KR100720982B1 - Curable composition for optical parts - Google Patents

Abstract

The curable composition for an optical part of the present invention is a composition comprising (meth) acrylic acid ester (A) of a compound having no two or more hydroxyl groups per molecule without containing an aromatic hydrocarbon structure. The ether structure is at least 5% by weight, and the sulfonic acid and / or sulfonic acid ester content in the composition is 100 ppm or less in terms of sulfur atoms.

[Formula 1]

-(O-CH ₂ -CHR ¹ ) _n-

In the above formula, n = 1 to 100 and R ¹ is one or two or more selected from hydrogen, a methyl group and an ethyl group.

When the curable composition is cured, an optical part that is transparent and hardly causes coloring, alteration or deterioration can be obtained even with light from a light source having a light emission wavelength distribution in an ultraviolet region in a short wavelength region of visible light.

Description

Curable composition for optical parts

The present invention relates to a curable composition for an optical component, and more particularly, to an optical component that is transparent and hardly causes coloration, deterioration or deterioration even with respect to light from a light source having a light emission wavelength distribution in an ultraviolet region in a short wavelength region of visible light. A curable composition for forming.

Since transparent plastics have good moldability compared with transparent inorganic materials, such as glass, transparency plastics are used suitably for various uses, such as an optical member, an illumination member, and an automobile member.

As a material for obtaining a transparent plastic having excellent mechanical strength and moldability, a curable (meth) acrylic composition is known and ester diacryl of dimethacrylate, hydroxypivalic acid and neopentyl glycol of bisphenol A modified with ethylene oxide. An optical component formed by a curable (meth) acrylic composition comprising a rate and phenoxy (ethoxy) ethylacrylate is disclosed (see, for example, Japanese Unexamined Patent Publication No. Hei 6-263831).

However, since the transparent plastic formed from the curable (meth) acrylic composition disclosed has an aromatic hydrocarbon structure, it is not sufficient as a light resistance level for light from a light source having a light emission wavelength distribution in an ultraviolet region in the short wavelength region of visible light.

As described above, the transparent plastics obtained by curing the curable (meth) acrylic composition are still low in terms of colorless transparency and light resistance as they are discolored over time compared to transparent inorganic materials such as glass. It is used in optical parts such as batteries and outdoor electronic boards, which are used in the outdoors directly exposed to sunlight, or in optical parts such as light emitting diodes, optical cables, and display devices using light sources having light emission wavelength distribution in the ultraviolet region in the short wavelength region of visible light. To do this, a big problem remains in terms of discoloration and deterioration with time.

Also disclosed are photocurable compositions containing alkylene (oxy) di (meth) acrylates, specific photopolymerization initiators, and specific ultraviolet absorbers in specific proportions (see, for example, Japanese Patent No. 3055068).

However, the curable (meth) acrylic composition disclosed is relatively good in colorless transparency and light resistance. However, when the (poly) oxyalkylene chain is short, it is not sufficient in terms of poor molding or dimensional stability due to shrinkage during curing. When the alkylene chain was long, it was not enough in terms of water resistance and the like of the cured product.

Therefore, there is a great demand for the development of a transparent plastic having excellent colorless transparency and light resistance at an excellent level of transparent inorganic materials, and excellent in dimensional stability, moldability and water resistance of the cured product.

An object of the present invention is an optical component that is transparent, hardly colored, deteriorated or deteriorated even with respect to light from a light source having a light emission wavelength distribution in an ultraviolet region in a short wavelength region of visible light, and excellent in dimensional stability, moldability and water resistance of a cured product. It is to provide a curable (meth) acrylic composition for molding.

MEANS TO SOLVE THE PROBLEM This inventor earnestly examined in order to solve the said subject.

First, in a conventional composition comprising a (meth) acrylic acid ester of a compound having two or more hydroxyl groups per molecule, the composition of the composition with respect to light from a light source having a light emission wavelength distribution in a short wavelength region of visible light and an ultraviolet region In order to explore the factors of coloration, deterioration and deterioration of the cured product, the kind, content, manufacturing conditions and the like of the composition components contained in the composition were examined.

As a result, the present inventors

(1) When (meth) acrylic acid esters of compounds having two or more hydroxyl groups per molecule are used that do not contain an aromatic hydrocarbon structure, the light from a light source having a light emission wavelength distribution in the ultraviolet region in the short wavelength region of visible light is used. That coloration, deterioration or deterioration are suppressed,

(2) Light emission of the ultraviolet region in the short wavelength region of visible light by sulfonic acid and / or sulfonic acid ester contained in trace amounts in a conventional composition which does not contain a (meth) acrylic acid ester compound of a compound having two or more hydroxyl groups per molecule. Being one of the factors of coloration, deterioration or deterioration of light from a light source having a wavelength distribution,

(3) It was found that by containing the ether structure of the formula (1) in the composition, coloration, deterioration or deterioration of light from a light source having a light emission wavelength distribution in the ultraviolet region in the short wavelength region of visible light was remarkably suppressed:

-(O-CH ₂ -CHR ¹ ) _n-

In the above formula, n = 1 to 100 and R ¹ is one or two or more selected from hydrogen, a methyl group and an ethyl group.

And the ether structure content in the composition containing the (meth) acrylic acid esterified product of the compound having two or more hydroxyl groups per molecule is 5% by weight or more, and the sulfonic acid and / or sulfonic acid ester content in the composition is a sulfur atom. It was found that by setting it as 100 ppm or less, it is possible to obtain a curable composition for an optical part having colorless transparency and light resistance with an excellent level of transparent inorganic material.

Moreover, by using the (meth) acrylic acid ester of the compound which does not contain (beta) hydrogen with respect to a hydroxyl group as (meth) acrylic acid ester (A) of the compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule It has been found that a curable composition for an optical part having more excellent colorless transparency and light resistance can be obtained.

Further, (meth) acrylic acid esters (A) of a compound which does not contain an aromatic hydrocarbon structure and have two or more hydroxyl groups per molecule, wherein (meth) of a compound having an ether structure of the formula (1) and two or more hydroxyl groups in the molecule By using the acrylic acid ester, it is possible to remarkably improve the light resistance according to the introduction of the ether structure, and furthermore, to suppress the decrease in the water resistance and increase in the water absorption of the cured product due to the introduction of the ether bond as an unreacted component in the polymerizable component. Also revealed.

Furthermore, (meth) acrylic acid ester (A) of a compound containing no two or more hydrogen groups per molecule without containing an aromatic hydrocarbon structure, and having ethylene oxide, propylene oxide and butylene oxide in a compound having two or more hydroxyl groups per molecule By using a (meth) acrylic acid ester of a compound to which one or two or more kinds of alkylene oxides selected from are added, coloration, alteration of light from a light source having a light emission wavelength distribution in the ultraviolet region in the short wavelength region of visible light, Deterioration is further reduced, the water resistance fall of hardened | cured material, the increase in water absorption can be suppressed, and the composition for optical parts with favorable strength physical properties can be obtained.

In addition, a small amount of sulfonic acid and / or sulfonic acid ester is contained in a conventional composition comprising a (meth) acrylic acid ester of a compound having two or more hydroxyl groups per molecule. When (meth) acrylates an excited compound, it is common and common practice to perform a dehydration condensation method using a sulfonic acid-based catalyst (especially p-toluenesulfonic acid) as a catalyst from problems such as manufacturing cost. However, even after the distillation process, a small amount of sulfonic acid catalyst remains irreversibly. And (meth) acrylic acid esters of compounds having two or more hydroxyl groups per molecule by methods other than dehydration condensation using a sulfonic acid catalyst (for example, transesterification using a metal alcoholate or the like) , Due to problems such as manufacturing cost and the like, are rarely performed industrially at present.

In addition, it is found that by including the polymer and / or copolymer (B) of the (meth) acrylic acid ester in the composition, problems such as poor molding or dimensional stability due to shrinkage during curing can be solved while maintaining light resistance. Came out.

Moreover, the polymer and / or copolymer (B) of a (meth) acrylic acid ester can superpose | polymerize with the (meth) acrylic acid ester (A) of the compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule. By having it, the curable composition for optical components with more favorable strength physical property can be obtained.

That is, the curable composition for an optical part of the present invention is a composition containing (meth) acrylic acid ester (A) of a compound having no two or more hydroxyl groups per molecule without containing an aromatic hydrocarbon structure, wherein the chemical formula in the composition The content of the ether structure of (1) is 5% by weight or more, and the sulfonic acid and / or sulfonic acid ester content in the composition is 100 ppm or less in terms of sulfur atoms.

EMBODIMENT OF THE INVENTION Hereinafter, although this invention is demonstrated in detail, the scope of the present invention is not restrict | limited to these description, It can change suitably in the range which does not impair the meaning of this invention other than the following illustration.

In the present invention, the (meth) acrylic acid ester (A) of a compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule does not contain an aromatic hydrocarbon structure and also has two or more hydroxyl groups per molecule. It will not specifically limit, if it is the (meth) acrylic acid ester of the compound which has.

As a (meth) acrylic acid ester compound of the compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule, for example,

Ethylene glycol, propylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octane Diol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol, 1,14-tetradecanediol, 1, 15-pentadecandiol, 1,16-hexadecanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 1,2-cyclohexanediol, 1,3 Mono (meth) acrylates or di () of alkanediols such as cyclohexanediol, 1,4-cyclohexanediol, tricyclodecanedimethanol, cyclohexanedimethanol, hydrogenated bisphenol A, neopentylglycol and butylethylpropanediol Meth) acrylates;

Mono (meth) acrylates or di (meth) acrylates of alkanediols of mono or diesterates of neopentyl glycol and hydroxypivalic acid;

mono (meth) acrylates or di (meth) such as β, β, β ', β'-tetramethyl-2,4,8,10-tetraoxaspiro [5,5] undecane-3,9-dienol ) Acrylate.

Furthermore, mono (meth) acrylate or poly (meth) acryl, such as trimethylol ethane, trimethylol propane, trimethylol butane, trimethylol hexane, ditrimethylol propane, pentaerythritol, dipentaerythritol, glycerin, and polyglycerol The rate etc. are mentioned.

Among these, compounds which do not contain β-hydrogen to hydroxyl groups and which contain two or more hydroxyl groups per molecule, for example, mono or di (meth) acrylates of alkanediols such as neopentyl glycol and butylethylpropanediol; Mono (meth) acrylates or di (meth) acrylates of alkanediols of mono or diesterates of neopentyl glycol and hydroxypivalic acid; mono (meth) acrylate or di (meth) acrylic of β, β, β'β'-tetramethyl-2,4,8,10-tetraoxaspiro [5,5] undecane-3,9-dienol Rate; Mono (meth) acrylates or poly (meth) acrylates such as trimethylolethane, trimethylolpropane, trimethylolbutane, trimethylolhexane, ditrimethylolpropane, pentaerythritol, and dipentaerythritol are degraded by light or discolored. Particularly preferred is high resistance to.

Although it does not specifically limit as a manufacturing method of the (meth) acrylic acid ester (A) of the compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule, Preferably it is the dealcoholization reaction of a polyol and a (meth) acrylic acid ester. The method (ester exchange method) manufactured by this method, and the method (dehydration condensation method) manufactured by the dehydration reaction of a polyol and (meth) acrylic acid are mentioned.

When performing the transesterification method, the supply molar ratio of the polyol and the (meth) acrylic acid ester (hydroxyl group in the polyol: (meth) acrylic acid ester) is preferably from 1: 1 to 1:20, and from 1: 1.5 to 1:10. More preferably, 1: 2-1: 5 are still more preferable.

When performing the transesterification method, examples of the catalyst include alkali metal alcoholate, magnesium alcoholate, aluminum alcoholate, titanium alcoholate, dibutyltin oxide, anion exchange resin and the like. The amount of the catalyst used is preferably 0.01 to 10 parts by weight, more preferably 0.05 to 5 parts by weight, even more preferably 0.1 to 3 parts by weight, based on 100 parts by weight of the total supply of the reaction. It is also preferable to remove the catalyst after the reaction.

When performing the transesterification method, a solvent can be used. Examples of the solvent that can be used include pentane, cyclopentane, hexane, cyclohexane, methylcyclohexane, heptane, cycloheptane, octane, isooctane, benzene, toluene and cymene. The amount of the solvent used is preferably 1 to 70 parts by weight, more preferably 5 to 50 parts by weight, even more preferably 10 to 30 parts by weight, based on 100 parts by weight of the total supply of the reaction.

In the case of performing the transesterification method, the reaction temperature is preferably 50 to 150 ° C, more preferably 70 to 140 ° C, even more preferably 90 to 130 ° C.

In the case of carrying out the dehydration condensation method, the supply molar ratio of the polyol and (meth) acrylic acid (hydroxyl group in the polyol: (meth) acrylic acid) is preferably 1: 1 to 1: 5, and 1: 1.01 to 1: 2 More preferably, 1: 1.05-1: 1.5 are still more preferable.

In the case of performing the dehydration condensation method, examples of the catalyst include acid catalysts such as sulfuric acid, hydrochloric acid, phosphoric acid, p-toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and cation exchange resins. have. Among these, in order to fully exhibit the effect of this invention, a cation exchange resin is preferable. Examples of the cation exchange resin include Anbarite (registered trademark), Anbarate (registered trademark), and Mition (manufactured by Mitsubishi Chemical Corporation) manufactured by Rohm and Haas Corporation. The cation exchange resin is more preferably washed with an organic solvent such as toluene, methanol, and water before use so that the sulfur component does not flow out. The amount of the catalyst used is the total supply amount of the reaction. 0.01-10 weight part is preferable with respect to 100 weight part, 0.05-5 weight part is more preferable, 0.1-3 weight part is still more preferable. It is also preferable to remove the catalyst after the reaction.

When performing the dehydration condensation method, for example, pentane, cyclopentane, hexane, cyclohexane, methylcyclohexane, heptane, cycloheptane, octane, isooctane, benzene, toluene, cymene and the like can be mentioned. As for the usage-amount of a catalyst, 1-70 weight part is preferable with respect to 100 weight part of total feed amounts of reaction, 5-50 weight part is more preferable, 10-30 weight part is still more preferable.

In the case of performing the dehydration condensation method, the reaction temperature is preferably 50 to 150 ° C, more preferably 70 to 140 ° C, even more preferably 90 to 130 ° C.

In the curable composition for optical parts of the present invention, the content ratio of (meth) acrylic acid ester (A) of a compound containing no aromatic hydrocarbon structure and having two or more hydroxyl groups per molecule is not particularly limited, but the curable composition for optical parts It is preferable to contain the (meth) acrylic acid ester (A) of the compound which does not contain an aromatic hydrocarbon structure with respect to the whole, and has two or more hydroxyl groups per molecule in the ratio of 10 to 95 weight%, More preferably, it is 20- 90 weight%, More preferably, it is 30-85 weight%. By including the (meth) acrylic acid ester compound (A) of the compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule in the above-mentioned ratio, the effects of the present invention can be sufficiently exhibited, and particularly heat resistance, dimensional stability and The hardened | cured material which balanced the moldability can be obtained. If it is out of the said ratio, there exists a possibility that it may not fully exhibit the effect of this invention.

The ether structure of the said general formula (1) in the curable composition for optical components of this invention may be contained in any form in a composition, and is not specifically limited. For example, it may be contained as a non-reactive component or may be contained as a reactive component.

If the ether structure is contained as a non-reactive component, for example

Ethylene glycol dialkyl ether, polyethylene glycol dialkyl ether, propylene glycol dialkyl ether, polypropylene glycol dialkyl ether, butylene glycol dialkyl ether, polybutylene glycol dialkyl ether, ethylene glycol monoalkyl ether acetate, polyethylene glycol mono Alkyl ether acetates, propylene glycol monoalkyl ether acetates, polypropylene glycol monoalkyl ether acetates, butylene glycol monoalkyl ether acetates, polybutylene glycol monoalkyl ether acetates;

Diols (e.g. 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, neopentylglycol, neopentylglycol mono or diesters of hydroxypivalanic acid, butylethylpropanediol 1 or 2 or more types of alkylene oxide adducts selected from ethylene oxide, propylene oxide, butylene oxide of hydrogenated bisphenol A, etc.);

Ethylene oxide, propylene oxide, butylene oxide of polyols (e.g., trimethylol ethane, trimethylolpropane, trimethylolbutane, trimethylolhexane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, glycerin, polyglycerol, etc.) It can be contained in the form of the 1 type (s) or 2 or more types of alkylene oxide adducts chosen from these, Only 1 type of these may be used and 2 or more types may be used together.

It is preferable to introduce an ether structure as the reactive component, because it is possible to suppress a decrease in water resistance and increase in water absorption of the cured product due to the ether structure.

Mono (meth) acrylates and di (meth) acrylates such as polyethylene ring, polypropylene glycol, polybutylene glycol, random ring-opening polymers of ethylene oxide and propylene oxide, block ring-opening polymers, and polyalkylene glycols;

Methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, methoxyethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, etc. ;

Glycols containing no aromatic hydrocarbon structure (e.g., 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, neopentylglycol, monopentylglycol of neopentylglycol and hydroxypivalic acid) Mono (meth) acrylates or dimers of one or two or more alkylene oxide adducts selected from ethylene oxide, propylene oxide and butylene oxide of esterified products, butylethylpropanediol, cyclohexanedimethanol, hydrogenated bisphenol A, etc.) (Meth) acrylates;

Ethylene oxide, propylene oxide and butylene oxide of polyols (e.g., trimethylolethane, trimethylolpropane, trimethylolbutane, trimethylolhexane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, glycerin, polyglycerine, etc.) Mono (meth) acrylate or poly (meth) acrylate of one or two or more alkylene oxide adducts selected from among them;

Methoxyethyl vinyl ether, ethoxy ethyl vinyl ether, methoxy ethoxy ethyl vinyl ether, ethoxy ethoxy ethyl vinyl ether, methoxy polyethylene glycol vinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether Monofunctional vinyl ethers such as diethylene glycol monovinyl ether and polyethylene glycol vinyl ether;

Ethylene glycol divinyl ether, diethylene glycol divinyl ether, polyethylene glycol divinyl ether, propylene glycol divinyl ether, butylene glycol divinyl ether, bisphenol A alkylene oxide divinyl ether, bisphenol F alkylene oxide divinyl ether, Polyfunctional vinyl ether, such as ethylene oxide addition trimethylol propane trivinyl ether, ethylene oxide addition ditrimethylol propane tetravinyl ether, ethylene oxide addition pentaerythritol tetravinyl ether, and ethylene oxide addition dipentaerythritol hexavinyl ether, can be contained, 1 type of these may be used and 2 or more types may be used together.

Among them, compounds which do not contain aromatic hydrocarbon structures and which do not contain β-hydrogen to hydroxyl groups and which contain two or more hydroxyl groups per molecule, for example neopentylglycol, butylethylpropanediol, neopentylglycol and hydroxypivalic acid Mono or diesters of; β, β, β ', β'-tetramethyl-2,4,8,10-tetraoxaspiro [5,5] undecane-3,9-dienol, trimethylolethane, trimethylolpropane, trimethylolbutane Mono (meth) of one or two or more kinds of alkylene oxide adducts selected from ethylene oxide, propylene oxide, and butylene oxide of polyols such as trimethylol hexane, ditrimethylol propane, pentaerythritol, and dipentaerythritol Acrylate or poly (meth) acrylate is the most preferable because it is hard to receive discoloration and deterioration by light, and also excellent in water resistance. Only 1 type may be used among these and 2 or more types may be used together.

The curable composition for optical components of this invention may contain polymeric monomers other than the (meth) acrylic acid ester compound (A) of a compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule.

As the polymerizable monomer, for example

Methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-nonyl (meth) acrylate, lauryl ( Meth) acrylate, cyclohexyl (meth) acrylate, cyclohexylmethyl (meth) acrylate, (meth) acrylic acid, adamantyl (meth) acrylate, norbornyl (meth) acrylate, N, N-dimenyl Monofunctional (meth) acrylates such as aminoethyl (meth) acrylate and α-hydroxymethyl acrylate;

Monofunctional (meth) acrylamides such as N, N-dimethyl (meth) acrylamide and N-methylol (meth) acrylamide;

Monofunctional vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, 2-ethylhexyl vinyl ether, n-nonylvinyl ether, lauryl vinyl ether, cyclohexyl vinyl ether, and chlorethyl vinyl ether;

Monofunctional N-vinyl compounds such as N-vinylpyrrolidone, N-vinyl caprolactam, N-vinyl-N-methylformamide, N-vinylimidazole, N-vinylformamide, and N-vinylacetamide;

Monofunctional vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, allyl acetate, vinyl acetate, vinyl propionate and vinyl benzoate;

Maleic anhydride, maleic acid, dimethyl maleate, diethyl maleate, monomethyl maleate, monoethyl maleate, fumaric acid, dimethyl fumarate, diethyl fumarate, monomethyl fumarate, monoethyl fumarate, itaconic acid, itaconic acid, dimethyl itaconic acid, itaconic acid Diethyl acid, monomethyl itaconate, monoethyl itaconate, methylenemalonic acid, dimethyl methylene malonic acid, monomethyl methylenemalonic acid, cinnamic acid, methyl cinnamic acid, ethyl cinnamic acid, crotonic acid, methyl crotonate, ethyl crotonate, etc. Monofunctional α, β-unsaturated compounds of;

Polyfunctional vinyl, such as hexanediol divinyl ether, trimethylol propane trivinyl ether, ditrimethylol propane tetravinyl ether, glycerin trivinyl ether, pentaerythritol tetravinyl ether, dipentaerythritol pentavinyl ether, and dipentaerythritol hexavinyl ether ether;

Polyfunctional vinyl compounds such as divinylbenzene;

Polyfunctional (meth) acryl other than the (meth) acrylic acid ester (A) of the compound which does not contain aromatic hydrocarbon structure, such as the di (meth) acrylate of the alkylene oxide compound of bisphenol A, and has two or more hydroxyl groups per molecule The rate etc. are mentioned, Among these, only 1 type may be used and 2 or more types may be used together.

It is preferable that the curable composition for optical components of this invention contains the polymer and / or copolymer (B) of (meth) acrylic acid ester.

It will not specifically limit, if it is a polymer obtained by superposing | polymerizing the monomer component containing 50 mol% or more of (meth) acrylic acid ester and / or (meth) acrylic acid as a polymer and / or copolymer (B) of (meth) acrylic acid ester.

The polymerizable monomer which can be used as a raw material of the polymer and / or copolymer (B) of (meth) acrylic acid ester is the above-mentioned monofunctional (meth) acrylate, monofunctional (meth) acrylamide, monofunctional vinyl ether, and monofunctional In addition to the N-vinyl compound, the monofunctional vinyl compound, the monofunctional α, β-unsaturated compound, and the like, a trace amount of the polyfunctional monomer may be used.

The polymer and / or copolymer of the (meth) acrylic acid ester may include only one type and may contain two or more types.

In addition, the polymer and / or copolymer (B) of the (meth) acrylic acid ester has a reactor capable of polymerizing with (meth) acrylic acid ester (A) of a compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule. Particular preference is given to the optical properties of the optical parts obtained by curing the composition of the present invention.

Process for preparing polymer and / or copolymer (B) of (meth) acrylic acid ester having a reactor capable of polymerizing with (meth) acrylic acid ester (A) of a compound containing no aromatic hydrocarbon structure and having at least two hydroxyl groups per molecule With

(1) A method of reacting a polymerizable monomer containing a glycidyl group with a copolymer of a polymerizable monomer containing a carboxyl group and a (meth) acrylic acid ester, or a polymerizable monomer containing a glycidyl group and a (meth) acrylic acid ester A method of reacting a polymerizable monomer containing a carboxyl group with a copolymer of;

(2) A method of reacting a polymerizable monomer containing an isocyanate group with a copolymer of a polymerizable monomer containing a hydroxyl group and a (meth) acrylic acid ester, or a copolymer of a polymerizable monomer containing an isocyanate group and a (meth) acrylic acid ester A method of reacting a polymerizable monomer containing a hydroxyl group;

(3) A method of reacting a copolymer of a polymerizable monomer containing a hydroxyl group and / or a carboxyl group with a (meth) acrylic acid ester with a polymerizable monomer containing a vinyl ether group and another polymerizable group, or containing a vinyl ether group and another polymerizable group A method of reacting a copolymer of a polymerizable monomer and a (meth) acrylic acid ester with a polymerizable monomer containing a hydroxyl group and / or a carboxyl group;

(4) A method of reacting a polymerizable monomer containing an acid anhydride group with a copolymer of a polymerizable monomer containing a hydroxyl group and a (meth) acrylic acid ester, or an air of a polymerizable monomer containing an acid anhydride group and a (meth) acrylic acid ester A method of reacting a polymerizable monomer containing a hydroxyl group with the copolymer;

(5) Although the method of partially polymerizing the polymerizable monomer composition containing a polyfunctional monomer, and leaving a part of double bond in the side chain of a polymer, etc. are mentioned, It is not specifically limited to these methods.

Although the content rate of the polymer and / or copolymer (B) of the (meth) acrylic acid ester in the curable composition for optical parts of this invention is not specifically limited, The ratio of 5-50 weight% with respect to the whole curable composition for optical parts. It is preferable to include it, More preferably, it is 10-40 weight%, More preferably, it is 15-30 weight%. By including the polymer and / or copolymer (B) of (meth) acrylic acid ester in the said ratio, the effect of this invention can fully be exhibited, especially the shrinkage at the time of hardening is suppressed, and the favorable molded object can be obtained. . If it is out of the said ratio, there exists a possibility that it may not fully exhibit the effect of this invention.

The curable composition for optical components of this invention may contain a polymeric oligomer.

As the polymerizable oligomer, for example

Saturated or unsaturated polybasic acids or anhydrides thereof (e.g. maleic acid, succinic acid, adipic acid, phthalic acid, isophthalic acid, terephthalic acid, tetrahydroxyphthalic acid, etc.) and saturated or unsaturated polyhydric alcohols (e.g., ethylene glycol, propylene glycol, Neopentyl glycol, 1,4-butanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, polyethylene glycol, polypropylene glycol, 1,4-dimethylolbenzene, trimethylolpropane, pentaerythritol, etc. Polyesters (meth) acrylates obtained by the reaction of a) with (meth) acrylic acid;

Polyfunctional epoxy compounds (e.g., bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexenyl-3 ', 4'-epoxycyclohexene carboxylate, hexahydrophthalic acid Diglycidyl ether, triglycidyl isocyanurate, etc.) and epoxy (meth) acrylates obtained by the reaction of (meth) acrylic acid;

Polyfunctional oxetane compounds (eg, 4,4'-bis [(3-ethyl-3-oxetanyl) methoxymethyl] biphenyl, bis [1 -4-benzenedicarboxylic acid] Tinyl-3-oxetanyl) methyl] ester, 9,9-bis [2-methyl-4- {2- (3-oxetanyl)} butoxyphenyl] fluorene, 9,9-bis [4 [ Oxetane (meth) acrylate obtained by the reaction of 2- {2- (3-oxetanyl)} butoxy] ethoxyphenyl] fluorene and the like) with (meth) acrylic acid;

Saturated or unsaturated polyhydric alcohols (e.g., ethylene glycol, neopentylglycol, polytetramethylene glycol, polyester polyols, polycaprolactone polyols, etc.) and organic polyisocyanates (e.g., triylene diisocyanates, isoborone diisocyanates, Xylene diisocyanate etc.) and hydroxyl-containing (meth) acrylate (for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 1,4-butanediol mono (meth) acryl) Polyurethane (meth) acrylates obtained by the reaction of late);

Polysiloxane poly (meth) acrylates obtained by the reaction of polysiloxanes with (meth) acrylic acid; The polyamide poly (meth) acrylate etc. which are obtained by reaction of polyamide and (meth) acrylic acid are mentioned, Only 1 type may be used and 2 or more types may be used together.

The curable composition for optical components of this invention may also contain other polymers other than the polymer and / or copolymer (B) of a (meth) acrylic acid ester.

As another polymer, a polycarbonate, polystyrene, a silicon resin, polyimide, polyamide, saturated polyester, polyvinyl acetate, polyvinyl chloride, polyvinyl alcohol, polyvinyl acetal, AS resin, EVA resin etc. are mentioned, for example. One type of these may be used and two or more types may be used together.

The curable composition for optical components of this invention may also contain a polymerization initiator. Although it does not specifically limit as a polymerization initiator, It is preferable to contain at least 1 sort (s) chosen from a photoinitiator (C1) and a thermal polymerization initiator (C2), and it is more preferable to contain a photoinitiator (C1). By using a photoinitiator, the manufacturing efficiency of an optical component can be improved. By using a photoinitiator (C1) and a thermal polymerization initiator (C2) together, the fall of the light resistance by a photoinitiator can be suppressed to the minimum, and the manufacturing efficiency of an optical component can be improved, and it is more preferable.

As a photoinitiator (C1), for example

Diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone , 1-hydroxycyclohexylphenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) Acetophenones such as butanone and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone oligomer;

Benzoin such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether;

Benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenylsulfide, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone , 2,4,6-trimethylbenzophenone, 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2-propenyloxy) ethyl] benzenemethanealuminum bromide, (4-benzoylbenzyl Benzophenones such as trimethylammonium chloride;

2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichloro thioxanthone, 1-chloro-4-propoxy thioxanthone, 2- ( Thioxanthones such as 3-dimethylamino-2-hydroxy) -3,4-dimethyl-9H-thioxanthone-9-one mesochloride;

2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl-pentylphosphine oxide, bis (2,4,6-trimethylbenzoyl) Acyl phosphine oxides, such as -phenyl phosphine oxide, etc. are mentioned, It is preferable not to contain aromatic hydrocarbon structure among these. As a photoinitiator (C1), only 1 type may be used and 2 or more types may be used together.

As a thermal polymerization initiator (C2), for example

Methyl ethyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, methyl acetate acetate peroxide, acetyl acetate peroxide, 1,1-bis (t-hexyl peroxy) -3,3,5-trimethylcyclohexane , 1,1-bis (t-hexylperoxy) -cyclohexane, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-butylper Oxy) -2-methylcyclohexane, 1,1-bis (t-butylperoxy) -cyclohexane, 1,1-bis (t-butylperoxy) cyclododecane, 1,1-bis (t-butyl Peroxy) butane, 2,2-bis (4,4-di-t-butylperoxycyclohexyl) propane, p-methanehydroperoxide, diisopropylbenzenehydroperoxide, 1,1,3,3- Tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-hexyl hydroperoxide, t-butylhydroperoxide, α, α'-bis (t-butylperoxy) diisopropylbenzene, dicumylperoxide, 2, 5- Methyl-2,5-bis (t-butylperoxy) hexane, t-butylcumylperoxide, di-t-butylperoxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexyne -3, isobutyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide, succinic acid peroxide, m-toluoylbenzoyl peroxide, benzoyl peroxide , Di-n-propylperoxydicarbonate, diisopropylperoxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxyethylperoxydicarbonate, di-2-ethoxyhexyl perox CDicarbonate, di-3-methoxybutylperoxydicarbonate, di-s-butylperoxydicarbonate, di (3-methyl-3-methoxybutyl) peroxycarbonate, α, α'-bis (neodecanoylfur Oxy) diisopropylbenzene, cumylperoxy neodecanoate, 1,1,3,3-tetramethylbutylperoxy neodecanoate, 1- Ichlorohexyl-1-methylethylperoxy neodecanoate, t-hexyl peroxy neodecanoate, t-butylperoxy neodecanoate, t-hexyl peroxy pivalate, t-butyl peroxy pivalate , 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis (2-ethylhexanoylperoxy) hexanoate, 1-cyclohexyl -1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-hexylperoxyisopropyl monocarbonate , t-butylperoxy isobutylate, t-butylperoxymaleate, t-butylperoxy-3,5,5-trimetholhexanoate, t-butylperoxylaurate, t-butylperoxyiso Propyl monocarbonate, t-butylperoxy-2-ethylhexyl monocarbonate, t-butylperoxy acetate, t-butylperoxy-m-toluylbenzoate, t-butylperoxybenzoate, bis (t-butyl Peroxy) iso Talate, 2,5-dimethyl-2,5-bis (m-toluylperoxy) hexane, t-hexylperoxybenzoate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, t -Butyl peroxyallyl monocarbonate, t-butyl trimethylsilyl peroxide, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 2,3-dimethyl-2,3-di Organic peroxide initiators such as phenylbutane;

2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 1-[(1-cyano-1-methylethyl) azo] formamide, 1,1'-azobis (cyclohexane- 1-carbonitrile), 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvalero Nitrile), 2,2'-azobis (2-methylpropionamidine) dihydrochloride, 2,2'-azobis (2-methyl-N-phenylpropionamidine) dihydrochloride, 2,2'- Azobis [N- (4-chlorophenyl) -2-methylpropionamidine) dihydrochloride, 2,2'-azobis [N- (4-hydrophenyl) -2-methylpropionamidine] dihydrochloride , 2,2'-azobis [2-methyl-N- (phenylmethyl) propionamidine] dihydrochloride, 2,2'-azobis [2-methyl-N- (2-propenyl) propionamidine ] Dihydrochloride, 2,2'-azobis [N- (2-hydroxyethyl) -2-methylpropionamidine] dihydrochloride, 2,2'- Azobis [2- (5-methyl-2-imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane] di Hydrochloride, 2,2'-azobis [2- (4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl) propane] dihydrochloride, 2,2'-azo Bis [2- (3,4,5,6-tetrahydropyridin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (5-hydroxy-3,4,5,6 -Tetrahydropyridin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- [1- (2-hydroxyethyl) -2-imidazolin-2-yl] propane] dihydro Chloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane], 2,2'-azobis [2-methyl-N- [1,1-bis (hydroxymethyl ) -2-hydroxyethyl] propionamide], 2,2'-azobis [2-methyl-N- [1,1-bis (hydroxymethyl) ethyl] propionamide], 2,2'-azobis [2-methyl-N- (2-hydroxyethyl) propionamide], 2,2'-azo (2-methylpropionamide), 2,2'-azobis (2,4,4-trimethylpentane), 2,2'-azobis (2-methylpropane), dimethyl-2,2-azobis ( Azo initiators, such as 2-methyl propionate), 4,4'- azobis (4-cyanopentanoic acid), and 2,2'- azobis [2- (hydroxymethyl) propionitrile], etc. are mentioned. One type of these may be used and two or more types may be used together.

The curable composition for an optical component of the present invention may include a thermal polymerization accelerator together with the thermal polymerization initiator (C2).

As a thermal polymerization accelerator, for example

Metal soaps such as cobalt, copper, tin, zinc, manganese, iron, zirconium, chromium, vanadium, calcium and potassium; Primary, secondary and tertiary amine compounds; Quaternary ammonium salts; Thiourea compounds; Ketone compounds etc. are mentioned, Preferably they are acetyl acetone and methyl acetoacetate. These may use only 1 type and may use 2 or more types together.

When the curable composition for an optical component of the present invention contains the polymerization initiator, the content ratio of the polymerization initiator in the composition is preferably 0.001 to 10% by weight, more preferably 0.001 to 5% by weight, even more preferably 0.001 to 3% by weight, particularly preferably 0.001 to 2% by weight, most preferably 0.01 to 2% by weight. When the said content rate is less than 0.001 weight%, there exists a possibility that a polymerizability may fall, and when it exceeds 10 weight%, there exists a possibility that light resistance may fall.

In the curable composition for optical parts of this invention, when using a photoinitiator (C1) and a thermal polymerization initiator (C2) together, the ratio (thermal polymerization initiator / photoinitiator (weight ratio)) of these content has a range of 1-100. Preferably, more preferably in the range of 2 to 100, even more preferably in the range of 2 to 50, even more preferably in the range of 2 to 30, particularly preferably in the range of 3 to 20, most preferably 5 to 20 Range. If the content ratio is less than 1, the effect on improving weather resistance may be reduced. If the content is more than 100, the active energy ray curability may be lowered.

Moreover, an inorganic fine particle (D) can be mix | blended with the curable composition for optical components of this invention as needed. Inorganic fine particles reduce the cure shrinkage at the time of curing the composition, reproduce the precise shape and dimensions of the cracks and parts as designed, or improve the heat resistance and thermal conductivity. Although it depends also on the optical component which uses this composition, in the case of the use which emphasizes transparency, it is essential to use what is suitable for the hardened | cured material and refractive index of this composition, or what is called nanoparticles whose maximum particle diameter is 50 nm or less.

As an inorganic fine particle which can be used for the curable composition for optical components of this invention, glass, alumina, aluminum hydroxide, fused silica, crystalline silica, ultra fine amorphous silica, hydrophobic ultra fine silica, talc etc. are mentioned, for example. . Among them, ultrafine powdered amorphous silica and hydrophobic ultrafine silica are preferable in terms of the balance of various physical properties, and in particular, nanosilica fine particles having a polymer coating on the surface thereof are particularly preferable in terms of both optical and thermal properties. Moreover, when using for sealing of white LED, various fluorescent substance can be mix | blended.

The curable composition for an optical part of the present invention may include other components such as a plasticizer, a ultraviolet absorber, an antioxidant, an inorganic filler, an antifoaming agent, a thickener, a thixotropic agent, a leveling agent, a releasing agent, and the like within the scope of not impairing the effects of the present invention. It may be. In particular, the choice of release agents is important when molding precise optical components.

As a release agent, for example

Metal soaps such as zinc stearate, calcium stearate, magnesium stearate, lithium stearate, barium stearate, and sodium stearate; Sodium bistridecylsulfosuccinate, sodium dioctylsulfosuccinate, sodium dihexylsulfosuccinate, sodium dicyclohexylsulfosuccinate, sodium diamylsulfosuccinate, sodium diisobutylsulfosuccinate, sodium N-octadecylsulfosuccinate amide, sodium N Sulfosuccinic ester-based surfactants such as-(1,2-dicarboxyethyl) -N-octadecylsulfosuccinate amide tetrasodium;

Capric acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoseric acid, myristic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, 12 Fatty acids such as hydroxystearic acid and ricinolic acid;

Higher alcohols such as lauryl alcohol, stearyl alcohol and behenyl alcohol;

Fatty acid esters such as methyl stearate, stearyl stearate, behenyl behenate and sorbitan monostearate;

Silicone release agents such as KF96, KF965, KF410, KF412, KF4701, KF54, KS61, KM244F, KS702, KF725, KS707, and KS800P, which are products of Shinsung Chemical Industrial Co., Ltd .;

Fluorine-based interfaces such as polypox PF-136A, PF-156A, PF-151N, PF-636, PF-6320, PF-656, PF-6520, PF-651, PF-652, and PF-3320, which are products of OMNOVA An activator etc. are mentioned, Only 1 type may be used among these and 2 or more types may be used together. Among these, sulfosuccinic acid ester-based surfactants, fatty acids, higher alcohols, fatty acid esters, and fluorine-based surfactants are preferable because they can express release properties while maintaining transparency.

The curable composition for optical parts of this invention can contain a hydroxyl-containing compound as an additive which improves light resistance.

Examples of the hydroxyl group-containing compound include methanol, ethanol, propanol, butanol, pentanol, 1,4-butanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, and 1,3. -Hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 1,3-heptanediol, 1,4-heptanediol, 1,5-heptanediol, 1,6- Heptanediol, 1,7-heptanediol, 1,3-octanediol, 1,4-octanediol, 1,5-octanediol, 1,6-octanediol, 1,7-octanediol, 1,8-octane Diol, 1,3-nonanediol, 1,4-nonanediol, 1,5-nonanediol, 1,6-nonanediol, 1,7-nonanediol, 1,8-nonanediol, 1,9-nonanediol , Neopentylglycol, hydrogenated bisphenol A, trimethylolpropane, pentaerythritol, dipentaerythritol, glycerin, polyglycerol, trimethylolpropane, etc. may be mentioned, Only 1 type may be used and 2 or more types may be used together. have.

It is important for the curable composition for optical parts of this invention that the sulfonic acid and / or sulfonic acid ester content in this composition is 100 ppm or less in conversion of sulfur atom, and the ether structure content in a composition is 5 weight% or more.

The sulfonic acid and / or sulfonic acid ester content in the present composition is preferably 50 ppm or less, more preferably 30 ppm or less, even more preferably 20 ppm or less, particularly preferably 10 ppm or less in terms of sulfur atoms.

In addition, the ether structure content in the present composition is preferably at least 7% by weight, more preferably at least 10% by weight, even more preferably at least 15% by weight, particularly preferably at least 20% by weight.

The sulfonic acid and / or sulfonic acid ester component contained in a trace amount in the conventional methacrylic resin composition is one of the factors of discoloration over time, that is, the presence of the sulfonic acid and / or sulfonic acid ester component is responsible for the decrease in light resistance. It is a point which is not known at all until now, and what suppresses the fall of light resistance by introducing an ether structure is not known at all. Further, it was found that by optimizing these two factors, it is possible to drastically suppress the decrease in light resistance. And based on the present knowledge obtained by the present inventors, the content of sulfonic acid and / or sulfonic acid ester in the composition is lowered to an extremely low level of 100 ppm or less in terms of sulfur atoms, and at least 5% by weight of ether structure in the composition. It was found that the transparent inorganic material level provides a transparent plastic having extremely excellent colorless transparency and light resistance, and also excellent heat resistance, dimensional stability, surface hardness and moldability.

In the method for producing a curable composition for an optical component of the present invention, the sulfonic acid and / or sulfonic acid ester content in the composition is 100 ppm or less in terms of sulfur atoms, and the ether structure content in the composition is 5% by weight or more, It will not specifically limit, if it is a method which adjusted various manufacturing conditions.

The curable composition for an optical part of the present invention preferably contains a (meth) acrylic acid ester (A), a polymer of (meth) acrylic acid ester, and / or a compound containing no two or more hydroxyl groups per molecule, containing no aromatic hydrocarbon structure. It can be obtained by mixing the copolymer (B), and other optional components. In addition, by partially polymerizing the polymer and / or copolymer (B) of the (meth) acrylic acid ester, a mixture of the (meth) acrylic polymer and / or copolymer and the (meth) acrylic monomer is prepared, and further contains an aromatic hydrocarbon structure. Can be obtained by mixing the (meth) acrylic acid ester (A) and other optional components of the compound having two or more hydroxyl groups per molecule. Furthermore, the polymer and / or copolymer of the (meth) acrylic acid ester which has a functional group are obtained by partial polymerization, and it mixes and reacts the methacrylate which has the other functional group which can react with the functional group, and contains an aromatic hydrocarbon structure. And (meth) acrylic acid esters of compounds having two or more hydroxyl groups per molecule (A), polymers and / or copolymers of (meth) acrylic acid esters (B), and other optional components .

As a means for making the amount of sulfonic acid and / or sulfonic acid ester in the curable composition for optical parts 100 ppm or less in terms of sulfur atoms, for example, the following means may be mentioned.

(1) The use of sulfonic acid and / or sulfonic acid ester components is prohibited in all production steps until a curable composition for an optical part is obtained.

(2) In the manufacturing process of the curable composition for an optical part, when using a sulfonic acid and / or a sulfonic acid ester component, the process of fully removing a sulfonic acid and / or a sulfonic acid ester component is performed.

As said means (1), it is a sulfonic acid and / or sulfide as a catalyst used, for example, when manufacturing the (meth) acrylic acid ester (A) of a compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule. Prohibiting use of a phonic acid ester is mentioned.

As described above, in the industrial production process of the (meth) acrylic acid ester (A) of a compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule, a sulfonic acid catalyst as a catalyst from a problem such as production cost. It is common and common practice to carry out the dehydration condensation method using p-toluenesulfonic acid (in particular, a transesterification method using a dehydration condensation method using a sulfonic acid catalyst (for example, a metal alcoholate or the like) as a catalyst). The production of (meth) acrylic acid esters (A) of compounds having no two or more hydroxyl groups per molecule without containing an aromatic hydrocarbon structure is almost done industrially due to problems such as manufacturing cost. not. Therefore, in the above means (1), the use of sulfonic acid derivatives as a catalyst for the production of (meth) acrylic acid esters (A) of compounds having no two or more hydroxyl groups per molecule without containing an aromatic hydrocarbon structure Avoiding this may be disadvantageous compared with the conventional one in terms of manufacturing cost and the like. Therefore, according to the present invention, a transparent plastic having excellent colorless transparency and light resistance, which is excellent in compensating for such disadvantages, that is, a transparent inorganic material level, and also excellent in heat resistance, dimensional stability, surface hardness, and moldability is provided. It can express the effect of providing.

As a method for curing the curable composition for optical parts of the present invention into a cured product, a conventionally known curing method of the curable resin composition can be applied, and can be performed by, for example, heating or irradiation of an active ether wire. Although taking into consideration the properties of the curable (meth) acrylic resin composition and the like, it is preferable to use active energy rays or heat such as electromagnetic waves, ultraviolet rays, visible rays, infrared rays, electron beams, and gamma rays.

In this invention, it is preferable that the curable composition hardened | cured in order to obtain an optical component contains a photoinitiator (C1) and a thermal-polymerization initiator (C2) further for the same reason as mentioned above, and of the composition in this case It is preferable to harden | cure by irradiating an active energy ray.

In the case of curing by ultraviolet rays, it is preferable to use a light source containing light in the wavelength range of 150 to 450 nm. As such a light source, sunlight, a low pressure mercury lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp, a gallium lamp, a xenon lamp, a carbon arc lamp, etc. are preferable. Together with these light sources, it is also possible to use heat by infrared rays, far infrared rays, hot air, high frequency heating and the like together.

The curing of the electron beam preferably has a lower limit of the acceleration voltage of 10 kV or more, more preferably 20 kPa or more, even more preferably 30 kPa or more, and an upper limit of the acceleration voltage of 500 kW or less, and more preferably 300 kPa or less. More preferably, an electron beam of 200 kPa or less may be used. The lower limit of the irradiation amount of the electron beam is preferably 2 kGy or more, more preferably 3 kGy or more, even more preferably 5 kGy or more, even more preferably 500 kGy, more preferably 300 kGy or less, further preferably 200 kGy. The following is even more preferable. It is also possible to use heat together with infrared rays, far infrared rays, hot air, high frequency heating, etc. together with the electron beam.

When hardening the curable composition for optical components by irradiating an active energy ray, the temperature is not specifically limited, Preferably it is -20-150 degreeC, More preferably, it is 0-120 degreeC, More preferably, it is 20-100 degreeC to be.

In the present invention, the curable composition for an optical part includes the above-described thermal polymerization initiator and, if necessary, a thermal polymerization accelerator to form a thermosetting (meth) acrylic resin composition which is cured at room temperature or by heating.

When hardening the curable composition for optical components at room temperature, as a minimum, -20 degreeC or more is preferable and as an upper limit, 50 degreeC or less is preferable. If the curing temperature is lower than -20 ° C, the curing speed may be remarkably lowered, resulting in poor productivity, or incomplete curing, resulting in poor physical properties of the cured product. Moreover, when hardening temperature exceeds 50 degreeC, since hardening advances rapidly, there exists a possibility that a problem, such as foaming and a crack, or a molded article bends in hardened | cured material may arise. As a minimum, 0 degreeC or more is more preferable, and as an upper limit, 40 degreeC or less is more preferable.

When hardening a thermosetting (meth) acrylic-type resin composition by heating, 40 degreeC or more is preferable at the minimum, and 180 degrees C or less is preferable at the upper limit. If the curing temperature is lower than 40 ° C., the curing speed may be remarkably lowered, resulting in poor productivity, or incomplete curing, resulting in poor physical properties of the cured product. Moreover, when hardening temperature exceeds 180 degreeC, since hardening advances rapidly, there exists a possibility that a problem, such as foaming and a crack, or a molded article bends in hardened | cured material may arise. As a minimum, 50 degreeC or more is more preferable, 60 degreeC or more is still more preferable, As an upper limit, 150 degreeC or less is more preferable, and 120 degreeC or less is further more preferable.

The hardened | cured material obtained by hardening | curing the curable composition for optical components of this invention is the (meth) acrylic acid ester compound (A) and polyfunctional (meth) acryl of the compound which has two or more hydroxyl groups per molecule which does not contain an aromatic hydrocarbon structure. In addition to being a (meth) acrylic resin cured product obtained by curing a (meth) acrylic resin composition containing a rate, and having the aforementioned properties, the transparent inorganic material level has excellent colorless transparency and light resistance and heat resistance. It is a transparent plastic with excellent dimensional stability, surface hardness and formability.

Example

Although an Example and a comparative example demonstrate this invention further more concretely below, this invention is not limited to these.

Synthesis Example 1

135 g of fully dehydrated neopentyl glycol (hereinafter abbreviated as NPG) and a methyl methacrylate (hereinafter abbreviated as MMA) in a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube. ) 400 g, potassium t-butoxide (hereinafter abbreviated as t-BuOK) 1.35 g and 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-octyl (hereafter 4H-TEMPO) 13.5 mg was added and stirred, and it heated up at 110 degreeC. Only methanol produced by the reaction was distilled off and transesterification was carried out over 4 hours. The unreacted MMA was distilled from the obtained reaction solution, and then washed with water to remove unreacted neopentyl glycol, neopentyl glycol monomethacrylate and the catalyst to obtain neopentyl glycol dimethacrylate. This was made into compound (M-1).

The sulfur atom content in the obtained compound (M-1) was measured by Inductively Coupled Plasma (hereinafter abbreviated as ICP). No sulfur atom was observed.

Synthesis Example 2

311 g of ethylene oxide 4-mole adduct (hereinafter abbreviated as NPG-4EO) to a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube (hereinafter abbreviated as NPG-4EO), MMA 400 g, 6.22 g of dibutyltin oxide (hereinafter abbreviated as DBTO) and 31.1 mg of 4H-TEMPO were added thereto, stirred, and the mixture was heated to 100 ° C. Only methanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. After distilling MMA from the obtained reaction liquid, ethylene oxide dimethacrylate to neopentyl glycol was obtained. This was referred to as compound (M-2).

When the content rate of the sulfur atom contained in the obtained compound (M-2) was measured by ICP, the sulfur atom was not observed.

Synthesis Example 3

NPG-4EO 311 g, MMA 400 g, t-BuOK 3.11 g and 31.1 mg 4H-TEMPO were added to a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, and stirred at 110 ° C. It heated up as. Only methanol produced by the reaction was distilled off and transesterification was carried out over 4 hours. MMA was distilled from the obtained reaction liquid to obtain dimethacrylate of ethylene oxide adducts for neopentyl glycol. This was made into compound (M-3).

When the content rate of the sulfur atom contained in obtained compound (M-3) was measured by ICP, the sulfur atom was not observed.

Synthesis Example 4

A flask equipped with a stirring apparatus, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube was washed three times with 311 g of NPG-4EO, 189 g of methacrylic acid (hereinafter abbreviated as MAA), toluene and water three times. 25 g of dried cation exchange resin (manufactured by Organo Corporation, Anbarist 15D), 50 g of toluene and 31.1 mg of 4H-TEMPO were added thereto, and the mixture was stirred, and the temperature was raised to 110 ° C. The water produced by the reaction was distilled off and transesterification was carried out over 6 hours. After completion of the reaction, the cation exchange resin was removed by filtration, and toluene and unreacted MAA were further removed by heating and decompression to obtain dimethacrylate of ethylene oxide adducts for neopentylglycol. This was made into compound (M-4).

The content of sulfur atoms contained in the obtained compound (M-4) was measured by ICP, and the content of sulfur atoms was 7 ppm.

Synthesis Example 5

In a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, 311 g of NPG-4EO, 189 g of methacrylic acid (hereinafter abbreviated as MMA), and p-toluenesulfonic acid ( Hereinafter, 10 g of PTS), 50 g of toluene, and 31.1 mg of 4H-TEMPO were added thereto, stirred, and the temperature was raised to 110 ° C. The water produced by the reaction was distilled off and dehydration esterification was carried out over 6 hours. After completion of the reaction, washing with water and standing to separate the aqueous layer part was repeated three times. Toluene and unreacted MAA were removed by heating and decompression to obtain dimethacrylate of ethylene oxide adducts for neopentyl glycol. This was made into compound (M-5).

The content of sulfur atoms contained in the obtained compound (M-5) was measured by ICP, and the content of sulfur atoms was 340 ppm.

Synthesis Example 6

Into a flask equipped with a stirrer, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, 311 g of NPG-4EO, 400 g of ethyl acrylate, 6.22 g of DBTO and 31.1 mg of 4H-TEMPO were added to the flask and stirred at 110 ° C. It heated up. Only ethanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. Ethyl acrylate was distilled off from the reaction solution to obtain diacrylate of ethylene oxide adducts for neopentyl glycol. This was made into compound (M-6).

When the content rate of the sulfur atom contained in obtained compound (M-6) was measured by ICP, the sulfur atom was not observed.

Synthesis Example 7

To a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, 339 g of a compound containing 2 moles of neopentyl glycol ethylene oxide and 2 moles of propylene oxide, 400 g of MMA, 6.78 g of DBTO, and 4H -33.9 mg of TEMPO was added and stirred, and the temperature was raised to 110 ° C. Only methanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. MMA was distilled from the obtained reaction liquid to obtain dimethacrylate of ethylene oxide and propylene oxide adducts for neopentyl glycol. This was made into compound (M-7).

When the content rate of the sulfur atom contained in obtained compound (M-7) was measured by ICP, no sulfur atom was observed.

Synthesis Example 8

In a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, 336 g of an ethylene oxide 4-mole adduct of butylethylpropanediol, 400 g of MMA, 6.72 g of DBTO, and 33.6 mg of 4H-TEMPO were added. It put and stirred, and it heated up at 110 degreeC. Only methanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. MMA was distilled from the obtained reaction liquid to obtain dimethacrylate of ethylene oxide adducts for butylethylpropanediol. This was made into compound (M-8).

When the content rate of the sulfur atom contained in obtained compound (M-8) was measured by ICP, the sulfur atom was not observed.

Synthesis Example 9

Into a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, 530 g of ethylene oxide 9 mole adduct of trimethylolpropane, 600 g of MMA, 10.6 g of DBTO and 53.0 mg of 4H-TEMPO were added. It stirred and heated up at 110 degreeC. Only methanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. MMA was distilled from the obtained reaction liquid and the trimethacrylate of 9 mol addition products of ethylene oxide with respect to trimethylolpropane was obtained. This was taken as compound (M-9).

When the content rate of the sulfur atom contained in obtained compound (M-9) was measured by ICP, no sulfur atom was observed.

Synthesis Example 10

To a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, 200 g of polyethylene glycol (number average molecular weight 200), 400 g of MMA, 4.0 g of DBTO and 20.0 mg of 4H-TEMPO were stirred. , The temperature was raised to 110 ° C. Only methanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. MMA was distilled from the obtained reaction liquid to obtain polyethylene glycol dimethacrylate. This was made into compound (M-10).

When the content of sulfur atoms contained in the obtained compound (M-10) was measured by ICP, sulfur atoms were not observed.

Synthesis Example 11

487 g of neopentyl glycol ethylene oxide 8 mole adduct (hereinafter abbreviated as NPG-8EO) to a flask equipped with a stirring device, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube (hereinafter abbreviated as NPG-8EO), MMA 400 g, DBTO 9.74 g and 48.7 mg of 4H-TEMPO were added and stirred, and the temperature was raised to 110 ° C. Only methanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. MMA was distilled from the obtained reaction liquid to obtain dimethacrylate of ethylene oxide adducts for neopentylglycol. This was made into compound (M-11).

When the content rate of the sulfur atom contained in obtained compound (M-11) was measured by ICP, the sulfur atom was not observed.

Synthesis Example 12

Into a flask equipped with a stirrer, a thermometer, a condenser, and an air and nitrogen mixed gas introduction tube, 228 g of an ethylene oxide 2 mole adduct of bisphenol A, 400 g of MMA, 4.56 g of DBTO, and 22.8 mg of 4H-TEMPO were added to the flask. And it heated up at 110 degreeC. Only methanol produced by the reaction was distilled off and transesterification was carried out over 6 hours. MMA was distilled from the obtained reaction liquid to obtain dimethacrylate of ethylene oxide adducts for bisphenol A. This was made into compound (M-12).

When the content rate of the sulfur atom contained in obtained compound (M-12) was measured by ICP, the sulfur atom was not observed.

Synthesis Example 13

190 g of MMA, 8.6 g of MAA, and 463 g of toluene were added to a flask equipped with a stirring apparatus, a thermometer, a condenser, and a mixed gas introduction tube of air and nitrogen, and nitrogen-substituted, and the temperature was raised to 70 ° C. Then, a solution obtained by diluting 0.99 g of 2,2'-azobis (2,4-dimethylvaleronitrile) (Wako Pure Chemical Industries, Ltd. V-65) in 50 g of toluene was slowly added dropwise while paying attention to exotherm. After reacting at 70 ° C for 3 hours, the mixture was reacted at 90 ° C for 2 hours to complete radical polymerization.

Then, 0.68 g of methoxy, 156 g of methacrylic acid glycidyl and 2.71 g of tetraphenylphosphonium bromide were added, and the temperature was raised to 100 ° C. while blowing a mixed gas of air and nitrogen until the acid value became 5 or less. The reaction was carried out. The polymer solution obtained was reprecipitated in n-hexane, and then n-hexane was removed under reduced pressure to obtain compound (P-1).

The molecular weight of the obtained compound (P-1) was measured by gel permeation chromatography (GPC), and the number average molecular weight (Mn) was 35,000 and the weight average molecular weight (Mw) was 78,000.

In addition, when the content rate of the sulfur atom contained in obtained compound (P-1) was measured by ICP, the sulfur atom was not observed.

Synthesis Example 14

In a flask equipped with a stirring device, a thermometer, a condenser and a nitrogen introduction tube, 85 g of MMA, 15 g of polyethylene glycol monomethyl ether methacrylate (Wako Pure Chemical Industries, Ltd., trade name NK ester M-90G), toluene 100 g was added and nitrogen-substituted, and it heated up at 70 degreeC. Then, a solution obtained by diluting 1.5 g of 2,2'-azobis (2,4-dimethylvaleronitrile) (Wako Pure Chemical Industries, Ltd. V-65) in 50 g of toluene was slowly added dropwise while paying attention to exotherm. After 4 hours of reaction at 70 ° C, the reaction was completed at 90 ° C for 1 hour to complete the radical polymerization. The polymer solution obtained was reprecipitated in n-hexane, and then n-hexane was removed under reduced pressure to obtain compound (P-2).

The molecular weight of Compound (P-2) obtained was measured by gel permeation chromatography (GPC). The number average molecular weight (Mn) was 14,000 and the weight average molecular weight (Mw) was 25,000.

In addition, sulfur content was not observed when the content rate of the sulfur atom contained in obtained compound (P-2) was measured by ICP.

15 to composite

The flask equipped with a stirring device, a thermometer and a condenser was washed three times each with 145 g of tetramethoxysilane, 23.6 g of γ-methacryloxypropyltrimethoxysilane, 19 g of water, 30 g of methanol, and toluene and water, respectively. 5.0 g of Anvalist 15 (registered trademark) (Rom and Haas Japan cation exchange resin) was added, and the mixture was stirred at 65 ° C for 2 hours to react. Subsequently, the condenser was replaced with a distillation column, the temperature was raised to 90 ° C., methanol was distilled off, and the ion exchange resin was filtered to obtain a polymerizable polysiloxane.

200 g of toluene was put in the flask equipped with the stirring apparatus, the thermometer, the condenser, the dropping port, and the gas introduction tube, nitrogen gas was introduced, and the internal temperature was raised to 100 ° C while stirring. Subsequently, a solution obtained by mixing 20 g of the polymerizable polysiloxane obtained above, 180 g of MMA, and 6 g of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours to the polymerization. After completion of the dropwise addition, the reaction was carried out at the same temperature for 4 hours to obtain an organic polymer solution.

Subsequently, 200 g of butyl acetate and 50 g of methanol were put into the flask provided with the stirring apparatus, the thermometer, the condenser, and two dropping ports, and the internal temperature was adjusted to 20 degreeC. While stirring the flask, a mixture of 20 g of the organic polymer solution obtained above, 30 g of tetramethoxysilane, and 30 g of butyl acetate was added from one dropping drop to another dropping mixture of 20 g of 25% aqueous ammonia and 20 g of methanol. Was dripped over 1 hour from the. After dripping, stirring was continued for 2 hours at the same temperature to obtain an organic polymer composite silica fine particle dispersion (S-1).

Examples 1-19, Comparative Examples 1-3

In the compounding ratios shown in Tables 1 and 2, the curable compositions for optical parts of Examples 1 to 19 and Comparative Examples 1 to 6 were combined.

The curable compositions of Examples 1-18 and Comparative Examples 1-3 were fully mixed in the ratio as shown in Tables 1 and 2 to make a uniform solution. The curable composition of Example 19 was sufficiently mixed in the ratio as shown in Table 2, and then heated and reduced to remove the solvent, thereby obtaining a curable composition in which the inorganic fine particles were dispersed. About these curable compositions, ether structure content and sulfonic acid and / or sulfonic acid ester content were measured by the following method. Moreover, the sheet-like optical component was shape | molded by the following hardening method, and this molded object was subjected to the accelerated weathering test as follows. Yellow index change rate, volume shrinkage rate and water absorption rate were measured.

These results are summarized in Table 1 and Table 2. In addition, what was abbreviated and described in Table 1 and Table 2 is a compound shown below, respectively.

D-1173: 2-hydroxy-2-methyl-1-phenylpropan-1-one (made by Chiba Specialty Chemicals, brand name: Tarocure 1173)

PBO: t-butylperoxy-2-ethylhexanoate (made by Nippon Yushi Co., Ltd., brand name: Patch Roll O)

PMMA: Polymethyl methacrylate (manufactured by Sumitomo Chemical Co., Ltd., brand name: Smipex LG-6A)

PEG200: polyethylene glycol (average molecular weight 200) made by Wako Pure Chemical Industries, Ltd.

PF-656: fluorine-based surfactant (manufactured by Omnova Corporation, trade name Polyfox)

ot-100: Dioctyl sulfosuccinate sodium (made by Cytec Corporation)

HSTA: 12-hydroxystearic acid

<Measurement method of ether structure content>

15 mg of curable composition and 200 mg of 45% hydrobromic acid were placed in a 5 ml aluminal vial, sealed through Teflon® silicone septam, heated in an oven at 150 ° C. for 2 hours to carry out bromic acid decomposition reaction. It was. Dibromoethane produced by bromination of ether structures such as polyethylene glycol, polypropylene glycol, polybutylene glycol, polytetramethylene glycol, 1,2-dibromopropane, 1,2-dibromobutane, 1, Based on the calibration curve which 4-dibromobutane etc. were made previously, it quantified by gas chromatography and the ether structure content in curable composition was measured.

<Measurement method for sulfonic acid and / or sulfonic acid ester content>

The curable composition was dissolved in toluene and water was added to extract the sulfonic acid and / or sulfonic acid salt into the separating lot. The aqueous layer containing sulfonic acid and / or sulfonic acid salt was separated, concentrated in an evaporator, further dehydrated in a hot air dryer, redissolved in acetone, and the amount of sulfonic acid was measured by gas chromatography.

Subsequently, water was further added to the toluene layer containing the curable composition separated by the separating lot, and the sulfonic acid ester was decomposed into sulfonic acid by heating and stirring at 100 ° C for 10 hours. Into a separating lot, only the aqueous layer was taken out and concentrated by an evaporator. Further, after removing water completely in a hot air dryer, it was redissolved in acetone and the amount of sulfonic acid ester was quantified by gas chromatography. The sulfonic acid and / or sulfonic acid ester content in curable composition was calculated | required in conversion of sulfur atom from the sum total of the sulfonic acid amount and sulfonic acid ester quantity calculated | required previously.

<Hardening method>

Thermosetting: A methacryl-based resin composition containing a thermal initiator was injected into a case in which a spacer of 1 mm thick silicone rubber was sandwiched between two glass plates, and then cured slowly in hot water at 60 ° C. for 1 hour. Furthermore, after postcure over 2 hours in a 110 degreeC dryer, the glass plate was removed and the 1-mm-thick sheet-like optical component (molded object) was obtained.

Ultraviolet (UV) curing: A 1 mm thick silicone rubber spacer was placed on a glass plate, and a methacrylic resin composition containing a photopolymerization initiator was introduced into a portion wrapped with the spacer. A 250 μm-thick PET film was coated thereon, and a sheet-shaped optical component (molded product) was obtained by irradiating 93.2 seconds of ultraviolet light having a dominant wavelength of 365 nm and an irradiation intensity of 43 mJ / cm 2 · second using a 250 mW ultrahigh pressure mercury lamp. .

<Promoting Weather Resistance Test>

6 hours (irradiation intensity 100 mW / cm 2, wavelength 295-450 nm, humidity 70% Rh, temperature 60 ° C) and condensation 6 hours using a super-energy irradiation tester (Suga Test Instruments Co., Ltd.) (Humidity 90% Rh or more, temperature 30 degreeC), 10 cycles (that is, 120 minutes) were tested using this as 1 set.

Discoloration of the test pieces before and after the test in the transmission mode using a color difference meter (Japanese Sigma Co., Ltd., Sigma 90 system) was measured and expressed as a yellow index change rate (ΔY1).

In addition, the discoloration in 10 cycles of the accelerated weathering test was almost equivalent to the discoloration of 2.5 years in the actual outdoor exposure test.

<Measurement of volumetric shrinkage rate>

In accordance with JIS K 6901, the density before curing (a) and the density after curing (b) of the curable composition were measured using a hydrometer (Toyoseiki Kyogo Co., Ltd., automatic hydrometer D-H01 type), Thus, volumetric shrinkage was obtained.

Volume Shrinkage (%) = [(density after hardening (b)-density before hardening (a)) / density after hardening (b)] × 100

〈Measurement of Absorption Rate〉

Except having made the size of the test piece into 40 mm x 40 mm x 1 mm, the mass (W1) of the test piece before absorption and the mass (W2) of the test piece after absorption were measured according to JIS K 6911, and the water absorption was calculated | required by the following formula.

Absorption rate (%) = [(mass of specimen after absorption (W2)-mass of specimen before absorption (W1)) / mass of specimen before absorption (W1)] × 100

According to the present invention, it is transparent and hardly causes coloring, discoloration or deterioration even with respect to light from a light source having a light emission wavelength distribution in an ultraviolet region in a short wavelength region of visible light, and excellent in dimensional stability, moldability and water resistance of a cured product. A curable composition can be provided.

Since the curable composition for optical parts of the present invention has a colorless transparency and light resistance which is very excellent in the level of a transparent inorganic material, and becomes a material of a transparent plastic which is also excellent in dimensional stability, moldability and water resistance of the cured product, the level of a transparent inorganic material is high. For applications requiring very good colorless transparency and light resistance, for example, optical parts used outdoors directly exposed to sunlight, such as solar cells or outdoor billboards, or light sources having an emission wavelength distribution in the ultraviolet region in the short wavelength region of visible light. It can be used suitably for various uses, such as optical components, such as a light emitting diode, an optical cable, and a display apparatus which use this.

Claims (10)

A composition comprising (meth) acrylic acid ester (A) of a compound having no two or more hydroxyl groups per molecule without containing an aromatic hydrocarbon structure, wherein the content of the ether structure of the formula (1) Curable composition for optical parts, characterized in that the content of sulfonic acid or sulfonic acid ester in the composition is 100 ppm or less in terms of sulfur atoms. [Formula 1] -(O-CH ₂ -CHR ¹ ) _n- In the above formula, n = 1 to 100 and R ¹ is one or two or more selected from hydrogen, a methyl group and an ethyl group. The (meth) acrylic acid ester of a compound according to claim 1, wherein the (meth) acrylic acid ester (A) of the compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule does not contain β hydrogen to the hydroxyl group. Curable composition for optical components characterized by being a cargo. The (meth) acrylic acid ester compound (A) of the compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule has two or more ether structures represented by the formula (1) in the molecule. It is (meth) acrylic acid ester compound of the compound which has a hydroxyl group, The curable composition for optical components characterized by the above-mentioned. The (meth) acrylic acid ester compound (A) of the compound according to claim 1 or 3, which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule, has an ethylene oxide in a compound having two or more hydroxyl groups per molecule. And (meth) acrylic acid esters of compounds to which one or two or more alkylene oxides selected from propylene oxide and butylene oxide are added. 5. The (meth) acrylic acid ester compound (A) of the compound according to claim 4, which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule, contains two or more hydroxyl groups per molecule without containing β hydrogen to the hydroxyl group. The curable composition for optical components of Claim 1 which is a (meth) acrylic acid ester compound of the compound which added 1 type, or 2 or more types of alkylene oxides chosen from ethylene oxide, a propylene oxide, and butylene oxide to the possessed compound. The curable composition for an optical part according to claim 1, further comprising a polymer or copolymer (B) of (meth) acrylic acid ester. The polymer or copolymer (B) of the (meth) acrylic acid ester is polymerizable with (meth) acrylic acid ester (A) of a compound which does not contain an aromatic hydrocarbon structure and has two or more hydroxyl groups per molecule. Curable composition for optical components characterized by having a reactor. The curable composition for an optical part according to claim 1, further comprising a photopolymerization initiator (C1) and a thermal polymerization initiator (C2). The curable composition for an optical part according to claim 1, further comprising inorganic fine particles (D). The curable composition for an optical part according to claim 1, which is used for a light source having a light emission wavelength distribution ranging from a short wavelength region of visible light to an ultraviolet region.