Epoxy compounds and use thereof

Abstract

An object of the present invention is to provide a novel epoxy compound and use thereof. Specifically, an object of the present invention is to provide a novel epoxy compound, a resin composition containing the epoxy compound, and a cured product of the composition. The present invention relates to an epoxy compound represented by formula (I); a resin composition containing the epoxy compound; and a cured product of the composition. (In formula (I), X represents an iodine atom, and n represents an integer of 1 to 4.)

Description

Technical Field

[0001] This invention relates to novel epoxy compounds, resin compositions containing such epoxy compounds, and cured products thereof. Background Technology

[0002] Known examples of thermosetting resins used as electrical insulation materials, structural materials, etc., include epoxy resins, polyester resins, and phenolic resins. Among them, epoxy resins are widely used because they achieve an excellent balance between cost-effectiveness and performance.

[0003] For example, PLT 1 proposes a curable epoxy composition containing an aromatic polyglycidyl ester compound and discloses glycidyl phthalate, diglycidyl terephthalate, etc. as examples of aromatic polyglycidyl ester compounds.

[0004] However, there is still room for improvement in the curability of resin compositions containing such aromatic polyglycidyl ester compounds.

[0005] Reference List Patent documents PTL 1: WO2014 / 148538 Summary of the Invention

[0006] Technical issues The purpose of this invention is to provide a novel epoxy compound and its uses. Specifically, the purpose of this invention is to provide a novel epoxy compound, a resin composition containing the epoxy compound, and a cured product thereof.

[0007] Problem Solving Methods To achieve the above objectives, the inventors conducted extensive research and discovered that the epoxy compound obtained by reacting a specific iododicarboxylic acid with epichlorohydrin is a novel compound, and resin compositions containing this compound exhibit good curing properties (short gel time). This led to the completion of the present invention.

[0008] Specifically, the first invention provides an epoxy compound represented by formula (I). Where X represents an iodine atom, and n represents an integer from 1 to 4.

[0009] The second invention provides a resin composition comprising the epoxy compound of the first invention.

[0010] The third invention provides a resin composition of the second invention, which further includes a curing agent and / or a curing accelerator.

[0011] The fourth invention provides a cured product obtained by curing the resin composition of the second or third invention.

[0012] The fifth invention provides a method for manufacturing an epoxy compound represented by formula (I), the method comprising reacting an iododicarboxylic acid represented by formula (II) with an epichlorohydrin represented by formula (III): Beneficial effects of the invention The epoxy compound molecule of the present invention has two oxirane rings (epoxyethyl / glycidyl) in the molecule and is intended to be used as a resin material.

[0013] The epoxy compounds of the present invention, which contain iodine atoms in their molecules, exhibit good curability compared to conventional epoxy compounds when used as materials in resin compositions, and are expected to provide cured products with excellent heat resistance and electrical properties. Detailed Implementation

[0014] The present invention will now be described in detail.

[0015] Epoxy compounds The present invention relates to epoxy compounds represented by formula (I) (hereinafter sometimes referred to as "the epoxy compounds of the present invention").

[0016] The epoxy compounds represented by formula (I) include those represented by formulas (I-1) to (I-3): Where X and n are as described above.

[0017] The epoxy compounds represented by formula (I-1) include, for example, the epoxy compounds represented by formulas (I-1-1) to (I-1-6).

[0018] The epoxy compounds represented by formula (I-2) include, for example, the epoxy compounds represented by formulas (I-2-1) to (I-2-11).

[0019] The epoxy compounds represented by formula (I-3) include, for example, the epoxy compounds represented by formulas (I-3-1) to (I-3-8). Synthesis method The epoxy compounds of the present invention can be synthesized by reacting iododicarboxylic acid represented by formula (II) with epichlorohydrin represented by formula (III) (see reaction route (A)).

[0020] Reaction route (A) Where X and n are as described above.

[0021] Iododicarboxylic acids represented by formula (II) include those represented by formulas (II-1) to (II-3). Where X and n are as described above.

[0022] Iodinated dicarboxylic acid compounds represented by formula (II-1) include, for example, iodinated dicarboxylic acid compounds represented by formulas (II-1-1) to (II-1-6).

[0023] Iodinated dicarboxylic acid compounds represented by formula (II-2) include, for example, iodinated dicarboxylic acid compounds represented by formulas (II-2-1) to (II-2-11).

[0024] Iodinated dicarboxylic acid compounds represented by formula (II-3) include, for example, iodinated dicarboxylic acid compounds represented by formulas (II-3-1) to (II-3-8). These iododicarboxylic acids can be purchased as commercially available reagents, or synthesized by, for example, iodination of commercially available dicarboxylic acids or iodination of xylene followed by oxidation of the methyl group.

[0025] The epichlorohydrin represented by formula (III) can be purchased as a commercially available reagent.

[0026] Preferably, the amount of epichlorohydrin represented by formula (III) can be appropriately set within the range of 2 to 100 times the molar amount of iododicarboxylic acid represented by formula (II).

[0027] In carrying out this reaction, a phase transfer catalyst (i) and / or a base (ii) may be used. A reaction solvent (iii) may be used if necessary.

[0028] Examples of phase transfer catalysts (i) include: tetramethylammonium chloride, tetrabutylammonium bromide, methyltrioctylammonium chloride, methyltridecylammonium chloride, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, N,N-dimethylpyrrolidineonium chloride, N-ethyl-N-methylpyrrolidineonium iodide, N-butyl-N-methylpyrrolidineonium bromide, N-benzyl-N-methylpyrrolidineonium chloride, N-ethyl ... N-methylpyrrolidone bromide, N-butyl-N-methylmorpholinon bromide, N-butyl-N-methylmorpholinon iodide, N-allyl-N-methylmorpholinon bromide, N-methyl-N-benzylpiperidineonium chloride, N-methyl-N-benzylpiperidineonium bromide, N,N-dimethylpiperidineonium iodide, N-methyl-N-ethylpiperidineonium acetate, and N-methyl-N-ethylpiperidineonium iodide.

[0029] Preferably, the amount of phase transfer catalyst (i) can be appropriately set in the range of 0.005 to 0.5 times the molar amount of iododicarboxylic acid represented by formula (II).

[0030] Examples of bases (ii) include lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate. These bases may be used alone or in combination of two or more.

[0031] Preferably, the amount of base (ii) can be appropriately set in the range of 2 to 20 times the molar amount of iododicarboxylic acid represented by formula (II).

[0032] The reaction solvent (iii) is not particularly limited, as long as it does not inhibit the reaction. Examples include: water; alcohols, such as methanol, ethanol, and isopropanol; aliphatic hydrocarbons, such as hexane and heptane; esters, such as ethyl acetate and butyl acetate; aromatic hydrocarbons, such as benzene, toluene, and xylene; halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, trifluorochloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers, such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and diethylene glycol dimethyl ether; amides, such as formamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and hexamethylphosphoramide; and sulfoxides, such as dimethyl sulfoxide. These solvents can be used alone or in combination of two or more.

[0033] In the reaction, the reaction temperature is preferably set in the range of -10 to 150°C. The reaction time is appropriately set according to the set reaction temperature, preferably in the range of 1 to 48 hours.

[0034] After the reaction is complete, the epoxy compound of the present invention, as the target product, can be extracted from the obtained reaction mixture by means of, for example, concentrating the reaction mixture by distillation of the reaction solvent or solvent extraction.

[0035] In addition, epoxy compounds can be purified as needed by means such as washing with water, activated carbon treatment, silica gel chromatography, recrystallization, etc.

[0036] Resin Composition The resin compositions of the present invention contain the epoxy compounds of the present invention as an essential component. The resin compositions may contain one or more of the epoxy compounds of the present invention.

[0037] The content of the epoxy compound of the present invention in the resin composition of the present invention is preferably 0.001 to 99 wt%.

[0038] In addition to the epoxy compounds of the present invention, the resin compositions of the present invention may also contain other epoxy compounds, curing agents, curing accelerators, and additives as needed. In this invention, the term "resin composition" refers to a mixture before curing.

[0039] Cured products can be obtained by polymerizing the epoxy compounds of the present invention. When other epoxy compounds (note: sometimes referred to as "epoxy resins") are present together with the epoxy compounds of the present invention during the polymerization process, cured products of copolymerization of the epoxy compounds of the present invention with other epoxy compounds can be obtained.

[0040] Any epoxy compound can be used as another epoxy compound, as long as it has an ethylene oxide ring (epoxy ethyl / glycidyl group) in its molecule. Examples include the following: polyglycidyl ethers (e.g., bisphenol A epoxy resin and bisphenol F epoxy resin) obtained by reacting polyphenols (e.g., bisphenol A, bisphenol F, bisphenol AD, catechol, and resorcinol) or polyols (e.g., glycerol and polyethylene glycol) with epichlorohydrin; glycidyl ether esters obtained by reacting hydroxycarboxylic acids (e.g., p-hydroxybenzoic acid and β-hydroxynaphthoic acid) with epichlorohydrin; polyglycidyl esters obtained by reacting polycarboxylic acids (e.g., phthalic acid and terephthalic acid) with epichlorohydrin; glycidyl glycoluril compounds having two or more epoxy groups in the molecule, such as 1,3,4,6-tetraglycidyl glycoluril; alicyclic epoxy compounds, such as 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate. 3,4-epoxycyclohexanecarboxylate); and nitrogen-containing cyclic epoxy resins, such as triglycidyl isocyanurate and hydantoin-based epoxy resins. Examples also include epoxidized phenol novolacresins, epoxidized cresol novolac resins, epoxidized polyolefins, cycloaliphatic epoxy resins, urethane-modified epoxy resins, and epoxy-modified organopolysiloxane compounds obtained by hydrosilylation addition reaction between organic compounds having carbon-carbon double bonds and glycidyl groups and silicon compounds having SiH groups (e.g., epoxy-modified organopolysiloxane compounds disclosed in JP 2004-99751 and JP 2006-282988). These compounds can be used in combination.

[0041] In the resin composition of the present invention, the content of the epoxy compound and other epoxy compounds is preferably set appropriately in the range of 0 to 1000 times, more preferably in the range of 0.01 to 100 times, relative to the weight of the epoxy compound of the present invention, with regard to the respective content of the epoxy compound of the present invention and other epoxy compounds.

[0042] Examples of curing agents include compounds with phenolic hydroxyl groups, acid anhydrides, amines, and thiols, such as mercaptopropionic esters and thiol compounds that are epoxy resin-terminated.

[0043] Examples of compounds having a phenolic hydroxyl group include bisphenol A, bisphenol F, bisphenol S, tetramethylbisphenol A, tetramethylbisphenol F, tetramethylbisphenol S, tetrachlorobisphenol A, tetrabromobisphenol A, dihydroxynaphthalene, phenol novolac, cresol novolac, bisphenol A novolac, brominated phenol novolac, and resorcinol.

[0044] Examples of acid anhydrides include methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, trimellitic anhydride, nadic anhydride, hisic anhydride, methylnadic anhydride, methylbicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, and methylnorbornane-2,3-dicarboxylic acid.

[0045] Examples of amines include diethylenediamine, triethylenetetramine, hexamethylenediamine, dimeracid-modified ethylenediamine, 4,4'-diaminodiphenyl sulfone, and 4,4'-diaminodiphenyl ether.

[0046] These curing agents can be used alone, or in combination of two or more.

[0047] The content of curing agent in the resin composition of the present invention is preferably 10 to 300 parts by weight, more preferably 100 to 200 parts by weight, relative to 100 parts by weight of epoxy compound (the total amount of epoxy compound and other epoxy compounds of the present invention).

[0048] Examples of curing accelerators include amine compounds, imidazole compounds, organophosphorus compounds (such as triphenylphosphine, diphenylnaphthylphosphine, and diphenylethylphosphine), aromatic phosphonium salts, aromatic diazonium salts, aromatic iodonium salts, and aromatic selenium salts.

[0049] Examples of curing accelerators include: amine compounds, such as 1,8-diazabicyclo[5.4.0]undec-7-ene, diethylenetriamine, triethylenetetramine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, and tris(dimethylaminomethyl)phenol; imidazole compounds, such as 2-methylimidazolium, 2-ethyl-4-methylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, and 2-heptadecylimidazolium; organophosphorus compounds, such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine, diphenylphosphine, and phenylphosphine; phosphonium compounds, such as tetrabutylphosphonium bromide and tetrabutylphosphonium diethyldithiophosphate; tetraphenylborates, such as tetraphenylphosphine tetraphenylborate, 2-methyl-4-methylimidazolium tetraphenylborate, and N-methylmorpholinium tetraphenylborate; and aliphatic acid metal salts, such as lead acetate, tin octoate, and cobalt hexanoate. Some of these curing accelerators are known to be used as the curing agents described above.

[0050] These curing accelerators can be used alone, or in combination of two or more.

[0051] The content of curing agent accelerator in the resin composition of the present invention is preferably 0.01 to 10.0 parts by weight, more preferably 0.1 to 5 parts by weight, relative to 100 parts by weight of epoxy compound (the total amount of epoxy compound and other epoxy compounds of the present invention).

[0052] In the resin composition of the present invention, the curing agent or the curing accelerator may be used alone or in combination.

[0053] Provided that the effects of the invention are not impaired, the resin composition of the present invention may contain inorganic fillers, such as amorphous silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesium oxide, clay, talc, calcium silicate, and titanium dioxide; various polymers, such as phenolic resins and unsaturated polyesters; aliphatic polyols, such as ethylene glycol and propylene glycol; aliphatic or aromatic carboxylic acid compounds; carbon dioxide generation inhibitors, such as phenolic compounds; flexibility imparting agents, such as polyalkylene glycols; antioxidants; plasticizers; lubricants; coupling agents, such as silane coupling agents; surface treatment agents for inorganic fillers; flame retardants; antistatic agents; colorants; leveling agents; ion-trapping agents; sliding property improvers; various rubbers; impact resistance improvers, such as organic polymer beads and inorganic fillers (including glass beads). (beads) and glass fibers); and additives (modifiers), such as thixotropy imparting agents, surfactants, surface tension reducing agents, defoamers, anti-settling agents, light diffusing agents, ultraviolet absorbers, antioxidants, mold release agents, fluorescent agents and conductive fillers.

[0054] The epoxy compounds of the present invention can be used as materials in epoxy resin compositions for coatings, sealants, adhesives, resist inks, etc., for printed circuit boards and electronic components; materials in epoxy resin compositions for wood coatings; and materials in epoxy resin compositions for coatings protecting the surfaces of optical fibers, plastics, and cans. The epoxy compounds can also be used as materials in epoxy resin compositions for the formation of ball grid array semiconductor encapsulation, optoelectronic semiconductor device encapsulation, semiconductor encapsulation used as underfill, and resist underlayer films for lithography.

[0055] Example The invention will now be described in more detail with reference to the following embodiments. However, the invention is not limited thereto.

[0056] The main raw materials used in the synthesis of epoxy compounds are as follows.

[0057] - 4-Iodobenzoic acid (obtained from Fujifilm Wako Pure Chemical Corporation, see formula (II-3-2)) - 2,3,5-Triiodoterephthalic acid (synthesized according to the methods of Synthetic Examples 1 and 2, see formula (II-1-5)) - 2,4,5,6-Tetraiodophthalic acid (synthesized according to the method disclosed in JPH06-345705, see formula (II-2-11)) - Epichlorohydrin (obtained from Fujifilm Wako Pure Chemical Corporation) - Tetramethylammonium chloride (obtained from Fujifilm Wako Pure Chemical Corporation) - Sodium hydroxide (available from Fujifilm Wako Pure Chemical Corporation) - Chloroform (obtained from Fujifilm Wako Pure Chemical Corporation) - Ethyl acetate (obtained from Fujifilm Wako Pure Chemical Corporation) - Methanol (obtained from Fujifilm Wako Pure Chemical Corporation) The main raw materials used in the preparation of the resin composition are as follows: (A) Epoxy compounds - Diglycidyl isophthalate (synthesized according to the method disclosed in Chinese Patent Application Publication No. 103864724; see formula (1)) (B) Curing accelerator - 2-Ethyl-4-methylimidazol (trade name "CURESOL 2E4MZ", hereinafter referred to as "2E4MZ", obtained from Shikoku Chemicals Corporation) Synthesis example 1 Synthesis of 2-amino-3,5-diiodoterephthalic acid 2-Aminoterephthalic acid (7.25 g, 40 mmol) and acetic acid (16 mL) were placed in a 200 mL flask. While stirring at room temperature, a mixture of iodine monochloride (25.9 g, 160 mmol), 36% concentrated hydrochloric acid (3.0 g, 30.2 mmol), and deionized water (52 g) was added dropwise. The mixture was then stirred at 50 °C for 85 hours. After filtering the reaction mixture, tetrahydrofuran and toluene were added to the resulting solid for recrystallization. The recrystallized product was filtered and dried to give 14.3 g of a yellow solid (yield: 82%).

[0058] The resulting yellow solid 1 The H-NMR spectral data are as follows.

[0059] - 1 H-NMR (CDCl3) δ: 8.11 (s, 1H).

[0060] Based on spectral data, the obtained yellow solid was identified as the title compound (2-amino-3,5-diiodoterephthalic acid).

[0061] Synthesis example 2 Synthesize 2,3,5-triiodoterephthalic acid (Formula (II-1-5)) 2-Amino-3,5-diiodoterephthalic acid (4.33 g, 10 mmol), deionized water (10.00 g), acetonitrile (10.00 g), and 95% sulfuric acid (2.06 g, 20 mmol) were placed in a 1000 mL flask. After purging with nitrogen, 40% sodium nitrite aqueous solution (5.18 g, 30 mmol) was added dropwise while stirring at -10 °C. After stirring at -10 °C for 1 hour, 53% sodium iodide aqueous solution (11.31 g, 40 mmol) was added dropwise at -10 °C, and stirring was continued for 12 hours. After quenching with 35% sodium bisulfite aqueous solution, the solid was collected by filtration. The filter cake was re-pulped with deionized water (25 g), filtered, and then dried to give 4.24 g of brown solid (yield: 78%).

[0062] The resulting brown solid 1 The H-NMR spectral data are as follows.

[0063] - 1 H-NMR (CDCl3) δ: 7.88 (s, 1H).

[0064] Based on the spectral data, the obtained brown solid was identified as the title compound (2,3,5-triiodoterephthalic acid) represented by formula (II-1-5).

[0065] Example 1 Synthesize 4-iodophthalic acid diglycidyl ester (Formula (I-3-2)) 4-Iodophthalic acid (2.92 g, 10 mmol), epichlorohydrin (37.01 g, 400 mmol), and tetramethylammonium chloride (54.8 mg, 0.5 mmol) were placed in a 100 mL three-necked flask and stirred at 80 °C for 6 hours. The reaction mixture was then cooled to 2 °C, and 48% sodium hydroxide aqueous solution (2.00 g, 24 mmol) was added. The mixture was then stirred at 30 °C for 14 hours. Deionized water (10.0 g) was added to the reaction mixture, and the aqueous layer was removed by liquid-liquid separation. The organic layer was concentrated. The concentrate was purified by silica gel column chromatography (chloroform / ethyl acetate = 30 / 1 (w / w)) to give 1.33 g of a colorless liquid (yield: 33%).

[0066] The resulting colorless liquid 1 The H-NMR spectral data are as follows.

[0067] - 1 H-NMR (DMSO-d6) δ: 8.12-8.08 (m, 2H), 7.60-7.55 (m, 1H), 4.65 (dd,2H), 4.09 (dd, 2H), 3.31-3.25 (m, 2H), 2.83 (dt, 2H), 2.70-2.66 (m, 2H).

[0068] Based on the spectral data, the obtained colorless liquid was identified as the title compound (4-iodophthalic acid diglycidyl ester) represented by formula (I-3-2).

[0069] Example 2 Synthesize 2,3,5-triiodoterephthalic acid diglycidyl ester (Formula (I-1-5)) 2,3,5-Triiodoterephthalic acid (10.88 g, 20 mmol), epichlorohydrin (37.01 g, 400 mmol), and tetramethylammonium chloride (110 mg, 1 mmol) were placed in a 100 mL three-necked flask and stirred at 80 °C for 6 hours. The reaction mixture was then cooled to 2 °C, and 48% sodium hydroxide aqueous solution (4.00 g, 48 mmol) was added, followed by stirring at 30 °C for 20 hours. Deionized water (24.0 g) was added to the reaction mixture, the aqueous layer was removed by liquid-liquid separation, and the organic layer was concentrated. The concentrate was purified by silica gel column chromatography (chloroform / methanol = 20 / 1 (w / w)) to give 4.07 g of a pale yellow solid (yield: 31%).

[0070] The resulting pale yellow solid 1 The H-NMR spectral data are as follows.

[0071] -1 H-NMR (DMSO-d6) δ: 8.02 (s, 1H), 4.73-4.60 (m, 2H), 4.17-4.03 (m, 2H), 3.40-3.30 (m, 2H), 2.90-2.82 (m, 2H), 2.80-2.70 (m, 2H).

[0072] Based on spectral data, the obtained pale yellow solid was identified as the title compound (2,3,5-triiodoterephthalic acid diglycidyl ester) represented by formula (I-1-5).

[0073] Example 3 Synthesize 2,4,5,6-tetraiodophthalic acid diglycidyl ester (Formula (I-2-11)) 2,4,5,6-Tetraiodophthalic acid (13.39 g, 20 mmol), epichlorohydrin (37.01 g, 400 mmol), and tetramethylammonium chloride (110 mg, 1 mmol) were placed in a 100 mL three-necked flask and stirred at 80 °C for 6 hours. The reaction mixture was then cooled to 2 °C, and 48% sodium hydroxide aqueous solution (4.00 g, 48 mmol) was added, followed by stirring at 30 °C for 20 hours. Deionized water (24.00 g) was added to the reaction mixture, the aqueous layer was removed by liquid-liquid separation, and the organic layer was concentrated. The concentrate was purified by silica gel column chromatography (chloroform / methanol = 20 / 1 (w / w)) to give 8.76 g of a pale yellow solid (yield: 56%).

[0074] The resulting pale yellow solid 1 The H-NMR spectral data are as follows.

[0075] - 1 H-NMR (DMSO-d6) δ: 4.65 (dd, 2H), 4.09 (dd, 2H), 3.40-3.30 (m, 2H), 2.86 (t, 2H), 2.75 (dd, 2H).

[0076] Based on spectral data, the obtained pale yellow solid was identified as the title compound (2,4,5,6-tetraiodoisophthalic acid diglycidyl ester) represented by formula (I-2-11).

[0077] Example 4 The epoxy compound (10.0 g) of Example 1, which is used as the epoxy compound, was mixed with 2E4MZ (0.5 g) as a curing accelerator to prepare a resin composition (epoxy resin composition).

[0078] The curing properties of the resin composition at 150°C were evaluated by measuring the gel time using the hot plate method (JIS C-2105).

[0079] The results are shown in Table 1.

[0080] Example 5 and Comparative Example 1 Resin compositions having the formulations shown in Table 1 were prepared in the same manner as in Example 4. The curing properties of these resin compositions were evaluated by measuring the gel time.

[0081] The evaluation results are shown in Table 1.

[0082] Table 1 Table 1 shows that when the epoxy compound of the present invention is used as the epoxy compound (Examples 4 and 5), the gel time is shorter than when a conventional epoxy compound is used (Comparative Example 1), confirming its excellent curability.

[0083] Therefore, the epoxy compounds of the present invention are considered to be more suitable resin materials than conventional epoxy compounds.

[0084] Industrial application When the epoxy compounds of the present invention, which have iodine atoms in their molecules, are used as materials in resin compositions, they exhibit good curability compared to conventional epoxy compounds, and are expected to provide cured products with excellent heat resistance and electrical properties.

[0085] Therefore, the epoxy compound of the present invention is considered a suitable resin material.

Claims

1. An epoxy compound represented by formula (I), in, X represents an iodine atom, and n represents an integer from 1 to 4.

2. A resin composition comprising the epoxy compound according to claim 1.

3. The resin composition according to claim 2, further comprising a curing agent and / or a curing accelerator.

4. A cured product obtained by curing the resin composition according to claim 2 or 3.

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