Xylene diisocyanate preparations, polymerizable preparations, resins, molded items, optical elements and lenses.

Abstract

The invention relates to a xylene diisocyanate composition comprising xylene diisocyanate and isocyanatomethylbenzoyl chloride.

Description

Xylylene diisocyanate composition, polymerizable composition, resin, molded article, optical element, and lens

[0001] The present invention relates to a xylylene diisocyanate composition, a polymerizable composition, a resin, a molded article, an optical element, and a lens.

[0002] It has been known to produce a resin that can be used for optical elements such as lenses by reacting a xylylene diisocyanate composition with a polythiol (see Patent Document 1 below).

[0003] International Publication No. 2018 / 190290

[0004] In the production of a resin such as that described in Patent Document 1, there are cases where it is desired to further improve heat resistance while suppressing a decrease in light resistance.

[0005] The present invention provides a xylylene diisocyanate composition and a polymerizable composition that can be used to produce a resin having excellent light resistance and heat resistance, as well as a resin, a molded article, an optical element, and a lens having excellent light resistance and heat resistance.

[0006] The present invention [1] includes a xylylene diisocyanate composition containing xylylene diisocyanate and isocyanatomethylbenzoic acid chloride.

[0007] The present invention [2] includes the xylylene diisocyanate composition according to the above [1], in which the proportion of isocyanatomethylbenzoic acid chloride in the xylylene diisocyanate composition is 1 ppm or more by mass.

[0008] The present invention [3] includes the xylylene diisocyanate composition according to the above [1] or [2], in which the proportion of isocyanatomethylbenzoic acid chloride in the xylylene diisocyanate composition is 2000 ppm or less by mass.

[0009] The present invention [4] includes the xylylene diisocyanate composition according to any one of the above [1] to [3], which further contains isocyanatomethylbenzoic acid.

[0010] The present invention [5] includes a polymerizable composition containing the xylylene diisocyanate composition according to any one of the above [1] to [4] and an active hydrogen group-containing component.

[0011] The present invention [6] is a copolymer of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, ... The polymerizable composition according to [5] above contains at least one polythiol selected from the group consisting of 1,3-dimethyl-2,4-dimethyl-1,5 ...

[0012] The present invention [7] includes a resin that is a cured product of the polymerizable composition of the above [5] or [6].

[0013] The present invention [8] includes a molded article made of the resin of the above [7].

[0014] The present invention [9] includes an optical element which is the molded article according to the above [8].

[0015] The present invention

[10] includes a lens, which is the optical element of the above [9].

[0016] The xylylene diisocyanate composition and the polymerizable composition of the present invention contain isocyanatomethylbenzoic acid chloride.

[0017] By using a xylylene diisocyanate composition and a polymerizable composition containing isocyanatomethylbenzoic acid chloride as raw materials, a resin having excellent light resistance and heat resistance can be produced.

[0018] The resin of the present invention is a cured product of a polymerizable composition containing the xylylene diisocyanate composition.

[0019] The molded article, optical element, and lens of the present invention are made of the above resin.

[0020] Therefore, the resin, molded article, optical element and lens of the present invention have excellent light resistance and heat resistance.

[0021] 1. Xylylene diisocyanate composition The xylylene diisocyanate composition (XDI composition) contains xylylene diisocyanate (XDI) as a main component. Note that the "XDI composition" described here is the "second XDI composition" obtained by the "method for producing an XDI composition" described below.

[0022] Examples of XDI include 1,2-XDI (o-XDI), 1,3-XDI (m-XDI), and 1,4-XDI (p-XDI).

[0023] As XDI, preferably, 1,3-XDI (m-XDI) is used.

[0024] The XDI composition may contain two or more types of XDI.

[0025] The proportion (purity) of XDI in the XDI composition is, for example, 98.00% by mass or more, 99.00% by mass or more, 99.30% by mass or more, or 99.60% by mass or more.

[0026] The proportion of XDI in the XDI composition is, for example, 99.95 mass % or less.

[0027] The range of the XDI content in the XDI composition can be set by combining the upper and lower limits of the XDI content in the XDI composition described above. The XDI content in the XDI composition may be 98.00% by mass to 99.95% by mass, 99.00% by mass to 99.95% by mass, 99.30% by mass to 99.95% by mass, or 99.60% by mass to 99.95% by mass.

[0028] The proportion of XDI in the XDI composition is measured by the method described in the Examples below.

[0029] The XDI composition contains isocyanatomethylbenzoic acid chloride as a minor component.

[0030] Examples of isocyanatomethylbenzoic acid chloride include 2-isocyanatomethylbenzoic acid chloride (o-isocyanatomethylbenzoic acid chloride), 3-isocyanatomethylbenzoic acid chloride (m-isocyanatomethylbenzoic acid chloride), and 4-isocyanatomethylbenzoic acid chloride (p-isocyanatomethylbenzoic acid chloride).

[0031] As the isocyanatomethylbenzoic acid chloride, preferably, 3-isocyanatomethylbenzoic acid chloride (m-isocyanatomethylbenzoic acid chloride) is used.

[0032] The XDI composition may contain two or more types of isocyanatomethylbenzoic acid chloride.

[0033] The proportion of isocyanatomethylbenzoic acid chloride in the XDI composition is, for example, 1 ppm or more, 3 ppm or more, 5 ppm or more, 7 ppm or more, 10 ppm or more, 15 ppm or more, 20 ppm or more, 25 ppm or more, 30 ppm or more, 35 ppm or more, 40 ppm or more, 45 ppm or more, or 50 ppm or more by mass.

[0034] When the proportion of isocyanatomethylbenzoic acid chloride in the XDI composition is equal to or greater than the above lower limit, the heat resistance of a resin produced using the XDI composition can be improved.

[0035] The proportion of isocyanatomethylbenzoic acid chloride in the XDI composition is, for example, 5000 ppm or less, 2000 ppm or less, 1900 ppm or less, 1500 ppm or less, 1000 ppm or less, 800 ppm or less, 500 ppm or less, 300 ppm or less, 200 ppm or less, 100 ppm or less, 90 ppm or less, or 70 ppm or less by mass.

[0036] When the proportion of isocyanatomethylbenzoic acid chloride in the XDI composition is equal to or less than the upper limit, a decrease in the light resistance of a resin produced using the XDI composition can be suppressed.

[0037] The range of the proportion of isocyanatomethylbenzoic acid chloride in the XDI composition can be set by combining the upper and lower limits of the proportion of isocyanatomethylbenzoic acid chloride in the XDI composition described above. The proportion of isocyanatomethylbenzoic acid chloride in the XDI composition may be, by mass, 1 ppm to 5000 ppm, 3 ppm to 2000 ppm, 5 ppm to 1900 ppm, 7 ppm to 1500 ppm, 10 ppm to 1000 ppm, 15 ppm to 800 ppm, 20 ppm to 500 ppm, 25 ppm to 300 ppm, 30 ppm to 200 ppm, 35 ppm to 100 ppm, 40 ppm to 90 ppm, 45 ppm to 70 ppm, or 50 ppm to 70 ppm.

[0038] The proportion of isocyanatomethylbenzoic acid chloride in the XDI composition is measured by the method described in the Examples below.

[0039] The XDI composition may further contain isocyanatomethylbenzoic acid as a minor component.

[0040] The proportion of isocyanatomethylbenzoic acid in the XDI composition is, by mass, for example, 0.1 ppm or more, 0.3 ppm or more, 0.5 ppm or more, 0.7 ppm or more, 1.0 ppm or more, 1.5 ppm or more, 2.0 ppm or more, 2.5 ppm or more, 3.0 ppm or more, 3.5 ppm or more, 4.0 ppm or more, 4.5 ppm or more, or 5.0 ppm or more.

[0041] When the proportion of isocyanatomethylbenzoic acid in the XDI composition is equal to or greater than the above lower limit, the heat resistance of a resin produced using the XDI composition can be improved.

[0042] The proportion of isocyanatomethylbenzoic acid in the XDI composition is, for example, 100.0 ppm or less, 80.0 ppm or less, 50.0 ppm or less, 30.0 ppm or less, 20.0 ppm or less, 10.0 ppm or less, 9.0 ppm or less, or 7.0 ppm or less by mass.

[0043] When the proportion of isocyanatomethylbenzoic acid in the XDI composition is equal to or less than the upper limit, a decrease in the light resistance of a resin produced using the XDI composition can be suppressed.

[0044] The range of the proportion of isocyanatomethylbenzoic acid in the XDI composition can be set by combining the upper and lower limits of the proportion of isocyanatomethylbenzoic acid in the XDI composition described above. The proportion of isocyanatomethylbenzoic acid in the XDI composition may be, by mass, 0.1 ppm to 100.0 ppm, 0.3 ppm to 80.0 ppm, 0.5 ppm to 50.0 ppm, 0.7 ppm to 30.0 ppm, 1.0 ppm to 20.0 ppm, 1.5 ppm to 10.0 ppm, 2.0 ppm to 9.0 ppm, 2.5 ppm to 7.0 ppm, 3.0 ppm to 7.0 ppm, 3.5 ppm to 7.0 ppm, 4.0 ppm to 7.0 ppm, 4.5 ppm to 7.0 ppm, or 5.0 ppm to 7.0 ppm.

[0045] The proportion of isocyanatomethylbenzoic acid in the XDI composition is measured by gas chromatography mass spectrometry and gas chromatography analysis under the same measurement conditions as those for isocyanatomethylbenzoic acid chloride described above.

[0046] The XDI composition may further contain, as a secondary component, at least one of monochloromethylbenzyl isocyanate (CBI), dichloromethylbenzyl isocyanate (DCI), and dichloromethaneiminomethylbenzyl isocyanate (dichloroimine form) represented by the following chemical formula (1):

[0047] Chemical formula (1):

[0048] Examples of DCI include 2-(dichloromethyl)benzyl isocyanate (o-DCI), 3-(dichloromethyl)benzyl isocyanate (m-DCI), and 4-(dichloromethyl)benzyl isocyanate (p-DCI).

[0049] As the DCI, preferably, 3-(dichloromethyl)benzyl isocyanate (m-DCI) is used.

[0050] The XDI composition may contain two or more types of DCI.

[0051] The proportion of DCI in the XDI composition is, for example, 0.1 ppm or more, 0.3 ppm or more, 0.6 ppm or more, or 1.0 ppm or more by mass.

[0052] The proportion of DCI in the XDI composition is, for example, 60 ppm or less, 50 ppm or less, 30 ppm or less, or 20 ppm or less by mass.

[0053] The range of the DCI content in the XDI composition can be set by combining the upper and lower limits of the DCI content in the XDI composition described above, and the DCI content in the XDI composition may be 0.1 ppm to 60 ppm, 0.3 ppm to 50 ppm, 0.6 ppm to 30 ppm, or 1.0 ppm to 20 ppm by mass.

[0054] When the proportion of DCI in the XDI composition is within the above range, the yellowness of the resin produced from the XDI composition can be reduced.

[0055] The proportion of DCI in the XDI composition is measured by the method described in the Examples below.

[0056] Examples of CBI include 2-(monochloromethyl)benzyl isocyanate (o-CBI), 3-(monochloromethyl)benzyl isocyanate (m-CBI), and 4-(monochloromethyl)benzyl isocyanate (p-CBI).

[0057] As the CBI, preferably, 3-(monochloromethyl)benzyl isocyanate (m-CBI) is used.

[0058] The XDI composition may contain two or more CBIs.

[0059] The proportion of CBI in the XDI composition is, for example, 0.2 ppm or more, 6 ppm or more, or 100 ppm or more by mass.

[0060] The proportion of CBI in the XDI composition is, for example, 5000 ppm or less, 4000 ppm or less, 3000 ppm or less, 1600 ppm or less, or 1000 ppm or less by mass.

[0061] The range of the CBI content in the XDI composition can be set by combining the upper and lower limits of the CBI content in the XDI composition described above, and the CBI content in the XDI composition may be, by mass, 0.2 ppm to 5000 ppm, 6 ppm to 4000 ppm, 100 ppm to 3000 ppm, 100 ppm to 1600 ppm, or 100 ppm to 1000 ppm.

[0062] When the proportion of CBI in the XDI composition is within the above range, the yellowness of the resin produced from the XDI composition can be reduced. In particular, when the content of CBI in the XDI composition is equal to or less than the above upper limit, yellowing of the resin can be suppressed, and the urethane reaction during the production of the resin can proceed smoothly, thereby reliably improving the mechanical properties of the resin.

[0063] The CBI content is, for example, 2 times or more, 10 times or more, or 20 times or more relative to the DCI content. The CBI content is, for example, 800 times or less, 300 times or less, or 50 times or less relative to the DCI content. The CBI content may be 2 to 800 times, 10 to 300 times, or 20 to 50 times relative to the DCI content.

[0064] The proportion of CBI in the XDI composition is measured by the method described in the Examples below.

[0065] Examples of dichloroimine compounds include 2-(dichloromethaneiminomethyl)benzyl isocyanate, 3-(dichloromethaneiminomethyl)benzyl isocyanate, and 4-(dichloromethaneiminomethyl)benzyl isocyanate.

[0066] A preferred example of the dichloroimine compound is 3-(dichloromethaneiminomethyl)benzyl isocyanate.

[0067] The XDI composition may contain two or more types of dichloroimine forms.

[0068] The proportion of the dichloroimine compound in the XDI composition is, for example, 0.1 ppm or more, 0.2 ppm or more, 0.5 ppm or more, 1.0 ppm or more, or 2.0 ppm or more by mass.

[0069] The proportion of dichloroimine compounds in the XDI composition is, for example, 200 ppm or less, 150 ppm or less, 100 ppm or less, 80 ppm or less, or 60 ppm or less by mass.

[0070] The range of the proportion of the dichloroimine compound in the XDI composition can be set by combining the upper and lower limits of the proportion of the dichloroimine compound in the XDI composition described above. The proportion of the dichloroimine compound in the XDI composition may be, by mass, 0.1 ppm to 200 ppm, 0.2 ppm to 150 ppm, 0.5 ppm to 100 ppm, 1.0 ppm to 80 ppm, or 2.0 to 60 ppm.

[0071] The proportion of dichloroimine compounds in the XDI composition is measured by the method described in the Examples below.

[0072] 2. Method for Producing XDI Composition The method for producing the XDI composition will now be described.

[0073] The method for producing the XDI composition includes, for example, a synthesis step, a purification step, and a purification step.

[0074] In the synthesis step, XDI is synthesized. In the synthesis step, XDI is synthesized by, for example, a hydrochloride method. When the hydrochloride method is used, the synthesis step includes a salt formation step and an isocyanate formation step.

[0075] In the salt formation step, xylylenediamine (XDA) and hydrogen chloride are mixed to produce xylylenediamine hydrochloride (XDA hydrochloride).

[0076] Examples of XDA include 1,2-XDA (o-XDA), 1,3-XDA (m-XDA), and 1,4-XDA (p-XDA), and preferably 1,3-XDA (m-XDA).

[0077] In the salt formation step, for example, XDA is reacted with hydrogen chloride in the presence of an inert solvent. Specifically, hydrogen chloride gas is mixed with a solution of XDA dissolved in an inert solvent, and the XDA and hydrogen chloride are reacted.

[0078] Examples of inert solvents include those described in paragraph

[0059] of WO 2018 / 190290. The inert solvents can be used alone or in combination of two or more. Among the inert solvents, halogenated aromatic hydrocarbons are preferred, and chlorobenzene and dichlorobenzene are more preferred.

[0079] The proportion of XDA relative to the sum of the masses of XDA and the inert solvent (total amine concentration) is, for example, 3% by mass to 30% by mass, 5% by mass to 20% by mass, or 5% by mass to 15% by mass.

[0080] The supply ratio of hydrogen chloride is, for example, 2 to 10 moles, 2 to 6 moles, or 2 to 4 moles per mole of XDA.

[0081] The reaction temperature in the salt formation step is, for example, 30°C to 160°C, 50°C to 150°C, or 50°C to 140°C.

[0082] The reaction pressure (gauge pressure) in the salt production step is, for example, 0 MPaG (atmospheric pressure) to 1.0 MPaG, or 0.01 MPaG to 0.5 MPaG.

[0083] XDA reacts with hydrogen chloride to produce XDA hydrochloride, and a slurry containing XDA hydrochloride is obtained.

[0084] Next, in the isocyanation step, XDA hydrochloride is reacted with carbonyl dichloride to produce a reaction mass containing XDI. In the isocyanation step, carbonyl dichloride is mixed with a slurry containing XDA hydrochloride, and the XDA hydrochloride and carbonyl dichloride are reacted while removing the by-product hydrogen chloride gas. XDI is produced by the reaction between XDA hydrochloride and carbonyl dichloride. In other words, XDI is obtained by the reaction between XDA hydrochloride and carbonyl dichloride.

[0085] The supply ratio of carbonyl dichloride is, for example, 4 to 50 moles, 5 to 40 moles, or 6 to 30 moles per mole of XDA hydrochloride.

[0086] The reaction time of the isocyanation step is, for example, 4 hours to 25 hours, 6 hours to 20 hours, or 6 hours to 15 hours.

[0087] The reaction temperature in the isocyanation step is, for example, 90°C to 190°C, 100°C to 180°C, or 110°C to 160°C.

[0088] The reaction pressure (gauge pressure) in the isocyanation step is, for example, 0 MPaG to 0.6 MPaG, 0.0005 MPaG to 0.4 MPaG, 0.001 MPaG to 0.2 MPaG, 0.003 MPaG to 0.2 MPaG, 0.01 MPaG to 0.2 MPaG, 0.02 MPaG to 0.2 MPaG, or 0.03 MPaG to 0.2 MPaG. The reaction pressure (gauge pressure) in the isocyanation step preferably exceeds 0 MPaG (atmospheric pressure).

[0089] The isocyanation step is preferably carried out continuously, i.e., the slurry containing XDA hydrochloride is continuously fed to a reaction vessel used in the isocyanation step, and the XDA hydrochloride is reacted with carbonyl dichloride in the reaction vessel while the reaction mass is continuously removed from the reaction vessel.

[0090] Next, gas components, inert solvents, and tar components are removed from the reaction mass.

[0091] The gaseous components include carbonyl dichloride that remains in the reaction mass without reacting with XDA hydrochloride in the isocyanation step and hydrogen chloride gas that is by-produced in the isocyanation step, and are removed from the reaction mass using, for example, a known degassing tower.

[0092] The inert solvent is distilled off from the reaction mass, for example, using a known distillation column.

[0093] Tar components are removed from the reaction mass, for example, using a known detarring device.

[0094] After the gas components, the inert solvent, and the tar components are removed, the proportion of XDI in the reaction mass is, for example, 80.0 mass% to 99.0 mass%, 90.0 mass% to 98.5 mass%, or 95.0 mass% to 98.0 mass%.

[0095] Next, in the purification step, the reaction mass is purified. The purification step includes, for example, a low boiling point removal step and a rectification step.

[0096] In the low boiling point removal step, low boiling point components are removed from the reaction mass. The low boiling point components have a boiling point lower than that of XDI. In the low boiling point removal step, for example, the reaction mass is distilled in a low boiling point removal column to distill off the low boiling point components from the reaction mass.

[0097] Examples of the low boiling point removal tower include a tray tower and a packed tower, and preferably a packed tower. The number of theoretical plates of the low boiling point removal tower is, for example, 3 to 40 plates, 5 to 20 plates, or 7 to 15 plates.

[0098] The temperature at the bottom of the low boiling separation tower is, for example, 130°C to 200°C, 140°C to 190°C, or 150°C to 180°C.

[0099] The top temperature of the low boiling separation tower is, for example, 90°C to 160°C, 100°C to 150°C, or 110°C to 140°C.

[0100] The pressure at the top of the low boiling separation tower is, for example, 0.05 kPa to 3.0 kPa, 0.1 kPa to 2.0 kPa, or 0.2 kPa to 1.0 kPa.

[0101] The reflux ratio at the top of the low boiling separation tower is, for example, 1 to 80, 5 to 60, or 10 to 50.

[0102] The residence time in the low boiling removal tower is, for example, 0.1 to 10 hours, 0.2 to 5 hours, or 0.3 to 3 hours.

[0103] By distillation using the low boiling point removal column, the reaction mass from which the low boiling point components have been distilled off is obtained as bottoms.

[0104] Next, in the rectification step, the reaction mass after the low boiling point removal step is further distilled (rectified) using a rectification column.

[0105] Examples of the rectification column include a plate column and a packed column, and preferably a packed column. The number of theoretical plates of the rectification column is, for example, 1 to 20, 1 to 10, or 1 to 5.

[0106] The bottom temperature of the rectification column is, for example, 120°C to 190°C, 130°C to 180°C, or 140°C to 170°C.

[0107] The temperature at the top of the rectification column is, for example, 90°C to 180°C, 110°C to 170°C, or 130°C to 160°C.

[0108] The pressure at the top of the rectification column is, for example, 0.05 kPa to 3.0 kPa, 0.1 kPa to 2.0 kPa, or 0.2 kPa to 1.0 kPa.

[0109] The top reflux ratio of the rectification column is, for example, 0.1 to 50, 0.2 to 20, or 0.3 to 10.

[0110] The residence time in the rectification column is, for example, 0.2 to 20 hours, 0.5 to 10 hours, or 1.0 to 10 hours.

[0111] The fraction containing XDI (first XDI composition) is obtained by the rectification step. The first XDI composition contains DCI, CBI, and dichloroimine compounds.

[0112] Next, in the production step, isocyanatomethylbenzoic acid and isocyanatomethylbenzoic acid chloride are produced.

[0113] Specifically, in the producing step, compressed air is blown into a first XDI composition.

[0114] The temperature of the first XDI composition in the production step is, for example, 10°C to 80°C, 15 to 70°C, 20°C to 50°C, or 20°C to 30°C.

[0115] The flow rate of the compressed air is, for example, 10 ml / min to 30 ml / min, or 15 ml / min to 25 ml / min, per 100 g of the first XDI composition.

[0116] The time for blowing compressed air is, for example, 10 minutes to 20 hours, 1 hour to 15 hours, 2 hours to 10 hours, or 5 hours to 10 hours.

[0117] The formation step produces isocyanatomethylbenzoic acid and isocyanatomethylbenzoic acid chloride. Specifically, it is believed that blowing compressed air into the first XDI composition causes a by-product in the first XDI composition to react with oxygen to produce isocyanatomethylbenzoic acid. It is believed that the formed isocyanatomethylbenzoic acid then reacts with hydrolyzable chlorine in the first XDI composition to produce isocyanatomethylbenzoic acid chloride.

[0118] The production step yields the above-described XDI composition (second XDI composition).

[0119] The method for producing an XDI composition may not include the production step, but may include, for example, a salt formation step, an isocyanation step, a purification step, and a mixing step.

[0120] In the mixing step, isocyanatomethylbenzoic acid or isocyanatomethylbenzoic acid chloride is added to the first XDI composition and mixed.

[0121] This method also makes it possible to obtain the above-mentioned XDI composition.

[0122] The XDI composition described above is used as a raw material for resins, which are produced by reacting an isocyanate component containing the XDI composition with an active hydrogen group-containing component containing an active hydrogen group-containing compound.

[0123] The active hydrogen group-containing compound contains an active hydrogen group. The active hydrogen group is a functional group capable of generating active hydrogen. Examples of the active hydrogen group include a hydroxy group, a mercapto group, and an amino group. Examples of the active hydrogen group-containing compound include a polyol, a polythiol, and a polyamine.

[0124] The active hydrogen group-containing compound can be used alone or in combination of two or more kinds.

[0125] From the viewpoint of optical properties, the active hydrogen group-containing compound is preferably a polythiol. The active hydrogen group-containing component is preferably a polythiol composition containing a polythiol as a main component.

[0126] The proportion of polythiol in the polythiol composition is, for example, 50% by mass or more, 60% by mass or more, 70% by mass or more, or 80% by mass or more.

[0127] The proportion of polythiol in the polythiol composition is measured, for example, by high performance liquid chromatography.

[0128] The polythiol has a plurality of mercapto groups. The polythiol does not contain the subcomponents described below. Examples of the polythiol include an aliphatic polythiol, an aromatic polythiol, and a heterocyclic polythiol.

[0129] Examples of aliphatic polythiols include methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, 1,2-cyclohexanedithiol, bis(2-mercaptoethyl)ether, tetrakis(mercaptomethyl)methane, diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), ), trimethylolpropane tris(3-mercaptopropionate), trimethylolethane tris(2-mercaptoacetate), trimethylolethane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptomethyl)sulfide, bis(mercaptomethyl)disulfide, bis(mercaptoethyl)sulfide, bis(mercaptoethyl)disulfide, bis(mercaptopropyl)sulfide, bis (mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, bis(3-mercaptopropylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio)ethane, 1,2-bis(3-mercaptopropylthio)ethane, 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercaptopropylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7 -dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, bis(2,3-dimercaptopropyl)sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-Dimercapto-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, and their esters of thioglycolic acid and mercaptopropionic acid, hydroxymethyl sulfide bis(2-mercaptoacetate), hydroxymethyl sulfide bis(3-mercaptopropionate), hydroxyethyl sulfide bis(2-mercaptoacetate), hydroxyethyl sulfide bis(3-mercaptopropionate), hydroxymethyl disulfide bis(2-mercaptoacetate), hydroxymethyl disulfide bis(3-mercaptopropionate), hydroxyethyl disulfide bis(2-mercaptoacetate), hydroxyethyl disulfide bis(3-mercapto propionate), thiodiglycolic acid bis(2-mercaptoethyl ester), thiodipropionic acid bis(2-mercaptoethyl ester), dithiodiglycolic acid bis(2-mercaptoethyl ester), dithiodipropionic acid bis(2-mercaptoethyl ester), 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, and tris(mercaptoethylthio)methane.

[0130] Examples of aromatic polythiols include 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,3,5-trimercaptobenzene, 1,3,5-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyleneoxy)benzene, 1,3,5-tris(mercaptoethyleneoxy)benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,5-naphthalenedithiol, and 2,6-naphthalenedithiol.

[0131] Heterocyclic polythiols include, for example, 2-methylamino-4,6-dithiol-sym-triazine, 3,4-thiophenedithiol, and bismuthiol.

[0132] The polythiols can be used alone or in combination of two or more kinds.

[0133] Furthermore, preferred examples of polythiol include 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, ... and at least one selected from the group consisting of 1,3-dimethyl-2,4-dithiapentane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, ethylene glycol bis(3-mercaptopropionate), and diethylene glycol bis(3-mercaptopropionate).

[0134] The polythiol composition may contain minor components.

[0135] Examples of the secondary component include a compound in which at least one of the multiple mercapto groups of the above-mentioned polythiol is substituted with a functional group represented by the following chemical formula (2) (hereinafter referred to as compound A).

[0136] Chemical formula (2):

[0137] When the polythiol composition contains compound A, in high performance liquid chromatography measurement of the polythiol composition, the peak area (R1) of compound A relative to the peak area of ​​the polythiol (100) is, for example, 0.01 to 3.0, 0.01 to 1.5, or 0.01 to 0.5.

[0138] The "peak area (R1) of compound A relative to 100 of the peak area of ​​polythiol" refers to the peak area (P ｔｈｉｏｌ ) is set to 100, the peak area of ​​compound A (P Ａ ) and is calculated by the following formula (1).

[0139] Formula (1): R1=(P Ａ / P ｔｈｉｏｌ ) × 100 When determining the "peak area (R1) of compound A relative to 100 of the peak area of ​​polythiol," high performance liquid chromatography measurement is performed under the measurement conditions described in paragraph

[0041] of WO 2022 / 102625.

[0140] When the peak area (R1) of compound A relative to the peak area 100 of the polythiol falls within the above range, it is possible to maintain a good pot life of the polymerizable composition obtained from the polythiol composition and the polyisocyanate composition, and further, by curing the polymerizable composition, it is possible to obtain a plastic lens made of a polythiourethane resin that is excellent in quality, such as hue, transparency, and striae.

[0141] Furthermore, when the polythiol composition contains at least one polythiol selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, the polythiol composition may further contain a compound represented by the following chemical formula (3) (hereinafter referred to as compound B) as a minor component.

[0142] Chemical formula (3):

[0143] (In chemical formula (3), m and n each independently represent 0 or 1, and m+n=1.)

[0144] When the polythiol composition contains compound B, in high performance liquid chromatography measurement of the polythiol composition, the peak area (R2) of compound B relative to the total peak area of ​​100 of the compounds contained in the polythiol composition is, for example, more than 0 and 10.0 or less, 0.02 to 9.0, 0.04 to 8.0, 1.0 to 7.0, 2.0 to 6.0, 3.0 to 6.0, or 4.0 to 6.0.

[0145] The "peak area (R2) of compound B relative to the total peak area of ​​the compounds contained in the polythiol composition (100)" is the total peak area (P ｓｕｍ ) is set to 100, the peak area of ​​compound B (P Ｂ The total peak area (P ｓｕｍ ) is the sum of the peak areas of all peaks detected in high performance liquid chromatography measurement of the polythiol composition.

[0146] Formula (2): R2=(P Ｂ / P ｓｕｍ ) × 100 When determining the "peak area (R2) of compound B relative to the total peak area of ​​the compounds contained in the polythiol composition (100)," the high performance liquid chromatography measurement is carried out under the measurement conditions described in paragraph

[0049] of WO 2022 / 138865.

[0147] When the peak area (R2) of compound B relative to the total peak area 100 of the compounds contained in the polythiol composition is the upper limit or less, the light resistance of the resin produced from the polythiol composition can be improved. Furthermore, when the peak area (R2) of compound B relative to the total peak area 100 of the compounds contained in the polythiol composition is the lower limit or more, the dyeability of the resin produced from the polythiol composition can be improved.

[0148] For example, the resin is produced by cast molding. In cast molding, an isocyanate component and an active hydrogen group-containing component are first mixed in a ratio such that the ratio of active hydrogen groups (amino groups, thiol groups, or hydroxyl groups) in the active hydrogen group-containing component to isocyanate groups in the isocyanate component is 0.8 to 1.2. The resulting mixture is a polymerizable composition containing the XDI composition and the active hydrogen group-containing component.

[0149] The polymerizable composition may contain known additives, such as curing catalysts, stabilizers (acidic phosphate esters), and ultraviolet absorbers.

[0150] Next, the polymerizable composition is poured into a mold and then heated and cured, thereby obtaining a molded article made of resin. In other words, the resin is a cured product of the polymerizable composition.

[0151] When the active hydrogen group-containing component contains a polythiol, the resulting molded article has excellent transparency.

[0152] Furthermore, since the above-mentioned XDI composition contains XDI and isocyanatomethylbenzoic acid chloride, the obtained molded article has low yellowness and excellent heat resistance.

[0153] Specifically, the glass transition temperature (Tg) of the obtained molded article is, for example, 85.0°C or higher, 87.0°C or higher, or 87.5°C or higher. The glass transition temperature (Tg) of the obtained molded article is, for example, 90.0°C or lower, or 88.0°C or lower. The glass transition temperature (Tg) of the obtained molded article may be 85.0°C to 90.0°C, 87.0°C to 88.0°C, or 87.5°C to 88.0°C.

[0154] The YI value of the obtained molded article is, for example, 5.85 or less, 5.65 or less, 5.60 or less, 5.55 or less, 5.50 or less, 5.45 or less, or 5.43 or less. The YI value of the obtained molded article is, for example, 5.40 or more. The YI value of the obtained molded article may be 5.40 to 5.85, 5.40 to 5.65, 5.40 to 5.55, 5.40 to 5.50, 5.40 to 5.45, or 5.40 to 5.43.

[0155] The obtained molded article also has a high refractive index. The refractive index (ne) of the obtained molded article is, for example, 1.650 or more, or 1.660 or more. The refractive index (ne) of the obtained molded article is, for example, 1.670 or less. The refractive index (ne) of the obtained molded article may be 1.650 to 1.670, or 1.660 to 1.670.

[0156] The Abbe number (νe) of the obtained molded article is, for example, 30 or more, or 31 or more. The Abbe number (νe) of the obtained molded article is, for example, 35 or less, or 33 or less. The Abbe number (νe) of the obtained molded article may be 30 to 35, or 31 to 33.

[0157] When the molded article has the above-mentioned physical properties, it is suitable as an optical element.

[0158] Examples of the optical element include a lens, a sheet, and a film, and preferably a lens.

[0159] Examples of lenses include clear lenses, sunglasses lenses, polarized lenses, eyeglass lenses, camera lenses, pickup lenses, and contact lenses.

[0160] The uses of the XDI composition are not limited to the optical materials described above. Examples of uses of the XDI composition include inks, transfer foils, pressure sensitive adhesives, binders, gels, elastomers, foams, adhesives, one-component curing sealants, RIM molded products, micro-foamed polyurethanes, various microcapsules, aqueous resins, thermosetting resins, active energy ray (e.g., electron beams, ultraviolet rays, etc.) curable resins, artificial and synthetic leathers, slush powders, robot components, mobility components, healthcare materials, base resins for carbon fiber reinforced plastics (CFRP), transparent rubbers, transparent hard resins, Examples of applications include waterproof materials, films, sheets, tubes, blades, speakers, sensors, organic electroluminescent (EL) components, solar power generation components, android components, wearable components, sporting goods, leisure goods, medical supplies, nursing care products, housing components, acoustic components, lighting components, chandeliers, outdoor lights, packing, vibration-proofing, vibration-damping and seismic isolation components, soundproofing components, daily necessities, miscellaneous goods, cushions, bedding, stress absorbing materials, stress relaxation materials, interior and exterior parts of automobiles, transportation equipment components, office automation equipment components, surface protection components for miscellaneous goods, self-repairing materials, and health equipment.

[0161] Preferred applications of the XDI composition include the above-mentioned optical materials, elastomers, foams, and one-component curing sealants.

[0162] 4. Effects and Effects The xylylene diisocyanate composition and polymerizable composition of the present invention contain isocyanatomethylbenzoic acid chloride.

[0163] By using a xylylene diisocyanate composition and a polymerizable composition containing isocyanatomethylbenzoic acid chloride as raw materials, a resin having excellent light resistance and heat resistance can be produced.

[0164] The resin of the present invention is a cured product of a polymerizable composition containing the xylylene diisocyanate composition.

[0165] The molded article, optical element, and lens of the present invention are made of the above resin.

[0166] Therefore, the resin, molded article, optical element and lens of the present invention have excellent light resistance and heat resistance.

[0167] 5. Variations (1) The synthesis method of XDI is not limited to the hydrochloride method described above. Examples of the synthesis method of XDI include a gas-phase method in which vaporized XDA is reacted with carbonyl dichloride, a one-stage method in which XDA is directly reacted with carbonyl dichloride in one stage, and a cold-hot two-stage method in which XDA is reacted with carbonyl dichloride at a low temperature and then subsequently reacted at a high temperature. In these methods, XDI is obtained by the reaction of XDA with carbonyl dichloride. Another example of the synthesis method of XDI is a non-phosgene method in which XDI is obtained by thermally decomposing xylylene dicarbamate.

[0168] (2) The production of the XDI composition does not have to be carried out continuously in the same plant. For example, a first XDI composition produced in a first plant can be used to carry out the purification step in a second plant.

[0169] The present invention will be described in more detail below with reference to examples, but is not limited thereto. The specific numerical values ​​of the blending ratios (content ratios), physical property values, parameters, etc. used in the following description can be replaced with the upper limit values ​​(numeric values ​​defined as "equal to or less than") or lower limit values ​​(numeric values ​​defined as "equal to or more than" or "exceeding") of the corresponding blending ratios (content ratios), physical property values, parameters, etc. described in the above "Form for Carrying Out the Invention." The "ratio" of each component is based on mass.

[0170] 1. Production of XDI Composition (1) Example 1 A dropping solution was prepared by mixing 136 g (1.0 mol) of m-xylylenediamine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 621 g of o-dichlorobenzene (ODCB) in an Erlenmeyer flask.

[0171] Next, 845 g of ODCB was placed in a 1 L flask equipped with a reflux condenser, a thermometer, and a gas inlet tube.

[0172] The temperature of ODCB was raised to 100°C, and the above-mentioned solution was added dropwise to the mixture at a flow rate of 2 mL per minute over 3 hours using a feed pump (HPLC pump PU-980 manufactured by JASCO Corporation) while stirring. Simultaneously with the addition of the solution, 230 g of hydrochloric acid gas was blown in over 3 hours.

[0173] Next, the blowing of hydrochloric acid gas was stopped, and the mixture was heated and stirred for 30 minutes, thereby obtaining a slurry of m-xylylenediamine hydrochloride (salt production step).

[0174] Next, nitrogen gas was bubbled through the slurry for 1 hour to remove unreacted hydrochloric acid gas from the slurry.

[0175] Next, the temperature of the slurry was raised to 160°C, and 1200 g of carbonyl dichloride gas was blown into the slurry over 6 hours, thereby reacting m-xylylenediamine hydrochloride with carbonyl dichloride to obtain a reaction mass containing m-XDI (isocyanation step).

[0176] Next, nitrogen gas was bubbled through the reaction mass for 1 hour to remove unreacted carbonyl dichloride from the reaction mass.

[0177] The reaction mass was then filtered under reduced pressure to remove precipitates in the reaction mass.

[0178] Next, the reaction mass after removing the precipitate was subjected to desolvation to distill off ODCB in the reaction mass (desolvation step).

[0179] Next, the reaction mass was distilled under reduced pressure (vacuum degree 0.5 to 1.0 Torr) using a rectification column packed with four trays, and 158 g of a first XDI composition containing m-XDI was obtained as a fraction from the reaction mass (purification step).

[0180] Next, 100 g of the first XDI composition was placed in a 200 ml recovery flask, and compressed air was blown into the first XDI composition (temperature of the first XDI composition: 25°C, flow rate of compressed air: 20 ml / min, blowing time: 20 minutes) (production process).

[0181] Thereafter, the mixture was filtered through a 1 μm Teflon (registered trademark) filter, and 75 mg of phenol (stabilizer) was added to prepare an XDI composition (second XDI composition).

[0182] (2) Example 2 An XDI composition was prepared in the same manner as in Example 1, except that compressed air was blown in for 2 hours in the production step.

[0183] (3) Example 3 An XDI composition was prepared in the same manner as in Example 1, except that compressed air was blown in for 6 hours in the production step.

[0184] (4) Example 4 An XDI composition was prepared in the same manner as in Example 1, except that compressed air was blown in for 15 hours in the production step.

[0185] (5) Example 5 An XDI composition was prepared in the same manner as in Example 1, except that in the production step, the first XDI composition was heated to 60° C. and compressed air was blown into it for 5 hours.

[0186] (6) Example 6 An XDI composition was prepared in the same manner as in Example 1, except that in the production step, the first XDI composition was heated to 60° C. and compressed air was blown into it for 10 hours.

[0187] (7) Comparative Example An XDI composition was prepared in the same manner as in Example 1, except that in the production step, hydrochloric acid gas equivalent to 20 ppm was blown in instead of compressed air.

[0188] 2. Measurement of component amounts of XDI compositions The proportions of XDI, isocyanatomethylbenzoic acid chloride (acid chloride), dichloroimine, DCI, and CBI in the XDI compositions obtained in each Example and Comparative Example were measured by the following method. The results are shown in Table 1.

[0189] (1) Identification of Isocyanatomethylbenzoic Acid Chloride The XDI composition obtained in Example 1 was subjected to gas chromatography mass spectrometry under the following conditions.

[0190] (Measurement conditions) Apparatus: Agilent 6890 / 5973N Column: HP19091L-433 HP-50+ (inner diameter 0.25 mm × length 30 m, film 0.25 μm) Oven temperature: hold at 50°C for 1 minute, heat from 50°C to 280°C at 10°C / min, hold for 10 minutes after reaching 280°C Carrier gas: contact flow mode, He, 1.0 mL / min Injection method: pulsed splitless method (150 kPa, at 0.5 min) Injection amount: 1.0 μL Sample concentration: 1.0 mass% dichloromethane solution Injection temperature: 200°C Interface temperature: 280°C Quadrupole temperature: 150°C Ion source temperature: 230°C Detection method: Scan method (m / z: 10 to 500) The mass spectrum of the peak appearing at a retention time of 19.87 minutes in the obtained total ion chromatogram was collated with the library data.

[0191] The mass spectrum contained a fragment peak with a maximum peak at a molecular weight of 195, and the degree of agreement with isocyanatomethylbenzoic acid chloride was 70% or more.

[0192] Therefore, the compound corresponding to the peak appearing at a retention time of 19.87 minutes in the total ion chromatogram was identified as isocyanatomethylbenzoic acid chloride.

[0193] (2) Proportions of XDI, isocyanatomethylbenzoic acid chloride, and dichloroimine in the XDI composition 100 mg of the XDI composition was mixed with 100 mg of 1,2,4,5-tetrachlorobenzene as an internal standard. The resulting mixture was then diluted with dichloromethane and adjusted to a constant volume of 10 mL to obtain a sample. The resulting sample was then analyzed by gas chromatography under the following measurement conditions.

[0194] (Measurement conditions) Apparatus: SHIMADZU 2014 (Shimadzu Corporation) Packing material: DB-1 (film thickness) 1.5 μm Column: inner diameter 0.53 mm × length 60 m (Shimadzu Corporation) Oven temperature: heated from 130°C to 220°C at 3°C / min, and after reaching 220°C, heated to 300°C at 10°C / min Split ratio: pulsed splitless method Injection port temperature: 280°C Detector temperature: 300°C Carrier gas: N２ 158 kPa, H ２ 55 kPa, Air 45 kPa (constant pressure control) Injection volume: 2 μL Detection method: FID The proportion of XDI in the XDI composition was calculated from the area ratio between the peak of the internal standard appearing at a retention time of 8.8 minutes and the peak of XDI appearing at a retention time of 13.8 minutes.

[0195] The proportion of isocyanatomethylbenzoic acid chloride in the XDI composition was calculated from the area ratio between the peak of the internal standard and the peak of isocyanatomethylbenzoic acid chloride appearing at a retention time of 17.8 minutes.

[0196] The proportion of the dichloroimine compound in the XDI composition was calculated from the area ratio between the peak of the internal standard and the peak of the dichloroimine compound appearing at a retention time of 15.6 minutes.

[0197] (3) Proportion of DCI in XDI Composition The proportion of DCI in the XDI composition was measured by the method described in paragraphs

[0375] to

[0376] of WO 2018 / 190290.

[0198] (4) Proportion of CBI in XDI Composition The proportion of CBI in the XDI composition was measured by the method described in paragraphs

[0376] to

[0377] of WO 2018 / 190290.

[0199] 2. Production of Molded Article 52 parts by mass of the XDI composition shown in Table 1 was mixed and dissolved at 20°C with 0.01 part by mass of dimethyltin dichloride as a curing catalyst, 0.10 part by mass of Zelec UN (trade name, manufactured by Stepan; acidic phosphate ester), and 1.5 parts by mass of Biosorb 583 (manufactured by Sakai Chemical Industry Co., Ltd.; ultraviolet absorber) to obtain Mixture 1.

[0200] Next, 48 parts by mass of 4,8-dimercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (manufactured by Mitsui Chemicals, Inc.) was uniformly mixed with the mixed liquid 1 to obtain a mixed liquid 2 (polymerizable composition).

[0201] Mixture 2 was degassed at 600 Pa for 1 hour, and then filtered through a 1 μm Teflon (registered trademark) filter.

[0202] Next, the filtered mixed solution 2 was poured into a mold consisting of a glass mold and tape.

[0203] Next, the mold into which the mixed liquid 2 had been poured was placed in an oven, the temperature was raised from 10° C. to 120° C., and the mixture was cured at 120° C. for 38 hours.

[0204] Thereafter, the mold was removed from the oven, the cured product was released from the mold, and the resulting cured product was annealed at 120° C. for 1 hour.

[0205] As a result of the above, cured products (molded articles) of the respective Examples and Comparative Examples were obtained.

[0206] 3. Evaluation of Physical Properties of Molded Articles (1) Light Resistance A 2 mm thick plate was prepared from the obtained molded article and subjected to a QUV test (light source: UVA-340, intensity: 0.50 W / m) using a Q-Lab accelerated weather resistance tester. ２ , test conditions: 50°C x 150 hours).

[0207] The yellowness index (YI value) of the molded article was measured before and after the QUV test, and the difference between the yellowness index of the molded article before the QUV test and the yellowness index of the molded article after the QUV test (yellowness index change, ΔYI) was calculated. The smaller the ΔYI, the better the light resistance.

[0208] The ΔYI values ​​of the examples and comparative examples are shown in Table 1.

[0209] (2) Yellowness Index (YI Value) A disk having a thickness of 9 mm and a diameter of 75 mm was prepared from the obtained resin, and the YI value was determined using a spectrophotometer CM-5 manufactured by Konica Minolta, Inc.

[0210] The smaller the YI value, the less yellow the resin is, and the larger the YI value, the more yellow the resin is.

[0211] The YI values ​​of each of the Examples and Comparative Examples are shown in Table 1.

[0212] (3) Heat Resistance Test pieces measuring 10 mm in length, 10 mm in width, and 2.5 mm in thickness were prepared from the obtained resin, and the glass transition temperature (Tg) was measured by the TMA penetration method (50 g load, pin tip 0.5 mmφ, heating rate 10°C / min) using a thermomechanical analyzer TMA-60 manufactured by Shimadzu Corporation. The higher the glass transition temperature (Tg), the better the heat resistance.

[0213] Table 1 shows the glass transition temperature (Tg) of each of the examples and comparative examples.

[0214] (4) Refractive index (ne) and Abbe number (νe) Test pieces measuring 10 mm in length, 10 mm in width, and 2.5 mm in thickness were prepared from the obtained resin, and the refractive index (ne) at a wavelength of 546.1 nm (mercury e-line), the refractive index (nF') at a wavelength of 480.0 nm (Cd F'-line), and the refractive index (nC') at a wavelength of 643.9 nm (Cd C'-line) were measured using a Pulfrich refractometer KPR-30 manufactured by Shimadzu Corporation. The Abbe number (νe) was calculated based on the refractive index (ne), the refractive index (nF'), and the refractive index (nC').

[0215] In all examples and comparative examples, the refractive index (ne) was 1.665 and the Abbe number (νe) was 31. The above inventions are provided as exemplary embodiments of the present invention, but these are merely examples and should not be interpreted as being limiting. Modifications of the present invention that are obvious to those skilled in the art are included in the scope of the following claims.

[0216] The xylylene diisocyanate composition, polymerizable composition, resin, and molded article of the present invention can be used, for example, in the production of optical elements such as lenses.

Claims

1. A xylylene diisocyanate composition comprising xylylene diisocyanate and isocyanatomethylbenzoic acid chloride.

2. The xylylene diisocyanate composition according to claim 1, wherein the proportion of isocyanatomethylbenzoic acid chloride in the xylylene diisocyanate composition is 1 ppm or more by mass.

3. The xylylene diisocyanate composition according to claim 1, wherein the proportion of isocyanatomethylbenzoic acid chloride in the xylylene diisocyanate composition is 2000 ppm or less on a mass basis.

4. The xylylene diisocyanate composition of claim 1, further comprising isocyanatomethylbenzoic acid.

5. A polymerizable composition comprising the xylylene diisocyanate composition according to any one of claims 1 to 4 and an active hydrogen group-containing component.

6. The active hydrogen group-containing component is selected from the group consisting of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bis(mercaptomethyl)-1,4-dithiane, 6. The polymerizable composition according to claim 5, comprising at least one polythiol selected from the group consisting of 1,2,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate).

7. A resin which is a cured product of the polymerizable composition according to claim 5.

8. A molded article made of the resin according to claim 7.

9. An optical element which is the molded article according to claim 8.

10. A lens which is the optical element according to claim 9.