Harnessing the Power of CCS for Routine Screening Applications on the UNIFI Informatics Platform
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1 Harnessing the Power of CCS for Routine Screening Applications on the UNIFI Informatics Platform Cristina Nerín I3A, Dept. Anal. Chem. University of Zaragoza (Spain) 1
2 Outline Introduction: Food Packaging Materials Migration IAS and NIAS Analytical protocols Case Study 1: PSA Case study 2: NIAS and set-off migration (1) Case study 3: NIAS and set-off migration (2) Risk assessment 2
3 FOOD PACKAGING MATERIALS Monomaterial/monolayer Multilayer&multimaterial Material A + Printing Inks + Lacquer/varnish Material A + Adhesive + material B + Printing inks + Lacquer/varnish Adhesives directly applied on food: PSA Cardboard packaging High Barrier Materials (multilayers) 3
4 MIGRATION FROM PACKAGING TO FOOD Monolayer packaging Multilayer packaging K,D food food printing ink adhesive TOXIC EFFECTS IN FOOD CONSUMERS CHANGES IN FOOD SENSORY PROPERTIES PHYSICO-CHEMICAL CHANGES ON PACKAGING
5 From manufacturing processes SET OFF (ink transference) Direct contact Pressure
6 MIGRANTS ORIGIN IAS INTENTIONALLY ADDED SUBSTANCES Polymer additives: antioxidants, flame retardants, UV absorbers, Additives from adhesives, varnishes, printing inks NIAS NON INTENTIONALLY ADDED SUBSTANCES Degradation processes: Polymer degradation Additives degradation Impurities of raw materials Residual monomers, catalysts Reaction Products Contaminants 6
7 Well known NIAS ADDITIVES DEGRADATION Irgafos 168 (antioxidant) POLYMER DEGRADATION PET bottles O O P O [ H 2 O ] O P O + 2,4-DTBP Formaldehyde and acetaldehyde (off-flavours) O P + [Dabrowska et al. Food Addit. Contam. 20 (2003) 1170] [Bach et al. Water Res. 46 (2012) 571] O O P O [O] O O P O O Factors that can affect: temperature oxygen irradiation [Burman et al. J. Chromatogr. A 1080 (2005) 107] [Alin et al. J. Agric. Food Chem. 59 (2011) 5418] [Bertoldo et al. Polymer 45 (2004) 8751] 7
8 NIAS NEOFORMED COMPOUNDS BY-PRODUCTS Polyurethane adhesives Epoxy phenolic coatings: BADGE +H2O, +HCl BADGE-H2O BADGE-2H2O BADGE-HCl [Sendon Garcia et al. J. Chromatogr. A 1032 (2004) 37] [Perez-Lamela, et al. Int. J. Environ. Anal. Chem. 82 (2002) 123] Isocyanates +H2O + Primary aromatic amines Polyols PU ADHESIVES lactones LACTONES Migration test C. Nerin et al. Scientific reports (NATURE) F. Isella, E. Canellas, O. Bosetti, C. Nerin, Journal of Mass Spectrometry, 48, 4, , April /jms.3165, 2013 Juliana S. Félix, Francesca Isella, Osvaldo Bosetti, Cristina Nerín Analytical and Bioanalytical Chemistry, Volume 403, Number 10 (2012), [Aznar et al. J. Chromatogr. A 1216 (2009) 5176] 8
9 Analytical Challenges Sample treatment developments Decision about the analytical procedure: Usually working with blind samples (no information about the composition or the likely migrants). What is the target? Identification of unknowns Origin of the migrants: responsibility!! Low concentration of many migrants Complex analysis of food Analytical artifacts
10 General scheme for sample treatment MIGRATION CELL POLYMER Direct Analysis Migration Test Food simulant Polymer Tenax Liquid Food Simulants EU/10/2011 Thermal Desorption Solid / Liquid extraction HS SPME LLE LLME HS SPME Purge & Trap HS: Headspace SPME: Solid Phase Microextraction LLE: Liquid Liquid extraction LLME: Liquid Liquid microextraction 10
11 Decision tree for the analytical procedure in NIAS identification GC - M S I d e n t i f i c a t i on b y : N I S T libr a ry Ko v a t s in d ex Volatiles ANA L Y SIS Non - volatiles L C - M S (Q T OF ) S e l e ct i on o f p a r e n t i on e m p i r i c a l f o r m u l a Ele m e n t s s ele c t i o n M a s s t olera n c e I s o t o pi c f it Y es No C on f i r mat i on b y St a nd a r d GC - M S ( Q T O F ) No Y es S e l e c t i o n o f c a nd i d a te s t r u c t u r e C h e m i c al d a t ab a s e s Sa m ple in f or m a t i o n Bibli o gra p hi c s e ar c h C a ndid a t e prop e r t i e s C on f i r mat i on b y f r a g m e n t a t i o n C. Nerin*, P. Alfaro, M. Aznar, C. Domeño Anal. Chim. Acta. Volume 775, 2 May 2013, Pages DOI: /j.aca Q u a n t i f i c a t i o n Y es No No Y es C on f i r mat i on b y Sta nd a r d 11
12 Examples Reprotoxic compounds identified in plastic bags for semen dosis By-products resulting from interaction between ingredients in common adhesives Contamination of food from Set-off of printing inks NIAS from adhesives in high barrier materials Degradation compounds from gamma irradiation on packaging materials Oligomers and NIAS in Polymers Migrants from the packaging in food NIAS from active packaging materials Degradation compounds from interaction with the packaged product 12
13 Case study 1 Migration of Volatile compounds from PSA adhesives APGC-MS-QTOF versus GC-MS-Q 1 Identification of volatiles by GC-MS (EI) 2 Identification of volatiles by APGC-MS (TOF) 3 Comparison of both techniques 4 Specific migration analysis and Risk Asssessment 13
14 Case study 1 Migration from Pressure Sensitive Adhesive GC-MS APGC-MS-QTOF
15 Case study 1 Migration from Pressure Sensitive adhesive Function 1 cone voltage 30 V Function 2 High energy30 v in cone voltage and a collision ramp energy in the collision cell from 20 to 40 v 15
16 Case study 1 Migration from Pressure Sensitive adhesive Phosphorous was confirmed by ICP-MS 16
17 Case study 1 Migration from Pressure Sensitive adhesive adhesive Smoking thin paper tenax Migration through pork intestine to isoctane 17
18 Case study 1 Migration from Pressure Sensitive adhesive Canellas,E., Vera, P, Nerín. C. J. Mass Spectrometry, 2014,
19 Case study 1 Migration of PSA adhesives in meat(longaniza) and simulants Dicyclohexylphosphino isomer 3 (III) 19
20 Case study 2 PET: polyethylene terephtalate OPP: Oriented Polypropylene Al: aluminum PE: polyethylene Set D Migration tests with food Simulants
21 Case study 2 Set D / EtOH 95% Material 2 Set D / Tenax Material 2
22 Case study 2 PET AL PE Food 1A INK PET AL PE Food SCR1
23 Case study 2 INK PET AL PE Food SCR1 LAQUER MATT INK PET AL PE Food 4A
24 Case study 2 Table 1: Migrants coming from ink due to set-off (material 2), I (1: low intensity, 2: medium intensity, 3: high intensity), molecular formula, candidates and relative changes of intensity in migration from materials 3 and 4 ( total decrease, partial decrease, = same intensity) Mat. 4 Mat. 3 Mat. 2 Mat. 1 Set D / Tenax Ink migrants (ID_code) M.2 Molecular formula Candidates Mat. 3 Mat _ C10H16O5 Cyclic polyester 4.62_ C12H22O6 Adipate structure 5.35_ C12H20O4 Cyclic polyester (I M3 =40%I M2 ) 5.44_ C22H28O10 Cyclic polyester 5.50_ C24H24O10 Cyclic polyester 5.71_ C16H26O6 Di(tetrahydrofurfuryl)adipate (I M3 =150%I M2 ) 6.50_ C15H28O4 Dibutyl pimelate 6.50_ C14H26O4 Diethyl sebacate 6.82_ <1 C14H20N4O7S n.i. 6.97_ C20H34O8 ATBC 7.05_ C16H30O4 Dipropyl sebacate 7.19_ C16H34O3 n.i. 7.22_ C18H38O4 Triethylene glycol monododecyl ether 7.23_ C20H42O5 Tetraethylene glycol monododecyl ether 7.36_ C18H34O4 Dibutyl sebacate = = 7.62_ C20H38O4 Glycol ricinolate = (I M4 =20%I M2 ) 7.80_ C22H42O4 Di-hexyl sebacate (I M3 =200%I M2 ) (I M4 =15%I M2 )
25 LAQUER MATT PET INK AL PE Case study 2 LAQUER MATT INK PET AL PE Food Scores Comp[1] vs. Comp[2] colored by Sample Group Food t[2] A 3A3A 3A 3A 2A 2A 2A 2A 4A 4A 4A 2A 2A 2A 4A 4A 4A SCR1 SCR1 SCR1 LAQUER GLOSS PET INK AL PE Food 2A A1A SCR1 SCR1 SCR1 SCR PET AL PE t[1] 100 INK PET AL PE Food Food 1A PCA of migration data SCR1
26 Case study 2 Identification by RT and MS fragments Candidates Identification by IM (CCS) CCS Pure standards
27 Case study 2
28
29 Case study 3 OPP Food simulant INK OPP Food simulant Migrats from ink Elemental composition Molecular formula Candidates CCS 4.93_ C12H20O7Na C12H20O7 Citric acid triethyl ester _ C17H37N2O C17H36N2O 5.92_ C13H28O4Na C13H28O4 Schercodine L (lauramidopropyl-dimethylamine) Tripropyleneglycol monobutyl ether _ C14H28O5Na C14H28O5 Triethylene glycol caprylate No standard 6.09_ C19H41N2O C19H4ON2O Schercodine M (Myristamidopropyldimethylamine) No standard 6.39_ C19H39N2O3 C19H38N2O3 Lauraimidopropyl betaine No standard 6.98_ C20H34O8Na C20H34O8 Acetyltributylcitrate (ATBC)
30 DIRECT ANALYSIS OF SAMPLE 1 Case study 3 DESI-TOF ATBC Schercodine L m/z
31 Schercodine L Case study 3 DESI-TOF m/z m/z m/z Phthalate? Sample 2 ATBC
32 What to do after identification? RISK ASSESSMENT OF NIAS EUROPEAN LEGISLATION (EU/10/2011) NATIONAL LEGISLATION TOXICITY REPORTS NO TOXICITY DATA Threshold of Toxicological Concern (TTC) approach (not suitable for carcinogenic, mutagenic or teratogenic compounds) CRAMER RULES 32
33 Threshold of Toxicological Concern (TTC) TOXICITY CLASIFICATION-Cramer rules (Toxtree v1.51) Class I (Low) <1.8 mg/person/day Class II (Medium) <0.54 mg/person/day BHT Class III (High) 0.09 mg/person/day EDI (Estimated Dayly Intake) (mg/person/day)= Mig (mg/kg) x 3 Kg /day/person x CF 33
34 Migration estimation EDI (mg/person/day)= Mig (mg/kg) x 3 Kg* /day/person x CF Where Estimated Daily Intake is the Cramer value Mig: Migration limit (proposal) 3Kg/1Kg is the daily food intake (including beverage) CF is the fraction of the daily diet expected to be in contact with a specific packaging material (e.g.for adhesives this is 0.14). Consumption factors exist in FDA but not in Europe
35 Acknowledgements Research Projects: SAFEMTECH (IAPP-Marie Curie) SAENMA (AGL-2012) MAGAPOR MIGREFILMS MIGRESIVES (EU) NANOFLEXIPACK R&D&i with several companies Collaboration with Waters GUIA GROUP, UNIVERSITY OF ZARAGOZA, SPAIN 35
36 Thank you very much for your attention! 36
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