Compound, epoxy resin, curable composition, material for recycling, cured article, method for producing cured article, method for producing decomposition product, and decomposition method

Abstract

Provided is a compound represented by formula (1). [Chemical formula 1] R1 represents H, a C1-20 alkyl group, a C1-20 alkoxy group, a C5-10 aryl group which may have a C1-10 alkyl group, a C1-10 alkoxy group, OH or a halogen atom as a substituent, OH, or a halogen atom; R2 represents H, a C1-10 alkyl group, a hydroxyalkyl group, a glycidyl ether group, a methyl glycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group or a methacryloyloxyalkyl group; n represents a numerical value of 0-4; and X1 and X2 each represent H or a group represented by general formula (11), wherein at least one of X1 and X2 is represented by general formula (11). [Chemical formula 2] R3 represents H or a methyl group.

Description

Compound, epoxy resin, curable composition, recyclable material, cured product, method for producing cured product, method for producing decomposition product, and decomposition method

[0001] The present invention relates to a compound, and more particularly to a glycidyl ether compound having a 1,3-dioxane skeleton.

[0002] Epoxy resins are widely used industrially as components or raw materials for coating materials, adhesives, and various molding materials.

[0003] Epoxy resins include aromatic epoxy resins, alicyclic epoxy resins, and aliphatic epoxy resins, and are used for various purposes depending on their properties. For example, Patent Document 1 proposes an epoxy resin having an acetal skeleton.

[0004] China Publication No. 111704711

[0005] However, although epoxy resin materials can provide strong materials by curing with heat or light, they are difficult to reuse. Therefore, an object of the present invention is to provide a compound capable of forming a cured product with excellent acid decomposition properties.

[0006] That is, the present invention provides a compound represented by the following general formula (1):

[0007] In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, or an aryl group having 5 to 10 carbon atoms which may have a halogen atom as a substituent, a hydroxyl group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２represents a hydrogen atom or a group represented by the following general formula (11): １ or X ２ At least one of the above is a group represented by the general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond.

[0008] The present invention also provides an epoxy resin containing at least one compound represented by the following general formula (1):

[0009] The present invention also provides a method for producing a compound represented by the following general formula (1), the method comprising an epoxidation step of reacting a compound represented by the following general formula (2) with epihalohydrin:

[0010] In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, or an aryl group having 5 to 10 carbon atoms which may have a halogen atom as a substituent, a hydroxyl group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２ represents a hydrogen atom or a group represented by the following general formula (11): １ or X ２ At least one of the above is a group represented by the general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond.

[0011] In the formula, R １represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 10 carbon atoms which may have a hydroxyl group or a halogen atom as a substituent, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group, and n represents a number from 0 to 4.

[0012] Furthermore, the present invention provides a composition containing the compound represented by formula (1) and a curing agent.

[0013] According to the present invention, a compound capable of forming a cured product having excellent acid decomposability can be provided.

[0014] FIG. 1 is a GC chart of the epoxy resin material obtained in Example 1. FIG. 2 is an MS spectrum of peak 1 in FIG. 1. FIG. 3 is an MS spectrum of peak 2 in FIG. 1. FIG. 4 is an MS spectrum of peak 3 in FIG. 1. FIG. 5 is an NMR chart of o-DOP-EP1 obtained in Example 1. FIG. 6 is an NMR chart of o-DOP-EP2 obtained in Example 1. FIG. 7 is a GC chart of resin 3 obtained in Example 2.

[0015] The compound of the present invention, its production method and composition will be described in detail below.

[0016] A. Compound First, the compound of the present disclosure will be described. The compound of the present disclosure (hereinafter, sometimes referred to as "compound (1)") is characterized by being represented by the following general formula (1).

[0017] In the formula, R １represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, or an aryl group having 5 to 10 carbon atoms which may have a halogen atom as a substituent, a hydroxyl group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２ represents a hydrogen atom or a group represented by the following general formula (11): １ or X ２ At least one of the above is a group represented by the general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond.

[0018] In the general formula (1), R １ Examples of the alkyl group having 1 to 20 carbon atoms represented by the formula (I) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an amyl group, an isoamyl group, a tert-amyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, a decyl group, an isodecyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, a benzyl group, and a phenethyl group.

[0019] In the general formula (1), R １ Examples of the alkoxy group having 1 to 20 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, an amyloxy group, a hexyloxy group, a pentyloxy group, an octyloxy group, a nonyloxy group, and a decyloxy group.

[0020] In the general formula (1), R１ Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0021] In the general formula (1), R １ Examples of the aryl group represented by the formula (I) which may have a substituent include a phenyl group and a naphthyl group. １ The number of carbon atoms of the aryl group which may have a substituent represented by the following formula is preferably 6 or more. Examples of the alkyl group having 1 to 10 carbon atoms and the alkoxy group having 1 to 10 carbon atoms which are used as a substituent to substitute a hydrogen atom in the aryl group include R １ Among the alkyl groups having 1 to 20 carbon atoms and alkoxy groups having 1 to 20 carbon atoms described as groups used in R, groups having a predetermined number of carbon atoms can be used. As the halogen atom used as a substituent to replace a hydrogen atom in the aryl group, R １ The halogen atoms used in the above formula (1) can be the same as those described above.

[0022] In the general formula (1), R ２ The alkyl group having 1 to 10 carbon atoms represented by R １ Among the alkyl groups having 1 to 20 carbon atoms described as groups used in R, groups having a predetermined number of carbon atoms can be used. ２ However, in the case of an alkyl group, it is preferably an alkyl group having 1 to 5 carbon atoms, among which an alkyl group having 1 to 4 carbon atoms is preferred, among which an alkyl group having 1 to 3 carbon atoms is particularly preferred, among which a methyl group or an ethyl group is particularly preferred, and especially an ethyl group is preferred. ２ This is because compound (1) having the above group can produce a cured product with excellent acid decomposability. Furthermore, compound (1) can form a cured product with excellent adhesiveness. Furthermore, due to these properties, compound (1) is preferred from the viewpoint of being useful as a chemically recycled material. Furthermore, compound (1) is preferred because raw materials are easily available.

[0023] In the general formula (1), R ２Examples of the hydroxyalkyl group represented by R include a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group. ２ In the case where the hydroxyalkyl group is used, the hydroxymethyl group is preferred because the raw material is easily available.

[0024] In the general formula (1), R ２ Examples of the glycidyloxyalkyl group represented by the formula (I) include a glycidyloxymethyl group and a glycidyloxyethyl group.

[0025] In the general formula (1), R ２ Examples of the β-methylglycidyloxyalkyl group represented by the formula (I) include a β-methylglycidyloxymethyl group and a β-methylglycidyloxyethyl group.

[0026] In the general formula (1), R ２ Examples of the acryloyloxyalkyl group represented by the formula (I) include an acryloyloxymethyl group and an acryloyloxyethyl group.

[0027] In the general formula (1), R ２ Examples of the methacryloyloxyalkyl group represented by the formula (I) include a methacryloyloxymethyl group and a methacryloyloxyethyl group.

[0028] In the general formula (1), n ​​is preferably 0 or 1, and n is particularly preferably 0. This is because a cured product having excellent acid decomposability and adhesiveness can be formed. １ may be a group other than a hydrogen atom. When n is 1 to 4, R １ is preferably an alkyl group having 1 to 4 carbon atoms or a methoxy group, and R １ is a methyl group. This is because the compound (1) can form a cured product that is excellent in acid decomposition property. In addition, the compound (1) can form a cured product that is excellent in adhesiveness. Furthermore, R ２is preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a glycidyloxymethyl group, and is preferably an alkyl group having 1 to 5 carbon atoms, particularly preferably an alkyl group having 1 to 4 carbon atoms, and of these, particularly preferably an alkyl group having 1 to 3 carbon atoms, and of these, particularly preferably an alkyl group having 1 to 2 carbon atoms, and of these, particularly preferably an ethyl group. This is because compound (1) can form a cured product that is excellent in acid decomposability. Also, compound (1) can form a cured product that is excellent in adhesiveness. X １ and X ２ are each independently a hydrogen atom or a group represented by the general formula (11), and for example, X １ and X ２ are both groups represented by the general formula (11), １ is a group represented by the general formula (11), and X ２ is a hydrogen atom, １ is a hydrogen atom, and X ２ In the present disclosure, X may be a group represented by the general formula (11). １ and X ２ are both groups represented by the general formula (11), or X １ is a group represented by the general formula (11), and X ２ is preferably a hydrogen atom, and particularly preferably １ and X ２ is preferably a group represented by the general formula (11). This is because the compound (1) can form a cured product that is excellent in acid decomposition property. Furthermore, the compound (1) can form a cured product that is excellent in adhesiveness. In the present disclosure, R in the general formula (11) can be ３ is preferably a hydrogen atom. This is because the compound (1) can form a cured product that is excellent in acid decomposition property. Furthermore, the compound (1) can form a cured product that is excellent in adhesiveness. In particular, in the general formula (1), n ​​is 0 and R ２is an ethyl group. In particular, in the general formula (1), n ​​is 0 and R ２ is an ethyl group, and X １ and X ２ are both groups represented by formula (11), and X １ and X ２ R in the formula (11) ３ are preferably hydrogen atoms. This is because compound (1) within the above range can form a cured product with excellent acid decomposability. Furthermore, compound (1) can form a cured product with excellent adhesiveness.

[0029] The compound represented by the general formula (1) is a compound represented by any one of the following general formulas (1a), (1b) and (1c):

[0030]

[0031]

[0032]

[0033] In addition, R in the compound represented by the general formula (1a), (1b) or (1c) １ , R ２ , X １ , X ２ and n is one represented by the formula (1). Among the compounds represented by the general formula (1a), (1b), or (1c), compounds represented by (1b) or (1c) are particularly preferred, and among these, compounds represented by (1c) are particularly preferred. This is because compounds represented by the formula can form cured products with excellent adhesion to metal materials. Furthermore, compounds represented by the formula can form cured products that are easily decomposed by acid.

[0034] Specific examples of the compounds represented by the general formula (1a), (1b) or (1c) are given below.

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044] The compounds represented by formula (1) and mixtures thereof of the present disclosure preferably have a total chlorine content of 10,000 ppm or less by mass. If the total chlorine content exceeds 10,000 ppm, the chloride ion concentration is high, making the material prone to ion migration, which may reduce reliability when used, for example, as an adhesive or sealant for electrical and electronic components. The total chlorine content can be measured according to ASTM D5808.

[0045] The compound (1) can be used as an epoxy resin either alone or in combination with other epoxy compounds. Specific uses of such epoxy resins are similar to those described in the section "D. Curable compositions" below.

[0046] B. Method for Producing Compound Next, a method for producing the compound of the present disclosure will be described. The method for producing the compound of the present disclosure is a method for producing a compound represented by the following general formula (1), and is characterized by having an epoxidation step of reacting a compound represented by the following general formula (2) with epihalohydrin.

[0047] The production method of the present disclosure includes an epoxidation step.

[0048] 1. Epoxidation Step This step is a step in which the compound represented by the general formula (2) (hereinafter, sometimes referred to as "compound (2)") is reacted with epihalohydrin.

[0049] The reaction method in this step may be any method that can react compound (2) with epihalohydrin to form the compound represented by general formula (1). Such a reaction method is preferably a method in which compound (2) and epihalohydrin are reacted in the presence of a phase transfer catalyst. The use of a phase transfer catalyst can promote the reaction between an alcoholic hydroxyl group and epihalohydrin.

[0050] Examples of epihalohydrin include epichlorohydrin, epibromohydrin, and β-methylepichlorohydrin.

[0051] Examples of the phase transfer catalyst include cetyltrimethylammonium chloride, tetramethylammonium chloride, tetrabutylammonium bromide, methyltrioctylammonium chloride, methyltridecylammonium chloride, N,N-dimethylpyrrolidinium chloride, N-ethyl-N-methylpyrrolidinium iodide, N-butyl-N-methylpyrrolidinium bromide, N-benzyl-N-methylpyrrolidinium chloride, N-ethyl-N-methylpyrrolidinium bromide, N-methyl-N-methylpyrrolidinium chloride ... tylpyrrolidinium bromide, N-butyl-N-methylmorpholinium bromide, N-butyl-N-methylmorpholinium iodide, N-allyl-N-methylmorpholinium bromide, N-methyl-N-benzylpiperidinium chloride, N-methyl-N-benzylpiperidinium bromide, N,N-dimethylpiperidinium iodide, N-methyl-N-ethylpiperidinium acetate, N-methyl-N-ethylpiperidinium iodide, etc. From the viewpoint of high reactivity, cetyltrimethylammonium chloride is preferred.

[0052] The amount of the phase transfer catalyst used is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5.0 parts by mass, and particularly preferably 0.5 to 3.2 parts by mass, relative to 100 parts by mass of the compound represented by formula (2). Use within this range provides an excellent effect of improving reactivity and prevents the generation of by-products.

[0053] The reaction method is preferably a method in which the reaction is carried out in the presence of an alkali, because the use of an alkali can particularly promote the reaction between an alcoholic hydroxyl group and epihalohydrin.

[0054] Examples of alkalis include metal hydroxides such as sodium hydroxide, potassium hydroxide, and calcium hydroxide.

[0055] The alkali may be added by dropping an aqueous alkali solution or by adding a solid alkali, preferably in several batches.

[0056] The amount of alkali used is preferably 0.1 to 10 moles, more preferably 0.2 to 5.0 moles, and particularly preferably 0.5 to 3.2 moles, per mole of the compound represented by formula (2). By using the alkali in this amount, the generation of by-products is suppressed and reactivity is obtained.

[0057] The reaction method is preferably a method in which the reaction is carried out under heated conditions, since this allows the reaction to proceed more quickly.

[0058] The heating temperature is preferably 25° C. or higher and 120° C. or lower, more preferably 30° C. or higher and 100° C. or lower, and particularly preferably 40° C. or higher and 80° C. or lower. By carrying out the reaction within this temperature range, the reaction can proceed quickly and by-products are not generated.

[0059] Furthermore, the reaction can be carried out under increased pressure or reduced pressure as required, and is particularly preferred when carried out under reduced pressure, as this reduces the amount of by-products and allows for a high reaction rate.

[0060] 2. Others The production method of the present disclosure includes the epoxidation step, but may include other steps as necessary. Such other steps include a purification step, etc.

[0061] C. Epoxy Resin Next, the epoxy resin of the present disclosure will be described. The epoxy resin of the present disclosure is characterized by containing the above-mentioned compound (1).

[0062] In the present disclosure, the compound (1) may contain only one type, but it is preferable to contain two or more types. This is because the inclusion of two or more types is expected to improve the adhesive strength of the cured product using the compound (1). In the present disclosure, the compound (1) represented by the general formula (1) and X １ and X ２ is a group represented by the general formula (11) (hereinafter, may be referred to as compound (1x)), and in particular, １ is a group represented by the general formula (11), and X ２ is a hydrogen atom (hereinafter, may be referred to as compound (1y)), and １ is a hydrogen atom, and X ２ is a group represented by general formula (11) (hereinafter, may be referred to as compound (1z)), and it is particularly preferable to contain compound (1x) and compound (1y). This is because the use of such an epoxy resin makes it possible to form a cured product with excellent acid decomposition properties. Furthermore, the use of such an epoxy resin makes it possible to form a cured product with excellent adhesive properties.

[0063] In the present disclosure, the content of the compound (1x) is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, and particularly preferably 65 parts by mass or less, per 100 parts by mass of the compound (1). The lower limit is preferably 20 parts by mass or more, more preferably 40 parts by mass or more, even more preferably 50 parts by mass or more, and particularly preferably 55 parts by mass or more, per 100 parts by mass of the compound (1). The content of the compound (1x) is preferably 20 parts by mass or more and 80 parts by mass or less, more preferably 40 parts by mass or more and 80 parts by mass or less, even more preferably 50 parts by mass or more and 70 parts by mass or less, and particularly preferably 55 parts by mass or more and 65 parts by mass or less, per 100 parts by mass of the compound (1). This is because the use of such an epoxy resin allows for the formation of a cured product with excellent adhesive properties. Furthermore, the use of such an epoxy resin allows for the formation of a cured product that is easily decomposed by acid.

[0064] In the present disclosure, the content of the compound (1y) is preferably 80 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, and particularly preferably 45 parts by mass or less, per 100 parts by mass of the compound (1). The lower limit is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, and particularly preferably 35 parts by mass or more, per 100 parts by mass of the compound (1). The content of the compound (1y) is preferably 20 parts by mass or more and 80 parts by mass or less, more preferably 20 parts by mass or more and 60 parts by mass or less, particularly preferably 30 parts by mass or more and 50 parts by mass or less, and particularly preferably 35 parts by mass or more and 45 parts by mass or less, per 100 parts by mass of the compound (1). The content of the compound (1y) within the above range is preferred because it allows for the production of a curable composition and a cured product with excellent adhesion.

[0065] In the present disclosure, the total content of the compounds (1y) and (1x) is preferably 40 parts by mass or more, more preferably 70 parts by mass or more, even more preferably 80 parts by mass or more, particularly preferably 90 parts by mass or more, even more preferably 95 parts by mass or more, even more preferably 98 parts by mass or more, and most preferably 99 parts by mass or more, per 100 parts by mass of the compound (1). This is because the compound (1) can form a cured product with excellent adhesion to metal materials. Also, the compound (1) can form a cured product that is easily decomposed by acid.

[0066] The total chlorine content of the epoxy resin of the present disclosure is preferably 10,000 ppm or less by mass, more preferably 4,000 ppm or less, and even more preferably 1,000 ppm or less, from the viewpoint of suppressing ion migration. Using an epoxy resin having a total chlorine content within the above range is also preferred in that the cured product obtained from the resin has excellent adhesion to adherends.

[0067] The viscosity of the epoxy resin of the present disclosure is preferably 500 to 30,000 mPa·s, and more preferably 500 to 20,000 mPa·s. Epoxy resins with a viscosity within this range are preferred because they have excellent workability. Viscosity can be measured by the following method. <Method for measuring viscosity using a Brookfield viscometer> After attaching a rotor and measurement container appropriate for the viscosity of the measurement sample to a Brookfield viscometer, the measurement container is immersed in a thermostatic water bath set to 25°C. The sample is left to stand until it reaches a constant temperature, and the rotation speed appropriate for the viscosity is selected. Measurement is carried out for the specified time, and the automatically calculated measurement value is read from the digital display.

[0068] D. Curable Composition Next, the curable composition of the present disclosure will be described in detail. The curable composition of the present disclosure is characterized by containing the compound (1) described above and a curing agent.

[0069] 1. Compound (1) The compound (1) can be the same as described in the section "A. Compound."

[0070] In the present disclosure, the composition may contain only one type of the compound (1), but may also contain two or more types. This is because a cured product excellent in acid decomposability and adhesiveness can be formed. In the present disclosure, when two or more types of the compound (1) are contained, the details of the two or more types of compound (1) can be the same as those described in the section "C. Epoxy resin" above.

[0071] The content of the compound (1) is preferably 10 parts by mass or more and 99 parts by mass or less, and more preferably 15 parts by mass or more and 97 parts by mass or less, in 100 parts by mass of the curable composition. Among these, from the viewpoint of ease of decomposition with an acid and usefulness for chemical recycling, it is preferably 50 parts by mass or more and 97 parts by mass or less, and more preferably 70 parts by mass or more and 95 parts by mass or less, and particularly preferably 80 parts by mass or more and 93 parts by mass or less.

[0072] 2. Other Epoxy Compounds The curable composition may contain an epoxy compound other than the compound (1) (hereinafter, sometimes referred to as "other epoxy compounds"). Examples of the other epoxy compounds include known epoxy compounds. Examples of the epoxy compound include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, biphenol, methylene bisphenol (bisphenol F), methylene bis(ortho-cresol), ethylidene bisphenol, isopropylidene bisphenol (bisphenol A), isopropylidene bis(ortho-cresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis(4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfonyl bisphenol, oxybisphenol, phenol novolac, orthocresol novolac, ethylphenol novolac, butylphenol novolac, and octylphenol novolac. Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as resorcinol novolak and terpene phenol; polyglycidyl ethers of polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, hexanediol, polyglycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-alkylene oxide adducts, and dicyclopentadiene dimethanol diglycidyl ether; glycidyl esters of aliphatic, aromatic, or alicyclic polybasic acids such as maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimer acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, and endomethylenetetrahydrophthalic acid; homopolymers or copolymers of glycidyl methacrylate;Examples of epoxy resins include epoxidized cyclic olefin compounds such as vinylcyclohexene diepoxide, dicyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylate, and bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; epoxidized conjugated diene polymers such as epoxidized polybutadiene and epoxidized styrene-butadiene copolymers; and heterocyclic compounds such as triglycidyl isocyanurate. These epoxy resins may also be internally crosslinked with a terminal isocyanate prepolymer, or may be polymerized using a polyvalent active hydrogen compound (such as a polyhydric phenol, a polyamine, a carbonyl group-containing compound, or a polyphosphate ester).

[0073] Commercially available epoxy resins include, for example, Denacol EX-313, Denacol EX-314, Denacol EX-321, Denacol EX-411, Denacol EX-421, Denacol EX-512, Denacol EX-521, Denacol EX-611, Denacol EX-612, Denacol EX-614, Denacol EX-622, Denacol EX-830, Denacol EX-832, Denacol EX-841, Denacol EX-861, Denacol EX-920, Denacol EX-931, Denacol EX-201, Denacol EX-711, and Denacol EX-721 (manufactured by Nagase ChemteX Corporation); Epolite 200E, ... Polite 400E, Epolite 70P, Epolite 200P, Epolite 400P (manufactured by Kyoeisha Chemical Co., Ltd.), ADEKA RESIN EP-4088S, EP-4088L, EP-4080E, ADEKA RESIN EP-4000, ADEKA RESIN EP-4005, ADEKA RESIN EP-4100, ADEKA RESIN EP-4901 (manufactured by ADEKA Corporation); Oxol PG-100, Oxol EG-200, Oxol EG-210, Oxol EG-250 (manufactured by Osaka Gas Chemicals Co., Ltd.); YD series, YDF series, YDPN series, TDCN series (Nippon Steel & Sumikin Chemical Co., Ltd.); CELLOXIDE 2021P, CELLOXIDE 2081 (manufactured by Daicel Corporation); TECHMORE Examples of such a resin include VG-3101L (manufactured by Printec Co., Ltd.); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, and NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); YX8800 (manufactured by Mitsubishi Chemical Corporation); and HP4032, HP4032D, and HP4700 (manufactured by DIC Corporation).

[0074] The total content of the compound (1) and other epoxy compounds is preferably 50 parts by mass or more and 99 parts by mass or less, more preferably 60 parts by mass or more and 98 parts by mass or less, and particularly preferably 70 parts by mass or more and 95 parts by mass or less, per 100 parts by mass of the curable composition. By setting the content within this range, the resulting cured product can be easily decomposed by acid, making it suitable for chemical recycling applications.

[0075] 3. Curing Agent Preferred examples of the curing agent include phenol-based curing agents, acid anhydride-based curing agents, polythiol compounds, and amine-based curing agents. Among these curing agents, amine-based curing agents are preferred. This is because the use of an amine-based curing agent makes it possible to form a cured product that is excellent in acid decomposability and adhesiveness. The curing agent may be a heat-curing agent that is heated, or a light-curing agent that is irradiated with light, but a heat-curing agent is preferred. This is because a cured product can be easily formed.

[0076] Examples of phenol-based curing agents include polyhydric phenol compounds such as phenol novolac resins, cresol novolac resins, aromatic hydrocarbon formaldehyde resin-modified phenolic resins, dicyclopentadiene phenol adduct resins, phenol aralkyl resins (Xyloc resins), naphthol aralkyl resins, trisphenylolmethane resins, tetraphenylolethane resins, naphthol novolac resins, naphthol-phenol co-condensed novolac resins, naphthol-cresol co-condensed novolac resins, biphenyl-modified phenolic resins (polyhydric phenol compounds in which phenol nuclei are linked via bismethylene groups), biphenyl-modified naphthol resins (polyhydric naphthol compounds in which phenol nuclei are linked via bismethylene groups), aminotriazine-modified phenolic resins (compounds having a phenol skeleton, a triazine ring, and a primary amino group in the molecular structure), and alkoxy group-containing aromatic ring-modified novolac resins (polyhydric phenol compounds in which phenol nuclei and alkoxy group-containing aromatic rings are linked via formaldehyde).

[0077] Examples of acid anhydride curing agents include himic anhydride, phthalic anhydride, maleic anhydride, methyl himic anhydride, succinic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride adduct, benzophenone tetracarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and hydrogenated methylnadic anhydride.

[0078] Examples of the polythiol compound include pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(thioglycolate), dipentaerythritol hexakis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptobutyrate), 1,3,4,6-tetrakis(2-mercaptoethyl)-1,3,4,6-tetraazaochydropentalene-2,5-dione, 1,3,5-tris(3-mercaptopropyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8-, 4,7-, or 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaoctane, and the like. Undecane, 1,3,4,6-tetrakis(2-mercaptoethyl)glycoluril, 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercaptopropylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11 -dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethyl thio)-1,3-dithiane, 1,1,5,5-tetrakis(mercaptomethylthio)-3-thiapentane, 1,1,6,6-tetrakis(mercaptomethylthio)-3,4-dithiahexane, 2,2-bis(mercaptomethylthio)ethanethiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-bis(mercaptomethylthio)-1,9-dimercapto-2,5,8-trithianonane, 3-mercaptomethylthio-1,6-dimercapto-2,5-Dithiahexane, 1,1,9,9-tetrakis(mercaptomethylthio)-5-(3,3-bis(mercaptomethylthio)-1-thiapropyl)3,7-dithianonane, tris(2,2-bis(mercaptomethylthio)ethyl)methane, tris(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, tetrakis(2,2-bis(mercaptomethylthio)ethyl)methane, tetrakis(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, 3,5,9,11-tetrakis(mercaptomethylthio)-1,13-dimercapto 1,19-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexakis(mercaptomethylthio)-1,19-dimercapto-2,6,8,12,14,18-hexathianonadecane, 9-(2,2-bis(mercaptomethylthio)ethyl)-3,5,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3,4,8,9-tetrakis(mercaptomethylthio)-1,11-dimercapto-2,5,7,10-tetrathiaundecane, 3,4,8 , 9,13,14-hexakis(mercaptomethylthio)-1,16-dimercapto-2,5,7,10,12,15-hexathiahexadecane, 8-[bis(mercaptomethylthio)methyl]-3,4,12,13-tetrakis(mercaptomethylthio)-1,15-dimercapto-2,5,7,9,11,14-hexathiapentadecane, 4,6-bis[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-1,3-dithiane, 4-[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithia heptylthio]-6-mercaptomethylthio-1,3-dithiane, 1,1-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-1,3-bis(mercaptomethylthio)propane, 1-[4-(6-mercaptomethylthio)-1,3-dithianylthio]-3-[2,2-bis(mercaptomethylthio)ethyl]-7,9-bis(mercaptomethylthio)-2,4,6,10-tetrathiaundecane, 1,5-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-3-[2-(1,3-dithietanyl)]methyl-2,4-Dithiapentane, 3-[2-(1,3-dithietanyl)]methyl-7,9-bis(mercaptomethylthio)-1,11-dimercapto-2,4,6,10-tetrathiaundecane, 9-[2-(1,3-dithietanyl)]methyl-3,5,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3-[2-(1,3-dithietanyl)]methyl-7,9,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,4,6,10,12,16 -Hexathiaheptadecane, 3,7-bis[2-(1,3-dithietanyl)]methyl-1,9-dimercapto-2,4,6,8-tetrathianonane, 4,6-bis{3-[2-(1,3-dithietanyl)]methyl-5-mercapto-2,4-dithiapentylthio}-1,3-dithiane, 4,6-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-6-[4-(6-mercaptomethylthio)-1,3-dithianylthio]-1,3-dithiane, 4-[3,4,8,9-tetrakis(mercaptomethylthio)-11-mercapto-2,5 ,7,10-tetrathiaundecyl]-5-mercaptomethylthio-1,3-dithiolane, 4,5-bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]-1,3-dithiolane, 4-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]-5-mercaptomethylthio-1,3-dithiolane, 4-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl]-5-mercaptomethylthio-1 ,3-dithiolane, 2-{bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]methyl}-1,3-dithietane, 2-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]mercaptomethylthiomethyl-1,3-dithietane, 2-[3,4,8,9-tetrakis(mercaptomethylthio)-11-mercapto-2,5,7,10-tetrathiaundecylthio]mercaptomethylthiomethyl-1,3-dithietane, 2-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl]mercaptomethylthiomethyl-1,3-dithietane, 4,5-bis{1-[2-(1,3-dithietanyl)]-3-mercapto-2-thiapropylthio}-1,3-dithiolane, 4-{1-[2-(1,3-dithietanyl)]-3-mercapto-2-thiapropylthio}-5-[1,2-bis(mercaptomethylthio) Examples of suitable polythiol compounds include 2-(4-(5-mercaptomethylthio-1,3-dithiolanyl)thio)-4-mercapto-3-thiabutylthio]-1,3-dithiolane, 2-{bis[4-(5-mercaptomethylthio-1,3-dithiolanyl)thio]methyl}-1,3-dithietane, and 4-[4-(5-mercaptomethylthio-1,3-dithiolanyl)thio]-5-{1-[2-(1,3-dithietanyl)]-3-mercapto-2-thiapropylthio}-1,3-dithiolane. Commercially available polythiol compounds include TS-G manufactured by Shikoku Chemical Industry Co., Ltd., DPMP and PEMP manufactured by SC Organic Chemical Co., Ltd., and PETG manufactured by Yodo Chemical Co., Ltd. In particular, the use of a polythiol compound with a valence of 4 or more is preferred because it provides excellent curability.

[0079] Examples of the amine-based curing agent include alkylenediamines such as ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,3-diaminobutane, 1,4-diaminobutane, and hexamethylenediamine; polyalkylpolyamines such as diethylenetriamine, triethylenetriamine, and tetraethylenepentamine; 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 1,3-diaminomethylcyclohexane, 1,2-diaminocyclohexane, and 1,4-diamino-3 alicyclic polyamines such as 1,6-diethylcyclohexane, 4,4'-diaminodicyclohexylmethane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 4,4'-diaminodicyclohexylpropane, bis(4-aminocyclohexyl)sulfone, 4,4'-diaminodicyclohexyl ether, 2,2'-dimethyl-4,4'-diaminodicyclohexylmethane, isophoronediamine, and norbornenediamine; m-xylylenediamine, diaminodiphenyl Aromatic polyamines such as methane, diaminodiphenyl sulfone, diethyltoluenediamine, 1-methyl-3,5-diethyl-2,4-diaminebenzene, 1-methyl-3,5-diethyl-2,6-diaminobenzene, 1,3,5-triethyl-2,6-diaminobenzene, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 3,5,3',5'-tetramethyl-4,4'-diaminodiphenylmethane, etc.; guanamines such as benzoguanamine and acetoguanamine; 2-methylimidazole, 2-ethyl imidazoles such as 2-methyl-4-imidazole, 2-isopropylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 2-aminopropylimidazole; dihydrazides such as oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, and phthalic acid dihydrazide;N,N-dimethylaminoethylamine, N,N-diethylaminoethylamine, N,N-diisopropylaminoethylamine, N,N-diallylaminoethylamine, N,N-benzylmethylaminoethylamine, N,N-dibenzylaminoethylamine, N,N-cyclohexylmethylaminoethylamine, N,N-dicyclohexylaminoethylamine, N-(2-aminoethyl)pyrrolidine, N-(2-aminoethyl)piperidine, N-(2-aminoethyl)morpholine, N-(2-aminoethyl)piperazine, N-(2-aminoethyl)-N'-methylpiperazine, N,N-dimethylaminopropylamine, N,N-diethylaminopropylamine, N,N-diisopropylaminopropylamine, N,N-diallylaminopropylamine, N,N-benzylmethylaminopropylamine, N,N-dibenzylaminopropylamine, N,N-cyclohexylmethylaminopropylamine, N,N-dicyclohexylaminopropylamine, N-(3-aminopropyl)pyrrolidine, N-(3-aminopropyl)piperidine, N-(3-aminopropyl)morpholine, N-(3-aminopropyl)piperazine, N-(3-aminopropyl)-N'-methylpiperidine, 4-(N,N-dimethylamino)benzylamine, 4-(N,N-diethylamino)benzylamine, 4-(N,N-diisopropylamino)benzylamine, N,N,-dimethylisophoronediamine, N,N-dimethylbisaminocyclohexane, N,N,N'-trimethylethylenediamine, N'-ethyl-N,N-dimethylethylenediamine, N,N,N'-trimethylethylenediamine, N'-ethyl-N,N-dimethylpropanediamine, N'-ethyl-N,N-dibenzylaminopropylamine;Examples include N,N-(bisaminopropyl)-N-methylamine, N,N-bisaminopropylethylamine, N,N-bisaminopropylpropylamine, N,N-bisaminopropylbutylamine, N,N-bisaminopropylpentylamine, N,N-bisaminopropylhexylamine, N,N-bisaminopropyl-2-ethylhexylamine, N,N-bisaminopropylcyclohexylamine, N,N-bisaminopropylbenzylamine, N,N-bisaminopropylallylamine, bis[3-(N,N-dimethylaminopropyl)]amine, bis[3-(N,N-diethylaminopropyl)]amine, bis[3-(N,N-diisopropylaminopropyl)]amine, bis[3-(N,N-dibutylaminopropyl)]amine, and the like;

[0080] Among the amine-based curing agents, amine-based latent curing agents that do not react with the epoxy compound when mixed but react and cure by heating can also be used. Examples of the amine-based latent curing agents include dibasic acid dihydrazides such as oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, and phthalic acid dihydrazide; guanamines such as benzoguanamine and acetoguanamine; dicyandiamide; melamine; and modified amines such as dehydration condensation products of amine compounds and carboxylic acids, adducts of amine compounds and epoxy compounds, adducts of amine compounds and isocyanate compounds, Michael adducts of amine compounds, Mannich reaction products of amine compounds, condensates of amine compounds and urea, and condensates of amine compounds and ketones.

[0081] Among the above-mentioned amine-based latent curing agents, preferred are adducts of an amine compound having one or more active hydrogens with a polyepoxy compound and / or a polyisocyanate compound, or those obtained by combining this with a phenolic resin.

[0082] Examples of the amine compound having one or more active hydrogens include alkylenediamines such as ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,3-diaminobutane, 1,4-diaminobutane, and hexamethylenediamine; polyalkylpolyamines such as diethylenetriamine, triethylenetriamine, and tetraethylenepentamine; 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 1,3-diaminomethylcyclohexane, 1,2-diaminocyclohexane, and 1, Alicyclic polyamines such as 4-diamino-3,6-diethylcyclohexane, 4,4'-diaminodicyclohexylmethane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 4,4'-diaminodicyclohexylpropane, bis(4-aminocyclohexyl)sulfone, 4,4'-diaminodicyclohexyl ether, 2,2'-dimethyl-4,4'-diaminodicyclohexylmethane, isophoronediamine, and norbornenediamine; m-xylylenediamine, diaminodicyclohexylmethane, ... aromatic polyamines such as diaminodiphenylmethane, diaminodiphenyl sulfone, diethyltoluenediamine, 1-methyl-3,5-diethyl-2,4-diaminobenzene, 1-methyl-3,5-diethyl-2,6-diaminobenzene, 1,3,5-triethyl-2,6-diaminobenzene, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 3,5,3',5'-tetramethyl-4,4'-diaminodiphenylmethane; guanamines such as benzoguanamine and acetoguanamine; 2-methylimidazole, 2 imidazoles such as 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 2-aminopropylimidazole; dihydrazides such as oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, and phthalic acid dihydrazide;N,N-dimethylaminoethylamine, N,N-diethylaminoethylamine, N,N-diisopropylaminoethylamine, N,N-diallylaminoethylamine, N,N-benzylmethylaminoethylamine, N,N-dibenzylaminoethylamine, N,N-cyclohexylmethylaminoethylamine, N,N-dicyclohexylaminoethylamine, N-(2-aminoethyl)pyrrolidine, N-(2-aminoethyl)piperidine, N-(2-aminoethyl)morpholine, N-(2-aminoethyl)piperazine, N-(2-aminoethyl)-N'-methylpiperazine, N,N-dimethylaminopropylamine, N,N-diethylaminopropylamine, N,N-diisopropylaminopropylamine, N,N-diallylaminopropylamine, N,N-benzylmethylaminopropylamine, N,N-dibenzylaminopropylamine, N,N-cyclohexylmethylaminopropylamine, N,N-dicyclohexylaminopropylamine, N-(3-aminopropyl)pyrrolidine, N-(3-aminopropyl)piperidine, N-(3-aminopropyl)morpholine, N-(3-aminopropyl)piperazine, N-(3-aminopropyl)-N'-methylpiperidine, 4-(N,N-dimethylamino)benzylamine, 4-(N,N-diethylamino)benzylamine, 4-(N,N-diisopropylamino)benzylamine, N,N,-dimethylisophoronediamine, N,N-dimethylbisaminocyclohexane, N,N,N'-trimethylethylenediamine, N'-ethyl-N,N-dimethylethylenediamine, N,N,N'-trimethylethylenediamine, N'-ethyl-N,N-dimethylpropanediamine, N'-ethyl-N,N-dibenzylaminopropylamine;Examples include N,N-(bisaminopropyl)-N-methylamine, N,N-bisaminopropylethylamine, N,N-bisaminopropylpropylamine, N,N-bisaminopropylbutylamine, N,N-bisaminopropylpentylamine, N,N-bisaminopropylhexylamine, N,N-bisaminopropyl-2-ethylhexylamine, N,N-bisaminopropylcyclohexylamine, N,N-bisaminopropylbenzylamine, N,N-bisaminopropylallylamine, bis[3-(N,N-dimethylaminopropyl)]amine, bis[3-(N,N-diethylaminopropyl)]amine, bis[3-(N,N-diisopropylaminopropyl)]amine, bis[3-(N,N-dibutylaminopropyl)]amine, and the like;

[0083] Examples of the polyepoxy compound include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol, and phloroglucinol; and polynuclear polyhydric phenols such as dihydroxynaphthalene, biphenol, methylenebisphenol (bisphenol F), methylenebis(ortho-cresol), ethylidenebisphenol, isopropylidenebisphenol (bisphenol A), isopropylidenebis(ortho-cresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis(4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfonylbisphenol, oxybisphenol, phenol novolac, orthocresol novolac, ethylphenol novolac, butylphenol novolac, octylphenol novolac, resorcinol novolac, and terpene phenol. polyglycidyl ether compounds of alcohol compounds; polyglycidyl ethers of polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, hexanediol, polyglycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, and bisphenol A-alkylene oxide adducts; maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimer acid, Glycidyl esters of aliphatic, aromatic, or alicyclic polybasic acids, such as phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, and endomethylenetetrahydrophthalic acid, and homopolymers or copolymers of glycidyl methacrylate; epoxy compounds having a glycidylamino group, such as N,N-diglycidylaniline, bis(4-(N-methyl-N-glycidylamino)phenyl)methane, and diglycidyl orthotoluidine;Examples include epoxidized products of cyclic olefin compounds such as vinylcyclohexene diepoxide, dicyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylate, and bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; epoxidized conjugated diene polymers such as epoxidized polybutadiene and epoxidized styrene-butadiene copolymers; and heterocyclic compounds such as triglycidyl isocyanurate.

[0084] Examples of the polyisocyanate compound include aromatic diisocyanates such as 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, diphenylmethane-4,4'-diisocyanate, phenylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, 1,5-naphthylene diisocyanate, 1,5-tetrahydronaphthalene diisocyanate, 3,3'-dimethyldiphenyl-4,4'-diisocyanate, dianisidine diisocyanate, and tetramethylxylylene diisocyanate; isophorone diisocyanate, dicyclohexylmethane-4,4'-diisocyanate; Examples of suitable isocyanate compounds include alicyclic diisocyanates such as trans-1,4-cyclohexyl diisocyanate and norbornene diisocyanate; aliphatic diisocyanates such as tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4 and / or (2,4,4)-trimethylhexamethylene diisocyanate and lysine diisocyanate; isocyanurate trimerization products, biuret trimerization products, and trimethylolpropane adducts of the above-exemplified diisocyanates; triphenylmethane triisocyanate, 1-methylbenzene-2,4,6-triisocyanate, dimethyltriphenylmethane tetraisocyanate, etc. Furthermore, these isocyanate compounds may be used in a carbodiimide-modified, isocyanurate-modified, biuret-modified, or other modified form, or may be used in the form of a blocked isocyanate blocked with various blocking agents.

[0085] Examples of the phenolic resin include polyhydric phenol compounds such as phenol novolac resin, cresol novolac resin, aromatic hydrocarbon formaldehyde resin-modified phenolic resin, dicyclopentadiene phenol addition type resin, phenol aralkyl resin (Xyloc resin), naphthol aralkyl resin, trisphenylolmethane resin, tetraphenylolethane resin, naphthol novolac resin, naphthol-phenol co-condensed novolac resin, naphthol-cresol co-condensed novolac resin, biphenyl-modified phenolic resin (a polyhydric phenol compound in which phenol nuclei are linked via bismethylene groups), biphenyl-modified naphthol resin (a polyhydric naphthol compound in which phenol nuclei are linked via bismethylene groups), aminotriazine-modified phenolic resin (a compound having a phenol skeleton, a triazine ring, and a primary amino group in its molecular structure), and alkoxy group-containing aromatic ring-modified novolac resin (a polyhydric phenol compound in which phenol nuclei and alkoxy group-containing aromatic rings are linked via formaldehyde).

[0086] Commercially available amine-based latent curing agents include, for example, ADEKA HARDNER EH-3636S (manufactured by ADEKA Corporation; dicyandiamide-type latent curing agent), ADEKA HARDNER EH-4351S (manufactured by ADEKA Corporation; dicyandiamide-type latent curing agent), ADEKA HARDNER EH-5011S (manufactured by ADEKA Corporation; imidazole-type latent curing agent), ADEKA HARDNER EH-5046S (manufactured by ADEKA Corporation; imidazole-type latent curing agent), ADEKA HARDNER EH-4357S (manufactured by ADEKA Corporation; polyamine-type latent curing agent), ADEKA HARDNER EH-5057P (manufactured by ADEKA Corporation; polyamine-type latent curing agent), and ADEKA HARDNER Examples include EH-5057PK (manufactured by ADEKA Corporation; polyamine-type latent curing agent), Amicure PN-23 (manufactured by Ajinomoto Fine-Techno Co., Ltd.; amine adduct-based latent curing agent), Amicure PN-40 (manufactured by Ajinomoto Fine-Techno Co., Ltd.; amine adduct-based latent curing agent), Amicure VDH (manufactured by Ajinomoto Fine-Techno Co., Ltd.; hydrazide-based latent curing agent), and Fujicure FXR-1020 (manufactured by T&K TOKA Corporation; latent curing agent).

[0087] The content of the curing agent is preferably 0.1 parts by mass or more and 50 parts by mass or less, more preferably 1 part by mass or more and 30 parts by mass or less, and particularly preferably 3 parts by mass or more and 20 parts by mass or less, per 100 parts by mass of the curable composition. This is because, by being in this range, a cured product having excellent acid decomposability can be formed. Also, a cured product having excellent adhesiveness can be formed.

[0088] The content of the curing agent is preferably 1 part by mass or more and 80 parts by mass or less, more preferably 3 parts by mass or more and 70 parts by mass or less, and particularly preferably 5 parts by mass or more and 30 parts by mass or less, relative to 100 parts by mass of the total of the compound (1) and the other epoxy compounds. The content within the above range is preferred because a curable composition having excellent curability and adhesiveness and a cured product having excellent adhesiveness can be obtained.

[0089] 4. Other Components The curable composition may contain other components in addition to the above-described compound (1), other epoxy compounds, and curing agents. Examples of such other components include commonly used additives such as curing catalysts, inorganic fillers, diluents, reinforcing materials, silane coupling agents, lubricants, pigments, thickeners, thixotropic agents, antioxidants, light stabilizers, UV absorbers, antifoaming agents, rust inhibitors, colloidal silica, and colloidal alumina. In the present disclosure, adhesive resins such as xylene resins and petroleum resins may also be used in combination.

[0090] Examples of the curing catalyst include phosphine compounds such as triphenylphosphine; phosphonium salts such as tetraphenylphosphonium bromide; 2-methylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 1-cyanoethyl-2-methylimidazole, 1-{3-[(3-trimethoxysilyl)propylaminocarbonylamino]propyl}-2-methylimidazole, 1-[3-trimethoxysilylpropylaminomethyl]-4-methylimidazole, 1-[3-(trimethoxysilylpropyl)]imidazole, and 1-[3-(trimethoxysilylpropyl)]imidazole. Examples of the curing accelerator include imidazoles; imidazole salts formed by the imidazoles with trimellitic acid, isocyanuric acid, boron, or the like; amines such as benzyldimethylamine and 2,4,6-tris(dimethylaminomethyl)phenol; quaternary ammonium salts such as trimethylammonium chloride; ureas such as 3-(p-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-phenyl-1,1-dimethylurea, isophorone diisocyanate-dimethylurea, and tolylene diisocyanate-dimethylurea; and complex compounds of boron trifluoride with amines, ether compounds, or the like. These curing accelerators may be used alone or in combination of two or more.

[0091] The content of the curing catalyst in the curable composition is preferably 0.01 to 20 parts by mass per 100 parts by mass of the total of the compound (1) and the other epoxy compounds.

[0092] Examples of the filler include silica such as fused silica and crystalline silica, powders such as magnesium hydroxide, aluminum hydroxide, zinc molybdate, calcium carbonate, silicon carbonate, calcium silicate, potassium titanate, beryllium, zirconia, zircon, fosterite, steatite, spinel, mullite, and titania, or beads obtained by spheronizing these, and inorganic fillers such as glass fiber. The content of the filler in the curable composition of the present disclosure is preferably about 0 to 90% by mass, and more preferably 1 to 30% by mass.

[0093] Examples of the diluent include non-reactive diluents (plasticizers) such as dioctyl phthalate, dibutyl phthalate, benzyl alcohol, and coal tar.

[0094] Examples of the reinforcing material include fibrous fillers such as glass fiber, pulp fiber, synthetic fiber, and ceramic fiber; and reinforcing materials such as glass cloth, aramid cloth, and carbon fiber.

[0095] Examples of the silane coupling agent include γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-N'-β-(aminoethyl)-γ-aminopropyltriethoxysilane, γ-anilinopropyltriethoxysilane, γ-glycidoxypropyltriethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, vinyltriethoxysilane, N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, and γ-mercaptopropyltrimethoxysilane.

[0096] Examples of the lubricant include candelilla wax, carnauba wax, Japan wax, Ibota wax, beeswax, lanolin, spermaceti, montan wax, petroleum wax, aliphatic wax, aliphatic esters, aliphatic ethers, aromatic esters, and aromatic ethers.

[0097] The curable composition of the present disclosure can be used in a wide range of applications, such as paints, adhesives, pressure-sensitive adhesives, coatings, fiber sizing agents, building materials, and electronic components. In particular, because it can be easily decomposed by acid, it is useful as a recycled material. More specifically, it can be used as a recycled paint, recycled adhesive, recycled pressure-sensitive adhesive, recycled coatings, recycled fiber sizing agents, recycled building materials, recycled electronic components, and the like. The term "recycled" as used herein includes applications in which the cured product is decomposed by acid decomposition or the like, and the adherend to which the cured product is adhered is recovered and reused. Furthermore, compounds such as hydroxyaldehyde and trimethylolpropane can be recovered by neutralizing, solvent extraction, purifying, or the like, as necessary, from the decomposition product obtained by acid decomposition. These compounds can be reused as starting materials for the compound represented by Formula (1). In addition, in the above applications, the material to which the curable composition is applied, such as the adherend when used as an adhesive or coating, may be any of metal materials, inorganic materials other than metal materials, polymeric materials, and the like, but metal materials are preferred. This is because the cured product of the curable composition of the present disclosure exhibits excellent adhesiveness. Examples of the metal material include iron, zinc, nickel, copper, aluminum, titanium, stainless steel, mild steel, plated steel, etc. Examples of the inorganic material include glass substrates such as quartz glass substrates, Pyrex (registered trademark) glass substrates, and synthetic quartz substrates.Examples of the polymer material include cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl cellulose, and nitrocellulose; polyamide; polyimide; polyurethane; epoxy resin; polycarbonate; polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4'-dicarboxylate, and polybutylene terephthalate; polystyrene; polyolefins such as polyethylene, polypropylene, and polymethylpentene; vinyl compounds such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; acrylic resins such as polymethyl methacrylate and polyacrylate; polycarbonate; polysulfone; polyethersulfone; polyetherketone; polyetherimide; polyoxyethylene, norbornene resin, and cycloolefin polymer (COP).

[0098] E. Cured Product Next, the cured product of the present disclosure will be described in detail. The cured product of the present disclosure is characterized by being a cured product of a curable composition containing the compound (1) described above.

[0099] The cured product of the present disclosure can be decomposable by acid and can also have excellent adhesion to an adherend such as a substrate.

[0100] The cured product of the present disclosure is formed using a curable composition. The content of such a curable composition can be the same as that described in the section "D. Curable composition" above, and therefore a description thereof will be omitted here. Furthermore, the method for forming the cured product may be any method capable of curing the curable composition, and can be, for example, the same as that described in the section "F. Method for producing a cured product" below, and therefore a description thereof will be omitted here.

[0101] F. Method for Producing Cured Product Next, a method for producing a cured product of the present disclosure will be described in detail. The method for producing a cured product of the present disclosure is characterized by having a curing step of curing a curable composition containing the compound (1) described above.

[0102] According to the present disclosure, a cured product that is decomposable by acid and has good adhesion to an adherend can be easily obtained.

[0103] The manufacturing method of the present disclosure includes a curing step. The curing step included in the manufacturing method of the present disclosure will be described in detail below.

[0104] 1. Curing Step This step is a step of curing the curable composition. The details of such a curable composition can be the same as those described in the section "D. Curable Composition" above, and therefore a description thereof will be omitted here. Furthermore, the method for forming a cured product may be any method capable of curing the curable composition, and may be the same as those described in the section "F. Method for Producing a Cured Product" described below, and therefore a description thereof will be omitted here. The method for curing the curable composition is not particularly limited as long as it can cure the curable composition, and examples thereof include a method of heating the curable composition and a method of irradiating the curable composition with light. In the present disclosure, the curing method is preferably a method of heating the curable composition. The heating temperature can be, for example, 100°C or higher and 180°C or lower. This is because a cured product can be easily formed.

[0105] 2. Other Steps The manufacturing method of the present disclosure may include steps other than the curing step. Examples of such steps include a step of applying the curable composition.

[0106] G. Method for Producing Decomposition Product Next, the method for producing the decomposition product of the present disclosure will be described in detail. The production method of the present disclosure is characterized by including a decomposition step of decomposing a cured product of the curable composition containing the compound (1) described above.

[0107] According to the present disclosure, a cured product can be easily decomposed to obtain a decomposition product.

[0108] The manufacturing method of the present disclosure includes a decomposition step. The decomposition step included in the manufacturing method of the present disclosure will be described in detail below.

[0109] 1. Decomposition Step This step is a step of decomposing a cured product of the curable composition containing the compound (1) described above. The details of the curable composition and the cured product can be the same as those described in the sections "D. Curable Composition" and "E. Cured Product" above, and therefore a description thereof will be omitted here. The method for decomposing the cured product is not particularly limited as long as it can decompose the cured product, but for example, a method of contacting the cured product with an acidic solution is preferred. This is because this allows for more effective curing of the cured product of the curable composition containing the compound (1).

[0110] Examples of methods for bringing the cured product into contact with the acidic solution include a method of applying the acidic solution by spraying or the like, and a method of immersing the cured product in the acidic solution.

[0111] Examples of acids used in the acidic solution include hydrochloric acid, sulfuric acid, nitric acid, acetic acid, etc., and hydrochloric acid is preferred, as this facilitates decomposition. The solvent used in the acidic solution is not particularly limited, and examples include organic solvents and water that are suitable for decomposition and its recovery. The pH of the acidic solution can be 0 or more and 6 or less, preferably 0.5 or more and 5 or less, and particularly preferably 1 or more and 4 or less, as this facilitates decomposition. The pH may be the pH at the temperature of the acidic solution.

[0112] 2. Others The manufacturing method of the present disclosure includes the decomposition step, but may also include other steps as necessary. Examples of such other steps include a neutralization step of neutralizing an acidic solution after the decomposition step, and an extraction step of extracting decomposition products from the cured product.

[0113] H. Decomposition Method Next, the decomposition method of the present disclosure will be described in detail. The decomposition method of the present disclosure is characterized by having a decomposition step of decomposing a cured product of a curable composition containing the compound (1) described above.

[0114] According to the present disclosure, a cured product can be easily decomposed to obtain a decomposition product.

[0115] The decomposition method of the present disclosure includes a decomposition step. The content of such a decomposition step can be the same as that described in the section "G. Method for producing decomposition products" above, and therefore a description thereof will be omitted here. The decomposition method may also include steps other than the decomposition step. The content of such other steps can also be the same as that described in the section "G. Method for producing decomposition products" above, and therefore a description thereof will be omitted here.

[0116] I. Others [1] A compound represented by the following general formula (1): In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 10 carbon atoms which may have a hydroxyl group or a halogen atom as a substituent, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２ represents a hydrogen atom or a group represented by the following general formula (11): １ or X ２ At least one of the above is a group represented by the general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond. [2] The compound according to [1], which is a compound represented by the following general formula (1b) or (1c): R in the formulas (1b) and (1c) １ , R ２ , X １ , X ２and n is R in formula (1). １ , R ２ , X １ , X ２ and n. [3] X １ and X ２ is a group represented by the general formula (11). [4] An epoxy resin containing the compound according to any one of [1] to [3]. [5] An epoxy resin according to [4], containing two or more compounds represented by the following general formula (1): [6] A compound represented by the general formula (1), wherein X １ and X ２ [7] The epoxy resin according to [4] or [5], which contains at least a compound represented by the general formula (1), wherein X １ and X ２ is a group represented by the general formula (11), and a compound represented by the general formula (1), １ is a group represented by the general formula (11), and X ２ is a hydrogen atom, and a compound represented by the general formula (1), １ is a hydrogen atom, and X ２ and at least one compound represented by the general formula (11). [8] The epoxy resin according to [5] or [6], wherein X is a group represented by the general formula (1), １ and X ２ [9] The epoxy resin according to any one of items [5] to [7], wherein the content of the compound represented by the general formula (11) is 20 parts by mass or more and 80 parts by mass or less in 100 parts by mass of the total of the compounds represented by the general formula (1). １ is a group represented by the general formula (11), and X ２ is a hydrogen atom is 20 parts by mass or more and 80 parts by mass or less in 100 parts by mass of the total of the compounds represented by the general formula (1).

[10] A method for producing a compound represented by the following general formula (1), comprising an epoxidation step of reacting a compound represented by the following general formula (2) with epihalohydrin: In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 10 carbon atoms which may have a hydroxyl group or a halogen atom as a substituent, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２ represents a hydrogen atom or a group represented by the following general formula (11): １ or X ２ At least one of the above is a group represented by the following general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond. In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, or an aryl group having 5 to 10 carbon atoms which may have a halogen atom as a substituent, a hydroxyl group, or a halogen atom; R ２represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methyl glycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4.

[11] A method for producing the compound according to

[10] , wherein the epoxidation step is a step of reacting the compound represented by general formula (2) with an epihalohydrin in the presence of a phase transfer catalyst.

[12] A curable composition containing the compound according to any one of [1] to [3] and a curing agent.

[13] A recyclable material containing the compound according to any one of [1] to [3].

[14] A cured product of the curable composition containing the compound according to any one of [1] to [3].

[15] A method for producing a cured product, comprising a curing step of curing a curable composition containing the compound according to any one of [1] to [3].

[16] A method for producing a decomposition product, comprising a decomposition step of decomposing a cured product of a curable composition containing the compound according to any one of [1] to [3].

[17] A decomposition method, comprising a decomposition step of decomposing a cured product of a curable composition containing the compound according to any one of [1] to [3].

[0117] The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples.

[0118] Example 1: Preparation of Epoxy Resin No. 1 In a 500 mL flask equipped with a reflux apparatus, a stirrer, and a dropping apparatus, 25.8 g (0.11 mol) of o-DOP (a compound represented by the formula below) and 200 g (2.2 mol, 20 equivalents) of epichlorohydrin were charged, and 8.5 g (0.10 mol, 0.95 equivalents) of a 48% by weight aqueous sodium hydroxide solution was added dropwise at 65-70°C and 19.0 kPa over 2 hours. After the addition was completed, the mixture was aged for 1 hour while distilling off water. After the reaction was completed, the reaction solution was filtered to remove by-product salts, and the solution was transferred again to a 500 mL four-neck flask equipped with a reflux apparatus, a stirrer, and a dropping apparatus. 0.79 g (2.5 mmol, 0.02 equivalents) of cetyltrimethylammonium chloride was charged as a phase transfer catalyst, and 22.1 g (0.24 moles, 2.0 equivalents) of a 48% by weight aqueous sodium hydroxide solution was added dropwise at 58-60°C and 14.0 kPa over 1.5 hours. After the dropwise addition was completed, the mixture was aged for 2 hours while distilling off water. After the reaction was completed, 10 g each of Kyoward 600 and 700SL was added to remove excess base, and the solution was filtered to separate the by-product salt and Kyoward. The excess epichlorohydrin was distilled off under reduced pressure, and the resulting mixture was filtered through Celite to obtain Epoxy Resin No. 1, a pale yellow liquid. The components contained in Epoxy Resin No. 1 were analyzed by gas chromatography. １ The epoxy resins were identified by H-NMR. As a result, it was found that Epoxy Resin No. 1 contained the following o-DOP-EP1 and o-DOP-EP2 in a mass ratio of 41 / 59.

[0119]

[0120]

[0121]

[0122] <Gas Chromatography Analysis> Epoxy Resin No. 1 obtained in Example 1 was diluted 50 times by mass with chloroform and analyzed using a GC / MS system [Shimadzu QP2010plus (CI method, reagent gas: isobutane)] under the following measurement conditions. Measurement Conditions) Column: HP-5MS (0.25 mm x 30 m, 0.25 μm) Oven: 80°C (2 min) - 20°C / min - 200°C (0 min) - 10°C / min - 300°C (2 min) Flow: 1.5 mL / min Split ratio: 1 / 10 Injection temp: 300°C Interface temp: 250°C Ion source temp: 200°C Scans: m / z 80-550

[0123] <NMR Analysis> The epoxy resin No. 1 obtained above was fractionated using a recycling preparative HPC (Japan Analytical Industry Co., Ltd.; LaboACE LC-5060) under the following fractionation conditions, and the resulting o-DOP-diEP (81.11 mg) and o-DOP-monoEP (52.25 mg) were subjected to NMR analysis. [Fraction Conditions] Column: JAIGEL 2HR x 2 Flow rate: 10 ml / min, isocratic injection volume: 2 mL Solvent: CHCl3 (Fujifilm Wako Pure Chemical Industries, Ltd., for GPC) Detector: RI Sample: 0.20793 g / 2 mL Number of recycles: 10 The fractionated samples were evaporated, air-dried, and their masses were measured. (These fractions have not been confirmed by other analyses.) o-DOP-diEP 81.11 mg o-DOP-monoEP 52.25 mg

[0124] [Adhesion Evaluation] One-component epoxy resin compositions were prepared according to the formulations shown in Table 1 (the formulation units are "parts by mass"), and the shear strength of the cured product of each composition was measured. The materials used in the formulations are as follows. Compound (1): Epoxy resin No. 1 Other epoxy compounds: EP-4100E: bisphenol A epoxy resin, manufactured by ADEKA Corporation Curing agent: 2E4MZ: 2-ethyl-4-methylimidazole Inorganic filler RY-200S: fumed silica (manufactured by Nippon Aerosil Co., Ltd.) (Method for measuring shear strength) Shear strength was measured as follows. A silicone sheet with a hole 4 mm in diameter and 1 mm in height was placed on each substrate, and the resin composition was placed inside the hole. This was cured at 150°C for 2 hours to produce a cylindrical molded product 4 mm in diameter and 1 mm in height. Thereafter, shear strength (MPa) was measured using a 4000Plus bond tester (manufactured by Nordson DAGE). The following substrates were used. The results are shown in Table 1 and Figure 7. Ni substrate: Ni-plated SPCC-SB (manufactured by Test Piece Co., Ltd.) Cu substrate: C1100 (manufactured by Engineering Test Service Co., Ltd.) Al substrate: A5052P (manufactured by Test Piece Co., Ltd.)

[0125]

[0126] As shown in Table 1 and Fig. 7, the one-component epoxy resin composition of the present disclosure was found to have superior adhesive strength, particularly with Cu and Al, compared to a resin composition not using Epoxy Resin No. 1.

[0127] [Decomposition Test] One-component epoxy resin compositions were prepared according to the formulations shown in Table 2 (the formulation units are "parts by mass"), and the decomposition behavior of the cured products of each composition in an acid solvent was confirmed. Other epoxy compounds: EP-4088S: dicyclopentadiene-type epoxy resin, manufactured by ADEKA Corporation

[0128] (Method for confirming degradability) The resin composition was uniformly spread on a Teflon (registered trademark) plate to a thickness of 30 μm and cured at 150°C for 2 hours. The mass of the resulting cured product was measured, and then it was immersed at room temperature for 24 hours in a mixed solution of tetrahydrofuran (THF) and water in a volume ratio of 9:1, containing HCl at a concentration of 0.1 mol / L, and the behavior was observed. The mass of the cured product remaining after immersion was measured. The results are shown in Table 2.

[0129]

[0130] In Example 2, the cured product had crumbled into small pieces after 2 hours of immersion and was completely dissolved after 24 hours. As shown in Table 2, the one-component epoxy resin composition of the present disclosure was found to have superior decomposition properties in an acid solvent compared to a resin composition that did not use Epoxy Resin No. 1.

[0131] According to the present invention, a compound capable of forming a cured product with excellent acid decomposability can be provided. The compound of the present disclosure has excellent adhesive strength to metal materials such as nickel, copper, and aluminum, and can be easily decomposed by acid, and is therefore considered to be useful as a chemically recycled material.

Claims

1. A compound represented by the following general formula (1): In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms as a substituent, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 10 carbon atoms which may have a hydroxyl group or a halogen atom, a hydroxyl group, a glycidyl ether group, a β-methyl glycidyl ether group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２ represents a hydrogen atom or a group represented by the following general formula (11): １ Or X ２ At least one of the above is a group represented by general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond.

2. The compound according to claim 1, which is a compound represented by the following general formula (1b) or (1c): R in formulas (1b) and (1c) １ , R ２ , X １ , X ２ and n is R in formula (1). １ , R ２ , X １ , X ２ and n is the same.

3. X １ and X ２ The compound according to claim 1 or 2, wherein:

4. An epoxy resin containing the compound according to claim 1.

5. The epoxy resin according to claim 4, which contains two or more compounds represented by the following general formula (1): In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms as a substituent, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 10 carbon atoms which may have a hydroxyl group or a halogen atom, a hydroxyl group, a glycidyl ether group, a β-methyl glycidyl ether group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２ represents a hydrogen atom or a group represented by the following general formula (11): １ Or X ２ At least one of the above is a group represented by the following general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond.

6. Represented by the general formula (1), X １ and X ２ The epoxy resin according to claim 4, which contains at least a compound which is a group represented by the general formula (11).

7. Represented by the general formula (1), X １ and X ２ is a group represented by the general formula (11), and １ is a group represented by the general formula (11), and X ２ is a hydrogen atom, and １ is a hydrogen atom, and X ２ The epoxy resin according to claim 4, comprising at least one compound represented by the general formula (11):

8. Represented by the general formula (1), X １ and X ２ is a group represented by general formula (11), is 20 parts by mass or more and 80 parts by mass or less in 100 parts by mass of the compound represented by general formula (1).

9. Represented by the general formula (1), X １ is a group represented by the general formula (11), and X ２ The epoxy resin according to claim 7, wherein the content of the compound in which is a hydrogen atom is 20 parts by mass or more and 80 parts by mass or less per 100 parts by mass of the compound represented by the general formula (1).

10. A method for producing a compound represented by the following general formula (1), comprising an epoxidation step of reacting a compound represented by the following general formula (2) with epihalohydrin. In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms as a substituent, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 5 to 10 carbon atoms which may have a hydroxyl group or a halogen atom, a hydroxyl group, a glycidyl ether group, a β-methyl glycidyl ether group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number from 0 to 4. X １ and X ２ represents a hydrogen atom or a group represented by the following general formula (11): １ Or X ２ At least one of the above is a group represented by the following general formula (11). In the formula, R ３ is a hydrogen atom or a methyl group, where * represents a bond. In the formula, R １ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms as a substituent, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, a glycidyl ether group, a β-methylglycidyl ether group, an aryl group having 5 to 10 carbon atoms which may have a halogen atom, a hydroxyl group, or a halogen atom; R ２ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group, a glycidyl ether group, a methylglycidyl ether group, a glycidyloxyalkyl group, a β-methylglycidyloxyalkyl group, an acryloyloxyalkyl group or a methacryloyloxyalkyl group, and n represents a number from 0 to 4.

11. The method for producing the compound according to claim 10, wherein the epoxidation step is a step of reacting the compound represented by general formula (2) with epihalohydrin in the presence of a phase transfer catalyst.

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

13. A material for recycling containing the compound according to claim 1.

14. A cured product of a curable composition containing the compound according to claim 1.

15. A method for producing a cured product, comprising a curing step of curing a curable composition containing the compound according to claim 1.

16. A method for producing a decomposition product, comprising a decomposition step of decomposing a cured product of a curable composition containing the compound according to claim 1.

17. A method for decomposing a cured product of a curable composition containing the compound according to claim 1, comprising a decomposition step.

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