JP2013181076A - (meth)acrylate-based composition, resin, and molded article - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a (meth)acrylate-based composition having excellent processability because of high viscosity while keeping favorable heat resistance, shape stability and optical performance such as refractive index or transparency; and to provide a resin obtained from the composition, and a molded article obtained by molding the resin.SOLUTION: A (meth)acrylate-based composition includes a (meth)acrylate compound (A) having an adamantyl group represented by general formula (I), a (meth)acrylate compound (B) represented by general formula (II) and a (meth)acrylate compound (C) represented by general formula (III).

Description

  The present invention relates to a (meth) acrylate composition, a resin obtained by polymerizing the composition, and a molded body formed by molding the resin. Specifically, a (meth) acrylate-based composition that is a resin raw material for optical parts, including a (meth) acrylate compound having an adamantyl group, a resin for optical parts obtained by polymerizing the composition, and molding the resin The present invention relates to an optical component.

  As the transparent resin, polymethyl methacrylate resin, polycarbonate resin, polystyrene resin, alicyclic olefin polymer, epoxy resin and the like are known. These transparent resins are produced in large quantities industrially and are used in large quantities in various fields by taking advantage of their good transparency.

In addition to its good transparency, transparency resin is used as a substitute for glass by taking advantage of its light weight and moldability, and can be applied to lenses for camera modules mounted on camera phones. It has been. Here, reflecting the recent miniaturization and reduction in the number of parts, a transparent resin that can withstand the solder reflow process is desired. To that end, in addition to optical characteristics such as light transmittance, extremely high heat resistance Sex is required.
However, the above-described transparent resin does not necessarily have sufficient heat resistance. For example, among the above transparent resins, even a polycarbonate resin, which is considered to have the highest heat resistance, has a glass transition temperature of about 150 ° C., which is an index of heat resistance, and development of a new transparent resin having higher heat resistance. Is desired.

  Polymethyl acrylate, which is known as a transparent resin, is inferior in performance such as heat resistance, heat stability, and solvent resistance, and has high water absorption and poor water resistance. It cannot be used in certain fields. Polymethylmethacrylate is used for a resin material for optical parts, but cannot be applied to fields that require extremely high heat resistance and heat stability that can withstand a solder reflow process.

  As a method for improving such a problem, a polycyclic alicyclic alkyl (meth) acrylate homopolymer, a polycyclic alicyclic alkyl (meth) acrylate and various (meth) acrylate monomers A method using a resin composition for an optical material containing a copolymer has been proposed (see, for example, Patent Document 1). The material disclosed in Patent Document 1 is excellent in heat resistance while maintaining excellent transparency.

JP 2006-213851 A

  Such an optical component is produced through a manufacturing process in which a liquid composition at room temperature is placed in a mold and cured by heating, pressurizing, or the like. At this time, if the viscosity of the liquid composition used as the raw material of the optical component is small, the composition leaks from the clearance between the mold and the tool when the composition is injected into the mold and pressurized. May end up. Such an adverse effect can be prevented by using a mold having a special structure. However, there is a demand for a method of manufacturing an optical component that can prevent the phenomenon that the composition leaks from the clearance without using such a special mold.

When a special mold is not used, it is conceivable to increase the viscosity of the composition in order to prevent the phenomenon of the composition leaking from the clearance. As a means for increasing the viscosity of the composition, a method of increasing the molecular weight of each component contained in the composition is conceivable. However, if the molecular weight of each component is increased, the crosslinking reaction at the time of curing hardly proceeds, and the resulting cured product is obtained. Since the crosslinking density of the cured product becomes low, the heat resistance and shape stability of the cured product, and the optical performance such as the refractive index and transparency often deteriorate. In addition, a method of blending a polymer component in the composition is also conceivable, but since the crosslinking density of the cured product is further lowered, there is a problem that the heat resistance, shape stability, and linear expansion coefficient of the cured product are deteriorated. is there.
In addition, in said patent document 1, the examination about the means which prevents the phenomenon in which a composition leaks from clearance without using a special metal mold | die is not performed.

  The present invention has been made in view of the above problems, and has excellent workability because of its high viscosity while maintaining good heat resistance, shape stability, and optical performance such as refractive index and transparency. It is an object of the present invention to provide a (meth) acrylate-based composition, a resin obtained from the composition, and a molded body obtained by molding the resin.

The present inventors have found that a composition containing a (meth) acrylate compound having a relatively bulky group together with a (meth) acrylate compound having an adamantyl group can solve the above-mentioned problems, and completed the present invention. did.
That is, the present invention provides the following [1] to [10].

[1] A (meth) acrylate compound (A) having an adamantyl group represented by the following general formula (I), a (meth) acrylate compound (B) represented by the following general formula (II), and the following general formula The (meth) acrylate type composition containing the (meth) acrylate compound (C) represented by (III).

(In the formula (I), each R ¹ independently represents a hydrogen atom or a methyl group, and each X independently represents a single bond, an alkylene group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms. Represents an oxyalkylene group, U represents an alkyl group having 1 to 4 carbon atoms, a halogen group, a hydroxyl group, or two U formed together, k represents an integer of 0 to 15, and m represents 1 Represents an integer of ~ 4.)

(In the formula (II), each R ² independently represents a hydrogen atom or a methyl group, and Y ¹ represents a substituted or unsubstituted acyclic hydrocarbon group having 5 to 30 carbon atoms and / or —R. An acyclic organic group containing a group represented by '(OR') _L- (wherein R 'each independently represents a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms, and L is 1 And n is an integer of 1 to 8.)

(In the formula (III), each G independently represents a single bond, an alkylene group having 1 to 4 carbon atoms, or an oxyalkylene group having 1 to 4 carbon atoms, and each R ⁴ independently represents a hydrogen atom. Or a methyl group, and each R ⁵ independently represents an alkylene group having 1 to 4 carbon atoms or an alkylene group having 1 to 4 carbon atoms substituted with a hydroxy group, and a represents an integer of 2 to 8. And b are each independently a positive number of 1 to 4. Z represents an organic group represented by the following formulas (III-1) to (III-11).

(In the above formula, each R ⁶ is independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, and R ⁷ is each independently a divalent organic group. In addition, p represents an integer of 0 to 4, q represents an integer of 0 to 3, and * represents a bonding portion.)

[2] The (meth) acrylate composition according to [1], wherein the content of the component (C) is 30 to 85% by mass with respect to the total amount of the components (A) to (C).
[3] Further, as the component (D), a reaction compound (D1) of an epoxy compound and (meth) acrylic acid and / or a urethane (meth) acrylate compound (D2) other than the compound corresponding to the component (C) is included. The (meth) acrylate composition according to [1] or [2] above.
[4] The (meth) acrylate composition according to [3], wherein the content of the component (D) is 2 to 50 parts by mass with respect to 100 parts by mass of the total of the components (A) to (C). object.
[5] The (meth) acrylate composition according to any one of [1] to [4], wherein the (meth) acrylate composition has a viscosity at 25 ° C. of 500 to 50,000 mPa · s.
[6] A resin obtained by polymerizing the (meth) acrylate composition according to any one of [1] to [5].
[7] A molded product obtained by molding the resin according to [6].
[8] The molded article according to [7], wherein the molded article has a total light transmittance of 85% or more.
[9] The molded body according to claim 7 or 8, wherein the molded body has a refractive index of 1.45 to 1.65 at the d-line.
[10] The molded body according to any one of [7] to [9], wherein the molded body is an optical component.

  The (meth) acrylate composition of the present invention has excellent workability because of its high viscosity while maintaining good heat resistance and shape stability, and optical performance such as refractive index and transparency. Therefore, by using the above composition, it is possible to improve the productivity and produce a molded body such as an optical component without using a special mold or the like.

[(Meth) acrylate-based composition]
The (meth) acrylate-based composition of the present invention (hereinafter also simply referred to as “composition”) is a (meth) acrylate compound (A) having an adamantyl group represented by the general formula (I), the general formula (II) The (meth) acrylate compound (B) represented by general formula (III), the (meth) acrylate compound (C) which has an isocyanurate structure are included.
In addition, the composition of the present invention preferably further contains a reaction compound (D1) of an epoxy compound and (meth) acrylic acid and / or a urethane (meth) acrylate compound (D2). You may mix | blend other additives, such as an inhibitor, a polymerization initiator, and a light stabilizer.

Hereinafter, each component contained in the (meth) acrylate composition of the present invention will be described in detail.
In the present specification, the (meth) acrylate compound is used to mean both an acrylate compound and a methacrylate compound (and other synonymous terms are also the same).

[(A) component: (meth) acrylate compound (A) having an adamantyl group represented by formula (I)]
The composition of this invention contains the (meth) acrylate compound which has an adamantyl group represented by the following general formula (I) as (A) component. The component (A) mainly becomes a hard segment when the composition of the present invention is polymerized into a resin, and becomes a portion having low mobility between molecules. Moreover, the heat resistance of the molded object obtained from this composition can be improved by containing (A) component.

In said formula (I), R < ¹ > shows a hydrogen atom or a methyl group each independently.
Moreover, X shows a single bond, a C1-C4 alkylene group, or a C1-C4 oxyalkylene group each independently.
Examples of the alkylene group having 1 to 4 carbon atoms include a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a butylene group, and a 2-methyltrimethylene group.
Examples of the oxyalkylene group having 1 to 4 carbon atoms include an oxymethylene group, an oxyethylene group, an oxypropylene group, and an oxybutylene group.
Among these X, a single bond is preferable from the viewpoint of improving the heat resistance of a molded product obtained from the composition.

In the above formula (I), U represents an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxyl group, or ═O formed by combining two U together.
Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, and an isobutyl group.
In addition, several U may be the same and may differ.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
In addition, k shows the number of the substituent U in an adamantyl skeleton, shows the integer of 0-15, Preferably it is an integer of 0-10.

Moreover, in said formula (I), m shows the integer of 1-4, Preferably it is an integer of 1-2.
In the general formula (I), examples of the compound in which m is 1 include adamantylmethanol (meth) acrylate and adamantylethanol (meth) acrylate.
Examples of the compound in which m is 2 include adamantyl dimethanol di (meth) acrylate, adamantyl diethanol di (meth) acrylate, and the like.
Examples of the compound in which m is 3 include adamantyltrimethanol tri (meth) acrylate and adamantyltriethanoltri (meth) acrylate.
Examples of the compound in which m is 4 include adamantyl tetramethanol tetra (meth) acrylate and adamantyl tetraethanol tetra (meth) acrylate.

These components (A) may be used alone or in combination of two or more.
As content of (A) component in the composition of this invention, from a viewpoint of improving the heat resistance of the molded object obtained from this composition, Preferably it is 5 with respect to the total amount of (A)-(C) component. -60 mass%, More preferably, it is 8-45 mass%, More preferably, it is 12-30 mass%.
In the present invention, the total amount of the components (A) to (C) does not exceed 100% by mass (the same applies hereinafter).

[Component (B): (Meth) acrylate Compound (B) Represented by General Formula (II)]
The composition of this invention contains the (meth) acrylate compound represented by the following general formula (II) as (B) component. When component (B) is a resin obtained by polymerizing the composition of the present invention, the component is mainly a soft segment that is a site having many flexible sites, and the mobility of the polymer chain is increased in the molecule. It becomes a flexible part. Moreover, generation | occurrence | production of the crack at the time of obtaining a molded object from this composition can be suppressed by containing (B) component.

In said formula (II), R < ² > shows a hydrogen atom or a methyl group each independently.
Y ¹ represents a substituted or unsubstituted acyclic hydrocarbon group having 5 to 30 carbon atoms and / or an acyclic organic group including a group represented by —R ′ (OR ′) _L — (provided that , R ′ each independently represents a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms, and L is an integer of 1 to 20). In addition, the hydrogen atom of the said acyclic hydrocarbon group and alkylene group may be substituted by the halogen atom, the hydroxyl group, the amino group, etc., for example. L is an integer of 1 to 20, preferably 2 to 15, and more preferably 2 to 10.
n represents an integer of 1 to 8, and is preferably an integer of 2 to 7, more preferably an integer of 3 to 6, from the viewpoint of improving the crosslinking density of the resin obtained from the composition of the present invention.

An acyclic group containing a substituted or unsubstituted acyclic hydrocarbon group having 5 to 30 carbon atoms and / or a group represented by —R ′ (OR ′) _L — represented by Y ¹ in the above formula (II). The organic group may have an ether bond, and may further include a linear hydrocarbon group having less than 5 carbon atoms, a branched hydrocarbon group, or the like.
The above group represented by Y ¹ is a site corresponding to the soft segment in the resin obtained from the composition, and the mobility of the polymer chain is increased in the molecule, which becomes a flexible site.

Here, when Y ¹ in the above formula (II) is a substituted or unsubstituted acyclic hydrocarbon group having 5 to 30 carbon atoms, the component (B) is represented by the following general formula (II-a) It is preferable that it is a (meth) acrylate compound (B1) represented by these.

In the above formula (II-a), R ² and n are the same as in formula (II). Q ¹ is one or more organic groups selected from a linear hydrocarbon group having 1 to 30 carbon atoms and a branched hydrocarbon group having 3 to 30 carbon atoms, and these organic groups include an ether bond. It may be substituted with a halogen atom, a hydroxyl group, an amino group or the like.
Y ² is an acyclic hydrocarbon group having 5 to 30 carbon atoms, may contain an ether bond, and may be substituted with a halogen atom, a hydroxyl group, an amino group, or the like.

Examples of the linear hydrocarbon group having 1 to 30 carbon atoms in Q ¹ in the general formula (II-a) include a methylene group, an ethylene group, an n-propylene group, an n-butylene group, and an n-pentylene group. N-hexylene group, n-heptylene group, n-octylene group, 2-ethylhexylene group, n-nonylene group, n-decylene group, n-undecylene group, n-dodecylene group, n-tridecylene group, n- An alkylene group having 1 to 30 carbon atoms such as a tetradecylene group, an n-pentadecylene group, an n-hexadecylene group, an n-heptadecylene group and an n-octadecylene group, and an oxymethylene group, an oxyethylene group, an oxypropylene group and an oxybutylene group C1-C30 oxyalkylene groups, such as, etc. are mentioned.

Examples of the branched hydrocarbon group having 3 to 30 carbon atoms in Q ¹ in the general formula (II-a) include isopropyl group, isobutyl group, s-butyl group, t-butyl group, isopentyl group, and neopentyl. Group, t-pentyl group, isohexyl group and the like.

The acyclic hydrocarbon group having 5 to 30 carbon atoms of Y ^{2 in} the general formula (II-a) is represented by, for example, — (CH ₂ ) _r1 — or — (CH ₃ CH) _r1 —. alkylene group (r1 5-30 ^{integer), - (CR c -CR d} ) r2 - propylene group (R ^c represented, while the hydrogen atoms of R ^d, the other is a methyl group, r2 is 2 15), an alkoxy group represented by — (CH ₂ O) _r3 — or — (CH ₃ CHO) _r3 — (wherein r3 is an integer of 5 to 30).
Among these, an alkylene group represented by — (CH ₂ ) _r1 — (r1 is an integer of 5 to 30), a propylene group represented by — (CR ^c —CR ^d ) _r2 — (R ^c , R ^d One is a hydrogen atom, the other is a methyl group, and r2 is preferably an integer of 2 to 15.

  Of the (meth) acrylate compound (B1) represented by the general formula (II-a), examples of the compound in which n is 2 include 1,5-pentanediol di (meth) acrylate and 1,6-hexane. Examples include diol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,12-dodecanediol dimethacrylate, polybutadiene di (meth) acrylate, and hydrogenated polybutadiene di (meth) acrylate.

  In addition, among the (meth) acrylate compounds (B1) represented by the general formula (II-a), examples of compounds in which n is 3 or more include pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, polyfunctionality, and the like. Examples include polyester (meth) acrylate.

When Y ¹ in the above formula (II) is an acyclic organic group containing a group represented by —R ′ (OR ′) _L —, the component (B) has the following general formula ( It is preferable that it is the (meth) acrylate compound (B2) represented by II-b).

In the above formula (II-b), R ² and n are the same as those in the formula (II), and Y ² is an acyclic hydrocarbon group having 5 to 30 carbon atoms as in the formula (II-a). It may contain an ether bond and may be substituted with a halogen atom, a hydroxyl group, an amino group or the like.
R ′ each independently represents a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms. L is an integer of 1-20, preferably 2-15, more preferably 2-10.

Among the (meth) acrylate compounds (B2) represented by the general formula (II-b), examples of the compound where n is 2 include diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, L 2-20 polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polybutylene glycol di (meth) acrylate, ethoxylated bisphenol A di (meth) acrylate, alkoxylated neopentyl glycol diacrylate, tetraethylene Examples include glycol di (meth) acrylate and alkoxylated cyclohexanediol diacrylate (manufactured by Sartomer Japan, Inc.).
Among these, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polybutylene glycol di (meth) acrylate, and tetraethylene glycol di (meth) acrylate having L of 2 to 20 are preferable.

  In addition, among the (meth) acrylate compounds (B2) represented by the general formula (II-b), examples of the compound in which n is 3 or more include, for example, ethoxylated trimethylolpropane tri (meth) acrylate and propoxylated tri Methylolpropane tri (meth) acrylate, alkoxylated trimethylolpropane tri (meth) acrylate with L of 2 to 20, ethoxylated glyceryl tri (meth) acrylate, propoxylated glyceryl tri (meth) acrylate, alkoxylated glyceryl tri (meth) Acrylate, ethoxylated pentaerythritol tetra (meth) acrylate, propoxylated pentaerythritol tetra (meth) acrylate, alkylated trimethylolpropane tri (meth) acrylate, alkoxylated pentaerythritol with L of 2 to 20 Rutetra (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa (meth) acrylate, alkylated dipentaerythritol hexa (meth) acrylate, alkoxylated dipentaerythritol with L of 2 to 20 Hexa (meth) acrylate, ethoxylated dipentaerythritol penta (meth) acrylate, propoxylated dipentaerythritol penta (meth) acrylate, alkylated dipentaerythritol hexa (meth) acrylate, alkoxylated dipentaerythritol penta with L of 2 or more (Meth) acrylate, alkylated dipentaerythritol penta (meth) acrylate and the like.

These components (B) may be used alone or in combination of two or more.
The content of the component (B) in the composition of the present invention is preferably relative to the total amount of the components (A) to (C) from the viewpoint of suppressing deformation and discoloration of the molded product obtained from the composition. Is 5 to 50% by mass, more preferably 10 to 45% by mass, and still more preferably 18 to 40% by mass.

  The molecular weight of the component (B) is preferably 140 to 2500, more preferably 250 to 2000, and still more preferably 350 to 1300, from the viewpoint of adjusting the viscosity of the composition and suppressing shape change after thermal history.

[(C) component: (meth) acrylate compound (C) represented by general formula (III)]
The composition of this invention contains the (meth) acrylate compound (C) represented by the following general formula (III) as (C) component. By including a compound having a bulky group such as component (C) in the composition, the viscosity of the composition can be increased. In addition, the optical performance of the molded product obtained from the composition is good, and in particular, the refractive index can be improved.

In the formula (III), each G independently represents a single bond, an alkylene group having 1 to 4 carbon atoms, or an oxyalkylene group having 1 to 4 carbon atoms, and each R ⁴ independently represents a hydrogen atom or R ⁵ represents a methyl group, and each R ⁵ independently represents an alkylene group having 1 to 4 carbon atoms or an alkylene group having 1 to 4 carbon atoms substituted with a hydroxy group. a represents an integer of 2 to 8, and b is independently a positive number of 1 to 4, preferably 1 to 3, more preferably 1 to 2. In addition, when R < ⁵ > is a C1-C4 alkylene group, the value of b shows the average value of the addition mole number of alkylene oxide each independently.
Examples of the alkylene group having 1 to 4 carbon atoms in G include a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a butylene group, and a 2-methyltrimethylene group. Examples of the oxyalkylene group 4 include an oxymethylene group, an oxyethylene group, an oxypropylene group, and an oxybutylene group.
Examples of the alkylene group having 1 to 4 carbon atoms in R ⁵ include a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a butylene group, and a 2-methyltrimethylene group.
Examples of the alkylene group having 1 to 4 carbon atoms substituted with a hydroxy group include groups in which a hydrogen atom in the groups listed as the alkylene group having 1 to 4 carbon atoms is substituted with a hydroxy group. Groups represented by formulas (III-a) to (III-c) are preferred.

（上記式（III−ａ）〜（III−ｃ）中、＊は結合部分を示す。）

(In the above formulas (III-a) to (III-c), * represents a binding moiety.)

  Z represents an organic group represented by the following general formulas (III-1) to (III-11).

In the above formulas (III-1) to (III-11), R ⁶ is each independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, and R ⁷ is Each independently is a divalent organic group. P represents an integer of 0 to 4, and q represents an integer of 0 to 3. * Represents a bonding part, but the organic groups represented by the above formulas (III-1) to (III-6) are preferably bonded at the para position.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ⁶ include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a pentyl group, and a hexyl group. It is done.
The alkoxy group having 1 to 6 carbon atoms R ⁶ represents, for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, pentyloxy group, and a hexyloxy group.

Examples of the divalent organic group represented by R ⁷ include divalent aliphatic groups such as linear or branched alkylene groups, oxyalkylene groups, alkylidene groups, alkenylene groups, phenylene groups, and biphenylene groups. And divalent aromatic groups such as a naphthylene group.

Among these, (meth) acrylates in which Z in the above formula (IV) is an organic group represented by the above formula (III-1) from the viewpoint of improving the heat distortion resistance of a molded article obtained from the composition Compounds are preferred.
As the (meth) acrylate compound in which Z is an organic group represented by the above formula (III-1), for example, a (meth) acrylic acid adduct of bisphenol A diglycidyl ether, a hydrogenated bisphenol A diglycidyl ether ( Examples include commercially available products such as epoxy esters 3002M, 3002A, 3000M, 3000MK, and 3000A (above, manufactured by Kyoeisha Chemical Co., Ltd.).

  As content of (C) component in the composition of this invention, from a viewpoint of a moldability and a refractive index, Preferably it is 30-85 mass% with respect to the total amount of (A)-(C) component, More preferably It is 40-80 mass%, More preferably, it is 45-70 mass%. If the said content is 30 mass% or more, it can improve a viscosity and can be set as the composition excellent in workability. On the other hand, if the said content is 85 mass% or less, the viscosity of a composition will not rise too much and the moldability of the composition obtained can be made favorable.

[Component (D): Reaction compound (D1) of epoxy compound and (meth) acrylic acid other than the compound corresponding to component (C), urethane (meth) acrylate compound (D2)]
The composition of the present invention further comprises, as component (D), a reaction compound (D1) of an epoxy compound and (meth) acrylic acid other than the compound corresponding to component (C) and / or a urethane (meth) acrylate compound ( D2) is preferably included.
In component (D1), due to the influence of hydrogen bonding between the oxygen atom of the carbonyl group and the hydrogen atom of the hydroxyl group formed by ring opening of the epoxy group of the epoxy compound, in component (D2), oxygen in the urethane bond Due to the influence of hydrogen bonding between atoms and hydrogen atoms, the viscosity of the composition containing these components can be increased.

  The content of the component (D) (the total content of the component (D1) and the component (D2)) is preferably 2 to 50 parts by mass with respect to the total of 100 parts by mass of the components (A) to (C). More preferably, it is 6-42 mass parts, More preferably, it is 8-38 mass parts. If it is 2 mass parts or more, the viscosity of a composition can fully be raised and the workability of a composition can be improved. On the other hand, if it is 50 parts by mass or less, the viscosity of the composition does not become too high, and an appropriate viscosity optimum for workability can be obtained.

[(D1) component: reaction compound (D1) of epoxy compound and (meth) acrylic acid other than the compound corresponding to component (C)]
The component (D1) is a compound other than the compound corresponding to the component (C), and is generated by the ring opening of the epoxy group of the epoxy compound and the reaction with (meth) acrylic acid.
Examples of the epoxy compound include alkyl glycidyl ether and allyl glycidyl ether.

Moreover, as an epoxy compound, the compound which has a 2 or more epoxy group is preferable.
Examples of the reaction compound of an epoxy compound having two or more epoxy groups and (meth) acrylic acid include (meth) acrylic acid adduct of propylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether ( (Meth) acrylic acid adduct, ethylene glycol diglycidyl ether (meth) acrylic acid adduct, 1,4-butanediol diglycidyl ether (meth) acrylic acid adduct, 1,5-pentanediol diglycidyl ether ( (Meth) acrylic acid adduct, (meth) acrylic acid adduct of 1,6-hexanediol diglycidyl ether, (meth) acrylic acid adduct of 1,9-nonanediol diglycidyl ether, neopentyl glycol diglycidyl ether (Meth) acrylic acid adduct, glycerin di The glycidyl ether (meth) acrylic acid adduct and the like.

As a commercial item of (D1) component, epoxy ester 40EM, 70PA, 200PA, 80MFA (above, Kyoeisha Chemical Co., Ltd.) etc. are mentioned, for example.
In addition, you may use these (D1) components individually or in combination of 2 or more types.

[(D2) component: urethane (meth) acrylate compound (D2)]
The urethane (meth) acrylate compound (D2) is preferably a compound synthesized from a polyol component, an isocyanate component, and a hydroxy group-containing (meth) acrylate component. In addition, the number of functional groups of the component (D2) is preferably 2 or more, more preferably 2 to 4, and still more preferably from the viewpoint of improving the high hardness, high elastic modulus, and heat distortion resistance of the molded product obtained from the composition. Is 2-3.

  Examples of the bifunctional urethane (meth) acrylate compound include U-108A, UA-112P, UA-5201, UA-512, UA-412A, UA-4200, UA-4400, UA-340P, UA-2235PE, UA-160TM, UA-122P, UA-512, UA-W2, UA-7000, UA-7100 (above, trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.); CN962, CN963, CN964, CN965, CN980, CN981, CN982, CN983, CN996, CN9001, CN9002, CN9788, CN9873, CN978, CN9782, CN9783 (above, trade name, manufactured by Sartomer Japan, Inc.); M-1100, M-1200, M-1210, M-1310, M- 1600 (above, product name, East Made by Synthetic Chemical Industry); UN-9000PEP, UN-9200A, UN-7600, UN-333, UN-1255, UN-6060PTM, UN-6060P, SH-500B (above, trade name, manufactured by Negami Kogyo); AH- 600, AT-600 (above, trade name, manufactured by Kyoeisha Chemical Co., Ltd.);

  As trifunctional urethane (meth) acrylate compounds, for example, CN929, CN944B85, CN989, CN9008 (above, trade name, manufactured by Sartomer Japan, Inc.); EVERCRYL 294 / 25HD, EVERCRYL 4820 (trade name, manufactured by Daicel-Cytec);

Examples of tetrafunctional or higher urethane (meth) acrylate compounds include U-6HA, U-6H, U-15HA, UA-32P, U-324A, and UA-7200 (above, trade names, manufactured by Shin-Nakamura Chemical Co., Ltd.). CN968, CN9006, CN9010 (above, trade name, manufactured by Sartomer Japan, Inc.); UN-3320HA, UN-3320HB, UN-3320HC, UN-3320HS, UN-904, UN-901T, UN-905, UN -952 (above, trade name, manufactured by Negami Kogyo Co., Ltd.);
These components (D2) may be used alone or in combination of two or more.

The composition of this invention may contain components other than the said (A)-(D) component in the range which does not inhibit the effect of this invention. For example, a (meth) acrylate compound that does not correspond to the components (A) to (D) may be included. However, the total content of the components (A) to (D) is preferably 60 to 100% by mass, more preferably 75 to 100% by mass, based on the total amount of the (meth) acrylate compound contained in the composition. %, More preferably 90 to 100% by mass.
Moreover, you may mix | blend additives, such as antioxidant, a polymerization initiator, and a light stabilizer, as needed.

〔Antioxidant〕
The composition of this invention can contain antioxidant as needed.
Examples of antioxidants include hindered phenol antioxidants, phosphorus antioxidants, sulfur antioxidants, thioether antioxidants, vitamin antioxidants, lactone antioxidants, and amine antioxidants. Etc.
Among these antioxidants, hindered phenol antioxidants are preferable from the viewpoint of heat resistance and yellowing resistance.
The molecular weight of the antioxidant is preferably 300 to 1500, more preferably 330 to 1300, from the viewpoints of heat resistance and yellowing resistance.

  Examples of the hindered phenol antioxidant include Irganox 1010, 1076, 1330, 3114, 3125 (all are trade names, manufactured by BASF), ADK STAB AO-20, AO-50, and AO. -60, AO-80, AO-30, AO-40 (all are trade names, manufactured by ADEKA Corporation), BHT (trade names, manufactured by Takeda Pharmaceutical Co., Ltd.), Cyanox 1790 (trade names, Cyanamide Co., Ltd.), Sumilizer GP, GM, GS, and GA-80 (all are trade names, manufactured by Sumitomo Chemical Co., Ltd.).

  Examples of phosphorus antioxidants include IRAGAFOS168, 12, 12, 38, P-EPQ, 126 (all are trade names, manufactured by BASF), ADKSTAB329K, PEP-36, PEP-8, Commercial products such as HP-10, 2112, 260, 522A (all are trade names, manufactured by ADEKA Co., Ltd.), Weston 618, 619G, 624 (all are trade names, manufactured by GE). Is mentioned.

  Examples of sulfur-based antioxidants include DSTP “Yoshitomi”, DLTP “Yoshitomi”, DLTOIB, DMTP “Yoshitomi” (all of which are trade names, manufactured by Yoshitomi Co., Ltd.), Seenox 412S (trade name, Sipro Kasei Co., Ltd.) )), Cyanox 1212 (trade name, manufactured by Cyanamide), TP-D, TPS, TPM, TPL-R (all of which are trade names, manufactured by Sumitomo Chemical Co., Ltd.).

  Examples of the thioether-based antioxidant include commercially available products such as ADK STAB AO-412S and AO-503 (all of which are trade names, manufactured by ADEKA Corporation).

  Examples of vitamin-based antioxidants include commercially available products such as tocopherol (trade name, manufactured by Eisai Co., Ltd.) and Irganox E201 (trade name, manufactured by BASF).

  Examples of the lactone antioxidant include commercially available products such as compounds described in JP-A-7-233160 and JP-A-7-247278, and HP-136 (trade name, manufactured by BASF). .

  Examples of the amine-based antioxidant include commercially available products such as Irgastab FS042 (trade name, manufactured by BASF) and GENOX EP (trade name, manufactured by Crompton).

These antioxidants can be used alone or in combination of two or more.
The blending amount of the antioxidant is preferably based on 100 parts by mass of the total of the components (A) to (C) from the viewpoint of improving the transparency of the molded product obtained from the composition and suppressing yellowing. Is 0.1 to 20 parts by mass, more preferably 1 to 15 parts by mass, and still more preferably 1.5 to 10 parts by mass.

(Polymerization initiator)
The composition of this invention can mix | blend a polymerization initiator as needed.
As the polymerization initiator, any one of a thermal polymerization initiator that is cleaved by heat to generate an initiation radical, and a photopolymerization initiator that generates an initiation radical by irradiation with active energy rays such as light, electron beam, and radiation can be used. it can.
In the case of using a thermal polymerization initiator, the polymerization reaction can be promoted by heating the composition containing the thermal polymerization initiator at 40 to 200 ° C. On the other hand, in the case of using a photopolymerization initiator, the composition containing the photopolymerization initiator is irradiated with ultraviolet rays or the like with a cumulative light quantity of 50 to 2000 mJ / cm ² using a mercury xenon lamp or the like as a light source, It can be polymerized.

  Examples of the thermal polymerization initiator include ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, cyclohexanone peroxide, and methylcyclohexanone peroxide; 1,1,3,3-tetramethylbutyl Hydroperoxides such as hydroperoxide, cumene hydroperoxide, and t-butyl hydroperoxide; diisobutyryl peroxide, bis-3,5,5-trimethylhexanol peroxide, lauroyl peroxide, benzoyl peroxide, and diacyl peroxides such as m-toluylbenzoyl peroxide; dicumyl peroxide, 2,5-dimethyl-2,5-di (t-butyl peroxide); B) Hexane, 1,3-bis (t-butylperoxyisopropyl) hexane, t-butylcumyl peroxide, di-t-butyl peroxide, and 2,5-dimethyl-2,5-di (t-butylperoxy) ) Dialkyl peroxides such as hexene; 1,1-di (t-butylperoxy-3,5,5-trimethyl) cyclohexane, 1,1-di-t-butylperoxycyclohexane, and 2,2-di (t Peroxyketals such as -butylperoxy) butane; 1,1,3,3-tetramethylbutylperoxyneodicarbonate, α-cumylperoxyneodicarbonate, t-butylperoxyneodicarbonate, t-hexylperoxypivalate, t -Butylperoxypivalate, 1,1,3,3-tetramethylbutyl Peroxy-2-ethylhexanoate, t-amylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyisobutyrate, di-t-butylperoxyhexahydroterephthalate 1,1,3,3-tetramethylbutylperoxy-3,5,5-trimethylhexanate, t-amylperoxy-3,5,5-trimethylhexanoate, t-butylperoxy-3,5,5 Alkyl peroxyesters such as trimethylhexanoate, t-butylperoxyacetate, t-butylperoxybenzoate, and dibutylperoxytrimethyladipate; di-3-methoxybutylperoxydicarbonate, di-2-ethylhexylperoxydicarbonate, Screw 1,1-butylcyclohexaoxydicarbonate), diisopropyloxydicarbonate, t-amylperoxyisopropylcarbonate, t-butylperoxyisopropylcarbonate, t-butylperoxy-2-ethylhexyl carbonate, and 1,6-bis (t- Peroxycarbonates such as butylperoxycarboxy) hexane; 1,1-di (t-hexylperoxy) cyclohexane and (4-t-butylcyclohexyl) peroxydicarbonate. Among these, diacyl peroxides, peroxyketals, alkyl peroxy esters, and 1,1-di (t-hexylperoxy) cyclohexane are preferable. Lauroyl peroxide and 1,1-di-t-butylperoxycyclohexane are preferable. T-butylperoxy-2-ethylhexanoate and 1,1-di (t-hexylperoxy) cyclohexane are more preferable.

  Examples of the photopolymerization initiator include benzoin ether, 2,2-dimethoxy-1,2-diphenylethane-1-one (commercially available product: “IRGACURE651 (trade name, manufactured by BASF)”), 1-hydroxy-cyclohexyl. -Phenyl-ketone (commercial product: “IRGACURE184 (trade name) manufactured by BASF)”, 2-hydroxy-2-methyl-1-phenyl-propan-1-one (commercial product: “DAROCUR1173 (commercial product, product of BASF) Name) "), 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one (commercially available product:" IRGACURE 2959 (trade name, manufactured by BASF) " ), 2-hydroxy-1- [4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl -2-methyl-propan-1-one (commercially available product: “IRGACURE127 (trade name) manufactured by BASF)”, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one ( Commercial product: “IRGACURE907 (trade name, manufactured by BASF)”), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 (commercial product: “IRGACURE369 (commercial product, manufactured by BASF) Name) ”), 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-monophorinyl) phenyl] -1-butanone (commercially available product:“ IRGACURE 379 (manufactured by BASF) , Product name) "), 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (commercially available product:" DAROCUR TPO (B ASF Corp., trade name) "), bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (commercial product:" IRGACURE 819 (BASF trade name, trade name) "), bis (η5-2,4- Cyclopentadien-1-yl) -bis (2,6-difluoro-3- (1H-pyrrol-1-yl) -phenyl) titanium (commercially available product: “IRGACURE784 (trade name, manufactured by BASF)”), 1, 2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)] (commercially available product: “IRGACURE OXE 01 (trade name, manufactured by BASF)”), Ethanone-1- [9- Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime) (commercial product: “IRGACURE OXE 02 (manufactured by BASF, trade name) ").

These polymerization initiators can be used alone or in combination of two or more.
The blending amount of the polymerization initiator is preferably 0.01 to 12 parts by mass, more preferably 0 with respect to 100 parts by mass in total of the components (A) to (C), from the viewpoint of effectively promoting the polymerization reaction. 0.1-8 parts by mass, more preferably 0.3-5 parts by mass.

[Other additives]
The composition of the present invention includes a light stabilizer, an ultraviolet absorber, a lubricant, a plasticizer, an antistatic agent, an inorganic filler, a colorant, an antistatic agent, a release agent, as long as the effects of the present invention are not impaired. You may mix | blend additives, such as a flame retardant. Further, for the purpose of improving the adhesion with inorganic compounds such as titanium oxide and silicon oxide, additives such as a silane coupling agent containing a methacryloxy group or an acryloxy group of the silane compound may be blended.

[Physical properties of the composition]
The viscosity at 25 ° C. of the composition of the present invention containing the above components is preferably 500 to 50000 mPa · s, more preferably 700 to 40000 mPa · s, and still more preferably 800 to 5000 mPa · s, from the viewpoint of workability. More preferably, it is 1000-2000 mPa * s.
In addition, the value of the viscosity in 25 degreeC of said composition is a value measured based on the method as described in an Example.

[Molded body]
The molded body of the present invention is a molded body formed by molding a resin obtained by polymerizing the above-described composition of the present invention.
In polymerizing the composition, it is preferable to include the above-described polymerization initiator in the composition from the viewpoint of efficiency of the polymerization reaction.
As the polymerization and molding method, a method similar to the molding of a normal thermosetting resin can be used. For example, using the composition of the present invention or a prepolymer obtained by polymerizing the composition in advance, these methods can be used. Examples thereof include a method of proceeding simultaneously with the polymerization and the molding step in injection molding, compression molding, transfer molding, insert molding and the like of the liquid composition. Moreover, a molded object can also be obtained by a potting process, a coating process, etc., and a molded object can also be obtained by the method similar to shaping | molding of photocuring resin, such as UV hardening molding.

Since the composition of the present invention has high viscosity while maintaining optical performance, it is suitable for producing a molded body using a liquid resin molding method.
Liquid resin molding methods include liquid resin injection molding in which a raw material composition that is liquid at room temperature or a prepolymer thereof is pressed into a high-temperature mold and heat-cured, and a liquid raw material composition is placed in a mold and pressed by a press. Examples thereof include compression molding for pressing and curing, transfer molding for curing the raw material composition by applying pressure to the heated liquid raw material composition and press-fitting it into a mold.

Each optical performance and physical property of the molded article of the present invention produced as described above will be described.
The total light transmittance of the molded article of the present invention is preferably 85% or more, more preferably 88% or more, and still more preferably 90% or more.
Further, the amount of decrease in light transmittance (absolute value of the light transmittance) at a wavelength of 440 nm between the molded body after thermal history left at 260 ° C. for 10 minutes and the molded body before thermal history is preferably It is 5.0% or less, more preferably 3.0% or less, and still more preferably 1.5% or less.

The refractive index of the molded product of the present invention at the d-line (wavelength 589.3 nm) is preferably 1.45 to 1.65, more preferably 1.50 to 1.63, still more preferably 1.53 to 1. 60.
The Abbe number at the d-line (wavelength 589.3 nm) of the molded product of the present invention is preferably 30 to 60, more preferably 33 to 52, and still more preferably 36 to 45.

The linear expansion coefficient of the molded product of the present invention is preferably 110 ppm or less, more preferably 90 ppm or less, and still more preferably 80 ppm or less.
The flexural modulus of the molded article of the present invention is preferably 2.0 GPa or more, more preferably 2.4 GPa or more, and still more preferably 2.8 GPa or more.
The bending strength of the molded article of the present invention is preferably 50 MPa or more, more preferably 60 MPa or more, and further preferably 70 MPa or more.
The Shore D hardness of the molded article of the present invention is preferably 60 or higher, more preferably 70 or higher, and still more preferably 77 or higher.
In particular, when the molded article of the present invention is an optical component, a certain degree of mechanical strength is required so as not to be deformed during manufacturing.
In addition, the value of each said physical property of a molded object means the value measured by the method as described in an Example.

  As described above, since the molded article of the present invention is excellent in various optical performances, it is suitable as an optical component such as a lens used in various devices and a lens for optical communication.

Examples The present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples.
In addition, about each physical property of the composition obtained by the following Example and comparative example, and a molded object, it measured and evaluated based on the following method.

(1) Viscosity The viscosity at 25 ° C. of the obtained composition was measured using a viscometer (manufactured by Brooksfield, product name “LVDV-I +”) based on JIS K7117-1.
(2) Total light transmittance As a test piece, using the obtained molded body having a thickness of 3 mm, based on JIS K7105, with a haze meter (product name “HGM-2DP” manufactured by Suga Test Instruments Co., Ltd.), The total light transmittance was measured.
(3) Decrease in light transmittance at 440 nm after thermal history As a test piece, a 1 mm-thick molded article was used, and a spectrophotometer (manufactured by Hitachi High-Tech Fielding Co., Ltd., product name “U-4100 spectrometer”). )), The light transmittance at a wavelength of 440 nm was measured.
Next, the test piece was placed on a stainless steel plate having a thickness of 1 mm and left at 260 ° C. for 10 minutes (hereinafter, this operation is also referred to as “thermal history 1”). For the test piece after heat history 1, the light transmittance at a wavelength of 440 nm was measured in the same manner as described above, and the amount of decrease in light transmittance at a wavelength of 440 nm before and after heat history 1 (absolute value of the difference in light transmittance). (%) Was calculated.
(4) Refractive index, Abbe number As a test piece, a d-line at 20 ° C. was used for a molded article obtained with a thickness of 3 mm using a refractometer (manufactured by Metricon, product name “Model 2010 Prism Coupler”). The refractive index and Abbe number at a wavelength of 589.3 nm were measured.
(5) Linear expansion coefficient About the obtained molded object, it is 20-90 by the compression method of the load 49mN using the linear expansion measuring apparatus (the product name "TMA / SS6100" by Seiko Instrumental, Inc.) based on ASTM E831. The linear expansion coefficient in the temperature range of ° C. was measured and the linear expansion coefficient was calculated.
(6) Shape stability evaluation Using a plate-like molded body of 25 mm long × 25 mm wide × 2 mm thick, the three plate-like bodies were placed on a stainless steel plate having a thickness of 3 mm and left at 260 ° C. for 10 minutes. After (Heat History 1), the degree of deformation of the edge of the plate-like molded product was visually confirmed and evaluated according to the following criteria.
A: The edge portion is the same as before the heat history, and the shape stability is excellent.
B: The edge portion is uniformly rounded and inferior in shape stability.
(7) Bending strength and flexural modulus About the obtained molded body, based on JIS K6911, using a testing machine (product name "INSTRON 5567" manufactured by Instron Japan Company Limited), bending strength (unit: MPa) ) And flexural modulus (unit: GPa).
(8) Shore D Hardness Based on JIS-K 6253, Shore D hardness was measured using a testing machine (manufactured by Kobunshi Keiki Co., Ltd., product name “ASKER P1”).

[Examples 1 to 8, Comparative Examples 1 and 2]
Each component shown in Table 1 was added at the stated blending amount (solid content ratio) and mixed to obtain a composition. Each component used in the present Example described in Table 1 is as follows.
And when producing a molded object from this composition, between the two stainless steel plates (length 70 mm x width 70 mm x thickness 3 mm), two sheets of mirror-finished aluminum plates (length 70 mm x width 70 mm x A container obtained by sandwiching a Teflon (registered trademark) spacer (length 70 mm × width 70 mm × thickness 3 mm) between the sheets was used. A Teflon (registered trademark) spacer portion of the container is provided with a window of 30 mm length × 30 mm width × 3 mm thickness, and the composition can be poured into the container from the window.
The composition is poured from the window of the container, and the container is held so as not to leak, and heated in an oven under a nitrogen atmosphere (oxygen concentration of 5% by volume or less) at 110 ° C. for 3 hours and then at 160 ° C. for 1 hour. After performing polymerization and molding, a plate-like molded body was obtained by cooling to room temperature.

  About the obtained composition and molded object, various physical-property values were measured with the above-mentioned method. The results are shown in Table 1. Moreover, each component contained in the compositions of Examples and Comparative Examples shown in Table 1 is as follows.

<(A) component>
-"AM": 1-adamantyl methacrylate (made by Osaka Organic Chemical Industry Co., Ltd.) represented by the following formula (a1).

・「ＳＲ−４９９」：下記式（ｂ２）で表される、エトキシ化（６）トリメチロールプロパントリアクラレート（サートマー・ジャパン（株）製、分子量５６０）。

・「ＳＲ−２９５」：下記式（ｂ３）で表される、ペンタエリスリトールテトラアクリレート（サートマー・ジャパン（株）製、平均分子量３５２）。

<(B) component>
"SR-399": Dipentaerythritol pentaacrylate represented by the following formula (b1) (Sartomer Japan, Inc., molecular weight 525).

"SR-499": Ethoxylated (6) trimethylolpropane triclarate represented by the following formula (b2) (Sartomer Japan, Inc., molecular weight 560).

"SR-295": Pentaerythritol tetraacrylate represented by the following formula (b3) (manufactured by Sartomer Japan KK, average molecular weight 352).

・「ＳＲ−３４９」：下記式（ｃ２）で表される、エトキシ化ビスフェノールＡ型ジアクリレート（サートマー・ジャパン（株）製）。

・「エポキシエステル３０００ＭＫ」：下記式（ｃ３）で表される、ビスフェノールＡジグリシジルエーテルメタクリル酸付加物（共栄社化学（株）製）。

・「エポキシエステル３０００Ａ」：下記式（ｃ４）で表される、ビスフェノールＡジグリシジルエーテルアクリル酸付加物（共栄社化学（株）製）。

<(C) component>
“BPE-80N”: ethoxylated bisphenol A type dimethacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.) represented by the following formula (c1).

"SR-349": Ethoxylated bisphenol A type diacrylate (Sartomer Japan Co., Ltd.) represented by the following formula (c2).

“Epoxy ester 3000MK”: bisphenol A diglycidyl ether methacrylic acid adduct represented by the following formula (c3) (manufactured by Kyoeisha Chemical Co., Ltd.).

“Epoxy ester 3000A”: a bisphenol A diglycidyl ether acrylic acid adduct represented by the following formula (c4) (manufactured by Kyoeisha Chemical Co., Ltd.).

<(D) component>
“CN929”: trifunctional urethane acrylate (manufactured by Sartomer Japan, Inc.).

・「酸化防止剤（アデカスタブＡ−８０）」：下記式（ｅ２）で表される、ヒンダードフェノール系酸化防止剤（株式会社ＡＤＥＫＡ社製、分子量：７４１）。

<Other ingredients>
“Thermal polymerization initiator”: 1,1-di (t-hexylperoxy) cyclohexane (manufactured by NOF Corporation) represented by the following formula (e1).

-"Antioxidant (ADK STAB A-80)": A hindered phenol-based antioxidant represented by the following formula (e2) (manufactured by ADEKA Corporation, molecular weight: 741).

Each of the compositions of Examples 1 to 8 has a high viscosity at 25 ° C. of 500 mPa · s or more, and is excellent in workability. Moreover, the result that the various optical performance of the molded object obtained from the composition of Examples 1-8 was favorable about all was obtained.
On the other hand, the compositions of Comparative Examples 1 and 2 both had low viscosities at 25 ° C., which resulted in problems with workability.

  The (meth) acrylate composition of the present invention has excellent workability because of its high viscosity while maintaining good heat resistance and shape stability, and optical performance such as refractive index and transparency. Therefore, from the composition of the present invention, optical components such as lenses used for various devices and lenses for optical communication having excellent optical properties can be produced with high productivity.

Claims (10)

The (meth) acrylate compound (A) having an adamantyl group represented by the following general formula (I), the (meth) acrylate compound (B) represented by the following general formula (II), and the following general formula (III) The (meth) acrylate type composition containing the (meth) acrylate compound (C) represented by these.

(In the formula (I), each R ¹ independently represents a hydrogen atom or a methyl group, and each X independently represents a single bond, an alkylene group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms. Represents an oxyalkylene group, U represents an alkyl group having 1 to 4 carbon atoms, a halogen group, a hydroxyl group, or two U formed together, k represents an integer of 0 to 15, and m represents 1 Represents an integer of ~ 4.)

(In the formula (II), each R ² independently represents a hydrogen atom or a methyl group, and Y ¹ represents a substituted or unsubstituted acyclic hydrocarbon group having 5 to 30 carbon atoms and / or —R. An acyclic organic group containing a group represented by '(OR') _L- (wherein R 'each independently represents a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms, and L is 1 And n is an integer of 1 to 8.)

(In the formula (III), each G independently represents a single bond, an alkylene group having 1 to 4 carbon atoms, or an oxyalkylene group having 1 to 4 carbon atoms, and each R ⁴ independently represents a hydrogen atom. Or a methyl group, and each R ⁵ independently represents an alkylene group having 1 to 4 carbon atoms or an alkylene group having 1 to 4 carbon atoms substituted with a hydroxy group, and a represents an integer of 2 to 8. And b are each independently a positive number of 1 to 4. Z represents an organic group represented by the following formulas (III-1) to (III-11).

(In the above formula, each R ⁶ is independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, and R ⁷ is each independently a divalent organic group. In addition, p represents an integer of 0 to 4, q represents an integer of 0 to 3, and * represents a bonding portion.)   The (meth) acrylate composition according to claim 1, wherein the content of the component (C) is 30 to 85 mass% with respect to the total amount of the components (A) to (C).   Furthermore, as the component (D), other than the compound corresponding to the component (C), a reaction compound (D1) of an epoxy compound and (meth) acrylic acid and / or a urethane (meth) acrylate compound (D2) is included. The (meth) acrylate composition according to 1 or 2.   The (meth) acrylate composition according to claim 3, wherein the content of the component (D) is 2 to 50 parts by mass with respect to 100 parts by mass of the total of the components (A) to (C).   The (meth) acrylate composition according to any one of claims 1 to 4, wherein the (meth) acrylate composition has a viscosity at 25 ° C of 500 to 50,000 mPa · s.   Resin obtained by superposing | polymerizing the (meth) acrylate type composition in any one of Claims 1-5.   The molded object formed by shape | molding resin of Claim 6.   The molded product according to claim 7, wherein the molded product has a total light transmittance of 85% or more.   The molded object of Claim 7 or 8 whose refractive index in d line | wire of the said molded object is 1.45-1.65.   The molded body according to any one of claims 7 to 9, wherein the molded body is an optical component.