Analytical method of isopropylated phenylphosphate

Abstract

To provide an analytical method of isopropylated phenylphosphate with high reliability.SOLUTION: An analytical method of isopropylated phenylphosphate includes the steps of: thermally extracting a specimen; obtaining mass spectrum of one or more compounds contained in the specimen by analyzing the thermally extracted specimen by gas chromatograph mass analysis method; and determining whether or not fragment ion or / and parent ion that is specific mass-to-charge ratio (m / z) are contained in mass spectrum.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] An embodiment of the present invention relates to isopropylated phenyl phosphate. [Background technology]

[0002] In recent years, regulations on chemical substances have become stricter, and for companies that manufacture electrical and electronic equipment, it has become extremely important to manage the chemical substances contained in the constituent materials used in their products.

[0003] Aromatic phosphate esters, typified by isopropylated phenyl phosphate, are flame retardant, hydrophobic, plastic, insulating, and have lubricating properties against metals under high pressure. They are also inexpensive, and are therefore used as flame retardants, plasticizers for polyvinyl chloride, lubricating oil additives, etc.

[0004] Tris(isopropylphenyl)phosphate, also known as PIP(3:1), is a substance subject to regulation under the U.S. Toxic Substances Control Act, and analytical methods for propylated phenyl phosphate are being investigated. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 4090847 Summary of the Invention [Problem to be solved by the invention]

[0006] Embodiments of the present invention provide a reliable method for the analysis of isopropylated phenyl phosphate. [Means for solving the problem]

[0007] An embodiment of a method for analyzing isopropylated phenyl phosphate includes the steps of thermally extracting a sample, analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample, and determining whether the mass spectrogram contains fragment ions and / or parent ions having a particular mass-to-charge ratio (m / z). [Brief description of the drawings]

[0008] [Figure 1] 1 is a flowchart according to an embodiment. [Diagram 2] FIG. 1 is a conceptual diagram showing the configuration of an analysis device according to an embodiment. [Diagram 3] 1 is a chemical formula of an isopropylated phenyl phosphate of an embodiment. [Figure 4] 1 is a chemical formula of triphenyl phosphate according to an embodiment. [Diagram 5] 1 is a table of preliminary experiments of an embodiment. [Figure 6] 1 is a flowchart according to an embodiment. [Figure 7] Table of Examples. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] A preferred embodiment will be described in detail below with reference to the drawings. In the embodiment, unless otherwise specified, the conditions are those when carried out at 25°C and atmospheric pressure (100 [kPa]). In the formula, "X" is a multiplication symbol. In the formula, " / " is a division symbol.

[0010] The compounds in the present specification include isomers.

[0011] (First embodiment) The first embodiment relates to a method for analyzing isopropylated phenyl phosphate, and includes the steps of: thermally extracting a sample (S01); analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample (S02); and determining whether or not the mass spectrogram contains fragment ions (product ions) and / or parent ions (precursor ions) having a specific mass-to-charge ratio (m / z), as shown in the flow chart of the embodiment in Fig. 1.

[0012] A specific first embodiment of a method for analyzing isopropylated phenyl phosphate includes the steps of: thermally extracting a sample (S01); analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample (S02); and determining whether the mass spectrogram contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, 277, 293, 335, 353, 377, and 452 (S03).

[0013] A specific first embodiment of an analytical method for isopropylated phenyl phosphate includes a step (S01) of thermally extracting a sample at a thermal extraction temperature of 400°C or more and 700°C or less, a step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample, and a step (S03) of determining whether the mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 335.

[0014] A specific first embodiment of a method for analyzing isopropylated phenyl phosphate includes a step (S01) of thermally extracting a sample, a step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample, and a step (S03) of determining whether the mass spectrogram contains one or more fragment ions having mass-to-charge ratios (m / z) of 118, 251, and 335.

[0015] A specific first embodiment of a method for analyzing isopropylated phenyl phosphate includes a step (S01) of thermally extracting a sample, a step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample, and a step (S03) of determining whether the mass spectrogram contains fragment ions (first group) having a mass-to-charge ratio (m / z) of 118 or / and 251 and further contains fragment ions (second group) having a mass-to-charge ratio (m / z) of 145 or / and 160.

[0016] A specific first embodiment of a method for analyzing isopropylated phenyl phosphate includes a step (S01) of thermally extracting a sample, a step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample, and a step (S03) of determining whether the mass spectrogram contains fragment ions having a mass-to-charge ratio (m / z) of 145 and / or 160.

[0017] A specific first embodiment of a method for analyzing isopropylated phenyl phosphate includes a step (S01) of thermally extracting a sample, a step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample, and a step (S03) of determining whether the mass spectrogram contains two or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, and 335.

[0018] A schematic diagram of the configuration of an analytical device used in the analysis of the first embodiment is shown in Fig. 2. The analytical device 100 in Fig. 2 includes a pyrolysis device (pyrolyzer) 10, a first interface 20, a gas chromatograph 30, a second interface 40, a mass spectrometer 50, and a control device 60. The schematic diagram of the configuration of the analytical device 100 in Fig. 2 is an example of a configuration example of a pyrolysis gas chromatograph mass spectrometer (Py-GC / MS).

[0019] The pyrolysis apparatus 10 has a heating furnace 11 for heating a sample. In the pyrolysis apparatus 10, the sample is thermally extracted to generate gas. The heating furnace 11 has a heater 12, and the temperature inside the heating furnace 11 is adjusted by the heater 12. It is preferable that a carrier gas is introduced into the heating furnace 11. The carrier gas is, for example, helium and nitrogen. The step (S01) of thermally extracting the sample is performed in the pyrolysis apparatus 10.

[0020] The gas generated by decomposing the sample in the pyrolysis device 10 passes through the first interface 20 and is introduced into the gas chromatograph 30 .

[0021] The gas chromatograph 30 has an injection port 31, a capillary column 32, and a capillary heater 33. The generated gas is separated by the gas chromatograph 30. The generated gas is injected into the injection port 31 and introduced into the capillary column 32. The temperature of the capillary column 32 is adjusted by the capillary heater 33.

[0022] The separated gases are introduced into a mass spectrometer 50 through a second interface 40 .

[0023] Mass spectrometer 50 has an ionization section 51, a mass separation section 52, and a detector 53. Compounds contained in the separated gas are ionized in ionization section 51. The ionized compounds are separated according to their mass-to-charge ratio in mass separation section 52, and a mass spectrogram is created for each compound in detector 53. A total ion chromatogram (TIC) is obtained by adding up all the mass-to-charge ratios of the obtained mass spectrograms. A step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain mass spectrograms of one or more compounds contained in the sample is performed in mass spectrometer 50.

[0024] The control device 60 is connected to the pyrolysis device 10, the gas chromatograph 30, the mass spectrometer 50, etc. via wiring (not shown) and controls these devices. The control device 60 controls the conditions for carrying out the analysis method of the first embodiment. The control device 60 is, for example, a computer. The step (S03) of determining whether or not the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z) is performed by the control device 60.

[0025] The sample is preferably a substance containing a resin or a lubricant. Isopropylated phenyl phosphate contained in the sample is thermally extracted using a pyrolysis device 10. The sample is decomposed in a step (S01) of thermally extracting the sample and used for analysis. When the sample is heated, a gas containing a compound to be analyzed is generated. In an embodiment, the compound contained in the generated gas is qualitatively analyzed to determine whether the sample contains isopropylated phenyl phosphate.

[0026] In the analytical method of the embodiment, isopropylated phenyl phosphates other than tris(isopropylphenyl) phosphate can be analyzed.

[0027] Figure 3 shows the chemical formula of isopropylated phenyl phosphate. Figure 4 shows the chemical formula of triphenyl phosphate. Isopropylated phenyl phosphate has three phenyl groups (a first phenyl group, a second phenyl group, and a third phenyl group) and the phenyl groups contain a total of 1 to 6 isopropyl groups. Each phenyl group contains 0 to 2 isopropyl groups. Gas chromatography distinguishes between isomers, but the chemical formula in Figure 3 and others do not distinguish between isomers.

[0028] The numerical values ​​such as IPPP 3(111) shown in FIG. 3 and FIG. 4 are, from the left, the total number of isopropyl groups, the number of isopropyl groups contained in the first phenyl group, the number of isopropyl groups contained in the second phenyl group, and the number of isopropyl groups contained in the third phenyl group.

[0029] The isopropylated phenyl phosphate shown in formula (1) in Figure 3 is represented in the figure as IPPP 1(100). The isopropylated phenyl phosphate of formula (1) contains one isopropyl group on the first phenyl group, the second phenyl group is unsubstituted, and the third phenyl group is unsubstituted.

[0030] The isopropylated phenyl phosphate shown in chemical formula (2) in Figure 3 is represented as IPPP 2(110) in the figure. The isopropylated phenyl phosphate of chemical formula (2) contains one isopropyl group in the first phenyl group, one isopropyl group in the second phenyl group, and the third phenyl group is unsubstituted.

[0031] The isopropylated phenyl phosphate shown in chemical formula (3) in Figure 3 is represented in the figure as IPPP 2(200). The isopropylated phenyl phosphate of chemical formula (3) contains two isopropyl groups in the first phenyl group, the second phenyl group is unsubstituted, and the third phenyl group is unsubstituted.

[0032] The isopropylated phenyl phosphate shown in chemical formula (4) in Figure 3 is represented as IPPP 3 (111) in the figure. The isopropylated phenyl phosphate of chemical formula (4) contains one isopropyl group in the first phenyl group, one isopropyl group in the second phenyl group, and one isopropyl group in the third phenyl group. The isopropylated phenyl phosphate shown in chemical formula (4) in Figure 3 is tris(isopropylphenyl) phosphate.

[0033] The isopropylated phenyl phosphate shown in chemical formula (5) in Figure 3 is represented in the figure as IPPP 3 (210). The isopropylated phenyl phosphate of chemical formula (5) contains two isopropyl groups in the first phenyl group, one isopropyl group in the second phenyl group, and the third phenyl group is unsubstituted.

[0034] The isopropylated phenyl phosphate shown in formula (6) in Figure 3 is represented as TPP 4 (220) in the figure. The isopropylated phenyl phosphate of formula (6) contains two isopropyl groups in the first phenyl group, two isopropyl groups in the second phenyl group, and the third phenyl group is unsubstituted.

[0035] The isopropylated phenyl phosphate shown in chemical formula (7) in Figure 3 is represented as IPPP 4 (211) in the figure. The isopropylated phenyl phosphate of chemical formula (7) contains two isopropyl groups in the first phenyl group, one isopropyl group in the second phenyl group, and one isopropyl group in the third phenyl group.

[0036] The isopropylated phenyl phosphate shown in chemical formula (8) in Figure 3 is represented as IPPP 5 (221) in the figure. The isopropylated phenyl phosphate of chemical formula (8) contains two isopropyl groups in the first phenyl group, two isopropyl groups in the second phenyl group, and one isopropyl group in the third phenyl group.

[0037] The isopropylated phenyl phosphate shown in chemical formula (9) in Figure 3 is represented as IPPP 6 (222) in the figure. The isopropylated phenyl phosphate of chemical formula (9) contains two isopropyl groups in the first phenyl group, two isopropyl groups in the second phenyl group, and two isopropyl groups in the third phenyl group.

[0038] Triphenyl phosphate shown in chemical formula (10) in Figure 4 is represented as TPP 0 (000) in the figure. It has three phenyl groups (the first phenyl group, the second phenyl group, and the third phenyl group), and all of the phenyl groups are unsubstituted.

[0039] In the step (S01) of thermally extracting the sample, the temperature at which the sample is thermally extracted (temperature inside the heating furnace 11) is preferably 400°C or more and 700°C or less. If the sample is thermally extracted at a temperature of 300°C, which is a common temperature, it is sufficient for the analysis of tris(isopropylphenyl)phosphate present in the GC / MS library, but when an analysis is performed including isopropylated phenyl phosphate not present in other GC / MS libraries, it is difficult to analyze some isopropylated phenyl phosphates with large molecular weights because the temperature is not high enough. In addition, if the thermal extraction temperature exceeds 700°C, isopropylated phenyl phosphate is easily decomposed. Therefore, the thermal extraction temperature of the sample is preferably 400°C or more and 700°C or less, and more preferably 450°C or more and 650°C or less.

[0040] The temperature of the first interface 20 through which the gas generated in the step (S01) of thermally extracting the sample passes is typically 300° C., but is not limited thereto.

[0041] In the step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample, the generated gas is separated into components. The generated gas that has passed through the first interface 20 is separated in the capillary column 42 of the gas chromatograph 30.

[0042] The temperature of the inlet 31 is typically 300° C., but is not limited thereto.

[0043] For example, a capillary column 32 using dimethylpolysiloxane or diphenyldimethylpolysiloxane as the stationary phase is preferable. When the inner diameter of the capillary column 32 is, for example, 0.25 [mm], the split ratio is preferably, for example, 50:1 to 100:1.

[0044] It is preferable to use a temperature increase method for adjusting the temperature of the capillary column 32. For example, after flowing a carrier gas such as He at room temperature, for example, a gas generated at 40°C is injected, and the temperature is increased to 300°C or more and 350°C or less at 10°C / min after 2 minutes.

[0045] The gas separated into each component is ionized, for example, by electron impact (EI) method. Parent ions ionized from compounds contained in each component and fragment ions generated by decomposition (fragmentation) of the compounds contained in each component during ionization are separated according to their mass-to-charge ratio in mass separation section 52. The separated ions are detected by detector 53 to obtain a mass spectrogram of the compound. In detector 53, the mass range m / z is preferably 10 or more and 600 or less.

[0046] From the obtained mass spectrogram, it is determined whether or not the sample contains isopropylated phenyl phosphate. The determination may be made automatically by the control device 60 or by an analyst.

[0047] Here, a preliminary experiment will be described to explain whether a sample contains isopropylated phenyl phosphate. The conditions of the preliminary experiment are as follows:

[0048] (Condition 1) Pyrolyzer heat extraction temperature: 600 [℃] Pyrolyzer interface temperature: Auto Gas chromatograph column: 5% diphenyl dimethyl polysiloxane, length 30[m], internal diameter 0.25[mm], film thickness 0.05[μm] Gas chromatograph injection temperature: 300[℃] Gas chromatograph column oven temperature: 40°C (hold for 2 minutes), increase at 10°C / min, up to 320°C Gas chromatograph injection mode: Split 1 / 50 Gas chromatograph carrier gas: He 1 [mL / min], constant flow Mass spectrometer ionization method: EI (electron ionization impact method) 70 [eV] Mass spectrometer ion source temperature: 230[℃] Mass spectrometer scan range: m / z 10-600

[0049] When samples containing various isopropylated phenyl phosphates were measured using the above method, the results shown in the preliminary experiment table in Figure 5 were obtained. The table in Figure 5 shows the retention time, compound, fragment ion, and parent ion. The results shown in the table in Figure 5 also provided information on the mass-to-charge ratio (m / z) of isopropylated phenyl phosphates that were not present in the GC / MS library.

[0050] From these results, it is possible to make a judgment regarding isopropylated phenyl phosphates other than tris(isopropylphenyl) phosphate, taking into consideration the number of phenyl groups into which isopropyl has been introduced.

[0051] When using a GC / MS library as a standard, it is not possible to judge compounds that are not in the library, but the method of the embodiment allows judgment to be made under analytical conditions freely selected by the analyst without relying on a library.

[0052] When only the parent ion is considered, a sample that contains a compound of the same molecular weight but does not contain isopropylated phenyl phosphate may be determined to contain isopropylated phenyl phosphate.

[0053] Regarding whether a sample contains a substance subject to regulation (2021) under Section 6(h) of the Toxic Substances Control Act (TSCA) (isopropylated phenyl phosphate, in which one or more isopropyl groups have been introduced into all three phenyl groups, commonly known as PIP(3:1)), when focusing on the parent ion, it is not possible to determine whether isopropylated phenyl phosphate is PIP(3:1) if the total number of isopropyl groups contained in the isopropylated phenyl phosphate is up to four.

[0054] Therefore, a highly reliable analysis can be performed by first making a judgment based on the fragment ions and then supplementarily making a judgment based on the parent ions.

[0055] In an embodiment, in the step (S03) of determining whether or not a mass spectrogram contains a fragment ion and / or a parent ion having a specific mass-to-charge ratio (m / z), whether or not isopropylated phenyl phosphate is contained in a sample is determined by the following methods A to F. It is also preferable to further determine whether or not the mass spectrogram contains a mass-to-charge ratio (m / z) corresponding to a parent ion of isopropylated phenyl phosphate.

[0056] (Method A) Regarding the step (S03) of determining whether the mass spectrogram contains fragment ions and / or parent ions with a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains one or more fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 145, 160, 251, 277, 293, 335, 353, 377, and 452.

[0057] The mass spectrograms of the isopropylated phenyl phosphates of formulas (1) to (9) in FIG. 3 contain one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, 277, 293, 335, 353, 377, and 452.

[0058] By using method A, it is possible to determine whether a sample contains isopropylated phenyl phosphate in which an isopropyl group has been introduced into one or more of the phenyl groups. In the determination by method A, a total ion chromatogram is not used. In the determination by method A, the determination can be made without evaluating the similarity between each mass spectrogram and the mass spectrogram of an isopropylated phenyl phosphate present in the library, and thus method A is useful as a simple screening method.

[0059] When using method A, the reliability of the analysis can be improved by setting the heat extraction temperature to 400°C or higher and 700°C or lower, or 450°C or higher and 650°C or lower.

[0060] When the determination is made by Method A, it is preferable to determine that the sample contains isopropylated phenyl phosphate from the mass spectrum obtained by Method A for two or more compounds. It is preferable to determine that the sample contains two or more isopropylated phenyl phosphates, in which isomers are regarded as separate compounds, by Method A. It is also preferable to determine that the sample contains isomers of isopropylated phenyl phosphate by Method A. By making a determination based on a plurality of compounds by these methods, the reliability of the analysis is improved.

[0061] When determining by method A, the reliability of the analysis can be improved by further determining whether a mass spectrogram containing one or more fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 145, 160, 251, 277, 293, 335, 353, 377, and 452 also contains one or more parent ions selected from the group consisting of mass-to-charge ratios (m / z) of 368, 410, 452, 494, 536, and 578.

[0062] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 118, and the mass-to-charge ratio (m / z) of a parent ion in the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 118 is 368, 410, 452, 494, 536, or 578, it can be determined that the sample contains isopropylated phenyl phosphate.

[0063] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 145, and the mass-to-charge ratio (m / z) of the parent ion in the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 145 is (m / z) 410, 452, 494, or 536, it can be determined that the sample contains isopropylated phenyl phosphate.

[0064] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 160, and the mass-to-charge ratio (m / z) of a parent ion in the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 160 is (m / z) 410, 452, 494, or 536, it can be determined that the sample contains isopropylated phenyl phosphate.

[0065] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 251, and the mass-to-charge ratio (m / z) of the parent ion in the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 251 is 368, 410, 452, 494, 536, or 578, it can be determined that the sample contains isopropylated phenyl phosphate.

[0066] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 277, and the parent ion of the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 277 has a mass-to-charge ratio (m / z) of 452, it can be determined that the sample contains isopropylated phenyl phosphate.

[0067] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 293, and the parent ion of the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 293 has a mass-to-charge ratio (m / z) of 452, it can be determined that the sample contains isopropylated phenyl phosphate.

[0068] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 335, and the mass-to-charge ratio (m / z) of the parent ion in the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 335 is (m / z) 410, 452, 494, 536 or 578, it can be determined that the sample contains isopropylated phenyl phosphate.

[0069] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 353, and the parent ion of the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 353 has a mass-to-charge ratio (m / z) of 410, it can be determined that the sample contains isopropylated phenyl phosphate.

[0070] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 377, and the parent ion of the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 377 has a mass-to-charge ratio (m / z) of 494, it can be determined that the sample contains isopropylated phenyl phosphate.

[0071] When a mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 452, and the parent ion of the mass spectrogram containing the fragment ion having a mass-to-charge ratio (m / z) of 452 has a mass-to-charge ratio (m / z) of 536, it can be determined that the sample contains isopropylated phenyl phosphate.

[0072] (Method B) Regarding the step (S03) of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 335.

[0073] By using method B, it is possible to determine whether a sample contains isopropylated phenyl phosphate, which has one or more isopropyl groups introduced into all three phenyl groups. It is possible to determine whether a sample contains a substance (isopropylated phenyl phosphate, which has one or more isopropyl groups introduced into all three phenyl groups, so-called PIP(3:1)) that is subject to regulations (2021) under Section 6(h) of the Toxic Substances Control Act (TSCA).

[0074] By using method B, it is possible to determine whether a sample contains isopropylated phenyl phosphate in which one or more isopropyl groups have been introduced into all three phenyl groups, without focusing on the mass-to-charge ratios of many fragment ions.

[0075] By using method B, it is possible to correctly determine whether a sample contains isopropylated phenyl phosphate, in which one or more isopropyl groups have been introduced into all three phenyl groups other than tris(isopropylphenyl) phosphate present in the GC / MS library.

[0076] Total ion chromatograms are not used in the judgment of Method B. The judgment of Method B can be performed without evaluating the similarity between each mass spectrogram and the mass spectrogram of isopropylated phenyl phosphate present in the library, and Method B is useful as a simple screening method.

[0077] When using method B, the reliability of the analysis can be improved by setting the heat extraction temperature to 400°C or higher and 700°C or lower, or 450°C or higher and 650°C or lower.

[0078] When determining using Method B, the reliability of the analysis can be improved by further determining whether a mass spectrogram containing a fragment ion with a mass-to-charge ratio (m / z) of 335 contains one or more parent ions selected from the group consisting of 452, 494, 536, and 578.

[0079] When the determination is made by method B, it is preferable to determine that the sample contains isopropylated phenyl phosphate from the mass spectrum obtained by method B for two or more compounds. It is preferable to determine that the sample contains two or more isopropylated phenyl phosphates, with isomers considered as separate compounds, by method B. It is also preferable to determine that the sample contains isomers of isopropylated phenyl phosphate by method B. By making a determination based on a plurality of compounds by these methods, the reliability of the analysis is improved.

[0080] (Method C) Regarding the step (S03) of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 251, and 335.

[0081] In method C, it is preferred to determine whether the mass spectrogram contains two or more fragment ions having mass to charge ratios (m / z) selected from the group consisting of 118, 251, and 335. It is more preferred to determine whether the mass spectrogram contains all fragment ions having mass to charge ratios (m / z) selected from the group consisting of 118, 251, and 335.

[0082] In method C, the reliability of the analysis is improved by determining whether the mass spectrogram contains two or more or all of the fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 251, and 335. For example, in the case of a compound with a duration of 27.4 [min] or a compound with a duration of 29.2 [min] in the table of FIG. 5, all of the fragment ions with mass-to-charge ratios (m / z) of 118, 251, and 335 are contained in the mass spectrogram.

[0083] In the judgment by method C, a total ion chromatogram is not used. In the judgment by method C, it is possible to judge whether or not isopropylated phenyl phosphate is contained in a sample, regardless of the presence or absence of tris(isopropylphenyl) phosphate, which is a representative of isopropylated phenyl phosphate. In the judgment by method C, it is possible to judge without evaluating the similarity between each mass spectrogram and the mass spectrogram of isopropylated phenyl phosphate present in the library, and thus method C is useful as a simple screening method.

[0084] When using method C, the reliability of the analysis can be improved by setting the heat extraction temperature to 400°C or higher and 700°C or lower, or 450°C or higher and 650°C or lower.

[0085] When determining by method C, the reliability of the analysis can be improved by further determining whether a mass spectrogram containing one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 251, and 335 also contains one or more parent ions having mass-to-charge ratios (m / z) selected from the group consisting of 368, 410, 452, 494, 536, and 578.

[0086] When the determination is made by method C, it is preferable to determine that the sample contains isopropylated phenyl phosphate from the mass spectrum obtained by method C for two or more compounds. It is preferable to determine that the sample contains two or more isopropylated phenyl phosphates, with isomers considered as separate compounds, by method C. It is also preferable to determine that the sample contains isomers of isopropylated phenyl phosphate by method C. By making a determination based on a plurality of compounds by these methods, the reliability of the analysis is improved.

[0087] (Method D) Regarding the step (S03) of determining whether the mass spectrogram contains fragment ions and / or parent ions with a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains fragment ions (first group) with mass-to-charge ratios (m / z) of 118 or / and 251, and further whether the mass spectrogram contains fragment ions (second group) with mass-to-charge ratios (m / z) of 145 or / and 160.

[0088] For the most part, compounds whose mass spectrograms contain fragment ions with a mass-to-charge ratio (m / z) of 118 have in common with compounds whose mass spectrograms contain fragment ions with a mass-to-charge ratio (m / z) of 251. Also, compounds whose mass spectrograms contain fragment ions with a mass-to-charge ratio (m / z) of 145 have in common with compounds whose mass spectrograms contain fragment ions with a mass-to-charge ratio (m / z) of 160. Therefore, when one or both of these two groups are present, it is determined that the sample contains isopropylated phenyl phosphate.

[0089] With respect to the step (S03) of determining whether the mass spectrogram contains fragment ions and / or parent ions with a particular mass-to-charge ratio (m / z), it is preferred to determine whether the mass spectrogram contains fragment ions (first group) with mass-to-charge ratios (m / z) of 118 and 251, and further whether the mass spectrogram contains fragment ions (second group) with mass-to-charge ratios (m / z) of 145 and 160.

[0090] By using method D, it is possible to determine whether many types of isopropylated phenyl phosphate are contained in a sample even if the number of fragment ions of interest is small. In the determination by method D, a total ion chromatogram is not used. In the determination by method D, the determination can be made without evaluating the similarity between each mass spectrogram and the mass spectrogram of the isopropylated phenyl phosphate present in the library, and method D is useful as a simple screening method.

[0091] When using method D, the reliability of the analysis can be improved by setting the heat extraction temperature to 400°C or higher and 700°C or lower, or 450°C or higher and 650°C or lower.

[0092] When determining using method D, the reliability of the analysis can be improved by further determining whether a mass spectrogram containing fragment ions (first group) with mass-to-charge ratios (m / z) of 118 and / or 251 and further containing fragment ions (second group) with mass-to-charge ratios (m / z) of 145 and / or 160 contains one or more parent ions selected from the group consisting of mass-to-charge ratios (m / z) of 368, 410, 452, 494, 536 and 578.

[0093] When the determination is made by Method D, it is preferable to determine that the sample contains isopropylated phenyl phosphate from the mass spectrum obtained by Method D for two or more compounds. It is preferable to determine that the sample contains two or more isopropylated phenyl phosphates, in which isomers are regarded as separate compounds, by Method D. It is also preferable to determine that the sample contains isomers of isopropylated phenyl phosphate by Method D. By making a determination based on a plurality of compounds by these methods, the reliability of the analysis is improved.

[0094] (Method E) Regarding the step (S03) of determining whether the mass spectrogram contains fragment ions and / or parent ions with a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains fragment ions with a mass-to-charge ratio (m / z) of 145 and / or 160.

[0095] In the determination of method E, it is preferable to determine whether fragment ions having mass-to-charge ratios (m / z) of 145 and 160 are contained in the mass spectrogram.

[0096] In the judgment by method E, a total ion chromatogram is not used. In the judgment by method E, it is possible to judge whether or not isopropylated phenyl phosphate is contained in a sample, regardless of the presence or absence of tris(isopropylphenyl) phosphate, which is a representative of isopropylated phenyl phosphate. In the judgment by method E, it is possible to judge without evaluating the similarity between each mass spectrogram and the mass spectrogram of isopropylated phenyl phosphate present in the library, and thus method E is useful as a simple screening method.

[0097] When using method E, the reliability of the analysis can be improved by setting the heat extraction temperature to 400°C or higher and 700°C or lower, or 450°C or higher and 650°C or lower.

[0098] When determining using Method E, the reliability of the analysis can be improved by further determining whether a mass spectrogram containing fragment ions with mass-to-charge ratios (m / z) of 145 and / or 160 also contains one or more parent ions selected from the group consisting of mass-to-charge ratios (m / z) of 410, 452, 494 and 536.

[0099] When the determination is made by Method E, it is preferable to determine that the sample contains isopropylated phenyl phosphate from the mass spectrum obtained by Method E for two or more compounds. It is preferable to determine that the sample contains two or more isopropylated phenyl phosphates, in which isomers are regarded as separate compounds, by Method E. It is also preferable to determine that the sample contains an isomer of isopropylated phenyl phosphate by Method E. By making a determination based on a plurality of compounds by these methods, the reliability of the analysis is improved.

[0100] (Method F) Regarding the step (S03) of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains two or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, and 335.

[0101] In the judgment by method F, a total ion chromatogram is not used. In the judgment by method F, it is possible to judge whether or not isopropylated phenyl phosphate is contained in a sample, regardless of the presence or absence of tris(isopropylphenyl) phosphate, which is a representative of isopropylated phenyl phosphate. In the judgment by method F, it is possible to judge without evaluating the similarity between each mass spectrogram and the mass spectrogram of isopropylated phenyl phosphate present in the library, and thus method F is useful as a simple screening method.

[0102] When using Method F, the reliability of the analysis can be improved by setting the heat extraction temperature to 400°C or higher and 700°C or lower, or 450°C or higher and 650°C or lower.

[0103] When determining using Method F, the reliability of the analysis can be improved by further determining whether a mass spectrogram containing two or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, and 335 also contains one or more parent ions having mass-to-charge ratios (m / z) selected from the group consisting of 368, 410, 452, 494, 536, and 578.

[0104] When the determination is made by Method F, it is preferable to determine that the sample contains isopropylated phenyl phosphate from the mass spectrum obtained by Method F for two or more compounds. It is preferable to determine that the sample contains two or more isopropylated phenyl phosphates, in which isomers are regarded as separate compounds, by Method F. It is also preferable to determine that the sample contains an isomer of isopropylated phenyl phosphate by Method F. By making a determination based on a plurality of compounds by these methods, the reliability of the analysis is improved.

[0105] Second embodiment The second embodiment relates to a method for analyzing isopropylated phenyl phosphate, and includes the steps of: thermally extracting a sample (S01); analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample (S02); and determining the concentration of isopropylated phenyl phosphate contained in the sample from the peak area of ​​a parent ion in the mass spectrogram (S04), as shown in the flow chart relating to the embodiment in Fig. 6.

[0106] The analysis method of the first embodiment and the analysis method of the second embodiment have some in common, and a description of the contents common to the first embodiment and the second embodiment will be omitted.

[0107] The step (S01) of thermally extracting a sample and the step (S02) of analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample are common to the analysis method of the first embodiment and the analysis method of the second embodiment.

[0108] The analysis device used in the analysis of the second embodiment is the same as the analysis device 100 used in the analysis of the first embodiment.

[0109] The analysis method of the second embodiment differs from the first embodiment in that it includes a step (S04) of determining the concentration of isopropylated phenyl phosphate contained in the sample from the peak area of ​​the parent ion in the mass spectrogram. The second embodiment may include a step (S03) of determining whether or not the mass spectrogram of the first embodiment includes a fragment ion and / or a parent ion having a specific mass-to-charge ratio (m / z).

[0110] In the step (S04) of determining the concentration of isopropylated phenyl phosphate contained in the sample from the peak area of ​​the parent ion in the mass spectrogram, the concentration is determined from the peak area of ​​the parent ion, not from the total ion chromatogram. The peaks in the total ion chromatogram include all peaks of the parent ion and fragment ions. In gas chromatography, quantitative evaluation is usually performed based on the total ion chromatogram, but it was found that there are cases where a large error occurs when quantifying isopropylated phenyl phosphate based on the total ion chromatogram.

[0111] Therefore, in the embodiment, the amount of isopropylated phenyl phosphate is quantified from the peak area of ​​the parent ion, rather than from the total ion chromatogram.

[0112] The step (S04) of determining the concentration of isopropylated phenyl phosphate contained in the sample from the peak area of ​​the parent ion in the mass spectrogram specifically determines the concentration of isopropylated phenyl phosphate contained in the sample from the ratio of the peak area of ​​the parent ion of isopropylated phenyl phosphate in the mass spectrogram of the sample to the peak area of ​​the parent ion of tris(isopropylphenyl) phosphate in the mass spectrum obtained by analyzing a standard sample containing tris(isopropylphenyl) phosphate by gas chromatography mass spectrometry.

[0113] The concentration of isopropylated phenyl phosphate in a sample can be calculated, for example, from the following formula. [Concentration of isopropylated phenyl phosphate in the sample] = [peak area of ​​parent ion of isopropylated phenyl phosphate in the mass spectrogram of the sample] / [peak area of ​​parent ion of tris(isopropylphenyl) phosphate in the mass spectrum of the standard sample] x [mass of the sample used in the analysis] / [mass of the standard sample used in the analysis] x [concentration of tris(isopropylphenyl) phosphate in the standard sample]

[0114] The concentration of isopropylated phenyl phosphate in a sample can be determined, for example, using the equation for a calibration curve prepared from the peak area of ​​the parent ion of tris(isopropylphenyl) phosphate in the mass spectrum of a standard sample.

[0115] The preferred conditions for the pyrolysis-gas chromatography-mass spectrometry of the second embodiment are the same as the preferred conditions for the pyrolysis-gas chromatography-mass spectrometry of the first embodiment.

[0116] Tris(isopropylphenyl)phosphate is available as a reagent, so a standard sample containing tris(isopropylphenyl)phosphate adjusted to a specific concentration is analyzed by thermal extraction gas chromatography mass spectrometry to obtain a mass spectrogram of tris(isopropylphenyl)phosphate. The mass-to-charge ratio (m / z) of the parent ion of tris(isopropylphenyl)phosphate is 452. The peak area of ​​the parent ion in the obtained mass spectrogram is then calculated.

[0117] When a standard sample is analyzed and multiple mass spectrograms with a parent ion mass-to-charge ratio (m / z) of 452 are obtained, it is preferable to treat the sum of the parent ion peak areas of multiple mass spectrograms with a parent ion mass-to-charge ratio (m / z) of 452 (for example, the sum of the parent ion peak area of ​​the mass spectrogram with a duration of 27.4 [min] and the parent ion peak area of ​​the mass spectrogram with a duration of 28.3 [min] in Figure 5) as the peak area of ​​the parent ion of tris(isopropylphenyl) phosphate of the standard sample.

[0118] When multiple mass spectrograms of isopropylated phenyl phosphate are obtained, the sum of the peak areas of the parent ions of isopropylated phenyl phosphate in multiple (part or all) mass spectrograms is treated as the peak area of ​​the parent ion of isopropylated phenyl phosphate in the mass spectrogram of the sample.

[0119] Next, the sample is analyzed by gas chromatography mass spectrometry under the same or substantially the same conditions as those of the standard sample to obtain a mass spectrogram. From the obtained mass spectrograms, the following selected mass spectrograms are selected. From the selected mass spectrograms, the peak areas of parent ions in all of one or more mass spectrograms are determined, and the isopropylated phenyl phosphate contained in the sample is quantitatively analyzed from the peak areas of the determined parent ions.

[0120] The selected mass spectrograms are one or more mass spectrograms or one or more mass spectrograms of parent ions having a mass-to-charge ratio (m / z) of 368, 410, 452, 494, 536 or 578 selected in the step (S03) of determining whether the mass spectrogram of the first embodiment contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z).

[0121] The selected mass spectrograms are preferably further selected based on one or more of the following criteria:

[0122] (Standard A) The selected mass spectrograms further selected in criterion A preferably include all applicable mass spectrograms.

[0123] (Standard B) The selected mass spectrograms further selected by criterion B preferably include, among all the corresponding mass spectrograms, mass spectrograms of compounds whose parent ion mass-to-charge ratio is 410, 452, 494, 536 or 578 and whose phenyl group of isopropylated phenyl phosphate contains a total of 1 to 6 isopropyl groups.

[0124] (Criteria C) The selected mass spectrograms further selected by criterion C preferably include, among all the corresponding mass spectrograms, mass spectrograms of compounds in which the mass-to-charge ratio of the parent ion is 410, 452, 494, 536 or 578 and one or more isopropyl groups are introduced into each of the three phenyl groups of isopropylated phenyl phosphate.

[0125] (Criteria D) The selected mass spectrograms further selected by criterion D preferably include all mass spectrograms of compounds whose ion mass-to-charge ratio (m / z) is 410, 452, 494, 536 or 578 and which contain a total of 1 to 6 isopropyl groups in the phenyl group of isopropylated phenyl phosphate.

[0126] (Criterion E) The selected mass spectrograms further selected by criterion E preferably include mass spectrograms of compounds having an ion mass-to-charge ratio (m / z) of 452, 494, 536 or 578 and containing a total of 2 to 6 isopropyl groups on the phenyl group of isopropylated phenyl phosphate.

[0127] (Criteria F) The selected mass spectrograms further selected by criterion F preferably include mass spectrograms of compounds having an ion mass-to-charge ratio (m / z) of 452, 494, 536 or 578, and in which one or more but not more than two isopropyl groups have been introduced into each of the three phenyl groups of an isopropylated phenyl phosphate.

[0128] When quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 368, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 368 preferably contains fragment ions with mass-to-charge ratios (m / z) of 118 and / or 251.

[0129] When a quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 410, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 410 preferably contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 251, 293, and 353.

[0130] When a quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 452, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 452 preferably contains one or more fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 145, 160, 251, and 335.

[0131] When a quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 452, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 452 preferably contains one or more fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 251, and 335, and more preferably contains fragment ions with mass-to-charge ratios (m / z) of 118, 251, and 335.

[0132] When a quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 494, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 494 preferably contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, and 335.

[0133] When a quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 494, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 494 preferably contains one or more fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 251, and 335, and more preferably contains fragment ions with mass-to-charge ratios (m / z) of 118, 251, and 335.

[0134] When a quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 536, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 536 preferably contains one or more fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 145, 160, 251, and 335, and more preferably contains fragment ions with mass-to-charge ratios (m / z) of 118, 251, and 335.

[0135] When a quantitative analysis is performed using a mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 578, the mass spectrogram in which the mass-to-charge ratio (m / z) of the parent ion is 578 preferably contains one or more fragment ions selected from the group consisting of mass-to-charge ratios (m / z) of 118, 251, and 335, and more preferably contains fragment ions with mass-to-charge ratios (m / z) of 118, 251, and 335.

[0136] The peak area of ​​the parent ion in the selected mass spectrogram used for quantitative analysis is preferably 50% or more and 100% or less, more preferably 70% or more and 100% or less, and even more preferably 90% or more and 100% or less, of the peak area of ​​the parent ion in the selected mass spectrogram.

[0137] The peak area of ​​the parent ion in the selected mass spectrogram used for quantitative analysis is preferably 50% to 100%, more preferably 70% to 100%, and even more preferably 90% to 100%, of the peak area of ​​the parent ion in a selected mass spectrogram further selected based on one criterion selected from the group consisting of the above-mentioned criterion A, criterion B, criterion C, criterion D, criterion E, and criterion F. The analytical method of the embodiment will be specifically described below using examples.

[0138] Example 1 A tris(isopropylphenyl)phosphate solution was used as a standard sample (calibration curve). 10 μL of a cyclohexane solution containing 100 μg / mL of tris(isopropylphenyl)phosphate was weighed out, the solvent was evaporated, and the solution was analyzed by Py-GC / MS under condition 2.

[0139] As a sample (analysis subject), 1 mg of resin sample 1 containing 0.1% PIP (3:1) raw material was weighed out (raw material component 1 μg), and analyzed by Py-GC / MS under the conditions 2 shown below.

[0140] (Condition 2) Pyrolyzer heat extraction temperature: 600[℃], Pyrolyzer interface temperature: Auto Gas chromatograph column: 100% dimethyl polysiloxane, length 15 [m], internal diameter 0.25 [mm], film thickness 0.05 [μm] Gas chromatograph injection temperature: 300[℃] Gas chromatograph column oven temperature: 40°C (hold for 2 minutes), increase at 10°C / min, up to 320°C Gas chromatograph injection mode: Split 1 / 50 Gas chromatograph carrier gas: He 52.1[cm / sec], constant flow Mass spectrometer ionization method: EI (electron ionization impact method) 70 [eV] Mass spectrometer ion source temperature: 230[℃] Mass spectrometer scan range: m / z 10-600

[0141] For the obtained mass spectrogram, the peak area value of the parent ion of the calibration sample tris(isopropylphenyl)phosphate, having a mass-to-charge ratio m / z of 452, was set to a value of 1.0 [μg].

[0142] After confirming the fragment ions of each mass spectrogram obtained during measurement of the sample to be analyzed, the peak area values ​​of the parent ions with mass-to-charge ratios m / z of 368, 410, 452, 494, and 536 were integrated and compared with the area value of the calibration curve sample, resulting in an integrated quantitative value of 0.90 [μm].

[0143] Comparative Example 1 As a standard sample (calibration curve), 10 μL of a cyclohexane solution of triphenyl phosphate (TPP) at 100 μg / mL was weighed out, the solvent was evaporated, and the solution was analyzed by Py-GC / MS under condition 2.

[0144] As a sample (analysis target), 1 mg of resin sample 1 containing 0.1% PIP (3:1) raw material (raw material component 1 μg) was weighed out and analyzed by Py-GC / MS under condition 2.

[0145] For the obtained mass spectrogram, the total ion chromatogram (TIC) area value of the calibration sample TPP was set to 1.0 [μg].

[0146] For each chromatogram obtained during the actual sample measurement, the qualitative ions were confirmed, and then the TIC area values ​​were integrated and compared with the area values ​​of the calibration curve samples. The integrated quantitative value was 1.3 [μg].

[0147] The table in Figure 7 shows the mass-to-charge ratio m / z and peak area value of each mass spectrogram of isopropylated phenyl phosphate contained in the sample to be analyzed. The numbers in the table in Figure 5 correspond to the numbers in the table in Figure 7. As shown in the table in Figure 7, many fragment ions are detected, but the Examples show that quantitative evaluation excluding these fragment ions is more reliable than quantitative evaluation using a total ion chromatogram.

[0148] The technical solutions of the embodiments are described below. Technical proposal 1 hot extracting the sample; analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample; determining whether the mass spectrogram contains fragment ions and / or parent ions of a particular mass to charge ratio (m / z); A method for analyzing isopropylated phenyl phosphate having the formula: Technical proposal 2 The analytical method according to Technical Proposal 1, in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), determines whether the mass spectrogram contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, 277, 293, 335, 353, 377, and 452. Technical proposal 3 The step of thermally extracting the sample has a thermal extraction temperature of 400° C. or more and 700° C. or less; The analytical method described in Technical Proposal 1, in the process of determining whether the mass spectrogram contains fragment ions and / or parent ions with a specific mass-to-charge ratio (m / z), determines whether the mass spectrogram contains fragment ions with a mass-to-charge ratio (m / z) of 335. Technical proposal 4 The analytical method described in Technical Proposal 1, in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), determines whether the mass spectrogram contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 251, and 335. Technical proposal 5 The analytical method according to Technical Proposal 1, in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions with a specific mass-to-charge ratio (m / z), determines whether the mass spectrogram contains fragment ions with a mass-to-charge ratio (m / z) of 118 or / and 251, and further determines whether the mass spectrogram contains fragment ions with a mass-to-charge ratio (m / z) of 145 or / and 160. Technical proposal 6 The analytical method described in Technical Proposal 1, in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions with a specific mass-to-charge ratio (m / z), determines whether the mass spectrogram contains fragment ions with a mass-to-charge ratio (m / z) of 145 and / or 160. Technical proposal 7 The analytical method described in Technical Proposal 1, in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions with a specific mass-to-charge ratio (m / z), determines whether the mass spectrogram contains two or more fragment ions with mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, and 335. Technical proposal 8 An analytical method according to any one of technical proposals 2, 4, 5, 6, and 7, wherein the thermal extraction temperature in the step of thermally extracting the sample is 400°C or higher and 700°C or lower. Technical proposal 9 An analytical method according to any one of technical proposals 2, 4, 5, 6, 7, and 8, further comprising determining whether the mass spectrogram contains a mass-to-charge ratio (m / z) corresponding to a parent ion of isopropylated phenyl phosphate in the step of determining whether the mass spectrogram contains a fragment ion and / or a parent ion having a specific mass-to-charge ratio (m / z). Technical proposal 10 hot extracting the sample; analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample; determining the concentration of isopropylated phenyl phosphate contained in the sample from the peak area of ​​a parent ion of isopropylated phenyl phosphate in the mass spectrogram; A method for analyzing isopropylated phenyl phosphate having the formula: Technical proposal 11 The analytical method described in Technical Proposal 10 determines the concentration of isopropylated phenyl phosphate contained in a standard sample from the ratio of the peak area of ​​the parent ion of tris(isopropylphenyl) phosphate in the mass spectrum obtained by analyzing the standard sample containing tris(isopropylphenyl) phosphate using gas chromatography mass spectrometry to the peak area of ​​the parent ion in the mass spectrogram of isopropylated phenyl phosphate of the sample.

[0149] Although some embodiments of the present invention have been described, these embodiments are presented as examples and are not intended to limit the scope of the invention. These embodiments can be implemented in various other forms, and various omissions, substitutions, and modifications can be made without departing from the spirit of the invention. These embodiments and their modifications are included in the scope of the invention and its equivalents described in the claims, as well as in the scope and spirit of the invention. [Explanation of symbols]

[0150] 100 Analytical equipment (pyrolysis gas chromatograph mass spectrometer (Py-GC / MS)) 10 Thermal decomposition equipment 11 Heating furnace 12 Heater 20 First Interface 30 Gas chromatograph 31 Inlet 32 Capillary Column 33 Capillary heater 40 Second Interface 50 mass spectrometer 51 Ionization section 52 Mass separation section 53 Detector 60 Control device

Claims

1. hot extracting the sample; analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample; determining whether the mass spectrogram contains fragment ions and / or parent ions of a particular mass to charge ratio (m / z); A method for analyzing isopropylated phenyl phosphate having the formula:

2. The analytical method according to claim 1, wherein in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, 277, 293, 335, 353, 377, and 452.

3. The step of thermally extracting the sample has a thermal extraction temperature of 400° C. or more and 700° C. or less; The analytical method according to claim 1, wherein in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains a fragment ion having a mass-to-charge ratio (m / z) of 335.

4. 2. The analytical method according to claim 1, wherein in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains one or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 251, and 335.

5. 2. The method according to claim 1, wherein in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains fragment ions having a mass-to-charge ratio (m / z) of 118 or / and 251, and further whether the mass spectrogram contains fragment ions having a mass-to-charge ratio (m / z) of 145 or / and 160.

6. The analytical method according to claim 1, wherein in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains fragment ions having a mass-to-charge ratio (m / z) of 145 and / or 160.

7. 2. The analytical method according to claim 1, wherein in the step of determining whether the mass spectrogram contains fragment ions and / or parent ions having a specific mass-to-charge ratio (m / z), it is determined whether the mass spectrogram contains two or more fragment ions having mass-to-charge ratios (m / z) selected from the group consisting of 118, 145, 160, 251, and 335.

8. 8. The analytical method according to claim 2, wherein the temperature of the thermal extraction step of the sample is 400[°C] or higher and 700[°C] or lower.

9. The analytical method according to any one of claims 2, 4, 5, 6 and 7, further comprising determining whether the mass spectrogram contains a fragment ion and / or a parent ion having a specific mass-to-charge ratio (m / z) and further determining whether the mass spectrogram contains a mass-to-charge ratio (m / z) corresponding to a parent ion of isopropylated phenyl phosphate.

10. hot extracting the sample; analyzing the thermally extracted sample by gas chromatography-mass spectrometry to obtain a mass spectrogram of one or more compounds contained in the sample; determining the concentration of isopropylated phenyl phosphate contained in the sample from the peak area of ​​a parent ion of isopropylated phenyl phosphate in the mass spectrogram; A method for analyzing isopropylated phenyl phosphate having the formula:

11. The analytical method according to claim 10, wherein the concentration of isopropylated phenyl phosphate contained in the sample is determined from the ratio of the peak area of ​​the parent ion of tris(isopropylphenyl) phosphate in a mass spectrum obtained by analyzing a standard sample containing tris(isopropylphenyl) phosphate by gas chromatography-mass spectrometry to the peak area of ​​the parent ion of the tris(isopropylphenyl) phosphate in a mass spectrum obtained by gas chromatography-mass spectrometry.

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