WO2013103276A1 - Composition copolymère comprenant un composé thioépoxy, un composé polyisocyanate et un composé polythiol pour lentille optique à indice de réfraction élevé et procédé de fabrication de lentille optique - Google Patents

Composition copolymère comprenant un composé thioépoxy, un composé polyisocyanate et un composé polythiol pour lentille optique à indice de réfraction élevé et procédé de fabrication de lentille optique Download PDF

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WO2013103276A1
WO2013103276A1 PCT/KR2013/000100 KR2013000100W WO2013103276A1 WO 2013103276 A1 WO2013103276 A1 WO 2013103276A1 KR 2013000100 W KR2013000100 W KR 2013000100W WO 2013103276 A1 WO2013103276 A1 WO 2013103276A1
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장동규
노수균
김종효
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주식회사 케이오씨솔루션
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Publication of WO2013103276A1 publication Critical patent/WO2013103276A1/fr

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    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/52—Polythioethers
    • 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
    • C08K5/378—Thiols containing heterocyclic rings
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • 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
    • 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
    • G02B1/043—Contact lenses

Definitions

  • the present invention relates to a copolymer composition for a high refractive optical lens comprising a thioepoxy compound, a polyisocyanate compound, and a polythiol compound.
  • the present invention relates to a copolymer composition in which surface ring defects do not occur even in a high temperature lens having a large radius of curvature of the mold. A method of manufacturing an optical lens.
  • Korean Patent Publication Nos. 1993-0006918, 1992-0005708 and the like propose a thiourethane lens in which a polythiol compound and a polyisocyanate compound are reacted.
  • Korean Patent Publication No. 10-0681218 proposes a thioepoxy watch plastic lens.
  • the thiourethane-based lens has the advantages of high refractive index and excellent impact strength, but there are disadvantages such as softness of the lens surface and central depression, and also a problem in that Abbe's number decreases rapidly as the refractive index increases.
  • the thioepoxy lens has the advantage of having a high refractive index and a high Abbe number, but there are problems such as fragile lens and poor dyeing.
  • Patent Documents No. 10-0417985, Japanese Patent Laid-Open No. Hei 11-292950, and Japanese Patent Laid-Open No. Hei 11-352302 have been proposed.
  • An object of the present invention is to provide a copolymer optical lens having a low surface ring defect and having excellent surface precision and a method of manufacturing the same.
  • the present inventors have concentrated on the surface ring defect phenomenon which is a problem in the method of forming a copolymer from a thioepoxy compound, an isocyanate compound, and a thiol compound by mold polymerization.
  • 3 has been mainly used in the polyurethane-based optical resin composition.
  • a polythiol compound having two or more thiol groups it was unexpectedly found that when the bis (2-mercaptoethyl) sulfide having two thiol groups was used, almost no surface ring defects appeared.
  • the lens thus obtained showed little surface ring defect even in the high temperature lens, and it was confirmed that the surface precision was very good.
  • a copolymer composition for a high refractive optical lens comprising a thioepoxy compound, a polyisocyanate compound and bis (2-mercaptoethyl) sulfide.
  • the copolymer composition of the present invention may preferably further include a phosphate ester compound added with ethylene oxide or propylene oxide as an internal mold release agent.
  • the copolymer composition of the present invention may further include other polythiol compounds other than the bis (2-mercaptoethyl) sulfide, and may further include an olefin compound as a reactive resin modifier.
  • the high refractive optical lens obtained by casting-polymerizing the said copolymer composition is provided.
  • the optical lens in particular comprises an spectacle lens or a polarizing lens.
  • high refractive index or “high refractive index” is meant to include both high refractive index and ultra high refractive index of 1.67 or more, unless otherwise specified.
  • the high refractive optical lens polymerized with the copolymer composition of the present invention has a very low ring defect on the lens surface, excellent surface precision, and can be produced with high yield even with a high temperature lens (about -6.00 degrees or more).
  • the thioepoxy compound is an episulfide compound having a thioepoxy group.
  • an episulfide compound having a thioepoxy group for example, bis (2, 3- epithiopropyl) sulfide, bis (2, 3- epithiopropyl) disulfide, 2, 3- epidithiopropyl (2, 3- epithiopropyl) disulfide, 2,3-epidithiopropyl (2,3-ethiothiopropyl) sulfide, 1,3 and 1,4-bis ( ⁇ -ethiothiopropylthio) cyclohexane, 1,3 and 1,4-bis ( ⁇ -epithiopropylthiomethyl) cyclohexane, bis [4- ( ⁇ -ethiothiopropylthio) cyclohexyl] methane, 2,2-bis [4- ( ⁇ -ethiothiopropylthio) cyclohexyl
  • halogen substituents such as chlorine substituents and bromine substituents of compounds having episulfide groups, alkyl substituents, alkoxy substituents, nitro substituents and prepolymer-modified compounds with polythiols can also be used.
  • thioepoxy compound Preferably, bis (2, 3- epithiopropyl) sulfide, bis (2, 3- epithiopropyl) disulfide, 2, 3- epidithiopropyl (2, 3- epithio Propyl) sulfide, 2,3-epidithiopropyl (2,3-epithiopropyl) disulfide, 1,3 and 1,4-bis ( ⁇ -ethiothiopropylthio) cyclohexane, 1,3 and 1 , 4-bis ( ⁇ -epithiopropylthiomethyl) cyclohexane, 2,5-bis ( ⁇ -ethiothiopropylthiomethyl) -1,4-dithiane, 2,5-bis ( ⁇ -ethiothiopropylthio One or more of ethylthiomethyl) -1,4-dithiane and 2- (2- ⁇ -epithiopropylthioethylthio)
  • the polyisocyanate compound in the copolymer composition of the present invention is not particularly limited, and a compound having at least one isocyanate group and / or isothiocyanate group may be used.
  • a compound having at least one isocyanate group and / or isothiocyanate group may be used.
  • halogen substituents such as chlorine substituents and bromine substituents, alkyl substituents and alkoxy of these isocyanate compounds.
  • Substituents, nitro substituents, prepolymer-modified products with polyhydric alcohols or thiols, carbodiimide-modified products, urea-modified products, biuret-modified or dimerized products, and trimerized reaction products can also be used.
  • isophorone diisocyanate IPDI
  • hexamethylene diisocyanate HDI
  • dicyclohexyl methane diisocyanate H12MDI
  • xylylene diisocyanate XDI
  • 3,8-bis (iso Cyanatomethyl) 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 2,5-bis (isocyanatomethyl) bicyclo [2,2,1] heptane
  • 2,6-bis iso One or more selected from cyanatomethyl) bicyclo [2,2,1] heptane is used.
  • the copolymer composition of the present invention includes bis (2-mercaptoethyl) sulfide having two thiol groups as the polythiol compound. Unlike polythiol compounds having three or more thiol groups conventionally used as polythiols in copolymer resins, surface ring defects occur in resins copolymerized using bis (2-mercaptoethyl) sulfide having two thiol groups. This rarely appeared.
  • the copolymer composition of the present invention may further contain another polythiol compound while containing bis (2-mercaptoethyl) sulfide as the main polythiol.
  • polythiol compounds examples include 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,3-bis (2-mercaptoethylthio) propane-1-thiol, 2, 2-bis (mercaptomethyl) -1,3-propanedithiol, tetrakis (mercaptomethyl) methane; 2- (2-mercaptoethylthio) propane-1,3-dithiol, 2- (2,3-bis (2-mercaptoethylthio) propylthio) ethanethiol, bis (2,3-dimercapto Propaneyl) sulfide, bis (2,3-dimercaptopropanyl) disulfide, 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane, 1,2-bis (2- ( 2-mercaptoethylthio) -3-mercaptopropylthio) ethane, bis (2-
  • the polymerization modified body obtained by the prepolymerization with an isocyanate, a thioepoxy compound, a ethane compound, or the compound which has an unsaturated bond as a resin modifier to a polythiol compound can also be used.
  • the copolymer composition of the present invention particularly preferably comprises a phosphate ester compound added with ethylene oxide or propylene oxide as an internal release agent.
  • a phosphate ester compound added with ethylene oxide or propylene oxide is used as an internal mold release agent, the problem of release separation in advance can be solved, thereby minimizing surface ring defects.
  • the internal release agent preferably 4-PENPP [polyoxyethylenenonylphenol 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 Mole added 5% by weight)], 8-PENPP [polyoxyethylenenonylphenol ether phosphate (3% by weight of 9 moles of ethylene oxide added, 80% by weight of 8 moles added, 5% by weight of 9 moles added) , 7 mole added 6% by weight, 6 mole added 6% by weight)], 12-PENPP [polyoxyethylenenonylphenol ether phosphate (13 mole added by ethylene oxide 3% by weight, 12 mole added by 80) Weight%, 11 mol added 8 wt%, 9 mol added 3 wt%, 4 mol added 6 wt%)], 16-PENPP [polyoxyethylene nonylphenol ether phosphate (17 mol added ethylene oxide added) 3% by weight, 79% by 16 mole added,
  • the copolymer composition of the present invention may further include an olefin compound as a reactive resin modifier for the purpose of controlling impact resistance, specific gravity, monomer viscosity, and the like.
  • olefin compound which can be added as a resin modifier for example, benzyl acrylate, benzyl methacrylate, butoxyethyl acrylate, butoxymethyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2 Hydroxyethyl acrylate, 2-hydroxymethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, phenoxy ethyl acrylate, phenoxy ethyl methacrylate, phenyl methacrylate, ethylene glycol di Acrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol Dimethacrylate, Polyethylene Glycol Diacrylate, Polyethylene Glycol Dimethac Latex,
  • the copolymer optical lens of the present invention is obtained through template polymerization. That is, the copolymer composition of this invention is inject
  • the thioepoxy compound, isocyanate compound, and thiol compound copolymer obtained by hardening may perform annealing etc. as needed.
  • Treatment temperature is normally performed between 50-150 degreeC, and it is preferable to carry out at 90-140 degreeC.
  • the composition of the present invention is preferably subjected to mold polymerization by adding a phosphate ester compound as an internal mold release agent.
  • a phosphate ester compound is the same as above.
  • various additives such as chain extenders, crosslinking agents, light stabilizers, ultraviolet absorbers, antioxidants, anti-colorants, oil-soluble dyes, fillers, adhesion improving agents, and the like may be added.
  • the catalyst used plays an important role. In the type of catalyst, epoxy curing agents are mainly used, but strong amines intensify the isocyanate reaction, so it is necessary to pay attention to its use.
  • amine salts, phosphonium salts, phosphines and tertiary amines having no electron withdrawing groups, Lewis acids, radical initiators and the like are mainly used, and the type and amount of the catalyst may vary depending on the case.
  • the copolymer resin of this invention can be obtained with the molded object of various shapes by changing the mold at the time of casting polymerization, and can be used for various optical lenses, such as an eyeglass lens, a polarizing lens, and a camera lens.
  • the coating layer include a primer layer, a hard coat layer, an antireflection film layer, an antifogging coat film layer, an antifouling layer, and a water repellent layer. These coating layers may be formed alone, or a plurality of coating layers may be formed in multiple layers. When providing a coating layer on both surfaces, you may give the same coating layer to each surface, or may give a different coating layer.
  • the optical lens obtained by casting and polymerizing a thioepoxy compound, a polyisocyanate compound, and a polythiol compound obtained in accordance with the present invention has very low surface ring defects on the lens surface, excellent surface precision, and can be easily manufactured with high yield.
  • Refractive index (nE), Abbe number It was measured at 20 °C using an Abe refractometer, IT and DR-M4 model of Atago.
  • the mixed solution was defoamed at 400 Pa for 1 hour. Then, it filtered with the 1 micrometer PTFE filter, and injected into the mold mold which consists of a glass mold and a tape. This mold was charged into a polymerization oven, and gradually heated to 25 ° C to 130 ° C over 21 hours to polymerize. After the end of the polymerization, the mold was taken out of the oven. Release property from the mold was good. The obtained resin was further annealed at 130 ° C. for 4 hours. The physical properties of the obtained resin were refractive index (nE) 1.697 and Abbe number 35.
  • the mixed solution was defoamed at 400 Pa for 1 hour. Then, it filtered with the 1 micrometer PTFE filter, and injected into the mold mold which consists of a glass mold and a tape. This mold was charged into a polymerization oven, and gradually heated to 25 ° C to 130 ° C over 21 hours to polymerize. After the end of the polymerization, the mold was taken out of the oven. Release property from the mold was good. The obtained resin was further annealed at 130 ° C. for 4 hours. The physical properties of the obtained resin were refractive index (nE) 1.738 and Abbe number 34.
  • the mixed solution was defoamed at 400 Pa for 1 hour. Then, it filtered with the 1 micrometer PTFE filter, and injected into the mold mold which consists of a glass mold and a tape. This mold was charged into a polymerization oven, and gradually heated to 25 ° C to 130 ° C over 21 hours to polymerize. After the end of the polymerization, the mold was taken out of the oven. Release property from the mold was good. The obtained resin was further annealed at 130 ° C. for 4 hours. The physical property of obtained resin was refractive index (nE) 1.666 and Abbe's number 36.
  • the mixed solution was defoamed at 400 Pa for 1 hour. Then, it filtered with the 1 micrometer PTFE filter, and injected into the mold mold which consists of a glass mold and a tape. This mold was charged into a polymerization oven, and gradually heated to 25 ° C to 130 ° C over 21 hours to polymerize. After the end of the polymerization, the mold was taken out of the oven. Release property from the mold was good. The obtained resin was further annealed at 130 ° C. for 4 hours. The physical properties of the obtained resin were refractive index (nE) 1.692 and Abbe number 35.
  • the mixed solution was defoamed at 400 Pa for 1 hour. Then, it filtered with the 1 micrometer PTFE filter, and injected into the mold mold which consists of a glass mold and a tape. This mold was charged into a polymerization oven, and gradually heated to 25 ° C to 130 ° C over 21 hours to polymerize. After the end of the polymerization, the mold was taken out of the oven. Release property from the mold was good. The obtained resin was further annealed at 130 ° C. for 4 hours. The physical properties of the obtained resin were refractive index (nE) 1.695 and Abbe number 35.
  • the mixed solution was defoamed at 400 Pa for 1 hour. Then, it filtered with the 1 micrometer PTFE filter, and injected into the mold mold which consists of a glass mold and a tape. This mold was charged into a polymerization oven, and gradually heated to 25 ° C to 130 ° C over 21 hours to polymerize. After the end of the polymerization, the mold was taken out of the oven. Release property from the mold was good. The obtained resin was further annealed at 130 ° C. for 4 hours. The physical property of obtained resin was refractive index (nE) 1.702 and Abbe's number 35.
  • Example 2 It carried out similarly to Example 1 except using it as the composition of Table 1 below.
  • the mold was taken out of the oven. Although the releasability from the mold was good, it was separated beforehand in high temperature water of -7.00 or more degrees, and the obtained resin was further annealed at 130 ° C for 4 hours. However, even after annealing, the surface ring defect phenomenon did not disappear. In the high water lens, stable lens quality was not obtained.
  • HOPBT 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole (2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole)
  • HTQA 1-hydroxy-4- (p-tolludine) -entroquinone (1-hydroxy-4- (p-toluidine) anthraquinone
  • EPDS Bis (2,3-Ethiothiopropyl) sulfide
  • IPDI isophorone diisocyanate
  • DMTMP 2,3-bis (2-mercaptoethylthio) propane-1-thiol
  • 8-PENPP polyoxyethylene nonylphenol ether phosphate (3% by weight of 9 moles of ethylene oxide added, 80% by weight of 8 moles added, 5% by weight of 9 moles added, 6% by weight of 7 moles added, 6 mol added 6% by weight)
  • 12-PENPP polyoxyethylene nonyl phenol ether phosphate (3% by weight of 13 moles of ethylene oxide, 80% by weight of 12 moles added, 8% by weight of 11 moles added, 3% by weight of 9 moles added, 4 mol added 6% by weight)
  • 8-PPNPP polyoxypropylene nonylphenol ether phosphate (3% by weight of 9 mole of propylene oxide, 80% by weight of 8 mole added, 5% by weight of 9 mole added, 6% by weight of 7 mole added, 6 mol added 6% by weight)
  • Zelec UN TM trade name with an acidic phosphate ester compound prepared in four Srepan Zelec UN TM
  • a thioepoxy optical material having very low ring defects on the lens surface and excellent surface precision can be manufactured with high lens yield.
  • the optical lens manufactured according to the present invention may be widely used in various fields in place of the existing optical lens, and specifically, may be used as an eyeglass lens, a polarizing lens, a camera lens, or the like.

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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)

Abstract

L'invention concerne une composition copolymère pour lentille optique à indice de réfraction élevé comprenant un composé thioépoxy, un composé polyisocyanate et un composé polythiol, et plus particulièrement, une composition copolymère et un procédé de fabrication de lentille optique qui ne présente pas de défauts annulaires de surface même dans une lentille à puissance élevée présentant un grand rayon de courbure de moule. L'invention concerne également la composition copolymère comprenant le composé thioépoxy, le composé polyisocyanate et un sulfure bis(2-mercaptoethyl), la lentille optique polymérisée au moyen de la composition et le procédé de fabrication de la lentille optique. Selon l'invention, la composition copolymère et la lentille optique polymérisée au moyen de la composition présentent très peu de défauts annulaires sur la surface de la lentille même dans une lentille à puissance élevée (ayant une puissance optique approximativement d'au moins -6,00), présentent une précision de surface supérieure, et peuvent être produites à un rendement élevé. Selon l'invention, les défauts annulaires sur les surfaces de lentilles sont rares même dans une lentille à indice de réfraction élevé et à puissance élevée, et un matériau optique à base thioepoxy qui présente une précision de surface élevée peut être fabriqué à un rendement élevé. La lentille optique fabriquée selon l'invention peut remplacer les lentilles optiques existant et peut être utilisée dans des applications variées notamment les lentilles pour lunette, les lentilles polarisées et les lentilles de caméra.
PCT/KR2013/000100 2012-01-06 2013-01-07 Composition copolymère comprenant un composé thioépoxy, un composé polyisocyanate et un composé polythiol pour lentille optique à indice de réfraction élevé et procédé de fabrication de lentille optique WO2013103276A1 (fr)

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CN116640361A (zh) * 2023-06-15 2023-08-25 益丰新材料股份有限公司 一种离型剂组合物及其应用

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KR102293898B1 (ko) 2019-09-16 2021-08-26 주식회사 트리엘 신규한 트리아진 유도체 및 이를 포함하는 열경화성 또는 감광성 조성물

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CN116640361A (zh) * 2023-06-15 2023-08-25 益丰新材料股份有限公司 一种离型剂组合物及其应用
CN116640361B (zh) * 2023-06-15 2023-12-22 益丰新材料股份有限公司 一种离型剂组合物及其应用

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