Table 4.
Studies published in the literature on degradation/breakdown products (NIAS) Identification in different plastic food packaging.
| Food Contact Material | NIAS | Method/Technique | Reference |
|---|---|---|---|
| Active packaging: Polypropylene (PP); PP + green tea; PP/poly (ethylene-co-vinyl alcohol) EVOH; PP/EVOH + oregano; PP/EVOH + citral; EVOH; Polyethylene terephthalate-PET/EVOH + citral; PET/EVOH + cinnamon; PP/EVOH/PP; PP/EVOH + oregano | Degradation of active compounds; impurities from the raw materials; additives used in the manufacture of the active polymer (citral thermal reaction products; oxidation product of citral; decomposition product of adipates used as plasticizers; impurity/reaction product/breakdown product for the additives used in the manufacture of PE materials; xanthenone derivates) | UPLC-QTOF-MS | [86] |
| Polyurethane adhesives in multilayer packaging materials | Silane unknown compounds; degradation of antioxidants Irgafos and Irganox (2,6-Di-tert-butylbenzoquinone; isomer 2,5-di-tert-butylbenzoquinone; 7,9-Di-tert-butyl-1-oxaspiro(4,5)deca-6,9-diene-2,8-dione; benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-methyl) | HS-SPME-GC-MS | [67] |
| Hot melt adhesives (Ethylene-vinyl acetate-EVA and amorphous polyolefin APAO enriched in propene) | Degradation of Irganox 1010: 3,5-di-tert-butyl-4-hydroxybenzaldehyde | UPLC-ESI-MS/QTOF | [72] |
| Polyethylene terephthalate-PET pellets | The degradation product of the antioxidants Irgafos 168 and Irganox 1010: 2,4-bis(1,1-dimethyl ethyl) phenol; 2-methyl-1,3-dioxolane; linear aldehydes; residual monomers: ethylene glycol (EG); thermal degradation products: toluene, ethylbenzene and xylene; phthalates (DEP, DIBP) | HS-SPME/GC-MS | [73] |
| Polycarbonate (PC) | Oligomers; PC-degradation products | UHPLC–ESI Q-orbitrap | [94] |
| Polypropylene (PP) films | Degradation products from Irgafos 168, Tinuvin 326 and Irganox 1076 | HPLC-DAD and GC-FID–MS | [74] |
| Candy wrappers based on plastic and paper materials | 2,6-Di-tert-butyl-4-methylene-2,5-cyclohexadienone, a degradation product of BHT, Diethyl maleate, Triacetin, Propanoic acid, 2-methyl-, 3-Hydroxy-2,4,4-trimethylpentyl ester, Diethyl phthalate, Diisobutyl phthalate, 7,9-Di-tert-butyl-1-oxaspiro(4,5)deca-6-9-diene-2,8-dione, Heneicosane, Tributyl aconitate, Docosane, Tricosane, Tetracosane, Pentacosane, Hexacosane, Heptacosane, Octocosane, Squalene, n-Nonacosane, Glycerol tricaprylate | GC-MS | [95] |
| Polypropylene (PP) | Degradation products derived from phenolic antioxidants, impurity/reaction product/breakdown product of the additives, Family 1: Family formed with the reference structure; was formed by the compounds that had a similar structure constituted by a group 3,5-di-tert-butyl-4-hydroxyphenyl; Family 2: With glycerol molecule (glyceryl monostearate, glyceryl palmitate and glyceryl dihexadecanoate, an ester of an acid chain bonded to a glycerol molecule); Family 3: Dihydroxy alquilamines (amine bonded to two ethanol molecules and also an alkyl hydrocarbon chain); Family 4: ceramide and dihydroceramide (a family of waxy lipid molecules which are composed of sphingosine (an 18 carbon amino alcohol with an unsaturated hydrocarbon chain) and a fatty acid); Family 5: amides bonded by ethylene (degradation products from a lubricant losing C2H4); Other compounds (amides come from the impurities or degradation products from erucamide and oleamide widely used as slip agents) | UPLC-MS-QTOF | [71] |
| Polypropylene (PP) | 2,4-di-tert-butylphenol (degradation product of Irgafos 168 and Irganox® 1010), tert-butyl-1-oxaspiro(4,5)deca-6-9-diene-2,8-dione (a by-product of the antioxidant Irganox 1010) and 2,6-di-tert-butyl-1,4-benzoquinone, a degradation product of antioxidants such as Irganox 1010, Irgafos 168 and Irganox PS 802 | GC-MS | [76] |
| Polypropylene random copolymer composite films | Irgafos 168 and its two degradation products, 2,4-di-tert-butylphenol (DP1) and tris (2,4-di-tert-butylphenyl) phosphate (DP2) | GC-MS | [70] |
| Plastic films (with and without printing ink) including PE: polyethylene. PET: Polyethylene terephthalate. PA: Polyamide. PP: Polypropylene. EVA: Ethylene-vinyl acetate. | 2,4-di-tert-butylphenol and 2,6-di-tert-butyl-1,4-benzoquinone. 2,4-di-tert-butylphenol is a degradation product of Irgafos 168 while 2,6-di-tert-butyl-1,4-benzoquinone is a degradation product of antioxidants such as Irganox 1010, Irgafos 168 and Irganox PS 802 | purge and trap (P&T) coupled to GC–MS | [75] |
| Polypropylene food storage containers | Degradation products, 2,4-di-tert-butylphenol and tris(2,4-di-tert-buthylphenyl)phosphate, methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, a compound identified as product of degradation of Irganox 1076 and/or Irganox 1010, 2,6-di-tert-butylbenzoquinone (isooctane fraction) and 7,9-di-tert-butyl-1-oxaspiro(4,5)deca-6,9-diene-2,8-dione, 2-ethylhexanoic acid, 2-ethylhexanol, phthalic acid, mono-2-ethylhexyl phthalate), and consequently suggested as possible degradation products of this phthalate, by-product Benzothiazole, degradation products N,N-bis-(2-hydroxyethyl)alkyl amine | GC × GC−ToF MS | [77] |
| Polyethylene-PE, low-density polyethylene-LDPE and HIGH-density polyethylene-HDPE | Dibutyl amine, N,N-bis(2-hydroxyethyl)alkylamines (impurity reaction or breakdown products), N,N-bis(2-hydroxyethyl) dodecylamine, tributylphosphine, tridodecylamine, Methyl (Ralox 35), ethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propanoate (breakdown of Irganox 1010 or Irganox 1076), Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, 1,1′-[2,2-bis(hydroxymethyl)-1,3-propanediyl] ester and benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, 1,1′-[2-[[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropoxy]methyl]-2-(hydroxymethyl)-1,3-propanediyl] ester (degradation of Irganox 1010), alkylamides N,N′-1,2-ethanediylbis-(breakdown or impurity products of the additive octadecanamide, N,N′-1,2-ethanediylbis), Irgafos 168 OXO (oxo-derivative of Irgafos 168), 11-eicosenamide (derived from oleamide) | UPLC IMS QTOF | [59] |
| Can coatings | Diisobutyl phthalate (DIBP), Degradation products formed from antioxidants (1,3-di-tert-butylbenzene and 2,4-di-tert-butylphenol degradation products from antioxidants Irgafos 168 or Irganox 1076, 2,6-di-tert-butyl-1,4-benzoquinone degradation products from antioxidants Irgafos 168 and Irganox 1010, 7,9-di-tert-butyl-1-oxaspiro(4,5)deca-6,9-diene-2,8-dione, a degradation product of Irganox 1010. | GC-MS and LC-MS/MS | [78] |
| Low-density polyethylene-LDPE and polyamide-PA added of NBBS, α-MSD, Irganox 1081, Irganox 1222, Santonox; LDPE 2/PA 6 2: Nonox A, Neozon D, Antioxidant 2246, Tinuvin P, TOTM | Degradation products of TOTM, including DEHP, isophthalate bis(2-ethylhexyl)benzene-1,3-dicarboxylate (DOIP); decomposition product of NBBS was N-ethyl-N-methylbenzenesulfonamide; The formation of the cyclic saturated isomer (1,1,3-trimethyl-3-phenyl-2H-indene) is triggered by the thermal impact, and so is the rearrangement of the carbon double bond to form isomer 2,4-diphenyl-4-methyl-2(E)-pentene). Decomposition product 2,3-dimethyl-3-phenylbutan-2-yl)benzene is formed by combining two cumyl radicals during pyrolysis of the pure additive and pyrolysis of LDPE entailing α-MSD. The degradation product of Neozon D and Nonox A identified in oxidative pyrolysis of the pure analyte was 10-methyl-benz[a]acridine; degradation products of Antioxidant 2246, Santonox, Irganox 1222/1081 and Tinuvin P: o-cresol, m-cresol or p-cresol, 2-tert-butyl-4-methylphenol and 2-tert-butyl-4,6-dimethylphenol, 3,5-di-tert-butyl-4-hydroxybenzaldehyde | Pyr-GC–MS and GC-EI-MS/MS | [104] |
| Recycled pellets obtained from post-consumer low-density polyethylene (PC-LDPE) and high-density polyethylene (PC-HPDE) | Polymer degradation products: octanal and nonanal (aldehydes); 3-decanone, 2-undecanone, 2,2,4,4,6,8,8-heptamethylnonanone and 3-dodecanone (ketones); hexane (others); Additives degradation products: 3,5-di-tert-butyl-4-hydroxybenzaldehyde (aldehyde); 2,6-di-tert-butyl-1,4-benzoquinone and 3,5-di-tert-butyl-4-hydroxyacetophenone (ketones); methyl tetradecanoate, ethyl tetradecanoate and ethyl palmitate(esters); 7,9-di-tert-butyl-1-oxaspiro (4,5)deca-6,9-diene-2,8-dione (others); Contaminants from external sources: methyl lactate, hexyl acetate, and dimethyl butanedioate, α-methylionone, 3-(4-Isopropylphenyl)-2-methylpropionaldehyde, α-amylcinnamaldehyde, (phenylmethylene)octanal and dipropylene glycol amog others (cosmetic ingredients); alkylbenzenes (breakdown products produced by the degradation of alkylbenzene sulfonates); contamination related to food: the lactones, 5-methylfurfural, furfural and methyl hexanoate (can derive from food flavors as well as from cosmetics ingredients); furfuryl alcohol, methyl pyruvate and 2-acetyl pyridine (food flavors), methyl-2-ethylhexanoate, acetic acid, propanoic acid, pyridine and dimethyl trisulfide (rotten food products), 2,6-diisopropylnaphthalene (paper labels). | GC/MS and HS-SPME-GC/MS | [79] |
GC × GC−ToF MS: two-dimensional gas chromatography-time-of-flight mass spectrometry; GC-FID–MS: gas chromatography-mass spectrometry and flame ionization detector; GC-MS: gas chromatography-mass spectrometry; HPLC-DAD: high-performance liquid chromatographic method with diode-array detection; HS-SPME-GC-MS: a combination of headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry; LC-MS/MS: Liquid chromatography-tandem mass spectrometry Pyr-GC–MS: Pyrolysis gas chromatography-mass spectrometry; UHPLC–ESI Q-orbitrap: ultra-high-performance liquid chromatography-electrospray ionization quadrupole Orbitrap mass spectrometry; UHPLC–Q-TOF/MSE: ultra-performance liquid chromatography coupled with a hybrid quadrupole time-of-flight mass spectrometry; UPLC IMS QTOF: ultra-performance liquid chromatography-ion mobility separation-quadruple time-of-flight; UPLC-ESI-MS/QTOF: ultra-performance liquid chromatography-electrospray ionization mass spectrometer quadrupole time of flight.