CN115166093B - OPPEA content detection method - Google Patents
OPPEA content detection method Download PDFInfo
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- CN115166093B CN115166093B CN202210826695.3A CN202210826695A CN115166093B CN 115166093 B CN115166093 B CN 115166093B CN 202210826695 A CN202210826695 A CN 202210826695A CN 115166093 B CN115166093 B CN 115166093B
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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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- 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
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
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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
- G01N30/60—Construction of the column
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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
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- G—PHYSICS
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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
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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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Abstract
The invention belongs to the technical field of chemical detection, and particularly relates to a method for detecting the content of OPPEA. The method adopts liquid chromatography to detect the content, and the chromatographic conditions include: the method uses a C18 column as a chromatographic column and uses a water-organic solvent as a mobile phase, wherein the organic solvent is methanol and/or acetonitrile, and the quantitative determination is carried out by adopting an area normalization method, so that the OPPEA content can be rapidly, simply, conveniently and accurately detected. The method provided by the invention is used for detecting the content of the synthesized OPPEA for the first time, so that the quality and the quality of the synthesized OPPEA can be better controlled, and the optical element can meet the requirement of high refractive index.
Description
Technical Field
The invention belongs to the technical field of chemical detection, and particularly relates to a method for detecting high-refractive-index UV monomer OPPEA by utilizing liquid chromatography.
Background
The UV curing is widely applied to the fields of paint, optical display, printing ink spraying and the like as a high-efficiency, environment-friendly, energy-saving and accurate curing mode. In some electronic devices such as OLED lighting or liquid crystal displays, there is a certain requirement for the refractive index of the optical element, since the refractive index of the optical element directly influences the light output effect of the OLED light source.
Previously, increasing the refractive index of an optical element was considered to increase the thickness and curvature of the optical element, and it was later found that increasing the thickness was detrimental to the weight reduction of the device, and therefore a high refractive index optical coating was introduced to increase the refractive index. The high refractive index optical coating can not only reduce the thickness of the optical element, but also increase the bending resistance, impact resistance and other properties of the element, and UV monomers are getting more and more attention as important components in the optical film or coating, wherein o-phenylphenoxyethyl acrylate (OPPEA) is widely used because of having excellent transparency and high refractive index, and the refractive index of the device can be effectively controlled by controlling the content of the OPPEA. Therefore, it is very necessary to perform the content detection of the newly prepared OPPEA, but no relevant report on the content detection of OPPEA has been found in the prior art.
Disclosure of Invention
In view of the above, it is an object of the present invention to provide a method capable of rapidly, simply and accurately detecting the OPPEA content in the synthesis of UV monomers.
The invention aims at realizing the following technical scheme:
the invention provides a method for detecting OPPEA content, which adopts liquid chromatography to detect the content, and chromatographic conditions comprise:
chromatographic column: a C18 column;
mobile phase: a water-organic solvent, wherein the organic solvent is methanol and/or acetonitrile;
detection wavelength: 254nm.
In an embodiment of the invention, water and acetonitrile in a volume ratio of 2:8 are used for isocratic elution.
In the embodiment of the invention, water and methanol with the volume ratio of 2-4:6-8 are adopted for isocratic elution.
In an embodiment of the present invention, the gradient elution is performed using water-methanol as a mobile phase, and the elution procedure includes: 0- > 3 min- > 10 min- > 13 min, the volume percentage of methanol in the mobile phase is 50% → 50% → 80% → 50% → 50%.
In an embodiment of the invention, the flow rate of the mobile phase is 0.8-1.2 mL/min.
In an embodiment of the invention, the column temperature of the chromatographic column is 25-40 ℃.
In an embodiment of the present invention, the method for detecting the OPPEA content further includes preparation of a test solution, including:
the sample was dissolved in HPLC grade methanol to prepare a solution with a concentration of 15 to 20mg/mL, and then filtered with a 0.45 μm filter membrane.
In an embodiment of the invention, the test sample is a synthetic OPPEA.
In an embodiment of the present invention, the method for detecting the OPPEA content further includes preparation of a control solution, including:
OPPEA standard is dissolved in HPLC grade methanol to prepare a solution with a concentration of 15-20 mg/mL, and then filtered by a 0.45 μm filter membrane.
In an embodiment of the present invention, the method for detecting the OPPEA content further includes calculating the OPPEA content in the test sample by using an area normalization method.
Compared with the prior art, the technical scheme of the invention has the following advantages:
the method for detecting the OPPEA content provided by the embodiment of the invention adopts a liquid chromatography method for content detection, and chromatographic conditions comprise: the method uses a C18 column as a chromatographic column, uses a water-organic solvent as a mobile phase, uses methanol and/or acetonitrile as an organic solvent, and adopts an area normalization method to quantify, thereby rapidly, simply, conveniently and accurately detecting the OPPEA content. The method provided by the invention is used for detecting the content of the synthesized OPPEA for the first time, so that the quality and the quality of the synthesized OPPEA can be better controlled, and the optical element can meet the requirement of high refractive index. The method fills the gap of lack of quality control for OPPEA at home and abroad, and is favorable for promoting the establishment and implementation of OPPEA quality control standard.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are needed in the description of the embodiments or the prior art will be briefly described, and it is obvious that the drawings in the description below are some embodiments of the present invention, and other drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
FIG. 1 is a chromatogram of a control obtained in example 1 of the present invention;
FIG. 2 is a chromatogram of a sample obtained in example 1 of the present invention;
FIG. 3 is a chromatogram of a test sample obtained in example 2 of the present invention;
FIG. 4 is a chromatogram of a test sample obtained in example 3 of the present invention.
Detailed Description
The following examples are provided for a better understanding of the present invention and are not limited to the preferred embodiments described herein, but are not intended to limit the scope of the invention, any product which is the same or similar to the present invention, whether in light of the present teachings or in combination with other prior art features, falls within the scope of the present invention.
The specific experimental procedures or conditions are not noted in the examples and may be followed by the operations or conditions of conventional experimental procedures described in the literature in this field. The reagents or apparatus used were conventional reagent products commercially available without the manufacturer's knowledge.
Example 1
The embodiment provides a method for detecting OPPEA content, which adopts liquid chromatography to detect the content and specifically comprises the following steps:
s1, preparation of reference substance solution
40mg of OPPEA industry standard (OPPEA content is 88%) is dissolved in 2mL of HPLC grade methanol to obtain a solution with the concentration of 20mg/mL, and then the solution is filtered by a filter membrane with the concentration of 0.45 mu m, and the solution is filled into a sample bottle to be measured.
S2, detection of reference substance solution
The prepared reference solution was analyzed by using a Shimadzu liquid chromatograph under the following chromatographic conditions:
chromatographic column: a Shim-pack GIST C18 column (4.6X1250 mm);
column temperature: 40 ℃;
mobile phase: (volume ratio) 20% pure water-80% methanol;
flow rate: 1mL/min;
detection wavelength: 254nm;
a detector: photodiode column detectors (PDAs).
A control chromatogram as shown in FIG. 1 was obtained, from which the liquid phase peak position of OPPEA was determined (9.296 min).
S3, preparation of sample solution
40mg of synthesized OPPEA was weighed, dissolved in 2mL of HPLC grade methanol, and then filtered with a 0.45 μm filter membrane, and filled into a sample bottle for use.
S4, detection of sample solution
Analyzing the sample solution by adopting the chromatographic condition in the step S2 to obtain a sample chromatogram shown in the figure 2, quantifying by adopting an area normalization method, wherein the content of OPPEA in the sample is 91.28%, and the content of OPPEA in the reference substance is 88.97%.
Example 2
The other contents were the same as in example 1 except for the following.
The mobile phase is 20% pure water-80% acetonitrile (volume ratio).
And obtaining a chromatogram of the test sample shown in fig. 3, wherein the peak time is advanced to 5.673min, the analysis is carried out by adopting an area normalization method, and the OPPEA content in the test sample is calculated to be 90.12%.
Example 3
The other contents were the same as in example 1 except for the following.
Gradient elution is carried out by taking water-methanol as a mobile phase, and the elution procedure comprises: 0- > 3 min- > 10 min- > 13 min, the volume percentage of methanol in the mobile phase is 50% → 50% → 80% → 50% → 50%.
And obtaining a chromatogram of the test sample shown in fig. 4, prolonging the peak time to 18.346min, quantifying by adopting an area normalization method, and calculating to obtain 90.86% of OPPEA in the test sample.
As can be seen from fig. 2, 3 and 4, when acetonitrile is used to replace methanol, the components in the sample are not separated from methanol, and errors are easily introduced. While the peaks can be separated significantly when switched to gradient elution, the peak shape is wider and the cost is higher than isocratic elution. Thus water is chosen: the volume ratio of methanol is 2:8, and detecting the isocratic elution condition.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (6)
1. A method for detecting the amount of OPPEA in a test sample, wherein the test sample is synthetic OPPEA; detecting the content by adopting a liquid chromatography method, wherein the chromatographic conditions comprise:
chromatographic column: a C18 column;
mobile phase: a water-organic solvent, the organic solvent being methanol;
detection wavelength: 254nm;
water and methanol with the volume ratio of 2:8 are adopted for isocratic elution; or alternatively
Gradient elution is carried out by taking water-methanol as a mobile phase, and the elution procedure comprises: 0- > 3 min- > 10 min- > 13 min, the volume percentage of methanol in the mobile phase is 50% → 50% → 80% → 50% → 50%.
2. The method for detecting the OPPEA content in a sample according to claim 1, wherein the flow rate of the mobile phase is 0.8-1.2 mL/min.
3. The method for detecting the OPPEA content in a sample according to claim 1, wherein the column temperature of the chromatographic column is 25-40 ℃.
4. The method for detecting the OPPEA content of a test sample according to any one of claims 1 to 3, wherein the method for detecting the OPPEA content of the test sample further comprises the steps of:
dissolving a test sample in HPLC grade methanol to prepare a solution with the concentration of 15-20 mg/mL, and filtering by a filtering membrane with the thickness of 0.45 mu m.
5. The method for detecting the OPPEA content of a test sample according to any one of claims 1 to 3, wherein the method for detecting the OPPEA content of the test sample further comprises the steps of:
dissolving the OPPEA standard into HPLC grade methanol to prepare a solution with the concentration of 15-20 mg/mL, and filtering by a filtering membrane with the thickness of 0.45 mu m.
6. The method of claim 4, wherein the method of detecting the amount of OPPEA in the sample further comprises calculating the amount of OPPEA in the sample by an area normalization method.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104803852A (en) * | 2015-03-11 | 2015-07-29 | 张家港康得新光电材料有限公司 | Post-processing method of ultraviolet curing monomer for optical film |
| CN106699523A (en) * | 2015-11-13 | 2017-05-24 | 上海飞凯光电材料股份有限公司 | Synthetic method of o-phenyl phenoxyethanol |
| WO2021131942A1 (en) * | 2019-12-26 | 2021-07-01 | 大阪ガスケミカル株式会社 | Fluorene derivative, method for producing same, and application of same |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104803852A (en) * | 2015-03-11 | 2015-07-29 | 张家港康得新光电材料有限公司 | Post-processing method of ultraviolet curing monomer for optical film |
| CN106699523A (en) * | 2015-11-13 | 2017-05-24 | 上海飞凯光电材料股份有限公司 | Synthetic method of o-phenyl phenoxyethanol |
| WO2021131942A1 (en) * | 2019-12-26 | 2021-07-01 | 大阪ガスケミカル株式会社 | Fluorene derivative, method for producing same, and application of same |
Non-Patent Citations (3)
| Title |
|---|
| Preparation and properties of photocurable, high refractive, 2-naphthol epoxy-modified urethane acrylate;Back Sun Kim et al;Polymer Bulletin;第68卷;2097-2105 * |
| 含氮杂环类丙烯酸酯的合成和性能研究;李潭等;化学世界;第59卷(第03期);140-147 * |
| 磺酸型钙粉分散剂的制备及其分散性能;王小荣等;高分子通报;第012卷;55-62 * |
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