Epoxy compounds and cured products

Abstract

To provide a novel epoxy compound capable of forming a cured product excellent in flexibility.SOLUTION: The epoxy compound is represented by general formula (1) in the figure. (In general formula (1), X is a divalent linking group in which the number of carbon atoms from hydrocarbon is from 2 to 10; and R1 and R2 are each independently a hydrocarbon group having 10-18 carbon atoms.)SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to epoxy compounds and cured products.

Background Art

[0002] Epoxy compounds are excellent in heat resistance, adhesiveness, flexibility, electrical properties, etc., and are used in various applications such as surface protective films, interlayer insulators, protective insulating films for printed wiring boards, and fiber reinforced composite materials of semiconductor elements and organic thin film elements (for example, organic electroluminescence elements and organic thin film solar cell elements).

[0003] In recent years, research has been conducted on using biomass-derived compounds (for example, cardanol, etc.) as raw materials for epoxy compounds.

[0004] For example, in Patent Document 1, it is disclosed that a bisphenol compound having a specific structure is used as a raw material for an epoxy compound, and it is disclosed that a compound derived from cardanol is used as a raw material for the bisphenol compound having the above specific structure.

[0005] However, in Patent Document 1, although it is disclosed that a bisphenol compound using a compound derived from cardanol as a raw material is used as a raw material for an epoxy compound, the structure and properties of the obtained epoxy compound have not been sufficiently studied.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] An object of the present invention is to provide a novel epoxy compound capable of obtaining a cured product excellent in flexibility.

[0008] As a result of intensive studies by the present inventors, a novel epoxy compound represented by the following general formula (1) was prepared. The present inventors have found that this novel epoxy compound is excellent in flexibility and useful for the above-mentioned applications, and have completed the present invention.

Means for Solving the Problems

[0009] The present invention is an epoxy compound represented by the following general formula (1).

Chemical Formula

[0010] In the epoxy compound of the present invention, in the above general formula (1), R 1 and / or R 2 preferably has 12 to 16 carbon atoms. In the epoxy compound of the present invention, the two aryl groups linked to X are preferably each derived from a cardanol hydrogenated product. In the epoxy compound of the present invention, in the above general formula (1), R 1 and / or R 2 is preferably in the meta position with respect to the oxygen atom (O 1 or O 2 ). In the epoxy compound of the present invention, in the above general formula (1), R 1 and / or R 2 is preferably in the para position with respect to X. In the epoxy compound of the present invention, in the above general formula (1), O 1 and / or O 2 is preferably in the ortho position with respect to X. In the epoxy compound of the present invention, X in the above general formula (1) preferably has 3 to 7 carbon atoms. The cured product of the present invention is a cured product obtained by curing the above epoxy compound or a composition containing the same. [Effects of the Invention]

[0011] The present invention can provide a novel epoxy compound that can produce a cured product with excellent flexibility. [Modes for carrying out the invention]

[0012] <Epoxy compounds> The epoxy compound of the present invention is represented by the following general formula (1). [ka] (In general formula (1), X is a divalent linking group derived from a hydrocarbon having 2 to 10 carbon atoms, and R 1 and R 2 Each of these is independently a hydrocarbon group with 10 to 18 carbon atoms.

[0013] In the above general formula (1), X is a divalent linking group derived from a hydrocarbon having 2 to 10 carbon atoms. The above-mentioned divalent linking groups having 2 to 10 carbon atoms may be linear, branched, or have a cyclic structure. Specifically, examples include alkylene groups, alkenylene groups, and alkynylene groups. In particular, from the viewpoint of the reactivity of the corresponding aldehydes and ketones, alkylene groups with 3 to 7 carbon atoms are preferred. Furthermore, the divalent linking groups having 2 to 10 carbon atoms may contain molecules other than carbon, such as oxygen atoms and nitrogen atoms, within the linking group. The above-mentioned divalent linking group having 2 to 10 carbon atoms may have substituents, and examples of substituents include alkyl groups, alkoxy groups, hydroxyl groups, alkoxy-substituted alkyl groups, and carboxyl groups.

[0014] In the above general formula (1), R 1and R 2 Each of these is independently a hydrocarbon group with 10 to 18 carbon atoms. The hydrocarbon group having 10 to 18 carbon atoms may be linear or branched. Furthermore, the hydrocarbon group having 10 to 18 carbon atoms may be saturated or unsaturated. Among these, alkyl groups having 10 to 18 carbon atoms are preferred, and from the viewpoint of the flexibility of the cured epoxy compound, alkyl groups having 11 to 17 carbon atoms are more preferred, and alkyl groups having 12 to 16 carbon atoms are even more preferred.

[0015] In particular, the two aryl groups linked to X are preferably derived from hydrogenated cardanol, from the viewpoint of the flexibility of the cured epoxy compound and the availability of the corresponding raw materials. Examples of structures derived from the above-mentioned hydrogenated cardanol include R 1 and R 2 Examples include those having a cardanol structure with 15 carbon atoms and a hydrocarbon group having 25 to 31 hydrogen atoms, but the alkyl group having 31 hydrogen atoms is most preferred.

[0016] In the above general formula (1), R 1 and / or R 2 is an oxygen atom (O 1 or O 2 The ortho, meta, or para position relative to the given element is preferred, but from the viewpoint of the availability of the corresponding raw materials, the meta position is preferred. R 1 O 1 It is meta-position relative to R 2 O 2 Being in the meta position relative to is more preferable.

[0017] In the above general formula (1), R 1 and / or R 2 The X may be in the ortho, meta, or para position, but it is preferably in the para position from the viewpoint of utilizing the reaction selectivity between the corresponding aldehyde or ketone and the phenol compound. R1 and R 2 It is more preferable that the position is para with respect to X.

[0018] In the above general formula (1), O 1 and / or O 2 X may be in the ortho, meta, or para position, but it is preferably in the ortho position from the viewpoint of utilizing the reaction selectivity between the corresponding aldehyde or ketone and the phenol compound. O 1 and O 2 It is more preferable that it is in the ortho position relative to X.

[0019] (Method for producing epoxy compounds) The epoxy compound of the present invention can be produced, for example, by the following method.

[0020] First, prepare the compound represented by the following general formula (2). [ka] (In general formula (2), R a This is R in the general formula (1) above. 1 or R 2 (It is the same substituent as [the other substituent].)

[0021] As for the compound represented by the above general formula (2), for example, hydrogenated alkyl-substituted monophenols derived from cardanol are preferred. The cardanol mentioned above is derived from cashew nut shell liquid, allowing for the effective utilization of cashew nut shells that were previously treated as waste.

[0022] Next, a compound represented by the following general formula (3), which is a dimer of the above general formula (2), is prepared. [ka] (In general formula (3), R a This is R in the general formula (1) above. 1 or R 2 It is the same substituent as Xa (This is the same substituent as X in the general formula (1) above.)

[0023] The compound represented by the above general formula (3) can be obtained, for example, by crosslinking the compound represented by the above general formula (2) with an aldehyde in the presence of a catalyst.

[0024] Examples of the above-mentioned aldehyde compounds include acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, pentylaldehyde, hexylaldehyde, heptylaldehyde, octylaldehyde, cyclohexanecarboxyaldehyde, benzaldehyde, p-tolualdehyde, cuminaldehyde, and 2,4-dimethylbenzaldehyde. The above aldehyde compounds may be linear, branched, or cyclic, as long as they have 2 to 10 carbon atoms.

[0025] The amount of aldehyde used is preferably 0.3 to 0.7 moles, and more preferably 0.4 to 0.6 moles, per mole of the compound represented by the general formula (2).

[0026] As catalysts, preferred examples include organic acid catalysts such as toluenesulfonic acid, xylenesulfonic acid, and oxalic acid, inorganic acid catalysts such as hydrochloric acid and sulfuric acid, and phosphotungstic acid, as well as heteropoly acids such as silicatungstic acid, phosphomolybdic acid, sodium phosphomolybdate, phosphotungstomolybdic acid, and phosphovanadomolybdic acid. The catalysts described above may be used individually or in combination of multiple types.

[0027] The amount of the catalyst used is preferably 0.001 to 1 mole, and more preferably 0.01 to 0.05 moles, per mole of the compound represented by the general formula (2).

[0028] In the reaction to obtain the compound represented by the above general formula (3), a solvent may be used as needed. The solvent is not particularly limited as long as it is reactive with the general formula (2) above, but alcohols, aprotic polar solvents, and aromatic hydrocarbons are preferred as solvents in that they readily dissolve the compound represented by the general formula (2).

[0029] Specific examples of the above solvents include, but are not limited to, alcohols such as methanol, ethanol, and isopropyl alcohol; aprotic polar solvents such as dimethyl sulfone, dimethyl sulfoxide, tetrahydrofuran, dioxane, methyl ethyl ketone, methyl isobutyl ketone, acetonitrile, methylene chloride, and dimethylformamide; aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as hexane; chloroform and carbon tetrachloride. The above solvents may be used individually or in combination of multiple types.

[0030] When using the above solvent, there are no particular restrictions on the amount used, but for example, 10 to 500 parts by mass can be used per 100 parts of the compound represented by the above general formula (2).

[0031] The reaction temperature for obtaining the compound represented by the above general formula (3) is preferably 10 to 150°C, more preferably 30 to 130°C, and even more preferably 50 to 120°C.

[0032] The reaction time for obtaining the compound represented by the above general formula (3) is preferably 0.5 to 20 hours, however, this is not limited to this range, as the reactivity varies depending on the type of compound used in the reaction to obtain the compound represented by the above general formula (3).

[0033] After the reaction to obtain the compound represented by the above general formula (3) is complete, the catalyst is quenched using a known method. If the above acidic catalyst is used, it may be neutralized with a basic compound or washed with water. The above basic compounds are not particularly limited, but preferred examples include metal hydroxides such as sodium hydroxide, potassium hydroxide, magnesium hydroxide, and calcium hydroxide; metal carbonates such as sodium carbonate and potassium carbonate; phosphates such as sodium phosphate, sodium hydrogen phosphate, and pentasodium tripolyphosphate; ion exchange resins; basic solids such as alumina; and ammonia. In this case, it is preferable to gradually add the basic compound as an aqueous solution dropwise in order to uniformly disperse it.

[0034] After the quenching of the reaction to obtain the compound represented by the above general formula (3), the compound represented by the above general formula (3) is extracted from the aqueous layer using an extraction solvent. The combined organic layers are dehydrated with sodium sulfate, and the sodium sulfate is removed by filtration. Subsequently, the solvent is removed under reduced pressure to obtain the crude product. The crude product is purified by column chromatography (silica gel / hexane-ethyl acetate) to obtain the compound represented by the general formula (3).

[0035] The above-mentioned extraction solvent is not particularly limited, but examples include hexane, heptane, octane, methylcyclohexane, ethylcyclohexane, toluene, ethylbenzene, ethyl acetate, diethyl ether, chloroform, methylene chloride, and the like. Among these, hexane is preferred from the viewpoint of its solubility for the bisphenol compound represented by the general formula (3) above and its ease of removal by distillation.

[0036] Subsequently, the epoxy compound of the present invention is obtained by reacting the compound represented by the above general formula (3) with an epihalohydrin in a solvent and epoxidizing it.

[0037] Examples of the above-mentioned epihalohydrins include epichlorohydrin, α-methylepichlorohydrin, β-methylepichlorohydrin, and epibromohydrin. Among these, epichlorohydrin, which is readily available industrially, is preferred.

[0038] The amount of epihalohydrin used is 2 to 100 moles per mole of hydroxyl group of the compound represented by the general formula (3), and is preferably 2 to 50 moles from an economic standpoint.

[0039] The above epoxidation reaction consists of a reaction in which an epihalohydrin is added in the presence of a basic catalyst, and a reaction in which the resulting 1,2-halohydrin ether group is cyclized in the presence of an alkali metal oxide to epoxidize it.

[0040] Examples of the basic catalysts mentioned above include alkali metal oxides such as sodium hydroxide and potassium hydroxide, and ammonium salts such as tetrabutylammonium bromide, tetraoctylammonium bromide, tetramethylammonium chloride, tetramethylammonium bromide, trimethylbenzylammonium chloride, and tetraethylammonium chloride. The alkali metal oxide or ammonium salt may be used as a solid or as an aqueous solution. When using an aqueous solution, the aqueous solution of the alkali metal hydroxide or ammonium salt may be continuously added to the reaction system, and the water may be removed by liquid-liquid extraction from a mixture of water and epihalohydrin continuously distilled under reduced or normal pressure, with only the epihalohydrin being continuously returned to the reaction system.

[0041] The amount of the basic catalyst used is preferably 0.05 to 3.0 moles, more preferably 0.1 to 2.0 moles, even more preferably 0.15 to 1.0 moles, and particularly preferably 0.2 to 0.5 moles, per mole of hydroxyl groups of the compound represented by the general formula (3).

[0042] The reaction temperature for the epihalohydrin addition reaction described above is preferably 40 to 120°C, and more preferably 60 to 100°C.

[0043] The reaction temperature for the epihalohydrin addition reaction described above is preferably 0.5 to 10 hours, and more preferably 1 to 8 hours.

[0044] Examples of the alkali metal oxides mentioned above include sodium hydroxide and potassium hydroxide. The alkali metal oxide may be used as a solid or as an aqueous solution. When using an aqueous solution, the aqueous solution of the alkali metal hydroxide may be continuously added to the reaction system, and the water may be removed by liquid-liquid extraction from a mixture of water and epihalohydrin continuously distilled under reduced or normal pressure, with only the epihalohydrin continuously returned to the reaction system.

[0045] The amount of alkali metal oxide used is preferably 0.5 to 15.0 moles, more preferably 1.0 to 10.0 moles, even more preferably 3.0 to 8.0 moles, and particularly preferably 4.0 to 6.0 moles, per mole of hydroxyl groups of the compound represented by the general formula (3).

[0046] The reaction temperature for the above epoxidation reaction is preferably -30 to 30°C, and more preferably -20 to 10°C.

[0047] The reaction time for the above epoxidation reaction is preferably 0.5 to 20 hours, and more preferably 1 to 10 hours.

[0048] After the epoxidation reaction described above is complete, the catalyst is quenched using a known method. If the basic catalyst described above is used, it may be neutralized with an acidic compound or washed with water. The above-mentioned acidic compound is not particularly limited, but hydrochloric acid is a preferred example.

[0049] After the quenching of the above epoxidation reaction is complete, the compound represented by the above general formula (1) is extracted from the aqueous layer using a solvent such as ethyl acetate. The combined organic layers are dehydrated with sodium sulfate, and the sodium sulfate is removed by filtration. Subsequently, the solvent is removed by distillation under reduced pressure to obtain the crude product. The crude product is purified by column chromatography (silica gel / hexane-ethyl acetate) to obtain the epoxy compound of the present invention.

[0050] After the epoxidation reaction described above is complete, the generated salt is removed by filtration, washing with water, etc., and the solvent is further removed by distillation under reduced pressure and heating to obtain the epoxy compound of the present invention.

[0051] <Cured product> The cured product of the present invention is a cured product obtained by curing the epoxy compound of the present invention or a composition containing the same described above. The cured product of the present invention can be obtained by curing the epoxy compound of the present invention or a composition containing the epoxy compound of the present invention using a conventionally known method. For example, the epoxy compound of the present invention, and optionally a curing agent, curing accelerator, phosphorus-containing compound, binder resin, inorganic filler, and compounding agent, are thoroughly mixed until uniform using an extruder, kneader, roll, etc., as needed, to obtain a resin composition. This resin composition is then molded using a potting, melting (without melting in the case of liquid) casting, or transfer molding machine, and further heated at 80 to 200°C for 2 to 10 hours to obtain the cured product of the present invention. Furthermore, a cured product may be obtained using a resin composition that mixes other epoxy compounds or epoxy resins in addition to the epoxy compound of the present invention.

[0052] The curing agent described above is not particularly limited as long as it is a compound that can undergo a curing reaction with the epoxy compound. Specific examples of curing agents include amine curing agents, phenol curing agents, acid anhydride curing agents, polymercaptan curing agents, polyaminoamide curing agents, isocyanate curing agents, and blocked isocyanate curing agents. The curing agent may be used alone or in combination of two or more types.

[0053] The above resin composition can be dissolved in solvents such as toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethylformamide, dimethylacetamide, and N-methylpyrrolidone as needed to form a curable resin composition varnish. This varnish can then be impregnated into a substrate such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, or paper, and the resulting prepreg is heat-dried. The resulting prepreg can then be hot-press-molded to produce the cured product of the present invention. The solvent in this case is preferably 10 to 70% by mass, and more preferably 15 to 70% by mass, in the mixture of the resin composition and the solvent. Furthermore, the above resin composition may also be in liquid form, and for example, a cured product containing carbon fibers can be obtained by the RTM method.

[0054] (Physical properties of the hardened material) The cured product of the present invention preferably has a cutting time of 10 seconds or more, more preferably 20 seconds or more, even more preferably 30 seconds or more, and particularly preferably 40 seconds or more.

[0055] The cured product of the present invention preferably has a cutting force of 10 N or less, more preferably 5 N or less, even more preferably 3 N or less, and particularly preferably 2 N or less.

[0056] The cured product of the present invention preferably has a tensile strength of 30 MPa or less at break, more preferably 20 MPa or less, even more preferably 10 MPa or less, particularly preferably 5 MPa or less, and most preferably 3 MPa or less.

[0057] The cured product of the present invention preferably has an elongation at break of 100% or more, more preferably 150% or more, and even more preferably 200% or more.

[0058] The cured product of the present invention has excellent flexibility because it has a cutting time, cutting force, tensile strength, and elongation within the above range. Furthermore, the measurement of cutting time, cutting force, tensile strength at cutting, and elongation at cutting can be performed in accordance with JIS K-6251:2017 in either the preparation of the test specimen or the tensile test, or both. For the preparation of the test specimen, for example, a dumbbell test specimen No. 7 conforming to the above JIS standard can be prepared, and for the tensile test, for example, a Bonding Tester PTR1102 manufactured by Resca Co., Ltd. can be used, and the test can be performed under standard conditions of temperature (27±2℃) and tensile speed of 1 mm / sec. [Examples]

[0059] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "%" means "mass%" and "parts" means "parts by mass".

[0060] (Example 1) 100 parts by mass of hydrogenated cardanol were weighed into a flask equipped with a stirrer, reflux condenser, and stirring device, while purging with nitrogen. 1.6 parts by mass of p-toluenesulfonic acid and 6 parts by mass of propionaldehyde were added. The reaction solution was then heated to 100°C and stirred under reflux for 3 hours. The reaction temperature was returned to room temperature and neutralized with aqueous sodium hydroxide solution. The aqueous layer was extracted three times with hexane, and the organic layer was dehydrated with sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed by evaporation. The resulting crude product was purified by column chromatography (silica gel / hexane-ethyl acetate), and the R of general formula (3) was determined. a is a straight chain of C 15 H 31 X a 35 parts by mass of a bisphenol-type compound represented by a straight chain of C3H6 were obtained. 1 The 1H-NMR spectrum was measured. 1H NMR (product name "ECX300", manufactured by JEOL Ltd., 300MHz, CDCl3): δ=7.17(d,2H),6.71(d,2H),6.58(s,2H),4.24(t,1H), 2.44(t,4H),2.13(quin,2H),1.50(quin,4H),1.25(m,48H),0.87(t+t,6H+3H)

[0061] In a flask equipped with a stirrer, reflux condenser, and stirring device, 100 parts by mass of the bisphenol-type compound were weighed out while purging with nitrogen, and 560 parts by mass of epichlorohydrin, 13 parts by mass of tetrabutylammonium bromide, and 3 parts by mass of water were added. The reaction solution was heated to 80°C and stirred under reflux for 4 hours. Subsequently, the reaction solution was cooled to 10°C, and 125 parts by mass of 50% sodium hydroxide aqueous solution were added in small amounts, and the reaction was carried out at 10°C for 10 hours. The reaction temperature was returned to room temperature and neutralized with hydrochloric acid. The aqueous layer was extracted three times with ethyl acetate, and the organic layer was dehydrated with sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed by evaporation. The obtained crude product was purified by column chromatography (silica gel / hexane-ethyl acetate) and the epoxy compound (in the above general formula (1), X is a linear C3H6, R) was extracted. 1 and R 2 is a straight chain of C 15 H 31 85 parts by mass were obtained. 1 The 1H-NMR spectrum was measured. 1 H NMR (product name "ECX300", manufactured by JEOL Ltd., 300MHz, CDCl3): δ=7.05(d,2H),6.71(d,2h),6.60(s,2H),4.60(t,1H),3.88-4.12(m,4H) ),3.26(quin,2H),2.85-2.63(m,4H),2.57(t,4H),1.95(quin,2H),1.50(quin,4H),1.25(m,48H),0.90(t+t,6H+3H)

[0062] 100 parts by mass of the epoxy compound described above was taken, and 23 parts by mass of a curing agent (KAYAHARD MCD, manufactured by Nippon Kayaku Co., Ltd.) and 2 parts by mass of trisdimethylaminomethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and mixed. The mixture was applied to a substrate such as a film and left to stand at 180°C for 1 hour to obtain the cured product of Example 1.

[0063] (Example 2) The reaction was carried out in the same manner as in Example 1, except that propionaldehyde was changed to n-hexylaldehyde, and the epoxy compound (in the above general formula (1), X is a straight-chain C6H) was obtained. 12 , R 1 and R 2 is a straight chain of C 15 H 31 ) was obtained. Furthermore, the cured product of Example 2 was obtained in the same manner as in Example 1, except that the epoxy compound obtained was used. The resulting bisphenol-type compound 1 The 1H-NMR spectrum was measured. 1 H NMR (product name "ECX300", manufactured by JEOL Ltd., 300MHz, CDCl3): δ=7.17(d,2H),6.72(d,2H),6.57(s,2H), 6.45(broad,2H),4.33(t,1H),2.44(t,4H),2.09(quin,2H),1.50(quin,4H),1.25(m, 56H),0.90(t+t,6H+3H) The resulting epoxy compound 1 The 1H-NMR spectrum was measured. 1 H NMR (product name "ECX300", manufactured by JEOL, 300MHz, CDCl3): δ=7.08(d,2H),6.77(d,2H),6.60(s,2H),4.69(t,1H),4.1-3.9(m,4H) ),3.26(quin,2H),2.9-2.6(m,4H),2.57(t,4H),1.90(quin,2H),1.57(quin,4H),1.25(m,56H),0.90(t+t,6H+3H)

[0064] (Comparative Example 1) 100 parts by mass of bisphenol A type epoxy resin jer-828 (manufactured by Mitsubishi Chemical Corporation) was taken, and 52 parts by mass of curing agent (KAYAHARD MCD, manufactured by Nippon Kayaku Co., Ltd.) and 1 part by mass of trisdimethylaminomethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and mixed. The mixture was applied to a substrate such as a film and left to stand at 180°C for 1 hour to obtain the cured product of Comparative Example 1.

[0065] (Comparative Example 2) 100 parts by mass of bisphenol F type epoxy resin EPICLON830 (manufactured by DIC Corporation) was taken, and 52 parts by mass of curing agent (KAYAHARD MCD, manufactured by Nippon Kayaku Co., Ltd.) and 1 part by mass of trisdimethylaminomethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and mixed. The mixture was applied to a substrate such as a film and left to stand at 180°C for 1 hour to obtain the cured product of Comparative Example 2.

[0066] <Comparison of physical properties of cured products> Dumbbell-shaped test specimens (Type 7) were prepared from the cured products of Examples 1 and 2, and Comparative Examples 1 and 2, in accordance with JIS K-6251:2017. Subsequently, tensile tests were performed at a standard temperature (27±2℃) to evaluate flexibility (measuring device: Bonding Tester PTR1102 manufactured by Resca Co., Ltd., tensile speed 1 mm / sec). The results are shown in Table 1. It was revealed that the cured product of the present invention exhibits excellent flexibility. [Table 1] [Industrial applicability]

[0067] The epoxy compound of the present invention can produce a cured product with excellent flexibility, and can therefore be used in a variety of applications such as surface protective films for semiconductor devices and organic thin-film devices (e.g., organic electroluminescent devices and organic thin-film solar cell devices), interlayer insulators, protective insulating films for printed circuit boards, and fiber-reinforced composite materials.

Claims

1. Containing monomer components, The monomer component is a composition comprising an epoxy compound represented by the following general formula (1). 【Chemistry 1】 (In general formula (1), X is a divalent linking group derived from a hydrocarbon having 2 to 10 carbon atoms, and R １ and R ２ (This is a hydrocarbon group with 15 carbon atoms and 31 hydrogen atoms.)

2. In the above general formula (1), R １ and / or R ２ is an oxygen atom (O １ or O ２ The composition according to claim 1, which is in the meta position relative to ).

3. In the above general formula (1), R １ and / or R ２ The composition according to either claim 1 or 2, wherein is in the para position relative to X.

4. In the general formula (1), O １ and / or O ２ is ortho to X. The composition according to any one of claims 1 to 3.

5. The composition according to any one of claims 1 to 4, wherein X has 3 to 7 carbon atoms in the general formula (1).

6. A cured product obtained by curing the composition according to any one of claims 1 to 5.

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