WO2010076942A1 - Composition de resine à haut indice de refraction, de faible poids, pour lentille optique, faisant appel à un compose thiol nouveau et lentille optique l'intégrant - Google Patents

Composition de resine à haut indice de refraction, de faible poids, pour lentille optique, faisant appel à un compose thiol nouveau et lentille optique l'intégrant Download PDF

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Publication number
WO2010076942A1
WO2010076942A1 PCT/KR2009/005604 KR2009005604W WO2010076942A1 WO 2010076942 A1 WO2010076942 A1 WO 2010076942A1 KR 2009005604 W KR2009005604 W KR 2009005604W WO 2010076942 A1 WO2010076942 A1 WO 2010076942A1
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Prior art keywords
compound
resin composition
diisocyanate
optical lens
hydroxy
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PCT/KR2009/005604
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English (en)
Korean (ko)
Inventor
장동규
노수균
김종효
Original Assignee
주식회사 케이오씨솔루션
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Publication of WO2010076942A1 publication Critical patent/WO2010076942A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/10—Metal compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4

Definitions

  • the present invention relates to a resin composition for plastic optical lenses, and more particularly to a lightweight high refractive resin composition for optical lenses using a novel thiol compound and an optical lens using the same.
  • Plastic lenses are used in the production of various optical lenses today because they are lightweight and have excellent impact resistance, and are easy to dye as compared to glass lenses.
  • a material of a plastic optical lens polyethyleneglycol bisallyl carbonate, polymethyl methacrylate (PMMA), a mixture of modified diaryl phthalate and ethylene glycol bisallyl carbonate, etc. have been generally used.
  • PMMA polymethyl methacrylate
  • these plastic lens materials have a low refractive index of about 1.50 to 1.55, the thickness of the lens is increased in order to increase the number of tap water. Therefore, there is a disadvantage that the aesthetics of the lens worsens, which cancels the superiority such as light weight of the plastic lens.
  • the myopia lens made of a mixture of diaryl phthalate and ethylene glycol bisallyl carbonate has a problem that birefringence and chromatic aberration occur, as well as aesthetic problems in which the edge thickness of the plastic lens becomes thick when the tap water is high. Accordingly, there is a need for a plastic lens material that can reduce the thickness of the lens due to its high refractive index and to reduce the chromatic aberration and exhibit low dispersion while making the most of the advantages of the low specific gravity plastic lens.
  • Korean Patent Publication No. 1992-0005708 provides a plastic lens material that can produce a thin lens thickness with a refractive index of 1.65 or more, but has high chromatic aberration and low heat resistance problems, and a high specific gravity of 1.33 to 1.36, resulting in a high lens density. There is a problem that becomes heavy.
  • Korean Patent Publication No. 1993-0006918 discloses an alicyclic isocyanate compound and a pentaerythritol tetrakismercaptopiopinate or 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane.
  • a high refractive index urethane-based plastic optical lens having a refractive index of 1.593 is manufactured, but the optical lens manufactured as described above has a problem that the lens is heavy due to its high specific gravity of 1.30 to 1.34.
  • the plastic spectacle lens obtained by thermosetting the said resin composition for optical lenses is provided.
  • the optical resin composition and the optical lens obtained in the present invention have high refractive index and low specific gravity, and are light and excellent in optical properties such as impact resistance, heat resistance, moldability, dyeing property, light transmittance and Abbe's number. Therefore, the edge thickness of the lens can be made thin even at high degrees of water, and at the same time, it can be usefully used for manufacturing glasses of high degree of water because of its light weight.
  • the specific gravity is lighter and heat distortion temperature is Its higher heat resistance makes it possible to reduce production costs by 30 ⁇ 40% due to lower raw material costs and higher yields.
  • the lightweight high refractive resin composition for an optical lens of the present invention includes a novel thiol compound and an isocyanate compound represented by Chemical Formula 1.
  • the resin composition of the present invention comprises 2,3-bis (2-mercaptoethylthio) propane-1-thiol; 2- (2-mercaptoethylthio) -3- ⁇ 2- [3-mercapto-2 (2-mercaptoethylthio) -propylthio] -ethylthio ⁇ -propane-1-thiol; And 2- (2-mercaptoethylthio) propane-1,3-dithiol, and may further include one or two or more thiol compounds selected from the group consisting of.
  • the isocyanate compound is an alkylene diisocyanate compound; Alicyclic diisocyanate compounds; Heterocyclic diisocyanate compounds; Aliphatic thiodiisocyanate compounds and the like.
  • alkylene diisocyanate compound for example, Ethylene diisocyanate; Trimethylene diisocyanate; Tetramethylene diisocyanate; 1,6-hexamethylene diisocyanate; Octamethylene diisocyanate; Nonamethylene diisocyanate; 2,2-dimethylpentane diisocyanate; 2,2,4-trimethylhexanediisocyanate; Decamethylene diisocyanate; Butene diisocyanate; 1,3-butadiene-1,4-diisocyanate; 2,4,4-trimethylhexamethylene diisocyanate; 1,6,11-undecanetriisocyanate; 1,3,6-hexamethylenetriisocyanate; 1,8-diisocyanato-4-isocyanatomethyloctane; 2,5,7-trimethyl-1,8-diisocyanato-5-isocyanatomethyloctane; Bis (isocyanatoethyl) carbonate
  • alicyclic diisocyanate compound for example, 3,8-bis (isocyanatomethyl) tricyclo [5,2,1,02,6] decane; 3,9-bis (isocyanatomethyl) tricyclo [5,2,1,02,6] Decane; 4,8-bis (isocyanatomethyl) tricyclo [5,2,1,02,6] decane; 4,9-bis (isocyanatomethyl) tricyclo [5,2,1,02,6] decane; 2,5 - Bis (isocyanatomethyl) bicyclo [2,2,1] heptane; 2,6-bis (isocyanatomethyl) bicyclo [2,2,1] heptane; Isophorone diisocyanate; Bis (isocyanatomethyl) cyclohexane; Dicyclohexyl methane diisocyanate; Cyclohexanediisocyanate; Methylcyclohexanediisocyanate; Dicyclohe
  • heterocyclic diisocyanate compound examples include thiophene-2,5-diisocyanate; Methyl thiophene-2,5-diisocyanate; 1,4-dithiane-2,5-diisocyanate; Methyl 1,4-dithiane-2,5-diisocyanate; 1,3-dithiolane-4,5-diisocyanate; Methyl 1,3-dithiolane-4,5-diisocyanate; Methyl 1,3-dithiolane-2-methyl-4,5-diisocyanate; Ethyl 1,3-dithiolane-2,2-diisocyanate; Tetrahydrothiophene-2,5-diisocyanate; Methyltetrahydrothiophene-2,5-diisocyanate; Ethyl tetrahydrothiophene-2,5-diisocyanate; Methyl tetrahydrothioph
  • aliphatic thiodiisocyanate compound For example, xylene thiodiisocyanate, 4-isocyanato-4'-isothiocyanato diphenyl sulfide; 2-isocyanato-2'-isothiocyanatodiethyl disulfide; Thiodiethyl diisocyanate; Thiodipropyl diisocyanate; Thiodihexyl diisocyanate; Dimethyl sulfon diisocyanate; Dithiodimethyl diisocyanate; Dithiodiethyl diisocyanate; Dithiodipropyl diisocyanate; Dicyclohexylsulphi-4,4'- diisocyanate; 1-isocyanatomethylthia-2,3-bis (2-isocyanatoethylthia) propane and the like.
  • the isocyanate compound is preferably isoprone diisocyanate; 1,6-hexamethylenedisocyananeate; And 4,4′-dicyclohexylmethane diisocyanate (H 12 MDI).
  • the reaction mixture may further include an activated hydrogen compound as a reactant.
  • activated hydrogen compound includes pentaerythritol tetrakismercaptopropionate; Pentaerythritol tetrakismercaptoacetate; Ethylene glycol; Diethylene glycol; Propylene glycol; Dipropylene glycol; Butylene glycol; Neopentyl glycol; glycerin; Trimethylol ethane; Butanetriol; 1,2-methylchloride; Pentaerythritol; Dipentaerythritol; Tripentaerythritol; Sorbitol; Ethylene glycol; Thritol libitol (Treitol, Ribitol); Arabinitol; Xylitol; Alitol; Mannitol; Dolitol; Hydritol; Glycols; Inositol; Hexanetriol;
  • pentaerythritol tetrakismercaptopropionate Pentaerythritol tetrakismecaptoacetate
  • 2- (2-mercaptoethylthio) -3- ⁇ 2- [3-mercapto-2 (2-mercaptoethylthio) propylthio] ethylthio ⁇ propane-1-thiol compound each alone or 2 More than one species can be used together.
  • the use ratio of the isocyanate compound to the mixture of the thiol compound represented by the formula (1) and the active hydrogen compound is in the range of 0.5 to 3.0 functional molar ratio of (NCO) / (OH + SH), preferably 0.5 to 1.5. to be.
  • the resin composition of the present invention obtained by reacting the thiol compound 30 to 70 wt% with the isocyanate compound 30 to 70 wt% has a solid phase refractive index (nD, 20 ° C) of 1.572 to 1.632, a liquid phase refractive index of 1.520 to 1.570, a solid phase specific gravity of 1.15 to 1.26, Abbe number 32-50 of a solid resin, and liquid viscosity (20 degreeC) 5-800 cps.
  • the resin composition of the present invention may include from 0.0007 to 9% by weight of the ultraviolet absorber based on the total weight of the reaction mixture, preferably 0.5 to 3% by weight in order to improve the light stability of the prepared resin. If the UV absorber is used in a smaller amount than the above range, it is difficult to effectively block ultraviolet rays harmful to the eyes, and when it is used beyond this range, it is difficult to dissolve in the optical lens composition, and spot patterns appear on the surface of the cured optical lens or transparency of the optical lens. Problem may occur.
  • the ultraviolet absorbent any known ultraviolet absorbent surface usable for the optical lens can be used.
  • ethyl-2-cyano-3,3-diphenyl acrylate 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- (2'-hydroxy-5-methylphenyl) -2H-benzotriazole 2-hydroxy having good ultraviolet absorption in the wavelength range of 400 nm or less and having good solubility in the composition of the present invention.
  • the lightweight resin for an optical lens of the present invention may include a known organic dye for improving the initial color of the lens and satisfying consumer's preference.
  • a known organic dye for improving the initial color of the lens and satisfying consumer's preference.
  • 1-hydroxy-4- (para- toluidine) anthraquinone [1-hydroxy-4- (p-toluidin) -anthraquinone], perinone dye (perinone dye) and the like for an optical lens composition 1
  • perinone dye perinone dye
  • the resin composition of the present invention may further include an internal mold release agent.
  • the internal mold release agent include fluorine-based nonionic surfactants having a perfluoroalkyl group, a hydroxyalkyl group or a phosphate ester group; Silicone nonionic surfactants having a dimethylpolysiloxane group, a hydroxyalkyl group or a phosphate ester group; Alkyl quaternary ammonium salts, ie, trimethylcetyl ammonium salt, trimethylstearyl, dimethylethylcetyl ammonium salt, triethyldodecyl ammonium salt, trioctylmethyl ammonium salt, diethylcyclohexadodecyl ammonium salt;
  • the component selected from the acidic phosphate ester can be used individually or in combination of 2 or more types.
  • acidic phosphate ester is used, and as acidic phosphate ester, isopropyl acid phosphate; Diisopropyl acid phosphate; Butyl phosphate; Octylic acid phosphate; Dioctyl acid phosphate; Isodecyl phosphate; Diisodecyl phosphate; Tridecanoic acid phosphate; Bis (tridecanoic acid) phosphate or the like may be used alone or in combination of two or more thereof.
  • ZELEC UN TM (DUPONT, Inc.), which is an acidic phosphate ester, showed the best demolding when demolding the mold from the lens after curing.
  • the internal mold release agent may be used in an amount of 0.0001 to 10% by weight based on the total weight of the reaction mixture. Preferably, 0.005 to 2% by weight of the mold release agent in the lens has a high polymerization yield. If the amount of the release agent is less than 0.005%, a phenomenon may occur in which the lens adheres to the surface of the glass mold when the molded optical lens is separated from the glass mold, and if more than 2% by weight, the lens is separated from the glass mold during the polymerization of the mold. There is a problem that may cause stains on the surface.
  • an amine or tin compound may be used as the polymerization initiator used to react the thiol compound and the isocyanate compound.
  • a tin type compound Butyl tin dilaurate; Dibutyl tin dichloride; Dibutyl tin diacetate; Stannous oxide; Dibutyl dilaurate; Tetrafluorotin; Tetrachlorotin; Tetrabromotin; Tetraidotin; 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
  • plastic optical lens When the resin composition for optical lenses of the present invention is thermoset, a plastic optical lens is obtained. Such plastic optical lenses include eyeglass lenses in particular.
  • Preferred embodiments for preparing the spectacle lens by thermal curing the composition of the present invention are as follows. First, a polymerization initiator is finally added to the composition constituting the resin of the present invention, substituted with nitrogen to remove air in the mixing vessel (reactor), and then stirred under reduced pressure for 2 to 5 hours, and the stirring is stopped, followed by degassing under reduced pressure. Inject into the mold.
  • the mold is preferably a glass mold or a metal mold fixed with polyester, polypropylene adhesive tape, or plastic gasket. The glass mold infused with the mixture was placed in a forced circulation oven, maintained at 33 to 37 ° C.
  • the solid is released from the mold to obtain an optical lens.
  • the optical lens thus obtained is annealed at a temperature of 120 to 140 ° C. for 1 to 4 hours to obtain a final desired plastic optical lens.
  • the optical lens obtained by the above method can be subjected to hard coating and multi-coating treatment in order to increase the 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 multi-coating layer that is, the anti-reflective coating layer
  • metal oxides such as silicon oxide, magnesium fluoride, aluminum oxide, zirconium oxide, titanium oxide, tantalum oxide, and yttrium oxide.
  • the silicon oxide film and the zirconium oxide film are alternately vacuum-deposited three times or more on both surfaces of the hard coating film of the lens, and finally, the silicon oxide film is vacuum deposited.
  • an indium tin oxide (ITO) layer may be further provided as a water film layer between the final silicon oxide and the zirconium oxide film as necessary.
  • the optical lens of the present invention may be used after coloring by adding a disperse dye or a photochromic dye to the hard liquid, if necessary.
  • the optical lens made of the light weight high refractive resin composition of the present invention has a low specific gravity, so that the lens is very light.
  • GST (2,3-bis (2-mercaptoethylthio) prepared according to the applicant's prior application "Lightweight high refractive resin for optical lenses and optical lenses using the same" (Patent Application No.
  • reaction solution was cooled to 30 ° C., 195.33 g (2.577 mol) of thiourea and 278.92 mL (3.208 mol) of 36% concentrated hydrochloric acid were added, and the mixture was refluxed at 110 ° C. for 3 hours 30 minutes. After the reaction was completed, the reaction solution was cooled and 240.18 ml of 25% aqueous ammonia was slowly added dropwise not to exceed 30 ° C. Then, 400 ml of toluene was added, hydrolyzed and cooled at 80 ° C.
  • reaction solution was cooled to 30 ° C., 195.33 g (2.577 mol) of thiourea and 278.92 mL (3.208 mol) of 36% concentrated hydrochloric acid were added, and the mixture was refluxed at 110 ° C. for 3 hours 30 minutes. After the reaction was completed, the reaction solution was cooled and 240.18 ml of 25% aqueous ammonia was slowly added dropwise not to exceed 30 ° C. Then, 400 ml of toluene was added, hydrolyzed and cooled at 80 ° C.
  • reaction solution was cooled to 30 ° C., 195.33 g (2.577 mol) of thiourea and 278.92 mL (3.208 mol) of 36% concentrated hydrochloric acid were added, and the mixture was refluxed at 110 ° C. for 3 hours 30 minutes. After the reaction was completed, the reaction solution was cooled and 240.18 ml of 25% aqueous ammonia was slowly added dropwise not to exceed 30 ° C. Then, 400 ml of toluene was added, hydrolyzed and cooled at 80 ° C.
  • reaction solution was cooled to 30 ° C., 195.33 g (2.577 mol) of thiourea and 278.92 mL (3.208 mol) of 36% concentrated hydrochloric acid were added, and the mixture was refluxed at 110 ° C. for 3 hours 30 minutes. After the reaction was completed, the reaction solution was cooled and 240.18 ml of 25% aqueous ammonia was slowly added dropwise not to exceed 30 ° C. Then, 400 ml of toluene was added, hydrolyzed and cooled at 80 ° C.
  • reaction solution was cooled to 30 ° C., 195.33 g (2.577 mol) of thiourea and 278.92 mL (3.208 mol) of 36% concentrated hydrochloric acid were added, and the mixture was refluxed at 110 ° C. for 3 hours 30 minutes. After the reaction was completed, the reaction solution was cooled and 240.18 ml of 25% aqueous ammonia was slowly added dropwise not to exceed 30 ° C. Then, 400 ml of toluene was added, hydrolyzed and cooled at 80 ° C.
  • the mixture was injected into a glass mold (diopta-5.00, center thickness 1.2 mm) fixed by using nitrogen gas.
  • the glass mold injected with the mixture was placed in a forced circulation oven, maintained at 33 ° C. for 2 hours, heated at 33 ° C. to 40 ° C. for 3 hours, heated at 40 ° C. to 90 ° C. for 10 hours, and heated at 90 ° C. to 130 ° C. for 4 hours, After holding for 2 hours at 130 ° C and cooling for 2 hours at 130 ° C to 70 ° C, the glass mold was detached to obtain a plastic optical lens.
  • the manufactured lens was evaluated for physical properties in the following manner and the results are shown in Table 1 below.
  • the manufactured lens had a high refractive index (nD) of 1.588, an Abbe number of 38, high optical properties such as impact resistance, light resistance, and transparency, and low specific gravity of 1.21.
  • Refractive index and Abbe's number It measured using the Abe refractometer (1T model) of Atago.
  • Tg Heat deflection temperature
  • a lens was placed on a USHIO mercury lamp (USH-102D) and visually observed to indicate non-uniformity.
  • Lenses prepared using the compounds of Y1S4B, Y1S4C, Y1S4D and Y1S4E having different equivalents prepared in Examples 2 to 5 had better deformability, heat resistance, and light resistance than the lenses prepared using the compounds of Y1S4A of Example 1 .
  • Their tendency was Y1S4A> Y1S4B> Y1S4C> Y1S4D> Y1S4E.
  • spectacle lenses made of Y1S4C, Y1S4D, and Y1S4E did not have better deformability than Y1S4A, and had severe yellowing.
  • the spectacle lens was manufactured using Y1S4C resin, demolding, striae, and poor polymerization were seen, but not severe.
  • the spectacle lens manufactured using the resins of Y1S4D and Y1S4E had a high bubble viscosity and poor defoaming, resulting in severe foaming and greatly increasing striae and poor polymerization.
  • the physical properties of the prepared lens were also evaluated in the same manner and shown in Tables 1 to 6 together.
  • the optical lens was manufactured in the same manner as in Example 6 except for using the composition shown in Table 7 below. Physical properties of the prepared spectacle lens were also evaluated in the same manner and shown in Table 7 together.
  • ETS4 2- (2-mercaptoethylthio) -3- ⁇ 2- [3-mercapto-2 (2-mercaptoethylthio) propylthio] ethylthio ⁇ propane-1-thiol
  • PETMP pentaerythritol tetrakismercaptopropionate
  • MMPPT 2- (2-mercaptoethylthio) -3- ⁇ 2- [3-mercapto-2 (2-mercaptoethylthio) -propylthio] -ethoxy ⁇ -propane-1-thiol
  • IPDI isopron diisocyanate
  • HOPBT 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole
  • the resin composition of the present invention can be usefully used in various optical lenses because of its high refractive index, light weight, and low production cost.
  • the resin composition of the present invention can thin the edge thickness of the lens even at a high degree of power and can reduce the production cost by 30% or more significantly compared to the existing lens. It is expected to be.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Eyeglasses (AREA)

Abstract

L'invention concerne une composition de résine que l'on peut utiliser pour fabriquer une lentille optique en plastique. Plus précisément, la composition de résine à haut indice de réfraction, de faible poids, pour lentilles optiques et une lentille optique l'utilisant sont obtenues par réaction d'un nouveau composé thiol avec un composé isocyanate. La lentille optique fabriquée à l'aide du composé de résine selon l'invention: est légère du fait d'un faible poids spécifique, a une résistance thermique élevée du fait d'une température de distorsion thermique élevée, et réduit les coûts de production du fait d'un faible taux de matières premières et d'un rendement élevé.
PCT/KR2009/005604 2008-12-29 2009-09-30 Composition de resine à haut indice de refraction, de faible poids, pour lentille optique, faisant appel à un compose thiol nouveau et lentille optique l'intégrant WO2010076942A1 (fr)

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KR1020080135911A KR101074450B1 (ko) 2008-12-29 2008-12-29 신규 티올 화합물을 이용한 광학렌즈용 경량성 고굴절 수지조성물 및 이를 이용한 광학렌즈
KR10-2008-0135911 2008-12-29

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US10745539B2 (en) 2013-09-30 2020-08-18 Hoya Lens Thailand Ltd. Transparent plastic substrate and plastic lens

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