In vitro intestinal digestibility of cyclic aromatic polyester oligomers from polyethylene terephthalate (PET) and polybutylene terephthalate (PBT)

References

• Ali J, Camilleri P, Brown MB, Hutt AJ, Kirton SB. 2012. Revisiting the general solubility equation: in silico prediction of aqueous solubility incorporating the effect of topographical polar surface area. J Chem Inf Model. 52:420–428.
   PubMed Web of Science ®Google Scholar
• Ashby R. 1988. Migration from polyethylene terephthalate under all conditions of use. Food Addit Contam. 5:485–492.
   Web of Science ®Google Scholar
• Begley TH, Dennison JL, Hollifield HC. 1990. Migration into food of polyethylene terephthalate (PET) cyclic oligomers from PET microwave susceptor packaging. Food Addit Contam. 7:797–803.
   PubMed Web of Science ®Google Scholar
• Brenz F, Linke S, Simat T. 2018. Linear and cyclic oligomers in polybutylene terephthalate for food contact materials. Food Addit Contam. 35:583–598.
   PubMed Web of Science ®Google Scholar
• Castle L, Jickells SM, Gilbert J, Harrison N. 1990. Migration testing of plastics and microwave‐active materials for high‐temperature food‐use applications. Food Addit Contam. 7:779–796.
   PubMed Web of Science ®Google Scholar
• Castle L, Mayo A, Crews C, Gilbert J. 1989. Migration of Poly(ethylene terephthalate) (PET) Oligomers from PET Plastics into Foods during Microwave and Conventional Cooking and into Bottled Beverages. J Food Prot. 52:337–342.
   PubMed Web of Science ®Google Scholar
• Cramer GM, Ford RA, Hall RL. 1976. Estimation of toxic hazard—A decision tree approach. Food Cosmet Toxicol. 16:255–276.
   Google Scholar
• Daina A, Michielin O, Zoete V. 2017. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 7:42717.
   Web of Science ®Google Scholar
• Daina A, Zoete V. 2016. A BOILED-egg to predict gastrointestinal absorption and brain penetration of small molecules. Chem Med Chem. 11:1117–1121.
   Web of Science ®Google Scholar
• Driffield M, Garcia-Lopez M, Christy J, Lloyd AS, Tarbin JA, Hough P, Bradley EL, Oldring PKT. 2018. The determination of monomers and oligomers from polyester-based can coatings into foodstuffs over extended storage periods. Food Addit Contam. 35:1200–1213.
   PubMed Web of Science ®Google Scholar
• Eckardt M, Hetzel L, Brenz F, Simat TJ. 2019. 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. 1–23. doi:10.1080/19440049.2019.1616831.
   Google Scholar
• Eckardt M, Kubicova M, Simat TJ. 2018. Universal response quantification approach using a Corona Charged Aerosol Detector (CAD) – application on linear and cyclic oligomers extractable from polycondensate plastics polyesters, polyamides and polyarylsulfones. J Chromatogr A. 1572:187–202.
   PubMed Web of Science ®Google Scholar
• EFSA CEF Panel. 2008. Note for Guidance For the Preparation of an Application for the Safety Assessment of a Substance to be used in Plastic Food Contact Materials. EFSA J 6(7):21r. doi:10.2903/j.efsa.2008.21r.
   Google Scholar
• EFSA CEF Panel. 2016. Scientific opinion on 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. 14:4357.
   Web of Science ®Google Scholar
• EFSA 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.
   Google Scholar
• EFSA Scientific Committee. 2019. Guidance on the use of the Threshold of Toxicological Concern approach in food safety assessment. EFSA J. 17:5708. doi:10.2903/j.efsa.2019.5708.
   Web of Science ®Google Scholar
• Ertl P, Rohde B, Selzer P. 2000. Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem. 43:3714–3717.
   PubMed Web of Science ®Google Scholar
• 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. OJEU. 12:1–89.
   Google Scholar
• Hamdani M, Thil L, Gans G, Feigenbaum AE. 2002. Safety assessment of polymeric additives for food packaging: hydrolysis of polymeric plasticizers by digestive fluids. J Appl Polym Sci. 83:956–966.
   Web of Science ®Google Scholar
• Herzog K, Müller R-J, Deckwer W-D. 2006. Mechanism and kinetics of the enzymatic hydrolysis of polyester nanoparticles by lipases. Polym Degrad Stab. 91:2486–2498.
   Web of Science ®Google Scholar
• Hoppe M, de Voogt P, 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.
   Web of Science ®Google Scholar
• Hoppe M, de Voogt P, Franz R. 2018. Oligomers in polyethylene naphthalate and polybutylene terephthalate – identification and exploring migration. Food Packag Shelf Life. 17:171–178.
   Web of Science ®Google Scholar
• Kim D-J, Lee K-T. 2012. 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.
   Web of Science ®Google Scholar
• Kroes R, Renwick AG, Cheeseman M, Kleiner J, Mangelsdorf I, Piersma A, Schilter B, Schlatter J, van Schothorst F, Vos JG, et al. 2004. Structure-based thresholds of toxicological concern (TTC): guidance for application to substances present at low levels in the diet. Food Chem Toxicol. 42:65–83.
   PubMed Web of Science ®Google Scholar
• Li C, Zhang M, Qin J, Zhang Y, Qiu J. 2015. Study on molecular modeling and the difference of PC lipase-catalyzed degradation of poly (butylene succinate) copolymers modified by linear monomers. Polym Degrad Stab. 116:75–80.
   Web of Science ®Google Scholar
• Marten E, Müller R-J, Deckwer W-D. 2003. Studies on the enzymatic hydrolysis of polyesters I. Low molecular mass model esters and aliphatic polyesters. Polym Degrad Stab. 80:485–501.
   Web of Science ®Google Scholar
• Marten E, Müller R-J, Deckwer W-D. 2005. Studies on the enzymatic hydrolysis of polyesters. II. Aliphatic–aromatic copolyesters. Polym Degrad Stab. 88:371–381.
   Web of Science ®Google Scholar
• Müller R-J, Kleeberg I, Deckwer W-D. 2001. Biodegradation of polyesters containing aromatic constituents. J Biotechnol. 86:87–95.
   PubMed Web of Science ®Google Scholar
• Munro IC, Renwick AG, Danielewska-Nikiel B. 2008. The Threshold of Toxicological Concern (TTC) in risk assessment. Toxicol Lett. 180:151–156.
   PubMed Web of Science ®Google Scholar
• Nasser ALM, Lopes LMX, Eberlin MN, Monteiro M. 2005. Identification of oligomers in polyethyleneterephthalate bottles for mineral water and fruit juice. J Chromatogr A. 1097:130–137.
   PubMed Web of Science ®Google Scholar
• Omer E, Cariou R, Remaud G, Guitton Y, Germon H, Hill P, Dervilly-Pinel G, Le Bizec B. 2018. Elucidation of non-intentionally added substances migrating from polyester-polyurethane lacquers using automated LC-HRMS data processing. Anal Bioanal Chem. 410:5391–5403.
   PubMed Web of Science ®Google Scholar
• Paseiro-Cerrato R, MacMahon S, Ridge CD, Noonan GO, Begley TH. 2016. Identification of unknown compounds from polyester cans coatings that may potentially migrate into food or food simulants. J Chromatogr A. 1444:106–113.
   PubMed Web of Science ®Google Scholar
• Patlewicz G, Wambaugh JF, Felter SP, Simon TW, Becker RA. 2018. Utilizing Threshold of Toxicological Concern (TTC) with high throughput exposure predictions (HTE) as a risk-based prioritization approach for thousands of chemicals. Comput Toxicol. 7:58–67.
   PubMedGoogle Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• EFSA CEF Panel. 2008. Note for guidance for the preparation of an application for the safety assessment of a substance to be used in plastic food contact materials. EFSA J. 6(7):21r. doi:10.2903/j.efsa.2008.21r.
   Google Scholar
• Sivalingam G, Madras G. 2004. Dynamics of lipase catalyzed enzymatic degradation of poly(bisphenol-A carbonate). J Appl Polym Sci. 91:2391–2396.
   Web of Science ®Google Scholar
• Welle F. 2014. Food law compliance of Poly(ethylene Terephthalate) (PET) food packaging materials. In: Komolprasert V, Turowski P, editors. Food additives and packaging (Vol. 1162). Washington (DC): American Chemical Society; p. 167–195.
   Google Scholar
• Wick G, Zeitler H. 1983. Cyclische oligomere in polyestern aus diolen und aromatischen dicarbonsäuren. Angew Makromol Chem. 112:59–94.
   Google Scholar
• Wildman SA, Crippen GM. 1999. Prediction of physicochemical parameters by atomic contributions. J Chem Inf Comput Sci. 39:868–873.
   Google Scholar