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

Abstract

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, and R2 represents H, a C1-10 alkyl group, a hydroxyalkyl group, a glycidyl ether, a methyl glycidyl ether, a glycidoxyalkyl group, a beta-methyl glycidoxyalkyl group, an acryloyloxyalkyl group or a methacryloyloxyalkyl group. And n represents a number of 0-4. X1 and X2 are H or a group represented by general formula (11). And at least one of X1 and X2 is represented by general formula (11). [Chemical Formula 2] R3 is H or a methyl group.

Description

TECHNICAL FIELD

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

[0002] Epoxy resins are widely used in industry as a component or raw material for forming paints, adhesives, and various molding materials.

[0003] As epoxy resins, there are aromatic epoxy resins, alicyclic epoxy resins, and aliphatic epoxy resins, which are separately used for various purposes according to their characteristics. For example, an epoxy resin having an acetal skeleton is proposed in Patent Document 1.

[0004] PRIOR ART DOCUMENTS

[0005] PATENT DOCUMENTS

[0006] Patent Document 1: Chinese Patent Publication No. 111704711 SUMMARY

[0007] However, epoxy resin materials can provide a strong material by curing using heat or light, but on the other hand, are difficult to reuse.

[0008] Therefore, an object of the present application is to provide a compound capable of forming a cured product excellent in acid decomposability.

[0009] That is, the present application provides a compound represented by the following general formula (1).

[0010] [Chemical Formula 1]

[0011]

[0012] 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 aryl group having 5 to 10 carbon atoms which can have, as a substituent, 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-methyl glycidyl ether group, or 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 methyl glycidyl ether group, a glycidoxyalkyl group, a β-methyl glycidoxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number of 0 to 4.

[0013] X 1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11).

[0014] wherein X 1 or X2 At least one of them is a group represented by the above-mentioned general formula (11).

[0015] [Chemical Formula 2]

[0016]

[0017] Where R 3 is a hydrogen atom or a methyl group.

[0018] Where * indicates the bonding point.

[0019] Furthermore, the present invention provides an epoxy resin comprising at least one compound represented by the following general formula (1).

[0020] Furthermore, the present invention provides a method for producing a compound represented by the following general formula (1):

[0021] The process comprises an epoxidation step of reacting a compound represented by the following general formula (2) with an epihalohydrin.

[0022] [Chemical Formula 3]

[0023]

[0024] Where 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 aryl group having 5 to 10 carbon atoms, a hydroxyl group, or a halogen atom which may have 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 a halogen atom as a substituent, and 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 of 0 to 4.

[0025] X 1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11).

[0026] Among them, X 1 or X 2 At least one of them is a group represented by the above-mentioned general formula (11).

[0027] [Chemical Formula 4]

[0028]

[0029] Where R 3 is a hydrogen atom or a methyl group.

[0030] wherein * represents a bonding point.

[0031] [Chemical Formula 5]

[0032]

[0033] wherein 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 aryl group having 5 to 10 carbon atoms which can have, as a substituent, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, 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 methyl glycidyl ether group, a glycidyloxyalkyl group, a β-methyl glycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number of 0 to 4.

[0034] Further, the present application provides a composition containing the compound represented by the above formula (1) and a curing agent.

[0035] Effects of the Invention

[0036] According to the present application, it is possible to provide a compound which can form a cured product having excellent decomposition properties. BRIEF DESCRIPTION OF DRAWINGS

[0037] Figure 1 is a GC spectrum of the epoxy resin material obtained in Example 1.

[0038] Figure 2 is a MS spectrum of peak 1 of Figure 1

[0039] Figure 3 is a MS spectrum of peak 2 of Figure 1

[0040] Figure 4 is a MS spectrum of peak 3 of Figure 1

[0041] Figure 5 is a NMR spectrum of o-DOP-EP1 obtained in Example 1.

[0042] Figure 6 is a NMR spectrum of o-DOP-EP2 obtained in Example 1.

[0043] Figure 7 is a GC spectrum of Resin 3 obtained in Example 2. DETAILED DESCRIPTION

[0044] ​​​Hereinafter, the compound of the present application, a method for producing the same, and a composition thereof will be described in detail.

[0045] A. Compound

[0046] First, the compound of the present disclosure will be described.

[0047] The compound of the present disclosure (hereinafter, sometimes referred to as "compound (1)"). is characterized in that it is represented by the following general formula (1).

[0048] [Chemical Formula 6]

[0049]

[0050] 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 aryl group having 5 to 10 carbon atoms which can have, as a substituent, 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-methyl glycidyl ether group, or 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 methyl glycidyl ether group, a glycidoxyalkyl group, a β-methyl glycidoxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number of 0 to 4.

[0051] X 1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11).

[0052] wherein X 1 or X 2 is a group represented by the above general formula (11).

[0053] [Chemical Formula 7]

[0054]

[0055] In the formula, R 3 is a hydrogen atom or a methyl group.

[0056] wherein * represents a bonding point.

[0057] In the above general formula (1), as R 1The alkyl group having 1 to 20 carbon atoms represented by R1may include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, t-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, benzyl, phenethyl, and the like.

[0058] In the general formula (1), R1may be an alkyl group having 1 to 20 carbon atoms. 1 The alkoxy group having 1 to 20 carbon atoms represented by R1may include, for example, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, pentoxy, octyloxy, nonyloxy, decyloxy, and the like.

[0059] In the general formula (1), R1may be an alkyl group having 1 to 20 carbon atoms. 1 The halogen atom represented by R1may include, for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

[0060] In the general formula (1), R1may be an alkyl group having 1 to 20 carbon atoms. 1 The aryl group having a substituent represented by R1may include, for example, a phenyl group, a naphthyl group, and the like. 1 The aryl group having a substituent represented by R1may include, for example, a phenyl group, a naphthyl group, and the like.

[0061] The alkyl group having 1 to 10 carbon atoms used as a substituent for replacing a hydrogen atom in an aryl group may include the alkyl group having a specified number of carbon atoms among the alkyl group having 1 to 20 carbon atoms described as a group used in R1. 1 The alkyl group having 1 to 20 carbon atoms described as a group used in R1may include the alkyl group having a specified number of carbon atoms among the alkyl group having 1 to 20 carbon atoms described as a group used in R1.

[0062] The halogen atom used as a substituent for replacing a hydrogen atom in an aryl group may include the same halogen atom described as a halogen atom used in R1. 1 The halogen atom used as a substituent for replacing a hydrogen atom in an aryl group may include the same halogen atom described as a halogen atom used in R1.

[0063] In the general formula (1), R1may be an alkyl group having 1 to 20 carbon atoms. 2 The alkyl group having 1 to 10 carbon atoms represented by R1may include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, t-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, benzyl, phenethyl, and the like. 1 The alkyl group having 1 to 20 carbon atoms described as a group used in R1may include the alkyl group having a specified number of carbon atoms among the alkyl group having 1 to 20 carbon atoms described as a group used in R1.

[0064] R1may be an alkyl group having 1 to 20 carbon atoms. 2 In the case where R1is an alkyl group, it is preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group or an ethyl group, and especially preferably an ethyl group. This is because R1 2The compound (1) described above can produce a cured product having excellent acid decomposition properties. Furthermore, a cured product having more excellent adhesion can be formed by the compound (1). In addition, such properties are preferred, for example, from the viewpoint of being a useful compound as a chemical recycling material. Furthermore, it is preferred for reasons such as ease of obtaining raw materials.

[0065] In the general formula (1) described above, the glycidyloxyalkyl group represented by R 2 The hydroxyalkyl group represented by R

[0066] The hydroxyalkyl group represented by R 2 In the case where R

[0067] In the general formula (1) described above, the glycidyloxyalkyl group represented by R 2 The glycidyloxyalkyl group represented by R

[0068] In the general formula (1) described above, the β-methylglycidyloxyalkyl group represented by R 2 The β-methylglycidyloxyalkyl group represented by R

[0069] In the general formula (1) described above, the acryloyloxyalkyl group represented by R 2 The acryloyloxyalkyl group represented by R

[0070] In the general formula (1) described above, the methacryloyloxyalkyl group represented by R 2 The methacryloyloxyalkyl group represented by R

[0071] In the general formula (1) described above, n is preferably 0 or 1, and n is particularly preferably 0. A cured product having more excellent acid decomposition properties and adhesion can be formed because of this.

[0072] In addition, R 1 may be a group other than a hydrogen atom. In the case where n is 1 to 4, R 1 is preferably an alkyl group or a methoxy group having 1 to 4 carbon atoms, and R 1 is particularly preferably a methyl group. A cured product having excellent acid decomposition properties can be formed because of this by the compound (1). Furthermore, a cured product having more excellent adhesion can be formed because of this by the compound (1).

[0073] Furthermore, R 2preferably a group represented by the above general formula (11), more preferably a group represented by the above general formula (11) having 1 to 5 carbon atoms, particularly preferably a group represented by the above general formula (11) having 1 to 4 carbon atoms, wherein particularly preferably a group represented by the above general formula (11) having 1 to 3 carbon atoms, wherein particularly preferably a group represented by the above general formula (11) having 1 to 2 carbon atoms, wherein particularly preferably an ethyl group. Since by this compound (1), a cured product excellent in acid-decomposability can be formed. Further, since by this compound (1), a cured product more excellent in adhesiveness can be formed.

[0074] may be set to X 1 and X 2 are each independently a hydrogen atom or a group represented by the above general formula (11), for example, X 1 and X 2 are each a group represented by the above general formula (11), X 1 is a group represented by the above general formula (11), X 2 is a hydrogen atom, X 1 is a hydrogen atom, X 2 is a group represented by the above general formula (11), and the like.

[0075] In the present disclosure, preferably X 1 and X 2 are each a group represented by the above general formula (11), or X 1 is a group represented by the above general formula (11), X 2 is a hydrogen atom, wherein preferably X 1 and X 2 are each a group represented by the above general formula (11). Since by this compound (1), a cured product excellent in acid-decomposability can be formed. Further, since by this compound (1), a cured product more excellent in adhesiveness can be formed.

[0076] In the present disclosure, R 3 is preferably a hydrogen atom. Since by this compound (1), a cured product excellent in acid-decomposability can be formed. Further, since by this compound (1), a cured product more excellent in adhesiveness can be formed.

[0077] Particularly preferably, in the above general formula (1), n is 0, R 2 is an ethyl group.

[0078] Especially preferably, in the above general formula (1), n is 0, R 2 is an ethyl group, X 1 and X 2 are each a group represented by the above general formula (11), X 1 and X 2 are each a group represented by the above general formula (11), R 3 in the above general formula (1) is a hydrogen atom.

[0079] Because of the compound (1) of the above range, a cured product having more excellent acid-decomposable property can be formed. Furthermore, because of the compound (1), a cured product having more excellent adhesion property can be formed.

[0080] The compound represented by the above general formula (1) is a compound represented by any one of the following general formulae (1a), (1b) or (1c).

[0081] [Chemical Formula 8]

[0082]

[0083] [Chemical Formula 9]

[0084]

[0085] [Chemical Formula 10]

[0086]

[0087] Note that R 1 , R 2 , X 1 , X 2 and n in the compound represented by the above general formulae (1a), (1b) or (1c) can be exemplified by the examples represented by the above formula (1).

[0088] Among the compounds represented by the above general formulae (1a), (1b) or (1c), the compound represented by (1b) or (1c) is particularly preferred, and the compound represented by (1c) is particularly preferred. Because of the compound represented by the above formula, a cured product having excellent adhesion to a metal material can be formed. Furthermore, because of the compound represented by the above formula, a cured product which is easily decomposed by an acid can be formed.

[0089] The following exemplifies specific examples of the compound represented by the above general formulae (1a), (1b) or (1c).

[0090] [Chemical Formula 11]

[0091]

[0092] [Chemical Formula 12]

[0093]

[0094] [Chemical Formula 13]

[0095]

[0096] [Chemical Formula 14]

[0097]

[0098] [Chemical Formula 15]

[0099]

[0100] [Chemical Formula 16]

[0101]

[0102] [Chemical Formula 17]

[0103]

[0104] [Chemical Formula 18]

[0105]

[0106] [Chemical Formula 19]

[0107]

[0108] The total chlorine amount of the compound represented by Formula (1) of the present disclosure and mixtures thereof is preferably 10,000 ppm or less on a mass basis. In the case where the total chlorine amount exceeds 10,000 ppm, the concentration of chloride ions becomes high, and the material is likely to cause ion migration, for example, in the case where it is used as an adhesive or a sealant for electrical / electronic parts, there is a possibility that the reliability is reduced.

[0109] The total chlorine amount can be measured based on ASTM D5808.

[0110] As the use of the above-mentioned compound (1), it can be used as an epoxy resin alone or in combination with other epoxy compounds.

[0111] Further, as the specific use of such an epoxy resin, it can be set as the same as the content described in the item of "D. Curing composition" described later.

[0112] B. Method for producing compound

[0113] Next, the method for producing the compound of the present disclosure will be described.

[0114] The method for producing the compound of the present disclosure is characterized in that it is a method for producing a compound represented by the following general formula (1), having an epoxidation step of reacting a compound represented by the following general formula (2) with an epoxy halopropane.

[0115] The production method of the present disclosure has an epoxidation step.

[0116] 1. Epoxidation step

[0117] This step is a step of reacting the compound represented by the above general formula (2) (hereinafter, sometimes referred to as "compound (2)".) with an epoxy halopropane.

[0118] As the reaction method in this step, any method can be used as long as it is a method capable of reacting the compound (2) with the epoxy halopropane to form the compound represented by the above general formula (1).

[0119] As such a reaction method, a method of reacting the compound (2) with the epoxy halopropane in the presence of a phase transfer catalyst is preferred. By using a phase transfer catalyst, the reaction of the alcoholic hydroxyl group with the epoxy halopropane can be promoted.

[0120] As the epoxy halopropane, an epoxy chloropropane, an epoxy bromopropane, a β-methyl epoxy chloropropane, and the like can be exemplified.

[0121] As the phase transfer catalyst, for example, 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-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-ethyllauryl piperidinium acetate, and N-methyl-N-ethyllauryl piperidinium iodide, and the like can be exemplified. From the viewpoint of high reactivity, cetyltrimethylammonium chloride is preferred.

[0122] As the amount of use of the phase transfer catalyst, relative to 100 parts by mass of the compound represented by formula (2), 0.01 parts by mass or more and 10 parts by mass or less are preferred, 0.1 parts by mass or more and 5.0 parts by mass or less are more preferred, and 0.5 parts by mass or more and 3.2 parts by mass or less are particularly preferred.

[0123] By using within the above range, the effect of improving reactivity is excellent, and no by-products are generated.

[0124] As the above reaction method, a method of reacting in the presence of a base is preferred.

[0125] By using a base, the reaction of the alcoholic hydroxyl group with the epoxy halopropane can be particularly promoted.

[0126] As the base, for example, metal hydroxides such as sodium hydroxide, potassium hydroxide, and calcium hydroxide can be exemplified.

[0127] As the method of adding the base, a method of adding an aqueous base solution dropwise and a method of adding a solid base preferably in multiple stages can be given.

[0128] As the amount of the base to be used, 0.1 mol or more and 10 mol or less, preferably 0.2 mol or more and 5.0 mol or less, and particularly preferably 0.5 mol or more and 3.2 mol or less, per 1 mol of the compound represented by formula (2) is preferable.

[0129] By setting the content as described above, the reactivity can be improved without generating a by-product.

[0130] As the reaction method, a method of reacting under heating is preferable.

[0131] The reaction proceeds faster.

[0132] As the heating temperature, 25°C or higher and 120°C or lower, preferably 30°C or higher and 100°C or lower, and particularly preferably 40°C or higher and 80°C or lower is preferable.

[0133] By carrying out the reaction in the above temperature range, the reaction can be carried out faster and a by-product is not generated.

[0134] Further, the reaction can be carried out under pressure or under reduced pressure as needed.

[0135] In particular, by carrying out the reaction under reduced pressure, a by-product is less generated and a high reaction rate can be obtained, and thus it is preferable.

[0136] 2. Other

[0137] The production method of the present disclosure has the above-described epoxidation step, but can have other steps as needed.

[0138] As such other steps, a purification step and the like can be given.

[0139] C. Epoxy Resin

[0140] Next, the epoxy resin of the present disclosure will be described.

[0141] The epoxy resin of the present disclosure is characterized by containing the above-described compound (1).

[0142] In the present disclosure, only one of the above-described compound (1) can be contained, but two or more are preferable.

[0143] By containing two or more, an improvement in the adhesive strength of the cured product using the compound (1) can be expected.

[0144] In the present disclosure, it is preferable to contain at least two or more of the above-described compound (1) represented by the above general formula (1) and X 1 and X2 As the compound represented by the above general formula (11) (hereinafter, sometimes referred to as compound (1x)), particularly preferred is one containing:

[0145] the compound (1x), and

[0146] the above compound represented by the above general formula (1), and X 1 the above compound represented by the above general formula (11), X 2 the above compound represented by the above general formula (1), and X 1 the above compound represented by the above general formula (11), X 2 at least one of the above compound represented by the above general formula (11) (hereinafter, sometimes referred to as compound (1z)),

[0147] Among them, particularly preferred are the compound (1x) and the compound (1y) because, by using the epoxy resin, a cured product excellent in the decomposition of acid can be formed. Further, because, by using the epoxy resin, a cured product more excellent in adhesion can be formed.

[0148] In the present disclosure, the content of the above compound (1x) is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, particularly preferably 65 parts by mass or less, based on 100 parts by mass of the total of the above compound (1). Further, the lower limit is preferably 20 parts by mass or more, more preferably 40 parts by mass or more, further more preferably 50 parts by mass or more, particularly preferably 55 parts by mass or more, based on 100 parts by mass of the total of the above compound (1). As the range, the content of the above 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, further more preferably 50 parts by mass or more and 70 parts by mass or less, particularly preferably 55 parts by mass or more and 65 parts by mass or less, based on 100 parts by mass of the total of the above compound (1).

[0149] Because, by using the epoxy resin, a cured product excellent in adhesion can be formed. Further, because, by using the epoxy resin, a cured product easy to decompose acid can be formed.

[0150] In the present disclosure, the content of the above-described compound (1y) is preferably 80 parts by mass or less, more preferably 60 parts by mass or less, further more preferably 50 parts by mass or less, particularly preferably 45 parts by mass or less, in 100 parts by mass in total of the above-described compound (1). In addition, the lower limit is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, particularly preferably 35 parts by mass or more, in 100 parts by mass in total of the above-described compound (1). As a range, the content of the above-described 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, further more preferably 30 parts by mass or more and 50 parts by mass or less, particularly preferably 35 parts by mass or more and 45 parts by mass or less, in 100 parts by mass in total of the above-described compound (1).

[0151] By the content of the above-described compound (1y) being in the above-described range, a cured product having excellent adhesion can be obtained, and thus is preferable.

[0152] In the present disclosure, the content of the total of the above-described compounds (1y) and (1x) is preferably 40 parts by mass or more, more preferably 70 parts by mass or more, further more preferably 80 parts by mass or more, particularly preferably 90 parts by mass or more, particularly preferably 95 parts by mass or more, particularly preferably 98 parts by mass or more, most preferably 99 parts by mass or more, in 100 parts by mass in total of the above-described compound (1).

[0153] By the compound (1), a cured product having excellent adhesion to a metal material can be formed. In addition, by the compound (1), a cured product in which decomposition of an acid is easy can be formed.

[0154] The total chlorine amount of the epoxy resin of the present disclosure is preferably 10,000 ppm or less, more preferably 4,000 ppm or less, further preferably 1,000 ppm or less, on a mass basis, from the aspect of suppressing ion migration. By using an epoxy resin having a total chlorine amount in the above-described range, a cured product obtained from the resin has excellent adhesion to an adherend, and thus is also preferable from this aspect.

[0155] The viscosity of the epoxy resin of the present disclosure is preferably 500 to 30,000 mPa-s, more preferably 500 to 20,000 mPa-s. An epoxy resin having a viscosity in the above-described range is excellent in workability, and thus is preferable.

[0156] The viscosity can be measured by the following method.

[0157] <Measurement method of viscosity using a B-type viscometer>

[0158] After installing a rotor corresponding to the viscosity of the sample and a measuring container on a B-type viscometer and measuring the viscosity of the sample, the measuring container is immersed in a constant-temperature water tank set to 25°C. After leaving until the sample reaches a constant temperature, a rotational speed corresponding to the viscosity is selected. A prescribed time measurement is performed, and the measured value of the digital display calculated automatically is read.

[0159] D. Curable composition

[0160] Next, the curable composition of the present disclosure is described in detail.

[0161] The curable composition of the present disclosure is characterized by containing the above-described compound (1) and a curing agent.

[0162] 1. Compound (1)

[0163] For the above-described compound (1), the same content as that described in the item of the above-described "A. Compound" can be set.

[0164] In the present disclosure, only one of the above-described compound (1) can be contained, but two or more can also be contained.

[0165] Because a cured product with more excellent decomposability and adhesiveness can be formed.

[0166] In the present disclosure, in the case where two or more of the above-described compound (1) are contained, the content of the two or more of the compound (1) can be set to the same as that described in the item of the above-described "C. Epoxy resin".

[0167] As the content of the above-described compound (1), 10 parts by mass or more and 99 parts by mass or less, preferably 15 parts by mass or more and 97 parts by mass or less, and more preferably 50 parts by mass or more and 97 parts by mass or less, and even 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, in 100 parts by mass of the above-described curable composition are preferable from the viewpoint of easy decomposition of the acid and usefulness for chemical recycling.

[0168] 2. Other epoxy compounds

[0169] The above-described curable composition can contain an epoxy compound other than the above-described compound (1) (hereinafter, sometimes referred to as "other epoxy compound").

[0170] As the other epoxy compounds described above, for example, known epoxy compounds can be listed. As the epoxy compounds described above, for example, polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol, and phloroglucinol; polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as dihydroxynaphthalene, bisphenol, methylene bisphenol (bisphenol F), methylene bis(o-cresol), ethylene bisphenol, isopropylidene bisphenol (bisphenol A), isopropylidene bis(o-cresol), tetrabromobisphenol A, 1,3-bis(4-hydroxy-cumylphenyl)benzene, 1,4-bis(4-hydroxy-cumylphenyl)benzene, 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, thio-bisphenol, sulfonyl-bisphenol, oxo-bisphenol, phenol novolak, o-cresol novolak, ethylphenol novolak, butylphenol novolak, octylphenol novolak, resorcinol novolak, terpene phenol, and the like; polyglycidyl ether compounds of polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, hexanediol, polyethylene glycol, thio-diglycol, glycerol, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-epoxyalkane adduct, dicyclopentadiene dimethylol diglycidyl ether, and the like; 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, endomethylenetetrahydrophthalic acid, and the like; homopolymers or copolymers of glycidyl methacrylate; epoxides of cyclic olefin compounds such as maleic anhydride, fumaric anhydride, itaconic anhydride, citraconic anhydride, mesaconic anhydride, glutaconic anhydride, muconic anhydride, phthalic anhydride, isophthalic anhydride, terephthalic anhydride, trimellitic anhydride, trimesic anhydride, pyromellitic anhydride, benzophenone anhydride, 1,2-cyclohexene dicarboxylic anhydride, 1,2-cyclohexene dicarboxylic acid, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylic acid, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylic acid, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, and the like; epoxidized polybutadiene, epoxidized styrene-butadiene copolymer, and the like; heterocyclic compounds such as isocyanuric acid triglycidyl ester. In addition, these epoxy resins can also be epoxy resins that are internally crosslinked using a prepolymer of terminal isocyanate or epoxy resins that are high-molecular-weightized using a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl-containing compound, polyphosphate, and the like).

[0171] As commercially available products of the above-mentioned epoxy resins, 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, DENACOL EX-721 (manufactured by Nagase Chemtex Corporation); EPOLIGHT 200E, EPOLIGHT 400E, EPOLIGHT 70P, EPOLIGHT 200P, EPOLIGHT 400P (manufactured by Kowa Chemical Industries, 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); OGSOL PG-100, OGSOL G-200, OGSOL EG-210, OGSOL EG-250 (manufactured by Osaka Gas Chemicals, Ltd.); YD series, YDF series, YDPN series, TDCN series (Nippon Steel Chemical Co., Ltd.); CELLOXIDE 2021P, CELLOXIDE 2081 (manufactured by Daicel Corporation); TECHMORE VG-3101L (manufactured by Printec Corporation); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); YX8800 (manufactured by Mitsubishi Chemical Corporation); HP4032, HP4032D, HP4700 (manufactured by DIC Corporation), and the like can be exemplified.

[0172] The total content of the above 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, in 100 parts by mass of the above curable composition.

[0173] By setting to the above range, the decomposition of the obtained cured product with acid becomes easy, and is suitable for chemical recycling use.

[0174] 3. Curing agent

[0175] As the above curing agent, for example, a phenol-based curing agent, an acid anhydride-based curing agent, a polythiol compound, an amine-based curing agent, and the like can be exemplified as preferable examples.

[0176] Among these curing agents, an amine-based curing agent is preferable.

[0177] By using an amine-based curing agent, a cured product having more excellent acid-decomposable property and adhesiveness can be formed.

[0178] The above curing agent can be a heat curing agent using heat or a photo curing agent using light irradiation, but a heat curing agent is preferable. Because the formation of the cured product is easy.

[0179] As the phenol-based curing agent, for example, a phenol novolak resin, a cresol novolak resin, an aromatic hydrocarbon formaldehyde resin-modified phenol resin, a dicyclopentadiene phenol addition-type resin, a phenol aralkyl resin (Xyloc resins), a naphthol aralkyl resin, a triphenol-based methane resin, a tetraphenol-based ethane resin, a naphthol novolak resin, a naphthol-phenol co-condensation novolak resin, a naphthol-cresol co-condensation novolak resin, a biphenyl-modified phenol resin (a polyphenol compound having a phenol nucleus linked by a bis-methylene), a biphenyl-modified naphthol resin (a poly-naphthol compound having a phenol nucleus linked by a bis-methylene), an aminotriazine-modified phenol resin (a compound having a phenol skeleton, a triazine ring, and a primary amino group in the molecular structure), and an alkoxyl group-containing aromatic ring-modified phenol novolak resin (a polyphenol compound having a phenol nucleus and an alkoxyl group-containing aromatic ring linked by formaldehyde), and the like can be exemplified.

[0180] As the acid anhydride-based curing agent, for example, norbornene diacid anhydride, phthalic anhydride, maleic anhydride, methyl norbornene diacid anhydride, succinic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, methyl hexahydrophthalic anhydride, trialkyl tetrahydrophthalic anhydride-maleic anhydride adduct, benzophenone tetracarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and hydrogenated methyl nadic anhydride, and the like can be exemplified.

[0181] As the above polythiol compound, for example, pentaerythritol tetra(3-mercaptopropionate), pentaerythritol tetra(mercaptoacetate), dipentaerythritol hexa(3-mercaptopropionate), dipentaerythritol hexa(3-mercaptobutyrate), 1,3,4,6-tetra(2-mercaptoethyl)-1,3,4,6-tetraazaoctahydro-pentalen-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-trithiaundecane, 1,3,4,6-tetra(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, tetra(mercaptomethylthiomethyl)methane, tetra(2-mercaptoethylthiomethyl)methane, tetra(3-mercaptopropylthiomethyl)methane, 1,1,3,3-tetra(mercaptomethylthio)propane, 1,1,2,2-tetra(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 1,1,5,5-tetra(mercaptomethylthio)-3-thiopentane, 1,1,6,6-tetra(mercaptomethylthio)-3,4-dithiahexane, 2,2-bis(mercaptomethylthio)ethane thiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaoctane, 3,6-bis(mercaptomethylthio)-1,9-dimercapto-2,5,8-trithianonane, 3-mercaptomethylthio-1,6-dimercapto-2,5-dithiahexane, 1,1,9,9-tetra(mercaptomethylthio)-5-(3,3-bis(mercaptomethylthio)-1-thiopropyl) 3,7-dithianonane, tris(2,2-bis(mercaptomethylthio)ethyl)methane, tris(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, tetra(2,2-bis(mercaptomethylthio)ethyl)methane, tetra(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, 3,5,9,11-tetra(mercaptomethylthio)-1,13-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexa(mercaptomethylthio)-1,19-dimercapto-2,6,8,12,14,18-hexathia-nonadecane, 9-(2,2-bis(mercaptomethylthio)ethyl)-3,5,13,15-tetra(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexadecathiopentacontane, 3,4,8,9-tetrakis(mercaptomethylthio)-l,l l-dimercapto-2,5,7,10-tetrathioundecane, 3,4,8,9,13,14-hexakis(mercaptomethylthio)-l,16-dimercapto-2,5,7,10,12,15-hexadecathiexacontane, 8-[bis(mercaptomethylthio)methyl]-3,4,12,13-tetrakis(mercaptomethylthio)-l,15-dimercapto-2,5,7,9,11,14-hexathiapentadecane, 4,6-bis[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiopentylthio]-l,3-dithiane, 4-[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiopentylthio]-6-mercaptomethylthio-l,3-dithiane, l,l-bis[4-(6-mercaptomethylthio)-l,3-dithianylthio]-l,3-bis(mercaptomethylthio)propane, l-[4-(6-mercaptomethylthio)-l,3-dithianylthio]-3-[2,2-bis(mercaptomethylthio)ethyl]-7,9-bis(mercaptomethylthio)-2,4,6,10-tetrathioundecane, l,5-bis[4-(6-mercaptomethylthio)-l,3-dithianylthio]-3-[2-(l,3-dithietanyl)methyl-2,4-dithiopentane, 3-[2-(l,3-dithietanyl)methyl-7,9-bis(mercaptomethylthio)-l,l l-dimercapto-2,4,6,10-tetrathioundecane, 9-[2-(l,3-dithietanyl)methyl-3,5,13,15-tetrakis(mercaptomethylthio)-l,17-dimercapto-2,6,8,10,12,16-hexadecathiheptadecane, 3-[2-(l,3-dithietanyl)methyl-7,9,13,15-tetrakis(mercaptomethylthio)-l,17-dimercapto-2,4,6,10,12,16-hexadecathiheptadecane, 3,7-bis[2-(l,3-dithietanyl)methyl-l,9-dimercapto-2,4,6,8-tetrathiannonane, 4,6-bis{3-[2-(l,3-dithietanyl)methyl-5-mercapto-2,4-dithiopentylthio}-l,3-dithiane, 4,6-bis[4-(6-mercaptomethylthio)-l,3-dithianylthio]-6-[4-(6-mercaptomethylthio)-l,3-dithianylthio]-l,3-dithiane, 4-[3,4,8,9-tetrakis(mercaptomethylthio)-l l-mercapto-2,5,7,10-tetrathioundecanyl]-5-mercaptomethylthio-l,3-dithietane, 4,5-bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiopentylthio]-l,3-dithietane, 4-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiopentylthio]-5-mercaptomethylthio-l,3-dithiolane, 4-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithioxanyl]-5-mercaptomethylthio-l,3-dithiolane, 2-{bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]methyl}-l,3-dithiolane, 2-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]mercaptomethylthiomethyl-l,3-dithiolane, 2-[3,4,8,9-tetra(mercaptomethylthio)-l l-mercapto-2,5,7,10-tetrathiaundecylthio]mercaptomethylthiomethyl-l,3-dithiolane, 2-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithioxanyl]mercaptomethylthiomethyl-l,3-dithiolane, 4,5-bis{ 1 -[2-( 1,3-dithiolanyl]-3-mercapto-2-thiopropylthio}- 1,3-dithiolane, 4-{ 1 -[2-( 1,3-dithiolanyl]-3-mercapto-2-thiopropylthio}-5-[l,2-bis(mercaptomethylthio)-4-mercapto-3-thiabutylthio]-l,3-dithiolane, 2-{bis[4-(5-mercaptomethylthio-l,3-dithiolanyl)thio]methyl}-l,3-dithiolane, 4-[4-(5-mercaptomethylthio-l,3-dithiolanyl)thio]-5-{ 1 -[2-( 1,3-dithiolanyl]-3-mercapto-2-thiopropylthio}- 1,3-dithiolane, and the like.

[0182] As commercially available products of these polythiol compounds, for example, TS-G, SC Organic Chemicals Co., Ltd., DPMP, PEMP, PETG, Shikoku Chemicals Corp., and the like can be listed.

[0183] In particular, by using a polythiol compound of 4 valence or more, a composition having excellent curability can be obtained, and thus is preferred.

[0184] As the above-mentioned amine-based curing agent, for example, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,3-diaminobutane, 1,4-diaminobutane, hexamethylenediamine, and the like alkylene diamine; diethylenetriamine, triethylenetriamine, tetraethylenepentamine, and the like polyalkyl polyamine; 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 1,3-diaminomethylcyclohexane, 1,2-diaminocyclohexane, 1,4-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, isophorone diamine, norbornene diamine, and the like alicyclic polyamine; m-xylylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, diethyltoluene diamine, 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, and the like aromatic polyamine; benzoguanamine, acetylguanamine, and the like guanamine; 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-aminopropylimidazole, and the like imidazole; oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, phthalic acid dihydrazide, and the like 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'-methylpiperazine, 4-(N,N- dimethylamino)benzylamine, 4-(N,N-diethylamino)benzylamine, 4-(N,N- diisopropylamino)benzylamine, N,N,-dimethylisophorone diamine, 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; N,N-(bisaminopropyl)-N-methylamine, N,N- bisaminopropyl ethylamine, 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.

[0185] Further, an amine-based latent curing agent which does not react when mixed with the epoxy compound but reacts and cures by heating can also be used. As the amine-based latent curing agent, for example, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, phthalic acid dihydrazide, and the like can be exemplified as dihydrazides of dibasic acids; benzoguanamine, acetoguanamine, and the like can be exemplified as guanamines; dicyandiamide; melamine; modified amines such as a dehydration condensate of an amine compound and a carboxylic acid, an adduct of an amine compound and an epoxy compound, an adduct of an amine compound and an isocyanate compound, a Michael adduct of an amine compound, a Mannich reaction product of an amine compound, a condensate of an amine compound and urea, a condensate of an amine compound and a ketone, and the like.

[0186] Among the above-mentioned amine-based latent curing agents, as a preferred example, an adduct of an amine compound having one or more active hydrogens and a polyepoxy compound and / or a polyisocyanate compound, or a substance obtained by combining a phenol-aldehyde resin therein can be exemplified.

[0187] As the above-mentioned amine compound having one or more active hydrogens, for example, ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,3-diaminobutane, 1,4-diaminobutane, hexamethylenediamine, and the like alkylene diamine; diethylenetriamine, triethylenetriamine, tetraethylenepentamine, and the like polyalkyl polyamine; 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 1,3-diaminomethylcyclohexane, 1,2-diaminocyclohexane, 1,4-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, isophorone diamine, norbornene diamine, and the like alicyclic polyamine; m-xylylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, diethyltoluene diamine, 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, and the like aromatic polyamine; benzoguanamine, acetylguanamine, and the like guanamine; 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-aminopropylimidazole, and the like imidazole; oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, phthalic acid dihydrazide, and the like 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'-methylpiperazine, 4-(N,N- dimethylamino)benzylamine, 4-(N,N-diethylamino)benzylamine, 4-(N,N- diisopropylamino)benzylamine, N,N,-dimethylisophorone diamine, 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; N,N-(bisaminopropyl)-N-methylamine, N,N- bisaminopropyl ethylamine, 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.

[0188] As the above polyepoxy compound, for example, polyglycidyl ether compounds of mononuclear polyphenol compounds such as hydroquinone, resorcinol, pyrocatechol, and phloroglucinol; polyglycidyl ether compounds of polynuclear polyphenol compounds such as dihydroxynaphthalene, bisphenol, methylene bisphenol (bisphenol F), methylene bis(o-cresol), ethylene bisphenol, isopropylidene bisphenol (bisphenol A), isopropylidene bis(o-cresol), tetrabromobisphenol A, 1,3-bis(4-hydroxy-cumylphenyl)benzene, 1,4-bis(4-hydroxy-cumylphenyl)benzene, 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, thio-bisphenol, sulfonyl-bisphenol, oxo-bisphenol, phenol novolak, o-cresol novolak, ethylphenol novolak, butylphenol novolak, octylphenol novolak, resorcinol novolak, terpene phenol, and the like; polyglycidyl ether compounds of polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, hexanediol, polyethylene glycol, thio-diglycol, glycerol, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-epoxyalkane adduct, and the like; 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, endomethylenetetrahydrophthalic acid, and the like, and homopolymers or copolymers of glycidyl methacrylate; epoxy compounds having a glycidyl amino group such as N,N-diglycidyl aniline, bis(4-(N-methyl-N-glycidylamino)phenyl)methane, diglycidyl o-toluidine, and the like; epoxides of cyclic olefin compounds such as vinylcyclohexene diepoxide, dicyclopentadiene diepoxide, 3,4-epoxy cyclohexylmethyl-3,4-epoxy cyclohexane carboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexane carboxylate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, and the like; epoxidized conjugated diene polymers such as epoxidized polybutadiene, epoxidized styrene-butadiene copolymer, and the like; and heterocyclic compounds such as isocyanuric acid triglycidyl ester.

[0189] As the above polyisocyanate compound, for example, there can be mentioned 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, diphenylmethane-4,4'-diisocyanate, phenylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, 1,5-naphthalene diisocyanate, 1,5-tetrahydronaphthalene diisocyanate, 3,3'-dimethyldiphenyl-4,4'-diisocyanate, dianisidine diisocyanate, tetramethylxylylene diisocyanate, and the like aromatic diisocyanates; isophorone diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, trans-1,4-cyclohexyl diisocyanate, norbornene diisocyanate, and the like alicyclic diisocyanates; tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4 and / or (2,4,4)-trimethylhexamethylene diisocyanate, lysine diisocyanate, and the like aliphatic diisocyanates; isocyanurate trimer, biuret trimer, trimethylolpropane adduct, and the like of the above exemplified diisocyanates; triphenylmethane triisocyanate, 1-methylbenzene-2,4,6-triisocyanate, dimethyltriphenylmethane tetraisocyanate, and the like.

[0190] Further, these isocyanate compounds can also be used in the form of carbodiimide-modified, isocyanurate-modified, biuret-modified, and the like, and can also be used in the form of blocked isocyanate blocked by various blocking agents.

[0191] As the above phenol resin, for example, there can be mentioned phenol novolak resin, cresol novolak resin, aromatic hydrocarbon formaldehyde resin-modified phenol resin, dicyclopentadiene phenol addition-type resin, phenol aralkyl resin (Xyloc resins), naphthol aralkyl resin, triphenol methane resin, tetraphenol ethane resin, naphthol novolak resin, naphthol-phenol co-condensation novolak resin, naphthol-cresol co-condensation novolak resin, biphenyl-modified phenol resin (polyphenol compound having a phenol nucleus linked by a bis-methylene), biphenyl-modified naphthol resin (polyphenol compound having a phenol nucleus linked by a bis-methylene), aminotriazine-modified phenol resin (compound having a phenol skeleton, triazine ring, and primary amino group in the molecular structure), and alkoxyl group-containing aromatic ring-modified novolak resin (polyphenol compound having a phenol nucleus and alkoxyl group-containing aromatic ring linked by formaldehyde), and the like polyphenol compounds.

[0192] As commercially available products of the above-mentioned amine-based latent curing agent, for example, Adeka Hardener EH-3636S (manufactured by ADEKA Corporation; dicyandiamide type latent curing agent), Adeka Hardener EH-4351S (manufactured by ADEKA Corporation; dicyandiamide type latent curing agent), Adeka Hardener EH-5011S (manufactured by ADEKA Corporation; imidazole type latent curing agent), Adeka Hardener EH-5046S (manufactured by ADEKA Corporation; imidazole type latent curing agent), Adeka Hardener EH-4357S (manufactured by ADEKA Corporation; polyamine type latent curing agent), Adeka Hardener EH-5057P (manufactured by ADEKA Corporation; polyamine type latent curing agent), Adeka Hardener EH-5057PK (manufactured by ADEKA Corporation; polyamine type latent curing agent), Amicure PN-23 (manufactured by Ajinomoto Fine Techno Co., Inc.; amine adduct type latent curing agent), Amicure PN-40 (manufactured by Ajinomoto Fine Techno Co., Inc.; amine adduct type latent curing agent), Amicure VDH (manufactured by Ajinomoto Fine Techno Co., Inc.; hydrazide type latent curing agent), Fujicure FXR-1020 (manufactured by T&K TOKA Corporation; latent curing agent), and the like can be exemplified.

[0193] As the content of the above-mentioned curing agent, it 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, in 100 parts by mass of the above-mentioned curable composition.

[0194] Because by being in the above-mentioned range, a cured product having more excellent acid decomposability can be formed. Furthermore because a cured product having more excellent adhesiveness can be formed.

[0195] As the content of the above-mentioned curing agent, it 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, in 100 parts by mass of the total of the above-mentioned compound (1) and other epoxy compounds.

[0196] By being in the above-mentioned range, a curable composition having excellent curability and adhesiveness and a cured product having excellent adhesiveness can be obtained, and thus it is preferable.

[0197] 4. Other Components

[0198] The above-mentioned curable composition can contain the above-mentioned compound (1), other epoxy compounds, other components than the curing agent.

[0199] As such other components, for example, commonly used additives such as a curing catalyst, an inorganic filler, a diluent, a reinforcing material, a silane coupling agent, a lubricant, a pigment, a thickening agent, a thixotropic agent, an antioxidant, a light stabilizer, an ultraviolet absorber, an antifoaming agent, an antirust agent, colloidal silica, colloidal alumina, and the like can be exemplified. In the present disclosure, an adhesive resin such as a xylene resin, a petroleum resin, or the like can also be further used in combination.

[0200] As the above-mentioned curing catalyst, for example, phosphine compounds such as triphenylphosphine; phosphonium salts such as tetraphenylphosphonium bromide; imidazoles such as 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 the like; imidazole salts of the above-mentioned imidazoles and trimellitic acid, isocyanuric acid, boron, and the like; amines such as benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and the like; 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, toluylene diisocyanate-dimethylurea, and the like; and complexes of boron trifluoride with amines, ether compounds, and the like can be exemplified. These curing accelerators can be used alone or in combination of two or more.

[0201] The content of the above-mentioned curing catalyst in the curable composition is preferably 0.01 to 20 parts by mass, relative to 100 parts by mass of the total of the compound (1) and other epoxy compounds.

[0202] As the above-mentioned filler, for example, powdered silica such as fused silica, crystalline silica, and the like; inorganic fillers such as magnesium hydroxide, aluminum hydroxide, zinc molybdate, calcium carbonate, silicon carbonate, calcium silicate, potassium titanate, beryllium oxide, zirconium oxide, zircon, forsterite, block talc, spinel, mullite, titanium dioxide, or the like; or beads obtained by spheroidizing these, and glass fibers can be exemplified.

[0203] The content of the filler in the curable composition of the present disclosure is preferably about 0 to 90% by mass, more preferably 1 to 30% by mass.

[0204] As the above diluent, for example, non-reactive diluents (plasticizers) such as dioctyl phthalate, dibutyl phthalate, benzyl alcohol, coal tar, and the like can be exemplified.

[0205] As the above reinforcing material, for example, fibrous fillers such as glass fibers, pulp fibers, synthetic fibers, ceramic fibers, and the like; reinforcing materials such as glass cloth, aramid cloth, carbon fibers, and the like can be exemplified.

[0206] As the above silane coupling agent, for example, silane coupling agents such as 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-methacryloyloxypropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, and the like can be exemplified.

[0207] As the above lubricant, for example, lubricants such as candelilla wax, carnauba wax, wood wax, white wax, beeswax, lanolin, whale wax, montan wax, petroleum wax, aliphatic wax, aliphatic ester, aliphatic ether, aromatic ester, aromatic ether, and the like can be exemplified.

[0208] The curable composition of the present disclosure can be used, for example, for a wide variety of applications such as paints, adhesives, sealants, coating agents, fiber bundling agents, building materials, electronic parts, and the like.

[0209] In particular, since decomposition by acid is easy, the curable composition is useful as a material for recycling. More specifically, a paint for recycling, an adhesive for recycling, a sealant for recycling, a coating agent for recycling, a fiber bundling agent for recycling, a building material for recycling, an electronic part for recycling, and the like can be produced. The term "recycling" used herein encompasses a use in which, after decomposition of the cured product by acid decomposition or the like, the adherend to which the cured product is adhered is recovered and reused. Furthermore, the decomposed product obtained by decomposition of the cured product by acid decomposition is neutralized, solvent-extracted, purified, or the like as necessary, and a compound such as a hydroxy aldehyde, a trihydroxymethylpropane, or the like can be obtained again. This compound can be used again as a starting material for the compound represented by formula (1).

[0210] Furthermore, in the above applications, the material to which the curable composition is applied, for example, the adherend in the case of an adhesive or a coating agent, can be any one of a metallic material, an inorganic material other than a metallic material, a high molecular material, and the like, but is preferably a metallic material. This is because the cured product of the curable composition of the present disclosure exhibits excellent adhesion.

[0211] As the metal material, iron, zinc, nickel, copper, aluminum, titanium, stainless steel, mild steel, plated steel, and the like can be exemplified.

[0212] As the inorganic material, a glass substrate such as a quartz glass substrate, a Pyrex (registered trademark) glass substrate, a synthetic quartz substrate, and the like can be exemplified.

[0213] As the high molecular material, cellulose esters such as diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetyl propionyl cellulose, and nitrocellulose; polyamides; polyimides; polyurethanes; epoxy resins; polycarbonates; polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-l,4-cyclohexane dimethanol terephthalate, polyethylene-l,2-diphenyloxyethane-4,4'-dicarboxylate, and polybutylene terephthalate; polystyrenes; 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; polycarbonates; polysulfones; polyethersulfones; polyetherketones; polyetherimides; polyethylene oxides; norbornene resins; and cyclic olefin polymers (COP) can be exemplified.

[0214] E. Cured product

[0215] Next, the cured product of the present disclosure is described in detail.

[0216] The cured product of the present disclosure is characterized by being a cured product of the curable composition containing the above-mentioned compound (1).

[0217] The cured product of the present disclosure can have acid-decomposable property. Furthermore, the cured product of the present disclosure can be produced as a cured product having excellent adhesiveness to an adherend such as a substrate.

[0218] The cured product of the present disclosure is formed using a curable composition.

[0219] As for the content of such a curable composition, the same content as described in the item of the above-mentioned "D. Curable composition" can be set, and the description here is omitted.

[0220] Furthermore, as for the method of forming the cured product, as long as it is a method capable of curing the above-mentioned curable composition, for example, the same content as described in the item of the later-described "F. Method of producing a cured product" can be set, and thus the description here is omitted.

[0221] F. Method of producing a cured product

[0222] Next, the method of producing a cured product of the present disclosure is described in detail.

[0223] The manufacturing method of the present disclosure is characterized by having a curing step of curing a curable composition containing the above-mentioned compound (1).

[0224] According to the present disclosure, a cured product having good adhesiveness to an adherend and good decomposability of acid can be easily obtained.

[0225] The manufacturing method of the present disclosure has a curing step.

[0226] Hereinafter, the curing step contained in the manufacturing method of the present disclosure is described in detail.

[0227] 1. Curing step

[0228] This step is a step of curing the above-mentioned curable composition.

[0229] As for the content of such a curable composition, it can be set to be the same as that described in the item of the above-mentioned "D. Curable composition", and thus the description here is omitted.

[0230] Further, as for the method of forming a cured product, it is only required to be a method capable of curing the above-mentioned curable composition, and for example, it can be set to be the same as that described in the item of the later-described "F. Manufacturing method of cured product", and thus the description here is omitted.

[0231] As the curing method of the above-mentioned curable composition, there is no particular limitation as long as it is a method capable of curing the above-mentioned curable composition, and for example, a method of heating the curable composition, a method of light irradiation to the curable composition, and the like can be exemplified.

[0232] In the present disclosure, the above-mentioned curing method is preferably a method of heating the curable composition.

[0233] As the heating temperature, for example, it can be set to be 100°C or higher and 180°C or lower. Because the formation of a cured product is easy.

[0234] 2. Other step

[0235] The manufacturing method of the present disclosure can also have a step other than the above-mentioned curing step.

[0236] As such an other step, for example, a step of applying the above-mentioned curable composition, and the like can be exemplified.

[0237] G. Manufacturing method of decomposed product

[0238] Next, the manufacturing method of the decomposed product of the present disclosure is described in detail.

[0239] The manufacturing method of the present disclosure is characterized by having a decomposition step of decomposing a cured product of a curable composition containing the above-mentioned compound (1).

[0240] According to the present disclosure, the cured product can be easily decomposed to obtain a decomposed product.

[0241] The manufacturing method of the present disclosure has a decomposition step.

[0242] Hereinafter, the decomposition step included in the manufacturing method of the present disclosure is described in detail.

[0243] 1. Decomposition step

[0244] This step is a step of decomposing the cured product of the curable composition containing the above-mentioned compound (1).

[0245] As to the contents of the above-mentioned curable composition, cured product, the same contents as those described in the above-mentioned "D. Curable composition", "E. Cured product" and the like can be set, and thus the description here is omitted.

[0246] As the decomposition method of the above-mentioned cured product, there is no particular limitation as long as it is a method capable of decomposing the above-mentioned cured product, but for example, a method of bringing an acidic solution into contact with the cured product is preferred. Because the curing of the cured product of the curable composition containing the above-mentioned compound (1) can be more effectively performed.

[0247] As the method of bringing an acidic solution into contact with the cured product, a method of applying an acidic solution by a sprayer or the like, a method of dipping in an acidic solution, and the like can be exemplified.

[0248] As the acid used in the acidic solution, hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and the like can be exemplified, and hydrochloric acid is preferred. Because the decomposition becomes easy.

[0249] As the solvent used in the acidic solution, there is no particular limitation, and a solvent suitable for the decomposition and recovery thereof in an organic solvent or water can be exemplified.

[0250] As the pH of the above-mentioned acidic solution, it can be set to 0 or more and 6 or less, and preferably 0.5 or more and 5 or less, and particularly preferably 1 or more and 4 or less. Because the decomposition becomes easy. The pH is the pH at the temperature of the acidic solution.

[0251] 2. Others

[0252] The manufacturing method of the present disclosure has the above-mentioned decomposition step, but other steps can also be included as needed.

[0253] As such other steps, for example, a neutralization step of neutralizing the acidic solution after the above-mentioned decomposition step, an extraction step of extracting the decomposed product of the above-mentioned cured product, and the like can be exemplified.

[0254] H. Decomposition method

[0255] Next, the decomposition method of the present disclosure is described in detail.

[0256] 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 above-mentioned compound (1).

[0257] According to the present disclosure, a cured product can be easily decomposed to obtain a decomposition product.

[0258] The decomposition method of the present disclosure has a decomposition step.

[0259] As to the content of such a decomposition step, it can be set to be the same as that described in the item of the above-mentioned "G. Method for producing a decomposition product", and thus the description here is omitted.

[0260] Further, the above-mentioned decomposition method can also have a step other than the above-mentioned decomposition step. As to such other step, it can be set to be the same as that described in the item of the above-mentioned "G. Method for producing a decomposition product", and thus the description here is omitted.

[0261] I. Other [1]

[0263] A compound represented by the following general formula (1).

[0264] [Chemical Formula 20]

[0265]

[0266] 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 aryl group having 5 to 10 carbon atoms which can have, as a substituent, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, 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 methyl glycidyl ether group, a glycidoxyalkyl group, a β-methyl glycidoxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number of 0 to 4.

[0267] X 1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11).

[0268] wherein at least one of X 1 or X 2 is a group represented by the above-mentioned general formula (11).

[0269] [Chemical Formula 21]

[0270]

[0271] in the formula, R 3 is a hydrogen atom or a methyl group.

[0272] wherein * indicates a bonding point. [2]

[0274] The compound according to [1] is a compound represented by the following general formula (1b) or (1c).

[0275] [Chemical Formula 22]

[0276]

[0277] [Chemical Formula 23]

[0278]

[0279] R 1 , R 2 , X 1 , X 2 , and n in the above formulae (1b) and (1c) are the same as R 1 , R 2 , X 1 , X 2 , and n in the formula (1). [3]

[0281] The compound according to [1] or [2], wherein X 1 and X 2 are groups represented by the above general formula (11). [4]

[0283] An epoxy resin containing the compound according to any one of [1] to [3]. [5]

[0285] The epoxy resin according to [4], wherein two or more compounds represented by the above general formula (1) are contained. [6]

[0287] The epoxy resin according to [4] or [5], wherein at least a compound represented by the above general formula (1) and X 1 and X 2 are groups represented by the above general formula (11) are contained. [7]

[0289] The epoxy resin according to [5] or [6], wherein a compound represented by the above general formula (1) and X 1 and X 2the compound represented by the above general formula (11), and the compound represented by the above general formula (1) and X 1 the compound represented by the above general formula (11), and the compound represented by the above general formula (1) and X 2 the compound in which X 1 the compound in which X 2 at least one of the compounds represented by the above general formula (11). [8]

[0291] The epoxy resin according to any one of [5] to [7], wherein the compound represented by the above general formula (1) and X 1 and X 2 The content of the compound represented by the above general formula (11) is 20 parts by mass or more and 80 parts by mass or less in 100 parts by mass in total of the compounds represented by the above general formula (1). [9]

[0293] The epoxy resin according to any one of [5] to [8], wherein the compound represented by the above general formula (1) and X 1 the compound represented by the above general formula (11), and the compound represented by the above general formula (1) and X 2 The content of the compound in which X

[10]

[0295] A method for producing a compound, which is a compound represented by the following general formula (1),

[0296] having an epoxidation step of reacting a compound represented by the following general formula (2) with an epoxy halopropane.

[0297] [Chemical Formula 24]

[0298]

[0299] 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 aryl group having 5 to 10 carbon atoms which can have, as a substituent, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, 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 methyl glycidyl ether group, a glycidyloxyalkyl group, a β-methyl glycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number of 0 to 4.

[0300] X1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11).

[0301] wherein X 1 or X 2 is a group represented by the following general formula (11).

[0302] [Chemical Formula 25]

[0303]

[0304] wherein R 3 is a hydrogen atom or a methyl group.

[0305] wherein * represents a bonding point.

[0306] [Chemical Formula 26]

[0307]

[0308] wherein 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 aryl group having 5 to 10 carbon atoms which can have, as a substituent, 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-methyl glycidyl ether group, or 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 methyl glycidyl ether group, a glycidyloxyalkyl group, a β-methyl glycidyloxyalkyl group, an acryloyloxyalkyl group, or a methacryloyloxyalkyl group. n represents a number of 0 to 4.

[11]

[0310] The production method of the compound according to

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

[12]

[0312] A curable composition containing the compound according to any one of [1] to [3] and a curing agent.

[13]

[0314] A material for recycling containing the compound according to any one of [1] to [3].

[14]

[0316] A cured product of a curable composition containing the compound according to any one of [1] to [3].

[15]

[0318] A cured product manufacturing method including a curing step of curing a curable composition containing the compound described in any one of [1] to [3].

[16]

[0320] A decomposition product manufacturing method including a decomposition step of decomposing a cured product of a curable composition containing the compound described in any one of [1] to [3].

[17]

[0322] A decomposition method including a decomposition step of decomposing a cured product of a curable composition containing the compound described in any one of [1] to [3].

[0323] Examples

[0324] Next, the present application is described in more detail by examples, but the present application is not limited by these examples.

[0325] Example 1: Manufacture of epoxy resin No. 1

[0326] Into a 500 mL flask equipped with a reflux device, a stirring device, and a dropping device, 25.8 g (0.11 mol) of o-DOP (a compound represented by the following formula), 200 g (2.2 mol, 20 equivalents) of epichlorohydrin were charged, and 8.5 g (0.10 mol, 0.95 equivalents) of a 48 mass% sodium hydroxide aqueous solution was dropped thereinto at 65 to 70°C under 19.0 kPa for 2 hours. After the dropping was completed, water was distilled off while ripening for 1 hour. After the reaction was completed, the reaction solution was filtered to filter out the by-produced salt, and the solution was again pipetted into a 500 mL four-necked flask equipped with a reflux device, a stirring device, and a dropping device. As a phase transfer catalyst, 0.79 g (2.5 mmol, 0.02 equivalents) of cetyltrimethylammonium chloride was charged, and 22.1 g (0.24 mol, 2.0 equivalents) of a 48 mass% sodium hydroxide aqueous solution was dropped thereinto at 58 to 60°C under 14.0 kPa for 1.5 hours. After the dropping was completed, water was distilled off while ripening for 2 hours. After the reaction was completed, 10 g each of KYOWA AD 600, 700 SL were added and the remaining base was removed, and the solution was filtered to filter out the by-produced salt and KYOWA AD. The remaining epichlorohydrin was removed by distillation under reduced pressure, and diatomite filtration was performed, thereby obtaining epoxy resin No. 1 as a light yellow liquid.

[0327] The components contained in the epoxy resin No. 1 were identified by gas chromatography, 1 H-NMR. As a result, o-DOP-EP1 and o-DOP-EP2 shown below were contained in the epoxy resin No. 1 at a mass ratio of 41 / 59.

[0328] [Chemical Formula 27]

[0329]

[0330] [Chemical Formula 28]

[0331]

[0332] [Chemical Formula 29]

[0333]

[0334] <Gas chromatography analysis>

[0335] The epoxy resin No. 1 obtained by Example 1 was diluted with chloroform to 50 times by mass, and measurement was performed using a GC / MS device (Shimadzu QP2010plus (CI method, reagent gas: isobutane)) under the following measurement conditions.

[0336] Measurement conditions) Column: HP-5MS (0.25 mm x 30 m, 0.25 μm)

[0337] Column temperature: 80°C (2 min) - 20°C / min - 200°C (0 min) - 10°C / min - 300°C (2 min)

[0338] Flow rate: 1.5 mL / min Split ratio: 1 / 10

[0339] Injection port temperature: 300°C Interface temperature: 250°C

[0340] Ion source temperature: 200°C

[0341] Scan: m / z 80-550

[0342] <NMR analysis>

[0343] The epoxy resin No. 1 obtained in the above was fractionated using a recycling fractionation HPC (Japan Analytical Industry; LaboACE LC-5060) under the following fractionation conditions, and NMR analysis was performed on the obtained o-DOP-diEP (81.11 mg) and o-DOP-monoEP (52.25 mg).

[0344] [Fractionation conditions]

[0345] Column: JAIGEL 2HR x 2

[0346] Flow rate: 10 ml / min, isocratic elution

[0347] Injection volume: 2 mL

[0348] Solvent: CHCl3(Fujifilm and GPC for GPC)

[0349] Detector: RI

[0350] Sample: 0.20793 g / 2 mL

[0351] Recycle number: 10 times

[0352] o The fractionated sample was evaporated and air-dried, and the mass was measured.

[0353] (Confirmation of the fractionated sample using other analysis was not performed)

[0354] o-DOP-diEP 81.11 mg

[0355] o-DOP-monoEP 52.25 mg

[0356] 〔Adhesiveness evaluation〕

[0357] A one-part epoxy resin composition was prepared using the formulation shown in Table 1 (the unit of the formulation is “parts by mass”). The cured product of each composition was measured for shear strength.

[0358] The materials used in the formulation are as follows.

[0359] Compound (1): Epoxy resin No. 1

[0360] Other epoxy compound: EP-4100E: bisphenol A type epoxy resin, (ADEKA Corporation)

[0361] Inorganic filler RY-200S: fumed silica (NIPPON AEROSIL Corporation)

[0362] (Measurement method of shear strength)

[0363] The measurement of shear strength was performed as follows.

[0364] A silicon wafer having a hole with a diameter of 4 mm and a height of 1 mm was placed on each substrate, and the resin composition was placed inside the hole. A cylindrical shaped product with a diameter of 4 mm and a height of 1 mm was produced by curing it at 150°C for 2 hours. The shear strength (MPa) was then measured by a 4000 Plus Bond Tester (Nordson DAGE Corporation). For each substrate, the following substrates were used. The results are shown in Table 1 and Figure 7 .

[0365] Ni substrate: Ni-plated SPCC-SB (TEST PIECE Corporation)

[0366] Cu substrate: C1100 (manufactured by Engineering Test Service Co., Ltd.)

[0367] Al substrate: A5052P (manufactured by Test Piece Co., Ltd.)

[0368] Table 1

[0369]

[0370] As shown in Table 1 and Figure 7 As shown in , it was found that the one-component epoxy resin composition of the present disclosure is superior in bonding strength to Cu and Al, particularly, compared to the resin composition not using epoxy resin No. 1.

[0371] 〔Decomposition test〕

[0372] One-component epoxy resin compositions were prepared with the formulations shown in Table 2 (the unit of formulation is "parts by mass"), and the decomposition behavior of the cured products of the respective compositions in an acid solvent was examined.

[0373] Other epoxy compounds: EP-4088S: dicyclopentadiene type epoxy resin, manufactured by ADEKA Co., Ltd.

[0374] (Method for confirming decomposability)

[0375] The resin composition was evenly spread onto a Teflon (registered trademark) plate to a thickness of 30 μm and cured at 150°C for 2 hours. The resulting cured product was mass-measured and then immersed in a mixed solution of tetrahydrofuran (THF) and water (9:1 by volume) containing 0.1 mol / L HCl at room temperature for 24 hours, and its behavior was observed. The mass of the remaining cured product after immersion was measured. The results are shown in Table 2.

[0376] Table 2

[0377]

[0378] *1A: Completely dissolved B: Swelled C: No change

[0379] In Example 2, the solidified material disintegrated finely after 2 hours of immersion and completely dissolved after 24 hours.

[0380] As shown in Table 2, it was found that the one-component epoxy resin composition of the present disclosure was superior in decomposability in an acid solvent compared to the resin composition not using epoxy resin No. 1.

[0381] Industrial applicability

[0382] According to the present invention, a compound capable of forming a solidified product having excellent acid decomposability can be provided.

[0383] The compound of the present disclosure is considered to be useful as a chemical recycling material because it has excellent bonding strength with metal materials such as nickel, copper, and aluminum and can be easily decomposed by acid.

Claims

1. A compound represented by the following general formula (1): Where 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 aryl group having 5 to 10 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, 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, and 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; X 1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11); in, X 1 or X 2 At least one of them is a group represented by general formula (11); Where R 3 is a hydrogen atom or a methyl group; Where * indicates the bonding point.

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

3. The compound according to claim 1 or claim 2, wherein X 1 and X 2 It is a group represented by the general formula (11). 4 . An epoxy resin comprising the compound according to claim 1 .

5. The epoxy resin according to claim 4, wherein Containing two or more compounds represented by the following general formula (1), Where 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 aryl group having 5 to 10 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, 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, and 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; X 1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11); Among them, X 1 or X 2 At least one of them is a group represented by the following general formula (11); Where R 3 is a hydrogen atom or a methyl group; Where * indicates the bonding point.

6. The epoxy resin according to claim 4, wherein At least containing the general formula (1) and X 1 and X 2 A compound having a group represented by the general formula (11).

7. The epoxy resin according to claim 4, wherein contain: Represented by the general formula (1), and X 1 and X 2 A compound which is a group represented by the general formula (11); and Represented by the general formula (1), and X 1 is a group represented by the general formula (11), X 2 is a hydrogen atom and is represented by the general formula (1), and X 1 is a hydrogen atom, X 2 At least one of the compounds represented by the group of the general formula (11).

8. The epoxy resin according to claim 7, wherein Represented by the general formula (1), and X 1 and X 2 The content of the compound which is a group 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).

9. The epoxy resin according to claim 7, wherein Represented by the general formula (1), and X 1 is a group represented by the general formula (11), X 2 The content of the compound which 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, which is a method for producing a compound represented by the following general formula (1): The method comprises the following steps of reacting a compound represented by the following general formula (2) with an epihalohydrin, Where 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 aryl group having 5 to 10 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, 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, and 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; X 1 and X 2 represents a hydrogen atom or a group represented by the following general formula (11); in, X 1 or X 2 At least one of them is a group represented by the following general formula (11); Where R 3 is a hydrogen atom or a methyl group; Where * indicates the bonding point; Where 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 aryl group having 5 to 10 carbon atoms, a hydroxyl group, or a halogen atom which may have 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 a halogen atom as a substituent, and 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 of 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 the general formula (2) with an 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, comprising the compound according to claim 1.

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

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