Comparative Analysis of Phthalates Migration into Mayonnaise and Mustard Sauce from Polyethylene Terephthalate (PET) Containers
محورهای موضوعی : food science
mahta samadi
1
,
maryam mizani
2
,
شهرام شعیبی
3
1 - Department of Food Science and Technology, Science and Research Branch, Islamic Azad University, Tehran, Iran.
2 - Department of Food Science and technology, Science and Research Branch, Islamic AzadUniversity, Tehran, Iran.
3 - عضو هیات علمی آزمایشگاه مرجع کنترل غذا و دارو، سازمان غذا و دارو، وزارت بهداشت و درمان و آموزش پزشکی، تهران، ایران.
کلید واژه: Mayonnaise, Migration, Mustard Sauce, Phthalates, Plasticizer, Polyethylene terephthalate ,
چکیده مقاله :
The use of sauces packaged in Polyethylene terephthalate (PET) bottles is widespread in households, restaurants, and fast-food establishments. This research focuses on comparing the migration of phthalates from PET bottles into mayonnaise and mustard sauces, adhering to guidelines set forth by the British Standard, European Union (EU) Commission Regulations, and the FDA. The study employed food simulants and PET bottle samples directly sourced from production lines to measure the Overall Migration Limit (OML). In this investigation, the presence of five types of phthalates, namely DEHP, DBP, BBP, DINP, and DIOP was analyzed in PET bottles used for packaging these sauces. The OML levels in the PET bottle samples for both mayonnaise and mustard sauces were significantly below the EU regulation limit. Only DIOP was detected in the PET bottles used for mayonnaise sauce. For mustard sauce, both DEHP and DIOP were detected simultaneously. The levels of DIOP in mayonnaise and mustard sauces were well below the EU's specified SML. However, DEHP levels in mustard sauce slightly exceeded the specified SML value. The ratio of migrant milligrams per kilogram of sauce and the migration percentage of phthalates were calculated, providing a comprehensive analysis of phthalate migration dynamics. These results underscore the importance of continuous monitoring and stringent compliance with regulatory guidelines to ensure the safety of PET-packaged food products.
The use of sauces packaged in Polyethylene terephthalate (PET) bottles is widespread in households, restaurants, and fast-food establishments. This research focuses on comparing the migration of phthalates from PET bottles into mayonnaise and mustard sauces, adhering to guidelines set forth by the British Standard, European Union (EU) Commission Regulations, and the FDA. The study employed food simulants and PET bottle samples directly sourced from production lines to measure the Overall Migration Limit (OML). In this investigation, the presence of five types of phthalates, namely DEHP, DBP, BBP, DINP, and DIOP was analyzed in PET bottles used for packaging these sauces. The OML levels in the PET bottle samples for both mayonnaise and mustard sauces were significantly below the EU regulation limit. Only DIOP was detected in the PET bottles used for mayonnaise sauce. For mustard sauce, both DEHP and DIOP were detected simultaneously. The levels of DIOP in mayonnaise and mustard sauces were well below the EU's specified SML. However, DEHP levels in mustard sauce slightly exceeded the specified SML value. The ratio of migrant milligrams per kilogram of sauce and the migration percentage of phthalates were calculated, providing a comprehensive analysis of phthalate migration dynamics. These results underscore the importance of continuous monitoring and stringent compliance with regulatory guidelines to ensure the safety of PET-packaged food products.
Aigotti, R.; Giannone, N.; Asteggiano, A.; Mecarelli, E.; Dal Bello, F.; Medana, C. Release of Selected Non-Intentionally Added Substances (NIAS) from PET Food Contact Materials: A New Online SPE-UHPLC-MS/MS Multiresidue Method. Separations 2022, 9, 188. https://doi.org/10.3390/
Alvarado Chacon, F., Brouwer, M. T., & Thoden van Velzen, E. U. (2020). Effect of recycled content and rPET quality on the properties of PET bottles, part I: Optical and mechanical properties. Packaging Technology and Science, 33(9), 347-357. https://doi.org/10.1002/pts.2490
Anggarkasih, M. G., Yuliana, N. D., Regiyana, Y., Massijaya, M. Y., & Budijanto, S. (2018). Analysis of Di-N-Butyl Phthalate (DBP) Residue in Commercial Food Packaging from Recycled Paper and Its Migration into Food Simulant. Jurnal Teknologi Industri Pertanian, 28(2). Retrieved from: https://jurnalpenyuluhan.ipb.ac.id/index.php/jurnaltin/article/view/24629
Ashby, R. (1988). Migration from polyethylene terephthalate under all conditions of use. Food Additives & Contaminants, 5(S1), 485-492. https://doi.org/10.1080/02652038809373681
Askar, M. K., Al-Kamaki, Y. S., & Hassan, A. (2023). Utilizing polyethylene terephthalate PET in concrete: A review. Polymers, 15(15), 3320. https://doi.org/10.3390/polym15153320
British Standard (2002a). BS EN 1186-1:2002, Materials and articles in contact with foodstuffs - Plastics - Part 1: Guide to the selection of conditions and test methods for overall migration. Available at: https://img.21food.cn/img/biaozhun/20090815/187/11183625.pdf
British Standard (2002b). BS EN 1186-3:2002, Materials and articles in contact with foodstuffs - Plastics - Part 3: Test methods for overall migration into aqueous food simulants by total immersion. Available at: http://files.foodmate.com/down.php?auth=B2MAY1swXTE
Cao, X. L. (2010). Phthalate esters in foods: sources, occurrence, and analytical methods. Comprehensive reviews in food science and food safety, 9(1), 21-43. https://doi.org/10.1111/j.1541-4337.2009.00093.x
Cao, X. L., Zhao, W., & Dabeka, R. (2015). Di-(2-ethylhexyl) adipate and 20 phthalates in composite food samples from the 2013 Canadian Total Diet Study. Food Additives & Contaminants: Part A, 32(11), 1893-1901. https://doi.org/10.1080/19440049.2015.1079742
Conroy, S., & Zhang, X. (2024). Theoretical insights into chemical recycling of polyethylene terephthalate (PET). Polymer Degradation and Stability, 110729. https://doi.org/10.1016/j.polymdegradstab.2024.110729
European Chemical Agency (ECHA) (2013). EC Number: 201-559-5, Dihexyl phthalate (DHP). Available at: https://echa.europa.eu/documents/10162/65336c46-c178-4b71-a927-15437e8b303a
European Chemical Agency (ECHA) (2014). EC Number: 201-553-2, Diisobutyl phthalate (DIBP). Available at: https://echa.europa.eu/documents/10162/12934bbe-ad6f-4671-a931-1ef44f51cb10
European Chemical Agency (ECHA) (2014). EC Number: 201-622-7, Benzyl butyl phthalate (BBP). Available at: https://echa.europa.eu/documents/10162/c5e7a581-db15-4e09-8be9-37d42c5409d8
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. Off J Eur Union, 12, pp.1-89. Available at: https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2011:012:0001:0089:en:PDF
Facts and factor (2023). Polyethylene Terephthalate (PET) Market Size, Share Global Analysis Report, 2022–2030. Available at: https://www.fnfresearch.com/polyethylene-terephthalate-pet-market
Fan, Y., Chen, H., Liu, H., Wang, F., Ma, S., Latipa, A., ... & Wang, C. (2017). Analysis of phthalate esters in dairy products—a brief review. Analytical methods, 9(3), 370-380. https://doi.org/10.1039/C6AY02885C
Fasano, E., Bono-Blay, F., Cirillo, T., Montuori, P., & Lacorte, S. (2012). Migration of phthalates, alkylphenols, bisphenol A and di (2-ethylhexyl) adipate from food packaging. Food control, 27(1), 132-138. https://doi.org/10.1016/j.foodcont.2012.03.005
Featherstone, S. (Ed.). (2015). A complete course in canning and related processes: Volume 3 Processing Procedures for Canned Food Products. Woodhead Publishing. eBook ISBN: 9780857096876
Gao, X., Yang, B., Tang, Z., Luo, X., Wang, F., Xu, H., & Cai, X. (2014). Determination of phthalates released from paper packaging materials by solid-phase extraction–high-performance liquid chromatography. Journal of chromatographic science, 52(5), 383-389. https://doi.org/10.1093/chromsci/bmt046
García‐Casal, M. N., Peña‐Rosas, J. P., & Malavé, H. G. (2016). Sauces, spices, and condiments: definitions, potential benefits, consumption patterns, and global markets. Annals of the New York Academy of Sciences, 1379(1), 3-16. https://doi.org/10.1111/nyas.13045
Haji Harunarashid, N. Z. I., Lim, L. H., & Harunsani, M. H. (2017). Phthalate sample preparation methods and analysis in food and food packaging: a review. Food Analytical Methods, 10, 3790-3814. https://doi.org/10.1007/s12161-017-0938-7
Heudorf, U., Mersch-Sundermann, V., & Angerer, J. (2007). Phthalates: toxicology and exposure. International journal of hygiene and environmental health, 210(5), 623-634. https://doi.org/10.1016/j.ijheh.2007.07.011
Hosseini, S. J., Homayouni, A., Ghanbarzadeh, B., Sobhani, Z., & Yousefi, G. H. (2016). Migration of dibutyl phthalate and dimethyl phthalate in rose water packaged in polyethylene terephthalate containers. Available at: https://nsft.sbmu.ac.ir/article-1-1957-en.pdf
IARC Working Group on the Evaluation of Carcinogenic Risks to Humans (2013). Di (2-ethylhexyl) phthalate. In Some Chemicals Present in Industrial and Consumer Products, Food and Drinking-Water. International Agency for Research on Cancer. ISBN-13: 978-9283213246
Joseph, T. M., Azat, S., Ahmadi, Z., Jazani, O. M., Esmaeili, A., Kianfar, E., ... & Thomas, S. (2024). Polyethylene terephthalate (PET) recycling: A review. Case Studies in Chemical and Environmental Engineering, 100673. https://doi.org/10.1016/j.cscee.2024.100673
Kiani, A., Ahmadloo, M., Shariatifar, N., Moazzen, M., Baghani, A. N., Khaniki, G. J., ... & Ghajarbeygi, P. (2018). Method development for determination of migrated phthalate acid esters from polyethylene terephthalate (PET) packaging into traditional Iranian drinking beverage (Doogh) samples: a novel approach of MSPE-GC/MS technique. Environmental Science and Pollution Research, 25, 12728-12738. https://doi.org/10.1007/s11356-018-1471-y
Liu, F. F., Liu, G. Z., Zhu, Z. L., Wang, S. C., & Zhao, F. F. (2019). Interactions between microplastics and phthalate esters as affected by microplastics characteristics and solution chemistry. Chemosphere, 214, 688-694. https://doi.org/10.1016/j.chemosphere.2018.09.174
Liu, J. M., Li, C. Y., Zhao, N., Wang, Z. H., Lv, S. W., Liu, J. C., ... & Wang, S. (2020). Migration regularity of phthalates in polyethylene wrap film of food packaging. Journal of Food Science, 85(7), 2105-2113. https://doi.org/10.1111/1750-3841.15181
Mordor Intelligence Research & Advisory. (2024, February). Polyethylene Terephthalate (PET) Market SIZE & SHARE ANALYSIS - GROWTH TRENDS & FORECASTS UP TO 2029. Mordor Intelligence. Retrieved May 23, 2024, from: https://www.mordorintelligence.com/industry-reports/polyethylene-terephtalate-market
Morley, W. G. (2016). Mayonnaise. https://doi.org/10.1016/B978-0-12-384947-2.00449-9
Mukhopadhyay, M., Jalal, M., Vignesh, G., Ziauddin, M., Sampath, S., Bharat, G. K., ... & Chakraborty, P. (2022). Migration of plasticizers from polyethylene terephthalate and low-density polyethylene casing into bottled water: a case study from India. Bulletin of Environmental Contamination and Toxicology, 109(6), 949-955. https://doi.org/10.1007/s00128-022-03474-x
National Center for Biotechnology Information (2024). PubChem Compound Summary for CID 2347, Benzyl butyl phthalate. Retrieved May 22, 2024 from https://pubchem.ncbi.nlm.nih.gov/compound/Benzyl-butyl-phthalate.
National Center for Biotechnology Information (2024). PubChem Compound Summary for CID 33599, Diisodecyl phthalate. Retrieved May 22, 2024 from: https://pubchem.ncbi.nlm.nih.gov/compound/Diisodecyl-phthalate.
National Center for Biotechnology Information (2024). PubChem Compound Summary for CID 590836, Diisononyl phthalate. Retrieved May 22, 2024 from: https://pubchem.ncbi.nlm.nih.gov/compound/Diisononyl-phthalate.
National Center for Biotechnology Information (2024). PubChem Compound Summary for CID 8559, Dipropyl phthalate. Retrieved May 22, 2024 from https://pubchem.ncbi.nlm.nih.gov/compound/Dipropyl-phthalate.
National Industrial Chemicals Notification And Assessment Scheme (Australian Governments) (2014). Dimethyl phthalate. Priority Existing Chemical Assessment Report No. 37. Available at: https://www.industrialchemicals.gov.au/sites/default/files/PEC37-Dimethyl-phthalate-DMP.pdf
National Industrial Chemicals Notification And Assessment Scheme (Australian Governments) (2015). Butyl benzyl phthalate. Priority Existing Chemical Assessment Report No. 40. Available at: https://www.industrialchemicals.gov.au/sites/default/files/PEC40-Butyl-benzyl-phthalate-BBP.pdf
Nerin, C., Canellas, E., & Vera, P. (2018). Plasticizer migration into foods. http://dx.doi.org/10.1016/B978-0-08-100596-5.21392-9
Nisticò, R. (2020). Polyethylene terephthalate (PET) in the packaging industry. Polymer Testing, 90, 106707. https://doi.org/10.1016/j.polymertesting.2020.106707
Oromiehie, A. (2010). Plastic packaging food and drug principles and testing methods. Tehran, Iran: Ideh Pardazan Fan & Honar Publications, pp. 29 & 81-82. ISBN: 978-964-2559-19-0
Rahimi, L., Ghanbarzadeh, B., & Dehghannya, J. (2016). Migration of phthalate esters from polyethylene terephthalate into a lemon juice simulant. Iranian Food Science and Technology Research Journal, 12(1), pp.79-87. Available at: https://ifstrj.um.ac.ir/article_35196_70f56ec45277c0d08204f7c024ce8c4d.pdf?lang=en
Robertson, Gordon L.. (2013). Food packaging : principles and practice (3rd ed.). Boca Raton: CRC Press. https://doi.org/10.1201/b21347
SHEETS, F. (2007). Breast Cancer & the Environment Research Centers. Available at: https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=7f48554bf7cd1fa683f45dc8bb43a6b1922050cb
Satish, A., Lasya, M., Harini, S., Padmavathi, S., & Baldev, R. (2013). Migration aspects for food contact materials with aqueous food simulating solvents as per different international standards. Agroalimentary Process and Technol, 19, 399-404. Available at : https://journal-of-agroalimentary.ro/admin/articole/38552L64_Vol_20(1)_2014_399-404_I.pdf
Sungur, S., Okur, R., Turgut, F. H., Ustun, I., & Gokce, C. (2015). Migrated phthalate levels into edible oils. Food Additives & Contaminants: Part B, 8(3), 190-194. https://doi.org/10.1080/19393210.2015.1041065
Taghilou, S., & Hosseini, M. (2015). Review of Phthalates Exposure and Toxicity. Jorjani Biomedicine Journal, 3(2), 1-13. Available at: https://goums.ac.ir/jorjanijournal/article-1-402-en.pdf
The European Parliament and The Council Of The European Union (2005). DIRECTIVE 2005/84/EC OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 14 December 2005. Official Journal of the European Union, 344, pp.40-43. Available at: https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2005:344:0040:0043:en:PDF
U.S Food & Drug Administration (2007). Guidance for Industry: Preparation of Premarket Submissions for Food Contact Substances (Chemistry Recommendations). Docket Number: FDA-2020-D-1925. Available at: https://www.fda.gov/regulatory-information/search-fda-guidance-documents/guidance-industry-preparation-premarket-submissions-food-contact-substances-chemistry#ai
United States Consumer Product Safety Commission (2010). Toxicity Review of Di(isodecyl) Phthalate. Available at: https://www.cpsc.gov/s3fs-public/toxicityDIDP.pdf
United States Consumer Product Safety Commission (2011). TOXICITY REVIEW FOR DIISOOCTYL PHTHALATE (DIOP). Available at: https://www.cpsc.gov/s3fs-public/diop.pdf
United States Consumer Product Safety Commission (2011). TOXICITY REVIEW FOR DIMETHYL PHTHALATE (DMP, CASRN 131-11-3). Available at: https://www.cpsc.gov/s3fs-public/dmp.pdf
United States Consumer Product Safety Commission (2011). TOXICITY REVIEW FOR DICYCLOHEXYL PHTHALATE (DCHP, CASRN 84-61-7). Available at: https://www.cpsc.gov/s3fs-public/ToxicityReviewOfDCHP.pdf
United States Consumer Product Safety Commission (2011). TOXICITY REVIEW FOR DIETHYL PHTHALATE (DEP). Available at: https://www.cpsc.gov/s3fs-public/ToxicityReviewOfDEP.pdf
Wang, X., Song, M., Liu, S., Wu, S., & Thu, A. M. (2020). Analysis of phthalate plasticizer migration from PVDC packaging materials to food simulants using molecular dynamics simulations and artificial neural network. Food chemistry, 317, 126465. https://doi.org/10.1016/j.foodchem.2020.126465.
Yan, Y., Zhu, F., Zhu, C., Chen, Z., Liu, S., Wang, C., & Gu, C. (2021). Dibutyl phthalate release from polyvinyl chloride microplastics: Influence of plastic properties and environmental factors. Water research, 204, 117597. https://doi.org/10.1016/j.watres.2021.117597
Journal of Food Biosciences and Technology,
Islamic Azad University, Science and Research Branch, Vol. 14, No. 4, 61-77, 2024
https://dorl.net/dor/20.1001.1.22287086.2021.11.2.1.5
Comparative Analysis of Phthalates Migration into Mayonnaise and Mustard Sauce from Polyethylene Terephthalate (PET) Containers
M. Samadi a, M. Mizani b *, Sh. Shoeibi c
a MSc Student of the Department of Food Science and Technology, Science and Research Branch, Islamic Azad University, Tehran, Iran.
b Professor of the Department of Food Science and Technology, Science and Research Branch, Islamic Azad University, Tehran, Iran.
c Associate Professor of Food and Drug Administration, Iran Ministry of Health and Medical Education, Tehran, Iran.
Received: 7 January 2025 Accepted: 27 February 2025
ABSTRACT: The use of sauces packaged in Polyethylene terephthalate (PET) bottles is widespread in households, restaurants, and fast-food establishments. This research focuses on comparing the migration of phthalates from PET bottles into mayonnaise and mustard sauces, adhering to guidelines set forth by the British Standard, European Union (EU) Commission Regulations, and the FDA. The study employed food simulants and PET bottle samples directly sourced from production lines to measure the Overall Migration Limit (OML). In this investigation, the presence of five types of phthalates, namely DEHP, DBP, BBP, DINP, and DIOP were analyzed in PET bottles used for packaging these sauces. The OML levels in the PET bottle samples for both mayonnaise and mustard sauces were significantly below the EU regulation limit. Only DIOP was detected in the PET bottles used for mayonnaise sauce. For mustard sauce, both DEHP and DIOP were detected simultaneously. The levels of DIOP in mayonnaise and mustard sauces were well below the EU's specified SML. However, DEHP levels in mustard sauce slightly exceeded the specified SML value. The ratio of migrant milligrams per kilogram of sauce and the migration percentage of phthalates were calculated, providing a comprehensive analysis of phthalate migration dynamics. These results underscore the importance of continuous monitoring and stringent compliance with regulatory guidelines to ensure the safety of PET-packaged food products.
Keywords: Mayonnaise, Migration, Mustard Sauce, Phthalates, Plasticizer, Polyethylene terephthalate
Introduction1
Packaging is widespread and necessary in modern day life. It improves, and safeguards the products from the stage of processing and manufacturing to the final consumer through storage and handling (Robertson, 2013). The packaging industry is the largest end-user industry, as it has the highest market share, primarily due to its applications in the food and beverage sectors, where it is used in bottles, jars, and containers (Mordorintelligence, 2023). Polyethylene terephthalate, usually abbreviated as PET, PETE, is one of the most widespread thermoplastic polymers. It is a popular choice for the safe packaging of food items in the food and beverage industry due to its exceptional
physical and chemical properties (Nisticò, 2020; fnfresearch, 2023; Joseph et al., 2024; Askar et al., 2023; Conroy & Zhang, 2024). This poylmer was patented in 1941 and is currently owned by DuPont Teijin Films (fnfresearch, 2023). It has recently become the third most commonly used plastic in the packaging industry, and its demand continues to rise (Nisticò, 2020).
This indicates it is readily reprocessable at high temperatures. It is colourless and can be either semitransparent (if it is semicrystalline) or transparent (if it is amorphous). It is a noteworthy feature because it facilitates consumers to observe the contents of the container (Nisticò, 2020; fnfresearch, 2023). The demand for the plastic packaging industry is being driven by the growth prospects of end-user segments, including fast-moving consumer goods (FMCG), food and beverages, pharmaceuticals, and others (Figure 1) (mordorintelligence, 2023).
In 2021, the global market for polyethylene terephthalate (PET) was reported to be $37.25 billion. With a compound annual growth rate (CAGR) of approximately 10% from 2022 to 2030, it is expected that the market will reach $41 billion by 2030 (fnfresearch, 2023).
Interactions between the product and the packaging material is one of the most essential and extensively investigated fields of food packaging. These interactions can be categorised into three primary forms:
o Migration (the transfer of mass from packaging components to food)
o Absorption/Scalping (mass transfer of food constituents to packaging)
o Permeation (water vapor or oxygen transfer through plastic packaging to food) (Oromiehie, 2009; Hosseini et al., 2016).
Plastic-forming monomers and additives (such as softeners, plasticisers, and antioxidants) penetrate the material in contact with them from the polymer structure during the migration process. This process leads to a variety of safety-related concerns, as numerous of these migrating compounds are toxicologically harmful and deleterious to the consumer's health (Oromiehie, 2009). The specific migration of plasticisers to food or food simulants has been the subject of numerous investigations. As of June 2017, Figure 2 illustrates the number of sources available regarding the migration of each plasticiser family into food (Nerin et al., 2018).
[1] * Corresponding Author: m.mizani@srbiau.ac.ir
It is clear that phthalates have been the subject of extensive research, with a total of 203 sources. Their importance originates not only from their abundance but also from their detrimental impacts on the health of both humans and animals. Phthalates account for more than 80% of the production of plasticizers due to their excellent plasticizing properties at low cost (Nerin et al., 2018).
Phthalates, or phthalic acid esters, are synthetic organic chemicals that were first introduced in the 1920s (Nerin et al., 2018). Figure 3 (R and R' = CnH2n+1) (SHEETS, 2007; Fan et al., 2017) illustrates the general chemical structure of phthalates:
Fig. 3. Chemical structure of PAEs
(R1 and R2 represent the alkane or aromatic hydrocarbon group) (SHEETS, 2007; Fan et al., 2017)
Phthalates are widely used in various applications, such as food packaging, printing inks, pharmaceuticals, films, coatings, regenerated cellulose layers, paper-aluminium foil sheets, sealed bottles, paints, aroma preservation, nutritional supplements, glues, and adhesives (Heudorf et al., 2007; Gao et al., 2013; X.-L. Cao et al., 2015; Harunarashid et al., 2017; Kiani et al., 2018). The free mobile phase of phthalates, which are not chemically bound to plastic materials, has the potential to migrate, leak, or evaporate in a variety of environments, including the open air, indoor air, atmosphere, drinking water, food, soil, personal care, cosmetics, and other materials (Heudorf et al., 2007; Fan et al., 2017; Taghilou & Hosseini, 2015). These compounds may be released from soft plastic over time into the environment or in the food products (Gao et al., 2013; X.-L. Cao et al., 2015; Liu et al., 2020). The structures and characteristics of phthalates that are typically investigated in food and food packaging materials are summarised in Table 1 (Cao, 2010; CPSC, 2010; CPSC, 2011; IARC, 2013; NICNAS, 2014; NICNAS, 2015; ECHA, 2013; ECHA, 2014; Pubchem, 2024).
Food is the primary source of human exposure to phthalates, despite the fact that consumer products and other domestic appliances are the most significant sources of phthalate exeposure (Heudorf et al., 2007; Harunarashid et al., 2017). Consequently, it is advantageous to monitor the concentrations of phthalates in a variety of materials in order to evaluate human exposure (Cao, 2010). The presence of phthalates in food contact materials, including packaging materials,
Table 1. The structures and characteristics of phthalates (Cao, 2010; CPSC, 2010; CPSC, 2011; IARC, 2013; NICNAS, 2014; NICNAS, 2015; ECHA, 2013; ECHA, 2014; Pubchem, 2024) | Log Kow | 1.6 | 2.21-3.27 | 3.4 | 4.27 | 4.27 | 4.84 | 3-4 | 6 | 7.73 | 7.73 | 8.39 | 9.37 | 9.46 |
Water solubility (mg/L) | 2800-4300 | 1000 | 108.1 (20 °C) | 0.01 | 11.2 | 3.8 | 4.0 (24 °C) | 0.159 | 0.27 | 2.49 × 10 -3 | 0.27 | <0.001 | 1.19 | |
Vapor Pressure (Pa) | 0.41 | 0.279 | 1.75 × 10 -2 | 634.61 | 4.73 × 10 -3 | 0.00112 | 13.3 (150 °C) | 3.45 × 10 -4 | 0.0255 (KPa) | 189.32 | 1330 (200 °C) | 0.0547 | 5.1 × 10 -5 | |
m.p. (°C) | 2 | -3 | -31 | -64 | -35 | <-35 | 66 | -27.4 | -55 | -25 | -45 | -48 | -50 | |
b.p. (°C) | 283.7 | 298 | 303.8-305 (760mmHg) | 327 | 340 | 370 | 222 to 228 (0.5 kPa) | 350 | 384 | 390 | 370 / 230 (0.53 kPa) | 370 | >400 | |
Density (g/mL) (25 °C ) | 1.19 | 1.12 | 1.078 | 1.039 | 1.045 (20 °C ) | 1.119 | 1.383 | 1.011 | 0.981 | 0.985 | 0.983 | 0.972 | 0.966 | |
Fw | 194.19 | 222.4 | 250.29 | 278.35 | 278.35 | 312.4 | 330.4 | 334.46 | 390.56 | 390.6 | 390.6 | 418.6 | 446.7 | |
Formula | C10H10O4 | C12H14O4 | C14H18O4 | C16H22O4 | C16H22O4 | C19H20O4 | C20H26O4 | C20H30O4 | C24H38O4 | C24H38O4 | C24H38O4 | C26H42O4 | C28H46O4 | |
CAS Number | 131-11-3 | 84-66-2 | 131-16-8 | 84-69-5 | 84-74-2 | 85-68-7 | 84-61-7 | 84-75-3 | 117-81-7 | 117-84-0 | 27554-26-3 | 68515-48-0; 28553-12-0 | 68515-49-1; 26761-40-0 | |
Phthalates | Dimethyl phthalate (DMP) | Diethyl phthalate (DEP) | Dipropyl phthalate (DPP) | Di-iso-butyl phthalate (DIBP) | Di-n-butyl phthalate (DBP) | Butyl benzyl phthalate (BBP) | Dicyclohexyl phthalate (DCHP) | Di-n-hexyl phthalate (DHP) | Di-2-ethylhexyl phthalate (DEHP) | Di-n-octyl phthalate (DOP) | Di-iso-octyl phthalate (DIOP) | Di-iso-nonyl phthalate (DINP) | Di-iso-decyl phthalate (DIDP) |
food processing machinery, and contaminated food and beverages, is suspected to be the primary cause of this exposure. Phthalates are typically found in fatty and acidic environments (Anggarkasih et al., 2018), and their solubility in water is limited (Sungur et al., 2015).
Mayonnaise is an emulsion of oil droplets in water, despite the fact that the oil concentration is often more than 80% (Featherstone, 2015; Morley, 2016). The compositional standards vary widely, but there is joint agreement on the critical ingredients of vegetable oil, acidifying agents, and egg components (Morley, 2016).
Mustard sauce is typically made by combining ground, defatted mustard seeds with water, vinegar, salt, oil, and other seasonings to form a slurry (Garcıa-Casal et al., 2016).
The migration of additives and degradable products from plastic packaging materials to food in mixed-use environments has become a global issue as a result of the excessive human exposure to these toxic pollutants. It is imperative to identify the migration of additives in various conditions and to thoroughly recognise the interaction between food and packaging in order to guarantee the quality and shelf life of food, as a result of the excessive use of additives in materials (Wang et al., 2020).
This study set out to achieve the following objectives: 1) Establishing a practical and appropriate method for measuring the migration rate of phthalates in mustard sauce and mayonnaise in a laboratory setting 2) Examining the migration rate of the phthalates that were evaluated to mayonnaise and mustard sauce in polyethylene terephthalate packaging 3) Examining the impact of pH value and fat content on the quantity of phthalates that migrate from packaging to mayonnaise and mustard sauce at a specific temperature and time. 4) Assessing the suitability of this packaging for the storage of mustard sauce and mayonnaise.
Materials and Methods
- Materials
Polyethylene terephthalate (PET) unfilled bottles used for mayonnaise and mustard sauce were prepared from one of the well-known food industry factories in Iran. The sample bottles were kept at room temperature and away from direct sunlight. Acetic acid and ethanol, used for the preparation of food simulant solutions, were purchased from Merck, Germany. Phthalate’s standards including di(2-ethylhexyl) phthalate (DEHP), dibutyl phthalate (DBP), benzyl butyl phthalate (BBP), diisononyl phthalate (DINP), and diisooctyl phthalate (DIOP) were also obtained from Merck, Germany.
- Methods
- Food Simulants Preparation
Migration tests were conducted using food simulants in accordance with the European Union Commission Regulation No 10/2011 and Regulation No 2020/1245, Directive 2005/84/EC, British Standard EN 1186-1:2002 and 1186-3:2002, and the American Food and Drug Administration (FDA) (British Standard, 2002a; British Standard, 2002b; FDA, 2007; European Commission, 2011a; European Commission, 2020b). This was necessary due to the complexity of the food matrix and the microstructures of packaging materials.
The food simulants were selected as follows:
1. Acidic food simulant: A simulant solution with a pH of 4.5 or less, such as 3% acetic acid, has been chosen due to the pH of mayonnaise and mustard sauce (4.1 and 3.8, respectively).
2. Fatty food simulants: Olive oil (simulant D2) was selected to test these samples. However, previous studies suggest that the dissolution of DBP in olive oil makes this type of simulant D2 unsuitable for the analysis of DBP residues. Therefore, Anggarkasih et al. (2018) suggested that 95% ethanol be employed as a food simulant for fatty food products. In addition, this simulant was the best option to provide acceptable results without temperature restrictions and approved by the European Union and the US Food and Drug Administration (FDA).
3. Fatty-acidic food simulant: an intermediate-natured simulant was also necessary. The most similar state to the combined nature of fatty-acidic foods was determined to be 10% ethanol. This solution has been classified by the US Food and Drug Administration as an acidic-aqueous substance. It may contain either salt, sugar, or both, as well as oil-in-water emulsions with either low or high fat content.
- Overall Migration Test
The migration tests were conducted according to the European Union Commission Regulation No 10/2011 and Regulation No 2020/1245, Directive 2005/84/EC, British Standard EN 1186-1:2002 and 1186-3:2002, and the American Food and Drug Administration (FDA) guidance document, at ambient temperature (24.6 °C) and 40% humidity as follows:
At first, the bottle samples of mayonnaise and mustard sauce were cut into strips with a scale of 10 cm x1 cm x 0.00543 cm and 10 cm x1 cm x 1.026 cm, respectively (Figure 4). Then, the test tubes were filled with three selected food simulants, and the pre-cut pieces of polyethylene terephthalate (PET) bottles were placed in each tube and tightly closed. For each type of food simulant, six test tubes were prepared for mayonnaise and six for mustard sauce PET bottles. Considering 4 repetitions to measure the overall migration test, 1 repetition to measure the number of migrated phthalates by gas chromatography (specific migration test), and 1 for blank simulant. The test tubes were kept at a temperature of 40°C in an oven (Fanazmagostar model CM55) for a period of 10 days before being used for further analysis (Figure 5).
Fig. 4. Pre-cut pieces of PET bottles used for mayonnaise and mustard sauces
The test tubes were taken out from the oven after 10 days, and the overall migration measurement was determined based on four treatments of each food sample. In addition, the contents of each tube were transferred to a pre-weighed beaker. The beakers were then heated to evaporate the food simulants, and subsequently placed in an oven at 70°C for 2 hours to ensure complete drying. Finaly, the beakers were placed in a desiccator for a minimum of 24 hours to reach a constant weight (Figure 5). All 30 beakers were re-weighed and the overall migration was calculated for each treatment according to BS EN 1186-1:2002 and 1186- 3:2002 (British Standard, 2002a, 2002b) through equation 1:
M = 
(
) (Eq 1)
Where M represents the overall migration in milligrammes per square decimetre of surface area of the sample, ma is the mass of the residue from the test specimen after evaporation of the simulant in which it was immersed in grammes, and mb is the mass of residue from the blank simulant in grammes (British Standard, 2002b).
The final overall migration was calculated using the average of the overall migrations in all of the three food simulants, which was measured separately for each PET pre-cut samples.
- Specific Migration Test
The specific migration tests were accomplished on pre-cut pieces of PET bottle samples as illustrated in Figure 5. The prepared samples were injected in gas chromatography equipped with flame ionization (GC-FID) [Varian CP 3800 (Palo Alto, California, USA), and Agilent capillary column (5 μm × 0.53 mm × 30 m, HP-5), using helium carrier gas with a pressure of 45 psi. The oven temperature was first set at 150 ºC and then increased to 280 ºC at a rate of 5 ºC / min, and finally kept constant for 5 min. The injector and detector temperatures were both set at 300 ºC. The injection mode was split with a split ratio of 1:5, and the injection volume was 1 μl.
- Identification and quantification of phthalates in PET bottle samples of mayonnaise and mustard sauce
Results and Discussion
- Pre-cut samples of mayonnaise and mustard sauce’ bottles
According to the dimensions of the pre-cut samples of PET bottles of mayonnaise and mustard sauce, the surface areas calculated were 0.2119 dm² and 0.2226 dm², respectively. Table 2 represent the overall migration results.
Table 2. Overall migration in selected food simulants for mustard sauce and mayonnaise PET samples by total immersion method | ||
PET bottle type | Simulant Type | Overall Migration (mg/dm2) |
Mustard Sauce | 95% Ethanol | 1.24 ± 0.31 |
10% Ethanol | 1.65 ± 0.26 | |
3% Acetic Acid | 1.46 ± 0.43 | |
Mayonnaise | 95% Ethanol | 2.83 ± 0.82 |
10% Ethanol | 1.18 ± 0.27 | |
3% Acetic Acid | 1.89 ± 0.54 | |
The European Union Commission's regulations, No. 10/2011, pointed out the rule requiring that plastic materials and articles not transfer their constituents to foodstuffs in quantities that exceed 10 milligrammes per square decimetre of the surface area of the materials or articles (overall migration limit) (European Commission, 2011) and the results presented in Table 2 indicate that the overall migration in this study is lower than the limit established by the European Union.
Ashby et al. 1988 analysed the impact of varying the surface-to-volume ratio by exposing a biaxially oriented 125-micrometre PET film to 110 cm³ of olive oil as a fatty food simulant at 40°C for 10 days, using contact areas of 1, 2, and 4 dm². The results indicate that there is no significant difference in migration levels. Agiotti et al. 2022 analyzed the release of selected non-intentionally added substances (NIAS) from PET food contact materials using 3% acetic acid as an aqueous food simulant at 60°C for 10 days, using a contact area of 4 dm². The amount of overall migration was lower than 0.1 mg/dm2. Satish et al. 2013 carried out a study on the migration aspects of food-contact materials using aqueous food-simulating solvents, in accordance with various international standards. A 10% ethanol solution was used as an aqueous food simulant at 40°C for 10 days with a contact area of 5 dm². The amount of overall migration was determined to be 0.38 ± 0.05 mg/dm². Hosseini et al. 2016 analyzed the migration of dibutyl phthalate and dimethyl phthalate into rose water packaged in PET containers using 3% acetic acid and 10% ethanol as acidic and aqueous food simulants, respectively, at 4, 25, and 42 °C for 2 days, 2 weeks, and 2 months, using a contact area of 1 dm². 1.1 mg/dm² was the overall migration for
aqueous food with a pH greater than 4.5, while 2.3 mg/dm² was the migration for aqueous food with a pH less than 4.5.
Therefore, the overall migration in all four above mentioned investigations is lower than the amounts obtained from the current study (Table 2), and the value approved by the EU Commission regulations, with the exception of the data results from Hosseini et al. 2016.
Despite the minor differences in the time and temperature conditions, the values for aqueous food with a pH higher than 4.5 were comparable to our findings for 10% ethanol (food simulant: mayonnaise PET bottle).
- Specific migrations from PET bottle samples into food simulants
The chromatograms for phthalate standard solutions including DEHP, DBP, BBP, DINP, and DIOP are illustrated in Figure 6. The chromatograms for the migration of pre-cut segments into food simulants (3% acetic acid, 10% ethanol, and 95% ethanol) for mayonnaise and mustard sauce are presented in Figures 7 and 8, respectively.
The results show that DEHP and DIOP, as phthalates, migrated from PET bottles of mayonnaise and mustard sauce into food simulants. Table 3 reports the specific migration quantities. The European Union Commission (2011/10) determined a special migration limit of mg/kg (mg/l) for the migrated DIOP, which is much lower
PET bottle type | Food Simulants | Phthalate compound | Specific Migration (mg/l) |
Mustard Sauce | 3% Acetic Acid | DEHP | 2.4 |
DIOP | 6.7 | ||
10% Ethanol | DEHP | 3.6 | |
DIOP | 3.4 | ||
%95 Ethanol | DIOP | 1.3 | |
Mayonnaise | 3% Acetic Acid | DIOP | 1.7 |
10% Ethanol | DIOP | 4.8 | |
%95 Ethanol | DIOP | 3.4 |
Fig. 6. Gas chromatogram of the examined phthalate standard with following retention times (minutes): DBP = 10.748, BBP = 17.665, DEHP = 18.249, DIOP = 20.660, and DINP = 25.486
Fig. 7. Identification of phthalates migrated into 3 food simulants including: a) 3% acetic acid, b) 10% ethanol, and c) 95% ethanol from mustard sauce PET bottles
Fig. 8. Identification of phthalates migrated into 3 food simulants including: a) 3% acetic acid, b) 10% ethanol, and c) 95% ethanol from mayonnaise PET bottles
than this limit. However, the value of DEHP is slightly higher than the specified limit of 1.5 mg/kg (mg/l) for this compound, which is identified as the main plasticizer of PET bottles (Mukhopadhyay et al. 2022).
- Identification and quantification of phthalates presented in the PET bottle samples
Figure 9 illustrate the two chromatograms that were obtained from analyzing the PET bottle samples. The quantity of different phthalate compounds detected in the PET bottle samples, are
given in Table 4.
At present, there is no established regulation that governs the permissible level of phthalates in PET containers. The only published investigation to date was the annex of the 2005/84/EC European Union Directive, which specified the permissible level of phthalates in toys and equipment for children. This document encompassed two groups of phthalates: three types DEHP, DBP, and BBP, and DINP, DIDP, and DNOP were mentioned in the first and second groups, respectively, with the maximum level of 0.1% by weight for each group.
Fig. 9. Identification of the phthalates presented in a) Mustard sauce and b) Mayonnaise PET bottles
DEHP was the only phthalate compound detected in both the mustard sauce and mayonnaise PET bottles with concentrations of 61.3 mg/l (0.00613%) and 49.7 mg/l (0.00497%), respectively (Table 4). Consequently, the quantity of DEHP that was identified in the PET bottle samples is substantially lower than the permissible limit specified in this document.
Table 4. The quantity of phthalates detected in PET bottle samples | ||
PET bottle type | Phthalate type | Phthalate Amount (mg/l) |
Mustard Sauce | DEHP | 61.3 |
DIOP | 92.1 | |
Mayonnaise | DEHP | 49.7 |
DIOP | 83.2 | |
- The amount (%) of migrated phthalates into food simulants as compared to the quantity presented in the PET bottles
Table 5 shows the results of making a comparison between the quantity of phthalate compounds potentially presented in PET bottle samples with the values migrated into different food simulants.
The milligram amount of migrants per kilogram of the food simulants can be determined separately for PET bottles of each type of sauce by taking into account the size of the surface area of the PET bottle, the volume of each food sample that is in contact with this surface area, and the overall migration in each food simulant (Table 6).
· Overall migration is significantly less than what the European Union Commission specified.
· The DIOP levels in both sauce were significantly lower than the EU's specific migration limit, while the DEHP level in mustard sauce slightly exceeded it.
· The permissible limit was not exceeded by the levels of DEHP and DIOP that were detected in both PET bottles.
In order to obtain a more precise and exhaustive interpretation of phthalate migration, it is imperative to investigate the solubility of phthalates, as indicated by the findings of this study. The nature and structure of the food matrix, as well as pH, temperature, and time, all have an impact on phthalates during the migration process. Consequently, it is essential to study solubility in the environment where migration takes place. As a result, the solubility of phthalate compounds should be assessed under the appropriate
Table 5. The amount (%) of phthalates migrated to food simulants as compared to the phthalates in the PET bottles
The type and amount of phthalates in polyethylene terephthalate (PET) bottles (mg/l) | The type and amount of phthalates migrated to the food simulants (mg/l) | The ratio of phthalates migrated from packaging to food simulants (%) | ||
Mustard Sauce | DEHP = 61.3
DIOP = 92.1 | 3% Acetic Acid | DEHP = 2.4 | DEHP = 3.91 |
DIOP = 6.7 | DIOP = 7.27 | |||
10% Ethanol | DEHP = 3.6 | DEHP = 5.87 | ||
DIOP = 3.4 | DIOP = 3.69 | |||
%95 Ethanol | DIOP = 1.3 | DIOP = 1.41 | ||
Mayonnaise | DEHP = 49.7
DIOP = 83.2 | 3% Acetic Acid | DIOP = 1.7 | DIOP = 2.04 |
10% Ethanol | DIOP = 4.8 | DIOP = 5.77 | ||
%95 Ethanol | DIOP = 3.4 | DIOP = 4.09 | ||
Table 6. The milligram amount of migrants per kilogram of the food simulant
Volume of Simulant / Surface Area | Type of food Simulants | Calculations (mg Migrant/Kg simulant) |
Mustard Sauce PET Bottle: 25 cc (Kg) Simulant Surface Area = 0.226 dm2 | 3% Acetic Acid | 13.19 |
10% Ethanol | 14.89 | |
%95 Ethanol | 11.17 | |
Mustard Sauce PET Bottle: 25 cc (Kg) Simulant Surface Area = 0.2119 dm2 | 3% Acetic Acid | 16.00 |
10% Ethanol | 9.99 | |
%95 Ethanol | 23.99 |
conditions in order to plan for future advances.
Acknowledgment
The authors gratefully acknowledge Khatam Polymer Knowledge Enterprise Company for providing its facilities to conduct the relevant tests.
References
Aigotti, R., Giannone, N., Asteggiano, A., Mecarelli, E., Dal Bello, F., Medana, C. (2022). Release of Selected Non-Intentionally Added Substances (NIAS) from PET Food Contact Materials: A New Online SPE-UHPLC-MS/MS Multiresidue Method. Separations, 9, 188. https://doi.org/10.3390/
Alvarado Chacon, F., Brouwer, M. T. & Thoden van Velzen, E. U. (2020). Effect of recycled content and rPET quality on the properties of PET bottles, part I: Optical and mechanical properties. Packaging Technology and Science, 33(9), 347-357. https://doi.org/10.1002/pts.2490
Anggarkasih, M. G., Yuliana, N. D., Regiyana, Y., Massijaya, M. Y. & Budijanto, S. (2018). Analysis of Di-N-Butyl Phthalate (DBP) Residue in Commercial Food Packaging from Recycled Paper and Its Migration into Food Simulant. Jurnal Teknologi Industri Pertanian, 28(2). Retrieved from: https://jurnalpenyuluhan.ipb.ac.id/index.php/jurnaltin/article/view/24629
Anon. (2024). National Center for Biotechnology Information. PubChem Compound Summary for CID 2347, Benzyl butyl phthalate. Retrieved May 22, 2024 from https://pubchem.ncbi.nlm.nih.gov/compound/Benzyl-butyl-phthalate.
Anon. (2024). National Center for Biotechnology Information . PubChem Compound Summary for CID 33599, Diisodecyl phthalate. Retrieved May 22, 2024 from: https://pubchem.ncbi.nlm.nih.gov/compound/Diisodecyl-phthalate.
Anon. (2024). National Center for Biotechnology Information. PubChem Compound Summary for CID 590836, Diisononyl phthalate. Retrieved May 22, 2024 from: https://pubchem.ncbi.nlm.nih.gov/compound/Diisononyl-phthalate.
Anon. (2024). National Center for Biotechnology Information. PubChem Compound Summary for CID 8559, Dipropyl phthalate. Retrieved May 22, 2024 from https://pubchem.ncbi.nlm.nih.gov/compound/Dipropyl-phthalate.
Anon. (2014). National Industrial Chemicals Notification And Assessment Scheme (Australian Governments). Dimethyl phthalate. Priority Existing Chemical Assessment Report No. 37. Available at: https://www.industrialchemicals.gov.au/sites/default/files/PEC37-Dimethyl-phthalate-DMP.pdf
Anon. (2015). National Industrial Chemicals Notification And Assessment Scheme (Australian Governments). Butyl benzyl phthalate. Priority Existing Chemical Assessment Report No. 40. Available at: https://www.industrialchemicals.gov.au/sites/default/files/PEC40-Butyl-benzyl-phthalate-BBP.pdf
Anon. (2002a). BS EN 1186-1:2002, Materials and articles in contact with foodstuffs - Plastics - Part 1: Guide to the selection of conditions and test methods for overall migration. Available at: https://img.21food.cn/img/biaozhun/20090815/187/11183625.pdf
Anon. (2002b). BS EN 1186-3:2002, Materials and articles in contact with foodstuffs - Plastics - Part 3: Test methods for overall migration into aqueous food simulants by total immersion. Available at: http://files.foodmate.com/down.php?auth=B2MAY1swXTE
Anon. (2013). European Chemical Agency (ECHA). EC Number: 201-559-5, Dihexyl phthalate (DHP). Available at: https://echa.europa.eu/documents/10162/65336c46-c178-4b71-a927-15437e8b303a
Anon. (2014). European Chemical Agency (ECHA). EC Number: 201-553-2, Diisobutyl phthalate (DIBP). Available at: https://echa.europa.eu/documents/10162/12934bbe-ad6f-4671-a931-1ef44f51cb10
Anon. (2014). European Chemical Agency (ECHA). EC Number: 201-622-7, Benzyl butyl phthalate (BBP). Available at: https://echa.europa.eu/documents/10162/c5e7a581-db15-4e09-8be9-37d42c5409d8
Anon. (2011). European Commission. Commission Regulation (EU) No 10/2011 of 14 January 2011 on plastic materials and articles intended to come into contact with food. Off J Eur Union, 12, pp.1-89. Available at: https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2011:012:0001:0089:en:PDF
Anon. (2023). Polyethylene Terephthalate (PET) Market Size, Share Global Analysis Report, 2022–2030. Available at: https://www.fnfresearch.com/polyethylene-terephthalate-pet-market
Anon. (2013). IARC Working Group on the Evaluation of Carcinogenic Risks to Humans. Di (2-ethylhexyl) phthalate. In Some Chemicals Present in Industrial and Consumer Products, Food and Drinking-Water. International Agency for Research on Cancer. ISBN-13: 978-9283213246
Anon. (2024). Mordor Intelligence Research & Advisory. Polyethylene Terephthalate (PET) Market SIZE & SHARE ANALYSIS - GROWTH TRENDS & FORECASTS UP TO 2029. Mordor Intelligence. Retrieved May 23, 2024, from: https://www.mordorintelligence.com/industry-reports/polyethylene-terephtalate-market
Anon. (2005). The European Parliament and The Council Of The European Union. DIRECTIVE 2005/84/EC OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 14 December 2005. Official Journal of the European Union, 344, pp.40-43. Available at: https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2005:344:0040:0043:en:PDF
Anon. (2007). U.S Food & Drug Administration. Guidance for Industry: Preparation of Premarket Submissions for Food Contact Substances (Chemistry Recommendations). Docket Number: FDA-2020-D-1925. Available at: https://www.fda.gov/regulatory-information/search-fda-guidance-documents/guidance-industry-preparation-premarket-submissions-food-contact-substances-chemistry#ai
Anon. (2010). United States Consumer Product Safety Commission. Toxicity Review of Di(isodecyl) Phthalate. Available at: https://www.cpsc.gov/s3fs-public/toxicityDIDP.pdf
Anon. (2011). United States Consumer Product Safety Commission. TOXICITY REVIEW FOR DIISOOCTYL PHTHALATE (DIOP). Available at: https://www.cpsc.gov/s3fs-public/diop.pdf
Anon. (2011). United States Consumer Product Safety Commission. TOXICITY REVIEW FOR DIMETHYL PHTHALATE (DMP, CASRN 131-11-3). Available at: https://www.cpsc.gov/s3fs-public/dmp.pdf
Anon. (2011). United States Consumer Product Safety Commission. TOXICITY REVIEW FOR DICYCLOHEXYL PHTHALATE (DCHP, CASRN 84-61-7). Available at: https://www.cpsc.gov/s3fs-public/ToxicityReviewOfDCHP.pdf
Anon. (2011). United States Consumer Product Safety Commission (2011). TOXICITY REVIEW FOR DIETHYL PHTHALATE (DEP). Available at: https://www.cpsc.gov/s3fs-public/ToxicityReviewOfDEP.pdf
Ashby, R. (1988). Migration from polyethylene terephthalate under all conditions of use. Food Additives & Contaminants, 5(S1), 485-492. https://doi.org/10.1080/02652038809373681
Askar, M. K., Al-Kamaki, Y. S. & Hassan, A. (2023). Utilizing polyethylene terephthalate PET in concrete: A review. Polymers, 15(15), 3320. https://doi.org/10.3390/polym15153320
Cao, X. L. (2010). Phthalate esters in foods: sources, occurrence, and analytical methods. Comprehensive reviews in food science and food safety, 9(1), 21-43. https://doi.org/10.1111/j.1541-4337.2009.00093.x
Cao, X. L., Zhao, W. & Dabeka, R. (2015). Di-(2-ethylhexyl) adipate and 20 phthalates in composite food samples from the 2013 Canadian Total Diet Study. Food Additives & Contaminants: Part A, 32(11), 1893-1901. https://doi.org/10.1080/19440049.2015.1079742
Conroy, S. & Zhang, X. (2024). Theoretical insights into chemical recycling of polyethylene terephthalate (PET). Polymer Degradation and Stability, 110729. https://doi.org/10.1016/j.polymdegradstab.2024.110729
Fan, Y., Chen, H., Liu, H., Wang, F., Ma, S., Latipa, A. & Wang, C. (2017). Analysis of phthalate esters in dairy products—a brief review. Analytical methods, 9(3), 370-380. https://doi.org/10.1039/C6AY02885C
Fasano, E., Bono-Blay, F., Cirillo, T., Montuori, P. & Lacorte, S. (2012). Migration of phthalates, alkylphenols, bisphenol A and di (2-ethylhexyl) adipate from food packaging. Food control, 27(1), 132-138. https://doi.org/10.1016/j.foodcont.2012.03.005
Featherstone, S. (Ed.). (2015). A complete course in canning and related processes: Volume 3 Processing Procedures for Canned Food Products. Woodhead Publishing. eBook ISBN: 9780857096876
Gao, X., Yang, B., Tang, Z., Luo, X., Wang, F., Xu, H. & Cai, X. (2014). Determination of phthalates released from paper packaging materials by solid-phase extraction–high-performance liquid chromatography. Journal of chromatographic science, 52(5), 383-389. https://doi.org/10.1093/chromsci/bmt046
García‐Casal, M. N., Peña‐Rosas, J. P. & Malavé, H. G. (2016). Sauces, spices, and condiments: definitions, potential benefits, consumption patterns, and global markets. Annals of the New York Academy of Sciences, 1379(1), 3-16. https://doi.org/10.1111/nyas.13045
Haji Harunarashid, N. Z. I., Lim, L. H. & Harunsani, M. H. (2017). Phthalate sample preparation methods and analysis in food and food packaging: a review. Food Analytical Methods, 10, 3790-3814. https://doi.org/10.1007/s12161-017-0938-7
Heudorf, U., Mersch-Sundermann, V. & Angerer, J. (2007). Phthalates: toxicology and exposure. International journal of hygiene and environmental health, 210(5), 623-634. https://doi.org/10.1016/j.ijheh.2007.07.011
Hosseini, S. J., Homayouni, A., Ghanbarzadeh, B., Sobhani, Z. & Yousefi, G. H. (2016). Migration of dibutyl phthalate and dimethyl phthalate in rose water packaged in polyethylene terephthalate containers. Available at: https://nsft.sbmu.ac.ir/article-1-1957-en.pdf
Joseph, T. M., Azat, S., Ahmadi, Z., Jazani, O. M., Esmaeili, A., Kianfar, E. & Thomas, S. (2024). Polyethylene terephthalate (PET) recycling: A review. Case Studies in Chemical and Environmental Engineering, 100673. https://doi.org/10.1016/j.cscee.2024.100673
Kiani, A., Ahmadloo, M., Shariatifar, N., Moazzen, M., Baghani, A. N., Khaniki, G. J. & Ghajarbeygi, P. (2018). Method development for determination of migrated phthalate acid esters from polyethylene terephthalate (PET) packaging into traditional Iranian drinking beverage (Doogh) samples: a novel approach of MSPE-GC/MS technique. Environmental Science and Pollution Research, 25, 12728-12738. https://doi.org/10.1007/s11356-018-1471-y
Liu, F. F., Liu, G. Z., Zhu, Z. L., Wang, S. C. & Zhao, F. F. (2019). Interactions between microplastics and phthalate esters as affected by microplastics characteristics and solution chemistry. Chemosphere, 214, 688-694. https://doi.org/10.1016/j.chemosphere.2018.09.174
Liu, J. M., Li, C. Y., Zhao, N., Wang, Z. H., Lv, S. W., Liu, J. C. & Wang, S. (2020). Migration regularity of phthalates in polyethylene wrap film of food packaging. Journal of Food Science, 85(7), 2105-2113. https://doi.org/10.1111/1750-3841.15181
Morley, W. G. (2016). Mayonnaise. https://doi.org/10.1016/B978-0-12-384947-2.00449-9
Mukhopadhyay, M., Jalal, M., Vignesh, G., Ziauddin, M., Sampath, S., Bharat, G. K. & Chakraborty, P. (2022). Migration of plasticizers from polyethylene terephthalate and low-density polyethylene casing into bottled water: a case study from India. Bulletin of Environmental Contamination and Toxicology, 109(6), 949-955. https://doi.org/10.1007/s00128-022-03474-x
Nerin, C., Canellas, E., & Vera, P. (2018). Plasticizer migration into foods. http://dx.doi.org/10.1016/B978-0-08-100596-5.21392-9
Nisticò, R. (2020). Polyethylene terephthalate (PET) in the packaging industry. Polymer Testing, 90, 106707. https://doi.org/10.1016/j.polymertesting.2020.106707
Oromiehie, A. (2010). Plastic packaging food and drug principles and testing methods. Tehran, Iran: Ideh Pardazan Fan & Honar Publications, pp. 29 & 81-82. ISBN: 978-964-2559-19-0
Rahimi, L., Ghanbarzadeh, B. & Dehghannya, J. (2016). Migration of phthalate esters from polyethylene terephthalate into a lemon juice simulant. Iranian Food Science and Technology Research Journal, 12(1), pp.79-87. Available at: https://ifstrj.um.ac.ir/article_35196_70f56ec45277c0d08204f7c024ce8c4d.pdf?lang=en
(2013). Food packaging: principles and practice (3rd ed.). Boca Raton: CRC Press. https://doi.org/10.1201/b21347
SHEETS, F. (2007). Breast Cancer & the Environment Research Centers. Available at: https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=7f48554bf7cd1fa683f45dc8bb43a6b1922050cb
Satish, A., Lasya, M., Harini, S., Padmavathi, S. & Baldev, R. (2013). Migration aspects for food contact materials with aqueous food simulating solvents as per different international standards. Agroalimentary Process and Technol, 19, 399-404. Available at : https://journal-of-agroalimentary.ro/admin/articole/38552L64_Vol_20(1)_2014_399-404_I.pdf
Sungur, S., Okur, R., Turgut, F. H., Ustun, I. & Gokce, C. (2015). Migrated phthalate levels into edible oils. Food Additives & Contaminants: Part B, 8(3), 190-194. https://doi.org/10.1080/19393210.2015.1041065
Taghilou, S. & Hosseini, M. (2015). Review of Phthalates Exposure and Toxicity. Jorjani Biomedicine Journal, 3(2), 1-13. Available at: https://goums.ac.ir/jorjanijournal/article-1-402-en.pdf
Wang, X., Song, M., Liu, S., Wu, S. & Thu, A. M. (2020). Analysis of phthalate plasticizer migration from PVDC packaging materials to food simulants using molecular dynamics simulations and artificial neural network. Food chemistry, 317, 126465. https://doi.org/10.1016/j.foodchem.2020.126465.
Yan, Y., Zhu, F., Zhu, C., Chen, Z., Liu, S., Wang, C. & Gu, C. (2021). Dibutyl phthalate release from polyvinyl chloride microplastics: Influence of plastic properties and environmental factors. Water research, 204, 117597. https://doi.org/10.1016/j.watres.2021.117597
