Abstract:The acetaldehyde (AA) scavenging mechanisms of anthranilamide, metaxylenediamine (MXDA), and alpha-cyclodextrin were investigated through a combination of proton nuclear magnetic resonance ( 1 H-NMR) and mass spectrometry techniques. AA was found to react with the amide and amine groups of anthranilamide to produce a two-ring structure with water as a byproduct. MXDA possesses two terminal, primary amines that make it difunctional. The aldehyde group of AA reacts with each primary amine to create an imine grou… Show more
“…88-68-6; anthranilamide) is widely used as a scavenging agent for acetaldehyde during PET pre-form production in order to reduce the concentration of acetaldehyde in the PET bottle wall. Figure 1 shows the proposed mechanism of the reaction between 2-aminobenzamide and acetaldehyde during pre-form manufacturing (Mrozinski et al 2012 , 2013 ). Figure 1.…”
Polyethylene terephthalate (PET) bottles are widely used as packaging material for natural mineral water. However, trace levels of acetaldehyde can migrate into natural mineral water during the shelf life and might influence the taste of the PET bottled water. 2-Aminobenzamide is widely used during PET bottle production as a scavenging agent for acetaldehyde. The aim of this study was the determination of the migration kinetics of 2-aminobenzamide into natural mineral water as well as into 20% ethanol. From the migration kinetics, the diffusion coefficients of 2-aminobenzamide in PET at 23 and 40°C were determined to be 4.2 × 10−
16 and 4.2 × 10−
15 cm2 s–1, respectively. The diffusion coefficient for 20% ethanol at 40°C was determined to be 7.7 × 10−
15 cm2 s–1, which indicates that 20% ethanol is causing swelling of the PET polymer. From a comparison of migration values between 23 and 40°C, acceleration factors of 9.7 when using water as contact medium and 18.1 for 20% ethanol as simulant can be derived for definition of appropriate accelerated test conditions at 40°C. The European Union regulatory acceleration test based on 80 kJ mol–1 as conservative activation energy overestimates the experimentally determined acceleration rates by a factor of 1.6 and 3.1, respectively.
“…88-68-6; anthranilamide) is widely used as a scavenging agent for acetaldehyde during PET pre-form production in order to reduce the concentration of acetaldehyde in the PET bottle wall. Figure 1 shows the proposed mechanism of the reaction between 2-aminobenzamide and acetaldehyde during pre-form manufacturing (Mrozinski et al 2012 , 2013 ). Figure 1.…”
Polyethylene terephthalate (PET) bottles are widely used as packaging material for natural mineral water. However, trace levels of acetaldehyde can migrate into natural mineral water during the shelf life and might influence the taste of the PET bottled water. 2-Aminobenzamide is widely used during PET bottle production as a scavenging agent for acetaldehyde. The aim of this study was the determination of the migration kinetics of 2-aminobenzamide into natural mineral water as well as into 20% ethanol. From the migration kinetics, the diffusion coefficients of 2-aminobenzamide in PET at 23 and 40°C were determined to be 4.2 × 10−
16 and 4.2 × 10−
15 cm2 s–1, respectively. The diffusion coefficient for 20% ethanol at 40°C was determined to be 7.7 × 10−
15 cm2 s–1, which indicates that 20% ethanol is causing swelling of the PET polymer. From a comparison of migration values between 23 and 40°C, acceleration factors of 9.7 when using water as contact medium and 18.1 for 20% ethanol as simulant can be derived for definition of appropriate accelerated test conditions at 40°C. The European Union regulatory acceleration test based on 80 kJ mol–1 as conservative activation energy overestimates the experimentally determined acceleration rates by a factor of 1.6 and 3.1, respectively.
“…AA scavengers are used in the PET bottles for mineral water to minimize AA content of the melt-processed polymeric materials, avoiding its migration into beverages, [7,[51][52][53]. Generally, to reduce the generation of AA during the PET pre-form production is used the 2-aminobenzamide, also known as anthranilamide [7,[51][52][53], for its low cost, efficiency, and ease of incorporation into PET material. It reacts with AA during the PET pre-form manufacturing as proposed by Mrozinski et al [51,52] (Scheme S1).…”
Section: Studies On Potential Functional Aldehydes Scavangersmentioning
confidence: 99%
“…Generally, to reduce the generation of AA during the PET pre-form production is used the 2-aminobenzamide, also known as anthranilamide [7,[51][52][53], for its low cost, efficiency, and ease of incorporation into PET material. It reacts with AA during the PET pre-form manufacturing as proposed by Mrozinski et al [51,52] (Scheme S1). In accord to the European Plastics Regulation No.…”
Section: Studies On Potential Functional Aldehydes Scavangersmentioning
This study focused on characterization of Volatile Organic Compounds (VOCs) as contaminants and non-volatile additives in Italian PET bottles, also suggesting potential functional aldehydes scavengers. Several VOCs, such as acetic aldehyde (AA), butanal, 3-methyl butanal, 1,3-dioxolane, pentanal, hexanal, octanal, 5-hepten-2-one, nonanal, and decanal, were identified by Head Space-Gas Chromatography/Mass Spectrometry (HS-GC/MS) in the PET bottles used for the packaging of six Italian brands mineral waters. AA, 1,3-dioxolane, octanal, 5-hepten-2-one, nonanal, and decanal were the most abundant compounds identified. These contaminants were also identified in the PET-bottled mineral waters. Different experiments using bottle-grade PET pellets (Btlg-PET) and PET bottles’ fragments with and without the addition of epoxidized soybean oil (ESBO) or erucamide as lubricant/plasticizer additives, poly(m-xylene adipamide) (MXD6), and/or anthranilamide (2-aminobenzamide) as potential aldehydes scavengers were carried out. Mostly VOCs observed in the PET bottles analysed were identified in a neat ESBO sample. The presence of the ESBO additive in the PET-bottle fragments was also observed by matrix-assisted laser desorption/ionization time of flight mass spectrometry analysis (MALDI–TOF MS). The ESBO sub-products were not observed in the virgin btlg-PET pellets analysed by both HS-GC/MS and MALDI–TOF MS. These results suggest that the VOCs come from an ESBO additive probably loaded during the blow-moulding processes used for the manufacturing of PET bottles. Further studies established that MXD6 (1%w), an efficient oxygen scavenger, could be also used as AA scavenger even in the presence of the commonly used anthranilamide.
“…After each cycle, the acetaldehyde-blocking agent anthranilamide was added with a concentration of 500 mg/kg. Anthranilamide reacts with acetaldehyde to form 2-methyl-4-hydroxy-1,3-diazanaphthalin (2-methyl-4hydroxy-chinazolin) [39]. Typical concentrations of anthranilamide in the PET bottle wall were found between 190 and 320 mg/kg [40].…”
With the European Green Deal, the importance of recycled products and materials has increased. Specifically, for PET bottles, a high content of recycled material (rPET) is demanded by the industry and consumers. This study was carried out in a lab environment replicating real-life industrial processes, to investigate the possible impacts on rPET quality over eleven recycling loops, aiming to use high amounts of rPET repetitively. A cycle included extrusion, solid state polycondensation (SSP), a second extrusion to simulate bottle production, hot wash and a drying step. 75% rPET and 25% virgin PET were extruded in eleven cycles to simulate a recycling and production process. Samples underwent chemical, physical and biological analysis. The quality of the rPET material was not adversely affected. Parameters such as coloring, intrinsic viscosity, concentration of critical chemicals and presence of mutagenic contaminants could be positively assessed. The quality of the produced material was likely influenced by the input material’s high standard. A closed loop PET bottle recycling process using an rPET content of up to 75% was possible when following the proposed process, indicating that this level of recycled content can be maintained indefinitely without compromising quality.
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