TW201124392A - Diepoxy compound, method for producing same, and composition containing said diepoxy compound - Google Patents

Abstract

The disclosed diepoxy compound is indicated by the formula (1) (wherein R1, R2, R3, and R4 each independently represent a hydrogen atom or an alkyl group having 1-3 carbon atoms, and R5 represents an alkyl group having 2-10 carbon atoms).

Description

[Technical Field] The present invention relates to a diepoxy compound, a process for producing the same, and a composition containing the epoxy compound. [Prior Art] The epoxy cured product obtained by curing the diepoxy compound is industrially widely used in addition to excellent heat resistance and moisture resistance, and exhibits excellent mechanical and electrical properties. In Macromol. C h em . Phy s . 199, 853~859 (1 9 9 8 ), the system has been described by formula (A)

The diepoxide compound shown and the cured product obtained by curing the diepoxide compound and the hardener. SUMMARY OF THE INVENTION The present invention provides: [1] a kind of diepoxide compound, which is represented by formula (1)

-5- 201124392 alkyl group of 1 to 3, R5 represents an alkyl group having a carbon number of ay); [2] a method for producing a diepoxide compound represented by the following formula (1),

(wherein Rl, R2, R3, R4 and R5 represent the same meaning as described above) and the characteristics are expressed by the formula (2)

(In the formula, R1, R2, R3 and the system independently represent a hydrogen atom or a carbon number of 1 to 3, and R5 represents a non-carbon number of 2 to 1 院.) 3) χ1^ΝΝς/° (3) (wherein, X1 represents a halogen atom) The epihalohydrin shown is a reaction in the presence of an ammonium salt and an inorganic base; [3] The production method according to [2], The reaction is carried out in the presence of an alcohol solvent; [4] The method according to [3], wherein the alcohol solvent is at least one selected from the group consisting of a secondary alcohol solvent and a tertiary alcohol solvent; [5] [2] The production method according to any one of [2], wherein the dihydroxy compound represented by the formula (2) and the epihalohydrin-6-201124392 and the ammonium compound represented by the formula (3) are mixed. The salt is reacted, and the mixture is further reacted by mixing; [6] The method for producing any one of [2] to [5], which is sodium hydroxide or potassium hydroxide; [7] a dihydroxy compound which is represented by the formula (2)

The alkyl group of 1 to 3, R5, represents an alkyl group having 2 to 1 carbon atoms, and is represented by a dihydroxy compound represented by the following formula (2).

) its characteristics are based on equation (4)

a dihydroxy compound represented by an alkyl group of 1 to 3) and an inorganic base of the formula (5), an inorganic base (2) or a carbon number (2), a meaning or a carbon number (5) (5) )201124392

(wherein, R5 represents an alkyl group having 2 to 10 carbon atoms) a compound represented by the reaction in the presence of an acid; [9] a composition which contains the formula (1)

(wherein R1, R2, R3 and R4 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R5 represents a dialkyl compound represented by an alkyl group having 2 to 10 carbon atoms) and a curing agent; [10] The composition of [9], wherein the hardener is at least one hardener selected from the group consisting of an amine hardener, a phenol hardener, and an acid anhydride hardener; [11] as in [10] The amine hardener is composed of 4,4,-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 1,5-diaminonaphthalene and p-phenylenediamine. At least one selected from the group consisting of: [1 2] a composition according to any one of [9] to [1 1], further comprising aluminum oxide; [1 3 ] composition of [1 2 ] And containing 75 parts by weight to 95 parts by weight of alumina with respect to 100 parts by weight of the total of the diepoxide compound and the hardener represented by the formula (1); [I4] as in [12] or [13] The composition, wherein the alumina is D50 (201124392 cumulative volume 50% of the particle size) is 2 " m or more l〇〇em below the oxidation of the Ming A, D50 is l " m above 10 / im of the alumina B, and D50 is 0.0 1 /zm or more and 5 // m The mixture of alumina C, the total ratio of alumina A to alumina B and alumina C, and the ratio of each alumina in the volume % of alumina is 50 to 90% by volume of alumina A, and alumina B is 5 to 40% by volume, and alumina C is 1 to 30% by volume; [1 5 ] a cured product obtained by hardening the composition of any one of [9] to [1 1 ] Π6] A prepreg obtained by coating a composition of any one of [9] to [1 1] after being impregnated into a substrate, and performing semi-hardening; [1 7 ] And the hardened material of the item [17], wherein the hardened material contains alumina, which is obtained by hardening the composition of any one of [1 2 ] to [14] The content ratio is 50 to 80% by volume; Π9] is a prepreg obtained by coating or impregnating the composition of any one of [12] to [14] and then performing semi-hardening. BEST MODE FOR CARRYING OUT THE INVENTION The diepoxide of the present invention is of the formula (1)

(In the formula, Ri, R2, r3 and r4 each independently represent a hydrogen atom or a carbon number of 3,000, and R5 represents a group having a carbon number of 2 to 1 Å). -9 - 201124392 Carbon number, preferably A1 R1 'R1 'R2 'R5 races such as ethyl and propyl ' with oxy compound 2-acetate}, 2-propionate}, 2-isoformate} · 2—butyrate}, 2-hexanoate}, 2-ethylbenzoic acid 2-ethylethyl benzo-2-propanol 1-3 alkyl group, for example, methyl, ethyl, propyl and isopropyl Base. R2, R3 and R4 each independently represent a hydrogen atom or a methyl group. R3 and R4 are more preferably a hydrogen atom. The alkyl group having a carbon number of 2 to 1 Å is an alkyl group having 2 to 10 carbon atoms, and a propyl group, an isopropyl group, a butyl group, a hexyl group and an octyl group are preferably an ethyl group. (1) The diepoxy compound shown (hereinafter abbreviated as a ring (i)) may, for example, be a group of _U4_phenylene-bis{4-(2,3·epoxypropoxy)benzene Methyl stretch phenyl-bis(4_(2,3-epoxypropoxy)benzylpropyl phenyl-bis(4-(2,3-epoxypropoxy)phenylphenylene-double {4_(2,3·epoxypropoxy)benzyl-indole, 4-phenylene-bis{4-(2,3-epoxypropoxy)benzyl-1,4_ Phenyl-bis(2,3-epoxypropoxy)-3-methyl ester}, phenyl-, 4-phenylene-bis(2,3-epoxypropoxy)_3_ ate } 'Base_1 4 -phenylene-biguanide 4-(2,3_epoxypropoxy)_3_ -10- 201124392 methyl benzoate}, , epoxy propoxy)-3 - -Epoxypropoxy)-3,5--epoxypropoxy)-3-propenyl-bis{4-( 2,3-epoxy 4-phenylene-double {4- (2,3- 2-propyl-1,4-phenylene-bis{4-(2,3 ethyl benzoate), 2-butyl-1,4-phenylene-double {4 - (2,3 dimethyl benzoate}, and, 2-hexyl-1,4-phenylene-bis{4-(2,3-based benzoate), preferably 2-ethyl· 1,4-extended propoxy)benzoate} and 2-propyl-1; epoxy propoxy Benzoate] (2) Diepoxide (1) is made by

ΟΗ (2) (In the formula, R1, R2, R3 and R4 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R5 represents an alkyl group having 2 to 10 carbon atoms) Hereinafter, it is abbreviated as compound (2)) and formula (3)

(3) (In the formula, X1 represents a halogen atom) The epihalohydrin (hereinafter abbreviated as epihalohydrin (3)) is produced by reacting in the presence of an ammonium salt and an inorganic base. The compound (2) is, for example, 2-ethyl-1,4-phenylene-bis(4-hydroxybenzoate), 2-propyl--11-201124392 1,4_phenylene-bis (4-hydroxybenzoate), 2-isopropyl-I,4-phenylenebis(4-hydroxybenzoate), 2-butyl-1,4-phenylene-bis ( 4-hydroxybenzoate), 2-hexyl-1,4-phenylene-bis(4-hydroxybenzoate), 2-ethyl-1,4-phenylene-bis(4-hydroxyl) -3-methylbenzoate), 2-ethyl-1,4-phenylene-bis(4-hydroxy-3-ethylbenzoate), 2-propyl-1,4-extension Phenyl-bis(4-hydroxy-3-methylbenzoate), 2-propyl-1,4-phenylene-bis('hydroxy-3-ethylbenzoate), 2-butyl phenyl-I,4·phenyl-bis(4-hydroxy-3,5-dimethylbenzoate) and 2-hexyl-I,4·phenyl-bis(4-hydroxy-3-propanyl) Benzoate). X1 in the epihalohydrin (3) represents a halogen atom, and the halogen atom may, for example, be a chlorine atom or a bromine atom, and is preferably a chlorine atom. The epihalohydrin (3) may, for example, be epichlorohydrin or epibromohydrin, and is preferably epichlorohydrin. It is also possible to use two or more epihalohydrin (3). The epihalohydrin (3) is used in an amount of usually 2 to 200 moles, preferably 5 to 150 moles, per mole of the compound 1 mole. The ammonium salt may, for example, be tetramethylammonium chloride, tetraethylammonium chloride, tetrabutylammonium chloride, benzyltrimethylammonium chloride, benzyltriethylammonium chloride or benzyl chloride. Dibutylammonium bromide, tetramethylammonium bromide, tetraethylammonium bromide, tetrabutylammonium bromide, benzyltrimethylammonium bromide, benzyltriethylammonium bromide, narrow four The halogenated 4- toluene of methylammonium, tetraethylammonium iodide, tetrabutylammonium iodide, benzyltributylammonium iodide or the like is preferably a quaternary ammonium bromide, more preferably tetrabutyl bromide. Ammonium and benzyltrimethylammonium bromide. It is also possible to use two or more kinds of ammonium salts. The amount of money salt used is relative to the compound (2) 1 mole, generally -12-201124392 0.0001~1 mole, preferably 0.001~0.5 mole. The inorganic base may, for example, be an alkali metal hydroxide such as lithium hydroxide, sodium hydroxide or potassium hydroxide, or an alkali metal carbonate such as sodium carbonate or potassium carbonate, preferably an alkali metal hydroxide, more preferably hydrogen. Sodium oxide and potassium hydroxide. It is also possible to use two or more inorganic bases. The amount of the inorganic base used is usually from 0.1 to 20 moles, preferably from 0 to 5 to 10 moles, per mole of the compound (2). An inorganic base in the form of a solid such as a granule or a solid base in the form of an aqueous solution having a concentration of from about 1 to about 60% by weight may also be used. The reaction of the compound (2) with the epihalohydrin (3) can be carried out without a solvent or in the presence of a solvent. The solvent may, for example, be methanol, ethanol, propanol-2-propanol, butanol, 2-butanol, ethylene glycol, propylene glycol, 2-pentanol, 3-pentanol, 2-hexanol or 3-hexanol. 2_heptanol, 3-heptanol, 2-octanol, 4-nonanol, 2-dodecanol, 3-methyl-2-butanol' 3,3-dimethyl-2-butanol, 3 -methyl-2-pentanol, 5-methyl-2-hexanol, 4-methyl-3-heptanol, 2-methyl-2-propanol, 2-methyl-2-butanol, 2 , 3-dimethyl-2-butanol, 2-methyl-2-pentanol, 3-methyl-3-pentanol, 3-ethyl-3-pentanol, 2,3-dimethyl- An alcohol solvent such as 3-pentanol, 3-ethyl-2,2-dimethyl-3-pentanol, 2-methyl-2-hexanol or 3,7-dimethyl-3-octanol; Ketone solvent such as methyl ethyl ketone or methyl isobutyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, acetonitrile, benzonitrile, two An aprotic polar solvent such as methyl hydrazine, an ether solvent such as diethyl ether, tert-butyl methyl ether, 1,2 dimethoxyethane, i,4-dioxane, tetrahydrofuran or anisole . It is also possible to use two or more solvents. Among them, it is preferably an alcohol solvent of -13 to 201124392, more preferably a 2-stage alcohol solvent such as 2-propanol or 2-butanol, and 2-methyl-2-propanol, 2-methyl-2-butanol, etc. The tertiary alcohol solvent is particularly preferably 2-methyl-2-propanol. When the reaction is carried out in the presence of a solvent, it is usually used in an amount of from 0.01 to 100 parts by weight, based on 1 part by weight of the compound (2), preferably from 0.1 to 50 parts by weight. The reaction is carried out under normal pressure conditions, under pressurized conditions, or under reduced pressure. Further, the reaction may be carried out in an inert gas atmosphere such as nitrogen or argon. The reaction system is generally carried out by mixing the compound (2), an epihalohydrin (3), an ammonium salt, an inorganic base, and a solvent as needed. The mixing sequence is not limited, but it is preferred to carry out the reaction by mixing the compound (2) with the epihalohydrin (3) and an ammonium salt, and mixing the obtained mixture with an inorganic base to further carry out the reaction. The reaction temperature is usually - 20 ° C to 150 ° C, preferably -10 ° C to 120 ° C. The reaction time is usually from 1 to 150 hours. By mixing the compound (2) and the epihalohydrin (3) with an ammonium salt, the reaction is carried out, and by mixing the obtained mixture with an inorganic base, the reaction is further carried out to make the compound (2) and epihalohydrin ( 3) The temperature of mixing with the ammonium salt is preferably -10 ° C to 150 ° C, more preferably 0 ° C to 120 ° C. The temperature of the mixture obtained by mixing with the inorganic base is preferably -20 ° C to 120 ° C, more preferably - i 〇 ° c ~ 80 ° C. The progress of the reaction can be confirmed by a general analytical method such as liquid chromatography analysis. -14- 201124392

After the completion of the reaction, for example, the reaction mixture is mixed with water and, if necessary, water-insoluble glutinous agent, and then subjected to liquid separation to obtain an organic layer containing the diepoxy compound (1). After the obtained organic layer is washed with water, for example, the insoluble matter is removed by filtration as needed, and concentrated, and the diepoxide compound can be taken out (the diepoxide compound (1) taken out from Ο D can be recrystallized or the like. Further, the purification method is further purified. The diepoxy compound (1) is a compound represented by the compound (2) and the formula (6) (6) (wherein, X2 represents a halogen atom) (hereinafter, abbreviated as the compound (6)). Reaction in the presence of a base to obtain the formula (7)

(In the formula, 'R1, R2', R3 and R4 are the same meanings as defined above) (hereinafter, abbreviated as compound (7)), and the obtained compound (7) can be produced by oxidation with an oxidizing agent. . X2 in the compound (6) represents a halogen atom, and examples of the halogen atom include a chlorine atom and a bromine atom. The compound (6) may, for example, be allyl chloride and allyl bromide. It is also possible to use two or more compounds (4). The compound (6) is used in an amount of 2 to 200 moles, preferably 2 to 100 moles, per mole of the compound (2) 1 mole -15 to 201124392. The base may be an inorganic base or may be an organic base, preferably an inorganic base. The inorganic test may, for example, be an alkali metal hydroxide such as lithium hydroxide, sodium hydroxide or potassium hydroxide, or a metal carbonate such as sodium carbonate or cesium carbonate. An organic test can be exemplified by acridine. Among them, it is preferably an alkali metal carbonate, more preferably sodium carbonate or potassium carbonate. It is also possible to use two or more bases. The amount of the base used is 1 to 10 moles per mole of the compound (2), and is usually 2 to 10 moles. When a liquid organic base is used under the reaction conditions, a solvent is used and a large excess amount of the organic base is used. The reaction of the compound (2) with the compound (6) can be carried out without a solvent, but is preferably carried out in a solvent. The solvent is, for example, the same as the solvent used for the reaction between the compound (2) and the epihalohydrin (3). Further, as described above, when a liquid organic base is used under the reaction conditions, the organic base can also be used as a solvent. The reaction of the compound (2) with the compound (6) is generally carried out by mixing the compound (2) 'compound (6), a base and a solvent as needed, and the order of mixing is not limited. The reaction is carried out under normal pressure, under pressurized conditions, or under reduced pressure. Further, the reaction can also be carried out under an inert gas atmosphere such as nitrogen or argon. The reaction temperature is generally -20 < 〇 ~ 120 ° 〇:, preferably -10 ° 0: ~ 1 〇〇 ° 〇. The progress of the reaction can be confirmed by a general analysis method such as liquid chromatography or the like, and it is preferred to carry out the reaction until the increase in the amount of the compound (7) is not observed. The reaction mixture containing the obtained compound (7) is usually washed directly with water or -16 - 201124392, and then mixed with an oxidizing agent to carry out a reaction of the compound (7) with an oxidizing agent. The oxidizing agent may be an oxidizing agent which converts a carbon-carbon double bond into an epoxy group, and specifically, a peracid such as m-chloroperbenzoic acid may be mentioned. The oxidizing agent is used in an amount of 2 to 20 moles per mole of the compound (7). The reaction of the compound (7) with an oxidizing agent is carried out under normal pressure conditions, under pressurized conditions, or under reduced pressure. Further, the reaction may be carried out under an inert gas atmosphere such as nitrogen or argon. The reaction temperature is generally - 20 ° C to 120 ° C, preferably - l 〇 t ~ l 〇〇 ° C. The reaction time is usually from 0.5 to 72 hours. The progress of the reaction can be confirmed by one of analytical methods such as liquid chromatography. After the end of the reaction, the bicyclooxy compound (1) can be taken out, for example, by concentrating the reaction mixture. The oxidizing agent remaining in the reaction mixture is decomposed and then concentrated. The extracted diepoxy compound (1) can be further purified by a general purification method such as recrystallization. Compound (2) is obtained by making formula (4) R1 R2

R4 R3 (wherein, R1, R2, R3 and R4 are not related to the above meaning) The compound (hereinafter, abbreviated as compound (4)) and formula (5) -17- 201124392

(In the formula, R5 represents the same meaning as described above) The compound (hereinafter, abbreviated as compound (5)) is produced by reacting with an acid. The compound (4) may, for example, be 4-hydroxybenzoic acid, 4-hydroxy; benzoic acid, 4-hydroxy-3-methylbenzoic acid, 4-hydroxy-2-benzoic acid, 4-hydroxy-3-ethyl Benzoic acid, 4-hydroxy-2.isopropanic acid, 4-hydroxy-3-propylbenzoic acid and 4-hydroxy-3,5-dicarboxylic acid, preferably 4-hydroxybenzoic acid and 4-hydroxy- The 3-methyl-safe 1 compound (5) may, for example, be 2-ethylhydroquinone, 2-propylhydrobutylhydroquinone, 2-pentylhydroquinone or 2-octylhydroquinone, which is preferably 2-ethyl and 2-propylhydroquinone. The compound (5) can be produced by a known method such as Synlet, 997', or the like, which is also commercially available, and is also reacted in the presence of lithium chloride (Synlet, 997', etc.) 5) The amount used is generally 1 to 10 moles, preferably 2 to 5 moles per mole of the compound (5). The acid may, for example, be sulfuric acid or p-toluene to extend acid. An acid may also be used. The amount used is preferably 0.001 to 0.3 mol per mol of the compound (4). The reaction of the compound (4) with the compound (5) is preferably carried out in a solvent, and examples of the solvent include hexane, heptane, xinyuan, and the like. a fatty solvent, and an aromatic hydrocarbon solvent such as benzene, toluene, ethylbenzene, xylene, trimethylbenzene or dichlorobenzene. The amount of the solvent used is relative to the presence of -18-ethyl-2-ethylethyl benzo The chlorinated acid can be used as the 2-ethylhydroquinone. The above is generally the presence of the lower hydrocarbon chlorobenzene, and the compound 201124392 (4) 1 part by weight, generally 1 to 200 parts by weight. It is preferably 5 to 100 parts by weight. The reaction of the compound (4) with the compound (5) can be carried out under normal pressure conditions, or under reduced pressure, or under reduced pressure. Further, the reaction can also be carried out under an inert gas atmosphere such as nitrogen or argon. The reaction temperature is generally from 50 ° C to 25 ° C, preferably from 60 t to 200 t:. The reaction time varies depending on the reaction temperature, but is generally 〇 5 to 7 2 hours. The reaction was carried out to generate water, but the reaction was carried out while removing the generated water to the reaction system. The method of removing the generated water to the outside of the reaction system may, for example, be a method using a dehydrating agent such as an azeotropic distillation method or a molecular sieve. Next, the composition containing the diepoxy compound (1) and the curing agent (hereinafter, abbreviated as the composition X) will be described. The composition X may contain two or more kinds of epoxide compounds (1). Further, the composition X may contain two or more kinds of curing agents. The composition X is a solvent and may contain a solvent in addition to the diepoxy compound (1) and a curing agent. Insofar as the preparation is easy, the composition X preferably contains a solvent. Examples of the solvent include a ketone solvent such as methyl ethyl ketone or methyl isobutyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, dimethyl hydrazine or N-methylpyrrolidone, and acetonate. The ester solvent such as an ester or the glycol solvent such as propylene glycol monomethyl ether is preferably a ketone solvent, more preferably methyl isobutyl ketone. The diepoxy compound (1) is excellent in solubility in methyl isobutyl ketone. Further, the epoxy compound is preferred because the solubility of the compound (1) in the above solvent other than methyl isobutyl ketone is also excellent. The hardener is preferably a functional group having at least one functional group which can be hardened with an epoxy group in the diepoxy compound (1 -19-201124392), or a catalyst in a hardening reaction of a diepoxide compound (n) Specifically, for example, the above-mentioned functional group is an amine-based amine curing agent, the aforementioned functional group is a hydroxyl group-based phenol curing agent, and the aforementioned functional group is cured with an acid group represented by -C0-0-C0-. The agent and the hardening catalyst are preferably an amine hardener, a phenol hardener and a hardening catalyst. The amine hardener may, for example, be ethylenediamine, trimethylenediamine, tetramethylenediamine or hexamethylenediamine. An aliphatic polyvalent amine having 2 to 20 carbon atoms such as diethylenetriamine or triethylenetetramine, p-xylenediamine, m-xylenediamine, 1,5-diaminonaphthalene, and m-benzene. Diamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylpropane, 4, 4'-Diaminodiphenyl ether, 1,1-bis(4-aminophenyl)cyclohexane, 4,4'-diaminodiphenylanthracene, bis(4-aminophenyl) Aromatic polyvalent amines such as phenylmethane, 4, 4 An alicyclic polyvalent amine such as diaminodicyclohexane or 1,3-bis(aminomethyl)cyclohexane; and dicyandiamide, wherein it is preferably an aromatic polyvalent amine and Cyanamide, more preferably 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 1,5-diaminonaphthalene, m-phenylenediamine and two Cyanamide: The phenolic hardener may, for example, be a phenol resin, a phenol aralkyl resin (having a pendant phenyl skeleton, a diphenyl structure, etc.), a naphthol aralkyl resin, and a polyoxystyrene resin. For example, an aniline-modified m-cresol resin, a dimethyl ether m-cresol resin, and the like may be a cresol type phenol resin, a phenol novolak resin, a cresol novolak resin, a third butyl phenol novolak resin, and a mercapto group. A phenolic phenol resin such as a phenol novolak resin, and a special phenol resin such as a dicyclopentadiene-modified oxime resin, a decene-modified phenol resin, or a trisphenol-methane resin -20- 201124392. Polyoxystyrene The resin may, for example, be poly(p-oxystyrene). Examples of the acid anhydride hardener include maleic anhydride, phthalic anhydride, pyromellitic anhydride, and trimellitic acid. Anhydride, cis-4 _cyclohexene-, 2 _ dicarboxylic anhydride and 5 _ (2,5-dioxotetrahydrofuranyl)-3_methyl-3_cyclohexene-indole, 2_dicarboxylic anhydride The cerium hardening catalyst may, for example, be 2-methylimidine D, 2-ethyl-4-methylimidazolium, 2-heptadecylamidyl imidazole or benzyldimethylamine. It suffices to select according to the type thereof. When an amine hardener or a phenol hardener is used, the total number of moles of the functional group which can be hardened with the epoxy group in the hardener is relative to the diepoxide compound (1). The epoxy group 1 mole can be used in an amount of 0.5 to 1.5 m, and it is preferably used in an amount of 0.9 to 1.1 mol. The composition X is in addition to the diepoxy compound (1), a hardener and a solvent, as long as it does not cause composition. The desired property of the cured product obtained by the hardening of the object X is lowered, and the ruthenium may contain a compound having other epoxy groups or various additives. Examples of the compound having another epoxy group include a bisphenol A type epoxy compound, an o-cresol type epoxy compound, a bisphenol diglycidyl ether, and a 4,4'-bis (3,4-epoxy group). Buten-1-yloxy)phenyl benzoate, naphthalene diglycidyl ether and α-methylstilbene-4,4'-diglycidyl ether. The additive may, for example, be a hardening accelerator such as triphenylphosphine, 1,8-azobiscyclo[5.4.0]-7-undecene or 2-phenylimidazole; r-propylene oxide propyltrimethoxy a coupling agent such as decane or the like; a coloring agent such as carbon black; a low stress component such as a polyoxyxane oil or a polyoxyxene rubber; a natural wax, a synthetic wax, a higher fat-21 - 201124392 fatty acid or a metal salt thereof, a paraffin wax, etc. Release agent; antioxidant; melt-crushed cerium oxide powder, molten spherical cerium oxide powder, crystalline cerium oxide powder, secondary agglomerated cerium oxide powder, etc.; alumina or transition alumina (r-alumina, θ Alumina such as alumina, 5-aluminum oxide, etc.: titanium white; aluminum hydroxide; talc; earth; mica; and glass fiber. The composition X preferably contains alumina from the viewpoint of improving the heat conductivity of the cured product obtained by curing the composition X. The composition X is preferably a composition containing a bicyclooxy compound (1), a hardener and alumina, and the composition X is preferably a solvent containing the above in terms of ease of preparation. When the composition X contains alumina, the content of the alumina is generally from 75 parts by weight to 95 parts by weight based on 100 parts by weight of the total of the diepoxy compound (1) and the hardener. The composition containing 75 parts by weight or more of the total amount of the epoxy compound (1) and the hardener is oxidized by the tendency of the heat resistance of the cured product obtained by hardening the composition to be improved with respect to 100 parts by weight of the total of the epoxy compound (1) and the curing agent. A composition having an aluminum content of 95 parts by weight or less tends to be easily formed. In the case of alumina, it is preferred that the powdered alumina has a particle diameter (average particle diameter) of 50% of the cumulative volume of the fine particle side derived from the weight cumulative particle size distribution of D50, and more preferably D50 of 2/zm or more and 100 μm. The following aluminas A and D50 are aluminas of a mixture of alumina B having a thickness of 1 #m or more and 10/zm or less and a mixture of alumina C having a D50 of 5 or less and above. Further, the ratio of alumina to alumina in a total of 100% by volume of alumina A and alumina C is preferably 50 to 90% by volume of alumina A, and 5 to 40% by volume of alumina B, and oxidation. Aluminum C is 1 to 3 steroids-22- 201124392%. Such an alumina system can be prepared, for example, by appropriately mixing alumina having various commercially available average particle diameters. Further, the content ratio of the alumina contained in the cured product is preferably 50 to 80% by volume based on 100% by volume of the cured product. The method for producing the cured product obtained by curing the composition X is, for example, a method in which the composition X is directly heated to a specific temperature and cured; and the composition X is heated and melted, injected into a mold or the like, and the mold is further heated to be formed. a method of melting a composition X, injecting the obtained melt into a preheated mold, and hardening; partially hardening the composition X, pulverizing the obtained partially cured product, and filling the obtained powder into a mold, a method of melt-molding the entangled powder; and, if necessary, the composition X is melted in a solvent as needed, and partially hardened while stirring, and the obtained solution is cast, and then the solvent is dried by air drying or the like, and a press machine or the like is required as needed. A method of applying pressure while heating for a specific time. Further, 'the composition X is diluted with a solvent as needed, and then applied or impregnated to the substrate, and then the obtained substrate is heated to semi-harden the diepoxide compound (1) in the substrate, and may be preliminarily produced. Dip body. A plurality of prepregs are laminated and pressed and heated by pressing or the like to obtain a laminate. The base material to be used for the prepreg may be, for example, a woven fabric of an inorganic fiber such as glass fiber or carbon fiber, or a woven fabric or a non-woven fabric of an organic fiber such as a nonwoven fabric or a polyester. The cured product obtained by curing the composition X is excellent in thermal conductivity, and the cured product obtained by curing the composition X containing alumina is more excellent in thermal conductivity. [Embodiment] Hereinafter, the present invention will be specifically described by way of examples and comparative examples, but the present invention is not limited to the examples. Example 1

In an autoclave, 5.0 g of 1,4-cyclohexanedione, 3.93 g of acetaldehyde, 1.89 g of lithium chloride, and 18.8 g of 1,3 -dimethyl-2-imidazolidinone were added at 〇 ° C. , seal the pressure cooker. After the mixture in the autoclave was stirred at 160 ° C for 6 hours, it was cooled to room temperature (about 25 ° C). After 100 mL of ion-exchanged water and 100 mL of ethyl acetate were added to the obtained reaction mixture, extraction was carried out. The obtained organic layer was washed 4 times with a saturated aqueous solution of sodium chloride (100 mL). After the obtained organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was filtered. The obtained filtrate was concentrated to give a crude product. Further, the above operation was carried out three times to obtain a crude product. The obtained crude product was mixed and purified by yttrium oxide gel column chromatography, and further washed with hexane to obtain a compound represented by the above formula (5-1) (hereinafter, abbreviated as a compound (5). -1)) Light gray crystal 9.9 6 g ° -24- 201124392 The crystal was analyzed by gas chromatography analysis and the content of the obtained area percentage was 92.0%, and the content in the crystal was assumed to be 92.9 wt%. The yield of the compound (5 -1 ) in terms of I,4-cyclohexane was 38%. Into a reaction vessel equipped with a Dean Stark apparatus, 8.0 g of 4-hydroxybenzoic acid, 5% of a compound (5-1), 4.0 g of bismuth acid, and about 60 g of xylene were placed. The resulting mixture was mixed for 6 hours to carry out a reaction. The Dean Stark apparatus was used to carry out the reaction and was continuously removed to the outside of the reaction system. The reaction mixture was allowed to cool to room temperature. The precipitated methanol was taken out by filtration and washed with methanol, and then dried under reduced pressure at 50 ° C for 4 hours. 3.90 g of pale gray crystals of the compound of the formula (2-1). After the layer analysis, the percentage of the peak area of the compound represented by the formula (2-1) is the assumed amount of the compound represented by the formula (2-1) in the crystal, and the compound (5-1) is used as a reference. The yield of the formula (2_1) was 37%. 1H-NMR spectral data (δ: ppm, dimethyl sulfoxide 10.54 (br, 2H), 7.80-8.16 (c, 4H) > c, 7H), 2.49 (m, 2H), 1.11 (m, 3H) Example 2 to the chromatographic compound (5 -1 diketone as a base at room temperature, p-toluene is stirred under reflux, the water system is used after the end of the solid, to obtain the above hydrazine in the chromatogram 96.8%. Take: the compound shown by the weight of 96.8, -d6) 6.77-7.32 ( -25- 201124392

In the reaction vessel equipped with the cooling device, 1.5 g of the compound represented by the formula (2_1) obtained in the above Example 1 and tetrabutylammonium bromide 〇.〇 64 g, epichlorohydrin were added at room temperature. 14.7 g and 2-methyl-propanol 9 · 6 8 g » The resulting mixture was stirred at 70 ° C for 1 hour and then cooled to 18 °C. To the obtained mixture, 3.17 g of a 15% by weight aqueous sodium oxychloride solution was slowly added. The resulting mixture was stirred at 18 ° C for 3 hours and then cooled to 〇 ° C. To the obtained reaction mixture, 40 ml of ion-exchanged water was added, and 80 ml of chloroform was added thereto at room temperature. After the resulting mixture was stirred, it was separated into a chloroform layer and an aqueous layer. After washing the chloroform layer three times with ion-exchanged water, the insoluble matter was removed by filtration. The obtained filtrate was concentrated to give a crude product. The obtained crude product, 8 ml of toluene and 17 ml of 2-propanol were placed in a reaction vessel equipped with a cooling apparatus, and the resulting mixture was stirred at 70 ° C for 1 hour. The obtained mixture was cooled to room temperature, and the precipitated solid was taken out by filtration, and the taken solid was washed with 2-propanol, followed by drying to obtain white crystals of the compound represented by the above formula (1-1). 1.16 g After the obtained crystal was subjected to liquid chromatography, the peak area percentage of the compound represented by the formula (1-1) in the chromatogram was 96.5%. The content of the compound represented by the formula (1-1) in the crystal is assumed to be 96.5 to -26 to 201124392% by weight, and the compound represented by the formula (2-1) is used as a reference formula (1 - 1). The yield of the compound was 59%. W-NMR spectral data (<5: ppm, CDC13) 8.11-8.25 (c > 4H ) , 6 · 9 5 - 7 · 2 5 ( c, 7 Η ) ' 4.28-

4.45 ( c,2H ) , 3.97-4.10 ( c,2H ) , 3.35-3.57 ( c,2H ), 2.95-3 _00 ( c,2H ) > 2.7 5-2.84 ( c > 2H ) , 2.62 ( q > 2H ) , 1 _22 ( t, 3H ) Example 3

0 C3H7 c3h7_ h〇-〇-〇h (5-2)

(5-2)

(2-2) In a reaction vessel equipped with a cooling device, add at room temperature, 14.0 g of 4-cyclohexanedione, 13.2 g of propionaldehyde, 6.43 g of lithium chloride, and 1,3-dimethyl -2-imidazolidinone 64.0 g. The resulting mixture was stirred at 160 ° C for 8 hours and then cooled to room temperature. After 300 ml of ion-exchanged water and 300 ml of ethyl acetate were added to the obtained reaction mixture, extraction was carried out. The obtained organic layer was washed 4 times with a saturated aqueous solution of sodium chloride (300 mL). After the obtained organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was filtered. The obtained filtrate was concentrated to give a crude product. The obtained crude product was purified by yttrium oxide gel column chromatography, and then washed with hexane to obtain a compound represented by the above formula (5-2) (hereinafter, abbreviated as a compound (5- 2)) Light gray crystals 11.5 g. -27- 201124392 Analysis of the crystal by gas chromatography analysis 'After calculating the area percentage of the obtained chromatogram, it is 97.1%, and if the content of the compound (5-2) in the crystal is assumed to be 97.1% by weight '1 The yield of the compound (5-2) having 4 -cyclohexanone as a reference is °. In the reaction vessel equipped with the Dean Stark apparatus, 4.54 g of 4-hydroxybenzoic acid is added at room temperature (about 25 t). 2.50 g of the compound (5-2), ruthenium 31.p of p-toluenesulfonate and about 4 g of xylene. The resulting mixture was stirred under reflux for 19 hours to carry out a reaction. The water produced by the reaction was continuously removed to the outside of the reaction system using a Dean Stark apparatus. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. The precipitated solid was taken out by filtration, washed with 3.0 ml of 2-propanol at 5 ° C, and then dried under reduced pressure at 50 ° C for 4 hours to obtain a pale gray crystal of the compound represented by the above formula (2-2). 3.5 1 g. After the obtained crystal was subjected to liquid chromatography, the peak area percentage of the compound represented by the formula (2-2) in the chromatography was 97.5%. The content of the compound represented by the formula (2-2) in the crystal was assumed to be 97.5 wt%, and the yield of the compound represented by the formula (2-2) based on the compound (5-2) was 55%. 'H-NMR spectral data (δ: ppm, dimethyl hydrazine-d6) 10.54 (br, 2H), 7.90-8.10 (c, 4H), 6.85-7.32 (c, 7H), 2.37-2.60 (m, 2H) , 1.54 (m, 2H), 0.82 ( t - 3H ) Example 4 -28- 201124392

qC3H7 ο (1-2)

In the reaction vessel equipped with the cooling device, the compound represented by the formula (2-2) obtained in the above Example 3 was added at room temperature. 50 g, tetrabutylammonium bromide, ruthenium 62 g, epichlorohydrin 14.2 g of alcohol and 9.32 g of 2-methyl-propanol. The resulting mixture was stirred at 70 ° C for 9 hours and then cooled to 18 ° C. To the obtained mixture, a suspension of 1 5 wt% aqueous sodium hydroxide was slowly added in an amount of 3 · 07 g. The resulting mixture was stirred at 18 ° C for 3 hours and then cooled to 〇 ° C. To the obtained reaction mixture, 23 ml of a 10% by weight aqueous ammonium chloride solution was added, and 40 ml of ion-exchanged water and 80 ml of chloroform were added thereto at room temperature. After the resulting mixture was stirred, it was separated into a chloroform layer and an aqueous layer. After washing the chloroform layer three times with ion-exchanged water, the insoluble matter was removed by filtration. The obtained filtrate was concentrated to give a crude product. The obtained crude product, 4 ml of toluene and 18 ml of 2-propanol were placed in a reaction vessel equipped with a cooling apparatus, and the resulting mixture was stirred at 70 ° C for 1 hour. The resulting mixture was allowed to cool to room temperature and further kept at -10 ° C overnight. Then, the precipitated solid was taken out by filtration, and the taken solid was washed with 2-propanol at 5 ° C, and then dried to obtain a white crystal of the compound represented by the above formula (1-2). 6 g. After the obtained crystal was subjected to liquid chromatography, the peak area percentage of the compound represented by the formula (I-2) in the chromatography was 91.1%. The content of the compound represented by the formula (1-2) in the crystal is assumed to be 91.1% by weight. The compound represented by the formula (2-2) is represented by the formula (1-2). The yield of the compound was 76%. W-NMR spectral data (<5: ppm, CDC13) 8.08-8.26 (c '4H) ' 6.96-7.28 (c,7H) * 4.28-

4.48 ( c ' 2H ) ' 3.93-4.12 ( c ' 2H) , 3.38-3.49 ( c, 2H ) &gt; 2.8 8 -3.00 ( c - 2H ) ' 2.7 4 - 2 · 8 6 ( c, 2 H ) , 2.56 ( m , 2H ) , 1.65 ( m, 2H ) , 0.92 ( t , 3H ) <Measurement of Solubility> The compound represented by formula (1 _ 1 ) obtained in Example 2 was obtained and the following Formula (A)

The solubility of methyl isobutyl ketone in the compounds shown at 4 ° C and 65 ° C (compound (g) xioo / [compound (g) + methyl isobutyl ketone (g)], % by weight ). The results are not shown in Table 1. From Table 1, it is understood that the solubility of the compound represented by the formula (1-1) of the bis(epoxy compound) of the present invention is more than 3 times higher than that of the compound represented by the formula (A). β -30 - 201124392

[Table 1J Solubility &lt;% by weight) 40 ° C 65. . Compound represented by formula (1-1) 3.59 13.84 Compound represented by formula (A) 1.10 2.00 Example 5

Mixing the compound of the formula (2-1) obtained in the first embodiment with potassium carbonate and allyl bromide and acetone, and stirring the obtained mixture at a specific temperature to obtain the above formula (7·1) The compound shown. The compound represented by the above formula (1-1) can be obtained by mixing the compound obtained by the formula (7-1), m-chlorobenzoic acid and chloroform at a specific temperature. Example 6 20 parts by weight of a compound represented by the formula (1-1) and 20 parts by weight of 4,4'-diaminodiphenylmethane (manufactured by Wako Pure Chemical Industries, Ltd.) as a curing agent were mixed. The solvent was N,N-dimethylformamide to give a solution in the form of a solution. 201124392 The obtained composition was concentrated by a centrifugal concentrating device to obtain a powdery composition. The obtained powdery composition was poured on an aluminum pan (Aluminum Pan). The aluminum disk filled with the composition was heated by a differential scanning calorimeter (DSC Q2000 manufactured by Sigma Instruments Co., Ltd.) to obtain a cured product (hardening condition: heating at 140 V for 20 minutes in a nitrogen atmosphere, heating at 1 / min To 180 ° C, further heated at 200 ° C for 30 minutes). The obtained cured product was cooled to 20 ° C, and the glass transition point of the cured product was measured by a differential scanning measurement measuring apparatus (temperature rising rate: 20 ° C /min) to be 144 ° C. Example 7 In addition to the use of 16 parts by weight of substituted 4,4'-diaminodiphenylmethane of 20 parts by weight of I,5-diaminonaphthalene (manufactured by Wako Pure Chemical Industries, Ltd.), the other system was used. The same procedure as in Example 6 was carried out to obtain a solution-like composition. The obtained solution-like composition was concentrated in a centrifugal concentrating device to obtain a powdery composition. The obtained powdery composition was heated in the same manner as in Example 6 to obtain a cured product. The glass transition point of the hardened material is 1 5 1 °C. Example 8 In Example 6, except for using cis_4·cyclohexene-1,2-dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 31 parts by weight of substituted 4,4'-diaminodiphenylmethane was used. 20 parts by weight, and 2.6 parts by weight of 2-phenylimidazole as a curing accelerator were further added, and the same procedure as in Example 6 was carried out, and -32-201124392 was obtained as a solution-like composition. The obtained solution-like composition was concentrated by a centrifugal concentration device to obtain a powdery composition. The obtained powdery composition was heated in the same manner as in Example 6 to obtain a cured product. The glass transition point of the hardened material was 105 °C. Example 9 In Example 6, except that 5-(2,5-dioxatetrahydrofuranyl)·3-methyl-3-cyclohexene-I,2-dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used. 27 parts by weight of the substituted 4,4'-diaminodiphenylmethane 20 parts by weight, and 2.5 parts by weight of 2-phenylimidazole as a curing accelerator were further added, and the same procedure as in Example 6 was carried out to obtain a solution. Composition. The obtained solution-like composition was concentrated by a centrifugal concentrator to obtain a powdery composition. The obtained powdery composition was heated in the same manner as in Example 6 to obtain a cured product. The glass transition point of the hardened material is 1 2 7 . (Example 1) In Example 6, except for using a phenol novolac curing agent "MEH-7851H" (manufactured by Mingwa Kasei Co., Ltd.), 84 parts by weight of substituted 4,4, dimethylaminodiphenylmethane 20 parts by weight In the same manner as in Example 6, except that 3 to 7 parts by weight of triphenylphosphine as a hardening accelerator was added, a solution having a solution-like composition was obtained. The obtained solution-like composition was subjected to a centrifugal concentration device. The mixture was concentrated to obtain a powdery composition, and the obtained powdery composition was heated in the same manner as in Example 6 to obtain a cured product. The glass transition point of the cured product was 1 〇3. (: -33-201124392 Example 1 1 In addition to the use of dicyandiamide (manufactured by Wako Pure Chemical Industries, Ltd.), 10 parts by weight of a substituted 4,4,-diaminodiphenylmethane 20 parts by weight, in addition, as a hardening accelerator The same procedure as in Example 6 was carried out except that 2.2 parts by weight of diphenylimidazole was used, and a solution-like composition was obtained. The obtained solution-like composition was concentrated by a centrifugal concentration device to obtain a powdery composition. Make income The powdery composition was heated in the same manner as in Example 6 to obtain a cured product. The glass transition point of the cured product was 146 ° C. Example 1 2 100 parts by weight of the compound of the formula (1-1) was mixed, 16 parts by weight of 1,5-diaminonaphthalene (Wako Pure Chemical Industries, Ltd.) and 1071 parts by weight of alumina powder as a hardener (α-alumina powder manufactured by Sumitomo Chemical Co., Ltd.; laser diffraction method) Alumina powder having an average particle diameter (D50) of 18 μm, alumina powder B1 having an average particle diameter (D50) of m, and alumina powder Cl having an average particle diameter (D50) of 0.4 μm, weight ratio (Alumina powder A1/alumina powder B1/alumina powder Cl)=793/15 0/129, volume ratio (alumina powder A1/alumina powder B1/alumina powder C1) = 74/14/12 for mixing And 370 parts by weight of methyl isobutyl ketone as a solvent and 60 parts by weight of N,N-dimethylformamide to prepare a solution-like composition. In polyethylene terephthalate (PET) On the film, the composition prepared by coating with a thin coater-34-201124392 becomes a thickness of 305 // m. The PET film was dried at room temperature for 1 hour, and further dried at 120 ° C for 5 minutes, and then the PET film was peeled off to obtain a sheet. The obtained sheet was stuck in an aluminum foil having a thickness of 40 // m, and subjected to vacuum press forming (stamping conditions). : Vacuum degree: lkPa, 6 MPa, 60 minutes from 1 to 15 °C to 180 °C.) Stripped aluminum foil to obtain a flaky solidified material with a thickness of 3 72 ym. Xenon Flash analyzer Nano fl The ash LFA 447 type has a thermal conductivity of 9 · 1 W / ( m · K ). The compound represented by the formula (1-1) and the 1,5-diaminonaphthalene are used to harden the composition containing no alumina powder, and the obtained cured product has a density of 1 · 2 g / cm 3 , alumina The density of the powder was 3.9 7 g/cm3, and the content ratio of the alumina powder in the obtained cured product was calculated to be 74% by volume. (Example 1) 16 parts by weight of 1,5-diaminonaphthalene (manufactured by Wako Pure Chemical Industries, Ltd.) as a curing agent by mixing 100 parts by weight of the compound represented by the formula (1-1) A solvent-like composition of 3 70 parts by weight of methyl isobutyl ketone and 60 parts by weight of N,N-dimethylformamide was obtained. The obtained composition was impregnated with a thick glass. After 2 mm of the glass fiber cloth, it was dried by heating to obtain a prepreg. Four sheets of the prepreg obtained were stacked and press-formed at a temperature of 175 ° C and a pressure of 4 MPa for 90 minutes to obtain a laminate. Example 1 4 - 35 - 201124392 A mixture of 100 parts by weight of the compound represented by the formula (1-1), and 1,5-diaminonaphthalene (Wako Pure Chemical Industries, Ltd.) as a curing agent, 16 parts by weight, oxidized 567 parts by weight of aluminum powder (α-alumina powder manufactured by Sumitomo Chemical Co., Ltd.: alumina powder having an average particle diameter (D50) of 18 // m), 160 parts by weight of methyl isobutyl ketone as a solvent, and N, 60 parts by weight of N-dimethylformamide, and a composition in the form of a solution was prepared. On a polyethylene terephthalate (PET) film, the composition prepared by coating with a thin coater became a thickness of 3 50 # m. The PET film coated with the composition was dried at room temperature for 1 hour, and further dried at 120 ° C for 10 minutes, and then the PET film was peeled off to obtain a sheet. The obtained sheet was smashed with an aluminum foil having a thickness of 40 Mm, and subjected to vacuum press forming (pressing temperature: 140 ° C, vacuum degree: 1 kPa, pressing pressure: 6 MPa). Thereafter, the press temperature was raised to 180 ° C for 40 minutes. The aluminum foil was peeled off to obtain a flaky cured product having a thickness of 3 3 5 y m. Using the NTEZSCH 氙 flash analyzer nanoflash LFA447, the heat transfer rate of the cured product was measured to be 5. 1 W/( m . K ). The compound represented by the formula (1-1) and the 1,5-diaminonaphthalene are contained, and the composition containing no alumina powder is hardened, and the obtained cured product has a density of 1.2 g/cm 3 and an alumina powder. The density was 3.97 g/cm3, and the content ratio of the alumina powder in the obtained cured product was calculated, and the content ratio of the alumina powder in the cured product was 60% by volume. In the examples 6 to 11, except that the compound represented by the formula (1-2) was used instead of the compound represented by the formula (1-1), the same procedure as in the examples 6 to 11 was carried out. A composition in the form of a solution, a composition of -36-201124392 in a powder form, and a cured product were obtained. In the examples I2 to 14, except that the compound represented by the formula (i_2) was used instead of the compound represented by the formula (1-1), the same was carried out in the same manner as in the examples 12 to 14. A composition containing alumina powder and a cured product were obtained. Industrial Applicability The diepoxy compound of the present invention is excellent in solubility in methyl isobutyl ketone. The cured product obtained by curing the composition containing the diepoxide has high thermal conductivity. -37-

Claims (1)

201124392 VII, the scope of application for patents: 1. A diepoxide compound, which is based on formula (1) R4 R3 R3 R4 (wherein R1, R2, R3 and R4 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R5 represents an alkyl group having 2 to 10 carbon atoms). 2. A method for producing a diepoxide compound represented by the following formula (1) ) its characteristics are based on equation (2) a hydroxy group of 1 to 3, R5 represents an alkyl group having 2 to 10 carbon atoms, and a dihydroxy compound represented by the formula (3) (wherein X1 represents a halogen atom) (3) -38 to 201124392 The epihalohydrin is reacted in the presence of an ammonium salt and an inorganic base. 3. The production method of claim 2, wherein the reaction is carried out in the presence of an alcohol solvent. The manufacturing method of claim 3, wherein the alcohol solvent is at least one selected from the group consisting of a secondary alcohol solvent and a tertiary alcohol solvent. 5. The method of claim 2, wherein the reaction is carried out by mixing a dihydroxy compound represented by the formula (2) with an epihalohydrin and an ammonium salt represented by the formula (3). The resulting mixture is mixed with an inorganic base and further reacted. 6. The method of manufacture of claim 2, wherein the inorganic base is sodium hydroxide or potassium hydroxide. 7 _ a kind of dihydroxy compound' which is based on formula (2) (wherein 'R, R2, R3 and Rj each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R5 means an alkyl group having 2 to 10 carbon atoms). - Method for producing di-based compound represented by the following formula S -39- 201124392 (wherein R1, R2, R3, R4, and r5 represent the same meaning as described above), and the characteristics are expressed by formula (4) a dihydroxy compound represented by an alkyl group of 1 to 3) and a formula (5) (5) (wherein R5 represents an alkyl group having 2 to 10 carbon atoms) The compound shown is reacted in the presence of an acid. 9- a composition' 0 (1) The alkyl group of 1 to 3 'R5 represents a bicyclic oxygen compound represented by an alkyl group having 2 to 10 carbon atoms and a curing agent. 10. The composition of claim 9, wherein the hardener is at least one hardener selected from the group consisting of an amine hardener, a phenol hardener, and an acid anhydride hardener. 1 1 · The composition of the first aspect of the patent application, wherein the amine hardening -40 - 201124392 agent is 4,4 '-diaminodiphenylmethane, 4,4,-diaminodiphenyl The at least one selected from the group consisting of alkane, 1,5-diaminonaphthalene and p-phenylenediamine. The composition of claim 9, which further comprises alumina. 1 3 . The composition of claim 12, wherein the total amount of the bismuth compound and the hardener represented by the formula (1) is 1 part by weight, and the content of the oxidized salt is 7 parts by weight to 9 5 parts by weight. 1 4 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ a mixture of alumina b of 10/m or less and alumina c of D50 of 0.01/im or more and 5/zm or less, and a total of 1% by volume of alumina A and alumina B and alumina C The ratio of each alumina is 50 to 90% by volume of alumina A, 5 to 40% by volume of alumina B, and 1 to 30% by volume of alumina C. A cured product obtained by hardening a composition according to any one of claims 9 to 11. A prepreg obtained by subjecting a composition according to any one of claims 9 to 11 to a substrate after semi-hardening. A cured product obtained by hardening a composition according to any one of claims 1 to 4 of the patent application. 18. The cured product of claim 17, wherein the content of the alumina contained in the hardened material is 50 to 80% by volume. -41 - 201124392 1 9. A prepreg obtained by coating or impregnating a composition according to any one of claims 1 to 14 to a semi-hardening. -42- 201124392 Four designated representative drawings: (1) The representative representative of the case is: No (2) The symbol of the representative figure is simple: No 201124392 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention. :no