食品接触材料中三聚氰胺检测、迁移及控制技术
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摘要
三聚氰胺（melamine，MEL）及其衍生物三聚氰酸二酰胺（ANE），三聚氰酸一酰胺（ADE）和三聚氰酸（CYA）本身的物质毒性很小，但同时被人体摄入后，三聚氰胺遇强酸或强碱水溶液水解会形成对人体有害的物质。以三聚氰胺-甲醛树脂为原料合成的密胺餐具、食品包装材料等，经光照、加热、遇酸或反复使用后时，残留的MEL、ANE、ADE、CYA等单体会向与之接触的食品发生迁移，污染食品、危害健康。本文建立了稳健的系列检测方法，研究了食品接触材料中三聚氰胺迁移规律，开展了风险评估及工艺控制研究。
论文共分五章，第一章为文献综述，系统介绍了食品接触材料的分类、迁移过程及分析方法。同时介绍了食品接触材料中三聚氰胺及其类似物检测方法研究进展，食品接触材料中三聚氰胺污染风险评估以及工业控制等方面的研究背景，提出了本论文的研究设想和主要研究内容，指出了本论文解决的关键问题及特色和创新之处。
在第二章中以色谱技术和电化学分析技术为手段建立了一系列检测食品接触材料中三聚氰胺及其衍生物迁移量的分析方法。本章分为六个部分：
（1）建立了一种用液相色谱技术检测分析食品接触材料中三聚氰胺与三聚氰酸单体迁移量的方法。在优化条件下，三聚氰胺和三聚氰酸分别在0.1～110mg/L和0.3～135mg/L范围内，峰面积和质量浓度的线性关系良好。在0.5mg/L的添加水平下，三聚氰胺和三聚氰酸的平均回收率分别为101.7%～102.2%和88.0%～88.9%，相对标准偏差分别为2.45%～3.42%和3.54%～4.10%，检出限分别为0.02mg/L和0.08mg/L。
（2）建立了高效液相色谱同时检测三聚氰胺（MEL）及其衍生物——三聚氰酸二酰胺(ANE)、三聚氰酸一酰胺(ADE)、三聚氰酸(CYA)单体迁移量的方法。在优化条件下，MEL、ANE、ADE和CYA的浓度在0.5~10mg/L范围内与其峰面积的线性关系良好，检出限分别为0.06、0.08、0.12和0.15mg/L（S/N=3）。在1.0mg/L的添加水平下，MEL、ANE、ADE和CYA的平均回收率在96.4%~101.6%之间，相对标准偏差在2.79%~4.39%之间。
（3）建立了液相色谱串联电喷雾正离子源质谱(LC–ESI-MS/MS)检测密胺餐具中三聚氰胺迁移量的方法。三聚氰胺在5.00–130.00μg/L浓度范围内，目标物的峰面积和质量浓度的线性关系良好，检测限为1.00–3μg/L。在10.00、50.00、80.00μg/L浓度添加水平，样品回收率在98.57–104.08%，RSD在3.05–3.65%之间。
（4）建立了一种用HILIC-MS/MS质谱联用技术检测分析食品接触材料中三聚氰胺及其衍生物单体迁移量的方法。三聚氰胺在浓度0.1-20μg/L、三聚氰酸二酰胺1-200μg/L、三聚氰酸一酰胺0.5-100μg/L、三聚氰酸1-200μg/L浓度范围内，峰面积和质量浓度的线性关系良好。在1μg/L,10μg/L，20μg/L水平添加回收率中，平均回收率分别为83.4–126.2%，相对标准偏差在2.89-3.37%。
（5）基于三聚氰胺能猝灭CdS-K_2S_2O_8电化学发光的性质建立了一种检测三聚氰胺的方法。在最优条件下，体系的ECL强度与三聚氰胺浓度在1.0×10~(-9)mol/L-1.0×10~(-7)mol/L范围内与成线性关系，检测限达8.0×10~(-10)mol/L (S/N=3)。
（6）基于三聚氰胺可猝灭鲁米诺的电化学发光，建立了一种对三聚氰胺的定量的新方法。三聚氰胺在1~100ng/mL浓度范围内与电化学发光强度成线性关系，检测限为0.1ng/mL。方法被应用于检测食品及食品接触材料中三聚氰胺的含量，对实际奶制品检测回收率在98.5%-103.7%，密胺餐具回收率在95.5-106.0%，相对标准偏差小于4.0%，且常见干扰物质对实验测量无影响。
第三章利用自主建立的灵敏稳健LC-MS/MS测定食品接触材料中三聚氰胺迁移量的方法，研究了代表性食品接触材料——密胺餐具中三聚氰胺单体的迁移规律和迁移模型。
（1）重点考察了食品模拟物种类、接触时间、接触温度、乙酸浓度、乙醇浓度、重复使用和微波加热等迁移条件下密胺餐具中三聚氰胺迁移量的变化情况。结果表明酸性食品和牛奶中的三聚氰胺迁移风险较高，且需控制密胺餐具的使用温度、盛放时间、重复使用次数及微波加热功率和时间以降低密胺餐具中三聚氰胺迁移风险。
（2）基于Fick定律，选择密胺餐具作为对象，对食品接触材料中三聚氰胺迁移数学模型进行研究。研究的迁移数学模型包括扩散系数和分配系数；研究的迁移模拟物包括4%乙酸、蒸馏水和10%乙醇；研究的迁移温度为40℃、70℃、90℃。结果表明，温度对扩散系数和分配系数影响较大，温度升高，三聚氰胺扩散系数均随之增大，在密胺餐具和模拟物之间的分配系数随之减小；三聚氰胺在模拟物中的扩散系数大小依次为4%乙酸>水>10%乙醇，在密胺餐具和模拟物之间的分配系数大小依次为4%乙酸<水<10%乙醇。
在第四章中对1-3岁儿童摄入盛装在密胺餐具中的食品进行安全风险评估。讨论了食品模拟物种类、乙酸浓度、迁移温度、迁移时间、重复使用次数、微波加热的时间和功率等因素的影响下，密胺餐具中三聚氰胺迁移以及1-3岁儿童每日摄入三聚氰胺量的变化规律；同时，通过每日摄入量与世界卫生组织规定的TDI（0.2mg/Kg·bw）比较，对1-3岁儿童摄入盛装在不同使用条件下密胺餐具中的食品进行安全风险评估，并作出相应的建议。
在第五章中选择代表性的密胺餐具作为研究对象，研究不同生产工艺条件对密胺餐具中三聚氰胺迁移量的影响情况。考察了生产工艺对三聚氰胺单体残留影响的主要环节，“表面贴花”工艺和“保压固化”过程涉及的三个因素（压模温度、压模压力和固化时间）对密胺餐具中三聚氰胺迁移量的影响。利用正交试验，结合考虑经济性分析因素选择了保压固化过程的最佳参数为：上/下模温度190/160℃、压模压力150kg/cm2、固化时间60s。
Melamine and its derivatives (ammeline (ANE), ammelide (ADE), and cyanuricacid (CYA)) are nontoxic by themselves, but if intaked by human, in case of strongacid or alkali solution, melamine will hydrolyse and form a harmful substances.Melamine tablewares and food packaging materials were prepared withmelamine-formaldehyde resin. When treated by light, heat, acid or repeated using,residues of MEL, ANE, ADE, CYA will migrate to the contacted food and cause thepollution to the food, which will be harmful to human. In this dissertation, weestablished several robust detection methods for melamine and its derivatives, andthen study the migration rule of of melamine from food contact materials to food, andcarried out the reasearch of risk assessment and process control of melaminetableware.
In Chapter1, we reviewed the materials used in food contact materials and therelated analytical methods. Specially, the analytical methods in determination ofmelamine and its analogues in food contact products had been reviewed in detail. Theresearch background of the melamine contamination in food contact materials and therelated risk assessment, and industrial control were introduced. The research ideas,main contents, characteristics and innovations of this thesis had been pointed out.
In the second chapter, including6parts, a series of methods for detection ofmelamine and its derivatives in food contact materials base on chromatography andelectrochemical analysis technology were established.
(1) A HPLC method was developed for determination of melamine and cyanuricacid. Under the optimum conditions, linear responses were in the range of0.1–110mg/L and0.3–135mg/L, respectively. And the recoveries were in the range of101.7-102.2%and88.0-88.9%with the concentration of0.5mg/L melamine and cyanuricacid, R.S.D. were2.45–3.42%and3.54–4.10%, respectively. The LOD were0.02mg/L for melamine and0.08mg/L for cyanuric acid.
(2) A novel HPLC method of determining monomer of melamine (MEL) and its derivatives including ammeline (ANE), ammelide (ADE) and cyanuric acid (CYA)was developed. Under the optimum conditions, the calibration curves were linearfrom0.5to10mg/L with LODs (S/N=3) of0.06mg/L,0.08mg/L,0.12mg/L and0.15mg/L for MEL, ANE, ADE and CYA, respectively. The method providedrecoveries of96.4–101.6%at the spiked concentration of1.0mg/kg, and RSD of thepeak height were between2.79~4.39%.
(3) A liquid chromatography electrospray ionization tandem mass spectrometric(LC–ESI-MS/MS) method was developed to determine melamine migration fromfood contact materials and melamine tableware. The result indicated that thecalibration curves were linear over melamine concentration in the range o f3.00-130.00μg/L for different simulant solutions with LODs of1.00–3μg/L. The averagerecoveries at three spiked concentration levels of10.00,50.00and80.00μg/kg werein the range o f98%-104%with RSDs of3.05–3.65%.
(4) HILIC-MS/MS was developed for simultaneously qualitative and quantitativedetermination of melamine and triazine-related by-products including ammelide,ammeline, and cyanuric acid in food contact materials. Linear responses wereobserved for samples ranging from0.1-20mg/L,1-200,0.5-100and1-200μg/Lfor melamine, ammelide, ammeline, and cyanuric acid, respectively. The methodprovided recoveries of83.4–126.2%at the spiked concentration of1μg/kg,10μg/kg,20μg/kg, and RSD of the peak height were between2.89-3.37%.
(5) Melamine was found to have the ability of significant quenching of the ECLof CdS-K_2S_2O_8system, based on which a highly sensitive approach for detection ofmelamine was proposed. Under the optimum conditions, the logarithmic plot of theinhibited ECL versus the concentration of melamine was linear over the range of1.0×10~(-9)mol/L~1.0×10~(-7)mol/L. The corresponding LOD was8.0×10~(-10)mol/L formelamine(S/N=3).
(6) An electrochemiluminescent (ECL) method has been developed for thedetermination of melamine based on the inhibition of luminol ECL system. Thedecrease of ECL intensity was linearly proportional to the logarithm of melamineconcentration in the range of1~100ng/mL with the detection limit of0.1ng/mL. Themethod has been successfully applied to determine melamine in dairy products andthe melamine tableware, and the recoveries were in the range98.5~103.7%and95.5~106.0%in dairy products and the melamine tableware, respectively. Some possibleco-existing species showed no interference in the determination of melamine.
In the third chapter, a LC-MS/MS method had been applied to determine themelamine migration from food contact materials, and melamine monomer migrationrule and migration model had been established. Specially two parts had been studied.
(1) The difference of melamine migration under different conditions such asdifferent types of food simulants, contact time and temperature, reuse times and thecondition of being heated by microwave had been studied in detail. The resultsshowed that melamine migration increases in acid foods and milk. In order to reducethe risk of melamine migration, the using temperature, bloom time, re-use frequencyand microwave heating power and time should be controlled when the melaminetableware is used.
(2) A mathematical model (including diffusion coefficients and partitioncoefficients) for melamine migration from the food contact materials had beenestablised based on Fick law. The effect of soaking solution (4%acetic acid, waterand10%elthanol) and soaking time (40℃,70℃and90℃) were discussed. Theresults show that temperature has great influence on the diffusion coefficient andpartition coefficient. Diffusion coefficient of melamine increases with temperature,meanwhile the partition coefficient between the melamine tableware and simulantsolutions decreases. The diffusion coefficient of simulant solutions was in sequence of4%acetic acid> water>10%ethanol, the partition coefficient was in sequence of4%acetic acid In Chapter4, a security risk assessment about the foods for1-3years old childrenin the melamine tableware had been performed. The effect of types of food, aceticacid concentration, migration temperature, migration time and frequency of repeatedusing dan the microwave heating time and power on the rules of melamine migrationand the daily intake amount of melamine of1-3years old children had been discussed.And the results reached had been compared with data from the WHO TDI (0.2mg/Kg·bw), security risk assessment on the food intake of1-3year-old children up indifferent conditions of use melamine tableware had been performed and theappropriate recommendations had been put forward also.
In Chapter5, the effect of different production process conditions on themigration of melamine in tableware melamine had been studied. The major processeswhich have great impact on melamine monomer residues were studied. In addition,we also examined the effects of the three factors (temperature, pressure and curing time) in "surface applique" and "pressure curing" process on melamine migrationfrom melamine tableware. Combined with the economic analysis, the orthogonal testresults showed that the optimal parameters of pressure and curing process was190/160℃for top/bottom temperature,150kg/cm~2for pressure and60s for curingtime.
论文共分五章，第一章为文献综述，系统介绍了食品接触材料的分类、迁移过程及分析方法。同时介绍了食品接触材料中三聚氰胺及其类似物检测方法研究进展，食品接触材料中三聚氰胺污染风险评估以及工业控制等方面的研究背景，提出了本论文的研究设想和主要研究内容，指出了本论文解决的关键问题及特色和创新之处。
在第二章中以色谱技术和电化学分析技术为手段建立了一系列检测食品接触材料中三聚氰胺及其衍生物迁移量的分析方法。本章分为六个部分：
（1）建立了一种用液相色谱技术检测分析食品接触材料中三聚氰胺与三聚氰酸单体迁移量的方法。在优化条件下，三聚氰胺和三聚氰酸分别在0.1～110mg/L和0.3～135mg/L范围内，峰面积和质量浓度的线性关系良好。在0.5mg/L的添加水平下，三聚氰胺和三聚氰酸的平均回收率分别为101.7%～102.2%和88.0%～88.9%，相对标准偏差分别为2.45%～3.42%和3.54%～4.10%，检出限分别为0.02mg/L和0.08mg/L。
（2）建立了高效液相色谱同时检测三聚氰胺（MEL）及其衍生物——三聚氰酸二酰胺(ANE)、三聚氰酸一酰胺(ADE)、三聚氰酸(CYA)单体迁移量的方法。在优化条件下，MEL、ANE、ADE和CYA的浓度在0.5~10mg/L范围内与其峰面积的线性关系良好，检出限分别为0.06、0.08、0.12和0.15mg/L（S/N=3）。在1.0mg/L的添加水平下，MEL、ANE、ADE和CYA的平均回收率在96.4%~101.6%之间，相对标准偏差在2.79%~4.39%之间。
（3）建立了液相色谱串联电喷雾正离子源质谱(LC–ESI-MS/MS)检测密胺餐具中三聚氰胺迁移量的方法。三聚氰胺在5.00–130.00μg/L浓度范围内，目标物的峰面积和质量浓度的线性关系良好，检测限为1.00–3μg/L。在10.00、50.00、80.00μg/L浓度添加水平，样品回收率在98.57–104.08%，RSD在3.05–3.65%之间。
（4）建立了一种用HILIC-MS/MS质谱联用技术检测分析食品接触材料中三聚氰胺及其衍生物单体迁移量的方法。三聚氰胺在浓度0.1-20μg/L、三聚氰酸二酰胺1-200μg/L、三聚氰酸一酰胺0.5-100μg/L、三聚氰酸1-200μg/L浓度范围内，峰面积和质量浓度的线性关系良好。在1μg/L,10μg/L，20μg/L水平添加回收率中，平均回收率分别为83.4–126.2%，相对标准偏差在2.89-3.37%。
（5）基于三聚氰胺能猝灭CdS-K_2S_2O_8电化学发光的性质建立了一种检测三聚氰胺的方法。在最优条件下，体系的ECL强度与三聚氰胺浓度在1.0×10~(-9)mol/L-1.0×10~(-7)mol/L范围内与成线性关系，检测限达8.0×10~(-10)mol/L (S/N=3)。
（6）基于三聚氰胺可猝灭鲁米诺的电化学发光，建立了一种对三聚氰胺的定量的新方法。三聚氰胺在1~100ng/mL浓度范围内与电化学发光强度成线性关系，检测限为0.1ng/mL。方法被应用于检测食品及食品接触材料中三聚氰胺的含量，对实际奶制品检测回收率在98.5%-103.7%，密胺餐具回收率在95.5-106.0%，相对标准偏差小于4.0%，且常见干扰物质对实验测量无影响。
第三章利用自主建立的灵敏稳健LC-MS/MS测定食品接触材料中三聚氰胺迁移量的方法，研究了代表性食品接触材料——密胺餐具中三聚氰胺单体的迁移规律和迁移模型。
（1）重点考察了食品模拟物种类、接触时间、接触温度、乙酸浓度、乙醇浓度、重复使用和微波加热等迁移条件下密胺餐具中三聚氰胺迁移量的变化情况。结果表明酸性食品和牛奶中的三聚氰胺迁移风险较高，且需控制密胺餐具的使用温度、盛放时间、重复使用次数及微波加热功率和时间以降低密胺餐具中三聚氰胺迁移风险。
（2）基于Fick定律，选择密胺餐具作为对象，对食品接触材料中三聚氰胺迁移数学模型进行研究。研究的迁移数学模型包括扩散系数和分配系数；研究的迁移模拟物包括4%乙酸、蒸馏水和10%乙醇；研究的迁移温度为40℃、70℃、90℃。结果表明，温度对扩散系数和分配系数影响较大，温度升高，三聚氰胺扩散系数均随之增大，在密胺餐具和模拟物之间的分配系数随之减小；三聚氰胺在模拟物中的扩散系数大小依次为4%乙酸>水>10%乙醇，在密胺餐具和模拟物之间的分配系数大小依次为4%乙酸<水<10%乙醇。
在第四章中对1-3岁儿童摄入盛装在密胺餐具中的食品进行安全风险评估。讨论了食品模拟物种类、乙酸浓度、迁移温度、迁移时间、重复使用次数、微波加热的时间和功率等因素的影响下，密胺餐具中三聚氰胺迁移以及1-3岁儿童每日摄入三聚氰胺量的变化规律；同时，通过每日摄入量与世界卫生组织规定的TDI（0.2mg/Kg·bw）比较，对1-3岁儿童摄入盛装在不同使用条件下密胺餐具中的食品进行安全风险评估，并作出相应的建议。
在第五章中选择代表性的密胺餐具作为研究对象，研究不同生产工艺条件对密胺餐具中三聚氰胺迁移量的影响情况。考察了生产工艺对三聚氰胺单体残留影响的主要环节，“表面贴花”工艺和“保压固化”过程涉及的三个因素（压模温度、压模压力和固化时间）对密胺餐具中三聚氰胺迁移量的影响。利用正交试验，结合考虑经济性分析因素选择了保压固化过程的最佳参数为：上/下模温度190/160℃、压模压力150kg/cm2、固化时间60s。
Melamine and its derivatives (ammeline (ANE), ammelide (ADE), and cyanuricacid (CYA)) are nontoxic by themselves, but if intaked by human, in case of strongacid or alkali solution, melamine will hydrolyse and form a harmful substances.Melamine tablewares and food packaging materials were prepared withmelamine-formaldehyde resin. When treated by light, heat, acid or repeated using,residues of MEL, ANE, ADE, CYA will migrate to the contacted food and cause thepollution to the food, which will be harmful to human. In this dissertation, weestablished several robust detection methods for melamine and its derivatives, andthen study the migration rule of of melamine from food contact materials to food, andcarried out the reasearch of risk assessment and process control of melaminetableware.
In Chapter1, we reviewed the materials used in food contact materials and therelated analytical methods. Specially, the analytical methods in determination ofmelamine and its analogues in food contact products had been reviewed in detail. Theresearch background of the melamine contamination in food contact materials and therelated risk assessment, and industrial control were introduced. The research ideas,main contents, characteristics and innovations of this thesis had been pointed out.
In the second chapter, including6parts, a series of methods for detection ofmelamine and its derivatives in food contact materials base on chromatography andelectrochemical analysis technology were established.
(1) A HPLC method was developed for determination of melamine and cyanuricacid. Under the optimum conditions, linear responses were in the range of0.1–110mg/L and0.3–135mg/L, respectively. And the recoveries were in the range of101.7-102.2%and88.0-88.9%with the concentration of0.5mg/L melamine and cyanuricacid, R.S.D. were2.45–3.42%and3.54–4.10%, respectively. The LOD were0.02mg/L for melamine and0.08mg/L for cyanuric acid.
(2) A novel HPLC method of determining monomer of melamine (MEL) and its derivatives including ammeline (ANE), ammelide (ADE) and cyanuric acid (CYA)was developed. Under the optimum conditions, the calibration curves were linearfrom0.5to10mg/L with LODs (S/N=3) of0.06mg/L,0.08mg/L,0.12mg/L and0.15mg/L for MEL, ANE, ADE and CYA, respectively. The method providedrecoveries of96.4–101.6%at the spiked concentration of1.0mg/kg, and RSD of thepeak height were between2.79~4.39%.
(3) A liquid chromatography electrospray ionization tandem mass spectrometric(LC–ESI-MS/MS) method was developed to determine melamine migration fromfood contact materials and melamine tableware. The result indicated that thecalibration curves were linear over melamine concentration in the range o f3.00-130.00μg/L for different simulant solutions with LODs of1.00–3μg/L. The averagerecoveries at three spiked concentration levels of10.00,50.00and80.00μg/kg werein the range o f98%-104%with RSDs of3.05–3.65%.
(4) HILIC-MS/MS was developed for simultaneously qualitative and quantitativedetermination of melamine and triazine-related by-products including ammelide,ammeline, and cyanuric acid in food contact materials. Linear responses wereobserved for samples ranging from0.1-20mg/L,1-200,0.5-100and1-200μg/Lfor melamine, ammelide, ammeline, and cyanuric acid, respectively. The methodprovided recoveries of83.4–126.2%at the spiked concentration of1μg/kg,10μg/kg,20μg/kg, and RSD of the peak height were between2.89-3.37%.
(5) Melamine was found to have the ability of significant quenching of the ECLof CdS-K_2S_2O_8system, based on which a highly sensitive approach for detection ofmelamine was proposed. Under the optimum conditions, the logarithmic plot of theinhibited ECL versus the concentration of melamine was linear over the range of1.0×10~(-9)mol/L~1.0×10~(-7)mol/L. The corresponding LOD was8.0×10~(-10)mol/L formelamine(S/N=3).
(6) An electrochemiluminescent (ECL) method has been developed for thedetermination of melamine based on the inhibition of luminol ECL system. Thedecrease of ECL intensity was linearly proportional to the logarithm of melamineconcentration in the range of1~100ng/mL with the detection limit of0.1ng/mL. Themethod has been successfully applied to determine melamine in dairy products andthe melamine tableware, and the recoveries were in the range98.5~103.7%and95.5~106.0%in dairy products and the melamine tableware, respectively. Some possibleco-existing species showed no interference in the determination of melamine.
In the third chapter, a LC-MS/MS method had been applied to determine themelamine migration from food contact materials, and melamine monomer migrationrule and migration model had been established. Specially two parts had been studied.
(1) The difference of melamine migration under different conditions such asdifferent types of food simulants, contact time and temperature, reuse times and thecondition of being heated by microwave had been studied in detail. The resultsshowed that melamine migration increases in acid foods and milk. In order to reducethe risk of melamine migration, the using temperature, bloom time, re-use frequencyand microwave heating power and time should be controlled when the melaminetableware is used.
(2) A mathematical model (including diffusion coefficients and partitioncoefficients) for melamine migration from the food contact materials had beenestablised based on Fick law. The effect of soaking solution (4%acetic acid, waterand10%elthanol) and soaking time (40℃,70℃and90℃) were discussed. Theresults show that temperature has great influence on the diffusion coefficient andpartition coefficient. Diffusion coefficient of melamine increases with temperature,meanwhile the partition coefficient between the melamine tableware and simulantsolutions decreases. The diffusion coefficient of simulant solutions was in sequence of4%acetic acid> water>10%ethanol, the partition coefficient was in sequence of4%acetic acid
In Chapter5, the effect of different production process conditions on themigration of melamine in tableware melamine had been studied. The major processeswhich have great impact on melamine monomer residues were studied. In addition,we also examined the effects of the three factors (temperature, pressure and curing time) in "surface applique" and "pressure curing" process on melamine migrationfrom melamine tableware. Combined with the economic analysis, the orthogonal testresults showed that the optimal parameters of pressure and curing process was190/160℃for top/bottom temperature,150kg/cm~2for pressure and60s for curingtime.
引文
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