CN115112795A - HPLC-UV detection method for purity of disodium sulfosuccinate intermediate - Google Patents
HPLC-UV detection method for purity of disodium sulfosuccinate intermediate Download PDFInfo
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- CN115112795A CN115112795A CN202210741371.XA CN202210741371A CN115112795A CN 115112795 A CN115112795 A CN 115112795A CN 202210741371 A CN202210741371 A CN 202210741371A CN 115112795 A CN115112795 A CN 115112795A
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- disodium sulfosuccinate
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- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 title claims abstract description 50
- 238000000825 ultraviolet detection Methods 0.000 title claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 22
- 239000012488 sample solution Substances 0.000 claims abstract description 12
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005695 Ammonium acetate Substances 0.000 claims abstract description 10
- 229940043376 ammonium acetate Drugs 0.000 claims abstract description 10
- 235000019257 ammonium acetate Nutrition 0.000 claims abstract description 10
- 238000010828 elution Methods 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 239000003085 diluting agent Substances 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 239000000543 intermediate Substances 0.000 claims description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000012071 phase Substances 0.000 claims description 11
- 238000001514 detection method Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000523 sample Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 229910003460 diamond Inorganic materials 0.000 claims description 3
- 239000010432 diamond Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 230000014759 maintenance of location Effects 0.000 abstract description 5
- 239000000337 buffer salt Substances 0.000 abstract description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 4
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 description 3
- 229960000789 guanidine hydrochloride Drugs 0.000 description 3
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- -1 1-oxoundec-10-enyl Chemical group 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- YRIDFQASBDRMBJ-UHFFFAOYSA-N undec-10-enamide Chemical compound NC(=O)CCCCCCCCC=C YRIDFQASBDRMBJ-UHFFFAOYSA-N 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
-
- 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
-
- 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
-
- 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
- G01N30/36—Control of physical parameters of the fluid carrier in high pressure liquid systems
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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
- G01N30/50—Conditioning of the sorbent material or stationary liquid
- G01N30/52—Physical parameters
- G01N30/54—Temperature
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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
- G01N30/6052—Construction of the column body
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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
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
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Abstract
The invention discloses an HPLC-UV detection method for the purity of disodium sulfosuccinate intermediate, which comprises the steps of taking a proper amount of disodium sulfosuccinate intermediate, dissolving the disodium sulfosuccinate intermediate by using ACN as a diluent to prepare a sample solution with the concentration of about 1mg/mL, injecting 10 mu L of the sample solution into a liquid chromatograph, and detecting the purity of a main component and related substances; the method adopts a C8 chromatographic column which well retains the moderately polar compounds and an ammonium acetate aqueous solution/acetonitrile reversed phase buffer salt chromatographic system, and can enhance the retention of the target compounds; the disodium sulfosuccinate intermediate is separated by gradient elution, so that the purity of the disodium sulfosuccinate intermediate can be quickly detected, the main component and related substances are effectively separated, and the reaction of the disodium sulfosuccinate intermediate is monitored.
Description
Technical Field
The invention belongs to a High Performance Liquid Chromatography (HPLC) method, and particularly relates to a method for detecting related substances and purity of a disodium sulfosuccinate intermediate by using HPLC.
Background
The undecylenic amide MEA-disodium sulfosuccinate is a chemical auxiliary agent, is used as a surfactant, and has a bactericidal effect.
The structural formula of the undeceneamide MEA-disodium sulfosuccinate is shown in the specification
Of the formula C 17 H 27 NNa 2 O 8 S, chemical name of Disodium 4- [2- [ (1-oxoundec-10-enyl) amino]ethyl]2-sulfonucocinate, the purity of the intermediate and the content of related substances need to be controlled in the production process, and DMF and maleic anhydride can be possibly used as the related substances.
Therefore, the separation of the undecenylamide MEA-disodium sulfosuccinate intermediate and related substances is significant to the reaction control in the production process of the undecenylamide MEA-disodium sulfosuccinate intermediate.
Disclosure of Invention
The invention aims to provide an HPLC-UV method for detecting the purity, related substance content and solvent residue of a key intermediate in a process of preparing a disodium sulfosuccinate starting material.
The technical scheme adopted by the invention for solving the technical problems is as follows: an HPLC-UV detection method for the purity of a disodium sulfosuccinate intermediate is provided, and the detection conditions are as follows: a chromatographic column: dikma Diamond C8, 150 x 4.6mm, 5 μm, with good retention for moderately polar compounds, column temperature 35 ℃; mobile phase: the water phase is ammonium acetate water solution, the organic phase is acetonitrile, and the flow rate is 0.6 mL/min; the elution procedure was a gradient elution: eluting with 5% acetonitrile for 2min, increasing methanol gradient to 75% for 15min, washing with 75% methanol for 3min, adjusting back to 5% acetonitrile at initial ratio with 0.1min, and balancing for 8 min; detection wavelength: 205 nm; disodium sulfosuccinate intermediate has fewer double bonds, and the detection wavelength of 205nm (short wavelength) is used to quantify disodium sulfosuccinate intermediate; the method comprises the following steps:
(1) respectively taking appropriate amount of disodium sulfosuccinate intermediate 1 and intermediate 2, dissolving samples by using CAN as a diluent, and respectively preparing sample solutions with the concentration of about 1mg of disodium sulfosuccinate intermediate 1 or intermediate 2 in every 1mL of diluent;
(2) injecting the solution obtained in the step (1) into a liquid chromatograph according to the sample injection volume of 10 mu L, recording a chromatogram, completing the separation of the disodium sulfosuccinate intermediate and related substances, and detecting the purity of the disodium sulfosuccinate intermediate and the content of the related substances, wherein the related substances possibly exist are DMF and maleic anhydride.
Wherein the aqueous phase is 8mM ammonium acetate aqueous solution.
Wherein, the liquid chromatograph is a Thermo Ultimate 3000/VC DAD detector.
The method adopts a C8 chromatographic column which well retains the moderately polar compounds and an ammonium acetate aqueous solution/acetonitrile reversed phase buffer salt chromatographic system, and can enhance the retention of the target compounds; gradient elution is used for separation, the purity of the disodium sulfosuccinate intermediate 1 and the purity of the intermediate 2 can be rapidly detected, main components and related substances are effectively separated, and the reaction of the disodium sulfosuccinate intermediate is monitored
The invention adopts 8mM ammonium acetate water solution as water phase, and enhances the retention of disodium sulfosuccinate intermediate in a mobile phase system.
The column temperature is set to be 35 ℃, so that the condition that ammonium acetate in a water phase is salted out due to too low temperature is avoided, and the column temperature tolerance range of the chromatographic column is also met.
The purity and the content of related substances of the disodium sulfosuccinate intermediate are calculated by a percentage area method, and the established method is simple and easy to implement.
The disodium sulfosuccinate intermediate and related substances are monitored at 205nm (short wavelength) so as to obtain appropriate UV absorbance and chromatographic peak height.
The method can simply and rapidly determine the purity and the content of related substances of the disodium sulfosuccinate intermediate, and solves the problem of reaction monitoring of the disodium sulfosuccinate intermediate in the production process.
Drawings
FIG. 1 is an HPLC overlay of disodium sulfosuccinate intermediate 1 and intermediate 2 of the process of the present invention;
figure 2 is an HPLC overlay of the disodium sulfosuccinate intermediate and related materials of the present invention.
Detailed Description
The invention is further described with reference to the following figures and specific embodiments.
The applicant finds that by using a C8 chromatographic column with good retention of moderately polar compounds and using ammonium acetate aqueous solution/acetonitrile as a mobile phase system, gradient elution can effectively separate disodium sulfosuccinate intermediates and related substances thereof, and has strong specificity, so that the purity and the content of the related substances of the disodium sulfosuccinate intermediates can be accurately determined, and the HPLC-UV method for detecting the purity, the content of the related substances and the residual solvent of key intermediates in the process of preparing disodium sulfosuccinate starting materials is provided.
The HPLC detection method can be realized according to the following method:
(1) taking appropriate amounts of disodium sulfosuccinate intermediate 1 and intermediate 2, respectively, dissolving the samples by using ACN as a diluent, and preparing sample solutions containing about 1mg of disodium sulfosuccinate intermediate 1 or intermediate 2 per 1mL of the diluent.
(2) And (2) injecting the solution obtained in the step (1) into a liquid chromatograph according to the sample injection volume of 10 mu L, wherein the detection conditions are as follows:
high performance liquid chromatograph: thermo Ultimate 3000, DAD detector.
A chromatographic column: dikma diamond C8, 150 × 4.6mm, 5 μm.
Mobile phase: 8Mm ammonium acetate aqueous solution (channel one), acetonitrile (channel two).
Elution procedure: eluting with 5% acetonitrile for 2min, increasing methanol gradient to 75% for 15min, washing with 75% methanol for 3min, adjusting to 5% acetonitrile at initial ratio by 0.1min, and balancing for 8 min.
Detection wavelength: 205 nm.
Flow rate: 0.6 mL/min.
Column temperature: 35 ℃ is carried out.
Sample introduction volume: 10 μ L.
The experimental steps are as follows: taking 10mg of each of guanidine hydrochloride and produced 2, 4-diamino-6-hydroxypyrimidine solid as starting materials, placing the starting materials in a 5mL volumetric flask, and adding ACN (Acrylonitrile-N-H) 2 O =1:1 (v/v) was dissolved and diluted to the scale, shaken up, as a sample solution for development of the method.
And taking the sample solution, carrying out high performance liquid chromatography analysis according to the conditions, and recording a chromatogram. As a result, referring to FIG. 1, in FIG. 1, the peak 1 is 2, 4-diamino-6-hydroxypyrimidine (main component) and the peak 2 is guanidine hydrochloride (known impurity of main component), and it can be seen that under these conditions, the peak patterns of 2, 4-diamino-6-hydroxypyrimidine and guanidine hydrochloride as a known impurity to be controlled are good.
Comparative example 1
Instruments and conditions.
High performance liquid chromatograph: thermo Ultimate 3000, DAD detector.
A chromatographic column: YMC-Pack ODS-AQ, 150 x 4.6mm, 3 μm.
Mobile phase: h 2 O (channel one), MeOH (channel two).
Elution procedure: eluting with 5% methanol for 5min, increasing methanol gradient to 90% for 9min, washing with 90% methanol for 1.5min, adjusting to 5% methanol at initial ratio with 0.1min, and balancing for 4.5 min.
Detection wavelength: and (4) full sweeping.
Flow rate: 1.0 mL/min.
Column temperature: at 35 deg.c.
Sample introduction volume: 1 μ L.
The experimental steps are as follows: taking 20mg of each of the intermediate 1 and the intermediate 2 of the disodium sulfosuccinate, placing the disodium sulfosuccinate and the intermediate 2 into a 20mL volumetric flask, adding ACN to dissolve and dilute the disodium sulfosuccinate to a scale, and shaking up the mixture to be used as a main component sample solution for developing the method.
Taking 20mg of DMF and maleic anhydride respectively, placing the DMF and the maleic anhydride in the same 20mL volumetric flask, respectively adding 0.2mL of prepared main component sample solutions of the intermediate 1 and the intermediate 2 of disodium sulfosuccinate respectively, dissolving and diluting the main component sample solutions to a scale by using ACN, and shaking up the solution to serve as an RS sample solution for developing the method.
Taking the sample solution, carrying out high performance liquid chromatography analysis according to the conditions, and recording a chromatogram. The results are shown in FIGS. 1 and 2. In figure 1, the peak M01 is disodium sulfosuccinate intermediate 1, and the peak M02 is disodium sulfosuccinate intermediate 2. As can be seen from the figure, under the condition, the peak patterns of the intermediate 1 and the intermediate 2 of disodium sulfosuccinate are good, the two can be completely separated, and the peak heights are proper. In the attached figure 2, the peak A is DMF, the peak B is maleic anhydride, the peak M01 is disodium sulfosuccinate intermediate 1, and the peak M02 is disodium sulfosuccinate intermediate 2. As can be seen from the figure, under the condition, the disodium sulfosuccinate intermediate 1 and intermediate 2 can be completely separated from related substances of DMF and maleic anhydride, the DMF and maleic anhydride at the concentration level of 100% have obvious peaks, and the disodium sulfosuccinate intermediate 1 and intermediate 2 at the concentration level of 1% have good response.
The above-described embodiments are merely illustrative of the principles and effects of the present invention, and some embodiments may be applied, and it will be apparent to those skilled in the art that various changes and modifications may be made without departing from the inventive concept of the present invention, and these embodiments are within the scope of the present invention.
Claims (3)
1. An HPLC-UV detection method for the purity of a disodium sulfosuccinate intermediate is characterized in that the detection conditions are as follows:
a chromatographic column: dikma Diamond C8, 150 × 4.6mm, 5 μm, column temperature 35 ℃;
mobile phase: the water phase is ammonium acetate water solution, the organic phase is acetonitrile, and the flow rate is 0.6 mL/min;
elution procedure: eluting with 5% acetonitrile for 2min, increasing methanol gradient to 75% at 15min, washing with 75% methanol for 3min, adjusting back to 5% acetonitrile at initial ratio at 0.1min, and balancing for 8 min;
detection wavelength: 205 nm;
the method comprises the following steps:
(1) respectively taking disodium sulfosuccinate intermediates, dissolving the disodium sulfosuccinate intermediates by using acetonitrile as a diluent, and preparing a sample solution with the concentration of 1mg of disodium sulfosuccinate intermediate in every 1mL of diluent;
(2) and (2) injecting the solution obtained in the step (1) into a liquid chromatograph according to the sample injection volume of 10 mu L, recording a chromatogram, completing the separation of the disodium sulfosuccinate intermediate and related substances, and detecting the purity of the disodium sulfosuccinate intermediate and the content of the related substances.
2. An HPLC-UV detection method for the purity of disodium sulfosuccinate intermediate according to claim 1, wherein the aqueous phase is 8mM ammonium acetate aqueous solution.
3. An HPLC-UV detection method for the intermediate purity of disodium sulfosuccinate according to claim 1, wherein the liquid chromatograph is a Thermo Ultimate 3000/VC, DAD detector.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07197078A (en) * | 1993-12-29 | 1995-08-01 | Kawaken Fine Chem Co Ltd | Polyoxyethylene fatty acid amide sulfosuccinic acid ester type surfactant, its production and detergent composition |
| WO2013186390A1 (en) * | 2012-06-15 | 2013-12-19 | Farma Grs, D.O.O. | Selective crystallization processes using reverse micelle and w/o microemulsion systems - multitask emulsion crystallization (mec) |
| CN108152316A (en) * | 2017-12-14 | 2018-06-12 | 中国日用化学工业研究院 | It is a kind of using maleic anhydride content and sulphonation rate as the quality inspection method of the glucosides sulfosuccinate ester salt product of index |
| CN109100454A (en) * | 2018-10-24 | 2018-12-28 | 中国日用化学研究院有限公司 | Method that is a kind of while measuring surfactant product sulfite salt and sulphates content |
| CN109115926A (en) * | 2018-10-24 | 2019-01-01 | 中国日用化学研究院有限公司 | The measuring method of sulfosuccinic acid content in Sulfosuccinate Surfactant product |
-
2022
- 2022-06-28 CN CN202210741371.XA patent/CN115112795B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07197078A (en) * | 1993-12-29 | 1995-08-01 | Kawaken Fine Chem Co Ltd | Polyoxyethylene fatty acid amide sulfosuccinic acid ester type surfactant, its production and detergent composition |
| WO2013186390A1 (en) * | 2012-06-15 | 2013-12-19 | Farma Grs, D.O.O. | Selective crystallization processes using reverse micelle and w/o microemulsion systems - multitask emulsion crystallization (mec) |
| CN108152316A (en) * | 2017-12-14 | 2018-06-12 | 中国日用化学工业研究院 | It is a kind of using maleic anhydride content and sulphonation rate as the quality inspection method of the glucosides sulfosuccinate ester salt product of index |
| CN109100454A (en) * | 2018-10-24 | 2018-12-28 | 中国日用化学研究院有限公司 | Method that is a kind of while measuring surfactant product sulfite salt and sulphates content |
| CN109115926A (en) * | 2018-10-24 | 2019-01-01 | 中国日用化学研究院有限公司 | The measuring method of sulfosuccinic acid content in Sulfosuccinate Surfactant product |
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Inventor after: Guan Danyingzi Inventor after: Mei Qing Inventor after: Hu Jin Inventor after: Chai Jinzhu Inventor before: Chai Jinzhu Inventor before: Guan Danyingzi Inventor before: Mei Qing Inventor before: Hu Jin |
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Effective date of registration: 20240204 Address after: C6324, C6522, C6523, C6524, Building C6, Optics Valley Biological City, No. 666, Gaoxin Avenue, Donghu New Technology Development Zone, Hongshan District, Wuhan, Hubei 430200 Applicant after: Wuhan Haite Bioinnovation Pharmaceutical Research Co.,Ltd. Country or region after: China Address before: 448000 No. 1, Xinghua Third Road, Duodao District, Jingmen City, Hubei Province Applicant before: Hanrui Pharmaceutical (Jingmen) Co.,Ltd. Country or region before: China |
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