Epoxy compounds

Abstract

To provide an epoxy compound that can give a cured product excelling in heat resistance, adhesion, water resistance, mechanical strength, electrical characteristics and the like.SOLUTION: The present invention provides an epoxy compound represented by the following formula 1. In the formula 1, R's independently represent a hydrogen atom or a C1-6 hydrocarbon group, a is an integer of 0-4, b is an integer of 0-3 and n is an integer of 0-20.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention reacts with a curing agent such as a phenolic compound to provide heat resistance, adhesiveness, water resistance, and mechanical strength. The present invention relates to an epoxy compound that can give a cured product having excellent properties such as viscosity and electrical characteristics. [Background technology]

[0002] The cured product obtained by reacting epoxy compounds with curing agents such as phenolic compounds has heat resistance and adhesive properties. It has excellent water resistance, mechanical strength, and electrical properties, making it suitable for use in adhesives, paints, and civil engineering and construction materials. It is used as an insulating material for electrical and electronic components. For example, Patent Document 1 discloses a semi-finished product using an epoxy resin having a dicyclopentadiene skeleton. An epoxy resin composition for encapsulating conductors is described. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-191200 Summary of the Invention [Problem to be solved by the invention]

[0004] In recent years, the amount of heat generated during use has increased due to the increasing density of semiconductors, and heating during soldering has become a problem. Resin compositions for encapsulating semiconductors are required to have higher performance. The epoxy resin having a dicyclopentadiene skeleton described in Patent Document 1 has sufficient heat resistance. cracks rather than breakdown, and adhesion to metal is insufficient, resulting in semiconductor elements and leads It was prone to peeling off from the frame. [Means for solving the problem]

[0005] The gist of the present invention resides in an epoxy compound having an alicyclic structure represented by the following formula 1.

[0006] [ka]

[0007] In formula 1, each R is independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. is an integer of 0 to 4, and b is an integer of 0 to 3. n is an integer of 0 to 20. [Effects of the Invention]

[0008] The epoxy compound of the present invention has heat resistance, adhesion to metals, adhesiveness, water resistance, and functionality. The cured product has excellent mechanical strength and electrical properties. Stoppers, machine parts, adhesives, paints, civil engineering and construction materials, insulating materials for electrical and electronic parts, optical materials It can be used for the following purposes: DETAILED DESCRIPTION OF THE INVENTION

[0009] The epoxy compound of the present invention has a structure represented by the following formula 1.

[0010] [ka]

[0011] The epoxy compound of the present invention has a structure derived from tricyclopentadiene, and the cured product thereof has The linear expansion coefficient and loss modulus are low, improving heat crack resistance. Sexuality also improves. In the formula 1, each R is independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. .

[0012] Examples of the hydrocarbon group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, and the like. Phenyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl In terms of fluidity and curing properties, R is preferably a methyl group. Of these, an ethyl group is preferred, and a methyl group is more preferred. The bonding position (substitution position) of the R to the hydroxyl group of the benzene ring is set to be 100% because of ease of production. The ortho or para position is preferred, and the para position is more preferred.

[0013] a is an integer of 0 to 4. In terms of fluidity, a is preferably an integer of 0 to 2, more preferably an integer of 0 to 1. 0 is particularly preferred. b is an integer of 0 to 3. From the viewpoint of fluidity, b is preferably an integer of 0 to 2, more preferably an integer of 0 to 1. 0 is particularly preferred. n is an integer of 0 to 20. In terms of fluidity and curability, n is preferably an integer of 0 to 10, and 0 A value of 0 to 5 is more preferred, and 0 to 2 is particularly preferred. Furthermore, in the present invention, the formula 1 is preferably an epoxy compound represented by the following formula 2: stomach.

[0014] [ka]

[0015] n is an integer of 0 to 20, preferably 0 to 10 from the viewpoint of fluidity and curability, and 0 to 5 is more preferred, and 0 to 2 is particularly preferred. The epoxy compound of the present invention has the advantage of being able to obtain a cured product having excellent crack resistance and adhesive strength. The epoxy equivalent is preferably 200 to 600 g / equivalent, and more preferably 250 to 500 g / equivalent. Preferably, the amount is 250 to 400 g / equivalent, and particularly preferably 250 to 400 g / equivalent.

[0016] In the present invention, the term "epoxy equivalent" means "an epoxy resin containing one equivalent of epoxy groups." It is defined as the "mass of fat" and can be measured in accordance with JIS K7236. An example of a method for producing the epoxy compound represented by the formula 1 is shown below. The epoxy compound of the present invention is a tricyclopentadiene-type phenolic compound represented by the following formula 3: It can be obtained by reacting the compound with epihalohydrin.

[0017] [ka]

[0018] In the formula 1, each R is independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. . Examples of the hydrocarbon group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, and the like. Phenyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl Examples of the aryl group include a cyclohexyl group and a cyclohexyl group. The R is preferably a methyl group or an ethyl group from the viewpoint of fluidity and curability, and more preferably a methyl group. More preferable. The bonding position (substitution position) of the R to the hydroxyl group of the benzene ring is set to be 100% because of ease of production. The ortho or para position is preferred, and the para position is more preferred.

[0019] a is an integer of 0 to 4. In terms of fluidity, a is preferably an integer of 0 to 2, more preferably an integer of 0 to 1. 0 is particularly preferred. b is an integer of 0 to 3. From the viewpoint of fluidity, b is preferably an integer of 0 to 2, more preferably an integer of 0 to 1. 0 is particularly preferred. n is an integer of 0 to 20. In terms of fluidity, n is preferably an integer of 0 to 10, more preferably an integer of 0 to 5. It is preferable that the number of ions is 0 to 2, and 0 to 2 is particularly preferable. Furthermore, in the present invention, the compound represented by formula 3 is preferably a phenol compound represented by formula 4 below: It's nice.

[0020] [ka]

[0021] n is an integer of 0 to 20, and from the viewpoint of fluidity, it is preferably an integer of 0 to 10, and more preferably an integer of 0 to 5. It is particularly preferably 0 to 2. Standards of the phenolic compounds of the present invention measured by gel permeation chromatography (GPC) The number average molecular weight (Mn) is preferably 400 to 1,000 in terms of polystyrene. The phenolic compounds of the present invention were also measured by gel permeation chromatography (GPC). The weight average molecular weight (Mw) is preferably 450 to 1,500 in terms of standard polystyrene.

[0022] The number average molecular weight and weight average molecular weight are preferably high from the viewpoint of curability of the resin composition, From the viewpoint of fluidity, a lower value is preferable. Furthermore, the hydroxyl equivalent of a phenolic compound can be determined by, for example, the acetylation of the compound in a pyridine-acetic anhydride solution. The hydroxyl equivalent of the chloride measured by alkali back titration is preferably 190 or more and 300 or less. A higher hydroxyl equivalent is preferable from the viewpoint of curability of the resin composition, and a lower hydroxyl equivalent is preferable from the viewpoint of fluidity. preferable.

[0023] As the epihalohydrin, epichlorohydrin or epibromohydrin is usually used. However, epichlorohydrin is preferred in the present invention. The amount of epihalohydrin used is 1 equivalent of the hydroxyl group of the phenol compound used as the raw material. Usually, 1.0 to 10.0 equivalents, preferably 2.0 to 8.0 equivalents, and more preferably 3.0 to 7.5 equivalents. The amount of epihalohydrin used is determined based on the control of the polymerizing reaction and the epoxy resin obtained. A higher value is preferable in terms of the resin having an appropriate epoxy equivalent, and a lower value is preferable in terms of production efficiency. I wish.

[0024] In the above reaction, an alkali metal hydroxide is used as a catalyst to promote the epoxidation process. The alkali metal hydroxide used here is usually sodium hydroxide. The alkali metal hydroxide may be in the form of a solid. Alternatively, an aqueous solution thereof may be used. The amount of alkali metal hydroxide used is usually 0.5g per equivalent of hydroxyl group of the raw phenol compound. 1 to 3.0 equivalents, preferably 0.5 to 2.0 equivalents, more preferably 0.9 to 1.6 equivalents The amount of alkali metal hydroxide used is preferably high from the viewpoint of controlling the polymerizing reaction. In order to suppress the generation of impurities due to side reactions, it is preferable that the temperature is low.

[0025] In addition, tetramethylammonium chloride, tetraethylammonium chloride, Quaternary ammonium salts such as ammonium bromide, benzyldimethylamine, 2,4,6-trimethylammonium bromide, tertiary amines such as 2-ethyl-4-methylimide, 2-methyl-4-methylisothiazolinone ... imidazoles such as 2-phenylimidazole, ethyltriphenylphosphonium Phosphonium salts such as ammonium iodide, phosphines such as triphenylphosphine, etc. It may also be added as a solvent.

[0026] In the above reaction, an alcohol having 1 to 5 carbon atoms is used in addition to the epihalohydrin. The alcohol having 1 to 5 carbon atoms is preferably methanol, ethanol, isopropyl alcohol, or the like. In the present invention, phenol compounds and alcohols such as propyl alcohol are included. In view of the solubility of the alkali metal hydroxide, alcohols having 1 to 3 carbon atoms are preferred, and in particular, Isopropyl alcohol is preferred.

[0027] The amount of alcohol used is usually 2 to 50% by weight relative to the amount of epihalohydrin used. The amount of alcohol used is preferably 4 to 40% by weight, and particularly preferably 7 to 30% by weight. The dosage is preferably higher in order to obtain an epoxy compound that gives a cured product with excellent crack resistance. It is preferable that the content is low in order to reduce the amount of hydrolyzable chlorine. The above reaction can be carried out under normal pressure or reduced pressure, and the reaction temperature is 20 to 150°C. The reaction temperature is preferably 40 to 100°C, more preferably 40 to 80°C. A higher concentration is preferable from the viewpoint of reactivity, and a lower concentration is preferable from the viewpoint of suppressing side reactions.

[0028] The reaction time is usually 0.5 to 10 hours, preferably 1 to 8 hours, particularly preferably 1 to 8 hours. In order to prevent a rapid reaction, the alkali metal hydroxide is preferably 0. Add small amounts intermittently or continuously over 1 to 8 hours, preferably 0.5 to 6 hours. The addition time of the alkali metal hydroxide is preferably long from the viewpoint of controlling the reaction temperature. From the viewpoint of economy, a shorter length is preferable.

[0029] After the reaction is complete, the insoluble by-product salts are removed by filtration or by washing with water, and then the unreacted epitaxial layer is removed. The epoxy compound of the present invention is obtained by removing the halohydrin, solvent, etc. by distillation under reduced pressure. In order to obtain an epoxy compound with a low hydrolyzable chlorine content, the recovered epoxy compound Ketone compounds with 4 to 7 carbon atoms (e.g., methyl isobutyl ketone, methyl ethyl ketone) Examples of the solvent include cyclohexane, cyclopentanone, and cyclohexanone. The reaction is carried out by adding an aqueous solution of an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide. In this case, the amount of alkali metal hydroxide used is preferably 100% by weight. Usually, 0.01 to 0.3 moles of hydroxyl group are added to 1 mole of the raw phenol mixture used for oxidation. The reaction temperature is usually 50 to 120°C, and the reaction time is preferably 0.05 to 0.2 mol. is usually 0.5 to 2 hours.

[0030] After the reaction is completed, the salt formed is removed by filtration, washing with water, etc., and the solvent is distilled off under heating and reduced pressure. By this, an epoxy compound with a small amount of hydrolyzable chlorine can be obtained. The resin composition containing the epoxy compound of the present invention and a curing agent has heat resistance, adhesiveness, water resistance, and functionality. A cured product with excellent mechanical strength and electrical properties can be obtained. As the curing agent, those generally known as epoxy resin curing agents can be used. For example, phenolic curing agents, aliphatic amines, polyether amines, alicyclic amines, Amine-based hardeners such as aromatic amines, acid anhydride-based hardeners, amide-based hardeners, tertiary amines The curing agent may be used alone or in combination of two or more. They may also be used in combination.

[0031] The curing agent is an agent that provides the cured product with excellent heat resistance, stress resistance, moisture absorption resistance, flame retardancy, etc. Therefore, it is preferable to contain a phenol-based curing agent. The phenol-based curing agent includes bisphenol A, bisphenol F, bisphenol S, bisphenol A, hydroquinone, resorcinol, methylresorcinol, biphenyl dihydroxydiphenyl, tetramethylbiphenol, dihydroxynaphthalene, dihydroxydiphenyl Ethers, thiodiphenols, phenol novolac resins, cresol novolac resins , phenol aralkyl resin, biphenyl aralkyl resin, naphthol aralkyl resin, Terpene phenolic resin, dicyclopentadiene phenolic resin, bisphenol A novo Lac resin, trisphenol methane type resin, naphthol novolac resin, brominated bisphenol Various polyhydric phenols such as phenol A and brominated phenol novolac resins.

[0032] Various phenols and benzaldehyde, hydroxybenzaldehyde, crotonaldehyde Polyhydric phenols obtained by condensation reaction with various aldehydes such as aldehyde and glyoxal. Resins, polyhydric phenol resins obtained by condensation reaction of xylene resins and phenols, polymers Co-condensation resin of heavy oil or pitch, phenol and formaldehyde. Phenol-benzaldehyde-xylylenedimethoxide polycondensate, phenol-benzaldehyde Polycondensation product of benzaldehyde and xylylene dihalide, phenol and benzaldehyde, 4, 4'-Dimethoxide biphenyl polycondensate, phenol-benzaldehyde-4,4'- Examples include various phenolic resins such as dihalide biphenyl polycondensates.

[0033] These phenolic curing agents may be used alone or in any combination of two or more. They may be used in combination at a given blend ratio. Among the phenol-based curing agents, phenol is preferred from the viewpoint of heat resistance and curability after curing of the composition. Nol novolac resin, phenol aralkyl resin, biphenyl aralkyl resin, naphtho Novolac resin, naphthol aralkyl resin, trisphenol methane resin, phenol Polycondensation of phenol, benzaldehyde, and xylylenedimethoxide, phenol, benzaldehyde, and xylylenedimethoxide Polycondensation product of phenol and benzaldehyde with xylylene dihalide, Dimethoxide biphenyl polycondensate, phenol-benzaldehyde-4,4'-dihalo Ido-biphenyl polycondensates are preferred, and phenol novolak resins are particularly preferred.

[0034] The resin composition may contain, as needed, an epoxy resin other than the epoxy compound of the present invention. , and additives such as a curing accelerator and an inorganic filler may also be included. Specific examples of other epoxy resins that can be used in combination with the epoxy compound used in the present invention include: Examples include bisphenol A epoxy resin, bisphenol F epoxy resin, and bisphenol Nol S type epoxy resin, bisphenol AD ​​type epoxy resin, resorcinol type epoxy resin Fat, hydroquinone type epoxy resin, catechol type epoxy resin, dihydroxynaphthalene Biphenol-type epoxy resin, tetramethylbiphenol-type epoxy resin Epoxy resins derived from divalent phenols such as resins.

[0035] Phenol novolac epoxy resin, cresol novolac epoxy resin, tris Phenolmethane type epoxy resin, tetraphenylethane type epoxy resin, dicyclopentasiloxane Polyethylene-phenol modified epoxy resin, phenol aralkyl epoxy resin, biphenyl Phenyl aralkyl type epoxy resin, naphthol novolac type epoxy resin, naphthol aralkyl type epoxy resin Ralalkyl type epoxy resin, naphthol-phenol co-condensed novolac type epoxy resin, naphthol Toluene-cresol co-condensed novolac epoxy resin, aromatic hydrocarbon formaldehyde resin 3 types of epoxy resins, such as oil-modified phenolic resin type epoxy resins and biphenyl-modified novolac type epoxy resins Epoxy resins derived from phenols of hydroxyl or higher, tetrabromobisphenol A type epoxy resins epoxy resin, brominated phenol novolac type epoxy resin, etc. Two or more of these epoxy resins may be used in combination.

[0036] Curing accelerators include phosphorus compounds, tertiary amines, imidazoles, organic acid metal salts, and Examples of the compound include phosphorus compounds, amine complex salts, etc., and phosphorus compounds are preferred. Good too. Inorganic fillers include fused silica, crystalline silica, glass powder, alumina, silicon nitride, and talc. , aluminum hydroxide, calcium carbonate, calcium sulfate, etc., and from the viewpoint of the amount of blending, molten silica These may be used in combination of two or more kinds.

[0037] The cured product obtained by curing the resin composition of the present invention has heat resistance, adhesiveness, water resistance, mechanical strength, electrical It has excellent mechanical properties and is used in circuit boards, semiconductor encapsulation materials, machine parts, adhesives, paints, civil engineering and building materials, It can be used as an insulating material for electrical and electronic components, optical material, etc. [Example]

[0038] The present invention will be described below with reference to examples. The present invention was evaluated by the following methods. .

[0039] <Number average molecular weight (Mn) and weight average molecular weight (Mw)> Measurement was performed using Tosoh Corporation's GPC "HLC-8220GPC" under the following measurement conditions: did. As standard polystyrene, TSK Standard Polystyrene:F- 450, F-128, F-20, F-4, F-2, A-2500, A-1000 A calibration curve was created, and the number average molecular weight and weight average molecular weight were measured as polystyrene equivalent values. Ta. Column: Tosoh Corporation "TSKGEL SuperHZM-N" x 3 Eluent: tetrahydrofuran Flow rate: 0.35ml / min Detection: RI Temperature: 40℃ Sample concentration: 0.1% by weight Injection volume: 10 μl

[0040] <Hydroxyl group equivalent> A method using an acetylating reagent in accordance with the neutralization titration method of JIS K0070-1992 The hydroxyl equivalent of the phenol compound was measured.

[0041] <Epoxy equivalent> The epoxy equivalent of the epoxy compound was measured in accordance with JIS K7236:2001.

[0042] <Expansion coefficient> Measurements were taken using a thermomechanical analyzer "TMA / SS6100" manufactured by Seiko Instruments Inc. did. The cured specimen was placed in compression mode, with the first temperature increase rate being 5°C / min (from 30°C to 250°C), and the second temperature increase rate being 100°C / min (from 30°C to 250°C). The first temperature drop was 10°C / min (from 250°C to 30°C), and the second temperature increase was 5°C / min (from 30°C to The temperature was changed from 250°C to 250°C, and the linear expansion coefficient α1 was measured for the second time. (The size of the test piece was Cylinder with a diameter of 1 cm and a thickness of 3 mm)

[0043] <Elastic modulus> Using the Seiko Instruments Inc. dynamic viscoelasticity measuring device "EXSTAR6100" In three-point bending mode, the temperature was increased from 30°C to 280°C at a rate of 5°C / min, and then at 250°C, The loss modulus E'' was measured (the size of the test piece was 5 cm length x 1 cm width x 3 mm thickness).

[0044] <Shear adhesive strength to metal> The test was conducted in accordance with JIS-K6850. Width: 25mm, length: 100mm, thickness: 1.6m Each ingredient is placed between two metal plates (double-sided mirror type manufactured by Yutaka Panel Service) in an aluminum dish. The curable resin composition was stirred at 120°C until it was homogeneous, and then placed in a container measuring 25 mm wide x 12.5 mm long. After coating, the film was placed in a thermostatic chamber and heated to 120°C. Test specimens were prepared by heating at 175°C for 2 hours and curing at 175°C for 6 hours. The prepared test specimen was subjected to a tensile test using an Instron 5582 tensile tester. Tensile shear tests were carried out at a speed of 5 mm / min with n = 3 tests, and the tensile shear strength was measured. The measurements were carried out on aluminum plates and nickel plates.

[0045] <Raw materials used> The raw materials used in the following examples and comparative examples are as follows. Tricyclopentadiene (TCPD): Applied Organometallics c Chemistry), 2014, Vol. 28, p. 152. The transition metal catalyst was Pd(dba)2, and the ligand was P(p-tolyl). 3 was used. Phenol: manufactured by Nacalai Tesque, Inc. p-Toluenesulfonic acid monohydrate: Fujifilm Wako Pure Chemical Industries, Ltd. Chloroform: Kanto Chemical Co., Ltd. Epichlorohydrin: manufactured by Tokyo Chemical Industry Co., Ltd. 50% sodium hydroxide aqueous solution: Fujifilm Wako Pure Chemical Industries, Ltd. 2-Propanol: Fujifilm Wako Pure Chemical Industries, Ltd. Dicyclopentadiene phenol compound (product name "ERM6115"): Songwon Made Phenol compound (product name "PSM4261"): manufactured by Gun-ei Chemical Industry Co., Ltd. Curing catalyst (product name "Hokuko TPP"): manufactured by Hokko Chemical Industry Co., Ltd.

[0046] <Production Example 1 (Production of Epoxy Compound 1)> In a four-neck flask equipped with a stirrer, a thermometer, and a dropping funnel, add 61.6 g (0.6 5 mol) and TCPD 31.0 g (0.16 mol) were added, and the mixture was purged with nitrogen gas. The internal temperature was raised to 90°C and the contents were heated to dissolve. Then, 2.4 g of p-toluenesulfonic acid monohydrate was dissolved in 3 mL of water in a dropping funnel. The aqueous solution was added and slowly dropped while keeping the internal temperature at 90-100°C. The temperature was raised to 140°C and the reaction was carried out for 7 hours. After the internal temperature was lowered to 90°C, 20% potassium hydroxide was added. The catalyst was deactivated by adding 4.2 g of aqueous ammonium hydroxide solution.

[0047] The reaction mixture was heated to 110°C, and the unreacted phenol was distilled off under reduced pressure. The mixture was cooled to 0°C and dissolved in chloroform, and then transferred to a separatory funnel. The mixture was washed with 20% aqueous potassium hydroxide solution, and then with water until the pH reached 7. After removing the solvent using an evaporator, phenol compound A (TCPD / PHL novolak The phenol compound A had an Mn of 668, an Mw of 934, and a hydroxyl equivalent of 1.0g. It was 258g / eq.

[0048] Next, 20 g of the phenol compound A (phenol compound B) was added to a four-neck flask equipped with a stirrer and a thermometer. The number of moles of phenolic hydroxyl groups: 0.08 mol) was added and the mixture was purged with nitrogen gas. Chlorohydrin 44.4 mL (0.57 mol), 2-propanol 26.0 mL, water 7 0.3mL was added and dissolved with stirring, and the temperature was raised from room temperature to 40°C. 5.52 mL of 50% aqueous sodium hydroxide solution was added in six portions over 1.5 hours, starting from 40°C. The mixture was added while heating to 65°C (amount added at one time: 0.92 mL). After the addition, the mixture was allowed to react for 0.5 hours. After the reaction was stopped, 14.2 mL of water was added, and the reaction mixture was transferred to a separatory funnel and the organic layer was extracted. I put it out. Methylene chloride was added to extract the organic layer again. After the solvent was removed by drying, epoxy compound 1 (TCPD / PHL novolac type epoxy) The epoxy equivalent of this epoxy compound was 368 g / eq.

[0049] <Production Example 2 (Production of Epoxy Compound 2)> Dicyclopentadiene phenol compound (E 20g of RM6115 was added and the mixture was purged with nitrogen gas. mL (0.75 mol), 34.5 mL of 2-propanol, and 9.7 mL of water were added and stirred. The mixture was heated from room temperature to 40°C.

[0050] 6.48 mL of 50% sodium hydroxide solution was added in six portions over 1.5 hours at 40°C. The mixture was added while heating to 5°C (amount added at one time: 1.08 mL). After the addition, the mixture was reacted for 0.5 hours. After the reaction was stopped, 18.9 mL of water was added, and the reaction mixture was transferred to a separatory funnel to extract the organic layer. did. Chloroform was added to extract the organic layer again. After solvent distillation by drying, epoxy compound 2 (DCPD / PHL novolac type epoxy) The epoxy equivalent of this epoxy compound was 268 g / eq.

[0051] Example 1 Epoxy compound 1 (TCPD / PHL novolac type epoxy) synthesized in Production Example 1 0 parts, hardener (PSM4261) 29 parts, curing catalyst (Hokuko TPP) 1 part, The raw materials were weighed into an aluminum dish and stirred at 120°C until homogeneous. The mixture was then heated at 120°C for 2 hours and then at 175°C for 6 hours to obtain a cured product. The test pieces were cut into the sizes required for each evaluation, and the adhesive strength, elastic modulus, and linear expansion coefficient were measured. The results are shown in Table 1.

[0052] <Comparative Example 1> Epoxy compound 2 (DCPD / PHL novolac type epoxy) 10 synthesized in Production Example 2 0 parts, hardener (PSM4261) 39 parts, curing catalyst (Hokuko TPP) 1 part, The raw materials were weighed into an aluminum dish and stirred at 120°C until homogenous. Then, the mixture was stirred at 120°C for 2 hours. The cured product was then heated at 175°C for 6 hours to obtain a cured product. The adhesive strength, modulus of elasticity, and coefficient of linear expansion were measured. The results are shown in Table 1.

[0053] [Table 1]

[0054] From Table 1, the epoxy compounds are those with a dicyclopentadiene skeleton. The cured product of Comparative Example 1 using the above compound had a high linear expansion coefficient and loss modulus, low heat resistance, and cracks. This is also likely to occur. Also, the adhesive strength to metal is reduced.

Claims

1. An epoxy compound represented by the following formula 1: 【Chemistry 1】 In formula 1, each R is independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, a is an integer of 0 to 4, b is an integer of 0 to 3, and n is an integer of 0 to 20.

2. The epoxy compound according to claim 1, wherein the formula 1 is represented by the following formula 2: 【Chemistry 2】 In formula 2, n is an integer of 0 to 20.

3. A curable composition comprising the epoxy compound according to claim 1 or 2 and a curing agent.

4. The curable composition of claim 3 wherein the curing agent is a phenolic curing agent.

5. The curable composition according to claim 4 , wherein the phenolic curing agent is contained in an amount of 0.1 or more and 1.5 or less in terms of hydroxyl group equivalents relative to 1 equivalent of epoxy groups of the epoxy compound in the curable composition.

6. A cured product obtained by curing the curable composition according to any one of claims 3 to 5.

7. An electric or electronic part comprising the cured product of claim 6.

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