Migration from can coatings: part 2. Identification and quantification of migrating cyclic oligoesters below 1000 Da. Food Addit Contam. 21:377–389. doi:10.1080/02652030310001637939
  • Schiraldi DA. 2003. New Poly(Ethylene Terephthalate) Copolymers. In: Scheirs J, Long TE, editors. Modern polyesters: chemistry and technology of polyesters and copolyesters. Hoboken (N.J.): John Wiley & Sons; p. 243–265.
  • Song J, Siskova A, Simons MG, Kowalski WJ, Kowalczuk MM, van den Brink OF. 2011. LC-multistage mass spectrometry for the characterization of poly(butylene adipate-co-butylene terephthalate) copolyester. J Am Soc Mass Spectrom. 22:641–648. doi:10.1007/s13361-010-0071-y
  • Thiele UK. 2007. Polyester bottle resins: [production, processing, properties and recycling]. Vol. 5. Heidelberg (Germany): Heidelberg Business Media; p. 320 S. ISBN: 3980749746.
  • Tsochatzis ED, Alberto Lopes J, Kappenstein O, Tietz T, Hoekstra EJ. 2020. Quantification of PET cyclic and linear oligomers in teabags by a validated LC-MS method – in silico toxicity assessment and consumer’s exposure. Food Chem. 317:126427. doi:10.1016/j.foodchem.2020.126427
  • Ubeda S, Aznar M, Nerín C. 2018. Determination of oligomers in virgin and recycled polyethylene terephthalate (PET) samples by UPLC-MS-QTOF. Anal Bioanal Chem. 410:2377–2384. doi:10.1007/s00216-018-0902-4
  • Wick G, Zeitler H. 1983. Cyclische Oligomere in Polyestern aus Diolen und aromatischen Dicarbonsäuren. Angew Makromol Chemie. 112:59–94. doi:10.1002/apmc.1983.051120106

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.