WO1998037114A1 - Composition durcissable et materiau optique prepare a partir de celle-ci - Google Patents

Composition durcissable et materiau optique prepare a partir de celle-ci Download PDF

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Publication number
WO1998037114A1
WO1998037114A1 PCT/JP1998/000643 JP9800643W WO9837114A1 WO 1998037114 A1 WO1998037114 A1 WO 1998037114A1 JP 9800643 W JP9800643 W JP 9800643W WO 9837114 A1 WO9837114 A1 WO 9837114A1
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WO
WIPO (PCT)
Prior art keywords
compound
curable composition
meth
mercapto
acrylate
Prior art date
Application number
PCT/JP1998/000643
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English (en)
Japanese (ja)
Inventor
Kouji Shimada
Katsumasa Yamamoto
Michio Suzuki
Takeo Ogihara
Yukio Ichikawa
Original Assignee
Sumitomo Seika Chemicals Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP9052318A external-priority patent/JPH10231343A/ja
Priority claimed from JP05231997A external-priority patent/JP3872155B2/ja
Application filed by Sumitomo Seika Chemicals Co., Ltd. filed Critical Sumitomo Seika Chemicals Co., Ltd.
Priority to AU58817/98A priority Critical patent/AU5881798A/en
Publication of WO1998037114A1 publication Critical patent/WO1998037114A1/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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/66—Mercaptans

Definitions

  • the present invention relates to a curable composition and an optical material comprising the same. More specifically, optical materials such as plastic lenses for eyeglasses, Fresnel lenses, lenticure lenses, optical disc substrates, plastic optical fibers, LCD prism sheets, light guide plates, and diffusion sheets, paints, adhesives, and seals
  • optical materials such as plastic lenses for eyeglasses, Fresnel lenses, lenticure lenses, optical disc substrates, plastic optical fibers, LCD prism sheets, light guide plates, and diffusion sheets, paints, adhesives, and seals
  • the present invention relates to a curable composition useful as a raw material for materials. Background art
  • polystyrene resin polymethyl methacrylate resin
  • polycarbonate resin diethylene glycol diaryl carbonate resin, etc.
  • resins for optical materials because they are lighter and easier to handle than glass. I have.
  • these resins for optical materials have the drawback that they have a low refractive index, a large birefringence and a large dispersing ability, and are inferior in heat resistance and impact resistance.
  • a second object of the present invention is to provide an optical material comprising the curable composition. Disclosure of the invention
  • the curable composition of the present invention has the formula (I):
  • the tetrakis (7-mercapto-2,5-dithiaheptyl) methane used in the present invention is prepared, for example, by the method described in JP-A-9-263575. _
  • the tetrakis- (7-mercapto-2,5-dithiaheptyl) methane is, for example, bis- (2-mercaptoethyl) sulfite and pentaerythrityltetrabromide such as pentaerythrityltetrabromide.
  • a base such as sodium hydroxide and the like
  • the reaction of bis- (2-mercaptoethyl) sulphite and phenol erythrityl tetrahalide can be carried out by mixing both and stirring the mixture under heating while adding the base.
  • the reaction temperature at this time is usually preferably set to 30 to 120 ° C.
  • the ratio of bis (2-mercaptoethyl) sulfite to pentaerythrityl tetrahalide is at least 4 times the molar ratio of bis- (2-mercaptoethyl) sulfite to pentaerythrityl tetrahalide. Is preferably set, and more preferably 4 to 50 times the molar amount.
  • the amount of the base used is usually preferably set to 4 to 6 times the molar amount of erythrityl tetrahalide.
  • the amount of the catalyst used is preferably set to 0.01 to 0.1 times the molar amount of erythrityl tetrahalide.
  • the above-mentioned 2,3-bis [(2-mercaptoethyl) thioethylthio] 111 propanthiol can be produced by the method described in Japanese Patent Application Laid-Open No. 9-287672. That is, the 2,3-bis [(2-mercaptoethyl) thioethylthio] 1-1-propanethiol is, for example, ephalohydrin or 1,3-dihalogeno-1-propanol and 2-[(2-mercaptoethyl) 1,3-bis [(2-hydroxyethyl) thioethylthio] —2-propanol was produced by reacting ethanol with ethanol in the presence of a base, and the resulting 1,3-bis [(2-hydroxy [Ethyl) thioethylthio] A reaction product is obtained by reacting 12-propanol with thiourea in the presence of a mineral acid.
  • the content of the mercapto compound in the curable composition of the present invention is 5% by weight or more, preferably 10% by weight or more, from the viewpoint of increasing the refractive index of a cured product obtained by using the curable composition of the present invention. From the viewpoint of enhancing the polymerizability of the curable composition of the present invention, that is, the curing reaction, the content is 90% by weight or less, preferably 80% by weight or less, and more preferably 75% by weight or less.
  • Representative examples of the compound copolymerizable with the mercapto compound include, for example,
  • each compound may be used alone or in combination of two or more.
  • the compound copolymerizable with the mercapto compound is selected from the group consisting of a polyisocyanate compound, a polyisothiocyanate compound, and an isothiocyanate compound having an isocyanate group. At least one selected may be used.
  • polyisocyanate compound examples include, for example, aliphatic polyisocyanate, alicyclic polyisocyanate, aromatic polyisocyanate, and sulfur-containing polyisocyanate. These polyisocyanate compounds can be used alone or in combination of two or more.
  • aliphatic polyisocyanate examples include, for example, ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, and hexane.
  • examples include samethylene diisocyanate, xylylene diisocyanate, bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, bis (isocyanatobutyl) benzene, and bis (isocyanatomethyl) naphthalene.
  • hexamethylene diisocyanate, xylylene diisocyanate and bis (isocyanatoethyl) benzene, particularly xylylene diisocyanate can be suitably used in the present invention.
  • alicyclic polyisocyanates include, for example, isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexane Xylmethane diisocyanate, 2,2'-dimethyldicyclohexylmethane diisocyanate, dicyclohexyldimethylmethane diisocyanate, and the like.
  • isophorone diisocyanate, cyclohexane diisocyanate and bis (isocyanatomethyl) cyclohexane can be suitably used in the present invention.
  • aromatic polyisocyanates include, for example, tolylene diisocyanate, phenylene diisocyanate, dimethyl phenylene diisocyanate, ethyl phenylene diisocyanate, Zentri isocyanate, trimethylbenzene triisocyanate, naphthalene diisocyanate, biphenyl diisocyanate, 4,4 'diphenylmethane diisocyanate, toluidine diisocyanate and the like.
  • tolylene diisocyanate can be suitably used in the present invention.
  • sulfur-containing polyisocyanate examples include, for example, thiogetyl diisocyanate, dithiogetyl diisocyanate, thiodipropyl diisocyanate, dithiodibutyl pill diisocyanate, diphenyl sulfide 4,4 'diisocyanate, diphenyl sulphide 2,4'-diisocyanate, bis (4 —Isocyanatomethylbenzene) sulfide, 1,4-dithiane-1,2,5-diisocyanate, diphenyldisulfide-1,4,4′-diisocyanate.
  • diphenyl sulfide-1,4,4'-diisocyanate can be suitably used in the present invention.
  • polyisothiocyanate compound examples include, for example, aliphatic or alicyclic polyisothiocyanate, aromatic polyisocyanate, and sulfur-containing polyisothiocyanate.
  • aliphatic or cycloaliphatic polyisothiocyanate include, for example, 1,2-dithithiocyanatopropane, 1,3-diisothiocyanatopropane, 1,4-diisothiocyanatobutane, p-phenyl Examples thereof include di-diisopropylidene diisothiocyanate and cyclohexanediisothiocyanate.
  • aromatic polyisocyanates include, for example, 1,2-diisothiocyanatobenzene, 1,3-diisothiocyanatobenzene, 1,4-diisothiocyanatobenzene, 2,4-diisothiocyanate Examples include natotoluene, 2,5-diisothiocyanate-m-xylene, 4,4'-diisothiocyanato 1,1'-biphenyl, 1, -methylenebis (4-isothiocyanato-benzene), and the like. Among them, 1,2-diisothiocyanatobenzene, 1,3-diisothiocyanatobenzene and 1,4-diisothiocyanatobenzene can be suitably used in the present invention.
  • sulfur-containing polyisothiocyanates include, for example, Tiobis (2-dithiocyanatoethane), dithiobis (2-isothiocyanatoethane), thiopis (3-itithiocyanatopropane), and Tiobis (4-isothiocyanatobenzene) and sulfonylbis (4-isothiocyanatobenzene).
  • isocyanate compound having an isocyanate group examples include, for example, aliphatic or alicyclic compounds, aromatic compounds, and sulfur-containing compounds. .
  • Representative examples of the aliphatic or alicyclic compounds include, for example, 1-isocyanato-to- 3-isothiocyanato-propane, 1-isocyanato-to-6-isothiocyanato-to-hexane, 1-isocyanato-to- 4-itthocyanato-to-cyclo Hexane and the like.
  • aromatic compound examples include, for example, 1-isocyanato- 4-isothiocyanato-benzene, 4-methyl-3-isocyanato-to 1-isothiocyanato-benzene, and the like.
  • sulfur-containing compound examples include, for example, 4-isocyanato-to 4'-isothiocyanato-todiphenyl sulfide.
  • a monomer having a polymerizable unsaturated bond can be used as the compound copolymerizable with the mercapto compound.
  • the monomer having a polymerizable unsaturated bond examples include, for example, an aromatic vinyl compound, an alicyclic vinyl compound, (meth) acrylic acid, a monofunctional (meth) atalylic acid derivative, a polyfunctional (meth) And acrylic acid derivatives.
  • (meth) acryl means both “acryl” and “methacryl” (hereinafter the same).
  • aromatic vinyl compound examples include, for example, styrene, permethylstyrene, vinyltoluene, chlorostyrene, bromostyrene, chloromethylstyrene, methoxystyrene, butylthiostyrene, divinylbenzene, and the like.
  • styrene and divinylbenzene can be suitably used in the present invention.
  • alicyclic vinyl compound examples include, for example, cyclohexene, 4-vinylcyclohexene, 1,5-cyclooctadiene, 5-vinylbicyclo [2,2, _
  • monofunctional (meth) acrylic acid derivatives include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, dodecyl (meth) acrylate, octadecyl (meth) ) Acrylate, cyclohexyl (meth) acrylate, methylcyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, vol (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, Phenyl (meth) acrylate, benzyl (meth) acrylate, 1-naphthyl (meth) acrylate, black phenyl (meth) acrylate, bromophenyl (meth) acrylate, tribromof Sulfony
  • Examples include (meth) acrylate, polyethylene glycol (meth) acrylate, N, N-dimethyl (meth) acrylamide, and N, N-getyl (meth) acrylamide. Among them, methyl (meth) acrylate, cyclohexyl (meth) acrylate and phenyl (meth) acrylate can be suitably used in the present invention.
  • polyfunctional (meth) acrylic acid derivatives include, for example, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol diacrylate.
  • ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate and bis (meth) acrylate (4-Methacryloylthiooffenyl) sulfide can be suitably used in the present invention.
  • an epoxy compound can be used as a compound copolymerizable with a mercapto compound.
  • the epoxy compound examples include a monomer having an epoxy group and an oligomer having an epoxy group. These epoxy compounds can be used alone or in combination of two or more.
  • monomers having an epoxy group and oligomers having an epoxy group include, for example, aryl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, 2-ethylhexyl glycidyl ether, sec-butyl Monofunctional glycidyl ethers such as tert-butyl glycidyl ether, tert-butyl phenyl glycidyl ether, and 2-methyloctyl glycidyl ether; 1,6-hexanediol glycidyl ether, trimethylolpropane triglycidyl ether, neopentyl Glycol diglycidyl ether, glycerol diglycidyl ether, glyceryl triglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, poly
  • Bis (4- (2,3-epoxypropylthio) phenyl) sulfide, glycidyl (meth) acrylate, bisphenol A glycidyl ether, brominated bisphenol A glycidyl ether and 3,4-epoxycyclohexylme Tyl-3,4-epoxycyclohexanecarboxylate can be suitably used in the present invention.
  • an epitio compound can be used as a compound copolymerizable with a mercapto compound.
  • epitio compound examples include, for example, bis [4- (2,3-epipiopropylthio) phenyl] sulfide, bis [4-1 (2,3-epipiopropylthio) -13-methylphenyl] sulfide, bis [ 4-(2,3-Epithiopropylthio) -1,3,5-dimethylphenyl] sulfide and other polyfunctional thioglycidyl thioethers.
  • These epipic compounds can be used alone or in combination of two or more.
  • the content of the compound copolymerizable with the mercapto compound is the balance of the mercapto compound. That is, the content of the compound copolymerizable with the mercapto compound is 95% by weight or less, preferably 90% by weight or less from the viewpoint of increasing the refractive index of a cured product obtained by using the curable composition of the present invention. Further, from the viewpoint of enhancing the polymerizability of the curable composition of the present invention, that is, the curing reaction, it is preferably at least 10% by weight, preferably at least 20% by weight, and more preferably at least 25% by weight. Is done.
  • the curable composition of the present invention contains a mercapto compound and a compound copolymerizable with the mercapto compound, but other copolymerization is possible as long as the object of the present invention is not impaired.
  • a compound may be contained.
  • the curable composition of the present invention may optionally include, for example, a light stabilizer, an ultraviolet absorber, an antioxidant, a coloring inhibitor, a polymerization inhibitor, a release agent, an antifoaming agent, a bluing agent, An additive such as a fluorescent dye may be appropriately compounded.
  • the curable composition of the present invention thus obtained gives a resin having a high refractive index and a low specific gravity, and is excellent in handleability.
  • the curable composition of the present invention can be used for optical materials such as plastic lenses for eyeglasses, Fresnel lenses, lenticure lenses, optical disk substrates, plastic optical fibers, prism sheets for LCDs, light guide plates, and diffusion sheets, paints, and adhesives. It can be suitably used as a raw material for agents, sealing materials and the like. In particular, the curable composition of the present invention can be suitably used for an optical material.
  • the optical material of the present invention is obtained by copolymerizing the curable composition.
  • the curable composition of the present invention may be an optical material that requires transparency. Considering the use, for example, a solution polymerization method and a bulk polymerization method are suitable.
  • the polymerization of the curable composition can be carried out, for example, by heating, irradiation with a light beam such as ultraviolet rays, or the like, if necessary, using a polymerization initiator according to a generally employed method.
  • a light beam such as ultraviolet rays, or the like
  • the curable composition is heated to a temperature of about 60 to 150 ° C. Is heated to effect copolymerization.
  • the copolymerization is carried out using a radical polymerization initiator such as 2,2′-azobis (2,4-dimethylvaleronitrile). be able to.
  • a radical polymerization initiator such as 2,2′-azobis (2,4-dimethylvaleronitrile).
  • the copolymerizable compound of the third embodiment for example, boron trifluoride.getyl ether complex, boron trifluoride.amine complex, aluminum chloride, titanium tetrachloride, -
  • the copolymerization can be carried out using a Lewis acid such as tin chloride, iron chloride (III), zinc chloride and the like; and a cationic polymerization initiator such as an ammonium salt, a sulfonium salt, an oxonium salt and a phosphonium salt.
  • a Lewis acid such as tin chloride, iron chloride (III), zinc chloride and the like
  • a cationic polymerization initiator such as an ammonium salt, a sulfonium salt, an oxonium salt and a phosphonium salt.
  • the polymerization temperature and the polymerization time when the curable composition is polymerized vary depending on the composition of the curable composition, the application, the type of the polymerization initiator used, the amount used, and the like, and cannot be unconditionally specified. .
  • the polymerization temperature may be about 0 to 200 ° C, preferably about 20 to 150 ° C.
  • the polymerization temperature is preferably about 60 to 150 ° C. It is desirable that the polymerization time is about 0.2 to 100 hours, preferably about 1 to 72 hours.
  • the optical material of the present invention was obtained by a method other than the above method as long as the optical material had the same structure as the optical material obtained by the above method, that is, the curable composition used in the present invention as a repeating unit. It may be something.
  • the optical material of the present invention thus obtained has excellent properties such as a high refractive index and a low specific gravity.
  • the optical material of the present invention can be suitably used such as a plastic lens for eyeglasses, a Fresnel lens, a lenticule lens, an optical disk substrate, a plastic optical fiber, a prism sheet for LCD, a light guide plate, and a diffusion sheet.
  • a plastic lens for eyeglasses a Fresnel lens, a lenticule lens, an optical disk substrate, a plastic optical fiber, a prism sheet for LCD, a light guide plate, and a diffusion sheet.
  • the curable composition After sufficiently degassing the curable composition, it is poured into a glass mold having a diameter of 5 cm and a thickness of 3 cm, heated at 60 ° C for 5 hours, and then heated to 100 ° C over 15 hours. The temperature was raised and the temperature was kept at 100 ° C. for 3 hours and then at 120 ° C. for 3 hours, and then the mold was released.
  • the obtained optical material was uniform and colorless and transparent. Each physical property of the obtained optical material was evaluated by the following methods. The results are shown in Table 1.
  • the refractive index and Abbe number at 20 ° C were measured using an Abbe refractometer (manufactured by Adago Co., Ltd., type 4T).
  • the curable composition was sufficiently degassed, poured into a glass mold having a diameter of 5 cm and a thickness of 0.3 cm, heated at 36 ° C for 7 hours, and then heated at 80 ° C for 7 hours. The temperature was raised to 80 ° C for 1 hour, and then the mold was released.
  • the obtained optical material was uniform and colorless and transparent.
  • Each physical property was evaluated in the same manner as in Example 1. The results are shown in Table 1
  • Example 3 -An optical material was prepared in the same manner as in Example 2 except that a curable composition having the composition shown in Table 1 was used, and each physical property was evaluated. The results are shown in Table 1.
  • Example 4
  • Example 5 After sufficiently degassing the curable composition, it was poured into a glass mold having a diameter of 5 cm and a thickness of 0.3 cm, and heated at 50 ° C for 2 hours. The temperature was raised to 100 ° C., kept at 80 ° C. for 5 hours, then raised to 100 ° C. over 3 hours, kept at 100 ° C. for 10 hours, and then demolded. The obtained optical material was uniform and colorless and transparent. Each physical property was evaluated in the same manner as in Example 1. The results are shown in Table 1. Example 5
  • Example 6 After sufficiently degassing the curable composition, it was poured into a glass mold having a diameter of 5 cm and a thickness of 3 cm, heated at 55 ° C for 7 hours, and then heated at 90 ° C for 4 hours. The temperature was raised to 90 ° C. for 2 hours, then raised to 130 ° C. over 1 hour, and kept at 130 ° C. for 1 hour, followed by demolding. The obtained optical material was uniform and colorless and transparent. Each physical property was evaluated in the same manner as in Example 1. The results are shown in Table 1. Example 6
  • a 500 ml four-necked flask equipped with a stirrer, thermometer and condenser was prepared. To this, 360 g (0.45 mol) of a 5% aqueous sodium hydroxide solution was added, and under a nitrogen atmosphere, 2—C (2-mercaptoethyl) thio] ethanol 62.1 g (0.4 (5 mol) was added dropwise to obtain a homogeneous solution.
  • reaction solution was cooled to room temperature, and then 10.9.3 g (1.8 mol) of 28% aqueous ammonia was added at 20 to 40 ° C to make the reaction solution alkaline. Stirred for hours.
  • reaction solution was cooled to room temperature, 250 ml of toluene was added for extraction, and the toluene layer was separated.
  • the toluene layer was washed with 100 ml of a 5% hydrochloric acid aqueous solution, further washed twice with 100 ml of water, and dried by adding 2 Og of magnesium sulfate.
  • the curable composition After sufficiently degassing the curable composition, it was poured into a glass mold having a diameter of 5 cm and a thickness of 0.3 cm. Next, this mold was heated at 60 ° C for 5 hours, heated to 100 ° C over 15 hours, and kept at 100 ° C for 3 hours and then at 120 ° C for 3 hours. After that, the mold was removed to obtain an optical material. The obtained optical material was uniform and colorless and transparent. .
  • Example 8 As physical properties of the obtained optical material, a refractive index, an Abbe number, and a specific gravity were evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • Example 8 As physical properties of the obtained optical material, a refractive index, an Abbe number, and a specific gravity were evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • the curable composition After sufficiently degassing the curable composition, it was poured into a glass mold having a diameter of 5 cm and a thickness of 0.3 cm. After heating at 70 ° C. for 7 hours, the temperature was raised to 80 ° C. over 7 hours, kept at 80 ° C. for 1 hour, and demolded to obtain an optical material.
  • the obtained optical material was uniform and colorless and transparent.
  • An optical material was obtained in the same manner as in Example 7, except that the curable composition having the composition shown in Table 2 was used.
  • the obtained optical material was uniform and colorless and transparent.
  • Example 10 The physical properties of the obtained optical material were evaluated in the same manner as in Example 1. The results are shown in Table 2. Example 10
  • the curable composition having the composition shown in Table 2
  • 0.5 parts by weight of 2-ethyl-4-methylimidazole as a curing accelerator was added and uniformly dissolved.
  • the curable composition was sufficiently degassed, and then poured into a glass mold having a diameter of 5 cm and a thickness of 0.3 cm.
  • the mold was heated at 50 ° C for 2 hours, heated to 80 ° C over 3 hours, kept at 80 ° C for 5 hours, and then heated to 100 ° C over 3 hours. After the temperature was raised and kept at 100 ° C. for 10 hours, it was released from the mold to obtain an optical material.
  • the obtained optical material was uniform and colorless and transparent.
  • An optical material was prepared in the same manner as in Example 7 except that a curable composition having a composition shown in Table 2 was used, and each physical property was evaluated. The results are shown in Table 2.
  • the curable composition of the present invention provides a resin having a high refractive index, a low specific gravity, and excellent handleability.
  • the curable composition of the present invention comprises a plastic lens for spectacles, a Fresnel lens, a lenticule lens, an optical disc substrate, a plastic optical fiber,
  • optical materials such as prism sheets for LCDs, light guide plates and diffusion sheets, paints, adhesives and sealing materials.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

L'invention concerne une composition durcissable comprenant 5 à 90 % en poids d'au moins un composé mercapto choisi dans le groupe consititué de tétrakis(7-mercapto-2,5-dithiaheptyl)méthane représenté par la formule structurelle (I): C(CH2SCH2CH2SCH2CH2SH)4, et de 2,3-bis[(2-mercaptoéthyl)thioéthylthio]-1-propanethiol de la formule structurelle (II), et 10 à 95 % en poids d'un composé copolymérisable avec le composé mercapto. La composition durcissable est capable de former une résine présentant une excellente maniabilité, un indice de réfraction élevé et un faible poids volumique et par conséquent elle est apte à l'utilisation ent tant que matériau optique ou analogue.
PCT/JP1998/000643 1997-02-19 1998-02-16 Composition durcissable et materiau optique prepare a partir de celle-ci WO1998037114A1 (fr)

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AU58817/98A AU5881798A (en) 1997-02-19 1998-02-16 Curable composition and optical material prepared therefrom

Applications Claiming Priority (4)

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JP9052318A JPH10231343A (ja) 1997-02-19 1997-02-19 硬化性組成物およびそれからなる光学材料
JP05231997A JP3872155B2 (ja) 1997-02-19 1997-02-19 硬化性組成物およびそれからなる光学材料
JP9/52319 1997-02-19
JP9/52318 1997-02-19

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001040175A1 (fr) * 1999-12-02 2001-06-07 Tokuyama Corporation Procede de production de composes sulfures
AU744901B2 (en) * 2000-03-15 2002-03-07 Hoya Corporation Plastic lenses for spectacles
US9584604B2 (en) 1999-08-31 2017-02-28 Nokia Technologies Oy Utilization of subscriber data in a telecommunication system
CN110499218A (zh) * 2019-09-17 2019-11-26 黄河三角洲京博化工研究院有限公司 一种高效环保型酸性皂洗剂及其制备方法

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AU744901B2 (en) * 2000-03-15 2002-03-07 Hoya Corporation Plastic lenses for spectacles
CN110499218A (zh) * 2019-09-17 2019-11-26 黄河三角洲京博化工研究院有限公司 一种高效环保型酸性皂洗剂及其制备方法

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