WO2014035121A1 - Polymerization composition for epoxy acrylic optical material and method for manufacturing epoxy acrylic optical material - Google Patents

Abstract

The present invention relates to a polymerization composition for an epoxy acrylic optical material and a method for manufacturing an epoxy acrylic optical material, and more specifically to a polymerization composition for an epoxy acrylic optical material having high yield without developing striae or white turbidity by maintaining an appropriate polymerization speed, and is colorless, transparent, and changeless. Provided is the polymerization composition for the epoxy acrylic optical material, comprising an epoxy acrylate compound, which comprises 0.1-2 wt. % of alpha methylstyrene dimer with respect to the total polymerization composition. In the present invention the high-quality epoxy acrylic optical material that does not develop striae or white turbidity can be easily manufactured by stably maintaining the appropriate polymerization speed.

Description

Polymeric composition for epoxy acrylic optical material and manufacturing method of epoxy acrylic optical material

The present invention relates to a polymerizable composition for an epoxy acrylic optical material and a method for producing an epoxy acrylic optical material. In particular, an epoxy acrylic optical material capable of obtaining a high-quality optical material without striae or whitening at a high yield by maintaining an appropriate polymerization rate. It relates to a method for producing a polymerizable composition for use and an optical material.

Plastic optical lenses were introduced as a replacement for the high specific gravity and low impact of glass lenses. Representative examples thereof include polyethylene glycol bisallylcarbonate, polymethyl methacrylate, diallyl phthalate, and the like. However, optical lenses made of these polymers are excellent in physical properties such as moldability, dyeability, hard coat coating adhesion, impact resistance, etc., but the refractive index is about 1.50 (nD) and 1.55 (nD), resulting in a problem of thickening the lens. . Therefore, various attempts have been made to develop optical materials having high refractive indexes to reduce the thickness of lenses.

In Korean Patent Nos. 10-0136698, 10-0051275, 10-0051939, 10-0056025, 10-0040546, 10-0113627, and the like, a polyisocyanate compound and a polythiol compound are thermally cured to obtain a thiourethane optical lens. The thiourethane-based optical lens has excellent optical properties such as dyeability, impact resistance, and transparency, but has a problem in that the Abbe number decreases as the refractive index increases. In addition, the manufacturing process of the lens is expensive because the material is expensive and sensitive to moisture. It is difficult and there is a problem of the center deformation of the lens due to moisture in the air even when the lens is stored.

Korean Patent Nos. 10-0496911, 10-0498896, etc., unlike such thiourethane-based lenses, have high refractive index and high optical properties such as transparency, light weight, and heat resistance, and have a high refractive index. The composition for this is disclosed. Such an epoxy acrylic optical material can produce a lens without requiring separate management of moisture in the air even in a high temperature and high humidity region, and there is no central deformation of the lens due to moisture in the air when the lens is stored. When preparing a lens by polymerizing an epoxy acrylate compound, a reactive diluent to control the viscosity and reaction rate is required. Such reactive diluents include conventional styrene, divinylbenzene, alphamethylstyrene, alphamethylstyrenedimer and benzyl. Methaacrylate, chlorostyrene, bromostyrene, methoxy styrene, dibenzyl maleate, etc. have been used alone or in combination of two or more thereof. However, even when using a reactive diluent, it is not easy to keep the polymerization rate stable. If the polymerization rate is not maintained, that is, the reaction rate is slow and suddenly accelerates with temperature rise, it may cause stria and whitening.On the contrary, if the polymerization proceeds too soon after mixing, incomplete polymerization results in refractive index, strength, and transparency. Various optical properties such as such are lowered, and the quality of the lens finally obtained is lowered, resulting in a lower lens yield. Therefore, maintaining an appropriate reaction rate during the polymerization is an important factor affecting the quality of the lens, and also an important factor in the production cost since it affects the yield.

[Preceding technical literature]

[Patent Documents]

(Patent Document 1) Republic of Korea Patent Publication 10-0496911

(Patent Document 2) Republic of Korea Patent Registration 10-0498896

 The inventors have found that, among the various reactive diluents used in the prior art, alphamethylstyrene dimer has a direct influence on the reaction rate, and then, when alphamethylstyrene dimer is used in a smaller amount than the conventional amount, that is, the former 4-10 weight When the alpha methyl styrene dimer, which has been used in the% range, is used in the range of 0.1 to 2 wt%, which is much smaller than this, the polymerization rate of the epoxy acrylic polymerizable composition is stably maintained in an appropriate range, thereby achieving a high yield of high-quality lenses without striae or whitening. It was unexpectedly found that it can be prepared as.

The present invention has confirmed and completed the present invention. In the present invention, by maintaining the polymerization rate of the composition appropriately, there is provided a polymerizable composition for an epoxy acrylic optical material that can obtain a lens having excellent optical properties without high striae, whitening, or the like in high yield. It aims to provide. "Stria" refers to a phenomenon that is locally different from the normal refractive index due to a difference in composition, such as striae and whitening may adversely affect the quality and performance of the optical material. An object of the present invention is to produce a colorless transparent high quality epoxy acrylic optical material without causing such a striae or whitening during lens manufacturing through the appropriate polymerization rate control of the composition.

In the present invention,

In the polymerizable composition for epoxy acrylic optical material comprising a compound represented by the formula (1), the polymerizable polymer for epoxy acrylic optical material, characterized in that it comprises alpha methyl styrene dimer in 0.1 to 2% by weight of the total polymerizable composition. A composition is provided. The polymerizable composition for an epoxy acrylic optical material of the present invention may further include a compound represented by Formula 2 below.

[Formula 1]

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

[Formula 2]

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

In the present invention,

When molding the polymerizable polymerizable composition for an epoxy acrylic optical material including the compound represented by Chemical Formula 1, an alphamethylstyrene dimer is added at 0.1 to 2% by weight of the total weight of the polymerizable composition to maintain an appropriate polymerization rate. Provided is a method for producing an epoxy acrylic optical material, including mixing and molding a polymer. In this case, the polymerizable composition may further include a compound represented by Chemical Formula 2.

Moreover, in this invention, the optical material obtained by casting-polymerizing the said polymeric composition and the optical lens which consists of this optical material are provided. The optical lens in particular comprises an spectacle lens or a polarizing lens.

The present invention provides a polymerizable composition for an epoxy acrylic optical material that can produce a high quality lens without striae or whitening in a high yield by stably maintaining an appropriate polymerization rate. According to the present invention, an epoxy acrylic optical material having high refractive index and high Abbe's number and excellent optical properties such as transparency, light weight and heat resistance can be manufactured with high quality without striae or whitening, and lowering production cost by improving yield. Can be.

The polymerizable composition for epoxy acrylic optical materials of the present invention includes one or two or more compounds represented by the following general formula (1) as a monomer component, and contains 0.1 to 2 wt% of alphamethylstyrene dimer in the total composition. The polymerizable composition of the present invention may preferably further include a compound represented by the following Chemical Formula 2.

[Formula 1]

N is 0 to 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 2]

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

In the polymerizable composition of the present invention, alpha methyl styrene dimer is included in a small amount of 0.1 to 2% by weight of the total composition to maintain a stable and constant polymerization rate of the composition. If the polymerizable composition does not maintain an appropriate polymerization rate during the polymerization reaction and the reaction rate suddenly increases with temperature rise, stria may occur. On the contrary, if the polymerization reaction proceeds too quickly immediately after the mixing of the composition, incomplete polymerization results in refractive index, Various optical characteristics, such as intensity and transparency, will fall. The rate of polymerization of the composition thus has a significant impact on the quality of the lens finally obtained and will influence the yield of the lens. Alphamethylstyrene dimer has conventionally been used as a reactive diluent to control the viscosity of the composition and to control the reaction rate.It was mainly used with other reactive diluents such as styrene, rather than alone, and even when used with styrene, 4 weight percent or more, generally 4-10 weight percent. In other words, there was a conventional recognition that at least 4% by weight or more of alphamethylstyrene dimer was used as a reactive diluent. However, in the present invention, it was found that among the various reactive diluents, the alpha methyl styrene dimer has the most direct effect on the reaction rate, and when the alpha methyl styrene dimer is used in the range of 0.1 to 2 wt%, which is much lower than the conventional amount, the polymerization rate of the composition is increased. I found that I could keep my schedule more effective. Alphamethylstyrene dimer in the epoxy acrylic polymerizable composition of the present invention is included in 0.1 to 2% by weight of the total composition, more preferably 0.2 to 1% by weight. If the content of the alpha methyl styrene dimer in the composition is less than 0.1% by weight has little effect on the polymerization rate of the composition, it may cause stria due to poor polymerization, and if it exceeds 2% by weight, the reaction rate is slow and sudden rise of temperature As a result, the reaction rate is increased, which may cause striae or whitening due to polymerization heterogeneity. On the other hand, alpha methyl styrene dimer contained in a low content of 0.1 to 2% by weight can maintain a constant reaction rate of the composition in a proper range, not too fast or slow, in particular, the rapid rise of the reaction rate according to the temperature rise Since it can suppress, a lens can be manufactured without a stria and whitening.

The polymerizable composition of the present invention may further contain other reactive diluents in addition to the alphamethylstyrene dimer. It is preferable to further include other reactive diluents for proper viscosity control of the polymerizable composition. Other reactive diluents are preferably styrene, divinylbenzene, alphamethylstyrene, benzyl methacrylate, chlorostyrene, bromostyrene, methoxystyrene, monobenzylmaleate, monobenzyl fumalate, dibenzyl maleate, di Benzyl fumarate, methylbenzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, dipentyl maleate, monopentyl fumarate, dipentyl fumal One or two or more compounds selected from the group consisting of latex and diethylene glycol bisaryl carbonate. The ratio of the total reactive diluent containing the alpha methyl styrene dimer and another reactive diluent is 30 to 300 based on 100 parts by weight of the total monomer components further comprising the compound represented by the formula (1) or the compound represented by the formula (2). The weight part is good. If the reactive diluent is used in less than 30 parts by weight, the viscosity of the composition is not easy to handle, so handling may be 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, This may adversely affect the polymerization reaction.

The epoxy acrylic polymerizable composition of the present invention 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) of 1.54 to 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.

The method for producing an epoxy acrylic optical material of the present invention is appropriate polymerization when casting a polymerizable composition comprising an epoxy acrylate compound represented by the formula (1) or a compound represented by the formula (2) as a monomer component. In order to maintain the rate, 0.1 to 2% by weight of the alpha-methylstyrene dimer is added and mixed in the total weight of the polymerizable composition, followed by mold polymerization. According to a preferred embodiment, prior to mold polymerization, the purity of all the raw materials is checked to purify low purity compounds and use high purity compounds without purification. Preferably, high purity compounds up to 70-99.99% purity are used. According to a preferred embodiment, the epoxy acrylate compound, the alpha methyl styrene dimer and other reactive diluents are mixed, then the reaction catalyst is added and stirred, and then the polymerizable composition is injected into the mold via vacuum degassing. The mold into which the polymerizable composition was injected 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 mold to obtain a lens.

EXAMPLE

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

Epoxy acrylate 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.

[Formula 3]

(n = 0-15)

2) Component (II) Compound

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

[Formula 4]

(n = 0 to 15)

3) Component (III) Compound

The component (III) compound is shown in the formula (5), and the acrylic acid is added to the YDB-400 epoxy resin of Kukdo Chemical, which has an equivalent weight of 400, to be acrylated (prepared by reacting at 105 DEG C for 20 hours) to give a compound having an equivalent weight of 472. And a mixture having an average molecular weight of 944.

[Formula 5]

(n = 0 to 15)

4) Component (IV) Compound

Component (IV) compound is shown in Chemical Formula 6, and acrylated (prepared by reacting for 20 hours at 105 ° C) by adding methacrylic acid to an epoxy resin having an equivalent weight of 400 to prepare a compound having an equivalent weight of 486. This is a mixture of 972.

[Formula 6]

(n = 0 to 15)

5) Component (V) Compound

Acrylic acid was added to an alcohol having ethylene oxide added to bisphenol A having an equivalent weight of 175, and then acrylated (prepared by reacting at 105 DEG C for 20 hours) to prepare a compound having an equivalent weight of 229. The mixture has an average molecular weight of 458, and the structural formula is shown in Chemical Formula 7 below.

[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

Methacrylic acid was added to an alcohol having ethylene oxide added to bisphenol A having an equivalent weight of 175 to acrylate (prepared by reacting at 105 ° C. for 20 hours) to prepare a compound having an equivalent weight of 243. The mixture has an average molecular weight of 486, and the structural formula is shown in Chemical Formula 8 below.

[Formula 8]

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

Example 1

In the epoxy acrylate compound obtained above, 0.5 g of alpha methyl styrene dimer, a polymerization regulator, was added to 15 g of component (I), 30 g of component (III), and 10 g of component (V), and 40 g of styrene and 5 g of alpha-methyl styrene as reaction diluents were added. Then, 2 g of DPDP, 1 g of DOP, 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 0.12g is added to the catalyst, 4-PENPP 0.05g and 8-PENPP 0.2g as an internal release agent is added and mixed to the polymerizable composition Made. The polymerizable composition for optical lenses thus prepared was stirred for 1 hour, degassed under reduced pressure for 10 minutes, filtered, and then injected into a glass mold assembled with a polyester adhesive tape. The glass mold in which the polymerizable 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 resulting lens was processed to a diameter of 72 mm and then ultrasonically washed with an alkaline aqueous washing solution, followed by annealing at 120 ° C. for 2 hours. The physical properties were measured by the following method, and the results are shown in Table 1 .

Property 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: It was measured using an Abbe refractometer, a DR-M4 model of Atago.

2) Specific gravity: It was measured by an underwater substitution method using an analytical balance.

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 is kept at 100 ° C for 10 hours, and when the APHA value changes to less than 2 in the measurement of color change, it is indicated by "○", and when the APHA value changes to 2 or more, it is indicated by "×" It was.

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 the polymerization, demolding, and then irradiated with roughness of 1800LUX or more without surface treatment, the percentage of visual observation of cloudy appearance in some or several parts of the lens was calculated.

Examples 2-6

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 1

To 15 g of component (I), 30 g of component (IV) and 10 g of component (V) in the epoxy acrylate compound obtained above, 0.05 g of alpha methyl styrene dimer as a polymerization regulator was added, and 40 g of styrene and alpha -methyl styrene, which were reaction diluents, were added. 5 g were added, and 2 g of DPDP, 1 g of TBP, and 1 g of TPP, which were thermal stabilizers, were added and stirred for about 30 minutes. Thereafter, the resultant was filtered with a filter paper of 0.45 µm or less, and thereto was added 0.05g of G65 and 0.13g of 3-M as a catalyst, and 8-PENPP 0.1g and 12-PENPP 0.1g were mixed as an internal release agent to prepare a resin composition for an optical lens. After the preparation, an optical lens was manufactured by the following method, and the physical properties of the lens were measured, and the results are shown in Table 1 .

Comparative Example 2

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

Table 1

Abbreviation

Internal release agent

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 mol of ethylene oxide added, 5% by weight of 1 mol of ethylene oxide added)

8-PENPP: polyoxyethylene nonylphenyl phosphate (5% by weight of 9 mol of ethylene oxide added, 80% by weight of 8 mol of ethylene oxide, 10% by weight of 7 mol of ethylene oxide, ethylene oxide 5 mole% added by 6 mol or less)

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: tributylphosphate

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, by maintaining a suitable polymerization rate stably, it is possible to easily produce an epoxy acrylic optical material having excellent quality without stria, whitening, etc. at a low manufacturing cost. The epoxy acrylic optical material prepared according to the present invention has excellent optical properties such as high refractive index, high Abbe's number, transparency, light weight and heat resistance, and has excellent quality without striae, whitening, etc. It can be widely used in various fields. In particular, it may be widely used as an eyeglass lens or a camera lens, and specifically, it may be used as a plastic eyeglass lens, a 3D polarizing lens having a polarizing film attached to the spectacle lens, or a recording medium used for a prism, an optical fiber, an optical disk, etc. It can be used in various optical products, such as a substrate, a coloring filter, and an ultraviolet absorption filter.

Claims (17)

1. In the polymerizable composition for epoxy acrylic optical material comprising a compound represented by the formula (1), the polymerizable polymer for epoxy acrylic optical material, characterized in that it comprises alpha methyl styrene dimer in 0.1 to 2% by weight of the total polymerizable composition. Composition.

   [Formula 1]

   

   (Where n = 0-15, R ₁ is H or CH ₃ and R ₂ is H or Br)
2. The polymerizable composition for an epoxy acrylic optical material according to claim 1, further comprising a compound represented by the following Chemical Formula 2.

   [Formula 2]

   

   (Where R is H or CH ₃ , m = 0-5, n = 0-5, m and n are not zero at the same time, m + n = 1-10)
3. The polymerizable composition for epoxy acrylic optical material according to claim 1 or 2, wherein the alpha methylstyrene dimer is contained in an amount of 0.2 to 1% by weight.
4. The polymerizable composition has a liquid phase 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). It is 1.54-1.63, The polymeric composition for epoxy acrylic optical materials characterized by the above-mentioned.
5. The styrene, divinylbenzene, alphamethyl styrene, benzyl methacrylate, chlorostyrene, bromostyrene, methoxy styrene and monobenzyl maleate according to claim 1 or 2, in addition to the alpha methyl styrene dimer. , Monobenzyl fumarate, dibenzyl maleate, dibenzyl fumarate, methylbenzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate, A polymerizable composition for epoxy acrylic optical materials further comprising one or two or more compounds selected from the group consisting of dipentyl maleate, monopentyl fumarate, dipentyl fumarate and diethylene glycol bisaryl carbonate.
6. The epoxy acrylic optical material according to claim 5, wherein the epoxy acrylic optical material comprises 30 to 300 parts by weight of the total reactive diluent based on 100 parts by weight of the compound represented by the formula (1) or the monomer component further comprising the compound represented by the formula (2). Polymerizable composition for.
7. The polymerizable composition for epoxy acrylic optical material according to claim 1 or 2, further comprising a phosphate ester compound as an internal release agent.
8. The method of claim 7, wherein the phosphate ester compound, polyoxyethylene nonyl phenol ether phosphate (5% by weight 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), dioctylic acid phosphate and Zelec UN ™ is one or two or more compounds selected from the group consisting of polymerizable composition for epoxy acrylic optical material.
9. The polymerizable composition for epoxy acrylic optical material according to claim 1 or 2, further comprising 0.01 to 5.00% by weight of the thermal stabilizer.
10. When molding the polymerizable polymerizable composition for epoxy acrylic optical material comprising the compound represented by the following formula (1), in order to maintain an appropriate polymerization rate, alpha methyl styrene dimer is added at 0.1 to 2% by weight of the total weight of the polymerizable composition, A method for producing an epoxy acrylic optical material comprising molding and mixing after mixing.

    [Formula 1]

    

    (Where n = 0-15, R ₁ is H or CH ₃ and R ₂ is H or Br)
11. The method of claim 10, wherein the polymerizable composition further comprises a compound represented by Chemical Formula 2 below.

    [Formula 2]

    

    (Where R is H or CH ₃ , m = 0-5, n = 0-5, m and n are not zero at the same time, m + n = 1-10)
12. The method for producing an epoxy acrylic optical material according to claim 10 or 11, wherein the alphamethylstyrene dimer is added and mixed at 0.2 to 1% by weight.
13. The method of claim 10 or 11, in addition to the alpha methyl styrene dimer, a reactive diluent, styrene, divinyl benzene, alpha methyl styrene, benzyl methacrylate, chlorostyrene, bromo styrene, methoxy styrene, monobenzyl mal Rate, monobenzyl fumarate, dibenzyl maleate, dibenzyl fumarate, methylbenzyl maleate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl fumarate, monobutyl maleate, monopentyl maleate Epoxy characterized in that the polymerization of the mold after further adding, mixing one or two or more compounds selected from the group consisting of, dipentyl maleate, monopentyl fumarate, dipentyl fumarate, diethylene glycol bisaryl carbonate Method for producing acrylic optical material.
14. According to claim 13, 30 to 300 parts by weight of the total reactive diluent is added and mixed with respect to 100 parts by weight of the compound represented by the formula (1) or a monomer component further comprising a compound represented by the formula (2). A method for producing an epoxy acrylic optical material.
15. The optical material obtained by casting-polymerizing the polymerizable composition of Claim 1 or 2.
16. An optical lens made of the optical material of claim 15.
17. The optical lens of claim 16, wherein the optical lens is an eyeglass lens or a polarizing lens.