Epoxy compound article

Abstract

Provided is an epoxy compound product which is less susceptible to curing shrinkage, is capable of forming a cured product having excellent heat resistance and transparency, and has a low viscosity. In the epoxy compound product, the purity of the compound represented by the following formula (1) is 90% or more, and the total content of the compound represented by the following formula (a), the compound represented by the following formula (b), the compound represented by the following formula (c) and the compound represented by the following formula (d) is 10 mass% or less. # imgabs0 #

Description

Technical Field

[0001] The present disclosure relates to an epoxy compound product with high purity. This application claims the priority of Japanese Patent Application No. 2022-177527 filed in Japan on November 4, 2022, the content of which is incorporated herein by reference. Background Art

[0002] Epoxy compounds can form cured products with excellent properties such as high strength, heat resistance, and transparency by reacting with various curing agents and curing catalysts. For example, alicyclic epoxy compounds having two or more epoxy groups are used as raw materials for sealing materials, coating agents, adhesives, inks, sealants, and the like.

[0003] As such alicyclic epoxy compounds, for example, 3,4-epoxycyclohexylmethyl (3',4'-epoxy) cyclohexanecarboxylate and 3,4-epoxy-6-methyl-cyclohexylmethyl (3',4'-epoxy-6'-methyl) cyclohexanecarboxylate are known (see Patent Documents 1 and 2).

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: International Publication No. 2019 / 138988

[0007] Patent Document 2: Specification of U.S. Patent No. 2890194 Summary of the Invention

[0008] Problems to be Solved by the Invention

[0009] In recent years, a curable compound that is less likely to undergo curing shrinkage has been demanded. In addition, although 3,4-epoxy-6-methyl-cyclohexylmethyl (3',4'-epoxy-6'-methyl) cyclohexanecarboxylate is less likely to undergo curing shrinkage, only products with low purity are available. When using such products, there are problems such as poor heat resistance and transparency of the cured product, and high viscosity and poor workability.

[0010] Therefore, an object of the present disclosure is to provide an epoxy compound product that is less likely to undergo curing shrinkage, can form a cured product with excellent heat resistance and transparency, and has a low viscosity.

[0011] Means for Solving the Problems

[0012] That is, the present disclosure provides an epoxy compound product, wherein the purity of the compound represented by the following formula (1) is 90% or more, and the total content ratio of the compounds represented by the following formula (a), the compound represented by the following formula (b), the compound represented by the following formula (c), and the compound represented by the following formula (d) is 10% by mass or less.

[0013] [Chemical Formula 1]

[0014]

[0015] Preferably, the Hazen color number of the above epoxy compound product is 105 or less.

[0016] Alternatively, for the above epoxy compound product, the total content ratio of the compound represented by the following formula (a), the compound represented by the following formula (b), the compound represented by the following formula (c), and the compound represented by the following formula (d) is 0.1% by mass or more.

[0017] In addition, the present disclosure provides a curable composition comprising the above epoxy compound product, a curing agent, and / or a curing catalyst.

[0018] In addition, the present disclosure provides a curable composition comprising the above epoxy compound product, other epoxy compounds, and / or oxetane compounds.

[0019] Preferably, the above curable composition is an adhesive, a sealant, or a coating agent.

[0020] In addition, the present disclosure provides a cured product which is a cured product of the above curable composition.

[0021] In addition, the present disclosure provides an optical member comprising the above cured product.

[0022] In addition, the present disclosure provides a method for manufacturing an epoxy compound product, which is a method for manufacturing the above epoxy compound product, and the epoxy compound product is manufactured through the following epoxidation step, the following low-boiling component removal step, and the following high-boiling component removal step.

[0023] Epoxidation step: A step of reacting 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate with an organic peroxy acid to obtain a reaction product.

[0024] Low-boiling component removal step: A step of removing low-boiling components from the reaction product.

[0025] High-boiling component removal step: A step of removing high-boiling components from the reaction product by thin-film evaporation.

[0026] Advantages of the Invention

[0027] The epoxy compound product of the present disclosure is less likely to undergo curing shrinkage, has excellent heat resistance and transparency, and has a low viscosity. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 Showing the alicyclic epoxy compound product 1 produced in Example 1 1H-NMR spectrum. Detailed implementation mode

[0029] [Epoxy compound product]

[0030] The epoxy compound product of the present disclosure contains 3,4-epoxy-6-methyl-cyclohexylmethyl (3',4'-epoxy-6'-methyl) cyclohexanecarboxylate (=the compound shown in the following formula (1)), and its purity (or content ratio) is 90% or more.

[0031] [Chemical formula 2]

[0032]

[0033] From the aspects of lower viscosity, excellent transparency, and the ability to obtain a cured product with particularly excellent heat resistance and transparency, the purity of the compound shown in the above formula (1) is preferably 91% or more, more preferably 94% or more, and further preferably 96% or more.

[0034] In addition, for the above epoxy compound product, with respect to the total amount (100% by mass) of the above epoxy compound product, the total content ratio of the compound shown in the following formula (a), the compound shown in the following formula (b), the compound shown in the following formula (c), and the compound shown in the following formula (d) is 10% by mass or less, preferably 9% by mass or less, more preferably 6% by mass or less, and further preferably 4% by mass or less. The above total content ratio is, for example, 0.1% by mass or more, and can also be 0.2% by mass or more, 1% by mass or more.

[0035] [Chemical formula 3]

[0036]

[0037] For the above epoxy compound product, from the aspects of lower viscosity, excellent transparency, and the ability to obtain a cured product with particularly excellent heat resistance and transparency, with respect to the total amount (100% by mass) of the above epoxy compound product, the content ratio (total content ratio) of impurities, especially compounds with a molecular weight of 100 or less and compounds with a molecular weight of 290 or more (impurities including the compounds shown in the above formulas (a) to (d)) is preferably 10% by mass or less, more preferably 5% by mass or less, further preferably 3% by mass or less, and particularly preferably 2% by mass or less. The above content ratio can be 0.1% by mass or more.

[0038] The content ratio of the compound represented by the above formula (a) is preferably 5% by mass or less, more preferably 3% by mass or less, and further preferably 1% by mass or less. The content ratio of the compound represented by the above formula (a) can be 0.1% by mass or more. The content ratio of the compound represented by the above formula (b) is preferably 1% by mass or less, more preferably 0.4% by mass or less, and further preferably 0.2% by mass or less. The content ratio of the compound represented by the above formula (b) can be 0.0001% by mass or more. The content ratio of the compound represented by the above formula (c) is preferably 5% by mass or less, more preferably 3% by mass or less, and further preferably 1% by mass or less. The content ratio of the compound represented by the above formula (c) can be 0.1% by mass or more. The content ratio of the compound represented by the above formula (d) is preferably 5% by mass or less, more preferably 2% by mass or less, and further preferably 1% by mass or less. The content ratio of the compound represented by the above formula (d) can be 0.1% by mass or more.

[0039] The purity of the compound represented by the above formula (1) in the above epoxy compound product can be calculated as a ratio of the peak area based on gel permeation chromatography (GPC). In the case where the shoulders of the peaks overlap, the above peak area is delimited by a perpendicular line to the baseline passing between the valleys of the peaks.

[0040] The content ratios of the compound represented by the above formula (a), the compound represented by the above formula (b), the compound represented by the above formula (c), the compound represented by the above formula (d), the compound having a molecular weight of 100 or less, and the compound having a molecular weight of 290 or more can be calculated as ratios of the peak areas based on gas chromatography and mass spectrometry (GC-MS), respectively.

[0041] The Hazen color number (APHA) of the above epoxy compound product is preferably 105 or less, more preferably 103 or less, further preferably 100 or less, further preferably 50 or less, and particularly preferably 15 or less.

[0042] From the viewpoint of excellent operability, the viscosity of the above epoxy compound product at 25°C is preferably 1300 mPa·s or less, more preferably 1200 mPa·s or less, further preferably 1000 mPa·s or less, and particularly preferably 900 mPa·s or less. The above viscosity is, for example, 50 mPa·s or more, and can also be 100 mPa·s or more, 300 mPa·s or more. It should be noted that the above viscosity is measured using a digital viscometer (model "DVU-E II type", manufactured by TOKIMEC, Inc.) under the conditions of rotor: standard 1°34'×R24, temperature: 25°C, and rotation speed: 0.5 to 10 rpm.

[0043] (Method for manufacturing an epoxy compound product)

[0044] The above-mentioned epoxy compound product can be manufactured through the following epoxidation process, the following low-boiling-point removal process, and the following high-boiling-point removal process. It should be noted that either the low-boiling-point removal process or the high-boiling-point removal process can be carried out first.

[0045] Epoxidation process: A process of reacting 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate with an organic peroxy acid to obtain a reaction product.

[0046] Low-boiling-point removal process: A process of subjecting the reaction product to low-boiling-point removal treatment.

[0047] High-boiling-point removal process: A process of subjecting the reaction product to high-boiling-point removal treatment through thin-film evaporation.

[0048] In addition, after the epoxidation process and before the low-boiling-point removal process (in the case of carrying out the high-boiling-point removal process - low-boiling-point removal process sequence, it is the high-boiling-point removal process), it is also possible to have: a process (washing process) of washing the obtained reaction product with water to remove the organic peroxy acid and its decomposition products used in the reaction. In addition, before the epoxidation process, it is also possible to have: a process (Diels-Alder reaction process) of subjecting crotonaldehyde and acrolein to the Diels-Alder reaction to obtain 6-methyl-1,3-cyclohexene-1-carbaldehyde and / or a process (Tishchenko reaction process) of subjecting 6-methyl-1,3-cyclohexene-1-carbaldehyde to the Tishchenko reaction to obtain 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate.

[0049] (1) Epoxidation process

[0050] The epoxidation process is a process of reacting 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate represented by the following formula (A) with an organic peroxy acid to obtain a reaction product. In this process, a reaction product containing the compound represented by the above formula (1) can be obtained.

[0051] [Chemical formula 4]

[0052]

[0053] Examples of the above-mentioned organic peroxy acid include: performic acid, peracetic acid, perpropionic acid, m-chloroperbenzoic acid, trifluoroperacetic acid, perbenzoic acid, etc. The above-mentioned organic peroxy acid can be used alone or in combination of two or more.

[0054] The usage amount of the organic peroxy acid is, for example, 0.5 to 3 moles relative to 1 mole of 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate.

[0055] The epoxidation reaction can be carried out in the presence of a solvent. Examples of the above-mentioned solvent include: aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, diethylbenzene, and p-cymene; alicyclic hydrocarbons such as cyclohexane and decalin; aliphatic hydrocarbons such as n-hexane, heptane, octane, nonane, and decane; alcohols such as cyclohexanol, hexanol, heptanol, octanol, nonanol, and furfuryl alcohol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; esters such as ethyl acetate, n-amyl acetate, cyclohexyl acetate, isopentyl propionate, and methyl benzoate; polyhydric alcohols and their derivatives such as ethylene glycol, propylene glycol, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether, and diethylene glycol monoethyl ether; halogen compounds such as chloroform, dimethyl chloride, carbon tetrachloride, and chlorobenzene; ethers such as 1,2-dimethoxyethane, etc. The above-mentioned solvents can be used alone or in combination of two or more.

[0056] The usage amount of the solvent is, for example, about 0.2 to 10 times the mass of 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate.

[0057] In the epoxidation reaction, stabilizers of organic peroxyacids (such as ammonium hydrogen phosphate, potassium pyrophosphate, 2-ethylhexyl tripolyphosphate, etc.), inhibitors (such as hydroquinone, piperidine, ethanolamine, phenothiazine, etc.) can be used as needed.

[0058] The reaction temperature of the epoxidation reaction is, for example, 0 to 70 °C. As the reaction atmosphere, there is no particular limitation as long as the reaction is not hindered. For example, it can be any one of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, etc.

[0059] (2) Water washing process

[0060] The above water washing process is a process of removing the organic peroxyacid and the organic acid as its decomposition product contained in the reaction product obtained through the epoxidation process by water washing.

[0061] As the usage amount of water, it is, for example, about 0.1 to 3 times (v / v) of the reaction product. Water washing can be carried out using a balance type extractor such as a mixer settler type, an extraction tower, a centrifugal extractor, etc.

[0062] (3) Low-boiling component removal process

[0063] The above low-boiling component removal process is a process of distilling and removing the components having a boiling point lower than that of the compound represented by the above formula (1) (such as solvent, water, etc.) contained in the reaction product. By implementing this process, the content of the compounds having a molecular weight of 100 or less mixed in the epoxy compound product can be reduced to an extremely low level.

[0064] In the low-boiling component removal step, distillation can be carried out using a thin-film evaporator or a distillation column. The distillation is preferably carried out under the conditions of a heating temperature in the range of 50 to 200 °C and a pressure in the range of 1 to 760 torr. The distillation can also be carried out in two stages by changing the pressure and temperature.

[0065] When performing the low-boiling component removal step on the reaction product, from the aspect of suppressing the ring-opening polymerization reaction of the compound represented by the above formula (1), it is preferable to add a polymerization inhibitor. The addition amount of the polymerization inhibitor varies slightly depending on its type and the distillation temperature, but is preferably in the range of, for example, 1 to 10,000 mass ppm (especially 10 to 2,000 mass ppm) relative to the reaction product.

[0066] In the low-boiling component removal step, components having a boiling point lower than that of the compound represented by the above formula (1) are evaporated and removed from the reaction product, and a mixture of the compound represented by the above formula (1) and components having a boiling point higher than that thereof is obtained as a residual liquid.

[0067] (4) High-boiling component removal step

[0068] The above high-boiling component removal step is a step of distilling and removing components having a boiling point higher than that of the compound represented by the above formula (1) (such as solvents, moisture, etc.) contained in the reaction product by thin-film evaporation. When the above high-boiling component removal step is carried out after the above low-boiling component removal step, the above high-boiling component removal step is a step of evaporating and distilling the compound represented by the above formula (1) from the residual liquid obtained through the above low-boiling component removal step, that is, a mixture of the compound represented by the above formula (1) and components having a boiling point higher than that thereof. By carrying out this step, the content of compounds having a molecular weight of 290 or more and containing the compounds represented by the above formulas (a) to (d) mixed in the epoxy compound product can be reduced to an extremely low level.

[0069] Preferably, the above residual liquid is introduced into a distillation column, the compound represented by the above formula (1) is recovered as a top distillate, and the bottom liquid containing high-boiling components is discharged out of the system.

[0070] In consideration of obtaining the following effects [1] to [4] and thus obtaining the above epoxy compound product containing the compound represented by the above formula (1) with high purity, it is preferable that the treatment in the high-boiling component removal step is carried out under the above conditions.

[0071] [1] Suppress the reaction of an organic acid, which is a decomposition product of an organic peroxyacid, with the compound represented by the above formula (1) to by-produce the compound represented by the above formula (a).

[0072] [2] Suppress the decrease in the yield of the compound represented by the above formula (1) by suppressing the by-production of the compound represented by the above formula (a).

[0073] [3]Suppress the reaction of the organic acid, which is a decomposition product of the organic peroxyacid, with the by-produced compound represented by formula (a) to by-produce the compound represented by formula (c) and the compound represented by formula (d).

[0074] [4]Suppress the reaction of the organic acid, which is a decomposition product of the organic peroxyacid, with the unreacted 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate remaining as it is to by-produce the compound represented by formula (b).

[0075] As the distillation column, a packed column, a plate column, etc. can be used, for example. The actual number of plates of the distillation column is, for example, 14 or more, and from the aspect of being able to suppress the mixing of the compounds represented by formulas (a) to (d) and further improve the purity of the product, it is preferably 14 to 100 plates, and particularly preferably 14 to 50 plates.

[0076] In the high-boiling component removal step, thin-film evaporators can be used for distillation. The distillation is carried out under the conditions of a heating temperature of 250 °C or lower (preferably 230 °C or lower) and a pressure of 3 torr or higher (preferably 0.7 torr or lower), which is preferable in terms of suppressing the decomposition of the compound represented by the above formula (1) and the increase in the coloring degree and the ring-opening polymerization of the epoxy group of the compound represented by the above formula (1) to cause gelation. The distillation temperature is preferably 170 °C or higher, and more preferably 180 °C or higher. From the viewpoint of being able to further improve the purity of the above epoxy compound product, the above pressure is preferably 0.01 torr or higher, and can also be 0.02 torr or higher. In addition, from the viewpoint of being able to further suppress the by-production of the compounds represented by the above formulas (a) to (d), the above pressure is preferably 0.5 Torr or lower, more preferably 0.2 Torr or lower, further preferably 0.16 Torr or lower, further preferably 0.1 Torr or lower, and particularly preferably 0.04 Torr or lower.

[0077] The wiping speed is preferably 100 to 800 rpm, and more preferably 200 to 600 rpm. If the wiping speed is too high, there is a tendency for the energy cost to become high. On the contrary, if the wiping speed is too low, there is a tendency for the compounds represented by formulas (a) to (d) to easily mix into the product.

[0078] The above-mentioned epoxy compound products have been difficult to manufacture by simply repeating distillation. The reason is that, especially in the distillation for separating high-boiling components, the compound represented by the above formula (1) and 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate, which is a precursor of the compound represented by the above formula (1), react with the organic acid that is a decomposition product of the organic peroxy acid upon heating to reproduce the compounds represented by the above formulas (a) to (d). Moreover, the boiling point of the compound represented by the above formula (1) is higher than that of 3,4-epoxycyclohexylmethyl (3',4'-epoxy) cyclohexanecarboxylate, and distillation needs to be carried out at a relatively high temperature. Therefore, in the high-boiling component removal step, the reaction to generate the compounds represented by the above formulas (a) to (d) is more likely to occur, and as a result, the purity of the obtained epoxy compound product is likely to decrease. However, by performing thin-film distillation in the high-boiling component removal step, the compound represented by the above formula (1) can be efficiently volatilized without excessive heating temperature, so the reaction to generate the compounds represented by the above formulas (a) to (d) in the high-boiling component removal step can be suppressed, and a high-purity epoxy compound product can be obtained. In addition, by controlling the pressure in the high-boiling component removal step, an epoxy compound product with higher purity can be obtained.

[0079] [Curable Composition]

[0080] The compound represented by the above formula (1) is a curable compound, and a curable composition can be obtained using the above-mentioned epoxy compound product. The curable composition contains the above-mentioned epoxy compound product.

[0081] (Curable Compound)

[0082] The curable composition contains at least the compound represented by the above formula (1) contained in the above-mentioned epoxy compound product as a curable compound. The curable composition may also contain other curable compounds in addition to the compound represented by the above formula (1). The above-mentioned other curable compounds may be only one kind or two or more kinds.

[0083] Examples of the above-mentioned other curable compounds include: other epoxy compounds other than the compound represented by the above formula (1), compounds having one or more oxetanyl groups in the molecule (sometimes referred to as "oxetane compounds"), compounds having one or more vinyl ether groups in the molecule (sometimes referred to as "vinyl ether compounds"), etc. The curable composition may also contain the above-mentioned other epoxy compounds and / or oxetane compounds as the above-mentioned other compounds.

[0084] The above-mentioned other epoxy compounds are compounds having one or more epoxy groups (oxiranyl groups) in the molecule. Among them, as the above-mentioned other epoxy compounds, compounds having two or more (preferably 2 to 6, more preferably 2 to 4) epoxy groups in the molecule are preferred.

[0085] Examples of the above-mentioned other epoxy compounds include alicyclic epoxy compounds, aromatic epoxy compounds, aliphatic epoxy compounds, etc.

[0086] Examples of the above-mentioned alicyclic epoxy compounds include known or conventional compounds having one or more alicyclic rings and one or more epoxy groups in the molecule, without particular limitation. For example, they include: (I) compounds having an epoxy group (referred to as "alicyclic epoxy group") formed by two adjacent carbon atoms and an oxygen atom constituting the alicyclic ring in the molecule; (II) compounds having an epoxy group directly bonded to the alicyclic ring by a single bond; (III) compounds having an alicyclic ring and a glycidyl ether group in the molecule (glycidyl ether type epoxy compound), etc.

[0087] Examples of the above-mentioned (I) compounds having an alicyclic epoxy group in the molecule include the compounds represented by the following formula (i).

[0088] [Chemical formula 5]

[0089]

[0090] In the above formula (i), Y represents a single bond or a linking group (a divalent group having one or more atoms). Examples of the above-mentioned linking group include, for example, a divalent hydrocarbon group, a vinylene group in which part or all of the carbon-carbon double bond is epoxidized, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide group, a group formed by linking a plurality of them, etc. It should be noted that one or more of the carbon atoms constituting the cyclohexane ring (epoxycyclohexyl) in formula (i) are optionally bonded to a substituent such as an alkyl group.

[0091] Examples of the above-mentioned divalent hydrocarbon group include linear or branched alkylene groups having 1 to 18 carbon atoms, divalent alicyclic hydrocarbon groups, etc. Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include, for example, methylene, methylmethylene, dimethylmethylene, ethylene, propylene, trimethylene, etc. Examples of the above-mentioned divalent alicyclic hydrocarbon group include, for example, 1,2-cyclopentylene, 1,3-cyclopentylene, cyclopentylidene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, cyclohexylidene and other divalent cycloalkyl groups (including cycloalkylidene).

[0092] As the alkenylene group (sometimes referred to as "epoxidized alkenylene group") in which part or all of the above carbon-carbon double bonds are epoxidized, for example, the following can be cited: vinylidene, propenylene, 1-butenylene, 2-butenylene, butadienylene group, pentenylene, hexenylene, heptenylene, octenylene, etc., linear or branched alkenylene groups having 2 to 8 carbon atoms. In particular, as the above epoxidized alkenylene group, an alkenylene group in which all of the carbon-carbon double bonds are epoxidized is preferred, and an alkenylene group having 2 to 4 carbon atoms in which all of the carbon-carbon double bonds are epoxidized is more preferred.

[0093] As representative examples of the alicyclic epoxy compound represented by the above formula (i), (3,4,3',4'-diepoxy)bicyclohexane, compounds represented by the following formula (i-1) to formula (i-9), etc. can be cited. It should be noted that l and m in the following formula (i-4) and formula (i-6) respectively represent integers of 1 to 30. R' in the following formula (i-4) is an alkylene group having 1 to 8 carbon atoms, and among them, linear or branched alkylene groups having 1 to 3 carbon atoms such as methylene, ethylene, propylene, and isopropyl are preferred. n1 to n6 in the following formula (i-8) and formula (i-9) respectively represent integers of 1 to 30. In addition, as the alicyclic epoxy compound represented by the above formula (i), for example, 2,2-bis(3,4-epoxycyclohexyl)propane, 1,2-bis(3,4-epoxycyclohexan-1-yl)ethane, 1,2-epoxy-1,2-bis(3,4-epoxycyclohexan-1-yl)ethane, bis(3,4-epoxycyclohexylmethyl)ether, etc. can also be cited.

[0094] [Chemical formula 6]

[0095]

[0096] [Chemical formula 7]

[0097]

[0098] In addition, as the compound having an alicyclic epoxy group in the molecule of the above (I), epoxy-modified silicone can be cited. As the above epoxy-modified silicone, for example, linear or cyclic polyorganosiloxanes having a structural unit represented by the following formula (i') can be cited.

[0099] [Chemical formula 8]

[0100]

[0101] In the above formula (i'), R 3 represents a substituent containing a group represented by the following formula (1a) or a substituent containing a group represented by the following formula (1b), R 4represents an alkyl group or an alkoxy group.

[0102] [Chemical Formula 9]

[0103]

[0104] In Formula (1a) and Formula (1b), R 1a , R 1b are the same or different and represent a linear or branched alkylene group. For example, examples thereof include linear or branched alkylene groups having 1 to 10 carbon atoms such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, and decamethylene.

[0105] The epoxy equivalent (based on JIS K7236) of the above epoxy-modified silicone is, for example, 100 to 400, preferably 150 to 300.

[0106] As the above epoxy-modified silicone, for example, commercially available products such as the compound represented by the following formula (i'-1) (trade name “KR-470”, manufactured by Shin-Etsu Chemical Co., Ltd.) can be used.

[0107] [Chemical Formula 10]

[0108]

[0109] As the compound in which an epoxy group is directly bonded to the alicyclic ring in the above (II), for example, the compound represented by the following formula (ii) can be cited.

[0110] [Chemical Formula 11]

[0111]

[0112] In Formula (ii), R" is a group formed by removing p hydroxyl groups (-OH) from the structural formula of a p-valent alcohol (p-valent organic group), and p and n each represent a natural number. As the p-valent alcohol [R"(OH) p , polyhydric alcohols such as 2,2-bis(hydroxymethyl)-1-butanol (alcohols having 1 to 15 carbon atoms, etc.) can be cited. p is preferably 1 to 6, and n is preferably 1 to 30. When p is 2 or more, n in the groups within each () (inside the outer parentheses) can be the same or different. As the compound represented by the above formula (ii), specifically, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol [for example, trade name “EHPE3150” (manufactured by Daicel Corporation), etc.] can be cited.

[0113] As the compound having an alicyclic ring and a glycidyl ether group in the molecule of the above (III), for example, the glycidyl ether of an alicyclic alcohol (especially an alicyclic polyol) can be cited. More specifically, for example, 2,2-bis[4-(2,3-epoxypropoxy)cyclohexyl]propane, 2,2-bis[3,5-dimethyl-4-(2,3-epoxypropoxy)cyclohexyl]propane and other compounds obtained by hydrogenating a bisphenol A type epoxy compound (hydrogenated bisphenol A type epoxy compound); bis[o,o-(2,3-epoxypropoxy)cyclohexyl]methane, bis[o,p-(2,3-epoxypropoxy)cyclohexyl]methane, bis[p,p-(2,3-epoxypropoxy)cyclohexyl]methane, bis[3,5-dimethyl-4-(2,3-epoxypropoxy)cyclohexyl]methane and other compounds obtained by hydrogenating a bisphenol F type epoxy compound (hydrogenated bisphenol F type epoxy compound); hydrogenated biphenol type epoxy compound; hydrogenated phenol novolak type epoxy compound; hydrogenated cresol novolak type epoxy compound; hydrogenated cresol novolak type epoxy compound of bisphenol A; hydrogenated naphthalene type epoxy compound; hydrogenated epoxy compound of an epoxy compound obtained from triphenylmethane; hydrogenated epoxy compound of other epoxy compounds having an aromatic ring, etc.

[0114] The above aromatic epoxy compound is a compound having one or more aromatic rings (aromatic hydrocarbon ring or aromatic heterocyclic ring) and one or more epoxy groups in the molecule. Among the aromatic epoxy compounds, a compound in which one or more carbon atoms constituting an aromatic ring having a carbon atom (especially an aromatic hydrocarbon ring) are bonded to a glycidoxy group (aromatic glycidyl ether type epoxy compound) is preferred.

[0115] As the above aromatic epoxy compound, for example, an Epi-Bis type glycidyl ether type epoxy resin obtained by the condensation reaction of bisphenols [for example, bisphenol A, bisphenol F, bisphenol S, bisphenol fluorene, etc.] and epihalohydrin can be cited; a high molecular weight Epi-Bis type glycidyl ether type epoxy resin obtained by further adding these Epi-Bis type glycidyl ether type epoxy resins to the above bisphenols; polyols obtained by the condensation reaction of phenols [for example, phenol, cresol, xylenol, resorcinol, catechol, bisphenol A, bisphenol F, bisphenol S, etc.] and aldehydes [for example, formaldehyde, acetaldehyde, benzaldehyde, hydroxybenzaldehyde, salicylaldehyde, etc.], and a novolak / alkyl type glycidyl ether type epoxy resin obtained by further condensing the polyols with epihalohydrin; an epoxy compound in which two phenolic skeletons are bonded to the 9-position of a fluorene ring, and the oxygen atoms after removing hydrogen atoms from the hydroxyl groups of these phenolic skeletons are directly or via an alkyleneoxy group bonded to a glycidyl group, etc.

[0116] As the above-mentioned aliphatic epoxy compounds, examples thereof include: glycidyl ethers of q-valent alcohols (q is a natural number) without a cyclic structure; glycidyl esters of mono- or polycarboxylic acids [such as acetic acid, propionic acid, butyric acid, stearic acid, adipic acid, sebacic acid, maleic acid, itaconic acid, etc.]; epoxides of oils having double bonds such as epoxidized linseed oil, epoxidized soybean oil, epoxidized castor oil; epoxides of polyolefins (including polyalkyl dienes) such as epoxidized polybutadiene, etc. It should be noted that as the above-mentioned q-valent alcohols without a cyclic structure, examples thereof include: monohydric alcohols such as methanol, ethanol, 1-propanol, isopropanol, 1-butanol; dihydric alcohols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol; polyhydric alcohols having three or more hydroxyl groups such as glycerol, diglycerol, erythritol, trimethylolethane, trimethylolpropane, pentaerythritol, dipentaerythritol, sorbitol, etc. In addition, the q-valent alcohol may be a polyether polyol, a polyester polyol, a polycarbonate polyol, a polyolefin polyol, etc.

[0117] As the above-mentioned oxetane compounds, known or commonly used compounds having one or more oxetane rings in the molecule can be cited, and there is no particular limitation. For example, 3,3-bis(ethenyloxymethyl)oxetane, 3-ethyl-3-(hydroxymethyl)oxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-[(phenoxy)methyl]oxetane, 3-ethyl-3-(hexyloxymethyl)oxetane, 3-ethyl-3-(chloromethyl)oxetane, 3,3-bis(chloromethyl)oxetane, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, bis{[1-ethyl(3-oxetanyl)]methyl}ether, 4,4'-bis[(3-ethyl-3-oxetanyl)methoxymethyl]bicyclohexane, 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]cyclohexane, 1,4-bis{[(3-ethyl-3-oxetanyl)methoxy]methyl}benzene, 3-ethyl-3-{[(3-ethyloxetane-3-yl)methoxy]methyl}oxetane, benzenedimethylenedioxetane, 3-ethyl-3-{[3-(triethoxysilyl)propoxy]methyl}oxetane, oxetanyl sesquisiloxane, phenol novolac oxetane, etc.

[0118] As the above vinyl ether compound, a known or conventional compound having one or more vinyl ether groups in the molecule can be used, and there is no particular limitation. For example, the following can be cited: 2-hydroxyethyl vinyl ether (ethylene glycol mono vinyl ether), 3-hydroxypropyl vinyl ether, 2-hydroxypropyl vinyl ether, 2-hydroxyisopropyl vinyl ether, 4-hydroxybutyl vinyl ether, 3-hydroxybutyl vinyl ether, 2-hydroxybutyl vinyl ether, 3-hydroxyisobutyl vinyl ether, 2-hydroxyisobutyl vinyl ether, 1-methyl-3-hydroxypropyl vinyl ether, 1-methyl-2-hydroxypropyl vinyl ether, 1-hydroxymethylpropyl vinyl ether, 4-hydroxycyclohexyl vinyl ether, 1,6-hexanediol mono vinyl ether, 1,6-hexanediol divinyl ether, 1,8-octanediol divinyl ether, 1,4-cyclohexanedimethanol mono vinyl ether, 1,4-cyclohexanedimethanol divinyl ether, 1,3-cyclohexanedimethanol mono vinyl ether, 1,3-cyclohexanedimethanol divinyl ether, 1,2-cyclohexanedimethanol mono vinyl ether, 1,2-cyclohexanedimethanol divinyl ether, p-xylene glycol mono vinyl ether, p-xylene glycol divinyl ether, m-xylene glycol mono vinyl ether, m-xylene glycol divinyl ether, o-xylene glycol mono vinyl ether, o-xylene glycol divinyl ether, ethylene glycol divinyl ether, diethylene glycol mono vinyl ether, diethylene glycol divinyl ether, triethylene glycol mono vinyl ether, triethylene glycol divinyl ether, tetraethylene glycol mono vinyl ether, tetraethylene glycol divinyl ether, pentaethylene glycol mono vinyl ether, pentaethylene glycol divinyl ether, oligoethylene glycol mono vinyl ether, oligoethylene glycol divinyl ether, polyethylene glycol mono vinyl ether, polyethylene glycol divinyl ether, dipropylene glycol mono vinyl ether, dipropylene glycol divinyl ether, tripropylene glycol mono vinyl ether, tripropylene glycol divinyl ether, tetrapropylene glycol mono vinyl ether, tetrapropylene glycol divinyl ether, pentapropylene glycol mono vinyl ether, pentapropylene glycol divinyl ether, oligopropylene glycol mono vinyl ether, oligopropylene glycol divinyl ether, polypropylene glycol mono vinyl ether, polypropylene glycol divinyl ether, isosorbide divinyl ether, oxanorbornene divinyl ether, phenyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, octyl vinyl ether, cyclohexyl vinyl ether, hydroquinone divinyl ether, 1,4-butanediol divinyl ether, cyclohexanedimethanol divinyl ether, trimethylolpropane divinyl ether, trimethylolpropane trivinyl ether, bisphenol A divinyl ether, bisphenol F divinyl ether, hydroxyoxanorbornane methanol divinyl ether, 1,4-cyclohexanediol divinyl ether, pentaerythritol trivinyl ether, pentaerythritol tetravinyl ether, dipentaerythritol pentavinyl ether, dipentaerythritol hexavinyl ether, etc.

[0119] The proportion of the compound represented by the above formula (1) in the total amount (100% by mass) of the curable compounds contained in the above curable composition is, for example, 50% by mass or more (e.g., 50 to 100% by mass), preferably 60% by mass or more, more preferably 70% by mass or more, and further preferably 80% by mass or more.

[0120] The above curable composition preferably contains, in addition to the curable compound, for example, one or more selected from the group consisting of a curing agent, a curing accelerator, and a curing catalyst. The above curable composition preferably contains a curing agent and / or a curing catalyst.

[0121] The total content ratio of the curable compound, the curing agent, and / or the curing accelerator in the total amount (100% by mass) of the above curable composition is, for example, 60% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and particularly preferably 95% by mass or more.

[0122] The total content ratio of the curable compound and the curing catalyst in the total amount (100% by mass) of the above curable composition is, for example, 60% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and particularly preferably 95% by mass or more.

[0123] With respect to the total amount (100% by mass) of the above curable composition, the content ratio of the compounds other than the curable compound, the curing agent, the curing accelerator, and the curing catalyst is, for example, 50% by mass or less, preferably 40% by mass or less.

[0124] (Curing agent)

[0125] As the above curing agent, for example, acid anhydrides (acid anhydride-based curing agents), amines (amine-based curing agents), polyamide resins, imidazoles (imidazole-based curing agents), polythiols (polythiol-based curing agents), phenols (phenol-based curing agents), polycarboxylic acids, dicyandiamides, organic acid hydrazides, etc., which are known or commonly used as curing agents for epoxy resins, can be used. The above curing agent can be used alone or in combination of two or more.

[0126] As the above-mentioned acid anhydrides, for example, the following can be cited: methyltetrahydrophthalic anhydride (4-methyltetrahydrophthalic anhydride, 3-methyltetrahydrophthalic anhydride, etc.), methylhexahydrophthalic anhydride (4-methylhexahydrophthalic anhydride, 3-methylhexahydrophthalic anhydride, etc.), dodecenyl succinic anhydride, methylendomethylene tetrahydrophthalic anhydride, phthalic anhydride, maleic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylcyclohexene dicarboxylic anhydride, pyromellitic dianhydride, trimellitic anhydride, benzophenone tetracarboxylic dianhydride, nadic anhydride, methyl nadic anhydride, hydrogenated methyl nadic anhydride, 4-(4-methyl-3-pentenyl)tetrahydrophthalic anhydride, succinic anhydride, adipic anhydride, sebacic anhydride, dodecanedioic anhydride, methylcyclohexene tetracarboxylic dianhydride, vinyl ether-maleic anhydride copolymer, alkylstyrene-maleic anhydride copolymer, etc. Among them, from the viewpoint of operability, an acid anhydride that is liquid at 25 °C is preferably used [for example, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, dodecenyl succinic anhydride, methylendomethylene tetrahydrophthalic anhydride, etc.].

[0127] As the above-mentioned amines, for example, the following can be cited: aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenediamine, diethylaminopropylamine, polypropylenetriamine; alicyclic polyamines such as menthene diamine, isophorone diamine, bis(4-amino-3-methylcyclohexyl)methane, diaminodicyclohexylmethane, bis(aminomethyl)cyclohexane, N-aminoethylpiperazine, 3,9-bis(3-aminopropyl)-3,4,8,10-tetraoxaspiro[5,5]undecane; mononuclear polyamines such as m-phenylenediamine, p-phenylenediamine, toluene-2,4-diamine, toluene-2,6-diamine, mesitylene-2,4-diamine, 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine; aromatic polyamines such as biphenylenediamine, 4,4-diaminodiphenylmethane, 2,5-naphthalenediamine, 2,6-naphthalenediamine, etc.

[0128] As the above-mentioned polyamide resin, for example, a polyamide resin having either or both of a primary amino group and a secondary amino group in the molecule can be cited.

[0129] As the above-mentioned imidazoles, for example, the following can be cited: 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2-methylimidazolium isocyanurate, 2-phenylimidazolium isocyanurate, 2,4-diamino-6-[2-methylimidazolyl-(1)]-ethyl-s-triazine, 2,4-diamino-6-[2-ethyl-4-methylimidazolyl-(1)]-ethyl-s-triazine, etc.

[0130] As the above-mentioned polythiols, for example, the following can be cited: liquid polythiols, polysulfide resins, etc.

[0131] As the above-mentioned phenols, for example, the following can be cited: novolak-type phenolic resins, novolak-type cresol resins, aralkyl resins such as p-phenylenedimethyl-modified phenolic resins, p-phenylenedimethyl / m-phenylenedimethyl-modified phenolic resins, terpene-modified phenolic resins, dicyclopentadiene-modified phenolic resins, triphenolpropane, etc.

[0132] As the above-mentioned polycarboxylic acids, for example, the following can be cited: adipic acid, sebacic acid, terephthalic acid, trimellitic acid, carboxyl group-containing polyesters, etc.

[0133] As the curing agent, from the viewpoints of the heat resistance and transparency of the obtained cured product, acid anhydrides (acid anhydride-based curing agents) are preferably used. For example, commercially available products such as the trade names "RIKACID MH-700" and "RIKACID MH-700F" (both manufactured by Shin Nippon Rika Co., Ltd.) and the trade name "HN-5500" (manufactured by Hitachi Chemical Co., Ltd.) can be used.

[0134] The content (mixing amount) of the curing agent is preferably 50 to 200 parts by mass, more preferably 80 to 150 parts by mass, relative to 100 parts by mass of the total amount of the epoxy compounds contained in the curable composition. More specifically, when using acid anhydrides as the curing agent, it is preferably used in a ratio of 0.5 to 1.5 equivalents per 1 equivalent of the epoxy groups in all the epoxy compounds contained in the above-mentioned curable composition. If the content of the curing agent is 50 parts by mass or more, the curing can proceed sufficiently, and there is a tendency for the toughness of the obtained cured product to increase. On the other hand, if the content of the curing agent is 200 parts by mass or less, there is a tendency for further suppression of coloring and for obtaining a cured product with excellent hue.

[0135] (Curing accelerator)

[0136] When the above curable composition contains a curing agent, it preferably further contains a curing accelerator. The curing accelerator has the following effect: when a compound having an epoxy group (oxiranyl group) reacts with the curing agent, it promotes the reaction rate.

[0137] Examples of the above curing accelerator include 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or its salts (such as phenolate, octoate, p-toluenesulfonate, formate, tetraphenylborate, etc.), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or its salts (such as phenolate, octoate, p-toluenesulfonate, formate, tetraphenylborate, etc.); tertiary amines such as benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, N,N-dimethylcyclohexylamine; imidazoles such as 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole; phosphate esters; phosphines such as triphenylphosphine, tris(dimethoxy)phosphine; phosphonium compounds such as tetraphenylphosphonium tetrakis(p-tolyl)borate; organometallic salts such as zinc octoate, tin octoate, zinc stearate; metal chelates such as aluminum acetylacetonate complex, etc. The above curing accelerator can be used alone or in combination of two or more.

[0138] Examples of the above curing accelerator that can be used include commercially available products such as the trade names "U-CAT SA 506", "U-CAT SA 102", "U-CAT 5003", "U-CAT 18X", "U-CAT 12XD" (development products) (above, manufactured by San-Apro Ltd.); the trade names "TPP-K", "TPP-MK" (above, manufactured by Kitakyo Chemical Industry Co., Ltd.); the trade name "PX-4ET" (manufactured by Nippon Chemical Industry Co., Ltd.).

[0139] The content (blending amount) of the above curing accelerator is preferably 0.01 to 5 parts by mass, more preferably 0.02 to 3 parts by mass, and still more preferably 0.03 to 3 parts by mass with respect to 100 parts by mass of the curing agent. If the content of the curing accelerator is 0.01 part by mass or more, there is a tendency to obtain a more efficient curing promotion effect. On the other hand, if the content of the curing accelerator is 5 parts by mass or less, there is a tendency to further suppress coloring and obtain a cured product with excellent hue.

[0140] (Curing catalyst)

[0141] The above curable composition may also contain a curing catalyst instead of a curing agent. The curing catalyst has the effect of curing the curable composition by initiating and / or promoting the curing reaction (polymerization reaction) of a cationically curable compound such as the compound represented by the above formula (1). Examples of the curing catalyst include cationic polymerization initiators (photo cationic polymerization initiators, thermal cationic polymerization initiators, etc.) that generate cationic species by performing light irradiation, heat treatment, etc. to initiate polymerization, Lewis acid-amine complexes, Bronsted acid ( acid) salts, imidazoles, etc. The above curing catalyst may be used alone or in combination of two or more.

[0142] Examples of the above photo cationic polymerization initiator include hexafluoroantimonate, pentafluoro-hydroxyantimonate, hexafluorophosphate, hexafluoroarsenate, etc. More specifically, examples include sulfonium salts such as triaryl sulfonium hexafluorophosphate (e.g., p-phenylthiophenyldiphenylsulfonium hexafluorophosphate, etc.), triaryl sulfonium hexafluoroantimonate, etc. (especially triaryl sulfonium salts); iodonium salts such as diaryl iodonium hexafluorophosphate, diaryl iodonium hexafluoroantimonate, bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, iodonium [4-(4-methylphenyl-2-methylpropyl)phenyl] hexafluorophosphate, etc.; phosphonium salts such as tetrafluorophosphonium hexafluorophosphate; pyridinium salts such as N-hexylpyridinium tetrafluoroborate, etc. In addition, as the photo cationic polymerization initiator, for example, commercially available products such as the trade name "UVACURE1590" (manufactured by DAICEL-ALLNEX Co., Ltd.); trade names "CD-1010", "CD-1011", "CD-1012" (above, manufactured by Sartomer Company, USA); trade name "Irgacure 264" (manufactured by BASF); trade name "CIT-1682" (manufactured by Nippon Soda Co., Ltd.) can be preferably used.

[0143] Examples of the above cationic polymerization initiator include aryl diazonium salts, aryl iodonium salts, aryl sulfonium salts, allene-ion complexes, etc. Commercially available products such as the trade names "PP-33", "CP-66", "CP-77" (above, manufactured by ADEKA Corporation); trade name "FC-509" (manufactured by 3M); trade name "UVE1014" (manufactured by G.E.); trade names "SAN-AID SI-60L", "SAN-AID SI-80L", "SAN-AID SI-100L", "SAN-AID SI-110L", "SAN-AID SI-150L" (above, manufactured by Sanshin Chemical Industry Co., Ltd.); trade name "CG-24-61" (manufactured by BASF) can be preferably used.

[0144] Examples of the above Lewis acid-amine complex include BF 3- n-Hexylamine, BF 3 - Monoethylamine, BF 3 - Benzylamine, BF 3 - Diethylamine, BF 3 - Piperidine, BF 3 - Triethylamine, BF 3 - Aniline, BF 4 - n-Hexylamine, BF 4 - Monoethylamine, BF 4 - Benzylamine, BF 4 - Diethylamine, BF 4 - Piperidine, BF 4 - Triethylamine, BF 4 - Aniline, PF 5 - Ethylamine, PF 5 - Isopropylamine, PF 5 - Butylamine, PF 5 - Laurylamine, PF 5 - Benzylamine, AsF 5 - Laurylamine, etc.

[0145] As the above-mentioned Bronsted acid salts, for example, aliphatic sulfonium salts, aromatic sulfonium salts, iodonium salts, phosphonium salts, etc. can be cited.

[0146] As the above-mentioned imidazoles, for example, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-undecylimidazolium trimesate, 1-cyanoethyl-2-phenylimidazolium trimesate, 2-methylimidazolium isocyanurate, 2-phenylimidazolium isocyanurate, 2,4-diamino-6-[2-methylimidazolyl-(1)]-ethyl-s-triazine, 2,4-diamino-6-[2-ethyl-4-methylimidazolyl-(1)]-ethyl-s-triazine, etc. can be cited.

[0147] The content (mixing amount) of the above-mentioned curing catalyst is preferably 0.01 to 5 parts by mass, more preferably 0.02 to 4 parts by mass, and further preferably 0.03 to 3 parts by mass with respect to 100 parts by mass of the cation-curable compound contained in the curable composition. If the content of the curing catalyst is within the above range, there is a tendency that the curing rate of the curable composition is increased and the balance between the heat resistance and transparency of the cured product is improved well.

[0148] In addition to containing the above-described respective components, the above curable composition may contain additives as needed. Examples of the above additives include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerol; defoamers, leveling agents, silane coupling agents, surfactants, inorganic fillers, flame retardants, colorants, ion adsorbents, pigments, phosphors, release agents, and the like. The above additives may be used singly or in combination of two or more.

[0149] The above curable composition can be prepared by stirring / mixing the above-described respective components in a heated state as needed. The above stirring / mixing can be carried out, for example, using the following known or conventional stirring / mixing units: various mixers such as dissolvers and homogenizers; kneaders; roll mills; bead mills; rotation-revolution type stirring devices, and the like. In addition, defoaming can be carried out under vacuum after stirring / mixing.

[0150] In the above curable composition, relative to the total amount (100% by mass) of the compound represented by the above formula (1), the compound represented by the above formula (a), the compound represented by the above formula (b), the compound represented by the above formula (c), and the compound represented by the above formula (d), the proportion of the compound represented by the above formula (1) is 90% by mass or more, preferably 91% by mass or more, more preferably 94% by mass or more, and further preferably 96% by mass or more. The above proportion can be calculated based on the proportion of the peak areas obtained by GC-MS.

[0151] In the above curable composition, relative to the total amount (100% by mass) of the compound represented by the above formula (1), the compound represented by the above formula (a), the compound represented by the above formula (b), the compound represented by the above formula (c), and the compound represented by the above formula (d), the total proportion of the compound represented by the above formula (a), the compound represented by the above formula (b), the compound represented by the above formula (c), and the compound represented by the above formula (d) is 10% by mass or less, preferably 9% by mass or less, more preferably 6% by mass or less, and further preferably 4% by mass or less. The above proportion can be calculated based on the proportion of the peak areas obtained by GC-MS.

[0152] The above curable composition has rapid curability, and the curing time (or gel time) at 120°C is, for example, 1100 seconds or less, preferably 1050 seconds or less. In addition, the curing time (or gel time) of the above curable composition at 80°C is, for example, 5000 seconds or less, preferably 4000 seconds or less, and more preferably 3000 seconds or less.

[0153] The heating temperature during curing (curing temperature) is preferably 45 to 200 °C, more preferably 100 to 190 °C, and still more preferably 100 to 180 °C. In addition, the heating time (or curing time) is preferably 30 to 600 minutes, more preferably 45 to 540 minutes. If the heating temperature and heating time are below the above ranges, curing will be insufficient. On the contrary, if the heating temperature and heating time are above the above ranges, decomposition of the resin component may sometimes occur, so neither is preferred. The curing conditions depend on various conditions. For example, appropriate adjustment can be made by shortening the heating time when increasing the heating temperature and extending the heating time when decreasing the heating temperature, etc.

[0154] [Cured product]

[0155] A cured product is obtained by curing the above curable composition. The cured product has excellent transparency and heat resistance.

[0156] The cured product has excellent transparency, and its light transmittance (thickness 3 mm) at a wavelength of 450 nm is preferably 80% or more, more preferably 85% or more, still more preferably 88% or more, and particularly preferably 90% or more. Since the above curable composition forms a cured product with excellent transparency, when used as a sealant for optical semiconductor elements, a chip mounting paste, etc. in an optical semiconductor device, there is a tendency for the luminous intensity emitted from the optical semiconductor device to be further increased.

[0157] The cured product has excellent heat resistance, and its glass transition temperature (Tg) is preferably 170 °C or higher, more preferably 175 °C or higher, still more preferably 180 °C or higher, still more preferably 190 °C or higher, and particularly preferably 200 °C or higher.

[0158] The cured product has excellent heat resistance, and its 5% weight loss temperature (Td5) is preferably 325 °C or higher, more preferably 330 °C or higher, still more preferably 335 °C or higher. In addition, the 10% weight loss temperature (Td10) of the above cured product is preferably 355 °C or higher, more preferably 360 °C or higher.

[0159] The curing shrinkage rate of the above cured product is preferably 1.5% or less, more preferably 1.2% or less, and still more preferably 1.1% or less. The above curing shrinkage rate is obtained by measuring the densities of the curable composition before curing and the cured product, and based on the following formula, according to the density change.

[0160] Volume shrinkage rate r = {(ds - dl) / dl} × 100

[0161] dl: Specific gravity of the liquid before curing. Measured using the density hydrometer "DA-640" (manufactured by Kyoto Electronics Industry Co., Ltd.).

[0162] ds: Specific gravity of the solid after curing. Measured by the solid specific gravity measurement method.

[0163] The above curable composition can be used, for example, in various applications such as sealants, adhesives, coating agents, electrical insulating materials, laminates, ink liquids, sealants, resists, composite materials, transparent substrates, transparent sheets, transparent films, optical elements, optical lenses, stereolithography, electronic paper, touch panels, solar cell substrates, optical waveguides, light guide plates, holographic memories, and the like.

[0164] [Sealant]

[0165] The above sealant contains the above curable composition. The above sealant can preferably be used for sealing a photonic semiconductor (photonic semiconductor element) in a photonic semiconductor device. When the above sealant is used, a photonic semiconductor element can be sealed with a cured product (=sealing material) having excellent transparency and heat resistance and less likely to cause curing shrinkage.

[0166] With respect to the total amount (100% by mass) of the above sealant, the content ratio of the above curable composition is preferably 50% by mass or more, more preferably 60% by mass or more, and further preferably 70% by mass or more. The above sealant can also be formed only of the above curable composition.

[0167] [Adhesive]

[0168] The above adhesive contains the above curable composition. The above adhesive can be used for bonding / fixing members and the like to adherends. Specifically, it can be used in various applications that require excellent transparency, heat resistance, and less likely to cause curing shrinkage: a die attach paste for bonding and fixing a photonic semiconductor element to a metal electrode in a photonic semiconductor device; a lens adhesive for fixing a lens of a camera or the like to an adherend or for bonding lenses to each other; an optical film adhesive for fixing an optical film (e.g., a polarizing plate, a polarizing plate protective film, a retardation film, etc.) to an adherend, or for bonding optical films to each other or for bonding an optical film to another film.

[0169] The above adhesive can be particularly preferably used as a die attach paste (or die bonding agent). By using the above adhesive as a die attach paste, a photonic semiconductor device in which a photonic semiconductor element is bonded to an electrode with a cured product having excellent transparency and heat resistance can be obtained.

[0170] With respect to the total amount (100% by mass) of the above adhesive, the content ratio of the above curable composition is preferably 50% by mass or more, more preferably 60% by mass or more, and further preferably 70% by mass or more. The above adhesive can also be formed only of the above curable composition.

[0171] [Coating agent]

[0172] The above coating agent contains the above curable composition. The above coating agent can be used for various applications that particularly require excellent workability, transparency, and heat resistance.

[0173] With respect to the total amount of the above coating agent (100% by mass), the content ratio of the above curable composition is preferably 50% by mass or more, more preferably 60% by mass or more, and still more preferably 70% by mass or more. The above coating agent may also be formed only of the above curable composition.

[0174] [Optical member]

[0175] The above cured product can be used to obtain an optical member. The above optical member includes a cured product of the above curable composition. Examples of the above optical member include: an optical semiconductor device in which a light semiconductor element is sealed with the above cured product; an optical semiconductor device in which a light semiconductor element is bonded to an electrode with the above cured product; and an optical semiconductor device in which a light semiconductor element is bonded to an electrode with the above cured product and the light semiconductor element is sealed with the above cured product. Since the above optical member has a structure sealed and bonded with the above cured product, it has excellent heat resistance and high light extraction efficiency.

[0176] Each aspect disclosed in this specification can also be combined with any other features disclosed in this specification. Each structure and the combination of each structure in each embodiment are examples, and appropriate addition, omission, substitution, and other changes of the structure can be made without departing from the gist of the present disclosure. In addition, each invention of the present disclosure is not limited by the embodiments and the following examples, but is only limited by the patent claims.

[0177] Examples

[0178] Hereinafter, one embodiment of the present disclosure will be described in more detail based on examples, but the present disclosure is not limited by these examples.

[0179] Example 1

[0180] In a 20 L reactor made of SUS316 with a jacket equipped with a stirrer, after adding 5000 g of 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate, the temperature was raised to make the internal temperature 25°C. 13790 g of a 30% ethyl acetate solution of peracetic acid was added dropwise over 6 hours, and aging was carried out for 3 hours. During the addition dropwise and aging, the internal temperature was maintained at 30°C. Thus, 18790 g of a reaction crude liquid containing 3,4-epoxy-6-methyl-cyclohexylmethyl (3',4'-epoxy-6'-methyl) cyclohexyl formate was obtained.

[0181] (Water washing process)

[0182] The crude reaction solution obtained above was diluted 1.7-fold with ethyl acetate, and the diluted liquid was fed from the light liquid inlet to a centrifugal extractor and treated with a water washing liquid / crude reaction liquid ratio of 2. As a result, a light liquid was obtained from the light liquid outlet at a rate of 968 g / min, and a heavy liquid was obtained from the heavy liquid outlet at a rate of 2191 g / min.

[0183] (Low-boiling component removal process)

[0184] 100 parts by mass of the obtained light liquid was charged into a forced stirring type thin film evaporator with a heat transfer area of 0.034 m 2 , and while maintaining an operating pressure of 1 mmHg and a heating temperature of 170 °C, 35 parts by mass of a residual liquid was obtained from the bottom of the column.

[0185] (High-boiling component removal process)

[0186] The residual liquid discharged from the bottom of the column was charged at a charging flow rate of 15 - 20 mL / 5 min to the 15th layer from the bottom of a high-boiling component removal distillation column with a column diameter of 40 mm composed of 20 actual trays of perforated trays, and the heating temperature was maintained at 200 °C, the pressure at 0.17 - 0.19 Torr, and the wiper rotation speed at 400 rpm. As a result, a distillate was distilled out from the top of the high-boiling component removal distillation column at a distillate flow rate of 10 - 15 mL / min. The distillate from the top of the column was recovered as the alicyclic epoxy compound product 1 of Example 1.

[0187] Example 2

[0188] In the high-boiling component removal process, the pressure was changed to 0.075 - 0.15 Torr, and otherwise, the alicyclic epoxy compound product 2 of Example 2 was obtained in the same manner as in Example 1.

[0189] Example 3

[0190] In the high-boiling component removal process, the pressure was changed to 0.030 - 0.038 Torr, and otherwise, the alicyclic epoxy compound product 3 of Example 3 was obtained in the same manner as in Example 1.

[0191] Comparative Example 1

[0192] The high-boiling component removal process was not carried out, and otherwise, the alicyclic epoxy compound product 4 of Comparative Example 1 was obtained in the same manner as in Example 1.

[0193] Comparative Example 2

[0194] The 3,4-epoxycyclohexylmethyl (3',4'-epoxy) cyclohexanecarboxylate product was used as the alicyclic epoxy compound product 5 of Comparative Example 2.

[0195] <Evaluation>

[0196] The following evaluations were performed on the alicyclic epoxy compound products of the examples and comparative examples. The results are shown in Table 1.

[0197] (1) 1 H-NMR

[0198] Using the device name "JNM-ECZ400S" (manufactured by JEOL Ltd.), solvent: deuterated chloroform, and measurement conditions: 20 °C, the alicyclic epoxy compound product 1 of Example 1 was 1 subjected to the measurement of the H-NMR spectrum. The 1 H-NMR spectrum of the alicyclic epoxy compound product 1 obtained in Example 1 is shown in Figure 1 .

[0199] (2) GPC

[0200] As a pretreatment, 0.04 g of the alicyclic epoxy compound product was dissolved in 2 g of tetrahydrofuran (THF) and filtered using a filter with a pore size of 0.50 μm (trade name "DISMIC13JP050AN", manufactured by Toyo Roshi Kaisha, Ltd.). The THF solution of the obtained alicyclic epoxy compound product was analyzed by GPC, and the ratio of the peak area of the component with the highest peak area ratio (the target alicyclic epoxy compound) was defined as the purity [area%] of the alicyclic epoxy compound product. The sum of the concentrations of the components eluted earlier than the target alicyclic epoxy compound was calculated as the high molecular weight component concentration. It should be noted that when the shoulders of adjacent peaks overlap, the peak area is calculated by dividing the peak area from the peak valley by a perpendicular line to the baseline. The GPC device and various conditions used are as follows.

[0201] Device: HLC-8220GPC (manufactured by Tosoh Corporation).

[0202] Detector: differential refractometer (RI detector).

[0203] Pre-column: TSKGUARDCOLUMN SUPER HZ-L 4.6 mm × 20 mm.

[0204] Column: sample side TSK-GEL SUPER HZM-N 4.6 mm × 150 mm × 4 columns.

[0205] Reference side TSK-GEL SUPER HZM-N 6.0 mm × 150 mm × 1 column + TSK-GEL SUPER H-RC 6.0 mm × 150 mm.

[0206] Thermostat temperature: 40 °C.

[0207] Mobile phase: THF.

[0208] Flow layer flow rate: 0.35 ml / min.

[0209] Sample injection volume: 10 μl.

[0210] Data acquisition time: 10 minutes to 26 minutes after sample injection.

[0211] (3) GC-MS

[0212] Analyze the alicyclic epoxy compound products of each example by gas chromatography according to the following measurement conditions. And, identify the components contained in the alicyclic epoxy compound products based on the molecular weight. It should be noted that the molecular weights of the detected peaks are analyzed by mass spectrometry. Under the following conditions, measure the total content ratio of compounds (a) to (d) and compounds with a molecular weight of 100 or less by gas chromatography, and calculate it as area%. It should be noted that for the examples and Comparative Example 1, compound (a) represents the compound represented by the above formula (a), compound (b) represents the compound represented by the above formula (b), compound (c) represents the compound represented by the above formula (c), and compound (d) represents the compound represented by the above formula (d). In addition, for Comparative Example 2, compound (a) represents a compound having a structure in which the methyl groups in two epoxycyclohexyl groups are removed from the compound represented by the above formula (a), compound (b) represents a compound having a structure in which the methyl groups in two epoxycyclohexyl groups are removed from the compound represented by the above formula (b), compound (c) represents a compound having a structure in which the methyl groups in two epoxycyclohexyl groups are removed from the compound represented by the above formula (c), and compound (d) represents a compound having a structure in which the methyl groups in two epoxycyclohexyl groups are removed from the compound represented by the above formula (d).

[0213] <Measurement conditions>

[0214] Measurement device: Trade name "Agilent7890GC5977B MSD", manufactured by Agilent Technologies Co., Ltd.

[0215] Column packing: (5% phenyl) methylsiloxane.

[0216] Column size: Length 15 m × inner diameter × film thickness 1.5 μm.

[0217] Column temperature: 100 °C → (heating at 10 °C / min) → 250 °C (15 minutes).

[0218] Detector: FID.

[0219] (4) Color phase (APHA)

[0220] Using a spectro-color difference - turbidity simultaneous measuring instrument (trade name "TZ6000", manufactured by Nippon Denshoku Industries Co., Ltd.) and a glass cell (optical path length 33 × cell width 20 × height 55), the Hazen color number APHA was determined, and the hue was evaluated therefrom. If it is 105 or less, it is judged to be good, and if it is 15 or less, it is judged to be excellent.

[0221] (5) Viscosity

[0222] Using a digital viscometer (model "DVU-EII type", manufactured by TOKIMEC, Inc.), the viscosity of the alicyclic epoxy compound product at 25 °C was measured under the conditions of rotor: standard 1°34' × R24, temperature: 25 °C, and rotation speed: 0.5 to 10 rpm. If it is 1300 mPa·s or less, it is judged to be good, and if it is 1000 mPa·s or less, it is judged to be excellent.

[0223] Example 4

[0224] To 100 parts by mass of the alicyclic epoxy compound product of each example, 0.6 part by mass of "SAN-AID SI-100L" (manufactured by Sanshin Chemical Industry Co., Ltd.), which is a thermal cationic catalyst, was added, and stirring was carried out using a planetary stirrer (trade name "Awatori Rentaro AR-250", manufactured by THINKY Corporation), and further defoaming was carried out to obtain each curable composition.

[0225] Example 5

[0226] The alicyclic epoxy compound product of each example, "RIKACID MH-700" (manufactured by Shin Nippon Rika Co., Ltd.), which is an acid anhydride curing agent, and "PX-4MP" (manufactured by Nippon Chemical Industry Co., Ltd.), which is a curing accelerator, were mixed in such a manner that the ratio of the epoxy equivalent to the acid anhydride equivalent of the compound represented by the above formula (1) in the above alicyclic epoxy compound product was 100:90, and stirring was carried out using a planetary stirrer (trade name "Awatori Rentaro AR-250", manufactured by THINKY Corporation), and further defoaming was carried out to obtain each curable composition.

[0227] (6) Curability

[0228] The curability of the curable compositions obtained in Example 4 and Example 5 was measured using a gel time measuring device (trade name “Rheometer MCR302”, manufactured by Anton Paar Japan Co., Ltd.). Specifically, the curable composition of Example 4 (thermal cationic catalyst) was heated to 80°C, and the curable composition of Example 5 (anhydride curing agent) was heated to 120°C. Then, the curing curve was measured by the rheometer method (dynamic viscoelasticity evaluation), and the temperature curve of the loss modulus at a fixed frequency was measured. The point where the two elastic modulus curves of the measured G' (storage modulus) and G'' (loss modulus) intersect was defined as the gelation point and determined. Then, starting from the time when the set temperature rise (80°C or 120°C) was reached, the time until the gelation point was reached was evaluated as the thermal gel time. In Example 4, if it was 1100 seconds or less, it was judged to be good, and if it was 1050 seconds or less, it was judged to be excellent. In Example 5, if it was 5000 seconds or less, it was judged to be good, and if it was 3000 seconds or less, it was judged to be excellent.

[0229] Example 6

[0230] Each curable composition obtained in Example 4 and Example 5 was filled into a mold and heated in a resin curing oven at 120°C for 5 hours to obtain each cured product.

[0231] (7) Curing shrinkage

[0232] For the cured products obtained from the curable compositions of Example 4, the density before and after curing was measured by the density measurement method (JIS K5600 2-4), and the curing shrinkage rate (volume shrinkage rate) was calculated based on the following formula from the density change. If it was 1.5% or less, it was judged to be good.

[0233] Volume shrinkage rate r = {(ds - dl) / dl} × 100

[0234] dl: Specific gravity of the liquid before curing. Measured using a density hydrometer “DA-640” (manufactured by Kyoto Electronics Industry Co., Ltd.).

[0235] ds: Specific gravity of the solid after curing. Measured using the solid specific gravity measurement method.

[0236] (8) Light transmittance

[0237] For each cured product (thickness: 3 mm) obtained in Example 6, the light transmittance (in the thickness direction) of light with a wavelength of 450 nm was measured using a spectrophotometer (trade name “UV-2450”, 10 mm square quartz cell, thickness 10 mm, manufactured by Shimadzu Corporation). In Example 4, if it was 80% or more, it was judged as good, and if it was 85% or more, it was judged as excellent. In Example 5, if it was 88% or more, it was judged as good, and if it was 90% or more, it was judged as excellent. (

[0239] (9) Glass transition temperature (Tg)

[0240] For each cured product obtained in Example 6, the glass transition temperature was determined under the following conditions. In Example 4, if it was 175 °C or higher, it was judged as good, and if it was 200 °C or higher, it was judged as excellent. In Example 5, if it was 180 °C or higher, it was judged as good, and if it was 190 °C or higher, it was judged as excellent.

[0241] Sample: Length 4 mm × width 5 mm × thickness 10 mm.

[0242] Measurement device: Thermomechanical analyzer (TMA), trade name “TMA / SS6000”, manufactured by Seiko Instruments Inc.

[0243] Measurement mode: Compression (penetration), constant load measurement.

[0244] Measurement temperature: From 25 °C to 300 °C.

[0245] Heating rate: 5 °C / minute.

[0246] (10) Weight loss temperature (TG / DTA)

[0247] For the cured products obtained from the respective curable compositions of Example 4, the 5% weight loss temperature (Td5) and the 10% weight loss temperature (Td10) were determined under the following conditions. If Td5 was 325 °C or higher, it was judged as good, and if Td5 was 335 °C or higher, it was judged as excellent. If Td10 was 355 °C or higher, it was judged as good, and if Td10 was 360 °C or higher, it was judged as excellent.

[0248] Sample: 5 - 10 μg.

[0249] Measurement device: Trade name “STA / 7200”, manufactured by Hitachi High-Tech Corporation.

[0250] (11) Light transmittance retention rate

[0251] For each cured product (thickness: 3 mm) obtained in Example 6, (i) while heating at 120°C, ultraviolet rays with an intensity of 10 mW / cm 2 were irradiated for 500 hours or (ii) after the treatment of heating at 120°C, a spectrophotometer (product name: "UV-2450", manufactured by Shimadzu Corporation) was used to measure the light transmittance (%) of ultraviolet rays (wavelength: 450 nm). Then, the value of the light transmittance after the treatment relative to the light transmittance before the treatment (the light transmittance in the above (8)) (the maintenance rate of the light transmittance of the cured product) was evaluated as the light transmittance maintenance rate (light resistance) (%). The larger the value of the light transmittance maintenance rate, the more excellent the light resistance of the cured product to ultraviolet rays.

[0252] [Table 1]

[0253] (Table 1)

[0254]

[0255] As shown in Table 1, the alicyclic epoxy compound products of the examples were evaluated to have low viscosity, good hue, and excellent transparency compared to the products with low purity. In addition, for the cured products, they were evaluated to have high light transmittance, excellent transparency, and high maintenance rate. Moreover, they had high Tg and excellent heat resistance. Furthermore, the alicyclic epoxy compound products of the examples were evaluated to have small curing shrinkage compared to the products of other alicyclic epoxy compounds.

[0256] Example 7

[0257] Relative to 100 parts by mass of the alicyclic epoxy compound product 1 obtained in Example 1, 2 parts by mass of a thermal cationic catalyst (trade name: "CPI-210S", manufactured by San-Apro Ltd.) as a curing catalyst was blended, and stirring was carried out using a rotation-revolution type stirring device (trade name: "Awatori Rentaro AR-250", manufactured by THINKY Corporation), and further defoaming was carried out to obtain a curable composition. Then, the above curable composition was filled into a mold, and ultraviolet rays with an intensity of 100 mW / cm 2 were irradiated for 30 seconds, and then heated in a resin curing oven at 150°C for 30 minutes to obtain a cured product.

[0258] Examples 8 to 16

[0259] The components and contents shown in Table 2 were used, and except for this, a curable composition and a cured product were produced in the same manner as in Example 7.

[0260] <Evaluation>

[0261] For the curable composition of the examples, evaluations were made on curability, Tg of the cured product, and weight loss temperature. The results are shown in Table 2. The evaluation methods for Tg and weight loss temperature were the same as those in Example 1. The evaluation method for curability is as follows.

[0262] (12) Curability

[0263] Using the apparatus: “DSC6220” manufactured by SII Corporation, the curability of the curable compositions obtained in Examples 8 to 16 was measured. Specifically, a light source with a wavelength of 365 nm was irradiated at 30 °C with 100 mW × 30 seconds, and the exothermic peak intensity was calculated. The higher the peak intensity, the better the curability was judged.

[0264] [Table 2]

[0265] (Table 2)

[0266]

[0267] Hereinafter, modifications of the invention of the present disclosure will be described.

[0268] [Supplementary Note 1] An epoxy compound product, wherein the purity of the compound represented by the following formula (1) is 90% or more, and the total content ratio of the compound represented by the following formula (a), the compound represented by the following formula (b), the compound represented by the following formula (c), and the compound represented by the following formula (d) is 10% by mass or less.

[0269] [Chemical Formula 1]

[0270]

[0271] [Supplementary Note 2] The epoxy compound product according to Supplementary Note 1, wherein the Hazen color number of the epoxy compound product is 105 or less.

[0272] [Supplementary Note 3] The epoxy compound product according to Supplementary Note 1 or 2, wherein the total content ratio of the compound represented by the following formula (a), the compound represented by the following formula (b), the compound represented by the following formula (c), and the compound represented by the following formula (d) is 0.1% by mass or more.

[0273] [Supplementary Note 4] A curable composition comprising the epoxy compound product according to any one of Supplementary Notes 1 to 3, a curing agent, and / or a curing catalyst.

[0274] [Supplementary Note 5] A curable composition comprising the epoxy compound product according to any one of Supplementary Notes 1 to 3, other epoxy compounds, and / or oxetane compounds.

[0275] [Supplementary Note 6] The curable composition according to Supplementary Note 4 or 5, wherein the curable composition is an adhesive, a sealant, or a coating agent.

[0276] [Supplementary Note 7] A cured product, which is a cured product of the curable composition according to any one of Supplementary Notes 4 to 6.

[0277] [Supplementary Note 8] An optical member, which includes the cured product according to Supplementary Note 7.

[0278] [Supplementary Note 9] A method for manufacturing an epoxy compound product, which is the method for manufacturing an epoxy compound product according to Supplementary Note 1 or 2, and manufactures the epoxy compound product through the following epoxidation step, the following low-boiling component removal step, and the following high-boiling component removal step.

[0279] Epoxidation step: A step of reacting 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate with an organic peroxyacid to obtain a reaction product.

[0280] Low-boiling component removal step: A step of subjecting the reaction product to low-boiling component removal treatment.

[0281] High-boiling component removal step: A step of subjecting the reaction product to high-boiling component removal treatment by thin-film evaporation.

Claims

1. An epoxy compound product, wherein, the purity of the compound represented by the following formula (1) is 90% or more, and the total content ratio of the compound represented by the following formula (a), the compound represented by the following formula (b), the compound represented by the following formula (c), and the compound represented by the following formula (d) is 10% by mass or less. [Chemical formula 1] 2. The epoxy compound product according to claim 1, wherein, the Hazen color number of the epoxy compound product is 105 or less.

3. The epoxy compound product according to claim 1, wherein, the total content ratio of the compound represented by the following formula (a), the compound represented by the following formula (b), the compound represented by the following formula (c), and the compound represented by the following formula (d) is 0.1% by mass or more.

4. A curable composition comprising the epoxy compound product according to claim 1, a curing agent, and / or a curing catalyst.

5. A curable composition comprising the epoxy compound product according to claim 1, another epoxy compound, and / or an oxetane compound.

6. The curable composition according to claim 4 or 5, wherein, the curable composition is an adhesive, a sealant, or a coating agent.

7. A cured product which is a cured product of the curable composition according to claim 4 or 5.

8. An optical member comprising the cured product according to claim 7.

9. A method for manufacturing an epoxy compound product, which is a method for manufacturing the epoxy compound product according to claim 1 or 2, and manufactures the epoxy compound product through the following epoxidation step, the following low-boiling component removal step, and the following high-boiling component removal step, Epoxidation step: a step of reacting 6-methyl-3-cyclohexenylmethyl (6'-methyl-3'-cyclohexenyl) formate with an organic peroxy acid to obtain a reaction product; Low-boiling component removal step: a step of performing low-boiling component removal treatment on the reaction product; High-boiling component removal step: a step of performing high-boiling component removal treatment on the reaction product by thin-film evaporation.

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