KR20140029275A - A method of preparing epoxy acryl based optical material - Google Patents

Abstract

The present invention relates to a polymerization composition for an epoxy acryl optical material and a method for manufacturing an epoxy acryl optical material and, specifically to a method for manufacturing a high quality optical material having high yield without developing striae, white residues, or microbubbles, and is colorless, transparent, and changeless. Provided is a method for manufacturing the epoxy acryl optical material in which a polymerization composition, comprising an epoxy acryl compound as a monomer component, is in-mold polymerized, and is characterized in that the polymerization composition is processed under a specific vacuum condition before being injected into a mold for in-mold polymerization so as to suppress development of striae, white turbidity, or fine bubbles. The epoxy acryl optical material manufactured according to the present invention can replace existing optical materials and be widely used in a variety of industries such as lens of glasses, camera lenses, etc.

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 free of deformation with no high yield without striae, whitening, or microbubbles.

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. By the way, when forming a lens by casting polymerization of the composition, a striae, whitening or microbubbles are often generated to deteriorate the quality of the lens. Such occurrence of striae, whitening, and microbubbles deteriorate the quality of the lens, and thus improvement has been required. In addition, the reduction of production costs has been a major concern in the lens field recently, the occurrence of striae, whitening, microbubbles are a 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 unexpectedly found that the degree of vacuum during defoaming prior to injecting the polymerizable composition including the monomer component into the mold has a significant correlation to the formation of striae, whitening, and microbubbles of the finally obtained lens. That is, when the polymerizable composition was treated with an appropriate vacuum, striae, whitening, and microbubbles were hardly generated in the lens finally obtained through mold polymerization. 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 without deformation in a high yield without generating striae, whitening, or microbubbles. "Stria" refers to a phenomenon that is locally different from the surrounding normal refractive index due to a difference in composition. The term "whitening" and "whitening" refers to a phenomenon in which the lens becomes cloudy, mainly "whitening" refers to a local phenomenon and "whitening" refers to a phenomenon of total clouding, but in the present invention, "whitening" is meant to include whitening. Streaks, bleaching and microbubbles adversely affect the quality and performance of optical materials.

In the present invention,

In the method for producing an optical material for polymerizing a polymerizable composition comprising a compound represented by the formula (1) as a monomer component, in order to suppress the occurrence of striae, whitening and micro-bubble, the polymerizable composition prior to the mold polymerization Provided is a method for producing an epoxy acrylic optical material, characterized in that the mold polymerization by injecting into a mold after vacuum treatment under the condition that the X value in the formula 1 is 0.02 ~ 2.5. 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)

[Formula 1]

X = T × 1 / t

(T is the degree of vacuum expressed in torr, t is the time to vacuum (min, min), and T is in the range of 0.05 to 300.)

(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 treating the polymerizable composition with an appropriate vacuum prior to the polymerization of the mold, it is possible to produce a colorless, transparent, high-quality lens free of striae, whitening, and microbubbles, and to lower the production cost by improving yield.

Method for producing an epoxy acrylic optical material of the present invention, after the vacuum treatment of a polymerizable composition comprising an epoxy acrylate compound represented by the formula (1) as a monomer component under the condition that the X value in the formula 1 below 0.02 ~ 2.5 It is injected into a mold and polymerized with a mold. 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.

[Formula 1]

X = T × 1 / t

(T is the degree of vacuum expressed in torr, t is the time to vacuum (min, min), and T is in the range of 0.05 to 300.)

(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 the production of epoxy acrylic optical materials, a monomer component, a reactive diluent, an internal mold release agent and other additives are usually mixed to obtain a polymerizable composition, and then injected into a mold to polymerize the mold. Was injected into the mold. However, the conventional defoaming process was recognized only to suppress the bubble generation during the polymerization as much as possible, there was a case in which microbubbles are generated even through such a defoaming process. In the present invention, for the first time it was found and confirmed that the degree of vacuum in the defoaming process has an important correlation not only to microbubbles but also to the striae and whitening of the lens. In the present invention, before the polymerization, the composition is evacuated to a specific vacuum degree, i.e., the condition that the X value is 0.02 to 2.5 in Equation 1, thereby suppressing the occurrence of striae, whitening, and microbubbles of the finally obtained lens. To produce an epoxy acrylic optical material. In Equation 1, T is defined as the initial pressure (torr) when the first vacuum condition is created.

The polymerizable composition may further include a reactive diluent. Preferably it comprises 30 to 300 parts by weight of the reactive diluent with respect to 100 parts by weight of the compound represented by the formula (1) or further comprising a compound represented by the formula (2). As the reactive diluent, for example, styrene, divinylbenzene, alpha methyl styrene, alpha methyl styrene dimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxy styrene, monobenzyl maleate, monobenzyl fumalate, dibenzyl Maleate, dibenzyl fumarate, methylbenzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, dipentyl maleate, monopentyl fumarate , Dipentyl fumarate, diethylene glycol bisaryl carbonate, and the like may 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. When the reactive diluent is used in less than 30 parts by weight, the viscosity of the composition is not easy to handle, so handling is poor. On the contrary, when the reactive diluent is used in excess of 300 parts by weight, the viscosity of the composition is too low, which adversely affects the refractive index. Streaking may occur. The polymerizable composition of the present invention comprising a reactive diluent preferably has a liquid viscosity of 20 to 1,000 cps at 25 ° C, a liquid refractive index (nE, 20 ° C) of 1.50 to 1.58, and a solid phase refractive index (nE, 20 ° C). This 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.

In addition, the polymerizable composition of the present invention 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 detach and remove the lens. Get

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). A compound having an equivalent weight of 259 was prepared by adding acrylic acid to the YD-128 epoxy resin of Kukdo Chemical having an equivalent weight of 187 (prepared by reacting at 105 ° C. for 20 hours), and 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) and 30 g of component (III) in the epoxy acrylate compound obtained above 0.5 g of alpha methyl styrene dimer as a polymerization regulator, 40 g of styrene and 5 m of alpha methyl styrene as a reaction diluent, 5 g of DPDP as a heat stabilizer, 1 g of DOP and 1 g of TPP were added to 10 g of component (V) and stirred for about 30 minutes. Thereafter, the resultant was filtered with a filter paper of 0.45 μm or less, 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 and stirred as an internal mold release agent to polymerize the optical lens. A sex composition was made.

(2) The polymerizable composition for an optical lens was degassed under reduced pressure at 5 torr for 2 minutes, filtered, and then poured into a glass mold assembled with a polyester adhesive tape.

(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

1) Refractive index and Abbe number: It was measured using an Abbe refractometer, a DR-M4 model of Atago.

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) Thermal Stability: The cured optical lens was maintained at 100 ° C. for 10 hours, and when the APHA value did not change by more than 2 in the measurement of color change, it was indicated by “○”, and when the APHA value changed by 2 or more, it was indicated by “×”. .

5) Streaks: 100 lenses were visually observed under a Mercury Arc Lamp, which is a USHIO USH-10D, and it was determined that a lens having a whistle had a stria, and a stria occurrence rate was calculated.

6) Whitening: After demolding, it was demolded and irradiated with roughness of 1800LUX or more without any surface processing to calculate the percentage of visual observation of cloudy phenomenon locally due to polymerization heterogeneity.

7) Microbubbles: 100 lenses were visually observed under a Mercury Arc Lamp, a USHIO USH-10D, and the number of microbubbles visually observed was calculated as a percentage.

Example  2 to 6

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

To 15 g of component (I), 30 g of component (III) and 10 g of component (V) in the epoxy acrylate compound, 0.5 g of alpha methyl styrene dimer, 40 g of styrene as a reaction diluent and 5 g of alpha methyl styrene were added, and heat After adding 2 g of DPDP and 1 g of TPP as stabilizers, the mixture was stirred 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 mold release agent as in Example 1 To prepare a resin composition for an optical lens, defoaming at 0.03 torr for 2 minutes, and filtered and then a resin composition was injected into the glass mold to prepare an optical lens. Lens production and physical properties of the lens were measured in the same manner as in Example 1, and the results are shown in Table 1 .

Comparative Example  2

Table 1 in the same manner as in Comparative Example 1 Compositions and optical lenses were prepared and tested for physical properties according to the described compositions, and the results are shown in Table 1 .

division
Example Comparative Example One 2 3 4 5 6 One 2 Torr,
Time (minutes, min.) 5 torr, 2 min. 0.05 torr, 1 min. 20 torr, 20 min. 50 torr, 40 min. 80 torr, 90 min. 100 torr, 120 min. 0.03 torr, 2 min. 310 torr, 120 min. basic
Suzy
(g)
Component I 15 15 15 15 15 Component II 15 15 15 Component III 30 30 30 30 30 Component IV 30 30 30 Component V 10 10 10 10 Component VI 10 10 10 10 diluent
(g)
Alphamethylstyrene Dimer 0.5 One 1.5 0.3 2 0.8 0.5 1.5 Styrene 40 40 40 40 40 40 40 40 Alpha-methylstyrene 5 5 5 5 5 5 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 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 1.5970 1.5969 1.5972 1.5972 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 ○ ○ ○ ○ ○ ○ × ○ Thermal stability ○ ○ ○ ○ ○ ○ ○ ○ McLee 3 3 One 3 6 8 30 51 all sorts of flowers 2 3 2 2 2 3 20 38 Microbubbles One 2 2 One 2 2 2 10

[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: diphenyldodecyl phosphate

DOP: dioctyl acid 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, it is possible to easily manufacture epoxy acrylic optical materials having excellent quality without striae, whitening, and microbubbles. The epoxy acrylic optical material prepared according to the present invention can be widely used in various fields in place of conventional optical materials including thiourethane based optical materials. 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 polymerizing a polymerizable composition comprising a compound represented by the formula (1) as a monomer component, in order to suppress the occurrence of striae, whitening and micro-bubble, the polymerizable composition prior to the mold polymerization Equation 1 is a method for producing an epoxy acrylic optical material, characterized in that the mold polymerization by injecting into a mold after vacuum treatment under the condition that the X value is 0.02 ~ 2.5.
[Chemical Formula 1]

(Where n = 0-15, R ₁ is H or CH ₃ and R ₂ is H or Br)
[Formula 1]
X = T × 1 / t
(T is the degree of vacuum expressed in torr, t is the time to vacuum (min, min), and T is in the range of 0.05 to 300.) The method of claim 1, wherein the polymerizable composition further comprises a compound represented by Formula 2 as a monomer component.
(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.) According to claim 1 or 2, wherein the polymerizable composition further comprises a reactive diluent 30 to 300 parts by weight based on 100 parts by weight of the monomer component, the reactive diluent is styrene, divinylbenzene, alpha methyl styrene, alpha methyl Styrenedimer, benzyl methacrylate, chlorostyrene, bromostyrene, methoxy styrene, monobenzyl maleate, monobenzyl fumarate, dibenzyl maleate, dibenzyl fumalate, methyl benzyl maleate, dimethyl maleate, diethyl Selected from the group consisting of maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, dipentyl maleate, monopentyl fumarate, dipentyl fumarate and diethylene glycol bisaryl carbonate It is 1 type, or 2 or more types of compound, The manufacturing method of the epoxy acrylic optical material characterized by the above-mentioned. 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 (with 11 moles of ethylene oxide added 3% by weight, 10 moles added 80% by weight, 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% , 11 mole added 8% by weight, 9 mole added 3% by weight, 4 mole added 6% by weight) , Polyoxyethylene nonylphenol ether phosphate (3% by weight of 17 mole added ethylene oxide, 79% by weight added 16 mole, 10% by weight added 15 mole, 4% by weight 14 mole added, 13 moles 4 weight% added), polyoxyethylene nonylphenol ether phosphate (5 weight% with 21 mol of ethylene oxide added, 20 weight added 78 weight percent, 19 weight added 7 weight percent, 18 mol added 6% by weight, 17% by weight added 4% by weight), dioctyl acid phosphate and Zelec UN ™ is one or two or more compounds selected from the group consisting of epoxy acrylic optical material Manufacturing method. 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.