CN104034822B - A kind of method measuring glyoxal content in Food Contact paper products - Google Patents
A kind of method measuring glyoxal content in Food Contact paper products Download PDFInfo
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- CN104034822B CN104034822B CN201410300744.5A CN201410300744A CN104034822B CN 104034822 B CN104034822 B CN 104034822B CN 201410300744 A CN201410300744 A CN 201410300744A CN 104034822 B CN104034822 B CN 104034822B
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Abstract
The present invention relates to a kind of method measuring glyoxal content in Food Contact paper products, the method is with 5, 6-diaminourea pyrimidine is derivative reagent, use post-column derivation-high performance liquid chromatography to glyoxal in Food Contact paper products content measure, and to derivative reaction temperature, the concentration of buffer solution, derivative reagent concentration, derivative reagent pH, derivative reagent flow velocity has carried out parameter optimization, after testing, under the derivatization conditions optimized and chromatographic condition, the retention time of glyoxal derivative is 4.2min, in good linear relation in mass concentration 0.1mg/L ~ 1.0mg/L, typical curve is y=9954760.9x+2416240 (R
2=0.9997), the recovery be 84.7% – 102.3%, RSD 0.7% ~ 5.6%, the method test is simple, subsidiary reaction is few, detection speed is fast and product is single is easy to quantitative, and gained test result is accurately and reliably, reproducible.
Description
Technical field
The present invention relates to a kind of method measuring glyoxal content in Food Contact paper products.
Background technology
China is defined as packaging to food contact material, holds the coating of the goods such as the paper of food, bamboo and wood, metal, enamel, plastics, rubber, natural fiber, man-made fiber, glass, compound package material and contact food; as the paper products of one of food contact material and our life closely bound up, we often can use various dixie cup, carton, paper bag.And glyoxal is applied widely as raw material in paper industry, it can improve wet strength and the tensile strength of paper, can be used as surperficial water resistant and water resistance that crosslinking chemical improves paper.But glyoxal has moderate toxicity, there is spread effect to eye and schneiderian membrane, can cause that animal hypermesises, slow poisoning, pancreatic damage, also report that glyoxal has the genetoxic such as carcinogenicity, mutagenesis.Because glyoxal harm, various countries and area the limitation of glyoxal in different product is specified.In European Union 76/768/EEC " member state is about the instruction being similar to law of cosmetic product " in regulation cosmetics glyoxal limitation be 100 mg/kg; Made clear stipulaties to paper for daily use safety evaluation in the 2009/568/EC paper for daily use eco-label instruction that European Union issues in July, 2009, restriction glyoxal content is 1.5mg/dm
2; In German federal risk assessment (BFR) regulation Food Contact paper products, the content of glyoxal monomer must not more than 1.5mg/dm
2china at present also not to glyoxal in Food Contact paper products content limit, also not relevant method measures the glyoxal content in Food Contact paper products, but for guaranteeing export food contact paper using quality of item, simultaneously also for exit does tachnical storage, be necessary to study the assay method of glyoxal content in Food Contact paper using.
At present, measure glyoxal analytical approach mainly contain ultraviolet spectrophotometry, high performance liquid chromatography, the chromatography of ions, volumetric method and chemoluminescence method, wherein, volumetric method utilizes the carbonyl in aldehyde and azanol generation addition reaction to generate acid, take bromophenol blue as indicator, use standard solution of sodium hydroxide titration, its complex operation, and indicator discoloration pole is not sharp, measures reappearance very poor, mensuration requirement cannot be met; Chemoluminescence method and chromatography of ions rule because of the reagent related to many, operation relative complex.What commonly use during glyoxal detects is ultraviolet spectrophotometry and high performance liquid chromatography, but the own acomia color group of glyoxal, when using ultraviolet spectrophotometry, high performance liquid chromatography, need to utilize derivative reagent and glyoxal reaction to generate the glyoxal derivative being with chromophoric group, conventional derivative reagent is DNPH, and glyoxal can react with it and generate glyoxal hydrazone, but this reaction subsidiary reaction many, product easily mutually transform and not easily quantitative.With 2-diazanyl-2 in DIN54603,3-dihydro-3-methylbenzothiazole salt (HMBT) is as derivative reagent, although this reaction does not have subsidiary reaction, but the method is only applicable to ultraviolet spectrophotometry, and react under normal temperature and at least need more than 50 minutes, analytical procedure is loaded down with trivial details, is not suitable for batch detection, and therefore finding a kind of suitable derivatization reagent and detection method is the key solving glyoxal test problems.
Technical matters to be solved by this invention is the present situation for prior art, a kind of method measuring glyoxal content in Food Contact paper products is provided, its method of testing is simple, subsidiary reaction is few, detection speed is fast and product is single is easy to quantitative, has better accuracy and repeatability.
The present invention solves the problems of the technologies described above adopted technical scheme: a kind of method measuring glyoxal content in Food Contact paper products, is characterized in that comprising the following steps:
(1) preliminary work before test:
A, be 7.5 ~ 11.0 with pH, 5, the 6-diaminourea pyrimidine derivates agent solutions of concentration to be the ammonium chloride buffer solution compound concentration of 0.05mol/L ~ 0.5mol/L be 50mg/L ~ 400mg/L;
In b, paper glyoxal extraction: sample paper is cut into 1cm
2~ 2cm
2paper fragment, then the paper fragment of 10g is taken, the paper fragment weighed up is moved in the conical flask of 500mL ~ 1000mL, then the ultrapure water getting 100mL ~ 200mL joins in conical flask, finally conical flask is put into the constant temperature oscillator of 20 DEG C ~ 25 DEG C, concussion 20h ~ 25h, afterwards solution poured out and repeatedly clean the conical flask leaving paper fragment with ultrapure water, filter, filtrate is moved in the volumetric flask of 250mL, be settled to scale with ultrapure water;
C, mocromembrane filtration is carried out to the material obtained in step a, b, then directly go up machine testing;
(2) detect:
A, instrument: 2695e-U.S. Butterworth is special, high performance liquid chromatograph;
B, liquid-phase condition: leacheate is V
acetonitrile: V
tertiary sodium phosphate buffer salt=3:97, sample size is 10 μ L, and flow velocity is 1mLmin
-1, post case temperature is 40 DEG C;
C, chromatographic condition: chromatographic column is Shim-PakC18 post, 250mm × 4.6mm, particle diameter 5 μm, fluorescence exciting wavelength is 350nm, emission wavelength 500nm;
D, post-column derivation condition: reaction tank volume is 1.4mL, reaction tank temperature is 40 DEG C ~ 110 DEG C, and after post, flow velocity is 0.1mL/min ~ 1mL/min;
(3) chromatogram of typical curve and derivative products measures:
Configure the glyoxal series standard solution of multiple variable concentrations respectively, and according to the method for step (1), (2), derivatization analysis detection is carried out to it, according to detection Plotting data typical curve, obtain the chromatogram of derivative products.
In such scheme, derivating agent solution 5,6-diaminourea pyrimidine and glyoxal reaction principle as follows:
In step (1) use the pH value of ammonium chloride buffer solution to be respectively 7.5,8.5,9.0,9.5,10,10.5,11.
In step (1) use the concentration of ammonium chloride buffer solution to be respectively 0.05mol/L, 0.1mol/L, 0.2mol/L, 0.3mol/L, 0.4mol/L, 0.5mol/L.
Described in step (1), the concentration of 5,6-diaminourea pyrimidine derivates agent solutions is respectively 50mg/L, 100mg/L, 200mg/L, 300mg/L, 400mg/L.
In described step (2) post-column derivation condition, the temperature of reaction tank is decided to be 40 DEG C, 50 DEG C, 60 DEG C, 70 DEG C, 80 DEG C, 90 DEG C, 100 DEG C, 110 DEG C respectively.
After described step (2) post-column derivation condition center pillar, flow velocity is decided to be 0.1mL/min, 0.2mL/min, 0.3mL/min, 0.4mL/min, 0.5mL/min, 0.8mL/min, 1mL/min respectively.
Compared with prior art, the invention has the advantages that: use post-column derivation-high performance liquid chromatography to glyoxal in Food Contact paper products content measure, and parameter optimization has been carried out to the concentration of derivative reaction temperature, buffer solution, derivative reagent concentration, derivative reagent pH, derivative reagent flow velocity, after testing, under the derivatization conditions optimized and chromatographic condition, the retention time of glyoxal derivative is 4.2min, in good linear relation in mass concentration 0.1mg/L ~ 20mg/L, typical curve is y=9954760.9x+2416240 (R
2=0.9997), the recovery be 84.7% – 102.3%, RSD 0.7% ~ 5.6%, the method test is simple, subsidiary reaction is few, detection speed is fast and product is single is easy to quantitative, and gained test result is accurately and reliably, reproducible.
Accompanying drawing explanation
Fig. 1 be in the embodiment of the present invention temperature to the interact relation figure of derivative reaction;
Fig. 2 be in the embodiment of the present invention pH to the interact relation figure of derivative reaction;
Fig. 3 is the interact relation figure of concentration to derivative reaction of ammonium chloride buffer solution in the embodiment of the present invention;
Fig. 4 be after the embodiment of the present invention center pillar flow velocity and 5,6-diaminourea pyrimidine derivates agent concentration to the interact relation figure of derivative reaction;
Fig. 5 be in the embodiment of the present invention glyoxal canonical plotting;
Fig. 6 is that in the embodiment of the present invention, under Optimal Parameters, glyoxal standard solution derives afterproduct 2,4-dioxidotetrahydro and to talk endlessly the chromatogram of pyridine.
Embodiment
Below in conjunction with accompanying drawing embodiment, the present invention is described in further detail.
In the mensuration Food Contact paper products of the present embodiment, the method for glyoxal content comprises the following steps:
(1) preliminary work before test:
A, with ammonium chloride buffer solution preparation 5,6-diaminourea pyrimidine derivates agent solution;
In b, paper glyoxal extraction: sample paper is cut into 1cm
2~ 2cm
2paper fragment, then the paper fragment of 10g is taken, the paper fragment weighed up is moved in the conical flask of 500mL, then the ultrapure water getting 200mL joins in conical flask, finally conical flask is put into the constant temperature oscillator of 25 DEG C, concussion 25h, afterwards solution poured out and repeatedly clean the conical flask leaving paper fragment with ultrapure water, filter, filtrate is moved in the volumetric flask of 250mL, be settled to scale with ultrapure water;
C, accurately take the tertiary sodium phosphate of 1.9006g, add ultrapure water and about use phosphoric acid adjust pH to 2.5 again to 800mL, be settled to 1L, 0.45 μm of membrane filtration, stand-by after ultrasonic process;
D, mocromembrane filtration is carried out to the material obtained in step a, b, then directly go up machine testing;
(2) detect:
A, instrument: 2695e-U.S. Butterworth is special, high performance liquid chromatograph;
B, liquid-phase condition: leacheate is V
acetonitrile: V
tertiary sodium phosphate buffer salt=3:97, sample size is 10 μ L, and flow velocity is 1mLmin
-1, post case temperature is 40 DEG C;
C, chromatographic condition: chromatographic column is Shim-PakC18 post, 250mm × 4.6mm, particle diameter 5 μm; Fluorescence exciting wavelength is 350nm, emission wavelength 500nm, and when determining above-mentioned wavelength, first scan respectively the excitation wavelength of fluorescence and emission wavelength, fixing excitation wavelength is 300nm, scanning maximum emission wavelength, and discovery maximum emission wavelength is about 460nm; Then fixing maximum emission wavelength is 460nm, scanning excitation wavelength, when finding that excitation wavelength is 350nm, the response of target compound is maximum, but background also has very large raising when experiment finds that emission wavelength is 460nm, therefore select background influence little, and target compound respond also larger 500nm as emission wavelength;
D, post-column derivation condition: reaction tank volume is 1.4mL;
(3) optimization of derivatization parameter:
(3.1) derivative reaction temperature
The glyoxal sample solution of a series of 10mg/L of sample introduction, change respectively reaction tank temperature to 40 DEG C, 50 DEG C, 60 DEG C, 70 DEG C, 80 DEG C, 90 DEG C, 100 DEG C, 110 DEG C, obtain the relation of temperature of reaction and derivative products content, as shown in Figure 1, can find out, temperature is higher for result, derivative products is more, although the higher reaction of temperature is more thorough, too high temperature may cause glyoxal instability, and then affect the fluctuation of product area.At 80 DEG C and 110 DEG C, repeat sample introduction 5 times actually by glyoxal solution, the RSD of both discoveries is respectively 2.3% and 5.1%, and too low temperature fluorescence intensity is large not, has impact to detection sensitivity, therefore the present embodiment preferably 80 DEG C be temperature of reaction.
(3.2) pH of derivative reagent
The glyoxal sample solution of a series of 10mg/L of sample introduction, change pH value respectively to 7.5 of ammonium chloride buffer solution, 8.5, 9.0, 9.5, 10, 10.5, 11, observe pH value to the impact of derivative products, as shown in Figure 2, can find out, when pH value equals 10, derivative products peak area is maximum, this is due to used 5, 6-diaminourea pyrimidine is sulfate, weak base is needed to be decomposed by salt during reaction, alkali is dissociated out, and glyoxal reaction then, and aldehyde radical and amine react the imines generated can be hydrolyzed in diluted acid, original aldehyde radical and amine can be become again, alkalescence is conducive to the carrying out reacted, but be greater than in the system of 10 at pH, maximum emission wavelength may have occurred change, therefore peak area declines on the contrary, the pH=10 of the preferred ammonium chloride buffer solution of the present embodiment.
(3.3) concentration of ammonium chloride buffer solution
The glyoxal sample solution of a series of 10mg/L of sample introduction, change the concentration of ammonium chloride buffer respectively to 0.05mol/L, 0.1mol/L, 0.2mol/L, 0.3mol/L, 0.4mol/L, 0.5mol/L, as shown in Figure 3, can find out, when the concentration of ammonium chloride buffer solution is 0.1mol/L, derivative products peak area is maximum, along with the increase of buffer concentration, the peak area of derivative products reduces on the contrary, this may be because damping fluid raises effect to fluorescence background, the peak area of product is diminished, when 0.05mo/L, the molten amount of buffering of damping fluid is inadequate, therefore there is maximum derivative products area during 0.1mol/L.Consider that sample may in acid and enough buffer capacity, avoid the error because pH causes, the preferred ammonium chloride buffer concentration of the present embodiment is 0.3mol/L.
(3.4) flow velocity and derivative reagent concentration after post
The glyoxal sample solution of a series of 10mg/L of sample introduction, after changing post respectively, flow velocity is to 0.1mL/min, 0.2mL/min, 0.3mL/min, 0.4mL/min, 0.5mL/min, 0.8mL/min, 1mL/min, derivative reagent concentration is to 50mg/L, 100mg/L, 200mg/L, 300mg/L, 400mg/L, investigate therebetween dynamic relationship on the impact of derivatization reaction, result as shown in Figure 4, can find out, peak area changes by the combined influence of flow velocity after post and derivative reagent concentration, the increase of derivative reagent causes to the existing increase because of amount of peak area the active influence that peak area becomes large, also negatively influencing peak area being diminished because derivative reagent increase causes background to increase is had.When after post, flow velocity is before 0.2mL/min, the content of derivative reagent is to peak areas mainly active influence.Namely along with the increase of derivative reagent, the peak area of product becomes large; When flow velocity after post is at 0.3mL/min ~ 1.0mL/min, derivative reagent concentration is when below 300mg/L, and the content of derivative reagent is active influence to peak areas, and peak area increases along with the increase of derivative reagent concentration; When being 400mg/L to derivative reagent concentration, peak area declines on the contrary, this is because flow velocity is accelerated to make to increase through the derivative reagent amount of detecting device in the unit interval, now derivative reagent concentration has humidification to background and peak areas is reduced, this effect is better than derivative reagent to be increased and causes the effect that peak area becomes large, therefore makes peak area diminish on the contrary.In fact, when derivative reagent concentration 300mg/L and above time reagent have larger humidification to background, will the detection limit of method be affected.Therefore in the present embodiment, the concentration of preferred derivative reagent is 200mg/L.
When derivative reagent concentration is 200mg/L, after post, flow velocity is watershed divide on the impact of peak areas when 0.2mL/min, when flow velocity is greater than 0.2mL/min, along with the increase peak areas of flow velocity reduces, this is because the increase flowing through the derivative reagent amount of reaction tank in the unit interval causes the increase of peak area, but this boost value is less than the decreasing value of the peak area caused ahead of time due to appearance time, therefore causes peak areas to diminish; After post, flow velocity is before 0.2mL/min, the increase of flow velocity makes appearance time become early and cause peak area to diminish, this value of diminishing is less than the added value produced because of the increase of unit interval amount of reagent, therefore, in the present embodiment derivative reagent post after flow velocity be preferably 0.2mL/min.
(4) range of linearity and detection limit
Configure the glyoxal series standard solution of 0.1mg/L, 0.5mg/L, 1.0mg/L, 2.0mg/L, 4.0mg/L, 10mg/L, 20mg/L respectively, by the method for testing of the present embodiment, measure under above-mentioned preferred chromatographic resolution testing conditions, glyoxal the range of linearity and detection limit (S/N=3) as shown in table 1, typical curve and standard colors spectrogram as shown in Figure 5,6, coefficient R
2=0.9997, detect and be limited to 0.01mg/L; By the glyoxal of continuous sample introduction 1mg/L 11 times, calculate the RSD of derivative afterproduct, each assay intervals is 5 minutes, carrys out the stability of appraisal procedure, and the RSD mean value measured for 11 times is 3.5%, shows that the stability of this method is better.
Table 1
(5) recovery of standard addition test and precision
Various sample extraction liquid in his-and-hers watches 2 add the glyoxal of basic, normal, high three different contents respectively, carry out the test of recovery of standard addition and precision, as shown in Table 2, glyoxal recovery of standard addition 84.7% ~ 102.3%, precision is 0.7% ~ 5.6%.The assay method that the test data of table 2 demonstrates the present embodiment further has good stability.
Table 2
General paper products, for slightly heavy paper disc, the minimum area of 10g paper disc sample is 0.1dm
2, the method operation according to the present embodiment converts, and detection limit can reach 0.025mg/dm
2, be minimumly quantitatively limited to 0.25mg/dm
2, the content that can meet glyoxal monomer in German federal risk assessment (BFR) regulation Food Contact paper products must not more than 1.5mg/dm
2testing requirement, further illustrate the detect delay methods and results of the present embodiment accurately and reliably, reproducible.
Claims (6)
1. measure a method for glyoxal content in Food Contact paper products, it is characterized in that comprising the following steps:
(1) preliminary work before test:
A, be 7.5 ~ 11.0 with pH, 5, the 6-diaminourea pyrimidine derivates agent solutions of concentration to be the ammonium chloride buffer solution compound concentration of 0.05mol/L ~ 0.5mol/L be 50mg/L ~ 400mg/L;
In b, paper glyoxal extraction: sample paper is cut into 1cm
2~ 2cm
2paper fragment, then the paper fragment of 10g is taken, the paper fragment weighed up is moved in the conical flask of 500mL ~ 1000mL, then the ultrapure water getting 100mL ~ 200mL joins in conical flask, finally conical flask is put into the constant temperature oscillator of 20 DEG C ~ 25 DEG C, concussion 20h ~ 25h, afterwards solution poured out and repeatedly clean the conical flask leaving paper fragment with ultrapure water, filter, filtrate is moved in the volumetric flask of 250mL, be settled to scale with ultrapure water;
C, mocromembrane filtration is carried out to the material obtained in step a, b, then directly go up machine testing;
(2) detect:
A, instrument: 2695e-U.S. Butterworth is special, high performance liquid chromatograph;
B, liquid-phase condition: leacheate is V
acetonitrile: V
tertiary sodium phosphate buffer salt=3:97, sample size is 10 μ L, and flow velocity is 1mLmin
-1, post case temperature is 40 DEG C;
C, chromatographic condition: chromatographic column is Shim-PakC18 post, 250mm × 4.6mm, particle diameter 5 μm, fluorescence exciting wavelength is 350nm, emission wavelength 500nm;
D, post-column derivation condition: reaction tank volume is 1.4mL, reaction tank temperature is 40 DEG C ~ 110 DEG C, and after post, flow velocity is 0.1mL/min ~ 1mL/min;
(3) chromatogram of typical curve and derivative products measures:
Configure the glyoxal series standard solution of multiple variable concentrations respectively, and according to the method for step (1), (2), derivatization analysis detection is carried out to it, according to detection Plotting data typical curve, obtain the chromatogram of derivative products.
2. the method for glyoxal content in mensuration Food Contact paper products according to claim 1, is characterized in that: in step (1) use the pH value of ammonium chloride buffer solution to be respectively 7.5,8.5,9.0,9.5,10,10.5,11.
3. the method for glyoxal content in mensuration Food Contact paper products according to claim 1, is characterized in that: in step (1) use the concentration of ammonium chloride buffer solution to be respectively 0.05mol/L, 0.1mol/L, 0.2mol/L, 0.3mol/L, 0.4mol/L, 0.5mol/L.
4. the method for glyoxal content in mensuration Food Contact paper products according to claim 1, it is characterized in that: described in step (1), the concentration of 5,6-diaminourea pyrimidine derivates agent solutions is respectively 50mg/L, 100mg/L, 200mg/L, 300mg/L, 400mg/L.
5. the method for glyoxal content in mensuration Food Contact paper products according to claim 1, is characterized in that: in described step (2) post-column derivation condition, the temperature of reaction tank is decided to be 40 DEG C, 50 DEG C, 60 DEG C, 70 DEG C, 80 DEG C, 90 DEG C, 100 DEG C, 110 DEG C respectively.
6. the method for glyoxal content in mensuration Food Contact paper products according to claim 1, is characterized in that: after described step (2) post-column derivation condition center pillar, flow velocity is decided to be 0.1mL/min, 0.2mL/min, 0.3mL/min, 0.4mL/min, 0.5mL/min, 0.8mL/min, 1mL/min respectively.
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| CN101539543A (en) * | 2009-02-05 | 2009-09-23 | 上海华谊（集团）公司 | Method for detecting glyoxylate and glyoxal by high performance liquid chromatography |
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| 高效液相色谱法同时测定乙二醛和乙醛;刘树彬等;《河北师范大学学报/自然科学版/》;20090930;第33卷(第5期);638-640、644 * |
| 高效液相色谱法测定乙醛溶液中的乙二醛和乙醛酸;朱鸭梅等;《色谱》;20100131;第28卷(第1期);59-63 * |
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