KR20120065885A - Internal mold release agent for production of epoxy acryl optical lens - Google Patents

Abstract

PURPOSE: An internal release agent is provided to improve releasing performance together with improving optical properties like lightness, moldability, dyeability, heat resistance, and transparency. CONSTITUTION: An internal release agent of a phosphate ester compound is comprised in a resin composition for optical lens by the amount of 0.001-10 weight%. The resin composition consists of 30.0-80.0 weight% of an epoxy acrylate main component in chemical formula 1, and 10.0-60.0 weight% of a reactive diluent of one or more kinds. In chemical formula 1, n is 0-15, R1 is H or Ch3, and R2 is H or Br. The phosphate ester compound is in chemical formula 2.

Description

Internal Mold Release Agent for Epoxy Acrylic Optical Material {Internal Mold Release Agent For Production of Epoxy Acryl Optical Lens}

The present invention relates to an internal releasing agent of a phosphate ester compound added to a resin composition for plastic optical lenses, and in particular, by using phosphate ester as an internal releasing agent in the resin composition for optical lenses, there is no clouding and excellent deformability, resulting in high optical lens yield. The present invention relates to a resin composition for an epoxy acrylic optical lens, which has been greatly increased and has excellent deformability, transparency, and thermal stability.

Plastic eyeglass lenses have been introduced as a substitute for high specific gravity and low impact resistance. Typical examples include polyethylglycol bis allyl carbonate, polymethyl methacrylate, polyethyl glycol bis allyl carbonate and diallyl phthalate. However, optical lenses made of these polymers have excellent physical properties such as moldability, dyeing property, hard coat coating adhesion, impact resistance, etc., but the refractive index is 1.50 (nD) and 1.55 (nD), so the edge of the lens is thick. Various attempts have been made to develop optical materials with high refractive index in order to reduce the edge thickness of the lens. In addition, the releasability of poor separation from the mold after polymerization significantly lowers the lens yield, so a solution is required.

As an optical resin composition based on urethane, in Korea Patent Application 10-1987-0001768, 10-1987-014268, 10-1989-001686, 10-1989-001865, 10-1989-001913, 10-1993-015515, A method of manufacturing a plastic optical lens for thermosetting an isocyanate and a polythiol composition is provided. This optical lens has excellent optical properties such as dyeability, hard coat coating and adhesiveness, impact resistance, Abbe's number and transparency, but the heat resistance is poor, so that the center of the lens is severely deformed when the lens is hard coated. Due to the weak surface strength of the production process there was a problem that a lot of surface scratches occur. In addition, when the resin composition is blended and exposed to moisture in the air until it is injected into the glass mold, there is a problem in that a cloudy phenomenon occurs in the lens.

As an optical material having excellent heat resistance, a resin composition of an epoxy acrylic optical lens, that is, Japanese Patent Application Nos. Hei 4-207607 and Hei 6-1052, tetrabromobisphenol A diacrylate, divinylbenzene, styrene or styrene, benzyl methacrylate, Although a method of manufacturing an optical lens using an isocyanate or the like has been proposed, these optical lenses have a problem in that color change occurs during lens hard coating due to low thermal stability.

In order to solve such a problem, Korean Patent Application No. 10-2003-0018653 proposes a resin composition for a high refractive optical lens mainly composed of epoxy acrylate. It uses a heat stabilizer to reduce the color change with respect to heat, and is excellent in transparency and heat resistance. However, depolymerization is poor due to poor separation from the mold after polymerization, and there is a problem in that polymerization imbalance occurs when the amount of the catalyst is increased, thereby separating the lens and the mold in advance.

In the present invention, by adding the internal releasing agent of the phosphate ester compound to the resin composition for high refractive optical lens containing epoxy acrylate as a main component, the problem of the whitening phenomenon or the deformation occurring in the existing silicone releasing agent is solved, and after the polymerization, The problem of polymerization imbalance and heat resistance, which is a phenomenon of separation between the mold and the mold, has been solved.

The present invention aims to solve such problems of the prior art. That is, in the present invention, in the resin composition for high refractive optical lens containing epoxy acrylate as a main component, the separation property with the mold is poor after polymerization, and thus, deforming is not good, and when the amount of the catalyst is increased, polymerization imbalance occurs and separation between the lens and the mold is previously separated. There is a problem. In addition, when the silicone type release agent is used, cloudiness may occur, and transparency may be degraded, thereby greatly decreasing the yield of the lens.

In the present invention, by adding the internal releasing agent of the phosphate ester compound to the resin for high refractive optical lens containing epoxy acrylate as a main component, the phenomenon of pre-separation between the lens and the mold caused by the whitening, deforming and polymerization imbalance of the silicone releasing agent, low To solve problems such as lens yield and thermal stability.

In the present invention to achieve the above object,

Epoxy acrylic optical resin composition is proposed to overcome the problems of urethane optical lens, low heat resistance, surface hardness, and lens manufacturing, which have excellent optical properties, that is, transparency and high refractive index without turbidity, and the aforementioned epoxy acrylic optical In order to solve the clouding, deforming and low lens yield occurring in the lens, to solve the problem by using a phosphate ester as an internal release agent in the resin composition for the optical lens. This is in the present invention 39.5 ~ 80.0% by weight of the resin represented by the formula (1) which is an epoxy acrylic high refractive optical resin

[Formula 1]

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

[Formula 2]

(X, Y, Z is hydrogen, halogen, linear and branched aliphatic, aromatic, aliphatic to aromatic, aliphatic to aliphatic, alicyclic, ethylene oxide or propylene oxide added to the aromatic residue and aliphatic hydrocarbon substituted by halogen atoms) Any one selected from the group consisting of the same or different from each other)

0.01 to 5.0% by weight of one or two or more of the thermal stabilizers, 10.0 to 60% by weight of one or two or more reactive diluents for viscosity control, and 0.01 to 10% by weight of a molecular regulator The resin composition for an optical lens obtained by mixing the composition with a phosphate ester, an internal mold release agent represented by the formula (2), has a liquid viscosity of 20 to 1,000 cps at 25 ° C., suitable for mold polymerization, and a liquid refractive index (nE, 20 ° C.) of the resin composition. The present invention provides a resin composition for epoxy-acrylic high refractive optical lens, transparent, deformable and thermally stable, without white turbidity having 1.50 to 1.58 and solid phase refractive index (nE, 20 ° C) of 1.57 to 1.63.

The resin composition for an optical lens of the present invention is prepared by adding a phosphate ester compound, an internal mold release agent, to an optical material based on a halogen bisphenol A diglycidyl diacrylate compound, which is light weight, moldability, dyeing resistance, heat resistance, Excellent optical properties such as transparency, but also excellent deformability, greatly reduced the polymerization imbalance, greatly increased the lens yield. Therefore, the lens of the present invention can be widely used in spectacle lenses or camera lenses by improving the existing problems, and recording media used in prisms, optical fibers, optical discs, etc. in addition to the plastic spectacle lens and the 3D polarizing lens equipped with a polarizing film on the spectacle lens It can also be used in various optical products such as substrates, color filters, and ultraviolet absorption filters.

The resin composition for an optical lens of the present invention is contained in 39.5 to 80.0% by weight of the resin represented by the formula (1).

0.01 to 5.0% by weight of one or two or more of the thermal stabilizers, 10.0 to 60% by weight of one or two or more reactive diluents for viscosity control, and 0.01 to 10% by weight of a molecular regulator The resin composition for an optical lens obtained by mixing a resin composition with a phosphate ester, which is an internal mold release agent represented by the formula (2), has a liquid viscosity of 20 to 1,000 cps at 25 ° C. and a liquid refractive index of the resin composition (nE, 20 ° C.). ) Is 1.50 ~ 1.58, and solid-state refractive index (nE, 20 ℃) is 1.57 ~ 1.63.

[Formula 1]

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

[Formula 2]

(X, Y, Z is hydrogen, halogen, linear and branched aliphatic, aromatic, aliphatic to aromatic, aliphatic to aliphatic, alicyclic, ethylene oxide or propylene oxide added to the aromatic residue and aliphatic hydrocarbon substituted by halogen atoms) Any one selected from the group consisting of the same or different from each other)

The phosphate ester compound used as the internal release agent in the present invention may be preferably represented by the formula (II).

Examples of the phosphate ester compound represented by the above formula (II) include (mono, di) methyl phosphoric acid; (Mono, di) ethyl phosphoric acid; (Mono, di) (n-propyl) phosphoric acid; (Mono, di) isopropyl phosphoric acid; (Mono, di) (n-butyl) phosphoric acid; (Mono, di) (n-pentyl) phosphate; (Mono, di) (n-hexyl) phosphoric acid; (Mono, di) (n-heptyl) phosphate; (Mono, di) (n-octyl) phosphate; (Mono, di) (2-ethylhexyl) phosphoric acid; (Mono, di) (n-nonyl) phosphoric acid; (Mono, di) (n-decyl) phosphoric acid; (Mono, di) (isodecyl) phosphoric acid; (Mono, di) (n-undecyl) phosphoric acid; (Mono, di) (n-dodecyl) phosphoric acid; (Mono, di) (tridecyl) phosphoric acid; (Mono, di) (n-tetradecyl) phosphoric acid; (Mono, di) (n-pentadecyl) phosphate; (Mono, di) (n-hexadecyl) phosphoric acid; (Mono, di) (n-octadecyl) phosphoric acid; (Mono, di) (o-methyldecyl) phosphate; (Mono, di) (p-methylphenyl) phosphoric acid; (Mono, di) (p-ethylphenyl) phosphate; (Mono, di) (p-propylphenyl) phosphoric acid; (Mono, di) (p-butylphenyl) phosphoric acid; (Mono, di) (p-nonylphenyl) phosphate; (Mono, di) (p-methylmethyl) phosphoric acid; (Mono, di) (2-phenylethyl) phosphoric acid; (Mono, di) (4-phenylbutyl) phosphoric acid; (Mono, di) (3-oxabutyl) phosphoric acid; (Mono, di) (3-oxapentyl) phosphate; (Mono, di) (3-oxahexyl) phosphoric acid; (Mono, di) (3-oxaheptyl) phosphoric acid; (Mono, di) (3-oxactylsil) phosphoric acid; (Mono, di) (3-oxanyl) phosphoric acid; (Mono, di) (3-oxoundecyl) phosphoric acid; (Mono, di) (3-oxatridecyl) phosphoric acid; (Mono, di) (3-oxapentadecyl) phosphoric acid; (Mono, di) (3-oxaheptadecyl) phosphoric acid; (Mono, di) (3-oxanonadecyl) phosphoric acid; (Mono, di) (3-oxahenoxyl) phosphoric acid; (Mono, di) (1-methyl-3-oxabutyl) phosphoric acid; (Mono, di) (1-methyl-3-oxapentyl) phosphate; (Mono, di) (1-methyl-3-oxaheptyl) phosphoric acid; (Mono, di) (1,2-dimethyl-3-oxaheptyl) phosphate; (Mono, di) (1-methyl-3-oxatridecyl) phosphoric acid; (Mono, di) (1-methyl-2- (o-methylphenoxy) ethyl) phosphoric acid; (Mono, di) (1-methyl2- (p-nonylphenoxyethyl) phosphate; (mono, di) (1-methyl-4-phenyl-3-oxabutyl) phosphate; (mono, di) (3, 6-dioxaheptyl) phosphate; (mono, di) (3,6-dioxaoctyl) phosphate; (mono, di) (3,6-dioxadecyl) phosphate; (mono, di) (3,6- Dioxatetradecyl) phosphate; (mono, di) (3,6-dioxahexadecyl) phosphate; (mono, di) (3,6-dioxaoctadecyl) phosphate; (3,6-dioxicosyl) Phosphoric acid; (3,6-dioxadocosyl) phosphate; (mono, di) (3,6-dioxatetracosyl) phosphoric acid; (mono, di) (1,4-dimethyl-3,6-dioxadecyl Phosphoric Acid; (mono, di) (3,6,9-trioxadecyl) phosphate; (mono, di) (3,6,9-trioxoundecyl) phosphate; (mono, di) (3,6, 9-trioxatridecyl) phosphate; (mono, di) (3,6,9-trioxaheptadecyl) phosphate; (mono, di) (3,6,9-trioxahenoxyl) phosphate; (mono, Di) (3,6,9-trioxaheptacosyl) phosphate; (mono, di) (1,4,7-trimethyl-3,6,9-trioxatridecyl) phosphate; (mono, di) ( 3,6,9,12-tetraoxahepsadecyl) phosphate; (parent No, di) (3,6,9,12-tetraoxaoctyldecyl) phosphate; (mono, di) (3,6,9,12-tetraoxicosyl) phosphate; (mono, di) (3, 6,9,12-tetraoxadodocyl) phosphate; (mono, di) (3,6,9,12-tetraoxatetracosyl) phosphate; (mono, di) (1,4,7,10-tetramethyl -3,6,9,12-tetraoxahexadecyl) phosphate; triisopropyl acid phosphate; tributyl acid phosphate; trioctylic acid phosphate; triisodecyl acid phosphate; tridecanoic acid phosphate; bis (tridecanoic acid) phosphate Trimethyl acid phosphate; triethyl acid phosphate; tripropyl acid ester; benzyl acid phosphate; dibenzyl acid phosphate; tribenzyl acid phosphate; polyoxyethylene nonyl phenolether phosphate; tri polyoxyethylene nonyl phenolether phosphate; bis (tridecane Oleic acid) phosphate; ethylene glycol monoethyl phosphate; diethylene glycol monoethyl phosphate Triethylene glycol mono ethyl phosphate, diethylene glycol monobutyl diphosphate, diethylene glycol monobutyl phosphate; Isopropylene glycol monoethyl phosphate; Diisopropylene glycol monoethyl phosphate; Compounds such as triisopropylene glycol monoethyl phosphate or the like may be used alone or in combination of two or more thereof. The phosphate ester compound is not limited to the above compounds, and specifically exemplified compounds are mixtures and compounds having a single composition. There is no need to decide.

In order to solve the problem of whitening or deforming of the epoxy acrylate optical lens, it is ideal to add 0.001 to 10.00 wt% of the internal releasing agent of the phosphate ester compound, and when it is less than 0.001 wt%, it does not act as a releasing agent and more than 10.00 wt% In this case, whitening of the lens occurs, and the lens and the mold are separated in advance. Preferably, at 0.01 to 1.00% by weight, a transparent optical lens without cloudiness could be obtained.

In the present invention, in order to improve the optical properties of the resin composition for an optical lens it was confirmed that it is ideal to add a heat stabilizer 0.01 ~ 5.00% by weight. The thermal stabilizer has a weak thermal stability effect when used at 0.01 wt% or less, and when used at 10.00 wt% or more, there is a problem in that the polymerization failure rate during curing is high and the thermal stability of the cured product is lowered. For example, calcium stearate which is a metal fatty acid salt type; Barium stearate; Zinc stearate; Cadmium stearate; Lead stearate; Magnesium stearate; Aluminum stearate; Potassium stearate; One or two or more of compounds such as zinc octoate can be used, and phosphorus-based triphenyl phosphite; Diphenyldecylphosphite; Phenyl didecyl phosphite; Diphenyldodecyl phosphite; Trinolylphenyl phosphite; Diphenylisooctylphosphite; Tributyl phosphite; Tripropyl phosphite; Triethyl phosphite; Trimethyl phosphite; Tris (monodecyl phosphite); One kind or two or more kinds of compounds such as tris (monophenyl) phosphite can be used, and lead-based 3PbO.PbSO4.4H ₂ O; 2PbO.Pb (C ₈ H ₄ O ₄ ); _{3PbO.Ph (C 4 H 2 O 4} ) .H be one species or two or more kinds of the compounds, such as O ₂ is used, and sealed organotin dibutyltin diahwoo rate; Dibutyl tin maleate; Dibutyltin bis (isooctyl maleate); Dioctyl maleate; Dibutyltin bis (monomethylmaleate); Dibutyltin bis (lauryl mercaptide); Dibutyl bis (isooxylmercaptoacetate); Monobutyl tin tris (isooctyl mercaptoacetate); Dimethyl tin bis (isooctyl mercaptoacetate); Tris (isooctyl mercaptoacetate); Bioctyl tin bis (isooctyl mercaptoacetate); Dibutyltin bis (2-mercaptoethylorate); Monobutyl tin tris (2-mercaptoethyrate); Dimethyltin bis (2-mercaptoethylate); One kind or two or more kinds of compounds such as monomethyl tin tris (2-mercaptoethyl laurate) can be used, and two or more kinds of the illustrated heat stabilizers can be used. More preferably, the lens formed by the use of a phosphorus-based heat stabilizer greatly improves the thermal stability of the optical lens as well as the initial color without deteriorating optical properties such as transparency, impact strength, heat resistance and polymerization yield.

As a reactive diluent for controlling the viscosity of the resin composition for an optical lens of the present invention, when mixed with 10.0 to 60.0% by weight, a liquid liquid having a viscosity of 20 to 1,000 cps at 25 ° C. is suitable for injection into a glass mold assembled with a tape or a synthetic resin gasket. A resin composition for epoxy acrylic high refractive engineering lenses can be obtained. If the liquid viscosity is 20 cps or less, the composition flows out of the mold when the liquid resin composition is injected into a glass mold assembled with a synthetic resin gasket. When the viscosity of the liquid is 1,000 cps or more, it is difficult to inject the composition into the mold. There is a difficult problem. More preferable viscosity is 30-500 cps. Reactive diluents for viscosity control of the resin composition for optical lenses, for example, styrene; Divinylbenzene; Alphamethylstyrene; Alphamethylstyrene dimer; Benzyl methacrylate; Chlorostyrene; Bromostyrene; Methoxy styrene; Monobenzylmaleate; Dibenzyl maleate; Monobenzyl fumalate; Dibenzyl fumalate; Methylbenzylmaleate; Dimethylmaleate; Diethylmaleate; Dibutyl maleate; Dibutyl fumarate; Monobutyl maleate; Monopentylmaleate; Dipentylmaleate; Monopentylfumalate; Dipentylfumalate; One kind or two or more kinds of compounds such as diethylene glycol bisaryl carbonate may be used, but are not limited to those exemplified above. All reactive diluents were purified and obtained in high purity and used in the resin composition for optical lenses.

In order to solve the polymerization imbalance of the resin composition for epoxy acrylate-based optical lens, when the molecular weight control agent is used in the range of 0.01 to 10.0% by weight, the separation between the lens and the glass mold is good and the polymerization imbalance prevents the separation between the lens and the mold in advance. Can be. However, using less than 0.01% by weight does not have an effect of solving the polymerization imbalance, when using more than 10.0% by weight polymerization imbalance occurs. In particular, the optical resin obtained by curing 2-mercaptoethanol in combination satisfies a sufficient resin strength with high refractive index, high Abbe number, high heat resistance and low specific gravity, and has excellent performance in dyeing property, resulting in desirable results. . The molecular weight modifier of the resin composition for optical lenses is a compound having at least one or / and two or more thiol groups on the terminal end of the molecule. For example, 2-mercaptoethanol; 1,2-ethanedithiol; 1,1-propanedithiol; 1,2-propanedithiol; 1,3-propanedithiol; 2,2-propanedithiol; 1,6-hexanedithiol; 1,2,3-propanethiol; 2- (2-mercaptoethylthio) propane-1,3-dithiol; 2,3-bis (2-mercaptoethylthio) propane-1-thiol; 2- (2,3-bis (2-mercaptoethylthio) propylthio) ethanethiol; 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane; 1,2-bis (2- (2-mercaptoethylthio) -3-mercaptopropylthio) -ethane; Bis (2- (2-mercaptoethylthio) -3-mercaptopropyl) sulfide; 2- (2-mercaptoethylthio) -3-2-mercapto-3- [3-mercapto-2- (2-mercaptoethylthio) -propylthio] propylthio-propane-1-thiol; 2,2-bis- (3-mercapto-propionyloxymethyl) -butyl ester; 2- (2-mercaptoethylthio) -3- (2-2- [3-mercapto-2- (2-mercaptoethylthio) -propylthio] ethylthioethylthio) propane-1-thiol; Trimethylolpropane tris (mercaptopropionate); Trimethylolethane tris (mercaptopropionate); Glycerol tris (mercaptopropionate); Trimethylolchloro tris (mercaptopropionate); Trimethylolpropane tris (mercaptoacetate); Trimethylolethane tris (mercaptoacetate); Pentaerythritol tetrakis (mercaptopropionate) (PETMP); Pentaerythritol tetrakis (mercaptoacetate) (PETMA); Bispentaerythritol-ether-hexakis (mercaptopropionate) (BPEHMP); Bispentaerythritol-ether-hexakis (2-mercaptoacetate) (BPEHMA); Bispentaerythritol hexa (2-mercaptoacetate) (BPEMA); Bistrimethylolpropanetetrakis (3-mercaptopropionate) (BTMPMP); Bistrimethylolpropane tetrakis (2-mercaptoacetate) (BTMPMA) and the like can be used alone or in combination of two or more, and the compound having at least one or two or more thiol groups in the terminal end of the molecule It is not limited to one.

The present invention provides a resin composition for an optical lens obtained by mixing an internal mold release agent represented by the formula (2) with a resin represented by the formula (1), a reactive diluent, or the like, and has a liquid viscosity of 25 to 1000 cps at 25 ° C. Epoxy acryl-based high refractive optical with excellent liquidity refractive index (nE, 20 ° C.) of 1.50 to 1.58 and no cloudiness with solid phase refractive index (nE, 20 ° C.) of 1.57 to 1.63. The resin composition for lenses can be obtained.

In particular, in the present invention, the epoxy acrylic resin compound and the reactive diluent compound used in the resin composition for an optical lens were refined prior to preparation, and the epoxy acrylic resin compound obtained by using high purity raw material of 90% or more was refined. The obtained 95% or more high purity epoxy acrylic resin compound was used for the resin composition for optical lenses, and the 99% or more high purity reactive diluent obtained by purifying 95% or more raw materials was used for the resin composition for optical lenses.

In addition, in the resin composition for an optical lens of the present invention, a known ultraviolet absorber, organic dye, coloring inhibitor, antioxidant, light stabilizer, catalyst, and the like may be included in a conventional method in order to improve optical properties. Further, in order to easily separate the molded optical lens from the glass mold, a silicone surfactant, a fluorine surfactant, or the like can be added.

[ 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 Acrylic Resin Compound

1) Component (I) Compound

Component (I) compound is a mixture represented by formula (3) with an equivalent weight of 259 and an average molecular weight of 518.

Formula (3)

(n = 0 to 15)

2) Ingredients II ) Compound

Component (II) compound is a mixture represented by formula (4) with an equivalent weight of 273 and an average molecular weight of 546.

Formula (4)

(n = 0 to 15)

3) Ingredients III ) Compound

Component (III) compound is a mixture represented by formula (5) with an equivalent weight of 472 and an average molecular weight of 944.

Formula (5)

(n = 0 to 15)

4) Ingredients IV ) Compound

Component (IV) compound is a mixture represented by formula (6) with an equivalent weight of 486 and an average molecular weight of 972.

Formula (6)

(n = 0 to 15)

Example  One

Resin composition for optical lens

Zelec UN 0.01 g was added to a mixture of 35 g of styrene, 2 g of TPP, 0.1 g of V65, and 0.25 g of 2-Me to 40 g of the epoxy acrylic optical resin component (I) and 25 g of the epoxy acrylic optical resin component (II) obtained above. The resin composition for was obtained.

Lens manufacturers

(1) The resin composition for optical lenses prepared as described above was stirred for 1 hour, degassed under reduced pressure for 10 minutes, and poured into a glass mold assembled with a polyester adhesive tape.

(2) The glass mold into which the resin composition for spectacle lens was injected was gradually heat-cured from 35 ° C. to 100 ° C. in a forced circulation oven, and then cooled to 70 ° C. to remove the glass mold to obtain a lens. The obtained lens was measured for physical properties in the following manner and the results are shown in Table 1 .

(3) The optical lens obtained in (2) 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.

(4) The surface of the lens obtained in (3) was etched in KOH 5% solution, then impregnated in hardener of Finecoder Co., Ltd., and then thermally cured. Silicon oxide, zirconium oxide, silicon oxide, ITO, zirconium oxide, Silicon oxide, zirconium oxide, and water film (fluorine resin) were vacuum deposited to obtain a hard coated and multi-coated optical lens.

Property test method

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

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

2) Release property: When the epoxy acrylic resin composition is thermally cured and separated from the plastic lens and the mold when demolded at 70 ° C., easily separated during separation, O is not easily separated, and when more than 3 of 100 glass molds are broken, It is indicated by X '.

3) Polymerization Imbalance: 100 lenses obtained in the process were observed with the naked eye and quartz lamps, and when three or more optical distortions appeared, 'X' was indicated, and optical distortion was indicated by 'X'.

Example  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  One

A resin composition for an optical lens was prepared by mixing 35 g of styrene, 2 g of TPP, 0.1 g of V65, 0.25 g of 2-Me, and 0.01 g of KF96 in 40 g of epoxy acrylic optical resin component (I) and 25 g of epoxy acrylic optical resin component (II). Except what was done, it carried out by the same method as Example 1, and the characteristic is shown in Table 1 .

Comparative example  2 to 4

According to the composition shown in Table 1 in the same manner as in Comparative Example 1 to prepare a resin composition and an optical lens for the optical lens, respectively, and tested the physical properties, the results are shown in Table 1 .

Example Comparative Example One 2 3 4 5 6 One 2 3 4
Basic resin
(g) Component I 40 40 40 40 40 40 40 40 Component II 40 40 Component III 25 25 25 25 25 25 25 Component IV 25 25 25 Thinner (g) Styrene 35 35 35 35 35 35 35 Alpha-methylstyrene 35 35 35 Heat stabilizer (g) TPP 2 2 2 2 2 2 2 2 2 2 Polymerization initiator (g) V65 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1
Internal release agent
(g) Zelec UN 0.01 0.01 0.005 0.005 OP  0.01 0.005 DOP 0.01 KF96 0.01 FZ-2108 0.01 Molecular Weight
Regulator (g) 2-Me 0.25 0.25 0.25 GST 025 0.25 0.25 PETMP 0.25 0.25 0.25 lens
Properties Refractive index (nE, 20 ℃) 1.597 1.597 1.597 1.596 1.596 1.595 1.597 1.595 1.597 1.596 Dysplasia O O O O O O X X X X Polymerization imbalance O O O O O O O O O X

According to the results shown in Table 1 , the silicone-based internal releasing agent is not good to be used as a releasing agent due to clouding, but the difference between the one with and without the phosphate ester is clearly shown. Was good and hardly noticed polymerization imbalance. However, when the molecular weight regulator and stabilizer are used in the comparative example, polymerization imbalance is good, but the problem of deforming remains. Therefore, by using an internal release agent that is a phosphate ester in the epoxy acrylic optical resin composition, the separation from the mold is excellent and the deforming is improved, and heat stability, weather resistance, dyeing, processability, transparency, initial color of the lens, heat resistance, etc. are excellent. The lens has greatly improved yield.

Abbreviation

Internal release agent

Zelec UN: acidic phosphate ester manufactured by Stapan, trade name Zelec UN

OP: octyl acid phosphate

DOP: dioctyl acid phosphate

PENPP: polyoxyethylene octyl phenol ether phosphate

KF96: A silicone release agent manufactured by Shin-Etsu Co., Ltd.

FZ-2018: Silicone release agent manufactured by Nippon Unicar, trade name FZ-2018

Heat stabilizer

TPP: triphenylphosphite

Polymerization initiator

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

Molecular Weight Initiator

2-Me: 2-mercaptoethanol

GST: 2,3-bis (2-mercaptoethylthio) propane-1-thiol

 (1,2-bis (2-mercaptoethylthio) propane-1-thiol)

PETMP: pentaerythritol tetrakis (mercaptopropionate)

(pentaerytritol-tetrakis (mercaptopropionate))

According to the present invention, the problem that the lens yield is greatly reduced due to the polymerization imbalance that is poorly separated from the mold after polymerization, or that the opacity occurs when the silicone-based release agent is used, is due to the use of the phosphate ester as the internal release agent. It is excellent in optical properties such as light weight, moldability, dyeing, heat resistance, transparency, etc. by solving the deforming or polymerization imbalance, and has excellent thermal stability. The optical lens according to the present invention can be applied to the spectacle lens and the camera lens, in particular, used in 3D polarized lenses equipped with a polarizing film on the spectacle lens, in addition to the spectacle lens used in the recording medium substrate, such as prism, optical fiber, optical disk, magnetic disk, It can be used as various optical products such as colored filters and ultraviolet absorption filters.

Claims (8)

Phosphoric acid ester compound added in an amount of 0.001 to 10.0% by weight to the resin composition for optical lenses comprising 30.0 to 80% by weight of the epoxy acrylate main component represented by the formula (I) and one or two or more 10.0 to 60.0% by weight of the reactive diluent. Internal release agent.
Formula (I)

(Where n = 0-15, R ₁ is H or CH ₃ and R ₂ is H or Br) The resin composition for an optical lens according to claim 1, wherein the phosphate ester compound is represented by the following general formula (II).
Chemical formula ( II )

(X, Y, Z is hydrogen, halogen, linear and branched aliphatic, aromatic, aliphatic to aromatic, aliphatic to aliphatic, alicyclic, ethylene oxide or propylene oxide added to the aromatic residue and aliphatic hydrocarbon substituted by halogen atoms) Any one selected from the group consisting of the same or different from each other) The compound of claim 1, wherein the reactive diluent compound is styrene; Divinylbenzene; Alphamethylstyrene; Alphamethylstyrene dimer; Benzyl methacrylate; Chlorostyrene; Bromostyrene; Methoxy styrene; Monobenzylmaleate; Dibenzyl maleate; Monobenzyl fumalate; Dibenzyl fumalate; Methylbenzylmaleate; Dimethylmaleate; Diethylmaleate; Dibutyl maleate; Dibutyl fumarate; Monobutyl maleate; Monopentylmaleate; Dipentylmaleate; Monopentylfumalate; Dipentylfumalate; 1 type or 2 or more types of diethylene glycol bisaryl carbonate compounds are used, The resin composition for optical lenses characterized by the above-mentioned. The resin composition for an optical lens according to claim 1, wherein a phosphorus thermal stabilizer is added. The method of claim 4, wherein the phosphorus thermal stabilizer is triphenyl phosphite; Diphenyldecylphosphite; Phenyl didecyl phosphite; Diphenyldodecyl phosphite; Trinolylphenyl phosphite; Diphenylisooctylphosphite; Tributyl phosphite; Tripropyl phosphite; Triethyl phosphite; Trimethyl phosphite; Tris (monodesilphosphite); 1 type or 2 types or more of a tris (monophenyl) phosphite compound is used, The resin composition for optical lenses characterized by the above-mentioned. The method of claim 1, wherein all the raw materials used in the preparation of the epoxy acrylic resin compound and the reactive diluent compound were purified and at least 95% high purity epoxy acrylic resin obtained by refining the epoxy acrylic resin compound obtained using at least 90% high purity raw material. A resin composition for an optical lens of at least 98% high purity reactive diluent obtained by purifying a compound and at least 95% of raw materials. A plastic spectacle lens obtained by thermosetting a resin composition for an optical lens obtained by mixing the internal mold release agent of claim 2. A polarizing lens having a polarizing film attached to a plastic lens obtained by thermosetting a resin composition for an optical lens obtained by mixing the internal mold release agent of claim 2.