Container containing xylylene diisocyanate, method for storing xylylene diisocyanate, and method for transporting xylylene diisocyanate

Abstract

To provide a container that contains xylylene diisocyanate with sufficiently low colorability, a storage method of xylylene diisocyanate and a transport method of xylylene diisocyanate.SOLUTION: In a xylylene diisocyanate-containing container 1 consisting of xylylene diisocyanate and a container that contains the xylylene diisocyanate, a resin layer 4 is provided on the inner surface of a container 2.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention relates to a container containing xylylene diisocyanate, a method for storing xylylene diisocyanate, and a method for transporting xylylene diisocyanate.

Background Art

[0002] It has been studied to form an optical lens that requires excellent transparency from a poly(thio)urethane resin. As a raw material for an optical lens made of a poly(thio)urethane resin, a xylylene diisocyanate composition containing xylylene diisocyanate is known (see, for example, Patent Document 1).

Prior Art Documents

[0007] The present invention [2] includes the xylylene diisocyanate-containing container described in [1] above, wherein the resin layer comprises an epoxy resin.

[0008] The present invention [3] includes a xylylene diisocyanate-containing container as described in [2] above, wherein the resin layer comprises an epoxyphenol resin. The present invention [4] includes a xylylene diisocyanate-containing container comprising xylylene diisocyanate having an acidity of less than 15 ppm and a container containing the xylylene diisocyanate, wherein the inner surface of the container is provided with a zinc phosphate coating.

[0009] The present invention [5] includes a method for storing xylylene diisocyanate in a container having a resin layer on its inner surface.

[0010] The present invention [6] includes a method for storing xylylene diisocyanate as described in [5] above, wherein the resin layer comprises an epoxy resin.

[0011] The present invention [7] includes a method for storing xylylene diisocyanate as described in [6] above, wherein the resin layer comprises an epoxyphenol resin. The present invention [8] includes a method for storing xylylene diisocyanate having an acid content of less than 15 ppm in a first container having a zinc phosphate coating on its inner surface. The present invention [9] includes a method for storing xylylene diisocyanate as described in [8] above, comprising the steps of: measuring the acidity of xylylene diisocyanate; if the measured acidity is 15 ppm or more, storing the xylylene diisocyanate in a second container having a resin layer on its inner surface; and if the measured acidity is less than 15 ppm, storing the xylylene diisocyanate in the first container.

[0012] The present invention

[10] includes a method for transporting xylylene diisocyanate, which involves storing and transporting xylylene diisocyanate in a container having a resin layer on its inner surface.

[0013] The present invention

[11] includes a method for transporting xylylene diisocyanate as described in

[10] above, wherein the resin layer comprises an epoxy resin.

[0014] The present invention

[12] includes a method for transporting xylylene diisocyanate as described in

[11] above, wherein the resin layer comprises an epoxyphenol resin. The present invention

[13] includes a method for transporting xylylene diisocyanate, in which xylylene diisocyanate having an acid content of less than 15 ppm is stored and transported in a first container having a zinc phosphate coating on its inner surface. The present invention

[14] includes a method for transporting xylylene diisocyanate as described in

[13] , comprising the steps of: measuring the acidity of xylylene diisocyanate; if the measured acidity is 15 ppm or more, placing the xylylene diisocyanate in a second container having a resin layer on its inner surface; and if the measured acidity is less than 15 ppm, placing the xylylene diisocyanate in the first container. [Effects of the Invention]

[0015] According to the xylylene diisocyanate-containing container of the present invention, since a resin layer is provided on the inner surface of the container, discoloration of the xylylene diisocyanate can be suppressed even when the xylylene diisocyanate is contained in the container and stored and transported for a long period of time. Furthermore, discoloration of the poly(thio)urethane resin produced from the xylylene diisocyanate can be suppressed. According to the container containing xylylene diisocyanate of the present invention, since a zinc phosphate film is provided on the inner surface of the container, even when xylylene diisocyanate with an acid content of less than 15 ppm is stored and transported in the container for a long time, coloring of the xylylene diisocyanate can be suppressed. Further, coloring of the poly(thio)urethane resin produced from the xylylene diisocyanate can be suppressed.

[0016] According to the storage method of xylylene diisocyanate of the present invention, since xylylene diisocyanate is stored in the above-described container, coloring of the xylylene diisocyanate can be suppressed, and coloring of the poly(thio)urethane resin can be suppressed.

[0017] According to the transportation method of xylylene diisocyanate of the present invention, since xylylene diisocyanate is stored and transported in the above-described container, coloring of the xylylene diisocyanate can be suppressed, and coloring of the poly(thio)urethane resin can be suppressed.

Brief Description of Drawings

[0018] [Figure 1] FIG. 1 is a schematic view showing an embodiment of a container containing xylylene diisocyanate of the present invention. [Figure 2] FIG. 2 is a graph showing the correlation between the storage period of a xylylene diisocyanate composition and the hue (APHA) of the xylylene diisocyanate composition in Example 1 and Comparative Example 1. [Figure 3] FIG. 3 is a graph showing the correlation between the storage period of a xylylene diisocyanate composition and the yellow index (Y.I.) of the xylylene diisocyanate composition in Example 1 and Comparative Example 1. [Figure 4] FIG. 4 is a graph showing the correlation between the storage period of a xylylene diisocyanate composition and b* of the xylylene diisocyanate composition in Example 1 and Comparative Example 1. [Figure 5]FIG. 5 is a graph showing the correlation between the storage period of the xylylene diisocyanate composition and the Y.I. of the optical lens produced from the xylylene diisocyanate composition in Example 1 and Comparative Example 1. [Figure 6] FIG. 6 is a graph showing the correlation between the storage period of the xylylene diisocyanate composition and the Y.I. of the optical lens produced from the xylylene diisocyanate composition in Examples 3 and 4. [Figure 7] FIG. 7 is a graph showing the correlation between the storage period of the xylylene diisocyanate composition and the Y.I. of the optical lens produced from the xylylene diisocyanate composition in Examples 5 and 6.

BEST MODE FOR CARRYING OUT THE INVENTION

[0019] As shown in FIG. 1, the container 1 containing xylylene diisocyanate includes xylylene diisocyanate (hereinafter referred to as XDI) and a container 2 in which the XDI is housed.

[0020] Examples of the XDI contained in the container 2 include 1,2-XDI (o-XDI), 1,3-XDI (m-XDI), 1,4-XDI (p-XDI), and the like.

[0021] These XDI can be used alone or in combination of two or more.

[0022] Among the XDI, preferably, 1,3-XDI (m-XDI) can be mentioned.

[0023] XDI can be obtained, for example, as a commercially available product (e.g., MR-7A manufactured by Mitsui Chemicals, Inc.), or it can be manufactured by known methods. Known methods include, for example, a gas-phase method in which evaporated xylylenediamine (hereinafter referred to as XDA) is reacted with phosgene; for example, a hydrochloride method in which the hydrochloride salt of XDA is reacted with phosgene; for example, a one-step method in which XDA and phosgene are reacted directly in one step; and for example, a two-step cold-hot method in which XDA and phosgene are reacted at a low temperature followed by a high temperature reaction.

[0024] Furthermore, XDI may be purified by known methods such as rectification (distillation) or extraction, if necessary.

[0025] The purity of XDI is, for example, 95% by mass or more, preferably 98% by mass or more, more preferably 99% by mass or more, even more preferably 99.5% by mass or more, and particularly preferably 99.9% by mass or more, for example, 100% by mass or less. The purity of XDI can be measured in accordance with the method described in the examples below.

[0026] If the purity of XDI is less than 100% by mass, the XDI contains other components. In this case, container 2 contains the XDI composition containing the XDI and the other components.

[0027] Other components include, for example, chloromethylbenzyl isocyanate, dichloromethylbenzyl isocyanate, and hydrolyzable chlorine (HC).

[0028] The content of chloromethylbenzyl isocyanate relative to the total mass of the XDI composition before it is contained in container 2 is, for example, 0.2 ppm or more, preferably 6 ppm or more, more preferably 100 ppm or more, for example 5000 ppm or less, preferably 4000 ppm or less, more preferably 3000 ppm or less, particularly preferably 1600 ppm or less, and especially preferably 1000 ppm or less. The content of chloromethylbenzyl isocyanate can be measured in accordance with the method described in paragraph

[0377] of Japanese Patent No. 6373536 (the same applies hereinafter).

[0029] The content of dichloromethylbenzyl isocyanate relative to the total mass of the XDI composition before it is contained in container 2 is, for example, 0.1 ppm or more, preferably 0.3 ppm or more, more preferably 0.6 ppm or more, more preferably 1.0 ppm or more, and for example, 60 ppm or less, preferably 50 ppm or less, more preferably 30 ppm or less, more preferably 20 ppm or less, more preferably 10 ppm or less, more preferably 5 ppm or less. The content of dichloromethylbenzyl isocyanate can be measured in accordance with the method described in paragraphs

[0375] and

[0376] of Japanese Patent No. 6373536 (the same applies hereinafter).

[0030] The concentration of hydrolyzable chlorine (HC) relative to the total mass of the XDI composition before it is contained in container 2 is, for example, 10 ppm or more, preferably 20 ppm or more, more preferably 30 ppm or more, for example, 1000 ppm or less, preferably 500 ppm or less, and more preferably 200 ppm or less. The concentration of hydrolyzable chlorine (HC) is measured in accordance with the method for determining hydrolyzable chlorine described in JIS K-1603-3 (2007) (the same applies hereinafter). The acidity of the XDI composition before it is placed in container 2 is, for example, 3000 ppm or less, preferably 2000 ppm or less, more preferably 1000 ppm or less, more preferably 100 ppm or less, more preferably 50 ppm or less, more preferably 30 ppm or less, and more preferably less than 15 ppm. The lower limit of the acidity of the XDI composition before it is contained in container 2 is not limited. For example, the acidity of the XDI composition before it is contained in container 2 is 1 ppm or more. The acid content is measured by the method described in the examples below (the same applies hereafter).

[0031] The XDI composition may contain only one of the other components, or it may contain two or more components.

[0032] Examples of container 2 include containers of various shapes such as 18-liter cans, drums, pails, and canisters, with 18-liter cans and drums being preferred. Figure 1 shows a drum-shaped container 2.

[0033] Furthermore, the size of container 2 is not particularly limited, and various sizes can be used. Specifically, the capacity of container 2 is, for example, 0.5L or more, preferably 1L or more, more preferably 16L or more, for example 20,000L or less, preferably 250L or less.

[0034] The material of such a container 2 typically contains iron and / or zinc. Furthermore, a resin layer 4 is provided on the inner surface of the container 2, as shown in the enlarged view of Figure 1. In other words, the container 2 comprises a container body 3 and, if necessary, a resin layer 4. Specifically, if the container 2 contains an XDI composition with an acid content of 15 ppm or more, the container 2 includes a resin layer 4. If the container 2 contains an XDI composition with an acid content of less than 15 ppm, the container 2 may or may not include a resin layer 4.

[0035] The container body 3 includes a metal plate 3a that forms the outer shape of the container 2. The container body 3 also includes a surface treatment layer 3b which is laminated on one side of the metal plate 3a (the inner surface of the container 2) as needed. Specifically, if the container 2 does not have a resin layer 4, the container body 3 includes a surface treatment layer 3b. If the container 2 does have a resin layer 4, the container body 3 does not need to include a surface treatment layer 3b.

[0036] The metal sheet 3a is not particularly limited, but for example, it is a metal sheet containing iron and / or zinc, specifically a steel sheet, more specifically a carbon steel sheet, and even more specifically a cold-rolled steel sheet, a hot-rolled steel sheet, and so on.

[0037] The thickness of the metal plate 3a is, for example, 0.5 mm or more, preferably 1.0 mm or more, for example 2.0 mm or less, preferably 1.6 mm or less.

[0038] The surface treatment layer 3b may be, for example, a chemical conversion film formed by a known chemical conversion treatment.

[0039] The chemical conversion coating is not particularly limited and includes iron plating, zinc plating, tin plating, chromium plating, aluminum plating, nickel plating, iron-zinc plating, aluminum-zinc plating, nickel-zinc plating, iron phosphate plating, and zinc phosphate plating. The chemical conversion coating can be used alone or in combination of two or more types.

[0040] The surface treatment layer 3b typically includes a film containing iron and / or zinc, specifically an iron plating film, a zinc plating film, an iron phosphate film, and a zinc phosphate plating film, more specifically an iron phosphate film and a zinc phosphate plating film, and even more specifically a zinc phosphate film.

[0041] The thickness of the surface treatment layer 3b is, for example, 2 μm or more, preferably 5 μm or more, and for example, 100 μm or less, preferably 50 μm or less.

[0042] Furthermore, if necessary, a coating layer, primer layer, etc., may be formed on, for example, one side of the metal plate 3a (the inner surface of the container 2), the other side of the metal plate 3a (the outer surface of the container 2), one side of the surface treatment layer 3b (the inner surface of the container 2), or the interface between the metal plate 3a and the surface treatment layer 3b.

[0043] The resin layer 4 is provided on the inner surface of the container body 3. The resin layer 4 is laminated on the inner surface of the container body 3. In Figure 1, the resin layer 4 is provided on the side opposite to the metal plate 3a in the surface treatment layer 3b. The resin layer 4 is formed by laminating resin on the inner surface of the container body 3.

[0044] Examples of resins include polyolefin resins (e.g., polyethylene resin, polypropylene resin, cyclic polyolefin resin, etc.), AS (acrylonitrile styrene) resin, ABS (acrylonitrile butadiene styrene) resin, polyvinyl chloride resin, fluoropolymer resin, polyester resin (e.g., polyethylene terephthalate resin, polyethylene naphthalate resin, etc.), phenolic resin, polyacrylic resin, epoxy resin (e.g., epoxyphenol resin, epoxyamine resin, etc.), polyimide resin, polyamide resin (e.g., various nylons, polyamide-imide resin, etc.), poly(thio)urethane resin, cellulose resin, silicone resin, and polycarbonate resin. Poly(thio)urethane resin includes polyurethane resin and polythiourethane resin. Polyurethane resin is a reaction product of isocyanate and polyol. Polythiourethane resin is a reaction product of isocyanate and polythiol.

[0045] These resins can be used individually or in combination of two or more types.

[0046] Preferably, the resin is an epoxy resin, more preferably an epoxyphenol resin or an epoxyamine resin, and even more preferably an epoxyphenol resin. In other words, the resin layer 4 preferably comprises an epoxy resin, more preferably an epoxyphenol resin and / or an epoxyamine resin, even more preferably an epoxyphenol resin, and particularly preferably an epoxyphenol resin.

[0047] If the resin layer 4 contains epoxy resin, the discoloration of the XDI composition contained in the container 2 can be reliably suppressed. In particular, if the resin layer 4 contains epoxyphenol resin, the discoloration of the poly(thio)urethane resin produced from the XDI composition contained in the container 2 can be reliably suppressed.

[0048] The method for forming the resin layer 4 is not particularly limited, and known methods can be used.

[0049] For example, the resin layer 4 is formed by coating the inner surface of the container body 3 with the resin using a known resin coating method such as spray coating, dip coating, electrostatic coating, or powder coating.

[0050] Furthermore, the resin layer 4 can also be formed by laminating a film of the above-mentioned resin (single-layer film, multi-layer film) onto the inner surface of the container body 3 using a known resin lamination method such as dry lamination or hot-melt lamination.

[0051] The thickness of the resin layer 4 is, for example, 5 μm or more, preferably 10 μm or more, for example 1000 μm or less, preferably 500 μm or less.

[0052] Examples of such containers 2 include epoxy-coated cans, preferably epoxy-phenol-coated cans and epoxy-amine-coated cans, and more preferably epoxy-phenol-coated cans.

[0053] Although not shown in the diagram, the gas barrier and water barrier properties can also be improved by depositing inorganic oxides or the like onto container 2.

[0054] Then, by storing the XDI composition (XDI) in such a container 2, an XDI-containing container 1 with excellent low coloration properties can be obtained.

[0055] Furthermore, if an XDI composition (XDI) with an acid content of 15 ppm or more is stored in a container without a resin layer 4, iron and / or zinc contained in the container body 3 may leach into the XDI composition, potentially causing the XDI composition to contain iron and / or zinc. Therefore, it is not advisable for a container 2 without a resin layer 4 to contain an XDI composition with an acid content of 15 ppm or more.

[0056] In contrast, in a container 2 with a resin layer 4 on its inner surface, even when an XDI composition (XDI) with an acid content of 15 ppm or more is stored in the container 2, the leaching of iron and / or zinc into the XDI composition can be suppressed. Therefore, a container 2 with a resin layer 4 on its inner surface can accommodate an XDI composition (XDI) with an acid content of 15 ppm or more. Furthermore, a container 2 with a resin layer 4 on its inner surface can also accommodate an XDI composition (XDI) with an acid content of less than 15 ppm. Furthermore, when an XDI composition with an acidity of less than 15 ppm is stored in a container 2 that does not have a resin layer 4 on its inner surface but does have a surface treatment layer 3b, the surface treatment layer 3b suppresses the elution of iron and / or zinc into the XDI composition. Therefore, while a container 2 that does not have a resin layer 4 on its inner surface but has a surface treatment layer 3b is not suitable for storing XDI compositions with an acidity of 15 ppm or more, it can store XDI compositions with an acidity of less than 15 ppm.

[0057] The iron content of the XDI composition stored in container 2 is, for example, 1 ppb or more, for example, 1000 ppb or less, preferably 500 ppb or less.

[0058] The zinc content of the XDI composition stored in container 2 is, for example, 1 ppb or more, for example, 1000 ppb or less, preferably 500 ppb or less.

[0059] Furthermore, the content ratio of chloromethylbenzyl isocyanate to the total mass of the XDI composition stored in container 2 is, for example, 0.2 ppm or more, preferably 6 ppm or more, more preferably 100 ppm or more, for example 5000 ppm or less, preferably 4000 ppm or less, more preferably 3000 ppm or less, particularly preferably 1600 ppm or less, and especially preferably 1000 ppm or less.

[0060] The content ratio of dichloromethylbenzyl isocyanate relative to the total mass of the XDI composition stored in container 2 is, for example, 0.1 ppm or more, preferably 0.3 ppm or more, more preferably 0.6 ppm or more, more preferably 1.0 ppm or more, and for example, 60 ppm or less, preferably 50 ppm or less, more preferably 30 ppm or less, more preferably 20 ppm or less, more preferably 10 ppm or less, and more preferably 5 ppm or less.

[0061] The concentration of hydrolyzable chlorine (HC) relative to the total mass of the XDI composition stored in container 2 is, for example, 10 ppm or more, preferably 20 ppm or more, more preferably 30 ppm or more, and for example, 1000 ppm or less, preferably 500 ppm or less, and more preferably 200 ppm or less.

[0062] Furthermore, the XDI-containing container 1 may be sealed with an inert gas such as nitrogen gas, if necessary.

[0063] In such an XDI-containing container 1, the XDI composition (XDI) is stored in the container 2 described above. In other words, an XDI composition (XDI) with an acid content of 15 ppm or more is stored in a container 2 having a resin layer 4 on its inner surface. Alternatively, an XDI composition (XDI) with an acid content of less than 15 ppm is stored in a container 2 that does not have a resin layer 4 on its inner surface but has a zinc phosphate coating. It is also possible to store an XDI composition (XDI) with an acid content of less than 15 ppm in a container 2 having a resin layer 4 on its inner surface. In detail, the acidity of xylylene diisocyanate is measured. If the measured acidity is 15 ppm or higher, the xylylene diisocyanate is placed in container 2 which has a resin layer on its inner surface. If the measured acidity is less than 15 ppm, the xylylene diisocyanate is placed in container 2 which does not have a resin layer 4 on its inner surface but has a zinc phosphate coating.

[0064] The storage conditions include a storage temperature of, for example, -5°C or higher, preferably 0°C or higher, for example 50°C or lower, preferably 40°C or lower, more preferably 30°C or lower, and even more preferably 25°C or lower. In addition, when storing at low temperatures, the storage temperature is, for example, 5°C or lower, preferably 1°C or lower.

[0065] If the storage temperature is below the above upper limit, the discoloration of the XDI composition can be reliably suppressed.

[0066] Furthermore, the storage period is, for example, 1 day or more, preferably 10 days or more, more preferably 1 month or more, even more preferably 3 months or more, particularly preferably 6 months or more, for example, 3 years or less, preferably 1 year or less.

[0067] Furthermore, if necessary, the XDI composition (XDI) is transported in the container 2 described above. In other words, XDI compositions (XDI) with an acid content of 15 ppm or more are stored and transported in a container 2 having a resin layer 4 on its inner surface. Alternatively, XDI compositions (XDI) with an acid content of less than 15 ppm are stored and transported in a container 2 that does not have a resin layer 4 on its inner surface but has a zinc phosphate coating. It is also possible to store and transport XDI compositions (XDI) with an acid content of less than 15 ppm in a container 2 having a resin layer 4 on its inner surface. The storage temperature described above can be applied as the temperature during transport.

[0068] The XDI in such an XDI-containing container 1 can be widely used as a raw material for poly(thio)urethane resin, and is suitably used, for example, in the manufacture of optical lenses and coatings.

[0069] Optical lenses are manufactured, for example, by the reaction of XDI with polythiol. In the manufacture of optical lenses, methods such as casting can be employed.

[0070] Examples of optical lenses include clear lenses, sunglass lenses, polarized lenses, eyeglass lenses, camera lenses, pickup lenses, and contact lenses.

[0071] The coating is manufactured, for example, from a two-component curing coating material containing component A as a curing agent and component B as a main component. XDI can be used for either component A or component B.

[0072] When XDI is used as agent A, agent A contains, for example, an XDI modified product derived from XDI (e.g., an isocyanurate modified product, a urethane modified product, etc.), and / or an isocyanate-terminated prepolymer which is a reaction product of XDI and a polyol.

[0073] When XDI is used as agent B, agent B contains, for example, a polyurethane polyol, which is a reaction product of XDI and a polyol.

[0074] Examples of coatings include paints and adhesives.

[0075] In the XDI-containing container 1 described above, a resin layer 4 is provided on the inner surface of the container 2, as shown in Figure 1. Therefore, even when XDI is contained in the container 2 and stored and transported over a long period of time, discoloration of the XDI (XDI composition) can be suppressed. Furthermore, discoloration of the poly(thio)urethane resin manufactured from the XDI (XDI composition) can be suppressed.

[0076] In particular, if the resin layer 4 contains epoxyphenol resin, the discoloration of XDI (XDI composition) can be suppressed even more reliably. [Examples]

[0077] Examples, comparative examples, and reference examples are shown below to explain the present invention more specifically, but the present invention is not limited thereto. Specific numerical values such as the blending ratio (content ratio), physical property values, parameters, etc. used in the following description may be replaced with the upper limit values (numerical values defined as "hereinafter" and "less than") or lower limit values (numerical values defined as "above" and "exceeding") of the corresponding blending ratio (content ratio), physical property values, parameters, etc. described in the above "Mode for Carrying Out the Invention". In addition, "parts" and "%" are based on mass unless otherwise specified.

[0078] Also, the measurement methods for various physical properties described below are as follows.

[0079] <Purity of m-XDI in the m-XDI composition> Using m-XDI with a purity of 99 mol% as a standard substance, it was analyzed by gas chromatography under the following conditions by the internal standard method, and a calibration curve was created from the area values of the obtained gas chromatogram.

[0080] Next, the m-XDI composition obtained by rectification was analyzed by gas chromatography under the following conditions to obtain the number of moles of m-XDI. This was converted to mass, and the content ratio (purity) of m-XDI in the m-XDI composition was calculated. The retention time of the internal standard substance was 8.8 minutes, and the retention time of m-XDI was 13.8 minutes. Apparatus; SHIMADZU GC-2014 (manufactured by Shimadzu Corporation) Column; DB-1 (film thickness 1.5 μm, inner diameter 0.53 mm × length 60 m) (manufactured by Shimadzu Corporation) Oven temperature; Heating from 130°C to 220°C at 3°C / min, and then heating from 220°C to 300°C at 10°C / min after reaching 220°C Split ratio; Pulsed splitless method Inlet temperature; 280°C Detector temperature; 300°C Carrier gas; N2 158 kPa (constant pressure control) Internal standard substance; 1,2,4,5-tetrachlorobenzene 100 mg Solvent; chloroform, Sample concentration: 2.0% by mass chloroform solution Injection volume; 2μL, Detection method: FID.

[0081] <NBDI purity in an NBDI composition containing a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane (hereinafter referred to as NBDI)> Using 99 mol% pure NBDI as the standard substance, the gas chromatogram was analyzed by gas chromatography under the following conditions using the internal standard method, and a calibration curve was created from the area values ​​of the resulting gas chromatograms.

[0082] Next, the NBDI composition obtained by rectification was analyzed by gas chromatography under the following conditions to obtain the number of moles of NBDI. This was converted to mass to calculate the NBDI content (purity) in the NBDI composition. The retention time of the internal standard was 8.8 minutes, and the retention time of NBDI was 13.0 minutes. Equipment: SHIMADZU GC-2014 (manufactured by Shimadzu Corporation) Column; DB-1 (film thickness 1.5 μm, inner diameter 0.53 mm x length 60 m) (manufactured by Shimadzu Corporation) Oven temperature: Increase temperature from 130°C to 220°C at a rate of 5°C / min, then increase temperature to 300°C at a rate of 20°C / min. Split ratio; pulsed splitless method, Inlet temperature: 280℃, Detector temperature: 300°C Carrier gas: N2 95.4kPa (constant pressure control) Internal standard substance: 1,2,4,5-tetrachlorobenzene 100 mg, Solvent; chloroform, Sample concentration: 2.0% by mass chloroform solution Injection volume; 2μL, Detection method: FID.

[0083] <Hue (APHA) of XDI Composition and NBDI Composition> It was measured by the method conforming to JIS K 0071 (1998). Specifically, APHA was determined by comparison with a diluted standard solution having the same concentration as the color of the sample using a standard solution prepared by dissolving platinum and cobalt reagents. The "degree number" was used as the measured value. The smaller this degree number, the better the hue.

[0084] <Yellow Index (Y.I.) and b of XDI Composition> * > It was measured using a MINOLTA color difference meter CT-210. First, distilled water was put into a cell CT-A20 with an optical path length of 20 mm, and white calibration was performed so that Y = 100.00, x = 0.3101, and y = 0.3162. Then, the sample was put into the same cell, and the chromaticity coordinates x, y, and b * were measured. Based on the measured values of x and y, Y.I. was calculated by the following formula (1). Y.I. = (234 × x + 106 × y + 106) / y (1) This Y.I. is used as the numerical value of the hue of the XDI composition. The higher the numerical value, the greater the degree of coloring.

[0085] When measuring the liquid XDI composition, it was put into a cell with a thickness of 10 mm and measured.

[0086] <Calculation of Yellow Index Value (Y.I. Value) of Optical Lens (Resin)> The resin was made into circular flat plastic lenses with a thickness of 9 mm and a diameter of 75 mm, respectively, and the chromaticity coordinates x and y were measured using a MINOLTA color difference meter CT-210. Based on the measured values of x and y, Y.I. was calculated by the above formula (1).

[0087] Note that the smaller the Y.I. value, the better the hue of the plastic lens, and there is a correlation that the larger the Y.I., the poorer the hue.

[0088] Preparation Example 1: Preparation of the First m-XDI Composition (Acid Content: 15 ppm or More) An autoclave with a pressure regulator (internal volume 2 m³) equipped with reflux condenser, stirring blades, thermometer, hydrogen chloride gas inlet tube, phosgene inlet tube, raw material tank, and raw material charging pump. 3 A reactor was used. 846 kg of orthodichlorobenzene was charged into this reactor as an inert solvent, and 136.2 kg (1.0 kmol) of m-xylylenediamine and 621 kg of orthodichlorobenzene were charged into the raw material tank (total amine concentration 8.5% by mass).

[0089] Next, the temperature inside the reactor was raised to 120°C, and the internal pressure was adjusted to 0.01 MPa higher than atmospheric pressure. Then, hydrogen chloride gas was introduced into the reactor at a rate of 43.8 kg / hr through the hydrogen chloride gas introduction pipe, and at the same time, m-xylylenediamine diluted with an inert solvent was introduced from the raw material tank at a rate of 379 kg / hr using the raw material charging pump, with the entire amount being charged over 2 hours. After that, hydrogen chloride gas was further charged at a rate of 20 kg / hr while the mixture was aged for 1 hour.

[0090] Next, the reaction mixture (hydrochloride slurry) was heated to 160°C in the reactor, and phosgene was introduced at a rate of 100 kg / hr (1.0 kmol / hr) through a phosgene inlet tube. The reaction was carried out for 8 hours while maintaining the temperature. After the reaction was complete, unreacted phosgene and hydrogen chloride gas were removed by purging nitrogen into the reactor. The reaction mixture was then filtered to remove 0.8 kg (dry weight) of unreacted hydrochloride. The resulting filtrate was desolvated to obtain 188.6 kg of m-XDI composition with an m-XDI purity of 98.10%.

[0091] Next, the obtained m-XDI composition was rectified to obtain an m-XDI composition with a purity of 99.99% by mass. Hydrochloric acid gas was blown into the obtained m-XDI composition to prepare an m-XDI composition with an acid content of 20 ppm. The acid content was measured by the following method. <Method for measuring acid content> Accurately weigh 20g of the sample into a 200ml beaker containing a stirring bar, add 100ml of solvent (a mixture of acetone and ethanol in a 1:1 ratio by volume), place the beaker on a hot plate, heat to dissolve the sample, and then allow to react at room temperature for 10-20 minutes while stirring. Next, using an automatic titrator (Hiranuma COM-500), the sample is titrated with an N / 100 methanolic potassium hydroxide solution (prepared in accordance with JIS K4101, by accurately diluting 0.1 mol / L methanolic potassium hydroxide, which has been adjusted and standardized using methanol, 10-fold) and the inflection point of the resulting titration curve is taken as the endpoint. A blank test is also performed under the same conditions. From the titration results, the acid content (%) is calculated according to the following formula. Formula: Acid content = [0.0365×(AB)×f] / S In the above formula, A is the volume (ml) of N / 100 methanolic potassium hydroxide solution used for titration of the sample, B is the volume (ml) of N / 100 methanolic potassium hydroxide solution used for the blank test, f is the factor of the N / 100 methanolic potassium hydroxide solution, and S is the weight (g) of the sample. Preparation Example 2: Preparation of a second m-XDI composition (acid content: less than 15 ppm) An m-XDI composition with a purity of 99.99% by mass was obtained in the same manner as in Preparation Example 1. Hydrochloric acid gas was blown into the obtained m-XDI composition to prepare an m-XDI composition with an acid content of 2 ppm.

[0092] Preparation Example 3: Preparation of NBDI Composition The same reactor as in Preparation Example 1 was used. 958 g of orthodichlorobenzene was charged into the reactor as the reaction solvent, and 154.2 g (1.0 mol) of a mixture of 2,5-bis(aminomethyl)bicyclo[2.2.1]heptane and 2,6-bis(aminomethyl)bicyclo[2.2.1]heptane and 702 g of orthodichlorobenzene were charged into the raw material tank (total amine concentration 8.5% by mass).

[0093] Next, the temperature inside the reactor was raised to 120°C, and the pressure inside the autoclave was adjusted to 0.01 MPa higher than atmospheric pressure. Then, hydrogen chloride gas was introduced into the reactor at a rate of 43.8 g / hr through the hydrogen chloride gas introduction pipe. Simultaneously, a mixture of 2,5-bis(aminomethyl)bicyclo[2.2.1]heptane and 2,6-bis(aminomethyl)bicyclo[2.2.1]heptane, diluted with solvent, was introduced from the raw material tank at a rate of 428.1 g / hr using the raw material charging pump, and the entire amount was charged over 2 hours. Further aging was carried out for 1 hour while hydrogen chloride gas was added at a rate of 20 g / hr.

[0094] Next, the hydrochloride slurry was heated to 160°C in the reactor, and phosgene was blown in at a rate of 100 g / hr (1.0 mol / hr) through a phosgene inlet tube. The reaction was carried out for 8 hours while maintaining the temperature. After the reaction was complete, unreacted phosgene and hydrogen chloride gas were removed by purging the system with nitrogen. The reaction solution was then filtered to remove 0.5 g (dry weight) of unreacted hydrochloride. The resulting filtrate was desolvated to obtain 206.9 g of an NBDI composition with an NBDI purity of 98.5% by mass.

[0095] Next, the obtained NBDI composition was rectified to obtain an NBDI composition with an NBDI purity of 99.99% by mass.

[0096] Examples 1, 2 and Comparative Example 1 The first or second m-XDI composition was placed in the container shown in Table 1 below, sealed thoroughly with nitrogen gas, and then sealed.

[0097] Subsequently, the samples were left undisturbed in a 20°C environment for 12 months from the time of manufacture (0 months).

[0098] Furthermore, samples were collected by opening each container at the timings shown in Table 1. Then, APHA, YI, and b of each sample (m-XDI composition) were collected. * The following measurements were taken. The results are shown in Table 1 and Figures 2-4.

[0099] Furthermore, optical lenses (polythiourethane resin) were prepared by reacting samples (m-XDI composition) collected at the timings shown in Table 1 with 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (active hydrogen compound). Specifically, 36.4 g of m-XDI composition, 0.001 g of dibutyltin dichloride, 0.07 g of Zelec UN (trade name, acidic phosphate ester, internal release agent, manufactured by Stepan), and 0.05 g of Biosorb 583 (trade name, ultraviolet absorber, manufactured by Sakai Chemical Industry Co., Ltd.) were weighed into a thoroughly dried flask and mixed and dissolved by stirring at 25°C for 1 hour. Then, 33.6 g of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane was added and mixed to prepare a mixture (polymerizable composition).

[0100] The mixture was degassed at 600 Pa for 1 hour and then filtered through a 3 μm PTFE filter. The mixture was then poured into a mold consisting of a glass mold and tape. This mold was placed in an oven and polymerized for 18 hours, gradually increasing the temperature from 10°C to 120°C. After polymerization, the mold was removed from the oven and demolded to obtain the resin. The obtained resin was further annealed at 130°C for 4 hours. The YI of the optical lens of the obtained resin was measured. The results are shown in Table 1 and Figure 5.

[0101] Example 1, in which the container is an epoxyphenol-coated can, compared with Comparative Example 1 (in which the acid content is 15 ppm or more and the container is a zinc phosphate-coated drum), showed differences in APHA, YI, and b of the m-XDI composition. * It was confirmed that the YI of the optical lens could be reduced. Furthermore, in Example 2, where the acid content was less than 15 ppm and the container was a zinc phosphate treated drum, it was confirmed that the APHA of the m-XDI composition could be reduced compared to Comparative Example 1.

[0102] <Storage container> • Containers equipped with a resin layer Example 1: Epoxyphenol coated can (a drum can with an epoxyphenol resin layer on the inner surface of the container), • Containers without a resin layer Example 2, Comparative Example 1: Zinc phosphate treated drum (Drum made of zinc phosphate treated steel sheet (manufactured by JFE Container Co., Ltd.)) Reference example 1 Except for changing the m-XDI composition to an NBDI composition, the NBDI composition was allowed to stand and a sample was taken in the same manner as in Example 1. The APHA of each sample (NBDI composition) was then measured in the same manner as described above. The results are shown in Table 1. In Reference Example 1, it was confirmed that the APHA of the NBDI composition did not deteriorate when the container was an epoxy phenol can.

[0103] Reference example 2 The NBDI composition was allowed to stand and a sample was taken in the same manner as in Comparative Example 1, except that the m-XDI composition was replaced with an NBDI composition. The APHA of each sample (NBDI composition) was then measured in the same manner as described above. The results are shown in Table 1. It was confirmed that the APHA of the NBDI composition did not deteriorate even when the container was a zinc phosphate-treated drum.

[0104] [Table 1] Examples 3 and 4 An m-XDI composition from a different manufacturing lot than the one used in Examples 1 and 2 and Comparative Example 1 was placed in each of the following containers, sealed thoroughly with nitrogen gas, and then sealed.

[0105] Subsequently, the samples were left to stand in a 20°C environment for 6 months from the time of manufacture (0 months).

[0106] Furthermore, samples were collected by opening each container at the timings shown in Table 2. The APHA content of each sample (m-XDI composition) was then measured. The results are shown in Table 2.

[0107] Furthermore, optical lenses (polythiourethane resin) were prepared by reacting samples (m-XDI composition) collected at the timings shown in Table 2 with pentaerythritol tetrakis mercaptopropionate (active hydrogen compound). Specifically, 43.5 g of m-XDI composition, 0.008 g of dibutyltin dichloride, 0.10 g of Zerec UN (trade name, acidic phosphate ester, internal release agent, manufactured by Stepan), and 0.05 g of Biosorb 583 (trade name, ultraviolet absorber, manufactured by Sakai Chemical Industry Co., Ltd.) were weighed into a thoroughly dried flask and mixed and dissolved by stirring at 25°C for 1 hour. Then, 56.5 g of pentaerythritol tetrakis mercaptopropionate was added and mixed to prepare a mixture (polymerizable composition).

[0108] The mixture was degassed at 600 Pa for 1 hour and then filtered through a 3 μm PTFE filter. The mixture was then poured into a mold consisting of a glass mold and tape. This mold was placed in an oven and polymerized for 22 hours, gradually increasing the temperature from 20°C to 120°C. After polymerization, the mold was removed from the oven and demolded to obtain the resin. The obtained resin was further annealed at 120°C for 2 hours. The YI of the obtained resin was measured. The results are shown in Table 2 and Figure 6.

[0109] In Example 3, it was confirmed that when the container is an epoxyphenol-coated can, the YI of the optical lens (resin) can be reduced more effectively than in Example 4 (where the container is an epoxyamine-coated can).

[0110] Examples 5 and 6 The m-XDI compositions used in Examples 3 and 4 were each filled into the following containers, sealed thoroughly with nitrogen gas, and then sealed.

[0111] Subsequently, the samples were left to stand in a 20°C environment for 6 months from the time of manufacture (0 months).

[0112] Furthermore, samples were collected by opening each container at the timings shown in Table 2. The APHA content of each sample (m-XDI composition) was then measured. The results are shown in Table 2.

[0113] Furthermore, optical lenses (polythiourethane resin) were prepared by reacting samples (m-XDI composition) collected at the timings shown in Table 2 with 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (active hydrogen compound). Specifically, 36.4 g of m-XDI composition, 0.001 g of dibutyltin dichloride, 0.07 g of Zelec UN (trade name, acidic phosphate ester, internal release agent, manufactured by Stepan), and 0.05 g of Biosorb 583 (trade name, ultraviolet absorber, manufactured by Sakai Chemical Industry Co., Ltd.) were weighed into a thoroughly dried flask and mixed and dissolved by stirring at 25°C for 1 hour. Then, 33.6 g of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane was added and mixed to prepare a mixture (polymerizable composition).

[0114] The mixture was degassed at 600 Pa for 1 hour and then filtered through a 3 μm PTFE filter. The mixture was then poured into a mold consisting of a glass mold and tape. This mold was placed in an oven and polymerized for 18 hours, gradually increasing the temperature from 10°C to 120°C. After polymerization, the mold was removed from the oven and demolded to obtain the resin. The obtained resin was further annealed at 130°C for 4 hours. The YI of the obtained resin was measured. The results are shown in Table 2 and Figure 7.

[0115] In Example 5, it was confirmed that when the container is an epoxyphenol-coated can, the YI of the optical lens (resin) can be reduced more effectively than in Example 6 (where the container is an epoxyamine-coated can).

[0116] <Storage container> • Containers equipped with a resin layer Examples 3 and 5: Epoxyphenol coated cans (drums with an epoxyphenol resin layer on the inner surface of the container), Examples 4 and 6: Epoxyamine coated cans (drums with an epoxyamine resin layer on the inner surface of the container).

[0117] [Table 2] [Explanation of Symbols]

[0118] 1. Container containing xylylene diisocyanate 2 containers 3. Container body 4 resin layer

Claims

1. A xylylene diisocyanate composition for optical lens manufacturing having a purity of 95% by mass or more of xylylene diisocyanate, A container containing the xylylene diisocyanate composition for optical lens manufacturing and Equipped with, A resin layer is provided on the inner surface of the aforementioned container. The resin layer contains epoxyphenol resin. A container containing a xylylene diisocyanate composition for optical lens manufacturing, characterized by the above.

2. A method for storing a xylylene diisocyanate composition for optical lens manufacturing, characterized by storing the xylylene diisocyanate composition having a purity of 95% by mass or more in a container having a resin layer containing epoxyphenol resin on its inner surface.

3. A method for transporting a xylylene diisocyanate composition for optical lens manufacturing, characterized by storing and transporting the xylylene diisocyanate composition for optical lens manufacturing, having a purity of 95% by mass or more of xylylene diisocyanate, in a container having a resin layer containing epoxyphenol resin on its inner surface.

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