KR20140030057A - A method of preparing epoxy acryl based optical material - Google Patents

Abstract

The present invention relates to a method for manufacturing an epoxy acrylic optical material, and more specifically to a method for manufacturing a high-quality optical material having high yield without developing striae, a ring, variable curing, white turbidity, or developing fine bubbles due to imbalanced polymerization, and is colorless, transparent, and changeless. Provided is a method for manufacturing the epoxy acrylic optical material in which a polymerization composition, comprising an epoxy acrylate compound and a reactive dilution agent, is in-mold polymerized, and is characterized in that mixing, defoaming, and injection into a mold are performed within the 5-40°C temperature range. The epoxy acrylic optical material according to the present invention can replace an existing optical material including thiourethane-based optical materials, and be widely used in a variety of industries.

Description

A method of preparing epoxy acryl based optical material

The present invention relates to a method for producing an epoxy acrylic optical material, and more particularly, to a method for producing a high-quality optical material that is colorless, transparent and without deformation without high occurrence of striae, rings and variable uncuring due to polymerization imbalance.

The plastic optical lens was introduced as a substitute for the high specific gravity and low impact properties of the glass lens. Representative examples thereof include polyethylene glycol bisallyl carbonate, polymethylmethacrylate, diallyl phthalate, and the like. However, the optical lens made of these polymers is excellent in physical properties such as main formation, dyeability, hard coat film adhesion and impact resistance, but has a refractive index as low as 1.50 (nD) and 1.55 (nD) . Therefore, various attempts have been made to develop an optical material having a high refractive index in order to reduce the thickness of the lens.

The epoxy acrylic optical material composition disclosed in Korean Patent Nos. 10-0496911 and 10-0498896 has a high refractive index, high Abbe number, excellent optical properties such as transparency, light weight, heat resistance, and low cost of materials. There is an advantage. However, when the composition is molded by polymerizing a lens, striae, rings, or variable uncurings due to polymerization imbalance may occur, thereby often degrading the quality of the lens. The occurrence of striae, rings and variable uncured deterioration of the quality of the lens has been required to improve. In addition, the reduction of production cost has become a major concern in the recent lens field, the occurrence of striae, ring, variable uncured is the factor to increase the production cost by lowering the lens yield, the improvement in the production cost reduction is urgently required.

Korean Patent Publication No. 10-0496911 Republic of Korea Patent Registration 10-0498896

 The inventors have unexpectedly found that the temperature in the process of blending, defoaming and injecting the polymerizable composition has a significant correlation to the occurrence of striae, rings and variable uncured lenses of the finally obtained lens. That is, when the polymerizable composition was blended, defoamed at a specific temperature, and injected into the mold to polymerize, striae, rings and variable uncured hardly occurred in the finally obtained lens. SUMMARY OF THE INVENTION The present invention has been confirmed and completed, and an object of the present invention is to provide a method for producing a high-quality optical material that is colorless, transparent and free of deformation with high yield by reducing occurrence of striae, rings, and variable uncuring. "Stria" refers to a phenomenon that is locally different from the surrounding normal refractive index due to a difference in composition, etc., may appear as a polymerization imbalance. The term "ring" means that the optical lens formed by polymerization and curing in the thermosetting process of the resin composition for an optical lens is separated between the mold and the mold before demolding so that a ring shape appears in the central portion of the optical lens. "Variable uncured" refers to a phenomenon in which a part of the variable uncured optical lens is polymerized and cured in the thermosetting process of the resin composition for optical lenses. Stria, rings and variable uncured materials adversely affect the quality and performance of optical materials.

In the present invention,

In the method for producing an optical material for molding a polymerizable composition comprising a compound represented by the formula (1) and a reactive diluent, the blending, degassing, and injection of the polymerizable composition in a temperature range of 5 ~ 40 ℃ There is provided a method for producing an epoxy acrylic optical material. The polymerizable composition may further include a compound represented by Formula 2 below.

[Chemical Formula 1]

(Where n = 0-15, R ₁ is H or CH ₃ and R ₂ is H or Br)

(2)

(Wherein R is H or CH ₃ , m = 0 to 5, n = 0 to 5, m and n are not 0 at the same time, and m + n = 1 to 10.)

Further, in the present invention, an optical material obtained by the above manufacturing method and an optical lens composed of the optical material are provided. The optical lens particularly includes a spectacle lens or a polarizing lens.

In the present invention, by blending, defoaming, mold injection of the polymerizable composition in a specific temperature range, it is possible to manufacture a colorless, transparent, high-quality lens without the striae, the ring, and the variable uncured polymer due to the polymerization imbalance, and to improve the production cost. It can also be lowered.

In the method for producing an epoxy acrylic optical material of the present invention, in the process of blending, defoaming, and mold injection of a polymerizable composition including an epoxy acrylate compound represented by Chemical Formula 1 below and a reactive diluent, mold polymerization is carried out. . The polymerizable composition may further include a compound represented by Formula 2 below.

[Chemical Formula 1]

Wherein n is 0-15, R ₁ is H or CH ₃ , and R ₂ is H or Br. Preferably n is 0-10, More preferably, it is 0-5.

(2)

(Wherein R is H or CH ₃ , m = 0 to 5, n = 0 to 5, m and n are not 0 at the same time, and m + n = 1 to 10.)

In this invention, mix | blending, defoaming, and mold injection of a polymeric composition are performed at 5-40 degreeC. Maintain a temperature of 5 to 40 ° C. in the blending process for making a polymerizable composition by mixing a monomer component, a reactive diluent, and other additives including an internal mold release agent as necessary, and a defoaming process after the blending and an injection into a mold. do. If the temperature is less than 5 ℃, striae, ring, variable uncured appears large, and if it exceeds 40 ℃, the pot life is a problem during mixing and infusion of the resin composition, the viscosity becomes high, the phenomenon appears to be solidified. The present invention is the first to discover that the temperature during the formulation, defoaming, and infusion of the polymerizable composition has a significant correlation with the striae of the lens, the ring, and the variable uncured resin. In the method, efforts to suppress the occurrence of striae, rings, and variable unhardening through different process conditions and raw material changes, etc. are made by the simple method of temperature control. Acrylic optical material can be manufactured.

The reactive diluent is preferably styrene, divinylbenzene, alpha methyl styrene, alpha methyl styrene dimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxy styrene, monobenzyl maleate, monobenzyl fumalate, di Benzyl maleate, dibenzyl fumarate, methyl benzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, dipentyl maleate, monopentyl fumal Rate, dipentyl fumarate, diethylene glycol bisaryl carbonate and the like can be used alone or in combination of two or more thereof. The reactive diluent serves to appropriately control the viscosity and polymerization rate of the polymerizable modulator. The reactive diluent may be used in an amount of 30 to 300 parts by weight based on 100 parts by weight of the total monomer component further comprising the compound represented by Formula 1 or the compound represented by Formula 2 herein. If the reactive diluent is less than 30 parts by weight, the viscosity of the composition may not be easily controlled, and thus handling may be degraded. On the contrary, when the reactive diluent is used in excess of 300 parts by weight, the viscosity of the composition may be too low, which may adversely affect the refractive index and may cause malt. Etc. may occur.

The polymerizable composition comprising a monomer component and a reactive diluent further comprising a compound represented by Formula 1 or a compound represented by Formula 2 herein, preferably has a liquid viscosity of 20 to 1,000 cps at 25 ° C., Refractive index (nE, 20 degreeC) is 1.50-1.58, and solid-state refractive index (nE, 20 degreeC) is 1.54-1.63. If the liquid viscosity is less than 20 cps, the liquid flows out of the mold when the liquid resin composition is injected into a glass mold assembled with a synthetic resin gasket. If the viscosity of the liquid exceeds 1,000 cps, the composition is injected into the mold. There is a difficult problem. More preferable viscosity is 30-500 cps.

The polymerizable composition may further include an internal mold release agent, a heat stabilizer, an ultraviolet absorber, an organic dye, an inorganic pigment, an anti-coloring agent, an antioxidant, a light stabilizer, a catalyst, and the like according to a conventional method.

As an internal mold release agent, a phosphate ester compound, a silicone type surfactant, a fluorine type surfactant, etc. can be used individually or in combination of 2 or more types, Preferably it can be contained in 0.001-10 weight% in a polymeric composition. As an internal mold release agent, Preferably, a phosphate ester compound can be used. The phosphate ester compound used as the internal release agent is, for example, polyoxyethylene nonyl phenol ether phosphate (5% by weight of 5 mole of ethylene oxide added, 80% by weight of 4 mole added, 10% by weight of 3 mole added, 1 Molar addition 5% by weight), polyoxyethylenenonylphenylphosphate (5% by weight of 9 moles of ethylene oxide added, 80% by weight of 8 moles of ethylene oxide added, 10 parts by weight of 7 moles of ethylene oxide added) %, 5 wt% of ethylene oxide added up to 6 mol), Polyoxyethylenenonylphenol ether phosphate (3 wt% of 11 mol added ethylene oxide, 80 wt% of 10 mol added, 9 mol added 5 Weight%, 7 mole added 6% by weight, 6 mole added 6% by weight), polyoxyethylene nonylphenol ether phosphate (13 mole added by ethylene oxide 3% by weight, 12 mole added by 80% by weight, 11 mol added 8 wt%, 9 mol added 3 wt%, 4 mol added 6 wt%), polyoxyethylene nonylphenol ether phosphate (17 wt% of ethylene oxide added, 3 wt% of 16 mol added, 79 wt% added, 15 mol added 10 wt%, 14 mol added 4 % By weight, 13 moles added 4% by weight), polyoxyethylene nonylphenol ether phosphate (21% by weight of ethylene oxide added 5%, 20 moles by 78% by weight, 19 moles by 7% by weight) , 18 mole added 6% by weight, 17 mole added 4% by weight), dioctyl acid phosphate and Zelec UN ™ are one or two or more compounds selected from the group consisting of.

The heat stabilizer may be included in the composition, preferably 0.01 to 5.00% by weight. When the thermal stabilizer is used at less than 0.01% by weight, the thermal stability effect is weak. When the thermal stabilizer is used at more than 5.00%, the polymerization failure rate during curing may be high and the thermal stability of the cured product may be lowered. Examples of the thermal stabilizer include calcium stearate, barium stearate, zinc stearate, cadmium stearate, lead stearate, magnesium stearate, aluminum stearate, potassium stearate and zinc octoate, which are metal fatty acid salts. One or two or more compounds selected from the compounds can be used. Preferably, triphenyl phosphite, diphenyldecyl phosphite, phenyl diddecyl phosphite, diphenyl dodecyl phosphite, trinolyl phenyl phosphite, diphenyl isooctyl phosphite, tributyl phosphite, and tripropyl One or two or more compounds selected from phosphite, triethyl phosphite, trimethyl phosphite, tris (monodecyl phosphite) and tris (monophenyl) phosphite can be used. In addition, one or two or more selected from compounds such as lead-based 3PbO.PbSO4.4H ₂ O, 2PbO.Pb (C ₈ H ₄ O ₄ ), 3PbO.Pb (C ₄ H ₂ O ₄ ) .H ₂ O and the like Also available. In addition, organotin-based dibutyltin diaurate, dibutyltin maleate, dibutyltin bis (isooctyl maleate), dioctyl maleate, dibutyltin bis (monomethyl maleate), dibutyltin bis (la Uryl mercaptide), dibutyl bis (isooxyl mercaptoacetate), monobutyl tin tris (isooctyl mercapto acetate), dimethyl tin bis (isooctyl mercapto acetate), tris (isooctyl mercapto acetate), fertility Tiltin bis (isooctyl mercaptoacetate), dibutyl tin bis (2-mercapto ethyl laurate), monobutyl tin tris (2- mercapto ethyl laurate), dimethyl tin bis (2- mercapto ethylate) And 1 type, or 2 or more types selected from compounds, such as a monomethyltin tris (2-mercapto ethyl laurate), can also be used. Moreover, it is also possible to mix and use 2 or more types of heat stabilizers from which the series differs among the heat stabilizers illustrated above. Most preferably, by using a phosphorus-based heat stabilizer, not only the initial color of the molded lens but also the thermal stability of the optical lens can be greatly improved without deteriorating optical properties such as transparency, impact strength, heat resistance, and polymerization yield.

According to a preferred embodiment, after injecting the polymerizable composition into the mold, the mold is placed in a forced circulation oven and gradually heat-cured from 30 ° C. to 100 ° C., and then cooled to about 70 ± 10 ° C. to remove the mold to obtain a lens. .

All raw materials in the present invention preferably use high purity compounds up to 70-99.99% purity. Preferably, the purity of all raw materials is checked to purify low purity compounds and use high purity compounds without purification.

[ Example ]

Hereinafter, the present invention will be described in more detail with reference to specific examples. However, these embodiments are only for describing the present invention more specifically, and the scope of the present invention is not limited by these embodiments.

Epoxy Acrylate series  compound

1) Synthesis of Component (I) Compound

Component (I) compound is represented by the formula (3). Acrylic acid was added to the YD-128 epoxy resin of Kukdo Chemical Co., Ltd., having an equivalent weight of 187, and acrylated (prepared by reaction at 105 ° C. for 20 hours) to prepare a compound having an equivalent weight of 259, and a mixture having an average molecular weight of 518.

(3)

(n = 0 to 15)

2) Component (II) Compound

Component (II) compound is represented by the formula (4). Methacrylic acid was added to an epoxy resin having an equivalent weight of 187 and acrylated (prepared by reacting at 105 DEG C for 20 hours) to prepare a compound having an equivalent weight of 273, which was a mixture having an average molecular weight of 546.

[Chemical Formula 4]

(n = 0 to 15)

3) Component (III) Compound

Component (III) compound is represented by the formula (5). Acrylic acid was added to the YDB-400 epoxy resin of Kukdo Chemical Co., Ltd. having an equivalent weight of 400 to prepare an acrylate compound.

[Chemical Formula 5]

(n = 0 to 15)

4) Component (IV) Compound

Component (IV) compound is represented by the formula (6). Methacrylic acid was added to an epoxy resin having an equivalent weight of 400 to acrylate (prepared by reacting at 105 DEG C for 20 hours) to prepare a compound having an equivalent weight of 486, and a mixture having an average molecular weight of 972.

[Chemical Formula 6]

(n = 0 to 15)

5) Component (V) Compound

Acrylic acid was added to an alcohol in which ethylene oxide was added to bisphenol A having an equivalent weight of 175 and acrylated (reaction was carried out at 105 DEG C for 20 hours) to prepare a compound having an equivalent weight of 229. [ Average molecular weight of 458, and the structural formula thereof is shown in the following chemical formula (7).

[Formula 7]

(m = 0 ~ 5, n = 0 ~ 5, m and n are not 0 at the same time, m + n = 1 ~ 10)

6) Component (VI) Compound

A compound having an equivalent weight of 243 was prepared by adding methacrylic acid to an alcohol in which ethylene oxide was added to bisphenol A having an equivalent weight of 175 and acrylating (reacting at 105 DEG C for 20 hours). Average molecular weight of 486, and the structural formula thereof is shown in the following formula (8).

[Formula 8]

(m = 0 to 5, n = 0 to 5, m and n are not 0 at the same time, and m + n = 1 to 10.)

Example  One

(1) 15 g of component (I), 30 g of component (III) and 10 g of component (V) in the epoxy acrylate compound obtained above while maintaining the temperature at 15 ° C., styrene 40 g, dimethyl methyl styrene 2 g, alpha methyl 1 g of styrene dimer and 5 g of dibenzyl maleate were added, and 2 g of DPDP, 1 g of DOP, and 1 g of TTP, which were thermal stabilizers, were added and stirred for about 30 minutes. Thereafter, the filter was filtered with a filter paper of 0.45 µm or less while maintaining the temperature in the above range, and V65 0.05g and 3-M 0.13g were added thereto as a catalyst, and 4-PENPP 0.05g and 8-PENPP 0.2g were mixed as an internal release agent. And stirring to make a polymerizable composition for an optical lens.

(2) The polymerizable composition for an optical lens obtained in (1) was degassed under reduced pressure for 10 minutes at 15 ° C. and filtered, and then injected into a glass mold made of polyester adhesive tape while maintaining the injection temperature of the resin composition at 15 ° C. It was.

(3) The glass mold into which the composition was injected was heat-cured in a forced circulation oven from 35 ° C. to 110 ° C. over 20 hours, and then cooled to 70 ° C. to remove the glass mold to obtain a lens. The obtained lens was processed to a diameter of 72 mm, ultrasonically washed with an aqueous alkaline washing solution, and annealed at 120 ° C for 2 hours. The physical properties were measured by the following method, and the results are shown in Table 1 .

Physical properties test method

The physical properties of the optical lenses manufactured by the following physical property test methods were measured and the results are reported in Table 1 below.

1) Refractive index and Abbe number: Measured using an Abbe refractometer, a model of Atago's DR-M4.

2) Specific gravity: An analytical balance was used and measured by an underwater substitution method.

3) Release property: The epoxy acrylic resin composition was thermally cured when the optical lens was manufactured, and was marked with “○” and “×” according to the breakage of the lens or the mold when the optical lens and the mold were separated when demolded at 70 ° C. "○" means that the lens or mold is not broken at all or one is broken during the separation of 100 optical lenses and the mold, and "x" means that 4 or more lenses or molds are removed during the separation of 100 optical lenses and the mold. It is shown as a broken case.

4) McTree: 100 lenses were visually inspected under a Mercury Arc Lamp, a USHIO USH-10D, and the lenses identified as arcs were judged to be striae, with 0 to 1 being "◎". , 2-3 are indicated by "○" and four or more by "x".

5) Ring: 100 lenses were visually observed under a Mercury Arc Lamp, a USHIO USH-10D, and the lens was identified as having a ring, which was identified locally and in several places. -1 is represented by "(◎)", 2-3 are represented by "(circle)", and 4 or more are represented by "x".

5) Variable uncured: When 100 lenses were demoulded from the mold, the variable of the optical lens was uncured and the sticky lens was determined as the uncured lens, with 0 to 1 being "◎" and 2 to 3 being ""4" and four or more were represented by "x".

Example  2 ~ 20

In the same manner as in Example 1, according to the composition shown in Table 1 , the composition and the optical lens were prepared and tested for physical properties, respectively, and the results are shown in Table 1 .

Comparative Example  One

While maintaining the temperature of 2 ° C., styrene 40g, alphamethylstyrene 2g, alphamethylstyrene-dimer 1g, and benzyl malt were reacted with 15 g of component (I), 30 g of component (IV) and 10 g of component (V) in the epoxy acrylate compound. 5 g of the rate (DB) was added, and 1 g of DPDP, 1 g of TBP, and 1 g of TPP, which were thermal stabilizers, were added, followed by stirring for about 30 minutes. Then, filtered with a filter paper of 0.45㎛ or less, V65 0.05g, 3-M 0.13g was added to the catalyst, and 8-PENPP 0.1g and 12-PENPP 0.1g was mixed with the internal release agent as in Example 1 An optical resin composition was prepared. An optical lens was produced from this composition, and the physical properties of the lens were measured, and the results are shown in Table 1 .

Comparative Example  2

The composition and the optical lens were prepared according to the composition shown in Table 1 in the same manner as in Comparative Example 1, and the physical properties were tested, and the results are shown in Table 1 .

division
Example Comparative Example One 2 3 4 5 6 One 2 Injection temperature (℃) 15 8 20 25 30 35 2 45 basic
Suzy
(g)
Component I 15 20 15 15 15 15 Component II 15 20 Component III 30 29 32 Component IV 35 29 36 30 30 Component V 10 10 10 Component VI 10 10 10 diluent
(g)
Styrene 40 40 40 40 40 40 40 40 Alpha methyl styrene 2 2 2 2 2 2 2 2 Alphamethylstyrene Dimer One One One One One One One One Dibenzylmaleate 5 5 6 6 4 3 5 5 Heat stabilizer
(g) DPDP 2 2 2 2 2 2 2 2 DOP One One 0.5 0.3 0.5 One TBP One 0.5 0.5 One DBTM One TPP One One One One DPP One One One inside
Release agent
(g) 4-PENPP 0.05 0.1 0.15 0.1 8-PENPP 0.2 0.2 0.1 0.1 12-PENPP 0.2 0.1 0.1 16-PENPP 0.05 0.2 0.1 Radical initiator
(g) V65 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 3-M 0.13 0.13 0.13 0.13 0.13 0.13 0.13 0.13 lens
Properties Refractive index (nE, 20 DEG C) 1.5972 1.5971 1.5970 1.5971 1.5970 1.5972 1.5971 1.5970 Abe number 32 32 32 32 32 32 32 32 importance 1.29 1.29 1.29 1.29 1.29 1.29 1.29 1.29 Dysplasia ○ ○ ○ ○ ○ ○ ○ ○ McLee ◎ ◎ ◎ ◎ ○ ○ × × ring ○ ○ ◎ ◎ ◎ ◎ × ○ Variable Uncured ○ ○ ◎ ◎ ◎ ◎ × ○

From Table 1, the lenses produced by Examples 1 to 6, in which the blending, defoaming, and injection of the polymerizable composition were carried out at a temperature range of 5 to 40 ° C., showed that the polymers had unbalanced striae, rings, and variances as compared with the comparative examples. Uncured was good. On the other hand, in Comparative Example 1 in which the injection temperature of the resin composition for the spectacle lens was lower than the above range, the occurrence of stria, rings, and variable uncuring was large, and in Comparative Example 2 in which the injection temperature was above the above range, a lot of stria occurred. As a result, it was confirmed that high quality acrylic optical materials without transparency and deformation could be prepared by controlling the injection temperature, such as the injection into the glass mold, during the manufacture of the spectacle lens, by suppressing the striae, the ring, and the uncured uncured resin.

[Abbreviation]

Inside brother

4-PENPP: polyoxyethylene nonylphenyl phosphate (5% by weight of 5 mol of ethylene oxide added, 80% by weight of 4 mol of ethylene oxide added, 10% by weight of 3 moles of ethylene oxide added, 5% by weight of 1 mole of ethylene oxide added)

8-PENPP: polyoxyethylene nonylphenyl phosphate (5 mol% of ethylene oxide, 9 mol% of ethylene oxide, 80 mol% of ethylene oxide, 10 mol% of ethylene oxide, 7 mol of ethylene oxide, 5 mol% or less added thereto)

12-PENPP: polyoxyethylene nonyl phenol ether phosphate (3% by weight of 13 mol of ethylene oxide added, 80% by weight of 12 mol added, 8% by weight of 11 mol added, 3% by weight 9 mol added , 4 mol added 6 wt%)

16-PENPP: polyoxyethylene nonylphenol ether phosphate (3% by weight of 17 moles of ethylene oxide added, 79% by weight of 16 moles added, 10% by weight of 15 moles added, 4% by weight 14 moles added) , 13 mol added 4 wt%)

Heat stabilizer

DPDP: diphenyldodecylphosphate

DOP: dioctylacid phosphate

TBP: tributylphosphite

DBTM: dibutyltinmaleate

TPP: triphenylphosphite

DPP: diphenylisodecylphosphite

Polymerization initiator

V65: 2,2'-azobis (2,4-dimethylbarrenonitrile) (2,2'-azobis (2,4-dimethylvaleronitrile)

3-M: 1,1-bis (t-butylperoxy) -3,3-5-trimethyl cyclohexane (1,1-bis (t-butylperoxy) -3,3,5-trimethyl cyclohexane)

According to the present invention, an epoxy acrylic optical material having excellent quality without striae, whitening, ring, and variable uncured resin can be easily manufactured, and the epoxy acrylic optical material prepared according to the present invention can be prepared using conventional optical materials including thiourethane optical materials. Alternatively, it can be widely used in various fields. Specifically, it can be used as a plastic glasses lens, a 3D polarizing lens equipped with a polarizing film on the spectacle lens, a camera lens, etc. In addition to a variety of optical, such as recording media substrates, color filters and ultraviolet absorption filters used in prisms, optical fibers, optical disks, etc. Can be used in the product.

Claims (9)

In the method for producing an optical material for molding a polymerizable composition comprising a compound represented by the formula (1) and a reactive diluent, the blending, degassing, and injection of the polymerizable composition in a temperature range of 5 ~ 40 ℃ Method for producing an epoxy acrylic optical material, characterized in that made.
[Chemical Formula 1]

(Where n = 0-15, R ₁ is H or CH ₃ and R ₂ is H or Br) The method of claim 1, wherein the polymerizable composition further comprises a compound represented by Formula 2 below.
(2)

(Wherein R is H or CH ₃ , m = 0 to 5, n = 0 to 5, m and n are not 0 at the same time, and m + n = 1 to 10.) The method of claim 1 or 2, wherein the reactive diluent is styrene, divinylbenzene, alpha methyl styrene, alpha methyl styrene dimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxy styrene, monobenzyl maleate, Monobenzyl fumarate, dibenzyl maleate, dibenzyl fumarate, methylbenzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, diphene A method for producing an epoxy acrylic optical material, characterized in that one or more compounds selected from the group consisting of tilmaleate, monopentyl fumarate, dipentyl fumarate and diethylene glycol bisaryl carbonate. The method for producing an epoxy acrylic optical material according to claim 1 or 2, wherein the polymerizable composition further comprises a phosphate ester compound as an internal mold release agent. The method of claim 4, wherein the phosphate ester compound, polyoxyethylene nonyl phenol ether phosphate (5% by weight of 5 mol ethylene oxide added, 80% by weight 4 mol added, 10% by weight 3 mol added, 1 mole added 5% by weight), polyoxyethylene nonylphenyl phosphate (9 mole added by 9 moles of ethylene oxide, 8 mole added by 8 moles of ethylene oxide, 7 mole added by ethylene oxide 10 % By weight, up to 6 moles of ethylene oxide added 5% by weight), polyoxyethylene nonylphenol ether phosphate (3% by weight of 11 moles of ethylene oxide added, 80% by weight of 8 moles added, 9 moles added) 5 weight%, 7 mol added 6 weight%, 6 mol added 6 weight%), polyoxyethylene nonyl phenol ether phosphate (13 mol added ethylene oxide 3 weight%, 12 mol added 80 weight% , 8% by weight of 11 moles added, 3% by weight of 9 moles added, 6% by weight of 4 moles added), Polyoxyethylene nonyl phenol ether phosphate (3% by weight of 17 mole added ethylene oxide, 79% by weight added 16 mole, 10% by weight 15 mole added, 4% by weight 14 mole added, 13 mole added 4% by weight), polyoxyethylenenonylphenol ether phosphate (with 21 moles of ethylene oxide added 5% by weight, 20 moles added 78% by weight, 19 moles added 7% by weight, 18 moles added 6% by weight, 17% by weight added 4% by weight), dioctylic acid phosphate and Zelec UN (TM) is one or more compounds selected from the group consisting of epoxy acrylic optical material characterized in that the production of Way. The method of claim 1 or 2, wherein the polymerizable composition further comprises a heat stabilizer in an amount of 0.01 to 5.00% by weight of the total polymerizable composition. An optical material manufactured by the manufacturing method of claim 1. An optical lens made of the optical material of claim 7. The optical lens of claim 8, wherein the optical lens is an eyeglass lens or a polarizing lens.