CN114755327A - 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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CN114755327A
CN114755327A CN202210329848.3A CN202210329848A CN114755327A CN 114755327 A CN114755327 A CN 114755327A CN 202210329848 A CN202210329848 A CN 202210329848A CN 114755327 A CN114755327 A CN 114755327A
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ethylene bis
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CN114755327B (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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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 detected and a series of concentration standard solutions; performing gas chromatography mass spectrometry detection on the series of concentration standard solutions, taking ions with the peak-out time of 21.8min and the m/z of 86 as quantitative ions, and drawing a standard curve according to the corresponding relation between the peak area and the concentration of the m/z 86 ions detected at each concentration in 21.8 min; and analyzing the sample solution to be detected by adopting the same gas chromatography-mass spectrometry detection conditions, quantifying according to the peak area of the m/z 86 ions to be detected in 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 high molecular material to be detected. The method has the advantages of higher sensitivity and accuracy, strong specificity, simpler processing steps, more applicable types of high polymer materials and more environment-friendly property.

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
The N, N '-Ethylene Bis Stearamide (EBS) structurally has two polar amide groups, so that the N, N' -ethylene bis stearamide 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. When 1-3% of EBS is added in the synthetic resin and rubber such as chloroprene rubber (Polychloroprene) and Styrene Butadiene Rubber (SBR), the anti-adhesion and anti-caking effects can be improved; the EBS is added into the paint to improve the performance of the paint remover and improve the leveling property of the surface of the baked enamel paint; EBS can act as a matting agent in furniture polishes and printing inks; in the chemical fiber industry, EBS can improve the heat resistance, weather resistance and flow property of polyester fibers and endow the polyester fibers with certain antistatic effect. The N, N' -ethylene bis stearamide has almost no ultraviolet absorption and is not suitable for high performance liquid chromatography analysis of a conventional ultraviolet absorption detector. The international scholars in the article "N, N '-Ethylenebistearamide Additive in innovative crude Drug Determined by NP-LC with ELSD" propose to detect N, N' -ethylene bis stearamide by using a liquid chromatograph equipped with an evaporative light scattering detector, and the method has low detection limit, but strong dependence on equipment and low domestic popularization rate of the equipment at present.
Zhang Fang et al in patent CN108872416A propose a method for simultaneously and quantitatively detecting erucamide and ethylene bis stearamide. The method comprises the steps of shearing a sample, immersing the sample in an extraction medium, placing the sample in a closed container for extraction, adding a mixed solvent and an internal standard stock solution after extraction, shaking up, layering, taking a lower layer solution, feeding the sample into a gas chromatograph, carrying out gas chromatography analysis, and respectively calculating peak areas to obtain the respective contents of erucamide and ethylene bis stearamide. The method has various pretreatment steps, a dimethyl phthalate internal standard solution is required in the test process, the method is complex to implement, and the sample is determined only by the peak-appearing time, so that certain accuracy is lacked.
Disclosure of Invention
Based on the above, the invention aims to overcome the defects of the prior art and provide a quantitative analysis method for N, N' -ethylene bis stearamide in a high polymer material.
In order to realize the purpose, the technical scheme adopted by the invention is as follows: a quantitative analysis method of N, N' -ethylene bis stearamide in a high molecular material comprises the following steps:
(1) extracting a high molecular material to be detected by adopting an organic solvent, and separating precipitates to obtain a sample solution to be detected;
(2) Dissolving N, N' -ethylene bis stearamide with different concentrations by using an organic solvent to obtain standard solutions with series concentrations;
(3) performing gas chromatography mass spectrometry detection on the standard solution with the series of concentrations in the step (2), taking ions with the peak-out time of 21.8min and the mass-to-charge ratio (m/z) of 86 as quantitative ions, and drawing a standard curve according to the corresponding relation between the peak area and the concentration of the m/z 86 ions detected at each concentration in 21.8 min;
(4) and (3) analyzing the sample solution to be detected in the step (1) by adopting 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 m/z 86 ions detected by the sample solution to be detected in 21.8min and the standard curve quantification in the step (3), thereby calculating the content of the N, N' -ethylene bis-stearamide in the high 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 condition. And (3) respectively drawing linear curves of ion peak areas of the peak-off time of 18.3min and the mass-to-charge ratio (m/z)57 and ion peak areas of the peak-off time of 21.8min and the mass-to-charge ratio (m/z)86 on the standard solution, wherein the standard curves of the peak-off time of 21.8min and the m/z 86 are more excellent in linearity.
Preferably, the polymer material to be detected in step (1) is polypropylene (PP), ethylene-vinyl acetate copolymer (EVA), Polystyrene (PS), Polyethylene (PE), acrylonitrile-styrene copolymer (AS), polyamide 6(PA6), or polyamide 66(PA 66).
Preferably, the polymer material to be detected in step (1) is pre-pulverized to 500-1000 meshes.
Preferably, the organic solvent in steps (1) and (2) is one or more of chloroform, dichloromethane, acetone, ethanol and methanol; more preferably, the organic solvent in steps (1) and (2) is dichloromethane and methanol in a volume ratio of 9: 1 proportion of mixed solvent.
Preferably, the extraction in the step (1) and the dissolution in the step (2) are both performed by means of ultrasound; more preferably, the extraction in the step (1) and the dissolution in the step (2) are carried out for 2-4h by ultrasonic treatment at 40-60 ℃.
Preferably, the precipitate is separated in step (1) by filtration with a 0.45 μm filter membrane.
Preferably, the N, N' -ethylene bis stearamide of step (2) is pre-milled.
Preferably, the gas chromatography-mass spectrometry detection conditions of step (3) are set as follows: column type DB-5MS (30m × 250 μm × 0.25 μm), injection port temperature: 280-300 ℃: detector temperature: and (3) heating at 300-320 ℃, and heating: the initial temperature was 100 ℃, increased to 320 ℃ at a rate of 50 ℃ per minute over 5 minutes, and held for 15 minutes; the ion source temperature is 230 ℃, the quadrupole rod temperature is 150 ℃, and the scanning range is 50-800 u.
Preferably, the correlation coefficient of the standard curve in 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 N, N' -ethylene bis stearamide in the high polymer material has higher sensitivity and accuracy, and the standard addition recovery rate reaches 90-110%. The method has the advantages of strong specificity, simpler processing steps, and more applicable types of high polymer materials, including PP, EVA, PS, PE, AS, PA6 and PA66, and is more environment-friendly.
Drawings
FIG. 1 is a GC-MS chromatogram of the sample of example 1.
FIG. 2 is a GC-MS chromatogram of N, N' -ethylenebisstearamide; wherein A is a solvent blank chromatogram and B is a standard solution chromatogram.
FIG. 3 is a line-type relationship diagram of a 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 ions with the mass-to-charge ratio of 86 at 21.8 min.
FIG. 4 is a gas chromatography-mass spectrometry chromatogram of the sample of example 2.
FIG. 5 is a GC analysis of a sample of comparative example 1.
FIG. 6 is a GC analysis of a sample of comparative example 2.
Detailed Description
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to specific examples.
In the examples, the experimental methods used were all conventional methods unless otherwise specified, and the materials, reagents and the like used were commercially available without otherwise specified.
Example 1
(1) Sample preparation of a sample: 30g of polypropylene (PP) plastic containing N, N' -ethylene bis stearamide 1 part (Guangzhou petrochemical, brand number PPR-4220) is frozen by liquid nitrogen for 5min, then the granules are crushed in a crushing device, and a sample with the particle size of 800 meshes is screened for next testing.
(2) Preparing a sample solution to be tested:
a. accurately weighing 2g of the crushed sample, putting the crushed sample into a brown closed container, adding 40mL of dichloromethane-methanol (volume ratio is 9:1) mixed solvent, and performing ultrasonic extraction for 3h at 50 ℃.
b. And filtering the extracted sample by using a 0.45 mu m filter membrane to obtain a sample solution to be detected.
(3) Preparation of standard solution:
a. the pure 1g N, N' -ethylene bis stearamide is ground in a grinding device to increase the contact area between the standard and the solvent.
b. Accurately weighing 2mg, 2.5mg, 4mg, 6mg and 8mg of N, N' -ethylene bis stearamide pure substances in an analytical balance into a brown closed container, adding 40mL of dichloromethane-methanol (volume ratio is 9:1) mixed solvent, and performing ultrasonic wave for 3h at 50 ℃ to completely dissolve a sample into the solvent to obtain standard solutions with the concentrations of 50 mu g/mL, 80 mu g/mL, 100 mu g/mL, 200 mu g/mL and 250 mu g/mL respectively.
(4) Gas chromatography-mass spectrometry test condition settings: type of chromatography column: DB-5MS (30m 250 μm 0.25 μm); sample inlet temperature: 290 ℃; detector temperature: 320 ℃; temperature rising procedure: the initial temperature was 100 ℃ and increased to 320 ℃ over 5 minutes at a rate of 50 ℃ per minute and held for 15 minutes. The ion source temperature is 230 ℃, the quadrupole rod temperature 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 detected in the step (2) into a sample injection vial, and marking. The sample sequence was set in the online software and the test was started after checking the sequence accuracy. To reduce interference, two solvent blanks were tested prior to sample testing. And (4) extracting the solution on the machine by a sample injection needle, and detecting according to the detection conditions set in the step (4). The GC-MS chromatogram of the sample is shown in FIG. 1.
(6) Drawing a standard curve: and (3) the N, N' -ethylene bis stearamide standard solution in the step (5) has two characteristic peaks at 18.3min and 21.8min, 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 of the peak area and the concentration of the m/z 86 ions measured at each concentration at 21.8 min. The gas chromatography-mass spectrometry (GCMS) chromatogram of the 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 N, N' -ethylene bis stearamide has good linear relation in the linear range and meets the requirement of the analysis method. The detection limit is 0.8mg/kg, which indicates that the method has better sensitivity.
Linear regression equation, linear range, correlation coefficient and detection limit for the method of Table 1
Figure BDA0003574838170000041
Wherein: y and x represent the corresponding quantitative ion integrated peak area of the analyte and the theoretical concentration of the analyte, respectively.
(7) And (3) determining the recovery rate: taking the sample prepared in the step (1), taking 3 samples in parallel, respectively adding 2mg, 4mg and 8mg of N, N' -ethylene bis stearamide pure substances to obtain the labeled samples, and carrying out sample treatment and test according to the steps (2), (4) and (5). The recovery rate was calculated by the following formula: r ═ C1-C0)/C*100％；
In the formula: r-recovery in units;
C1-the measured concentration of N, N' -ethylenebisstearamide in the spiked sample in μ g/mL;
C0determining the concentration of the N, N' -ethylene bis stearamide in the sample to be detected, wherein the unit is mu g/mL;
c-theoretical addition of N, N' -ethylene bis stearamide in spiked samples, in. mu.g/mL.
And the recovery rate of the added standard reaches 90-110%, which indicates that the quantitative analysis method has high sensitivity and accuracy.
Table 2 example 1 recovery on addition of a standard
Figure BDA0003574838170000051
Example 2
The test methods in example 2 are all the same as in example 1, except that the test sample substrate is replaced by a raw material of polypropylene (PP) containing N, N '-ethylene bis stearamide to a raw material of Polyamide (PA) containing N, N' -ethylene bis stearamide (du pont, usa, No. 103HSL), and the organic solvents used for the solution of the sample to be tested and the standard solvent are chloroform and methanol in a volume ratio of 8: 2 proportion of mixed solvent. The GC-MS chromatogram of the sample is shown in FIG. 4. The sample recovery results are shown in table 3.
Table 3 example 2 recovery on addition of a standard
Figure BDA0003574838170000052
Comparative example 1
(1) Sample preparation of a sample: 30g of polypropylene (PP)1 part (Guangzhou petrochemical, trade name K7227) containing no N, N' -ethylene bis stearamide but containing erucamide is frozen by liquid nitrogen for 5min, and then the granules are crushed in a crushing device, and a sample with the mesh number of 800 is screened for next testing. Taking about 1g of pure erucamide to grind in a grinding device to make the particle size of the sample smaller so as to increase the contact area between the standard sample and the solvent.
(2) Preparing a sample solution to be detected:
a. accurately weighing 2g of the crushed sample, putting the crushed sample into a brown closed container, adding 40mL of dichloromethane-methanol (volume ratio is 9:1) mixed solvent, and performing ultrasonic extraction for 3h at 50 ℃.
b. And filtering the dissolved solution by using a filter membrane of 0.45 mu m to obtain the sample solution to be detected.
(3) Gas chromatography-mass spectrometry test condition settings: type of column: DB-5MS (30m 250 μm 0.25 μm); sample inlet temperature: 290 ℃; detector temperature: 320 ℃; temperature rising procedure: the initial temperature was 100 ℃ and increased to 320 ℃ over 5 minutes at a rate of 50 ℃ per minute and held for 15 minutes. The ion source temperature is 230 ℃, the quadrupole rod temperature 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 detected in the step (2) into a sample injection vial, and marking. The sample sequence was set in the online software and the test was started after checking the sequence accuracy. To reduce interference, two solvent blanks were tested prior to sample testing. And extracting the solution on the machine by a sample injection needle, and detecting according to the set detection conditions.
The GC-MS chromatogram of this sample is shown in FIG. 6, in which erucamide has a strong characteristic peak at 10.5 min. However, the number of the hetero-peaks near the peak is large, and the quantification of erucamide is interfered by the near hetero-peaks when the sample components are complex.
(5) And (3) recovery rate determination: taking the sample prepared in the step (1), taking 4 samples in parallel, wherein 1 sample is not added with the pure erucamide substance, and the other 3 samples are respectively added with 2mg, 4mg and 8mg of the pure erucamide substance, and carrying out sample treatment and test according to the steps (2), (3) and (4). The recovery was calculated by the following formula:
R＝(C1-C0)/C*100％；
In the formula: r-recovery in units;
C1-the measured concentration of erucamide in μ g/mL in the spiked samples;
C0-the measured concentration of erucamide in the sample to be tested, in μ g/mL;
c-theoretical loading concentration of erucamide in the loaded sample, in μ g/mL.
TABLE 5 recovery of control 2 spiked
Figure BDA0003574838170000061
According to the recovery rates of the examples and the comparative examples, the detection sensitivity of the invention on the content of N, N' -ethylene bis stearamide is high, the invention has strong specificity and the accuracy on other amide lubricants is not high.
Carbon emission detection
The carbon emissions of the test procedure of example 1 were calculated according to ISO14010 and ISO 14044. The method is firstly divided into a series of unit processes: sample crushing, weighing, ultrasonic extraction, filtering, testing, and decomposing liquid chromatography and internal standard gas chromatography into a series of unit processes. Data were entered in the Simapro7 software and carbon emissions were calculated by the software for three different analytical methods. The results are shown in table 6, and the results show that the quantitative analysis method of the functional assistant N, N' -ethylene bis stearamide in the high molecular material has the minimum carbon emission and is more environment-friendly compared with other chemical analysis methods (liquid chromatography and internal standard gas chromatography), and the method meets the requirement of a green chemical analysis method.
TABLE 6 carbon footprint for different analytical methods
Analytical method Example 1 Liquid chromatography Internal standard gas chromatography
Carbon footprint (CO)2eq) 1.69 4.21 5.13
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.

Claims (10)

1. A quantitative analysis method of N, N' -ethylene bis stearamide in a high molecular material is characterized by comprising the following steps:
(1) extracting a high molecular material to be detected by adopting an organic solvent, and separating precipitates to obtain a sample solution to be detected;
(2) dissolving N, N' -ethylene bis stearamide with different concentrations by using an organic solvent to obtain standard solutions with series concentrations;
(3) performing gas chromatography mass spectrometry detection on the standard solution with the series of concentrations in the step (2), taking ions with the peak-out time of 21.8min and the mass-to-charge ratio (m/z) of 86 as quantitative ions, and drawing a standard curve according to the corresponding relation between the peak area and the concentration of the m/z 86 ions detected at each concentration in 21.8 min;
(4) And (2) analyzing the sample solution to be detected in the step (1) by adopting the same gas chromatography-mass spectrometry detection conditions in the step (3), and calculating the concentration of N, N '-ethylene bis-stearamide in the sample solution to be detected according to the peak area of m/z 86 ions detected in the sample solution to be detected in 21.8min and the standard curve quantification in the step (3), thereby calculating the content of the N, N' -ethylene bis-stearamide in the high polymer material to be detected.
2. The method for quantitatively analyzing N, N' -ethylene bis stearamide in a high molecular material according to claim 1, wherein the conditions for gas chromatography mass spectrometry in the step (3) are as follows: column type DB-5MS (30m X250. mu. m X0.25. mu.m), injection port temperature: 280-300 ℃: temperature of the detector: and (3) heating at 300-320 ℃, and heating: the initial temperature is 100 ℃, the temperature is increased to 320 ℃ in 5 minutes at a speed of 50 ℃ per minute, and the temperature is kept for 15 minutes; the ion source temperature is 230 ℃, the quadrupole rod temperature is 150 ℃, and the scanning range is 50-800 u.
3. The method for quantitatively analyzing N, N' -ethylene bis stearamide in a high molecular material as claimed in claim 1, wherein the high molecular material to be detected in step (1) is pre-crushed to 500-1000 mesh.
4. The method for quantitatively analyzing N, N' -ethylene bis stearamide contained in a polymer material according to claim 1,
The organic solvent in the steps (1) and (2) is one or more than two of trichloromethane, dichloromethane, acetone, ethanol and methanol.
5. The method for quantitatively analyzing N, N' -ethylene bis stearamide in a high molecular material according to claim 4, wherein the organic solvents in the steps (1) and (2) are dichloromethane and methanol in a volume ratio of 9: 1 proportion of mixed solvent.
6. The method for quantitatively analyzing N, N' -ethylene bis stearamide in a high molecular material according to claim 1, wherein the extraction in the step (1) and the dissolution in the step (2) are performed by ultrasonic means.
7. The method for quantitatively analyzing the N, N' -ethylene bis stearamide in the high polymer material according to claim 6, wherein the extraction in the step (1) and the dissolution in the step (2) are carried out by ultrasonic processing at 40-60 ℃ for 2-4 h.
8. The method for quantitative analysis of N, N' -ethylene bis stearamide in a high molecular material according to claim 1, wherein the high molecular material to be detected in step (1) is PP, EVA, PS, PE, AS, PA6 or PA 66.
9. The method for quantitatively analyzing N, N' -ethylene bis stearamide 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.
10. The method for quantitatively analyzing N, N '-ethylenebisstearamide in a high molecular material according to claim 1, wherein the N, N' -ethylenebisstearamide in the step (2) is ground in advance.
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Cited By (2)

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CN115266998A (en) * 2022-08-03 2022-11-01 成都普康唯新生物科技有限公司 Method for detecting content of sodium ions in sodium salt molecules
WO2024036983A1 (en) * 2022-08-16 2024-02-22 湖北鼎汇微电子材料有限公司 Polishing pad

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CN108872416A (en) * 2018-06-25 2018-11-23 上海市食品药品包装材料测试所 A kind of method of simultaneous quantitative detection erucyl amide and ethylene bis stearamide

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115266998A (en) * 2022-08-03 2022-11-01 成都普康唯新生物科技有限公司 Method for detecting content of sodium ions in sodium salt molecules
WO2024036983A1 (en) * 2022-08-16 2024-02-22 湖北鼎汇微电子材料有限公司 Polishing pad

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