JP3439583B2 - Sulfur-containing (meth) acrylate compounds and uses thereof - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel sulfur-containing (meth) acrylate compound, a composition for a plastic lens containing the compound, and a sulfur-containing resin obtained by polymerizing the composition.

[0002]

2. Description of the Related Art Plastic lenses are lighter and harder to break than inorganic lenses, and can be dyed. Therefore, plastic lenses have recently been rapidly used in optical elements such as spectacle lenses and camera lenses. Currently, resins widely used for these purposes include diethylene glycol bis (allyl carbonate)
(Hereinafter referred to as DAC) by radical polymerization. This resin has various characteristics such as being excellent in impact resistance, being lightweight, being excellent in dyeing properties, being excellent in workability such as cutting property and polishing property, and the like. . However, since this resin has a refractive index n _D of 1.50, which is smaller than that of an inorganic lens (n _D = 1.52), a resin for a lens having a higher refractive index has been desired.

[0003] Polyurethane-based lenses are known as lenses having a higher refractive index than DAC resins. The present inventors have proposed, for example, Japanese Patent Application Laid-Open
JP-A-63-46213 proposes a polyurethane lens made of a polymer of a xylylene diisocyanate compound and a polythiol compound, and is widely used as an optical lens such as an eyeglass lens. Also, JP-A-2-27
JP 0859 proposes a polyurethane lens having a high refractive index, light weight and excellent impact resistance by combining a specific polythiol compound and an isocyanate compound.
However, these resins tend to be non-uniform when polymerized in a short period of time, and the polymerization time needs to be increased in order to obtain an optically uniform lens, which may complicate workability. In addition, lenses made of these resins
It has the disadvantage that the scratch resistance is not sufficient and the surface of the lens is easily damaged. Therefore, further improvement has been desired to solve these problems.

[0004]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a polymer lens which can be polymerized in a short time, has good optical properties, particularly has a high refractive index, and has very excellent scratch resistance. To provide an optical sulfur-containing resin useful as an optical fiber.

[0005]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a certain sulfur-containing (meth) acrylate compound is effective. It has been completed. That is,
The present invention provides a sulfur-containing (meth) acrylate compound represented by the following formula (1) (formula 3), a composition for a plastic lens containing the sulfur-containing (meth) acrylate compound represented by the formula (1), and And a sulfur-containing resin obtained by polymerizing the composition.

[0006]

Embedded image [Wherein, R represents a hydrogen atom or a methyl group, X represents any group represented by the following formulas (2) to (4),

[0007]

Embedded image (In the above formula, r represents an integer of 1 to 3.) n represents an integer of 1 to 3, and m is 2 or 3. ]

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The sulfur-containing (meth) acrylate compound represented by the formula (1) of the present invention is a novel compound, and these compounds are manufactured using a polythiol compound of a sulfur-containing carboxylic acid derivative serving as a mother skeleton as a starting material. Can be. A polythiol compound of a sulfur-containing carboxylic acid derivative is disclosed in JP-A-1-9016.
It is manufactured by a method similar to the method described in Japanese Patent Publication No. 9-99.
That is, readily available sulfur-containing carboxylic acids, for example,
Thioglycolic acid, thiopropionic acid, thiobutanoic acid,
Thiomalic acid, 2,3-dimercaptosuccinic acid or the like, or an alkyl ester thereof or the like, and 2-mercaptoethanol, 3-mercaptopropanol, or the like, without solvent or in a solvent, p-toluenesulfonic acid, sulfuric acid, hydrochloric acid, In the presence of a catalyst such as this, it can be obtained by heating to 10 to 200 ° C. and esterifying while removing generated water or alcohol.

The sulfur-containing (meth) acrylate compound is prepared from a polythiol compound of a sulfur-containing carboxylic acid derivative in the following manner, ie, 1 to 1 mol of SH group of the polythiol compound.
1.5 mol of (meth) acrylic acid chloride, etc.
A method of reacting at 0 ° C to 60 ° C, or 1 to 1 mol of SH group of the polythiol compound.
1.5 mol of β-chloropropionyl chloride or β-chloro-α-methylpropionyl chloride
It is produced by a method of reacting at 20 ° C. to 80 ° C., and then reacting 1 to 2 mol of the base at −20 ° C. to 60 ° C.

[0010] In the above reaction, a base can be co-present as a hydrogen chloride scavenger in the reaction system in order to remove hydrogen chloride generated during the reaction. The base as the hydrogen chloride scavenger is not particularly limited, but examples of a commonly used base include trialkylamines such as trimethylamine and triethylamine, pyridine, sodium hydroxide, potassium hydroxide and the like. As the base used in the latter reaction, a trialkylamine such as trimethylamine and triethylamine is more preferable. In order to obtain a sulfur-containing (meth) acrylate compound with a high yield and a high purity, the above-mentioned reaction in the first step is carried out without causing a base to coexist as a hydrogen chloride scavenger in the reaction system. It is preferred that the reaction is carried out directly while removing from the system.

As another method, the above-mentioned first-stage reaction is performed in advance, followed by esterification with a sulfur-containing carboxylic acid, and then the second-stage reaction is performed to obtain a sulfur-containing (meth) acrylate compound. There are ways. That is,
1-1.5 mol of β-chloropropionyl chloride or β-chloro-α-methylpropionyl chloride is added at -20 ° C. to 80 ° C. with respect to 1 mol of SH groups such as 2-mercaptoethanol and 3-mercaptopropanol. The reaction product is then reacted with a sulfur-containing carboxylic acid or a sulfur-containing carboxylic acid alkyl ester in the presence of a catalyst such as p-toluenesulfonic acid, sulfuric acid, hydrochloric acid or the like for 10 to 2 times.
Heat to 00 ° C and esterify while removing the water or alcohol formed, then remove the base from -20 ° C to 6 ° C.
This is a method of reacting at 0 ° C.

In these reactions, if necessary,
An organic solvent may be used. The organic solvent used is not particularly limited, but those having no reactivity with the raw materials necessary for the reaction can be used. As the organic solvent, for example, benzene, toluene, xylene, hexane, heptane, petroleum ether, chloroform, methylene chloride, aliphatic or aromatic hydrocarbons such as ethylene chloride or halogenated hydrocarbons, diethyl ether, dioxane,
Ethers such as tetrahydrofuran; ketones such as acetone and methyl ethyl ketone; and N, N-dimethylformamide.

The composition for a plastic lens of the present invention comprises:
It contains the sulfur-containing (meth) acrylate compound represented by the formula (1) of the present invention, and further comprises a sulfur-containing (meth) acrylate compound of the present invention, and a monomer copolymerizable therewith. It contains at least one kind of polythiol compound. In the case of a composition for a plastic lens containing a copolymerizable monomer or a polythiol compound, the content of the sulfur-containing (meth) acrylate compound of the present invention is determined by the difference between the sulfur-containing (meth) acrylate compound and the other monomer. Alternatively, it is at least 20% by weight, preferably at least 40% by weight, more preferably at least 60% by weight, based on the total amount of the polythiol compound. The monomer or polythiol compound copolymerizable with the sulfur-containing (meth) acrylate compound of the present invention is used for adjusting optical properties such as refractive index, adjusting various physical properties such as impact resistance and specific gravity, It is selected according to the purpose such as adjusting viscosity and other handling, and is not particularly limited. These copolymerizable monomers or polythiol compounds can be used alone or in combination of two or more.

Examples of the copolymerizable monomer include benzyl acrylate, benzyl methacrylate, butoxyethyl acrylate, butoxymethyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl acrylate,
Hydroxymethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, phenyl methacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate , Tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, ethylene glycol bisglycidyl acrylic Over DOO, ethylene glycol bisglycidyl methacrylate, bisphenol A diacrylate, bisphenol A dimethacrylate, 2,2
Bis (4-acryloxydiethoxyphenyl) propane,
2,2-bis (4-methacryloxydiethoxyphenyl)
Propane, trimethylolpropane triacrylate,
Trimethylolpropane trimethacrylate, glycerol diacrylate, glycerol dimethacrylate,
Pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, methylthioacrylate, methylthiomethacrylate, phenylthioacrylate, benzylthiomethacrylate, xylylenedithiol diacrylate, xylylenedithiol dimethacrylate, mercaptoethyl sulfide diacrylate, mercaptoethyl sulfide Examples include dimethacrylate, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl carbonate, diethylene glycol bisallyl carbonate, styrene, chlorostyrene, methylstyrene, bromostyrene, and dibromostyrene.

Examples of the polythiol compound include 1,2-ethanedithiol, 1,3-propanedithiol,
2,3-propanetrithiol, 2,3-dimercapto-1-propanol, diethylene glycol bis (2-
Mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), trimethylolpropanebis (2-mercaptoacetate), trimethylolpropanebis (3-mercaptopropionate),
Pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2- Bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene,
1,4-bis (mercaptomethyl) benzene, 1,2,2
3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene,
1,2,3-tris (mercaptomethyl) benzene,
1,2,4-tris (mercaptomethyl) benzene,
1,3,5-tris (mercaptomethyl) benzene,
4,4'-thiobisbenzenethiol, bis (2-mercaptoethylthio) methane, bis (2-mercaptoethylthio) methane, 1,2-bis (2-mercaptoethylthio) ethane, 1,3-bis (2 -Mercaptoethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) propane, tetrakis (2-mercaptoethylthiomethyl) methane, 1,2-bis (2-mercaptoethylthio) -3-mercapto Propane, 4,8-bis (mercaptomethyl) -3,6,9-trithia-1,1
1-undecanedithiol, 2,5-dimercapto-
1,4-dithiane, 2,5-dimercaptomethyl-1,
4-dithiane and the like.

[0016] The sulfur-containing resin of the present invention is obtained by polymerizing the above composition, and is obtained by polymerizing the sulfur-containing (meth) acrylate compound of the present invention alone or sulfur-containing (meth) acrylate. A compound obtained by copolymerizing a compound with another copolymerizable monomer or polythiol compound. As a polymerization method for obtaining the sulfur-containing resin of the present invention,
There is no particular limitation, and a known radical polymerization method can be used. As the polymerization initiation means in this case,
Use of radical initiators such as various peroxides and azo compounds, or ultraviolet light, visible light, α-ray, β-ray, γ-ray,
Irradiation with an electron beam or the like, or a combination thereof may be used.

As the radical initiator, known ones can be used. Representative examples thereof include benzoyl peroxide, dicumyl peroxide, lauroyl peroxide, di-t-butylperoxyazelate, and t-butylperoxide. Oxy-2-ethylhexanoate, t-butylperoxylaurate, t-butylperoxybenzoate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxyacetate, bis ( Peroxides such as 4-t-butylcyclohexyl) peroxydicarbonate and t-butylperoxyisopropylcarbonate; and azo compounds such as azobisisobutyronitrile.

When the polymerization is started by irradiating ultraviolet rays or the like, a known sensitizer or the like can be used. Representative sensitizers include benzophenone, 4,4-diethylaminobenzophenone, 1-hydroxycyclohexylphenyl ketone, isoamyl p-dimethylaminobenzoate, methyl 4-dimethylaminobenzoate, benzoin, benzoin ethyl ether, benzoin Isobutyl ether, benzoin isopropyl ether, 2,2
-Diethoxyacetophenone, methyl o-benzoylbenzoate, 2-hydroxy-2-methyl-1-phenylpropan-1-one, acylphosphine oxide and the like.

A typical polymerization method for obtaining the sulfur-containing resin (for example, a plastic lens) of the present invention includes cast polymerization. That is, between a mold held by a gasket or a tape, a radical initiator or a sensitizer,
Alternatively, a plastic lens composition (also referred to as a monomer mixture) of the present invention containing both of them is injected. At this time, if necessary, any treatment such as defoaming may be performed. Then, the polymer can be irradiated with ultraviolet rays or the like, heated in an oven, or cured by using these together, and the polymer can be taken out.

The polymerization method, polymerization conditions, and the like for obtaining the sulfur-containing resin of the present invention cannot be unconditionally limited by the type and amount of the initiator and the like and the type and ratio of the monomer used. For example, when irradiating with ultraviolet rays or the like, processing such as cooling may be performed to prevent overheating of the monomer mixture, and when heating in an oven, temperature control may be performed to select optimal temperature conditions. There is also. When heating in an oven, generally, a method of gradually heating from a low temperature and holding at a high temperature to complete the polymerization is employed. The polymerization time is affected by the type and amount of the initiator used and the type and ratio of the monomer used, and thus cannot be unconditionally limited. However, in general, it is possible to shorten the polymerization time by irradiation with ultraviolet rays or the like. When molding the sulfur-containing resin of the present invention, depending on the purpose, as in the known molding method, a chain extender, a crosslinking agent, a light stabilizer, an ultraviolet absorber, an antioxidant, an oil-soluble dye, Various substances such as fillers may be added. The removed sulfur-containing resin may be subjected to a treatment such as annealing, if necessary.

The sulfur-containing resin obtained by using the sulfur-containing (meth) acrylate of the present invention has a high refractive index, low dispersion, excellent heat resistance, weather resistance, and scratch resistance, and particularly excellent dyeability. It has excellent characteristics. The sulfur-containing resin of the present invention can be obtained as molded articles of various forms by changing a mold at the time of casting polymerization, and is used for various uses as an optical element material such as an eyeglass lens, a camera lens, and a transparent resin. Can be used. In particular, it is suitable as an optical element material for eyeglass lenses, camera lenses, and the like. Further, in the lens using the sulfur-containing resin of the present invention, if necessary, improvements such as antireflection, high hardness, improved abrasion resistance, improved chemical resistance, antifogging property, and fashionability are made. Therefore, physical or chemical treatments such as surface polishing, antistatic treatment, hard coat treatment, anti-reflection coat treatment, dyeing treatment, and light control treatment can be performed.

[0022]

The present invention will be described below in more detail with reference to examples and comparative examples. In the performance test of the obtained sulfur-containing resin, the refractive index, Abbe number, appearance, and scratch resistance were evaluated by the following test methods.・ Refractive index, Abbe number: 20 ° C using a Pulfrich refractometer
Was measured.・ Appearance: Observed visually. Scratch resistance: The surface of the resin was rubbed with # 0000 steel wool to check the scratch resistance of the surface and determined as follows. ○… Does not hurt at all even if strongly rubbed.

Example 1 A reaction flask equipped with a Dean-Stark tube equipped with a stirrer, a thermometer and a condenser was charged with 21.2 g (0.20 mol) of methyl thioglycolate and 23.4 g (0.30 mol) of 2-mercaptoethanol. Mol), 750 ml of benzene,
0.25 g of p-toluenesulfonic acid was charged and an esterification reaction was performed at 80 ° C. for 40 hours. Next, the organic layer was washed with a 5% aqueous sodium bicarbonate solution, and further washed with water. After the organic layer was dried over anhydrous magnesium sulfate, benzene was distilled off under reduced pressure to give 24.7 g of a colorless liquid thioglycolic acid (2-mercaptoethyl ester).
(0.16 mol). Next, 40.0 g of β-chloropropionyl chloride was placed in a reaction flask equipped with a stirrer, a thermometer, a dropping funnel, a gas inlet tube and a discharge tube.
(0.32 mol) and heated to 55 ° C. while gently flowing nitrogen gas. 22.8 g of thioglycolic acid (2-mercaptoethyl ester) (0.1
5 mol) was slowly added dropwise with stirring. The hydrogen chloride gas generated at this time was absorbed in a trap of an aqueous sodium hydroxide solution outside the system. After the completion of dropping, add 15
The reaction was allowed to proceed with stirring for an hour. Next, 200 ml of toluene
Was added thereto, and while cooling, a 10% aqueous solution of NaOH was added dropwise to make the inside of the system alkaline and sufficiently stirred. afterwards,
The organic layer was separated and washed with water. The organic layer was charged into a reaction flask equipped with a stirrer, a thermometer, and a dropping funnel.
C. and cooled to below
3.4 g (0.33 mol) was gradually added dropwise. After completion of the dropwise addition, the mixture was further stirred at 25 ° C. for 3 hours. Thereafter, 300 ml of toluene and 200 ml of water were added, and the reaction product was extracted into an organic layer and separated, and then the organic layer was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate, and water. After the organic layer was dried over anhydrous magnesium sulfate, toluene was distilled off under reduced pressure, and the desired colorless and transparent sulfur-containing acrylate compound, acryloylthioacetic acid (acryloylthioethyl ester) 3
2.8 g (0.126 mol) were obtained. ¹ H-NMR (CDCl ₃ solvent, based on tetramethylsilane) δ = 3.24 (t, 2H, OCH ₂ CH ₂ SCO) 3.79 (s, 2H, COSC H ₂ CO) 4.29 ( _{t, 2H, OC H 2 CH} 2 SCO) 5.79 (m, 2H, C H = CH 2) 6.36 (m, 4H, CH = C H 2)

Example 2 A reaction flask equipped with a stirrer and a thermometer was charged with 30.0 g (0.20 mol) of thiomalic acid, 46.9 g (0.60 mol) of 2-mercaptoethanol, 200 ml of toluene,
2.0 g of p-toluenesulfonic acid and anhydrous calcium sulfate (Dryalite, WA HAMMO
ND DRIERITE Co.) 150g and 50 ℃ at 50 ℃
The dehydration esterification reaction was performed for hours. After completion of the reaction, the reaction solution was subjected to suction filtration to remove calcium sulfate. next,
The organic layer was washed with a 5% aqueous sodium bicarbonate solution and then further washed with water. After the organic layer was dried over anhydrous magnesium sulfate, toluene was distilled off under reduced pressure to obtain a colorless liquid bis (2-mercaptoethyl ester) thiomalate 2
8.2 g (0.104 mol) were obtained. 27.0 g of this bis (2-mercaptoethyl ester) thiomalate
(0.10 mol), an acrylic esterification reaction was carried out in the same manner as in Example 1, and 39.8 g of a colorless and transparent sulfur-containing acrylate compound, acryloylthiosuccinic acid bis (acryloylthioethyl ester) (39.8 g) 0.
092 mol). ¹ H-NMR (CDCl ₃ solvent, based on tetramethylsilane) δ = 2.96 (m, 2H, COCH ₂ CHCO) 3.22 (t, 4H, OCH ₂ CH ₂ SCO) 4.26 ( _{m, 4H, OC H 2 CH} 2 SCO) 4.61 (t, 1H, COCH 2 C H CO) 5.78 (m, 3H, C H = CH 2) 6.34 (m, 6H, CH = C H ₂ )

Example 3 In a reaction flask equipped with a stirrer and a thermometer, 36.4 g (0.20 mol) of 2,3-dimercaptosuccinic acid, 46.9 g (0.60 mol) of 2-mercaptoethanol, and toluene 200 ml, 2.5 g of p-toluenesulfonic acid, and 150 g of anhydrous calcium sulfate (Dryalite, manufactured by WA HAMMOND DRIERITE Co.) as a dehydrating agent were charged, and a dehydration esterification reaction was performed at 50 ° C. for 60 hours.
After completion of the reaction, the reaction solution was subjected to suction filtration to remove calcium sulfate. Next, the organic layer was washed with a 5% aqueous sodium bicarbonate solution, and further washed with water. After the organic layer was dried over anhydrous magnesium sulfate, toluene was distilled off under reduced pressure, and 30.5 g (0.1%) of a colorless liquid bis (2-mercaptoethyl ester) 2,3-dimercaptosuccinate was obtained.
01 mol). 30.2 g of this 2,3-dimercaptosuccinic acid bis (2-mercaptoethyl ester)
(0.10 mol), and an acrylic esterification reaction was carried out in the same manner as in Example 1 to obtain a colorless and transparent sulfur-containing acrylate compound, 2,3-bis (acryloylthio) bis (acryloylthio) succinate. Ethyl ester)
35.8 g (0.069 mol) were obtained. · ¹ H-NMR (CDCl ₃ solvent, tetramethylsilane reference) δ = 3.21 (t, 4H , OCH 2 C H 2 SCO) 3.75 (m, 2H, COC H C H CO) 4.27 _{(m, 4H, OC H 2} CH 2 SCO) 5.78 (m, 4H, C H = CH 2) 6.34 (m, 8H, CH = C H 2)

Example 4 70 mg of t-butylperoxy-2-ethylhexanoate as a radical polymerization initiator and 50 mg of acryloylthioacetic acid (acryloylthioethyl ester) obtained in Example 1 as a sensitizer 2-hydroxy-2-
100 mg of methyl-1-phenylpropan-1-one was added and mixed well. After sufficient degassing, the mixture was poured into a mold composed of a glass mold and a gasket. After irradiating with ultraviolet rays for 105 minutes while cooling,
The temperature was raised from 30 ° C to 130 ° C over 30 minutes, and further 13
The mixture was heated at 0 ° C. for 1 hour to carry out polymerization. After the completion of the polymerization, the mixture was gradually cooled and the molded product was taken out of the mold. The obtained molded body (lens) is colorless and transparent, and has a refractive index n _d =
1.591 and Abbe number ν _d = 38.6. Also,
The abrasion resistance was also very good, and the evaluation was “○”.

Example 5 To 50 g of bis (acryloylthioethyl ester) of acryloylthiosuccinate obtained in Example 2, 50 mg of t-butylperoxy-2-ethylhexanoate as a radical polymerization initiator was sensitized. 2-hydroxy-2-methyl-1-phenylpropan-1-one 10 as an agent
0 mg was added and mixed well. After sufficient degassing, the mixture was poured into a mold composed of a glass mold and a gasket. After being irradiated with ultraviolet rays for 10 minutes while cooling, the temperature was raised from 30 ° C. to 130 ° C. over 30 minutes, and further heated at 130 ° C. for 1 hour to carry out polymerization. After polymerization,
After gradually cooling, the molded body was taken out of the mold. The obtained molded body (lens) is colorless and transparent, and has a refractive index n _d
= 1.585 and Abbe number ν _d = 38.5. In addition, the abrasion resistance was also extremely excellent, and the evaluation was “○”.

Example 6 2,3-bis (acryloylthio) obtained in Example 3
Bis-succinic acid (acryloylthioethyl ester) 50
With respect to g, 50 mg of t-butylperoxy-2-ethylhexanoate as a radical polymerization initiator and 100 mg of acylphosphine oxide as a sensitizer were added and mixed well. After sufficient degassing, the mixture was poured into a mold composed of a glass mold and a gasket. Irradiate with ultraviolet rays for 5 minutes while cooling, then
The temperature was raised to 30 ° C. over 30 minutes, and further heated at 130 ° C. for 1 hour to perform polymerization. After the completion of the polymerization, the mixture was gradually cooled and the molded product was taken out of the mold. The obtained molded body (lens) was colorless and transparent, and had a refractive index n _d = 1.599 and an Abbe number ν _d = 37.8. In addition, the abrasion resistance was also extremely excellent, and the evaluation was “○”.

Example 7 To 45 g of bis (acryloylthioethyl ester) acryloylthiosuccinate obtained in Example 2, 1
5 g of 2-bis (2-mercaptoethylthio) -3-mercaptopropane, 50 mg of t-butylperoxy-2-ethylhexanoate as a radical polymerization initiator, and 2-hydroxy-2-methyl-1 as a sensitizer 100 mg of -phenylpropan-1-one was added and mixed well. After sufficient degassing, the mixture was poured into a mold composed of a glass mold and a gasket. After being irradiated with ultraviolet rays for 10 minutes while cooling, the temperature was raised from 30 ° C. to 130 ° C. over 30 minutes, and further heated at 130 ° C. for 1 hour to carry out polymerization. After the completion of the polymerization, the mixture was gradually cooled and the molded product was taken out of the mold. The obtained molded body (lens) is colorless and transparent, has a refractive index n _d = 1.595, and Abbe number ν _d
= 39.1. In addition, the abrasion resistance was also extremely excellent, and the evaluation was “○”.

[0030]

The sulfur-containing (meth) acrylate compound of the present invention is a novel compound, and the composition of the present invention has excellent optical properties, particularly high refractive index, and is excellent in short-time polymerization. To provide a plastic lens having abrasion resistance.

────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kenichi Fujii 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsui Toatsu Chemical Co., Ltd. (56) References JP-A-5-51412 (JP, A) (58) Survey Field (Int.Cl. ⁷ , DB name) CA (STN) CAOLD (STN) REGISTRY (STN)

Claims (4)

(57) [Claims] 1. A sulfur-containing (meth) acrylate compound represented by the following formula (1): Embedded image [Wherein, R represents a hydrogen atom or a methyl group, X represents any group represented by the following formulas (2) to (4), (In the above formula, r represents an integer of 1 to 3.) n represents an integer of 1 to 3, and m is 1 or 2. ] 2. A composition for a plastic lens, comprising the sulfur-containing (meth) acrylate compound according to claim 1. 3. The plastic lens composition according to claim 2, comprising at least one monomer or polythiol compound copolymerizable with the sulfur-containing (meth) acrylate compound. 4. A sulfur-containing resin obtained by polymerizing the composition according to claim 2 or 3.