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Development of Analytical Screening Methods for Migration Estimation of Adhesives Related Substances in Food Packaging Materials

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Development of Analytical Screening Methods for Migration Estimation of Adhesives Related Substances in Food Packaging Materials TECHNISCHE UNIVERSITÄT MÜNCHEN Lehrstuhl für Lebensmittelverpackungstechnik Development of analytical screening methods for migration estimation of adhesives related substances in food packaging materials Chan Suk Yoon Vollständiger Abdruck der von der Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt der Technischen Universität München zur Erlangung des akademischen Grades eines Doktors der Naturwissenschaften genehmigten Dissertation. Vorsitzender : Univ.- Prof. Dr. H. Briesen Prüfer der Dissertation : 1. Univ.- Prof. Dr. H.-Chr. Langowski 2. Univ.- Prof. Dr. K.-H. Engel Die Dissertation wurde am 18.03.2010 bei Technischen Universität München eingereicht und durch die Fakultät Wissenschaftzentrum Weihenstephan für Ernährung, Landnutzung und Umwelt am 23.07.2010 angenommen. Contents I Contents Contents -------------------------------------------------------------------------------------------- I Abbreviations -------------------------------------------------------------------------------------- V 1. Introducti on ------------------------------------------------------------------------------------ 1 1.1. Adhesive in food packging ------------------------------------------------------------------ 1 1.1.1. Application areas ------------------------------------------------------------------------ 1 1.1.2. Composition and Classification of adhesives for food packaging ---------------- 3 1.2. Overview German and EU regulation relate to adhesives used for manufacture of food packaging materials -------------------------------------------------------------------- 6 1.3. Principles of interaction between adhesive layers in food packaging materials and packed food ----------------------------------------------------------------------------------- 12 1.4. Analysis aspects for qualitative and quantitative determination of adhesvie related substances ------------------------------------------------------------------------------------- 14 1.5. Potential migrants in adhesive layers of food packaging materials ------------------- 15 2. Objectives of this study ---------------------------------------------------------------------- 18 3. Theoretical considerations ------------------------------------------------------------------ 20 3.1. General conceptual background of analytical methods for simultaneous determination of multiple analytes -------------------------------------------------------------- 20 3.2. Considerations on detector response factors ---------------------------------------------- 21 3.3. More specific considerations on analytical systems-------------------------------------- 24 3.3.1. Universal detection system for volatile and semi-volatile substances ------------ 24 3.3.2. Universal detection system for non-volatile substances ---------------------------- 24 3.3.3. Separation systems for volatile and semi-volatile substances --------------------- 26 3.3.4. Separation systems for non-volatile substances ------------------------------------- 27 3.3.5. Online two-dimensional chromatography -------------------------------------------- 28 3.4. Methods validation --------------------------------------------------------------------------- 31 3.5. Identification of volatile and semi-volatile substances ---------------------------------- 32 3.6. Practical applications of screening methods ---------------------------------------------- 33 3.6.1. Migration test ---------------------------------------------------------------------------- 33 Contents II 3.6.2. Extraction test ---------------------------------------------------------------------------- 34 4. Experimental ----------------------------------------------------------------------------------- 35 4.1. Chemicals ------------------------------------------------------------------------------------- 35 4.1.1. Representative adhesive related substances ------------------------------------------ 35 4.1.2. Test substances used for GC column selection -------------------------------------- 37 4.1.3. Test substances used for online two-dimensional chromatographic analysis ---- 38 4.1.4. Standard solution of n-Alkanes for determination of retention indices ---------- 38 4.1.5. Solvents and Reagents ------------------------------------------------------------------ 38 4.2. Preparation of standard solutions ---------------------------------------------------------- 39 4.2.1. Representative adhesive related substances and internal standards --------------- 39 4.2.2. Test substances and internal standard for GC column selection ------------------ 39 4.2.3. Test substances for online two-dimensional chromatographic analysis ---------- 40 4.2.4. n-Alkanes for determination of retention indices ------------------------------------ 40 4.3. Instrumental analysis for non-volatile substances --------------------------------------- 40 4.3.1. HPLC-CAD analysis for the representative adhesive related substances -------- 40 4.3.2. SEC×NP-HPLC×CAD analysis ------------------------------------------------------- 41 4.3.3. LC-MS analysis of dipropylene glycol dibenzoate ---------------------------------- 43 4.4. Instrumental analysis for volatile and semi-volatile substances ----------------------- 44 4.5. Statistical data analysis of relative response factor (RRF) values --------------------- 45 4.5.1. Normality test ---------------------------------------------------------------------------- 45 4.5.2. Estimation of the distribution range of RRF values -------------------------------- 46 4.6. Linearity and Limit of detection (LOD) --------------------------------------------------- 47 4.7. Practical applications ------------------------------------------------------------------------ 47 4.7.1. Sample generation ----------------------------------------------------------------------- 47 4.7.2. Sample preparation ---------------------------------------------------------------------- 48 4.7.3. Analysis of extracts and migrants using the developed screening methods ----- 50 5. Results ------------------------------------------------------------------------------------------- 51 5.1. Selection of representative adhesive related substances -------------------------------- 51 5.2. Development of screening method by HPLC-CAD ------------------------------------ 54 5.2.1. HPLC-CAD analysis data -------------------------------------------------------------- 54 Contents III 5.2.2. HPLC-CAD relative response factors ------------------------------------------------- 62 5.3. SEC×NP-HPLC×CAD two-dimensional chromatography ----------------------------- 68 5.3.1. Optimization of the SEC×NP-HPLC conditions ------------------------------------ 68 5.3.2. SEC×NP-HPLC×CAD two-dimensional separation -------------------------------- 69 5.4. Development of screening method by GC-FID ------------------------------------------ 72 5.4.1. Pre-selection of GC columns ----------------------------------------------------------- 74 5.4.2. GC-FID separation on non-polar DB-1 column ------------------------------------- 77 5.4.3. GC-FID separation on polar DB-FFAP column ------------------------------------- 82 5.4.4. GC-FID relative response factors ------------------------------------------------------ 85 5.4.5. Estimation of molecular weight by retention time ---------------------------------- 88 5.4.6. Characterisation of unknown substances by linear retention indices ------------- 89 5.5. Statistical data analysis of relative response factor (RRF) values --------------------- 94 5.5.1. Normality test for HPLC-CAD analysis data ---------------------------------------- 94 5.5.2. Distribution range estimation of HPLC-CAD analysis data ----------------------- 95 5.5.3. Normality test for GC-FID analysis data --------------------------------------------- 96 5.5.4. Distribution range estimation of GC-FID analysis data ---------------------------- 97 5.6. Practical application of the multi-screening methods ----------------------------------- 98 5.6.1. HPLC-CAD analysis data of extracts from adhesives and glued samples and of migrantion solutions ----------------------------------------------------------------- 98 5.6.2. GC-FID analysis data of extracts and migrantion solutions ----------------------- 102 5.6.3. Semi-quantification of adhesive related susbtances --------------------------------- 109 6. Discussion --------------------------------------------------------------------------------------- 112 6.1. Development of screening methods by using HPLC-CAD system -------------------- 112 6.1.1. HPLC-CAD analysis data -------------------------------------------------------------- 112 6.1.2. HPLC-CAD relative response factors ------------------------------------------------- 114 6.1.3. SEC×HPLC-CAD two-dimensional separation ------------------------------------- 117 6.2. Development of screening methods by GC-FID ----------------------------------------- 122 6.2.1. GC-FID analysis ------------------------------------------------------------------------- 122 6.2.2. GC-FID relative response factors ------------------------------------------------------ 123 6.2.3. Estimation of molecular weight by retention time ---------------------------------- 126 6.2.4. Characterisation of unknown substances by linear retention indices ------------- 127 6.3. Practical application of the developed screening methods ----------------------------- 131 Contents IV 6.3.1. HPLC-CAD analysis data of extracts and migrants --------------------------------- 131 6.3.2. GC-FID analysis data of extracts and migrants --------------------------------------
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