Epoxy compound and use of the same

Abstract

To provide a new epoxy compound and use of the same, specifically, a new epoxy compound, a resin composition containing the epoxy compound, and a cured product of the same.SOLUTION: An epoxy compound is represented by the chemical formula (I). In the formula, X represents iodine atoms and n represents integers 1 to 4.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a novel epoxy compound, a resin composition containing the epoxy compound, and a cured product thereof.

Background Art

[0002] As thermosetting resins used for electrical insulating materials, structural materials, etc., epoxy resins, polyester resins, phenolic resins, etc. are known. Among them, epoxy resins are widely used because they are excellent in terms of the balance between economy and performance.

[0003] For example, Patent Document 1 proposes a curable epoxy composition containing an aromatic polyvalent glycidyl ester compound, and as the aromatic polyvalent glycidyl ester compound, glycidyl phthalate, diglycidyl terephthalate, etc. are disclosed. However, the resin compositions containing these aromatic polyvalent glycidyl ester compounds still had room for improvement in terms of curability.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] An object of the present invention is to provide a novel epoxy compound and its uses. Specifically, an object is to provide a novel epoxy compound, a resin composition containing the epoxy compound, and a cured product thereof.

Means for Solving the Problems

[0006] As a result of intensive studies to solve the above problems, the inventors of the present invention have found that an epoxy compound obtained by reacting a certain iododicarboxylic acid with epichlorohydrin is a novel compound, and a resin composition containing the compound has good curability (short gel time), and thus completed the present invention. That is, the first invention is an epoxy compound represented by chemical formula (I).

[0007]

Chemical formula

[0008] The second invention is a resin composition characterized by containing the epoxy compound of the first invention. The third invention is the resin composition of the second invention containing a curing agent and / or a curing accelerator. The fourth invention is a cured product obtained by curing the resin composition of any one of the second to third inventions.

Advantages of the Invention

[0009] Since the epoxy compound of the present invention has two oxirane rings (epoxy group / glycidyl group) in the molecule, it is expected to be used as a resin material. And, since the epoxy compound of the present invention has an iodine atom in the molecule, when used as a material of a resin composition, it exhibits good curability compared to the case of using a conventional epoxy compound, and is expected to provide a cured product having excellent heat resistance and electrical properties.

Embodiments for Carrying Out the Invention

[0010] Hereinafter, the present invention will be described in detail. <Epoxy Compound> The present invention relates to an epoxy compound represented by the above chemical formula (I) (hereinafter sometimes referred to as "the epoxy compound of the present invention"). The epoxy compound represented by Chemical Formula (I) includes epoxy compounds represented by Chemical Formulas (I-1) to (I-3).

[0011]

Chem.

[0012] Examples of the epoxy compound represented by Chemical Formula (I-1) include epoxy compounds represented by Chemical Formulas (I-1-1) to (I-1-6). Examples of the epoxy compound represented by Chemical Formula (I-2) include epoxy compounds represented by Chemical Formulas (I-2-1) to (I-2-11). Examples of the epoxy compound represented by Chemical Formula (I-3) include epoxy compounds represented by Chemical Formulas (I-3-1) to (I-3-8).

[0013]

Chem.

[0014]

Chem.

[0015]

Chem.

[0016] <Synthesis Method> The epoxy compound of the present invention can be synthesized by reacting an iododicarboxylic acid represented by Chemical Formula (II) with epichlorohydrin represented by Chemical Formula (III) (see Reaction Scheme (A)).

[0017]

Chem.

[0018] The iododicarboxylic acid represented by Chemical Formula (II) includes iododicarboxylic acids represented by Chemical Formulas (II-1) to (II-3).

[0019]

Chem.

[0020] Examples of the iododicarboxylic acid compound represented by Chemical Formula (II-1) include iododicarboxylic acid compounds represented by Chemical Formulas (II-1-1) to (II-1-6). Examples of the iododicarboxylic acid compound represented by Chemical Formula (II-2) include iododicarboxylic acid compounds represented by Chemical Formulas (II-2-1) to (II-2-11). Examples of the iododicarboxylic acid compound represented by Chemical Formula (II-3) include iododicarboxylic acid compounds represented by Chemical Formulas (II-3-1) to (II-3-8).

[0021]

Chem.

[0022]

Chem.

[0023]

Chem.

[0024] These iododicarboxylic acids can be purchased as commercially available reagents and used. Alternatively, they can be synthesized, for example, by iodinating commercially available dicarboxylic acids or by iodinating xylene and then oxidizing the methyl group.

[0025] Epichlorohydrin represented by Chemical Formula (III) can be purchased and used as a commercially available reagent.

[0026] The amount of epichlorohydrin represented by Chemical Formula (III) used is preferably an appropriate ratio in the range of 2 to 100 times the molar amount of the iododicarboxylic acid represented by Chemical Formula (II).

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

[0028] Examples of the phase transfer catalyst (i) include tetramethylammonium chloride, tetrabutylammonium bromide, methyltrioctylammonium chloride, methyltridecylammonium chloride, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, N,N-dimethylpyrrolidinium chloride, N-ethyl-N-methylpyrrolidinium iodide, N-butyl-N-methylpyrrolidinium bromide, N-benzyl-N-methylpyrrolidinium chloride, N-ethyl-N-methylpyrrolidinium bromide, N-butyl-N-methylmorpholinium bromide, N-butyl-N-methylmorpholinium iodide, N-allyl-N-methylmorpholinium bromide, N-methyl-N-benzylpiperidinium chloride, N-methyl-N-benzylpiperidinium bromide, N,N-dimethylpiperidinium iodide, N-methyl-N-ethylpiperidinium acetate, N-methyl-N-ethylpiperidinium iodide, and the like.

[0029] The amount of the phase transfer catalyst (i) used is preferably an appropriate ratio in the range of 0.005 to 0.5 times the molar amount of the iododicarboxylic acid represented by Chemical Formula (II).

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

[0031] The amount of the base (ii) used is preferably an appropriate ratio in the range of 2 to 20 times the molar amount of the iododicarboxylic acid represented by the chemical 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 isopropyl alcohol; 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 methylene chloride, chloroform, carbon tetrachloride, chlorotrifluoromethane, 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; sulfoxides such as dimethyl sulfoxide, etc. These solvents may be used alone or in combination of two or more.

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

[0034] After completion of this reaction, the target epoxy compound of the present invention can be taken out from the obtained reaction solution by means such as concentration of the reaction solution by distilling off the reaction solvent or solvent extraction method. Furthermore, if necessary, it can be purified by means such as washing with water or the like, activated carbon treatment, silica gel chromatography, recrystallization, etc.

[0035] <Resin composition> The resin composition of the present invention contains the epoxy compound of the present invention as an essential component, but may contain one or more epoxy compounds of the present invention. The content of the epoxy compound of the present invention in the resin composition of the present invention is preferably in the range of 0.001 to 99% by weight.

[0036] In addition to the epoxy compound of the present invention, the resin composition of the present invention may contain, if necessary, another epoxy compound, a curing agent, a curing accelerator, and an additive. Also, in the present invention, the resin composition means the state of a mixture before curing.

[0037] When the epoxy compound of the present invention is polymerized, a cured product can be obtained. At the time of this polymerization, by coexisting another epoxy compound (note: sometimes referred to as an epoxy resin) different from the epoxy compound of the present invention, a cured product in which the epoxy compound of the present invention and another epoxy compound are copolymerized can be obtained.

[0038] As another epoxy compound, any compound having an oxirane ring (epoxy group / glycidyl group) in the molecule can be used without particular limitation. For example, Polyglycidyl ethers obtained by reacting polyhydric phenols such as bisphenol A, bisphenol F, bisphenol AD, catechol, resorcinol, etc. or polyhydric alcohols such as glycerin and polyethylene glycol with epichlorohydrin; Glycidyl ether esters obtained by reacting hydroxycarboxylic acids such as p-hydroxybenzoic acid and β-hydroxynaphthoic acid with epichlorohydrin; Polyglycidyl esters obtained by reacting polycarboxylic acids such as phthalic acid and terephthalic acid with epichlorohydrin; A glycidyl glycoluril compound having two or more epoxy groups in the molecule, such as 1,3,4,6-tetraglycidyl glycoluril; An alicyclic epoxy compound, such as 3′,4′-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate; A nitrogen-containing cyclic epoxy compound, such as triglycidyl isocyanurate and a hydantoin-type epoxy compound; Furthermore, in addition to an epoxidized phenol novolak resin, an epoxidized cresol novolak resin, an epoxidized polyolefin, an alicyclic epoxy resin, and a urethane-modified epoxy resin, An epoxy-modified organopolysiloxane compound by a hydrosilylation addition reaction of an organic compound having a carbon-carbon double bond and a glycidyl group and a silicon compound having an SiH group (for example, an epoxy-modified organopolysiloxane compound disclosed in JP-A-2004-99751 and JP-A-2006-282988), etc. may be mentioned, and these may be used in combination.

[0039] Regarding the ratio of the content of each of the epoxy compounds of the present invention and another epoxy compound in the resin composition of the present invention, the content of the other epoxy compound is preferably an appropriate ratio in the range of 0 to 1000 times (weight ratio) with respect to the content of the epoxy compound of the present invention, and more preferably an appropriate ratio in the range of 0.01 to 100 times (weight ratio).

[0040] Examples of the curing agent include compounds having a phenolic hydroxyl group, acid anhydrides, amines, and mercaptan compounds such as mercaptopropionic acid esters and epoxy resin terminal mercapto compounds.

[0041] Examples of the compound having a phenolic hydroxyl group include bisphenol A, bisphenol F, bisphenol S, tetramethyl bisphenol A, tetramethyl bisphenol F, tetramethyl bisphenol S, tetrachloro bisphenol A, tetrabromo bisphenol A, dihydroxynaphthalene, phenol novolak, cresol novolak, bisphenol A novolak, brominated phenol novolak, resorcinol, and the like.

[0042] Examples of the acid anhydride include methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, trimellitic anhydride, nadic anhydride, hymic anhydride, methyl nadic anhydride, methyl bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, methyl norbornane-2,3-dicarboxylic acid, and the like.

[0043] Examples of the amines include diethylenediamine, triethylenetetramine, hexamethylenediamine, dimer acid-modified ethylenediamine, 4,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenol ether, and the like. These may be used alone or in combination of two or more as the curing agent.

[0044] In the resin composition of the present invention, the content of the curing agent is preferably 10 to 300 parts by weight, more preferably 100 to 200 parts by weight, based on 100 parts by weight of the epoxy compound (the total of the epoxy compound of the present invention and another epoxy compound).

[0045] Examples of the curing accelerator include amine compounds, imidazole compounds, organic phosphine compounds such as triphenylphosphine, diphenylnaphthylphosphine, diphenylethylphosphine, aromatic phosphonium salts, aromatic diazonium salts, aromatic iodonium salts, aromatic selenium salts, and the like.

[0046] Examples of the curing accelerator include amine compounds such as 1,8-diazabicyclo[5.4.0]-7-undecene, diethylenetriamine, triethylenetetramine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, tris(dimethylaminomethyl)phenol, imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-heptadecylimidazole, organic phosphine compounds such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine, diphenylphosphine, phenylphosphine, phosphonium compounds such as tetrabutylphosphonium bromide, tetrabutylphosphonium diethyl phosphorodithioate, tetraphenylboron salts such as tetraphenylphosphonium·tetraphenylborate, 2-methyl-4-methylimidazole·tetraphenylborate, N-methylmorpholine·tetraphenylborate, and aliphatic acid metal salts such as lead acetate, tin octylate, cobalt hexanoate. It is already known that some of these curing accelerators can also be used as the aforementioned curing agents. These may be used alone or in combination of two or more as the curing accelerator.

[0047] In the resin composition of the present invention, the content of the curing accelerator is preferably 0.01 to 10.0 parts by weight, more preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the epoxy compound (the total of the epoxy compound of the present invention and another epoxy compound).

[0048] In the resin composition of the present invention, the curing agent and the curing accelerator may be used alone, either the curing agent or the curing accelerator only, or in combination of the curing agent and the curing accelerator.

[0049] The resin composition of the present invention, as long as it does not inhibit the effects of the present invention, Inorganic fillers such as amorphous silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesia, clay, talc, calcium silicate, titanium oxide, etc., various polymers such as phenolic resins, unsaturated polyesters, etc., aliphatic polyols such as ethylene glycol, propylene glycol, etc., 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-based, surface treatment agents for inorganic fillers, flame retardants, antistatic agents, colorants, antistatic agents, leveling agents, ion trap agents, sliding property improvers, various rubbers, organic polymer beads, inorganic fillers such as glass beads, glass fibers, etc., impact resistance improvers, thixotropy imparting agents, surfactants, surface tension reducing agents, defoaming agents, sedimentation inhibitors, light diffusing agents, ultraviolet absorbers, antioxidants, mold release agents, fluorescent agents, conductive fillers, etc. (modifying agents) may be contained.

[0050] The epoxy compound of the present invention is useful as a material for paints, encapsulants, adhesives, resist inks, etc. for printed wiring boards and electronic components, as well as epoxy resin compositions as coating agents for protecting the surfaces of woodworking paints, optical fibers, plastics, and cans, epoxy resin compositions for ball grid array semiconductor encapsulation, epoxy resin compositions for optical semiconductor element encapsulation, epoxy resin compositions for semiconductor encapsulation used as underfill, and epoxy resin compositions for forming resist lower layer films for lithography.

Examples

[0051] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited thereto. The main raw materials, etc. used in the synthesis of the epoxy compound are as follows.

[0052] · 4-Iodophthalic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., refer to Chemical Formula (II-3-2).) · 2,3,5-Triiodoterephthalic acid (synthesized by the methods of Synthesis Examples 1 and 2. Refer to Chemical Formula (II-1-5).) · 2,4,5,6 - Tetraiodoisophthalic acid (synthesized according to the method described in JP-A-06-345705. See Chemical formula (II-2-11).) · Epichlorohydrin (manufactured by Fujifilm Wako Pure Chemical Corporation) · Tetramethylammonium chloride (manufactured by Fujifilm Wako Pure Chemical Corporation) · Sodium hydroxide (manufactured by Fujifilm Wako Pure Chemical Corporation) · Chloroform (manufactured by Fujifilm Wako Pure Chemical Corporation) · Ethyl acetate (manufactured by Fujifilm Wako Pure Chemical Corporation) · Methanol (manufactured by Fujifilm Wako Pure Chemical Corporation)

[0053] The main raw materials and the like used in the preparation of the resin composition are as follows. (A) Epoxy compound · Diglycidyl isophthalate (synthesized according to the method described in Chinese Patent Application Publication No. 103864724. See Chemical formula (1).) (B) Curing accelerator · 2 - Ethyl - 4 - methylimidazole (manufactured by Shikoku Kasei Kogyo Co., Ltd., trade name "Curezol 2E4MZ", hereinafter referred to as "2E4MZ".)

[0054]

Chemical formula

[0055] [Synthesis Example 1] [Synthesis of 2 - Amino - 3,5 - diiodoterephthalic acid] Into a 200 mL flask, 7.25 g (40 mmol) of 2 - aminoterephthalic acid and 16 mL of acetic acid were charged, and a mixture of 25.9 g (160 mmol) of iodine monochloride, 3.0 g (30.2 mmol) of 36% concentrated hydrochloric acid, and 52 g of ion - exchanged water was added dropwise while stirring at room temperature. Subsequently, the mixture was stirred at 50 °C for 85 hours. After filtering the reaction solution, tetrahydrofuran and toluene were added to the obtained solid for recrystallization. This was filtered and dried to obtain 14.3 g of a yellow solid (yield: 82%).

[0056] Of the obtained yellow solid1 The 1H-NMR spectrum data was as follows. · 1 1H-NMR(CDCl 3 ) δ: 8.11(s, 1H). From this spectrum data, the obtained yellow solid was identified as the title compound (2-amino-3,5-diiodoterephthalic acid).

[0057] [Synthesis Example 2] [Synthesis of 2,3,5-triiodoterephthalic acid (Chemical formula (II-1-5))] To a 1000 mL flask, 4.33 g (10 mmol) of 2-amino-3,5-diiodoterephthalic acid, 10.00 g of ion-exchanged water, 10.00 g of acetonitrile, and 2.06 g (20 mmol) of 95% sulfuric acid were charged. After purging with nitrogen, while stirring at -10°C, 5.18 g (30 mmol) of a 40% aqueous sodium nitrite solution was added dropwise. After stirring at -10°C for 1 hour, 11.31 g (40 mmol) of a 53% aqueous sodium iodide solution was added dropwise at -10°C, and stirring was continued for another 12 hours. After quenching with a 35% aqueous sodium bisulfite solution, the solid was collected by filtration. 25 g of ion-exchanged water was added to the filtrate for reslurrying, and after filtration and drying, 4.24 g of a brown solid was obtained (yield: 78%).

[0058] The 1 1H-NMR spectrum data of the obtained brown solid was as follows. · 1 1H-NMR(CDCl 3 ) δ: 7.88(s, 1H). From this spectrum data, the obtained brown solid was identified as the title compound (2,3,5-triiodoterephthalic acid) represented by Chemical formula (II-1-5).

[0059] [Example 1] [Synthesis of diglycidyl 4-iodophthalate (Chemical formula (I-3-2))] Into a 100 mL three-necked flask, 2.92 g (10 mmol) of 4-iodophthalic acid, 37.01 g (400 mmol) of epichlorohydrin, and 54.8 mg (0.5 mmol) of tetramethylammonium chloride were charged, and the mixture was stirred at 80 °C for 6 hours. Next, the reaction solution was cooled to 2 °C, 2.00 g (24 mmol) of a 48% aqueous sodium hydroxide solution was added, and the mixture was stirred at 30 °C for 14 hours. After adding 10.0 g of ion-exchanged water to the reaction solution, the aqueous layer was removed by liquid separation, and the organic layer was concentrated. The obtained concentrate was purified by silica gel column chromatography (chloroform / ethyl acetate = 30 / 1 (w / w)) to obtain 1.33 g of a colorless liquid (yield: 33%).

[0060] For the obtained colorless liquid 1 The 1H-NMR spectral data was as follows. · 1 1H-NMR (DMSO-d 6 ) 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). From this spectral data, the obtained colorless liquid was identified as the title compound (4-iodophthalic acid diglycidyl ester) represented by chemical formula (I-3-2).

[0061] [Example 2] <Synthesis of 2,3,5-triiodoterephthalic acid diglycidyl ester (chemical formula (I-1-5))> Into a 100 mL three-necked flask, 10.88 g (20 mmol) of 2,3,5-triiodoterephthalic acid, 37.01 g (400 mmol) of epichlorohydrin, and 110 mg (1 mmol) of tetramethylammonium chloride were charged, and the mixture was stirred at 80 °C for 6 hours. Next, the reaction solution was cooled to 2 °C, 4.00 g (48 mmol) of a 48% aqueous sodium hydroxide solution was added, and the mixture was stirred at 30 °C for 20 hours. After adding 24.00 g of ion-exchanged water to the reaction solution, the aqueous layer was removed by liquid separation, and the organic layer was concentrated. The obtained concentrate was purified by silica gel column chromatography (chloroform / methanol = 20 / 1 (w / w)) to obtain 4.07 g of a pale yellow solid (yield: 31%).

[0062] The obtained pale yellow solid's 1 1H-NMR spectral data was as follows. · 1 1H-NMR (DMSO-d 6 ) 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). From this spectral data, the obtained pale yellow solid was identified as the title compound (2,3,5-triiodoterephthalic acid diglycidyl ester) represented by chemical formula (I-1-5).

[0063] [Example 3] [Synthesis of 2,4,5,6-tetraiodoisophthalic acid diglycidyl ester (chemical formula (I-2-11))] In a 100 mL three-necked flask, 13.39 g (20 mmol) of 2,4,5,6-tetraiodoisophthalic acid, 37.01 g (400 mmol) of epichlorohydrin, and 110 mg (1 mmol) of tetramethylammonium chloride were charged and stirred at 80 °C for 6 hours. Next, the reaction solution was cooled to 2 °C, 4.00 g (48 mmol) of a 48% aqueous sodium hydroxide solution was added, and the mixture was stirred at 30 °C for 20 hours. After adding 24.00 g of ion-exchanged water to the reaction solution, the aqueous layer was removed by liquid separation, and the organic layer was concentrated. The obtained concentrate was purified by silica gel column chromatography (chloroform / methanol = 20 / 1 (w / w)) to obtain 8.76 g of a pale yellow solid (yield: 56%).

[0064] For the obtained pale yellow solid 1 The 1H-NMR spectral data was as follows. · 1 1H-NMR (DMSO-d 6 ) δ: 4.65 (dd, 2H), 4.09 (dd, 2H), 3.40 - 3.30 (m, 2H), 2.86 (t, 2H), 2.75 (dd, 2H). From this spectral data, the obtained pale yellow solid was identified as the title compound (2,4,5,6-tetraiodoisophthalic acid diglycidyl ester) represented by chemical formula (I-2-11).

[0065] [Example 4] As an epoxy compound, 10.0 g of the epoxy compound of Example 1 and 0.5 g of 2E4MZ as a curing accelerator were mixed to prepare a resin composition (epoxy resin composition). For this resin composition, the gel time at 150 °C was measured by the hot plate method (JIS C-2105) to evaluate the curing performance. The obtained results were as shown in Table 1.

[0066] [Example 5, Comparative Example 1] In the same manner as in the case of Example 4, resin compositions having the compositions shown in Table 1 were prepared, and the gel times of these resin compositions were measured to evaluate the curing performance. The obtained evaluation results are shown in Table 1.

[0067]

Table 1

[0068] From Table 1, when the epoxy compound of the present invention was used as the epoxy compound (Examples 4 and 5), it was confirmed that the gelling time was shorter and the curability was excellent compared to the case where a conventional epoxy compound was used (Comparative Example 1). Therefore, the epoxy compound of the present invention is considered to be more suitable as a resin material than conventional epoxy compounds.

Industrial Applicability

[0069] Since the epoxy compound of the present invention has an iodine atom in the molecule, when used as a material for a resin composition, it is expected to exhibit good curability and give a cured product having excellent heat resistance and electrical properties as compared with the case where a conventional epoxy compound is used. Therefore, the epoxy compound of the present invention is considered to be suitable as a resin material.

Claims

1. An epoxy compound represented by chemical formula (I): 【Chemistry 1】 (In the formula, X represents an iodine atom, and n represents an integer of 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 any one of claims 2 to 3.

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