CN114755327B - Quantitative analysis method of N, N' -ethylene bis (stearamide) in high polymer material - Google Patents

Quantitative analysis method of N, N' -ethylene bis (stearamide) in high polymer material Download PDF

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CN114755327B
CN114755327B CN202210329848.3A CN202210329848A CN114755327B CN 114755327 B CN114755327 B CN 114755327B CN 202210329848 A CN202210329848 A CN 202210329848A CN 114755327 B CN114755327 B CN 114755327B
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ethylene bis
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ethylenebisstearamide
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CN114755327A (en
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吴博
庞承焕
刘佩
李卫领
谢晓琼
陈平绪
宁红涛
叶南飚
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Guogao High Polymer Material Industry Innovation Center Co Ltd
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    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
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    • G01N30/72—Mass spectrometers

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Abstract

The invention discloses a quantitative analysis method of N, N' -ethylene bis stearamide in a high polymer material, which comprises the following steps: preparing a sample solution to be measured and a series of concentration standard solutions; carrying out gas chromatography mass spectrometry detection on a series of concentration standard solutions, taking ions with peak time of 21.8min and m/z of 86 as quantitative ions, and drawing a standard curve according to the corresponding relation between the peak area of the measured m/z 86 ions at 21.8min and the concentration; and analyzing the sample solution to be detected by adopting the same gas chromatography mass spectrometry detection condition, quantifying according to the peak area of the measured m/z 86 ions at 21.8min and a standard curve, and calculating the concentration of the N, N '-ethylene bis stearamide in the sample solution to be detected, thereby calculating the content of the N, N' -ethylene bis stearamide in the polymer material to be detected. The method has the advantages of higher sensitivity and accuracy, strong specificity, simpler processing steps, various applicable high polymer materials and more environmental friendliness.

Description

Quantitative analysis method of N, N' -ethylene bis (stearamide) in high polymer material
Technical Field
The invention relates to the technical field of quantitative analysis of functional additives of high polymer materials, in particular to a quantitative analysis method of N, N' -ethylene bis-stearamide in a high polymer material.
Background
N, N' -Ethylene Bis Stearamide (EBS) has two polar amide groups structurally, so that the EBS has a lubricating effect and a low-temperature anti-sticking effect on the processing of polymer resin, and is widely applied to the processing process of high polymer materials such as PS, AS, PVC, PE, PP, PVAC, nylon, phenolic resin and the like. 1 to 3 percent of EBS is added in the synthetic resin and rubber such as Polychloroprene (SBR) and Styrene Butadiene Rubber (SBR), so that the anti-adhesion and anti-caking effects can be improved; the EBS is added into the paint, so that the paint remover performance can be improved, and the leveling property of the surface of the baked enamel paint can be improved; EBS can act as a matting agent in furniture polishes and printing inks; in the chemical fiber industry, the EBS can improve the heat resistance, weather resistance and flow property of the polyester fibers and endow the polyester fibers with a certain antistatic effect. N, N' -ethylene bis-stearamide has almost no ultraviolet absorption and is not suitable for high performance liquid chromatography analysis of conventional ultraviolet absorption detectors. Internationally, a learner in the text "N, N '-Ethylenebisstearamide Additive in Intravaginal Drug Delivery Device Determined by NP-LC with ELSD" proposed to detect N, N' -ethylene bis stearamide by using a liquid chromatograph equipped with an evaporative light scattering detector, the method has low detection limit, but has strong dependence on equipment, and the domestic popularization rate of the equipment is low at present.
Zhang Fangfang et al in patent CN108872416a propose a method for simultaneous quantitative detection of erucamide and ethylene bis stearamide. The method comprises the steps of cutting a sample, immersing the sample in an extraction medium, extracting the sample in a closed container, adding a mixed solvent and an internal standard stock solution after extracting, shaking uniformly, layering, taking a lower layer solution, feeding the lower layer solution to a gas chromatograph, carrying out gas chromatographic analysis, and respectively calculating peak areas to obtain the respective contents of erucamide and ethylenebisstearamide. The method has a plurality of pretreatment steps, the test process also needs to use dimethyl phthalate internal standard solution, the method is complex to implement, and the sample is characterized by only depending on the peak-off time, and the method lacks certain accuracy.
Disclosure of Invention
Based on the above, the present invention aims to overcome the shortcomings of the prior art, and provide a quantitative analysis method for N, N' -ethylene bis stearamide in a polymer material.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows: a quantitative analysis method of N, N' -ethylene bis stearamide in a high polymer material comprises the following steps:
(1) Extracting a high molecular material to be detected by adopting an organic solvent, and separating a precipitate to obtain a sample solution to be detected;
(2) Dissolving N, N' -ethylene bis (stearamide) with different concentrations by adopting an organic solvent to obtain a series of standard solutions with different concentrations;
(3) Carrying out gas chromatography mass spectrometry detection on the standard solution with the concentration of the series in the step (2), taking the ion with the peak time of 21.8min and the mass-to-charge ratio (m/z) of 86 as a quantitative ion, and drawing a standard curve according to the corresponding relation between the peak area of the measured m/z 86 ion at 21.8min and the concentration;
(4) And (3) analyzing the sample solution to be detected in the step (1) under the same gas chromatography mass spectrometry detection conditions in the step (3), and calculating the concentration of the N, N '-ethylene bis stearamide in the sample solution to be detected according to the peak area of the m/z 86 ions at 21.8min measured by the sample solution to be detected and the standard curve quantification in the step (3), thereby calculating the content of the N, N' -ethylene bis stearamide in the polymer material to be detected.
The N, N' -ethylene bis stearamide standard solution has two characteristic peaks around 18.3min and 21.8min under the test conditions. And (3) respectively carrying out linear curve drawing on the standard solution according to the peak outlet time of 18.3min, the ion peak area of the mass-to-charge ratio (m/z) 57, the peak outlet time of 21.8min and the ion peak area of the mass-to-charge ratio (m/z) 86, wherein the linearity of the standard curve of the peak outlet time of 21.8min and the standard curve of the m/z 86 is better.
Preferably, the polymer material to be detected in the step (1) is polypropylene (PP), ethylene-vinyl acetate copolymer (EVA), polystyrene (PS), polyethylene (PE), acrylonitrile-styrene copolymer (AS), polyamide 6 (PA 6), polyamide 66 (PA 66).
Preferably, the polymer material to be detected in the step (1) is crushed to 500-1000 meshes in advance.
Preferably, the organic solvent in the steps (1) and (2) is one or more of chloroform, dichloromethane, acetone, ethanol and methanol; more preferably, the organic solvent in the steps (1) and (2) is dichloromethane and methanol according to a volume ratio of 9:1 proportion of mixed solvent.
Preferably, both the extraction in step (1) and the dissolution in step (2) are performed by means of ultrasound; more preferably, the extraction in step (1) and the dissolution in step (2) are carried out by ultrasonic treatment at 40-60 ℃ for 2-4 hours.
Preferably, the separating precipitate in step (1) is a filtration with a 0.45 μm filter.
Preferably, the N, N' -ethylene bis stearamide of step (2) is pre-ground.
Preferably, the conditions for the gas chromatography mass spectrometry detection in step (3) are set as follows: type of column DB-5MS (30 m. Times.250 μm. Times.0.25 μm), sample inlet temperature: 280-300℃: detector temperature: 300-320 ℃, and heating up the program: the initial temperature is 100 ℃, the temperature is raised to 320 ℃ at a speed of 50 ℃ per minute within 5 minutes, and the temperature is kept for 15 minutes; the ion source temperature is 230 ℃, the temperature of the quaternary rod is 150 ℃, and the scanning range is 50-800 u.
Preferably, the correlation coefficient of the standard curve in the step (3) is 0.995.
Compared with the prior art, the invention has the beneficial effects that:
compared with other methods, the quantitative analysis method of the N, N' -ethylene bis-stearamide in the high polymer material has higher sensitivity and accuracy, and the standard adding recovery rate reaches 90-110%. And the special property is strong, the treatment steps are simpler, the applicable high polymer materials are various, and the method comprises PP, EVA, PS, PE, AS, PA and PA66, and is more environment-friendly.
Drawings
FIG. 1 is a gas chromatograph of a sample of example 1.
FIG. 2 is a gas chromatography-mass spectrometry chromatogram of N, N' -ethylene bis-stearamide; wherein A is a solvent blank chromatogram, and B is a standard solution chromatogram.
FIG. 3 is a graph of the linear relationship of the standard curve; wherein the abscissa is the concentration of the N, N' -ethylene bis stearamide standard solution, and the ordinate is the peak area of the ion with the mass-to-charge ratio of 86 of 21.8 min.
FIG. 4 is a gas chromatograph of a sample of example 2.
FIG. 5 is a gas chromatograph of a sample of comparative example 1.
FIG. 6 is a gas chromatograph of a sample of comparative example 2.
Detailed Description
For a better description of the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to the following specific examples.
In the examples, the experimental methods used are conventional methods unless otherwise specified, and the materials, reagents, etc. used, unless otherwise specified, are commercially available.
Example 1
(1) Sample preparation: 1 part (Guangzhou petrochemical, brand name PPR-4220) of Polypropylene Plastic (PP) containing N, N' -ethylene bis stearamide is taken, frozen for 5 minutes by liquid nitrogen, and then the granules are transferred into a crushing device to be crushed, and a sample with the particle size of 800 meshes is sieved for further testing.
(2) Preparing a sample solution to be tested:
a. accurately weighing 2g of crushed sample, placing the sample in a brown closed container, adding 40mL of dichloromethane-methanol (volume ratio is 9:1) mixed solvent, and extracting by ultrasonic waves at 50 ℃ for 3 hours.
b. Filtering the extracted sample with a filter membrane of 0.45 μm to obtain a sample solution to be detected.
(3) Preparation of standard solution:
a. 1g of N, N' -ethylene bis stearamide pure substance is taken and grinded in a grinding device so as to enlarge the contact area between the standard sample and the solvent.
b. 2mg, 2.5mg, 4mg, 6mg and 8mg of N, N' -ethylene bis stearamide pure substances are accurately weighed by an analytical balance and placed in a brown closed container, 40mL of methylene dichloride-methanol (volume ratio is 9:1) mixed solvent is added, ultrasonic waves are carried out for 3 hours at 50 ℃ to ensure that the samples are completely dissolved in the solvent, and thus, standard solutions with the concentrations of 50 mug/mL, 80 mug/mL, 100 mug/mL, 200 mug/mL and 250 mug/mL are respectively obtained.
(4) Gas chromatography-mass spectrometry test condition settings: type of column: DB-5MS (30 m.times.250 μm.times.0.25 μm); sample inlet temperature: 290 ℃; detector temperature: 320 ℃; heating program: the initial temperature was raised to 320℃over 5 minutes at a rate of 50℃per minute for 15 minutes. The ion source temperature is 230 ℃, the temperature of the quaternary rod is 150 ℃, and the scanning range is 50-800 u.
(5) Gas chromatography-mass spectrometry sample injection test: and (3) taking the sample solution to be tested in the step (2) into a sample injection small bottle, and marking. Sample sequences are set in the online software, and after checking the sequence accuracy, testing is started. To reduce interference, two solvent blanks were tested prior to sample testing. And (3) extracting the solution of the upper machine by the sample injection needle, and detecting according to the detection conditions set in the step (4). The gas chromatography-mass spectrometry chromatogram of the sample is shown in figure 1.
(6) Drawing a standard curve: the N, N' -ethylene bis stearamide standard solution in the step (5) has two characteristic peaks near 18.3min and 21.8min, the ions with the peak-out time of 21.8min and the mass-to-charge ratio (m/z) of 86 are taken as quantitative ions, and a standard curve is drawn according to the corresponding relation between the peak area of the measured m/z 86 ions at each concentration and the concentration at 21.8 min. The Gas Chromatography Mass Spectrometry (GCMS) chromatogram of N, N' -ethylene bis-stearamide standard solution is shown in FIG. 2. The linear relationship of the standard curve is shown in fig. 3.
The linear regression equation, the linear range, the correlation coefficient and the detection limit of the method are shown in table 1, and the N, N' -ethylene bis stearamide has good linear relation in the linear range, so that the analysis method requirement is met. The detection limit is 0.8mg/kg, which shows that the method has better sensitivity.
Table 1 method linear regression equation, linear range, correlation coefficient and detection limit
Wherein: y and x represent the integrated peak area of the corresponding quantitative ion of the analyte and the theoretical concentration of the analyte, respectively.
(7) And (3) recovery rate measurement: taking the sample prepared in the step (1)And (3) taking 3 samples in parallel, respectively adding 2mg, 4mg and 8mg of N, N' -ethylene bis stearamide pure substances to obtain a labeled sample, and carrying out sample treatment and test according to the steps (2), 4 and 5). Recovery calculations were performed by the following formula: r= (C 1 -C 0 )/C*100％；
Wherein: r-recovery in units of;
C 1 the measured concentration of N, N' -ethylene bis stearamide in μg/mL in the labeled sample;
C 0 the unit of the measured concentration of N, N' -ethylene bis stearamide in the sample to be measured is mug/mL;
theoretical standard concentration of N, N' -ethylene bis stearamide in the C-standard sample is given in μg/mL.
The labeling recovery rate reaches 90% -110%, which indicates that the quantitative analysis method has high sensitivity and accuracy.
TABLE 2 example 1 addition of standard recovery
Example 2
The test procedure in example 2 was identical to that of example 1 except that the test sample matrix was replaced with a Polyamide (PA) material containing N, N '-ethylenebisstearamide (dupont, trade mark 103 HSL) from a polypropylene (PP) material containing N, N' -ethylenebisstearamide, and the organic solvents used for the test sample solution and standard solvent were chloroform and methanol in a volume ratio of 8:2 proportion of mixed solvent. The gas chromatography for the samples is shown in figure 4. The sample recovery results are shown in Table 3.
TABLE 3 example 2 addition of standard recovery
Comparative example 1
(1) Sample preparation: 1 part (Guangzhou petrochemical, brand K7227) of 30g of Polypropylene Plastic (PP) which does not contain N, N' -ethylene bis stearamide but contains erucamide is frozen for 5 minutes by liquid nitrogen, and then the granules are transferred into a crushing device to be crushed, and a sample with the mesh number of 800 meshes is sieved for the next test. About 1g of erucamide pure substance is taken and grinded in a grinding device, so that the particle size of a sample is smaller, and the contact area between a standard sample and a solvent is increased.
(2) Preparing a sample solution to be tested:
a. accurately weighing 2g of crushed sample, placing the sample in a brown closed container, adding 40mL of dichloromethane-methanol (volume ratio is 9:1) mixed solvent, and extracting by ultrasonic waves at 50 ℃ for 3 hours.
b. Filtering the dissolved solution with a filter membrane with the diameter of 0.45 mu m to obtain a sample solution to be detected.
(3) Gas chromatography-mass spectrometry test condition settings: type of column: DB-5MS (30 m.times.250 μm.times.0.25 μm); sample inlet temperature: 290 ℃; detector temperature: 320 ℃; heating program: the initial temperature was raised to 320℃over 5 minutes at a rate of 50℃per minute for 15 minutes. The ion source temperature is 230 ℃, the temperature of the quaternary rod is 150 ℃, and the scanning range is 50-800 u.
(4) Gas chromatography-mass spectrometry sample injection test: and (3) taking the sample solution to be tested in the step (2) into a sample injection small bottle, and marking. Sample sequences are set in the online software, and after checking the sequence accuracy, testing is started. To reduce interference, two solvent blanks were tested prior to sample testing. And the sample injection needle extracts the solution of the upper machine and detects according to the set detection conditions.
The gas chromatography-mass spectrometry chromatogram of this example is shown in FIG. 6, in which erucamide has a strong characteristic peak at 10.5 min. However, in the case where the sample components are complex, the quantification of erucamide is disturbed by nearby peaks.
(5) And (3) recovery rate measurement: taking the samples prepared in the step (1), and taking 4 samples in parallel, wherein no erucamide pure substance is added to 1 sample, and 2mg, 4mg and 8mg erucamide pure substance are respectively added to the rest 3 samples, and carrying out sample treatment and test according to the steps (2), 3) and (4). Recovery calculations were performed by the following formula:
R＝(C 1 -C 0 )/C*100％；
wherein: r-recovery in units of;
C 1 -determining the concentration of erucamide in the sample in μg/mL;
C 0 the measured concentration of erucamide in the sample to be measured is given in μg/mL;
theoretical standard concentration of erucamide in C-standard sample is given in μg/mL.
Table 5 comparative example 2 addition of standard recovery
According to the recovery rates of the examples and the comparative examples, the invention has high detection sensitivity for the content of the N, N' -ethylene bis-stearamide, has strong specificity and has low accuracy for other amide lubricants.
Carbon emission detection
The carbon emission amount of the test procedure of example 1 was calculated according to ISO14010 and ISO 14044. The method comprises the steps of decomposing the operation steps into a series of unit processes: sample crushing, weighing, ultrasonic extraction, filtering and testing, and meanwhile, liquid chromatography and internal standard gas chromatography are also decomposed into a series of unit processes. Data were entered in Simapro7 software and the carbon emissions for three different analysis methods were calculated by the software. The results are shown in Table 6, and show that compared with other chemical analysis methods (liquid chromatography and internal standard gas chromatography), the quantitative analysis method of the functional additive N, N' -ethylene bis-stearamide in the high polymer material has the advantages of minimum carbon emission, environmental friendliness and more accordance with the requirement of a green chemical analysis method.
TABLE 6 carbon footprint for different analysis methods
Analysis method Example 1 Liquid chromatography Internal standard gas chromatography
Carbon footprint (CO) 2 eq) 1.69 4.21 5.13
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted equally without departing from the spirit and scope of the technical solution of the present invention.

Claims (8)

1. The quantitative analysis method of the N, N' -ethylene bis stearamide in the high polymer material is characterized by comprising the following steps of:
(1) Extracting a high molecular material to be detected by adopting an organic solvent, and separating a precipitate to obtain a sample solution to be detected;
(2) Dissolving N, N' -ethylene bis (stearamide) with different concentrations by adopting an organic solvent to obtain a series of standard solutions with different concentrations;
(3) Carrying out gas chromatography mass spectrometry detection on the standard solution with the concentration of the series in the step (2), taking the ion with the peak time of 21.8min and the mass-to-charge ratio (m/z) of 86 as a quantitative ion, and drawing a standard curve according to the corresponding relation between the peak area of the measured m/z 86 ion at 21.8min and the concentration;
(4) Taking the sample solution to be detected in the step (1), and adopting the gas chromatography mass spectrometry detection strip similar to the step (3)Analyzing the piece, and calculating N, N in the sample solution to be measured according to the peak area of m/z 86 ions measured in the sample solution to be measured at 21.8min and the standard curve quantification in the step (3) ’ -concentration of ethylene bis stearamide, thereby calculating the content of N, N' -ethylene bis stearamide in the polymeric material to be detected;
setting the conditions for gas chromatography mass spectrometry detection in the step (3): chromatographic column type DB-5MS,30m×250 μm×0.25 μm, sample inlet temperature: 280-300℃: detector temperature: 300-320 ℃, and heating up the program: the initial temperature is 100 ℃, the temperature is raised to 320 ℃ at a speed of 50 ℃ per minute within 5 minutes, and the temperature is kept for 15 minutes; the temperature of the ion source is 230 ℃, the temperature of the quaternary rod is 150 ℃, and the scanning range is 50-800 u;
the organic solvent in the step (1) and the step (2) is one or more of chloroform, dichloromethane, acetone, ethanol and methanol.
2. The method for quantitatively analyzing N, N' -ethylenebisstearamide in a polymer material according to claim 1, wherein the polymer material to be detected in the step (1) is pulverized into 500-1000 meshes in advance.
3. The method for quantitatively analyzing N, N' -ethylenebisstearamide in a high molecular material according to claim 1, wherein the organic solvent in the steps (1) and (2) is dichloromethane and methanol according to a volume ratio of 9:1 proportion of mixed solvent.
4. The method for quantitatively analyzing N, N' -ethylenebisstearamide in a high molecular material according to claim 1, wherein the extraction in the step (1) and the dissolution in the step (2) are both carried out by adopting an ultrasonic method.
5. The method for quantitatively analyzing N, N' -ethylenebisstearamide in a polymer material according to claim 4, wherein the extraction in the step (1) and the dissolution in the step (2) are carried out by ultrasonic treatment at 40-60 ℃ for 2-4 hours.
6. The method for quantitatively analyzing N, N' -ethylenebisstearamide in the high molecular material according to claim 1, wherein the high molecular material to be detected in the step (1) is PP, EVA, PS, PE, AS, PA and PA66.
7. The method for quantitatively analyzing N, N' -ethylenebisstearamide in a high molecular material according to claim 1, wherein the correlation coefficient of the standard curve in the step (3) is not less than 0.995.
8. The method for quantitatively analyzing N, N '-ethylenebisstearamide in a polymer material according to claim 1, wherein the N, N' -ethylenebisstearamide in the step (2) is ground in advance.
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