Compounds, compositions, cured products, and methods for producing cured products

Abstract

The primary objective of this disclosure is to provide a compound capable of forming a cured product with excellent heat resistance. [Solution] This disclosure achieves the above objective by providing a compound represented by the following general formula (1). JPEG2026047575000019.jpg49110 (In the formula, R 1 and R 5 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 2 and R 4 Each of these independently represents a hydrogen atom or a methyl group, and R 3 (This represents a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group with 6 to 20 carbon atoms, or a divalent heterocyclic group with 4 to 20 carbon atoms.)

Description

[Technical Field]

[0001] This disclosure relates to compounds, compositions containing the same, cured products, and methods for producing cured products. [Background technology]

[0002] Epoxy compounds are widely used as components in adhesives, paints, and the like. For example, Patent Document 1 describes a paint that uses an epoxy compound derived from bisphenol A as the epoxy compound. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] International Publication No. 2022 / 080048 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, the cured epoxy compound used in Patent Document 1 had the problem of insufficient physical strength, such as heat resistance.

[0005] This disclosure has been made in view of the above-mentioned problems, and its main purpose is to provide a compound that can form a cured product with excellent heat resistance. [Means for solving the problem]

[0006] As a result of diligent research, the inventors have discovered that a compound having a specific structure can form a cured product with excellent heat resistance.

[0007] In other words, this disclosure provides a compound represented by the following general formula (1).

[0008] [ka]

[0009] (In the formula, R 1 and R 5 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 2 and R 4 Each of these independently represents a hydrogen atom or a methyl group, and R 3 (This represents a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group with 6 to 20 carbon atoms, or a divalent heterocyclic group with 4 to 20 carbon atoms.) [Effects of the Invention]

[0010] According to this disclosure, it is possible to provide a compound that can form a cured product with excellent heat resistance. [Brief explanation of the drawing]

[0011] [Figure 1] This shows the 1H-NMR measurement results of diallyl structure 1, which was obtained as an intermediate in Example 1. [Figure 2] This shows the 13C-NMR measurement results of diallyl structure 1, which was obtained as an intermediate in Example 1. [Figure 3] This shows the 1H-NMR measurement results of compound 1 of the present disclosure obtained in Example 1. [Figure 4] This shows the 13C-NMR measurement results of Compound 1 of the present disclosure obtained in Example 1. [Modes for carrying out the invention]

[0012] The compounds disclosed herein, compositions containing them, cured products, and methods for producing cured products will be described in detail below.

[0013] A. Compound First, the compounds of this disclosure will be described. The compounds of this disclosure are compounds represented by the following general formula (1).

[0014] [ka]

[0015] (In the formula, R 1 and R 5 each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 2 and R 4 each independently represents a hydrogen atom or a methyl group, and R 3 represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heterocyclic group having 4 to 20 carbon atoms.)

[0016] According to the present disclosure, the compound of the present disclosure represented by the general formula (1) can form a cured product having excellent heat resistance. Here, the reason why the compound represented by the general formula (1) can form a cured product having excellent heat resistance is presumed as follows.

[0017] That is, the compound of the present disclosure is an epoxide having a dimerized structure of a compound having a skeleton having a three-dimensional cyclic structure that can be formed by the reaction of inositol and an orthoester compound, and an epoxy group, so that a cured product having excellent physical property strength such as heat resistance can be formed.

[0018] 1. Compound [[ID=二十七]]R in the general formula (1) 1 and R 5 each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms. Examples of the hydrocarbon group having 1 to 20 carbon atoms include an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and the like. Examples of the aliphatic hydrocarbon group having 1 to 20 carbon atoms include a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to

[0019] Examples of linear alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl groups.

[0020] Examples of branched alkyl groups having 3 to 20 carbon atoms include isopropyl group, t-butyl group, isopentyl group, isohexyl group, isoheptyl group, 2-ethylhexyl group, isooctyl group, isononyl group, isodecyl group, isoundecyl group, isododecyl group, isotridecyl group, isotetradecyl group, isopentadecyl group, isohexadecyl group, isoheptadecyl group, isooctadecyl group, isononadecyl group, and isoicosyl group.

[0021] Examples of linear alkenyl groups having 2 to 20 carbon atoms include vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, and icocenyl groups. These groups may have an unsaturated bond at the terminal end of the alkenyl group or an unsaturated bond internally.

[0022] Examples of branched alkenyl groups having 3 to 20 carbon atoms include branched allyl group, branched butenyl group, branched pentenyl group, branched hexenyl group, branched heptenyl group, branched octenyl group, branched nonenyl group, branched decenyl group, branched undecenyl group, branched dodecenyl group, branched tridecenyl group, branched tetradecenyl group, branched pentadecenyl group, branched hexadecenyl group, branched heptadecenyl group, branched octadecenyl group, branched nonadecenyl group, branched icocenyl group, etc. In these groups, the branched alkenyl group may have an unsaturated bond at one of its terminal ends, or it may have an unsaturated bond internally.

[0023] Examples of alicyclic hydrocarbon groups having 3 to 20 carbon atoms include cyclic hydrocarbon groups having 3 to 20 carbon atoms, and alicyclic hydrocarbon groups having 4 to 20 carbon atoms in which one or more hydrogen atoms of the cyclic hydrocarbon group are substituted with a linear alkyl group or a branched alkyl group. Among these, examples of cyclic hydrocarbon groups include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, and cyclodecyl group, and may also be polycyclic hydrocarbon groups such as adamantyl group.

[0024] Examples of alicyclic hydrocarbon groups having 4 to 20 carbon atoms, in which one or more hydrogen atoms of the cyclic hydrocarbon group are substituted with a linear alkyl group or a branched alkyl group, include cyclopropylmethyl group, 2-cyclobutylethyl group, 3-cyclopentylpropyl group, 4-cyclohexylbutyl group, cycloheptylmethyl group, cyclooctylmethyl group, 2-cyclononylethyl group, 2-cyclodecylethyl group, and 3-3-adamantylpropyl group.

[0025] Aromatic hydrocarbon groups having 6 to 20 carbon atoms are not particularly limited as long as they have 6 to 20 carbon atoms and contain an aromatic hydrocarbon group in their structure. Examples of such aromatic hydrocarbon groups include groups consisting only of aromatic rings such as phenyl groups, naphthyl groups, and anthracenyl groups, as well as groups in which these are substituted with one or more groups selected from the group consisting of linear alkyl groups, branched alkyl groups, linear alkenyl groups, and branched alkenyl groups.

[0026] Among these, in this disclosure, from the viewpoint of forming a cured product with superior heat resistance, R 1 and R 5 Each of these is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms, even more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom or a methyl group.

[0027] R in general formula (1) 2 and R 4 Each of these independently represents a hydrogen atom or a methyl group. Among these, in this disclosure, from the viewpoint of forming a cured product with superior heat resistance, R 2 and R 4 It is preferable that all of them are hydrogen atoms.

[0028] R in general formula (1) 3 This represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heterocyclic group having 4 to 20 carbon atoms. Examples of divalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms include divalent linear saturated aliphatic hydrocarbon groups having 1 to 20 carbon atoms, divalent branched saturated aliphatic hydrocarbon groups having 3 to 20 carbon atoms, divalent linear unsaturated aliphatic hydrocarbon groups having 2 to 20 carbon atoms, and divalent branched unsaturated aliphatic hydrocarbon groups having 3 to 20 carbon atoms.

[0029] Examples of divalent linear saturated aliphatic hydrocarbon groups having 1 to 20 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, and eicosilene.

[0030] Examples of divalent branched saturated aliphatic hydrocarbon groups having 3 to 20 carbon atoms include isopropylene, t-butylene, isopentylene, isohexylene, isoheptylene, isooctylene, isononylene, isodecylene, isounddecylene, isododecylene, isotridecylene, isotetradecylene, isopentadecylene, isohexadecylene, isoheptadecylene, isooctadeciylene, isononadecylene, and isoicosilene.

[0031] Examples of divalent linear unsaturated aliphatic hydrocarbon groups having 2 to 20 carbon atoms include groups having a structure in which one or more of the carbon-carbon bonds of the linear saturated aliphatic hydrocarbon group described above are unsaturated bonds.

[0032] Examples of divalent branched unsaturated aliphatic hydrocarbon groups having 3 to 20 carbon atoms include groups having a structure in which one or more of the carbon-carbon bonds of the branched saturated aliphatic hydrocarbon group described above are unsaturated bonds.

[0033] Examples of divalent aromatic hydrocarbon groups having 6 to 20 carbon atoms include groups consisting solely of aromatic rings such as phenylene groups, naphthylene groups, and anthracenylene groups, as well as groups in which these are substituted with one or more groups selected from the group consisting of linear alkyl groups, branched alkyl groups, linear alkenyl groups, and branched alkenyl groups.

[0034] Divalent heterocyclic groups having 4 to 20 carbon atoms are not particularly limited as long as they have 4 to 20 carbon atoms and contain a heterocyclic ring in their structure consisting of a carbon atom and an atom other than a carbon atom, such as a nitrogen atom, oxygen atom, or sulfur atom. Examples include groups having 4 to 20 carbon atoms and containing one or more heterocyclic rings selected from the group consisting of pyrrolidine rings, imidazolidine rings, pyrazolidine rings, pyrroline rings, pyrrole rings, pyrazole rings, imidazole rings, piperidine rings, piperazine rings, pyridine rings, pyrimidine rings, triazine rings, furan rings, dioxolane rings, thiophene rings, phlopyrrole rings, thienopyrrole rings, and pyrrolopyrrole rings.

[0035] Among these, in this disclosure, from the viewpoint of forming a cured product with superior heat resistance, R 3It is preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 12 carbon atoms, even more preferably a methylene group, ethylene group, propylene group, phenylene group, or naphthylene group, and particularly preferably a methylene group or a phenylene group.

[0036] 2. Method for producing the compound The method for producing the compound of the disclosure is not particularly limited as long as it yields the compound of general formula (1). For example, as shown below, one method may include a step of producing a diester structure, a diol structure, and a diallyl structure as intermediates, using a hydroxy compound obtained from myo-inositol or the like as a starting material, and then producing a diepoxide structure (the compound of the disclosure) as the final product.

[0037] [ka]

[0038] (1) Hydroxyl compounds as starting materials The hydroxy compound used as a starting material when producing the compounds of this disclosure by the method described above is a hydroxy compound represented by the following general formula (2).

[0039] [ka]

[0040] R in general formula (2) 6 R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and as a hydrocarbon group having 1 to 20 carbon atoms, R in the compound of the disclosure represented by the general formula (1) described above. 1 and R 5It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 6 It is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms, even more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom or a methyl group.

[0041] The hydroxy compound represented by general formula (2) may be obtained by known manufacturing methods or a commercially available product. For example, it may be obtained by methods described in J.Polym.Sci.2020,58,1973-1981, Japanese Patent Publication No. 2017-110204, etc.

[0042] (2) Manufacturing process of diester structures Next, the process for producing the diester structure as an intermediate will be described. In the method for producing the compound of this disclosure, the process for producing the diester structure is to produce the diester structure represented by the following general formula (3) using the hydroxy compound represented by general formula (2) as the starting material described above.

[0043] [ka]

[0044] R in general formula (3) 7 and R 9 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and as a hydrocarbon group having 1 to 20 carbon atoms, R in the compound of the disclosure represented by the general formula (1) described above. 1 and R 5 It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 7 and R 9Each of these is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms, even more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom or a methyl group. In general formula (3), t-Bu represents a tert-butyl group.

[0045] R in general formula (3) 8 R represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heterocyclic group having 4 to 20 carbon atoms. Specifically, R in the compound of the disclosure represented by the general formula (1) described above. 3 It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 8 It is preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 12 carbon atoms, even more preferably a methylene group, ethylene group, propylene group, phenylene group, or naphthylene group, and particularly preferably a methylene group or a phenylene group.

[0046] Specific methods for producing a diester structure represented by general formula (3) using a hydroxy compound represented by general formula (2) as described above include, for example, a method of reacting a hydroxy compound represented by general formula (2) with a compound represented by general formula (4) below.

[0047] [ka]

[0048] R in general formula (4) 10R represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heterocyclic group having 4 to 20 carbon atoms. Specifically, R in the compound of the disclosure represented by the general formula (1) described above. 3 It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 10 However, it is preferable to use a compound that is a divalent linear saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a compound that is a divalent linear saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 12 carbon atoms, even more preferably a compound that is a methylene group, ethylene group, propylene group, phenylene group, or naphthylene group, and particularly preferably a compound that is a methylene group or phenylene group. In general formula (4), Me represents a methyl group.

[0049] When reacting the hydroxy compound represented by general formula (2) with the compound represented by general formula (4), the ratio of each starting material used is not particularly limited. However, from the viewpoint of easily obtaining the diester structure represented by general formula (3) in good yield, it is preferable to use 0.1 mmol to 1 mmol of the compound represented by general formula (4) for every 1 mmol of the hydroxy compound represented by general formula (2), and more preferably 0.4 mmol to 0.6 mmol.

[0050] When reacting a hydroxy compound represented by general formula (2) with a compound represented by general formula (4), solvents, catalysts, etc., can be used as needed. Examples of such solvents include formamide, acetamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, ethyl acetate, propyl acetate, butyl acetate, acetonitrile, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, tetrachloroethylene, 1,3-dimethyl-2-imidazolidinone, benzene, toluene, xylene, dioxane, and dimethyl sulfoxide. Among these, from the viewpoint of easily obtaining the diester structure represented by general formula (3) in good yield, it is preferable to use one or more selected from the group consisting of benzene, toluene, and xylene.

[0051] The catalyst that can be used when reacting a hydroxy compound represented by general formula (2) with a compound represented by general formula (4) is not particularly limited, but examples include sulfonic acids such as p-toluenesulfonic acid, o-toluenesulfonic acid, benzenesulfonic acid, p-phenolsulfonic acid, 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, p-xylene-2-sulfonic acid, m-xylene-2-sulfonic acid, 4-ethylbenzenesulfonic acid, 10-camphorsulfonic acid, and hydrates thereof. Among these, from the viewpoint of easily obtaining the diester structure represented by general formula (3) in good yield, it is preferable to use at least one sulfonic acid as a catalyst, and more preferably to use one or more selected from the group consisting of p-toluenesulfonic acid, o-toluenesulfonic acid, benzenesulfonic acid, and 10-camphorsulfonic acid. Furthermore, when a catalyst is used in this process, from the viewpoint of easily obtaining the diester structure represented by general formula (3) in good yield, it is preferable to use 0.001 mmol to 2 mmol of catalyst per 1 mmol of the hydroxy compound represented by general formula (2) used, more preferably 0.01 mmol to 1 mmol, even more preferably 0.05 mmol to 0.5 mmol, and particularly preferably 0.05 mmol to 0.2 mmol.

[0052] The reaction conditions for reacting the hydroxy compound represented by general formula (2) with the compound represented by general formula (4) are not particularly limited and can be adjusted as appropriate. For example, the reaction can be carried out under pressure, reduced pressure, or atmospheric pressure, at a temperature of 30°C to 180°C, for 10 minutes to 72 hours.

[0053] (3) Manufacturing process of diol structures Next, the process for producing the diol structure as an intermediate will be described. In the compound production method of this disclosure, the process for producing the diol structure is to produce the diol structure represented by the following general formula (5) using the diester structure represented by general formula (3) obtained by the diester structure production process described above.

[0054] [ka]

[0055] R in general formula (5) 11 and R 13 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms. As a hydrocarbon group having 1 to 20 carbon atoms, R in the compound of the disclosure represented by the general formula (1) described above is... 1 and R 5 It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 11 and R 13 Each of these is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms, even more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom or a methyl group.

[0056] R in general formula (5) 12 R represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heterocyclic group having 4 to 20 carbon atoms. Specifically, R in the compound of the disclosure represented by the general formula (1) described above. 3 It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 12 It is preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 12 carbon atoms, even more preferably a methylene group, ethylene group, propylene group, phenylene group, or naphthylene group, and particularly preferably a methylene group or a phenylene group.

[0057] Specific methods for producing a diol structure represented by general formula (5) using a diester structure represented by general formula (3) as described above include, for example, a method of hydrolyzing the ester structure portion of the diester structure represented by general formula (3) in the presence of a base.

[0058] Examples of bases that can be used in this process include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, calcium carbonate, potassium carbonate, sodium sulfite, and sodium phosphate. Among these, from the viewpoint of easily obtaining the diol structure represented by general formula (5) in good yield, it is preferable to use one or more selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, calcium carbonate, and potassium carbonate as the base, and more preferably to use one or more selected from the group consisting of sodium hydroxide, potassium hydroxide, and calcium hydroxide. Furthermore, when using a base in this process, from the viewpoint of easily obtaining the diol structure represented by general formula (5) in good yield, it is preferable to use 2 mmol to 100 mmol of base per 1 mmol of the diester structure represented by general formula (3) used, more preferably 2 mmol to 20 mmol, and even more preferably 5 mmol to 10 mmol.

[0059] When hydrolyzing the ester structure of a diester structure represented by general formula (3) in the presence of a base, a solvent may be used as needed. Examples of such solvents include water, methanol, ethanol, isopropanol, n-propanol, isobutanol, n-butanol, amyl alcohol, t-butyl alcohol, diacetone alcohol, glycerin, monoacetylene, ethylene glycol, triethylene glycol, hexylene glycol, methoxypropanol, formamide, acetamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, acetonitrile, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, tetrachloroethylene, 1,3-dimethyl-2-imidazolidinone, benzene, toluene, xylene, dioxane, and dimethyl sulfoxide. Among these, from the viewpoint of easily obtaining the diol structure represented by general formula (5) in good yield, it is preferable to use one or more selected from the group consisting of methanol, ethanol, isopropanol, n-propanol, isobutanol, n-butanol, amyl alcohol, t-butyl alcohol, and dioxane.

[0060] The reaction conditions for hydrolyzing the ester structure of the diester structure represented by general formula (3) in the presence of a base are not particularly limited and can be adjusted as appropriate. For example, the reaction can be carried out under pressure, reduced pressure, or atmospheric pressure, at a temperature of 10°C to 120°C, for 10 minutes to 72 hours.

[0061] (4) Manufacturing process of diallyl structures Next, the process for producing the diallyl structure as an intermediate will be described. In the method for producing the compound of this disclosure, the process for producing the diallyl structure is to produce the diallyl structure represented by the following general formula (6) using the diol structure represented by general formula (5) obtained by the diol structure production process described above.

[0062] [ka]

[0063] R in general formula (6) 14 and R 16 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and as a hydrocarbon group having 1 to 20 carbon atoms, R in the compound of the disclosure represented by the general formula (1) described above. 1 and R 5 It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 14 and R 16 Each of these is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms, even more preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom or a methyl group.

[0064] In general formula (6), R 15 R represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heterocyclic group having 4 to 20 carbon atoms. Specifically, R in the compound of the disclosure represented by the general formula (1) described above. 3 It can be a similar group to the above. Among these, from the viewpoint of obtaining a compound that can form a cured product with better heat resistance, R 15 It is preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a divalent linear saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 12 carbon atoms, even more preferably a methylene group, ethylene group, propylene group, phenylene group, or naphthylene group, and particularly preferably a methylene group or a phenylene group.

[0065] Specific methods for producing the diallyl structure represented by general formula (6) using the diol structure represented by general formula (5) mentioned above include, for example, a method of reacting the diol structure represented by general formula (5) with one or more allyl halogenated compounds. Examples of allyl halogenated compounds that can be used in this process include allyl fluoride, allyl chloride, allyl bromide, allyl iodide, 2-methylallyl fluoride, 2-methylallyl chloride, 2-methylallyl bromide, and 2-methylallyl iodide. Among these, from the viewpoint of easily obtaining the diallyl structure represented by general formula (6) in good yield, it is preferable to use allyl chloride, allyl bromide, or a mixture thereof.

[0066] When reacting the diol structure represented by general formula (5) with the allyl halide compound, the ratio of each raw material used is not particularly limited. However, from the viewpoint of easily obtaining the diallyl structure represented by general formula (6) in good yield, it is preferable to use 2 mmol to 20 mmol of the allyl halide compound for every 1 mmol of the diol structure represented by general formula (5), more preferably 2.1 mmol to 10 mmol, and even more preferably 2.2 mmol to 5 mmol.

[0067] The reaction temperature when reacting the diol structure represented by general formula (5) with one or more allyl halogenated compounds is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of obtaining the diallyl structure represented by general formula (6) in good yield, a temperature of -20°C to 50°C is preferred, and -10°C to 40°C is more preferred. The reaction time when reacting the diol structure represented by general formula (5) with one or more allyl halogenated compounds is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of obtaining the diallyl structure represented by general formula (6) in good yield, a reaction time of 1 hour to 50 hours is preferred, and 2 hours to 40 hours is more preferred.

[0068] When reacting a diol structure represented by general formula (5) with one or more allyl halogenated compounds, solvents, basic compounds, etc., can be used as needed. Examples of such solvents include formamide, acetamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, ethyl acetate, propyl acetate, butyl acetate, acetonitrile, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, tetrachloroethylene, 1,3-dimethyl-2-imidazolidinone, benzene, toluene, xylene, dioxane, and dimethyl sulfoxide. Among these, from the viewpoint of easily obtaining the diallyl structure represented by general formula (6) in good yield, it is preferable to use one or more selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and N-methyl-2-pyrrolidone.

[0069] Examples of basic compounds that can be used in this process include sodium methoxide, sodium ethoxide, lithium methoxide, lithium ethoxide, pyridine, triethylamine, N,N-dimethylaniline, 4-dimethylaminopyridine, sodium hydroxide, lithium hydroxide, potassium hydroxide, barium hydroxide, sodium carbonate, sodium bicarbonate, lithium carbonate, potassium carbonate, sodium hydride, lithium hydride, potassium hydride, calcium hydride, trityllithium, tritylsodium, tritylpotassium, methyllithium, methylmagnesium chloride, ethylmagnesium chloride, ethylmagnesium bromide, sodium amide, potassium amide, lithium diisopropylamide, potassium diisopropylamide, lithium dicyclohexylamide, potassium dicyclohexylamide, and the like. Among these, from the viewpoint of easily obtaining the diallyl structure represented by general formula (6) in good yield, it is preferable to use one or more basic compounds selected from the group consisting of sodium hydride, lithium hydride, potassium hydride, calcium hydride, sodium hydroxide, lithium hydroxide, potassium hydroxide, sodium methoxide, and sodium ethoxide, and more preferably to use one or more basic compounds selected from the group consisting of sodium hydride, lithium hydride, potassium hydride, and calcium hydride. Furthermore, when using a basic compound in this step, from the viewpoint of easily obtaining the diallyl structure represented by general formula (6) in good yield, it is preferable to use 2 mmol to 20 mmol of the basic compound per 1 mmol of the diol structure represented by general formula (5) used, more preferably 4 mmol to 15 mmol, and even more preferably 5 mmol to 8 mmol.

[0070] (5) Manufacturing process 1 of the compound (diepoxide structure) of the present disclosure Next, the process for producing the diepoxide structure, which is the compound of this disclosure, will be described. Step 1 for producing the diepoxide structure in the method for producing the compound of this disclosure is a step for producing the diepoxide structure represented by the following general formula (1) using the diallyl structure represented by general formula (6) obtained by the diallyl structure production step described above.

[0071] [ka]

[0072] (In the formula, R 1 and R 5 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 2 and R 4 Each of these independently represents a hydrogen atom or a methyl group, and R 3 (This represents a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group with 6 to 20 carbon atoms, or a divalent heterocyclic group with 4 to 20 carbon atoms.)

[0073] Specific methods for producing a diepoxide structure represented by general formula (1) using the diallyl structure represented by general formula (6) mentioned above include, for example, a method of producing the diallyl structure represented by general formula (6) by oxidation in the presence of a peroxide.

[0074] Examples of peroxides that can be used in this process include organic peroxides such as performic acid, peracetic acid, trifluoroperacetic acid, perbenzoic acid, metachloroperbenzoic acid, and monoperoxyphthalic acid; inorganic peroxides such as permanganic acid; and peroxides such as di-t-butyl peroxide, dicumyl peroxide, and benzoyl peroxide. Among these, from the viewpoint of easily obtaining the compounds of this disclosure in good yield, it is preferable to use one or more selected from the group consisting of performic acid, peracetic acid, trifluoroperacetic acid, perbenzoic acid, metachloroperbenzoic acid, and monoperoxyphthalic acid, and it is more preferable to use one or more selected from the group consisting of performic acid, peracetic acid, perbenzoic acid, and metachloroperbenzoic acid.

[0075] The amount of peroxide used when oxidizing the diallyl structure represented by general formula (6) in the presence of a peroxide is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of easily obtaining the compound of this disclosure in good yield, it is preferable to use 2 mmol to 20 mmol of peroxide for every 1 mmol of the diallyl structure represented by general formula (6), and more preferably 4 mmol to 6 mmol.

[0076] The temperature at which the diallyl structure represented by general formula (6) is oxidized in the presence of a peroxide is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of obtaining the compound of this disclosure in good yield, a temperature of -30°C to 50°C is preferred, and more preferably -10°C to 30°C. Furthermore, the reaction time at which the diallyl structure represented by general formula (6) is oxidized in the presence of a peroxide is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of obtaining the compound of this disclosure in good yield, a reaction time of 1 hour to 50 hours is preferred.

[0077] When oxidizing the diallyl structure represented by general formula (6) in the presence of a peroxide, a solvent may be used as needed. Examples of such solvents include formamide, acetamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, ethyl acetate, propyl acetate, butyl acetate, acetonitrile, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, tetrachloroethylene, 1,3-dimethyl-2-imidazolidinone, benzene, toluene, xylene, dioxane, and dimethyl sulfoxide. Among these, from the viewpoint of easily obtaining the compounds of this disclosure in good yield, it is preferable to use one or more selected from the group consisting of dichloromethane, dichloroethane, trichloroethylene, tetrachloroethylene, 1,3-dimethyl-2-imidazolidinone, benzene, toluene, xylene, dioxane, and dimethyl sulfoxide.

[0078] (6) Manufacturing process 2 of the compound (diepoxide structure) of the present disclosure As a method for producing the compound of this disclosure, a method can also be used in which, after the steps of producing the diester structure and the diol structure described above, a step of producing a diepoxide structure (the compound of this disclosure) by introducing an epoxy group into the diol structure represented by general formula (5) is performed (step 2 for producing the diepoxide structure). In this case, a specific method for introducing an epoxy group into the diol structure represented by general formula (5) is, for example, a method of reacting the diol structure represented by general formula (5) with epichlorohydrin and / or methylepichlorohydrin. The ratio of each starting material used when reacting the diol structure represented by general formula (5) with epichlorohydrin and / or methylepichlorohydrin is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of easily obtaining the compound of this disclosure in good yield, it is preferable to use 2 mmol to 30 mmol of epichlorohydrin and / or methylepichlorohydrin for every 1 mmol of the diol structure represented by general formula (5), and more preferably 3 mmol to 20 mmol.

[0079] The reaction temperature when reacting the diol structure represented by general formula (5) with epichlorohydrin and / or methylepichlorohydrin is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of obtaining the compound of this disclosure in good yield, it is preferably 20°C to 150°C, and more preferably 30°C to 80°C. The reaction time when reacting the diol structure represented by general formula (5) with epichlorohydrin and / or methylepichlorohydrin is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of obtaining the compound of this disclosure in good yield, it is preferably 1 hour to 10 hours.

[0080] When reacting the diol structure represented by general formula (5) with epichlorohydrin and / or methylepichlorohydrin, alkali metal hydroxides, alkaline earth metal hydroxides, etc., can be used as needed. Examples of alkali metal hydroxides and alkaline earth metal hydroxides that can be used in this step include sodium hydroxide, lithium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, and barium hydroxide. Among these, sodium hydroxide and / or potassium hydroxide are preferred from the viewpoint of easily obtaining the compound of this disclosure in good yield. When alkali metal hydroxides and / or alkaline earth metal hydroxides are used in this step, from the viewpoint of easily obtaining a compound that can form a cured product with better heat resistance, it is preferable to use 2 mmol to 10 mmol of alkali metal hydroxide and / or alkaline earth metal hydroxide per 1 mmol of the diol structure represented by general formula (5), and more preferably 2 mmol to 5 mmol.

[0081] (7) Others As for the method of producing the compound of this disclosure, from the viewpoint of easily obtaining a compound that can form a cured product with excellent heat resistance, it is preferable to produce it by a method including (2) a step of producing a diester structure, (3) a step of producing a diol structure, (4) a step of producing a diallyl structure, and (5) a step of producing the compound of this disclosure (diepoxide structure) 1, using a hydroxy compound as a starting material obtained from myo-inositol, etc., or by a method including (2) a step of producing a diester structure, (3) a step of producing a diol structure, and (6) a step of producing the compound of this disclosure (diepoxide structure) 2, using a hydroxy compound as a starting material obtained from myo-inositol, etc. Among these, from the viewpoint of easily obtaining a compound that can form a cured product with excellent heat resistance in good yield, it is more preferable to produce it by a method including (2) a step of producing a diester structure, (3) a step of producing a diol structure, (4) a step of producing a diallyl structure, and (5) a step of producing the compound of this disclosure (diepoxide structure) 1, using a hydroxy compound as a starting material obtained from myo-inositol, etc.

[0082] 3. Uses of the compounds disclosed herein The applications of the compounds disclosed herein are not particularly limited and include various applications in which epoxy compounds are used. Specifically, applications of the compounds disclosed herein include semiconductor encapsulating materials, laminates for printed circuit boards, adhesives for electronic components, encapsulants for electronic components, casting materials, varnishes, paints, structural adhesives, fiber-reinforced composite materials, and the like.

[0083] B. Composition Next, the compositions of this disclosure will be described. The compositions of this disclosure are characterized by containing the compound represented by the general formula (1) described above. Because the compositions of this disclosure contain the compound represented by the general formula (1), they can form cured products with excellent heat resistance. In addition to the compound represented by the general formula (1), the compositions of this disclosure may also contain curing agents, solvents, other epoxy compounds, etc., depending on the purpose.

[0084] 1.Compound The compound represented by general formula (1) contained in the composition of this disclosure is the same as that described in section "A. Compounds" above, and therefore its description is omitted here.

[0085] The content of the compound represented by general formula (1) in the composition of this disclosure is not particularly limited and can be adjusted as appropriate depending on the purpose. However, from the viewpoint of forming a cured product with better heat resistance, the content of the compound represented by general formula (1) is preferably 1% to 99% by mass, more preferably 2% to 98% by mass, and even more preferably 4% to 96% by mass, based on the total amount of the composition of this disclosure.

[0086] 2. Hardener The compositions of this disclosure preferably contain a curing agent in order to improve curability and facilitate the formation of cured products with superior heat resistance. The curing agents that can be used in this disclosure are not particularly limited, and those commonly used as epoxy curing agents or polymerization initiators can be used, but examples include aliphatic amines, aromatic amines, isocyanates, polyfunctional hydroxyl-containing compounds, acid anhydrides, polyfunctional acids, imidazoles, polyfunctional mercaptans, boron trihalide complexes, dicyanamides, and mixtures thereof.

[0087] Aliphatic amines (including alicyclic amines) include those having one or more primary or secondary amino groups in the molecule and not having an aromatic carbocyclic ring. Specifically, examples include 1,2-diaminocyclohexane, 1,3-bisaminomethylcyclohexane, isophoronediamine, ethylenediamine, diethylenetriamine, hexamethylenediamine, triethylenetetraamine, tetraethylenepentaamine, ethanolamine, piperazine, aminoethylpiperazine, aminoethylethanolamine, diethylaminopropylamine, dimethylaminopropylamine, 2,5-dimethyl-2,5-hexanediamine, bis(aminocyclohexyl)methane, 3-amino-1-cyclohexylaminopropane, polyethanolamine, polypropanolamine, polyethyleneimine, and mixtures thereof. Among these, in this disclosure, from the viewpoint of forming a cured product with superior heat resistance, aliphatic amines having one or more primary amino groups in the molecule are preferred, and aliphatic amines having two or more primary amino groups in the molecule are more preferred.

[0088] Examples of aromatic amines include diaminobenzene, methylenedianiline, oxydianiline, diaminodiphenyl sulfide, diaminodiphenyl sulfone, 2,4-bis-(p-aminobenylu)aniline, diaminotoluene, ketimines, amidoamines, and mixtures thereof.

[0089] Examples of isocyanates include compounds having one or more isocyanate groups in their molecule. Specifically, examples include tolylene diisocyanate, methylcyclohexane diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, dimer acid diisocyanate, trimethylhexamethylene diisocyanate, lysine triisocyanate, and the like. Furthermore, polyisocyanate compounds obtained by reacting these isocyanate compounds with compounds having at least two active hydrogen atoms such as amino groups, hydroxyl groups, carboxyl groups, and water, as well as 3-5 mers of polyisocyanate compounds, can also be used.

[0090] Examples of polyfunctional hydroxyl-containing compounds include novolacs such as thermoplastic phenol-formaldehyde resins obtained by using an acid catalyst and excess phenol, resoles such as alkali-catalyzed thermosetting phenol-formaldehyde resins consisting of partially condensed phenol alcohols, and bisphenols such as bisphenol A (4,4'-isopropylidenediphenol), bisphenol F (bis(4-hydroxyphenyl)methane), and 2,2'-bisphenol.

[0091] Examples of acid anhydrides include phthalic anhydride, polyadipic acid polyanhydride, polyacerain polyanhydride, polysebacin polyanhydride, pyromellitic anhydride, chlorenic anhydride, succinic anhydride, dodecenyl succinic anhydride, hexahydrophthalic anhydride, maleic anhydride, methylhexahydrophthalic anhydride, tetrahydrophthalic anhydride, benzophenonetetracarboxylic anhydride, and mixtures thereof.

[0092] Examples of polyfunctional acids include adipic acid, sebacic acid, azelaic acid, terephthalic acid, isophthalic acid, cyclohexanedicarboxylic acid, and mixtures thereof.

[0093] Examples of imidazoles include 2-methylimidazole, 2-hydroxypropylimidazole, 2-heptadecylimidazole, 1-benzyl-2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cycloethyl-2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, and mixtures thereof.

[0094] Examples of polyfunctional mercaptans include dimercaptosuccinic acid, dimercaptoethane, dimercaptopropane, dimercaptobutane, dimercaptopentane, dimercaptohexane, dimercaptodecane, dimercaptodiethyl ether, dimercaptodiethyl sulfide, xylylene dimercaptan, 1,4-benzenedithiol, ethylene glycol bis(mercaptoacetate), polyethylene glycol bis(mercaptoacetate), propylene glycol bis(mercaptoacetate), and polypropylene Polyethylene glycol bis(mercaptoacetate), glycerin tris(mercaptoacetate), trimethylolethane tris(mercaptoacetate), trimethylolpropane tris(mercaptoacetate), pentaerythritol tetrakis(mercaptoacetate), dipentaerythritol hexakis(mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), polyethylene glycol bis(3-mercaptopropionate), propylene glycol bis(3-mercaptopropionate) Lucaptopropionate), polypropylene glycol bis(3-mercaptopropionate), glycerin tris(3-mercaptopropionate), trimethylolethane tris(mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), ethylene glycol bis(3-mercaptobutyrate), polyethylene glycol Examples include rubis (3-mercaptobutyrate), propylene glycol bis(3-mercaptobutyrate), polypropylene glycol bis(3-mercaptobutyrate), glycerin tris(3-mercapbutyrate), trimethylolethane tris(mercaptobutyrate), trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptobutyrate), dipentaerythritol hexakis(3-mercaptobutyrate), and mixtures thereof.

[0095] Examples of boron trihalide complexes include boron trifluoride-monoethylamine complexes, boron trifluoride-piperidine complexes, boron trifluoride-triethylamine complexes, boron trifluoride-aniline complexes, and mixtures thereof.

[0096] In this disclosure, a photoacid generator that generates acid by irradiation with energy rays such as ultraviolet light, a thermoacid generator that generates acid by heating, and a photobase generator that generates a base by irradiation with energy rays such as ultraviolet light can also be used as curing agents.

[0097] Specifically, examples of photoacid generators include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, thianthrenium salts, thiooxantonium salts, and (2,4-cyclopentadiene-1-yl)[(1-methylethylbenzene]-Fe cations, where the anionic portion is BF4 - PF6 - SbF6 - [BX4] - Examples include using an onium salt composed of (wherein X is a phenyl group substituted with at least two fluorine or trifluoromethyl groups) alone or in combination of two or more types, and more specifically, examples include those described as photocationic polymerization initiators in Japanese Patent Application Publication No. 2023-181911.

[0098] Examples of thermal acid generators include honate, triphenylsulfonium tetrafluoroborate, tri-p-tolylsulfonium hexafluorophosphate, tri-p-tolylsulfonium trifluoromethanesulfonate, bis(cyclohexylsulfonyl)diazomethane, bis(tert-butylsulfonyl)diazomethane, bis(p-toluenesulfonyl)diazomethane, triphenylsulfonium trifluoromethanesulfonate, diphenyl-4-methylphenylsulfonium trifluoromethanesulfonate, diphenyl-2,4,6-trimethylphenylsulfonium-p-toluenesulfonate, and diphenyl-p-phenylthiophenylsulfonium hexafluorophosphate. More specifically, examples include those described as thermal cationic polymerization initiators in Japanese Patent Publication No. 2023-181911.

[0099] Examples of photobase generators include 1-(anthraquinone-2-yl)ethyl N-cyclohexylcarbamate, 9-anthrylmethyl N,N-diethylcarbamate, 9-anthrylmethyl piperidine-1-carboxylic acid, 9-anthrylmethyl N,N-dicyclohexylcarbamate, 1-(anthraquinone-2-yl)ethyl N,N-dicyclohexylcarbamate, 1-(anthraquinone-2-yl)ethyl imidazole-1-carboxylic acid, 2-(3-benzoylphenyl)propionate, (E)-N-cyclohexyl-3-(2-hydroxyphenyl)acrylamide, 2-(3- Examples include benzoylphenyl)propionate, 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguanidium=n-butyltriphenyl borate, 1,2-diisopropyl3-[bis(dimethylamino)methylene]guanidium=2-(3-benzoylphenyl)propionate, 4-hydroxypiperidine-1-carboxylic acid (2-nitrophenyl)methyl, 4-(methacryloyloxy)piperidine-1-carboxylic acid (2-nitrophenyl)methyl, guanidium 2-(3-benzoylphenyl)propionate, (E)-1-piperidino-3-(2-hydroxyphenyl)-2-propen-1-one, and mixtures thereof.

[0100] From the viewpoint of further improving curability and making it easier to form a cured product with excellent heat resistance, the compositions of this disclosure preferably contain at least one aliphatic amine as a curing agent, more preferably contain an aliphatic amine having two or more primary amino groups in the molecule, even more preferably contain one or more selected from the group consisting of 1,2-diaminocyclohexane, 1,3-bisaminomethylcyclohexane, isophoronediamine, ethylenediamine, diethylenetriamine, hexamethylenediamine, and triethylenetetraamine, and particularly preferably contain one or more selected from the group consisting of 1,3-bisaminomethylcyclohexane, isophoronediamine, and hexamethylenediamine.

[0101] If the composition of the present disclosure contains a curing agent, the content of the curing agent in the composition of the present disclosure is not particularly limited and can be adjusted as appropriate depending on the purpose. However, from the viewpoint of forming a cured product with better heat resistance, the content of the curing agent is preferably 0.1% to 70% by mass, more preferably 0.5% to 50% by mass, and even more preferably 1% to 30% by mass, based on the total amount of the composition of the present disclosure.

[0102] Furthermore, if the composition of this disclosure contains a curing agent, the content of the curing agent relative to the content of the compound represented by general formula (1) in the composition of this disclosure is not particularly limited and can be adjusted as appropriate depending on the purpose. However, from the viewpoint of forming a cured product with better heat resistance, it is preferable that the content of the curing agent be 1 to 50 parts by mass, and more preferably 5 to 30 parts by mass, per 100 parts by mass of the compound represented by general formula (1) in the composition of this disclosure.

[0103] 3. Solvent Solvents that can be contained in the compositions of this disclosure include, for example, water, methanol, ethanol, propanol, isopropanol, butanol, hexanol, octanol, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, polyoxyethylene glycol, polyoxypropylene glycol, ethylene propylene glycol, ethyl cellosolve, butyl cellosolve, acetone, methoxypropanol, ethoxypropanol, tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, etc., and one or more of these can be used. In this disclosure, from the viewpoint of forming a cured product with superior heat resistance, it is preferable to use one or more solvents selected from the group consisting of tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide, and it is more preferable to use one or more solvents selected from the group consisting of tetrahydrofuran, dioxane, dimethylformamide, and N-methylpyrrolidone.

[0104] If the composition of the present disclosure contains a solvent, the solvent content in the composition of the present disclosure is not particularly limited and can be adjusted as appropriate depending on the purpose. However, from the viewpoint of forming a cured product with better heat resistance, the solvent content is preferably 1% to 99% by mass, more preferably 5% to 98% by mass, and even more preferably 10% to 96% by mass, based on the total amount of the composition of the present disclosure.

[0105] 4. Other epoxy compounds Other epoxy compounds that may be contained in the compositions of this disclosure include compounds other than those represented by general formula (1) that have one or more epoxy groups in their molecule. These other epoxy compounds can be either water-soluble or non-water-soluble epoxy compounds. Examples include: glycidyl ethers of monovalent phenols such as phenol, cresol, and butylphenol, or their alkylene oxide adducts; polyglycidyl ethers of polyvalent phenols having at least one aromatic ring, or their alkylene oxide adducts; phenol novolac type epoxy compounds; glycidyl ethers of phenols having two or more phenolic hydroxyl groups, such as resorcinol, hydroquinone, and catechol; polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups, such as benzenedimethanol, benzenediethanol, and benzenedibutanol; polyglycidyl esters of polybasic acid aromatic compounds having two or more carboxylic acids, such as phthalic acid, terephthalic acid, and trimellitic acid; glycidyl esters of benzoic acids such as benzoic acid, toluic acid, and naphthoic acid; and epoxides of styrene oxide or divinylbenzene.

[0106] 5. Uses of the composition Applications of the compositions disclosed herein include, for example, semiconductor encapsulating materials, laminates for printed circuit boards, adhesives for electronic components, encapsulants for electronic components, casting materials, varnishes, paints, structural adhesives, and fiber-reinforced composite materials.

[0107] C. Cured product Next, the cured product of the present disclosure will be described. The cured product of the present disclosure is characterized by being a cured product of the composition described above. The cured product of the present disclosure has excellent heat resistance because it cures a composition containing a compound represented by general formula (1). It can be said that the higher the glass transition temperature of the cured product, the better the heat resistance. In this case, the glass transition temperature of the cured product of the present disclosure is not particularly limited, but from the viewpoint of having better heat resistance, it is preferable that the glass transition temperature of the cured product is 90°C or higher, more preferably 100°C or higher, even more preferably 140°C or higher, and particularly preferably 160°C or higher. The upper limit of the glass transition temperature of the cured product of the present disclosure is not particularly limited, but for example it can be 300°C or lower, and preferably 260°C or lower.

[0108] The cured product of this disclosure can be obtained by curing the above-described composition by a desired method, specifically by curing it by the method described in "D. Method for producing the cured product" below.

[0109] Applications of the cured products of this disclosure include, for example, semiconductor encapsulating materials, laminates for printed circuit boards, adhesives for electronic components, encapsulating materials for electronic components, casting materials, varnishes, paints, structural adhesives, and fiber-reinforced composite materials.

[0110] D. Method for producing cured products Next, a method for manufacturing the cured product of this disclosure will be described. The method for manufacturing the cured product of this disclosure is characterized by having a curing step for curing the composition described above. Since the method for manufacturing the cured product of this disclosure cures a composition containing a compound represented by general formula (1), it is possible to produce a cured product with excellent heat resistance. The method for manufacturing the cured product of this disclosure has a curing step described later, but may have other steps depending on the purpose.

[0111] 1.Curing process The curing process in this disclosure is a process of curing the composition described above. The composition used in this disclosure is the same as that described in section B. Composition above, so its description is omitted here.

[0112] In this disclosure, the method for curing the composition is not particularly limited as long as it can form a desired cured product, but examples include heating the composition, irradiating the composition with light, and using a combination of these methods.

[0113] In the curing process described herein, when a method of heating the composition is used, the heating conditions are not particularly limited as long as they allow for the formation of the desired cured product and can be adjusted as appropriate. For example, a method of curing by heating at 30°C to 220°C for 1 minute to 120 hours under pressure, reduced pressure, or atmospheric pressure can be used. Among these, from the viewpoint of forming a cured product with superior heat resistance, it is preferable to use a method of curing by heating at 50°C to 200°C for 10 minutes to 96 hours, and more preferably a method of curing by heating at 60°C to 150°C for 1 hour to 72 hours.

[0114] In the curing process described herein, when a method of irradiating the composition with light is used, the light source is not particularly limited and can be selected as appropriate. For example, ultra-high pressure mercury lamps, high pressure mercury lamps, medium pressure mercury lamps, low pressure mercury lamps, mercury vapor arc lamps, xenon arc lamps, carbon arc lamps, metal halide lamps, fluorescent lamps, tungsten lamps, excimer lamps, germicidal lamps, light-emitting diodes, YAG lasers, CRT light sources, etc., can be used.

[0115] In the curing process described herein, when a method of irradiating the composition with light is used, the light irradiation conditions are not particularly limited and can be adjusted as appropriate. However, from the viewpoint of forming a cured product with excellent heat resistance, the light irradiation conditions should be such that the integrated light amount from irradiation is 10 mJ / cm². 2 ~20,000 mJ / cm 2 It is preferable to have the following conditions, 100 mJ / cm² 2 ~2,000 mJ / cm 2 It is more preferable to set the conditions to be such.

[0116] 2. Other processes Other steps that may be included in the method for producing the cured product of this disclosure are not particularly limited and can be appropriately selected depending on the purpose. For example, the method may include a coating step of applying the composition to various substrates before the curing step described above, and a step of washing the cured product and a step of removing the solvent after the curing step described above. In the coating step, known methods such as spin coaters, roll coaters, bar coaters, die coaters, curtain coaters, reverse coaters, various printing methods, and immersion methods can be used to apply the composition to the substrate. Furthermore, the material of the base material at this time is not particularly limited and can be appropriately selected according to the purpose, but for example, base materials such as aluminum, titanium, stainless steel, mild steel, plated steel, glass, diacetylcellulose, triacetylcellulose (TAC), propionylcellulose, butyrylcellulose, acetylpropionylcellulose, nitrocellulose, polyamide, polyimide, polyurethane, epoxy resin, polycarbonate, polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, polybutylene terephthalate, polystyrene, polyethylene, polypropylene, polymethylpentene, polyvinyl acetate, polyvinyl chloride, polyvinyl fluoride, polymethyl methacrylate, polyacrylate, polycarbonate, polysulfone, polyethersulfone, polyetherketone, polyetherimide, polyoxyethylene, norbornene resin, and cycloolefin polymer (COP) can be used.

[0117] In this disclosure, a pretreatment step may be included in which the substrate is subjected to surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high-frequency treatment, glow discharge treatment, activated plasma treatment, or laser treatment, prior to the coating step described above.

[0118] The steps for washing the cured product and removing the solvent are not particularly limited and known methods can be used. For example, after the curing step, the cured product may be washed with an insoluble solvent such as methanol or chloroform, and then dried at 20°C to 120°C under normal pressure or reduced pressure.

[0119] E. Others The following aspects are included in this disclosure:

[0120] [1] A compound represented by the following general formula (1). [ka] (In the formula, R 1 and R 5 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 2 and R 4 Each of these independently represents a hydrogen atom or a methyl group, and R 3 (This represents a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group with 6 to 20 carbon atoms, or a divalent heterocyclic group with 4 to 20 carbon atoms.)

[0121] [2] The above R 1 and R 5 The compound described in [1], wherein each is independently a hydrogen atom or a methyl group.

[0122] [3] A composition containing the compound described in [1] or [2].

[0123] [4] The composition according to [3], wherein the composition further contains a curing agent.

[0124] [5] A cured product of the composition described in [3] or [4].

[0125] A method for producing a cured product, comprising a curing step of curing the composition described in [6] [3] or [4].

[0126] This disclosure is not limited to the embodiments described above. The embodiments described above are illustrative, and any configuration that is substantially identical to the technical idea described in the claims and achieves similar effects is included within the technical scope of this disclosure. [Examples]

[0127] The invention will be described in more detail below with reference to examples and comparative examples, but this disclosure is not limited to these examples.

[0128] [Measurement method] 1 H-NMR and 13 ¹¹¹ NMR was performed using a nuclear magnetic resonance spectrometer (JEOL Ltd. JNM-AL400). Thermogravimetric analysis (TGA) was performed using a SHIMADZU TG / DTA simultaneous analyzer (DTG-60) under a nitrogen atmosphere. Each sample was heated from 50°C to 500°C at a rate of 10°C / min.

[0129] Differential scanning calorimetry (DSC) was performed using a SHIMADZU differential scanning calorimeter (DSC-60 Plus) under a nitrogen atmosphere. Each sample was heated from room temperature to 200°C or 250°C and cooled to -50°C at a rate of 20°C / min. Subsequently, while acquiring DSC data, the samples were heated from -50°C to 200°C or 250°C at a rate of 10°C / min.

[0130] [Example 1: Preparation of Compound 1] <Manufacturing of Diester Structure 1> Hydroxyl compound 1, represented by the following formula (2A), was obtained by synthesis from myo-inositol according to the method described in J.Polym.Sci.2020,58,1973-1981.

[0131] [ka]

[0132] The obtained hydroxy compound 1 (2.34 g; 8.12 mmol), 1,1,3,3-tetramethoxypropane (0.660 g; 4.03 mmol), 10-camphor sulfonic acid (0.200 g; 0.850 mmol), and toluene (6 mL) were mixed in a 20 mL round-bottom flask connected to a distillation apparatus, and the mixture was heated and stirred at 140 °C for 3.5 hours. During the reaction, the amount of toluene in the flask was maintained by adding toluene as needed. The reaction mixture was cooled to room temperature, transferred to a 100 mL round-bottom flask, and diluted with methanol (80 mL). The resulting mixture was left at room temperature overnight. Subsequently, the precipitate in the mixture was isolated by suction filtration, washed with methanol, and vacuum dried to obtain diester structure 1 (1.96 g; 3.20 mmol; yield 80%) represented by the following formula (3A) as a white powder. The obtained white powder was then used for further analysis. 1 1H-NMR (measuring instrument: JNM-AL400, manufactured by JEOL Ltd., measuring solvent: deuterated chloroform) and 13 By measuring with 1C-NMR (measuring instrument: JNM-AL400, manufactured by JEOL Ltd., measuring solvent: deuterated chloroform), it was confirmed that the compound is represented by the following formula (3A). Measured and confirmed 1 H-NMR and 13 The C-NMR peak information is shown below.

[0133] 1 H-NMR(in CDCl3 at rt) 5.36(m,4H),4.88(t,J=4.8,2H),4.73(t,J=4.8,4H),4.30(m,4H),1.82(t,J=4.8,2H),1.44(s,6H),1.26(s,18H)

[0134] 13 C-NMR(in CDCl3 at rt) 178.18,108.13,89.48,70.52,66.02,63.30,62.47,39.84,39.13,27.23,24.28

[0135] [ka]

[0136] <Manufacturing of Diol Structure 1> The obtained diester structure 1 (1.96 g; 3.20 mmol), sodium hydroxide in methanol (2.0 M, 11.0 mL), and 1,4-dioxane (10.0 mL) were mixed and stirred at 100 °C for 24 hours. The reaction mixture was then cooled to room temperature, diluted with purified water (80 mL), and the mixture was left to stand overnight. The precipitate in the mixture was then isolated by suction filtration, washed with purified water, and vacuum-dried to obtain diol structure 1 (1.28 g; 2.82 mmol; yield 88%) represented by the following formula (4A) as a white solid. Regarding the obtained white solid, 1 1H-NMR (measuring instrument: JNM-AL400, manufactured by JEOL Ltd., measuring solvent: deuterated chloroform) and 13 By measuring with 1C-NMR (measuring instrument: JNM-AL400, manufactured by JEOL Ltd., measuring solvent: deuterated chloroform), it was confirmed that the compound is represented by the following formula (4A). Measured and confirmed 1 H-NMR and 13 The C-NMR peak information is shown below.

[0137] 1 H-NMR(in CDCl3 at 80℃) 5.31(t,J=5.2,2H),5.00(d,J=8.0,2H),4.93(t,J=4.8,2H),4.61(t,J=4.8 ,4H),4.12-4.10(m,2H),4.04-4.02(m,4H),1.62(t,J=5.2,2H),1.32(s,6H)

[0138] 13 C-NMR(in CDCl3 at 80℃) 107.08,88.68,72.20,65.41,61.03,58.85,23.79

[0139] [ka]

[0140] <Manufacturing of Diallyl Structure 1> 60% sodium hydride (1.956 g; 81.51 mmol) in mineral oil was placed in a 500 mL eggplant flask and washed three times with 20 mL of hexane under an argon atmosphere to remove the mineral oil. Separately prepared diol structure 1 (6.176 g; 13.90 mmol) was added thereto, and the flask was purged with argon. Then, 300 mL of N,N-dimethylformamide was added. The resulting suspension was cooled in an ice bath, and allyl bromide (3.00 mL; 35.2 mmol) was slowly added dropwise over about 10 seconds. After the addition, the ice bath was removed, and the mixture was stirred at room temperature for 24 hours. Subsequently, 50 mL of purified water was added over about 1 minute to stop the reaction. The reaction solution was suction filtered to obtain a white powder. The white powder was washed with purified water and dried under heating and vacuum to obtain diallyl structure 1 (6.658 g; 12.69 mmol; yield 91%) represented by the following formula (5A). Regarding the obtained white powder, 1 1H-NMR (measurement apparatus: JNM-AL400, manufactured by JEOL Ltd., measurement solvent: deuterated chloroform) and 13 13C-NMR (measurement apparatus: JNM-AL400, manufactured by JEOL Ltd., measurement solvent: deuterated chloroform) were measured to confirm that it was a compound represented by the following formula (5A). The measured 1 1H-NMR and 13 13C-NMR results are shown in FIGS. 1 and 2, respectively. Also, the measured and confirmed 1 1H-NMR and 13 13C-NMR peak information is shown below.

[0141] 1 1H-NMR (in CDCl3 at rt) δ 6.03 - 5.93 (m, 2H), 5.33 (dd, J = 1.5, 2H), 5.28 - 5.24 (m, 4H), 4.83 (t, J = 4.6, 2H), 4.74 (t, J = 4.9, 4H), 4.31 (dd, J = 2.0, 4H), 4.19 (d, J = 5.8, 4H), 4.03 (t, J = 2.0, 2H), 1.65 (t, J = 5.4, 2H), 1.48 (s, 6H)

[0142] 1313C-NMR (in CDCl3 at rt): 134.66, 118.08, 108.17, 88.29, 70.70, 70.62, 66.42, 66.08, 62.35, 40.39, 24.29

[0143]

Chem.

[0144] <Production of Diepoxide Structure 1 (Compound 1)> The obtained diallyl structure 1 (0.512 g; 0.975 mmol) was dissolved in dichloromethane (10 mL) and cooled to 0 °C. Meta-chloroperbenzoic acid (69 - 75%; 0.878 g; 5.09 mmol) was added thereto, and the mixture was stirred at 0 °C for 1 hour and further stirred at room temperature for 23 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was washed with ethanol and filtered by suction. By heating and drying, diepoxide structure 1 (0.422 g; 0.758 mmol; yield 78%), which is a compound of the present disclosure represented by the following formula (1A), was obtained as a white powder. Regarding the obtained white powder, 1 1H-NMR (measurement apparatus: JNM-AL400, manufactured by JEOL Ltd., measurement solvent: deuterated chloroform) and 13 13C-NMR (measurement apparatus: JNM-AL400, manufactured by JEOL Ltd., measurement solvent: deuterated chloroform) were measured to confirm that it is a compound represented by the following formula (1A). The measured 1 1H-NMR and 13 13C-NMR results are shown in FIGS. 3 and 4, respectively. Also, the measured and confirmed 1 1H-NMR and 13 13C-NMR peak information is shown below.

[0145] 1H-NMR(in CDCl3 at rt) 5.32(t,J=4.6,2H),4.85(t,J=4.6,2H),4.74-4.73(m,4H),4.38(t,J=2.8,2H),4.33(t,J=2.8,2H),4.16(t,J=1.9,2H),4.06-4.03( dd,J=2.4,2H),3.55-3.51(dd,J=6.4,2H),3.26-3.22(m,2H),2.83(t,J=4.6,2H),2.66-2.64(m,2H),1.76(t,J=4.9,2H),1.47(s,6H)

[0146] 13 C-NMR(in CDCl3 at rt) 108.37,89.56,71.27,70.69,70.55,68.36,66.26,66.22,62.54,51.46,44.36,40.42,24.53

[0147] [ka]

[0148] [Example 2: Preparation of cured product 1 (polyadduct of compound 1 and hexamethylenediamine)] Compound 1 (0.223 g; 0.40 mmol) was placed in a sample tube, and hexamethylenediamine (0.023 g; 0.20 mmol) as a curing agent and N,N-dimethylformamide (dehydrated) (1 mL) were added. The mixture was stirred at 100°C for 24 hours, after which it became gel-like. After washing with methanol, the gel-like solid was removed by suction filtration and washed with chloroform. The solvent was removed by heating and vacuum drying to obtain a pale orange, lumpy solid (0.2231 g; yield 91%).

[0149] [Example 3: Preparation of cured product 2 (polyadduct of compound 1 and 1,3-bisaminomethylcyclohexane)] Compound 1 (0.223 g; 0.40 mmol), prepared separately, was placed in a sample tube, and 1,3-bisaminomethylcyclohexane (0.028 g; 0.20 mmol) as a curing agent and N,N-dimethylformamide (dehydrated) (1 mL) were added. The mixture was stirred at 100°C for 24 hours, after which it became gel-like. After washing with methanol, the gel-like solid was removed by suction filtration. The removed gel-like solid was washed with chloroform, and the solvent was removed by heating and vacuum drying to obtain a pale yellowish-white bulky solid (0.2058 g; yield 89%).

[0150] [Example 4: Preparation of cured product 3 (polyadduct of compound 1 and isophoronediamine)] Compound 1 (0.223 g; 0.40 mmol), prepared separately, was placed in a sample tube, and isophoronediamine (0.034 g; 0.20 mmol) as a curing agent and N,N-dimethylformamide (dehydrated) (1 mL) were added. The mixture was stirred at 100°C for 48 hours, after which it became gel-like. After washing with methanol, the gel-like solid was removed by suction filtration. The removed gel-like solid was washed with chloroform, and the solvent was removed by heating and vacuum drying to obtain a white powder-like solid (0.2010 g; yield 78%).

[0151] [Comparative Example 1: Production of cured product 4 (a polyaddition of 2,2-bis(4-glycidyloxyphenyl)propane and hexamethylenediamine)] 2,2-bis(4-glycidyloxyphenyl)propane (0.136 g; 0.40 mmol) was placed in a sample tube, and hexamethylenediamine (0.023 g; 0.20 mmol) as a curing agent and N,N-dimethylformamide (dehydrated) (1 mL) were added. After stirring at 100°C for 24 hours, a gel-like consistency was obtained. The mixture was washed with methanol, and the solvent was removed by heating and vacuum drying to obtain a pale yellow, lumpy solid (0.1403 g; yield 88%).

[0152] [Comparative Example 2: Production of Cured Product 5 (a polyadduct of 2,2-bis(4-glycidyloxyphenyl)propane and 1,3-bisaminomethylcyclohexane)] 2,2-bis(4-glycidyloxyphenyl)propane (0.136 g; 0.40 mmol) was placed in a sample tube, and 1,3-bisaminomethylcyclohexane (0.028 g; 0.20 mmol) as a curing agent and N,N-dimethylformamide (dehydrated) (1 mL) were added. After stirring at 100°C for 24 hours, a gel-like consistency was obtained. The mixture was washed with methanol, and the solvent was removed by heating and vacuum drying to obtain a pale yellow, lumpy solid (0.1604 g; yield 98%).

[0153] [Comparative Example 3: Production of Cured Product 6 (a polyadduct of 2,2-bis(4-glycidyloxyphenyl)propane and isophoronediamine)] 2,2-bis(4-glycidyloxyphenyl)propane (0.136 g; 0.40 mmol) was placed in a sample tube, and isophorone diamine (0.034 g; 0.20 mmol) as a curing agent and N,N-dimethylformamide (dehydrated) (1 mL) were added. After stirring at 100°C for 48 hours, a gel-like consistency was obtained. The mixture was washed with methanol, and the solvent was removed by heating and vacuum drying to obtain a pale yellow, lumpy solid (0.1694 g; yield 100%).

[0154] The glass transition temperature (Tg) was measured for the cured products obtained in Examples 2-4 and Comparative Examples 1-3. Specifically, approximately 5 mg of each cured product was first measured and placed in a differential scanning calorimeter pan. Using a SHIMADZU differential scanning calorimeter (DSC-60 Plus), the product was heated from room temperature to 200°C under a nitrogen atmosphere, cooled to -50°C at a rate of 20°C / min, and then measured from -50°C to 250°C at a rate of 10°C / min to confirm the glass transition temperature (Tg). A higher glass transition temperature of the cured product indicates superior heat resistance. The measurement results are shown in Table 1.

[0155] [Table 1]

[0156] [Example 5: Preparation of cured product 7 (a polyaddition of compound 1 and tris(3-mercaptopropionic acid)trimethylolpropane)] Tris(3-mercaptopropionic acid) trimethylolpropane (0.107 g; 0.27 mmol) and 2,4,6-tris(dimethylaminomethyl)phenol (0.015 g; 0.057 mmol) were added to a sample tube. Then, compound 1 (0.223 g; 0.40 mmol) prepared separately and N,N-dimethylformamide (dehydrated) (1 mL) were added. The mixture was stirred at 100°C for 24 hours, resulting in a gel. After washing with methanol, the gel-like solid was removed by suction filtration. The removed gel-like solid was washed with chloroform, and the solvent was removed by heating and vacuum drying to obtain a dark orange, lumpy solid (0.3198 g; yield 97%).

[0157] [Comparative Example 4: Production of cured product 8 (a polyadditive of 2,2-bis(4-glycidyloxyphenyl)propane and tris(3-mercaptopropionic acid)trimethylolpropane)] Tris(3-mercaptopropionic acid)trimethylolpropane (0.107 g; 0.27 mmol) and 2,4,6-tris(dimethylaminomethyl)phenol (0.015 g; 0.057 mmol) were added to a sample tube, followed by the addition of 2,2-bis(4-glycidyloxyphenyl)propane (0.136 g; 0.40 mmol) and N,N-dimethylformamide (dehydrated) (1 mL). The mixture was stirred at 100°C for 24 hours, resulting in a gel. After washing with methanol, the gel solid was removed by suction filtration. The removed gel solid was washed with chloroform, and the solvent was removed by heating and vacuum drying to obtain a dark orange, lumpy solid (0.2416 g; yield 99%).

[0158] [Example 6: Production of cured product 9 (ring-opening polymer of compound 1 using 2-ethyl-4-methylimidazole as an initiator)] 2-ethyl-4-methylimidazole (0.0044 g; 0.04 mmol), compound 1 (0.222 g; 0.40 mmol) prepared separately, and N,N-dimethylformamide (dehydrated) (0.2 mL) were added to a sample tube. After stirring at 100°C for 24 hours, a reddish-brown solid was obtained. After washing with methanol, the solid was removed by suction filtration. The removed solid was washed with chloroform, and the solvent was removed by heating and vacuum drying to obtain an orange powdery solid (0.2092 g; yield 92%).

[0159] [Comparative Example 5: Production of cured product 10 (ring-opening polymer of 2,2-bis(4-glycidyloxyphenyl)propane using 2-ethyl-4-methylimidazole as an initiator)] 2-ethyl-4-methylimidazole (0.0041 g; 0.037 mmol), 2,2-bis(4-glycidyloxyphenyl)propane (0.137 g; 0.40 mmol), and N,N-dimethylformamide (anhydrous) (0.2 mL) were added to a sample tube. After stirring at 100°C for 24 hours, a reddish-brown solid was obtained. After washing with methanol, the solvent was removed by heating and vacuum drying to obtain an orange powdery solid (0.1350 g; yield 96%).

[0160] The glass transition temperature (Tg) was measured for the cured products obtained in Examples 5-6 and Comparative Examples 4-5. Specifically, approximately 5 mg of each cured product was first measured and placed in a differential scanning calorimeter pan. Using a SHIMADZU differential scanning calorimeter (DSC-60 Plus), the product was heated from room temperature to 200°C under a nitrogen atmosphere, cooled to -50°C at a rate of 20°C / min, and then measured from -50°C to 250°C at a rate of 10°C / min to confirm the glass transition temperature (Tg). A higher glass transition temperature of the cured product indicates superior heat resistance. The measurement results are shown in Table 2.

[0161] [Table 2]

[0162] From the results described above, it was confirmed that the cured product obtained by curing a composition containing the compound represented by general formula (1) obtained in this disclosure has a higher glass transition temperature than the cured product of the comparative example obtained using a conventional epoxy compound. From these results, it can be seen that the compound of this disclosure can form a cured product with excellent heat resistance.

Claims

1. A compound represented by the following general formula (1). 【Chemistry 1】 (In the formula, R １ and R ５ Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R ２ and R ４ Each of these independently represents a hydrogen atom or a methyl group, R ３ (This represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heterocyclic group having 4 to 20 carbon atoms.)

2. R １ and R ５ The compound according to claim 1, wherein each is independently a hydrogen atom or a methyl group.

3. A composition containing the compound described in claim 1.

4. The composition according to claim 3, wherein the composition further contains a curing agent.

5. A cured product of the composition according to claim 3.

6. A method for producing a cured product, comprising a curing step for curing the composition described in claim 3.

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