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WO2015190809A1 - Nouveau composé de thiol et composition polymérisable le contenant - Google Patents

Nouveau composé de thiol et composition polymérisable le contenant Download PDF

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Publication number
WO2015190809A1
WO2015190809A1 PCT/KR2015/005792 KR2015005792W WO2015190809A1 WO 2015190809 A1 WO2015190809 A1 WO 2015190809A1 KR 2015005792 W KR2015005792 W KR 2015005792W WO 2015190809 A1 WO2015190809 A1 WO 2015190809A1
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WO
WIPO (PCT)
Prior art keywords
bis
mercaptoethylthio
diisocyanate
polymerizable composition
propane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2015/005792
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English (en)
Korean (ko)
Inventor
장동규
노수균
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KOC Solution Co Ltd
Original Assignee
KOC Solution Co Ltd
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Filing date
Publication date
Application filed by KOC Solution Co Ltd filed Critical KOC Solution Co Ltd
Priority to KR1020167030842A priority Critical patent/KR20170018305A/ko
Priority to CN201580030333.1A priority patent/CN106458876B/zh
Publication of WO2015190809A1 publication Critical patent/WO2015190809A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07C319/08—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by replacement of hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
    • C07C321/04—Thiols having mercapto groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to a novel thiol compound and a polymerizable 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.
  • a polyisocyanate compound and a polythiol compound are thermally cured to obtain a urethane optical lens.
  • Urethane-based optical materials have excellent optical properties such as formability, transparency, Abbe's number, heat resistance, light resistance, weather resistance, transmittance, and tensile strength compared to other optical materials, and have excellent coating and workability.
  • urethane-based optical materials have a higher production cost than other plastic optical materials and are mainly used for expensive high refractive lenses.
  • 2,3-bis (2-mercaptoethylthio) -3-propane-1-thiol (GST) and 2- (2-mercaptoethylthio) propane-1,3 which are currently used in many urethane optical materials -Thiol compounds, such as dithiol (GMT) and pentaerythritol tetrakis (3-methcaptopropionate) (PETMP), are expensive and cause the production cost of optical materials to increase.
  • thiol compounds are 3,8-bis (isocyanatomethyl) tricyclo [5,2,1,02,6] decane and 3,9-bis (isocyanatomethyl having excellent mixing properties as isocyanate compounds.
  • bicyclo [2,2,1] heptane to form a polymerizable composition
  • high quality optical materials can be obtained without any problems.
  • isophorone diisocyanate and dicyclohexyl methane-4,4- are an isocyanate compound.
  • H 12 MDI diisocyanate
  • the low quality such as 1,6-hexamethylene off during polymerization reactivity when using an isocyanate compound such as isocyanate for inexpensive multipurpose striae, birch, microbubbles This phenomenon often occurs.
  • Patent Document 1 Republic of Korea Patent Registration 10-0136698
  • Patent Document 2 Republic of Korea Patent Publication 10-0051275
  • Patent Document 3 Republic of Korea Patent Publication 10-0051939
  • Patent Document 4 Republic of Korea Patent Registration 10-0056025
  • Patent Document 5 Republic of Korea Patent Publication 10-0040546
  • An object of the present invention is to provide a new thiol compound, a polymerizable composition comprising the same, and a method of manufacturing the same, which can be used in place of a conventional thiol compound such as a urethane optical material.
  • a thiol compound represented by the following formula (1) is provided.
  • a method for preparing a thiol compound represented by the formula (1) comprising the step of putting malic acid and 2-mercaptoethanol in a reactor and esterifying under elevated temperature and reduced pressure.
  • a polymerizable composition comprising a thiol compound represented by Chemical Formula 1 is provided.
  • a plastic material obtained by polymerizing the polymerizable composition and an optical lens made of this plastic material are provided.
  • the optical lens in particular comprises an spectacle lens.
  • the thiol compound of the present invention may be used in place of a conventional thiol compound such as a urethane optical material.
  • a conventional thiol compound such as a urethane optical material.
  • the polymerizable composition containing the thiol compound of the present invention can produce a urethane-based optical material having a high colorless transparency with high yield even when a general purpose isocyanate compound having low reactivity with an isocyanate compound can be produced. It is effective to reduce.
  • the thiol compound of the present invention is represented by the formula (1) below.
  • the thiol compound of the present invention may be prepared by the method represented by Scheme 1 below.
  • the final product obtained further includes a polynuclear species represented by the following Chemical Formula 2 in addition to the mono product bis (2-mercaptoethyl) -2-hydroxysuccinate (bis). Can be.
  • the polynuclear species (Formula 2) some thioesterification reaction occurs in the esterification reaction in the preparation of bis (2-mercapto ethyl) -2-hydroxysuccinate (bis (2-mercaptoethyl) -2-hydroxysuccinate) Side products produced.
  • the polymerizable composition of the present invention contains a thiol compound represented by the formula (1).
  • This thiol compound makes it possible to obtain a plastic material that is clear and transparent, has a high initial heat deformation temperature, and has excellent heat resistance.
  • the thiol compound has particularly good compatibility with general purpose isocyanate compounds that are less reactive, so that even if a general purpose isocyanate compound is used in the polymerizable composition, a colorless transparent urethane optical material can be obtained.
  • the polymerizable composition of the present invention may further include other thiol compounds in addition to the thiol compound represented by Chemical Formula 1.
  • the other thiol compound is not particularly limited, and a compound having two or more thiol groups in one molecule may be used.
  • another thiol compound is a compound represented by the formula (2); 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane; 2,3-bis (2-mercaptoethylthio) -3-propane-1-thiol; 2,2-bis (mercaptomethyl) -1,3-propanedithiol; Bis (2-mercaptoethyl) sulfide; Tetrakis (mercaptomethyl) methane; 2- (2-mercaptoethylthio) propane-1,3-dithiol; 2- (2,3-bis (2-mercaptoethylthio) propylthio) ethanethiol; Bis (2,3-dimercaptopropanyl) sulfide; Bis (2,3-dimercaptopropanyl) disulfide; 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane; 1,2-bis (2- (2- (2-
  • the thiol 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'- thiodiethan
  • the polymerizable composition of the present invention may further contain an isocyanate compound.
  • an isocyanate compound a general-purpose isocyanate compound which is supplied at low cost may be used.
  • an isocyanate compound is 2, 5-bis (isocyanatomethyl) bicyclo [2, 2, 1] heptane (NBDI); Isophorone diisocyanate; Dicyclohexylmethane-4,4'-diisocyanate (H 12 MDI); Hexamethylene diisocyanate; Methylcyclohexanediisocyanate; Tolylene diisocyanate; Phenylene diisocyanate; 1,3,5-tris (6-isocyanato-hexyl)-[1,3,5] -trigianan-2,4,6-trione (HDI trimer); One or two or more isocyanates selected from the group consisting of o, m, p-xylene diisocyanate and tetramethylxy
  • the isocyanate compound usable in the polymerizable composition of the present invention is not limited to the above-mentioned general purpose isocyanate compound, and any compound can be used as long as it is a compound having at least one isocyanate and / or iso (thio) cyanate group. That is, one or two or more different iso (thio) cyanate compounds may be included instead of the general purpose isocyanate compound or together with the general purpose isocyanate compound.
  • such other iso (thio) cyanate compounds include 2,2-dimethylpentane diisocyanate; 2,2,4-trimethylhexanediisocyanate; Butane diisocyanate; 1,3-butadiene-1,4-diisocyanate; 2,4,4-trimethylhexamethylene diisocyanate; 1,6,11-undectriisocyanate; 1,3,6-hexamethylenetriisocyanate; 1,8-diisocyanate-4-isocyanatomethyloctane; Bis (isocyanatoethyl) carbonate; Aliphatic isocyanate compounds containing bis (isocyanatoethyl) ether,
  • One or two or more iso (thio) cyanate compounds selected from the group consisting of can be used.
  • the polymerizable composition of the present invention may be composed of a thiepoxy polymerizable composition by further including a thioepoxy compound.
  • the thioepoxy compound is, for example, bis (2, 3- epithiopropyl) sulfide; Bis (2,3-epiopropyl) disulfide; 2,3-epidithiopropyl (2,3-ethiothiopropyl) disulfide; 2,3- epidithiopropyl (2,3- epithiopropyl) sulfide; 1,3 and 1,4-bis ( ⁇ -ethiothiopropylthio) cyclohexane; 1,3 and 1,4-bis ( ⁇ -ethiothiopropylthiomethyl) cyclohexane; Bis [4- ( ⁇ -epithiopropylthio) cyclohexyl] methane; 2,2-bis [4- ( ⁇ -epithiopropylthio
  • halogen substituents such as chlorine substituents and bromine substituents, alkyl substituents, alkoxy substituents, nitro substituents and prepolymer-modified compounds with polythiol may be used.
  • the polymerizable composition of the present invention is a polymerizable composition containing, as a main component, a thiol compound of the present invention and a compound such as an isocyanate compound capable of polymerization reaction thereof, and an internal mold release agent, an ultraviolet absorber, a polymerization initiator, a dye, and a stabilizer, if necessary. It may further include an optional component such as a bluing agent.
  • the internal mold release agent may preferably include a phosphate ester compound.
  • Phosphate ester is prepared by adding 2-3 moles of 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 in the composition of the present invention as an internal mold release agent, an optical material having good release property and excellent quality can be obtained.
  • UV absorbers may be included in the polymerizable composition of the present invention for improving the light resistance of the optical material and blocking ultraviolet rays.
  • a known ultraviolet absorber can be used without limitation.
  • 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
  • 5-chloro-2H-benzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole and the like can be used.
  • Such an ultraviolet absorber can block 400 nm or more when used in an amount of 0.6 g or more with respect to 100 g of the optical resin composition.
  • the polymerization initiator may be an amine or tin compound.
  • a tin type compound Butyl tin dilaurate; Dibutyl tin dichloride; Dibutyl tin diacetate; Stannous oxyl acid; Dibutyl dilaurate; Tetrafluorotin; Tetrachlorotin; Tetrabromotin; Tetraiodine tin; Methyl tin trichloride; Butyltin trichloride; Dimethyltin dichloride; Dibutyltin dichloride; Trimethyltin chloride; Tributyltin chloride; triphenyltin chloride; Dibutyltin sulfide; Di (2-ethylsecyl) tin oxide and the like may be used alone or in combination of two or more thereof.
  • the optical material of the present invention can be produced by, for example, injecting and curing a polymerizable composition containing a thiol compound, an isocyanate compound of the present invention, and optional components selected as necessary into a mold for a lens. Moreover, it is also possible to further mix and polymerize here the epoxy compound, the thioepoxy compound, the compound which has a vinyl group or an unsaturated group, a metal compound, etc. which are copolymerizable with a urethane resin composition.
  • the urethane-based optical material for example, the urethane-based lens produced in the present invention is produced by mold polymerization.
  • vacuum degassing is performed while adding a thiol compound and cooling. Then, after a suitable time elapses, the glass mold is molded into a tape and cured by slowly applying heat from low temperature to high temperature for about 24 to 48 hours.
  • the urethane-based optical material produced by the present invention is characterized by low dispersion at high refractive index, excellent heat resistance and durability, light weight and excellent impact resistance, and good color. Therefore, it is suitable for the use of the urethane type optical lens, prism, etc. which concerns on this invention, and is especially suitable for the lens use, such as a spectacle lens and a camera lens.
  • the urethane-based optical material of the present invention is also very low in tape whitening and bubbles, it can be produced in a good yield.
  • the optical material of the present invention may be subjected to surface polishing, antistatic treatment, hard coat treatment, for the purpose of improving antireflection, high hardness, abrasion resistance, chemical resistance, antifouling, or fashion, as necessary. Physical and chemical treatments such as anti-reflective coating treatment, dyeing treatment, and dimming treatment can be performed.
  • Refractive index (nd and nE) and Abbe number It was measured at 20 ° C. using an Abbe refractometer, an IT and DR-M4 model of Atago.
  • TMA Initial heat deflection temperature
  • a Dean-stark device was mounted in a 1 L reactor capable of temperature control, malic acid (134.09 g, 1.00 mol), 2-mercaptoethanol (156.26 g, 2.00 mol), toluene 130 g, p-toluene sulphonic acid (11.41 g, 0.06 mol) was added and stirred, and the mixture was reacted for 7 hours while maintaining the reduced pressure at 100 torr and the internal temperature of 50 ° C. The water produced in the reaction was reacted while removing water using Dean-stark apparatus. The reaction was terminated when 36 g of theoretical water produced and the starting material 2-mercaptoethanol disappeared on HPLC.
  • the reactor was cooled down and at room temperature, the catalyst was removed by slowly neutralizing with 200 g of 5 wt% NaHCO 3 (aq) to remove the remaining p-toluenesulfonic acid, followed by deionized water to remove salt.
  • the organic layer was washed three times with 100 g of pure water and concentrated under reduced pressure to give 203 g of a thiol compound.
  • the yield was 80%, and the refractive index (nd, 20 ° C.) was 1.527.
  • the Dean-stark apparatus was mounted in a 1 L reactor capable of temperature control, and was equipped with malic acid (134.09 g and 1.00 moles), 2-mercaptoethanol (160.20 g and 2.05 moles), toluene 200 g, and p-toluene sulphonic acid (11.41 g, 0.06 mol) was added and stirred, and the mixture was reacted for 7 hours while maintaining the reduced pressure at 100 torr and the internal temperature of 50 ° C. The water produced in the reaction was reacted while being removed from the reactant using a Dean-stark apparatus. The reaction was terminated when the amount of theoretical water and the starting material 2-mercaptoethanol disappeared on HPLC.
  • the reactor was cooled down, and upon reaching room temperature, the catalyst was removed by slowly neutralizing with 200 g of 5 wt% NaHCO 3 (aq) to remove the remaining p-toluenesulfonic acid, and deionized water to remove salt.
  • the organic layer was washed three times with 100 g of pure water and concentrated under reduced pressure to give 212 g of a thiol compound.
  • the yield was 83%, and the refractive index (nd, 20 ° C.) was 1.527.
  • the thiol compound, the isocyanate compound, and the additive prepared in the synthesis example were mixed in the composition as shown in Table 1, and the polymerization was carried out to prepare a urethane-based optical lens, and the refractive index and the Abbe's number were evaluated.
  • the mixed solution was defoamed at 1 torr for 1 hour. Then, it filtered by the 1 micrometer PTFE filter, and inject
  • the 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. Mold release from the mold was good, and the obtained resin was further annealed at 130 ° C for 4 hours.
  • the physical properties of the obtained resin had a refractive index (nE) of 1.559, an Abbe number ( ⁇ e) 44, and an initial heat deformation temperature (Tg) of 120 ° C.
  • BMHS bis (2-mercaptocaptoethyl) -2-hydroxysuccinate (bis (2-mercaptoethyl) -2-hydroxysuccinate))
  • PETMP pentaerythritol tetra (3-mercaptopropionate) (pentaerythritol tetra (3-mercaptopropionate))
  • NBDI 2,5 (6) -bis (isocyanatomethyl) bicyclo [2.2.1] heptane (2,5 (6) -Bis (isocyanatomethyl) bicyclo [2.2.1] heptane)
  • HOPBT 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole (2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole)
  • HTAQ 1-hydroxy-4- (p-tolludine) -entroquinone (1-hydroxy-4- (p-toluidine) anthraquinone)
  • the plastic material obtained from the polymerizable composition containing the thiol compound of the present invention was clear and transparent in color, high initial heat deformation temperature and excellent heat resistance.
  • the thiol compound of the present invention and the polymerizable composition including the same are suitable for the production of urethane-based plastic materials satisfying both quality and economy, and are particularly suitable for the production of urethane-based plastic materials requiring colorless transparency and high or medium refractive index.
  • the present invention provides a variety of optical materials such as recording media substrates, color filters, UV absorbing filters, such as spectacle lenses, polarizing lenses, camera lenses, prisms, optical fibers, LCDs, optical disks, magnetic disks, LCDs, monitor screens, It can be widely used in a field where a transparent plastic such as a surface protective cover of an electronic product is required.

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

Abstract

L'invention concerne un nouveau composé de thiol et une composition polymérisable le contenant. La présente invention utilise un composé de thiol et une composition polymérisable le contenant. Le composé de thiol et la composition polymérisable le contenant de la présente invention sont appropriés pour la production de matériaux en plastique à base d'uréthane, satisfaisant à la fois la qualité du produit et la faisabilité économique, et sont appropriés pour la production, en particulier, de matériaux en plastique à base d'uréthane qui doivent présenter une transparence incolore et une propriété de réfraction élevée ou moyenne.
PCT/KR2015/005792 2014-06-09 2015-06-09 Nouveau composé de thiol et composition polymérisable le contenant Ceased WO2015190809A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020167030842A KR20170018305A (ko) 2014-06-09 2015-06-09 새로운 티올화합물과 이를 포함하는 중합성 조성물
CN201580030333.1A CN106458876B (zh) 2014-06-09 2015-06-09 新的硫醇化合物和包含其的聚合性组合物

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KR20140069669 2014-06-09
KR10-2014-0069669 2014-06-09

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
EP3505335A1 (fr) * 2017-12-28 2019-07-03 SKC Co., Ltd. Composition de polythiol pour une lentille optique en plastique

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Publication number Priority date Publication date Assignee Title
KR101894921B1 (ko) 2018-01-19 2018-09-04 에스케이씨 주식회사 플라스틱 광학 렌즈용 폴리티올 조성물
CN112759734A (zh) * 2020-12-28 2021-05-07 山东益丰生化环保股份有限公司 一种用于3d打印展示材料的聚硫氨酯树脂及其合成方法和应用
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