Abstract
The primary aromatic amines (PAAs) are food contaminants which may exist in packaged food. Polyurethane (PU) adhesives which are used in flexible packaging are the main source of PAAs. It is the unreacted diisocyanates which in fact migrate to foodstuff and then hydrolyze to PAAs. These PAAs include toluenediamines (TDAs) and methylenedianilines (MDAs), and the selected PAAs were 2,4-TDA, 2,6-TDA, 4,4′-MDA, 2,4′-MDA, and 2,2′-MDA. PAAs have genotoxic, carcinogenic, and allergenic effects. In this study, extraction methods were applied on a 3% acetic acid as food simulant which was spiked with the PAAs under study. Extraction methods were liquid-liquid extraction (LLE), dispersive liquid-liquid microextraction (DLLME), and solid-phase extraction (SPE) with C18 ec (octadecyl), HR-P (styrene/divinylbenzene), and SCX (strong cationic exchange) cartridges. Extracted samples were detected and analyzed by HPLC-UV. In comparison between methods, recovery rate of SCX cartridge showed the best adsorption, up to 91% for polar PAAs (TDAs and MDAs). The interested PAAs are polar and relatively soluble in water, so a cartridge with cationic exchange properties has the best absorption and consequently the best recoveries.
Highlights
Primary aromatic amines (PAAs) are food contaminants
E five primary aromatic amines (PAAs) (2,4-TDA, 2,6-TD, 4,4′-MDA, 2,4′-MDA, and 2,2′-MDA) used in this study were selected on the basis of their origin of PU adhesives used in food packaging
Toxicity of PAAs was evaluated and classified into three groups based on their levels of toxicity with 2,4-TDA, 2,6-TDA, and 4,4′MDA being in the high toxicity class [18]
Summary
Primary aromatic amines (PAAs) are food contaminants. Migration of PAAs into food is through colored plastics, printed paper, cooking utensils, and flexible packaging. One of the main sources of PAAs is polyurethane (PU) adhesives which are used extensively in lamination of multilayer films. PU adhesives might contain unreacted aromatic diisocyanates coming from the imperfect polymerization process of polyurethane; after packaging, water present in foods hydrolyzes residual aromatic diisocyanates, leading to PAA formation [1]. Toluene diisocyanate (TDI) and methylene diphenyl isocyanate (MDI) are used in the production of PU adhesives. TDIs are often a mixture (80 : 20) of the two isomers: 2,4-TDI and 2,6-TDI, while MDIs consist of a mixture of higher oligomer homologues, 4,4′-MDI (40–50%), 2,4′-MDI (2.5–4.0%), and 2,2′-MDI (0.1–0.2%) [2]
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