Compounds containing glycidyl ether groups and their manufacturing methods, curable resin compositions, cured products and laminates

Abstract

This invention provides a compound that, although a curable resin, can easily achieve disintegration / repairability / reforming properties in its cured form, as well as a curable resin composition and its cured form made using the aforementioned compound. Specifically, it uses a compound containing glycidyl ether groups, which is a compound containing glycidyl ether groups formed by linking structural unit A having one or more glycidyl ether groups with structural unit B, which is different from A, via ABA. The compound is characterized in that structural unit A contains a maleimide structure, structural unit B contains a furan structure, and the compound containing glycidyl ether groups is formed by linking structural unit A and structural unit B via a reversible bond resulting from the Diels-Adel reaction.

Description

Compounds containing glycidyl ether groups, curable resin compositions, cured products and laminates This invention relates to compounds containing glycidyl ether groups having a specific structure, curable resin compositions containing the same, cured products, and laminates containing layers composed of the cured products. Cured products derived from epoxy resins possess excellent heat resistance, mechanical strength, electrical properties, and adhesion, making them indispensable materials in various fields such as electrical / electronics, coatings, and adhesives. On the other hand, regarding cured products using thermosetting resins such as epoxy resin, there are examples of low long-term reliability. For instance, if the cured epoxy resin deteriorates due to oxidation, cracks may occur. Furthermore, once thermosetting resins such as epoxy resins harden to form a hardened product, they cannot be dissolved in solvents (insoluble) and will not melt at high temperatures (unmeltable). Therefore, they lack recyclability and reusability, and the hardened product becomes waste after use. Thus, reducing waste and alleviating environmental impact has become a challenge. Therefore, for hardened materials using epoxy resins, there is a need to address issues such as extending their lifespan and reducing waste. Among these solutions, imparting the hardened material with ease of disassembly and repair / remodeling properties is considered effective. Against this backdrop, a method has been disclosed in which a thermally decomposable compound is incorporated into the adhesive component of the reaction system beforehand, and then heated to a certain degree after use, thereby reducing the adhesive strength and enabling it to disintegrate (for example, see Patent Document 1). Another method for forming a sealing material has been disclosed, in which, even in the case of cracks or peeling in a sealing material using epoxy resin or the like, self-repair can be achieved by using microcapsule particles containing a first thermosetting resin and a second thermosetting resin precursor (for example, see Patent Document 2). In addition to the above, efforts are being made to utilize reversible bonds such as dynamic covalent bonds and supramolecular bonds in hardened materials to impart repair / reshaping properties. [Previous Art Literature] [Patent Literature] [Patent Document 1] Japanese Patent Application Publication No. 2013-256557 [Patent Document 2] Japanese Patent Application Publication No. 2017-041496 [The problem the invention aims to solve] In the technology provided in the aforementioned Patent Document 1, the disintegrated adhesive is discarded, while the substrate used as the adhesive can be recycled, but the overall recyclability remains insufficient. Furthermore, while the technology in the aforementioned Patent Document 2 possesses a certain degree of self-healing capability, it is not a solution from a reuse perspective, and the problem of it becoming waste when no longer needed remains. Moreover, in the aforementioned reversible bonding-related raw materials, molecular mobility must be ensured, thus limiting the use of only gel-like substances lacking mechanical strength as raw materials. Currently, improvements are required in both of these aspects. Therefore, the object of this invention is to provide a compound that, although a curable resin, can easily achieve disintegration / repairability / reforming properties in the cured product, and a curable resin composition made using the aforementioned compound and its cured product. [Means for solving the problem] The inventors of this case conducted a detailed study and discovered that by using a compound containing glycidyl ether groups with a specific structure and using it as a component of a curable resin, the aforementioned problems could be solved, thereby completing the invention. That is, the present invention includes the following states. [1] A compound containing glycidyl ether group, which is a compound containing glycidyl ether group formed by linking structural unit A having one or more glycidyl ether groups with structural unit B different from the above A by ABA, characterized in that: the above structural unit A contains a maleimide structure, the above structural unit B contains a furan structure, and the above compound containing glycidyl ether group is formed by linking the above structural unit A and the above structural unit B by a reversible bond obtained by the Diels-Alder reaction. [2] The compound containing glycidyl ether group as described in [1], wherein the above structural unit B has an alkyl chain or an alkyl ether chain. [3] The compound containing glycidyl ether group as described in [2], wherein the number of carbon atoms of the above alkyl chain is 4 to 16. [4] A compound containing an epoxypropyl ether group as described in any of [1] to [3] above, wherein the aforementioned structural unit B further has the same reversible bond as the reversible bond derived from the Diels-Adel reaction, which serves as the linking site between structural unit A and structural unit B. [5] A compound containing an epoxypropyl ether group represented by the following general formula (1): The furan-derived structure in formula (1) may also contain halogen atoms, alkoxy groups, arylalkoxy groups, aryloxy groups, nitro groups, amide groups, alkoxycarbonyl groups, aryloxycarbonyl groups, cyano groups, alkyl groups, cycloalkyl groups, aralkyl groups, or aryl groups as substituents. The average number of repetitions in the n-series is 0 to 10. 1 For the following formula (2), Z 2 For the following formula (3), Z 3It can be any of the structures represented by the following formula (4), and there can be multiple of them in one molecule, which can be the same or different. [The aromatic ring in formula (2) may be substituted or unsubstituted, and * indicates a bond site. G is glycidyl or 2-methylglycidyl, and -OG on the naphthalene ring in the formula indicates that it can be bonded at any location]. In formula (3), Ar is an independent structure containing an aromatic ring that is either unsubstituted or has substituents, and R 1 R 2 Each is independently a hydrogen atom, methyl, or ethyl; R is a hydrogen atom or methyl; R' is a divalent hydrocarbon group with 2 to 12 carbon atoms; n1 is an integer from 2 to 16; n2 is the average value of the repeating units, ranging from 2 to 30; k1 is the average number of repeating units, ranging from 0.5 to 10; p1 and p2 are independently 0 to 5; X is the structural unit represented by the following formula (3-1); Y is the structural unit represented by the following formula (3-2). In equations (3-1) and (3-2), Ar, R, and R 1 R 2 [R', n1, n2 are the same as above]. m1 and m2 are the average values ​​of the repetitions, each independently ranging from 0 to 25, and m1 + m2 ≥ 1. However, the bond between structural unit X represented by the aforementioned equation (3-1) and structural unit Y represented by the aforementioned equation (3-2) can be random or block, and the total number of structural units X and Y present in one molecule are m1 and m2, respectively. [In formula (4), n3 and n5 are the average values ​​of the number of repetitions, which are 0.5 to 10 respectively, n4 is an integer from 1 to 16, and R” is independently a hydrogen atom, methyl or ethyl]. [6] A curable resin composition, wherein the compound containing glycidyl ether group as described in any one of [1] to [5] above and the compound (I) that is reactive with the compound containing glycidyl ether group are essential components. [7] The curable resin composition as described in [6] above, wherein the compound (I) that is reactive with the compound containing glycidyl ether group is a hydroxyl-containing compound. [8] The curable resin composition as described in [6] or [7] above, wherein the compound (I) that is reactive with the compound containing glycidyl ether group is a hydroxyl-containing compound having reversible bonds. [9] The curable resin composition as described in [8] above, wherein the hydroxyl-containing compound having reversible bonds is a hydroxyl-containing compound represented by the following general formula. In formula (7), each Ar is an independent structure containing an aromatic ring, either unsubstituted or substituent. The structures derived from anthracene in formulas (5-1) and (5-2), and from furan in formulas (6-1) and (6-2), may also contain halogen atoms, alkoxy groups, arylalkoxy groups, aryloxy groups, nitro groups, amide groups, alkoxycarbonyl groups, aryloxycarbonyl groups, cyano groups, alkyl groups, cycloalkyl groups, aralkyl groups, or aryl groups as substituents. In the formula, ma is an integer from 1 to 10, mb is an integer from 1 to 4, and n is the average of the repetitions, ranging from 0 to 10. Z 5 For the following formula (8), Z 2 For the following formula (9), Z 3 For the following formula (10), Z 4 It can be any of the structures represented by the following formulas (11) and (12), and there can be multiple structures in one molecule, which can be the same or different. [The aromatic ring in formula (8) may be substituted or unsubstituted, and * indicates a bond site. The hydroxyl group on the naphthalene ring in the formula indicates that it can be bonded at any location.] In formula (9), Ar is an independent structure containing an aromatic ring that is either unsubstituted or has substituents, and R 1 R 2 Each is independently a hydrogen atom, methyl, or ethyl; R is a hydrogen atom or methyl; R' is a divalent hydrocarbon group with 2 to 12 carbon atoms; n1 is an integer from 2 to 16; n2 is the average value of the repeating units, ranging from 2 to 30; k1 is the average number of repeating units, ranging from 0.5 to 10; p1 and p2 are independently 0 to 5; X is the structural unit represented by the following formula (9-1); Y is the structural unit represented by the following formula (9-2). In equations (9-1) and (9-2), Ar, R, and R0 are... 1 R 2 [R', n1, n2 are the same as above]. m1 and m2 are the average values ​​of the repetitions, each independently ranging from 0 to 25, and m1 + m2 ≥ 1. However, the bond between structural unit X represented by the aforementioned equation (9-1) and structural unit Y represented by the aforementioned equation (9-2) can be random or block, and the total number of structural units X and Y present in one molecule are m1 and m2, respectively. [In formula (10), n3 and n5 are the average values ​​of the number of repetitions, which are 0.5 to 10 respectively, n4 is an integer from 1 to 16, and R” is a hydrogen atom, methyl or ethyl.] In equations (11) and (12), R 1 R 2

[10] The curing resin composition of any one of [6] to [9] above further includes an epoxy resin of 100 to 10,000 g / eq other than the compound containing glycidyl ether group of any one of [1] to [5] above.

[11] The curing resin composition of

[10] above, wherein the epoxy resin is represented by the following formula (13) and the epoxy equivalent is 500 to 10,000 g / eq. In formula (13), Ar is an independent structure containing an aromatic ring that is either unsubstituted or has substituents, X' is a structural unit represented by formula (13-1), and Y' is a structural unit represented by formula (13-2). In equations (13-1) and (13-2), Ar is the same as described above, and R... 1 R 2 Each is independently a hydrogen atom, methyl or ethyl, and R' is a divalent hydrocarbon group with 2 to 12 carbon atoms. 3 R 4 R 7 R 8 Each is independently a hydroxyl, glycidyl ether, or 2-methylglycidyl ether group, R 5 R 6 R 9 R 10 Each is independently a hydrogen atom or a methyl group, n 1 is an integer from 4 to 16, n The average value of the repeating units in series 2 is 2–30. 11 R 12 Each is independently an epoxypropyl ether group or a 2-methyl epoxypropyl ether group, R 13 R 14 Each is independently a hydroxyl, glycidyl ether, or 2-methylglycidyl ether group, R 15R 16 For hydrogen atoms or methyl groups, m3, m4, p1, p2, and q are the average of the number of repetitions, m3 and m4 are each independently 0 to 25, and m3 + m4 ≥ 1, p1 and p2 are each independently 0 to 5, and q is 0.5 to 5. However, the bond between the structural unit X' represented by the aforementioned formula (13-1) and the structural unit Y' represented by the aforementioned formula (13-2) can be random or block, and the total number of each structural unit X and Y present in 1 molecule is m3 and m4, respectively.

[12] As in any of the aforementioned [6] to

[11] , the concentration of reversible bonds is 0.10 mmol / g or more relative to the total mass of the curing components in the curing resin composition.

[13] As in any of the aforementioned [6] to

[12] , the curing resin composition is any one of a self-healing composition, a disintegrating composition, or a composition for reforming materials.

[14] A curable material formed by curing a curable resin composition described in any one of [6] to

[13] above.

[15] A laminate having a substrate and a layer comprising the curable material as described in

[14] above.

[16] A heat-resistant component comprising the curable material as described in

[14] above.

[17] A method for manufacturing a compound containing an epoxypropyl ether group, wherein the compound containing an epoxypropyl ether group is synthesized in situ using a conjugated diene intermediate represented by the following general formula (1)' and a maleimide compound having an epoxypropyl ether group, during a curing process with the aforementioned compound (I) which is reactive with the compound containing an epoxypropyl ether group. [In the formula, n and Z] 2 Z 3 [Same as above].

[18] A cured compound obtained by using the aforementioned formula (1)', a maleimide compound having an epoxypropyl ether group, and the aforementioned compound (I) which is reactive with compounds containing an epoxypropyl ether group as necessary raw materials and subjecting them to a curing reaction. [Effects of the Invention] According to the present invention, hardened articles composed of hardening resin compositions can be endowed with disintegration, repairability and reshaping properties, which contribute to the longevity of the hardened articles themselves and the reduction of waste. [The form in which the invention is carried out] The embodiments for carrying out the present invention will now be described in detail. The present invention is not limited to the embodiments described below. It should be understood that appropriate design changes and modifications can be made based on the common knowledge of those skilled in the art without departing from the spirit of the present invention. As one aspect of the present invention, a compound containing an oxypropyl ether group is a compound having one or more structural units A having an oxypropyl ether group and structural units B different from A linked by an ABA bond. The compound is characterized in that: the aforementioned structural unit A contains a maleimide structure, the aforementioned structural unit B contains a furan structure, and the aforementioned compound containing the oxypropyl ether group is formed by the aforementioned structural unit A and the aforementioned structural unit B being bonded by a reversible bond resulting from the Diels-Adel reaction. Furthermore, the oxypropyl ether group in the present invention refers not only to an unsubstituent oxypropyl ether group but also to one having substituents on the carbon atom. By having such a structure, compounds containing glycidyl ether groups are introduced into a cross-linked structure through a curing reaction based on these glycidyl ether groups. Furthermore, the hardened material retains reversibility, particularly since structural unit B can separate from the cross-linked structure, thus exhibiting high molecular mobility even within the hardened material. Therefore, when the hardened material is impacted and cracks or shatters, the aforementioned reversible bonds are easily severed, exhibiting easy disintegration. Moreover, these reversible bonds can reversibly reform into bonds even in low-temperature regions, including room temperature, thus performing functions such as repair and reshaping. Because structural unit B can separate from the cross-linked structure, it exhibits exceptionally high molecular mobility, demonstrating low-temperature repair and low-temperature reshaping. For example, even when a hardened material made using the compound containing glycidyl ether groups of this invention is shattered, by placing it in a low-temperature state, including room temperature, or under heating / heating conditions, the hardened material can be easily repaired based on the reversible bonds, and it can also be reshaped after shattering. To introduce the aforementioned furan-type addition structure (reversible bond) derived from the Diels-Adel reaction into a compound, from the viewpoint of ease of preparation, it is preferable to use a method involving furan with reactive functional groups on the ring and maleimide with reactive functional groups. The specific reversible bond structure can be represented by the following chemical formula. Based on the R portion of the formula derived from maleimide or various reactive functional groups on the ring derived from furan, these functional groups are bonded to other structural units, thereby introducing a reversible bond into the compound. In the Diels-Alder reaction, a conjugated diene undergoes an addition reaction with a diephile to form a 6-membered ring. The Diels-Alder reaction is an equilibrium reaction, therefore, at a given temperature, a reverse Diels-Alder reaction occurs, resulting in dissociation (de-crosslinking). When mechanical energy such as scratches or external forces are applied to the resulting hardened material, the C-C bonds of the Diels-Alder reaction units have lower bond energies than ordinary covalent bonds, thus the C-C bonds of the Diels-Alder reaction units are preferentially cleaved. Therefore, the hardened material exhibits easy disintegration. Furthermore, in temperature regions lower than the dissociation temperature, the equilibrium of the C-C bonds of the Diels-Alder reaction units shifts towards the bonding direction, leading to the re-formation of the adduct (Diels-Alder reaction unit), thus suggesting the potential for scratch repair and reforming. In reversible bonds derived from the Diels-Adel reaction, for example, the Diels-Adel reaction unit composed of anthracene and maleimide structures has a dissociation temperature as high as 250°C or higher, and will not dissociate at least around 200°C. On the other hand, reversible bonds derived from the Diels-Adel reaction of furan and maleimide structures undergo a reverse Diels-Adel reaction and dissociate (de-crosslinking) around 120°C. Therefore, the heating temperature required to make the cured material exhibit easy disintegration can be reduced, and it exhibits excellent easy disintegration in applications where high-temperature heating is not suitable. In the target compound containing glycidyl ether, there are at least two of the aforementioned reversible bonds. However, from the point of view that a structure with higher molecular mobility can be obtained and the mechanical strength and other physical properties of the hardened material can be easily adjusted, the preferred structural unit B also has multiple of the aforementioned reversible bonds. Furthermore, for the same reasons as described above, the molecular weight of structural unit B is preferably of a certain magnitude, for example, its average molecular weight (Mw) is preferably 28 or higher. When structural unit B has reversible bonds, the molecular weight between the reversible bonds is preferably 28 or higher. In addition, structural unit B may also contain the same crosslinking functional group as the glycidyl ether group in structural unit A, but from the viewpoint of more easily demonstrating the effects of the present invention, it is preferable that it does not have crosslinking (hardening) functional groups. In the aforementioned structural unit B, when the compound containing the epoxypropyl ether group of the present invention is used as, for example, a structural adhesive, from the viewpoint of further enabling the cured product to exhibit flexibility or conformability to the substrate, it is preferable to have an alkyl chain or an alkyl ether chain. In this case, as an alkyl chain, it is more preferably 2 to 30 carbon atoms, and particularly preferably 4 to 16 carbon atoms. As for the aforementioned alkyl ether chain, it is not particularly limited, but it is preferably an alkyl ether chain with 2 to 12 carbon atoms, and the average number of repetitions is preferably in the range of 2 to 30. The glycidyl ether group in the aforementioned structural unit A can be any group as long as it can easily react with other functional groups. From the viewpoint of ease of obtaining raw materials and curability, it is preferable to have a glycidyl ether group without substituents on the carbon atom. Furthermore, the number of glycidyl ether groups in the aforementioned structural unit A is not particularly limited. From the viewpoint of ease of obtaining raw materials in industry and ease of adjusting the crosslinking density when forming the cured product, it is preferable to be in the range of 1 to 3, and more preferably 1 to 2. The average molecular weight (Mw) of the aforementioned compounds containing glycidyl ether groups is not particularly limited, but from the viewpoint of possessing mechanical strength, flexibility, and a combination of disintegration and repair / reshaping properties when formed into a cured material, it is preferably 500 or more, and preferably 50,000 or less. Furthermore, apart from the range between A and B, in cases where structural unit B has multiple reversible bonds, from the viewpoint of disintegration / reshaping properties of the cured material, the molecular weight of each reversible bond is preferably in the range of 300 to 10,000. As one aspect of the present invention, the compound containing glycidyl ether is a compound represented by the following general formula. In formula (1), the furan-derived structure may also have halogen atoms, alkoxy groups, arylalkoxy groups, aryloxy groups, nitro groups, amide groups, alkoxycarbonyl groups, aryloxycarbonyl groups, cyano groups, alkyl groups, cycloalkyl groups, aralkyl groups, or aryl groups as substituents. The average number of repetitions in the n-series is 0–10. 1 For the following formula (2), Z 2 For the following formula (3), Z 3 It can be any of the structures represented by the following formula (4), and there can be multiple of them in one molecule, which can be the same or different. [The aromatic ring in formula (2) may be substituted or unsubstituted, and * indicates a bond site. G is glycidyl or 2-methylglycidyl, and -OG on the naphthalene ring in the formula indicates that it can be bonded at any location]. In formula (3), Ar is an independent structure containing an aromatic ring that is either unsubstituted or has substituents, and R 1 R 2 Each is independently a hydrogen atom, methyl, or ethyl; R is a hydrogen atom or methyl; R' is a divalent hydrocarbon group with 2 to 12 carbon atoms; n1 is an integer from 2 to 16; n2 is the average value of the repeating units, ranging from 2 to 30; k1 is the average number of repeating units, ranging from 0.5 to 10; p1 and p2 are independently 0 to 5; X is the structural unit represented by the following formula (3-1); Y is the structural unit represented by the following formula (3-2). In equations (3-1) and (3-2), Ar, R, and R 1 R 2 [R', n1, n2 are the same as above]. m1 and m2 are the average values ​​of the repetitions, each independently ranging from 0 to 25, and m1 + m2 ≥ 1. However, the bond between structural unit X represented by the aforementioned equation (3-1) and structural unit Y represented by the aforementioned equation (3-2) can be random or block, and the total number of structural units X and Y present in one molecule are m1 and m2, respectively. [In formula (4), n3 and n5 are the average values ​​of the number of repetitions, which are 0.5 to 10 respectively, n4 is an integer from 1 to 16, and R” is a hydrogen atom, methyl or ethyl.] The aforementioned general formula (1) contains, within the molecule, a reversible bond formed at the terminal end by a furan structure and a maleimide structure. The terminal maleimide structure in general formula (1) has a Z-shaped structure belonging to any of the structures represented by the aforementioned general formula (2). 1 The aforementioned glycidyl ether group or 2-methyl glycidyl ether group in the curing resin composition described later contributes to the curing reaction. Z in the formula 1 , refers to the structural unit represented by the aforementioned general formula (2) having an epoxypropyl ether group or a 2-methyl epoxypropyl ether group. Among these, from the viewpoint of ease of obtaining raw materials and reactivity, the following structural formula is preferred. G is an epoxypropyl ether group or a 2-methyl epoxypropyl ether group. In the aforementioned general formula (1), the site where the structure originating from furan is linked is designated as Z. 2 The site where the structure derived from maleimine is linked is designated Z. 3 , which are either structures represented by the aforementioned general formulas (3) and (4). Z in the formula 2 The above-mentioned general formula (3) represents the structure, and among these, from the viewpoint of balancing the ease of obtaining raw materials and reactivity, and the strength and softness of the resulting compound, the following structural formula is preferred. [In the formula, Ar, R, m1, m2, n1, n2, k1, p1, p2, X, and Y are the same as those mentioned above] In the aforementioned general formula (1), n ​​is the average number of repetitions, which is 0 to 10, preferably in the range of 0 to 5. In the aforementioned structural formula, Ar represents an aromatic ring that may have substituents and is not particularly limited. Examples of aromatic rings include: benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and genus rings. Examples of substituents include: halogen atoms, alkoxy groups, arylalkoxy groups, aryloxy groups, nitro groups, amide groups, alkoxycarbonyl groups, aryloxycarbonyl groups, cyano groups, alkyl groups, cycloalkyl groups, aralkyl groups, and aryl groups. Preferably, the substituents on Ar are those that will not undergo a curing reaction when used as a curable resin composition as described later, because they more readily exhibit the effects of the present invention. Of these, Ar is preferably any of the structures represented by the following structural formulas. [The aromatic ring in the formula may be substituted or unsubstituted, and * indicates a bond node]. Alternatively, the following structure can be used as Ar. (In the formula, the aromatic ring may be substituted or unsubstituted, n) 6 = 1 to 4, * indicates a key node. As for the aforementioned Ar structure, the following is preferred. * indicates a bond node. The repeating unit n in the aforementioned general formulas (3) and (3-1) 1 is an integer from 2 to 16. By making n When 1 is 4 or higher, the deformation mode during the formation of hardened material is more likely to become elastic deformation. Furthermore, by making n... A value of 16 or lower can suppress the decrease in crosslinking density. A value of 4–15 is preferred, and 6–12 is even better. R in the aforementioned general formulas (3) and (3-1) 1 R 2 Each of them is independently a hydrogen atom, a methyl group, or an ethyl group, and each of R is independently a hydrogen atom or a methyl group. Among these, it is preferred to be a hydrogen atom. In the aforementioned general formulas (3) and (3-2), n The average value of the repeating unit in the 2-series is 2 to 30. From the viewpoint that this range is favorable for achieving a good balance between the viscosity of the compound containing the glycidyl ether group and the crosslinking density of the resulting cured product, it is preferable. 2 to 25 is preferred, and 4 to 20 is even more preferred. In the aforementioned general formulas (3) and (3-2), R' is a divalent hydrocarbon group with 2 to 12 carbon atoms. Within this range, in addition to increased adhesion, the deformation mode of the hardened material is more likely to become elastic deformation. Preferably, R' is a divalent hydrocarbon group with 2 to 6 carbon atoms. There are no particular limitations on the aforementioned divalent hydrocarbon groups, and examples include: linear or branched alkyl groups, alkenyl groups, alkyne groups, cycloalkyl groups, aryl groups, and arylalkyl groups (divalent groups having both alkyl and aryl groups). Examples of alkyl groups include: methylene, ethyl, propyl, butyl, pentyl, hexyl, trimethylene, tetramethylene, pentamethylene, hexamethylene, etc. Examples of alkenyl groups include: vinyl, 1-methylvinyl, propenyl, butenyl, pentenyl, etc. Examples of ynyl groups include: ethynyl, propynyl, butynyl, pentynyl, hexynyl, etc. Examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. Examples of aryl groups include: phenyl, methylphenyl, dimethyl, naphthyl, etc. Among these, from the viewpoint of the ease of obtaining raw materials, the viscosity of the resulting compound containing glycidyl ether, and the balance of flexibility when forming a hardened product, ethyl, propyl, and tetramethylene are preferred. In the aforementioned general formulas (3) and (3-2), R is independently either a hydrogen atom or a methyl group. Among these, a hydrogen atom is preferred. In the aforementioned general formula (3), m1 and m2 are the average values ​​of the repetition counts of the aforementioned structural unit X and structural unit Y, respectively, each ranging from 0 to 25, and m1 + m2 ≥ 1. Preferably, m1 and m2 are in the range of 0.5 to 10. Furthermore, k1 in the aforementioned general formula (3) is the average of the number of repetitions, which is in the range of 0.5 to 5, preferably in the range of 0.5 to 2. In the aforementioned general formula (4), n3 and n5 are the average values ​​of the number of repetitions, which are 0.5 to 10 respectively, n4 is an integer from 1 to 16, and R” is independently a hydrogen atom, methyl or ethyl. Among these, from the viewpoint of ease of obtaining raw materials and mechanical properties of the resulting cured product, it is preferable that n3 is in the range of 0.5 to 10, n5 is in the range of 2 to 3, n4 is preferably an integer from 1 to 8, and R” is preferably a hydrogen atom. Examples of compounds containing glycidyl ether groups according to the present invention include, but are not limited to, those shown below. [In the formula, R' is a divalent hydrocarbon group with 2 to 12 carbon atoms, n is the average number of repeating units, which is 0 to 10, n1 is an integer from 4 to 16, n2 is the average number of repeating units, which is 2 to 30, and k1 is 0.5 to 5]. The method for manufacturing compounds containing glycidyl ether groups, as one embodiment of the present invention, is not particularly limited. It can be carried out by using known reactions in stages according to the target structure. Furthermore, the raw materials can also be obtained by appropriately combining commercially available products. Representative synthetic methods are described below. The aforementioned general formula (1) has two Diels-Adel reaction units as reversible bonds within the molecule. These Diels-Adel reaction units are addition reaction units formed by the Diels-Adel reaction, consisting of a furan structure and a maleimide structure. Furthermore, in general formula (1), it is possible to use a Z-shaped structure... 1 It was obtained by using maleimine compounds with the structure of [missing information]. The so-called Diels-Adel reaction, in which conjugated dienes such as furan structures undergo addition reactions with diephiles such as maleimides to form a 6-membered ring, is an equilibrium reaction. At temperatures higher than those at which the addition reaction occurs, the addition reaction part dissociates and undergoes a reverse reaction, reverting to the original conjugated diene and diephile, which is known as the reverse Diels-Adel reaction. As mentioned above, Z 1 Precursors to maleimide compounds with the structure described above, i.e., maleimide compounds containing hydroxyl groups, can be any of the compounds listed below. Among these, hydroxyphenyl maleimide is preferred in terms of curability, and monohydroxyphenyl maleimide is particularly preferred in terms of the balance between reactivity and the properties of the cured product, as well as its repair and reforming properties. Among monohydroxyphenyl maleimides, p-hydroxyphenyl maleimide is particularly preferred from the viewpoint of heat resistance. The hydroxyl groups in the compound can, for example, be glycidyl ether groups by the known methods described in the examples. Furthermore, the structures of the aforementioned maleimine compounds are independent of each other, and each contains a hydrogen atom, halogen atom, alkoxy group, arylalkoxy group, aryloxy group, nitro group, acetamyl group, alkoxycarbonyl group, aryloxycarbonyl group, cyano group, alkyl group, cycloalkyl group, aralkyl group, or aryl group as a substituent. Moreover, in the structures of the compounds listed above, alkoxy group, arylalkoxy group, aryloxy group, carboxyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkyl group, cycloalkyl group, aralkyl group, and aryl group also include those formed by further bonding various substituents to the carbon atoms of these compounds. The Diels-Adel reaction can be performed using well-known methods. For example, the conjugated diene compound can be mixed with a diephilic compound or, depending on the situation, one component can be in excess. The mixture can be heated to melt or dissolve in a solvent, stirred at room temperature to 110°C for 1 to 24 hours, and obtained by direct filtration and distillation to remove the solvent without purification. Alternatively, it can be obtained by commonly used single-isolation purification methods such as recrystallization, recrystallization, and chromatography. Regarding the synthesis of sites other than reversible bonds, known methods can be used. For example, by reacting an aliphatic dihydroxy compound with a diglycidyl ether or aliphatic divinyl ether with an aromatic hydroxy compound to obtain a compound with a terminal hydroxyl group, the compound is then reacted with furan methyl glycidyl ether to introduce a furan structure at the end. Then, as described above, the compound is subjected to a Diels-Adel reaction with a maleimine compound having a glycidyl ether group to obtain the compound represented by the aforementioned general formula (1). Alternatively, after obtaining a compound with a hydroxyl group at the end, it is epoxidized to make the end a glycidyl ether group, and then reacted with furfuryl alcohol, etc., thereby introducing a furan structure at the end. Then, as described above, it is reacted with a maleimine compound having a glycidyl ether group to undergo a Diels-Adel reaction, thereby obtaining the compound represented by the aforementioned general formula (1). Alternatively, an aromatic dihydroxy compound can be reacted with a dihalogenated alkyl compound or a dihalogenated aralkyl compound to obtain a compound with a terminal alkyl halide. Then, it can be reacted with furfuryl alcohol to introduce a furan structure at the end. Then, as described above, it can be reacted with a maleimine compound having an epoxypropyl ether group to undergo a Diels-Adel reaction to obtain the compound represented by the aforementioned general formula (1). Diglycidyl ethers, which are the aforementioned aliphatic dihydroxy compounds, are not particularly limited, and examples include: 1,11-undecanediol diglycidyl ether, 1,12-dodecanediol diglycidyl ether, 1,13-tridecanediol, 1,14-tetradecanediol diglycidyl ether, 1,15-pentadecande ... Among these, from the viewpoint of achieving a good balance between the softness and heat resistance of the resulting cured product, compounds with an alkyl chain having 12 to 14 carbon atoms having glycidyl groups linked to both ends through ether groups are preferred, with 1,12-dodecanediol diglycidyl ether, 1,13-tridecanediol, and 1,14-tetradecanediol diglycidyl ether being the most suitable. The aforementioned aliphatic diethylene ethers are not particularly limited, but can be exemplified by: straight-chain alkyl diethylene ethers such as polyethylene glycol diethylene ether, polypropylene glycol diethylene ether, polytetramethylene glycol diethylene ether, 1,3-butanediol diethylene ether, 1,4-butanediol diethylene ether, 1,6-hexanediol diethylene ether, 1,9-nonanediol diethylene ether, and 1,10-decanediol diethylene ether; branched alkyl diethylene ethers such as neopentyl glycol diethylene ether; diethylene ethers containing cycloalkane structures such as 1,4-cyclohexanediol diethylene ether, 1,4-cyclohexanediethanol diethylene ether, tricyclodecanediol diethylene ether, tricyclodecanediethanol diethylene ether, pentacyclopentadecanedimethanol diethylene ether, and pentacyclopentadecanedimethanol diethylene ether; bisphenol A diethylene ether, bisphenol F diethylene ether; and hydroquinone diethylene ether. These can be used alone or in combination of two or more. Among these, from the viewpoint of achieving an excellent balance between the softness and toughness of the resulting hardened material, diethylene ethers with a polyether structure or straight-chain extended alkyl chains having 9 to 10 carbon atoms are preferred, with polyethylene glycol diethylene ether, polypropylene glycol diethylene ether, polytetramethylene glycol diethylene ether, 1,9-nonanediol diethylene ether, and 1,10-decanediol diethylene ether being the most suitable. The aforementioned aromatic hydroxyl compounds are not specifically limited, but can include, for example: dihydroxybenzenes such as hydroquinone, resorcinol, and catechol; pyroquinone, 1,2,4-trihydroxybenzene, 1,3,5-trihydroxybenzene, and other trihydroxybenzenes; triphenylmethane-type phenols such as 4,4,4”-trihydroxytriphenylmethane; dihydroxynaphthalenes such as 1,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, and 2,6-dihydroxynaphthalene; and 1,1'-methylenebis(2,7-naphthalenediol) and 1,1'-dihydroxynaphthalene, which are obtained by coupling dihydroxynaphthalenes. Naphthalene-2,2',7,7'-tetraol, 1,1'-oxybis(2,7-naphthyldiol) and other tetrafunctional phenols, bis(4-hydroxyphenyl)methane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclohexane and 1,1-bis(4-hydroxyphenyl)-1-phenylethane and bis(4-hydroxyphenyl) benzo[a] bisphenols, 2,2'-biphenol, 4,4'-biphenol, (1,1'-biphenyl)-3,4-diol, 3,3'-dimethyl-(1,1'-biphenyl)-4,4'-diol, 3-methyl Biphenyl phenols containing alicyclic structures, such as 1,1'-biphenyl)-4,4'-diol, 3,3',5,5'-tetramethylbiphenyl-2,2'-diol, 3,3',5,5'-tetramethylbiphenyl-4,4'-diol, 5-methyl-(1,1'-biphenyl)-3,4'-diol, 3'-methyl-(1,1'-biphenyl)-3,4'-diol, 4'-methyl-(1,1'-biphenyl)-3,4'-diol, adducts of phenols with dicyclopentadiene, and adducts of phenols with terpenoids, as well as bis(2-hydroxy-1-naphthyl)methane and bis(2-hydroxy-1-naphthyl)propane. The condensation reaction products of naphthols, phenols, and dimethyl chloride or dimethyl chloride are known as Xylok-type phenolic resins, which can be used alone or in combination with two or more types. Furthermore, difunctional phenolic compounds with methyl, tertiary butyl, or halogen atoms as substituents on the aromatic nucleus of the aforementioned compounds can also be listed. In addition, the aforementioned phenols containing alicyclic structures and the aforementioned Xylok-type phenolic resins can not only simultaneously contain difunctional components but also simultaneously contain three or more functional components. They can be used directly or purified through column chromatography or other purification steps to extract only the difunctional components for use. Among these, bisphenols are preferred from the viewpoint of achieving an excellent balance between flexibility and toughness when forming a hardened product, especially from the viewpoint of significantly imparting toughness; bis(4-hydroxyphenyl)methane and 2,2-bis(4-hydroxyphenyl)propane are preferred. Furthermore, when the moisture resistance of the hardened product is important, phenols containing alicyclic structures are preferred. Regarding the reaction ratio of the aforementioned aliphatic dihydroxy compound diglycidyl ether to the aforementioned aromatic hydroxy compound, it is preferable to react them in a range of 1 / 1.01 to 1 / 5.0 (molar ratio). From the viewpoint that the resulting cured product has a good balance of flexibility and heat resistance, (a1) / (a2) is preferably 1 / 1.02 to 1 / 3.0 (molar ratio). The reaction of the aforementioned aliphatic dihydroxy compound diglycidyl ether with the aforementioned aromatic hydroxy compound is preferably carried out in the presence of a catalyst. Various catalysts can be used as the aforementioned catalysts, including, for example: alkali (earth) metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, and calcium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; phosphorus compounds such as triphenylphosphine; chlorides, bromides, and iodides of DMP-30, DMAP, tetramethylammonium, tetraethylammonium, tetrabutylammonium, and benzyltributylammonium; quaternary ammonium salts such as chlorides, bromides, and iodides of tetramethylphosphonium, tetraethylphosphonium, tetrabutylphosphonium, and benzyltributylphosphonium; triethylamine; N,N-dimethylbenzylamine; tertiary amines such as 1,8-diazabicyclo[5.4.0]undecene and 1,4-diazabicyclo[2.2.2]octane; and imidazoles such as 2-ethyl-4-methylimidazolium and 2-phenylimidazolium. It is also permissible to use two or more of these catalysts. From the viewpoint of rapid reaction and excellent reduction of impurities, sodium hydroxide, potassium hydroxide, triphenylphosphine, and DMP-30 are preferred. The amount of these catalysts used is not particularly limited, but 0.0001 to 0.01 mol is preferred compared to 1 mol of the phenolic hydroxyl group of the aforementioned aromatic hydroxyl compounds. The form of these catalysts is also not particularly limited; they can be used in aqueous solution or solid form. Furthermore, the reaction between the aforementioned aliphatic dihydroxy compound diglycidyl ether and the aforementioned aromatic dihydroxy compound can be carried out in the absence of a solvent or in the presence of an organic solvent. Examples of usable organic solvents include: methyl celecoxib, ethyl celecoxib, toluene, xylene, methyl isobutyl ketone, dimethyl sulfoxide, propanol, butanol, etc. The amount of organic solvent used, relative to the total mass of the raw materials, is typically 50–300% by mass, preferably 100–250% by mass. These organic solvents can be used alone or in combination. To ensure rapid reaction, a solvent-free reaction is preferred; however, from the viewpoint of reducing impurities in the final product, dimethyl sulfoxide is preferred. The reaction temperature for carrying out the aforementioned reaction is typically 50–180°C, and the reaction time is typically 1–10 hours. From the viewpoint of reducing impurities in the final product, a reaction temperature of 100–160°C is preferred. Furthermore, if the resulting compound exhibits significant coloration, antioxidants or reducing agents may be added to suppress this. Antioxidants are not particularly limited, and examples include hindered phenolic compounds such as 2,6-dialkylphenol derivatives, divalent sulfur compounds, or trivalent phosphorus-containing phosphite compounds. Reducing agents are not particularly limited, and examples include hypophosphorous acid, phosphorous acid, thiosulfate, sulfurous acid, bisulfite, or salts thereof. After the aforementioned reaction is complete, neutralization or washing can be performed until the pH of the reaction mixture reaches 3-7, preferably 5-7. Neutralization or washing can be carried out using conventional methods. For example, when using an alkaline catalyst, acidic substances such as hydrochloric acid, sodium hydrogen phosphate, p-toluenesulfonic acid, or oxalic acid can be used as neutralizing agents. After neutralization or washing, the solvent can be distilled off under reduced pressure and heating if necessary to concentrate the product and obtain the compound. Regarding the reaction ratio of the aforementioned aliphatic diethylene ether to the aforementioned aromatic hydroxyl compound, it is preferable to allow the reaction to proceed within the range of 1 / 1.01 to 1 / 5.0 (moles). From the viewpoint that the resulting cured product has a good balance of flexibility and heat resistance, (a1) / (a2) is preferably 1 / 1.02 to 1 / 3.0 (moles). The reaction between the aforementioned aliphatic dihydroxy compound diglycidyl ether and the aforementioned aromatic hydroxy compound can proceed sufficiently even without a catalyst. However, from the viewpoint of selecting raw materials and increasing the reaction rate, a catalyst may be appropriately used. Examples of catalysts that can be used here include: inorganic acids such as sulfuric acid, hydrochloric acid, nitric acid, and phosphoric acid; organic acids such as toluenesulfonic acid, methanesulfonic acid, xylenesulfonic acid, trifluoromethanesulfonic acid, oxalic acid, formic acid, trichloroacetic acid, and trifluoroacetic acid; and Lewis acids such as aluminum chloride, ferric chloride, tin chloride, gallium chloride, titanium chloride, aluminum bromide, gallium bromide, boron trifluoride ether complexes, and boron trifluoride phenol complexes. Generally, the amount of catalyst used is in the range of 10 ppm to 1% by weight relative to the mass of the diethylene ether compound. In this case, it is preferable to select the type and amount of catalyst in a way that avoids nucleoaddition of the vinyl group to the aromatic ring. Furthermore, the reaction between the aforementioned aliphatic diethylene ether and the aforementioned aromatic hydroxyl compound can be carried out in the absence of a solvent or in the presence of an organic solvent. Examples include: aromatic organic solvents such as benzene, toluene, and xylene; ketone organic solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; and alcohol organic solvents such as methanol, ethanol, isopropanol, and n-butanol. The amount of organic solvent used, relative to the total mass of the raw materials, is typically 50–300% by mass, preferably 100–250% by mass. These organic solvents can be used alone or in combination. The reaction temperature for carrying out the aforementioned reaction is typically 50–150°C, and the reaction time is typically 0.5–10 hours. To prevent the self-polymerization of the vinyl ether groups, the reaction is preferably carried out in an oxygen-rich environment. After the aforementioned reaction is completed, if an organic solvent is used, it is removed under reduced pressure and heating. If a catalyst is used, it is deactivated by an inactivating agent as needed, and then removed by washing or filtration to obtain the compound. The resulting compound, with a terminal hydroxyl group, is then reacted with furan methyl glycidyl ether, etc. Sodium hydroxide, potassium hydroxide, potassium carbonate, etc., can be used as catalysts, and toluene, acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, acetonitrile, dimethylformamide, etc., can be used as solvents. The reaction temperature is room temperature to 200°C, and the reaction time is 1 to 24 hours. The catalyst is then removed by filtration, and extraction and solvent removal are performed to obtain the target compound. The Diels-Adel reaction for this compound is described above. The aforementioned aliphatic hydroxyl compounds are not particularly limited, but examples include: 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol, 1,14-tetradecanediol, 1,15-pentadecanediol, 1... 16-Hexadecanediol, 2-methyl-1,11-undecanediol, 3-methyl-1,11-undecanediol, 2,6,10-trimethyl-1,11-undecanediol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polypentamethylene glycol diglycidyl ether, polyhexamethylene glycol diglycidyl ether, polyheptamethylene glycol diglycidyl ether, etc., can be used alone or in combination of two or more. From the viewpoint of achieving an excellent balance between the resulting hardened material's flexibility and heat resistance, it is preferable to use dihydroxy compounds with a polyether structure or a straight-chain extended alkyl chain having 12 to 14 carbon atoms. The most preferred compounds are polyethylene glycol, polypropylene glycol, polytetramethylene glycol, 1,12-dodecanediol, 1,13-tridecanediol, and 1,14-tetradecanediol. The aforementioned dihaloalkyl compounds are not particularly limited, and examples include: 1,4-dichlorobutane, 1,5-dichloropentane, 1,6-dichlorohexane, 1,7-dichloroheptane, 1,8-dichlorooctane, 1,9-dichlorononane, 1,10-dichlorodecane, 1,11-dichloroundecane, 1,12-dichlorododecane, 1,4-dibromobutane, 1,5-dibromopentane, 1,6-dibromohexane, 1,7-dibromoheptane, 1,8-dibromooctane, 1,9-dibromononane, 1,10-dibromodecane, 1,11-dibromoundecane, 1,12-dibromododecane, etc. They can be used alone or in combination of two or more. The aforementioned dihalogenated aralkyl compounds are not particularly limited, and examples include dichloroxylene, dichloromethylbiphenyl, dibromoxylene, dibromomethylbiphenyl, etc. They can be used alone or in combination of two or more. Regarding the reaction ratio of the aforementioned aromatic dihydroxy compound with the dihalogenated alkyl compound or the dihalogenated aralkyl compound, it is preferable to react the former / the latter in the range of 1 / 1.01 to 1 / 5.0 (molar ratio). From the viewpoint that the resulting cured product has a good balance of flexibility and heat resistance, (a1) / (a2) is preferably 1 / 1.02 to 1 / 3.0 (molar ratio). The reaction of the aforementioned aromatic dihydroxy compounds with dihaloalkyl compounds or dihaloaralkyl compounds is preferably carried out in the presence of a catalyst. Various catalysts can be used as the aforementioned catalyst, including, for example, alkali (earth) metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, and calcium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. Using two or more catalysts is also acceptable. From the viewpoint of rapid reaction and excellent reduction of impurities, sodium hydroxide, potassium hydroxide, and potassium carbonate are preferred. The amount of such catalyst used is not particularly limited, but 0.0001 to 10 mol is preferred relative to 1 mol of the phenolic hydroxyl group of the aforementioned aromatic dihydroxy compound. The form of such catalyst is also not particularly limited; it can be used in aqueous solution or in solid form. Furthermore, the aforementioned reaction of aromatic dihydroxy compounds with dihaloalkyl compounds or dihaloaralkyl compounds can be carried out in the absence of a solvent or in the presence of an organic solvent. Examples of usable organic solvents include toluene, acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, acetonitrile, and dimethylformamide. The amount of organic solvent used, relative to the total mass of the raw materials, is typically 50–300% by mass, preferably 100–1000% by mass. These organic solvents can be used alone or in combination. The reaction temperature for carrying out the aforementioned reaction is typically room temperature to 150°C, and the reaction time is typically 1 to 24 hours. From the viewpoint of reducing impurities in the final product, the reaction temperature is preferably room temperature to 100°C. The resulting compound with a terminal alkyl halide is reacted with furfuryl alcohol, etc. Sodium hydroxide, potassium hydroxide, potassium carbonate, etc., can be used as catalysts, and toluene, acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, acetonitrile, dimethylformamide, etc., can be used as solvents. The reaction temperature is room temperature to 200°C, and the reaction time is 1 to 24 hours. The catalyst is then removed by filtration, and extraction and solvent removal are performed to obtain the target compound. The Diels-Adel reaction for this compound is described above. The intermediate of the conjugated diene prior to the Diels-Adel reaction can be represented by the following general formula (1)'. [In the formula, n and Z] 2 Z 3 Same as above). The present invention relates to compounds containing glycidyl ether groups, which, by combining with a reactive compound (I) containing glycidyl ether groups, can form a curable resin composition. The curable resin composition is ideally suited for various electrical / electronic component applications such as adhesives, coatings, photoresists, printed wiring boards, and semiconductor sealing materials. Examples of compounds (I) that are reactive with the aforementioned compounds containing glycidyl ether groups include, for instance, various known epoxy resin curing agents such as amine compounds, acid anhydrides, amide compounds, compounds containing phenolic hydroxyl groups, carboxylic acid compounds, and thiols. The curing agent can be appropriately selected based on the physical properties of the target cured material; in particular, from the viewpoint of mechanical strength and adhesion to the substrate, compounds containing hydroxyl groups are preferred. Examples of the aforementioned amine compounds include: trimethylenediamine, ethylenediamine, N,N,N',N'-tetramethylethylenediamine, pentamethyldiethylenetriamine, triethylenediamine, dipropylenediamine, N,N,N',N'-tetramethylpropylenediamine, tetramethylenediamine, pentaethylenediamine, hexamethylenediamine, trimethylhexamethylenediamine, N,N,N',N'-tetramethylhexamethylenediamine, N,N-dimethylcyclohexylamine, and diethylenetriamine. Triethylenetetramine, tetraethylenepentamine, dimethylaminopropylamine, diethylaminopropylamine, dibutylaminopropylamine, 1,4-diazabicyclo(2,2,2)octane (triethylenediamine), polyoxyethylenediamine, polyoxypropylenediamine, bis(2-dimethylaminoethyl) ether, dimethylaminoethoxyethoxyethanol, triethanolamine, dimethylaminohexanol, benzylmethylamine, dimethylbenzylamine, m-xylenediamine, α-methylbenzylmethylamine and other aliphatic amine compounds; Piperidine, Piperidine Menthane diamine, isophorone diamine, methyl thioline, ethyl thioline, N,N',N”-tris(dimethylaminopropyl)hexahydro-s-tri 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxyspiro(5,5)undecane adduct, N-aminoethylpiperane Trimethylaminoethylpiperazine bis(4-aminocyclohexyl)methane, N,N'-dimethylpiperane Alicyclic and heterocyclic amine compounds such as 1,8-diazabicyclo-[5.4.0]-undecene (DBU); Aromatic amine compounds such as o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, diaminodiphenylmethane, diaminodiphenylmethane, pyridine, and methylpyridine; Modified amine compounds include epoxy addition polyamines, Mac addition polyamines, Mannich addition polyamines, thiourea addition polyamines, ketone-encapsulated polyamines, dicyandiamine, guanidine, organic acid acehydrazine, diaminocis-butene dinitrile, amino-acetylinide, boron trifluoride-piperidine complex, boron trifluoride-monoethylamine complex, and other modified amine compounds. Examples of the aforementioned acid anhydrides include: phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, maleic anhydride polypropylene glycol, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride, and methylhexahydrophthalic anhydride. Examples of compounds containing phenolic hydroxyl groups include: bis(4-hydroxyphenyl)methane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, and bis(4-hydroxyphenyl) benzoyl ether, as well as phenolic varnish resins, cresol varnish resins, aromatic hydrocarbon formaldehyde resins modified with phenolic resins. Dicyclopentadienol addition-type resin, phenolic alkyl resin (Sylco resin), naphthol alkyl resin, trimethylolmethane resin, tetraphenol ethane resin, naphthol phenolic varnish resin, naphthol-phenol cocondensed phenolic varnish resin, naphthol-cresol cocondensed phenolic varnish resin, biphenyl-modified phenolic resin (a polyphenolic compound with a phenolic core linked by dimethylene groups), biphenyl-modified naphthol resin (a polynatrol compound with a phenolic core linked by dimethylene groups), aminotrimethylol Modified phenolic resins (polyphenolic compounds in which the phenolic core is linked by melamine, benzoguanamine, etc.) or modified phenolic varnish resins containing alkoxy groups (polyphenolic compounds in which the phenolic core and the aromatic ring containing alkoxy groups are linked by formaldehyde) and other polyphenolic compounds. Examples of the aforementioned amide compounds include dicyandiamine or polyamidoamine. Examples of polyamidoamines include those obtained by reacting aliphatic dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, pimelic acid, octanoic acid, and azelaic acid, or carboxylic acid compounds such as fatty acids and dimer acids, with aliphatic polyamines or polyamines having polyoxyalkylene chains. Examples of the aforementioned carboxylic acid compounds include: carboxylic acid-terminated polyesters, polyacrylic acid, maleic acid-modified polypropylene glycol, and other carboxylic acid polymers. As for the aforementioned thiols, those containing two or more thiols in two molecules are preferred. Examples include: 3,3'-dithiodipropionic acid, trimethylolpropane (thioglycolate), neopentyl tert-thioglycolate, ethylene glycol dithioglycolate, 1,4-bis(3-mercaptobutyroxyl)butane, trimethylolpropane ((3-mercaptopropyroxyl)-ethyl)-triisocyanate, trimethylolpropane (3-mercaptopropionate), neopentyl tert-thioglycolate, neopentyl tert-thiobutyrate, dinepentyl tert-thioglycolate, 1,3,4,6-tetra(2-mercaptoethyl)ethynylurea, 4-butanedithiol, 1,6-hexanedithiol, 1,10-decanedithiol, etc. When using these hardeners, only one type of hardener may be used, or two or more may be mixed. Furthermore, in applications such as underfill materials and general coatings, the aforementioned amine compounds, carboxylic acid compounds, and / or anhydride compounds are preferred. Also, in applications such as adhesives or flexible wiring substrates, from the viewpoints of workability, curing properties, and long-term stability, amine compounds, especially dicyandiamine, are preferred. Also, in applications such as semiconductor sealing materials, from the viewpoint of the heat resistance of the cured product, solid-state phenolic compounds are preferred. Also, in battery applications, from the viewpoint of low-temperature curing, aliphatic amines or thiols are preferred. Furthermore, from the viewpoint that the effects of the present invention can be better demonstrated, the aforementioned compound (I) which is reactive with the compound containing glycidyl ether group is preferably a compound containing hydroxyl group with reversible bonds. Examples of hydroxyl-containing compounds with reversible bonds include: structural units A' having one or more hydroxyl groups and structural units B' different from the aforementioned A' linked by A'-B'-A', and the aforementioned structural units A' and B' being bonded by reversible bonds. Examples of reversible bonds mentioned above include those identical to those in compounds containing glycidyl ether groups in this invention. Examples of hydroxyl-containing compounds with reversible bonds, as described above, include those represented by the following formula. Examples of hydroxyl-containing compounds with reversible bonds, as described above, include those represented by the following formulas. Among these, from the viewpoint of the dissociation temperature of the reversible bond, compounds represented by the following formulas (6-1) and (6-2) are preferred. In formula (7), each Ar is an independent structure containing an aromatic ring, either unsubstituted or substituent. The structures derived from anthracene in formulas (5-1) and (5-2), and from furan in formulas (6-1) and (6-2), may also contain halogen atoms, alkoxy groups, arylalkoxy groups, aryloxy groups, nitro groups, amide groups, alkoxycarbonyl groups, aryloxycarbonyl groups, cyano groups, alkyl groups, cycloalkyl groups, aralkyl groups, or aryl groups as substituents. In the formula, ma is an integer from 1 to 10, mb is an integer from 1 to 4, and n is the average of the repetitions, ranging from 0 to 10. Z 5 For the following formula (8), Z 2 For the following formula (9), Z 3 For the following formula (10), Z 4 It can be any of the structures represented by the following formulas (11) and (12), and there can be multiple structures in one molecule, which can be the same or different. [The aromatic ring in formula (8) may be substituted or unsubstituted, and * indicates a bond site. The hydroxyl group on the naphthalene ring in the formula indicates that it can be bonded at any location.] In formula (9), Ar is an independent structure containing an aromatic ring that is either unsubstituted or has substituents, and R 1 R 2 Each is independently a hydrogen atom, methyl, or ethyl; R is a hydrogen atom or methyl; R' is a divalent hydrocarbon group with 2 to 12 carbon atoms; n1 is an integer from 2 to 16; n2 is the average value of the repeating units, which is 2 to 30; k1 is the average number of repeating units, which is in the range of 0.5 to 10; p1 and p2 are independently 0 to 5; X is the structural unit represented by the following formula (9-1); Y is the structural unit represented by the following formula (9-2). In equations (9-1) and (9-2), Ar, R, and R0 are... 1 R 2 [R', n1, n2 are the same as above]. m1 and m2 are the average values ​​of the repetitions, each independently ranging from 0 to 25, and m1 + m2 ≥ 1. However, the bond between structural unit X represented by the aforementioned equation (9-1) and structural unit Y represented by the aforementioned equation (9-2) can be random or block, and the total number of structural units X and Y present in one molecule are m1 and m2, respectively. [In formula (10), n3 and n5 are the average values ​​of the number of repetitions, which are 0.5 to 10 respectively, n4 is an integer from 1 to 16, and R” is a hydrogen atom, methyl or ethyl.] In equations (11) and (12), R 1 R 2 R', n1, and n2 are the same as described above. As a hydroxyl-containing compound with reversible bonds, one can specifically be shown in the following structural formula. [In the formula, R' is a divalent hydrocarbon group with 2 to 12 carbon atoms, n is the average number of repeating units, which is 0 to 10, n1 is an integer from 4 to 16, n2 is the average number of repeating units, which is 2 to 30, and k1 is 0.5 to 5]. Among these hydroxyl-containing compounds, those with reversible furan-maleimide bonds are equivalent to intermediates (precursors) of the aforementioned compounds containing glycidyl ether groups. Compounds with reversible anthracene-maleimide bonds can be obtained by using anthracene compounds instead of furan compounds. The preparation method of compounds having disulfide bonds as the reversible bond represented by the aforementioned general formula (7) is not particularly limited. The following are examples of compounds that can be used as raw materials for the aforementioned compounds containing disulfide bonds. Compounds containing disulfide bonds can be obtained using well-known methods. For example, compounds with thiol groups can be oxidatively bonded. Iodine or hydrogen peroxide is commonly used as the oxidizing agent. Alternatively, they can be obtained by heating and melting or dissolving in a solvent, stirring at room temperature to 200°C for 1 to 24 hours, and then directly filtering and distilling off the solvent without purification. Alternatively, they can be obtained by commonly used single-isolation purification methods such as recrystallization, reprecipitation, and chromatography. Furthermore, in the curable resin composition of the present invention, other epoxy resins besides the epoxypropyl ether group of the present invention may be used without impairing the effects of the present invention. Other epoxy resins mentioned above include, for example: bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD ​​type epoxy resin, polyhydroxybenzene type epoxy resin, polyhydroxynaphthalene type epoxy resin, biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, etc. (liquid epoxy resins); brominated epoxy resins such as brominated phenolic varnish type epoxy resin; solid bisphenol A type epoxy resin, phenolic varnish type epoxy resin, cresolic phenolic varnish type epoxy resin, triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin, and dicyclopentadiene type epoxy resin. Epoxy resins such as pentadiene-phenol addition reaction type, phenolic alkyl type, phenylene ether type, naphthylene ether type, naphthol phenolic varnish type, naphthol alkyl type, naphthol-phenol cocondensed phenolic varnish type, naphthol-cresol cocondensed phenolic varnish type, aromatic hydrocarbon formaldehyde resin modified phenolic resin type, and biphenyl modified phenolic varnish type can be used alone or in combination of two or more types. It is preferable to make various selections according to the target application and the physical properties of the cured material. Among these, from the viewpoint of achieving a good balance between curability and the crosslinking density of the resulting cured product, it is preferable to use an epoxy resin with an epoxy equivalent of 100 to 10,000 g / eq, and even more preferably to use an epoxy resin expressed by the following formula (13) with an epoxy equivalent of 500 to 10,000 g / eq. In formula (13), Ar is an independent structure containing an aromatic ring that is either unsubstituted or has substituents, X' is a structural unit represented by formula (13-1), and Y' is a structural unit represented by formula (13-2). In equations (13-1) and (13-2), Ar is the same as described above, and R... 1 R 2 Each is independently a hydrogen atom, methyl or ethyl, and R' is a divalent hydrocarbon group with 2 to 12 carbon atoms. 3 R 4 R 7 R 8 Each is independently a hydroxyl, glycidyl ether, or 2-methylglycidyl ether group, R 5 R 6 R 9 R 10 Each is independently a hydrogen atom or a methyl group, n 1 is an integer from 4 to 16, n The average value of the repeating units in series 2 is 2–30. 11 R 12 Each is independently an epoxypropyl ether group or a 2-methyl epoxypropyl ether group, R 13 R 14 Each is independently a hydroxyl, glycidyl ether, or 2-methylglycidyl ether group, R 15 R 16 For each hydrogen atom or methyl group, m3, m4, p1, p2, and q are the average values ​​of the repetition counts. m3 and m4 are each independently 0–25, and m3+m4≥1. p1 and p2 are each independently 0–5, and q is 0.5–5. However, the bond between the structural unit X' represented by the aforementioned formula (13-1) and the structural unit Y' represented by the aforementioned formula (13-2) can be random or block. The total number of each structural unit X and Y present in one molecule is m3 and m4, respectively. The epoxy resin represented by the aforementioned general formula (13) can be combined alone to form a curable resin composition. From the viewpoint of further imparting flexibility to the cured material and being able to easily exhibit disintegration, it is also preferable to further use an epoxy resin with an epoxy equivalent of 100 to 300 g / eq. As for the aforementioned epoxy resins that can be used together, their epoxy equivalent can be in the range of 100-300 g / eq, and their structure is not limited. Examples include: bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD ​​type epoxy resin, polyhydroxybenzene type epoxy resin, polyhydroxynaphthalene type epoxy resin, biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, etc. (liquid epoxy resins); brominated epoxy resins such as brominated phenolic varnish type epoxy resin; solid bisphenol A type epoxy resin, phenolic varnish type epoxy resin, cresolic phenolic varnish type epoxy resin, triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin, dicyclopentadiene- Phenolic addition reaction epoxy resins, phenolic alkyl epoxy resins, phenylene ether epoxy resins, naphthylene ether epoxy resins, naphthol phenolic varnish epoxy resins, naphthol alkyl alkyl epoxy resins, naphthol-phenol cocondensed phenolic varnish epoxy resins, naphthol-cresol cocondensed phenolic varnish epoxy resins, aromatic hydrocarbon formaldehyde resin modified phenolic resin epoxy resins, biphenyl modified phenolic varnish epoxy resins, etc., can be used alone or in combination of two or more types. It is preferable to make various selections according to the target application and the physical properties of the cured material. Among these, it is preferable to use epoxy resins with an epoxy equivalent of 100 to 300 g / eq, such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD ​​type epoxy resin, polyhydroxybenzene type epoxy resin, polyhydroxynaphthalene type epoxy resin, biphenyl type epoxy resin, and tetramethylbiphenyl type epoxy resin. It is particularly preferable to use epoxy resins with an epoxy equivalent of 100 to 300 g / eq, such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and bisphenol AD ​​type epoxy resin. The ratio of the epoxy resin represented by the aforementioned general formula (13) to the epoxy resin with an epoxy equivalent of 100 to 300 g / eq is not particularly limited. From the viewpoint of easy phase separation in the cured material, the mass ratio of the former to the latter is 97:3 to 3:97, preferably 10:90 to 90:10, and particularly preferably 80:20 to 20:80. By achieving phase separation in the cured material to form an island structure, it combines the adhesion and stress relief capabilities of the cured material, exhibits high adhesion in a wide temperature range, and has the effect of reducing the molding shrinkage rate of the resin composition before and after heat curing. The concentration of reversible bonds in the curable resin composition of the present invention is preferably 0.10 mmol / g or more relative to the total mass of the curing components in the curable resin composition. According to this configuration, the disintegration / repairability and reshaping properties of the cured product obtained from the curable resin composition are improved. The concentration of the aforementioned reversible bonds is more preferably 0.10 to 3.00 mmol / g, and even more preferably 0.15 to 2.00 mmol / g. Furthermore, in cases where the compound containing glycidyl ether groups of the present invention has multiple reversible bonds, or when the aforementioned hydroxyl-containing compound with reversible bonds is used alone as a curing agent or in combination with other curing agents, the total concentration of the reversible bonds is preferably 0.10 mmol / g or more relative to the total mass of the curing components in the curable resin composition, more preferably 0.10 to 3.00 mmol / g, and even more preferably 0.15 to 2.00 mmol / g. Furthermore, the concentration of reversible bonds can be appropriately selected based on factors such as the glass transition temperature of the target cured material as defined by the tanδ peak of a dynamic viscoelasticity analyzer (DMA). For example, using the glass transition temperature as a standard, if the glass transition temperature of the cured material is near room temperature, it easily exhibits sufficient repair and reforming properties even at lower concentrations within the preferred range. On the other hand, if the glass transition temperature of the target cured material exceeds 100°C as a standard, it easily exhibits properties at higher concentrations within the preferred range. However, in temperature regions exceeding the glass transition temperature determined by DMA, molecular mobility is generally high, and even at low concentrations of compounds containing glycidyl ether groups, sufficient repair and reforming properties are easily exhibited. Therefore, for example, the effect of repair and reforming properties can be adjusted by appropriately adjusting the aging temperature for repair or the heating temperature for reforming. Thus, the relationship between the glass transition temperature of the cured material and the concentration of reversible bonds is not limited to this. In the curable resin composition of the present invention, the ratio of the total amount of glycidyl ether groups to the total amount of active groups that can react with the glycidyl ether groups is not particularly limited. From the viewpoint of good mechanical properties of the resulting cured product, it is preferable that the amount of active groups that can react with the glycidyl ether groups is 0.4 to 1.5 equivalents relative to 1 equivalent of the total amount of glycidyl ether groups in the resin composition. Furthermore, the curing resin composition may also contain a curing accelerator. Various types of curing accelerators can be used, including, for example, urea compounds, phosphorus compounds, tertiary amines, imidazoles, imidazolines, organic acid metal salts, Lewis acids, and amine salts. When used as an adhesive, urea compounds, especially 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU), are preferred from the viewpoints of excellent workability and low-temperature curing properties. When used as a semiconductor sealing material, triphenylphosphine is preferred among phosphorus compounds, and 1,8-diazabicyclo-[5.4.0]-undecene is preferred among tertiary amines, considering its excellent curing properties, heat resistance, electrical properties, and moisture resistance reliability. Examples of the aforementioned phosphorus compounds include: alkylphosphines such as ethylphosphine and butylphosphine, primary phosphines such as phenylphosphine; dialkylphosphines such as dimethylphosphine and dipropylphosphine; secondary phosphines such as diphenylphosphine and methylethylphosphine; and tertiary phosphines such as trimethylphosphine, triethylphosphine, and triphenylphosphine. Examples of imidazoles mentioned above include: imidazole, 1-methylimidazolium, 2-methylimidazolium, 3-methylimidazolium, 4-methylimidazolium, 5-methylimidazolium, 1-ethylimidazolium, 2-ethylimidazolium, 3-ethylimidazolium, 4-ethylimidazolium, 5-ethylimidazolium, 1-n-propylimidazolium, 2-n-propylimidazolium, 1-isopropylimidazolium, 2-isopropylimidazolium, 1-n-butylimidazolium, 2-n-butylimidazolium, 1-isobutylimidazolium, 2-isobutylimidazolium, 2-undecyl-1H-imidazolium, 2-heptadecanyl-1H-imidazolium, 1,2-dimethylimidazolium, 1,3-dimethylimidazolium, 2,4-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 1-phenylimidazolium, 2-phenyl-1H-imidazolium, 4-methyl-2- Phenyl-1H-imidazolium, 2-phenyl-4-methylimidazolium, 1-benzyl-2-methylimidazolium, 1-benzyl-2-phenylimidazolium, 1-cyanoethyl-2-methylimidazolium, 1-cyanoethyl-2-ethyl-4-methylimidazolium, 1-cyanoethyl-2-undecylimidazolium, 1-cyanoethyl-2-phenylimidazolium, 2-phenylimidazolium isocyanurate adduct, 2-methylimidazolium isocyanurate adduct, 2-phenyl-4,5-dihydroxymethylimidazolium, 2-phenyl-4-methyl-5-hydroxymethylimidazolium, 1-cyanoethyl-2-phenyl-4,5-di(2-cyanoethoxy)methylimidazolium, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 1-benzyl-2-phenylimidazolium hydrochloride, etc. Examples of the aforementioned imidazoline compounds include 2-methylimidazoline and 2-phenylimidazoline. Examples of the aforementioned urea compounds include, for example, p-chlorophenyl-N,N-dimethylurea, 3-phenyl-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-N,N-dimethylurea, and N-(3-chloro-4-methylphenyl)-N',N'-dimethylurea. Furthermore, the curable resin composition of the present invention may also be used in combination with other thermosetting resins or thermoplastic resins, to the extent that it does not impair the effects of the present invention. Other thermosetting resins include, for example, cyanate ester resins, and resins containing benzo[a]... Resins with specific structures, reactive ester resins, vinyl benzyl compounds, acrylic compounds, copolymers of styrene and maleic anhydride, etc. When using other thermosetting resins as described above, the amount used is not particularly limited as long as it does not hinder the effect of the present invention; preferably, it is in the range of 1 to 50 parts by weight in 100 parts by weight of the thermosetting resin composition. Examples of cyanate ester resins mentioned above include: bisphenol A type cyanate ester resin, bisphenol F type cyanate ester resin, bisphenol E type cyanate ester resin, bisphenol S type cyanate ester resin, bisphenol sulfide type cyanate ester resin, phenylene ether type cyanate ester resin, naphthalene ether type cyanate ester resin, biphenyl type cyanate ester resin, tetramethylbiphenyl type cyanate ester resin, polyhydroxynaphthalene type cyanate ester resin, phenol phenolic varnish type cyanate ester resin, cresol phenolic varnish type cyanate ester resin, triphenylmethane type cyanate ester resin, tetraphenylethane type cyanate ester resin, dicyclopentadiene-phenol addition reaction type cyanate ester resin, phenol aralkyl type cyanate ester resin, naphthol phenolic varnish type cyanate ester resin, naphthol aralkyl type cyanate ester resin, naphthol-phenol cocondensed phenolic varnish type cyanate ester resin, naphthol-cresol cocondensed phenolic varnish type cyanate ester resin, aromatic hydrocarbon formaldehyde resin modified phenol resin type cyanate ester resin, biphenyl modified phenolic varnish type cyanate ester resin, anthracene type cyanate ester resin, etc. These can be used individually or in combination of two or more. Among these cyanate resins, especially from the viewpoint of obtaining a cured product with excellent heat resistance, bisphenol A type cyanate resin, bisphenol F type cyanate resin, bisphenol E type cyanate resin, polyhydroxynaphthalene type cyanate resin, naphthyl ether type cyanate resin, and phenolic varnish type cyanate resin are preferred. From the viewpoint of obtaining a cured product with excellent dielectric properties, dicyclopentadiene-phenol addition reaction type cyanate resin is preferred. As a product with benzo[a] The resin structure is not particularly limited; examples include the reaction product of bisphenol F with formalin and aniline (Fa-type benzo[a]). Resin), the reaction product of diaminodiphenylmethane with formalin and phenol (Pd-type benzo[a]) Resins), reaction products of bisphenol A with formalin and aniline, reaction products of dihydroxydiphenyl ether with formalin and aniline, reaction products of diaminodiphenyl ether with formalin and phenol, reaction products of dicyclopentadiene-phenol addition-cure resin with formalin and aniline, reaction products of phenolphthalein with formalin and aniline, reaction products of diphenyl sulfide with formalin and aniline, etc. These can be used individually or in combination of two or more. There are no particular limitations on the aforementioned reactive ester resins. Generally, compounds with two or more highly reactive ester groups per molecule, such as phenolic esters, thiophenolic esters, N-hydroxyamine esters, and heterocyclic hydroxyl compounds, are preferred. The aforementioned reactive ester resins are preferably obtained through the condensation reaction of carboxylic acid compounds and / or thiocarboxylic acid compounds with hydroxyl compounds and / or thiols. Especially from the viewpoint of improving heat resistance, reactive ester resins obtained from carboxylic acid compounds or their halides with hydroxyl compounds are preferred, and reactive ester resins obtained from carboxylic acid compounds or their halides with phenolic compounds and / or naphthol compounds are even more preferred. Examples of carboxylic acid compounds include, for example, benzoic acid, acetic acid, succinic acid, maleic acid, itconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, etc., or their halides. Examples of phenolic or naphthol compounds include: hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, dihydroxydiphenyl ether, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthol, 1,6-dihydroxynaphthol, 2,6-dihydroxynaphthol, dihydroxydiphenyl ketone, trihydroxydiphenyl ketone, tetrahydroxydiphenyl ketone, phloroglucin, benzenetriol, and dicyclopentadiene-phenol addition resins. Specifically, the active ester resins are preferably: active ester resins containing a dicyclopentadiene-phenol addition structure, active ester resins containing a naphthalene structure, active ester resins that are acetylated derivatives of phenolic varnishes, and active ester resins that are benzoyl derivatives of phenolic varnishes. From the viewpoint of effectively improving peel strength, active ester resins containing a dicyclopentadiene-phenol addition structure and active ester resins containing a naphthalene structure are more preferred. Furthermore, it can also be used in combination with various phenolic varnish resins, addition polymerization resins of alicyclic dienes such as dicyclopentadiene and phenolic compounds, modified phenolic varnish resins containing phenolic hydroxyl groups and aromatic compounds containing alkoxy groups, phenolic alkyl resins (Sylco resins), naphthol alkyl resins, trimethylolmethane resins, tetraphenol ethane resins, biphenyl-modified phenolic resins, biphenyl-modified naphthol resins, and aminotrimethylolmethane resins. Modified phenolic resins and various vinyl polymers. More specifically, the aforementioned phenolic varnish resins can be categorized as polymers obtained by reacting compounds containing phenolic hydroxyl groups, such as phenol, phenylphenol, resorcinol, biphenyl, bisphenol A or bisphenol F, naphthol, and dihydroxynaphthalene, with aldehyde compounds under acidic catalytic conditions. Examples of the aforementioned vinyl polymers include: homopolymers or copolymers of vinyl compounds such as polyhydroxystyrene, polystyrene, polyvinylnaphthalene, polyvinylanthracene, polyvinylcarbazole, polyindene, polyacenaphthene, polynorcampene, polycyclodecene, polytetracyclododecene, polynortricyclene, and poly(meth)acrylate. The so-called thermoplastic resin refers to resin that can be melted and molded by heating. Specific examples include: polyethylene resin, polypropylene resin, polystyrene resin, rubber-modified polystyrene resin, acrylonitrile-butadiene-styrene (ABS) resin, acrylonitrile-styrene (AS) resin, polymethyl methacrylate resin, acrylic resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyethylene terephthalate resin, ethylene vinyl alcohol resin, cellulose acetate resin, ionomer resin, polyacrylonitrile resin, polyamide resin, polyacetal resin, polybutylene terephthalate resin, polylactic acid resin, polyphenylene ether resin, modified polyphenylene ether resin, polycarbonate resin, polyurethane resin, polyphenylene sulfide resin, polyetherimide resin, polyetherurethane resin, polyaryl ester resin, thermoplastic polyimide resin, polyamideimide resin, polyetheretherketone resin, polyketone resin, liquid crystal polyester resin, fluoropolymer resin, syndiotactic polystyrene resin, cyclic polyolefin resin, etc. One or more of these thermoplastic resins may be used. When using other resins, the blending ratio of the compound containing glycidyl ether groups of the present invention with other resins can be arbitrarily set according to the application. From the viewpoint of not hindering the restorative and reshaping properties of the present invention, it is preferable that the ratio of other resins is 0.5 to 100 parts by mass relative to 100 parts by mass of the compound containing glycidyl ether groups of the present invention. Furthermore, in applications where high flame retardancy is required for the curable resin composition of the present invention, a non-halogenated flame retardant that does not substantially contain halogen atoms may also be incorporated. Examples of non-halogenated flame retardants include: phosphorus-based flame retardants, nitrogen-based flame retardants, polysiloxane-based flame retardants, inorganic flame retardants, and organometallic salt-based flame retardants. There are no restrictions on their use; they can be used alone, multiple flame retardants of the same type can be used together, or flame retardants of different types can be used in combination. The aforementioned phosphorus-based flame retardants can be either inorganic or organic. Examples of inorganic compounds include: red phosphorus, monoammonium phosphate, diammonium phosphate, triammonium phosphate, ammonium polyphosphate, and other ammonium phosphates, as well as nitrogen- and phosphorus-containing inorganic compounds such as amide phosphate. Furthermore, for the purpose of preventing hydrolysis, it is preferable to perform surface treatment on the aforementioned red phosphorus. Examples of surface treatment methods include: (i) coating treatment with inorganic compounds such as magnesium hydroxide, aluminum hydroxide, zinc hydroxide, titanium hydroxide, bismuth oxide, bismuth hydroxide, bismuth nitrate, or mixtures thereof; (ii) coating treatment with a mixture of inorganic compounds such as magnesium hydroxide, aluminum hydroxide, zinc hydroxide, and titanium hydroxide and thermosetting resins such as phenolic resin; and (iii) double coating treatment with thermosetting resins such as phenolic resin on a film of inorganic compounds such as magnesium hydroxide, aluminum hydroxide, zinc hydroxide, and titanium hydroxide. The aforementioned organophosphorus compounds, for example, in addition to general organophosphorus compounds such as phosphate esters, phosphonites, phosphonic acids, phosphine oxides, phosphine compounds, and organic nitrogen- and phosphorus-containing compounds, include: cyclic organophosphorus compounds such as 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, and 10-(2,7-dihydroxynaphthyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, as well as derivatives formed by reacting them with compounds such as epoxy resins or phenolic resins. The amount of such phosphorus-based flame retardant can be appropriately selected according to the type of phosphorus-based flame retardant, other components of the resin composition, and the expected degree of flame retardancy. For example, in 100 parts by weight of a resin composition containing all components such as non-halogenated flame retardants, fillers, and additives, when red phosphorus is used as a non-halogenated flame retardant, it is preferably blended in the range of 0.1 parts by weight to 2.0 parts by weight. When organophosphorus compounds are used, it is also preferably blended in the range of 0.1 parts by weight to 10.0 parts by weight, and more preferably blended in the range of 0.5 parts by weight to 6.0 parts by weight. Furthermore, when using the aforementioned phosphorus-based flame retardants, hydrotalcite, magnesium hydroxide, boron compounds, zirconium oxide, black dyes, calcium carbonate, zeolite, zinc molybdate, activated carbon, etc., can also be added to the phosphorus-based flame retardant. Examples of the aforementioned nitrogen-based flame retardants include: three Compounds, cyanuric acid compounds, isocyanuric acid compounds, phenoxythiazolinone Etc., preferably three Compounds, cyanuric acid compounds, isocyanuric acid compounds. The aforementioned three Compounds, for example, besides melamine, acetoguanamine, benzoguanamine, melamine, melam, succinoguanamine, ethylenedimelamine, melamine polyphosphate, triguanamine, etc., can be listed as: (1) formamidinyl melamine sulfate, melam sulfate, melam sulfate, etc., amyl sulfate triguanamine sulfate, etc. Compounds, (2) co-condensates of phenols such as phenol, cresol, xylenol, butylphenol, and nonylphenol with melamines such as melamine, benzoguanamine, ethylguanamine, and formguanamine, and formaldehyde, (3) mixtures of the co-condensates of (2) and phenol-formaldehyde condensates, and (4) compounds further modified by tung oil, isomerized linseed oil, etc., of the above (2) and (3). Examples of the aforementioned cyanuric acid compounds include cyanuric acid, melamine cyanurate, etc. The amount of nitrogen-based flame retardant added can be appropriately selected according to the type of nitrogen-based flame retardant, other components of the resin composition, and the expected degree of flame retardancy. For example, in 100 parts by weight of a resin composition containing non-halogenated flame retardants and other fillers, additives, etc., it is preferable to add 0.05 to 10 parts by weight, and more preferably to add 0.1 to 5 parts by weight. Furthermore, when using the aforementioned nitrogen-based flame retardants, metal hydroxides, molybdenum compounds, etc., may also be used in combination. The aforementioned polysiloxane flame retardants are not particularly limited in their use as long as they are organic compounds containing silicon atoms; examples include polysiloxane oils, polysiloxane rubbers, and polysiloxane resins. The amount of the aforementioned polysiloxane flame retardant can be appropriately selected based on the type of polysiloxane flame retardant, other components of the resin composition, and the desired degree of flame retardancy. For example, in 100 parts by weight of a resin composition containing non-halogenated flame retardants and other fillers, additives, etc., it is preferable to use 0.05 to 20 parts by weight. Furthermore, when using the aforementioned polysiloxane flame retardants, molybdenum compounds, alumina, etc., can also be used in combination. Examples of inorganic flame retardants include: metal hydroxides, metal oxides, metal carbonate compounds, metal powders, boron compounds, and low-melting-point glasses. Examples of the aforementioned metal hydroxides include: aluminum hydroxide, magnesium hydroxide, dolomite, hydrotalcite, calcium hydroxide, barium hydroxide, zirconium hydroxide, etc. Examples of the aforementioned metal oxides include: zinc molybdate, molybdenum trioxide, zinc stannate, tin oxide, aluminum oxide, iron oxide, titanium oxide, manganese oxide, zirconium oxide, zinc oxide, molybdenum oxide, cobalt oxide, bismuth oxide, chromium oxide, nickel oxide, copper oxide, and tungsten oxide. Examples of the aforementioned metal carbonate compounds include: zinc carbonate, magnesium carbonate, calcium carbonate, barium carbonate, basic magnesium carbonate, aluminum carbonate, iron carbonate, cobalt carbonate, and titanium carbonate. Examples of the aforementioned metal powders include: aluminum, iron, titanium, manganese, zinc, molybdenum, cobalt, bismuth, chromium, nickel, copper, tungsten, and tin. Examples of the aforementioned boron compounds include zinc borate, zinc metaborate, barium metaborate, boric acid, and borax. Examples of low-melting-point glasses mentioned above include: Cepree (Bokusui-Brown), and hydrated SiO₂ glass. 2-MgO-H 2O, PbO-B 2O 3-series, ZnO-P 2O 5-MgO series, P 2O 5-B 2O 3-PbO-MgO series, P-Sn-OF series, PbO-V 2O 5-TeO 2 series, Al 2O 3-H Glassy compounds such as 2O series and lead borosilicate series. The amount of the aforementioned inorganic flame retardant can be appropriately selected based on the type of inorganic flame retardant, other components of the resin composition, and the expected degree of flame retardancy. For example, in 100 parts by weight of a resin composition containing non-halogenated flame retardants and other fillers, additives, etc., it is preferable to blend in the range of 0.05 parts by weight to 20 parts by weight, and more preferably in the range of 0.5 parts by weight to 15 parts by weight. Examples of organometallic salt flame retardants include: ferrocene, acetoacetone metal complexes, organometallic carbonyl compounds, organocobalt salts, organosulfonic acid metal salts, and compounds formed by ionic or coordinate bonding of metal atoms with aromatic or heterocyclic compounds. The amount of the aforementioned organometallic salt flame retardant can be appropriately selected according to the type of organometallic salt flame retardant, other components of the resin composition, and the expected degree of flame retardancy. For example, in 100 parts by weight of a resin composition containing non-halogenated flame retardants and other fillers, additives, etc., it is preferable to blend it in the range of 0.005 parts by weight to 10 parts by weight. The curable resin composition of the present invention may also contain fillers. Examples of fillers include inorganic fillers and organic fillers. Examples of inorganic fillers include inorganic microparticles. As inorganic microparticles, those with excellent heat resistance include alumina, magnesium oxide, titanium oxide, zirconium oxide, and silicon dioxide (quartz, fumed silicon dioxide, settled silicon dioxide, silicic anhydride, fused silicon dioxide, crystalline silicon dioxide, ultrafine amorphous silicon dioxide, etc.); those with excellent thermal conductivity include boron nitride, aluminum nitride, alumina, titanium oxide, magnesium oxide, zinc oxide, silicon oxide, and diamond; those with excellent electrical conductivity include metal fillers and / or metal-coated fillers using elemental metals or alloys (e.g., iron, copper, magnesium, aluminum, gold, silver, platinum, zinc, manganese, stainless steel, etc.); and those with excellent barrier properties include minerals such as mica, clay, kaolin, talc, zeolite, silash, and chlorite, or potassium titanate and sulfuric acid. Magnesium, sepiolite, calcareous silica, aluminum borate, calcium carbonate, titanium dioxide, barium sulfate, zinc oxide, and magnesium hydroxide; those with high refractive index include barium titanate, zirconium oxide, and titanium dioxide; those exhibiting photocatalytic properties include photocatalytic metals such as titanium, cerium, zinc, copper, aluminum, tin, indium, phosphorus, carbon, sulfur, ruthenium, nickel, iron, cobalt, silver, molybdenum, strontium, chromium, barium, and lead, as well as compounds and oxides of the aforementioned metals; those with excellent wear resistance include metals such as silicon dioxide, aluminum oxide, zirconium oxide, and magnesium oxide, as well as compounds and oxides of these metals; those with excellent electrical conductivity include metals such as silver and copper, tin oxide, and indium oxide; those with excellent insulation properties include silicon dioxide; and those with excellent ultraviolet shielding properties include titanium dioxide and zinc oxide. These inorganic microparticles can be selected appropriately according to the application and can be used alone or in combination without problem. Furthermore, in addition to the properties listed above, the aforementioned inorganic microparticles possess various other properties, so they can be selected appropriately according to their intended use. For example, when using silicon dioxide as an inorganic microparticle, there are no particular limitations; known silicon dioxide microparticles such as powdered silicon dioxide or colloidal silicon dioxide can be used. Examples of commercially available powdered silicon dioxide microparticles include: AEROSIL 50 and 200 manufactured by Nippon Aerosil Co., Ltd.; SHIELDEX H31, H32, H51, H52, H121, and H122 manufactured by Asahi Glass Co., Ltd.; E220A and E220 manufactured by Nihon Silica Kogyo Co., Ltd.; SYLYSIA 470 manufactured by FUJI SILYSIA Co., Ltd.; and SG FLAKE manufactured by Nippon Sheet Glass Co., Ltd. Furthermore, commercially available colloidal silica products include, for example, methanol silica sol manufactured by Nissan Chemical Industries, Ltd., IPA-ST, MEK-ST, NBA-ST, XBA-ST, DMAC-ST, ST-UP, ST-OUP, ST-20, ST-40, ST-C, ST-N, ST-O, ST-50, ST-OL, etc. Surface-modified silica microparticles can also be used. Examples include those obtained by surface treatment of the aforementioned silica microparticles with a reactive silane coupling agent having a hydrophobic group, and those obtained by modifying the aforementioned silica microparticles with a compound having a (meth)acrylic group. Examples of commercially available powdered silica modified with a compound having a (meth)acrylic group include AEROSILRM50 and R711 manufactured by Nippon Aerosil Co., Ltd. Examples of commercially available colloidal silica modified with a compound having a (meth)acrylic group include MIBK-SD manufactured by Nissan Chemical Industries, Ltd. The shape of the aforementioned silicon dioxide microparticles is not particularly limited; they can be spherical, hollow, porous, rod-shaped, plate-shaped, fibrous, or irregular in shape. Furthermore, the primary particle size is preferably in the range of 5–200 nm. As titanium dioxide microparticles, they can be used not only as extender pigments but also as UV-responsive photocatalysts, such as anatase, rutile, and brookite titanium dioxide. Furthermore, particles designed to respond to visible light can be used by doping the crystalline structure of titanium dioxide with different elements. Ideally, anionic elements such as nitrogen, sulfur, carbon, fluorine, and phosphorus, or cationic elements such as chromium, iron, cobalt, and manganese can be used as dopants in titanium dioxide. In terms of form, they can be powders, gels, or slurries dispersed in organic solvents or water. Commercially available powdered titanium dioxide microparticles include, for example, AEROSIL P-25 manufactured by Nippon Aerosil Co., Ltd., and ATM-100 manufactured by TAYCA Co., Ltd. Commercially available slurry-like titanium dioxide microparticles include, for example, TKD-701 manufactured by TAYCA Co., Ltd. The curable resin composition of the present invention may further contain a fibrous matrix. The aforementioned fibrous matrix is ​​not particularly limited, but is preferably used in fiber-reinforced resins, and can include inorganic fibers or organic fibers. In addition to inorganic fibers such as carbon fiber, glass fiber, boron fiber, alumina fiber, and silicon carbide fiber, other inorganic fibers include: carbon fiber, activated carbon fiber, graphite fiber, tungsten carbide fiber, silicon carbide fiber, ceramic fiber, natural fiber, mineral fibers such as basalt, boron nitride fiber, boron carbide fiber, and metal fiber. Examples of metal fibers include: aluminum fiber, copper fiber, brass fiber, stainless steel fiber, and steel fiber. Examples of organic fibers include: synthetic fibers made of resins such as polyindole (polybenzazole), polyarylamide, PBO (poly(p-phenylenebenzoazole)), polyphenylene sulfide, polyester, acrylic acid, polyamide, polyolefin, polyvinyl alcohol, and polyarylate; and regenerated fibers such as cellulose, pulp, cotton, wool, silk, protein, polypeptide, and alginic acid. Among them, carbon fiber and glass fiber are preferred due to their wide range of industrial applications. One type may be used alone, or multiple types may be used simultaneously. The aforementioned fibrous matrix can be an aggregate of fibers, which can be continuous or discontinuous, woven or non-woven. It can also be a fiber bundle formed by arranging fibers neatly in one direction, or a sheet formed by arranging fiber bundles. Furthermore, it can also be a three-dimensional shape formed by giving the aggregate of fibers thickness. In the curable resin composition of the present invention, a dispersion medium may also be used to adjust the amount of solids and viscosity of the resin composition. As a dispersion medium, any liquid medium that does not impair the effects of the present invention is acceptable; various organic solvents, liquid organic polymers, etc., are examples. Examples of organic solvents mentioned above include ketones such as acetone, methyl ethyl ketone (MEK), and methyl isobutyl ketone (MIBK); cyclic ethers such as tetrahydrofuran (THF) and dioxolane; esters such as methyl acetate, ethyl acetate, and butyl acetate; aromatics such as toluene and xylene; and alcohols such as carbitol, celusol, methanol, isopropanol, butanol, and propylene glycol monomethyl ether. These solvents can be used alone or in combination. Among them, methyl ethyl ketone is preferred in terms of volatility and solvent recovery during coating. The aforementioned liquid organic polymers are liquid organic polymers that do not directly contribute to the curing reaction. Examples include: acrylic polymers (FLOREN WK-20: Kyoeisha), amine salts of specially modified phosphate esters (HIPLAAD ED-251: Kusumoto Kasei), and modified acrylic block copolymers (DISPERBYK2000; BYK), etc. The resin composition of the present invention may contain other admixtures. Examples include: catalysts, polymerization initiators, inorganic pigments, organic pigments, extender pigments, clay minerals, waxes, surfactants, stabilizers, flow modifiers, coupling agents, dyes, leveling agents, rheology control agents, ultraviolet absorbers, antioxidants, flame retardants, plasticizers, reactive diluents, etc. By curing the resin composition of the present invention, a cured product can be obtained. Curing can be carried out at room temperature or by heating. When heat curing is performed, curing can be done in a single heating step, or through multiple heating steps. Furthermore, the curable resin composition of the present invention can also be cured using an active energy beam. In this case, a photocationic polymerization initiator can be used as the polymerization initiator. As the active energy beam, visible light, ultraviolet light, X-rays, electron beams, etc., can be used. Examples of photocationic polymerization initiators include aryl-strontium salts and aryl-iodonium salts, specifically arylstrontium hexafluorophosphate, arylstrontium hexafluoroantimonate, arylstrontium tetra(pentafluoro)borate, and tri(alkylphenyl)strontium hexafluorophosphate. Photocationic polymerization initiators can be used alone or in combination of two or more. The curable resin composition of the present invention can be prepared simply by uniformly mixing the aforementioned components, and the method is not particularly limited. For example, it can be prepared by uniformly mixing using a pot mill, ball mill, bead mill, roller mill, homogenizer, ultramill, homogenizer, universal mixer, Bamboo mixer, kneading machine, etc. The curable resin composition of the present invention is prepared by dissolving the aforementioned compound containing glycidyl ether groups and the aforementioned compound (I) which is reactive with the compound containing glycidyl ether groups, and further, as needed, the aforementioned compatible curing agent, filler, fibrous matrix, dispersion medium, and resin other than the aforementioned compounds, in the aforementioned organic solvent or other dispersion medium. After dissolution, the solvent is distilled off, and the mixture is dried under reduced pressure using a vacuum oven or similar method to obtain the curable resin composition. Furthermore, the curable resin composition of the present invention can also be a uniform mixture of the aforementioned constituent materials. In this case, uniform mixing using a mixer or similar device is preferred. The mixing ratio of each constituent material can be appropriately prepared according to the desired mechanical strength, heat resistance, repairability, and reformability of the cured product. Moreover, the specific mixing order of the constituent materials is not particularly limited in the preparation of the curable resin composition. The cured product of the present invention is formed by curing the aforementioned compound (I), which is reactive with the aforementioned compound containing glycidyl ether groups, using the compound of the present invention containing glycidyl ether groups. The curing method can be appropriately selected from known methods according to the properties of the aforementioned compound (I), which is reactive with the compound containing glycidyl ether groups. The cured product of the present invention, as described above, exhibits a moderate crosslinking density because it is cured by a compound containing glycidyl ether groups, thereby maintaining good mechanical strength. Furthermore, when mechanical energy such as scratches or external forces are applied to the cured product of the present invention, although the reversible bonds are broken, the equilibrium system shifts towards the bond direction, thus it is believed that adducts will re-form, allowing for scratch repair and reshaping. The structure of the obtained hardened material can be confirmed by infrared absorption (IR) spectroscopy using Fourier transform infrared spectroscopy (FT-IR), elemental analysis, X-ray scattering, etc. As described above, the cured product of one embodiment of the present invention can be obtained by using the compound containing glycidyl ether group of the present invention as a component of a curable resin composition. Alternatively, the aforementioned conjugated diene intermediate, which is an intermediate of the compound containing glycidyl ether group, can be used, along with a compound that can undergo an addition reaction with it via the Diels-Adel reaction. During the curing process, the compound containing glycidyl ether group is formed (in situ synthesis) and becomes a cured product. For example, when a compound represented by the aforementioned formula (1)', a maleimide having an epoxypropyl ether group, and the aforementioned compound (I) which is reactive with the compound containing the epoxypropyl ether group are used as necessary raw materials and a curing reaction is carried out, the compound containing the epoxypropyl ether group represented by the aforementioned formula (1) can be obtained during the curing reaction, and further, as the curing reaction proceeds, a cured product can be obtained. The maleimide having the epoxypropyl ether group that can be used at this time is the same as that described above. The curable resin composition of the present invention and the cured articles made by means of the curable resin composition have both excellent heat resistance and repairability, and have reformability, and can be used for the following applications. The curable resin composition of the present invention can be laminated with a substrate to form a laminate. The substrate for the laminate can be an inorganic material such as metal or glass, or an organic material such as plastic or wood, depending on the application. It can be in the shape of a laminate, and can have a flat, sheet-like, or three-dimensional structure, or even a three-dimensional shape. It can also have any shape depending on the purpose, such as having curvature on the entire surface or a portion thereof. Furthermore, the hardness and thickness of the substrate are not limited. It can also be a multilayer laminate formed by sequentially laminating a first substrate, a layer composed of the cured resin composition of the present invention, and a second substrate. Because the cured resin composition of this embodiment has excellent adhesion, it can ideally be used as an adhesive to bond the first substrate and the second substrate. Furthermore, the cured resin composition of the present invention can also be used as a substrate, and the cured resin composition of the present invention can be further laminated. Furthermore, the curable resin curing material of the present invention can alleviate stress, and is particularly ideal for bonding different materials. For example, even in laminates of different materials, such as a metal and / or metal oxide substrate and a plastic layer as the second substrate, the stress-relieving ability of the curing material of the present invention can maintain the adhesion. In a laminate formed by layering the cured material of the present invention with a substrate, the layer containing the cured material can also be formed by directly coating or molding the substrate, and it is also acceptable to laminate a pre-formed material. In the case of direct coating, there are no particular limitations on the coating method, and examples include: spraying, spin coating, dip coating, roller coating, doctor blade coating, doctor roll coating, doctor blade coating, curtain coating, slot coating, screen printing, inkjet printing, etc. In the case of direct molding, examples include: in-mold molding, insert molding, vacuum molding, extrusion lamination molding, compression molding, etc. In the case of laminating pre-formed components, uncured or semi-cured component layers can be laminated and then cured, or a layer containing a fully cured component can be laminated onto the substrate. Furthermore, the hardened material of the present invention can be coated with a precursor that can become a substrate and then hardened to perform lamination. Alternatively, the substrate precursor or the composition of the present invention can be bonded in an unhardened or semi-hardened state before being hardened. The substrate precursor is not particularly limited, and various hardenable resin compositions can be listed. The cured product obtained using the curable resin composition of this invention exhibits particularly high adhesion to metals and / or metal oxides, and therefore can be used particularly well as a primer for metals. Examples of metals include: copper, aluminum, gold, silver, iron, platinum, chromium, nickel, tin, titanium, zinc, various alloys, and materials composed of these. Examples of metal oxides include: individual oxides and / or composite oxides of these metals. Especially due to its excellent adhesion to iron, copper, and aluminum, it can be used well as an adhesive for iron, copper, and aluminum. The curable resin composition of this invention is ideally suited for use as an adhesive for structural components in the automotive, tram, civil engineering, electronics, aircraft, and aerospace industries. This adhesive, for example, maintains high adhesion even when used for bonding dissimilar materials such as metals and non-metals, unaffected by temperature variations and is resistant to peeling. Furthermore, in addition to structural component applications, this adhesive can also be used for general office applications, medical applications, carbon fiber applications, battery units, modules, or housings, as well as for bonding optical components, optical discs, printed circuit board mounting, die bonding, semiconductor applications such as underfill, BGA reinforcement underfill, and mounting adhesives for anisotropic conductive films and anisotropic conductive pastes. In cases where the curable resin composition of the present invention has a fibrous matrix and the fibrous matrix is ​​a reinforcing fiber, the curable resin composition containing the fibrous matrix can be used as a fiber-reinforcing resin. The method of incorporating the fibrous matrix into the composition is not particularly limited, as long as it does not impair the effects of the present invention. Examples include methods such as mixing, coating, impregnation, injection, and pressing to composite the fibrous matrix with the composition. The appropriate method can be selected based on the morphology of the fiber and the intended use of the fiber-reinforcing resin. There are no particular limitations on the methods for molding fiber-reinforced resins. For sheet-like products, extrusion molding is generally used, but planar pressing can also be employed. Other methods include extrusion molding, blow molding, compression molding, vacuum forming, and injection molding. For film-like products, in addition to melt extrusion, solution casting can be used. Examples of melt molding methods include blown film forming, casting, extrusion lamination, calendering, sheet forming, fiber forming, blow molding, injection molding, rotational molding, and coating molding. Furthermore, for resins cured by active energy lines, various curing methods utilizing active energy lines can be used to manufacture cured products. Especially in cases where thermosetting resin is the main component of the matrix resin, molding methods that involve pre-impregnating the molding material and then pressurizing and heating it using a pressing or autoclave can be listed. Other examples include: Resin Transfer Molding (RTM), Vacuum Assisted Resin Transfer Molding (VaRTM), Lamination Molding, and Hand Lay-up Molding. The curable resin composition of the present invention produces cured products with good heat resistance and repairability, as well as reformability. Therefore, it can be used in molding materials such as large housings or motor housings, internal molding profiles, gears, or pulleys. These can be cured products made of resin alone or cured products reinforced with fibers such as glass chips. Fiber-reinforced resins can be formed in an uncured or semi-cured state, known as a prepreg. Alternatively, the product can be circulated in the prepreg state and then undergo final curing to form a cured product. In the case of forming a laminate, it is preferable to form a tightly bonded laminate by laminating other layers after forming the prepreg and then undergoing final curing. There is no particular limitation on the mass ratio of the component used in this case to the fibrous matrix, but it is generally preferred to prepare it with the resin component in the prepreg being 20-60% by mass. The cured material of this invention exhibits excellent heat resistance and repairability, and is reformable, making it suitable for use as a heat-resistant material and electronic material. It is particularly ideal for use in semiconductor sealing materials, circuit boards, extension films, extension substrates, adhesives, or photoresist materials. Furthermore, it is ideally suited as a matrix resin for fiber-reinforced resins, especially as a high-heat-resistant prepreg. The resulting heat-resistant or electronic components are ideally suited for a wide variety of applications, including, but not limited to, industrial machinery parts, general machinery parts, automotive / railway / vehicle parts, aerospace-related parts, electronic / electrical parts, building materials, container / packaging components, consumer goods, sports / leisure products, and wind power generation frame components. This invention leverages the excellent flexibility of hardened materials, making it ideal for use as an adhesive for structural components in the automotive, tram, civil engineering, electronic equipment, aircraft, and aerospace industries. Even when bonding dissimilar materials such as metals and non-metals, the adhesive maintains high adhesion regardless of temperature variations and is resistant to peeling. Furthermore, besides its application in structural components, the adhesive can also be used for general office applications, medical applications, and for bonding carbon fiber, battery units, modules, or housings. Examples include adhesives for bonding optical components, optical discs, printed circuit board mounting, die bonding, semiconductor adhesives such as underfills, BGA reinforcement underfills, and mounting adhesives for anisotropic conductive films and anisotropic conductive pastes. The following examples illustrate representative products. 1. A method for obtaining a semiconductor sealing material from the resin composition of the present invention includes, for example, using an extruder, kneader, roller, etc., to fully melt and mix the aforementioned resin composition, curing accelerator, and inorganic filler, etc., until homogeneous, as required. In this case, fused silica is typically used as the inorganic filler. However, when used as a high thermal conductivity semiconductor sealing material for power transistors and power ICs, highly filled materials such as highly crystalline silica, alumina, and silicon nitride, or fused silica, crystalline silica, alumina, and silicon nitride, which have higher thermal conductivity than fused silica, can be used. The preferred filling ratio is 30-95% by mass per 100 parts by mass of the curable resin composition. More preferably, it is 70 parts by mass or more, and even more preferably 80 parts by mass or more, to achieve improved flame retardancy, moisture resistance, and resistance to weld cracking, as well as a reduced coefficient of linear expansion. 2. Semiconductor device as a semiconductor package forming of semiconductor device obtained from the curable resin composition of the present invention, for example: molding the above-mentioned semiconductor sealing material, or forming it using a transfer molding machine, injection molding machine, etc., and further heating it at 50 to 250°C for 2 to 10 hours. 3. A method for obtaining a printed circuit board as a component of the present invention includes: a method of conventionally laminating the above-mentioned prepreg, appropriately overlapping copper foil, and heating and pressing it at 170 to 300°C for 10 minutes to 3 hours under a pressure of 1 to 10 MPa. 4. A method for manufacturing a flexible substrate from the crosslinked resin composition of the present invention can be exemplified by a method comprising the following three steps: Step 1 is to coat a crosslinked resin composition containing resin components and organic solvents onto an electrically insulating film using a coating machine such as a reverse roller coater or a dot coater; Step 2 is to heat the electrically insulating film coated with the crosslinked resin composition at 60–170°C for 1–15 minutes using a heating machine to allow the solvent to evaporate from the electrically insulating film, thereby B-stageing the crosslinked resin composition; Step 3 is to hot-press a metal foil onto an adhesive using a heated roller or the like (preferably, the pressing pressure is 2–200 N / cm, and the pressing temperature is preferably 40–200°C) on the electrically insulating film after B-stageing of the crosslinked resin composition. Alternatively, if sufficient adhesion can be achieved through the above three steps, it is acceptable to stop here. However, if complete adhesion is required, it is preferable to further cure the resin composition at 100–200°C for 1–24 hours. The thickness of the finally cured resin composition layer is preferably in the range of 5–100 μm. 5. A method for obtaining an augmentation substrate from the composition of the present invention can be exemplified by the following steps. First, the composition, appropriately mixed with rubber, filler, etc., is applied to a circuit board on which circuits are formed using a spraying method, curtain coating method, etc., and then cured (step 1). Next, as needed, predetermined through-holes are made, and the surface is treated with a roughening agent, and its surface is cleaned with hot water to form an uneven surface, and then a metal plating process such as copper is performed (step 2). This operation is repeated sequentially as needed to form an augmentation layer of resin insulating layer and conductor layer of predetermined circuit pattern (step 3). In addition, the through-holes are made after the outermost resin insulating layer is formed. Furthermore, the augmentation substrate of the present invention can also be formed by heating and pressing a copper foil coated with resin, which is semi-cured on a copper foil, onto a wiring board on which circuits are formed at 170 to 300°C to form a roughened surface, thereby omitting the plating process to produce the augmentation substrate. 6. As a method for obtaining a thickened film from the composition of the present invention, the thickened film can be manufactured by coating the above composition onto the surface of a support film (Y) serving as a substrate, and further drying the organic solvent by heating or hot air blowing, etc., to form a layer (X) of the composition. The organic solvents used here are preferably ketones such as acetone, methyl ethyl ketone, and cyclohexanone; acetates such as ethyl acetate, butyl acetate, celusone acetate, propylene glycol monomethyl ether acetate, and carbitol acetate; carbitols such as celusone and butyl carbitol; aromatic hydrocarbons such as toluene and xylene; dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; and preferably, the non-volatile components are used in a proportion of 30 to 60% by mass. The thickness of the formed layer (X) is typically set to be greater than or equal to the thickness of the conductor layer. The thickness of the conductor layer in a circuit board is typically in the range of 5 to 70 μm; therefore, the thickness of the resin composition layer is preferably 10 to 100 μm. Furthermore, the aforementioned composition layer (X) in this invention can also be protected by a protective film described later. By using a protective film, dirt or scratches can be prevented from adhering to the surface of the resin composition layer. The aforementioned support film and protective film can be exemplified by: polyolefins such as polyethylene, polypropylene, and polyvinyl chloride; polyesters such as polyethylene terephthalate (hereinafter referred to as "PET") and polyethylene naphthalate; polycarbonate; and polyimide. Further examples include: release paper or metal foils such as copper foil and aluminum foil. In addition to matte treatment and corona treatment, the support film and protective film can also undergo release treatment. The thickness of the support film is not particularly limited, typically ranging from 10 to 150 μm, preferably from 25 to 50 μm. The thickness of the protective film is preferably set to 1 to 40 μm. The aforementioned support film (Y) is peeled off after being laminated onto the circuit board or after forming an insulating layer through heat curing. Peeling off the support film (Y) after the curable resin composition layer constituting the laminate has been heat-cured prevents the adhesion of contaminants or other contaminants during the curing process. Peeling off after curing typically involves pre-molding the support film. The build-up film obtained as described above can be used to manufacture multilayer printed circuit boards. For example, if layer (X) is protected by a protective film, after peeling off the protective film, layer (X) is laminated onto one or both sides of the circuit board in direct contact with the circuit board, for example, by vacuum lamination. The lamination method can be batch lamination or continuous lamination using rollers. Furthermore, depending on the requirements, the build-up film and the circuit board can be preheated before lamination. The lamination conditions are preferably a lamination temperature of 70–140°C and a lamination pressure of 1–11 kgf / cm². 2 (9.8×10 4 ~107.9×10 4 N / m 2It is preferable to perform lamination under reduced pressure, with the air pressure below 20 mmHg (26.7 hPa). 7. As a method for obtaining conductive paste from the composition of the present invention, examples include: a method of dispersing conductive particles in the composition. The conductive paste described above can be used as a paste resin composition for circuit connection or an anisotropic conductive adhesive, depending on the type of conductive particles used. [Examples] Next, the present invention will be specifically described through examples and comparative examples. Unless otherwise specified, "parts" and "%" are mass measurements. The present invention is not limited thereto. 1 H and 13 C-NMR, FD-MS, and GPC measurements were performed under the following conditions. 1 1H-NMR: JEOL RESONANCE "JNM-ECA600" Magnetic field strength: 600MHz Number of cycles: 32 Solvent: CDCl 3. DMSO-d 6. Sample concentration: 30% by mass 13 C-NMR: JEOL RESONANCE "JNM-ECA600" Magnetic field strength: 150MHz Number of cycles: 320 Solvent: DMSO-d 6. Sample concentration: 30% by mass FD-MS: JMS-T100GC AccuTOF manufactured by Nippon Electronics Co., Ltd. Measurement range: m / z = 50.00~2000.00 Rate of change: 25.6 mA / min Final current: 40 mA Cathode voltage: -10 kV GPC: HLC-8320GPC manufactured by Tosoh Corporation; Column: TSK-GEL G2000HXL + TSK-GEL G3000HXL + TSK-GEL G4000HXL manufactured by Tosoh Corporation; Detector: RI (Differential Refractive Index Meter); Measurement Conditions: 40℃; Mobile Phase: Tetrahydrofuran; Flow Rate: 1 ml / min; Standards: PStQuick A, PStQuick B, PStQuick E, PStQuick F manufactured by Tosoh Corporation. The epoxy equivalent of the synthesized epoxy resin was determined according to JIS K7236, and the epoxy equivalent (g / eq) was calculated. As an example of a method for calculating the number of repeating units, calculations can be made from the results of GPC molecular weight determination or analysis using appropriate equipment such as FD-MS and NMR. Synthesis Example 1: 420 g (2.0 equivalents) of diglycidyl ether of 1,12-dodecanediol (manufactured by Yokkaichi Synthetic Co., Ltd.: epoxy equivalent 210 g / eq) and 456 g (4.0 equivalents) of bisphenol A (hydroxyl equivalent 114 g / eq) were added to a flask equipped with a thermometer, cooling tube, and stirrer. The mixture was heated to 140°C over 30 minutes, and then 4.0 g of a 4% sodium hydroxide aqueous solution was added. The temperature was then increased to 150°C over 30 minutes, and the reaction was carried out at 150°C for 6 hours. Afterwards, a neutralization amount of sodium phosphate was added to obtain 858 g of the hydroxyl compound (Ph-1). This hydroxyl compound (Ph-1) showed a peak at M+=771, corresponding to the theoretical structure of m=1 in the following structural formula (Ph-1), thus confirming the presence of the target hydroxyl compound. The hydroxyl equivalent of this hydroxyl compound (Ph-1) calculated by GPC is 388 g / eq, and the average value of the repeating unit m is 0.8. Synthesis Example 2: The 420 g (2.0 equivalent) of 1,12-dodecanediol diglycidyl ether (epoxy equivalent 210 g / eq) in Synthesis Example 1 was replaced with 884 g (2.0 equivalent) of polytetramethylene glycol diglycidyl ether (Nagase ChemteX "Denacol EX-991L": epoxy equivalent 442 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 1, yielding 1313 g of the hydroxyl compound (Ph-2). This hydroxyl compound (Ph-2) showed a peak at M+=1380, corresponding to the theoretical structure of the following structural formula (Ph-2) with m=1 and n2=11, thus confirming the presence of the target hydroxyl compound. The hydroxyl equivalent of this hydroxyl compound (Ph-2) calculated by GPC was 600 g / eq, and the average value of the repeating unit m was 0.8. Synthesis Example 3: The 420 g (2.0 equivalent) of 1,12-dodecanediol diglycidyl ether (epoxy equivalent 210 g / eq) from Synthesis Example 1 was replaced with 962 g (2.0 equivalent) of polypropylene glycol diglycidyl ether (Nagase ChemteX "Denacol EX-931": epoxy equivalent 481 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 1, yielding 1390 g of the hydroxyl compound (Ph-3). This hydroxyl compound (Ph-3) showed a peak at M+=1226, corresponding to the theoretical structure of the following structural formula (Ph-3) with m=1 and n2=11, thus confirming the presence of the target hydroxyl compound. The hydroxyl equivalent of this hydroxyl compound (Ph-3) calculated by GPC was 593 g / eq, and the average value of the repeating unit m was 0.8. Synthesis Example 4: In a flask equipped with a thermometer, dropping funnel, cooling tube, and stirrer, 388 g (388 g / eq hydroxyl equivalent) of the hydroxy compound (Ph-1) obtained in Synthesis Example 1, 1110 g (12.0 moles) of epichlorohydrin, and 300 g of n-butanol were added and dissolved while purging with nitrogen. The temperature was then raised to 65°C, and the pressure was reduced to azeotropic pressure. 122.4 g (1.5 moles) of a 49% sodium hydroxide aqueous solution was added dropwise over 5 hours. The mixture was then stirred continuously under the same conditions for 0.5 hours. During this time, the distillate from the azeotropic reaction was separated using a Dean-Stark trap to remove the water layer, while the oil layer was returned to the reaction system. Unreacted epichlorohydrin was then removed by vacuum distillation. 1000g of methyl isobutyl ketone and 110g of n-butanol were added to the obtained crude epoxy resin for dissolution. Then, 20.0g of a 10% sodium hydroxide aqueous solution was added to this solution, and the mixture was reacted at 80°C for 2 hours. The solution was then washed three times with 300g of water until the pH of the washing solution became neutral. Next, the system was dehydrated by azeotropic distillation, and after precision filtration, the solvent was removed under reduced pressure to obtain 399g of epoxy compound (Ep-1). The epoxy equivalent of the obtained epoxy compound (Ep-1) was 488g / eq. This epoxy resin was analyzed by mass spectrometry, and the results showed that the m=1, q=1, and p values ​​in the following structural formula (Ep-1) were consistent with those in the following structure. 1=0, p The theoretical structure of 2=0 corresponds to the peak value of M+=883, thus confirming the presence of the target epoxy compound (Ep-1). The obtained epoxy compound (Ep-1) contains compounds with q=0, which was confirmed by GPC. The results showed that the mixture contained compounds with q=0 at a proportion of 20.5%, and the average value of the repeating unit q was 0.8. Synthesis Example 5: The 388 g (hydroxyl equivalent 388 g / eq) of hydroxyl compound (Ph-1) from Synthesis Example 4 was replaced with 600 g (hydroxyl equivalent 600 g / eq) of hydroxyl compound (Ph-2). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 4, yielding 591 g of epoxy compound (Ep-2). The epoxy equivalent of the obtained epoxy compound (Ep-2) was 722 g / eq. Mass spectrometry revealed a peak at M+=1492, corresponding to the theoretical structure of the following structural formula (Ep-2) with m=1, n2=11, q=1, p1=0, p2=0, confirming the presence of the target epoxy compound (Ep-2). The obtained epoxy compound (Ep-2) contained a compound with q=0. GPC analysis confirmed that the mixture contained the compound with q=0 at a proportion of 17.2%, with an average repeating unit q value of 0.8. Synthesis Example 6: The 388 g (hydroxyl equivalent 388 g / eq) of hydroxy compound (Ph-1) from Synthesis Example 4 was replaced with 593 g (hydroxyl equivalent 593 g / eq) of hydroxy compound (Ph-3). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 4 to obtain 584 g of epoxy compound (Ep-3). The epoxy equivalent of the obtained epoxy compound (Ep-3) was 714 g / eq. Mass spectrometry of this epoxy compound yielded a peak at M+=1336, corresponding to the theoretical structure of the following structural formula (Ep-3) with m=1, n2=11, q=1, p1=0, p2=0, thus confirming the presence of the target epoxy compound (Ep-3). The obtained epoxy compound (Ep-3) contained a compound with q=0. GPC analysis confirmed that the mixture contained the compound with q=0 at a proportion of 16.8%, with an average value of 0.8 for the repeating unit q. Synthesis Example 7: An epoxy compound (Ep-4) was synthesized according to the method described in J. Network Polym., Jpn., Vol. 29, 208; 2008. The epoxy equivalent of the obtained epoxy compound (Ep-4) was 450 g / eq. Synthesis Example 8: A maleimide compound containing a phenolic hydroxyl group, 4-epoxypropyloxyphenyl maleimide (Ep-M-1), was synthesized according to the method described in Bull. Korean. Chem. Soc. Vol. 31 No. 8, 2272-2278; 2010. Synthesis Example 9: In a flask equipped with a thermometer, dropping funnel, cooling tube, and stirrer, 48.8 g (epoxy equivalent 488 g / eq) of the epoxy resin (Ep-1) obtained in Synthesis Example 4 and 19.6 g (0.2 mol) of furfuryl alcohol were added and dissolved while purging with nitrogen. Then, 0.7 g (0.007 mol) of triethylamine was added, and the mixture was heated to 70°C over 30 minutes and reacted at 70°C for 9 hours. Afterward, the mixture was heated to 150°C, and excess furfuryl alcohol was distilled off under reduced pressure to obtain 53 g of furan compound (F-1). The molecular weight of this furan compound (F-1), determined by GPC, was Mn = 1600 and Mw = 4900. This furan compound (F-1) was derived from... 1 The molecular weight of the furan structure calculated by H-NMR was 575 g / eq per mol. The resulting furan compound (F-1) contained compounds with q=0, which were confirmed by GPC. The results showed that the mixture contained compounds with q=0 at a proportion of 18.2%, and the average value of the repeating unit q was 0.8. Synthesis Example 10: 29 g of the furan compound (F-1, furan equivalent 575 g / eq) obtained in Synthesis Example 9, 5.3 g of 1,6'-bismaleimine-(2,2,4-trimethyl)hexane (BMI-THM manufactured by Yamato Chemical Industry Co., Ltd.), and 50 g of toluene were added to a flask equipped with a thermometer, stirrer, and cooling pipe. After nitrogen substitution, the mixture was reacted at 60°C for 20 hours. Subsequently, the toluene was removed by vacuum distillation to obtain 34 g of the furan compound (F-2). The molecular weight determined by GPC was Mn = 2000 and Mw = 7900. Furthermore,... 1 The molecular weight of the furan structure calculated by ¹H NMR is 2043 g / eq per mole. The obtained furan compound (F-2) contains compounds with n=0 and q=0, which were confirmed by GPC. The results showed that the mixture contained compounds with n=0 and q=0 at a proportion of 1.9%, with an average value of 1.1 for repeating units and an average value of 0.8 for repeating units. Furthermore, in all chemical formulas above the next two lines, * indicates a direct bond with the position of * in the next line. Example 1: In a flask equipped with a thermometer, stirrer, and cooling tube, 34 g of the furan compound (F-2, furan equivalent 2043 g / eq) obtained in Synthesis Example 10, 4.1 g of 4-epoxypropyloxyphenylmaleimide (Ep-M-1) obtained in Synthesis Example 8, and 50 g of toluene were added. After nitrogen substitution, the mixture was reacted at 60°C for 12 hours. Then, the tetrahydrofuran was removed under reduced pressure by distillation to obtain 34 g of a compound (D-1) containing an epoxypropyl ether group. The molecular weight determined by GPC was Mn = 2300 and Mw = 8200. Furthermore, ... 1 The epoxy equivalent calculated by H-NMR was 2288 g / eq. The obtained compound (D-1) containing glycidyl ether groups included compounds with n=0 and q=0. GPC analysis confirmed that the mixture contained compounds with n=0 and q=0 at a proportion of 1.2%, with an average value of 1.1 for repeating units n and an average value of 0.8 for repeating units q. Synthesis Example 11: The 48.8 g (epoxy equivalent 488 g / eq) of epoxy resin (Ep-1) in Synthesis Example 9 was replaced with 72.2 g (epoxy equivalent 722 g / eq) of epoxy resin (Ep-2). Otherwise, the reaction was carried out in the same manner as in Example 1 to obtain 74 g of furan compound (F-3). The molecular weight of this furan compound (F-3), determined by GPC, was Mn = 2400 and Mw = 8100. This furan compound (F-3) was derived from... 1 The molecular weight of the furan structure calculated by H-NMR was 804 g / eq per mol. The resulting furan compound (F-3) contained compounds with q=0, which were confirmed by GPC. The results showed that the mixture contained compounds with q=0 at a proportion of 16.5%, and the average value of the repeating unit q was 0.8. Synthesis Example 12: The 29 g of furan compound (F-1, furan equivalent 575 g / eq) in Synthesis Example 10 was replaced with 40 g of furan compound (F-3, furan equivalent 804 g / eq). Otherwise, the reaction was carried out in the same manner as in Example 2 to obtain 45 g of furan compound (F-4). The molecular weight determined by GPC was Mn = 2800 and Mw = 12100. Furthermore, with... 1 The molecular weight of the furan structure calculated by H-NMR was 2730 g / eq per mol. The obtained furan compound (F-4) contained compounds with n=0 and q=0, which were confirmed by GPC. The results showed that the mixture contained compounds with n=0 and q=0 at a proportion of 1.8%, with an average value of 1.1 for repeating unit n and an average value of 0.8 for repeating unit q. Example 2: 34 g of the furan compound (F-2, furan equivalent 2043 g / eq) from Example 1 was replaced with 45 g of the furan compound (F-4, furan equivalent 2730 g / eq). Otherwise, the reaction was carried out in the same manner as in Example 3 to obtain 44 g of a compound containing glycidyl ether (D-2). The molecular weight, determined by GPC, was Mn = 3100 and Mw = 13200. Furthermore, with... 1The hydroxyl equivalent calculated by H-NMR was 2975 g / eq. The obtained compound (D-2) containing glycidyl ether groups included compounds with n=0 and q=0. GPC analysis showed that the mixture contained compounds with n=0 and q=0 at a proportion of 1.4%, with an average value of 1.1 for repeating units n and an average value of 0.8 for repeating units q. Synthesis Example 13: The 48.8 g (epoxy equivalent 488 g / eq) of epoxy resin (Ep-1) in Synthesis Example 9 was replaced with 71.4 g (epoxy equivalent 714 g / eq) of epoxy resin (Ep-3). Otherwise, the reaction was carried out in the same manner as in Example 1 to obtain 73 g of furan compound (F-5). The molecular weight of this furan compound (F-5), determined by GPC, was Mn = 1900 and Mw = 5100. This furan compound (F-5) was derived from... 1 The molecular weight of the furan structure calculated by H-NMR was 796 g / eq per mol. The resulting furan compound (F-5) contained compounds with q=0, which were confirmed by GPC. The results showed that the mixture contained compounds with q=0 at a proportion of 14.7%, and the average value of the repeating unit q was 1.1. Synthesis Example 14: The 29 g of furan compound (F-1, furan equivalent 575 g / eq) in Synthesis Example 10 was replaced with 40 g of furan compound (F-5, furan equivalent 796 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 10 to obtain 46 g of furan compound (F-6). The molecular weight determined by GPC was Mn = 2300 and Mw = 9000. Furthermore, with... 1 The molecular weight of the furan structure calculated by H-NMR was 2706 g / eq per mol. The obtained furan compound (F-6) contained compounds with n=0 and q=0, which were confirmed by GPC. The results showed that the mixture contained compounds with n=0 and q=0 at a proportion of 2.9%, with an average value of 1.1 for repeating unit n and an average value of 0.8 for repeating unit q. Example 3: The 34g of furan compound (F-2, furan equivalent 2043g / eq) in Example 1 was replaced with 45g of furan compound (F-6, furan equivalent 2706g / eq). Otherwise, the reaction was carried out in the same manner as in Example 1 to obtain 44g of a compound containing glycidyl ether (D-3). The molecular weight, determined by GPC, was Mn=2800 and Mw=10500. Furthermore, with... 1The hydroxyl equivalent calculated by H-NMR was 2951 g / eq. The obtained compound (D-3) containing glycidyl ether groups included compounds with n=0 and q=0. GPC analysis showed that the mixture contained compounds with n=0 and q=0 at a proportion of 1.2%, with an average value of 1.1 for repeating units n and an average value of 0.8 for repeating units q. Synthesis Example 15: The 48.8 g (epoxide equivalent 488 g / eq) of the epoxy compound (Ep-1) in Synthesis Example 9 was replaced with 21 g of diglycidyl ether of 1,12-dodecanediol (manufactured by Yokkaichi Synthetic Co., Ltd.: epoxy equivalent 210 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 9 to obtain 29 g of furan compound (F-7). This furan compound, when analyzed by mass spectrometry, showed a peak at M+=510, corresponding to the theoretical structure of the following structural formula (F-7), thus confirming the presence of the target epoxy compound (Ep-3). The molecular weight of this furan compound (F-7), determined by GPC, was Mn=800 and Mw=1300. This furan compound (F-5) was derived from... 1 The molecular weight of furan structure calculated by H-NMR is 302 g / eq per mol. Synthesis Example 16: The 29 g of furan compound (F-1, furan equivalent 575 g / eq) in Synthesis Example 10 was replaced with 15 g of furan compound (F-7, furan equivalent 302 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 10 to obtain 20 g of furan compound (F-8). The molecular weight determined by GPC was Mn = 1500 and Mw = 2100. Furthermore, with... 1 The molecular weight of the furan structure calculated by H-NMR was 1224 g / eq per mol. The resulting furan compound (F-8) contained a compound with n=0, which was confirmed by GPC. The result showed that the mixture contained the compound with n=0 at a proportion of 1.9%, and the average value of the repeating unit n was 1.1. Example 4: The 34g of furan compound (F-2, furan equivalent 2043g / eq) in Example 1 was replaced with 20g of furan compound (F-8, furan equivalent 1224g / eq). Otherwise, the reaction was carried out in the same manner as in Example 1 to obtain 22g of a compound containing glycidyl ether (D-4). The molecular weight, determined by GPC, was Mn=1700 and Mw=2500. Furthermore, with... 1The hydroxyl equivalent calculated by H-NMR was 1469 g / eq. The obtained compound (D-3) containing glycidyl ether groups included compounds with n=0, which were confirmed by GPC. The results showed that the mixture contained compounds with n=0 at a proportion of 1.2%, and the average value of the repeating unit n was 1.1. Synthesis Example 17: The 48.8 g (epoxy equivalent 488 g / eq) of epoxy resin (Ep-1) in Synthesis Example 9 was replaced with 45.0 g (epoxy equivalent 450 g / eq) of epoxy resin (Ep-4). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 9 to obtain 49 g of furan compound (F-9). The molecular weight of this furan compound (F-9), determined by GPC, was Mn = 1100 and Mw = 1900. This furan compound (F-9) was derived from... 1 The molecular weight of the furan structure calculated by H-NMR was 537 g / eq per mol. The resulting furan compound (F-9) contained a compound with m=0, which was confirmed by GPC, showing that the mixture contained the compound with m=0 at a proportion of 20.1%. Synthesis Example 18: The 29 g of furan compound (F-1, furan equivalent 575 g / eq) in Synthesis Example 10 was replaced with 27 g of furan compound (F-9, furan equivalent 537 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 10 to obtain 32 g of furan compound (F-10). The molecular weight determined by GPC was Mn = 2000 and Mw = 3900. Furthermore, with... 1 The molecular weight of the furan structure calculated by H-NMR was 1929 g / eq per mol. The resulting furan compound (F-10) contained compounds with m=0 and n=0, which were confirmed by GPC. The results showed that the mixture contained compounds with m=0 and n=0 at a proportion of 2.1%, and the average value of the repeating unit n was 1.1. Example 5: The 34g of furan compound (F-2, furan equivalent 2043g / eq) in Example 1 was replaced with 32g of furan compound (F-10, furan equivalent 1929g / eq). Otherwise, the reaction was carried out in the same manner as in Example 1 to obtain 33g of a compound containing glycidyl ether (D-5). The molecular weight, determined by GPC, was Mn=2300 and Mw=4800. Furthermore, with... 1 The hydroxyl equivalent calculated by H-NMR was 2174 g / eq. The obtained compound containing glycidyl ether (D-5) contained compounds with m=0 and n=0, which were confirmed by GPC. The results showed that the mixture contained compounds with m=0 and n=0 at a proportion of 1.7%, and the average value of the repeating unit n was 1.1. Synthesis Example 19: The 48.8 g (epoxy equivalent 488 g / eq) of epoxy resin (Ep-1) in Synthesis Example 9 was replaced with 18.8 g (epoxy equivalent 188 g / eq) of bisphenol A type liquid epoxy resin "E-850S" (manufactured by DIC Corporation). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 9 to obtain 26 g of furan compound (F-11). The molecular weight of this furan compound (F-11), determined by GPC, was Mn=800 and Mw=1300. This furan compound (F-11) was derived from... 1 The molecular weight of the furan structure calculated by H-NMR was 286 g / eq per mol. The resulting furan compound (F-11) contained compounds with m=0, which were confirmed by GPC. The results showed that the mixture contained compounds with p1=0 at a proportion of 66.1%, and the average value of the repeating unit p1 was 0.1. Synthesis Example 20: The 29 g of furan compound (F-1, furan equivalent 575 g / eq) in Synthesis Example 10 was replaced with 14 g of furan compound (F-11, furan equivalent 286 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 10 to obtain 19 g of furan compound (F-12). The molecular weight determined by GPC was Mn = 1500 and Mw = 2400. Furthermore, with... 1 The molecular weight of the furan structure calculated by H-NMR was 1158 g / eq per mol. The obtained furan compound (F-12) contained compounds with p1=0 and n=0, which were confirmed by GPC. The results showed that the mixture contained compounds with p1=0 and n=0 at a proportion of 7.0%, with an average value of 0.1 for repeating unit p1 and an average value of 1.1 for repeating unit n. Example 6: The 34g of furan compound (F-2, furan equivalent 2043g / eq) in Example 1 was replaced with 19g of furan compound (F-12, furan equivalent 1158g / eq). Otherwise, the reaction was carried out in the same manner as in Example 1 to obtain 21g of a compound containing glycidyl ether (D-6). The molecular weight, determined by GPC, was Mn=1800 and Mw=2700. Furthermore, with... 1 The hydroxyl equivalent calculated by H-NMR was 1403 g / eq. The obtained compound (D-6) containing glycidyl ether groups included compounds with m=0 and n=0. GPC analysis confirmed that the mixture contained compounds with m=0 and n=0 at a proportion of 1.7%, with an average value of 0.1 for repeating unit p1 and an average value of 1.1 for repeating unit n. Synthesis Example 21: The 420 g (2.0 equivalent) of diglycidyl ether of 1,12-dodecanediol (epoxide equivalent 210 g / eq) in Synthesis Example 1 was changed to 798 g (3.8 equivalent). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 1, yielding 1207 g of the hydroxyl compound (Ph-4). This hydroxyl compound (Ph-4) showed a peak at M+=771, corresponding to the theoretical structure with m=1 in the following structural formula (Ph-4), thus confirming the presence of the target hydroxyl compound. The hydroxyl equivalent of this hydroxyl compound (Ph-4) calculated by GPC was 2000 g / eq, and the average value of the repeating unit m was 6.9. Synthesis Example 22: The 420 g (2.0 equivalent) of diglycidyl ether of 1,12-dodecanediol (epoxy equivalent 210 g / eq) in Synthesis Example 1 was replaced with 1603 g (3.3 equivalent) of diglycidyl ether of polypropylene glycol (Nagase ChemteX "Denacol EX-931": epoxy equivalent 481 g / eq). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 1, yielding 2012 g of the hydroxyl compound (Ph-5). This hydroxyl compound (Ph-5) showed a peak at M+=1226, corresponding to the theoretical structure of the following structural formula (Ph-5) with m=1 and n2=11, thus confirming the presence of the target hydroxyl compound. The hydroxyl equivalent of this hydroxyl compound (Ph-5) calculated by GPC was 1802 g / eq, and the average value of the repeating unit m was 3.4. Synthesis Example 23: The 388 g (hydroxyl equivalent 388 g / eq) of hydroxyl compound (Ph-1) in Synthesis Example 4 was replaced with 2000 g (hydroxyl equivalent 2000 g / eq) of hydroxyl compound (Ph-4). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 4 to obtain 2120 g of epoxy compound (Ep-5). The epoxy equivalent of the obtained epoxy compound (Ep-5) was 2320 g / eq. Mass spectrometry of this epoxy resin yielded a peak at M+=883, corresponding to the theoretical structure of the following structural formula (Ep-5) with m=1, q=1, p1=0, p2=0, thus confirming the presence of the target epoxy compound (Ep-5). The obtained epoxy compound (Ep-1) contained a compound with q=0. GPC analysis confirmed that the mixture contained a compound with q=0 at a proportion of 0.7%, with an average repeating unit q value of 6.3. Synthesis Example 24: The 388 g (hydroxyl equivalent 388 g / eq) of hydroxy compound (Ph-1) from Synthesis Example 4 was replaced with 1802 g (hydroxyl equivalent 1802 g / eq) of hydroxy compound (Ph-5). Otherwise, the reaction was carried out in the same manner as in Synthesis Example 4 to obtain 1851 g of epoxy compound (Ep-6). The epoxy equivalent of the obtained epoxy compound (Ep-6) was 1895 g / eq. Mass spectrometry of this epoxy compound yielded a peak at M+=1336, corresponding to the theoretical structure of the following structural formula (Ep-6) with m=1, n2=11, q=1, p1=0, p2=0, thus confirming the presence of the target epoxy compound (Ep-6). The obtained epoxy compound (Ep-6) contained a compound with q=0, which was confirmed by GPC. The result showed that the mixture contained a compound with q=0 at a proportion of 2.8%, and the average value of the repeating unit q was 3.1. The composition and cured material were prepared according to the formulations in Tables 1 to 4 (the numbers in the tables are based on mass). Each compound was uniformly mixed using a mixer (THINKY Co., Ltd., "Awatori Rentaro ARV-200") to obtain a curable resin composition. Using a silicone tube as a spacer, this curable resin composition was sandwiched between an aluminum mirror panel (Engineering Test Service Co., Ltd., "JIS H 4000 A1050P") and heat-cured under predetermined conditions to obtain a cured material with a thickness of 0.7 mm. <Tension Elongation> The hardened material was punched into a dumbbell shape (JIS K 7161-2-1BA) using a punching blade, and this was used as a test piece. Tensile tests were performed on this test piece using a tensile testing machine (Autograph AG-IS, manufactured by Shimadzu Corporation) according to JIS K 7162-2, and its elongation at the breaking point in a test environment of 23°C was evaluated (test speed: 2 mm / min). <Reforming Test> The prepared hardened material was cryogenically pulverized. 0.07g of the pulverized hardened material was placed in a 10mm square, 0.5mm thick mold frame and vacuum-pressed at 150℃ / 4 hours / 10MPa, followed by curing at 60℃ / 24 hours. The appearance of the resulting hardened material was visually observed. Judgment criteria are as follows: A: Joints disappear, hardened material is integrated. B: Some joints are visually visible, but the hardened material is integrated. C: A clump is formed, which easily disperses with slight force. <Repair Test> The hardened material was cut with a razor, and the resulting fracture surfaces were brought into contact. It was then cured in a dryer at 130°C for 30 minutes followed by 60°C for 24 hours. After removal from the dryer, the cross-sections of the hardened material were visually inspected to confirm whether they were joined together. The judgment criteria are as follows: A: Joined, even when the hardened material is bent at 90°, the joint does not separate. B: Joined, if the hardened material is bent, the joint separates. C: Not joined. <Disintegration Test> Following the formulations in Tables 1-4 (the numbers in the tables are based on mass), each compound was uniformly mixed using a mixer (THINKY Co., Ltd. "Awatori Rentaro ARV-200") to obtain a curable resin composition. This resin composition was applied to one of two cold-rolled steel sheets (TP Giken Co., Ltd. "SPCC-SD", 1.0mm × 25mm × 100mm), with glass beads (Potters Ballotini Co., Ltd. "J-80") added as spacers, and the other SPCC-SD sheet (adhesion area: 25mm × 12.5mm) was then bonded together. The sheets were heat-cured according to the temperatures in Tables 1-3 to obtain test pieces. These test pieces were suspended in a 120°C dryer, and a 500g weight was applied to one side of the substrate. The substrate was left to stand for 30 minutes, and the adhesion was evaluated. The judgment criteria are as follows: A: The bonded portion deviates, and the substrate on the side with the applied weight falls off. B: Then a partial deviation occurred. C: The substrate remained unchanged. [Table 1] [Table 2] [Table 3] [Table 4] Additionally, the blends shown in the table are as follows: E-850S: Bisphenol A type liquid epoxy resin (manufactured by DIC Corporation, epoxy equivalent 188 g / eq) BMI-TMH: 1,6'-bismaleimine-(2,2,4-trimethyl)hexane; PMI: Phenylamimine (manufactured by Kanto Chemical); DICY: Dicyandiamine (manufactured by Mitsubishi Chemical Corporation, "DICY7"); DCMU: 3-(3,4-dichlorophenyl)-1,1-dimethylurea (manufactured by DIC Corporation, "B-605-IM"); DTA: Diethylenetriamine (manufactured by Kanto Chemical). Comparative Examples 3 and 4 could not be cured by heating. It is believed that this is because the compound containing reversible bonds, consisting of "conjugated diene intermediate + bismaleimide compound + maleimide compound", does not have an epoxypropyl ether group, and therefore does not crosslink with the epoxy resin and curing agent used together. none none. none.

Claims

1. A compound containing an epoxypropyl ether group represented by the following general formula (1): [In the furan-derived structure of formula (1), halogen atoms, alkoxy groups, arylalkoxy groups, aryloxy groups, nitro groups, amide groups, alkoxycarbonyl groups, aryloxycarbonyl groups, cyano groups, alkyl groups, cycloalkyl groups, arylalkyl groups, or aryl groups may be used as substituents; n is the average number of repetitions, which is 0 to 10; Z1 is any one of the structures represented by the following formula (2), Z2 is any one of the following formula (3), and Z3 is any one of the structures represented by the following formula (4), and multiple Z1 and Z3 may be present in one molecule, and they may be the same or different; [The aromatic ring in formula (2) may be substituted or unsubstituted, * indicates a bond point; G is epoxypropyl or 2-methylepoxypropyl, and -OG on the naphthalene ring in the formula indicates that it can be bonded at any location]; [In formula (3), Ar is independently a structure containing an unsubstituted or substituted aromatic ring, and R1 and R2 are independently hydrogen atoms, methyl or ethyl groups, R is a hydrogen atom or a methyl group, R' is a divalent hydrocarbon group with 2 to 12 carbon atoms, n1 is an integer from 2 to 16, n2 is the average value of the repeating units, which is 2 to 30, k1 is the average number of repeating units, which is in the range of 0.5 to 10, p1 and p2 are each independently 0 to 5, X is the structural unit represented by the following formula (3-1), Y is the structural unit represented by the following formula (3-2), [In formulas (3-1) and (3-2), Ar, R, R1, R2, R', n1, and n2 are the same as those mentioned above]; m1 and m2 are the average values ​​of the repeating units, which are each independently 0 to 25, and m1 + m2 ≥ 1; However, the bond between the structural unit X represented by formula (3-1) and the structural unit Y represented by formula (3-2) can be random or block, and the total number of structural units X and Y present in 1 molecule are m1 and m2 respectively]; [In formula (4), n3 and n5 are the average values ​​of the number of repetitions, which are 0.5 to 10 respectively, n4 is an integer from 1 to 16, and R” is a hydrogen atom, methyl or ethyl.] 2. A curable resin composition comprising, as an essential component, a compound containing an epoxypropyl ether group as claimed in claim 1 and a reactive compound containing an epoxypropyl ether group (I).

3. The curable resin composition as claimed in claim 2, wherein, Compound (I), which is reactive with compounds containing glycidyl ether groups, is a compound containing hydroxyl groups.

4. The curable resin composition as claimed in claim 3, wherein, The compound (I) that is reactive with compounds containing glycidyl ether groups is a compound containing hydroxyl groups with reversible bonds.

5. The curable resin composition as claimed in claim 4, wherein, The hydroxyl-containing compound with reversible bonds is a hydroxyl-containing compound represented by the following general formula: [In formula (7), Ar is independently a structure containing an aromatic ring that is unsubstituted or has a substituent. The structures derived from anthracene in formulas (5-1) and (5-2), and the structures derived from furan in formulas (6-1) and (6-2), may also have halogen atoms, alkoxy, arylalkoxy, aryloxy, nitro, acetylamino, alkoxycarbonyl, aryloxycarbonyl, cyano, alkyl, cycloalkyl, aralkyl or aryl as substituents; in the formula, ma is an integer from 1 to 10, mb is an integer from 1 to 4, n is the average value of the number of repetitions, which is from 0 to 10; Z5 is any of the structures represented by formula (8), Z2 is any of the structures represented by formula (9), Z3 is any of the structures represented by formula (10), Z4 is any of the structures represented by formulas (11) and (12), and there are multiple structures in one molecule, which may be the same or different; [The aromatic ring in formula (8) can be substituted or unsubstituted, * indicates a bond point; the hydroxyl group on the naphthalene ring in the formula indicates that it can be bonded at any point]; [In formula (9), Ar is independently a structure containing an unsubstituted or substituted aromatic ring, R1 and R2 are independently hydrogen atoms, methyl or ethyl, R is a hydrogen atom or methyl, R' is a divalent hydrocarbon group with 2 to 12 carbon atoms, n1 is an integer from 2 to 16, n2 is the average value of the repeating units, which is 2 to 30, k1 is the average number of repeating units, which is in the range of 0.5 to 10, p1 and p2 are independently 0 to 5, X is the structural unit represented by the following formula (9-1), Y is the structural unit represented by the following formula (9-2), [In formulas (9-1) and (9-2), Ar, R, R1, R2, R', n1, and n2 are the same as those mentioned above]; m1 and m2 are the average values ​​of the number of repetitions, each of which is 0 to 25 independently, and m1 + m2 ≥ 1; however, the bond between the structural unit X represented by formula (9-1) and the structural unit Y represented by formula (9-2) can be random or block, and the total number of each structural unit X and Y present in 1 molecule is m1 and m2 respectively; [In formula (10), n3 and n5 are the average values ​​of the number of repetitions, which are 0.5 to 10 respectively, n4 is an integer from 1 to 16, and R” is a hydrogen atom, methyl or ethyl respectively]; [In formulas (11) and (12), R1, R2, R', n1, and n2 are the same as those mentioned above].

6. The curable resin composition of claim 2 further comprises an epoxy resin having an epoxy equivalent of 100 to 10,000 g / eq, other than the compound containing glycidyl ether group of claim 1.

7. The curable resin composition as claimed in claim 6, wherein, The epoxy resin is represented by the following formula (13), and the epoxy equivalent is 500 to 10000 g / eq; [In formula (13), Ar is independently a structure containing an unsubstituted or substituent aromatic ring, X' is a structural unit represented by the following formula (13-1), Y' is a structural unit represented by the following formula (13-2), [In formulas (13-1) and (13-2), Ar is the same as above, R1 and R2 are independently hydrogen atoms, methyl or ethyl, R' is a divalent hydrocarbon group with 2 to 12 carbon atoms, R3, R4, R7 and R8 are independently hydroxyl, epoxypropyl ether or 2-methyl epoxypropyl ether, R5, R6, R9 and R10 are independently hydrogen atoms or methyl, n1 is an integer from 4 to 16, and n2 is the average value of the repeating units, which is 2 to 30]; R11 and R12 are each independently glycidyl ether or 2-methyl glycidyl ether; R13 and R14 are each independently hydroxyl, glycidyl ether or 2-methyl glycidyl ether; R15 and R16 are hydrogen atoms or methyl groups; m3, m4, p1, p2, and q are the average number of repetitions; m3 and m4 are each independently 0 to 25, and m3 + m4 ≥ 1; p1 and p2 are each independently 0 to 5; and q is 0.5 to 5. However, the bond between structural unit X' represented by formula (13-1) and structural unit Y' represented by formula (13-2) can be random or block; the total number of structural units X and Y present in one molecule is m3 and m4, respectively.

8. The curable resin composition as claimed in claim 2, wherein, The concentration of reversible bonding is above 0.10 mmol / g relative to the total mass of the curing components in the curing resin composition.

9. The curing resin composition of claim 2 is any one of a self-healing composition, a disintegrating composition, or a composition for remolding materials.

10. A curing compound formed by curing a curing resin composition as claimed in claim 2.

11. A laminate having a substrate and a layer comprising a hardened material as claimed in claim 10.

12. A heat-resistant component comprising a hardened material as claimed in claim 10.

13. A method for manufacturing a compound containing an epoxypropyl ether group as claimed in claim 1, wherein the compound containing an epoxypropyl ether group as claimed in claim 1 is synthesized in situ using a conjugated diene intermediate represented by the following general formula (1)' and a maleimide compound having an epoxypropyl ether group, in a hardening process with a compound (I) that is reactive with the compound containing the epoxypropyl ether group; [wherein, n, Z2, Z3 are the same as described above].

14. A cured compound obtained by subjecting a conjugated diene intermediate represented by general formula (1)' as described in the method of manufacturing a compound containing an epoxypropyl ether group as claimed in claim 13, a maleimine compound having an epoxypropyl ether group, and a compound (I) that is reactive with the compound containing an epoxypropyl ether group as necessary raw materials to a curing reaction.