WO2014035126A1 - Procédé de fabrication de matériau optique à base de thioépoxy - Google Patents

Procédé de fabrication de matériau optique à base de thioépoxy Download PDF

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Publication number
WO2014035126A1
WO2014035126A1 PCT/KR2013/007706 KR2013007706W WO2014035126A1 WO 2014035126 A1 WO2014035126 A1 WO 2014035126A1 KR 2013007706 W KR2013007706 W KR 2013007706W WO 2014035126 A1 WO2014035126 A1 WO 2014035126A1
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WIPO (PCT)
Prior art keywords
weight
added
bis
thioepoxy
optical material
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PCT/KR2013/007706
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English (en)
Korean (ko)
Inventor
장동규
노수균
김종효
Original Assignee
주식회사 케이오씨솔루션
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Publication of WO2014035126A1 publication Critical patent/WO2014035126A1/fr

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Classifications

    • 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
    • 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
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • 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
    • C08L75/04—Polyurethanes
    • 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
    • G02B3/00—Simple or compound 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
    • C08K5/49—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 method for producing a thioepoxy clock optical material, and more particularly, to a method for producing a high-quality optical material that is colorless, transparent, and free of deformation without high occurrence of stria and turbidity due to polymerization imbalance.
  • Plastic optical lenses were introduced as a replacement for the high specific gravity and low impact of glass lenses.
  • Representative examples thereof include polyethylene glycol bisallylcarbonate, polymethyl methacrylate, diallyl phthalate, and the like.
  • optical lenses made of these polymers are excellent in physical properties such as moldability, dyeability, hard coat coating adhesion, impact resistance, etc., but the refractive index is about 1.50 (nD) and 1.55 (nD), resulting in a problem of thickening the lens. . Therefore, various attempts have been made to develop optical materials having high refractive indexes to reduce the thickness of lenses.
  • Korean Patent No. 10-0681218 proposes a thioepoxy watch plastic lens.
  • the thioepoxy lens has a high refractive index and an excellent property of having a high Abbe number, but also has a problem that the lens is fragile and poorly dyed.
  • a method of copolymerizing these two kinds of resins that is, a method of copolymerizing a thioepoxy compound, a polythiol compound, and a polyisocyanate compound, is disclosed in Korean Patent Registration No. 10-0417985, Japanese Patent Laid-Open No. 11 -352302 et al.
  • Both thioepoxy lenses and thioepoxy lenses copolymerizing thioepoxy and thiourethane often cause stria and turbidity due to polymerization imbalance when polymerizing the polymerizable composition, thereby degrading the quality of the lens. Since the occurrence of stria and turbidity degrade the quality of the lens, improvement has been required in the meantime. In addition, the production cost reduction has been a major concern in the recent lens field, the occurrence of striae, turbidity is a factor that increases the production cost by lowering the lens yield, the improvement is also urgently required in terms of production cost reduction.
  • Patent Document 1 Republic of Korea Patent Registration 10-0681218
  • Patent Document 2 Republic of Korea Patent Registration 10-0417985
  • Patent Document 3 JP 11-352302 A
  • stria and turbidity may occur due to polymerization imbalance.
  • “Stria” refers to a phenomenon that is locally different from the surrounding normal refractive index due to a difference in composition.
  • “Cloudy” means that when the resin composition for an optical lens is cured, turbidity appears in the optical lens due to polymerization heterogeneity. McLean and turbidity adversely affect the quality and performance of optical materials.
  • the present invention is a method for producing a high quality thioepoxy optical material with a high yield without the occurrence of striae or turbidity using a polymerizable composition comprising a compound having at least one thioepoxy group The purpose is to provide.
  • an optical material obtained by the above manufacturing method and an optical lens composed of the optical material are provided.
  • the optical lens in particular comprises an spectacle lens or a polarizing lens.
  • a colorless, transparent, and high-quality lens can be manufactured without a marrow or turbidity due to polymerization imbalance.
  • the mold polymerization is carried out by maintaining the temperature in a specific range.
  • die is performed in the temperature range of -5-20 degreeC. If the temperature is less than -5 °C, the polymerization reaction does not occur smoothly, the reaction time is long, and partial polymerization imbalance may occur. On the other hand, when the temperature exceeds 20 ° C, the curing speed of the resin is fast, and the reaction proceeds explosively due to the overheating reaction during polymerization, resulting in a gas accompanied by a severe smell, and the resin becomes black and cannot be used.
  • a polymeric composition is mix
  • the reaction should be performed at a low temperature, and the polymerization has been carried out at the lowest possible temperature.
  • the composition and defoaming temperature of the composition had a significant correlation with the striae and turbidity of the final obtained lens.
  • it is confirmed that a high quality lens without striae and turbidity is obtained by a smooth polymerization reaction when maintained at -5 to 15 ° C.
  • Compounds having at least one thioepoxy group include, for example, bis (2,3-ethiothiopropyl) sulfide, bis (2,3-ethiothio) disulfide, 1,3-bis ( ⁇ -ethiothiopropylthio) cyclo Hexane, 1,4-bis ( ⁇ -epithiopropylthio) cyclohexane, 1,3-bis ( ⁇ -ethiothiopropylthiomethyl) cyclohexane, 1,4-bis ( ⁇ -ethiothiopropylthiomethyl) cyclo Hexane, bis [4- ( ⁇ -ethiothiopropylthio) cyclohexyl] methane, 2,2-bis [4- ( ⁇ -ethiothiopropylthio) cyclohexyl] propane, bis [4- ( ⁇ -ethiothiopropyl Episulfide compounds having an alicyclic skeleton such as
  • halogen substituents such as chlorine substituents and bromine substituents, alkyl substituents, alkoxy substituents, nitro substituents and prepolymer-type modified compounds with polythiol may be used.
  • the compound having at least one thioepoxy group preferably bis (2,3-ethiothiopropyl) sulfide, bis (2,3-ethiothio) disulfide, 1,3-bis ( ⁇ -ethiothiopropylthio) ) Cyclohexane, 1,4-bis ( ⁇ -ethiothiopropylthio) cyclohexane, 1,3-bis ( ⁇ -ethiothiopropylthiomethyl) cyclohexane, 1,4-bis ( ⁇ -ethiothiopropylthiomethyl ) Cyclohexane, 2,5-bis ( ⁇ -ethiothiopropylthiomethyl) -1,4-dithiane, 2,5-bis ( ⁇ -ethi
  • the polymerizable composition may further include a polyisocyanate compound and a polythiol compound, and may be made of a thioepoxy clock optical material copolymerizing thioepoxy and thiourethane.
  • the polyisocyanate compound is not particularly limited and a compound having at least one isocyanate and / or isothiocyanate group may be used.
  • one or two or more kinds thereof may be mixed, and also halogen substituents such as chlorine substituents and bromine substituents, alkyl substituents and alkoxy substituents of these isocyanate compounds. And 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.
  • polyisocyanate compound Preferably, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexyl methane diisocyanate, bis (isocyanatomethyl) tricyclo [5,2,1,02,06] decane, bis ( At least one selected from isocyanatomethyl) bicyclo [2,2,1] is used.
  • the said polythiol compound is not specifically limited, If it is a compound which has at least 1 or more thiol groups, 1 type (s) or 2 or more types can be mixed and used for it.
  • 1 type (s) or 2 or more types can be mixed and used for it.
  • the polymerization modified body obtained by 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 polythiol compound preferably, at least one other polythiol compound may be mixed with bis (2-mercaptoethyl) sulfide or bis (2-mercaptoethyl) sulfide.
  • the polymerizable composition may further include an olefin compound as a reactive resin modifier for the purpose of controlling impact resistance, specific gravity, monomer viscosity, etc., in order to improve optical properties of the copolymer optical resin (optical material).
  • an olefin compound which can be added as a reactive 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 Diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glyco
  • the polymerizable composition of the present invention may further include an internal mold release agent, a heat stabilizer, an ultraviolet absorber, an organic dye, an inorganic pigment, an anti-coloring agent, an antioxidant, a light stabilizer, a catalyst, and the like according to a conventional method.
  • a phosphate ester compound, a silicone type surfactant, a fluorine type surfactant, etc. can be used individually or in combination of 2 or more types, respectively.
  • the internal mold release agent is preferably included at 0.001 to 10% by weight in the polymerizable composition.
  • a phosphate ester compound is used as an internal mold release agent.
  • the phosphate ester compound is prepared by adding 2-3 moles of alcohol compound to phosphorus pentoside (P 2 O 5 ), where various forms of phosphate ester compounds can be obtained, depending on the type of alcohol used.
  • Typical examples include those in which ethylene oxide or propylene oxide is added to the aliphatic alcohol, or ethylene oxide or propylene oxide is added to the nonylphenol group.
  • the phosphate ester compound added with ethylene oxide or propylene oxide is included as an internal mold release agent, an optical material having good release property and excellent quality can be obtained.
  • the phosphate ester compound used as the internal mold release agent is preferably polyoxyethylene nonylphenol ether phosphate (5 wt% with 5 mol of ethylene oxide added, 80 wt% with 4 mol added, 10 wt with 3 mol added).
  • polyoxyethylene nonylphenyl phosphate (9% added by 9 moles of ethylene oxide, 8 mole added by 8 moles of ethylene oxide, 7 mole added by ethylene oxide 10% by weight, 5% by weight of ethylene oxide added up to 5%), polyoxyethylenenonylphenol ether phosphate (3% by weight of 11 moles of ethylene oxide added, 80% by weight, 10 moles added, 9 moles added 5% by weight, 7% by weight 6% by weight, 6% by weight 6% by weight), polyoxyethylene nonylphenol ether phosphate (13% by weight of ethylene oxide 3% by weight, 12 moles by weight 80 Wt%, 11 mol added 8 wt%, 9 mol added 3 wt%, 4 mol Added 6% by weight), polyoxyethylene nonylphenol ether phosphate (added 17% by 17 mol of ethylene oxide, 79% by 16 mol added, 10% by weight 15 mol added, 14 mol added 4 weight%, 13
  • the polymerizable composition is defoamed while maintaining a constant temperature condition and injected into a mold to obtain a thioepoxy optical material through mold polymerization.
  • the polymerizable composition degassed under constant temperature conditions (-5 to 20 ° C.) is injected between polymerizing molds held by gaskets or tapes under the same temperature conditions and polymerized.
  • Polymerization conditions are not limited because the conditions vary greatly depending on the polymerizable composition, the type and amount of the catalyst, the shape of the mold, and the like, but are carried out over a period of 1 to 50 hours at a temperature of about -50 to 130 ° C. In some cases, it is preferable to maintain or gradually raise the temperature in a temperature range of 10 to 130 ° C. and to cure in 1 to 48 hours.
  • the optical material obtained by hardening may process annealing etc. as needed.
  • Treatment temperature is normally performed between 50-130 degreeC, and it is preferable to carry out at 90-100 degreeC.
  • a chain extender such as a chain extender, a crosslinking agent, a light stabilizer, a ultraviolet absorber, antioxidant, a coloring inhibitor, a useful dye, a filler, and an adhesive improvement agent.
  • the catalyst used plays an important role. As the type of catalyst, known epoxy curing agents are mainly used, but strong amines violate the isocyanate reaction, so it is necessary to pay attention to its use.
  • amine salts, phosphonium salts, phosphines, tertiary amines, Lewis acids, radical initiators, etc., which do not have an electron withdrawing group are mainly used, and the type and amount of catalysts are appropriately suited by those skilled in the art as necessary. You can choose.
  • the optical material of the present invention can be obtained in a molded body having various shapes by changing the mold during casting polymerization, and can be used for various optical materials such as spectacle lenses, camera lenses, and light emitting diodes (LEDs).
  • various optical materials such as spectacle lenses, camera lenses, and light emitting diodes (LEDs).
  • LEDs light emitting diodes
  • it is suitable as optical materials, such as an eyeglass lens, a camera lens, a light emitting diode, and an optical element.
  • the lens made of the optical material of the present invention may be used by providing a coating layer on one or both surfaces as necessary.
  • 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.
  • Each of these coating layers may be performed alone, or may be performed by multilayering a plurality of coating 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.
  • BEPS bis (2,3-ethiothio) sulfide
  • 8-PENPP polyoxyethylene nonylphenyl phosphate, acidic phosphoric acid ester, as an internal release agent, containing 5% by weight of 9 mol of ethylene oxide, 80% by weight of 8 mol of ethylene oxide, and 7 mol of ethylene oxide 10 wt%, 5 wt% of ethylene oxide added up to 6 mole
  • UV absorber HOPBT 1.5 g It mixed at 5 degreeC and set it as the homogeneous solution.
  • Refractive index and Abbe number It was measured using an Abbe refractometer, a DR-M4 model of Atago.
  • BEPS-1 bis (2,3-ethiothio) sulfide
  • isophorone diisocyanate as an isocyanate compound
  • bis (2-mercaptoethyl) as a thiol compound while maintaining the temperature at -10 ° C.
  • the filtration was performed with a 1 ⁇ m PTFE filter, and injected into the mold made of a glass mold and a tape while maintaining -10 °C.
  • This mold was charged into a polymerization oven, and gradually heated to 25 ° C to 130 ° C over 21 hours to polymerize. After the completion of the polymerization, the mold was removed from the oven, and the mold was released from the mold to obtain a lens. The obtained resin was further annealed at 130 ° C. for 4 hours. In this way, 100 lenses were prepared, and the stria and the turbidity were checked in the same manner as in Example 1, and the results are shown in Table 1 below.
  • composition and the optical lens were prepared according to the composition shown in Table 1 in the same manner as in Comparative Example 1, and the physical properties were tested, and the results are shown in Table 1.
  • BEPS bis (2,3-epithiopropyl) sulfide
  • ETPDS 2,3-epoxypropyl (2,3-epoxypropyl (2,3-epithiopropyl) disulfide)
  • IPDI isophorone diisocyanate
  • BMES bis (2-mercaptoethyl) sulfide (bis (2-mercaptoethyl) sulfide)
  • 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)
  • the present invention it is possible to easily manufacture a thioepoxy optical material having excellent quality without striae and turbidity, and the thioepoxy optical material prepared according to the present invention can be widely used in various fields in place of existing optical materials.
  • it can be used as a plastic glasses lens, a 3D polarizing lens equipped with a polarizing film on the spectacle lens, a camera lens, etc.
  • optical such as recording media substrates, color filters and ultraviolet absorption filters used in prisms, optical fibers, optical disks, etc. Can be used in the product.

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

Abstract

L'invention concerne un procédé de fabrication de matériau optique à base de thioépoxy, et plus spécifiquement un procédé de fabrication de matériau optique de qualité élevée à rendement élevé sans développer de stries ou de turbidité blanche provoquées par un déséquilibre de polymérisation , ce matériau étant incolore, transparente et inchangé. L'invention concerne également un procédé de fabrication d'un matériau optique à base de (thio)époxy dans lequel une composition de polymérisation comprenant un composé ayant au moins un groupe thioépoxy, est polymérisée dans un moule et est caractérisée en ce que le mélange, l'écumage et l'injection dans un moule sont effectués dans une plage de températures comprise entre 5-20 C. Le matériau optique à base de thioépoxy fabriqué selon l'invention peut remplacer la matière optique existante et être utilisée à grande échelle dans de nombreuses industries.
PCT/KR2013/007706 2012-08-28 2013-08-28 Procédé de fabrication de matériau optique à base de thioépoxy WO2014035126A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2012-0094533 2012-08-28
KR20120094533 2012-08-28

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WO2014035126A1 true WO2014035126A1 (fr) 2014-03-06

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WO (1) WO2014035126A1 (fr)

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USD1001252S1 (en) 2019-05-23 2023-10-10 Samsung Electronics Co., Ltd. Air conditioner

Citations (5)

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KR20040060966A (ko) * 2002-03-12 2004-07-06 미쓰이 가가쿠 가부시키가이샤 티오에폭시계 중합성 조성물 및 그 제조방법
US20070149639A1 (en) * 2002-07-08 2007-06-28 Hiroshi Horikoshi Polymerizable composition, optical material comprising the composition and method for producing the material
KR20080015186A (ko) * 2006-08-14 2008-02-19 (주)지론테크놀러지 (티오)에폭시기를 지닌 술피드-페놀 유도체, 이를 함유한수지 조성물
KR20080053958A (ko) * 2001-04-06 2008-06-16 미츠비시 가스 가가쿠 가부시키가이샤 중합 조정제 및 수지용 조성물
KR20090082719A (ko) * 2008-01-28 2009-07-31 주식회사 신대특수재료 신규 티오에폭시 화합물을 포함하는 초고굴절 광학수지조성물 및 이를 이용한 광학렌즈

Family Cites Families (2)

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Publication number Priority date Publication date Assignee Title
JP4161411B2 (ja) 1998-06-10 2008-10-08 セイコーエプソン株式会社 プラスチックレンズの製造方法及びプラスチックレンズ
CA2337955C (fr) 2000-03-15 2006-07-25 Hoya Corporation Lentilles en plastique pour lunettes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080053958A (ko) * 2001-04-06 2008-06-16 미츠비시 가스 가가쿠 가부시키가이샤 중합 조정제 및 수지용 조성물
KR20040060966A (ko) * 2002-03-12 2004-07-06 미쓰이 가가쿠 가부시키가이샤 티오에폭시계 중합성 조성물 및 그 제조방법
US20070149639A1 (en) * 2002-07-08 2007-06-28 Hiroshi Horikoshi Polymerizable composition, optical material comprising the composition and method for producing the material
KR20080015186A (ko) * 2006-08-14 2008-02-19 (주)지론테크놀러지 (티오)에폭시기를 지닌 술피드-페놀 유도체, 이를 함유한수지 조성물
KR20090082719A (ko) * 2008-01-28 2009-07-31 주식회사 신대특수재료 신규 티오에폭시 화합물을 포함하는 초고굴절 광학수지조성물 및 이를 이용한 광학렌즈

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KR20160150623A (ko) 2016-12-30
KR20140029251A (ko) 2014-03-10
KR20200085258A (ko) 2020-07-14
KR20190057237A (ko) 2019-05-28

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