CN115480018A - Method for determining content of mosaic - Google Patents

Method for determining content of mosaic Download PDF

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CN115480018A
CN115480018A CN202210906638.6A CN202210906638A CN115480018A CN 115480018 A CN115480018 A CN 115480018A CN 202210906638 A CN202210906638 A CN 202210906638A CN 115480018 A CN115480018 A CN 115480018A
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mobile phase
solution
mosaic
volume percent
standard
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钱瑶
李玉博
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Jiahua Science and Technology Development Shanghai Ltd
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    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02Column chromatography
    • G01N30/04Preparation or injection of sample to be analysed
    • G01N30/06Preparation
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02Column chromatography
    • G01N30/62Detectors specially adapted therefor
    • G01N30/74Optical detectors

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Abstract

The invention provides a method for determining the content of a mosaic, which comprises the following steps: preparing a test solution and a standard solution; (2) liquid chromatography determination: determining chromatograms of the test solution and the standard solution by adopting a liquid chromatography, and calculating the content of the mosaic in the test solution; wherein, the chromatogram adopts octane silane bonded silica gel as a filling agent, acetonitrile as a mobile phase B and aqueous solution containing phosphoric acid as a mobile phase A to carry out gradient elution, and the gradient procedure is as follows: 0-3min:5% mobile phase B;3-15min:5% mobile phase B → 100% mobile phase B;15-20min:100% mobile phase B → 5% mobile phase B. Not only realizes the effective separation of the mosaic from other impurities in the industrial product, but also has good peak shape, does not generate the phenomena of shoulder peak, bifurcation peak and the like, and can realize the accurate determination of the content of the mosaic.

Description

Method for determining content of mosaic
Technical Field
The invention relates to the technical field of analysis and test, in particular to a method for determining the content of a mosaic.
Background
Tris (2-hydroxyethyl) isocyanurate (THEIC, also known as mosaic) is an important fine chemical product which is rapidly developed along with the gradual industrialization of cyanuric acid in recent years. The cyazone is a compound which contains a stable rigid six-membered carbon nitrogen heterocyclic ring structure and has excellent chemical and thermal stability. The three hydroxyethyl groups have strong derivatization potential, have the same property with the hydroxyl groups of the fatty alcohol, and can easily react with other organic functional groups to generate new compounds or polycondensates. For example, the trihydroxyethyl isocyanurate is added into polyvinyl chloride and widely used as a calcium-zinc composite heat stabilizer, and generates a synergistic effect with a main stabilizer, so that the heat resistance and the heat stability of a system are remarkably improved. When the flame retardant is added into a polyurethane coating, the heat resistance and the flame resistance of the coating can be improved. The trihydroxyethyl isocyanurate can be used for synthesizing polyester, polyester-imide, polyester-amide-imide, polyurethane and the like, and is widely used for producing polyester insulating paint, polyurethane flame retardants, fiber treatment raw materials and the like. The coating is the most widely used product of the trihydroxyethyl isocyanurate, and is used as a surface coating of steel, other special coatings, adhesives, films, laminated materials, molded products and the like besides wire enamel and insulating impregnating varnish.
The existing document 'purity of trihydroxyethyl isocyanurate detected by high performance liquid chromatography' discloses a method for detecting the content of trihydroxyethyl isocyanurate, however, the method is only suitable for detecting a mosaic product with low impurity content and high purity, and shoulder seams, forked peaks or trailing phenomena easily occur to general commercial mosaic industrial products due to high impurity content, so that the content of the mosaic cannot be accurately detected.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to overcome the defect that the content of the mosaic cannot be accurately detected due to the fact that the shoulder seam, the bifurcation peak or the tailing of the test sample of the method in the prior art is serious, so that the method for determining the content of the mosaic is provided.
Therefore, the invention provides a method for determining the content of the mosaic, which comprises the following steps:
(1) Preparing a test solution and a standard solution;
(2) And (3) liquid chromatography determination: determining chromatograms of the test solution and the standard solution by adopting a liquid chromatography, and calculating the content of the mosaic in the test solution; wherein, the chromatogram adopts octane silane bonded silica gel as a filling agent, acetonitrile as a mobile phase B and aqueous solution containing phosphoric acid as a mobile phase A to carry out gradient elution, and the gradient elution procedure is as follows: 0-3min:5% by volume of mobile phase B,95% of mobile phase A;3-15min: mobile phase B at 5% volume, mobile phase a at 95% volume → mobile phase B at 100% volume, mobile phase a at 0% volume; 15-20min: volume percent 100% mobile phase B, volume percent 0% mobile phase a → volume percent 5% mobile phase B, volume percent 95% mobile phase a.
Further, in the determination process of the liquid chromatography, the column temperature is 30-40 ℃.
Further, the flow rate during the measurement by liquid chromatography is 0.8 to 1.2ml/min, preferably 1ml/min.
Further, the phosphate is at least one selected from sodium dihydrogen phosphate and potassium dihydrogen phosphate; and/or the mass percent of the phosphate in the phosphate-containing aqueous solution is 3-6%; and/or, the column is a Shim-pack GIST C8 μm column.
Furthermore, the test sample is a mosaic industrial product with the content of 90-100%.
Further, the preparation method of the test solution comprises the steps of dissolving the test by using a solvent to obtain a solution, filtering the solution, and taking the filtrate to obtain the test solution.
Further, in the preparation of the test solution, the solvent is at least one selected from the group consisting of water, methanol and ethanol; and/or the concentration of the test sample in the solution is 0.2-0.7 mg/ml.
Further, the preparation method of the standard substance solution comprises the steps of dissolving the saxok standard substance by using a solvent to obtain a solution, filtering the solution, and taking the filtrate to obtain the saxok standard substance.
Further, during the preparation of the standard solution, the solvent is at least one selected from water, methanol and acetonitrile; and/or the concentration of the standard solution is 0.02-1 mg/mL.
Further, preparing N standard substance solutions with the concentration of 0.02-1mg/ml in the step (1), wherein N is an integer more than or equal to 3; preferably, N is an integer ≧ 5 (e.g., 5, 6, 7, 8, 9, 10), and more preferably, the concentrations of saxok in the N standard solutions are: 0.02mg/ml, 0.1mg/ml, 0.2mg/ml, 0.5mg/ml and 1mg/ml.
The technical scheme of the invention has the following advantages:
1. according to the method for determining the content of the mosaic, provided by the invention, the chromatographic column which takes octane silane bonded silica gel as a filling agent, acetonitrile as a mobile phase B, a phosphate-containing aqueous solution as a mobile phase A and a specific elution program are adopted, so that the main component in the mosaic industrial product is effectively separated from other impurities, the peak shape symmetry is good, the phenomena of shoulder peaks, forked peaks and the like cannot occur, and the accurate determination of the content of the mosaic can be realized.
2. The method for measuring the content of the mosaic can further improve the symmetry of the peak shape and the stability of the base line by controlling the column temperature to be 25-40 ℃, particularly 30-40 ℃.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a chromatogram of a test solution of example 1;
FIG. 2 is a chromatogram of the test solution in comparative example 1;
FIG. 3 is a chromatogram of the test solution in comparative example 2;
FIG. 4 is a chromatogram of the test solution in comparative example 3;
FIG. 5 is a chromatogram of the test solution in comparative example 4.
Detailed Description
The following examples are provided to better understand the present invention, not to limit the best mode, and not to limit the content and protection scope of the present invention, and any product that is the same or similar to the present invention and is obtained by combining the present invention with other features of the prior art and the present invention falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
In the examples, the sample was purchased from national chemical group, chemical reagents, inc. using a Seik standard, and the purity was 99%; the sake industry is offered by the advanced chemical technology (shanghai) ltd.
Example 1
This example provides a method for determining the content of a mosaic, comprising the steps of:
(1) Dissolving the mosaic standard substance with ultrapure water respectively to prepare solutions with the concentrations of 0.02, 0.1, 0.2, 0.5 and 1mg/ml respectively, and filtering with a 0.45 mu m filter membrane to obtain the standard substance solution.
(2) Dissolving the mosaic industrial product by adopting ultrapure water to obtain a sample solution of 0.2mg/mL, and filtering the prepared solution by a filter membrane of 0.45 mu m to obtain a test sample solution.
(3) Measuring the standard solution and the test solution by liquid chromatography, making a standard curve according to the test result, and calculating the concentration of the test solution, wherein the chromatographic conditions are as follows: the detection wavelength is as follows: 210nm, and a chromatographic column is Shim-pack GIST C8 μm; a column oven is 40 ℃; the flow rate is 1ml/min; mobile phase: phase A: 5wt% sodium dihydrogen phosphate aqueous solution, phase B: acetonitrile; the gradient elution procedure was as follows: 0-3min:5% by volume of mobile phase B,95% of mobile phase a;3-15min: mobile phase B at 5% volume, mobile phase a at 95% volume → mobile phase B at 100% volume, mobile phase a at 0% volume; 15-20min:100% by volume of mobile phase B, 0% by volume of mobile phase A → 5% by volume of mobile phase B,95% by volume of mobile phase A, and a sample size of 50. Mu.l.
TABLE 1 results of standard curves
Figure BDA0003772718520000051
According to the results in table 1, linear regression is performed with the concentration of the standard solution as abscissa and the peak area as ordinate to obtain a regression equation: y =2 × 10 6 X+10944;r 2 =0.9999. Wherein y is the peak area and X is the concentration.
The chromatogram of the test solution is shown in figure 1, the peak emergence time of the mosaic is 6.3min, the content of the mosaic in the test solution is calculated to be 92% according to the peak area and the regression equation of the test solution, the baseline is stable, no shoulder seam and split peak exist, the separation degree is 1.64, the tailing factor is 1.02, both meet the analysis requirements, and the test result is accurate and reliable.
Comparative example 1
This example provides a method for determining the content of saxoke, which uses liquid chromatography to detect the sample solution in the same batch as in example 1, the chromatographic conditions are basically the same as in example 1, the difference is only the column temperature, and the column temperature used in this example is 25 ℃.
The chromatogram of the test solution is shown in fig. 2, the peak time of the mosaic is 6.6min, although no shoulder seam and split peak exist, the separation degree is 1.41, the sample has a tail, the base line is slightly unstable, the tail factor is 1.156, the sample does not meet the analysis requirement (the separation degree is more than 1.5, and the tail factor is between 0.95 and 1.05), and the content of the mosaic in the test solution is calculated to be 90% according to the peak area and the regression equation of the test solution.
Comparative example 2
This comparative example provides a method for measuring the content of seek by detecting a test solution of the same lot as in example 1 by liquid chromatography under substantially the same chromatographic conditions as in example 1 except for the difference in mobile phase, and replacing the 5% sodium dihydrogen phosphate aqueous solution of example 1 with ultrapure water.
The chromatogram of the test solution is shown in FIG. 3, which shows a bifurcation peak with a resolution of 1.39, and does not meet the analysis requirements. And the tailing factor is 1.124, which does not meet the requirement of liquid phase analysis.
Comparative example 3
The comparative example provides a method for determining the content of the mosaic, a liquid chromatography method is adopted to detect the sample solution of the same batch as the sample solution in the example 1, the chromatographic conditions are basically the same as the sample solution in the example 1, and the difference is only that the comparative example adopts a method with the volume ratio of 95:5, 5wt% of sodium dihydrogen phosphate aqueous solution and acetonitrile are used as mobile phases for isocratic elution.
The chromatogram of the test solution is shown in FIG. 4, the obvious tailing phenomenon of the Securic peak occurs, the tailing factor is 1.272, and the requirement of liquid phase analysis is not met.
Comparative example 4
The content of the mosaic in the same batch of mosaic industrial products in example 1 of the invention is determined by a method disclosed in the document 'high performance liquid chromatography for detecting purity of trihydroxyethyl isocyanurate', amino acid and biological resources, 2010 (03) by Wujian army, and the result is shown in figure 5.
As shown in fig. 5, the seek peak has an obvious tailing phenomenon, and the tailing factor is 1.294, which does not meet the requirement of liquid phase analysis.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (10)

1. A method for determining the content of the mosaic is characterized by comprising the following steps:
(1) Preparing a test solution and a standard solution;
(2) And (3) liquid chromatography determination: respectively measuring chromatograms of the test solution and the standard solution by adopting a liquid chromatography, and calculating the content of the cycie in the test solution; the chromatographic column uses octane silane bonded silica gel as a filler, acetonitrile as a mobile phase B and a phosphate-containing aqueous solution as a mobile phase A to carry out gradient elution, and the gradient elution program is as follows: 0-3min:5% by volume of mobile phase B,95% of mobile phase a;3-15min: mobile phase B at 5% volume percent, mobile phase a at 95% volume percent → mobile phase B at 100% volume percent, mobile phase a at 0% volume percent; 15-20min: volume percent 100% mobile phase B, volume percent 0% mobile phase a → volume percent 5% mobile phase B, volume percent 95% mobile phase a.
2. The method according to claim 1, wherein the column temperature during the measurement by liquid chromatography is 30 to 40 ℃.
3. The method according to claim 1 or 2, characterized in that the flow rate during the liquid chromatography determination is 0.8-1.2ml/min, preferably 1ml/min.
4. The method according to claims 1 to 3, wherein the phosphate is selected from at least one of sodium dihydrogen phosphate and potassium dihydrogen phosphate; and/or the mass percent of the phosphate in the phosphate-containing aqueous solution is 3-6%; and/or, the chromatographic column is a Shim-pack GIST C8 μm chromatographic column; and/or the detection wavelength is 208-212nm.
5. The method of any one of claims 1-4, wherein the test article is a sample of saxok industry at a level of 90% to 100%.
6. The method of any one of claims 1 to 5, wherein the sample solution is prepared by dissolving the sample in a solvent to obtain a solution, filtering the solution, and collecting the filtrate.
7. The method according to claim 6, wherein the solvent is at least one selected from the group consisting of water, methanol and acetonitrile during the preparation of the test solution; and/or the concentration of the test sample in the solution is 0.2-0.7 mg/ml.
8. The method according to any one of claims 1 to 7, wherein the standard solution is prepared by dissolving a saxok standard in a solvent to obtain a solution, filtering the solution, and collecting the filtrate.
9. The method according to claim 8, wherein the solvent is at least one selected from the group consisting of water, methanol and acetonitrile; and/or the concentration of the standard solution is 0.02-1 mg/ml.
10. The method according to any one of claims 1 to 9, wherein in step (1), N standard solutions with a concentration of 0.02-1mg/ml are prepared, wherein N is an integer of 3 or more; preferably, N is an integer of more than or equal to 5, and more preferably, the concentration of the mosaic in the N standard solutions is respectively as follows: 0.02mg/ml, 0.1mg/ml, 0.2mg/ml, 0.5mg/ml and 1mg/ml.
CN202210906638.6A 2022-07-29 2022-07-29 Method for determining content of mosaic Pending CN115480018A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002316980A (en) * 2001-02-16 2002-10-31 Nissan Chem Ind Ltd Method for producing cyanuric acid derivative
JP2004269464A (en) * 2003-03-11 2004-09-30 Nippon Shokubai Co Ltd Method for producing tris(2-hydroxyalykyl)isocyanurate and tris(2-hydroxyalykyl)isocyanurate composition
CN114149376A (en) * 2021-10-28 2022-03-08 佳化化学科技发展(上海)有限公司 Preparation method of tris (2-hydroxyethyl) isocyanurate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002316980A (en) * 2001-02-16 2002-10-31 Nissan Chem Ind Ltd Method for producing cyanuric acid derivative
JP2004269464A (en) * 2003-03-11 2004-09-30 Nippon Shokubai Co Ltd Method for producing tris(2-hydroxyalykyl)isocyanurate and tris(2-hydroxyalykyl)isocyanurate composition
CN114149376A (en) * 2021-10-28 2022-03-08 佳化化学科技发展(上海)有限公司 Preparation method of tris (2-hydroxyethyl) isocyanurate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
郭卫荣等: "高效液相 色谱法检测三羟乙基异氰尿酸酯的纯度", 氨基酸和生物资源, vol. 34, no. 03, pages 73 - 75 *

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Application publication date: 20221216