Identification and quantification of oligomers as potential migrants in plastic food contact materials with a focus on condensation polymers - a review (2023)

Plastic packaging contains residues of substances used in the manufacturing process, such as B. solvents, and unintentionally added substances (NIAS), etc. B. Impurities, oligomers, or degradation products. A search of the peer-reviewed literature revealed at least 10,259 chemicals associated with plastic packaging materials, including those used in manufacturing and/or contained in end-of-line packaging items. We then summarize and discuss their chemical structures, analytical tools, migration characteristics and hazard classes where possible. For plastic packaging chemicals, a literature review shows that gas chromatography and liquid chromatography are often combined with various high-resolution mass spectrometry-based precision mass analyzers in order to identify unknown migrated species in plastic packaging. Chemical migration from food packaging is influenced by several parameters, including the type and complexity of the food, contact time, system temperature, type of packaging contact layer, and the identity of the migrated species. A review of the specialized literature shows that information on adverse effects is only available for about 1600 substances. Of these, additives appear to be more toxic to wildlife and humans than monomers. Neurotoxicity accounted for the highest proportion of all chemical types, and benzene, organic acids and their derivatives were the most toxic chemical types. In addition, studies have shown that hydrocarbon derivatives, organonitrogen compounds, and organometallic compounds are the most dermally toxic, while organohalogen compounds are the most hepatotoxic. The main cause of skin allergies is organic salts. The research lays the groundwork for widespread dissemination of information about chemicals in plastics and contributes to a better understanding of their potential risks to the environment and humans.

The COVID-19 pandemic has been a topic of conversation around the world as it has swept the world population and changed many aspects. The pandemic has directly or indirectly affected all sectors. The food industry took a direct hit. The food packaging industry has taken this opportunity to serve and feed those affected by the pandemic, but there have also been interactions, reactions and consequences throughout the course of the pandemic. The purpose of this perspective is to highlight the importance of the food packaging industry (from a COVID-19 perspective) and to highlight that food packaging materials are not ready for such times. Regardless, as the world is being asked to live with corona, improvisation is necessary, bugs in systems have to be fixed, and the entire packaging industry has to crunch to be able to live with corona or to face something much worse than corona worse. The purpose of this discussion is to understand the seriousness of the actual situation and process the information from the scattered fragments of the report. The use of food packaging materials generates a lot of plastic waste. Single-use plastics have become popular due to fears of contamination, leading to a massive turnover of waste. Due to the fear of corona, a large number of disinfectants and disinfectants are sprayed on the surface of food packaging materials to disinfect the surface. Food packaging is tailored to the needs of food containers and has never been used for sanitizing sprays. The consequences of these sanitation procedures are unprecedented, neglected, and no action appears to be taken in the post-COVID-19 phase. The coronavirus took us by surprise this time, but next time at least the food packaging industry needs to be well prepared. The speculative consequences are examined and sound recommendations are made. Emphasize the need for comprehensive research in this direction in soil reality studies.

This chapter deals with the emergence of plastic components in food by touching on different types of plastic packaging, films and coatings. It describes the mechanisms that occur when food is contaminated by different packaging materials, and how the type of food and packaging affects the degree of contamination. The main types of contaminant phenomena, as well as the applicable regulations for the use of plastic food packaging, are considered and discussed extensively. In addition, the types of migration phenomena and factors affecting migration are comprehensively studied. In addition, the chemical structures of migrating components, adverse effects on food, health, migration factors, and the regulated residue levels of these components related to packaging polymers (monomers and oligomers) and packaging additives are discussed separately.

A technique for the detection and control of cycloesterification (CE) in biodegradable polyesters is presented. It should be noted that CE can be extracted by extraction or migration and then detected by GC-MS or LC-MS depending on the volatility, LC-MS technique is more commonly used since CE is usually less volatile. CE has been detected in several typical biodegradable polyesters, such as polylactic acid (PLA), polybutylene succinate (PBS), and polybutylene adipate terephthalate with repeat units less than 10 Alcohol esters (PBAT); the improvement of the polymerization process and the use of organic solvents to wash biodegradable polyester particles can effectively reduce the CE content, and the washing strategy is relatively more convenient and efficient.

Phenolic and substituted phenolic resole resins are commonly used in the formulation of can coatings. However, migration analysis of these coatings has been poorly described compared to other coating techniques. While epoxies and polyesters are known to have migrations with established mechanisms of formation, unintentionally added substances (NIAS) specifically related to phenolic resins are rarely explored in the literature. The purpose of this publication is to further investigate the effect of resole resins used in can coating formulations on the properties of the extracted NIAS. Six different polyester phenolic can coating models were formulated with specific phenol, cresol or tert-butylphenol based resole resins. Can coating films were extracted in acetonitrile at 40°C for 24 hours prior to analysis. NIAS identification was performed using gas chromatographic separation coupled with high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance spectroscopy (NMR). Cyclic polyester oligomers were found in all extracts at concentrations ranging from 10 μg/dm²Double 226μg/dm², not specifically affected by the resole resin used in the formulation. While few or no peaks were observed for cresyl and phenol-based resoles, 48 ​​were specifically observed in paint extracts containing tert-butylphenol-based resoles and their respective resole formulations peak. The strongest peaks were identified as aldehydes by HRMS and NMR analysis. These aldehydes were semiquantified in similar proportions as polyester oligomers. The presence of such aldehydes has never been reported in the literature on NIAS in can coatings. Further studies are then required to better understand the mechanism of aldehyde formation and to assess the toxicological profile of this class of chemicals.

Current Opinion in Food Science, Band 6, 2015, S. 33-37

There is growing concern about the presence of unintentionally added substances (NIAS) in food contact materials. These substances cannot be excluded from food contact materials and end up in our food. Their identification is often difficult, or in some cases impossible, making it difficult to assess their safety if exposed. This overview provides an overview of current European regulatory requirements and the latest innovations in NIAS safety assessments. The main conclusion is that an innovative, pragmatic and science-based approach was recently published that can be used to prioritize NIAS based on their exposure and hazards.

Journal of Chromatography A, Band 1444, 2016, S. 106–113

Cross-linked polyester resins are being marketed as an alternative to epoxy resins as coatings for metal food cans. Due to the diversity of substances used in the manufacture of paints, identifying potential migration of these paints into food is a significant analytical challenge. However, this identification is needed to assess migration from can coatings to food and to assess dietary exposure quantification. Polyester can coatings were extracted with acetonitrile at 40°C for 24 hours, and the extracts were analyzed using various analytical techniques, including GC-MS, HPLC-DAD/MS, HPLC-DAD/CAD, and UHPL C-HRMS. Twenty-nine non-volatile oligomers were tentatively identified using retention time, UV spectroscopy, and accurate mass measurements. The oligomers identified indicated that the food can coating used was a polyester coating mainly based on the monomers isophthalic, terephthalic and nadic acids. To ensure certainty of identification, one of the provisionally identified oligomers was synthesized and analyzed¹³C and¹H NMR and UHPL-C HRMS. NMR and HRMS results confirmed the presence of the compound in the jar extract. Finally, to determine if rapid, direct detection of oligomers was feasible, the coating was analyzed using DART-HRMS. 23 of 29 oligomers in the coating were identified within minutes by direct measurement using DART-HRMS.

Talanta，Band 172，2017，S.68-77

Controlling chemical migration of novel functionalized food contact materials (FCMs) is a challenge in meeting food safety requirements. Intentionally Added Substances (NIAS) represent a group of chemical substances that are not used but may be introduced or formed during FCM production. This study describes a multi-analytical approach to assess migration of unknown substances from FCM. A case study was performed using a developed polymer consisting of a monolayer film containing polylactic acid (PLA), polylimonene (PL), and zinc oxide nanoparticles (ZnO NPs). The method included an ICP-MS (inductively coupled plasma mass spectrometry) platform to determine the transfer of ZnO NPs used as antimicrobial agents, as well as GC-MS and LC-MS (gas/liquid chromatography coupled to a quadrupole). Orbitrap mass spectrometer) to characterize the chemical structure of NIAS using specific signatures of molecular mass and mass fragmentation. Screening of unknown compounds involved retrospective analysis and data processing using mass spectral libraries and databases of GC and LC data, respectively. This method provided preliminary identification and quantification of seven NIAS, 3 by GC (tripropylene glycol diacrylate, 10-eicosene, and α-tocopheryl acetate) and 4 by LC (N,N -Diethyldodecylamide, N-[(9Z)-9-octadecen-1-yl]acetamide, 1-palmitoylglycerol and glyceryl stearate). This migration study was carried out according to the standard protocol set out in the EU Food Contact Materials Regulation.

Journal of Chromatography A, Band 1372, 2014, S. 133–144

Chemosphere, Volume 251, 2020, Number 126373

Food Packaging and Shelf Life, Volume 20, 2019, Article 100318

Recycled materials such as expanded polystyrene (EPS) are increasingly found in the food market, and recycled PS resin may contain some harmful chemicals. Therefore, the approach of solid-phase microextraction and gas chromatography coupled with mass spectrometry, followed by the application of chemometric tools to the obtained data, can identify markers of new and recovered EPS. A multivariate statistical analysis was developed to characterize the volatile organic compound (VOC) signature in new and recycled EPS containers and to identify potential VOC markers that lead to EPS container discrimination. A total of 99 compounds were identified in new and recycled EPS containers. Among them, 17 compounds that contributed most to the discrimination were selected according to their variable importance in the predicted value (VIP), including o-xylene, acetophenone, ethylbenzene, α-ethylstyrene, 2- Phenylacrolein, propylbenzene, 2-phenyl-1-propene, undecanal, ethyl benzoate, 2-ethyl-1-hexanol, decanal, benzyl formaldehyde, cumene, 2, 4-Diphenyl-1-butene, dodecanal, benzaldehyde and nonanal. To assess the health risks of EPS containers, migration tests were performed on EPS containers in two food simulants (10% ethanol, 3% acetic acid). It should be emphasized that a large amount of styrene was detected. Nevertheless, the analyzed material complies with the current EU Regulation No. 10/2011. The proposed method finds distinguishing marks and provides a reliable tool to distinguish new and recycled EPS containers, which may be an additional tool for quality control of EPS containers.