CN116381122A - Method for testing sulfur distribution of ethoxysilane coupling agent by high performance liquid chromatography-mass spectrometer - Google Patents
Method for testing sulfur distribution of ethoxysilane coupling agent by high performance liquid chromatography-mass spectrometer Download PDFInfo
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- CN116381122A CN116381122A CN202310582440.1A CN202310582440A CN116381122A CN 116381122 A CN116381122 A CN 116381122A CN 202310582440 A CN202310582440 A CN 202310582440A CN 116381122 A CN116381122 A CN 116381122A
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- coupling agent
- mass
- ethoxysilane
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- ethoxysilane coupling
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 19
- 239000011593 sulfur Substances 0.000 title claims abstract description 19
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000007788 liquid Substances 0.000 title claims abstract description 17
- 239000007822 coupling agent Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000001819 mass spectrum Methods 0.000 claims abstract description 6
- 238000001514 detection method Methods 0.000 claims abstract description 5
- 238000000534 ion trap mass spectrometry Methods 0.000 claims abstract description 5
- 238000004949 mass spectrometry Methods 0.000 claims abstract description 5
- 239000012528 membrane Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000007865 diluting Methods 0.000 claims description 2
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 9
- 238000000275 quality assurance Methods 0.000 abstract description 2
- 238000003908 quality control method Methods 0.000 abstract description 2
- 238000004458 analytical method Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000009614 chemical analysis method Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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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
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention relates to the application field of industries such as tires, rubber products and the like, in particular to a method for testing the sulfur distribution of an ethoxysilane coupling agent by using a high performance liquid chromatography-mass spectrometer. The method comprises the following steps: 1) The mobile phase is acetonitrile/water solution with the proportion of 97/3; column temperature 40 ℃; the liquid chromatograph adopts an ultraviolet detector to detect the wavelength of 254nm; the chromatographic column is a C18 flash column; the flow rate is 0.1-0.3ml/min; 2) Mass spectrometry conditions: ion trap mass spectrometry: ESI source positive ion detection; mass scan range: m/z is 50-1000; 3) The ethoxysilane coupling agent sample to be tested is filtered through a 0.22 mu m filter membrane, 5 mu l-10 mu l of solution is injected by an automatic sampler, a liquid chromatogram is measured according to conditions, and each component with different sulfur content is determined according to the peak time and mass spectrum of the solution. The method can accurately determine the distribution condition of sulfur in each component in the silane coupling agent, and has important significance for quality control and quality assurance of the silane coupling agent.
Description
Technical Field
The invention relates to the application field of industries such as tires, rubber products and the like, in particular to a method for testing the sulfur distribution of an ethoxysilane coupling agent by using a high performance liquid chromatography-mass spectrometer.
Background
In order to increase the affinity between white carbon black and rubber, a small amount of a silane coupling agent is generally added to the filler. Therefore, the two materials can be effectively connected, and the rubber material can be modified, so that the tensile strength, the tearing strength and the wear resistance of the rubber are enhanced, and the viscosity of the rubber material is reduced. Ethoxysilane is one of the commonly used silane coupling agents, among which are mainly bis (triethoxysilane) tetrasulfide (Si 69) and bis (triethoxysilane) disulfide (Si 75). In practice, the silane coupling agent is a mixture of polysulfides of varying S chain length, with Si69 having a maximum content of components containing 4S atoms and Si75 having a maximum content of components containing 2S atoms. Because the difference of sulfur content can affect the performances of wear resistance, heat resistance, ageing resistance and the like of the tire, accurate analysis of the silane coupling agent is required.
The difference of the silane coupling agent is usually determined by using a chemical analysis method to analyze indexes such as ash, heating decrement, specific gravity, sulfur content, pH value, flash point and the like, wherein the sulfur content determination method comprises an elemental analyzer and an oxygen bottle combustion method, but the two methods can only determine the total sulfur content, and cannot effectively determine the distribution of sulfur of each component.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a method for testing the sulfur distribution of an ethoxysilane coupling agent by using a high performance liquid chromatography-mass spectrometer, which uses acetonitrile-water as a mobile phase system to develop a relatively simple, green and environment-friendly liquid phase analysis method. The method can accurately determine the distribution condition of sulfur in each component in the silane coupling agent, and has important significance for quality control and quality assurance of the silane coupling agent.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a method for testing sulfur distribution of ethoxysilane coupling agent by high performance liquid chromatography-mass spectrometer, comprising the following steps:
1) The mobile phase is acetonitrile/water solution with the proportion of 97/3; column temperature 40 ℃; the liquid chromatograph adopts an ultraviolet detector to detect the wavelength of 254nm; the chromatographic column is a C18 flash column; the flow rate is 0.1-0.3ml/min;
2) Mass spectrometry conditions: ion trap mass spectrometry: ESI source positive ion detection; mass scan range: m/z is 50-1000;
3) The ethoxysilane coupling agent sample to be tested is filtered through a 0.22 mu m filter membrane, 5 mu l-10 mu l of solution is injected by an automatic sampler, a liquid chromatogram is measured according to conditions, and each component with different sulfur content is determined according to the peak time and mass spectrum of the solution.
Preferably, the preparation of the ethoxysilane coupling agent to be tested in step 3) is as follows: and (3) taking a certain amount of ethoxysilane coupling agent, and diluting to 1000 times or more by using liquid chromatographic grade acetonitrile.
Preferably, the ethoxysilane coupling agent is Si69 or Si75.
Due to the adoption of the technical scheme, the method has the advantages that the method can well separate the compounds with different sulfur contents, and has good accuracy and simple and convenient operation.
Drawings
FIG. 1 is a liquid chromatogram of bis (triethoxysilane) tetrasulfide (Si 69);
FIG. 2 is a mass spectrum of the retention time of 3.99min in FIG. 1;
FIG. 3 is a liquid chromatogram of bis (triethoxysilane) disulfide (Si 75);
FIG. 4 is a mass spectrum of FIG. 3 with a retention time of 2.89 min.
Detailed Description
In the following, an overview and complete description of the technical solutions in the embodiments of the present invention will be given in connection with the embodiments of the present invention, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. Given the embodiments of the present invention, all other embodiments that would be obvious to one of ordinary skill in the art without making any inventive effort are within the scope of the present invention.
Example 1
The mobile phase is acetonitrile/water solution with the proportion of 97/3; the column temperature is 40 ℃, and the liquid chromatography adopts an ultraviolet detector to detect the wavelength of 254nm; the chromatographic column is a C18 flash column; the flow rate is 0.1-0.3ml/min; preparing Si69 acetonitrile solution; putting the mixture into an ultrasonic cleaner for dissolution; filtering through a 0.22 μm filter membrane, and injecting 5 μl-10 μl of the solution with an autosampler; obtaining the peak outlet time and peak area of each component of the Si69 acetonitrile solution; mass spectrometry conditions: ion trap mass spectrometry: ESI source positive ion detection; mass scan range: m/z is 50-1000; the mass spectrograms of the components of the Si69 acetonitrile solution are shown in figures 1 and 2; the results of the liquid chromatography-mass spectrometry analysis of Si69 are shown in table 1.
TABLE 1 results of liquid chromatography-mass spectrometry analysis of Si69
Example 2
The mobile phase is acetonitrile/water solution with the proportion of 97/3; the column temperature is 40 ℃, and the liquid chromatography adopts an ultraviolet detector to detect the wavelength of 254nm; the chromatographic column is a C18 flash column; the flow rate is 0.1-0.3ml/min; preparing Si75 acetonitrile solution; putting the mixture into an ultrasonic cleaner for dissolution; filtering through a 0.22 μm filter membrane, and injecting 5 μl-10 μl of the solution with an autosampler; obtaining the peak outlet time and peak area of each component of the Si75 acetonitrile solution; mass spectrometry conditions: ion trap mass spectrometry: ESI source positive ion detection; mass scan range: m/z is 50-1000; the mass spectrograms of the components of the Si75 acetonitrile solution are shown in figures 3 and 4; the results of the liquid chromatography-mass spectrometry analysis of Si69 are shown in table 2.
| Retention time/min | Mass spectrum measured value/(m/z) | Molecular weight | Sulfur content | Liquid phase peak area/% |
| 2.89 | 497.05 | 474 | S2 | 60.60 |
| 3.42 | 529.05 | 506 | S3 | 33.10 |
| 3.99 | 561.05 | 538 | S4 | 4.02 |
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art. The generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (3)
1. The method for testing the sulfur distribution of the ethoxysilane coupling agent by using the high performance liquid chromatography-mass spectrometer is characterized by comprising the following steps of:
1) The mobile phase is acetonitrile/water solution with the proportion of 97/3; column temperature 40 ℃; the liquid chromatograph adopts an ultraviolet detector to detect the wavelength of 254nm; the chromatographic column is a C18 flash column; the flow rate is 0.1-0.3ml/min;
2) Mass spectrometry conditions: ion trap mass spectrometry: ESI source positive ion detection; mass scan range: m/z is 50-1000;
3) The ethoxysilane coupling agent sample to be tested is filtered through a 0.22 mu m filter membrane, 5 mu l-10 mu l of solution is injected by an automatic sampler, a liquid chromatogram is measured according to conditions, and each component with different sulfur content is determined according to the peak time and mass spectrum of the solution.
2. The method according to claim 1, wherein the ethoxysilane coupling agent to be tested in step 3) is prepared as follows: and (3) taking a certain amount of ethoxysilane coupling agent, and diluting to 1000 times or more by using liquid chromatographic grade acetonitrile.
3. The method of claim 1, wherein the ethoxysilane coupling agent is Si69 or Si75.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310582440.1A CN116381122A (en) | 2023-05-19 | 2023-05-19 | Method for testing sulfur distribution of ethoxysilane coupling agent by high performance liquid chromatography-mass spectrometer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310582440.1A CN116381122A (en) | 2023-05-19 | 2023-05-19 | Method for testing sulfur distribution of ethoxysilane coupling agent by high performance liquid chromatography-mass spectrometer |
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| Publication Number | Publication Date |
|---|---|
| CN116381122A true CN116381122A (en) | 2023-07-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310582440.1A Pending CN116381122A (en) | 2023-05-19 | 2023-05-19 | Method for testing sulfur distribution of ethoxysilane coupling agent by high performance liquid chromatography-mass spectrometer |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116381122A (en) |
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2023
- 2023-05-19 CN CN202310582440.1A patent/CN116381122A/en active Pending
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