Epoxy resin, method for producing epoxy resin, epoxy composition, curable composition, cured product, method for producing cured product, and compound

Abstract

Provided is an epoxy resin characterized by having an internal triple bond and a weight-average molecular weight of not less than 500.

Description

Epoxy resin, method for producing epoxy resin, epoxy composition, curable composition, cured product, method for producing cured product, and compound

[0001] The present disclosure relates to an epoxy resin, a method for producing an epoxy resin, an epoxy composition, a curable composition, a cured product, a method for producing a cured product, and a compound.

[0002] Epoxy resins are widely used as components of adhesives, paints, coating agents, etc. For example, Patent Document 1 describes a paint that uses a bisphenol A epoxy compound as the epoxy resin.

[0003] International Publication No. 2022 / 080048

[0004] However, the epoxy-based curable composition containing the epoxy resin used in Patent Document 1 and the like has a problem in that it has insufficient low cure shrinkage. Therefore, in recent years, there has been a demand for an epoxy-based curable composition having excellent low cure shrinkage.

[0005] The present disclosure has been made in view of the above problems, and a main object of the present disclosure is to provide an epoxy resin capable of forming a curable composition having excellent low cure shrinkage.

[0006] As a result of extensive research, the present inventors have found that a curable composition with excellent low cure shrinkage can be formed by using an epoxy resin having a specific structure and specific properties.

[0007] That is, the present disclosure provides an epoxy resin characterized by having an internal triple bond and a weight average molecular weight of 500 or more.

[0008] According to the present disclosure, an epoxy resin can be obtained that can form a curable composition that has excellent low cure shrinkage.

[0009] In the present disclosure, the weight average molecular weight is preferably 500 or more and 10,000 or less, because the epoxy resin has low cure shrinkage and can form an excellent curable composition.

[0010] In the present disclosure, the content of the internal triple bonds in the epoxy resin is preferably 1 mmol / g or more and 2.5 mmol / g or less, and more preferably 1 mmol / g or more and 2.3 mmol / g or less, because the epoxy resin can form a curable composition with excellent low cure shrinkage.

[0011] In the present disclosure, the epoxy equivalent of the epoxy resin is preferably 200 g / eq or more and 1000 g / eq or less, and more preferably 300 g / eq or more and 1000 g / eq or less, because the epoxy resin can form a curable composition with excellent low cure shrinkage.

[0012] In the present disclosure, the epoxy resin preferably contains a reaction product of a first compound having an epoxy group and a second compound having an internal triple bond and a second functional group that bonds to the epoxy group, because this facilitates the formation of the epoxy resin.

[0013] In the present disclosure, the epoxy resin preferably contains a compound represented by the following general formula (1), because the epoxy resin can form an excellent curable composition with low cure shrinkage.

[0014]

[0015] (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24 each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more.

[0016]

[0017] (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents the bonding site.

[0018] The present disclosure provides a method for producing an epoxy resin, comprising a reaction step of synthesizing an epoxy resin by reacting a first compound having an epoxy group with a second compound having an internal triple bond and a second functional group that bonds to the epoxy group.

[0019] According to the present disclosure, it is possible to easily produce an epoxy resin capable of forming a curable composition having excellent low cure shrinkage.

[0020] The present disclosure provides an epoxy composition comprising the above-described epoxy resin and an epoxy compound other than the above-described epoxy resin.

[0021] According to the present disclosure, since the epoxy resin described above is contained, an epoxy composition can be obtained that can form a curable composition with excellent low cure shrinkage.

[0022] The present disclosure provides a curable composition comprising the above-described epoxy resin and a curing agent.

[0023] According to the present disclosure, since the above-described epoxy resin is contained, a curable composition having excellent low cure shrinkage can be obtained.

[0024] The present disclosure provides a cured product of the above-described curable composition.

[0025] According to the present disclosure, by using the above-described curable composition, it is possible to obtain a cured product that undergoes little change in shape before and after curing.

[0026] The present disclosure provides a method for producing a cured product, which includes a curing step of curing the above-described curable composition.

[0027] According to the present disclosure, by using the above-described curable composition, a method for producing a cured product that undergoes little change in shape before and after curing can be achieved.

[0028] The present disclosure provides a compound represented by the following general formula (1):

[0029]

[0030] (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24 each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more.

[0031]

[0032] (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34 each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents the bonding site.

[0033] According to the present disclosure, an epoxy resin having excellent low cure shrinkage can be formed.

[0034] According to the present disclosure, it is possible to provide an epoxy resin capable of forming a curable composition having excellent low cure shrinkage.

[0035] 1 is a GPC chart of the epoxy composition 1 obtained in Example 1. 1 1H-NMR measurement results of Resin 1 obtained in Example 1. 13 1 is a C-NMR measurement result of the epoxy composition 2 obtained in Example 2. 1 1H-NMR measurement results of Resin 2 obtained in Example 2. 13 1 is a C-NMR measurement result of the epoxy composition 3 obtained in Example 3. 11H-NMR measurement results of Resin 3 obtained in Example 3. 13 1 shows the results of C-NMR measurement. 2 shows a GPC chart of epoxy composition 4 obtained in Example 4. 3 shows a GPC chart of epoxy composition 5 obtained in Example 5. 4 shows a GPC chart of epoxy composition 6 obtained in Example 6. 5 shows a GPC chart of epoxy composition 7 obtained in Example 7. 6 shows a GPC chart of epoxy composition 8 obtained in Example 8.

[0036] The present disclosure relates to an epoxy resin, a method for producing an epoxy resin, an epoxy composition, a curable composition, a cured product, a method for producing a cured product, and a compound. The epoxy resin, the method for producing an epoxy resin, the epoxy composition, the curable composition, the cured product, the method for producing a cured product, and the compound of the present disclosure are described in detail below.

[0037] A. Epoxy Resin First, the epoxy resin of the present disclosure will be described. The epoxy resin of the present disclosure is characterized by having an internal triple bond and a weight average molecular weight of 500 or more.

[0038] The epoxy resin of the present disclosure can form a curable composition that exhibits excellent low cure shrinkage.

[0039] The reason why the above-mentioned epoxy resins enable the formation of curable compositions with excellent low cure shrinkage is presumed to be as follows. Specifically, the epoxy resins have internal triple bonds and a weight-average molecular weight within a predetermined range, resulting in a compactly packed structure within the curable composition. As a result, the curable composition has a high resin density before curing, and the density change before and after curing is small, making it possible to form curable compositions with excellent low cure shrinkage. Furthermore, the epoxy resins have internal triple bonds and a weight-average molecular weight within a predetermined range, allowing the number and density of internal triple bonds in a molecule to be appropriately controlled. This allows the epoxy resins to exhibit low cure shrinkage and other properties while suppressing gelation during storage due to the internal triple bonds acting as reaction sites. Therefore, for example, when an epoxy composition is formed using the epoxy resins in combination with an epoxy compound other than the above-mentioned epoxy resins, or when a curable composition is formed, the epoxy resins exhibit excellent storage stability.

[0040] Furthermore, the epoxy resin has internal triple bonds, which allow the internal triple bonds to interact with the surface of the adherend, resulting in excellent adhesive strength. Furthermore, as described above, the epoxy resin has a high resin density before curing, i.e., is in a contracted state in which the epoxy resin molecules are entangled, and a cured product formed using the epoxy resin has high flexibility, allowing room for the resin molecules to untangle and expand. As a result, even if an external force acts between the adherend and the cured product, the external force can be flexibly absorbed, resulting in excellent adhesive strength. Therefore, when the epoxy resin is formed into a curable composition, it can form a cured product with excellent adhesive strength. Therefore, the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0041] The epoxy resin of the present disclosure has an internal triple bond and a predetermined weight average molecular weight.

[0042] 1. Properties of Epoxy Resin The weight-average molecular weight (Mw) of the epoxy resin is 500 or more, preferably 500 to 10,000, more preferably 1,000 to 5,000, even more preferably 1,200 to 2,000, and particularly preferably 1,300 to 1,800. This is because the epoxy resin exhibits excellent properties such as low cure shrinkage, storage stability, and adhesive strength. In the present disclosure, the weight-average molecular weight and number-average molecular weight refer to the weight-average molecular weight and number-average molecular weight calculated in terms of standard polystyrene measured by gel permeation chromatography (GPC). The following measurement conditions can be used for GPC measurement.

[0043] (GPC Measurement Conditions) GPC apparatus: GL7700 series (manufactured by GL Sciences) Column: Shodex KF-802.5 + KF-801 (manufactured by Showa Denko) Column temperature: 40°C Eluent: tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI Sample concentration: 0.1 g / 2 mL Polystyrene standards for calibration curve: Mw 96,400, 37,900, 18,100, 10,200, 5,970, 2,630, 1,010, 578, 474, 370, 266 (TSKgel standard polystyrene manufactured by Tosoh Corporation)

[0044] In the present disclosure, the weight-average molecular weight of the epoxy resin refers to the weight-average molecular weight of the entire epoxy resin, excluding the raw materials used in the synthesis of the epoxy resin (including unreacted raw material compounds, catalysts, and solvents). For example, when the epoxy resin is a reaction product of a first compound having an epoxy group and a second compound having an internal triple bond and a second functional group bonded to the epoxy group, the weight-average molecular weight can refer to the weight-average molecular weight of the entire reaction product. Furthermore, unless otherwise specified, the number-average molecular weight (Mn), internal triple bond content, epoxy equivalent, and hydroxyl equivalent of the epoxy resin described below can also be measured for the entire reaction product, which is the epoxy resin.

[0045] The number average molecular weight (Mn) of the epoxy resin is preferably 500 or more and 3,000 or less, more preferably 900 or more and 1,500 or less, and even more preferably 1,000 or more and 1,200 or less, because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0046] The internal triple bond refers to a triple bond in which both of the two carbon atoms constituting the triple bond are bonded to atoms other than hydrogen atoms. For example, a terminal triple bond in which one of the two carbon atoms constituting the triple bond is bonded to a hydrogen atom, as represented by the following formula (b1), does not fall under the category of the internal triple bond.

[0047]

[0048] The presence or absence of the internal triple bond is determined for the epoxy resin. 13 C nuclear magnetic resonance spectroscopy ( 13 This can be confirmed by C-NMR.

[0049] The content of internal triple bonds in the epoxy resin is preferably 1 mmol / g or more and 2.5 mmol / g or less, more preferably 1 mmol / g or more and 2.3 mmol / g or less, more preferably 1.5 mmol / g or more and 2 mmol / g or less, and even more preferably 1.6 mmol / g or more and 1.8 mmol / g or less. This is because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength. The content of internal triple bonds is measured by the method using an internal standard. 13 It can be quantified by C-NMR.

[0050] The epoxy equivalent of the epoxy resin is preferably 200 g / eq or more and 1000 g / eq or less, preferably 300 g / eq or more and 1000 g / eq or less, more preferably 400 g / eq or more and 1000 g / eq or less, even more preferably 500 g / eq or more and 800 g / eq or less, and particularly preferably 560 g / eq or more and 700 g / eq or less. This is because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc. The epoxy equivalent can be measured in accordance with JIS K 7236:2001 (corresponding to ISO 3001:1999).

[0051] The hydroxyl value of the epoxy resin is preferably 50 mgKOH / g or more and 300 mgKOH / g or less, more preferably 100 mgKOH / g or more and 250 mgKOH / g or less, and even more preferably 150 mgKOH / g or more and 230 mgKOH / g or less. This is because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc. The hydroxyl value can be measured in accordance with JIS K 0070-1992.

[0052] The total chlorine content of the epoxy resin is preferably 10,000 ppm or less by mass, more preferably 3,000 ppm or less, even more preferably 10 ppm or more and 1,500 ppm or less, and even more preferably 30 ppm or more and 1,000 ppm or less. This is because there is no risk of ion migration occurring, and when used as, for example, an adhesive or sealant for electrical and electronic components, a product with good reliability can be obtained. The total chlorine content can be measured in accordance with JIS K7243-3.

[0053] 2. First Epoxy Compound The epoxy resin contains an epoxy compound having an internal triple bond (hereinafter, sometimes referred to as the first epoxy compound). The epoxy resin may contain one type of first epoxy compound, or two or more types. The first epoxy compound may be any compound having an internal triple bond and an epoxy group, and may be any compound that allows the epoxy resin to satisfy the above-mentioned weight average molecular weight.

[0054] As such a first epoxy compound, for example, it is preferable to use a reaction product of a first compound having an epoxy group with a second compound having an internal triple bond and a second functional group bonding to the epoxy group, that is, it is preferable that the epoxy resin contains the reaction product, because this makes it easier to form the epoxy resin.

[0055] (1) First Compound The first compound is a compound having an epoxy group. Examples of such a first compound include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds; polyglycidyl ether compounds of polynuclear polyhydric phenol compounds or alkylene oxide adducts of the polynuclear polyhydric phenol compounds; polyglycidyl ethers of polyhydric alcohols; homopolymers or copolymers of glycidyl esters of aliphatic, aromatic, or alicyclic polybasic acids and glycidyl methacrylate; epoxy compounds having a glycidylamino group; epoxidized products of cyclic olefin compounds; epoxidized conjugated diene polymers; heterocyclic compounds, etc. In the present disclosure, the first compound is preferably a polyglycidyl ether compound of a polynuclear polyhydric phenol compound or an alkylene oxide adduct of the polynuclear polyhydric phenol compound, a polyglycidyl ether of polyhydric alcohols, or an epoxy compound having a glycidylamino group, more preferably a polyglycidyl ether compound of a polynuclear polyhydric phenol compound or an alkylene oxide adduct of the polynuclear polyhydric phenol compound, and even more preferably a polyglycidyl ether compound of a polynuclear polyhydric phenol compound. This is because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0056] Examples of the polynuclear polyhydric phenol compound include those having two or more aromatic rings and two or more phenolic hydroxyl groups. Examples of such polynuclear polyhydric phenol compounds include compounds without heterocycles, such as compounds having a naphthalene structure, compounds having a biphenol structure, compounds having a bisphenol structure, and novolac phenolic resins. In the present disclosure, the polynuclear polyhydric phenol compound is preferably a compound having a bisphenol structure. This is because the epoxy resin exhibits excellent properties such as low cure shrinkage, storage stability, and adhesive strength. Examples of the compound having a naphthalene structure include dihydroxynaphthalene. Examples of the compound having a biphenol structure include biphenol.

[0057] Examples of compounds having a bisphenol structure include compounds having a bisphenol structure in which two hydroxyphenyl groups are bonded by one atom, and compounds having a bisphenol structure in which two hydroxyphenyl groups are bonded by two or more atoms. Examples of compounds having a bisphenol structure in which two hydroxyphenyl groups are bonded by one atom include methylene bisphenol (bisphenol F), methylenebis(ortho-cresol); ethylidene bisphenol; compounds having a bisphenol A structure such as isopropylidene bisphenol (bisphenol A), isopropylidene bis(ortho-cresol), and tetrabromobisphenol A; 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, and oxybisphenol. The phrase "two hydroxyphenyl groups bonded by one atom" refers to a linking chain length of one atom that connects the benzene rings of the two hydroxyphenyl groups. The bisphenol A structure refers to a structure in which two hydroxyphenyl groups are bonded to each other on a benzene ring via an isopropylidene group, and polyglycidyl ether compounds of polyhydric phenol compounds having this structure include so-called bisphenol A epoxy resins. Furthermore, examples of compounds having the above bisphenol structure in which two hydroxyphenyl groups are bonded via two or more atoms include 1,3-bis(4-hydroxycumylbenzene) and 1,4-bis(4-hydroxycumylbenzene).

[0058] Examples of the novolac type phenolic resin include phenol novolac, orthocresol novolac, ethylphenol novolac, butylphenol novolac, octylphenol novolac, resorcinol novolac, and terpene phenol. Examples of the alkylene oxide constituting the alkylene oxide adduct of the polynuclear polyhydric phenol compound include ethylene oxide and propylene oxide.

[0059] Examples of the polyhydric alcohols include compounds that do not have an aromatic hydrocarbon ring or a heterocyclic ring. Examples of such polyhydric alcohols include chain polyhydric alcohols that do not have an aliphatic hydrocarbon ring, and alicyclic polyhydric alcohols that have an aliphatic hydrocarbon ring. Examples of chain polyhydric alcohols include ethylene glycol, propylene glycol, butylene glycol, hexanediol, polyglycol, neopentyl glycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, and sorbitol. Examples of alicyclic polyhydric alcohols include tricyclodecane dimethanol, dicyclopentadiene dimethanol, and the like, as well as hydrogenated products of the above-mentioned mononuclear polyhydric phenol compounds and polynuclear polyhydric phenol compounds.

[0060] Examples of the epoxy compound having a glycidylamino group include N,N-diglycidylaniline, bis(4-(N-methyl-N-glycidylamino)phenyl)methane, and diglycidyl orthotoluidine.

[0061] The mononuclear polyhydric phenol compound may be a compound having one aromatic hydrocarbon ring and two or more phenolic hydroxyl groups, and examples thereof include hydroquinone, resorcinol, pyrocatechol, and phloroglucinol.

[0062] Examples of the aliphatic, aromatic, or alicyclic polybasic acid constituting the homopolymer or copolymer of the glycidyl esters of aliphatic, aromatic, or alicyclic polybasic acids and glycidyl methacrylate include maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimer acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, and endomethylenetetrahydrophthalic acid.

[0063] Examples of the epoxidized cyclic olefin compound include those in which a ring structure derived from a cyclic olefin and an epoxy ring form a condensed ring, such as vinylcyclohexene diepoxide, dicyclopentadiene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, etc. Examples of the epoxidized conjugated diene polymer include epoxidized polybutadiene, epoxidized styrene-butadiene copolymer, etc.

[0064] Examples of the heterocyclic compound include triglycidyl isocyanurate.

[0065] As the first compound, commercially available epoxy resins can be used, for example, Denacol EX-313, Denacol EX-314, Denacol EX-321, Denacol EX-411, Denacol EX-421, Denacol EX-512, Denacol EX-521, Denacol EX-611, Denacol EX-612, Denacol EX-614, Denacol EX-615, Denacol EX-616, Denacol EX-617, Denacol EX-618, Denacol EX-619, Denacol EX-620, Denacol EX-621, Denacol EX-622, Denacol EX-623, Denacol EX-624, Denacol EX-625, Denacol EX-626, Denacol EX-627, Denacol EX-628, Denacol EX-629, Denacol EX-630, Denacol EX-631, Denacol EX-632, Denacol EX-633, Denacol EX-634, Denacol EX-635, Denacol EX-636, Denacol EX-637, Denacol EX-638, Denacol EX-639, Denacol EX-640, Denacol EX-641, Denacol EX-642, Denacol EX-643, Denacol EX-644, Denacol EX-645, Denacol EX-646, Denacol EX-647, Denacol EX-648, Denacol EX-649 ...9 Denacol EX-622, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol EX-861, Denacol EX-920, Denacol EX-931, Denacol EX-201, Denacol EX-711, Denacol EX-721 (manufactured by Nagase ChemteX Corporation); Epolight 200E, Epolight 400E, Epolight 70P, Epolight 200P, Epolight 400P (manufactured by Kyoeisha Chemical Co., Ltd.), ADEKA RESIN EP-4088 series, ADEKA RESIN EP-4080E, ADEKA RESIN EP-4000 series, ADEKA RESIN EP-4005, ADEKA RESIN EP-4100 series, ADEKA RESIN EP-4901 series, ADEKA RESIN EP-3980S, ADEKA GLYCIROL ED-523 series (manufactured by ADEKA Corporation); OGSOL PG-100, OGSOL EG-200, OGSOL EG-210, OGSOL EG-250 (manufactured by Osaka Gas Chemicals Co., Ltd.); YD series, YDF series, YDPN series, TDCN series (Nippon Steel & Sumikin Chemical Co., Ltd.); CELLOXIDE 2021P, CELLOXIDE 2081 (manufactured by Daicel Corporation); TECHMORE Examples of such a polymer include VG-3101L (manufactured by Printec Co., Ltd.); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, and NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); YX8800 (manufactured by Mitsubishi Chemical Corporation); HP4032, HP4032D, and HP4700 (manufactured by DIC Corporation); and KDS-8128 and KDS-8170 (manufactured by Kokudo Chemical Co., Ltd.).

[0066] The epoxy equivalent of the first compound is preferably 50 g / eq or more and 2,000 g / eq or less, more preferably 70 g / eq or more and 1,000 g / eq or less, even more preferably 100 g / eq or more and 500 g / eq or less, and particularly preferably 150 g / eq or more and 300 g / eq or less, because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0067] The number of epoxy groups contained in the first compound is preferably 2 or more and 10 or less, more preferably 2 or more and 4 or less, and even more preferably 2. This is because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0068] The first compound is preferably a compound represented by the following general formula (A), because the epoxy resin has better adhesive strength, low cure shrinkage, and the like.

[0069]

[0070] (In the formula, L 1 represents a group represented by the above general formula (a1) or a group represented by the above general formula (a2).

[0071]

[0072] (In the formula, L 2 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 3 and L 4 each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; p1 and p2 each independently represent an integer of 0 to 10; R 1 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents the bonding site.

[0073] L 2 Examples of the divalent hydrocarbon group used in the formula (1) include an aliphatic hydrocarbon group and an aromatic hydrocarbon ring-containing group.

[0074] Examples of the aliphatic hydrocarbon group include a linear or branched alkylene group having 1 to 30 carbon atoms and a divalent group containing an aliphatic ring having 3 to 30 carbon atoms. Examples of the linear or branched alkylene group having 1 to 30 carbon atoms include a methylene group, an ethylidene group, a propylidene group, and an isopropylidene group. The aliphatic ring may have a monocyclic structure or a fused ring structure. The aliphatic ring may be any ring that does not have aromaticity, and may be a saturated aliphatic ring that does not have an unsaturated bond such as an unsaturated double bond as a ring-constituting bond, or an unsaturated aliphatic ring that has an unsaturated bond as a ring-constituting bond, such as cyclohexene. Examples of the aliphatic ring having a monocyclic structure include a cyclohexane ring, a cycloheptane ring, and a cyclodecane ring. Examples of the fused aliphatic ring, which is an aliphatic ring having a fused ring structure, include fused aliphatic hydrocarbon rings such as an adamantane ring, a bornane ring, a norbornane ring, a tricyclodecane ring, a tetracyclododecane ring, a decalin ring, a cyclopentadiene ring, a dicyclopentadiene ring, and a tetrahydrodicyclopentadiene ring. 2 Examples of the divalent group containing an aliphatic ring used in include aliphatic ring groups obtained by removing two hydrogen atoms from such an aliphatic ring, and groups in which the aliphatic ring group is bonded to an alkylene group having 1 to 4 carbon atoms, such as a group represented by the following general formula (a3):

[0075]

[0076] (In the formula, L 5 represents an aliphatic cyclic group; 6 and L 7 represents an alkylene group having 1 to 4 carbon atoms, and * represents the bonding point.

[0077] The aromatic hydrocarbon ring-containing group is a group having an aromatic hydrocarbon ring. As the aromatic hydrocarbon ring-containing group, an aromatic hydrocarbon ring-containing group having 6 to 30 carbon atoms can be used. The aromatic hydrocarbon ring-containing group may have a monocyclic structure or a polycyclic structure. An aromatic hydrocarbon ring-containing group having a polycyclic structure may have a fused ring structure or may be formed by linking two aromatic hydrocarbon rings. An aromatic hydrocarbon ring-containing group having two linked aromatic hydrocarbon rings may be formed by linking two aromatic hydrocarbon rings having a monocyclic structure, a group in which an aromatic hydrocarbon ring having a monocyclic structure and an aromatic hydrocarbon ring having a fused ring structure are linked, or a group in which an aromatic hydrocarbon ring having a fused ring structure and an aromatic hydrocarbon ring having a fused ring structure are linked. The linking group connecting the two aromatic hydrocarbon rings may be any group that can impart aromaticity to the aromatic hydrocarbon ring-containing group as a whole, and examples thereof include a single bond, an alkylidene group, a sulfide group (—S—), and a carbonyl group. Examples of the alkylidene group include groups having 1 to 10 carbon atoms, such as methylene, ethylidene, 1-methylethylidene, and 1,1-propylidene. Examples of aromatic hydrocarbon rings having a monocyclic structure include benzene, toluene, ethylbenzene, and 2,4,6-trimethylbenzene. Examples of aromatic hydrocarbon rings having a fused ring structure include naphthalene, anthracene, phenanthrene, and pyrene. Examples of aromatic hydrocarbon ring-containing groups in which two aromatic hydrocarbon rings are linked together include groups in which aromatic hydrocarbon rings having a monocyclic structure are linked together via an alkylidene group, as represented by the following general formula (a4):

[0078]

[0079] (In the formula, L 8 represents a direct bond or an alkylidene group having 1 to 10 carbon atoms; R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a halogen atom, and * represents the bonding site.

[0080] R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 Examples of the alkyl group having 1 to 4 carbon atoms used in the above include a methyl group, an ethyl group, a propyl group, and a butyl group.

[0081] L 3 and L 4 The divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms used in L 2 Among the divalent hydrocarbon groups having 1 to 30 carbon atoms listed as groups usable in (1), those having the predetermined number of carbon atoms can be used.

[0082] R 1 Examples of the hydrocarbon group having 1 to 20 carbon atoms used in the formula (1) include an aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms.

[0083] The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be a hydrocarbon group that does not contain an aromatic hydrocarbon ring or a heterocycle, and examples thereof include a chain aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aliphatic ring-containing group having 3 to 20 carbon atoms. Examples of the chain aliphatic hydrocarbon group having 1 to 20 carbon atoms include an alkyl group having 1 to 20 carbon atoms and an alkenyl group having 2 to 20 carbon atoms. Examples of the aliphatic ring-containing group having 3 to 20 carbon atoms include a cycloalkyl group having 3 to 20 carbon atoms and a cycloalkylalkyl group having 4 to 20 carbon atoms.

[0084] The alkyl group having 1 to 20 carbon atoms may be linear or branched. Examples of linear alkyl groups include methyl, ethyl, propyl, butyl, iso-amyl, tert-amyl, hexyl, heptyl, and octyl groups. Examples of the branched alkyl group include an isopropyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, an isopentyl group, a tert-pentyl group, a 2-hexyl group, a 3-hexyl group, a 2-heptyl group, a 3-heptyl group, an isoheptyl group, a tert-heptyl group, an isooctyl group, a tert-octyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, a decyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group.

[0085] The alkenyl group having 2 to 20 carbon atoms may be linear or branched. It may also be a terminal alkenyl group having an unsaturated bond at the terminal, or an internal alkenyl group having an internal unsaturated bond. Examples of terminal alkenyl groups include vinyl, allyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of internal alkenyl groups include 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, and 4,8,12-tetradecatrienylallyl.

[0086] Examples of the cycloalkyl group having 3 to 20 carbon atoms include saturated monocyclic alkyl groups having 3 to 20 carbon atoms, saturated polycyclic alkyl groups having 3 to 20 carbon atoms, and groups having 4 to 20 carbon atoms in which one or more hydrogen atoms in the ring of these groups have been substituted with an alkyl group. Examples of the saturated monocyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. Examples of the saturated polycyclic alkyl group include an adamantyl group, a decahydronaphthyl group, an octahydropentalene group, and a bicyclo[1.1.1]pentanyl group. Examples of the alkyl group substituting a hydrogen atom in the ring of a saturated monocyclic or saturated polycyclic alkyl group include the groups exemplified above as the alkyl group having 1 to 20 carbon atoms. Examples of groups in which one or more hydrogen atoms in the ring of a saturated polycyclic alkyl group have been substituted with an alkyl group include a bornyl group.

[0087] The cycloalkylalkyl group having 4 to 20 carbon atoms refers to a group having 4 to 20 carbon atoms in which a hydrogen atom of an alkyl group is substituted with a cycloalkyl group. The cycloalkyl group in the cycloalkylalkyl group may be monocyclic or polycyclic. Examples of cycloalkylalkyl groups having 4 to 20 carbon atoms and in which the cycloalkyl group is monocyclic include a cyclopropylmethyl group, a 2-cyclobutylethyl group, a 3-cyclopentylpropyl group, a 4-cyclohexylbutyl group, a cycloheptylmethyl group, a cyclooctylmethyl group, a 2-cyclononylethyl group, and a 2-cyclodecylethyl group. Examples of cycloalkylalkyl groups having 4 to 20 carbon atoms and in which the cycloalkyl group is polycyclic include a 3-3-adamantylpropyl group and a decahydronaphthylpropyl group.

[0088] The aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms is a hydrocarbon group that contains an aromatic hydrocarbon ring but does not contain a heterocycle, and may have an aliphatic hydrocarbon group. Examples of such aromatic hydrocarbon ring-containing groups include aryl groups having 6 to 20 carbon atoms and arylalkyl groups having 7 to 20 carbon atoms.

[0089] The aryl group having 6 to 20 carbon atoms may have a monocyclic structure, a fused ring structure, or two linked aromatic hydrocarbon rings. The aryl group having two linked aromatic hydrocarbon rings may be two linked aromatic hydrocarbon rings having a monocyclic structure, a linked aromatic hydrocarbon ring having a monocyclic structure and a linked aromatic hydrocarbon ring having a fused ring structure, or a linked aromatic hydrocarbon ring having a fused ring structure and an linked aromatic hydrocarbon ring having a fused ring structure. The linking group connecting the two aromatic hydrocarbon rings may be any group that can impart aromaticity to the aryl group as a whole, and examples thereof include a single bond, a sulfide group (—S—), and a carbonyl group. Examples of aryl groups having a monocyclic structure include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, and a 2,4,6-trimethylphenyl group. Examples of aryl groups having a fused ring structure include a naphthyl group, an anthracenyl group, a phenanthryl group, and a pyrenyl group. Examples of the aryl group in which two monocyclic aromatic hydrocarbon rings are linked together include a biphenyl group, a diphenyl sulfide group, and a benzoylphenyl group.

[0090] The arylalkyl group having 7 to 20 carbon atoms refers to a group in which one or more hydrogen atoms in an alkyl group have been substituted with an aryl group. Examples of the arylalkyl group having 7 to 20 carbon atoms include a benzyl group, a fluorenyl group, an indenyl group, a 9-fluorenylmethyl group, an α-methylbenzyl group, an α,α-dimethylbenzyl group, a phenylethyl group, and a naphthylpropyl group.

[0091] In the present disclosure, a substituted hydrocarbon group refers to a group in which a hydrogen atom in a hydrocarbon group is substituted with a substituent, and a substituted heterocyclic group refers to a group in which a hydrogen atom in a heterocyclic group is substituted with a substituent. Examples of the substituent substituting the hydrogen atom in such a hydrocarbon group or heterocyclic group include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, and a carboxyl group.

[0092] In the present disclosure, the number of carbon atoms in a group refers to the number of carbon atoms in the entire group. For example, in a "divalent group containing an aliphatic ring having 3 to 30 carbon atoms," "3 to 30 carbon atoms" does not refer to the number of carbon atoms in the aliphatic ring, but rather refers to the number of carbon atoms in the "divalent group containing an aliphatic ring." Furthermore, when a hydrogen atom in the group is substituted with a substituent, the number of carbon atoms in the group after the substitution is specified. For example, in the case of a "group in which the hydrogen atom of an alkyl group having 1 to 20 carbon atoms is substituted with a substituent," the number of carbon atoms of 1 to 20 refers to the number of carbon atoms in the alkyl group after the hydrogen atom has been substituted with a substituent, not the number of carbon atoms in the alkyl group before the hydrogen atom is substituted. Furthermore, in the present disclosure, the number of carbon atoms in a group in which a methylene group in a group with a specified number of carbon atoms has been replaced with a divalent group refers to the number of carbon atoms in the group after the substitution. For example, in the case of "a group in which a methylene group in an alkyl group having 1 to 20 carbon atoms is replaced with a divalent group," the number of carbon atoms of 1 to 20 refers to the number of carbon atoms in the alkyl group after the methylene group has been replaced with the divalent group, and does not refer to the number of carbon atoms in the alkyl group before the replacement.

[0093] In the present disclosure, L 1 is preferably a group represented by the above general formula (a1), because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0094] In the present disclosure, L 2 is preferably an aromatic hydrocarbon ring-containing group, because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0095] L 2 The aromatic hydrocarbon ring-containing group used in is preferably an aromatic hydrocarbon ring-containing group having 8 to 20 carbon atoms, more preferably an aromatic hydrocarbon ring-containing group having 10 to 18 carbon atoms, and even more preferably an aromatic hydrocarbon ring-containing group having 12 to 16 carbon atoms, because the epoxy resin will have excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0096] In the present disclosure, L 2The aromatic hydrocarbon ring-containing group used in is preferably a group in which two aromatic hydrocarbon rings are linked, more preferably a group in which aromatic hydrocarbon rings of a monocyclic structure are linked, even more preferably a group in which two aromatic hydrocarbon rings of a monocyclic structure are linked via an alkylidene group, and particularly preferably a group represented by the above general formula (a4), because this provides the epoxy resin with excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0097] L 8 The alkylidene group used in is preferably a direct bond or an alkylidene group having 1 to 6 carbon atoms, more preferably a direct bond or an alkylidene group having 1 to 4 carbon atoms, and even more preferably an alkylidene group having 1 or 3 carbon atoms, i.e., a methylene group or an isopropylidene group, because the epoxy resin is superior in low cure shrinkage, storage stability, adhesive strength, etc.

[0098] R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 is preferably a hydrogen atom. This is because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength. This is because the epoxy resin is easy to synthesize. Furthermore, the raw materials for the epoxy resin are easy to obtain.

[0099] In the present disclosure, p1 and p2 are preferably 0 or more and 4 or less, more preferably 0 or more and 1 or less, and even more preferably 0. This is because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0100] (2) Second Compound The second compound is a compound having an internal triple bond and a second functional group. The second functional group can be one capable of forming a covalent bond with an epoxy group, and examples thereof include an amino group, a hydroxyl group, a carboxyl group, a thiol group, and an acid anhydride group. In the present disclosure, the second functional group is preferably an amino group or a hydroxyl group, and more preferably a hydroxyl group. This is because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0101] The hydroxyl group used for the second functional group may be a phenolic hydroxyl group bonded to an aromatic ring, but is preferably an alcoholic hydroxyl group bonded to a carbon atom other than the carbon atoms constituting the aromatic ring, because this facilitates the formation of the epoxy resin.

[0102] The number of the second functional groups in the second compound may be one or more, but is preferably from 2 to 10, more preferably from 2 to 4, and even more preferably 2. This is because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0103] The molecular weight of the second compound is preferably 50 or more and 300 or less, more preferably 60 or more and 200 or less, and even more preferably 70 or more and 150 or less, because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0104] In the present disclosure, the second compound is preferably a compound represented by the following general formula (B), because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0105]

[0106] (In the formula, L 11 and L 12 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms.

[0107] L 11 and L12 The hydrocarbon group used in the above L 2 The groups exemplified above can be used.

[0108] Specific examples of such second compounds include butynediol (HOCH2-C≡C-CH2OH), dimethylhexynediol [CH3C(CH3)(OH)-C≡C-C(CH3)(OH)CH3], dimethyloctynediol [C2H5C(CH3)(OH)-C≡C-C(CH3)(OH)C2H5], dimethyldecynediol [C3H7C(CH3)(OH)-C≡C-C(CH3)(OH)C3H7], dimethyldodecynediol [C4H9C(CH3)(OH)-C≡C-C(CH3)(OH)CH4H9], tetramethyldecynediol [CH3CH(CH3)CH2C(CH3)(OH)-C≡C-C(CH3)(OH)CH2CH(CH3)CH3], and dimethyltetradecynediol [C5H 11 C(CH3)(OH)-C≡C-C(CH3)(OH)C5H 11 ], dimethylhexadecynediol [C H 13 C(CH3)(OH)-C≡C-C(CH3)(OH)C6H 13 ], dimethyloctadecynediol [C7H 15 C(CH3)(OH)-C≡C-C(CH3)(OH)C7H 15 ], dimethyl eicosinediol [C H 17 C(CH3)(OH)-C≡C-C(CH3)(OH)C8H 17 ], tetramethyloctadecynediol [C H 11 CH(CH3)CH2C(CH3)(OH)-C≡C-C(CH3)(OH)CH2CH(CH3)C5H 11], diethyloctynediol [C2H5C(C2H5)(OH)-C≡C-C(C2H5)(OH)C2H5], diethyldecynediol [C3H7C(C2H5)(OH)-C≡C-C(C2H5)(OH)C3H7], diethyldodecynediol [C4H9C(C2H5)(OH)-C≡C-C(C2H5)(OH)C4H9], dimethyldiethyldecynediol [CH3CH(CH3)CH2C(C2H5)(OH)-C≡C-C(C2H5)(OH)CH2CH(CH3)CH3], diethyltetradecynediol [C5H 11 C(C2H5)(OH)-C≡C-C(C2H5)(OH)C5H 11 ], diethylhexadecynediol [C H 13 C(C2H5)(OH)-C≡C-C(C2H5)(OH)C6H 13 ], diethyloctadecynediol [C H 15 C(C2H5)(OH)-C≡C-C(C2H5)(OH)C7H 15 ], diethyl eicosinediol [C H 17 C(C2H5)(OH)-C≡C-C(C2H5)(OH)C8H 17 ], dimethyldiethyloctadecynediol [C H 11 CH(CH3)CH2C(C2H5)(OH)-C≡C-C(C2H5)(OH)CH2CH(CH3)C5H 11 ], dipropyldecynediol [C3H7C(C3H7)(OH)-C≡C-C(C3H7)(OH)C3H7], dipropyldodecynediol [C4H9C(C3H7)(OH)-C≡C-C(C3H7)(OH)C4H9], dimethyldipropyldecynediol [CH3CH(CH3)CH2C(C3H7)(OH)-C≡C-C(C3H7)(OH)CH2CH(CH3)CH3], dipropyltetradecynediol [C5H 11 C(C3H7)(OH)-C≡C-C(C3H7)(OH)C5H 11 ], dipropylhexadecynediol [C H 13 C(C3H7)(OH)-C≡C-C(C3H7)(OH)C6H 13 ], dipropyloctadecynediol [C7H 15C(C3H7)(OH)-C≡C-C(C3H7)(OH)C7H 15 ], dipropyl eicosinediol [C8H 17 C(C3H7)(OH)-C≡C-C(C3H7)(OH)C8H 17 ], dimethyldipropyloctadecynediol [C5H 11 CH(CH3)CH2C(C3H7)(OH)-C≡C-C(C3H7)(OH)CH2CH(CH3)C5H 11 ], dibutyldodecynediol [C4H9C(C4H9)(OH)-C≡C-C(C4H9)(OH)C4H9], dimethyldibutyldecynediol [CH3CH(CH3)CH2C(C4H9)(OH)-C≡C-C(C4H9)(OH)CH2CH(CH3)CH3], dibutyltetradecynediol [C5H 11 C(C4H9)(OH)-C≡C-C(C4H9)(OH)C5H 11 ], dibutylhexadecynediol [C H 13 C(C4H9)(OH)-C≡C-C(C4H9)(OH)C6H 13 ], dibutyloctadecynediol [C7H 15 C(C4H9)(OH)-C≡C-C(C4H9)(OH)C7H 15 ], dibutyl eicosine diol [C H 17 C(C4H9)(OH)-C≡C-C(C4H9)(OH)C8H 17 ], dimethyldibutyloctadecynediol [C5H 11 CH(CH3)CH2C(C4H9)(OH)-C≡C-C(C3H7)(OH)CH2CH(CH3)C5H 11 ], dipentyltetradecynediol [CH 11 C(CH 11 )(OH)-C≡C-C(C5H 11 )(OH)CH 11 ], dipentylhexadecynediol [C H 13 C(CH 11 )(OH)-C≡C-C(C5H 11 )(OH)CH 13 ], dipentyl octadecyne diol [C7H 15 C(CH 11)(OH)-C≡C-C(C5H 11 )(OH)CH 15 ], dipentyl eicosinediol [C8H 17 C(CH 11 )(OH)-C≡C-C(C5H 11 )(OH)CH 17 ], dimethyldipentyloctadecynediol [C5H 11 CH(CH3)CH2C(C5H 11 )(OH)-C≡C-C(C5H 11 )(OH)CH2CH(CH3)C5H 11 and other acetylenic diol compounds such as methyl butynediol [HOCH2-C≡C-CH(CH3)OH], methyl pentynediol [HOCH2-C≡C-CH(CH3)2OH], methyl ethyl heptynediol [CH3C(C2H5)(OH)-C≡C-C(CH3)(OH)CH3], and trimethyl octyne diol [CH3CH(CH3)CH2C(CH3)(OH)-C≡C-C(CH3)(OH)CH3].

[0109] In the present disclosure, L 11 and L 12 The hydrocarbon group used in is preferably an aliphatic hydrocarbon group, more preferably a chain aliphatic hydrocarbon group, and even more preferably a straight-chain hydrocarbon group, because this provides the epoxy resin with excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0110] In the present disclosure, L 11 and L 12 The number of carbon atoms in the hydrocarbon group used is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, even more preferably 1 or more and 2 or less, and it is particularly preferable that the number is 1, that is, the second compound is butynediol, because this provides the epoxy resin with excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0111] (3) First Epoxy Compound In the present disclosure, the first epoxy compound is preferably a compound represented by the following general formula (1), because the epoxy resin has excellent properties such as low cure shrinkage, storage stability, and adhesive strength.

[0112]

[0113] (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24 each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more.

[0114]

[0115] (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34 each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents the bonding site.

[0116] L 32 The hydrocarbon group used in the above L 2 The groups exemplified as those used in L can be used. 32 The preferred structures of the groups are also as described above for L 2 The preferred groups of L can be the same as those described above. 33 and L 34 The aliphatic hydrocarbon group used in 3 and L 4 The groups exemplified as those used in L can be used. 33 and L 34 The preferred structures of the groups are also as described above for L 3 and L4 The preferred groups of R 11 The hydrocarbon group used in R 1 The groups exemplified as those used in R can be used. 11 The preferred structures of the groups are also as described above for R 1 The preferred ranges of r1 and r2 can be the same as those described above as the preferred ranges of p1 and p2. In the present disclosure, n1 is preferably 1 or more and 10 or less, more preferably 2 or more and 10 or less, even more preferably 2 or more and 8 or less, and particularly preferably 2 or more and 5 or less. This is because the epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0117] 3. Others The epoxy resins are preferably used in applications requiring a small cure shrinkage rate, and can be used in various applications where epoxy compounds are used. Specific examples of such applications include adhesives, sealants, paints, fiber-reinforced composite materials, and the like for various applications such as transportation equipment such as automobiles, electrical equipment, and building materials. Other examples of such applications include molded products such as miscellaneous goods, toys, industrial parts, and electrical parts.

[0118] B. Method for Producing Epoxy Resin Next, a method for producing an epoxy resin according to the present disclosure will be described. The method for producing an epoxy resin according to the present disclosure is characterized by comprising a reaction step of synthesizing an epoxy resin by reacting a first compound having an epoxy group with a second compound having an internal triple bond and a second functional group bonded to the epoxy group.

[0119] According to the present disclosure, it is possible to easily produce an epoxy resin capable of forming a curable composition having excellent low cure shrinkage. Furthermore, the obtained epoxy resin has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0120] The method for producing an epoxy resin according to the present disclosure includes the reaction steps described above. The reaction steps included in the method for producing an epoxy resin according to the present disclosure will be described in detail below.

[0121] 1. Reaction Step This step is a step of reacting the first compound with the second compound. The first compound and the second compound can be the same as those described in the above section "A. Epoxy Resin," and therefore, a description thereof will be omitted here. An example of such a reaction method is a method in which a mixture of the first compound and the second compound is heated.

[0122] The method for preparing the mixture of the first compound and the second compound may be a method in which a solvent is used to mix the two compounds in the solvent, or a method in which no solvent is used.

[0123] As a method for mixing the first compound and the second compound, a known mixing method such as using various stirring devices equipped with stirring blades can be used.

[0124] When mixing, a heat treatment may be performed to dissolve the first compound and the second compound. The heating temperature may be any temperature that can suppress the progress of the reaction between the first compound and the second compound, and is preferably, for example, 50° C. or higher and 100° C. or lower, because this facilitates the production of the epoxy resin.

[0125] The amount of the second compound can be adjusted according to the desired weight-average molecular weight of the resulting epoxy resin, and is, for example, preferably 1 part by mass or more and 30 parts by mass or less, more preferably 3 parts by mass or more and 20 parts by mass or less, even more preferably 4 parts by mass or more and 15 parts by mass or less, and particularly preferably 5 parts by mass or more and 10 parts by mass or less, relative to 100 parts by mass of the first compound, because this facilitates the production of the epoxy resin.

[0126] In this step, a catalyst may be used in combination. Examples of such catalysts include phosphines such as triphenylphosphine; phosphonium salts such as tetraphenylphosphonium bromide; imidazoles such as 2-methylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, and 1-cyanoethyl-2-methylimidazole; imidazole salts obtained by combining the above imidazoles with trimellitic acid, isocyanuric acid, boron, or the like; benzyldimethylamine, 2,4,6-tris(trimethylsilyl)amine, and the like; Examples of suitable catalysts include amines such as (dimethylaminomethyl)phenol; quaternary ammonium salts such as trimethylammonium chloride; ureas such as 3-(p-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-phenyl-1,1-dimethylurea, isophorone diisocyanate-dimethylurea, and tolylene diisocyanate-dimethylurea; and complex compounds of boron trifluoride with amines, ether compounds, and the like. In this step, the catalyst is preferably a phosphine, as this facilitates the production of the epoxy resin.

[0127] The amount of the catalyst added can be adjusted according to the desired weight-average molecular weight of the resulting epoxy resin, and is, for example, preferably 0.05 parts by mass or more and 5 parts by mass or less, and more preferably 0.1 parts by mass or more and 3 parts by mass or less, relative to 100 parts by mass of the first compound, because this facilitates the production of the epoxy resin.

[0128] In this step, a curing agent can also be used in combination within the range that allows the production of the desired epoxy resin. Examples of such curing agents that can be used include those described in the section "D. Curable Composition" below. The content of the curing agent is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 1 part by mass or less, relative to 100 parts by mass of the first compound. It is particularly preferred that the content be 0, i.e., a method in which no curing agent is used in combination in this step. This is because the production of the epoxy resin becomes easier.

[0129] The heating temperature for reacting the first compound and the second compound is preferably 110° C. or higher and 150° C. or lower, more preferably 115° C. or higher and 140° C. or lower, and even more preferably 120° C. or higher and 130° C. or lower, because this facilitates the production of the epoxy resin.

[0130] The reaction time at the heating temperature for the reaction is preferably 1 hour or more and 10 hours or less, more preferably 3 hours or more and 8 hours or less, and even more preferably 4 hours or more and 7 hours or less, because this facilitates the production of the epoxy resin.

[0131] 2. Other Steps The above-described method for producing an epoxy resin includes a reaction step, but may include other steps as necessary.

[0132] The other steps include a purification step of removing unreacted materials after the reaction step.

[0133] 3. Epoxy Resin The epoxy resin produced by the method for producing an epoxy resin according to the present disclosure and its uses can be similar to those described in the section "A. Epoxy Resin" above, and therefore further description thereof will be omitted here.

[0134] C. Epoxy Composition Next, the epoxy composition of the present disclosure will be described. The epoxy composition of the present disclosure is characterized by containing the above-mentioned epoxy resin and an epoxy compound other than the above-mentioned epoxy resin (hereinafter, may be referred to as a second epoxy compound).

[0135] According to the present disclosure, since the epoxy resin described above is contained, it is possible to obtain an epoxy composition capable of forming a curable composition that is excellent in low cure shrinkage, storage stability, adhesive strength, and the like.

[0136] 1. Epoxy Resin The epoxy resin may be the same as that described in the above section "A. Epoxy Resin," and therefore, a description thereof will be omitted here.

[0137] The content of the epoxy resin is preferably 1 part by mass or more and 90 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and even more preferably 20 parts by mass or more and 40 parts by mass or less, per 100 parts by mass of the epoxy composition, because the epoxy composition can form a curable composition that is excellent in low cure shrinkage, storage stability, adhesive strength, etc.

[0138] The content of the epoxy resin is preferably 1 part by mass or more and 90 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and even more preferably 20 parts by mass or more and 40 parts by mass or less, per 100 parts by mass of the epoxy resin and the second epoxy compound combined, because the epoxy composition can form a curable composition that is excellent in low cure shrinkage, storage stability, adhesive strength, etc.

[0139] The content of the epoxy resin and the second epoxy compound is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, and even more preferably 90 parts by mass or more, per 100 parts by mass of the epoxy composition, because the epoxy composition can form a curable composition that is excellent in low cure shrinkage, storage stability, adhesive strength, etc.

[0140] 2. Second Epoxy Compound The second epoxy compound is a compound other than the above-mentioned epoxy resins.

[0141] Examples of such second epoxy compounds include those exemplified as the first compound described in the above section "A. Epoxy Resins." In addition, the preferred structure of the second epoxy compound may be the same as that described as the preferred structure of the first compound described in the above section "A. Epoxy Resins."

[0142] The content of the second epoxy compound is preferably 10 parts by mass or more and 95 parts by mass or less, more preferably 30 parts by mass or more and 90 parts by mass or less, and even more preferably 50 parts by mass or more and 80 parts by mass or less, per 100 parts by mass of the epoxy composition, because the epoxy composition can form a curable composition that is excellent in low cure shrinkage, storage stability, adhesive strength, etc.

[0143] The content of the second epoxy compound is preferably 10 parts by mass or more and 95 parts by mass or less, more preferably 30 parts by mass or more and 90 parts by mass or less, and even more preferably 50 parts by mass or more and 80 parts by mass or less, per 100 parts by mass of the epoxy resin and the second epoxy compound combined, because the epoxy composition can form a curable composition that is excellent in low cure shrinkage, storage stability, adhesive strength, etc.

[0144] The hydroxyl value of the epoxy composition is preferably from 10 mgKOH / g to 1000 mgKOH / g, more preferably from 20 mgKOH / g to 500 mgKOH / g, even more preferably from 30 mgKOH / g to 300 mgKOH / g, and particularly preferably from 50 mgKOH / g to 200 mgKOH / g. This is because the epoxy composition exhibits excellent properties such as low cure shrinkage, storage stability, and adhesive strength. The hydroxyl value can be measured in accordance with JIS K 0070-1992.

[0145] The total chlorine content of the epoxy composition is preferably 10,000 ppm or less by mass, more preferably 3,000 ppm or less, even more preferably 10 ppm or more to 1,500 ppm or less, and even more preferably 30 ppm or more to 1,000 ppm or less. This is because there is no risk of ion migration occurring, and when used, for example, as an adhesive or sealant for electrical and electronic components, a product with good reliability can be obtained. The total chlorine content can be measured in accordance with JIS K7243-3.

[0146] 3. Others The epoxy composition of the present disclosure contains both an epoxy resin and a second epoxy compound, but may also contain other components as needed. Examples of other components include fillers, plasticizers, colorants, antioxidants, foaming agents, diluents, and ultraviolet absorbers.

[0147] D. Curable Composition Next, the curable composition of the present disclosure will be described. The curable composition of the present disclosure is characterized by containing the above-described epoxy resin and a curing agent.

[0148] According to the present disclosure, since the above-described epoxy resin is contained, a curable composition having excellent properties such as low cure shrinkage, storage stability, and adhesive strength can be obtained.

[0149] 1. Epoxy Resin The epoxy resin may be the same as that described in the above section "A. Epoxy Resin," and therefore, a description thereof will be omitted here.

[0150] The content of the epoxy resin is preferably 1 part by mass or more and 90 parts by mass or less, more preferably 10 parts by mass or more and 50 parts by mass or less, and even more preferably 20 parts by mass or more and 40 parts by mass or less, per 100 parts by mass of the curable composition, because the curable composition has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0151] 2. Curing Agent The curing agent can be one that can increase the molecular weight of the epoxy resin. As such a curing agent, one that is generally used as an epoxy curing agent can be used, and the curing agents described in JP-A-2005-506402 can be used.

[0152] More specifically, examples of the curing agent include an acid anhydride curing agent, a phenolic curing agent, an amine curing agent, a polythiol curing agent, and an imidazole curing agent. In the present disclosure, the curing agent preferably includes an amine curing agent or an imidazole curing agent, and more preferably includes an imidazole curing agent. This is because the curable composition has excellent low cure shrinkage, storage stability, adhesive strength, and the like.

[0153] Examples of the imidazole-based curing agent include imidazoles and modified imidazoles obtained by modifying imidazoles. In the present disclosure, the curing agent is preferably an imidazole or a modified imidazole obtained by modifying an imidazole, and more preferably an imidazole. This is because the curable composition has excellent properties such as low cure shrinkage, storage stability, and adhesive strength. In addition, the curable composition has excellent compatibility and heat resistance.

[0154] Methods for modifying imidazoles include dehydration condensation with carboxylic acid, addition reaction with an epoxy compound, addition reaction with an isocyanate, Michael addition reaction, Mannich reaction, condensation reaction with urea, and condensation reaction with a ketone. As the epoxy compound used for the modification, the epoxy compounds described as the first compound in "A. Epoxy resins" above can be used.

[0155] Examples of the imidazoles include 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-aminopropylimidazole, 1-phenylmethyl-2-imidazole, 1-phenylmethyl-2-ethyl-4-methylimidazole, 1-phenylmethyl-2-phenylimidazole, 1-butoxycarbonylethyl-2-methylimidazole, 1-butoxycarbonylethyl-2-methylimidazole, and 1-butoxycarbonylethyl-2-methylimidazole. carbonylethyl-2-ethyl-4-methylimidazole, 1-butoxycarbonylethyl-2-phenylimidazole, 1-(2-ethylhexyl)carbonylethyl-2-methylimidazole, 1-(2-ethylhexyl)carbonylethyl-2-ethyl-4-methylimidazole, 1-(2-ethylhexyl)carbonylethyl-2-phenylimidazole, 1-octyloxycarbonylethyl-2-methylimidazole, 1-octyloxycarbonylethyl-2-ethyl-4-methylimidazole, 1-octyloxycarbonylethyl nylethyl-2-phenylimidazole, hexanediol bis(2-methylimidazolyl ethanoate) ester, hexanediol bis(2-ethyl-4-methylimidazolyl ethanoate) ester, hexanediol bis(2-phenylimidazolyl ethanoate) ester, decanediol bis(2-methylimidazolyl ethanoate) ester, decanediol bis(2-ethyl-4-methylimidazolyl ethanoate) ester, decanediol bis(2-phenylimidazolyl ethanoate) ester, tricyclopentane dimethanoate tricyclopentane dimethanol bis(2-methylimidazolyl ethanoate) ester, tricyclopentane dimethanol bis(2-ethyl-4-methylimidazolyl ethanoate) ester, tricyclopentane dimethanol bis(2-phenylimidazolyl ethanoate) ester, 1-(2-hydroxynaphthylmethyl)-2-methylimidazole, 1-(2-hydroxynaphthylmethyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxynaphthylmethyl)-2-phenylimidazole, and imidazole silane (for example, manufactured by Shikoku Chemical Industry Co., Ltd.;2MUSIZ), which can also be used in the form of a salt with trimellitic acid, isocyanuric acid, boron, etc.;

[0156] Commercially available products of the curing agent include, for example, ADEKA HARDNER (registered trademark) EH-3636AS, ADEKA HARDNER EH-4351S (manufactured by ADEKA Corporation; amine-based curing agent), ADEKA HARDNER EH-5011S, ADEKA HARDNER EH-5046S (manufactured by ADEKA Corporation; imidazole-based curing agent), ADEKA HARDNER EH-4357S, ADEKA HARDNER EH-5057P, ADEKA HARDNER EH-5057PK (manufactured by ADEKA Corporation; amine-based curing agent), AMICURE (registered trademark) PN-23, AMICURE PN-40 (manufactured by Ajinomoto Fine-Techno; amine-based curing agent), AMICURE VDH (manufactured by Ajinomoto Fine-Techno; amine-based curing agent), and FUJICURE FXR-1020 (manufactured by T&K Examples of such curing agents include PEG-100 (manufactured by Toka Chemical Industry Co., Ltd.; imidazole-based curing agent), TS-G (manufactured by Shikoku Chemical Industry Co., Ltd.; polythiol-based curing agent), DPMP, PEMP (manufactured by SC Organic Chemical Industry Co., Ltd.; polythiol-based curing agent), and PETG (manufactured by Yodo Chemical Industry Co., Ltd.; polythiol-based curing agent). These curing agents may be used alone or in combination of two or more.

[0157] As the curing agent, an acid generator or a base generator can also be used.

[0158] Examples of the acid generator include photoacid generators that generate acid upon irradiation with energy rays such as ultraviolet rays, and thermal acid generators that generate acid upon heating. Examples of such photoacid generators and thermal acid generators include those described as photocationic polymerization initiators and thermal cationic polymerization initiators in JP-A-2023-181911. Specific examples of the photoacid generator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, thianthrhenium salts, thioxanthonium salts, and (2,4-cyclopentadien-1-yl)[(1-methylethylbenzene]-Fe cations in which the anion moiety is BF4 - , PF6 - , SbF6 - , [BX4]- (wherein X is a phenyl group substituted with at least two or more fluorine atoms or trifluoromethyl groups), and these onium salts may be used alone or in combination. Examples of the thermal acid generator include phonate, 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.

[0159] Examples of the base generator include a photobase generator that generates a base upon irradiation with energy rays such as ultraviolet rays. The photobase generator is preferably a salt containing a borate anion because it has good sensitivity to light.

[0160] The amount of the curing agent added is preferably 0.1 parts by mass or more and 20 parts by mass or less, more preferably 1 part by mass or more and 10 parts by mass or less, and even more preferably 3 parts by mass or more and 7 parts by mass or less, per 100 parts by mass of the curable composition. When the amount of the curing agent added is within the above range, the curable composition becomes superior in low cure shrinkage, storage stability, adhesive strength, etc.

[0161] The amount of the curing agent added is preferably 0.1 parts by mass or more and 20 parts by mass or less, more preferably 1 part by mass or more and 10 parts by mass or less, and even more preferably 3 parts by mass or more and 7 parts by mass or less, relative to 100 parts by mass of the total of the epoxy resin and the second epoxy compound described below, because the curable composition has excellent low cure shrinkage, storage stability, adhesive strength, etc.

[0162] 3. Second Epoxy Compound The curable composition may contain a second epoxy compound as an epoxy compound other than the epoxy resin. Such a second epoxy compound may be the same as that described in the section "2. Second Epoxy Compound" in "C. Epoxy Composition" above.

[0163] 4. Others The uses of the curable composition may be the same as those described in the above section "A. Epoxy Resin." The curable composition of the present disclosure may contain other components as needed, in addition to the epoxy resin, curing agent, and second epoxy compound. Examples of other components include those similar to those described in the above section "C. Epoxy Composition."

[0164] E. 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 above-described curable composition.

[0165] According to the present disclosure, by using the above-described curable composition, it is possible to obtain a cured product that undergoes little change in shape before and after curing.

[0166] The details of the curable composition can be the same as those described in the above section "D. Curable composition," and therefore a description thereof will be omitted here. Furthermore, the method for producing the cured product may be any method capable of forming a cured product in a desired cured state, and for example, the method described in the below-described section "F. Method for producing cured product" can be used. The uses of the cured product of the present disclosure can be the same as those described in the above section "A. Epoxy resin," for example.

[0167] F. Method for Producing a Cured Product Next, a method for producing a cured product according to the present disclosure will be described. The method for producing a cured product according to the present disclosure is characterized by having a curing step of curing the above-described curable composition.

[0168] According to the present disclosure, by using the above-described curable composition, a method for producing a cured product that undergoes little change in shape before and after curing can be achieved.

[0169] The method for producing a cured product according to the present disclosure includes the curing step described above. Each step of the method for producing a cured product according to the present disclosure will now be described.

[0170] 1. Curing Step This step is a step of curing the curable composition. The content of the curable composition can be the same as that described in the section "D. Curable composition" above, and therefore, a description thereof will be omitted here.

[0171] The method for curing the curable composition may be any method capable of forming a desired cured product, and for example, at least one of a heating method and a light irradiation method may be used. In this step, when the method is a heating method, the heating temperature may be any temperature capable of forming a desired cured product, and may be, for example, 70°C or higher and 200°C or lower.

[0172] 2. Others The method for producing a cured product according to the present disclosure includes the curing step described above, but may also include other steps as necessary. Examples of the other steps include a coating step of coating the curable composition.

[0173] The uses of the cured product produced by the method for producing a cured product according to the present disclosure can be similar to those described in the section "A. Epoxy resins" above, for example.

[0174] G. Compound Next, the compound of the present disclosure will be described. The compound of the present disclosure is characterized by being represented by the following general formula (1).

[0175]

[0176] (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24 each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more.

[0177]

[0178] (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34 each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents the bonding site.

[0179] According to the present disclosure, it becomes easy to form a curable composition that is excellent in low cure shrinkage, storage stability, adhesive strength, etc. Furthermore, according to the present disclosure, it is possible to form an epoxy resin that is excellent in low cure shrinkage, storage stability, adhesive strength, etc.

[0180] The compound of the present disclosure is represented by the above general formula (1). The details of such a compound can be the same as those described in the section "(3) First epoxy compound" in "A. Epoxy resin" above, and therefore further explanation will be omitted here.

[0181] H. Others The present disclosure includes the following aspects. [1] An epoxy resin having an internal triple bond and a weight-average molecular weight of 500 or more. [2] The epoxy resin according to [1], characterized in that the weight-average molecular weight is 500 or more and 10,000 or less. [3] The epoxy resin according to [1] or [2], characterized in that the content of internal triple bonds in the epoxy resin is 1 mmol / g or more and 2.5 mmol / g or less. [4] The epoxy resin according to any one of [1] to [3], characterized in that the content of internal triple bonds in the epoxy resin is 1 mmol / g or more and 2.3 mmol / g or less. [5] The epoxy resin according to any one of [1] to [4], characterized in that the epoxy equivalent of the epoxy resin is 200 g / eq or more and 1000 g / eq or less. [6] The epoxy resin according to any one of [1] to [5], characterized in that the epoxy equivalent of the epoxy resin is 300 g / eq or more and 1000 g / eq or less. [7] The epoxy resin according to any one of [1] to [6], characterized in that the epoxy resin contains a reaction product of a first compound having an epoxy group with a second compound having an internal triple bond and a second functional group bonded to the epoxy group. [8] The epoxy resin according to [7], characterized in that the first compound is at least one selected from a polynuclear polyhydric phenol compound or a polyglycidyl ether compound of an alkylene oxide adduct of the polynuclear polyhydric phenol compound, a polyglycidyl ether of a polyhydric alcohol, and an epoxy compound having a glycidylamino group. [9] The epoxy resin according to [7] or [8], characterized in that the second functional group is a hydroxyl group.

[10] The epoxy resin according to any one of [1] to [9], characterized in that the epoxy resin contains a compound represented by the following general formula (1): (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more. (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34 each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents a bonding site.)

[11] A method for producing an epoxy resin, comprising a reaction step of synthesizing an epoxy resin by reacting a first compound having an epoxy group with a second compound having an internal triple bond and a second functional group bonded to the epoxy group.

[12] An epoxy composition, comprising the epoxy resin according to any one of [1] to

[10] and an epoxy compound other than the epoxy resin.

[13] The epoxy composition according to

[12] , wherein the total chlorine content of the epoxy composition is 10 ppm or more and 1500 ppm or less.

[14] A curable composition, comprising the epoxy resin according to any one of [1] to

[10] and a curing agent.

[15] A cured product of the curable composition according to

[14] .

[16] A method for producing a cured product, comprising a curing step of curing the curable composition according to

[14] .

[17] A compound represented by the following general formula (1): (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24 each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more. (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents a bonding site.

[18] The compound according to

[17] , wherein n1 is an integer of 2 to 10.

[0182] The present disclosure is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any configuration that is substantially identical to the technical idea described in the claims of the present disclosure and that provides similar effects is included within the technical scope of the present disclosure.

[0183] The present disclosure will be described in more detail below with reference to examples and comparative examples, but the present disclosure is not limited to these examples.

[0184] Example 1 A 1-L separable flask equipped with a stirrer, a nitrogen flow tube, a thermometer, and a reflux device was charged with 100 g (0.29 mol) of bisphenol A epoxy resin (manufactured by Nippon Steel Chemical & Material Co., Ltd., product name: YD-8125, epoxy equivalent = 170 g / eq) and 8.5 g (0.10 mol) of butynediol, and the mixture was stirred at an internal temperature of 60°C to dissolve the butynediol. Next, 0.26 g (0.98 mmol) of triphenylphosphine was charged, and the mixture was heated and stirred at 90°C. The temperature was then gradually increased to 125°C over 3 hours, and heating was continued at 125°C for 5 hours to obtain Epoxy Composition 1. The resulting Epoxy Composition 1 had an epoxy equivalent of 263 g / eq, a hydroxyl value of 101 mgKOH / g, and a total chlorine content of 500 ppm. GPC analysis of the resulting Epoxy Composition 1 was performed. The results are shown in Figure 1. In addition, the epoxy resin shown in FIG. 1 (hereinafter sometimes referred to as resin 1) was extracted from epoxy composition 1 by preparative GPC. 1 H-NMR and 13 C-NMR measurement was carried out. 1 H-NMR and 13 The results of C-NMR measurement are shown in Figures 2 and 3, respectively. 1 H-NMR and13 From the results of C-NMR measurement, it was confirmed that the resin 1 contains a compound represented by the following general formula (11). The hydroxyl value of the resin 1 was 183 mgKOH / g. From the weight average molecular weights of region A and region B in Figure 1, it was confirmed that region A is a compound in which n11 = 4 in the following general formula (11), and region B is a compound in which n11 = 1 in the following general formula (11).

[0185]

[0186] (In the formula, n11 represents an integer of 1 or more.)

[0187] [Example 2] Epoxy composition 2 was obtained by the same procedure as in Example 1, except that the amount of butynediol used in Example 1 was changed to 5.1 g (0.06 mol) and the amount of triphenylphosphine was changed to 0.16 g (0.59 mmol). The epoxy equivalent of the obtained epoxy composition 2 was 214 g / eq, the hydroxyl value was 63 mg KOH / g, and the total chlorine content was 520 ppm. The obtained epoxy composition 2 was subjected to GPC measurement. The results are shown in Figure 4. In addition, the epoxy resin shown in Figure 4 (hereinafter, sometimes referred to as resin 2) was extracted from epoxy composition 2 by preparative GPC, and the extracted resin 2 was analyzed by GPC. 1 H-NMR and 13 C-NMR measurement was carried out. 1 H-NMR and 13 The results of C-NMR measurement are shown in Figures 5 and 6, respectively. 1 H-NMR and 13 From the results of C-NMR measurement, it was confirmed that Resin 2 contains the compound represented by General Formula (11). The hydroxyl value of Resin 2 was 189 mgKOH / g. From the weight average molecular weights of Region A and Region B in Figure 4, it was confirmed that Region A is a compound in which n11 = 4 in General Formula (11), and Region B is a compound in which n11 = 1 in General Formula (11).

[0188] [Example 3] Epoxy composition 3 was obtained by the same procedure as in Example 1, except that the amount of butynediol used in Example 1 was changed to 12.8 g (0.15 mol) and the amount of triphenylphosphine used in Example 1 was changed to 0.39 g (1.47 mmol). The epoxy equivalent of the obtained epoxy composition 3 was 413 g / eq, the hydroxyl value was 146 mg KOH / g, and the total chlorine content was 490 ppm. The obtained epoxy composition 3 was subjected to GPC measurement. The results are shown in Figure 7. In addition, the epoxy resin shown in Figure 7 (hereinafter, sometimes referred to as resin 3) was extracted from epoxy composition 3 by preparative GPC, and the extracted resin 3 was analyzed by GPC. 1 H-NMR and 13 C-NMR measurement was carried out. 1 H-NMR and 13 The results of C-NMR measurement are shown in Figures 8 and 9, respectively. 1 H-NMR and 13 From the results of C-NMR measurement, it was confirmed that Resin 3 contains the compound represented by General Formula (11). The hydroxyl value of Resin 3 was 180 mgKOH / g. From the weight average molecular weights of Region A and Region B in Figure 7, it was confirmed that Region A is a compound in which n11 = 6 in General Formula (11), and Region B is a compound in which n11 = 1 in General Formula (11).

[0189] Example 4 Epoxy composition 4 was obtained by the same procedure as in Example 1, except that the bisphenol A epoxy resin used in Example 1 was replaced with 300 g (0.94 mol) of bisphenol F epoxy resin (manufactured by Kookdo Chemical Co., Ltd., product name: KDS-8170, epoxy equivalent = 160 g / eq), 27.6 g (0.32 mol), and 0.84 g (3.2 mmol) of triphenylphosphine. The epoxy equivalent of the obtained epoxy composition 4 was 259 g / eq, the hydroxyl value was 109 mg KOH / g, and the total chlorine content was 600 ppm. GPC measurement was performed on the obtained epoxy composition 4. The results are shown in Figure 10. Furthermore, the epoxy resin shown in Figure 10 (hereinafter, sometimes referred to as resin 4) was extracted from epoxy composition 4 by preparative GPC, and the extracted resin 4 was analyzed by GPC. 1 H-NMR and 13When C-NMR measurement was carried out, it was confirmed that Resin 4 contained a compound represented by the following general formula (12). The hydroxyl value of Resin 4 was 186 mgKOH / g. From the weight average molecular weights of Region A and Region B in Figure 10, it was confirmed that Region A was a compound in which n12 = 5 in the following general formula (12), and Region B was a compound in which n12 = 1 in the following general formula (12).

[0190]

[0191] Example 5 Epoxy composition 5 was obtained by the same procedure as in Example 1, except that the bisphenol A epoxy resin used in Example 1 was changed to 100 g (0.29 mol) of ADEKA Resin EP-4088L (manufactured by ADEKA Corporation, epoxy equivalent = 170 g / eq) and the triphenylphosphine was changed to 0.36 g (0.98 mmol) of ethyltriphenylphosphonium bromide. The epoxy equivalent of the obtained epoxy composition 5 was 240 g / eq, the hydroxyl value was 101 mg KOH / g, and the total chlorine content was 590 ppm. GPC measurement was performed on the obtained epoxy composition 5. The results are shown in Figure 11. In addition, the epoxy resin shown in Figure 11 (hereinafter, sometimes referred to as resin 5) was extracted from epoxy composition 5 by preparative GPC, and the extracted resin 5 was analyzed by GPC. 1 H-NMR and 13 When C-NMR measurement was carried out, it was confirmed that Resin 5 contained a compound represented by the following general formula (13). The hydroxyl value of Resin 5 was 223 mgKOH / g. From the weight average molecular weights of Region A and Region B in Figure 11, it was confirmed that Region A was a compound in which n13 = 4 in the following general formula (13), and Region B was a compound in which n13 = 1 in the following general formula (13).

[0192]

[0193] Example 6 Epoxy composition 6 was obtained by the same procedure as in Example 1, except that the bisphenol A epoxy resin used in Example 1 was changed to 100 g (0.43 mol) of ADEKA RESIN EP-3980S (manufactured by ADEKA Corporation, epoxy equivalent = 115 g / eq), 13.1 g (0.15 mol) of butynediol, and 0.39 g (1.52 mmol) of triphenylphosphine. The epoxy equivalent of the obtained epoxy composition 6 was 253 g / eq, the hydroxyl value was 150 mg KOH / g, and the total chlorine content was 620 ppm. GPC measurement was performed on the obtained epoxy composition 6. The results are shown in Figure 12. In addition, the epoxy resin shown in Figure 12 (hereinafter, sometimes referred to as resin 6) was extracted from epoxy composition 6 by preparative GPC, and the extracted resin 6 was analyzed. 1 H-NMR and 13 When C-NMR measurement was carried out, it was confirmed that Resin 6 contained a compound represented by the following general formula (14). The hydroxyl value of Resin 6 was 226 mgKOH / g. From the weight average molecular weights of Region A and Region B in Figure 12, it was confirmed that Region A was a compound in which n14 = 3 in the following general formula (14), and Region B was a compound in which n14 = 1 in the following general formula (14).

[0194]

[0195] Example 7 Epoxy composition 7 was obtained by the same procedure as in Example 1, except that the bisphenol A epoxy resin used in Example 1 was changed to 100 g (0.20 mol) of ADEKA Resin EP-4000L (manufactured by ADEKA Corporation, epoxy equivalent = 255 g / eq), 5.7 g (0.07 mol) of butynediol, and 0.37 g (1.00 mmol) of ethyltriphenylphosphonium bromide. The epoxy equivalent of the obtained epoxy composition 7 was 337 g / eq, the hydroxyl value was 69 mg KOH / g, and the total chlorine content was 280 ppm. GPC measurement was performed on the obtained epoxy composition 7. The results are shown in Figure 13. In addition, the epoxy resin shown in Figure 13 (hereinafter, sometimes referred to as resin 7) was extracted from epoxy composition 7 by preparative GPC, and the extracted resin 7 was analyzed. 1 H-NMR and13 When C-NMR measurement was carried out, it was confirmed that Resin 7 contained a compound represented by the following general formula (15). The hydroxyl value of Resin 7 was 199 mgKOH / g. From the weight average molecular weights of Region A and Region B in Figure 13, it was confirmed that Region A was a compound in which n15 = 2 in the following general formula (15), and Region B was a compound in which n15 = 1 in the following general formula (15).

[0196]

[0197] Example 8 Epoxy composition 8 was obtained by the same procedure as in Example 1, except that the bisphenol A epoxy resin used in Example 1 was replaced with 100 g (0.45 mol) of ADEKA Glysilol ED-523L (manufactured by ADEKA Corporation, epoxy equivalent = 110 g / eq), 13.0 g (0.15 mol) of butynediol, and 0.56 g (1.52 mmol) of ethyltriphenylphosphonium bromide. The epoxy equivalent of the obtained epoxy composition 8 was 173 g / eq, the hydroxyl value was 150 mg KOH / g, and the total chlorine content was 440 ppm. GPC measurement was performed on the obtained epoxy composition 8. The results are shown in Figure 14. Furthermore, the epoxy resin shown in Figure 14 (hereinafter, sometimes referred to as resin 8) was extracted from epoxy composition 8 by preparative GPC, and the extracted resin 8 was analyzed. 1 H-NMR and 13 When C-NMR measurement was carried out, it was confirmed that the resin 8 contained a compound represented by the following general formula (16). The hydroxyl value of the resin 8 was 210 mgKOH / g. From the weight average molecular weights of the regions A and B in FIG. 14, it was confirmed that the region A was a compound in which n16 = 5 in the following general formula (16), and the region B was a compound in which n16 = 1 in the following general formula (16).

[0198]

[0199] Comparative Example 1 A 1 L separable flask equipped with a stirrer, a nitrogen flow tube, a thermometer, and a reflux device was charged with 100 g (0.29 mol) of bisphenol A epoxy resin (manufactured by Nippon Steel Chemical & Material Co., Ltd., product name: YD-8125, epoxy equivalent = 170 g / eq) and 13.0 g (0.15 mol) of butenediol, and the mixture was stirred at an internal temperature of 60°C. Next, 0.23 g (0.99 mmol) of boron trifluoride monomethylamine was charged, and the mixture was heated and stirred at 120°C for 6 hours. After the reaction, the contents were cooled to 80°C, and 54.7 g of n-butanol and 5.0 g of synthetic hydrotalcite adsorbent (Kyowa Chemical Industry Co., Ltd., Kyoward (registered trademark) 500SN) were added, followed by stirring at 80°C. Kyoward 500SN was filtered off by vacuum filtration, and n-butanol was distilled off under reduced pressure to obtain Epoxy Composition 9. GPC measurement was performed on the obtained Epoxy Composition 9. In addition, an epoxy resin (hereinafter sometimes referred to as Resin 9) composed of a reaction product of bisphenol A epoxy resin and butenediol was extracted from Epoxy Composition 9 by preparative GPC.

[0200] Comparative Example 2: 58.2 g (0.68 mol) of butynediol, 500 g (5.40 mol) of epichlorohydrin, and 1.5 g (6.76 mmol as tetramethylammonium chloride) of 50% aqueous solution of tetramethylammonium chloride were charged into a 1 L flask equipped with a stirrer, a pressure reducing device, a dropping device, a thermometer, and a reflux device, and 112 g (1.35 mol as sodium hydroxide) of 48% aqueous solution of sodium hydroxide was placed into the dropping device. The pressure was reduced to an internal temperature of 60°C and an internal pressure of 110 to 140 hPa, and the 48% aqueous solution of sodium hydroxide was added dropwise over 5 hours. Water generated by the reaction during the dropwise addition and water present in the aqueous solution of sodium hydroxide were removed by azeotropic dehydration. The reaction was continued for another hour, and after confirming that the water in the system had been completely removed, the contents were cooled to 40°C, and 10 g each of magnesium silicate adsorbent (Kyoward (registered trademark) 600S, manufactured by Kyowa Chemical Industry Co., Ltd.) and aluminum silicate adsorbent (Kyoward (registered trademark) 700SL, manufactured by Kyowa Chemical Industry Co., Ltd.) were added and stirred. Kyoward and the resulting salt were removed by vacuum filtration. The resulting solution was heated to 120-130°C, and excess epichlorohydrin was removed by atmospheric pressure and then reduced pressure, yielding butynediol diglycidyl ether (epoxy equivalent = 114 g / eq, Mw = 198, saponifiable chlorine content 0.37%) as Resin 10.

[0201] Comparative Example 3 As resin 11, butynediol (2-Butyne-1,4-Diol Flakes, molecular weight 86, manufactured by INEOS Solvents) was prepared.

[0202] Comparative Example 4 As the resin 12, a bisphenol A type epoxy compound (EP-4100E, epoxy equivalent=190 g / eq, Mw=380) manufactured by ADEKA Corporation was prepared.

[0203] 1. Weight-average molecular weight and number-average molecular weight GPC measurement was performed on the epoxy compositions obtained in Examples 1 to 8 and Comparative Example 1, and the weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the peaks in Regions A and B of Resins 1 to 9 in the GPC chart were determined. The results are shown in Tables 1 and 2 below. Note that the weight-average molecular weight (Mw) values ​​of Resins 10 and 11 in Table 1 are molecular weight values ​​calculated from the compound structure. Furthermore, the weight-average molecular weight (Mw) value of Resin 12 in Table 1 is the value obtained from the manufacturer. GPC measurement was performed under the following conditions:

[0204] (GPC measurement conditions) GPC apparatus: GL7700 series (manufactured by GL Sciences) Measurement and analysis software: Agilent OpenLab EZChrom Column: Shodex KF-802.5 + KF-801 (manufactured by Showa Denko) Column temperature: 40°C Eluent: tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI Sample concentration: 0.1 g / 2 mL Polystyrene standards for calibration curve: Mw 96,400, 37,900, 18,100, 10,200, 5,970, 2,630, 1,010, 578, 474, 370, 266 (TSKgel standard polystyrene manufactured by Tosoh Corporation)

[0205] The peak of the epoxy resin was measured from the rising edge of the peak on the high molecular weight side to the inter-peak inflection point with the peak of the bisphenol A epoxy resin. The inter-peak inflection point was measured as the lowest vertical point (valley peak) between adjacent peaks. If the lowest points were consecutive, the midpoint was measured. Vertical division was performed using the waveform separation function in the GPC measurement and analysis software based on the inflection points described above, and the weight average molecular weight and area ratio of the peaks of each component were calculated after division. The boundaries between Region A and the peak adjacent to Region A, and between Region B and the peak adjacent to Region B, were similarly set as inter-peak inflection points.

[0206] As shown in the GPC charts of Epoxy Compositions 1 to 8 ( FIGS. 1 , 4 , 7 , and 10 to 14 ), Epoxy Compositions 1 to 8 were confirmed to be mixtures of an epoxy resin that was a reaction product of a first compound (bisphenol A epoxy resin, bisphenol F epoxy resin, ADEKA RESIN EP-4088L, ADEKA RESIN EP-3980S, ADEKA RESIN EP-4000L, or ADEKA GLYCILOR ED-523L) with a second compound (butynediol), and unreacted first compound (second epoxy compound). Similar GPC measurements were also performed on Epoxy Composition 9 obtained in Comparative Example 1, confirming that Epoxy Composition 9 was a mixture of an epoxy resin that was a reaction product of a bisphenol A epoxy resin with butenediol, and unreacted bisphenol A epoxy resin.

[0207] 2. Epoxy Resin Content The epoxy resin content was determined from the peak area ratio of each component obtained from the GPC chart of the epoxy composition measured based on the above "1. Weight-average molecular weight and number-average molecular weight of epoxy resin." In this case, the range counted as the epoxy composition was calculated by taking the sum of the peak areas derived from the bisphenol A epoxy resin and butynediol used as raw materials and the epoxy resin as a reactant as 100%, and calculating the mass ratio from the ratio of each peak area.

[0208] For example, it was confirmed from FIG. 1 that the content of Resin 1 in Epoxy Composition 1 was 64 mass %, the content of the unreacted bisphenol A epoxy resin was 36 mass %, and no unreacted butynediol was observed.

[0209] 3. Epoxy Equivalent Weight Resins 1 to 9 obtained by preparative GPC in Examples 1 to 8 and Comparative Example 1, and resin 10 obtained in Comparative Example 2 were measured using a potentiometric titrator in an environment of 25°C in accordance with JIS K 7236:2001 (corresponding to ISO 3001:1999). The epoxy equivalent weight value of resin 12 in Table 1 was entered based on information obtained from the manufacturer.

[0210] 4. Hydroxyl Value The hydroxyl value was measured in accordance with JIS K 0070-1992.

[0211] 5. Total Chlorine Content The total chlorine content was measured in accordance with JIS K7243-3.

[0212] 6. Preparative GPC Using preparative GPC, resins 1 to 9 were isolated from the epoxy compositions obtained in Examples 1 to 8 and Comparative Example 1. Extraction by preparative GPC was carried out under the following conditions.

[0213] (Preparative GPC conditions) Preparative GPC apparatus: LaboACE LC-5060 (manufactured by Japan Analytical Industry Co., Ltd.) Column: JAIGEL 2HR x 2 Eluent: chloroform Flow rate: 10 mL / min, isocratic Detector: RI, UV (254 nm) Injection volume: 10 mL Sample concentration: 0.1 g / 2 mL

[0214] 7. Content of internal triple bonds The presence or absence of internal triple bonds is determined by: 13 The presence or absence of a peak in the range of 80 ppm to 85 ppm in C-NMR was confirmed. The content of internal triple bonds was calculated from the amount of butynediol added as a raw material in the examples and the content of the epoxy resin obtained from the GPC.

[0215] 8. Storage Stability A first evaluation composition (epoxy composition) was prepared by mixing 33 parts by mass of Resins 1 to 3 and 9 to 12 prepared in the Examples and Comparative Examples with 67 parts by mass of a blending epoxy compound (bisphenol A-type epoxy compound (EP-4100E) manufactured by ADEKA Corporation, epoxy equivalent = 190 g / eq, Mw = 380)). Note that since Resin 12 prepared in Comparative Example 4 and the blending epoxy compound are the same material (bisphenol A-type epoxy compound (EP-4100E) manufactured by ADEKA Corporation), the first evaluation composition using Resin 12 in Comparative Example 4 is a composition consisting only of bisphenol A-type epoxy compound (EP-4100E) manufactured by ADEKA Corporation. The obtained first evaluation composition was allowed to stand at 80°C for one month. After standing, the container was tilted 45°C in an atmosphere of 50°C, and the fluidity of the first evaluation composition was visually observed and evaluated according to the following criteria. The results are shown in Table 1 below.

[0216] <Formulation of first evaluation composition (epoxy composition)> Resin (resins 1 to 3 and 9 to 12 of the examples and comparative examples): 33 parts by mass Epoxy compound (bisphenol A type epoxy compound (EP-4100E) manufactured by ADEKA Corporation): 67 parts by mass

[0217] <Evaluation criteria> ◯: Flowability was confirmed within 10 seconds. Δ: Flowability was confirmed between 10 and 30 seconds. ×: Flowability was not confirmed even after 30 seconds. The shorter the time until flowability was confirmed, the more excellent the storage stability.

[0218] 9. Adhesion Strength A second evaluation composition (epoxy composition) was prepared by mixing 100 parts by mass of the first evaluation composition prepared in "8. Storage Stability" above with 5 parts by mass of curing agent and 3 parts by mass of additive, as shown below. A silicon sheet with a hole 4 mm in diameter and 1 mm in height was placed on a Ni substrate (Ni-plated SPCC-SB (manufactured by Engineering Test Services)), and the hole was filled with the second evaluation composition. This was cured at 80°C for 2 hours, 100°C for 30 minutes, 120°C for 30 minutes, and 150°C for 1 hour to form a cylindrical cured product with a diameter of 4 mm and a height of 1 mm on the substrate. Next, a 4000Plus Bond Tester (manufactured by Nordson DAGE) was used to apply a horizontal force to the cylindrical cured product at 25°C to measure the load at which the cured product peeled from the substrate, thereby measuring the shear strength (MPa) and evaluating the properties according to the following criteria. The results are shown in Table 1 below.

[0219] <Formulation of second evaluation composition (epoxy composition)> Resin (resins 1 to 3 and 9 to 12 of the examples and comparative examples): 33 parts by mass Epoxy compound (bisphenol A type epoxy compound (EP-4100E) manufactured by ADEKA Corporation): 67 parts by mass Curing agent: 2E4MZ (2-ethyl-4-methylimidazole manufactured by Shikoku Chemicals Corporation) 5 parts by mass Additive: RY-200S (fumed silica, thixotropy agent manufactured by Nippon Tokushu Toryo Co., Ltd.) 3 parts by mass

[0220] <Evaluation criteria> ◯: The shear strength of the cured product is 5 MPa or more. Δ: The shear strength of the cured product is 3 MPa or more and less than 5 MPa. ×: The shear strength of the cured product is less than 3 MPa. Note that the higher the shear strength, the better the adhesive strength can be judged to be.

[0221] 10. Cure Shrinkage The composition for second evaluation prepared in "9. Adhesive Strength" above was poured into a silicone tube with an inner diameter of 4 mm and a length of 10 mm. This was cured at 80°C for 2 hours, 100°C for 30 minutes, 120°C for 30 minutes, and 150°C for 1 hour to form a cylindrical cured product with a diameter of 4 mm and a height of 10 mm. The density of the cured product was then measured using an Accupyc II 1340 density / specific gravity meter (Shimadzu Corporation) at 25°C using helium gas in accordance with JIS Z 8837:2018. The density of the composition for second evaluation before curing was also measured in the same way, and the cure shrinkage (%) was calculated according to the following formula (A) and evaluated according to the following criteria. The results are shown in Table 1 below. Cure shrinkage (%) = (1 - density of composition for second evaluation / density of cured product) x 100 (A)

[0222] <Evaluation Criteria> ◯: Curing shrinkage rate is less than 2% X: Curing shrinkage rate is 2% or more The smaller the curing shrinkage rate, the less curing shrinkage there is, and the better the low curing shrinkage property can be judged to be.

[0223]

[0224]

[0225] From Table 1, it was confirmed that Resins 1 to 3 of the Examples were excellent in low cure shrinkage, storage stability, adhesive strength, etc.

Claims

1. An epoxy resin characterized by having an internal triple bond and a weight average molecular weight of 500 or more.

2. The epoxy resin according to claim 1, characterized in that the weight average molecular weight is 500 or more and 10,000 or less.

3. The epoxy resin according to claim 1, wherein the content of the internal triple bonds in the epoxy resin is 1 mmol / g or more and 2.5 mmol / g or less.

4. The epoxy resin according to claim 1, wherein the content of the internal triple bonds in the epoxy resin is 1 mmol / g or more and 2.3 mmol / g or less.

5. The epoxy resin according to claim 1, characterized in that the epoxy equivalent of the epoxy resin is 200 g / eq or more and 1000 g / eq or less.

6. The epoxy resin according to claim 1, characterized in that the epoxy equivalent of the epoxy resin is 300 g / eq or more and 1000 g / eq or less.

7. The epoxy resin of claim 1, characterized in that the epoxy resin contains the reaction product of a first compound having an epoxy group and a second compound having an internal triple bond and a second functional group that bonds to the epoxy group.

8. The epoxy resin according to claim 1, characterized in that the epoxy resin contains a compound represented by the following general formula (1): (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24 each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more. (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34 each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents the bonding site.

9. A method for producing an epoxy resin, comprising a reaction step of synthesizing an epoxy resin by reacting a first compound having an epoxy group with a second compound having an internal triple bond and a second functional group that bonds to the epoxy group.

10. An epoxy composition comprising the epoxy resin according to claim 1 and an epoxy compound other than said epoxy resin.

11. The epoxy composition according to claim 10, characterized in that the total chlorine content of the epoxy composition is 10 ppm or more and 1500 ppm or less.

12. A curable composition comprising the epoxy resin according to claim 1 and a curing agent.

13. A cured product of the curable composition according to claim 12.

14. A method for producing a cured product, comprising a curing step of curing the curable composition according to claim 12.

15. A compound represented by the following general formula (1): (In the formula, L 21 and L 22 each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 23 and L 24 each independently represents a group selected from a group represented by the following general formula (1a) and a group represented by the following general formula (1b), and n1 represents an integer of 1 or more. (In the formula, L 32 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms; L 33 and L 34 each independently represents a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms; r1 and r2 each independently represent an integer of 0 to 10; R 11 represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and * represents the bonding site.

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