CN116359398A - Method for measuring content of p-hydroxyanisole in acrylic ester product - Google Patents
Method for measuring content of p-hydroxyanisole in acrylic ester product Download PDFInfo
- Publication number
- CN116359398A CN116359398A CN202310456947.2A CN202310456947A CN116359398A CN 116359398 A CN116359398 A CN 116359398A CN 202310456947 A CN202310456947 A CN 202310456947A CN 116359398 A CN116359398 A CN 116359398A
- Authority
- CN
- China
- Prior art keywords
- hydroxyanisole
- para
- sample
- high performance
- performance liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 title claims abstract description 224
- 238000000034 method Methods 0.000 title claims abstract description 43
- -1 acrylic ester Chemical class 0.000 title abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 75
- 239000012086 standard solution Substances 0.000 claims abstract description 26
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 7
- 238000005303 weighing Methods 0.000 claims description 15
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 14
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004364 calculation method Methods 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 abstract description 5
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 238000005259 measurement Methods 0.000 description 14
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 12
- 238000011084 recovery Methods 0.000 description 12
- 238000002798 spectrophotometry method Methods 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- HDPISCIDKUMRDI-UHFFFAOYSA-M N(=O)[O-].[Na+].[N+](=O)([O-])[O-].[Al+3] Chemical compound N(=O)[O-].[Na+].[N+](=O)([O-])[O-].[Al+3] HDPISCIDKUMRDI-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Images
Classifications
-
- 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
- G01N30/60—Construction of the column
-
- 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
-
- 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
- G01N30/86—Signal analysis
- G01N30/8675—Evaluation, i.e. decoding of the signal into analytical information
- G01N30/8679—Target compound analysis, i.e. whereby a limited number of peaks is analysed
-
- 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
- G01N2030/042—Standards
- G01N2030/047—Standards external
Landscapes
- 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)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Library & Information Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of analytical chemistry, and particularly discloses a method for measuring the content of para-hydroxyanisole in an acrylic ester product, which comprises the steps of dissolving 0.1283g of para-hydroxyanisole standard substance with a proper amount of methanol, and then pouring the dissolved para-hydroxyanisole standard substance into a 250mL volumetric flask to prepare a standard solution of 0.5 mg/mL; and respectively transferring a certain volume of p-hydroxyanisole standard solution with the concentration of 0.5mg/mL, fixing the volume of the p-hydroxyanisole standard solution to a volumetric flask with the volume of 100mL by using methanol to obtain p-hydroxyanisole standard solutions with different concentrations, placing the standard solutions with different concentrations under the selected high performance liquid chromatography condition, measuring the peak areas of the high performance liquid chromatography and the quality of the p-hydroxyanisole corresponding to the standard solutions with different concentrations by using a high performance liquid chromatograph, and drawing a working curve. The method has simple steps, less reagents used in the measuring process, short analysis time and effectively shortened working efficiency, and the method can be suitable for various acrylic monomers, and the measured deviation values are less than 5%.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and particularly relates to a method for measuring the content of p-hydroxyanisole in an acrylate product.
Background
When the acrylate product is used on a photosensitive material, a reactive diluent is usually used, and the reactive diluent is usually called a monomer or a functional monomer, is an important component of the photo-curing material, not only dissolves and dilutes an oligomer and adjusts the viscosity of the system, but also participates in the photo-curing process, and influences the photo-curing rate of the photo-curing product and various properties of a cured film. Reactive diluents can be classified into monofunctional reactive diluents and polyfunctional reactive diluents according to the number of reactive groups they contain per molecule.
The reactive diluent of the photo-curing coating is mainly acrylic esters with high polymerization activity, is extremely easy to polymerize under the influence of external light, heat and the like, and a proper amount of polymerization inhibitor is required to be added. The polymerization inhibitor can terminate free radicals to stop the polymerization reaction. Typical polymerization inhibitors include phenols, aromatic amines, aromatic nitro compounds, and the like.
The polymerization inhibitor commonly used in the acrylate photo-curing monomer material is p-hydroxyanisole, which is also called: p-methoxyphenol, hydroquinone monomethyl ether, 4-methoxyphenol, p-hydroxyanisole, 4-methoxyphenol. The method has the greatest advantages that the added monomer and other monomers do not need to be removed when in copolymerization, can be directly copolymerized in a ternary way, and can also be used as an anti-aging agent, an antioxidant and the like.
The appearance of the para-hydroxyanisole is white flaky or waxy crystals. Melting point 52.5 ℃, boiling point 243 ℃, relative density 1.55 (20/20 ℃). Is easily soluble in ethanol, ether, acetone, benzene and ethyl acetate, and is slightly soluble in water. It is mainly used for polymerization inhibitor, ultraviolet inhibitor, dye intermediate, etc. of vinyl plastic monomer.
But the dosage of the para-hydroxyanisole can directly influence the polymerization condition of the polymer in the reactant, and simultaneously has direct influence on the quality guarantee period of the product. The concentration index ranges of the para-hydroxyanisole in the HG/T4947-2016 trimethylolpropane triacrylate for the photosensitive material and the HG/T4948-2016 tripropylene glycol diacrylate for the photosensitive material are respectively set to be 100 mug/g-400 mug/g. Other types of monomer industries do not set an index for para-hydroxyanisole, but in actual production, downstream customers often have requirements. In European and American, the para-hydroxyanisole belongs to the list of management and control, and foreign clients often require to reduce the content of the para-hydroxyanisole on the premise of ensuring the stable quality of products.
Currently, various methods for detecting and analyzing the concentration of para-hydroxyanisole have been developed, including spectrophotometry, gas chromatography, and gas chromatography-mass spectrometry. High performance liquid chromatography is not currently available for detecting the hydroxyanisole. GB/T7717.15-2018 (determination of the content of p-hydroxyanisole in section 15 of industrial acrylonitrile) lists a detection method of direct spectrophotometry and gas chromatography; GB/T17530.5-1998 "determination of polymerization inhibitor in Industrial acrylic acid and esters" uses the reaction of para-hydroxyanisole with nitrous acid in an acidic medium to give a yellow nitrous acid derivative, which is determined by spectrophotometry at a wavelength of 420 nm. The p-hydroxyanisole in the photo-curable monomer was analyzed using this standard. There is a literature disclosure of a method for analysis using a sodium nitrite-aluminum nitrate solution instead of a sodium nitrite-glacial acetic acid system. However, the method is generally complicated in sample pretreatment, more in reagents and longer in analysis time, so that the method for measuring the content of the p-hydroxyanisole in the acrylate product is urgently needed.
Disclosure of Invention
The invention aims to provide a method for measuring the content of para-hydroxyanisole in an acrylic ester product, which solves the problems of complex prior measuring method, more reagents and longer analysis time.
In order to solve the technical problems, the invention provides a method for measuring the content of para-hydroxyanisole in an acrylate product, which comprises the following steps:
s1, configuring the operation condition of a high performance liquid chromatograph;
s2, preparing a standard solution, namely dissolving 0.1283g of a para-hydroxyanisole standard substance with methanol, transferring the dissolved para-hydroxyanisole standard substance into a 250mL volumetric flask, and then fixing the volume to 250mL with methanol to prepare a standard solution with the para-hydroxyanisole concentration of 0.5132 mg/mL;
s3, drawing a standard working curve, namely respectively transferring p-hydroxyanisole standard solutions with different volumes, fixing the volumes to a volumetric flask with 100mL by using methanol to obtain p-hydroxyanisole standard solutions with different concentrations, placing the standard solutions with different concentrations into a region to be tested of a high performance liquid chromatograph under the configured high performance liquid chromatograph condition, measuring the high performance liquid chromatograph peak areas corresponding to the different concentrations of the standard solutions and the mass of the p-hydroxyanisole by using the high performance liquid chromatograph, and drawing the standard working curve by using the measured high performance liquid chromatograph peak areas and the measured mass of the p-hydroxyanisole to obtain a fitting equation of the correlation relationship and the correlation relationship between the two;
s4, measuring the para-hydroxyanisole of the sample to be measured, namely weighing a certain amount of the sample to be measured, fixing the volume of the sample to be measured to a volume bottle of 100mL by using methanol, placing the sample to be measured under the configured high performance liquid chromatography condition, measuring and recording the peak area of the para-hydroxyanisole, substituting the recorded peak area into a working curve, and calculating the mass of the para-hydroxyanisole in the sample to be measured by using a fitting equation;
s5, calculating the mass of the para-hydroxyanisole according to the sample weighing amount of the sample to be detected and the S4, and calculating the concentration of the para-hydroxyanisole in the sample to be detected.
Further, the operating conditions of the high performance liquid chromatograph in S1: the liquid chromatographic column is an EC-C184.6mm.250 mm,4 μm or C18 chromatographic column with equal division capacity, the mobile phase is acetonitrile and water in a ratio of 50:50, the sample injection amount is 5 mu L, the flow rate is 1.5mL/min, and the detector wavelength is 278nm.
Further, the fitting equation of the correlation between the peak area of the high performance liquid chromatography in S3 and the quality of the para-hydroxyanisole is y= 34.841x-98.907, x represents the peak area of the para-hydroxyanisole recorded by the high performance liquid chromatography under the wavelength of 278nm, and y represents the quality of the para-hydroxyanisole in the standard solution.
Further, the sample to be measured in the step S4 is an acrylic acid monomer, and the acrylic acid monomer is one of tripropylene glycol diacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate or 1, 6-propylene glycol diacrylate.
Further, the acrylic acid monomer has a sample weight of 4.5g to 5.5g.
Further, the calculation mode in S5 is that the concentration of para-hydroxyanisole=mass of para-hydroxyanisole ≡the sample weighing amount of the sample to be measured.
The method has the beneficial effects that the method has simple steps, fewer reagents are used in the measuring process, the analysis time is short, the working efficiency is effectively shortened, the method can be suitable for various acrylic monomers, and the measured deviation values are less than 5%;
the calculating and measuring method can calculate the mass of the para-hydroxyanisole in the sample to be measured by the calculated mass of the para-hydroxyanisole and the sample weighing amount of the sample to be measured.
Drawings
In order to more clearly illustrate the technical solutions of the present invention, the following description will briefly explain the drawings used in the embodiments or the description of the prior art, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and that other drawings can be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a linear fitting working graph of the correlation between the peak area of a high performance liquid chromatography and the quality of the para-hydroxyanisole in the method for measuring the content of the para-hydroxyanisole in the acrylate product;
Detailed Description
The following description of the embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
In three specific embodiments of the present invention, as shown in fig. 1, a method for measuring the content of para-hydroxyanisole in an acrylate product is specifically disclosed as follows:
preparing a concentration solution, namely dissolving 0.1283g of p-hydroxyanisole standard substance with a proper amount of methanol, then fixing the volume by using the methanol to a volume of 250mL, and pouring the solution into a volumetric flask to prepare 0.5132mg/mL of standard solution;
drawing a standard working curve, namely respectively transferring 1mL, 3mL, 5mL, 8mL and 10mL of standard solution with the concentration of 0.5mg/mL of para-hydroxyanisole, and fixing the volume to a volumetric flask with 100mL by using methanol. The mass of p-hydroxyanisole in each 100mL of solution was 513.2 μg, 1539.6 μg, 2566.0 μg, 4105.6 μg and 5132.0 μg, respectively.
And (3) selecting a C18 chromatographic column, taking acetonitrile and water in a ratio of 50:50 as mobile phases, taking 5 mu L of sample injection amount and 1.5mL/min of flow rate, measuring a standard solution with a detector wavelength of 278nm, recording the chromatographic peak area of the p-hydroxyanisole after the measurement is completed, drawing a working curve according to the peak area of the high performance liquid chromatography obtained by the measurement and the quality of the p-hydroxyanisole, and obtaining the correlation relationship of the two after the drawing is completed.
TABLE 1 mass of para-hydroxyanisole (ug) and high Performance liquid chromatography peak area
From fig. 1, it can be seen that the equation of the mass fitting effect of the peak area of the high performance liquid chromatography and the para-hydroxyanisole is y= 34.841x-98.907, r2=0.9998, and the relation index R on the working curve 2 The correlation is good when the mass of the p-hydroxyanisole in the sample is more than or equal to 0.999, wherein x represents the peak area of the p-hydroxyanisole recorded by high performance liquid chromatography under the wavelength of 278nm, and y represents the mass of the p-hydroxyanisole in the sample, and the unit is mug.
The concentration of para-hydroxyanisole in the sample (μg/g) is equal to the mass of para-hydroxyanisole calculated from the curve (μg) divided by the weighed amount of the sample (g).
Spectrophotometry in the following examples is a method according to GB/T17530.5-1998 determination of polymerization inhibitor in industrial acrylic acid and esters, in which the concentration of p-hydroxyanisole is detected by spectrophotometry, and the deviation value= (quality result of p-hydroxyanisole detected by liquid phase method-quality result of p-hydroxyanisole detected by spectrophotometry)/liquid phase result×100% absolute value;
example 1
Determination of para-hydroxyanisole in trimethylolpropane triacrylate: 5.0940g of trimethylolpropane triacrylate sample is weighed, dissolved with a small amount of methanol, and the volume is fixed to a 100mL volumetric flask and shaken well. Under the selected high performance liquid chromatography condition, the peak area of the p-hydroxyanisole is 44.1 recorded by sample injection, and the p-hydroxyanisole is substituted into a standard working curve to obtain the mass of the p-hydroxyanisole in the sample of 1437.58 mug, and the mass of the p-hydroxyanisole is divided by the weighing weight of the sample to obtain the concentration of the p-hydroxyanisole in the sample of 282.21 mug/g.
Determination of recovery of para-hydroxyanisole in trimethylolpropane triacrylate: weighing 5.0054g of trimethylolpropane triacrylate sample, transferring 4mL of p-hydroxyanisole with the concentration of 513.2 mug/mL as a standard solution, using methanol to fix the volume into a 100mL volumetric flask, shaking uniformly, and under the selected high performance liquid chromatography condition, recording the peak area of the p-hydroxyanisole as 120.9 by sample injection, wherein the calculated formula of the recovery rate is as follows: recovery rate= (mass after adding mark-mass before adding mark)/adding amount 100% to calculate the recovery rate of the para hydroxy anisole, the measurement result of the recovery rate is shown in table 2, the result is 98.39%, and the method is accurate and reliable.
Table 2 determination of the labeled recovery of para-hydroxyanisole in trimethylolpropane triacrylate
Determination of the repeatability of para-hydroxyanisole in trimethylolpropane triacrylate: the same sample is weighed 5.0+/-0.5 g, accurately to 0.0001g, dissolved by methanol, and is fixed to a volume of 100mL in a volumetric flask, and shaken well. Sample injection is carried out under the selected liquid chromatography condition, the peak area of the para-hydroxyanisole is recorded, and the measurement result is shown in Table 3. The RSD of the 6 results was 1.10%, indicating a better reproducibility of the method.
TABLE 3 labeling repeatability determination results of para-hydroxyanisole in trimethylolpropane triacrylate
Data of liquid phase determination method of para hydroxy anisole in trimethylolpropane triacrylate is compared with spectrophotometry detection: weighing 5.0+/-0.5 g of trimethylolpropane triacrylate of 6 different batches, accurately reaching 0.0001g, dissolving with methanol, fixing the volume in a 100mL volumetric flask, and shaking uniformly. Under the selected liquid chromatography condition, the peak area of the p-hydroxyanisole is recorded by sample injection. And compared with the national standard method measurement results, the deviation values of the method are less than 5%, which shows that the method has good accuracy adaptability to the determination of the para-hydroxyanisole in the trimethylolpropane triacrylate, meets the measurement requirements, and has the specific results shown in Table 4.
Table 4 data comparison of quality high performance liquid phase and spectrophotometry of para-hydroxyanisole in trimethylolpropane triacrylate
Example 2
Determination of para-hydroxyanisole in tripropylene glycol diacrylate: weighing 5.0244g of tripropylene glycol diacrylate sample, dissolving with methanol, fixing the volume to a 100mL volumetric flask, and shaking uniformly; and (3) sampling under the selected high performance liquid chromatography condition, recording that the peak area of the para-hydroxyanisole is 76.1, substituting the peak area into a standard working curve to obtain the mass of the para-hydroxyanisole in the sample as 2552.4 mug, and dividing the mass by the weighing weight of the sample to obtain the concentration (mug/g) of the para-hydroxyanisole in the sample as 508.0.
Measurement of recovery rate of para-hydroxyanisole in tripropylene glycol diacrylate A5.0192 g tripropylene glycol diacrylate sample is weighed, 2mL of standard solution of para-hydroxyanisole with concentration of 513.2 mug/mL is removed, methanol is used for constant volume to a 100mL volumetric flask, and shaking is carried out uniformly. Under the selected high performance liquid chromatography condition, the peak area of the p-hydroxyanisole is 104.3 in the sample injection record. The measurement results of the recovery rate are shown in Table 5, and the result is 96.0%, which indicates that the method is accurate and reliable.
TABLE 5 determination of the labeling recovery of para-hydroxyanisole in tripropylene glycol diacrylate
Measuring the repeatability of the para-hydroxyanisole in tripropylene glycol diacrylate, namely weighing 5.0+/-0.5 g of the same sample, accurately reaching 0.0001g, dissolving the same sample in methanol, and uniformly shaking the same sample in a volumetric flask with a volume of 100 mL; sampling under the selected high performance liquid chromatography condition, and recording the peak area of the p-hydroxyanisole; the measurement results are shown in Table 6, and the RSD of the 6 times results is 1.85%, which shows that the method repeatability is good.
TABLE 6 determination of repeatability of para-hydroxyanisole in tripropylene glycol diacrylate
The liquid phase measurement of para-hydroxyanisole in tripropylene glycol diacrylate is compared with spectrophotometry data, 6 batches of tripropylene glycol diacrylate (5.0+ -0.5 g) are weighed, 0.0001g is accurately obtained, dissolved in methanol, and the volume is fixed in a 100mL volumetric flask, and the mixture is shaken uniformly. Under the selected high performance liquid chromatography condition, the peak area of the p-hydroxyanisole is recorded by sample injection. Compared with the national standard method, the deviation values of the method are less than 5%, which shows that the method has good accuracy adaptability to the determination of the para-hydroxyanisole in tripropylene glycol diacrylate, meets the measurement requirements, and has the specific results shown in Table 7.
TABLE 7 high Performance liquid phase and spectrophotometric data comparison of para-hydroxyanisole in tripropylene glycol diacrylate
Example 3
Determination of para-hydroxyanisole in 1, 6-hexanediol diacrylate: a5.1290 g sample of 1, 6-hexanediol diacrylate was weighed, dissolved in a small amount of methanol, and the volume was set to 100mL volumetric flask and shaken well. Under the selected high performance liquid chromatography condition, the peak area of the p-hydroxyanisole is 46.0, and the peak area is substituted into a standard working curve to obtain the mass of the p-hydroxyanisole in the sample which is 1503.73 mug, and the p-hydroxyanisole concentration (mug/g) in the sample is 293.2. Determination of recovery of para-hydroxyanisole in 1, 6-hexanediol diacrylate: 5.0064g of 1, 6-hexanediol diacrylate sample is weighed, 4mL of standard solution of p-hydroxyanisole with the concentration of 513.2 mug/mL is removed, methanol is used for constant volume to a 100mL volumetric flask, and shaking is carried out uniformly. Under the selected high performance liquid chromatography condition, the peak area of the p-hydroxyanisole is 109.5 in the sample injection record. The measurement results of the recovery rate are shown in Table 8, and the result is 107.8%, which indicates that the method is accurate and reliable.
TABLE 8 determination of the labeled recovery of para-hydroxyanisole in 1, 6-hexanediol diacrylate
Determination of the repeatability of para-hydroxyanisole in 1, 6-hexanediol diacrylate: the same sample was weighed 5.0.+ -. 0.5g (accurate to 0.0001 g), dissolved in methanol, and fixed to volume in a 100mL volumetric flask and shaken well. And (3) sampling under the selected high performance liquid chromatography condition, and recording the peak area of the p-hydroxyanisole. The measurement results are shown in Table 9. The RSD of the 6 results was 1.16%, indicating a better reproducibility of the method.
TABLE 9 determination of the repeatability of para-hydroxyanisole in 1, 6-hexanediol diacrylate
High performance liquid phase determination of para-hydroxyanisole in 1, 6-hexanediol diacrylate is compared with spectrophotometry data: weighing 5.0+/-0.5 g (accurate to 0.0001 g) of 1, 6-hexanediol diacrylate in 6 different batches, dissolving the 1, 6-hexanediol diacrylate in methanol, fixing the volume into a 100mL volumetric flask, and shaking the flask uniformly. Under the selected high performance liquid chromatography condition, the peak area of the p-hydroxyanisole is recorded by sample injection. Compared with the national standard method, the deviation values of the method are less than 5%, which shows that the method has good accuracy adaptability to the determination of the p-hydroxyanisole in the 1, 6-hexanediol diacrylate, and meets the measurement requirements, and the specific results are shown in Table 10.
Table 10 high performance liquid phase of para-hydroxyanisole in 1, 6-hexanediol diacrylate was compared with spectrophotometric data.
From the above three examples, it can be seen that the measurement method of the present application can measure p-hydroxyanisole in acrylic monomers, and the measurement method can be general.
The above disclosure is only a preferred embodiment of the present invention, and it is needless to say that the scope of the invention is not limited thereto, and therefore, the equivalent changes according to the claims of the present invention still fall within the scope of the present invention.
Claims (6)
1. The method for measuring the content of the p-hydroxyanisole in the acrylate product is characterized by comprising the following steps of:
s1, configuring the operation condition of a high performance liquid chromatograph;
s2, preparing a standard solution, namely dissolving 0.1283g of a para-hydroxyanisole standard substance with methanol, transferring the dissolved para-hydroxyanisole standard substance into a 250mL volumetric flask, and then fixing the volume to 250mL with methanol to prepare a standard solution with the para-hydroxyanisole concentration of 0.5132 mg/mL;
s3, drawing a standard working curve, namely respectively transferring p-hydroxyanisole standard solutions with different volumes, fixing the volumes to a volumetric flask with 100mL by using methanol to obtain p-hydroxyanisole standard solutions with different concentrations, placing the standard solutions with different concentrations into a region to be tested of a high performance liquid chromatograph under the configured high performance liquid chromatograph condition, measuring the high performance liquid chromatograph peak areas corresponding to the different concentrations of the standard solutions and the mass of the p-hydroxyanisole by using the high performance liquid chromatograph, and drawing the standard working curve by using the measured high performance liquid chromatograph peak areas and the measured mass of the p-hydroxyanisole to obtain a fitting equation of the correlation relationship and the correlation relationship between the two;
s4, measuring the para-hydroxyanisole of the sample to be measured, namely weighing a certain amount of the sample to be measured, fixing the volume of the sample to be measured to a volume bottle of 100mL by using methanol, placing the sample to be measured under the configured high performance liquid chromatography condition, measuring and recording the peak area of the para-hydroxyanisole, substituting the recorded peak area into a working curve, and calculating the mass of the para-hydroxyanisole in the sample to be measured by using a fitting equation;
s5, calculating the mass of the para-hydroxyanisole according to the sample weighing amount of the sample to be detected and the S4, and calculating the concentration of the para-hydroxyanisole in the sample to be detected.
2. The method for determining the content of para-hydroxyanisole in an acrylate product according to claim 1, wherein the operating conditions of the high performance liquid chromatograph in S1: the liquid chromatographic column is an EC-C184.6mm.250 mm,4 μm or C18 chromatographic column with equal division capacity, the mobile phase is acetonitrile and water in a ratio of 50:50, the sample injection amount is 5 mu L, the flow rate is 1.5mL/min, and the detector wavelength is 278nm.
3. The method for measuring the content of the para-hydroxyanisole in the acrylate product according to claim 1, wherein a fitting equation of the correlation between the peak area of the high performance liquid chromatography in the S3 and the mass of the para-hydroxyanisole is y= 34.841x-98.907, x represents the peak area of the para-hydroxyanisole recorded by the high performance liquid chromatography under the wavelength of 278nm, and y represents the mass of the para-hydroxyanisole in the standard solution.
4. The method for measuring the content of para-hydroxyanisole in an acrylate product according to claim 1, wherein the sample to be measured in S4 is an acrylic acid monomer, and the acrylic acid monomer is one of tripropylene glycol diacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, or 1, 6-propanediol diacrylate.
5. The method for measuring the content of the para-hydroxyanisole in the acrylate product according to claim 4, wherein the sample weighing amount of the acrylic acid monomer is 4.5 g-5.5 g.
6. The method for measuring the content of para-hydroxyanisole in an acrylate product according to claim 1, wherein the calculation mode in S5 is that the concentration of para-hydroxyanisole=the mass of para-hydroxyanisole ≡the sample weighing amount of the sample to be measured.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310456947.2A CN116359398A (en) | 2023-04-26 | 2023-04-26 | Method for measuring content of p-hydroxyanisole in acrylic ester product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310456947.2A CN116359398A (en) | 2023-04-26 | 2023-04-26 | Method for measuring content of p-hydroxyanisole in acrylic ester product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116359398A true CN116359398A (en) | 2023-06-30 |
Family
ID=86933812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310456947.2A Pending CN116359398A (en) | 2023-04-26 | 2023-04-26 | Method for measuring content of p-hydroxyanisole in acrylic ester product |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116359398A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102818874A (en) * | 2012-08-31 | 2012-12-12 | 国家烟草质量监督检验中心 | Detection method of determining 16 types of photoinitiators in paper printing and packaging material |
| RU2537125C1 (en) * | 2013-06-24 | 2014-12-27 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Курский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Method of determining substituted 2-methoxyhydroxybenzene in biological material |
| CN105954436A (en) * | 2016-07-21 | 2016-09-21 | 常州工学院 | Method for measuring transporting quantity of para-hydroxy benzaldehyde in food contact material |
| CN110501434A (en) * | 2019-08-12 | 2019-11-26 | 广州茂丰药业有限公司 | The detection method of residual solvent, monomer and decomposition of initiator product in a kind of tertiary-amino-containing methacrylate copolymer |
| CN115047089A (en) * | 2022-04-02 | 2022-09-13 | 辽宁省检验检测认证中心 | Method for detecting p-tert-butyl catechol in 2-vinylpyridine |
-
2023
- 2023-04-26 CN CN202310456947.2A patent/CN116359398A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102818874A (en) * | 2012-08-31 | 2012-12-12 | 国家烟草质量监督检验中心 | Detection method of determining 16 types of photoinitiators in paper printing and packaging material |
| RU2537125C1 (en) * | 2013-06-24 | 2014-12-27 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Курский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Method of determining substituted 2-methoxyhydroxybenzene in biological material |
| CN105954436A (en) * | 2016-07-21 | 2016-09-21 | 常州工学院 | Method for measuring transporting quantity of para-hydroxy benzaldehyde in food contact material |
| CN110501434A (en) * | 2019-08-12 | 2019-11-26 | 广州茂丰药业有限公司 | The detection method of residual solvent, monomer and decomposition of initiator product in a kind of tertiary-amino-containing methacrylate copolymer |
| CN115047089A (en) * | 2022-04-02 | 2022-09-13 | 辽宁省检验检测认证中心 | Method for detecting p-tert-butyl catechol in 2-vinylpyridine |
Non-Patent Citations (7)
| Title |
|---|
| WANG, YH等: "Determination of α-Arbutin, β-Arbutin, Kojic Acid, Nicotinamide, Hydroquinone, Resorcinol, 4-Methoxyphenol, 4-Ethoxyphenol and Vitamin C from Cosmetic Products Using LC-UV Method", PLANTA MEDICA, vol. 79, no. 10, pages 885, XP009190720 * |
| WANG, YH等: "Quantitative Determination of α-Arbutin, β-Arbutin, Kojic Acid, Nicotinamide, Hydroquinone, Resorcinol, 4-Methoxyphenol, 4-Ethoxyphenol, and Ascorbic Acid from Skin Whitening Products by HPLC-UV", JOURNAL OF AOAC INTERNATIONAL, vol. 98, no. 01, pages 5 - 12, XP009190714 * |
| 兰瑞桦等: "二甲基丙烯酸乙二醇酯中阻聚剂对苯二酚和对羟基苯甲醚含量测定", 中国化工贸易, no. 30, pages 149 * |
| 张博;赵沁;彭学成;张宁;苏旭;: "苯乙烯精馏阻聚剂DNBP的液相色谱分析", 齐鲁石油化工, no. 03, pages 245 - 248 * |
| 张爱平;王红卫;王华;侯晋;方禹之;: "进口甲基丙烯酸甲酯中阻聚剂快速测定方法及其作用机理研究", 分析科学学报, no. 01, pages 131 - 133 * |
| 李素真, 张博, 岳秀英: "高效液相色谱法分析甲基丙烯酰氧乙基三甲基氯化铵中的阻聚剂", 山东化工, no. 03, pages 34 - 35 * |
| 段志兴, 张自义, 赵和英: "液相色谱法测定MMA中的痕量阻聚剂2, 2, 6, 6-四甲基-4-羟基哌啶-1-氧自由基", 合成橡胶工业, no. 05, pages 334 - 336 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104007218B (en) | The assay method of bisphenol S migration amount in a kind of plastic food packaging materials | |
| CN109324004A (en) | The method of content of bisphenol A is remained in a kind of measurement polycarbonate | |
| CN104820041B (en) | A kind of analyze the method for multiple residual organic solvent in fluorene kind derivative | |
| CN114544803B (en) | HPLC analysis method for photoresist resin monomer acrylic ester compound | |
| CN116359398A (en) | Method for measuring content of p-hydroxyanisole in acrylic ester product | |
| CN114152691A (en) | Method for analyzing contents of cyclopentane and extractant by gas chromatography | |
| WO2024001060A1 (en) | Method for detecting benzenesulfonate impurities in cisatracurium besilate injection | |
| CN115047089A (en) | Method for detecting p-tert-butyl catechol in 2-vinylpyridine | |
| CN116626087A (en) | Method for quantitatively analyzing allyl sucrose ether content through nuclear magnetic resonance hydrogen spectrum | |
| CN102798688A (en) | Method for determining contents of methyl propionate, methyl methacrylate and propionic acid by gas chromatography internal standard method | |
| CN110243971A (en) | The method for detecting Cyclen and its derivative content using HPLC-ELSD | |
| CN109738555B (en) | Method for measuring content of orthoformate in crude orthoformate | |
| CN111044640B (en) | Method for determining content of gamma-aminobutyric acid in feed additive by GC (gas chromatography) method | |
| CN113030342A (en) | Method for detecting glutamic acid residue in gamma-aminobutyric acid | |
| CN111665312A (en) | Method for detecting content of N-methylimidazole in water phase system | |
| CN112557573B (en) | Method for measuring AEEA-AEEA content | |
| CN100535657C (en) | Method for measuring purity of 9-fluorenemethanol | |
| CN115453022B (en) | Method for rapidly judging formaldehyde content in white spirit | |
| CN109507327B (en) | Quantitative determination of TNT content by GC-AED independent calibration curve method (CIC method) | |
| CN109521120B (en) | Quantitative determination of DNTF content by GC-AED independent calibration curve method (CIC method) | |
| CN112305100B (en) | Method for detecting content of genotoxic impurity benzyl bromide in medicine | |
| CN102507785B (en) | Method for analyzing highly active thermal cross-linked acid polymer through gel permeation chromatograph | |
| CN117405789A (en) | Method for determining content of acrylamide impurities in polyacrylamide hydrochloride solution | |
| CN115078278A (en) | Detection method of L-fucose and application thereof | |
| CN117451907A (en) | Analysis method for detecting chlorovaleric acid and valerolactone impurities from acyl chloride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |