KR100704314B1 - Super-high refractive index optical resin composition having high thermal resistance and method of preparing optical lens using it - Google Patents

Abstract

The present invention relates to a urethane-based optical resin composition having excellent heat resistance and a manufacturing method of an optical lens using the same, more specifically, excellent in light weight, moldability, dyeing, Abbe's number, transparency, impact resistance and the like and particularly excellent heat resistance The present invention relates to a plastic optical resin composition having no central deformation, which was a problem of a urethane-based plastic optical lens during post-processing, and a method of manufacturing an optical lens using the same. In the present invention, the liquid phase refractive index (nD) 1.460 to 1.635, the solid phase refractive index (nD) 1.587 to 1.675, the Abbe number 28 to 48, the liquid phase viscosity (20 ℃) 20 to 360cps, the specific gravity is the liquid specific gravity 1.10 to 1.35 and the solid phase specific gravity 1.15 to 1.45 There is provided an ultra-high refractive optical resin composition having excellent optical properties and excellent heat resistance, and an optical lens obtained by thermal curing the same.

Optical resin composition, optical lens, heat resistance, impact resistance, urethane lens, plastic lens, multi-coating, spectacle lens

Description

Super high refractive index optical resin composition having excellent heat resistance and manufacturing method of optical lens using same {Super-High Refractive Index Optical Resin Composition Having High Thermal Resistance and Method of Preparing Optical Lens Using It}

The present invention relates to a urethane-based optical resin composition having excellent heat resistance and a manufacturing method of an optical lens using the same, more specifically, excellent in light weight, moldability, dyeing, Abbe's number, transparency, impact resistance and the like and particularly excellent heat resistance The present invention relates to a plastic optical resin composition having no central deformation, which was a problem of a urethane-based plastic optical lens during post-processing, and a method of manufacturing an optical lens using the same.

Urethane-based plastic optical lenses have excellent transparency, Abbe's number, and tensile strength as compared with other plastic lenses, and have been recognized for their superiority as optical lens materials. However, urethane-based plastic optical lenses have low heat resistance, which causes problems in the center deformation of the lens during hard and multi-coating (anti-reflective coating) on the lens surface after casting. There is a problem that is getting worse.

In Korean Patent Publication No. 1987-0008928, a urethane-based high refractive plastic optical lens having excellent transparency, Abbe's number, and tensile strength is prepared by thermosetting 0.05 moles of xylene diisocyanate and 0.025 moles of pentaerythritol tetrakiscapcaptopropionate. However, the urethane-based high refractive plastic optical lens manufactured as described above has a problem in that the lens center portion is deformed during hard and multi-coating on the lens surface due to low heat resistance.

Korean Patent Publication No. 1993-0006918 discloses an alicyclic isocyanate compound, a pentaerythritol tetrakismercaptopropionate or 1,2-bis [(2-mercaptoethyl) in order to solve the problem of central deformation of a urethane optical lens. Thio] -3-mercaptopropane is thermosetted, and the urethane plastic optical lens is manufactured. Although the urethane-based plastic optical lens is slightly improved in heat resistance, the hard part and the multi-coating on the surface of the lens have a problem in that the center portion of the lens is deformed.

Also in Korean Patent Publication No. 1992-0005708, xylene diisocyanate and 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane are thermally cured to produce a urethane-based ultra high refractive plastic optical lens. In addition, there is a problem that the lens center portion is deformed during hard and multi-coating on the lens surface.

According to the present invention, a urethane-based optical resin composition having excellent light weight, moldability, dyeing property, transparency, impact resistance, and high Abbe's number, and having excellent heat resistance without center deformation due to heat during hard and multi-coating on the lens surface, and an optical lens using the same The purpose is to provide.

In the present invention, as a result of research and study to improve the above conventional problems,

(a) A mixture of component (I) and xylene diisocyanate represented by the following formula (1), or a mixture of component (I) and isophorone diisocyanate, or a mixture of component (I) and hexamethylene diisocyanate, or component (I ) To 25 to 65% by weight of a mixture of isophorone diisocyanate and hexamethylene diisocyanate,

(b) Component (II) represented by the following formula (2), or mixture of Component (II) and pentaerythritol tetrakiscapcappropionate, or a mixture of component (II) and pentaerythritol tetrakiscapcaptoacetate 35 To 75 wt%

(c) 0.05 to 6% by weight of the ultraviolet absorbent based on the total weight of the mixture obtained in (b) above; 0.01-5% by weight of a release agent and 0.01-5% by weight of a polymerization initiator are added and mixed to obtain an optical resin composition,

When heat-cured, it was found that a light-weight, moldability, dyeing property, transparency, impact resistance, Abbe's optical properties, as well as excellent heat resistance, it is possible to obtain a urethane-based optical lens without the center deformation due to heat during hard and multi-coating It became.

[Formula 1]

이다.R is C ₆ H ₁₂ or

to be.

[Formula 2]

In the present invention,

(a) A mixture of component (I) and xylene diisocyanate represented by the following formula (1), or a mixture of component (I) and isophorone diisocyanate, or a mixture of component (I) and hexamethylene diisocyanate, or component (I ) To 25 to 65% by weight of a mixture of isophorone diisocyanate and hexamethylene diisocyanate,

(b) Component (II) represented by the following formula (2), or mixture of Component (II) and pentaerythritol tetrakiscapcappropionate, or mixture of component (II) and pentaerythritol tetrakiscapcaptoacetate 35 To 75 wt%

(c) 0.05 to 6% by weight of the ultraviolet absorbent based on the total weight of the mixture obtained in (b) above; An optical resin composition obtained by adding and mixing 0.01 to 5% by weight of a release agent and 0.01 to 5% by weight of a polymerization initiator,

Liquid refractive index (Ne) 1.460 to 1.635, solid phase refractive index (Ne) 1.587 to 1.675, Abbe number 28 to 48, liquid phase viscosity (20 ° C) 20 to 360 cps, specific gravity is optical with liquid specific gravity of 1.10 to 1.35 and solid specific gravity of 1.15 to 1.45 A resin composition is provided.

이다.R is C ₆ H ₁₂ or

to be.

In addition, the present invention provides a plastic optical lens obtained by thermosetting the composition and a manufacturing method thereof.

As an isocyanate compound in this invention, component (I) and xylene diisocyanate which are represented by following General formula (1) are mixed, or component (I) and isophorone diisocyanate are mixed, or component (I) and hexamethylene diisocyanate Or by mixing component (I) with isophorone diisocyanate and hexamethylene diisocyanate. In the case of producing an ultra high refractive optical lens, in order to obtain a lens having excellent heat resistance, 0.05 to 0.3 mol of component (I) and 0.3 to 0.95 mol of xylene diisocyanate are preferably used. In the case of producing a high refractive optical lens, in order to obtain a lens having excellent heat resistance, preferably, 0.5 to 0.95 mol of a mixture of isophorone diisocyanate and hexamethylene diisocinate is mixed with 0.05 to 0.5 mol of component (I). use. In this case, the mixing ratio of isophorone diisocyanate to hexamethylene diisocinate is preferably about 0.3 to 0.8 mole.

If 0.5 mole or more of the component (I) is used as the isocyanate compound in the composition, the heat resistance can be greatly increased, but there is a problem in that the viscosity of the resin composition is increased. If the viscosity is high, since bubbles generated when injecting the composition into the mold are not removed well, there is a problem that a lot of bubbles are generated on the surface of the optical lens during curing. At this time, the temperature of the composition at 30 ℃ or more when the vacuum degassing stirring can reduce the bubble to some extent, but also the viscosity of the composition according to the start of the self-reaction increases the injection time takes a lot, and bubbles generated during injection There is a hard problem to remove enough.

In the present invention, as the polythiol compound, component (II) is used alone, or component (II) and pentaerythritol tetrakiscapcappropionate are used in combination, or component (II) and pentaerythritol Tetrakismercaptoacetate is mixed and used. Preferably, 0.1-0.6 mol of pentaerythritol tetrakismercaptopropionate is mixed and used per 1 mol of component (II). Even when component (II) and pentaerythritol tetrakiscapcaptoacetate are mixed and used, it is preferable to use about 0.1-0.6 mol of pentaerythritol tetrakiscapcaptoacetate with respect to 1 mol of components (II).

In addition, when the component (I) and xylene diisocyanate are mixed with an isocyanate compound to produce an ultra high refractive optical lens, component (II) is preferably used as the polythiol compound. In the present invention, when the pentaerythritol tetrakismercaptoacetate is mixed with the polythiol compound in component (II), the heat resistance of the lens may be slightly increased, but the reaction rate is increased during curing, resulting in a problem of high polymerization failure rate. Can be.

In the composition of the present invention, the ultraviolet absorber is added at 0.05 to 6% by weight (50 to 60,000 ppm), preferably 0.1 to 3% by weight (100 to 30,000 ppm), based on the total weight of the mixed composition of the isocyanate compound and the polythiol compound. . If the amount of the ultraviolet absorber is less than 0.05% by weight, no effective ultraviolet absorbing capacity can be obtained, and yellowing may be severe when the lens is exposed to ultraviolet rays. In addition, when it is 6% by weight or more, not only it is difficult to dissolve in the composition, but also a poor polymerization may occur during curing. As the ultraviolet absorbent, any known ultraviolet absorbent usable for spectacle lenses can be used without limitation. For example, 2- (2'-hydroxy-5-methylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -5-chloro-2H-benzotriazole; 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5-chloro-2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-amylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-5'-t-butylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole; 2,4-dihydroxybenzophenone; 2-hydroxy-4-methoxybenzophenone; 2-hydroxy-4-octyloxybenzophenone; 4-dodecyloxy-2-hydroxybenzophenone; 4-benzooxy-2-hydroxybenzophenone; 2,2 ', 4,4'-tetrahydroxybenzophenone; 2,2'- dihydroxy-4,4'- dimethoxy benzophenone etc. can be used individually or in mixture of 2 or more types. Preferably, 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole or 2 having good ultraviolet absorption in the wavelength range of 400 nm or less and having good solubility in the composition of the present invention; , 2'-dihydroxy-4,4'-dimethoxybenzophenone and the like can be used.

In the present invention, the release agent may be used alone or in combination of two or more components selected from fluorine-based nonionic surfactants, silicone-based nonionic surfactants, alkyl quaternary ammonium salts, acidic phosphate esters and acidic phosphonic acid esters. Preferably acidic phosphate esters or acidic phosphonic acid esters are used. The use of the composition by applying it to a metal or glass mold also makes excellent deforming. As acidic phosphate ester, isopropyl acid four-state; Diisopropyl acid phosphate; Butyl phosphate; Octylic acid phosphate; Dioctyl acid phosphate; Isodecyl phosphate; Diisodecyl acid phosphate; Tridecanoic acid phosphate; Bis (tridecanoic acid) phosphate or the like may be used alone or in combination of two or more thereof. As used in the examples of the present invention, it was found that ZZLEC UN (DUPONT), which is an acidic phosphate ester system, exhibited the best deforming when the mold was demolded from the lens after curing. The amount of the releasing agent added may be used in an amount of 0.01 to 5% by weight relative to the monomer, but preferably 0.05 to 2% by weight of the mold release agent and good polymerization yield.

The polymerization initiator used in the present invention may be an amine-based or tin-based compound. As a tin type compound, Butyl tin dilaurate; Dibutyl tin dichloride; Dibutyl tin diacetate; Oxalic acid stannous; Dibutyl dilaurate; Tetrafluorotin; Tetrachlorotin; Tetrabromotin; Tetraiodine tin; Methyl tin trichloride; Butyltin trichloride; Dimethyltin dichloride; Dibutyltin dichloride; Trimethyltin chloride; Tributyltin chloride; triphenyltin chloride; Dibutyltin sulfide; Di (2-ethylsecyl) tin oxide and the like may be used alone or in combination of two or more thereof. When such a tin compound was used, the polymerization yield was high and there was no bubble generation. It is preferable to use the usage-amount in 0.01-5 weight% of the whole composition.

In the composition of the present invention, a known organic dye may be preferably further contained. In one embodiment of the present invention, Kyungin Yang Co., Ltd. 1-hydroxy-4- (p- toludine) enthraquinone [1-HYDROXY-4- (P-TOLUIDIN) ANTHRAQUINONE], Perinone dye (PERINONE DYE) ) And the like. Such organic dyes may be added in the range of 0.01 to 1,000 ppm, more preferably 0.03 to 500 ppm, based on the total weight of the composition. By including a small amount of the organic dye in this way it is possible to prevent the lens from becoming yellow.

The optical resin composition of the present invention is thermally cured to obtain plastic optical lenses, in particular spectacle lenses. Preferred embodiments for preparing the spectacle lens by thermal curing the composition of the present invention are as follows. First, after finally adding the polymerization initiator to the composition of the present invention, by substituting with nitrogen to remove air in the mixing vessel (reactor), stirring under reduced pressure is carried out for 2 to 5 hours, stopping stirring, and then degassing under reduced pressure. Inject into the mold. The mold is preferably a glass mold or a metal mold fixed with a plastic gasket or polyester or polypropylene adhesive tape. The glass mold injected with the mixture was placed in a forced circulation oven, held at 33-37 ° C. for 2 hours, heated at 38-42 ° C. for 3 hours, heated at 115-125 ° C. for 12 hours, held at 115-125 ° C. for 2 hours, After cooling to 60 to 80 ° C. over 2 hours, the solid is released from the mold to obtain an optical lens. The optical lens thus obtained is subjected to annealing at a temperature of 100 to 120 ° C. for 1 to 4 hours to obtain a final desired plastic optical lens.

In addition, the optical lens obtained by the above method was subjected to hard coating and multi-coating treatment in order to increase optical characteristics. The hard coat layer may be formed of at least one silane compound having functional groups such as an epoxy group, an alkoxy group, a vinyl group, and at least one metal oxide colloid such as silicic acid oxide, titanium oxide, antimony oxide, tin oxide, tungsten oxide, and aluminum oxide. The coating composition was coated with a thickness of 0.5 to 10 μm on the surface of the optical lens by impregnation or spin coating, followed by heating or UV curing to complete the coating film.

The multi-coating layer, that is, the anti-reflective coating layer may be formed by vacuum deposition or sputtering of metal oxides such as silicon oxide, magnesium fluoride, aluminum oxide, zirconium oxide, titanium oxide, tantalum oxide and yttrium oxide. Most preferably, the silicon oxide film and the zirconium oxide film are repeatedly vacuum-deposited three times on both surfaces of the lens and the silicon oxide film is finally vacuum deposited. In addition, depending on demand, an ITO layer may be further provided between the silicon oxide and zirconium oxide film as a water film layer in the last layer.

The optical lens of the present invention may be used after coloring treatment using a disperse dye or a photochromic dye, as necessary.

The optical resin composition of the present invention is not limited to plastic eyeglass lenses, and can be used in various optical products.

Hereinafter, the present invention will be described in more detail with reference to specific examples. However, the scope of the present invention is not limited by the following examples, and those skilled in the art to which the present invention pertains should be within the equivalent scope of the technical concept of the present invention and the claims to be described below. Of course, various modifications and variations are possible.

Example 1

(1) 0.2 mole of component (I) represented by Formula 1; 1.7 moles of xylene diisocyanate; 1.0 mole of component (II) represented by Formula 2; 20 g of 2- (2'-hydroxy-5-methylphenyl) -2H-benzotriazole as an ultraviolet absorber; 0.1 g of isopropyl acid four state as a release agent; 20 ppm of 1-hydroxy-4- (p-toluidino) anthraquinone (blue) and 10 ppm of perrinone di (Red) as a 1% organic dye solution; 1.0 g of butyl tin dilaurate as a polymerization initiator was placed in a mixing vessel equipped with a stirrer, replaced with nitrogen to remove air from the mixing vessel, and then stirred under reduced pressure for 2 hours. The stirring was stopped, followed by degassing under reduced pressure using a polyester adhesive tape. It was injected into a fixed glass mold (diopta -5.00).

(2) The glass mold in which the mixture was injected was kept at 35 ° C. for 2 hours in a forced circulation oven, 3 hours at 40 ° C., 12 hours at 120 ° C., 2 hours at 120 ° C., and 2 hours at 70 ° C. After cooling to heat curing, the mold was released from the solid to obtain an optical lens having a center thickness of 1 mm.

(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 lens obtained in (3) was impregnated with hard solution of Finecoder ST11 Water-8H, and then thermally cured. Silicon oxide, zirconium oxide, silicon oxide, ITO, oxide, zirconium film, silicon oxide, Zirconium oxide and a water film (fluorine resin) were vacuum-deposited to obtain hard-coated and multi-coated optical lenses.

Experiment method

The physical properties of each optical lens were measured by the following experimental method, and the results are reported in Table 1.

1. Refractive index and Abbe number: It was measured using an Abbe refractometer, an Atacota Co 1T model.

2. Light transmittance: It measured using the spectrophotometer.

3. Heat resistance: 5 g was added to the test specimens using a thermomechanical analyzer (manufactured by Parkin Elmar Co., Ltd.) and heated at 2.5 ° C. per minute to measure the heat deformation start temperature.

4. Light resistance: The optical lens (degree of -5.00) was exposed to QUV / Spray model (5w) of Q-Pannellad products for 200 hours, and the color of the lens was expressed as O, if there was no change in color.

Examples 2-16

According to the same method as in Example 1, the compositions and the lenses were prepared in the compositions shown in Tables 1 and 2, respectively, and the experimental results are shown in Tables 1 and 2.

Comparative Example 1

Except that 1 mol of xylene diisocyanate and 0.5 mol of pentaerythritol tetrakiscapcaptopropionate were mixed to prepare an optical resin composition, the same procedure as in Example 1 was carried out, and the properties thereof are shown in Table 3.

Comparative example  2 to 5

According to the same method as in Comparative Example 1, a composition and a lens were prepared using the compositions shown in Table 3, and the experimental results are shown in Table 3.

Abbreviation of Tables 1 to 3

Monomer

IPDI: diisophorone diisocyanate

HMDI: hexamethylene diisocyanate

PETMP: pentaerythritol tetrakismercaptopropionate

PETMA: pentaerythritol tetrakismercaptoacetate

XDI: Xylene Diisocyanate

UV absorbers

HMBT: 2- (2'-hydroxy-5-methylphenyl) -2H-benzotriazole

HBCBT: 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -5-chloro-2H-benzotriazole

HBMCBT: 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5-chloro-2H-benzotriazole

HAPBT: 2- (2'-hydroxy-3 ', 5'-di-t-amylphenyl) -2H-benzotriazole

HDBPBT: 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -2H-benzotriazole

HBPBT: 2- (2'-hydroxy-5'-t-butylphenyl) -2H-benzotriazole

HOPBT: 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole

DHBP: 2,4-dihydroxybenzophenone

HMBP: 2-hydroxy-4-methoxybenzophenone

HOOBP: 2-hydroxy-4-octyloxybenzophenone

DOHBP: 4-dodecyloxy-2-hydroxybenzophenone

BHBP: 4-benzooxy-2-hydroxybenzophenone

THBP: 2,2 ', 4,4'-tetrahydroxybenzophenone

DHMBP: 2,2'-dihydroxy-4,4'-dimethoxybenzophenone

BHMCBT: 2- (3'-t-butyl-2'-hydroxy-5'-methylphenyl) -5-chlorobenzenetriazole

Release agent

IPPT: Isopropyl Acid Four State

DIPP: Diisopropyl Acid Phosphate

BP: Butyric acid phosphate

OP: octylic acid phosphate

DOP: Dioctylate Phosphate

IDP: Isodecyl Phosphate

DIDP: Diisodecyl Phosphate

TDP: Tridecanoic Acid Phosphate

BTDP: Bis (tridecanoic acid) phosphate

1% dye solution

1 g of each of the following organic dyes was dissolved in 99 g of toluene and used as a 1% organic dye solution.

HTAQ: 1-hydroxy-4- (p-toludine) entroquinone [1-HYDROXY-4- (P-TOLUIDIN) ANTHRAQUINONE]

PRD: PERINONE DYE

Pigment Dispersion: To 100 g of CR-39, 0.9 g of PB-80 (pigment particles 0.3 to 2 µm manufactured by Daiichi Kasei Kogyo Co., Ltd.), 0.1 g of 500RS (pigment manufactured by Tosoh Corporation), and 0.175 g of polyoxyethylene nonyl ether The liquid obtained by disperse | distributing with a ball mill for 2 hours, and filtering by a 2 micrometer paper filter.

Polymerization initiator

BTL: Butyl Tin Dilaurate

BTC: Dibutyl Tin Dichloride

BTA: dibutyl tin diacetate

TEA: Triethylamine

IPP: Diisopropylperoxydicarbonate

NPP: Di-n-propylperoxydicarbonate

The optical resin composition and the optical lens using the same according to the present invention have excellent heat resistance while having excellent lightness, moldability, dyeing property, Abbe's number, transparency, impact resistance, and the like. There is no central deformation. According to the present invention, the problem of the center strain caused by heat, which was a problem of the urethane plastic optical lens, can be solved, and a urethane plastic optical lens having no thermal strain phenomenon can be obtained.

Claims (12)

(a) A mixture of component (I) and xylene diisocyanate represented by the following formula (1), or a mixture of component (I) and isophorone diisocyanate, or a mixture of component (I) and hexamethylene diisocyanate, or component (I ) To 25 to 65% by weight of a mixture of isophorone diisocyanate and hexamethylene diisocyanate, (b) Component (II) represented by the following formula (2), or mixture of Component (II) and pentaerythritol tetrakiscapcappropionate, or a mixture of component (II) and pentaerythritol tetrakiscapcaptoacetate 35 To 75 wt% (c) 0.05 to 6% by weight of the ultraviolet absorbent based on the total weight of the mixture obtained in (b) above; An optical resin composition obtained by adding and mixing 0.01 to 5% by weight of a release agent and 0.01 to 5% by weight of a polymerization initiator, Liquid refractive index (Ne) 1.460 to 1.635, solid phase refractive index (Ne) 1.587 to 1.675, Abbe number 28 to 48, liquid phase viscosity (20 ° C) 20 to 360 cps, specific gravity is optical with liquid specific gravity of 1.10 to 1.35 and solid specific gravity of 1.15 to 1.45 Resin composition. [Formula 1]

R is C ₆ H ₁₂ or

to be. [Formula 2]

The optical resin composition according to claim 1, wherein 0.05 to 0.3 mol of component (I) and 0.3 to 0.95 mol of xylene diisocyanate are mixed in (a). The optical resin composition according to claim 1, wherein 0.05 to 0.5 mol of component (I) and 0.5 to 0.95 mol of a mixture of isophorone diisocyanate and hexamethylene diisocinate are mixed in (a). The ultraviolet absorbent according to any one of claims 1 to 3, wherein the ultraviolet absorbent is selected from 2- (2'-hydroxy-5-methylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -5-chloro-2H-benzotriazole; 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) -5-chloro-2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-amylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-5'-t-butylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole; 2,4-dihydroxybenzophenone; 2-hydroxy-4-methoxybenzophenone; 2-hydroxy-4-octyloxybenzophenone; 4-dodecyloxy-2-hydroxybenzophenone; 4-benzooxy-2-hydroxybenzophenone; 2,2 ', 4,4'-tetrahydroxybenzophenone; Optical resin composition, characterized in that it is selected from the group consisting of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone and mixtures thereof. The optical resin composition according to any one of claims 1 to 3, wherein the release agent is an acidic phosphate ester or an acidic phosphonic acid ester or a mixture thereof. The method of claim 5, wherein the acidic phosphate ester, isopropyl acid formate; Diisopropyl acid phosphate; Butyl phosphate; Octylic acid phosphate; Dioctyl acid phosphate; Isodecyl phosphate; Diisodecyl acid phosphate; Tridecanoic acid phosphate; Optical resin composition, characterized in that selected from the group consisting of bis (tridecanoic acid) phosphate and mixtures thereof. The optical resin composition according to any one of claims 1 to 3, wherein a tin or amine compound is used as the polymerization initiator. The method of claim 7, wherein the tin compound is butyl tin dilaurate; Dibutyl tin dichloride; Dibutyl tin diacetate; Oxalic acid stannous; Dibutyl dilaurate; Tetrafluorotin; Tetrachlorotin; Tetrabromotin; Tetraiodine tin; Methyl tin trichloride; Butyltin trichloride; Dimethyltin dichloride; Dibutyltin dichloride; Trimethyltin chloride; Tributyltin chloride; Triphenyltin chloride; Dibutyltin sulfide; An optical resin composition, characterized in that it is selected from the group consisting of di (2-ethylsecyl) tin oxide and mixtures thereof. The plastic optical lens obtained by thermosetting the optical resin composition of any one of Claims 1-3. 10. The plastic optical lens of claim 9, wherein the optical lens is an eyeglass lens. (a) 0.05 to 6% by weight of an ultraviolet absorbent based on the total weight of the mixture of 25 to 65% by weight of the following A material and 35 to 75% by weight of the B material; 0.01-5% by weight of the release agent and 0.01-5% by weight of the polymerization initiator are added and mixed, followed by substitution with nitrogen to remove air in the reactor, stirring under reduced pressure for 2 to 5 hours, stopping stirring, degassing under reduced pressure, and injecting into the mold. To do that, A: A mixture of component (I) and xylene diisocyanate represented by the following formula (1), or a mixture of component (I) and isophorone diisocyanate, or a mixture of component (I) and hexamethylene diisocyanate, or component (I) And mixtures of isophorone diisocyanate and hexamethylene diisocyanate B: Component (II) represented by the following formula (2) or mixture of component (II) and pentaerythritol tetrakiscapcappropionate, or mixture of component (II) and pentaerythritol tetrakiscapcaptoacetate [Formula 1]

R is C ₆ H ₁₂ or

to be. [Formula 2]

(b) the mold injected with the mixture was placed in an oven, held at 33-37 ° C. for 2 hours, heated at 38-42 ° C. for 3 hours, heated at 115-125 ° C. for 12 hours, held at 115-125 ° C. for 2 hours, Cooling to 60 to 80 ° C. over 2 hours, and then releasing the solid from the mold to obtain an optical lens, (c) a method for producing a plastic optical lens comprising annealing the released optical lens at a temperature of 100 to 120 ° C. for 1 to 4 hours. 12. The method of manufacturing a plastic spectacle lens according to claim 11, further comprising a hard coating and a multi coating step following the step (c).