WO2012112014A2 - Nouveau composé de polythiol, procédé pour le préparer et composition de résine pour matériau optique à base d'uréthane l'employant - Google Patents

Nouveau composé de polythiol, procédé pour le préparer et composition de résine pour matériau optique à base d'uréthane l'employant Download PDF

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WO2012112014A2
WO2012112014A2 PCT/KR2012/001276 KR2012001276W WO2012112014A2 WO 2012112014 A2 WO2012112014 A2 WO 2012112014A2 KR 2012001276 W KR2012001276 W KR 2012001276W WO 2012112014 A2 WO2012112014 A2 WO 2012112014A2
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WO
WIPO (PCT)
Prior art keywords
bis
diisocyanate
isocyanatomethyl
tris
mercaptoethylthio
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PCT/KR2012/001276
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English (en)
Korean (ko)
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WO2012112014A3 (fr
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장동규
노수균
김종효
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주식회사 케이오씨솔루션
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Publication of WO2012112014A2 publication Critical patent/WO2012112014A2/fr
Publication of WO2012112014A3 publication Critical patent/WO2012112014A3/fr

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    • 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
    • C07C323/01—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/02—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/03—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to a novel polythiol compound having usefulness for optical lens materials, a method for producing the same, and a resin composition for an optical material using the same, and particularly to a resin composition for a polythiourethane-based optical material having high refractive index and excellent heat resistance and reactivity. It is about.
  • Urethane-based plastic optical lenses manufactured using mercapto compounds and isocyanates have been widely used as optical lens materials because of excellent optical properties, ie, transparency, Abbe number, and tensile strength.
  • urethane-based plastic optical lenses have a low heat distortion temperature, which causes problems when the lens is hard and multi-coated (anti-reflective coating) on the surface of the lens after casting, causing deformation of the center of the lens. When exposed to heat, the thermal deformation of the lens is severe, causing a problem of severe cracking of the multi-film. This creates a cloudy film on the surface of the lens, which sharply degrades the transparency of the lens.
  • urethane-based high refractive plastic optical lens manufactured as described above has a problem in that thermal deformation is severe when exposed to high temperature, so that the multi-film is easily cracked, and the lens center portion is deformed during hard and multi-coating on the lens surface.
  • urethane-based ultrahigh refractive plastic optical lenses are manufactured by thermosetting xylylene diisocyanate and 2,3-bis (2-mercaptoethylthio) -propane-1-thiol.
  • This lens has a high refractive index of 1.655, There is a problem in that the center portion of the lens is deformed during hard and multi-coating on the lens surface, and when the film is exposed to high temperature, the thermal deformation is severe and the multi-film easily breaks.
  • Korean Patent Publication No. 1993-0006918 describes bis (isocyanatomethyl) triscyclo [5,2,1,02,6] decane and bis (isocyanato) in the production of urethane optical lenses.
  • Thermosetting methyl) bicyclo [2,2,2] heptane compound and PETMP (pentaerythritol tetrakismercaptopropionate) or 1,2-bis (2-mercaptoethylthio) -3-mercaptopropane To produce a urethane plastic optical lens.
  • the urethane-based plastic optical lens thus prepared has a bis (isocyanatomethyl) triscyclo [5,2,1,02,6] decane, bis (isocyanatomethyl) bicyclo [2, 2,2] has a problem that is expensive to prepare heptane.
  • a method of prepolymerizing a mercapto compound and an isocyanate compound to produce a resin composition for an optical material is disclosed in Korean Patent No. 10-0472837.
  • the optical lens is manufactured by curing a compound having a dihydric alcohol added to a polyisocyanate and a polythiol compound, but the resin composition and optical lens for optical materials having a high Abbe number and high impact resistance It could not be manufactured.
  • the resin for the optical material resin optical material introduced in this patent is difficult to inject, there is a problem that a large amount of polymerization failure occurs during curing of the resin composition.
  • the manufactured lens has a refractive index of 1.545 to 1.556, which has a problem that the edge of the lens becomes thick due to its low refractive index.
  • Korean Patent Registration Nos. 10-0237664 and 10-0241989 disclose that a component obtained by prepolymerizing a polythiol compound having a specific structure with a polyisocyanate compound comprises a component consisting of a (meth) acrylate compound and a compound copolymerizable with them. Polymerization curing with the composition provided an optical lens resin and an optical lens excellent in both physical properties and productivity of the lens.
  • the prepolymer obtained by reacting the -SH / -NCO molar ratio of the resin composition for optical materials in the range of 3.0 to 7.0 can be blended with acrylic, but the viscosity is so high that it is directly blended with polyisocyanate, a urethane curing agent, and injected into the mold. Injecting is difficult, and there is a problem that a lot of polymerization failure occurs.
  • the prepolymer having a -SH / -NCO molar ratio of 0.5 to 2.0 as disclosed in Japanese Patent Laid-Open No. 5-25240 has a higher viscosity and thus has the above problems in manufacturing a urethane-based optical lens.
  • GST 2,3-bis (2-mercaptoethylthio) propane-1-thiol
  • XDI xylylene diisocyanate
  • the present inventors have developed a method of mixing isophorone diisocyanate or dicyclohexyl methane diisocyanate with 1,6-hexamethylene diisocyanate as a method of increasing the heat resistance of a lens while using a general-purpose isocyanate compound which is inexpensive. Has been elected.
  • this method can achieve good heat resistance when the content of isophorone diisocyanate or dicyclohexyl methane diisocyanate in the isocyanate content is 40% by weight or more, in which case the reactivity with the mercapto compound decreases, resulting in high temperature.
  • the present invention in order to solve the above problems, obtain a higher refractive index and increase the heat resistance, it is to provide a novel polythiol compound disulfide without using a thiol compound as it is.
  • a higher refractive index can be obtained, and the heat resistance is increased to increase the viscosity, thereby reducing the solubility of the resin composition for optical materials, thereby solving the problem of tape whitening.
  • R 1 and R 2 represent an aromatic organic residue, an alicyclic organic residue, an aliphatic organic residue, a heterocyclic organic residue, an aromatic organic residue containing one or more sulfur atoms, an aliphatic organic residue containing one or more sulfur atoms, and one It is any one of the heterocyclic organic residue containing the above sulfur atom,
  • x + y is an integer from 3 to 10
  • n is an integer from 1 to 5.
  • the resin composition for optical materials containing the polythiol compound of said Formula 1 is provided.
  • the resin composition for an optical material of the present invention may further include an isocyanate compound or a thioisocyanate compound.
  • the resin composition for an optical material of the present invention may further include other thiol compounds in addition to the polythiol compound of Formula 1.
  • the resin composition for an optical material containing the polythiol compound of the present invention having disulfide had no problem of whitening or bubble generation during lens manufacture.
  • the optical material resin obtained by hardening the said resin composition for optical materials and the optical product which consists of this optical material resin are provided.
  • Optical products include spectacle lenses, 3D polarized lenses, polarized lenses, prismatic films, optical fibers, optical disks, magnetic disks, recording medium substrates, color filters, ultraviolet absorbing filters.
  • the whitening phenomenon did not appear at the edges of the lens due to the adhesive elution of the adhesive tape by lowering the solubility and maintaining an appropriate viscosity. No bubble problems at the edges of the lens due to leakage.
  • the polythiol compound having disulfide is used as a raw material for optical materials, and the optical material obtained by using the same can increase the refractive index, and has excellent heat resistance and reactivity, such as lenses of glasses, camera lenses, prisms, optical pipes, optical disks, It can be usefully used for optical products, such as recording medium engines, such as a magnetic disk, a coloring filter, and an infrared absorption filter.
  • the novel polythiol compound provided by this invention has at least 1 or more disulfide, and is represented by following formula (1).
  • R 1 and R 2 represent an aromatic organic residue, an alicyclic organic residue, an aliphatic organic residue, a heterocyclic organic residue, an aromatic organic residue containing one or more sulfur atoms, an aliphatic organic residue containing one or more sulfur atoms, and one It is any one of the heterocyclic organic residue containing the above sulfur atom,
  • x + y is an integer from 3 to 10
  • n is an integer from 1 to 5.
  • the polythiol compound of the present invention has at least one or more disulfide bonds formed in the reaction of the thiol compound and the oxidant, and is prepared by reacting the thiol compound and the oxidant.
  • a halogen group compound, a radical catalyst, a peroxide such as sodium chlorite, etc. may be used, but is not limited thereto. More specific examples of the oxidizing agent may include oxygen, hydrogen peroxide, sodium hypochlorite, iodine, sulfyl chloride, iron (III) chloride, nitrogen oxide, and the like, but are not limited thereto.
  • the amount of the chain extender to be used is preferably 0.05 to 1.5 moles with respect to the -SH molar ratio of the thiol compound, and preferably about 0.1 to 0.8 molar ratio.
  • the use of less than 0.05 molar ratio did not help the problem of viscosity and tape whitening due to the small increase in viscosity and the equivalent, and the use of more than 1.5 molar ratio is too suitable for the resin composition for optical materials because the viscosity is too high to increase the molecular weight. Did not do it.
  • thiol compound which may be used to prepare the polythiol compound of Chemical Formula 1, 2,2-bis (mercaptomethyl) -1,3-propanedithiol; Tetrakis (mercaptomethyl) methane; 2- (2-mercaptoethylthio) propane-1,3-dithiol; 2,3-bis (2-mercaptoethylthio) propane-1-thiol; Bis (2,3-dimercaptopropanyl) sulfide; Bis (2,3-dimercaptopropanyl) disulfide; 2- (2,3-bis (2-mercaptoethylthio) propylthio) ethanethiol; 1,1,3,3-tetrakis (mercaptomethylthio) propane; 1,1,2,2-tetrakis (mercaptomethylthio) ethane; 4,6-bis (mercaptomethylthio) -1,3-dithiane; 2- (2,2-bis (mercaptomethylthio)
  • thiol compounds that can be used include a thiol compound having an aromatic organic residue, an alicyclic organic residue, an aliphatic organic residue, and a heterocyclic organic residue, including a halogen group and / or a hydroxy group or episulfide and thiethane. It may include.
  • mercaptomethanol For example, mercaptomethanol; 2-mercaptoethanol; 1-chloro-3-mercapto-propan-2-ol; Thiethane-3-thiol; Oxylenyl methane thiol; Thylenyl methane thiol; 2-mercaptopropionic acid; 3-mercaptobutyric acid; 2-mercaptoisobutyric acid; 3-mercaptoisobutyric acid; Methanedithiol; 1,2-ethanedithiol; 1,1-propanedithiol, etc. can be used 1 or more types. However, it is not limited thereto.
  • a resin composition for an optical material including the polythiol compound of Formula 1 is provided, and the resin composition for the optical material may further include an isocyanate compound or a thioisocyanate compound.
  • the resin composition for an optical material of the present invention may further include other thiol compounds in addition to the polythiol compound of Formula 1.
  • isocyanate compound or isothiocyanate compound examples include hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, 1,3-butadiene-1,4 -Diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecanetriisocyanate, 1,3,6-hexamethylenetriisocyanate, 1,8-diisocyanato-4-iso Aliphatic polyisocyanate compounds such as cyanatomethyloctane, bis (isocyanatoethyl) carbonate, bis (isocyanatoethyl) ether, lysine diisocyanatomethyl ester and lysine triisocyanate; 1,2-diisocyanatobenzene, 1,3-diisocyanatobenzene, 1,4-diiso
  • thiol compound which can be used in addition to the polythiol compound of Formula 1, 1,2-ethanedithiol; 1,1-propanedithiol; 1,2-propanedithiol; 1,3-propanedithiol; 2,2-propanedithiol; 2,5-hexanedithiol; 1,6-hexanedithiol; 2,9-decanedithiol; 1,4-bis (1-mercaptoethyl) benzene; Cyclohexanedithiol; 1,2,3-propanethiol; 1,1-bis (mercaptomethylcyclohexane); 1,2-dimercaptopropylmethyl ether; 2,3-dimercaptopropylmethyl ether; 2,2-bis (mercaptomethyl) -1,3-propanedithiol; Bis (2-mercaptoethyl) ether; Tetrakis (mercaptomethyl) methane; 2- (2-mercaptoethyl
  • the resultant is purified using a purification method such as distillation under reduced pressure, washing, filtration, or the like, and more preferably, purified using high purity.
  • a compound for controlling other reactions may be added, and as the compound to be added for this purpose, a compound such as a vinyl group, a compound having a thioepoxy group, an epoxy compound, thiethane, or the like may be used alone or in combination. Can be.
  • the resin composition for optical materials of this invention may contain the additive for improving optical characteristics.
  • Additives include in particular ultraviolet absorbers, stabilizers, internal mold release agents, color correctors (pigments, dyes), antioxidants, mold release agents and the like.
  • any known ultraviolet absorbent surface usable for the optical lens can be used.
  • any known ultraviolet absorbent surface usable for the optical lens can be used.
  • 2- (2'-hydroxy-5-methylphenyl) -2H-benzotriazole 2-hydroxy having good ultraviolet absorption in the wavelength range of 400 nm or less and having good solubility in the composition of the present invention.
  • the stabilizer for improving the optical characteristic of the resin composition for optical materials in 0.01 to 5.00 weight% of all the compositions.
  • the stabilizer is used at 0.01% by weight or less, the stability effect is weak, and when using at least 10.00% by weight, there is a problem in that the polymerization failure rate during curing is high and the stability of the cured product is lowered.
  • calcium stearate which is a metal fatty acid salt type; Barium stearate; Zinc stearate; Cadmium stearate; Lead stearate; Magnesium stearate; Aluminum stearate; Potassium stearate;
  • One or two or more of compounds such as zinc octoate can be used, and phosphorus-based triphenyl phosphite; Diphenyldecylphosphite; Phenyl didecyl phosphite; Diphenyldodecyl phosphite; Trinolylphenyl phosphite; Diphenylisooctylphosphite; Tributyl phosphite; Tripropyl phosphite; Triethyl phosphite; Trimethyl phosphite; Tris (monodecyl phosphite); One kind or two or more kinds of compounds such as
  • a phosphorus stabilizer is used.
  • the molded lens was able to greatly improve the stability of the optical lens without deteriorating the optical characteristics such as transparency, impact strength, heat resistance, and polymerization yield.
  • Fluorine-type nonionic surfactant which has a perfluoroalkyl group, a hydroxyalkyl group, or a phosphate ester group; Silicone nonionic surfactants having a dimethylpolysiloxane group, a hydroxyalkyl group or a phosphate ester group; Alkyl quaternary ammonium salts, ie, trimethylcetyl ammonium salt, trimethylstearyl, dimethylethylcetyl ammonium salt, triethyldodecyl ammonium salt, trioctylmethyl ammonium salt, diethylcyclohexadodecyl ammonium salt;
  • the component selected from the acidic phosphate ester can be used individually or in combination of 2 or more types.
  • acidic phosphate ester is used, and as acidic phosphate ester, isopropyl acid phosphate; Diisopropyl acid phosphate; Butyl phosphate; Octylic acid phosphate; Dioctyl acid phosphate; Isodecyl phosphate; Diisodecyl phosphate; Tridecanoic acid phosphate; Bis (tridecanoic acid) phosphate or the like may be used alone or in combination of two or more thereof.
  • ZELEC UN TM (Stepan), which is an acidic phosphate ester, was found to exhibit the best demolding when demolding the mold from the lens after curing.
  • the internal mold release agent may be used in an amount of 0.0001 to 10% by weight based on the total weight of the reaction mixture. Preferably, 0.005 to 2% by weight of the mold release agent in the lens has a high polymerization yield. If the amount of the release agent is less than 0.005%, a phenomenon may occur in which the lens adheres to the surface of the glass mold when the molded optical lens is separated from the glass mold, and if more than 2% by weight, the lens is separated from the glass mold during the polymerization of the mold. There is a problem that may cause stains on the surface.
  • a hard coat coating may be provided on the outer surface of the cast resin to increase the wear resistance of the surface. Further, by inserting a primer layer between the surface of the resin and the hard coat film, the adhesion of the resin to the hard coat film can be improved.
  • a completely cured and annealed resin is first coated with a primer solution, and then a conventional known method such as immersion method or spin-film method. And a hard coat agent according to the flow-coating method, the spraying method and other methods.
  • an anti-reflection film can be installed on the surface of the cast resin to prevent surface reflection on the surface of the optical element, thereby increasing the transmittance of visible light.
  • the resin composition for an optical material including the polythiol compound of the present invention having disulfide had no problem of whitening or bubble generation during lens manufacture.
  • the optical material resin obtained by hardening the said resin composition for optical materials and the optical product which consists of this optical material resin are provided.
  • Optical products include spectacle lenses, 3D polarized lenses, polarized lenses, prismatic films, optical fibers, optical disks, magnetic disks, recording medium substrates, colored filters, ultraviolet absorbing filters and the like.
  • BDPS bis (2,3-dimercaptopropanyl) sulfide
  • BDPSS bis (2,3-dimercaptopropanyl) disulfide
  • optical lens obtained in (2) was processed to a diameter of 72 mm, ultrasonically washed with an alkaline aqueous washing solution, and then annealed at 120 ° C. for 2 hours.
  • Refractive index It was measured using an Abbe refractometer of Atago Co., 1T and DR-M4 models.
  • compositions and lens were prepared according to the composition described in Table 1 and the physical properties were tested in the same manner as in Example 1, and the results are shown in Table 1.
  • IPDI isophorone diisocyanate
  • PETMP pentaerythritol tetrakis (3-mercaptopropionate) (pentaerythritol-tetrakis (3-mercaptopropionate))
  • GMTDS 2- (2-mercaptoethylthio-3- [3-mercapto-2- (2-mercaptoethylthio) -propyldithio) -propane-1-thiol (2- (2-mercaptoethylthio-3 Oligomeric Disulfide Polythiol Compounds of-[3-mercapto-2- (2-mercapto ethylthio) -propyldithio] propane-1-thiol)
  • BDPSS 3- ⁇ 3- [3- (2,3-Dimercaptopropylthio) -2-mercaptopropylthio] -2-mercaptopropylthio ⁇ -propane-1,2-dithiol (3- ⁇ Oligomeric Disulfide Polythiol Compounds of 3- [3- (2,3-dimercaptopropylthio) -2-mercaptopropyldithio] -2-mercapto-propylthio ⁇ propane-1,2-dithiol)
  • BDPSDS 3- ⁇ 2- [3- (2,3-dimercaptopropylthio) -2-mercaptopropyldithio] -3-mercaptopropyldithio ⁇ -propane-1,2-dithiol (3 Oligomeric Disulfide Polythiol Compounds of-(2- [3- (2,3-dimercaptopropyldithio) -2-mercaptopropyldithio] -3-mercapto-propyldithio ⁇ propane-1,2-dithiol)
  • ZELEC UN An acidic phosphate ester compound manufactured by Stepan, trade name ZELEC UN TM
  • HOPBT 2- (2'-hydroxy-5'-t-octylphenyl) -2H-benzotriazole
  • the novel polythiol compound is used as a raw material of the optical material and the optical material obtained by using the same can increase the refractive index, and excellent in heat resistance and reactivity.
  • the optical lens according to the present invention in particular, can be applied to the spectacle lens, and used in 3D polarized lenses equipped with a polarizing film on the spectacle lens, recording medium substrate, coloring used in prism, optical fiber, optical disk, magnetic disk, etc. in addition to the spectacle lens It can be usefully used as various optical products, such as a filter and an ultraviolet absorption filter.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un nouveau composé de polythiol ayant une utilité pour un matériau de lentille optique, un procédé pour le préparer, et une composition de résine pour un matériau optique employant le nouveau polythiol. Une composition de résine pour un matériau optique contenant le composé de polythiol de la présente invention présente une excellente résistance à la chaleur et une excellente réactivité tout en présentant un indice de réfraction élevé et peut donc être utilisé pour divers produits optiques comprenant des lentilles comme des lentilles de lunette et des lentilles de caméra, un prisme, un tube optique, un système de support d'enregistrement comme un disque optique et un disque magnétique, un filtre coloré et un filtre absorbant les infrarouges.
PCT/KR2012/001276 2011-02-18 2012-02-20 Nouveau composé de polythiol, procédé pour le préparer et composition de résine pour matériau optique à base d'uréthane l'employant WO2012112014A2 (fr)

Applications Claiming Priority (2)

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KR20110014821 2011-02-18
KR10-2011-0014821 2011-02-18

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CN105601549A (zh) * 2015-12-25 2016-05-25 四川大学 刺激敏感型二异氰酸酯
CN108219109A (zh) * 2017-12-28 2018-06-29 山东益丰生化环保股份有限公司 一种超高韧性的树脂镜片及其制备方法
EP3486272A4 (fr) * 2016-07-14 2020-01-22 SKC Co., Ltd. Composé polythiol aromatique pour matériau optique
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US11583389B2 (en) 2019-04-05 2023-02-21 Amo Groningen B.V. Systems and methods for correcting photic phenomenon from an intraocular lens and using refractive index writing
US11678975B2 (en) 2019-04-05 2023-06-20 Amo Groningen B.V. Systems and methods for treating ocular disease with an intraocular lens and refractive index writing
WO2023167262A1 (fr) * 2022-03-01 2023-09-07 三井化学株式会社 Résine, article moulé, matériau optique, lentille, 2,5-bis(isocyanatométhyl)furane, et composition polymérisable
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US11678975B2 (en) 2019-04-05 2023-06-20 Amo Groningen B.V. Systems and methods for treating ocular disease with an intraocular lens and refractive index writing
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US11944574B2 (en) 2019-04-05 2024-04-02 Amo Groningen B.V. Systems and methods for multiple layer intraocular lens and using refractive index writing
WO2023167262A1 (fr) * 2022-03-01 2023-09-07 三井化学株式会社 Résine, article moulé, matériau optique, lentille, 2,5-bis(isocyanatométhyl)furane, et composition polymérisable

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