JP3403590B2 - Sulfur-containing epoxy compound and sulfur-containing epoxy resin - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel sulfur-containing epoxy compound, a method for producing the same, a resin obtained by using the sulfur-containing epoxy compound, and a method for producing the same.

The epoxy compound of the present invention is a synthetic resin raw material,
It has a wide range of uses such as plastic lens resin raw materials, medical and agricultural chemical raw materials and intermediates, epoxy resin coating raw materials, adhesive raw materials, and semiconductor sealing raw materials.

[0003]

2. Description of the Related Art Polymethyl methacrylate resin, polycarbonate resin, diethylene glycol bisallyl carbonate resin and the like have been conventionally used as resins for optical applications.

Of these, the most widely used for plastic lens applications is diethylene glycol bisallyl carbonate resin. This resin has a low refractive index of 1.50, and when used in a lens, the edge thickness, The central thickness was increased, resulting in deterioration of appearance and weight.

Therefore, a material having a higher refractive index and improving the drawbacks of the diethylene glycol bisallyl carbonate resin is required, and Japanese Patent Publication No. 5-4404 discloses a resin in which halogen is introduced into an aromatic ring. ing. However, although this resin has a high refractive index of 1.60, it has a drawback that the specific gravity becomes high, 1.37.
Moreover, these resins are not always satisfactory in terms of physical properties such as heat resistance and impact resistance.

A thiourethane resin formed by polymerizing an isocyanate compound and a thiol compound has a high refractive index, but further improvement is required in terms of balance with the Abbe number.

By the way, generally, epoxy resins have excellent properties in terms of impact resistance. For optical applications, a method for producing a lens by casting polymerization of an epoxy compound having two or more epoxy groups in one molecule and a thiol compound having two or more thiol groups in one molecule is an international method. It is disclosed in publication number WO 89/10575. This lens has a high refractive index and low dispersion, but is not satisfactory in terms of impact resistance. That is, it has been delayed to apply and put into practical use the excellent properties of epoxy resin in terms of both refractive index and impact resistance.

[0008]

In order to solve the above problems, the present invention provides a novel epoxy compound which gives a resin having a high refractive index, a low dispersion and an excellent impact resistance, as well as a polymerizing agent for the epoxy compound or another curing agent. It is intended to provide a resin obtained by copolymerizing with.

[0009]

Means for Solving the Problems The inventors of the present invention have made extensive studies to solve the above problems. As a result, a novel sulfur-containing epoxy compound was found and the present invention was achieved.

That is, the present invention has the formula (I)

[Chemical 4] And a method of producing the same, and a compound represented by formula (I) or a compound represented by formula (I) and one or more curing agents are polymerized in the presence of a polymerization catalyst. The present invention relates to a method for producing a characteristic resin and the resin.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by the formula (I) is a compound represented by the formula (II) and bismercaptoethylsulfide.

[Chemical 5] (In the formula, X represents Br or Cl.) The reaction is carried out in the presence of an inorganic base in bismercaptoethylsulfide and an organic solvent inert to the compound of the formula (II) or in water or a mixed solvent of the organic solvent and water. It is obtained by

The organic solvent used here is an aromatic hydrocarbon compound such as benzene, toluene, xylene, or methanol, ethanol, n-propanol, i.
-Propanol, n-butanol, i-butanol, s
Examples thereof include lower alcohols such as ec-butanol, ethers such as tetrahydrofuran and diethyl ether, and aliphatic chlorides such as dichloromethane, chloroform, carbon tetrachloride, and the like, and one kind or a mixture of two or more kinds can be used. Preferably benzene, toluene,
Examples include xylene, methanol and ethanol.

Examples of inorganic bases used next include sodium hydroxide, potassium hydroxide, calcium hydroxide,
Alkali metal hydroxides and alkaline earth metal hydroxides such as barium hydroxide, sodium carbonate, potassium carbonate, calcium carbonate, alkali metal carbonates and alkaline earth metal carbonates such as barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or Metal alkoxides such as sodium methoxide and sodium ethoxide are preferred, and sodium hydroxide and potassium hydroxide are preferred.

The reaction temperature is -20 ° C to the reflux temperature of the reaction solvent, preferably 0 ° C to 25 ° C.

The reaction time varies depending on the temperature, but is usually 10
Minutes to 100 hours. The pressure during the reaction is atmospheric pressure to 10 at
m, preferably near normal pressure. In addition, a quaternary ammonium salt can be added to accelerate the reaction. Examples of the quaternary ammonium salt used include tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium hydroxide, tetraethylammonium bromide and tetra-n bromide.
-Butylammonium, tetrabutylammonium hydrogensulfate, tetra-n-butylammonium iodide, triethylbenzylammonium chloride, trimethylphenylammonium bromide and the like.

Next, regarding the amount of each of the raw materials, the inorganic base and the quaternary ammonium salt used, the amount of the compound of the formula (II) is 1.0 with respect to 1.0 mol of bismercaptoethyl sulfide.
Mol to 10.0 mol. Preferably from 1.80 mol
It is 2.60 mol. Inorganic base is added in an amount of 1.0 mol to 10.0 with respect to 1.0 mol of bismercaptoethyl sulfide.
Use mol. It is preferably 1.80 mol to 5.00 mol. The amount of the quaternary ammonium salt is 0.001 mol-based on 1.0 mol of bismercaptoethylsulfide.
Use 1.0 mol. Preferably 0.01 mol-0.10
It is a mole.

As a method for obtaining a reaction product from the reaction solution obtained by the above method, there are an extraction method, a desolvation method and the like. The solvent used in the extraction method here is ethyl acetate, acetic acid-n-
Butyl, isobutyl acetate, methyl ethyl ketone, diethyl ether, diisopropyl ether, carbon tetrachloride, methylene chloride, chloroform, benzene, toluene, xylene, n-butyl alcohol, t-butyl alcohol,
An organic solvent used in the reaction such as n-amyl alcohol.

As a method for purifying the compound represented by the formula (I) obtained by the above method, a distillation method, a column purification method, a water washing method, a pickling method and the like can be used.

Further, in the present invention, a compound represented by the formula (III) is prepared from the compound represented by the formula (II) and bismercaptoethylsulfide.

[Chemical 6] (In the formula, X represents Br or Cl.) After the compound represented by formula (I) is isolated, the compound represented by formula (I) may be produced by reacting with an inorganic base without isolation. it can.

The compound represented by the formula (III) is a compound represented by the formula (II) with bismercaptoethylsulfide, and an organic solvent inert to the bismercaptoethylsulfide and the compound represented by the formula (II) or water or an organic compound. It can be obtained by reacting in a mixed solvent of a solvent and water in the presence of an inorganic base.

The organic solvent used here is an aromatic hydrocarbon compound such as benzene, toluene, xylene, or methanol, ethanol, n-propanol, i.
-Propanol, n-butanol, i-butanol, s
Examples thereof include lower alcohols such as ec-butanol, ethers such as tetrahydrofuran and diethyl ether, and aliphatic chlorides such as dichloromethane, chloroform, carbon tetrachloride, and the like, and one kind or a mixture of two or more kinds can be used. Preferably benzene, toluene,
Examples include xylene, methanol and ethanol.

Examples of inorganic bases used next include sodium hydroxide, potassium hydroxide, calcium hydroxide,
Alkali metal hydroxides and alkaline earth metal hydroxides such as barium hydroxide, sodium carbonate, potassium carbonate, calcium carbonate, alkali metal carbonates and alkaline earth metal carbonates such as barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or Metal alkoxides such as sodium methoxide and sodium ethoxide are preferred, and sodium hydroxide and potassium hydroxide are preferred.

The reaction temperature is -20 ° C to the reflux temperature of the reaction solvent, preferably 0 ° C to 25 ° C.

The reaction time varies depending on the temperature, but is usually 10
Minutes to 100 hours. The pressure during the reaction is atmospheric pressure to 10 at
m, preferably near normal pressure. In addition, a quaternary ammonium salt can be added to accelerate the reaction. Examples of the quaternary ammonium salt used include tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium hydroxide, tetraethylammonium bromide and tetra-n bromide.
-Butylammonium, tetrabutylammonium hydrogensulfate, tetra-n-butylammonium iodide, triethylbenzylammonium chloride, trimethylphenylammonium bromide and the like.

Next, regarding the amount of each raw material, the inorganic base and the quaternary ammonium salt used, 1.0 mol of the compound of the formula (II) is used per 1.0 mol of bismercaptoethyl sulfide.
Mol to 10.0 mol. Preferably from 1.80 mol
It is 2.60 mol. The amount of the inorganic base used is 0.001 mol to 2.0 mol with respect to 1.0 mol of bismercaptoethyl sulfide. Preferably 0.01 mol to 0.1
It is 0 mol. The amount of the quaternary ammonium salt is 0.001 with respect to 1.0 mol of bismercaptoethyl sulfide.
Mol to 1.0 mol is used. Preferably from 0.01 mol
It is 0.10 mol.

As a method for obtaining a reaction product from the reaction solution obtained by the above method, there are an extraction method, a desolvation method and the like. The solvent used in the extraction method here is ethyl acetate, acetic acid-n-
Butyl, isobutyl acetate, methyl ethyl ketone, diethyl ether, diisopropyl ether, carbon tetrachloride, methylene chloride, chloroform, benzene, toluene, xylene, n-butyl alcohol, t-butyl alcohol,
An organic solvent used in the reaction such as n-amyl alcohol.

As a method for purifying the compound represented by the formula (III) obtained by the above method, a distillation method, a column purification method, a water washing method, a pickling method and the like can be used.

Next, the compound represented by the formula (I) has the formula (II
It can also be obtained by a method of reacting the compound represented by I) with an inorganic base in an organic solvent inert to the formula (III) or water or a mixed solvent of an organic solvent and water. In that case, the compound of the formula (III) used may be either isolated or not isolated.

The organic solvent used here is an aromatic hydrocarbon compound such as benzene, toluene, xylene, or methanol, ethanol, n-propanol, i.
-Propanol, n-butanol, i-butanol, s
Examples thereof include lower alcohols such as ec-butanol, ethers such as tetrahydrofuran and diethyl ether, and aliphatic chlorides such as dichloromethane, chloroform, carbon tetrachloride, and the like, and one kind or a mixture of two or more kinds can be used. Preferably benzene, toluene,
Examples include xylene, methanol and ethanol.

Examples of inorganic bases used next include sodium hydroxide, potassium hydroxide, calcium hydroxide,
Alkali metal hydroxides and alkaline earth metal hydroxides such as barium hydroxide, sodium carbonate, potassium carbonate, calcium carbonate, alkali metal carbonates and alkaline earth metal carbonates such as barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or Metal alkoxides such as sodium methoxide and sodium ethoxide are preferred, and sodium hydroxide and potassium hydroxide are preferred.

The reaction temperature is -20 ° C to the reflux temperature of the reaction solvent, preferably 0 ° C to 25 ° C.

The reaction time varies depending on the temperature, but is usually 10
Minutes to 100 hours. The pressure during the reaction is atmospheric pressure to 10 at
m, preferably near normal pressure. In addition, a quaternary ammonium salt can be added to accelerate the reaction. Examples of the quaternary ammonium salt used include tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium hydroxide, tetraethylammonium bromide and tetra-n bromide.
-Butylammonium, tetrabutylammonium hydrogensulfate, tetra-n-butylammonium iodide, triethylbenzylammonium chloride, trimethylphenylammonium bromide and the like.

Next, regarding the amount of each inorganic base and quaternary ammonium salt used, 1.0 mol to 10.0 mol of the inorganic base is used with respect to 1.0 mol of the compound of the formula (III). It is preferably 1.80 mol to 5.00 mol. The amount of quaternary ammonium salt is 1.
0.001 to 1.0 mol is used with respect to 0 mol.
It is preferably 0.01 mol to 0.10 mol.

As a method for obtaining a reaction product from the reaction solution obtained by the above method, there are an extraction method, a desolvation method and the like. The solvent used in the extraction method here is ethyl acetate, acetic acid-n-
Butyl, isobutyl acetate, methyl ethyl ketone, diethyl ether, diisopropyl ether, carbon tetrachloride, methylene chloride, chloroform, benzene, toluene, xylene, n-butyl alcohol, t-butyl alcohol,
An organic solvent used in the reaction such as n-amyl alcohol.

Further, the method for purifying the obtained compound represented by the formula (I) is as follows: distillation method, column purification method, water washing method,
A pickling method or the like can be used.

Next, the sulfur-containing epoxy resin of the present invention can be obtained by subjecting the compound represented by the formula (I) to heat treatment, if necessary, in the presence of a polymerization catalyst.

Further, the compound represented by the formula (I) and another type of epoxy compound may be subjected to heat treatment, if necessary, in the presence of a polymerization catalyst to obtain a resin.

Other types of epoxy compounds include aliphatic compounds such as bisphenol type epoxy compounds, ethylene glycol modified bisphenol type epoxy compounds, alicic diepoxy acetals, alicic diepoxy adipates, alicic diepoxy carboxylates, and vinylcyclohexene diepoxides. Glycidyl ester epoxy compounds such as epoxy compounds, diglycidyl phthalate, diglycidyl tetrahydrophthalate, diglycidyl hexahydrophthalate, dimethylglycidyl phthalate, dimethylglycidyl hexahydrophthalate.

Tetraglycidyldiaminodiphenylmethane, triglycidyl-paraaminophenol, triglycidyl-metaaminophenol, diglycidylaniline, diglycidyl toluidine, tetraglycidyl metaxylenediamine, diglycidyl tribromaniline, tetraglycidyl bisaminomethylcyclohexane, etc. Examples thereof include glycidyl amine compounds and heterocyclic epoxy compounds such as triglycidyl isocyanate.

The polymerization catalyst to be used is 1,8-diazabicyclo [5,4,0] -7-undecene, triethylenediamine, N, N-dimethylpiperazine, pyridine, picoline, triethylamine and other tertiary amines, and trifluoride. Examples thereof include boron fluoride, Lewis acids such as trifluoromethanesulfonic acid, acids, and salts thereof.

During the polymerization, heating can be carried out if necessary. The heating temperature is 25 ° C to 170 ° C, preferably 25 ° C to 130 ° C. Heating time is 10 minutes to 100
The time is preferably 10 minutes to 5 hours.

Copolymerization with other curing agents is also possible. As a curing agent, ethylenediamine, diethylenetriamine, triethylenetetramineisophoronediamine, aliphatic amines such as xylylenediamine, metaphenylenediamine, diaminodiphenylmethane, aromatic amines such as diaminodiphenylsulfone, dodecenyl succinic anhydride, polyadipic anhydride, Aliphatic acid anhydrides such as polyazelaic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, alicyclic acid anhydrides such as hexahydrophthalic anhydride, phthalic anhydride, trimellitic anhydride, pyropyrolic anhydride Aromatic acid anhydrides such as mellitic acid, Het anhydride, Halogen acid anhydrides such as tetrabromophthalic anhydride, Basic active hydrogen compounds such as dicyandiamide, Imidazole compounds, Polymercaptan curing agents, Tri Isocyanate compounds such as emissions diisocyanate, and the like.

Further, if necessary, an internal mold release agent, a light stabilizer, an ultraviolet absorber, an antioxidant, a dyeing agent, a filler and the like can be added.

When the lens is produced according to the present invention, the cast polymerization method is usually suitable. Specifically, the sulfur-containing epoxy compound represented by the formula (I) or the compound represented by the formula (I) is mixed with one or more curing agents by adding a polymerization catalyst, and the mixed solution is mixed if necessary. After defoaming by a suitable method, it is poured into a mold and polymerized at a temperature of 25 ° C to 170 ° C. At this time, the mold may be subjected to a known mold release treatment or an internal mold release agent may be added in order to facilitate the mold release property after the polymerization. The sulfur-containing epoxy resin according to the present invention thus obtained is colorless and transparent, and has characteristics of high refractive index, low dispersion, and excellent impact resistance, such as eyeglass lenses and optical material materials such as camera lenses. It is suitable as a glazing material. Further, the lens according to the present invention is subjected to surface polishing, antistatic treatment, hard coat treatment in order to improve antireflection, high hardness, abrasion resistance, antifogging property, fashionability, etc., if necessary. A physical or chemical treatment such as a non-reflective coating treatment, a dyeing treatment, or a light control treatment can be performed.

[0045]

EXAMPLES Next, the production method of the compound of the present invention will be specifically explained with reference to examples. In addition, the impact resistance test of resin is 3c in diameter
A sample having a thickness of 1.5 mm and a thickness of 1.5 mm was prepared, and an iron ball having a predetermined weight was dropped from a height of 127 cm.

Example 1 20 g (0.13 mol) of bismercaptoethyl sulphide
And methanol 500ml, sodium hydroxide 10.4g
(0.26 mol) was charged to a 2 liter reaction flask, and
Stir until completely dissolved. Next, epichlorohydrin 2
5.2 g (0.273 mol) was added dropwise at room temperature over 1 hour.
Defeated Then, it stirred at room temperature for 3 hours. Then 10
Stir at room temperature for hours. Then add 300 ml of water and
The solvent was removed with a evaporator. After cooling, ethyl acetate 200
ml was added for extraction. After repeating this twice, 0.1N
After washing with 100 ml of hydrochloric acid aqueous solution, 100 ml of saturated saline solution
After washing with water and desolvation with an evaporator, 4,7,10-tri
Thia-1,12-n-tridecadiene dioxide 1
5.0 g was obtained. (44% yield) IRνneatcm^-1: 2916, 1424. NMR
(270MHz, CDCl ₃) Δppm: 2.58 ~
2.90 (16H, m), 3.12 to 3.18 (2H,
m) ,.

Example 2 20 g (0.13 mol) of bismercaptoethyl sulphide
80 ml of methanol and 0.10 g of sodium hydroxide
(0.0025 mol) into a 300 ml reaction flask.
And stirred until completely dissolved. Then epichlorohydride
Phosphorus 25.2 g (0.273 mol) at room temperature for 1 hour
It was dropped. Then, it stirred at room temperature for 3 hours. Evapo
After removing the solvent with a shaker, silica gel chromatography
Separated with (ethyl acetate: n-hexane = 1: 3) 1,1
3-dichloro-2,12-dihydroxy-4,7,10
35.2 g of -trithia-n-tridecane was obtained. (yield
80%) IRνneatcm^-1: 3400, 1430. NMR
(270MHz, CDCl ₃) Δppm: 2.80 ~
3.10 (14H, m), 3.65 to 3.75 (4H,
m), 3.95-4. 05 (2H, m).

Example 3 1,13-dichloro-2,12-dihi shown in Example 1
Droxy-4,7,10-trithia-n-tridecane 3
5.2 g (0.104 mol) and toluene 400 ml, water
700 g of sodium oxide 15.1 g (0.378 mol)
Sodium hydroxide dissolved in 1 ml of water was added to 1 l of reaction flask.
I trained in Sco. Then tetra-n-butylammonium
1.6 g of bromide was added, and the mixture was stirred at room temperature for 3 hours. vinegar
Ethyl acid (300 ml) was added for extraction. Do this twice
After repeating, wash with 100 ml of 0.1N hydrochloric acid aqueous solution
After that, wash with 100 ml of saturated saline and use an evaporator.
Desolvation, 4,7,10-trithia-1,12-n-to
22.1 g of lidecadiene dioxide was obtained. (Yield 8
0%) IRνneatcm^-1: 2916, 1424. NMR
(270MHz, CDCl ₃) Δppm: 2.58 ~
2.90 (16H, m), 3.12 to 3.18 (2H,
m) ,.

Example 4 20 g (0.13 mol) of bismercaptoethyl sulphide
80 ml of methanol and 0.10 g of sodium hydroxide
(0.0025 mol) was charged into a 300 ml reaction flask and stirred until completely dissolved. Next, 25.2 g (0.273 mol) of epichlorohydrin was added dropwise at room temperature over 1 hour. Then, it stirred at room temperature for 3 hours. Then, it stirred at room temperature for 10 hours. Next, dissolve the reaction product after desolvation with an evaporator in 400 ml of toluene,
15.1 g of sodium hydroxide dissolved in 700 ml of water
(0.378 mol) was charged to a 1 l reaction flask. Next, 1.6 g of tetra-n-butylammonium bromide was added, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate 3
00 ml was added for extraction. After repeating this twice, 0.
After washing with 100 ml of 1N aqueous hydrochloric acid solution, saturated saline solution 100
After washing with ml, the solvent was removed with an evaporator and then 4,7,10-
18.0 g of trithia-1,12-n-tridecadiene dioxide was obtained (yield 52%).

Example 5 4,7,10-Trithia-1,12-shown in Example 2
10.0 g of n-tridecadiene dioxide and 0.1 g of triethylamine, Zelec-UN as an internal release agent
What stirred 0.01 g was put into a 100 ml glass sample tube, and it oven-heated at 120 degreeC for 1 hour, and the colorless resin was obtained. nd = 1.63 νd = 39.3 Impact resistance test 100 g = ○

Example 6 4,7,10-Trithia-1,12-shown in Example 2
10.0 g of n-tridecadiene dioxide, 12.8 g of 4-methyltetrahydrophthalic anhydride and 0.1 g of triethylamine, and Zelec-UN as an internal release agent.
What stirred 0.1 g was put into a 100 ml glass sample tube, and oven-heated at 120 degreeC for 2 hours, and the pale yellow resin was obtained. nd = 1.54 νd = 50.5

Example 7 4,7,10-Trithia-1,12-shown in Example 2
10.0 g of n-tridecadiene dioxide, 5.8 g of bismercaptoethylsulfide and 0.3 of triethylamine.
1 g, 0.1 g of Zelec-UN as an internal mold release agent was stirred and placed in a 100 ml glass sample tube,
It was heated in an oven at 120 ° C. for 2 hours to obtain a pale yellow resin. nd = 1.67 νd = 36.0 Impact resistance test 100 g = ○

Example 8 4,7,10-Trithia-1,12-shown in Example 2
30.0 g of n-tridecadiene dioxide and 0.3 g of triethylamine, Zelec-UN as an internal release agent
0.03 g was stirred to form a uniform solution, which was sufficiently defoamed and poured into a mold composed of a glass mold and a gasket. It was heated in an oven at 120 ° C. for 3 hours to obtain a colorless minus lens. nd = 1.63 νd = 39.3 In the impact resistance test, a minus lens having a center thickness of 1.5 mm was prepared, and an iron ball having a predetermined weight was dropped from a height of 127 cm, and what was not cracked was ◯ and was cracked. The thing was marked as x. 1
14g = ○

Comparative Example 1 10.0 g of ethylene glycol diglycidyl ether and 0.1 g of triethylamine, Zele as an internal release agent
A mixture of 0.01 g of c-UN was put in a 100 ml glass sample tube, and heated in an oven at 120 ° C. for 2 hours to obtain a pale yellow resin. nd = 1.50 νd = 61.3

Comparative Example 2 Vinylcyclohexene diepoxide 10.0 g and tetrakis (2-mercaptoethylthiomethyl) methane 4.4
g and triethylamine 0.05 g, Z as an internal release agent
100 ml of a mixture of 0.01 g of elec-UN
It was put in a glass sample tube of and heated in an oven at 50 ° C. for 2 hours to obtain a pale yellow resin. nd = 1.64 νd = 44.0 Impact resistance test 100 g = ×

[0056]

Effect of the Invention 4,7,10-Trithia-according to the present invention
Found 1,12-n-tridecadiene dioxide,
It was possible to provide a resin having a high refractive index obtained by polymerizing the compound.

─────────────────────────────────────────────────── ─── Continuation of front page (58) Fields surveyed (Int.Cl. ⁷ , DB name) C07D 303/00-303/34 C08G 59/30 CA (STN) REGISTRY (STN)

Claims (7)

(57) [Claims] 1. Formula (I): A sulfur-containing epoxy compound represented by. 2. A compound of the formula (I
Compound represented by I) (Wherein X represents Br or Cl) in the presence of an inorganic base, the method for producing a sulfur-containing epoxy compound represented by the formula (I) according to claim 1. 3. A compound represented by the formula (III) is produced by reacting bismercaptoethyl sulfide with a compound represented by the formula (II) according to claim 2 in the presence of an inorganic base, and then: ] (In the formula, X is the same as the formula (II).) Isolation or without isolation, the reaction is carried out in the presence of an inorganic base, and the compound represented by the formula (I) according to claim 1. Method for producing sulfurized epoxy compound. 4. A method for producing a resin, which comprises polymerizing the compound represented by the formula (I) according to claim 1 in the presence of a polymerization catalyst. 5. A resin obtained by the production method according to claim 4. 6. A compound represented by the formula (1) according to claim 1 and an aliphatic amine, an aromatic amine, an aliphatic acid anhydride, an alicyclic acid anhydride, an aromatic acid anhydride, a halogen-based acid. A method for producing a resin, which comprises polymerizing at least one curing agent selected from an anhydride, a basic active hydrogen compound, an imidazole compound, a polymercaptan curing agent, and an isocyanate compound in the presence of a polymerization catalyst. 7. A resin obtained by the production method according to claim 6.