CN108072718A - A kind of method that high performance liquid chromatography measures MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride content - Google Patents
A kind of method that high performance liquid chromatography measures MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride content Download PDFInfo
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- CN108072718A CN108072718A CN201810136363.6A CN201810136363A CN108072718A CN 108072718 A CN108072718 A CN 108072718A CN 201810136363 A CN201810136363 A CN 201810136363A CN 108072718 A CN108072718 A CN 108072718A
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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
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
Abstract
Present invention relates particularly to a kind of method that high performance liquid chromatography measures MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride, including step：The preparation of standard solution will contain MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride standard items diluent preparing into detection solution；The pretreatment of sample, uses mobile phase sample dissolution；Liquid chromatogram separates, and surfactant chromatographic column uses inorganic salt buffer organic phase as mobile phase and carry out isocratic elution, record HPLC spectrograms as stationary phase.The method of the present invention using high performance liquid chromatography can MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride in qualitative exactly, quantitative determination product, and this method have the characteristics that analysis method it is accurate, quickly, interference is small, disengaging time is short.
Description
Technical field
The invention belongs to analysis of compounds technical fields, and in particular to a kind of high performance liquid chromatography measures methacryloxypropyl
The method of ethyl-trimethyl salmiac content.
Background technology
MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride（Abbreviation DMC）, belong to the cationic surfactant of quaternary,
With double bond in its strand, homopolymerization can be both carried out, can also be copolymerized with many activated monomers.Its homopolymer and copolymerization
Object has the advantages that relative molecular mass is controllable, cationic degree is adjustable, stability is high and good water solubility, in papermaking, coal mining, oil
The industries such as work, biological medicine, water process have extensive use.
Analysis for quarternary ammonium salt compound detects, in early days using diphasic titration, iodimetric titration and argentometry etc., but
The sensitivity of these methods is relatively low.Established spectrophotometry, fluorescence analysis, capillary electrophoresis, chromatography and matter later
Spectrometry etc..Most of alkyls quaternary cationicses have the features such as not volatile, polarity is strong, usually make at present
Quantitative analysis is carried out with high performance liquid chromatography.
For example, Yang Yanwei etc. is disappeared with the hplc simultaneous determination of C8 chromatographic columns and diode array detector
Dodecyl benzyl dimethyl ammonium chloride in toxic agent, rice rummy this fourth, myristyl benzyl dimethyl ammonium chloride and cetyl
4 kinds of quaternary ammonium salts of dimethyl benzyl ammonium chloride；Xie Nan etc. is surveyed with the high performance liquid chromatography of C18 splitters and variable-wavelenght detector
5 kinds of cetrimonium bromide, cetalkonium chloride, miristalkonium chloride, Lauralkonium Chloride and benzethonium chloride quaternary ammonium salt preservatives in cosmetics are determined；
It is splitter that Cheng Xiao, which waits quietly with C18 columns, and ion-pairing agent (sodium heptanesulfonate etc.) is added in mobile phase, uses high performance liquid chromatography
Method determines the average molecular mass of fatty alkyl dimethylbenzyl based quaternary ammonium salt.
DMC is the highly polar compound of long-chain, cannot be effectively retained on common C8 and C18 columns；Use reverse phase C18 colors
Ion exchange interaction is too strong between its surface silanol and quaternary amine when composing column, is often difficult to obtain sharp symmetrical peak.And
And ion-pairing agent is added in high aqueous phase stream moves phase for a long time, it be easy to cause the decline of chromatographic column column effect, the lost of life.Thus,
The report of high-efficient liquid phase chromatogram technique analysis detection DMC is had no at present.
The content of the invention
In order to solve it is in the prior art cannot be exactly in qualitative, quantitative measurment product using high performance liquid chromatography
The problem of DMC, the present invention provides a kind of high performance liquid chromatography can exactly it is qualitative, quantitative determination product in methacryl
The detection method of oxy-ethyl-trimethyl salmiac, this method have analysis method is accurate, quick, interference is small, disengaging time is short etc.
Feature.
The technical problem to be solved in the present invention is achieved through the following technical solutions：
A kind of method that high performance liquid chromatography measures MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride, which is characterized in that including such as
Lower step：
1）The preparation of standard solution
MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride standard items diluent preparing will be contained into detection solution；
2）The pretreatment of sample
With flowing phased soln MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride to be measured；
3）Liquid chromatogram separates
Surfactant chromatographic column uses inorganic salt buffer-organic phase as mobile phase and carries out isocratic elution as stationary phase,
Record HPLC spectrograms.
Further, above-mentioned surfactant chromatographic column is to utilize reverse-phase chromatography and anionite to be chemically bonded work
A kind of mixed mode chromatographic column that skill combines.For reverse phase C18 chromatographic columns, stationary phase adds weak anionic friendship
The effect of changing.
Further, in above-mentioned detection solution the standard items containing MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride concentration
For 50~250mg/L；
The dilution is the one or more in water, acetonitrile, methanol and ammonium acetate.
Further, the inorganic salts in above-mentioned inorganic salt buffer are one in ammonium acetate, ammonium dihydrogen phosphate and ammonium carbonate
Kind is a variety of；
The organic phase is the one or more in methanol, acetonitrile and isopropanol.
Further, it is glacial acetic acid or phosphoric acid that above-mentioned inorganic salt buffer, which adjusts pH agents useful for same,.
Further, the concentration of inorganic salts is 0.01~0.03mol/L in above-mentioned inorganic salt buffer；The inorganic salts delay
The pH value range of fliud flushing is 4.0~6.0.
Further, the volume ratio of inorganic salts buffer salt system and organic phase (40 ~ 50) in above-mentioned mobile phase：(60~50).
Further, the flow velocity of above-mentioned mobile phase is 0.8~1.2mL/min.
Further, the column temperature of above-mentioned stationary phase is 20 DEG C~40 DEG C.
Further, above-mentioned HPLC spectrograms are the HPLC spectrograms in Detection wavelength 210nm records.
Compared with prior art, beneficial effects of the present invention：
Report at present on quaternary ammonium salt cationic analysis detection is more, but has no the report of related DMC analyses detection.The present invention
Using surfactant chromatographic column（AcclaimTMSurfactant Plus）, using inorganic buffer salt solution-organic phase as flowing
Phase using UV detector, establishes the HPLC analytical method of DMC.This method is quick, accurate, reappearance is high, and
Without using ion-pairing agent, available for the qualitative and quantitative analysis of DMC in scientific research and production field, also can further genralrlization arrive other
The analysis detection of quaternary ammonium salt containing unsaturated bond.
Description of the drawings
Fig. 1 is the chromatogram of MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride in embodiment 3；Fig. 2 is first in embodiment 4
The chromatogram of base acrylyl oxy-ethyl-trimethyl salmiac；
Fig. 3 is the chromatogram of MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride in embodiment 5；Fig. 4 is methyl-prop in embodiment 7
The chromatogram of alkene acyloxyethyl trimethyl ammonium chloride.
Specific embodiment
Further detailed description is done to the present invention with reference to specific embodiment, but embodiments of the present invention are not limited to
This.
Material employed in the present embodiment is as follows：
Liquid chromatogram separation process is efficient using Thermo Fisher Scientific company's Ts hermoU3000 in the present embodiment
Liquid chromatograph, equipped with VWD-3400RS UV detector and Chromeleon work stations；
The acidometer used when measuring pH value after mobile phase acidifying in the present embodiment.
The methanol that is used in the present embodiment, acetonitrile, isopropanol is chromatographically pures；Water is deionized water；Ammonium acetate, biphosphate
Ammonium is that analysis is pure with ammonium carbonate；MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride reference substance is purchased from Shandong West Asia chemistry share
Co., Ltd.
The test sample used in the present embodiment is commercially available Henan factory methylacryoyloxyethyl trimethyl ammonia chloride
Ammonium industrial goods.
The reference substance solution used in the present embodiment, preparation method are as follows：Weigh 0.6667g methylacryoyloxyethyls three
Ammonio methacrylate is dissolved with dilution in 100mL volumetric flasks, and constant volume, obtains content as 5000mg/L Standard Stock solutions（24
It is prepared again after hour）, using diluted into be made into mass concentration be respectively 50,75,100,150, the control of 250mg/L
Product solution.
Embodiment 1：
Instrument：ThermoU3000 high performance liquid chromatographs, UV detector；
Chromatographic column：Surfactant chromatographic column（AcclaimTMSurfactant column）, 4.6 × 250mm, 5 μm；
Mobile phase：0.01mol/L ammonium dihydrogen phosphates buffer solution-acetonitrile (50:50)；
Detection wavelength：210nm；
Flow velocity：1.0mL/min；
Sample size：20μL；
Column temperature：30℃；
Dilution：0.01mol/L ammonium dihydrogen phosphates buffer solution-acetonitrile (50:50)；
The reference substance solution of 200mg/L is taken, is measured by above-mentioned chromatographic condition, records chromatogram.From chromatogram, when slow
Rush salting liquid for 0.01mol/L diammonium hydrogen phosphates when, retention time is long, so as to be unfavorable for quickly analyzing.
Embodiment 2：
Instrument：ThermoU3000 high performance liquid chromatographs, UV detector；
Chromatographic column：Surfactant chromatographic column（AcclaimTM Surfactant column）, 4.6 × 250mm, 5 μm；
Mobile phase：0.01mol/L ammonium carbonates buffer solution-acetonitrile (50:50)；
Detection wavelength：210nm；
Flow velocity：1.0mL/min；
Sample size：20μL；
Column temperature：30℃；
Dilution：0.01mol/L ammonium carbonates buffer solution-acetonitrile (50:50)；
The reference substance solution of above-mentioned same concentration is taken, is measured by above-mentioned chromatographic condition, records chromatogram.It can by chromatogram
Know, when buffer salt solution is 0.01mol/L ammonium carbonates, peak shape is wide, and hangover is serious.In conjunction with the embodiments 1 with embodiment 2, when
For ammonium dihydrogen phosphate or carbonic acid on time, the buffering dynamics of mobile phase are inadequate, cause to retain for inorganic salt buffer in mobile phase
The problems such as overlong time, peak shape hangover.
Embodiment 3：
Instrument：ThermoU3000 high performance liquid chromatographs, UV detector；
Chromatographic column：Surfactant chromatographic column（AcclaimTMSurfactant column）, 4.6 × 250mm, 5 μm；
Mobile phase：0.01mol/L ammonium acetate buffers-acetonitrile (40:60)；
Detection wavelength：210nm；
Flow velocity：1.0mL/min；
Sample size：20μL；
Column temperature：30℃；
Dilution：0.01mol/L ammonium acetate buffers-acetonitrile (40:60)；
The reference substance solution of above-mentioned same concentration is taken, is measured by above-mentioned chromatographic condition, records chromatogram, the result is shown in Figure 1.From
Fig. 1 can be seen that peak shape hangover seriously, be disturbed be subject to solvent.
Embodiment 4：
Instrument：ThermoU3000 high performance liquid chromatographs, UV detector；
Chromatographic column：Surfactant chromatographic column（AcclaimTMSurfactant column）, 4.6 × 250mm, 5 μm；
Mobile phase：0.01mol/L ammonium acetate buffers-acetonitrile (45:55)；
Detection wavelength：210nm；
Flow velocity：1.0mL/min；
Sample size：20μL；
Column temperature：30℃；
Dilution：0.01mol/L ammonium acetate buffers-acetonitrile (45:55)；
The reference substance solution of above-mentioned same concentration is taken, is measured by above-mentioned chromatographic condition, records chromatogram, the result is shown in Fig. 2.From
Fig. 2, which can be seen that peak shape, still hangover, but has improvement compared to Fig. 1.
Embodiment 5：
Instrument：ThermoU3000 high performance liquid chromatographs, UV detector；
Chromatographic column：Surfactant chromatographic column（AcclaimTMSurfactant column）, 4.6 × 250mm, 5 μm；
Mobile phase：0.01mol/L ammonium acetate buffers-acetonitrile (50:50)；
Detection wavelength：210nm；
Flow velocity：1.0mL/min；
Sample size：20μL；
Column temperature：30℃；
Dilution：0.01mol/L ammonium acetate buffers-acetonitrile (50:50)；
The standard solution of above-mentioned same concentration is taken, is measured by above-mentioned chromatographic condition, records chromatogram, the result is shown in Fig. 3.From figure
3 as can be seen that retention time 2.633min, peak shape is sharp and symmetrical, and compared with Fig. 1, Fig. 2, Fig. 3 retention times are short, and rings
It should increase.MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride can reach good with its each impurity and separate, and meet Chinese Pharmacopoeia
Requirement.
Embodiment 6：
Instrument：ThermoU3000 high performance liquid chromatographs, UV detector；
Chromatographic column：Surfactant chromatographic column（AcclaimTMSurfactant column）, 4.6 × 250mm, 5 μm；
Mobile phase：0.01mol/L ammonium acetate buffers-acetonitrile (50:50)；It is 4 ~ 6 to adjust pH value with glacial acetic acid；
Detection wavelength：210nm；
Flow velocity：1.0mL/min；
Sample size：20μL；
Column temperature：30℃；
Dilution：0.01mol/L ammonium acetate buffers-acetonitrile (50:50)；
The reference substance solution of above-mentioned same concentration is taken, is measured by above-mentioned chromatographic condition, records chromatogram.It can by chromatogram
Know, increase with the increase DMC peaks retention time of pH, tailing factor increases to 1.27 by 0.98.In ± 0.1 scopes of pH5.00
Interior, tailing factor is 0.98 ~ 1.10, and chromatography peak symmetry is good.Therefore pH value of pH5.00 ± 0.1 as mobile phase is selected.
Embodiment 7：
Instrument：ThermoU3000 high performance liquid chromatographs, UV detector；
Chromatographic column：Surfactant chromatographic column（AcclaimTMSurfactant column）, 4.6 × 250mm, 5 μm；
Mobile phase：0.01mol/L ammonium acetate buffers (with glacial acetic acid tune pH to 5.0)-acetonitrile (50:50)；
Detection wavelength：210nm；
Flow velocity：1.0mL/min；
Sample size：20μL；
Column temperature：30℃；
Dilution：0.01mol/L ammonium acetate buffers (with glacial acetic acid tune pH to 5.0 ± 0.1)-acetonitrile (50:50)；
The standard solution of above-mentioned same concentration is taken, is measured by above-mentioned chromatographic condition, records chromatogram, the result is shown in Fig. 4.Chromatography
Peak shape is symmetrically good, and baseline is steady.
7 performance test of embodiment：
1st, line style scope：
Using diluted into be made into mass concentration be respectively 50,75,100,150, the reference substance solution of 250mg/L.According to
Chromatographic condition in example 3 is measured, and does calibration curve with peak area and reference substance concentration, Y represents peak area, and X represents dense
Degree, obtained regression equation are：Y=0.3795X+0.9334, r=0.9994.
2nd, recovery of standard addition：
Precision weighs totally 6 parts of each 1g of test sample, the reference substance solution of various concentration is separately added into, by the chromatostrip of embodiment 3
Part method measures, and calculates recovery of standard addition.
3rd, reappearance：
3 parts of samples are taken, each sample measures five times, calculates relative standard deviation（RSD%）.
4th, quantitative limit, the detection limit of sample concentration calculating and method：
Standard curve is done with peak area and normal concentration by external standard method, calculates methylacryoyloxyethyl trimethyl ammonia chloride in sample
The content of ammonium.
With signal-to-noise ratio（S/N=10）The quantitative limit of computational methods, signal-to-noise ratio（S/N=3）The Monitoring lower-cut of computational methods.
5th, 3 batch samples of test result analysis, are measured according to the chromatographic condition of example 3, and pass through by parallel 3 parts
The mass fraction of DMC in regression equation calculation sample, obtain result be respectively 60.12%, 59.97%, 60.35%, 60.63%,
60.47%、60.15%、58.90%、59.23%、58.45%。
The present embodiment method quantitative limit 0.167mg/L (signal-to-noise ratio >=10) and detection limit 0.020mg/L (signal-to-noise ratio >=
3)；Method linear relationship in the concentration range of 50mg/L~250mg/L is good, and correlation coefficient r reaches more than 0.999；Mark-on
The rate of recovery is in the range of 91%~109%；Relative standard deviation is less than 0.35%.
The dilution or water or methanol of above-described embodiment, organic phase or methanol or isopropanol；Inorganic salts
The concentration of inorganic salts is 0.01~0.03mol/L in buffer solution, the pH value range of inorganic salt buffer is 4.0~6.0；It surveys
During amount, the flow velocity of mobile phase is 0.8~1.2mL/min, and the column temperature of stationary phase is 20 DEG C~40 DEG C, is recorded in Detection wavelength
For the HPLC spectrograms of 200~235nm.
The above content is a further detailed description of the present invention in conjunction with specific preferred embodiments, it is impossible to assert
The specific implementation of the present invention is confined to these explanations.For those of ordinary skill in the art to which the present invention belongs, exist
On the premise of not departing from present inventive concept, several simple deduction or replace can also be made, should all be considered as belonging to the present invention's
Protection domain.
Claims (10)
1. a kind of method that high performance liquid chromatography measures MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride, which is characterized in that including
Following steps：
1）The preparation of standard solution
MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride standard items diluent preparing will be contained into detection solution；
2）The pretreatment of sample
With flowing phased soln MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride to be measured；
3）Liquid chromatogram separates
Surfactant chromatographic column uses inorganic salt buffer-organic phase as mobile phase and carries out isocratic elution as stationary phase,
Record HPLC spectrograms.
2. according to the method described in claim 1, it is characterized in that, the surfactant chromatographic column is by reverse-phase chromatography and the moon
A kind of mixed mode chromatographic column that ion-exchanger is combined using technique is chemically bonded.
3. according to the method described in claim 1, it is characterized in that, contain methylacryoyloxyethyl three in the detection solution
The concentration of the reference substance of ammonio methacrylate is 50~250mg/L；
The dilution is the one or more in water, acetonitrile, methanol and ammonium acetate.
4. according to the method described in claim 1, it is characterized in that, inorganic salts in the inorganic salt buffer be ammonium acetate,
Ammonium dihydrogen phosphate and the one or more in ammonium carbonate；
The organic phase is the one or more in methanol, acetonitrile and isopropanol.
5. according to the method described in claim 1, it is characterized in that, it is ice vinegar that the inorganic salt buffer, which adjusts pH agents useful for same,
Acid or phosphoric acid.
6. according to the method described in claim 1, it is characterized in that, the concentration of inorganic salts is 0.01 in the inorganic salt buffer
~0.03mol/L；
The pH value range of the inorganic salt buffer is 4.0~6.0.
7. according to the method described in claim 1, it is characterized in that, the flow velocity of the mobile phase is 0.8~1.2mL/min.
8. according to the method described in claim 1, it is characterized in that, the column temperature of the stationary phase is 20 DEG C~40 DEG C.
9. according to the method described in claim 1, it is characterized in that, inorganic salts buffer salt system and organic phase in the mobile phase
Volume ratio (40 ~ 50)：(60~50).
10. according to the method described in claim 1, it is characterized in that, the HPLC spectrograms are in 200~235nm of Detection wavelength
The HPLC spectrograms of record.
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| CN115436513A (en) * | 2022-09-05 | 2022-12-06 | 中轻日用化学检验认证有限公司 | Method for measuring average relative molecular mass of fatty alkyl trimethyl ammonium chloride |
| CN115436513B (en) * | 2022-09-05 | 2023-11-28 | 中轻日用化学检验认证有限公司 | Method for measuring average relative molecular weight of fatty alkyl trimethyl ammonium chloride |
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