WO2013112001A1 - Procédé de production d'un composé polythiol pour matériaux optiques à base de résine thioépoxyde et composition copolymère comprenant ce composé pour matériaux optiques à base de résine thioépoxyde - Google Patents

Procédé de production d'un composé polythiol pour matériaux optiques à base de résine thioépoxyde et composition copolymère comprenant ce composé pour matériaux optiques à base de résine thioépoxyde Download PDF

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WO2013112001A1
WO2013112001A1 PCT/KR2013/000628 KR2013000628W WO2013112001A1 WO 2013112001 A1 WO2013112001 A1 WO 2013112001A1 KR 2013000628 W KR2013000628 W KR 2013000628W WO 2013112001 A1 WO2013112001 A1 WO 2013112001A1
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bis
mol
added
weight
thioepoxy
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PCT/KR2013/000628
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Korean (ko)
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장동규
노수균
김종효
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주식회사 케이오씨솔루션
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of 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
    • C08G18/40—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
    • C08G18/28—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
    • C08G18/58—Epoxy resins
    • 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

Definitions

  • the present invention relates to a method for producing a polythiol compound used in a thioepoxy optical material and a copolymer composition for a thioepoxy optical material containing the polythiol compound. It relates to a polythiol compound for a material and a copolymer composition comprising the same.
  • Plastic optical materials are lighter and less easily broken than optical materials made of inorganic materials, and can be dyed. In recent years, plastic materials of various resins have been used for optical materials, and their required properties are also increasing day by day.
  • the thioepoxy lens has a high refractive index and an excellent characteristic of having a high Abbe number, but there are problems such as fragile lens and poor dyeing.
  • a method of copolymerizing 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 Publication No. 352302 et al.
  • the color of resin may worsen by coloring in the thio epoxy clock optical material which copolymerized thio epoxy and thio urethane.
  • the coloring of a polyurethane-based resin is caused by the coloring of a polythiol compound, and the coloring of the polythiol compound is an impurity, particularly calcium content, in thiourea, which is one of the raw materials used in the manufacturing process. It is revealed that there is a cause, and a method for producing a polythiol compound in which a thiourea having a calcium content of 1.0% by weight or less is reacted with a (poly) halogen compound or a (poly) alcohol compound is proposed.
  • the present inventors examined the cause of the coloring which appears in the thioepoxy optical material obtained by copolymerizing a thioepoxy compound, a polythiol compound, and a polyisocyanate compound, and, as a result, coloring a polythiol compound for coloring of the thioepoxy optical material obtained by copolymerization. In this critical role, it was found that the calcium content in the starting material directly affects the coloring of the polythiol compound in question.
  • the present invention relates to a method for producing a polythiol compound with less coloring by controlling the calcium content in thiourea used for the synthesis of polythiol compounds for thioepoxy optical materials, in particular for the copolymerization of thioepoxy optical materials. It is an object to provide a method for producing a (2-hydroxyethyl) sulfide compound and a copolymer composition for a thioepoxy optical material containing the polythiol compound thus obtained.
  • a method for producing a bis (2-mercaptoethyl) sulfide for a thioepoxy optical material is provided, wherein the calcium content in the thiourea is less than 1% by weight.
  • the polythiol compound is prepared by a method comprising synthesizing a (poly) thiol by reacting a (poly) halogen compound or a (poly) alcohol compound with a thiourea to form an isothiuronium salt, followed by hydrolysis.
  • copolymer composition for a thioepoxy optical material wherein the content of calcium in the thiourea is less than 1% by weight.
  • the present invention provides a method for producing a thioepoxy optical material comprising casting a polymer of the copolymer composition, a thioepoxy optical material obtained by this method, and an optical lens made of the optical material.
  • the optical lens in particular comprises an spectacle lens.
  • a polythiol compound in particular a bis (2-mercaptoethyl) sulfide, from which coloring can be suppressed and a good color thioepoxy optical material can be obtained, can be produced, and coloring can be suppressed and color is good.
  • polymerized the same can be obtained.
  • the polythiol compound is a known production method comprising a step of synthesizing (poly) thiol by reacting a (poly) halogen compound or a (poly) alcohol compound with thiourea to generate an isothiuronium salt, followed by hydrolysis. It can be prepared as.
  • a bis (2-hydroxyethyl) sulfide compound is prepared under the base catalyst of ethylene oxide and 2-mercaptoethanol or in the reaction of 2-chloroethanol and 2-mercaptoethanol, and the calcium content is It can be prepared by a method of producing a bis (2-mercaptoethyl) sulfide compound by reacting with thiourea which is less than 1% by weight to produce an isothiuronium salt and hydrolyzing the obtained isothiuronium salt.
  • the following schemes 1 and 2 are examples of the preparation method.
  • the polythiol compound of the present invention is not particularly limited, and a compound having two or more thiol groups in one molecule may be used.
  • the polythiol compound is not particularly limited, and a compound having two or more thiol groups in one molecule may be used.
  • the polythiol compound is not particularly limited, and a compound having two or more thiol groups in one molecule may be used.
  • the polythiol compound is not particularly limited, and a compound having two or more thiol groups in one molecule may be used.
  • the polythiol compound is not particularly limited, and a compound having two or more thiol groups in one molecule may be used.
  • the polythiol compound is 2- (2-mercaptoethylthio) propane-1,3-dithiol; 2,3-bis (2-mercaptoethylthio) propane-1-thiol; 2- (2,3-bis (2-mercaptoethylthio) propylthio) ethanethiol; 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane; 1,2-bis (2- (2-mercaptoethylthio) -3-mercaptopropylthio) -ethane; Bis (2- (2-mercaptoethylthio) -3-mercaptopropyl) sulfide; 2- (2-mercaptoethylthio) -3-2-mercapto-3- [3-mercapto-2- (2-mercaptoethylthio) -propylthio] propylthio-propane-1-thiol; 2,2'-thiodietanth
  • a compound in which some of the unreacted hydroxy groups are mixed may also be included in the polythiol compound of the present invention.
  • the polymerization modified body obtained by prepolymerization with an isocyanate, a thioepoxy compound, a ethane compound, or the compound which has an unsaturated bond with a resin modifier can also be used for a polythiol compound.
  • polythiol compound Preferably, 1 or more types of other polythiol compounds other than bis (2-mercaptoethyl) sulfide to bis (2-mercaptoethyl) sulfide or bis (2- mercaptoethyl) sulfide are preferable. It can be mixed and used.
  • copolymer composition for thioepoxy clock optical materials of the present invention contains a polythiol compound, a polyisocyanate compound and a thioepoxy compound obtained by the above production method.
  • copolymer composition for optical material means a composition for copolymerization for copolymerizing with an optical material.
  • the polyisocyanate compound contained in the copolymer composition for optical materials of the present invention is not particularly limited, and a compound having at least one isocyanate and / or isothiocyanate group may be used.
  • a compound having at least one isocyanate and / or isothiocyanate group may be used.
  • halogen substituents such as chlorine substituents and bromine substituents, alkyl substituents, alkoxy substituents and nitros of these isocyanate compounds.
  • Substituents, prepolymer-modified products with polyhydric alcohols or thiols, carbodiimide-modified products, urea-modified products, biuret-modified or dimerized, trimerized reaction products, and the like 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 thioepoxy compound contained in the copolymer composition for optical materials of this invention is an episulfide type compound which has a thioepoxy group.
  • an episulfide type compound which has a thioepoxy group.
  • 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 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 composition of the present invention may preferably further include an internal mold release agent, and more preferably may include a phosphate ester compound as an internal mold release agent.
  • Phosphoric acid ester compounds are usually prepared by adding 2-3 moles of an alcohol compound to phosphorus pentoside (P 2 O 5 ).
  • P 2 O 5 phosphorus pentoside
  • 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 internal mold release agent particularly 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, 9 moles of ethylene oxide added, 80% by weight, 8 moles added, 5 parts of 9 moles added) %, 7 mol added 6 wt%, 6 mol added 6 wt%)], 12-PENPP [polyoxyethylenenonylphenol ether phosphate (13 mol added ethylene oxide 3 wt%, 12 mol added 80 wt%, 11 mol added 8 wt%, 9 mol added 3 wt%, 4 mol added 6 wt%)], 16-PENPP [polyoxyethylene nonylphenol ether phosphate (17 mol ethylene oxide) 3 weight percent added, 16 mol added 79 weight percent
  • the copolymer composition for optical materials of this invention may further contain arbitrary components, such as a catalyst, an internal mold release agent, a ultraviolet absorber, a dye, a stabilizer, a bluing agent, as needed.
  • a catalyst such as a catalyst, an internal mold release agent, a ultraviolet absorber, a dye, a stabilizer, a bluing agent, as needed.
  • the compound which has a vinyl group or an unsaturated group which can be copolymerized, a metal compound, etc. can further be included.
  • the optical material of the present invention can be produced by molding polymerizing the copolymer composition for the optical material, that is, a polythiol compound, a polyisocyanate compound, a thioepoxy compound, and a copolymer composition further comprising an optional component as necessary. That is, the composition of this invention is inject
  • the polymerization conditions are not limited because the conditions largely vary 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 150 ° C. In some cases, it is preferable to maintain or gradually raise the temperature in a temperature range of 10 to 150 ° C. and to cure in 1 to 48 hours.
  • the copolymer of the thioepoxy compound, the isocyanate compound, and the thiol compound obtained by curing may be subjected to treatment such as annealing as necessary.
  • 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 polymerized by adding a phosphate ester compound as an internal mold release agent.
  • a phosphate ester compound is the same as above.
  • the catalyst used plays an important role.
  • the type of catalyst is mainly used for epoxy curing agents, but strong amines violate 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 by the molded object of various shapes by changing the mold at the time of casting polymerization, and can be used for various optical materials, such as an eyeglass lens, a camera lens, and a light emitting diode (LED).
  • various optical materials such as an eyeglass lens, a camera lens, and a light emitting diode (LED).
  • it is suitable as optical materials, such as an eyeglass lens, a camera lens, a light emitting diode, and an optical element.
  • 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 used alone, or may be used 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.
  • the compound was analyzed by the following method.
  • the color of the obtained polythiol and resin was evaluated by the YI and APHA values, and the YI and APHA values were evaluated by the following test method.
  • YI Yellow Index
  • dYI Color of polythiol
  • the YI (Yellow Index) value was measured by using a color analyzer equipped with an IRS-2200 condenser on Model UV-2450 of SHIMADZU. Distilled water was put in two identical silica cells having a length of 1 cm, the base line was set, polythiol was placed in the silica cell containing distilled water, and the color YI value was measured.
  • the value of YI represents the yellow index and can be measured by the color chrominometer. The smaller the YI value, the better the color.
  • Color (YI or dYI) of a polythiourethane-based plastic lens Measured using a color analyzer equipped with an IRS-2200 condenser on Model UV-2450 of SHIMADZU.
  • the color YI value was measured by fixing the air as a reference point and fixing the apparatus to fix the lens.
  • the value of YI represents a yellow index and can be measured by a color chrominometer. The smaller the YI value, the better the color.
  • APHA of Polythiol In the present invention, APHA was measured using Hunterlab's ColorQuest XE. The permeation length was measured by placing the sample in a 1 cm quartz cell, and the concentration of the standard solution prepared by dissolving the platinum and cobalt reagents was data. The APHA value obtained from the comparison between the built-in program and the sample solution was measured. The smaller the measured value, the better the color.
  • APHA of the polythiourethane-based plastic lens was measured using Hunter's ColorQuest XE, and the plastic lens was directly measured.
  • concentration of the standard solution prepared by dissolving the reagents of platinum and cobalt was made into data, and the APHA value obtained from the comparison between the built-in program and the sample solution was used as the measurement value. The smaller the measured value, the better the color.
  • reaction progress was confirmed by the GC analysis of the production of bis (2-hydroxyethyl) sulfide compound, and when the reaction was completed, the temperature was lowered to 15 °C, 2079 g (19.97 mol) of 35% by weight hydrochloric acid and calcium content 1286 g (16.89 mol) of thiourea (0.02 weight%) were charged, it aged at 110 degreeC reflux for 3 hours, and performed thiuronium chloride.
  • polythiol having a bis (2-mercaptoethyl) sulfide compound as a main component.
  • APHA of the obtained polythiol was 7 and YI value was 0.75.
  • the reaction progress was confirmed by the GC analysis of the production of bis (2-hydroxyethyl) sulfide compound, and when the reaction was completed, the temperature was lowered to 15 °C, 2079 g (19.97 mol) of 35% by weight hydrochloric acid and calcium content 1286 g (16.89 mol) of 0.1 weight% thiourea was charged, it aged at 110 degreeC reflux for 3 hours, and the thironium chloride was performed.
  • reaction progress was confirmed by the GC analysis of the production of bis (2-hydroxyethyl) sulfide compound, and when the reaction was completed, the temperature was lowered to 15 °C, 2079 g (19.97 mol) of 35% by weight hydrochloric acid and calcium content 1286 g (16.89 mol) of thiourea (0.5 weight%) were charged, it aged for 3 hours at 110 degreeC reflux, and the thironium chloride was performed.
  • polythiol having a bis (2-mercaptoethyl) sulfide compound as a main component.
  • the APHA of the obtained polythiol was 11 and the YI value was 0.85.
  • reaction progress was confirmed by the GC analysis of the production of bis (2-hydroxyethyl) sulfide compound, and when the reaction was completed, the temperature was lowered to 15 °C, 2079 g (19.97 mol) of 35% by weight hydrochloric acid and calcium content 1286 g (16.89 mol) of thiourea (0.9 weight%) were charged, it aged at 110 degreeC reflux for 3 hours, and thironium chloride was performed.
  • reaction progress was confirmed by the GC analysis of the production of bis (2-hydroxyethyl) sulfide compound, and when the reaction was completed, the temperature was lowered to 15 °C, 2079 g (19.97 mol) of 35% by weight hydrochloric acid and calcium content 1286 g (16.89 mol) of thiourea (1.5 weight%) were charged, it aged at 110 degreeC reflux for 3 hours, and thironium chloride was performed.
  • polythiol having a bis (2-mercaptoethyl) sulfide compound as a main component.
  • the APHA of the obtained polythiol was 18 and the YI value was 1.87.
  • reaction progress was confirmed by the GC analysis of the production of bis (2-hydroxyethyl) sulfide compound, and when the reaction was completed, the temperature was lowered to 15 °C, 2079 g (19.97 mol) of 35% by weight hydrochloric acid and calcium content 1286 g (16.89 mol) of thiourea (2.1 weight%) were charged, it aged at 110 degreeC reflux for 3 hours, and the thironium chloride was performed.
  • polythiol having a bis (2-mercaptoethyl) sulfide compound as a main component.
  • APHA of the obtained polythiol was 20 and YI value was 2.16.
  • reaction progress was confirmed by the GC analysis of the production of bis (2-hydroxyethyl) sulfide compound, and when the reaction was completed, the temperature was lowered to 15 °C, 2079 g (19.97 mol) of 35% by weight hydrochloric acid and calcium content 1286 g (16.89 mol) of thiourea (3.0 weight%) were charged, it aged at 110 degreeC reflux for 3 hours, and the thironium chloride was performed.
  • polythiol having a bis (2-mercaptoethyl) sulfide compound as a main component.
  • the APHA of the obtained polythiol was 24 and the YI value was 2.28.
  • BEPS bis (2,3-epithiopropyl) sulfide
  • Phosphoric acid ester 8-PENPP polyoxyethylenenonylphenol ether phosphate (3% by weight of 9 moles of ethylene oxide added, 80% by weight of 8 moles added, 9% by weight 5% by weight, 7 moles of phosphate ester) 6 wt% added, 6 mol added 6 wt%)] 0.15 g, tetrabutylphosphonium bromide 0.2 g, triphenylphosphine 0.1 g, organic dyes HTAQ (20 ppm) and PRD (10 ppm), and an ultraviolet absorber HOPBT 1.5g was mixed at 20 degreeC, and it
  • the mixed solution was defoamed at 400 Pa for 1 hour. Then, it filtered by 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 completion of the polymerization, the mold was taken out of the oven, and releasability 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) 1.699 and Abbe's number 35. The state dissolved before injection into the mold was visually observed. After demolding, it was confirmed that the surface ring was defective. There was no abnormality, no whitening was observed, the YI value was 0.9, and stable quality was obtained.
  • Example 1 In the same manner as in Example 1, according to the composition shown in Table 1, the composition and the optical lens were prepared and evaluated, respectively, and the results are shown in Table 1.
  • Example 1 In the same manner as in Example 1, according to the composition shown in Table 1, the composition and the optical lens were prepared and evaluated, respectively, and the results are shown in Table 1.
  • BEPS bis (2,3-epithiopropyl) sulfide
  • IPDI isophorone diisocyanate
  • HOPBT 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole (2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole)
  • HTQA 1-hydroxy-4- (p-toluidine) -entroquinone (1-hydroxy-4- (p-toluidine) anthraquinone
  • the polythiol compound for optical materials of the thio epoxy clock of which coloring is suppressed and a color is good can be obtained, and, using this polythiol compound, a thio epoxy clock of good color which suppresses coloring and has a low yellowness is used.
  • the copolymer optical material of can be obtained.
  • the polythiol compound of the present invention can be used for the production of copolymer optical materials of thioepoxy clocks, and the thioepoxy optical lenses having good color obtained according to the present invention can be widely used in various fields in place of existing optical lenses. In particular, it can be used as a spectacle lens, a polarizing lens, a camera lens.

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
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Abstract

La présente invention concerne un procédé de production d'un composé polythiol utilisé dans des matériaux optiques à base de résine thioépoxyde et une composition copolymère qui contient le composé polythiol et est destinée à des matériaux optiques à base de résine thioépoxyde, et notamment un composé polythiol de haute qualité pour matériaux optiques présentant des caractéristiques souhaitables d'un point de vue de la coloration, ainsi qu'une composition copolymère contenant ledit composé. La présente invention concerne un procédé de production d'un composé polythiol possédant une coloration réduite au moyen de la régulation de la teneur en calcium de la thio-urée utilisée dans la synthèse d'une composition polythiol pour matériaux optiques à base de résine thioépoxyde et, notamment, un procédé de production d'un composé de bis(2-hydroxyéthyl)sulfure utilisé dans la copolymérisation de matériaux optiques à base de résine thioépoxyde, ainsi qu'une composition copolymère contenant un composé polythiol obtenu au moyen de ce procédé. La lentille optique à base de résine thioépoxyde qui possède une bonne coloration obtenue grâce à la présente invention peut remplacer des lentilles existantes et être largement utilisée dans divers domaines, notamment, en tant que lentilles pour lunettes, lumières polarisées, et caméras.
PCT/KR2013/000628 2012-01-25 2013-01-25 Procédé de production d'un composé polythiol pour matériaux optiques à base de résine thioépoxyde et composition copolymère comprenant ce composé pour matériaux optiques à base de résine thioépoxyde WO2013112001A1 (fr)

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KR20120007442 2012-01-25
KR10-2012-0007442 2012-01-25

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WO2013112001A1 true WO2013112001A1 (fr) 2013-08-01

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160130883A (ko) * 2015-05-04 2016-11-15 주식회사 케이오씨솔루션 티오에폭시계 광학재료의 제조방법과 티오에폭시계 광학재료용 중합성 조성물
JP2018058772A (ja) * 2016-09-30 2018-04-12 ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ 光学材料用ポリチオール化合物の製造方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3059272B1 (fr) * 2013-10-15 2018-02-21 Mitsubishi Gas Chemical Company, Inc. Composition de matériau optique et matériau optique l'utilisant

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR920005917B1 (ko) * 1988-12-22 1992-07-24 미쯔이도오아쯔가가꾸 가부시기가이샤 메르캅토화합물 및 그 제조방법
KR0180926B1 (ko) * 1994-01-26 1999-05-15 사토 아키오 폴리티올 그 제조방법 이것을 사용한 황함유우레탄계수지 그 수지의 제조방법 및 렌즈
KR100417985B1 (ko) * 2000-03-15 2004-02-14 호야 가부시키가이샤 안경용 플라스틱 렌즈
KR20080086993A (ko) * 2006-04-19 2008-09-29 미쓰이 가가쿠 가부시키가이샤 광학재료용 (폴리)티올 화합물의 제조방법 및 그것을포함하는 중합성 조성물

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR920005917B1 (ko) * 1988-12-22 1992-07-24 미쯔이도오아쯔가가꾸 가부시기가이샤 메르캅토화합물 및 그 제조방법
KR0180926B1 (ko) * 1994-01-26 1999-05-15 사토 아키오 폴리티올 그 제조방법 이것을 사용한 황함유우레탄계수지 그 수지의 제조방법 및 렌즈
KR100417985B1 (ko) * 2000-03-15 2004-02-14 호야 가부시키가이샤 안경용 플라스틱 렌즈
KR20080086993A (ko) * 2006-04-19 2008-09-29 미쓰이 가가쿠 가부시키가이샤 광학재료용 (폴리)티올 화합물의 제조방법 및 그것을포함하는 중합성 조성물

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160130883A (ko) * 2015-05-04 2016-11-15 주식회사 케이오씨솔루션 티오에폭시계 광학재료의 제조방법과 티오에폭시계 광학재료용 중합성 조성물
WO2016178522A3 (fr) * 2015-05-04 2017-02-23 주식회사 케이오씨솔루션 Procédé de production de matériau optique à base de thioépoxy, et composition polymère pour matériau optique à base de thioépoxy
CN107548409A (zh) * 2015-05-04 2018-01-05 可奥熙搜路司有限公司 硫代环氧基系光学材料的制备方法和硫代环氧基系光学材料用聚合性组合物
KR102502695B1 (ko) 2015-05-04 2023-02-22 미쓰이 가가쿠 가부시키가이샤 티오에폭시계 광학재료의 제조방법과 티오에폭시계 광학재료용 중합성 조성물
JP2018058772A (ja) * 2016-09-30 2018-04-12 ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ 光学材料用ポリチオール化合物の製造方法

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