JP2003026735A - Resin composition containing highly refractive (meth) acrylate compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel resin composition which can readily give a cured product by irradiating an actinic radiation such as ultraviolet rays, the resultant cured product being highly refractive and lowly water-absorptive, excellent in chemical resistance and transparency, and hence primarily suitable for lens uses. SOLUTION: A (meth)acrylate compound is synthesized by reacting a diphenylmethanol derivative or a triphenylmethanol derivative with 2(meth) acryloyloxyethylisocyanate, and the resultant compound is mixed with a photopolymerization initiator to prepare the resin composition.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel high-refractive index (meth) acrylate compound and a resin composition containing the same, and the cured product thereof has a high refractive index and low water absorption. Further, the present invention relates to a novel resin composition which is excellent in chemical resistance and transparency and which is mainly suitable for lens applications and a cured product thereof.

[0002]

2. Description of the Related Art In recent years, plastic materials having a high refractive index have been remarkably advanced into optical lenses and optoelectronics, and eyeglass lenses, Fresnel lenses, lenticular lenses, prism lens sheets for TFTs, aspherical lenses,
Optical discs, optical fibers, optical waveguides, etc. are being actively studied. Among them, in the case of an eyeglass lens, a plastic material having a high refractive index has been widely used due to its features such as easy molding and light weight. The mainstream of transparent plastics used as spectacle lenses is thermosetting plastics such as diethylene glycol bisallyl carbonate. Important properties required of such plastic lenses include refractive index, low specific gravity, moldability, heat resistance, restoration, impact resistance, low water absorption, surface accuracy of molded products, dyeability, etc. Can be mentioned. In recent years, further improvement of these properties has been demanded, and a method of producing a plastic lens using various monomers and oligomers instead of diethylene glycol bisallyl carbonate has been proposed. When a plastic material is used as a casting such as an optical lens, the cured product is molded by a method such as a pressing method or a casting method. When the cured product is molded by the pressing method, the productivity is not good because it is manufactured by a cycle of heating, pressing and cooling steps. Further, in the case of the casting method, there is a problem that the manufacturing time becomes long because the resin is poured into the mold to be cured, and a large number of molds are required, resulting in a high manufacturing cost. Regarding the use of an active energy ray-curable resin composition for solving such a problem, for example, JP-A-61-1772.
15, JP-A-61-248707 and JP-A-61-248
708, JP-A-63-163330, JP-A-63-16
7301, JP-A-63-199302, JP-A-64-6
Various proposals are described in 935 and the like.

[0003]

In recent years, a lens material having a higher refractive index than conventionally used thermosetting plastics such as diethylene glycol bisallyl carbonate has been demanded, and a new high refractive index material has been demanded. Many attempts have been made to develop transparent plastics. However, due to the chemical structure of plastic materials, it is generally not easy to obtain materials having a high refractive index. When a plastic material has a structurally high refractive index, it introduces a π-electron system structure such as an aromatic ring or an unsaturated group into the molecular structure of the resin for plastic material. There is a method of introducing an atom having an lone electron pair such as an atom or a phosphorus atom. When an aromatic ring is introduced into the molecular structure of the resin for plastic materials, the refractive index can be effectively increased depending on the number of aromatic rings introduced. However, if too many aromatic rings are included in one molecule of the resin for plastic materials, the plastic lens itself after curing will turn yellow, the impact resistance will be poor, and the specific gravity of the cured product will increase. There are drawbacks. Further, when a large amount of unsaturated groups are introduced, the effective improvement of the refractive index cannot be expected, and there is a concern that the stability against heat or light may deteriorate. Further, the method of introducing a halogen atom other than a fluorine atom into the molecular structure of the resin for a plastic material has a large effect of increasing the refractive index of the resin, but the more it is introduced, the higher the specific gravity of the cured product becomes, and If too many halogen atoms are introduced, a cured product having a transparent feeling cannot be obtained, and there are problems in impact resistance and dyeability with general disperse dyes. The method of introducing a sulfur atom also has a large effect of increasing the refractive index of the resin, but in general, the resin itself or a cured product is liable to produce an odor. Even when phosphorus atoms are introduced, if the phosphorus atoms are introduced too much, the cured product itself becomes brittle, which may cause problems such as inferior restorability and transparency.

[0004]

Means for Solving the Problems As a result of intensive studies for solving the above-mentioned problems, the present inventor has synthesized a high refractive index compound having a specific structure and using it as a component to obtain a high refractive index compound. The present invention has been accomplished by finding a resin composition that can obtain a cured product having a high rate of water absorption, low water absorption, and excellent chemical resistance and transparency. That is, the present invention is
[1] Formula (1)

[0005]

[Chemical 2]

(Wherein R 1 is a hydrogen atom or a methyl group, R 2 is a hydrogen atom or a phenyl group, and n is 0
Represents an integer of 2; ), A (meth) acrylate compound (A) represented by the formula (1), a (meth) acrylate compound (A) represented by the formula (1) described in [2] and [1], and an unsaturated group other than the component (A). A resin composition containing a compound (B), [3] containing a (meth) acrylate compound (A) represented by the formula (1) described in [1] and a photopolymerization initiator (C) [4] a resin composition characterized by
It is characterized by containing a photopolymerization initiator (C) [2]
[5] The resin composition according to any one of [2] to [4], wherein [5] is an optical article, and [6] is for a lens. A resin composition according to any one of [2] to [5], and a cured product of the resin composition according to any one of [7] [2] to [6]. It is a thing.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The above formula (1) used in the present invention.
The (meth) acrylate compound (A) represented by can be obtained by reacting a compound represented by the following formula (2) with 2- (meth) acryloyloxyethyl isocyanate.

[0008]

[Chemical 3]

(In the formula, R2 represents a hydrogen atom or a phenyl group, and n represents an integer of 0 to 2.)

Specific examples of the compound represented by the above formula (2) include, for example, diphenylmethanol, triphenylmethanol, 2,2-diphenylethanol, 2,2,2.
2-triphenyl ethanol, 3,3-diphenyl propanol, 3,3,3-triphenyl propanol and the like can be mentioned.

In the method of synthesizing the (meth) acrylate compound (A) represented by the above formula (1) used in the present invention, the charged amount of 2- (meth) acryloyloxyethyl isocyanate is the above formula (2). It is preferable to charge 0.80 to 1.20 mol relative to 1.00 mol of the compound represented by, more preferably 0.98 to
It is preferable to charge the mixture so that the amount becomes 1.00 mol. In addition, this reaction is carried out by reacting with the terminal hydroxyl group of the compound represented by the above formula (2).
In order to accelerate the reaction of the terminal isocyanate group of (meth) acryloyloxyethyl isocyanate, for example, tertiary amines such as triethylamine and benzyldimethylamine, and dilaurylates such as dibutyltin dilaurylate and dioctyltin dilaurylate are used. It can be used as a catalyst. The amount of the catalyst added is preferably 0.001 to 5.0% by weight, and more preferably 0.01 to 1.0% by weight, based on the whole reaction mixture.
The reaction time is preferably 1 to 10 hours. The reaction temperature is preferably 30 to 100 ° C, more preferably 40 to 80 ° C.
℃.

In the method for synthesizing the (meth) acrylate compound (A) represented by the above formula (1), the reaction can be carried out without solvent. However, in some cases, acetone,
A solvent inert to an isocyanate group such as methyl ethyl ketone, methyl isobutyl ketone, n-heptane, n-hexane, cyclohexane, toluene, xylene can be used as a reaction solvent.

The resin composition of the present invention may use only the (meth) acrylate compound (A) represented by the above formula (1), but for the purpose of adjusting physical properties such as refractive index and viscosity. The unsaturated group-containing compound (B) other than the component (A) may be mixed and used. The unsaturated group-containing compound other than the component (A) that can be used here is a monofunctional (meth)
Examples thereof include reactive monomers such as acrylate compounds, bifunctional to polyfunctional (meth) acrylate compounds, vinyl compounds and allyl compounds, and reactive oligomers such as epoxy (meth) acrylates and urethane (meth) acrylates.

Specific examples of the reactive monomer used as the unsaturated group-containing compound (B) include, for example, methyl (meth) acrylate, ethyl (meth) acrylate,
2-propyl (meth) acrylate, n-butyl (meth) acrylate, n-pentyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, lauryl ( (Meth) acrylate, stearyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, glycidyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, N, N -Diethylaminoethyl (meth) acrylate, 2-cyanoethyl (meth) acrylate, polyethylene glycol monoalkyl ether (meth) acrylate, polypropylene glycol monoalkyl ether (meth) acrylate, - hydroxyethyl (meth)
Acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate,
Tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth)
Acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, p-phenylphenyloxyethyl (meth) acrylate, p-phenylphenyloxyethyloxyethyl (meth) acrylate, o-phenylphenyloxyethyl (meth) acrylate, o
-Phenylphenyloxyethyloxyethyl (meth)
Monofunctional (meth) acrylate compounds such as acrylate,
Ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, tetrabutylene Glycol di (meth) acrylate, polybutylene glycol di (meth)
Acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, ethylene of bisphenol F Di (meth) acrylate of oxide adduct, di (meth) acrylate of ethylene oxide adduct of bisphenol A, trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, Dipentaerythritol penta and hexa (meth) acrylate,
Bis (4- (meth) acryloyloxyethoxyphenyl) sulfin, Bis (4- (meth) acryloyloxyethoxy-3-phenylphenyl) sulfin, Bis (4- (meth) acryloyloxyphenyl) sulfide, Bis (4- ( Bifunctional to polyfunctional (meth) acrylate compounds such as (meth) acryloyloxydiethoxyphenyl) sulfide and 2,4-di (meth) acryloyloxynaphthalene, styrene, chlorostyrene, divinylbenzene, 1-vinylbenzene, 1-vinyl Naphthalene,
Examples thereof include vinyl compounds such as 2-vinylnaphthalene and N-vinylpyrrolidone, and allyl compounds such as diethylene glycol bisallyl carbonate, trimethylolpropane diallyl and diallyl phthalate.

Specific examples of the reactive oligomer used as the unsaturated group-containing compound (B) include, for example,
Epoxy (meth) acrylate compounds which are reaction products of epoxy resins and (meth) acrylic acid, diisocyanates and (meth) acrylates containing one hydroxyl group in the molecule, or diols and diisocyanates and molecules. Examples thereof include urethane (meth) acrylate compounds which are reaction products of (meth) acrylates containing one hydroxyl group.

The epoxy resins used to obtain the epoxy (meth) acrylate compound used as the unsaturated group-containing compound (B) include, for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, and phenol novolac type epoxy resin. Resin, fluorene epoxy resin, etc. can be mentioned.

When the urethane (meth) acrylate compound used as the unsaturated group-containing compound (B) is obtained by reacting a diisocyanate with a (meth) acrylate containing one hydroxyl group in the molecule, it is used as a raw material. Specific examples of diisocyanates include, for example, hexamethylene diisocyanate, isophorone diisocyanate, methylene bis (4-cyclohexyl isocyanate), trimethylhexamethylene diisocyanate,
4,4-diphenylmethane diisocyanate, xylylene diisocyanate and the like can be mentioned. Further, specific examples of (meth) acrylates containing one hydroxyl group in the molecule to be reacted with diisocyanates include, for example, 2
-Hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 1,4-butanediol mono (meth) acrylate, ε-caprolactone adduct of 2-hydroxyethyl (meth) acrylate,
Examples thereof include pentaerythritol tri (meth) acrylate. When the urethane (meth) acrylate compound used as the unsaturated group-containing compound (B) is obtained by reacting a diol, a diisocyanate, and a (meth) acrylate containing one hydroxyl group in the molecule, as a raw material Specific examples of the diols used include, for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol,
Dipropylene glycol, tripropylene glycol,
1,3-butanediol, 1,4-butanediol,
1,5-pentanediol, neopentyl glycol,
Low molecular weight diols such as 1,6-hexanediol, 3-methyl-1,5-pentanediol, 1,8-octanediol, 1,9-nonanediol and 2-methyl-1,8-octanediol, Polyethylene glycol,
Polyether polyols such as polypropylene glycol and polytetramethylene glycol, succinic acid, adipic acid, azelaic acid, sebacic acid, phthalic acid, terephthalic acid, 1,2-cyclohexanedicarboxylic acid, 1,3-
Dibasic acids such as cyclohexanedicarboxylic acid and 1,4-cyclohexanedicarboxylic acid, and ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1, Examples thereof include polyester polyols obtained by reaction with diols such as 6-hexanediol, poly-ε-caprolactone-modified polyols, polymethylvalerolactone-modified polyols, and polycarbonate polyols. In addition, the diisocyanates used for the reaction and the (meth) acrylates containing one hydroxyl group in the molecule are the urethane (meth) acrylate compounds used as the unsaturated group-containing compound (B) and the hydroxyl groups in the diisocyanates and the molecule. The same compounds as those obtained by reacting one containing (meth) acrylate can be used.

Only one of these unsaturated group-containing compound (B) components exemplified above may be selected and used.
It is also possible to use two or more types in combination.

Of these unsaturated group-containing compound (B) components, preferred examples include those having an aromatic group in the molecular structure or having an aromatic group as a substituent,
It is a monofunctional or bifunctional (meth) acrylate monomer having a refractive index of 1.50 or more at 25 ° C. Specific examples of such monofunctional or bifunctional (meth) acrylate monomers include, for example, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, p-
Phenylphenyloxyethyl (meth) acrylate,
p-phenylphenyloxyethyloxyethyl (meth) acrylate, o-phenylphenyloxyethyl (meth) acrylate, o-phenylphenyloxyethyloxyethyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate Acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, tetrabutylene glycol di (meth) acrylate, polybutylene glycol di (meth ) Acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate,
Neopentyl glycol di (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, ethylene oxide adduct di (meth) acrylate of bisphenol F, ethylene oxide adduct di (meth) acrylate of bisphenol A, bis ( 4- (meth) acryloyloxyethoxyphenyl) sulfine, bis (4- (meth) acryloyloxyethoxy-
3-phenylphenyl) sulfine, bis (4- (meth) acryloyloxyphenyl) sulfide, bis (4- (meth) acryloyloxydiethoxyphenyl) sulfide, 2,4-di (meth) acryloyloxynaphthalene and the like. You can

The ratio of the (meth) acrylate compound (A) represented by the formula (1) and the unsaturated group-containing compound (B) used in the resin composition of the present invention is preferably a weight ratio. Is 5:95 to 90:10, and particularly preferably 20:80 to 80:20.

When the resin composition of the present invention is cured by irradiation with active energy rays such as ultraviolet rays, it is preferable to use a photopolymerization initiator (C). As the photopolymerization initiator (C) used in the resin composition of the present invention, any known photopolymerization initiator may be used, but it is required to have good storage stability after blending. Specific examples of such a photopolymerization initiator (C) include, for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one, diethoxyacetophenone, benzyldimethylketal, 4
-(2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one and the like can be mentioned. . Only one kind of these photopolymerization initiators (C) may be used, but two or more kinds thereof may be mixed and used at an arbitrary ratio. The amount of the photopolymerization initiator (C) added is the (meth) acrylate compound (A) represented by the formula (1).
The total amount of the component and the unsaturated group-containing compound (B) component,
Usually, it is preferably 0.1 to 10.0 w%, more preferably 0.5 to 5.0 w%.

The resin composition of the present invention has the above (A)
In addition to the component (C), if necessary, a release agent, an antifoaming agent,
Leveling agent, light stabilizer (for example, hindered amine, etc.), thermal polymerization initiator, antioxidant, polymerization inhibitor, antistatic agent, colorant (for example, dye, pigment, etc.), inorganic filler, organic filler, etc. are used in combination. be able to. The resin composition of the present invention can be obtained by uniformly mixing and dissolving the above components.

The cured product of the resin composition of the present invention can be obtained by irradiating with active energy rays. Specific examples of the light source used when the resin composition of the present invention is irradiated with active energy rays such as ultraviolet rays to be cured are, for example, a xenon lamp, a carbon arc, a germicidal lamp, an ultraviolet fluorescent lamp, and a copying machine. High pressure mercury lamp, medium pressure mercury lamp,
Examples thereof include a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, an electrodeless lamp, a metal halide lamp, or an electron beam by a scanning type or curtain type electron beam accelerating path.

The resin composition of the present invention is useful as a material for plastic lenses such as spectacle lenses, Fresnel lenses, lenticular lenses, prism lens sheets for TFTs, aspherical lenses, etc.
It can also be used for applications such as optical fibers and optical waveguides for optoelectronics, printing inks, paints, coating agents, varnishes, adhesives and the like.

As a method for producing a plastic lens using the resin composition obtained in the present invention, a gasket made of polyvinyl chloride, ethylene vinyl acetate copolymer or the like and two glass molds having a desired shape are used. Make a mold,
After injecting the resin composition obtained in the present invention into this, the active energy ray such as ultraviolet rays is irradiated to cure the resin composition obtained in the present invention, and the cured product is peeled from the mold.

In addition, the resin composition obtained by the present invention is used in applications other than castings such as plastic lenses.
The resin composition of the present invention can be used by coating it on a substrate. Examples of the method for applying the resin composition of the present invention to a substrate include, for example, brush coating, bar coater, applicator, roll coater, roller brush or the like, direct coating, spray coating by air spray or airless spray coating machine, etc. Method, a flow coating method using a shower coater, a curtain flow coater, or the like, a dipping method, a casting method, a spinner coating method, or the like can be used. In addition, it is desirable to appropriately use these coating methods according to the material, shape, and application of the base material.

[0027]

EXAMPLES The present invention will be specifically described below with reference to examples. The present invention is not limited to the following examples.

Synthesis Example of (Meth) Acrylate Compound (A) Represented by Formula (1) Example 1: In a 300 ml separable flask, 2-methacryloyloxyethyl isocyanate (trade name: Karenz MOI, Showa Denko ( 209.0 g (manufactured by K.K.) and 0.2 g of di-n-butyltin dilaurate 4 with stirring.
The temperature was raised to 0 ° C. To this solution, 248.0 g of diphenylmethanol was slowly charged so that the temperature of the reaction solution did not exceed 50 ° C. After the diphenylmethanol was charged, the mixture was stirred as it was at 40 to 50 ° C. for 2 hours, further heated and stirred at 70 to 80 ° C. for 2 hours to obtain a colorless transparent viscous liquid reaction product. When the NCO value of this reaction product was measured, the NCO value was 0.1 w% or less,
The viscosity at 25 ° C is 4570 mPa · s,
The refractive index at ° C was 1.5522. The obtained reaction product is a compound represented by the following formula (3). The results of elemental analysis of the obtained compound are shown in Table 1.

[0029]

[Chemical 4]

Table 1 Element Measured value (wt%) Calculated value (wt%) C 70.77 70.77 H 6.27 6.25 N 4.11 4.13

Example of Composition Example 2: 100.0 g of the reaction product obtained in Example 1 and 1-hydroxycyclohexyl phenyl ketone (trade name: Irgacure 184, manufactured by Ciba Specialty Chemicals) 2. 1 g was blended to obtain a colorless and transparent resin composition. The refractive index of this product at 25 ° C is 1.5.
524, and the viscosity at 25 ° C is 4030 mPa · s.
It was s. This resin composition is applied on an aluminum plate 15
After coating with a bar coater to a thickness of 0 to 200 μm, a colorless and transparent PET film is placed on the surface of the coating to adhere it to the surface of the coating, and then 600 mJ / c with a high pressure mercury lamp.
Ultraviolet rays were irradiated at an irradiation intensity of m ² to obtain a cured product. Table 2 shows the physical properties of the obtained cured product.

Example 3: Reaction product 8 obtained in Example 1
0.6 g, phenoxyethyl acrylate (trade name: Biscoat # 192, manufactured by Osaka Organic Chemical Industry Co., Ltd.) 20.
0 g and 1-hydroxycyclohexyl phenyl ketone 2.0 g were blended in the same manner as in Example 2 to obtain a colorless and transparent resin composition. This product has a refractive index of 1.5454 at 25 ° C and a viscosity of 360 m at 25 ° C.
It was Pa · s. This resin composition was irradiated with ultraviolet rays in the same manner as in Example 2 to obtain a cured product. Table 2 shows the physical properties of the obtained cured product.

Example 4: Reaction product 6 obtained in Example 1
0.1 g, 2-hydroxy-3-phenoxypropyl acrylate (trade name: KAYARAD R-128H,
40.2 g of Nippon Kayaku Co., Ltd. and 2.0 g of 1-hydroxycyclohexyl phenyl ketone were blended in the same manner as in Example 2 to obtain a colorless and transparent resin composition. The refractive index of this product at 25 ° C. is 1.5414, which is 25
The viscosity at 0 ° C. was 710 mPa · s. This resin composition was irradiated with ultraviolet rays in the same manner as in Example 2 to obtain a cured product. Table 2 shows the physical properties of the obtained cured product.

Example 5: Reaction product 6 obtained in Example 1
0.5 g, o-phenylphenyloxyethyl acrylate (trade name: KAYARAD OPP-1, manufactured by Nippon Kayaku Co., Ltd.) 40.1 g, and 1-hydroxycyclohexyl phenyl ketone 2.1 g were treated in the same manner as in Example 2. By blending, a colorless and transparent resin composition was obtained. 25 of this thing
The refractive index at ° C was 1.5618, and the viscosity at 25 ° C was 620 mPa · s. This resin composition was irradiated with ultraviolet rays in the same manner as in Example 2 to obtain a cured product. Table 2 shows the physical properties of the obtained cured product.

[0035] Table 2                                     Example                            2 3 4 5 Refractive index (25 ℃) * 1 1.5771 1.5749 1.5703 1.5879 Abbe number * 1 36 37 34 32 Water absorption rate (%) * 2 0.4 0.4 0.5 0.4 Chemical resistance * 3 ○ ○ ○ ○ Transparency * 4 ○ ○ ○ ○

Note) * 1 Refractive index and Abbe number: Multiwavelength Abbe refractometer DR
-M2 (manufactured by Atago Co., Ltd.) was used for measurement. * 2 Water absorption rate: The cured film was immersed in pure water at 23 ° C. for 24 hours, and the weight increase was expressed in%. * 3 Chemical resistance: The surface of the cured product was wiped 20 times with absorbent cotton impregnated with methyl ethyl ketone, and changes in the surface of the cured product were observed. ◯: No change is observed on the surface of the cured product. * 4 Transparency: The cured film was observed to confirm the presence or absence of a whitened and opaque portion. ○: There is no whitened part in the cured film.

[0037]

As is clear from the results of Examples 2 to 5 and Table 2, the resin composition of the present invention can be rapidly cured by irradiation with active energy rays such as ultraviolet rays. Since the cured product has a high refractive index, a low water absorption rate, and excellent chemical resistance and transparency, it can be used for optical applications such as spectacle lenses.

   ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 4H006 AA01 AB46 AC48 AC56 RA06                       RB28                 4H039 CA65 CA66                 4J100 AB02Q AB08Q AB16Q AL03Q                       AL04Q AL05Q AL08P AL08Q                       AL09Q AL11Q AL61Q AL62Q                       AL63Q AL66Q AQ08Q BA02Q                       BA03Q BA07Q BA08Q BA31Q                       BA38P BA38Q BA40Q BA51Q                       BA55Q BC04Q BC43P BC43Q                       BC45Q BC49Q BC53Q BC54Q                       CA04 DA28 DA62 DA63 EA01                       FA03 FA18 FA19 JA33

Claims (7)

[Claims] 1. A formula (1): (In the formula, R1 is a hydrogen atom or a methyl group, R2 is a hydrogen atom or a phenyl group, and n is an integer of 0 to 2.) A (meth) acrylate compound (A). 2. A (meth) acrylate compound (A) represented by the formula (1) according to claim 1 and an unsaturated group-containing compound (B) other than the component (A). Resin composition. 3. A resin composition comprising a (meth) acrylate compound (A) represented by the formula (1) according to claim 1 and a photopolymerization initiator (C). 4. The resin composition according to claim 2, containing a photopolymerization initiator (C). 5. The resin composition according to any one of claims 2 to 4, which is used as an optical article. 6. The resin composition according to any one of claims 2 to 5, which is used for a lens. 7. A cured product of the resin composition according to claim 2.