Compound, composition, cured product, and method for producing cured product

Abstract

To provide, mainly, a compound capable of forming a cured product which is excellent in water solubility and also excellent in heat resistance.SOLUTION: The present disclosure provides a compound represented by the general formula (1) in the figure.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Epoxy compounds are widely used as components of adhesives, paints, etc. For example, Patent Document 1 describes a paint that uses a bisphenol A type epoxy compound as the epoxy compound. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2022 / 080048 Summary of the Invention [Problem to be solved by the invention]

[0004] In recent years, from the viewpoint of environmental issues, there has been a demand for materials that do not use organic solvents, and there is also a demand for epoxy compounds that are highly water-soluble so that water can be used as a solvent. However, the epoxy compounds used in Patent Document 1 and the like often have insufficient water solubility, which makes it difficult to use water as a solvent. Furthermore, even if an epoxy compound is water-soluble, it has not yet been found that can be used to form a cured product having excellent physical strength such as heat resistance.

[0005] The present disclosure has been made in view of the above problems, and has as its main object to provide a compound that can form a cured product that has excellent water solubility and heat resistance. [Means for solving the problem]

[0006] As a result of extensive research, the present inventors have found that by using a compound having a specific structure, it is possible to form a cured product that is excellent in water solubility and heat resistance.

[0007] That is, the present disclosure provides a compound represented by the following general formula (1):

[0008] [ka]

[0009] (In the formula, R 1 , R 2 and R 3 each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group A>, or a group represented by the following general formula (2): R 1 , R 2 and R 3 At least one of the above is a group represented by the following general formula (2): <Group A> is -O-, -CO-, -COO-, -OCO-, -NR 101 -, -NR 101 CO- and -S- R 101 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

[0010] [ka]

[0011] (In the formula, R 4 represents a hydrogen atom or a methyl group, L 1 represents a direct bond, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group B>, * represents a binding site <Group B> is -O-, -CO-, -COO-, -OCO-, -NR 111-, -NR 111 CO- and -S- R 111 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

[0012] According to the present disclosure, it is possible to provide a compound that can form a cured product that has excellent water solubility and heat resistance.

[0013] In the present disclosure, the above R 1 , R 2 and R 3 are preferably groups represented by the general formula (2) above, because the compound is capable of forming a cured product having superior water solubility and heat resistance.

[0014] The present disclosure provides a composition comprising the compound described above.

[0015] According to the present disclosure, since the composition contains the above-mentioned compound, water can be used as a solvent, and the composition has excellent compatibility with water-soluble materials.

[0016] In the present disclosure, the composition preferably contains water as a solvent, because the composition has excellent dispersion stability and the amount of organic solvent used can be easily reduced.

[0017] In the present disclosure, the composition preferably contains a curing agent, because this provides the composition with excellent curability.

[0018] The present disclosure provides a cured product of the above-described composition.

[0019] According to the present disclosure, since the above-mentioned compound is used, it is possible to provide a cured product that can be easily formed using a composition containing water as a solvent.

[0020] The present disclosure provides a method for producing a cured product, which comprises a curing step of curing the above-described composition.

[0021] According to the present disclosure, since the above-mentioned compound is used, a method can be provided that can easily form a cured product using a composition containing water as a solvent. [Effects of the Invention]

[0022] According to the present disclosure, it is possible to provide a compound that can form a cured product that has excellent water solubility and heat resistance. [Brief explanation of the drawings]

[0023] [Figure 1] 1 shows the results of 1H-NMR measurement of the compound obtained in Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0024] The present disclosure relates to compounds, compositions containing the same, cured products, and methods for producing the cured products. The compound, composition, cured product, and method for producing the cured product of the present disclosure will be described in detail below.

[0025] A. Compound First, the compounds of the present disclosure will be described. The compound of the present disclosure is characterized by being represented by the following general formula (1):

[0026] [ka]

[0027] (In the formula, R 1 , R 2 and R 3 each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group A>, or a group represented by the following general formula (2): R 1 , R 2 and R 3At least one of the above is a group represented by the following general formula (2): <Group A> is -O-, -CO-, -COO-, -OCO-, -NR 101 -, -NR 101 CO- and -S- R 101 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

[0028] [ka]

[0029] (In the formula, R 4 represents a hydrogen atom or a methyl group, L 1 represents a direct bond, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group B>, * represents a binding site <Group B> is -O-, -CO-, -COO-, -OCO-, -NR 111 -, -NR 111 CO- and -S- R 111 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

[0030] According to the present disclosure, the compound represented by the above general formula (1) (hereinafter, sometimes referred to as compound 1) can form a cured product that is excellent in water solubility and heat resistance. The reason why Compound 1 can form a cured product with excellent water solubility and heat resistance is presumed to be as follows.

[0031] That is, Compound 1 has a skeleton that can be formed by the reaction of inositol with a trialkyl orthoformate compound (hereinafter, sometimes simply referred to as a specific orthotrialkyl skeleton), and has reduced hydrophobicity compared to, for example, compounds having a skeleton formed by the reaction of inositol with a trialkyl orthoacetate compound, etc., and therefore has excellent water solubility. Furthermore, as a result of the excellent water solubility, when a composition is formed using Compound 1, water can be used as a solvent, and the amount of organic solvent used can be easily reduced. Furthermore, Compound 1 has a three-dimensional cyclic structure such as the specific orthotrialkyl skeleton described above, and thus can form a cured product having excellent physical strength such as heat resistance. For these reasons, Compound 1 is excellent in water solubility and can form a cured product having excellent physical strength such as heat resistance.

[0032] Compound 1 of the present disclosure will now be described in detail.

[0033] 1. Compound 1 Above R 1 , R 2 and R 3 , R 101 and R 111 (Hereinafter, R 1 The hydrocarbon group used in (the formula (2)) includes an aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms.

[0034] The aliphatic hydrocarbon group having 1 to 20 carbon atoms may be a hydrocarbon group that does not contain an aromatic hydrocarbon ring or a heterocyclic ring, and examples thereof include a chain aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aliphatic ring-containing group having 3 to 20 carbon atoms. Examples of the chain aliphatic hydrocarbon group having 1 to 20 carbon atoms include alkyl groups having 1 to 20 carbon atoms and alkenyl groups having 2 to 20 carbon atoms. Examples of the aliphatic ring-containing group having 3 to 20 carbon atoms include a cycloalkyl group having 3 to 20 carbon atoms and a cycloalkylalkyl group having 4 to 20 carbon atoms.

[0035] The alkyl group having 1 to 20 carbon atoms may be linear or branched. Examples of linear alkyl groups include methyl, ethyl, propyl, butyl, isoamyl, tert-amyl, hexyl, heptyl, and octyl. Examples of branched alkyl groups include isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, 2-hexyl, 3-hexyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, hebrotadecyl, and octadecyl.

[0036] The alkenyl group having 2 to 20 carbon atoms may be linear or branched. It may be a terminal alkenyl group having an unsaturated bond at the terminal, or an internal alkenyl group having an internal unsaturated bond. Examples of terminal alkenyl groups include vinyl, allyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of internal alkenyl groups include 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, and 4,8,12-tetradecatrienylallyl.

[0037] Examples of the cycloalkyl group having 3 to 20 carbon atoms include saturated monocyclic alkyl groups having 3 to 20 carbon atoms, saturated polycyclic alkyl groups having 3 to 20 carbon atoms, and groups having 4 to 20 carbon atoms in which one or more hydrogen atoms in the ring of these groups have been substituted with an alkyl group. Examples of the saturated monocyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. Examples of the saturated polycyclic alkyl group include an adamantyl group, a decahydronaphthyl group, an octahydropentalene group, and a bicyclo[1.1.1]pentanyl group. Examples of the alkyl group substituting a hydrogen atom in the ring of a saturated monocyclic or saturated polycyclic alkyl group include the groups exemplified above as the alkyl group having 1 to 20 carbon atoms. Examples of groups in which one or more hydrogen atoms in the ring of a saturated polycyclic alkyl group have been substituted with an alkyl group include a bornyl group.

[0038] The cycloalkylalkyl group having 4 to 20 carbon atoms refers to a group having 4 to 20 carbon atoms in which a hydrogen atom of an alkyl group is substituted with a cycloalkyl group. The cycloalkyl group in the cycloalkylalkyl group may be monocyclic or polycyclic. Examples of cycloalkylalkyl groups having 4 to 20 carbon atoms and a monocyclic cycloalkyl group include a cyclopropylmethyl group, a 2-cyclobutylethyl group, a 3-cyclopentylpropyl group, a 4-cyclohexylbutyl group, a cycloheptylmethyl group, a cyclooctylmethyl group, a 2-cyclononylethyl group, and a 2-cyclodecylethyl group. Examples of cycloalkylalkyl groups having 4 to 20 carbon atoms and a polycyclic cycloalkyl group include a 3-3-adamantylpropyl group, and a decahydronaphthylpropyl group.

[0039] The aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms is a hydrocarbon group that contains an aromatic hydrocarbon ring but does not contain a heterocycle, and may contain an aliphatic hydrocarbon group. Examples of such aromatic hydrocarbon ring-containing groups include aryl groups having 6 to 20 carbon atoms and arylalkyl groups having 7 to 20 carbon atoms.

[0040] The aryl group having 6 to 20 carbon atoms may have a monocyclic structure, a fused ring structure, or a structure in which two aromatic hydrocarbon rings are linked together. The aryl group in which two aromatic hydrocarbon rings are linked may be one in which two aromatic hydrocarbon rings of a monocyclic structure are linked, one in which an aromatic hydrocarbon ring of a monocyclic structure and an aromatic hydrocarbon ring of a fused ring structure are linked, or one in which an aromatic hydrocarbon ring of a fused ring structure and an aromatic hydrocarbon ring of a fused ring structure are linked. The linking group connecting two aromatic hydrocarbon rings may be any group that can impart aromaticity to the aryl group as a whole, and examples thereof include a single bond, a sulfide group (-S-), a carbonyl group, etc. Examples of aryl groups having a monocyclic structure include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, and a 2,4,6-trimethylphenyl group. Examples of aryl groups having a fused ring structure include a naphthyl group, an anthracenyl group, a phenanthryl group, and a pyrenyl group. Examples of aryl groups having two monocyclic aromatic hydrocarbon rings linked together include a biphenyl group, a diphenyl sulfide group, and a benzoylphenyl group.

[0041] The arylalkyl group having 7 to 20 carbon atoms refers to a group in which one or more hydrogen atoms in an alkyl group are substituted with an aryl group. Examples of the arylalkyl group having 7 to 20 carbon atoms include a benzyl group, a fluorenyl group, an indenyl group, a 9-fluorenylmethyl group, an α-methylbenzyl group, an α,α-dimethylbenzyl group, a phenylethyl group, and a naphthylpropyl group.

[0042] The above L 1 The divalent hydrocarbon group used in R 1 Examples of the hydrocarbon groups used in the above include groups in which one hydrogen atom has been removed.

[0043] In the present disclosure, a substituted hydrocarbon group refers to a group in which a hydrogen atom in the hydrocarbon group has been substituted with a substituent. Examples of the substituent that substitutes the hydrogen atom in such a hydrocarbon group include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, and a carboxyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0044] A hydrocarbon group in which one or more methylene groups have been substituted with a divalent group selected from Group A does not have a structure in which multiple divalent groups are adjacent to each other. The multiple divalent groups may be the same or different. The divalent group selected from the above <Group A> does not substitute the methylene group at the ether group side end of the hydrocarbon group. 1 , R 2 and R 3 The ether group to which is bonded is not bonded to a divalent group selected from the above <Group A>. The same can be said for <Group B> as for the above <Group A>. Also, the above R 1 , R 2 and R 3 However, when one or more methylene groups in the hydrocarbon group are substituted with a divalent group selected from the above <Group A>, the group in which one or more methylene groups in the hydrocarbon group are substituted with a divalent group selected from the above <Group A> does not include the group represented by the above general formula (2).

[0045] In the present disclosure, the number of carbon atoms in a group refers to the total number of carbon atoms in the group. Therefore, when a hydrogen atom in a group is substituted with a substituent, the number of carbon atoms in the group after the substitution is specified. For example, in the case of a "group in which a hydrogen atom of an alkyl group having 1 to 20 carbon atoms is substituted with a substituent," the number of carbon atoms of 1 to 20 refers to the number of carbon atoms in the alkyl group after the hydrogen atom is substituted with the substituent, not the number of carbon atoms in the alkyl group before the hydrogen atom is substituted. Furthermore, in the present disclosure, the number of carbon atoms in a group in which a methylene group in a group with a specified number of carbon atoms is replaced with a divalent group refers to the number of carbon atoms in the group after the substitution. For example, in the case of a "group in which a methylene group in an alkyl group having 1 to 20 carbon atoms is replaced with a divalent group," the "1 to 20 carbon atoms" refers to the number of carbon atoms in the alkyl group after the methylene group is replaced with the divalent group, not the number of carbon atoms in the alkyl group before the substitution.

[0046] Above R 1 , R 2 and R 3 At least one of the above is a group represented by the above general formula (2). In the present disclosure, the above R 1 , R 2 and R 3 It is preferable that at least two of the R 1 , R 2 and R 3 It is more preferable that all of are groups represented by the above general formula (2), because Compound 1 is a compound that can form a cured product with superior water solubility and heat resistance.

[0047] Above R 1 , R 2 and R 3 When is a group other than the group represented by the general formula (2), it is preferably a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, because Compound 1 is a compound that can form a cured product with superior water solubility and heat resistance.

[0048] Above R 1 , R 2 and R 3 The number of carbon atoms in the substituted or unsubstituted hydrocarbon group used is preferably 1 to 15, more preferably 2 to 10, and even more preferably 3 to 5. This is because Compound 1 is a compound that can form a cured product with superior water solubility and superior heat resistance. Also, Compound 1 is easy to synthesize.

[0049] Above R 1 , R 2 and R 3 The hydrocarbon group used in is preferably an aliphatic hydrocarbon group, more preferably a chain aliphatic hydrocarbon group, even more preferably an alkyl or alkenyl group, and particularly preferably an alkenyl group. This is because Compound 1 is a compound that can form a cured product with excellent water solubility and heat resistance. Also, Compound 1 is easy to synthesize. Above R 1 , R 2 and R 3 The alkenyl group used in is preferably a terminal alkenyl group, more preferably a vinyl group, an allyl group, or a 2-methyl-2-propenyl group, and even more preferably an allyl group or a 2-methyl-2-propenyl group. This is because Compound 1 is a compound that can form a cured product with excellent water solubility and heat resistance. In addition, Compound 1 is easy to synthesize.

[0050] The above L 1 It is preferable that the bond is a direct bond, that is, the group represented by the above general formula (2) is a group represented by the following general formula (2a). This is because Compound 1 is a compound that can form a cured product with excellent water solubility and heat resistance. In addition, Compound 1 is easy to synthesize.

[0051] [ka]

[0052] (In the formula, R 4 represents a hydrogen atom or a methyl group, * indicates a binding site.)

[0053] Above R 4 is preferably a hydrogen atom, because Compound 1 is a compound that can form a cured product with excellent water solubility and heat resistance.

[0054] 2. Method for producing compound 1 The method for producing Compound 1 may be any method that can produce a compound of the desired structure. Examples of such methods include a method (Method 1) having an epoxy group introduction step of introducing an epoxy group into a hydroxyl group of an inositol orthoester using epichlorohydrin or methylepichlorohydrin, and a method (Method 2) having an unsaturated bond introduction step of introducing an unsaturated bond into a hydroxyl group of an inositol orthoester, and an oxidation step of oxidizing the introduced unsaturated bond with a peroxide. The following (S1) is a process diagram showing an example of the manufacturing method according to the above method 1, and the following (S2) is a process diagram showing an example of the manufacturing method according to the above method 2. In the following process diagrams (S1) and (S2), (b1) represents an example of an inositol orthoester, and (c1) represents an example of a structure after the introduction of an unsaturated bond.

[0055] [ka]

[0056] (1) Epoxy group introduction step The epoxy group introduction step is a step of introducing an epoxy group into a hydroxyl group of an inositol orthoester using epichlorohydrin or methylepichlorohydrin.

[0057] The inositol orthoester used in this step, for example, when it is the compound represented by (b1) above, can be obtained by a synthesis method in which myo-inositol and a trialkyl orthoformate compound are used as raw materials and heated in a solvent, if necessary, using an acid catalyst. In addition to the compound represented by (b1) above, the inositol orthoester can also be one in which hydrocarbon groups have been introduced into some of the three hydroxyl groups of the compound represented by (b1) above. Such an inositol orthoester may be, for example, a compound represented by the following general formula (11).

[0058] [ka]

[0059] (In the formula, R 11 , R 12 and R 13 each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group C>, R 11 , R 12 and R 13 at least one of is a hydrogen atom, <Group C> is -O-, -CO-, -COO-, -OCO-, -NR 121 -, -NR 121 CO- and -S- R 121 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

[0060] Above R 11 , R 12 and R 13 and R 121 The hydrocarbon group used in R 1 The hydrocarbon groups in <Group C> can be the same as those in <Group A> above. Furthermore, groups in which one or more methylene groups in a hydrocarbon group have been substituted with a divalent group selected from the above <Group C> do not include groups represented by the above general formula (2).

[0061] In this disclosure, R 11 , R 12 and R 13 Preferably, at least two of R are hydrogen atoms, 11 , R 12 and R 13 It is more preferable that all of R are hydrogen atoms, that is, the inositol orthoester is a compound represented by the above formula (b1).1 , R 2 and R 3 This is because it becomes easy to synthesize Compound 1 in which all of are groups represented by the above general formula (2).

[0062] The heating temperature in the above synthesis method is preferably 30° C. or higher and 180° C. or lower, and more preferably 80° C. or higher and 150° C. or lower, because this results in an excellent yield. The heating time in the above synthesis method is preferably 1 hour or more and 72 hours or less, because this results in an excellent yield.

[0063] Examples of the solvent include alcohols such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol, t-butyl alcohol, diacetone alcohol, glycerin, monoacetylene, ethylene glycol, triethylene glycol, and hexylene glycol; and amides such as formamide, acetamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, and 1,3-dimethyl-2-imidazolidinone. In this step, the solvent is preferably an amide, since this results in an excellent yield. The amount of the solvent used can be 0.1 mL or more and 100 mL or less, and preferably 0.5 mL or more and 10 mL or less, per 1 mmol of the raw material myo-inositol, because this results in an excellent yield.

[0064] Examples of the trialkyl orthoformate compound include trimethyl orthoformate, triethyl orthoformate, and triisopropyl orthoformate. In this step, the trialkyl orthoformate compound is preferably trimethyl orthoformate or triethyl orthoformate, since this results in an excellent yield.

[0065] The amount of the trialkyl orthoformate compound used is preferably 1 mmol to 10 mmol, more preferably 1.5 mmol to 3 mmol, per 1 mmol of the raw material myo-inositol, because this provides an excellent balance between the yield and the removal of excess trialkyl orthoformate compound.

[0066] Examples of the acid catalyst include sulfonic acids such as p-toluenesulfonic acid, o-toluenesulfonic acid, benzenesulfonic acid, 1-naphthalenesulfonic acid, and 2-naphthalenesulfonic acid, and hydrates of sulfonic acids. In this step, the acid catalyst is preferably a hydrate of a sulfonic acid, since this results in an excellent yield. In this step, the amount of the acid catalyst used is preferably 0.001 mmol or more and 1 mmol or less, and more preferably 0.01 mmol or more and 0.3 mmol or less, relative to 1 mmol of the raw material myo-inositol, because this results in an excellent yield.

[0067] In this step, a known epoxidation method can be used as a method for reacting epichlorohydrin or methylepichlorohydrin with the hydroxyl group of the inositol orthoester compound. The epoxidation method may, for example, be a method in which an inositol orthoester is mixed with epichlorohydrin or methylepichlorohydrin and then heated.

[0068] The amount of epichlorohydrin or methylepichlorohydrin used is preferably 1.5 to 30 equivalents, and more preferably 2 to 15 equivalents, relative to 1 equivalent of the hydroxyl group of the inositol orthoester, because this provides an excellent yield.

[0069] The heating temperature in the above epoxidation method is preferably 20° C. or higher and 150° C. or lower, and more preferably 30° C. or higher and 80° C. or lower, because this results in an excellent yield. The reaction time in the above epoxidation method is preferably 1 hour or more and 10 hours or less, because this results in an excellent yield.

[0070] The epoxidation process is preferably carried out in the presence of an alkali metal hydroxide. Examples of the alkali metal hydroxide include sodium hydroxide and potassium hydroxide. The amount of the alkali metal hydroxide used is preferably 0.8 to 1.5 equivalents, more preferably 0.9 to 1.2 equivalents, relative to 1 equivalent of the hydroxyl group of the inositol orthoester, because this provides an excellent yield.

[0071] (2) Unsaturated bond introduction step The unsaturated bond introduction step is a step of introducing an unsaturated bond into the hydroxyl group of the inositol orthoester compound.

[0072] The inositol orthoester used in this step can be the same as that described in the above section "(1) Epoxy group introduction step." In this step, when the inositol orthoester is a compound represented by the above general formula (11), R 11 , R 12 and R 13 The hydrocarbon group used in is preferably a group other than an alkenyl group, more preferably an alkyl group, an aliphatic ring-containing group, an aryl group, or an arylalkyl group, and even more preferably an alkyl group, because this makes the introduction of an unsaturated bond in this step more effective.

[0073] Examples of the unsaturated bond include an ethylenically unsaturated double bond and an ethylenically unsaturated triple bond, but an ethylenically unsaturated double bond is preferred, because this facilitates the formation of an epoxy group in the oxidation step described below.

[0074] The inositol orthoester after introduction of an unsaturated bond formed by this step (hereinafter, sometimes referred to as an unsaturated group-introduced inositol orthoester) can be, for example, a compound represented by the following formula (21) when the unsaturated bond is an ethylenically unsaturated double bond.

[0075] [ka]

[0076] (In the formula, R 21 , R 22 and R 23 each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group D>, R 21 , R 22 and R 23 at least one of the above is a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms or a group in which one or more methylene groups in the alkenyl group are substituted with a divalent group selected from the following <Group D> (hereinafter, may be referred to as an alkenyl group), <Group D> is -O-, -CO-, -COO-, -OCO-, -NR 131 -, -NR 131 CO- and -S- R 131 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

[0077] Above R 21 , R 22 and R 23 and R 131 The hydrocarbon group and alkenyl group used in R 1 The hydrocarbon groups and alkenyl groups can be the same as those used in the above <Group D>. In addition, the hydrocarbon groups and alkenyl groups can be the same as those used in the above <Group A>. Furthermore, groups in which one or more methylene groups in a hydrocarbon group or an alkenyl group are substituted with a divalent group selected from the above <Group D> do not include groups represented by the above general formula (2).

[0078] In this disclosure, R 21 , R 22 and R 23 At least two of R are preferably alkenyl groups, 21 , R 22 and R 23 It is more preferable that all of R are alkenyl groups. 1 , R 2 and R 3 This is because it becomes easy to synthesize Compound 1 in which all of are groups represented by the above general formula (2).

[0079] Above R 21 , R 22 and R 23 The alkenyl group used in is preferably an alkenyl group, because this facilitates the formation of an epoxy group in the oxidation step described below. The preferred types of alkenyl groups are described above in R 1 , R 2 and R 3 The preferred alkenyl groups used in the above can be the same as those described above.

[0080] In this step, an example of a method for introducing an unsaturated bond is to react an inositol orthoester with an allyl halide compound.

[0081] The inositol orthoester used in this step can be the same as that described in the above section "(1) Epoxy group introduction step," and therefore, further explanation will be omitted here.

[0082] The halogenated allyl compound may be a compound having a structure in which the alkenyl group is bonded to a halogen atom, and more specific examples thereof include halogenated allyl compounds and halogenated 2-methylallyl compounds. The allyl halide compound includes allyl halides such as allyl fluoride, allyl chloride, allyl bromide, and allyl iodide. Examples of the 2-methylallyl halide compound include 2-methylallyl chloride, 2-methylallyl bromide, and 2-methylallyl iodide.

[0083] The amount of the allyl halide compound used is preferably 1 mmol to 10 mmol, more preferably 3.2 mmol to 3.8 mmol, per 1 mmol of the inositol orthoester, because this provides an excellent yield.

[0084] The reaction temperature when reacting the allyl halide compound is preferably −78° C. or higher and 30° C. or lower, and more preferably −20° C. or higher and 30° C. or lower, because this results in an excellent yield. The reaction time is preferably 1 hour or more and 50 hours or less, since this results in an excellent yield.

[0085] In this step, the reaction of the allyl halide compound may be carried out in a solvent. As the solvent, for example, the above-mentioned amides can be used. The amount of the solvent used is preferably 0.1 mL or more and 100 mL or less, and more preferably 0.5 mL or more and 10 mL or less, per 1 mmol of the inositol orthoester, because this results in an excellent yield.

[0086] In this step, the reaction of the allyl halide compound is preferably carried out in the presence of a basic compound, since this results in an excellent yield. Examples of the basic compound include superbasic compounds such as sodium amide, sodium hydride, n-butyllithium, and 1,8-diazabicyclo[5.4.0]undec-7-ene; strong basic compounds such as potassium methoxy, potassium ethoxy, and potassium t-butoxy; and weak basic compounds such as triethylamine and tri-n-butylamine. In this step, the basic compound preferably contains a superbasic compound, and more preferably contains sodium hydride, because this leads to an excellent yield. The amount of the basic compound used is not particularly limited, but is preferably 3 mmol to 15 mmol, more preferably 4 mmol to 10 mmol, per 1 mmol of the inositol orthoester, because this provides an excellent balance between the yield and the removal of excess basic compound by hydrolysis.

[0087] (3) Oxidation process The oxidation step is a step in which the introduced unsaturated bond is oxidized with a peroxide.

[0088] The introduced unsaturated bond refers to the unsaturated bond possessed by the unsaturated group-introduced inositol orthoester.

[0089] The temperature during the oxidation is preferably −30° C. or higher and 50° C. or lower, and more preferably −10° C. or higher and 30° C. or lower, because this results in an excellent yield. The oxidation time is preferably 1 hour or more and 50 hours or less, since this results in an excellent yield.

[0090] Examples of the peroxides include organic peroxides such as performic acid, peracetic acid, trifluoroperacetic acid, perbenzoic acid, metachloroperbenzoic acid, and monoperoxyphthalic acid; inorganic peroxides such as permanganic acid; and peroxides such as di-t-butyl peroxide, dicumyl peroxide, and benzoyl peroxide. In this step, the peroxide is preferably an organic peroxide, since this results in an excellent yield. The amount of the peroxide used is preferably 3 mmol to 10 mmol, more preferably 4 mmol to 7 mmol, per 1 mmol of the unsaturated group-introduced inositol orthoester, because this provides an excellent balance between the yield and the removal of excess peroxide.

[0091] In this step, the oxidation may be carried out in a solvent. Examples of the solvent include the above-mentioned alcohols; aromatic hydrocarbon solvents such as benzene, toluene, xylene, n-butylbenzene, diethylbenzene, methoxybenzene, 1,2-dimethoxybenzene, mesitylene, and tetralin; halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, tetrachloroethylene, and methylene chloride; halogenated aromatic hydrocarbon solvents such as chlorobenzene; acetonitrile, and carbon disulfide. In this step, the solvent is preferably a halogenated aliphatic hydrocarbon solvent, since this results in an excellent yield. The amount of the solvent used is preferably 0.5 mL to 50 mL, more preferably 1 mL to 10 mL, per 1 mmol of the compound into which an unsaturated bond has been introduced relative to the hydroxyl groups of the inositol orthoester, because this will result in an excellent yield.

[0092] (4) Hydrocarbon group introduction step The method for producing the compound may include a hydrocarbon group introduction step of introducing a hydrocarbon group into the hydroxyl group derived from the inositol, as a step other than the epoxy group introduction step, unsaturated bond introduction step, and oxidation step.

[0093] The method for introducing such a hydrocarbon group may be any method that can bond a hydrocarbon group to the oxygen atom constituting the hydroxyl group derived from the inositol, and examples thereof include a method of reacting the inositol orthoester or the unsaturated group-introduced inositol orthoester with a hydrocarbon group-introducing agent. That is, the timing for carrying out this step may be before the epoxy group introduction step or before the unsaturated bond introduction step, or between the unsaturated bond introduction step and the oxidation step.

[0094] Examples of the hydrocarbon group-introducing agent include dialkyl sulfates such as dimethyl sulfate, diethyl sulfate, di-n-propyl sulfate, diisopropyl sulfate, di-n-butyl sulfate, di-n-pentyl sulfate, di-n-hexyl sulfate, di-n-heptyl sulfate, di-n-octyl sulfate, di-n-nonyl sulfate, and di-n-decyl sulfate; methyl bromide, ethyl bromide, n-propyl bromide, isopropyl bromide, n-butyl bromide; alkyl bromides such as n-pentyl iodide, n-hexyl bromide, n-heptyl bromide, n-octyl bromide, n-nonyl bromide, and n-decyl bromide; and alkyl iodides such as methyl iodide, ethyl iodide, n-propyl iodide, isopropyl iodide, n-butyl iodide, n-pentyl iodide, n-hexyl iodide, n-heptyl iodide, n-octyl iodide, n-nonyl iodide, and n-decyl iodide.

[0095] The reaction temperature when reacting the hydrocarbon group-introducing agent is preferably 0° C. or higher and 100° C. or lower, and more preferably 10° C. or higher and 50° C. or lower, because this results in an excellent yield. The reaction time is preferably from 1 hour to 50 hours, since this results in an excellent yield.

[0096] When the hydrocarbon group-introducing agent is reacted, it is preferable to carry out the reaction in a solvent, since this results in an excellent yield. The solvent used when reacting the hydrocarbon group-introducing agent includes the above-mentioned amides, because this leads to an excellent yield.

[0097] When the hydrocarbon group-introducing agent is reacted, it is preferable to carry out the reaction in the presence of a basic compound, since this results in an excellent yield. As the basic compound, the same compounds as those used in the unsaturated bond introduction step can be used.

[0098] 3.Other Compound 1 is preferably used in applications requiring excellent water solubility, etc., and can be used in various applications where epoxy compounds are used. Specific examples of the applications include semiconductor encapsulation materials, laminating agents for printed wiring boards, adhesives for electronic components, encapsulating materials for electronic components, casting materials, varnishes, paints, structural adhesives, and fiber-reinforced composite materials.

[0099] B. Composition Next, the composition of the present disclosure will be described. The composition of the present disclosure is characterized by containing Compound 1.

[0100] According to the present disclosure, water can be used as a solvent because the composition contains Compound 1. Furthermore, the composition has excellent compatibility with water-soluble materials.

[0101] 1. Compound 1 Compound 1 can be the same as that described in the above section "A. Compound," and therefore, a description thereof will be omitted here.

[0102] The content of Compound 1 is preferably 1 part by mass or more and 90 parts by mass or less, more preferably 2 parts by mass or more and 40 parts by mass or less, and even more preferably 4 parts by mass or more and 15 parts by mass or less, per 100 parts by mass of the composition. When the content of Compound 1 is within the above range, the composition has excellent curability.

[0103] 2. Hardener The composition preferably contains a curing agent, as this provides the composition with excellent curability.

[0104] The curing agent may be one that can react with the epoxy group of compound 1 to form a high molecular weight compound. As such a curing agent, those generally used as epoxy curing agents can be used, and for example, those described in JP-A-2005-506402 can be used. Specific examples of the curing agent include aliphatic amines, aromatic amines, isocyanates, polyfunctional hydroxyl-containing compounds, anhydrides, polyfunctional acids, imidazoles, polyfunctional mercaptans, boron trihalide complexes, dicyanamides, and mixtures thereof. In the present disclosure, the curing agent preferably contains an aliphatic amine, because the composition has excellent curing properties. In addition, since the aliphatic amine has excellent water solubility, the composition can effectively exhibit the effects of using Compound 1.

[0105] Examples of the aliphatic amine include those having a primary or secondary amino group and not having an aromatic carbon ring. Specific examples include 1,2-diaminocyclohexane, isophoronediamine, ethylenediamine, diethylenetriamine, hexamethylenediamine, triethylenetetraamine, tetraethylenepentamine, ethanolamine, piperazine, aminoethylpiperazine, aminoethylethanolamine, diethylaminopropylamine, dimethylaminopropylamine, 2,5-dimethyl-2,5-hexanediamine, bis(aminocyclohexyl)methane, 3-amino-1-cyclohexylaminopropane, polyethanolamine, polypropanolamine, polyethyleneimine, and mixtures thereof. In the present disclosure, the aliphatic amine is preferably a compound having a primary amino group, and more preferably includes a chain primary amine compound such as ethylenediamine or hexamethylenediamine. This is because the composition has excellent curability. Furthermore, since the aliphatic amine has excellent water solubility, the composition can effectively exhibit the effects of using Compound 1.

[0106] Specific examples of the aromatic amine include diaminobenzene, methylenedianiline, oxydianiline, diaminodiphenyl sulfide, diaminodiphenyl sulfone, 2,4-bis-(p-aminobenzoyl)aniline, diaminotoluene, ketimine, amidoamine, and mixtures thereof.

[0107] The polyfunctional hydroxyl-containing compounds include novolaks, resols, bisphenols, and the like. Examples of novolaks include thermoplastic phenol-formaldehyde resins obtained by using an acid catalyst and an excess of phenol. Resoles include, for example, alkali-catalyzed thermosetting phenol-formaldehyde resins made from partially condensed phenol alcohols. Examples of bisphenols include bisphenol A (4,4'-isopropylidenediphenol), bisphenol F (bis(4-hydroxyphenyl)methane), and 2,2'-bisphenol.

[0108] Specific examples of the anhydride include benzophenonetetracarboxylic anhydride, chlorenic anhydride, succinic anhydride, dodecenylsuccinic anhydride, hexahydrophthalic anhydride, maleic anhydride, methylhexahydrophthalic anhydride, tetrahydrophthalic anhydride, NADIC methyl anhydride (3a,4,7,7a-tetrahydromethyl-4,7-methanoisobenzofuran-1,3-dione), phthalic anhydride, polyadipic polyanhydride, polyacerine polyanhydride, polysebacic polyanhydride, pyromellitic anhydride, and mixtures thereof.

[0109] Specific examples of the polyfunctional acid include adipic acid, sebacic acid, azelaic acid, terephthalic acid, isophthalic acid, cyclohexanedicarboxylic acid, and mixtures thereof.

[0110] Specific examples of the imidazole include 2-methylimidazole, 2-hydroxypropylimidazole, 2-heptadecylimidazole, 1-benzyl-2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cycloethyl-2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, and mixtures thereof.

[0111] Specific examples of the boron trifluoride complex include boron trifluoride diethyl etherate.

[0112] As the curing agent, an acid generator or a base generator can also be used.

[0113] Examples of the acid generator include a photoacid generator that generates an acid when irradiated with energy rays such as ultraviolet rays, and a thermal acid generator that generates an acid when heated. Examples of such photoacid generators and thermal acid generators include those described as photocationic polymerization initiators and thermal cationic polymerization initiators in JP-A-2023-181911. Specific examples of the photoacid generator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, thianthrhenium salts, thioxanthonium salts, and (2,4-cyclopentadien-1-yl)[(1-methylethylbenzene]-Fe cations in which the anion moiety is BF4. - , PF6 - , SbF6 - , [BX4] - (wherein X is a phenyl group substituted with at least two fluorine atoms or trifluoromethyl groups) may be used alone or in combination of two or more kinds. Examples of the thermal acid generator include phonate, triphenylsulfonium tetrafluoroborate, tri-p-tolylsulfonium hexafluorophosphate, tri-p-tolylsulfonium trifluoromethanesulfonate, bis(cyclohexylsulfonyl)diazomethane, bis(tert-butylsulfonyl)diazomethane, bis(p-toluenesulfonyl)diazomethane, triphenylsulfonium trifluoromethanesulfonate, diphenyl-4-methylphenylsulfonium trifluoromethanesulfonate, diphenyl-2,4,6-trimethylphenylsulfonium-p-toluenesulfonate, and diphenyl-p-phenylthiophenylsulfonium hexafluorophosphate.

[0114] The base generator may be a photobase generator that generates a base upon irradiation with energy rays such as ultraviolet rays. The photobase generator is preferably a salt containing a borate anion because it has good sensitivity to light.

[0115] The content of the curing agent is preferably 0.1 to 70 parts by mass, more preferably 0.5 to 30 parts by mass, and even more preferably 1 to 10 parts by mass, per 100 parts by mass of the composition, because this gives the composition excellent curability.

[0116] The content of the curing agent is preferably 0.1 parts by mass or more and 70 parts by mass or less, and more preferably 10 parts by mass or more and 30 parts by mass or less, relative to 100 parts by mass of the total of Compound 1 and the epoxy compound described below, because this gives the composition excellent curability.

[0117] 3. Solvent The composition may include a solvent. The solvent preferably contains water, specifically, is preferably water or an aqueous solvent. Furthermore, organic solvents can also be preferably used as the solvent, because they can effectively exhibit the effects of using Compound 1, such as excellent dispersion stability. Here, the aqueous solvent refers to a mixed solvent of water and an organic solvent.

[0118] The organic solvent is preferably one that has a high affinity for water, and examples thereof include alcohols such as methanol, ethanol, propanol, butanol, isopropanol, and octanol; ether alcohols and esters thereof such as ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether; glycols such as ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, polyoxyethylene glycol, polyoxypropylene glycol, and ethylene propylene glycol; ethyl cellosolve, butyl cellosolve, acetone, methoxypropanol, ethoxypropanol, and other alkoxy alcohols; cyclic ethers such as tetrahydrofuran and dioxane; amides such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; and dimethyl sulfoxide. In the present disclosure, the organic solvent is preferably dimethyl sulfoxide or a cyclic ether, because the composition can effectively exhibit the effects of using Compound 1.

[0119] The content of the solvent is preferably 0.1 parts by mass or more and 95 parts by mass or less in 100 parts by mass of the composition, because this allows Compound 1 to be dispersed stably.

[0120] 4. Epoxy compounds The composition may contain an epoxy compound other than Compound 1. As such an epoxy compound, either a water-soluble epoxy compound or a water-insoluble epoxy compound can be used. As such water-soluble epoxy compounds and water-insoluble epoxy compounds, for example, those listed as water-soluble epoxy resins and water-insoluble epoxy resins, respectively, in JP-A No. 2023-093943 can be used.

[0121] 5.Other The use of the composition can be the same as that described in the section "3. Others" under "A. Compounds" above.

[0122] C. Cured product Next, the cured product of the present disclosure will be described. The cured product of the present disclosure is characterized by being a cured product of the above-described composition.

[0123] According to the present disclosure, the above-mentioned compounds are used, and therefore a cured product can be easily formed using a composition containing water as a solvent.

[0124] The contents of the composition can be the same as those described in the section "B. Composition" above, and therefore a description thereof will be omitted here. The method for producing the cured product may be any method that can form a cured product in the desired cured state, and for example, the method described in the section "D. Method for producing cured product" below can be used.

[0125] The uses of the cured product of the present disclosure can be similar to those described in the section "3. Others" of "A. Compounds" above.

[0126] D. Manufacturing method of cured product Next, a method for producing the cured product of the present disclosure will be described. The method for producing a cured product according to the present disclosure is characterized by having a curing step of curing the above-described composition.

[0127] According to the present disclosure, since the above-mentioned compound is used, a cured product can be easily formed using a composition containing water as a solvent.

[0128] Each step of the method for producing a cured product according to the present disclosure will be described below.

[0129] 1.Curing process This step is a step of curing the composition. The contents of the composition can be the same as those described in the section "B. Composition" above, and therefore a description thereof will be omitted here.

[0130] The composition may be cured by any method that can form a desired cured product, and for example, at least one of a heating method and a light irradiation method can be used. In this step, when the method is a heating method, the heating temperature may be any temperature that allows the formation of a desired cured product, and may be, for example, 40°C or higher and 200°C or lower.

[0131] 2.Other The method for producing a cured product according to the present disclosure includes the curing step described above, but may also include other steps as necessary. The other steps include, for example, a coating step of coating the composition.

[0132] The uses of the cured product produced by the production method of the present disclosure can be similar to those described in the above section "3. Others" under "A. Compounds," for example.

[0133] E. Other The present disclosure includes the following aspects. [1] A compound represented by the following general formula (1): [ka] (In the formula, R 1 , R 2 and R 3each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group A>, or a group represented by the following general formula (2): R 1 , R 2 and R 3 At least one of the above is a group represented by the following general formula (2): <Group A> is -O-, -CO-, -COO-, -OCO-, -NR 101 -, -NR 101 CO- and -S- R 101 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. [ka] (In the formula, R 4 represents a hydrogen atom or a methyl group, L 1 represents a direct bond, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group B>, * represents a binding site <Group B> is -O-, -CO-, -COO-, -OCO-, -NR 111 -, -NR 111 CO- and -S- R 111 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. [2] R above 1 , R 2 and R 3 The compound according to [1], wherein all of are groups represented by the above general formula (2). [3] L above 1 is a direct bond. [4] A composition comprising the compound according to any one of [1] to [3]. [5] The composition according to [4], characterized in that the composition contains water as a solvent. [6] The composition according to [4] or [5], characterized in that the composition contains a curing agent. [7] A cured product of the composition according to any one of [4] to [6]. [8] A method for producing a cured product, comprising a curing step of curing the composition according to any one of [4] to [6].

[0134] The present disclosure is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any embodiment that has substantially the same configuration as the technical idea described in the claims of the present disclosure and exhibits similar effects is included within the technical scope of the present disclosure. [Example]

[0135] The present disclosure will be described in more detail below with reference to examples and comparative examples, but the present disclosure is not limited to these examples.

[0136] [Example 1] The inositol orthoester (b1) was synthesized according to Takagi, A.; Usuguchi, K.; Takashima, I.; Okuda, K., "Total Synthesis of Antiausterity Agent (±)-Uvaridacol L by Regioselective Axial Diacylation of a myo-Inositol Orthoester", Org. Lett. 2021, 23, 11, pp. 4083-4087. Under an argon atmosphere, sodium hydride (2.0 g of a mineral oil dispersion with a sodium hydride content of 60% was weighed out; net sodium hydride amount was 1.2 g, 50 mmol) was washed three times with 10 mL of hexane. 25 mL of dehydrated N,N-dimethylformamide (DMF) was added thereto. Furthermore, a solution of inositol orthoester (b1) (1.00 g, 5.26 mmol) in 10 mL of dehydrated DMF was added thereto. The reaction vessel was cooled to 0°C in an ice bath, and allyl bromide (1.6 mL, density 1.4 g / cm) was added thereto. 3To the resulting solution, 2.2 g (18 mmol) of ethyl acetate (c1) was added over 5 minutes. After 1 hour, the ice bath was removed and the mixture was stirred at 25°C for 23 hours. Water (20 mL) was then added over 10 minutes. The resulting solution was extracted four times with ethyl acetate (20 mL). Sodium sulfate was added to the organic layer and the mixture was stirred for 1 hour. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to azeotropic distillation with toluene and hexane to obtain triallyl compound (c1) (1.61 g (5.19 mmol), 99% yield) as a colorless, transparent, viscous liquid. Triaryl compound (c1) (1.61 g, 5.19 mmol) was dissolved in dichloromethane (15 mL), and the reaction vessel was cooled to 0 °C in an ice bath. Metachloroperbenzoic acid (8.4 g of a water-containing compound with a metachloroperbenzoic acid content of 69% was weighed; net metachlorobenzoic acid amount was 5.8 g, 34 mmol) was added. After 1 hour, the ice bath was removed, and the mixture was stirred at 25 °C for 23 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in diethyl ether (50 mL) and extracted three times with water (30 mL). Sodium bicarbonate (5 g) was added to the resulting aqueous layer, followed by extraction four times with ethyl acetate (80 mL). Sodium sulfate was added to the organic layer, and the mixture was stirred for 1 hour and filtered. The filtrate was concentrated under reduced pressure and dried in vacuo to obtain compound 1 (compound 1-1) as a colorless viscous liquid (1.26 g, 3.52 mmol, 68% yield). Regarding the obtained compound 1-1, 1 H-NMR (measuring device: JMN-AL400, manufactured by JEOL Ltd., measuring solvent: deuterated chloroform) was measured, and it was confirmed that the compound was the compound represented by the following formula (1-1). 1 The results of H-NMR measurements are shown in Figure 1.

[0137] [ka]

[0138] [Comparative Example 1] The compound represented by the following formula (1'-1) (compound 1'-1) was obtained according to Shimokawaji, T.; Sudo, A., "Synthesis of Partially Bio-based Triepoxides from Naturally Occurring myo-Inositol and Their Polyadditions", J. Polym. Sci. 2020, 58(9), pp. 1229-1235.

[0139] [ka]

[0140] Comparative Example 2 A compound represented by the following formula (1'-2) (compound 1'-2) was obtained according to Japanese Patent No. 6812062.

[0141] [ka]

[0142] The compounds obtained in the Examples and Comparative Examples were evaluated for water solubility and heat resistance according to the following procedures. 1. Water solubility evaluation In a four-neck flask equipped with a three-one motor and a half-moon stirring blade, compound 1-1 and water were mixed so that the concentration of compound 1-1 was 10 mass%, and the mixture was stirred at 25° C. for 10 minutes to obtain an evaluation sample. Similarly, evaluation samples were obtained for compound 1′-1 and compound 1′-2. The obtained evaluation samples were visually observed and evaluated according to the following criteria. ◯: Completely dissolved and transparent. ×: Insoluble matter was present and the mixture was cloudy.

[0143] 2. Heat resistance evaluation Compound 1-1 (0.207 g, 0.578 mmol) was placed in a sample vial and dissolved in 1,4-dioxane (1 mL). To this was added hexamethylenediamine (0.0510 g, 0.439 mmol) dissolved in 1,4-dioxane (0.5 mL). After stirring at 60°C for 72 hours, a white solid was obtained. The solid was washed with methanol and then heated and vacuum dried to obtain a yellow cured product (0.2171 g, 84% yield). Approximately 5 mg of the obtained cured product was weighed out and placed in a pan for differential scanning calorimetry, and using a differential scanning calorimeter (DSC-60 Plus, manufactured by Shimadzu Corporation) it was heated from room temperature to 200°C under a nitrogen stream, cooled to -50°C at a rate of 20°C / min, and then measured from -50°C to 250°C at a rate of 10°C / min to confirm the glass transition point (Tg). Similarly, the Tg of Compound 1'-1 and Compound 1'-2 was confirmed after obtaining cured products. The obtained Tg was evaluated according to the following criteria. ◯: Tg was 150°C or higher. ×: Tg was less than 150°C.

[0144] [Table 1]

[0145] From the above results, it was confirmed that the compounds of the examples have excellent water solubility, and that the compounds of the examples can form compositions with excellent dispersion stability even when containing water as a solvent. Furthermore, it was confirmed that the compounds of the Examples were capable of forming cured products with higher glass transition temperatures than the compounds of the Comparative Examples, and thus it was confirmed that the compounds of the Examples were capable of forming cured products with excellent heat resistance. From the above, it was confirmed that the compound of the present disclosure can form a cured product that has excellent water solubility and heat resistance.

Claims

1. A compound represented by the following general formula (1): 【Chemical 1】 (In the formula, R １ , R ２ and R ３ each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group A>, or a group represented by the following general formula (2): R １ , R ２ and R ３ At least one of the above is a group represented by the following general formula (2): <Group A> is —O—, —CO—, —COO—, —OCO—, —NR １０１ -, -NR １０１ CO— and —S—, R １０１ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. 【Chemistry 2】 (In the formula, R ４ represents a hydrogen atom or a methyl group, L １ represents a direct bond, a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been substituted with a divalent group selected from the following <Group B>, * represents a binding site; <Group B> is —O—, —CO—, —COO—, —OCO—, —NR １１１ -, -NR １１１ CO— and —S—, R １１１ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

2. The R １ , R ２ and R ３ The compound according to claim 1, wherein all of the above are groups represented by the general formula (2).

3. A composition comprising the compound of claim 1.

4. The composition of claim 3, wherein the composition contains water as a solvent.

5. The composition of claim 3, wherein the composition contains a curing agent.

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

7. A method for producing a cured product, comprising a curing step of curing the composition according to claim 3.

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