WO2022113955A1 - Procédé de production de matériau optique, composition polymérisable pour matériau optique, système de production de matériau optique, procédé de production d'élément optique, film de production d'élément optique, moule de production d'élément optique et produit durci - Google Patents

Procédé de production de matériau optique, composition polymérisable pour matériau optique, système de production de matériau optique, procédé de production d'élément optique, film de production d'élément optique, moule de production d'élément optique et produit durci Download PDF

Info

Publication number
WO2022113955A1
WO2022113955A1 PCT/JP2021/042848 JP2021042848W WO2022113955A1 WO 2022113955 A1 WO2022113955 A1 WO 2022113955A1 JP 2021042848 W JP2021042848 W JP 2021042848W WO 2022113955 A1 WO2022113955 A1 WO 2022113955A1
Authority
WO
WIPO (PCT)
Prior art keywords
optical
polymerizable composition
optical material
mass
optical materials
Prior art date
Application number
PCT/JP2021/042848
Other languages
English (en)
Japanese (ja)
Inventor
勇輔 松井
幸治 末杉
伸介 伊藤
忠史 鳥居
Original Assignee
三井化学株式会社
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
Application filed by 三井化学株式会社 filed Critical 三井化学株式会社
Priority to CN202180078034.0A priority Critical patent/CN116529048A/zh
Priority to JP2022565339A priority patent/JPWO2022113955A1/ja
Publication of WO2022113955A1 publication Critical patent/WO2022113955A1/fr

Links

Images

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
    • B29C39/12—Making multilayered or multicoloured articles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/22—Component parts, details or accessories; Auxiliary operations
    • B29C39/24—Feeding the material into the mould
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/22—Component parts, details or accessories; Auxiliary operations
    • B29C39/26—Moulds or cores
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/22—Component parts, details or accessories; Auxiliary operations
    • B29C39/44—Measuring, controlling or regulating
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2011/00—Optical elements, e.g. lenses, prisms

Definitions

  • the present disclosure relates to a method for manufacturing an optical material, a polymerizable composition for an optical material, an optical material manufacturing system, a method for manufacturing an optical member, a film for manufacturing an optical member, a mold for manufacturing an optical member, and a cured product.
  • a casting polymerization method in which a polymerizable composition containing a monomer is injected into a mold and cured by heating can be mentioned.
  • a polymerizable composition is prepared and degassed, then the polymerizable composition is injected into a mold (mold), and after heat curing (polymerization reaction), the product is taken out from the mold (demolding). ), Annealing is performed to obtain an optical material (for example, a lens, a semi-finished blank, etc.).
  • Patent Document 1 it is described that the mold into which the polymerizable composition is injected is gradually heated to 10 ° C to 120 ° C and polymerized in 20 hours to obtain a molded product.
  • the mold in which the polymerizable composition is injected is gradually heated from 25 ° C. over 16 hours to 120 ° C. and heated at 120 ° C. for 4 hours to form a molded product. It is stated that it was obtained.
  • Patent Document 1 International Publication No. 2014/027427
  • Patent Document 2 International Publication No. 2014/133111
  • the problem to be solved by one embodiment of the first embodiment of the present disclosure is a method for manufacturing an optical material capable of suppressing pulse in the obtained optical material and shortening the manufacturing time of the optical material, described above. It is an object of the present invention to provide a polymerizable composition for an optical material used in a method for producing an optical material.
  • An object to be solved by one embodiment of the second embodiment of the present disclosure is to provide a method for manufacturing an optical material and an optical material manufacturing system capable of suppressing a U-shaped pulse in the obtained optical material. Is.
  • the problem to be solved by one embodiment of the third embodiment of the present disclosure is a method for manufacturing an optical member capable of manufacturing an optical member having a smooth outer peripheral surface, a film for manufacturing the optical member, and a mold for manufacturing the optical member.
  • the problem to be solved by one embodiment of the fourth embodiment of the present disclosure is a method for manufacturing an optical member capable of manufacturing an optical member having a smooth outer peripheral surface, a film for manufacturing the optical member, and a mold for manufacturing the optical member. And to provide a cured product.
  • Specific means for solving the above-mentioned problems include the following aspects.
  • ⁇ 1> A method for producing an optical material using a total of 100 parts by mass of two or more different monomers for optical materials and a polymerization catalyst of 0.010 parts by mass to 2.0 parts by mass as raw materials.
  • a part of the two or more different monomers for optical materials and at least a part of the polymerization catalyst are mixed, and at least a part of the two or more different monomers for optical materials is polymerized to prepolymerize.
  • a curing step of obtaining an optical material which is a cured product of the polymerizable composition for an optical material by curing two or more different monomers for an optical material in the polymerizable composition for an optical material is included.
  • the method for producing an optical material according to ⁇ 2> which is a step of obtaining a mixture containing the prepolymer by polymerizing at least a part thereof to obtain a prepolymer.
  • a part of the two or more different optical material monomers is all of one optical material monomer among the two or more different optical material monomers, and the one optical material monomer.
  • the method for producing an optical material according to ⁇ 3> which comprises a part of a monomer for an optical material other than the above.
  • ⁇ 5> In the prepolymerization step, a part of the two or more kinds of monomers for different optical materials and a part of the polymerization catalyst are mixed, and a part of the two or more kinds of monomers for different optical materials.
  • the method for producing an optical material according to ⁇ 2> which is a step of obtaining a polymerizable composition for an optical material containing the above-mentioned different monomers for an optical material, the prepolymer, and the polymerization catalyst.
  • the two or more different monomers for optical materials contain an isocyanate compound (A).
  • a part of the two or more kinds of monomers for different optical materials contains a part of the isocyanate compound (A), and the balance of the two or more kinds of monomers for different optical materials contains the balance of the isocyanate compound (A) ⁇ 5>.
  • the method for manufacturing an optical material according to. ⁇ 7> The method for producing an optical material according to ⁇ 5> or ⁇ 6>, wherein a part of the polymerization catalyst is 5 parts by mass to 80 parts by mass in 100 parts by mass of the polymerization catalyst.
  • a part of the two or more kinds of monomers for different optical materials is 5 parts by mass to 95 parts by mass out of 100 parts by mass of the two or more kinds of monomers for different optical materials ⁇ 2> to ⁇ 7.
  • the method for manufacturing an optical material according to any one of. ⁇ 9> After the prepolymerization step and before the step of producing the polymerizable composition for an optical material, the viscosity measured with a B-type viscosity meter of the mixture containing the prepolymer under the conditions of 25 ° C. and 60 rpm is measured.
  • the remnants of the two or more kinds of monomers for different optical materials and the remnants of the polymerization catalyst are mixed, and at least a part of the remnants of the two or more kinds of monomers for different optical materials is polymerized.
  • a polymerizable composition for an optical material containing the prepolymer, the second prepolymer, and the polymerization catalyst by adding the mixture containing the second prepolymer to the mixture containing the prepolymer.
  • a liquid feeding step of feeding the polymerizable composition for optical materials to a casting mold after the step of manufacturing the polymerizable composition for optical materials and before the curing step is further included.
  • the liquid feeding step is one of ⁇ 2> to ⁇ 10>, which is a step of feeding the polymerizable composition for an optical material to a casting mold while remixing it in a static mixer.
  • the method for manufacturing an optical material according to the description. ⁇ 12> The curing step includes any one of ⁇ 2> to ⁇ 11> including a step of curing the polymerizable composition for optical materials by allowing the polymerizable composition for optical materials to stand still.
  • the method for manufacturing an optical material according to the description. ⁇ 13> The curing step includes a step of curing the polymerizable composition for an optical material by allowing the polymerizable composition for an optical material to stand in a closed system space ⁇ 2> to ⁇ 12>.
  • the curing step includes a step of curing the polymerizable composition for an optical material by allowing the polymerizable composition for an optical material to stand without being heated from the outside ⁇ 2> to ⁇ 13>.
  • the curing step of ⁇ 2> to ⁇ 14> includes a step of curing the polymerizable composition for an optical material by allowing the polymerizable composition for an optical material to stand for 2 to 10 hours. The method for manufacturing an optical material according to any one of them.
  • the two or more different monomers for optical materials are an isocyanate compound (A), a polythiol compound having two or more mercapto groups, and a hydroxythiol having one or more mercapto groups and one or more hydroxyl groups.
  • ⁇ 17> The method for producing an optical material according to ⁇ 16>, wherein the isocyanate compound (A) contains at least one of an alicyclic isocyanate compound and an aromatic isocyanate compound.
  • the polymerization catalyst is one of ⁇ 1> to ⁇ 17>, which comprises at least one selected from the group consisting of a basic catalyst having a pKa value of 4 to 8 and an organometallic catalyst.
  • ⁇ 19> The method for producing an optical material according to any one of ⁇ 1> to ⁇ 18>, wherein the polymerization catalyst contains at least one selected from the group consisting of an amine-based catalyst and an organic tin-based catalyst.
  • the polymerization catalyst is 3,5-lutidine, 2,4,6-cholidine, triethylenediamine, N, N-dimethylethanolamine, triethylamine, N-ethylmorpholine, dibutyltin dichloride, dimethyltin dichloride, dibutyltin dilaurate and
  • the content of the polymerization catalyst is 0.010 parts by mass to 2.0 parts by mass with respect to 100 parts by mass in total of the two or more different monomers for optical materials and the prepolymer. thing.
  • a curing step of curing the polymerizable composition for optical materials by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold.
  • Viscosity Va measured at 25 ° C. and 60 rpm with a B-type viscometer of the first raw material composition, and 2.
  • the absolute value V of the difference between the viscosity Vb measured under the condition of 25 ° C. and 60 rpm with a B-type viscometer of the second raw material composition is in the range of 20 mPa ⁇ s to 1500 mPa ⁇ s. Manufacturing method of optical material.
  • the second raw material composition is a polythiol compound having two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, and a polyol compound containing two or more hydroxyl groups.
  • the method for producing an optical material according to any one of ⁇ 23> to ⁇ 26> which comprises at least one active hydrogen compound selected from the group consisting of amine compounds.
  • ⁇ 28> Any of ⁇ 23> to ⁇ 27> in which the viscosity measured at 25 ° C. and 60 rpm with a B-type viscometer of the polymerizable composition for optical materials in the casting step is 10 mPa ⁇ s to 1000 mPa ⁇ s.
  • ⁇ 29> The method for producing an optical material according to any one of ⁇ 23> to ⁇ 28>, wherein the polymerization catalyst satisfies the following condition 1.
  • the polymerization catalyst is any one of ⁇ 23> to ⁇ 29>, which comprises at least one selected from the group consisting of a basic catalyst having a pKa value of 4 to 8 and an organometallic catalyst. The method for manufacturing an optical material according to.
  • a system for producing an optical material using a polymerizable composition for an optical material containing two or more different monomers for an optical material and a polymerization catalyst A shearing portion that applies a shearing force to the first raw material composition and the second raw material composition to produce the polymerizable composition for an optical material, and a shearing portion.
  • a stirring unit that applies stirring force to the polymerizable composition for optical materials, and a stirring unit.
  • a cured portion that cures the polymerizable composition for optical materials by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold.
  • the fixed quantity liquid delivery unit and Optical material manufacturing system including. ⁇ 32> Further, the shearing force of the sheared portion, the temperature of the polymerizable composition for optical material in the stirring portion, and the optical quality of the cured product obtained by curing the polymerizable composition for optical material in the cured portion.
  • the stirring unit according to at least one condition selected from the group consisting of feature quantities correlating with the viscosity measured at 25 ° C. and 60 rpm with a B-type viscosity meter of the polymerizable composition for optical materials.
  • the optical material manufacturing system according to ⁇ 31> comprising a viscosity control unit for controlling the viscosity measured under the condition of 25 ° C.
  • the film comprises an injection step of injecting a polymerizable composition and a curing step of curing the polymerizable composition injected into the space to obtain a cured product, and the film is attached to glass and heat-resistant at 85 ° C.
  • a film that completely peels off from the glass when an exponential test is performed, and the film is a method for manufacturing an optical member having a thermal deformation temperature of 70 ° C. or higher.
  • ⁇ 36> The method for manufacturing an optical member according to ⁇ 34> or ⁇ 35>, wherein the curing time is 10 hours or less in the curing step.
  • ⁇ 37> The method for manufacturing an optical member according to any one of ⁇ 34> to ⁇ 36>, wherein the film is subjected to a glass ball tack test at 80 ° C. and the moving distance of the glass balls is 200 mm or less. ..
  • the polymerizable composition comprises two or more kinds of monomers for different optical materials and a polymerization catalyst, and the content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more kinds of monomers for different optical materials. Is 0.010 part by mass to 2.0 parts by mass, and the viscosity measured with a B-type viscometer at 25 ° C.
  • the polymerizable composition is a polymer of two or more kinds of monomers for different optical materials, a polymerization catalyst, and a prepolymer containing a polymerizable functional group, which is a polymer of the two or more kinds of monomers for different optical materials.
  • the two or more different monomers for optical materials are polythiol compounds containing two or more mercapto groups, hydroxythiol compounds containing one or more mercapto groups and one or more hydroxyl groups, and two or more hydroxyl groups.
  • the method for producing an optical member according to ⁇ 39> or ⁇ 40> which comprises at least one active hydrogen compound selected from the group consisting of a polyol compound containing a thiol compound and an amine compound.
  • ⁇ 42> The method for manufacturing an optical member according to any one of ⁇ 39> to ⁇ 41>, wherein the polymerization catalyst satisfies the following condition 1. [Condition 1] -Ea / R is -7100 or more and -2900 or less.
  • a film for manufacturing an optical member that includes at least a base material layer and an adhesive layer and is completely peeled off from the glass when the film is attached to glass and subjected to a heat resistance index test at 85 ° C. ⁇ 45>
  • a film is attached to the outer peripheral surfaces of two molded substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two molded substrates and the film, and a polymerizable composition is formed in the space.
  • the outer peripheral surface of the cured product is a mirror surface, and the shape between the intersection of one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface is a substantially straight line.
  • ⁇ 47> The cured product according to ⁇ 46>, wherein the intersection of the one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface include a protrusion substantially parallel to the outer peripheral surface.
  • ⁇ 48> The cured product according to ⁇ 46> or ⁇ 47>, wherein the amine content measured by gas chromatograph mass spectrometry is 0.03% by mass or more and 2.5% by mass or less.
  • ⁇ 49> The cured product according to any one of ⁇ 46> to ⁇ 48>, which contains a thiourethane resin.
  • the film comprises an injection step of injecting a polymerizable composition and a curing step of curing the polymerizable composition injected into the space to obtain a cured product, and the film is attached to glass and heat-resistant at 85 ° C.
  • ⁇ 52> The method for manufacturing an optical member according to ⁇ 50> or ⁇ 51>, wherein the curing time is 10 hours or less in the curing step.
  • ⁇ 53> The method for manufacturing an optical member according to any one of ⁇ 50> to ⁇ 52>, wherein the film is subjected to a glass ball tack test at 80 ° C. and the moving distance of the glass balls is 200 mm or less. ..
  • the polymerizable composition injected into the space is allowed to stand in a closed space to cure the polymerizable composition to any one of ⁇ 50> to ⁇ 53>.
  • the polymerizable composition comprises two or more kinds of monomers for different optical materials and a polymerization catalyst, and the content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more kinds of monomers for different optical materials. 1 The method for manufacturing an optical member according to the above.
  • the polymerizable composition is a polymer of two or more kinds of monomers for different optical materials, a polymerization catalyst, and a prepolymer containing a polymerizable functional group, which is a polymer of the two or more kinds of monomers for different optical materials.
  • the two or more different monomers for optical materials are a polythiol compound containing two or more mercapto groups, a hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups, and two or more hydroxyl groups.
  • the method for producing an optical member according to ⁇ 55> or ⁇ 56> which comprises at least one active hydrogen compound selected from the group consisting of a polyol compound containing a thiol compound and an amine compound.
  • ⁇ 58> The method for manufacturing an optical member according to any one of ⁇ 55> to ⁇ 57>, wherein the polymerization catalyst satisfies the following condition 1.
  • -Ea / R is -7100 or more and -2900 or less.
  • Ea is the activation energy calculated by the Arrhenius plot from the reaction rate constants of the two or more different optical material monomers at two or more different temperatures
  • R is the gas constant (8.314 J / mol / K).
  • ⁇ 59> The method for producing an optical member according to any one of ⁇ 55> to ⁇ 58>, wherein the polymerization catalyst contains at least one selected from the group consisting of an amine-based catalyst and an organic tin-based catalyst.
  • a film is attached to the outer peripheral surfaces of two mold substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two mold substrates and the film, and a polymerizable composition is formed in the space. Is a film for manufacturing an optical member for manufacturing an optical member by arranging the film and curing the polymerizable composition in 10 hours or less to obtain a cured product.
  • optical members including at least a base material layer and an adhesive layer, and having a heat resistance index of 1 mm or more (except when completely peeling off from the glass) when attached to glass and subjected to a heat resistance index test at 85 ° C.
  • Film for. ⁇ 61> A film is attached to the outer peripheral surfaces of two molded substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two molded substrates and the film, and a polymerizable composition is formed in the space.
  • a mold for manufacturing an optical member by arranging and curing the polymerizable composition to obtain a cured product, wherein the main surface of the mold has a substantially diameter of 60 cm to 80 cm. ..
  • ⁇ 62> A cured product of two or more different optical monomers having no vein having a length of 1.0 mm or more within a radius of 15 mm from the center of the cured product.
  • the outer peripheral surface of the cured product is a mirror surface, and the shape between the intersection of one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface is a concave curve.
  • ⁇ 63> The cured product according to ⁇ 62>, wherein the intersection of the one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface include a protrusion substantially parallel to the outer peripheral surface.
  • ⁇ 64> The cured product according to ⁇ 62> or ⁇ 63>, wherein the amine content measured by gas chromatograph mass spectrometry is 0.03% by mass or more and 2.5% by mass or less.
  • ⁇ 65> The cured product according to any one of ⁇ 62> to ⁇ 64>, which contains a thiourethane resin.
  • a method for producing an optical material capable of suppressing pulse in the obtained optical material and shortening the production time of the optical material, the production of the above-mentioned optical material It is possible to provide a polymerizable composition for an optical material used in the method.
  • a method for manufacturing an optical material and an optical material manufacturing system capable of suppressing a U-shaped pulse in the obtained optical material According to one embodiment of the third embodiment of the present disclosure, a method for manufacturing an optical member capable of manufacturing an optical member having a smooth outer peripheral surface, a film for manufacturing the optical member, a mold for manufacturing the optical member, and a cured product are provided. Can be provided.
  • a method for manufacturing an optical member capable of manufacturing an optical member having a smooth outer peripheral surface, a film for manufacturing the optical member, a mold for manufacturing the optical member, and a cured product are provided. Can be provided.
  • the numerical range represented by using “-” means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
  • the amount of each component in the composition is the total amount of the plurality of substances present in the composition, unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition. means.
  • the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in another stepwise description. ..
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • the term "process” is included in this term not only as an independent process but also as long as the intended purpose of the process is achieved even if it cannot be clearly distinguished from other processes. ..
  • the present disclosure includes the following first to fourth embodiments. Each embodiment will be described in detail.
  • the method for producing an optical material according to the first embodiment uses, in total, 100 parts by mass of two or more different monomers for optical materials and 0.010 parts by mass to 2.0 parts by mass of a polymerization catalyst as raw materials.
  • a method for producing an optical material which is a preparatory step for preparing a total of 100 parts by mass of two or more different monomers for different optical materials and a polymerization catalyst of 0.010 parts by mass to 2.0 parts by mass.
  • a part of the two or more different monomers for optical materials and at least a part of the polymerization catalyst are mixed, and at least a part of the two or more different monomers for optical materials is polymerized to pre-polymerize. It comprises a prepolymerization step of obtaining a mixture containing the prepolymer by obtaining the polymer.
  • the method for producing an optical material according to the first embodiment includes a preparation step and a prepolymerization step, whereby the pulse in the obtained optical material can be suppressed and the production time of the optical material can be shortened.
  • the refractive index refers to a state in which the refractive index of a specific portion is different from the normal refractive index of the surroundings. Pulsation in optical materials is one of the factors that deteriorate quality.
  • the method for producing an optical material in addition to the preparation step and the prepolymerization step described above, at least the balance of the two or more different monomers for the optical material is added to the mixture containing the prepolymer.
  • a polymerizable composition for an optical material containing the two or more different monomers for an optical material, the prepolymer, and the polymerization catalyst.
  • the method for producing an optical material according to the first embodiment further includes, in addition to a preparation step and a prepolymerization step, a step of manufacturing a polymerizable composition for an optical material and a curing step, so that a pulse in the obtained optical material can be obtained. It is possible to suppress the process better and to shorten the manufacturing time of the optical material better.
  • the content of the polymerization catalyst with respect to a total of 100 parts by mass of two or more different monomers for optical materials is 0.010 parts by mass to 2. It is 0 parts by mass.
  • the content of this polymerization catalyst is large as compared with the conventional method for producing an optical material.
  • the above reaction heat can be used to accelerate the polymerization reaction of the monomer for optical material in the polymerizable composition for optical material, a high-quality optical material whose pulse is suppressed in a shorter time than before can be obtained. Obtainable.
  • the polymerizable composition for an optical material is heated to generate a polymerization reaction.
  • the polymerizable composition for an optical material is heated. Is not always necessary.
  • the method for producing an optical material according to the first embodiment includes a preparation step, a prepolymerization step, a polymerizable composition manufacturing step for an optical material, and a curing step, whereby a molding in which a polymerization reaction is carried out is performed. It is possible to suppress the convection in the inside, and it is possible to suppress the generation of pulsation in the obtained cured product.
  • the prepolymer in the method for producing an optical material according to the first embodiment can maintain good storage stability. For example, even when the prepolymer is stored for a certain period of time, the curing of the prepolymer can be suppressed. That is, a long-term pot life can be secured.
  • the method for producing an optical material according to the first embodiment is a preparatory step for preparing a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 parts by mass to 2.0 parts by mass of a polymerization catalyst.
  • the types of two or more different types of monomers for optical materials may be, for example, five or less, or three or less.
  • Examples of the monomer for optical materials include isocyanate compounds, polythiol compounds having two or more mercapto groups, hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups, and polyol compounds having two or more hydroxyl groups. Examples thereof include amine compounds.
  • Two or more different monomers for optical materials are an isocyanate compound (A), a polythiol compound having two or more mercapto groups, and a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups. It is preferable to contain the above-mentioned polyol compound having a hydroxyl group and the active hydrogen compound (B) which is at least one selected from the group consisting of amine compounds.
  • isocyanate compound (A) examples include an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound, and a heterocyclic isocyanate compound, and one type or a mixture of two or more types is used. These isocyanate compounds may include dimers, trimers and prepolymers. Examples of these isocyanate compounds include the compounds exemplified in International Publication No. 2011/0555540.
  • the alicyclic isocyanate compound refers to an isocyanate compound containing an alicyclic structure and may contain a structure other than the alicyclic structure such as a heterocyclic structure.
  • the aromatic isocyanate compound refers to an isocyanate compound containing an aromatic structure and which may contain any one of an aliphatic structure, an alicyclic structure and a heterocyclic structure, or a combination thereof.
  • the heterocyclic isocyanate compound refers to an isocyanate compound containing a heterocyclic structure and not containing an alicyclic structure and an aromatic structure.
  • Aliphatic isocyanate compounds refer to isocyanate compounds that do not contain aromatic, alicyclic and heterocyclic structures.
  • the isocyanate compound (A) preferably contains at least one selected from an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound and a heterocyclic isocyanate compound, and preferably contains an alicyclic isocyanate compound and an aromatic isocyanate compound. It is more preferable to include at least one of the above.
  • the isocyanate compound (A) is 2,5-bis (isocyanatomethyl) bicyclo- [2. 2.1] -Heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -Heptane, m-xylylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate , Dicyclohexylmethane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate.
  • m-xylylene diisocyanate 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, and 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane It is more preferable to include at least one selected from.
  • active hydrogen compound examples include polythiol compounds having two or more mercapto groups, hydroxythiol compounds having one or more mercapto groups and one or more hydroxyl groups, polyol compounds having two or more hydroxyl groups, amine compounds and the like. Can be mentioned.
  • an oligomer of the active hydrogen compound or a halogen-substituted product of the active hydrogen compound for example, a chlorine-substituted product, a bromine-substituted product, etc.
  • the active hydrogen compound may be used alone or in combination of two or more.
  • the polythiol compound is a compound having two or more mercapto groups, and examples thereof include the compounds exemplified in International Publication No. 2016/125736.
  • the polythiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiane octane, 5 , 7-Dimercaptomethyl-1,11-Dimercapto-3,6,9-Trithiane undecane, 4,7-Dimercaptomethyl-1,11-Dimercapto-3,6,9-Trithiane undecane, 4,8 -Dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, pentaerythritol tetrakis (3-mercaptopropionate), bis (mercaptoethyl) sul
  • Hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups examples include 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerinbis (mercaptoacetate), 4-mercaptophenol, 2,3-dimercapto-1-propanol, and pentaerythritol.
  • Tris (3-mercaptopropionate), pentaerythritol tris (thioglycolate) and the like can be mentioned, but are not limited to these exemplified compounds.
  • polyol compound having two or more hydroxyl groups examples include one or more aliphatic or alicyclic alcohols. Specifically, a linear or branched fatty alcohol, an alicyclic alcohol, or an alcohol obtained by adding at least one selected from the group consisting of ethylene oxide, propylene oxide, and ⁇ -caprolactone to these alcohols. And so on. More specifically, the compounds exemplified in International Publication No. 2016/125736 can be mentioned.
  • the polyol compound is preferably ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1 , 3-Cyclohexanediol, 1,4-Cyclohexanediol is at least one selected from.
  • amine compound examples include ethylenediamine, 1,2- or 1,3-diaminopropane, 1,2-, 1,3- or 1,4-diaminobutane, 1,5-diaminopentane, and 1,6-diaminohexane.
  • the active hydrogen compound (B) preferably contains a polythiol compound having two or more mercapto groups.
  • the content of the polythiol compound having two or more mercapto groups is preferably 60% by mass or more, more preferably 70% by mass or more, and more preferably 80% by mass, based on the total mass of the active hydrogen compound (B). It is more preferably mass% or more.
  • the total content of the active hydrogen compound (B) in the first embodiment is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and pentaerythritol tetrakis (3-mercaptopropionate). However, it is preferably 60% by mass or more, more preferably 70% by mass or more, and further preferably 80% by mass or more with respect to the total mass of the active hydrogen compound (B).
  • the molar ratio of the sum of the hydroxyl group (OH group) and the mercapto group (SH group) in the active hydrogen compound to the isocyanate group (NCO group) in the isocyanate compound (A) (NCO group / (OH group + SH group) )) Is preferably 0.8 to 1.2, more preferably 0.85 to 1.15, and even more preferably 0.9 to 1.1.
  • the polymerization catalyst in the preparatory step is used, at least in part, to obtain a prepolymer in the prepolymerization step described later.
  • the polymerization catalyst is not particularly limited, and for example, a basic catalyst, an organic metal catalyst, a zinc carbamic acid salt, an ammonium salt, a sulfonic acid, or the like can be used.
  • the above-mentioned polymerization catalyst may be used alone or in combination of two or more as appropriate.
  • Base catalyst examples include an amine-based catalyst and an imidazole-based catalyst.
  • tertiary amine-based catalysts such as triethylenediamine, N, N-dimethylethanolamine, triethylamine, and N-ethylmorpholin, 2-methylpyrazine, pyridine, ⁇ -picoline, ⁇ -picoline, ⁇ -picoline, 2 , 6-Lutidine, 3,5-Lutidine, 2,4,6-cholidine, 3-chlorpyridine, N, N-diethylaniline, N, N-dimethylaniline, hexamethylenetetramine, quinoline, isoquinoline, N, N-dimethyl-p-toluidine, N, N-dimethyl Examples thereof include piperazine, quinaldine, 4-methylmorpholine, triallylamine, trioctylamine, 1.2-dimethylimidazole, 1-benzyl-2-methylimidazole and the like.
  • an amine-based catalyst is preferable among the above.
  • the amine-based catalyst include tertiary amine-based catalysts such as 3,5-lutidine, 2,4,6-cholidine, triethylenediamine, N, N-dimethylethanolamine, triethylamine, and N-ethylmorpholine. ..
  • the amine-based catalyst preferably contains at least one selected from 3,5-lutidine, 2,4,6-colysine, triethylenediamine, N, N-dimethylethanolamine, triethylamine and N-ethylmorpholine.
  • the basic catalyst preferably contains a compound represented by the following general formula (2) and / or a compound represented by the following general formula (3).
  • R 1 represents a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a halogen atom, and there are a plurality of them. R 1 may be the same or different.
  • Q indicates a carbon atom or a nitrogen atom.
  • m represents an integer from 0 to 5.
  • R 2 , R 3 and R 4 are independently each of a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, and a cycloalkyl group having 3 to 20 carbon atoms. Indicates a group or an allyl group
  • the pKa value is preferably 1 to 9, more preferably 3 to 8, and even more preferably 4 to 8.
  • the pKa value is, for example, (a) The Journal of Physical Chemistry vol. It can be measured by the method described in 68, number 6, page 1560 (1964), (b) a method using an automatic potential difference titrator (AT-610 (trade name), etc.) manufactured by Kyoto Electronics Manufacturing Co., Ltd., and ( c) The acid dissociation index, etc. described in the Chemistry Handbook edited by the Chemical Society of Japan (Revised 3rd Edition, June 25, 1984, published by Maruzen Co., Ltd.) can be used.
  • the organometallic catalyst includes an organotin-based catalyst; organic acid salts such as iron, nickel, and zinc; an acetylacetonate complex; a catalyst composition composed of a carboxylate metal compound and a quaternary ammonium salt compound; Examples thereof include a catalyst composition composed of an amine compound and a quaternary ammonium salt compound; a metal catalyst in which an alkoxy group, a carboxy group or the like is coordinated with titanium or aluminum; and the like.
  • the organometallic catalyst is preferable as the organometallic catalyst.
  • the organotin catalyst include dibutyltin dichloride (DBC), dimethyltindichloride (DMC), dibutyltin dilaurate (DBTDL), dibutyltin diacetate and the like.
  • the organotin catalyst contains at least one selected from dibutyltin dichloride, dimethyltindichloride, dibutyltin dilaurate and dibutyltin diacetate.
  • the polymerization catalyst preferably contains at least one selected from the group consisting of a basic catalyst having a pKa value of 4 to 8 and an organometallic catalyst.
  • the polymerization catalyst contains at least one selected from an amine-based catalyst and an organic tin-based catalyst.
  • Polymerization catalysts include 3,5-lutidine, 2,4,6-cholidine, triethylenediamine, N, N-dimethylethanolamine, triethylamine, N-ethylmorpholine, dibutyltin dichloride, dimethyltin dichloride, dibutyltin dilaurate and dibutyltin diacetate. It is also preferred to include at least one selected from the group consisting of.
  • a total of 100 parts by mass of two or more different monomers for optical materials and 0.010 parts by mass to 2.0 parts by mass of a polymerization catalyst are prepared. That is, in the method for producing an optical material of the first embodiment, a polymerization catalyst of 0.010 part by mass to 2.0 parts by mass is used with respect to a total of 100 parts by mass of two or more different monomers for optical materials. As described above, the amount of the polymerization catalyst used in the first embodiment is large as compared with the conventional method for producing an optical material. Thereby, when the monomer for the optical material in the polymerizable composition for the optical material is polymerized in the curing step, the reaction heat of the polymerizable composition for the optical material can be generated in a short time. By further utilizing this heat of reaction for polymerization, the polymerization reaction can be satisfactorily promoted, and a high-quality optical material in which pulse is suppressed can be obtained in a shorter time than before.
  • the polymerization catalyst By using a polymerization catalyst of 0.010 parts by mass or more with respect to 100 parts by mass of two or more different monomers for optical materials, the polymerization reaction can be satisfactorily promoted, so that the pulse is suppressed in a short time. High quality optical material can be obtained. Further, by satisfactorily promoting the polymerization reaction, it is possible to improve the releasability when the cured product is taken out from the mold. From the above viewpoint, the polymerization catalyst preferably uses 0.015 parts by mass or more, more preferably 0.038 parts by mass or more, with respect to 100 parts by mass of two or more different monomers for optical materials. It is more preferable to use 0.10 parts by mass or more, and it is particularly preferable to use 0.17 parts by mass or more.
  • the range of the content of the above-mentioned polymerization catalyst may be appropriately changed depending on the type of the monomer for optical materials and the polymerization catalyst.
  • the monomers for optical materials are 2,5 (6) -bis (isocyanatomethyl) -bicyclo- [2.2.1] -heptane, pentaerythritol tetrakis (3-mercaptopropionate), and 4-mercaptomethyl.
  • the polymerization catalyst is 0.10 with respect to 100 parts by mass of two or more different monomers for optical materials. It is preferable to use parts by mass or more, and it is more preferable to use parts by mass or more of 0.17.
  • the monomers for optical materials are m-xylylene diisocyanate, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-.
  • dimercapto-3,6,9-trichiaundecan and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane are contained and the polymerization catalyst contains 3,5-lutidine.
  • the polymerization catalyst preferably uses 0.015 parts by mass or more, and more preferably 0.020 parts by mass or more, with respect to 100 parts by mass of two or more different monomers for optical materials.
  • the polymerization catalyst is 2. It is preferable to use 0.010 parts by mass or more, and more preferably 0.015 parts by mass or more with respect to 100 parts by mass of the monomers for different types of optical materials.
  • the monomers for optical materials are dicyclohexylmethanediisocyanate and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane and 4,7-dimercaptomethyl-1,11-dimercapto.
  • the polymerization catalyst is 3,5-lutidine.
  • the polymerization catalyst preferably uses 1.0 part by mass or more, and more preferably 1.5 parts by mass or more with respect to 100 parts by mass of two or more different monomers for optical materials.
  • the monomer for optical materials contains 1,3-bis (isocyanismethyl) cyclohexane, pentaerythritol tetrakis (2-mercaptoacetate) and 2,5-bis (mercaptomethyl) -1,4-dithian, and the polymerization catalyst is
  • 3,5-lutidine it is preferable to use 0.03 parts by mass or more, and 0.07 parts by mass or more of the polymerization catalyst with respect to 100 parts by mass of two or more different monomers for optical materials. Is more preferable.
  • the handleability when injecting a polymerizable composition for optical materials into a mold is improved. be able to.
  • the polymerization catalyst may be used in an amount of 1.0 part by mass or less, and 0.3 part by mass or less, based on 100 parts by mass of two or more different monomers for optical material. It may be used, or 0.15 part by mass or less may be used.
  • the amount of the polymerization catalyst can be appropriately set depending on the type of the polymerization catalyst, the type and amount of the monomers (isocyanate compound, active hydrogen compound, other components, etc.) used, and the desired shape of the molded product. ..
  • the method for producing an optical material according to the first embodiment is a method of mixing a part of two or more kinds of monomers for different optical materials and at least a part of a polymerization catalyst, and a part of two or more kinds of monomers for different optical materials. Including a prepolymerization step of obtaining a mixture containing a prepolymer by polymerizing at least a part of the above to obtain a prepolymer.
  • the present inventors considered that the occurrence of convection due to the non-uniform temperature distribution in the mold in which the polymerization reaction is carried out is one of the causes of the occurrence of pulse in the obtained cured product. Therefore, the present inventors have produced a prepolymer by prepolymerizing a part of the monomer for an optical material, and the polymerizable composition for an optical material contains the prepolymer, so that the viscosity of the polymerizable composition for an optical material is high. Focused on increasing. This makes it possible to suppress convection in the mold.
  • the method for manufacturing an optical material of the first embodiment it is possible to prevent a temperature difference between the inside and the outside of the mold from being generated by preventing the self-heating from escaping to the outside. Combined with the above viewpoints, it is presumed that the method for producing the optical material of the first embodiment can suppress the pulsation of the obtained cured product.
  • the method for producing an optical material according to the first embodiment includes all of the monomers for one type of optical material among two or more different monomers for optical material, and the monomer for one type of optical material other than the above-mentioned monomer for optical material.
  • the method for producing an optical material according to the first embodiment includes all of the monomers for one type of optical material among two or more different monomers for optical material, and the monomer for one type of optical material other than the above-mentioned monomer for optical material.
  • a part of two or more kinds of monomers for different optical materials is not particularly limited.
  • a part of two or more kinds of monomers for different optical materials may be an amount of a part of each of two or more kinds of monomers for different optical materials.
  • a part of two or more kinds of monomers for different optical materials may be all of one or more kinds of monomers for optical materials among two or more kinds of monomers for different optical materials.
  • a part of the polymerization catalyst may be used or the whole may be used.
  • a part is used as the polymerization catalyst, there is no particular limitation on the aspect of "a part of the polymerization catalyst” as well as "a part of two or more kinds of monomers for different optical materials".
  • a part of the polymerization catalyst may be a part of the amount of the polymerization catalyst.
  • the part of the polymerization catalyst is preferably 5 parts by mass to 80 parts by mass out of 100 parts by mass of the polymerization catalyst from the viewpoint of ensuring a long-term pot life, preferably 10 parts by mass. It is more preferably parts to 60 parts by mass, and even more preferably 15 parts by mass to 50 parts by mass.
  • a part of two or more kinds of monomers for different optical materials shall be 5 parts by mass to 95 parts by mass out of 100 parts by mass of two or more kinds of monomers for different optical materials from the viewpoint of ensuring a long-term pot life. It is more preferable, it is more preferably 20 parts by mass to 80 parts by mass, and further preferably 30 parts by mass to 70 parts by mass.
  • prepolymerization step in the first embodiment is not limited to the following embodiments.
  • a part of two or more different optical material monomers is all of one optical material monomer among two or more different optical material monomers, and other than one optical material monomer. It is preferably composed of a part of a monomer for other optical materials.
  • the prepolymerization step of embodiment b is a mixture of a part of two or more different monomers for optical materials and a part of a polymerization catalyst, and at least a part of a part of two or more different monomers for optical materials. Is a step of obtaining a mixture containing a prepolymer by polymerizing the above to obtain a prepolymer.
  • the step of producing a polymerizable composition for an optical material which will be described later, differs from the mixture containing the prepolymer by at least two or more kinds.
  • a polymerizable composition for an optical material containing two or more different monomers for an optical material, a prepolymer, and a polymerization catalyst by adding a residue of a monomer for an optical material and a residue of a polymerization catalyst.
  • two or more different monomers for optical materials are isocyanate compounds (A).
  • the residue of two or more different optical material monomers may contain a portion of the isocyanate compound (A), and the balance of the two or more different optical material monomers may contain the remainder of the isocyanate compound (A). preferable.
  • the method for producing the optical material of the first embodiment is after the prepolymerization step and before the step of producing the polymerizable composition for the optical material, using a B-type viscometer of the mixture containing the prepolymer at 25 ° C. and 60 rpm. It is preferable to further include a viscosity adjusting step of adjusting the viscosity measured under the conditions (also simply referred to as viscosity in the present disclosure) to 30 mPa ⁇ s to 2000 mPa ⁇ s.
  • the polymerizable composition for optical materials produced in the process for producing the polymerizable composition for optical materials is produced from the viewpoint of suppressing the pulse in the obtained optical material.
  • the viscosity can be within an appropriate range. As a result, the pulse in the obtained optical material can be suppressed.
  • the viscosity of the mixture containing the prepolymer is preferably 40 mPa ⁇ s to 2000 mPa ⁇ s, and more preferably 50 mPa ⁇ s to 1800 mPa ⁇ s.
  • the viscosity is measured using a B-type viscometer under the conditions of 25 ° C. and 60 rpm (revolutions per minute).
  • the method for adjusting the viscosity of the mixture containing the prepolymer is not particularly limited.
  • the viscosity of the mixture containing the prepolymer may be adjusted by a method such as heating or stirring.
  • the temperature at which the mixture containing the prepolymer is prepared is not particularly limited as long as the temperature at which the prepolymer can be obtained by the polymerization reaction. For example, it may be 20 ° C to 50 ° C or 25 ° C to 45 ° C.
  • the stirring time for preparing the mixture containing the prepolymer is not particularly limited as long as the stirring time is such that the prepolymer can be obtained by the polymerization reaction. For example, it may be 30 minutes to 5 hours, or 1 hour to 5 hours.
  • a method for preparing a mixture containing a prepolymer specifically, a method for preparing a mixture containing a prepolymer while adjusting the viscosity by stirring at 40 ° C. for 3 hours may be used.
  • the method for producing an optical material according to the first embodiment is to add at least the balance of two or more different optical material monomers to a mixture containing a prepolymer to obtain two or more different optical material monomers. It comprises a step of manufacturing a polymerizable composition for an optical material for obtaining a polymerizable composition for an optical material containing a prepolymer and a polymerization catalyst.
  • a mixture containing a prepolymer is prepared with two or more different monomers for an optical material by adding at least the balance of two or more different monomers for the optical material.
  • This is a step of obtaining a polymerizable composition for an optical material containing a polymer and a polymerization catalyst. This causes polymerization of the prepolymer with the remnants of the two or more different optical material monomers until the mixture is mixed with the mixture containing the prepolymer and the remnants of the two or more different optical material monomers. Can be prevented.
  • the step of producing the polymerizable composition for optical materials by performing the step of producing the polymerizable composition for optical materials at an appropriate time, it is possible to improve the handleability when, for example, the polymerizable composition for optical materials is injected into a mold.
  • the remnants of at least two or more different monomers for an optical material are added to a mixture containing a prepolymer, the remnants of two or more different monomers for an optical material are simply added. It may be mixed in multiple times, or it may be mixed in a plurality of times.
  • the temperature at which each of the above components is mixed is not particularly limited, but is preferably 30 ° C. or lower, and more preferably room temperature (25 ° C.) or lower. It may be preferable that the temperature at which each component is mixed is lower than 25 ° C. However, if the solubility of the additive such as an internal mold release agent and each of the above-mentioned components is not good, the temperature of each of the above-mentioned components may be raised in advance to dissolve the above-mentioned additive in each of the above-mentioned components. ..
  • an additive for example, an internal mold release agent
  • an additive for example, an internal mold release agent
  • This mixture is stirred at 25 ° C. for 1 hour to completely dissolve each component, and then degassed to obtain a first mixture.
  • the balance of the monomer for the optical material and the balance of the polymerization catalyst, if necessary, are stirred at 25 ° C. for 30 minutes to completely dissolve them to obtain a second mixed solution.
  • the first mixture and the second mixture are mixed, stirred and then degassed to obtain a polymerizable composition for an optical material as a uniform solution.
  • the method for producing an optical material according to the first embodiment is to feed the polymerizable composition for an optical material into a casting mold after the step of producing the polymerizable composition for the optical material and before the curing step. It may further include a liquid step.
  • the liquid feeding step may be a step of feeding the polymerizable composition for an optical material to a casting mold while remixing it in a static mixer.
  • the liquid feeding step may be a step of feeding the polymerizable composition for an optical material to a casting mold while remixing it with a dynamic mixer.
  • the non-uniformity of the distribution of the polymerizable composition for optical materials can be eliminated while the polymerizable composition for optical materials is sent to the mold, so that the pulse of the obtained cured product is suppressed. be able to.
  • the polymerizable composition for an optical material of the first embodiment comprises two or more kinds of monomers for different optical materials, a polymerization catalyst, and at least two kinds of monomers for optical materials among two or more kinds of monomers for different optical materials.
  • the content of the polymerization catalyst includes the prepolymer obtained by polymerization, and the content of the polymerization catalyst is 0.010 parts by mass to 2.0 parts by mass with respect to 100 parts by mass in total of the monomers and prepolymers for two or more different kinds of different optical materials. It is a department.
  • the reaction heat that is, the heat due to self-heating
  • the polymerizable composition for optical material can be increased.
  • the polymerization reaction of the monomer for optical material in the polymerizable composition for optical material can be promoted, and a high-quality optical material in which pulse is suppressed can be obtained in a shorter time than before. be able to.
  • the polymerizable composition for an optical material of the first embodiment has the above-mentioned structure, so that convection in the mold in which the polymerization reaction is carried out can be suppressed, and the generation of veins in the obtained cured product can be suppressed. It can be suppressed.
  • the content of the polymerization catalyst is 0.015 parts by mass or more with respect to 100 parts by mass in total of the two or more different monomers and prepolymers for optical materials. It is preferably 0.038 parts by mass or more, further preferably 0.10 parts by mass or more, and particularly preferably 0.17 parts by mass or more.
  • the content of the polymerization catalyst is 1.5 parts by mass or less with respect to 100 parts by mass in total of the two or more different monomers and prepolymers for optical materials. It is preferably 1.0 part by mass or less, and more preferably 1.0 part by mass or less.
  • the polymerizable composition for optical materials of the first embodiment has a viscosity (also simply referred to as viscosity in the present disclosure) of 70 mPa ⁇ s measured under the condition of 25 ° C. and 60 rpm with a B-type viscometer from the viewpoint of suppressing pulse.
  • a viscosity also simply referred to as viscosity in the present disclosure
  • the above is preferable, 80 mPa ⁇ s or more is more preferable, 100 mPa ⁇ s or more is further preferable, and 120 mPa ⁇ s or more is particularly preferable.
  • the polymerizable composition for an optical material of the first embodiment preferably has a viscosity of 1000 mPa ⁇ s or less, preferably 700 mPa ⁇ s or less, from the viewpoint of maintaining good handleability when molding the optical material into a desired shape. It is more preferably 400 mPa ⁇ s or less, and further preferably 400 mPa ⁇ s or less.
  • the method for measuring the viscosity is as described above.
  • the polymerizable composition for an optical material of the first embodiment may contain any additive.
  • Optional additives include photochromic compounds, internal mold release agents, brewing agents, UV absorbers and the like.
  • a photochromic compound is a compound in which the molecular structure is reversibly changed by irradiation with light of a specific wavelength, and the absorption characteristics (absorption spectrum) are changed accordingly.
  • Examples of the photochromic compound used in the first embodiment include compounds whose absorption characteristics (absorption spectrum) change with respect to light having a specific wavelength.
  • the photochromic compound is not particularly limited, and any conventionally known compound that can be used for a photochromic lens can be appropriately selected and used.
  • any conventionally known compound that can be used for a photochromic lens can be appropriately selected and used.
  • one or more of spiropyran compounds, spirooxazine compounds, flugide compounds, naphthopyran compounds, bisimidazole compounds and the like can be used depending on the desired coloring.
  • Vivid's Reversacol Huber Blue polydimethylsiloxane chain, naphthopylan-based chromophore, Reversacol Calder Blue (polydimethylsiloxane chain, naphthopylan-based chromophore, Reversalcol Trent Blue).
  • Examples of the internal mold release agent include acidic phosphoric acid esters.
  • Examples of the acidic phosphoric acid ester include a phosphoric acid monoester and a phosphoric acid diester, which can be used alone or in combination of two or more.
  • a monomer for an optical material having a high polymerizability is used as the monomer for an optical material, it is preferable to use an internal mold release agent having a relatively low releasability.
  • the monomer for optical materials having high polymerizable properties include an isocyanate compound having an aromatic ring, a trifunctional polythiol compound (specifically, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, etc.) and the like. Can be mentioned.
  • These highly polymerizable monomers for optical materials are likely to be exfoliated from the mold earlier than expected (for example, during the polymerization of the optical monomers) (also referred to as early release).
  • the occurrence of the early release can be suppressed by using an internal mold release agent having a relatively low mold release property.
  • an internal mold release agent having a relatively low releasability for example, an acidic phosphoric acid ester having a relatively low releasability is preferable, and specifically, JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.) is more preferable.
  • JP-506H manufactured by Johoku Chemical Industry Co., Ltd.
  • the content of the internal release agent is preferably 1000 mass ppm or less.
  • the timing of adding the internal mold release agent to the mixture containing the prepolymer, the polymerizable composition for optical materials, and the like is not particularly limited.
  • the internal mold release agent may be added during the prepolymerization step, may be added to the mixture containing the prepolymer after the prepolymerization step, and two or more kinds may be added to the mixture containing the prepolymer. It may be added to the rest of the polymers for different optical materials.
  • an internal mold release agent such as an acidic phosphoric acid ester that may form a salt with the polymerization catalyst
  • the catalytic activity of the polymerization catalyst decreases due to the formation of the salt, and the reaction time. May be longer. Therefore, from the viewpoint of suppressing the extension of the polymerization reaction time in the prepolymerization step, it is preferable not to add the internal mold release agent at the stage where the polymerization reaction is in progress in the prepolymerization step.
  • the internal mold release agent is a mixture containing the prepolymer in a stable state after the polymerization reaction has progressed to some extent, or a monomer for two or more different optical materials. It is preferable to add it to the balance.
  • the internal release agent is used in the prepolymerization step for the purpose of suppressing the activity of the polymerization catalyst in the mixture containing the prepolymer. It is preferable to add it to the mixture containing the prepolymer when the polymerization reaction is stable to some extent or when it is desired to be stabilized.
  • the bluing agent examples include those having an absorption band in the orange to yellow wavelength range in the visible light region and having a function of adjusting the hue of an optical material made of resin. More specifically, the bluing agent contains a substance showing a blue color to a purple color.
  • UV absorbers used include 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, 2-hydroxy-.
  • Benzophenone-based UV absorbers such as 4-acryloyloxy-2', 4'-dichlorobenzophenone,
  • UV absorbers can be used alone or in combination of two or more.
  • the method for producing an optical material according to the first embodiment is an optical material which is a cured product of a polymerizable composition for an optical material by curing two or more different monomers for an optical material in the polymerizable composition for an optical material. Includes a curing step to obtain.
  • a cured product can be obtained by polymerizing a polymerizable composition for an optical material, and this cured product can be used as an optical material.
  • a polymerizable composition for an optical material is heated to generate a polymerization reaction.
  • the polymerizable composition for an optical material according to the first embodiment has a reaction heat (reaction heat) associated with the polymerization reaction. That is, by increasing the heat due to self-heating), the polymerization reaction of the monomer for optical materials in the polymerizable composition for optical materials can be promoted.
  • reaction heat reaction heat
  • the polymerizable composition for an optical material may be heated, but from the above viewpoint, the polymerizable composition for an optical material may not be heated. That is, in the curing step of the first embodiment, the polymerizable composition for optical materials can be cured by polymerization by allowing the polymerizable composition for optical materials to stand still.
  • the curing step may include a step of curing the polymerizable composition for optical materials by allowing the polymerizable composition for optical materials to stand still.
  • the polymerizable composition for an optical material may be allowed to stand in a closed system space or in an open system space, but the closed system space may be allowed to stand still. It is preferable to leave it still inside.
  • the closed system space refers to an environment in which heat is retained inside and heat conduction between the inside and the outside is suppressed.
  • An environment in which heat conduction between the inside and the outside is suppressed means that when the polymerizable composition for an optical material is allowed to stand in the closed system space, the heat conductivity between the inside and the outside of the closed system space is high. It means an environment in which the polymerizable composition for an optical material can be cured.
  • Examples of the closed space include a heat insulating environment.
  • An open space means a space other than a closed space.
  • the curing step preferably includes a step of curing the polymerizable composition for optical materials by allowing the polymerizable composition for optical materials to stand in a closed space.
  • the polymerization reaction of the polymerizable composition for optical materials is hindered by the reaction heat, or the polymerization reaction of the polymerizable composition for optical materials is excessively caused by heating from the outside. It is preferable to heat the adiabatic reaction tank to a constant temperature state (constant temperature reaction tank) within a range that does not promote it. As a result, the environmental temperature in the reaction vessel (constant temperature reaction vessel) in which the mold is placed can be kept warm or constant temperature according to the temperature rise state due to the self-heating of the monomer for optical material. The polymerization reaction can be promoted satisfactorily.
  • the adiabatic reaction tank or the constant temperature reaction tank as described above can be used.
  • adiabatic polymerization in an adiabatic environment using an adiabatic reaction vessel can be performed by the following procedure. can.
  • the inner surface of the vacuum vessel is covered with a member having heat insulating or heat-retaining properties such as urethane foam and cork, and the mold in which the monomer is injected is wrapped with a member such as a waste cloth as needed. Then, the mold in which the monomer is injected is allowed to stand in the vacuum container.
  • the curing step may include a step of curing the polymerizable composition for optical materials (that is, a non-heating step) by allowing the polymerizable composition for optical materials to stand without being heated from the outside.
  • a step of curing the polymerizable composition for optical materials that is, a non-heating step
  • heating of the polymerizable composition for optical materials may be performed, but heating of the polymerizable composition for optical materials is not always necessary.
  • an apparatus may be used, which may increase the burden economically.
  • the optical material can be manufactured by a simple method, so that the economic burden can be reduced.
  • the curing step preferably includes a step of curing the polymerizable composition for optical materials by allowing the polymerizable composition for optical materials to stand for 2 to 10 hours.
  • the polymerization reaction is carried out over several hours to several tens of hours (for example, about 20 hours to 48 hours) while gradually raising the temperature by heating.
  • the time for carrying out the polymerization reaction is short, the polymerizable composition for an optical material is not completely cured, so that the optical material cannot be obtained, or the quality of the optical material is deteriorated.
  • the method for manufacturing an optical material of the first embodiment it is possible to manufacture the optical material in a short time while suppressing the pulse in the obtained optical material.
  • the optical material can be produced by allowing the polymerizable composition for an optical material to stand for 10 hours or less. From the above viewpoint, it is more preferable to allow the polymerizable composition for an optical material to stand for 8 hours or less in the curing step. Further, from the viewpoint of obtaining a well-cured optical material by carrying out a polymerization reaction, it is preferable to allow the polymerizable composition for an optical material to stand for 2 hours or more.
  • a microwave irradiation step of irradiating the polymerizable composition for an optical material with microwaves for a predetermined time may be provided.
  • Step a The polymerizable composition for an optical material is injected (casted) into a mold (inside the cavity of the mold).
  • Step b The mold in which the polymerizable composition for an optical material is injected is allowed to stand for a predetermined time to be cured.
  • Step a First, the polymerizable composition is injected into a molding mold (mold) held by a gasket, tape or the like. At this time, depending on the physical characteristics required for the obtained optical material, it is preferable to perform a degassing treatment under reduced pressure, a filtration treatment under pressure, a reduced pressure, or the like, if necessary.
  • Step b the mold in which the polymerizable composition for an optical material is injected may be allowed to stand in an open system space for a predetermined time for polymerization, or may be allowed to stand in a closed system space for adiabatic polymerization. You may.
  • the polymerization conditions are not limited, but are preferably adjusted appropriately depending on the composition of the polymerizable composition for optical materials, the type and amount of the catalyst used, the shape of the mold, and the like.
  • the mold in which the polymerizable composition for an optical material is injected may be allowed to stand in an adiabatic environment for 2 to 4 hours for polymerization.
  • a heating step may be added after the adiabatic polymerization process in which the mold in which the polymerizable composition for optical materials is injected is allowed to stand in an adiabatic environment for a certain period of time.
  • step b in parallel with the step of allowing the mold into which the polymerizable composition for an optical material is injected to stand in an adiabatic environment (adiabatic polymerization), if necessary, in the adiabatic polymerization process continuously or intermittently.
  • the mold in which the polymerizable composition for optical materials is injected is heated at a temperature not exceeding the self-heating generated by the polymerizable composition for optical materials, or the inside of the adiabatic reaction tank is heated to keep the environmental temperature in the adiabatic reaction tank warm. You may do it.
  • the curing step may include a step of heating and curing the polymerizable composition for an optical material (that is, a heating step).
  • a heating step As described above, in the method for producing an optical material of the first embodiment, heating of the polymerizable composition for an optical material is not always necessary, but the heating step may be included in the curing step. That is, the curing step in the first embodiment may be a combination of the non-heating step and the heating.
  • the heating step is preferably performed for a period of 1% to 40%, more preferably 1% to 35% with respect to the entire period of the curing step.
  • ⁇ Second prepolymerization step> In the method for producing an optical material of the first embodiment, in addition to the above-mentioned preparation step and prepolymerization step, the balance of the two or more different monomers for the optical material and the balance of the polymerization catalyst are further mixed.
  • a polymerizable composition for an optical material containing the prepolymer, the second prepolymer, and the polymerization catalyst by adding the mixture containing the second prepolymer to the mixture containing the prepolymer.
  • the method for producing an optical material according to the first embodiment includes the above-mentioned constitution, and is a mixture containing a prepolymer obtained by a prepolymerization step and a mixture containing a second prepolymer obtained by a second prepolymerization step. And can be obtained. As a result, the viscosities of the mixture containing the prepolymer and the mixture containing the second prepolymer can be brought close to each other, so that both can be mixed more easily.
  • two or more different monomers for optical materials, a polymerization catalyst, specific embodiments, preferred embodiments and the like are described as two or more different monomers for optical materials, polymerization catalysts, specific embodiments in the prepolymerization step. It is the same as the embodiment, the preferred embodiment and the like.
  • the step of producing a polymerizable composition for an optical material is a mixture containing the second prepolymer with respect to the mixture containing the prepolymer.
  • a step of obtaining a polymerizable composition for an optical material containing the prepolymer, the second prepolymer, and the polymerization catalyst is a step of producing a polymerizable composition for an optical material.
  • the mixture containing the prepolymer, specific embodiments, preferred embodiments and the like are the same as the above-mentioned specific embodiments and preferred embodiments in the above-mentioned ⁇ process for producing a polymerizable composition for optical materials>. Is.
  • the curing step cures the prepolymer and the second prepolymer in the polymerizable composition for an optical material.
  • the prepolymer, specific embodiments, preferred embodiments, etc. are the same as the specific embodiments, preferred embodiments, etc. in the above-mentioned ⁇ curing step>.
  • the method for producing an optical material according to the first embodiment may include an annealing step of annealing a cured polymerizable composition for an optical material, if necessary.
  • the temperature at which the annealing treatment is performed is usually 50 to 150 ° C, preferably 90 to 140 ° C, and more preferably 100 to 130 ° C.
  • the optical material in the first embodiment is a cured product of a polymerizable composition for an optical material.
  • the optical material in the first embodiment is a high quality optical material with suppressed pulse.
  • the thicker the optical material the more likely it is that pulse will occur.
  • the optical material produced by using the method for producing an optical material according to the first embodiment can satisfactorily suppress pulse even if the thickness is relatively thick.
  • the optical material in the first embodiment may have a thickness of 1 mm to 20 mm or 4 mm to 16 mm.
  • the optical material in the first embodiment can be used for a plastic lens, a prism, an optical fiber, an information recording board, a filter, a light emitting diode and the like.
  • the optical material in the first embodiment can be suitably used for a plastic lens, and can be more preferably used for a plastic lens for spectacles.
  • the method for producing an optical material according to the second embodiment is a method for producing an optical material using a polymerizable composition for an optical material containing two or more different monomers for an optical material and a polymerization catalyst.
  • a raw material composition preparation step for preparing a first raw material composition and a second raw material composition, and a shearing force are applied to the first raw material composition and the second raw material composition to produce the polymerizable composition for an optical material.
  • “Applying a stirring force to a polymerizable composition for an optical material” means that the polymerizable composition for an optical material is allowed to flow, and the flow direction is mainly (that is, the composition) with respect to the polymerizable composition for an optical material. Applying force in substantially parallel and opposite directions on the virtual line connecting the part (inlet) that enters the process of applying the stirring force (inlet) and the part (exit) that exits (the direction from the inlet to the outlet), or stopping the flow and the optics It means stirring the polymerizable composition for materials.
  • the method for producing an optical material according to the second embodiment can suppress U-shaped veins in the obtained optical material by including each of the above steps.
  • U-shaped veins are likely to occur after a certain amount of time has passed since the polymerizable composition for an optical material was cast into a mold.
  • the present inventors focused on the step of shearing and stirring the first raw material composition and the second raw material composition from the viewpoint of suppressing the U-shaped pulse. Further, as a result of continuing to study the mode and order of shearing and stirring, the optical material obtained by the method for producing the optical material of the second embodiment has the above-mentioned configuration including the above-mentioned shearing step and the above-mentioned stirring step.
  • the first raw material composition is formed by applying a force to the first raw material composition and the second raw material composition in a direction intersecting the flow direction while flowing the first raw material composition and the second raw material composition. And it is considered that orientation occurs as the second raw material composition is sheared. While flowing the obtained polymerizable composition for optical materials, a force is applied to the polymerizable composition for optical materials in substantially parallel and opposite directions in the flow direction to make the concentration unevenness uniform before and after the flow direction. At the same time, the orientation can be relaxed or made uniform. As a result, it is considered that the U-shaped pulse can be suppressed.
  • the polymerizable composition for an optical material in the second embodiment contains two or more different monomers for an optical material and a polymerization catalyst. Further, the polymerizable composition for an optical material is produced by applying a shearing force to the first raw material composition and the second raw material composition. Therefore, the first raw material composition and the second raw material composition include two or more different kinds of monomers for optical materials and a polymerization catalyst as a whole including the first raw material composition and the second raw material composition.
  • the first raw material composition and the second raw material composition may each contain different types of monomers for optical materials, and at least one of the first raw material composition and the second raw material composition may contain a polymerization catalyst. (See, for example, the section of examples).
  • the first raw material composition and the second raw material composition contains a mixture containing the prepolymer in the first embodiment.
  • an optical material is produced using a polymerizable composition for an optical material containing two or more different monomers for an optical material and a polymerization catalyst.
  • a casting step of casting the polymerizable composition for an optical material into a mold After the stirring step, a casting step of casting the polymerizable composition for an optical material into a mold, and a casting step.
  • the raw material composition preparation step is a step of preparing the first raw material composition and the second raw material composition.
  • the first raw material composition and the second raw material composition are not particularly limited as long as they contain two or more different monomers for optical materials and a polymerization catalyst as a whole.
  • the first raw material composition and the second raw material composition ready-made products may be used, respectively, or a monomer for an optical material and a polymerization catalyst may be mixed and prepared.
  • the mixing method is not particularly limited, and a known method can be used.
  • the temperature at which each of the above components is mixed is not particularly limited, but is preferably 30 ° C. or lower, and more preferably room temperature (25 ° C.) or lower. From the viewpoint of the pot life of the prepared polymerizable composition for optical materials, it may be preferable to lower the temperature further than 25 ° C. However, if the solubility of the additive such as an internal mold release agent and each of the above-mentioned components is not good, the temperature of each of the above-mentioned components may be raised in advance to dissolve the above-mentioned additive in each of the above-mentioned components. ..
  • the polymerization catalyst may be mixed in advance with a part of two or more kinds of monomers for different optical materials, and then the rest of two or more kinds of monomers for different optical materials may be mixed in a single step. Well, it may be mixed in a plurality of times.
  • Specific embodiments of the raw material composition preparation step include, for example, the following embodiments.
  • a part of the monomer for optical material and an additive are charged to prepare a mixed solution.
  • This mixture is stirred at 25 ° C. for 1 hour to completely dissolve each component, and then a part of the rest of the monomer for optical material is further charged, and this is stirred to obtain a uniform solution.
  • Defoaming is performed on this solution to obtain a first raw material composition.
  • the rest of the monomer for the optical material and the catalyst are stirred at 25 ° C. for 30 minutes to completely dissolve them into a uniform solution. Defoaming is performed on this solution to obtain a second raw material composition.
  • the shearing step is a step of applying a shearing force to the first raw material composition and the second raw material composition to produce a polymerizable composition for an optical material.
  • the force applied in the direction intersecting the flow direction is also referred to as a shear force.
  • applying a force mainly in a direction intersecting the flow direction is also referred to as "shearing”.
  • “Floating” means that the composition can be made to flow by, for example, sending the composition from the tank to the power mixer, sending the composition from the power mixer to the stirring tank, and the like.
  • the flow rate of the first raw material composition and the second raw material composition should be 3 g / s or more from the viewpoint of increasing productivity while suppressing an increase in viscosity of the polymerizable composition for optical materials. It is more preferably 6 g / s or more, and even more preferably 9 g / s or more.
  • the flow rate of the first raw material composition and the second raw material composition is preferably 50 g / s or less from the viewpoint of suppressing the U-shaped vein of the polymerizable composition for optical materials. It is more preferably 45 g / s or less, and further preferably 40 g / s or less.
  • the rotation speed in the shearing step is preferably 200 rpm or more, more preferably 400 rpm or more, and even more preferably 500 rpm or more.
  • the rotation speed in the shearing step is preferably 3000 rpm or less, more preferably 2500 rpm or less, and even more preferably 2000 rpm or less.
  • the polymerizable composition for an optical material is produced by applying a shearing force to the first raw material composition and the second raw material composition.
  • the polymerizable composition for an optical material contains two or more different monomers for an optical material and a polymerization catalyst.
  • Polythiol compound having two or more mercapto groups Specific examples of the polythiol compound having two or more mercapto groups in the second embodiment, preferable embodiments, preferable contents and the like are details of the specific examples of the polythiol compound having two or more mercapto groups in the first embodiment, preferable. It is the same as the details such as an aspect and a preferable content.
  • Hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups Specific examples, preferred embodiments, preferred contents and the like of the hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups in the second embodiment refer to the one or more mercapto groups in the first embodiment. It is the same as the details of the specific example, the preferable embodiment, the preferable content and the like of the hydroxythiol compound having one or more hydroxyl groups.
  • polyol compound having two or more hydroxyl groups Specific examples, preferred embodiments, preferred contents and the like of the polyol compound having two or more hydroxyl groups in the second embodiment are specific examples of the polyol compound having two or more hydroxyl groups in the first embodiment, preferred embodiments. It is the same as the details such as a preferable content.
  • organometallic catalyst (Organometallic catalyst)
  • the details of the specific examples, preferred embodiments, etc. of the organometallic catalyst in the second embodiment are the same as the details of the specific examples, preferred embodiments, etc. of the organometallic catalyst in the first embodiment.
  • the polymerization catalyst preferably satisfies the following condition 1.
  • -Ea / R is -7100 or more and -2900 or less.
  • Ea is the activation energy calculated by the Arrhenius plot from the reaction rate constants of the two or more different optical material monomers at two or more different temperatures, and R is the gas constant (8.314 J / mol / K). ).
  • the polymerization catalyst satisfies the condition 1
  • the variation in the polymerization rate can be suppressed in the process of polymerizing and curing the polymerizable composition, and as a result, the occurrence of optical strain and fringes is suppressed, and the appearance is excellent.
  • Optical materials can be obtained.
  • the value of Ea is calculated by the following method.
  • the composition 1 containing the polymerization-reactive compound and a predetermined amount of the polymerization catalyst is heated and kept at a plurality of temperatures, the physical property values 1a derived from the functional group of the polymerization-reactive compound before heating and A physical property acquisition step of acquiring a physical property value 1b derived from a residual functional group after heat retention for a predetermined time, and a physical property acquisition step.
  • the specific embodiment of the method for calculating the value of Ea and the method for determining whether or not the polymerization catalyst satisfies the condition 1 is the same as the specific embodiment described in International Publication No. 2020/256057.
  • the stirring step is a step of applying a stirring force to the polymerizable composition for an optical material.
  • the force applied in the direction substantially parallel to the flow direction is also referred to as a stirring force.
  • the preferable range of the flow rate of the polymerizable composition for optical material is the same as the preferable range of the flow rate of the polymerizable composition for optical material in the above-mentioned ⁇ shearing step>. Is.
  • the rotation speed in the stirring step is preferably 50 rpm or more, more preferably 100 rpm or more, and even more preferably 200 rpm or more.
  • the rotation speed in the stirring step is preferably 800 rpm or less, more preferably 700 rpm or less, and even more preferably 600 rpm or less.
  • the method for producing an optical material according to the second embodiment continuously comprises a uniform polymerizable composition for an optical material from the viewpoint of suppressing a U-shaped pulse in the obtained optical material by including a shearing step and a stirring step. Can be produced as an optical device.
  • the method for producing the optical material of the second embodiment preferably includes a shearing step and a stirring step in this order from the viewpoint of suppressing the U-shaped pulse in the obtained optical material. That is, the method for producing an optical material according to the second embodiment is a method for producing an optical material using a polymerizable composition for an optical material containing two or more different monomers for an optical material and a polymerization catalyst.
  • the method for producing an optical material according to the second embodiment may further include a filtration step of filtering a polymerizable composition for an optical material.
  • the filtration step can be performed using a filter.
  • a filter for example, a capsule filter can be used.
  • the filtration accuracy of the filter is preferably 1.0 ⁇ m to 4.5 ⁇ m.
  • the method for producing an optical material of the second embodiment may further include a second stirring step of stirring the polymerizable composition for an optical material.
  • the second stirring step is a step for further stirring the polymerizable composition for an optical material in addition to the above-mentioned shearing step and stirring step.
  • the stirring step described in the above-mentioned ⁇ stirring step> is also referred to as a first stirring step.
  • a method of stirring the polymerizable composition for an optical material in the second stirring step for example, a method using a static mixer or the like can be mentioned.
  • the inner diameter ⁇ of the static mixer is preferably 5 to 8, more preferably 6 to 8.
  • the number of elements of the static mixer is preferably 16 to 48, more preferably 24 to 48.
  • the casting step is a step of casting the polymerizable composition for an optical material into a mold after the first or second stirring step.
  • the viscosity measured with a B-type viscometer of the polymerizable composition for optical materials in the casting step under the conditions of 25 ° C. and 60 rpm is preferably 10 mPa ⁇ s to 1000 mPa ⁇ s.
  • the casting step is preferably a step of adjusting the viscosity of the polymerizable composition for an optical material measured at 25 ° C. and 60 rpm with a B-type viscometer to 10 mPa ⁇ s to 1000 mPa ⁇ s and casting into a mold. ..
  • the viscosity of the polymerizable composition for optical materials is kept within an appropriate range, and the pulse in the obtained optical material is suppressed. Can be done.
  • the viscosity of the polymerizable composition for an optical material in the casting step is preferably 10 mPa ⁇ s or more, more preferably 40 mPa ⁇ s or more, and further preferably 70 mPa ⁇ s or more. It is particularly preferable that it is 80 mPa ⁇ s or more, further preferably 100 mPa ⁇ s or more, and even more preferably 120 mPa ⁇ s or more.
  • the viscosity of the polymerizable composition for an optical material in the casting step is preferably 1000 mPa ⁇ s or less, preferably 700 mPa ⁇ s or less, from the viewpoint of maintaining good handleability when molding the optical material into a desired shape. It is more preferably present, and further preferably 400 mPa ⁇ s or less.
  • the method for adjusting the viscosity of the polymerizable composition for an optical material is not particularly limited.
  • the viscosity of the polymerizable composition for an optical material may be adjusted by a method such as addition of a high-viscosity compound, heating, or stirring.
  • the casting step may be a step of casting a polymerizable composition for an optical material into a mold by a multi-axis method. Further, it may be a step of casting the polymerizable composition for an optical material into a mold by a mixing method immediately before casting.
  • the casting method may be manual casting or automatic mechanical casting.
  • the method of automatic casting may be pressure feeding by nitrogen, or may be liquid feeding by a pump (diaphragm pump, gear pump, etc.).
  • the casting step it is preferable to apply pressure (for example, back pressure) to the polymerizable composition for optical materials using nitrogen or the like to cast the polymerizable composition for optical materials into a mold.
  • pressure for example, back pressure
  • the polymerizable composition for an optical material can be cast into a mold by a multi-axis method.
  • the curing step is a step of curing the polymerizable composition for optical materials by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold.
  • the method for producing an optical material according to the second embodiment includes a curing step, the polymerizable composition for an optical material can be polymerized, and the optical material can be produced.
  • the method of polymerization is not particularly limited, but a known method may be used to generate a polymerization reaction by heating.
  • a method of injecting a polymerizable composition into a molding mold (mold) held by a gasket or tape and gradually raising the temperature while heating to accelerate the polymerization reaction may be used.
  • the polymerization method a method of carrying out a polymerization reaction without heating may be used. That is, in the curing step of the second embodiment, the polymerizable composition for optical materials may be cured by polymerization by allowing the polymerizable composition for optical materials to stand still.
  • the environment in which the curing step is performed is not particularly limited, and the mold can be cured by heating from the outside of the mold. It is preferable that the step is to cure the polymerizable composition for optical materials by allowing the polymerizable composition for materials to stand in a closed space.
  • the step is to cure the polymerizable composition for optical materials by allowing the polymerizable composition for materials to stand in a closed space.
  • the adiabatic environment refers to an environment in which heat is retained inside and heat conduction between the inside and the outside is suppressed.
  • An environment in which heat conduction between the inside and the outside is suppressed means that when the polymerizable composition for an optical material is allowed to stand in the closed system space, the heat conductivity between the inside and the outside of the closed system space is suppressed. It means an environment in which the polymerizable composition for an optical material can be cured.
  • the adiabatic environment can be formed, for example, using an adiabatic material. That is, by allowing the polymerizable composition for an optical material to stand in a heat insulating container made of a heat insulating material, heat can be retained inside the heat insulating container and heat conduction between the inside and the outside can be suppressed. ..
  • the thermal conductivity of the heat insulating material is preferably 0.50 W / mK or less, more preferably 0.10 W / mK or less, and even more preferably 0.05 W / mK or less.
  • the density of the heat insulating material is preferably 10 kg / m 3 or more, more preferably 15 kg / m 3 or more, and further preferably 20 kg / m 3 or more.
  • the polymerization reaction of the polymerizable composition for optical materials is hindered by the reaction heat, or the polymerization reaction of the polymerizable composition for optical materials is excessively caused by heating from the outside. It is preferable to heat the adiabatic reaction tank to a constant temperature state (constant temperature reaction tank) within a range that does not promote it. As a result, the environmental temperature in the reaction vessel (constant temperature reaction vessel) in which the mold is placed can be kept warm or constant temperature according to the temperature rise state due to the self-heating of the monomer for optical material. The polymerization reaction can be promoted satisfactorily.
  • the adiabatic reaction tank or the constant temperature reaction tank as described above can be used.
  • adiabatic polymerization in an adiabatic environment using an adiabatic reaction vessel can be performed by the following procedure. can.
  • the inner surface of the vacuum container is covered with a member having heat insulating and heat-retaining properties such as urethane foam and cork, and the mold in which the monomer is injected is wrapped with a member such as a waste cloth as needed. Then, the mold in which the monomer is injected is allowed to stand in the vacuum container.
  • the curing step may be a step of curing the polymerizable composition for optical materials by allowing the polymerizable composition for optical materials to stand without being heated from the outside.
  • heating of the polymerizable composition for an optical material is not always required.
  • an apparatus may be used, which may increase the burden economically. If the method is not heated from the outside, the optical material can be manufactured by a simple method, so that the economic burden can be reduced.
  • the curing step is preferably a step of curing the polymerizable composition for optical materials by allowing the polymerizable composition for optical materials to stand for 2 to 10 hours.
  • the polymerizable composition for an optical material is allowed to stand for 8 hours or less.
  • a microwave irradiation step of irradiating the polymerizable composition for an optical material with microwaves for a predetermined time may be provided.
  • the aspect described as one aspect of the curing step in the first embodiment can be mentioned.
  • the method for producing an optical material according to the second embodiment may include an annealing step of annealing a cured polymerizable composition for an optical material, if necessary.
  • the temperature at which the annealing treatment is performed is usually 50 to 150 ° C, preferably 90 to 140 ° C, and more preferably 100 to 130 ° C.
  • the optical material produced by the method for producing an optical material according to the second embodiment can be used for a plastic lens, a prism, an optical fiber, an information recording substrate, a filter, a light emitting diode, and the like.
  • the optical material can be suitably used for a plastic lens, and can be more preferably used for a plastic lens for spectacles.
  • the optical material manufacturing system of the second embodiment is a system for manufacturing an optical material using a polymerizable composition for an optical material containing two or more different monomers for an optical material and a polymerization catalyst.
  • a shearing portion that applies a shearing force to the first raw material composition and the second raw material composition to produce the polymerizable composition for an optical material, and a shearing portion.
  • a stirring unit that applies stirring force to the polymerizable composition for optical materials, and a stirring unit.
  • a cured portion that cures the polymerizable composition for optical materials by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold. Includes a fixed-quantity liquid delivery unit.
  • a shearing force is applied to the first raw material composition and the second raw material composition to produce the polymerizable composition for an optical material.
  • a method of applying a force in a direction intersecting the flow direction in the sheared portion for example, a method using a power mixer can be mentioned.
  • Preferred ranges such as the flow rate of the polymerizable composition for optical materials in the sheared portion and the rotation speed of the power mixer are the flow speed of the polymerizable composition for optical materials in the above-mentioned ⁇ shearing step>, the rotation speed of the power mixer, and the like. Similar to the preferred range.
  • a stirring force is applied to the polymerizable composition for optical materials.
  • a method of applying a force in the direction substantially parallel to the flow direction in the stirring unit for example, a method using a stirring tank containing a stirrer can be mentioned.
  • Preferred ranges such as the flow rate of the polymerizable composition for optical materials in the stirring section, the rotation speed of the stirring tank, and the like are the flow speed of the polymerizable composition for optical materials in the above-mentioned ⁇ stirring step>, the rotation speed of the stirring tank, and the like. Similar to the preferred range.
  • the polymerizable composition for an optical material is cast into a mold. Details such as the specific embodiment of the casting and the preferable range of the viscosity of the polymerizable composition for the optical material in the casting portion are described in the specific embodiment of the casting in the above-mentioned ⁇ casting step> and for the optical material in the casting portion. The same applies to the details such as the preferable range of the viscosity of the polymerizable composition.
  • the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold.
  • the details of the specific mode, the preferred mode, etc. in the cured portion are the same as the details of the specific mode, the preferred mode, etc. in the above-mentioned ⁇ curing step>.
  • ⁇ Quantitative liquid feeding unit> In the quantitative liquid feeding section, the first raw material composition and the second raw material composition are fed to the shearing section.
  • the fixed-quantity liquid feeding unit include pumps such as gear pumps and diaphragm pumps.
  • the speed at which the first raw material composition and the second raw material composition are fed to the shearing section may be appropriately adjusted.
  • the optical material manufacturing system of the second embodiment is obtained by further curing the shearing force of the sheared portion, the temperature of the polymerizable composition for optical material in the stirring portion, and the polymerizable composition for optical material in the cured portion. From the feature quantity that correlates with the optical quality of the cured product and the viscosity (also simply referred to as viscosity in the present disclosure) measured at 25 ° C. and 60 rpm with a B-type viscosity meter of the polymerizable composition for optical materials.
  • a viscosity control unit for controlling the viscosity measured at 25 ° C. and 60 rpm with a B-type viscosity meter of the polymerizable composition for optical materials in the stirring unit is provided according to at least one condition selected from the group. Is preferable.
  • the U-shaped pulse By controlling the viscosity of the polymerizable composition for optical materials in the stirring unit according to each of the above conditions, the U-shaped pulse can be suppressed more satisfactorily. In addition, the U-shaped pulsation can be better suppressed over a long period of time.
  • the optical material manufacturing system of the second embodiment is obtained by further curing the shearing force of the sheared portion, the temperature of the polymerizable composition for optical material in the stirring portion, and the polymerizable composition for optical material in the cured portion. At least one condition selected from the group consisting of the optical quality of the cured product obtained and the characteristic amount that correlates with the viscosity measured at 25 ° C. and 60 rpm with a B-type viscosity meter of the polymerizable composition for optical materials. Therefore, it is preferable to provide a temperature control unit that controls the temperature in the stirring unit.
  • the U-shaped pulse can be suppressed more satisfactorily.
  • the U-shaped pulsation can be better suppressed over a long period of time.
  • the viscosity control unit and the temperature control unit may determine whether or not the above conditions are satisfied inside the manufacturing apparatus, or may be performed online or the like outside the manufacturing apparatus. Further, it is also possible to determine whether or not each of the above conditions is satisfied by using a trained model generated in advance by statistical machine learning.
  • the viscosity control unit and the temperature control unit may control other than the viscosity and temperature.
  • the liquid level of the polymerizable composition for an optical material in the stirring unit may be controlled. That is, when the liquid level of the polymerizable composition for optical materials is lowered, the liquid level is raised by feeding the polymerizable composition for optical materials by a fixed quantity liquid feeding unit (for example, a pump).
  • FIG. 1 is a flowchart showing an example of a control routine when shear force information is acquired by a viscosity control unit and a temperature control unit.
  • FIG. 2 is a flowchart showing an example of a control routine when the viscosity control unit and the temperature control unit acquire temperature information of the polymerizable composition for an optical material in the stirring unit.
  • FIG. 3 is a flowchart showing an example of a control routine when the viscosity control unit and the temperature control unit acquire information on a feature amount that correlates with the viscosity of the polymerizable composition for optical materials.
  • FIG. 4 is a flowchart showing an example of a control routine when the viscosity control unit and the temperature control unit acquire optical quality information of the cured product.
  • the optical material manufacturing system of the second embodiment starts from the state of preparing the first raw material composition and the second raw material composition, and sends the prepared first raw material composition and the second raw material composition to the shearing portion. do.
  • the first raw material composition and the second raw material composition contain two or more different monomers for optical materials and a polymerization catalyst as a whole. While flowing the fed first raw material composition and the second raw material composition, a force is applied to the first raw material composition and the second raw material composition in a direction intersecting the flow direction.
  • the viscosity control unit and the temperature control unit acquire information on the shear force of the shear unit.
  • the acquired shear force information is determined in step 210.
  • the viscosity control unit and the temperature control unit determine whether or not the shear force of the shear unit is equal to or higher than a certain value.
  • control is executed in step 220.
  • the viscosity control unit reduces the viscosity of the polymerizable composition for optical materials in the stirring unit to an appropriate range.
  • the temperature control unit raises the temperature in the stirring unit to an appropriate range.
  • the viscosity control unit and the temperature control unit control the viscosity of the polymerizable composition for optical materials in the stirring unit, which will be described later, and the temperature in the stirring unit, according to the shearing force of the shearing unit. That is, in steps 200 to 220, it is determined whether or not the above conditions are satisfied, and if not, the viscosity control unit determines the viscosity of the polymerizable composition for optical material in the stirring unit by the temperature control unit. The temperature in the stirring unit is controlled within an appropriate range. After the steps 200 to 220 are completed, the sheared polymerizable composition for optical materials is sent to the stirring unit.
  • the stirring unit while the polymerizable composition for optical materials is being flowed, a force is applied to the polymerizable composition for optical materials in a direction substantially parallel to the flow direction to stir, or the flow is temporarily made. Stop and stir the polymerizable composition for optical materials.
  • the viscosity control unit and the temperature control unit acquire the temperature information of the polymerizable composition for an optical material in the stirring unit.
  • the acquired temperature information is determined in step 240.
  • the viscosity control unit and the temperature control unit determine whether or not the temperature of the polymerizable composition for an optical material in the stirring unit is equal to or higher than a certain value.
  • control is performed in step 250.
  • the viscosity control unit raises the viscosity of the polymerizable composition for optical materials in the stirring unit within an appropriate range.
  • the temperature control unit lowers the temperature in the stirring unit to an appropriate range.
  • steps 230 to 250 in the viscosity control unit and the temperature control unit, the viscosity of the polymerizable composition for optical material in the stirring unit and the temperature in the stirring unit are set according to the temperature of the polymerizable composition for optical material in the stirring unit. Control.
  • the viscosity control unit and the temperature control unit acquire information on the feature amount that correlates with the viscosity of the polymerizable composition for optical materials.
  • the acquired information on the feature amount is determined in step 270. Specifically, it is determined whether or not the feature amount that correlates with the viscosity of the polymerizable composition for optical materials deviates from a certain range.
  • the feature amounts that correlate with the viscosity of the polymerizable composition for optical materials are, for example, the resistance value of the polymerizable composition for optical materials in the stirring section, the refractive index of the polymerizable composition for optical materials in the stirring section, and the stirring section. Examples thereof include the electric conductivity of the polymerizable composition for optical materials in the above, and the optical spectrum of the polymerizable composition for optical materials in the stirring section.
  • the viscosity control unit and the temperature control unit execute control in step 280 when the feature amount that correlates with the viscosity of the polymerizable composition for optical materials deviates from a certain range.
  • the viscosity control unit and the temperature control unit may directly measure the viscosity of the polymerizable composition for optical materials in the stirring unit, or may calculate from the feature amount that correlates with the viscosity of the polymerizable composition for optical materials. good.
  • As a method of calculating the viscosity of the polymerizable composition for optical materials in the stirring section from the feature amount that correlates with the viscosity of the polymerizable composition for optical materials for example, the resistance of the polymerizable composition for optical materials in the stirring section.
  • a method of calculating the viscosity from the value can be mentioned.
  • control executed in step 280 is a viscosity control in order to control the viscosity calculated from the feature amount within a certain range, for example, when the feature amount deviates from a certain range.
  • the viscosity of the polymerizable composition for an optical material in the stirring unit is controlled by the unit, and the temperature in the stirring unit is controlled by the temperature control unit within an appropriate range.
  • the shearing force of the shearing portion is adjusted, the stirring force of the stirring portion is adjusted, and the polymerizable composition for an optical material is adjusted.
  • Examples include methods such as discarding a part of the object and renewing it, adjusting the liquid feeding speed of the fixed-quantity liquid feeding unit in the optical material manufacturing system, and the like.
  • the method of discarding and renewing a part of the polymerizable composition for optical materials is specifically, for example, discharging at least a part of the polymerizable composition for optical materials in the stirring part from the casting part and optical. It is a method of replacing at least a part of a polymerizable composition for a material.
  • Examples of the method of controlling the temperature in the stirring unit within an appropriate range include a method of controlling the rotation speed of stirring in the stirring unit, a method of controlling the temperature of the water bath in the stirring unit, and the like.
  • the polymerizable composition for optical materials is sent to the casting section.
  • the polymerizable composition for optical materials is cast into a mold.
  • the polymerizable composition for an optical material is sent to the cured portion.
  • the polymerizable composition for optical materials is cured by polymerizing two or more different monomers for optical materials in the polymerizable composition for optical materials in the mold.
  • the viscosity control unit and the temperature control unit acquire the optical quality information of the cured product obtained by curing the polymerizable composition for an optical material in the cured unit.
  • the optical quality information of the cured product include information on whether or not a pulse is generated in the cured product.
  • the acquired optical quality information is determined in step 300. Specifically, for example, the viscosity control unit and the temperature control unit determine whether or not pulse is generated in the cured product. If the cured product has pulse, control is performed in step 310. Specifically, the viscosity control unit increases or decreases the viscosity of the polymerizable composition for optical materials in the stirring unit within an appropriate range.
  • the temperature control unit raises or lowers the temperature in the stirring unit within an appropriate range.
  • steps 290 to 310 it is determined whether or not pulse is generated in the cured product obtained by curing the polymerizable composition for an optical material in the cured portion, and when pulse is generated, it is determined. Increases or decreases the viscosity of the polymerizable composition for optical materials in the stirring unit by the viscosity control unit, and raises or lowers the temperature in the stirring unit by the temperature control unit. This routine is completed when step 310 is completed.
  • FIG. 5 is a schematic diagram for explaining an example of an optical material manufacturing system.
  • a first raw material composition and a second raw material composition for producing a polymerizable composition for an optical material are prepared.
  • the first raw material composition and the second raw material composition are stirred to become a polymerizable composition for an optical material containing two or more different monomers for an optical material and a polymerization catalyst. Therefore, the first raw material composition and the second raw material composition may become a polymerizable composition for an optical material when agitated, and there are two types of the first raw material composition and the second raw material composition as a whole. It suffices to include the above-mentioned different monomers for optical materials and a polymerization catalyst. Further, the first raw material composition and the second raw material composition may contain a prepolymer obtained by partially polymerizing two or more different monomers for optical materials.
  • the first raw material composition prepared above is placed in the liquid A tank 1, and the second raw material composition is placed in the liquid B tank 2. Then, while adjusting the liquid temperature with the chiller 3, the first raw material composition is transferred from the A liquid tank 1 to the A liquid measuring unit 4 (for example, a gear pump) and the second raw material composition is B liquid by using nitrogen back pressure or the like. Liquid is sent from the tank 2 to the liquid B measuring unit 6 (for example, a gear pump). At this time, the speeds of the liquid feeding of the liquid A measuring unit 4 and the liquid B measuring unit 6 may be the same or different.
  • the first raw material composition is sent from the liquid A measuring unit 4 via the flow rate sensor head 5 for the liquid A
  • the second raw material composition is sent from the liquid B measuring unit 6 via the flow rate sensor head 7 for the liquid B.
  • the liquid is sent to the upper power mixer 8 which is a shearing portion.
  • the first raw material composition and the second raw material composition are sheared by applying a force in a direction intersecting the flow direction by the upper power mixer 8 to obtain a polymerizable composition for an optical material.
  • the polymerizable composition for an optical material may be sheared by the upper power mixer 8, filtered by the capsule filter 10, and further sent to the lower power mixer 9 which is a sheared portion. Then, in the lower power mixer 9, the polymerizable composition for optical materials may be sheared. Further, the polymerizable composition for an optical material may be sheared by a plurality of power mixers as described above, or may be sheared by one power mixer. For example, the polymerizable composition for an optical material may be sheared only by the upper power mixer 8.
  • the polymerizable composition for an optical material is sheared by a lower power mixer 9, filtered by a capsule filter 10, and sent to a stirring tank 11 which is a stirring unit.
  • the stirring tank 11 includes a stirrer 12.
  • the polymerizable composition for optical materials is stirred by applying a force in substantially parallel and opposite directions in the flow direction. Then, the polymerizable composition for an optical material is further mixed or stirred with a static mixer 13, and then cast into a mold 14 which is a cured portion by a casting portion. Then, in the mold 14, two or more different monomers for optical materials in the polymerizable composition for optical materials are polymerized to cure the polymerizable composition for optical materials.
  • the control panel 15 in FIG. 5 is a viscosity control unit and a temperature control unit. In the control panel 15, it is determined whether or not each of the above conditions is satisfied, and the viscosity of the polymerizable composition for optical materials in the stirring unit is measured or calculated. Depending on the result, the viscosity and temperature can be controlled as described above. For example, by turning on the foot switch 16, at least a part of the polymerizable composition for optical materials in the stirring part is discharged from the casting part in order to replace at least a part of the polymerizable composition for optical materials. be able to.
  • FIG. 6 is a diagram showing a configuration example of a computer that realizes a viscosity control unit and a temperature control unit.
  • the viscosity control unit and the temperature control unit can be realized by, for example, a computer 60 as shown in FIG.
  • the computer 60 that realizes the viscosity control unit and the temperature control unit includes a central processing unit (CPU) 61, a memory 62 as a temporary storage area, and a non-volatile storage unit 63.
  • the computer has an input / output interface (I / F) 64 to which an input / output device or the like (not shown) is connected, and a read / write (R / W) unit 65 that controls reading and writing of data to the recording medium 68.
  • I / F input / output interface
  • R / W read / write
  • the computer includes a network I / F66 connected to a network such as the Internet.
  • the CPU 61, the memory 62, the storage unit 63, the input / output I / F64, the R / W unit 65, and the network I / F66 are connected to each other via the bus 67.
  • the storage unit 63 can be realized by a Hard Disk Drive (HDD), a Solid State Drive (SSD), a flash memory, or the like.
  • a program for operating the computer is stored in the storage unit 63 as a storage medium.
  • the CPU 61 reads the program from the storage unit 63, expands the program into the memory 62, and sequentially executes the processes included in the program. As a result, the control routines of FIGS. 1 to 4 are realized.
  • a film is attached to the outer peripheral surfaces of two molded substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two molded substrates and the film.
  • the film comprises a space forming step of forming a space, an injection step of injecting the polymerizable composition into the space, and a curing step of curing the polymerizable composition injected into the space to obtain a cured product.
  • the film is a film that is completely peeled off from the glass when it is attached to glass and subjected to a heat resistance index test at 85 ° C., and the film has a thermal deformation temperature of 70 ° C. or higher.
  • the curing time is preferably 10 hours or less.
  • the method for manufacturing an optical member according to the third embodiment can manufacture an optical member having a smooth outer peripheral surface by including the above configuration.
  • the outer peripheral surface is smooth means that, for example, the outer peripheral surface of the cured product is mirror-like, the intersection of one main surface and the outer peripheral surface, and the other main surface and the outer peripheral surface. It is preferable that the shape between the intersections with the surfaces is substantially straight.
  • the method for manufacturing an optical member according to the third embodiment it is possible to manufacture an optical member having a smooth outer peripheral surface without performing polishing work or with a small amount of polishing.
  • the film in the third embodiment is a film having a relatively weak static adhesive force. Therefore, when the polymerizable composition is cured and shrunk in the curing step, it can be moved to the mold substrate on the contact surface with the film. Therefore, it is possible to suppress phenomena such as the contact surface between the film and the polymerizable composition being dented or uneven on the inner side.
  • the pressure-sensitive adhesive in a film having a relatively weak static adhesive force may elute into the polymerizable composition.
  • the pressure-sensitive adhesive eluted in the polymerizable composition can cause cloudiness, voids, etc. in the obtained cured product.
  • the cloudiness, voids, and the like can be satisfactorily suppressed by combining the above configurations.
  • the curing step of the third embodiment when the curing time is 10 hours or less, the elution amount of the pressure-sensitive adhesive tends to be remarkably suppressed, and the white turbidity, voids and the like can be suppressed better. can.
  • the space forming step in the third embodiment is a step of attaching a film to the outer peripheral surfaces of two molded substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two molded substrates and the film. Is. An example of the space forming process will be described with reference to FIG. 7.
  • FIG. 7 is a schematic diagram for explaining the space forming process.
  • a lens casting polymerization type 110 is produced.
  • a first mold substrate 111 for forming a convex surface and a second mold substrate 112 for forming a concave surface made of glass are prepared.
  • the outer diameters of the molded substrates 111 and 112 may be the same as the finished outer diameter dimensions of the plastic lens.
  • the film (for example, adhesive tape) 113 is wound around the outer peripheral surfaces of the mold substrates 111 and 112 a little more than one round, and the mold substrates 111 and 112 are adhered. It is fixed with tape and closes the gap between the molded substrates 111 and 112.
  • the film 113 may be a heat-peeling type or a re-peeling type adhesive tape.
  • a mold is used.
  • a film is attached to the outer peripheral surfaces of two mold substrates arranged so as to face each other at predetermined intervals, and the two mold substrates and the film are used.
  • the mold is for producing an optical member by forming an enclosed space, arranging the polymerizable composition in the space, and curing the polymerizable composition to obtain a cured product.
  • the mold in the third embodiment preferably has a main surface having a substantially diameter of 60 cm to 80 cm.
  • the method for manufacturing an optical member according to the third embodiment when used, it is possible to manufacture an optical member having a smooth outer peripheral surface without performing polishing work or with a small amount of polishing. Therefore, the substantially diameter of the main surface of the mold can be reduced by the amount that the polishing work is not performed.
  • the film (also referred to as a film for manufacturing an optical member) according to the third embodiment is used.
  • the film is attached to the outer peripheral surfaces of two molded substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two molded substrates and the film, and the space is formed. It is preferable that the film is for producing an optical member for producing an optical member by arranging the polymerizable composition in the film and curing the polymerizable composition in 10 hours or less to obtain a cured product.
  • the film (also referred to as a film for manufacturing an optical member) in the third embodiment preferably includes at least a base material layer and an adhesive layer.
  • the film in the third embodiment is a film that is completely peeled off from the glass when it is attached to glass and subjected to a heat resistance index test at 85 ° C.
  • the heat resistance index test can measure the static adhesive strength of the film.
  • the film in the third embodiment is a film that completely peels off from the glass when it is attached to glass and subjected to a heat resistance index test at 85 ° C., so that static adhesive force can be suppressed.
  • the film in the third embodiment is a film having a relatively weak static adhesive force.
  • the specific method of the heat resistance index test is as follows. (Method) At room temperature, of the exposed surface of the adhesive layer of the film having a width of 25 mm ⁇ 0.5 mm and a length of 80 mm ⁇ 0.5 mm, the part having an area of 625 mm 2 ⁇ 25 mm 2 was brought into close contact with the glass plate, and the load was 1 kg / cm 2 . Crimping. Then, a weight of 1 kg was attached to the end of the folded portion of the film which was not in close contact with the glass plate, and the glass plate was installed in a constant temperature bath at a temperature of 85 ° C. so as to be in the vertical direction. Thirty minutes after being placed in the constant temperature bath, the position of the upper end of the tape is measured, and the moving distance (mm) from the position immediately after attaching the 1 kg weight is calculated as the heat resistance index.
  • the heat resistance index is preferably 0.4 mm or less, and more preferably 0.3 mm or less.
  • the film can satisfactorily fix the molded substrate.
  • the film in the third embodiment may have a heat resistance index of 0 or more when the heat resistance index test is performed at 22 ° C.
  • the film in the third embodiment preferably has a heat distortion temperature of 70 ° C. or higher, and preferably a maximum temperature of the mold in the curing step.
  • the heat distortion temperature is 70 ° C. or higher, an optical member having a smooth outer peripheral surface can be manufactured.
  • the heat distortion temperature is preferably 80 ° C. or higher, more preferably 90 ° C. or higher, further preferably 120 ° C. or higher, and particularly preferably 150 ° C. or higher.
  • the heat distortion temperature may be 500 ° C. or lower, or 400 ° C. or lower.
  • the heat distortion temperature conforms to ASTM-D648-56 and is measured with a load of 4.6 kgf ⁇ cm 2 using a heat distortion temperature measuring device.
  • the film in the third embodiment preferably has a moving distance of the glass balls of 200 mm or less when the glass ball tack test is performed at 80 ° C.
  • the glass ball tack test can measure the dynamic adhesive strength of the film.
  • the film in the third embodiment is excellent in dynamic adhesive strength because the moving distance of the glass balls is 200 mm or less when the glass ball tack test is performed at 80 ° C. Thereby, the film in the third embodiment can better fix the molded substrate.
  • the glass ball tack test in the third embodiment is performed using a ball tack tester in accordance with JIS-Z0237.
  • the film in the third embodiment preferably has a moving distance of the glass balls of 200 mm or less when the glass ball tack test is performed at 25 ° C to 80 ° C. That is, when the glass ball tack test is performed at 25 ° C to 80 ° C, it is preferable that the moving distance of the glass ball is 200 mm or less in all the temperature ranges of 25 ° C to 80 ° C. It is also preferable that the film in the third embodiment has a moving distance of the glass balls of 200 mm or less when the glass ball tack test is performed at 120 ° C.
  • the film in the third embodiment preferably has a moving distance of the glass balls of 10 mm or more, more preferably 20 mm or more. It is more preferably 30 mm or more.
  • the moving distance of the glass balls is within the above range, the distance between the molded substrates becomes small at a suitable speed during curing, and leakage of the polymerizable composition is less likely to occur.
  • the problem that the adhesive layer of the tape remains on the outer peripheral surface of the cured product also referred to as adhesive residue
  • adhesive residue is less likely to occur.
  • the film in the third embodiment preferably has a storage elastic modulus at 80 ° C. of 1.0 ⁇ 10 10 Pa or more, more preferably 2.0 ⁇ 10 10 Pa or more, and more preferably 3.0 ⁇ 10 It is more preferably 10 Pa or more.
  • the film in the third embodiment preferably has a storage elastic modulus at 80 ° C. of 10.0 ⁇ 10 10 Pa or less, more preferably 8.0 ⁇ 10 10 Pa or less, and 6.0 ⁇ 10 It is more preferably 10 Pa or less.
  • Measurement method DMA single cantilever measurement / test model: DMA8000 ⁇ Test temperature: 0 to 120 ° C -Frequency: 1.0Hz ⁇ Temperature rise rate: 3 ° C / min ⁇ Measurement area: 1.2 (cm 2 ) ⁇ Distance between chucks: 12.5 mm
  • the injection step in the third embodiment is a step of injecting the polymerizable composition into the space.
  • An example of the injection process will be described with reference to FIG. FIG. 8 is a schematic view for explaining the injection process.
  • the adhesive tape 113 is peeled off to the extent that there is a gap in which the polymerizable composition can be injected into the cavity 114, the polymerizable composition 120 is injected into the cavity 114 through the gap, and the polymer composition 120 is injected again.
  • the gap is sealed with the adhesive tape 113.
  • the temperature in the injection step is preferably 30 ° C. or lower, more preferably 27 ° C. or lower, and even more preferably 25 ° C. or lower.
  • the temperature in the injection step is preferably 15 ° C. or higher, more preferably 18 ° C. or higher, and even more preferably 20 ° C. or higher.
  • the polymerizable composition in the third embodiment may be a polymerizable composition containing two or more different monomers for optical materials and a polymerization catalyst.
  • the slope of the thickening curve of the polymerizable composition at 25 ° C. is 0.4 or more, the time for contact between the relatively low-viscosity polymerizable composition and the film can be shortened.
  • the elution amount of the pressure-sensitive adhesive can be suppressed, and cloudiness, voids and the like can be suppressed more satisfactorily.
  • the slope of the thickening curve of the polymerizable composition is 0.5 or more, and further preferably 0.6 or more at 25 ° C.
  • the polymerizable composition according to the third embodiment is excellent in handleability of the polymerizable composition because the slope of the thickening curve is 8.0 or less at 25 ° C. From the same viewpoint as described above, it is more preferable that the slope of the thickening curve of the polymerizable composition is 7.0 or less, and further preferably 6.0 or less at 25 ° C.
  • the slope of the thickening curve at 25 ° C. of the polymerizable composition is measured by the following method.
  • the polymerizable composition is placed in a water bath temperature controlled at 25 ° C. and stirred. After that, the viscosity is measured at regular time intervals (for example, every 5 minutes, 1 hour, etc.) under the condition of 60 rpm with a B-type viscometer.
  • the polymerizable composition of the third embodiment contains two or more kinds of monomers for different optical materials and a polymerization catalyst, and the content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more kinds of monomers for different optical materials is It is preferably 0.010 part by mass to 2.0 parts by mass, and the viscosity measured with a B-type viscosity meter at 25 ° C. and 60 rpm is preferably 10 mPa ⁇ s to 1000 mPa ⁇ s.
  • the polymerizable composition of the third embodiment may contain two or more different monomers for optical materials.
  • the monomer for an optical material may be any monomer used for optics and is not particularly limited. For example, it may be a monomer used for producing an optical material having any of the following properties.
  • the optical material obtained by using the monomer for an optical material may have a total light transmittance of 10% or more.
  • the total light transmittance of the optical material may be measured in accordance with JIS K 7631-1 (1997).
  • the optical material obtained by using the monomer for an optical material may have a haze (that is, total haze) of 10% or less, preferably 1% or less, and more preferably 0.5% or less.
  • the haze of the optical material is a value measured at 25 ° C. using a haze measuring machine [TC-HIII DPK, manufactured by Tokyo Denshoku Co., Ltd.] in accordance with JIS-K7105.
  • the optical material obtained by using the monomer for an optical material has a refractive index of preferably 1.58 or more.
  • the optical material obtained by using the monomer for an optical material may have a refractive index of 1.80 or less, or may be 1.75 or less.
  • the refractive index of the optical material may be measured according to JIS K7142 (2014).
  • the shape of the optical material obtained by using the monomer for the optical material is not particularly limited, and may be a plate shape, a columnar shape, a rectangular parallelepiped shape, or the like.
  • Examples of the monomer for an optical material include a polymerizable monomer that polymerizes when a polymerization catalyst described later is used.
  • the details of the specific example, preferred embodiment, preferable content, etc. of the monomer for optical material in the third embodiment are the same as the details of the specific example, preferred embodiment, preferable content, etc. of the monomer for optical material in the first embodiment. ..
  • isocyanate compound examples include an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound, and a heterocyclic isocyanate compound, and one type or a mixture of two or more types is used. These isocyanate compounds may include dimers, trimers and prepolymers. Examples of these isocyanate compounds include the compounds exemplified in International Publication No. 2011/0555540.
  • examples of the isocyanate compound include halogen-substituted products (for example, chlorine-substituted products, bromine-substituted products, etc.), alkyl-substituted products, alkoxy-substituted products, carbodiimide-modified products, urea-modified products, and burette-modified products of the above-mentioned compounds.
  • halogen-substituted products for example, chlorine-substituted products, bromine-substituted products, etc.
  • alkyl-substituted products for example, alkyl-substituted products, alkoxy-substituted products, carbodiimide-modified products, urea-modified products, and burette-modified products of the above-mentioned compounds.
  • the definitions of the alicyclic isocyanate compound, the aromatic isocyanate compound, the heterocyclic isocyanate compound and the aliphatic isocyanate compound in the third embodiment are defined as the alicyclic isocyanate compound, the aromatic isocyanate compound, the heterocyclic isocyanate compound and the alicyclic isocyanate compound in the first embodiment. Similar to the definition of aliphatic isocyanate compounds.
  • the isocyanate compound preferably contains at least one selected from the group consisting of an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound and a heterocyclic isocyanate compound.
  • At least one kind of the monomer for optical materials in the third embodiment may be an isocyanate compound having an aromatic ring.
  • the isocyanate compound having an aromatic ring include an aromatic isocyanate compound, more specifically, an isocyanate compound in which an isocyanate group is directly bonded to the aromatic ring, and an isocyanate compound at the benzyl position of the aromatic ring. Examples thereof include an isocyanate compound to which a group is bonded.
  • the monomer for an optical material may contain an isocyanate compound other than the isocyanate compound having an aromatic ring, that is, an isocyanate compound having no aromatic ring.
  • the isocyanate compound other than the isocyanate compound having an aromatic ring is not particularly limited, and examples thereof include an isocyanate compound having no aromatic ring.
  • the monomer for optical material contains an isocyanate compound having no aromatic ring and an isocyanate compound having an aromatic ring
  • the number of moles of the isocyanate group in the isocyanate compound having no aromatic ring is the isocyanate group in the isocyanate compound having an aromatic ring. It is preferably less than the number of moles of.
  • the isocyanate compound is isophorone diisocyanate, 2,5-bis (isocyanatomethyl) bicyclo- [2. 2.1] -Heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -Heptane, m-xylylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate , Dicyclohexylmethane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate.
  • Isophorone diisocyanate 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, m-xyli It may contain at least one selected from the group consisting of range isocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, dicyclohexylmethane diisocyanate, and 1,3-bis (isosyanatomethyl) cyclohexane.
  • polythiol compound having two or more mercapto groups Specific examples of the polythiol compound having two or more mercapto groups in the third embodiment, preferable embodiments, preferable contents and the like are details of the specific examples of the polythiol compound having two or more mercapto groups in the first embodiment, preferable. It is the same as the details such as an embodiment and a preferable content.
  • polythiol compound having 3 or more mercapto groups examples include polythiol compounds having three or more mercapto groups.
  • the polymerizable composition of the third embodiment contains a polythiol compound having three or more mercapto groups as the active hydrogen compound, the polymerizable composition is contained in the polythiol compound having three or more mercapto groups from the viewpoint of accelerating the polymerization reaction. It is preferable that at least one of the three or more mercapto groups is substituted with a group represented by the following formula (N1) (also referred to as compound (N1)).
  • the polymerizable composition of the third embodiment has a peak area of 100 of the polythiol compound having three or more mercapto groups when the peak area is measured by high performance liquid chromatography from the viewpoint that the polymerization reaction can be easily adjusted.
  • the peak area of the compound (N1) is preferably 3.0 or less, and more preferably 1.5 or less.
  • the peak area of the compound (N1) is from the viewpoint of accelerating the polymerization reaction with respect to the peak area 100 of the polythiol compound having three or more mercapto groups. , 0.01 or more is preferable.
  • the peak area by high performance liquid chromatography can be measured by the method described in paragraph 0146 of International Publication No. 2014/027665.
  • Hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups Specific examples, preferred embodiments, preferred contents and the like of the hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups in the third embodiment are described in detail with the one or more mercapto groups in the first embodiment. It is the same as the details of the specific example of the hydroxythiol compound having one or more hydroxyl groups, a preferable embodiment, a preferable content and the like.
  • polyol compound containing two or more hydroxyl groups Specific examples, preferred embodiments, preferred contents and the like of the polyol compound having two or more hydroxyl groups in the third embodiment are specific examples of the polyol compound having two or more hydroxyl groups in the first embodiment, preferred embodiments. It is the same as the details such as a preferable content.
  • the pKa value is preferably 1 or more, more preferably 3 or more, and further preferably 4 or more.
  • the pKa value is preferably 9 or less, more preferably 8 or less.
  • the details of the specific examples, preferred embodiments, etc. of the organometallic catalyst in the third embodiment are the same as the details of the specific examples, preferred embodiments, etc. of the organometallic catalyst in the first embodiment.
  • the content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more different monomers for optical materials is 0.010 parts by mass or more, the polymerization reaction can be satisfactorily promoted, so that the polymerization reaction can be promoted in a short time. High quality optical materials can be obtained. Further, by satisfactorily promoting the polymerization reaction, it is possible to improve the releasability when the cured product is taken out from the mold. From the above viewpoint, the content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more different monomers for optical materials is preferably 0.02 parts by mass or more, and preferably 0.03 parts by mass or more. Is more preferable.
  • the handleability when injecting a polymerizable composition into a mold can be improved.
  • the content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more different monomers for optical materials is preferably 0.20 parts by mass or less, and preferably 0.10 parts by mass or less. Is more preferable, and it is further preferable that it is 0.09 part by mass or less.
  • the content of the polymerization catalyst may be appropriately set according to the type of the polymerization catalyst, the type and amount of the monomers (isocyanate compound, active hydrogen compound, other components, etc.) used, and the desired shape of the molded product. can.
  • the polymerization catalyst preferably satisfies the following condition 1.
  • -Ea / R is -7100 or more and -2900 or less.
  • Ea is the activation energy calculated by the Arrhenius plot from the reaction rate constants of the two or more different optical material monomers at two or more different temperatures, and R is the gas constant (8.314 J / mol / K). ).
  • the details of the significance of the condition 1 and the measurement method in the third embodiment are the same as the details of the significance of the condition 1 and the measurement method in the second embodiment.
  • the polymerizable composition of the third embodiment may contain any additive.
  • Optional additives include photochromic compounds, internal mold release agents, brewing agents, UV absorbers and the like. Details of specific examples of the photochromic compound, the internal mold release agent, the bluing agent, and the ultraviolet absorber in the third embodiment, preferable embodiments, and the like are described in detail in the photochromic compound, the internal mold release agent, the bluing agent, and the ultraviolet absorption in the first embodiment. The same applies to the details of specific examples of the agent, preferred embodiments, and the like.
  • the polymerizable composition of the third embodiment has a viscosity of 10 mPa ⁇ s or more measured under the condition of 25 ° C. and 60 rpm with a B-type viscometer from the viewpoint of suppressing pulse and elution of the pressure-sensitive adhesive. It is preferably 40 mPa ⁇ s or more, more preferably 70 mPa ⁇ s or more, further preferably 80 mPa ⁇ s or more, particularly preferably 100 mPa ⁇ s or more, and 120 mPa ⁇ s or more. Is even more preferable.
  • the polymerizable composition of the third embodiment has a viscosity of 1000 mPa ⁇ s or less measured under the condition of 25 ° C. and 60 rpm with a B-type viscometer from the viewpoint of maintaining good handleability when molding the optical material into a desired shape. It is preferably 700 mPa ⁇ s or less, and more preferably 400 mPa ⁇ s or less.
  • the viscosity of the polymerizable composition of the third embodiment may be adjusted depending on the intended use of the obtained cured product. For example, when a cured product is obtained by using a mold for a plus lens, the edge (or injection port) is narrow (for example, 1 mm to 3 mm), so that the polymerizable composition of the third embodiment is from the viewpoint of suppressing the viscosity.
  • the viscosity is preferably 10 mPa ⁇ s to 100 mPa ⁇ s.
  • the edge that is, the injection port
  • the edge is wide (for example, 5 mm to 15 mm), so that the polymerizable composition of the third embodiment has a pulse.
  • the viscosity is preferably 10 mPa ⁇ s to 1000 mPa ⁇ s, and more preferably 100 mPa ⁇ s to 1000 mPa ⁇ s.
  • the viscosity of the polymerizable composition By increasing the viscosity of the polymerizable composition, it is possible to suppress heat convection due to the temperature difference between the inside and outside of the composition when heat is applied to the composition from the outside, and the pulse derived from heat convection can be suppressed. Can be reduced. However, if the amount of catalyst is small, the thickening rate at the time of polymerization is not sufficient, so that the viscosity does not increase to the extent that heat convection can be suppressed, and the temperature cannot be raised rapidly in a short time. In addition, the time required to complete the polymerization also increases.
  • the viscosity of the entire composition can be increased more quickly by increasing the amount of the catalyst within the optimum range in consideration of the reactivity of the isocyanate compound.
  • heat convection due to a rapid temperature rise can be suppressed while suppressing unevenness in polymerization, and polymerization can proceed in a short time.
  • the polymerizable composition of the third embodiment is a B-type viscometer when the temperature of the polymerizable composition reaches 40 ° C. after the start of polymerization from the viewpoint of suppressing pulse and elution of the pressure-sensitive adhesive.
  • the viscosity measured at 40 ° C. and 60 rpm is preferably 100 mPa ⁇ s or more, more preferably 200 mPa ⁇ s or more, and even more preferably 500 mPa ⁇ s or more.
  • the polymerizable composition of the third embodiment has a B-type viscosity when the temperature of the polymerizable composition reaches 40 ° C. after the start of polymerization, from the viewpoint of maintaining good handleability when the polymerizable composition is injected.
  • the viscosity measured under the condition of 40 ° C. and 60 rpm in total is preferably 2000 mPa ⁇ s or less, and more preferably 1500 mPa ⁇ s or less.
  • the polymerizable composition of the third embodiment includes two or more kinds of monomers for different optical materials, a polymerization catalyst, and a prepolymer which is a polymer of two or more kinds of monomers for different optical materials and has a polymerizable functional group. It is preferable to include.
  • the prepolymer is a polymer of two or more different monomers for optical materials and has a polymerizable functional group.
  • a cured product obtained by polymerizing a prepolymer and two or more different monomers for optical materials can be used as an optical material.
  • the prepolymer for example, a polymer in which two kinds of monomers for optical materials are not polymerized at an equivalent ratio of 1: 1 among the monomers for optical materials, and two kinds of monomers for optical materials among the monomers for optical materials are balanced.
  • examples thereof include a polymer which is polymerized at an equivalent ratio in which the material is broken.
  • the above-mentioned polymerizable functional group is a functional group that can be polymerized with another polymerizable functional group, and specific examples thereof include functional groups having active hydrogen such as an isocyanate group and a mercapto group described later. ..
  • Polymerizing at an equivalent ratio of 1: 1 means that, for example, when polymerizing using an isocyanate compound and a polythiol compound, the isocyanate group of the isocyanate compound and the mercapto group of the polythiol compound become 1: 1 in molar ratio. It is to polymerize by the amount.
  • the curing step in the third embodiment is a step of curing the polymerizable composition injected into the space to obtain a cured product.
  • the method for producing an optical member according to the third embodiment includes a curing step, the polymerizable composition can be polymerized, and an optical material can be produced.
  • the curing time is preferably 10 hours or less.
  • the elution amount of the pressure-sensitive adhesive tends to be remarkably suppressed, and the white turbidity, voids and the like can be suppressed better. can.
  • the curing time in the third embodiment means the time from the time when the temperature of the polymerizable composition reaches 30 ° C. to the time when the polymerizable composition is completely cured.
  • the curing time is more preferably 7 hours or less, and further preferably 5 hours or less.
  • the curing time is preferably 1 hour or longer, more preferably 3 hours or longer.
  • the maximum curing temperature in the curing step is preferably 150 ° C. or lower, more preferably 130 ° C. or lower, further preferably 100 ° C. or lower, and particularly preferably 80 ° C. or lower.
  • the maximum curing temperature in the curing step is preferably 50 ° C. or higher, more preferably 60 ° C. or higher, and even more preferably 70 ° C. or higher.
  • FIG. 9 is a schematic diagram for explaining the movement of the molded substrate in the curing step.
  • the polymerizable composition 120 in the cavity 114 is cured.
  • the polymerizable composition 120 is polymerized by, for example, heating, active energy rays, or the like, and polymerization shrinkage occurs.
  • the film (for example, adhesive tape) 113 has a reduced holding force for holding the molded substrate.
  • the position where the upper mold substrate is mainly fixed in the space forming step due to the stress and its own weight due to the polymerization shrinkage of the polymerizable composition 120 in the cavity 114 (FIG. 9). It slides down from the inner surface of the film 113 (indicated by the broken line) and approaches the lower mold substrate. At this time, the amount of movement of the molded substrate is substantially equal to the amount of polymerization shrinkage of the polymerizable composition 120.
  • the volumetric shrinkage of the polymerizable composition 120 can be absorbed by the movement of the mold substrates 111 and 112, and the film 113 can be prevented from being deformed.
  • the shape of the film 113 that has not been deformed is transferred to the side surface of the obtained cured product (plastic lens) 130, resulting in a good-looking shape. Therefore, the outer diameters of the molded substrates 111 and 112 may be the same as the finished outer diameter dimensions of the plastic lens. This eliminates the waste of the outer peripheral portion of several mm, which has been conventionally scraped by the polishing work. In the case of a lens having a thick outer peripheral portion, the amount of the polymerizable composition can be reduced by more than 10%. In addition, there is an advantage that polishing work becomes unnecessary.
  • the polymerizable composition when the polymerization reaction is carried out, the polymerizable composition is heated to generate the polymerization reaction.
  • the polymerizable composition according to the third embodiment promotes the polymerization reaction of the monomer for optical material in the polymerizable composition by generating the reaction heat (that is, the heat due to self-heating) associated with the polymerization reaction in a short time. You can also. Therefore, in the method for producing an optical member according to the third embodiment, heating of the polymerizable composition is not always necessary, but heating may be performed. That is, in the curing step of the third embodiment, the polymerizable composition can be cured by polymerization by allowing the polymerizable composition to stand still.
  • the reaction heat associated with the polymerization reaction (that is, the heat due to self-heating) is generated in a short time to accelerate the polymerization reaction of the monomer for optical material in the polymerizable composition
  • the polymerization time can be shortened. ..
  • the reaction heat associated with the polymerization reaction (that is, the heat due to self-heating) is generated in a short time to accelerate the polymerization reaction of the monomer for optical material in the polymerizable composition
  • the curing time is several hours. It is often completed in up to 20 hours.
  • the curing step it is preferable to cure the polymerizable composition by allowing the polymerizable composition injected into the space to stand in a closed space.
  • a cured product having an excellent edge condition can be obtained.
  • the polymerizable composition by allowing the polymerizable composition to stand in the closed space, it is possible to prevent the heat generated by the self-heating of the polymerizable composition from being released to the outside. As a result, the heat generated by self-heating can be retained in the closed system space, so that the polymerization reaction can be promoted more efficiently, and the optical material can be produced in a shorter time.
  • the closed space include a heat insulating environment.
  • the adiabatic environment refers to an environment in which heat is retained inside and heat conduction between the inside and the outside is suppressed.
  • An environment in which heat conduction between the inside and the outside is suppressed means that when the polymerizable composition is allowed to stand in the closed system space, the heat conduction between the inside and the outside of the closed system space is the polymerizable composition. It means an environment in which an object can be cured.
  • the adiabatic environment can be formed, for example, using an adiabatic material. That is, by allowing the polymerizable composition to stand in a heat insulating container made of a heat insulating material, heat can be retained inside the heat insulating container and heat conduction between the inside and the outside can be suppressed.
  • the thermal conductivity of the heat insulating material is preferably 0.50 W / mK or less, more preferably 0.10 W / mK or less, and even more preferably 0.05 W / mK or less.
  • the density of the heat insulating material is preferably 10 kg / m 3 or more, more preferably 15 kg / m 3 or more, and further preferably 20 kg / m 3 or more.
  • the adiabatic reaction tank it is preferable to heat the adiabatic reaction tank to bring it into a constant temperature state (constant temperature reaction tank).
  • the environmental temperature in the reaction vessel (constant temperature reaction vessel) in which the mold is placed can be kept warm or constant temperature according to the temperature rise state due to the self-heating of the monomer for optical material. The polymerization reaction can be promoted satisfactorily.
  • the adiabatic reaction tank or the constant temperature reaction tank as described above can be used.
  • adiabatic polymerization in an adiabatic environment using an adiabatic reaction vessel can be performed by the following procedure. can.
  • the inner surface of the vacuum vessel is covered with a member having heat insulating and heat-retaining properties such as urethane foam and cork, and the mold in which the monomer is injected is wrapped with a member such as a waste cloth as needed. Then, the mold in which the monomer is injected is allowed to stand in the vacuum container.
  • the curing step may be a step of curing the polymerizable composition by allowing the polymerizable composition to stand without being heated from the outside.
  • heating of the polymerizable composition is not always necessary.
  • an apparatus may be used, which may increase the burden economically.
  • the optical material can be manufactured by a simple method, so that the economic burden can be reduced.
  • the curing step is preferably a step of curing the polymerizable composition by allowing the polymerizable composition to stand for 2 to 10 hours.
  • the polymerization reaction is carried out over several hours to several tens of hours (for example, about 20 hours to 48 hours) while gradually raising the temperature by heating.
  • the time for carrying out the polymerization reaction is short, the optical material cannot be obtained because the polymerizable composition is not completely cured, or the quality of the optical material is deteriorated.
  • the optical material can be manufactured in a short time while maintaining the quality of the obtained optical material. Specifically, the optical material can be produced by allowing the polymerizable composition to stand for 10 hours or less.
  • the polymerizable composition it is more preferable to allow the polymerizable composition to stand for 8 hours or less in the curing step. Further, from the viewpoint of performing a polymerization reaction to obtain a well-cured optical material, it is preferable to allow the polymerizable composition to stand for 2 hours or more, and more preferably to allow it to stand for 5 hours or more.
  • a microwave irradiation step of irradiating the polymerizable composition with microwaves for a predetermined time may be provided.
  • the curing step in the third embodiment there is an aspect including the step b described as one aspect of the curing step in the first embodiment.
  • the cured product of the third embodiment is a cured product of the polymerizable composition of the third embodiment.
  • the cured product of the third embodiment preferably has an amine content of 0.03% by mass or more, preferably 0.05% by mass, from the viewpoint of reducing pulse. The above is more preferable, and 0.07% by mass or more is further preferable.
  • the cured product of the third embodiment preferably has an amine content of 2.5% by mass or less, preferably 2.0% by mass or less, from the viewpoint of improving the handleability of the polymerizable composition for optical materials. Is more preferable, and 1.5% by mass or less is further preferable.
  • the amine content is the amine content measured by gas chromatograph mass spectrometry from the dichloromethane composition in which the cured product is dispersed in dichloromethane and ultrasonically extracted.
  • the cured product of the third embodiment preferably has a tin content of 0.05% by mass or more, preferably 0.1% by mass or more, when an organotin catalyst is used. It is more preferably present, and more preferably 0.2% by mass or more. Further, the cured product of the third embodiment preferably has a tin content of 2.5% by mass or less, preferably 2.0% by mass or less, from the viewpoint of improving the handleability of the polymerizable composition for optical materials. Is more preferable, and 1.5% by mass or less is further preferable.
  • the cured product of the third embodiment preferably has, for example, an amine content measured by gas chromatograph mass spectrometry of 0.03% by mass or more and 2.5% by mass or less.
  • the method for measuring the amine content in the cured product is as follows. 200 mg of the cured product powdered with a metal file and 3 mL of dichloromethane are placed in a centrifuge tube (volume 10 mL), ultrasonically extracted for 10 minutes at room temperature using an ultrasonic washer (UCHI, US-4), and centrifuged. Centrifuge is performed at 4000 rpm for 10 minutes using a separator (KUBOTA, desktop small centrifuge 2410). The supernatant is collected, the residue is dispersed again in 3 mL of dichloromethane, the above ultrasonic extraction and centrifugation are performed, and the supernatant is collected (hereinafter, also referred to as “residue extraction”).
  • the above-mentioned amine means an amine compound that can be used as a polymerization catalyst, or an amine compound derived from the above-mentioned amine compound.
  • the cured product of the third embodiment preferably has a devitrification of less than 50, more preferably less than 35.
  • the devitrification is measured by the following method.
  • a light source in a dark place for example, Luminar Ace manufactured by Hayashi Repic Co., Ltd.
  • Light from LA-150A is transmitted.
  • the image of the light transmitted through the cured product is taken into an image processing device (for example, an image processing device manufactured by Ube Information Systems Co., Ltd.), the captured image is subjected to shading processing, and the degree of shading of the processed image is determined for each pixel.
  • the devitrification is the value calculated as the average value of the numerical values of the degree of shading of each pixel.
  • the cured product of the third embodiment preferably has no veins having a length of 1.0 mm or more within a radius of 15 mm from the center of the cured product, and is within or outside the range of a radius of 15 mm from the center of the cured product. It is more preferable that there is no radius of 1.0 mm or more.
  • the cured product of the third embodiment is a cured product of two or more different optical monomers, and at least one of the two or more different optical material monomers has an aromatic ring. It is an isocyanate compound that does not have a pulse with a length of 1.0 mm or more within a radius of 15 mm from the center of the cured product, and the amine content measured by gas chromatograph mass analysis is 0.03% by mass or more. It may be a cured product having an amount of 2.5% by mass or less.
  • the cured product of the third embodiment is a cured product of two or more different optical monomers, and has no veins having a length of 1.0 mm or more within a radius of 15 mm from the center of the cured product.
  • the outer peripheral surface of the cured product is mirror-like, and the shape between the intersection of one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface is preferably a substantially straight line.
  • the cured product of the third embodiment preferably contains a protrusion substantially parallel to the outer peripheral surface at the intersection of the one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface. ..
  • a small gap is often provided in the mold at the intersection of the main surface of one mold and the film and the intersection of the main surface of the other mold and the film (also referred to as chamfering).
  • the protrusion is a portion formed by the polymerizable composition entering the gap and being cured.
  • the cured product of the third embodiment preferably contains at least one selected from the group consisting of urethane resin, thiourethane resin and episulfide resin, and more preferably contains thiourethane resin.
  • the method for producing an optical member according to the third embodiment may include an annealing step of annealing the cured polymerizable composition, if necessary.
  • the temperature at which the annealing treatment is performed is usually 50 to 150 ° C, preferably 90 to 140 ° C, and more preferably 100 to 130 ° C.
  • the cured product in the third embodiment can be suitably used as an optical member.
  • the optical member in the third embodiment may have a thickness of 1 mm to 20 mm or 4 mm to 16 mm.
  • the optical member in the third embodiment can be used for a plastic lens, a prism, an optical fiber, an information recording board, a filter, a light emitting diode and the like.
  • the optical member according to the third embodiment can be suitably used for a plastic lens, and can be preferably used for a plastic lens for spectacles.
  • a film is attached to the outer peripheral surfaces of two molded substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two molded substrates and the film.
  • the film comprises a space forming step of forming a space, an injection step of injecting the polymerizable composition into the space, and a curing step of curing the polymerizable composition injected into the space to obtain a cured product.
  • the heat resistance index is 1 mm or more (except when it is completely peeled off from the glass), and the film has a thermal deformation temperature of 120 ° C. or less. ..
  • the curing time is preferably 10 hours or less.
  • the polymerizable composition preferably has an inclination of a thickening curve of 0.4 or more at 25 ° C.
  • the method for manufacturing an optical member according to the fourth embodiment can manufacture an optical member having a smooth outer peripheral surface by including the above configuration.
  • the outer peripheral surface is smooth means that, for example, the outer peripheral surface of the cured product is mirror-like, the intersection of one main surface and the outer peripheral surface, and the other main surface and the outer peripheral surface. It is preferable that the shape between the intersections with the surface is a concave curve.
  • an optical member having a smooth outer peripheral surface without performing polishing work or with a small amount of polishing.
  • the polymerizable composition is cured and shrunk in the curing step, it is possible to prevent the molded substrate from moving on the contact surface with the film. Therefore, the contact surface between the film and the polymerizable composition can be recessed inward.
  • the pressure-sensitive adhesive in the film may elute into the polymerizable composition.
  • the pressure-sensitive adhesive eluted in the polymerizable composition can cause cloudiness, voids, etc. in the obtained cured product.
  • the cloudiness, voids, and the like can be satisfactorily suppressed by combining the above configurations.
  • the curing step of the fourth embodiment when the curing time is 10 hours or less and the viscosity of the polymerizable composition is a certain level or more as described later, the elution amount of the pressure-sensitive adhesive tends to be remarkably suppressed. It is possible to better suppress the above-mentioned wrinkles, cloudiness, voids and the like.
  • a mold is used.
  • the details of the specific embodiment, the preferred embodiment, etc. of the mold in the fourth embodiment are the same as the details of the specific embodiment, the preferred embodiment, etc. of the mold in the third embodiment.
  • the film (also referred to as a film for manufacturing an optical member) according to the fourth embodiment is used.
  • the film is attached to the outer peripheral surfaces of two molded substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two molded substrates and the film, and the space is formed. It is preferable that the film is for producing an optical member for producing an optical member by arranging the polymerizable composition in the film and curing the polymerizable composition in 10 hours or less to obtain a cured product.
  • the film (also referred to as a film for manufacturing an optical member) in the fourth embodiment preferably includes at least a base material layer and an adhesive layer.
  • the film in the fourth embodiment has a heat resistance index of 1 mm or more when it is attached to glass and subjected to a heat resistance index test at 85 ° C. (except when it is completely peeled off from the glass).
  • the heat resistance index test can measure the static adhesive strength of the film.
  • the film in the fourth embodiment is static because it has a heat resistance index of 1 mm or more (except when it is completely peeled off from the glass) when it is attached to glass and subjected to a heat resistance index test at 85 ° C.
  • the adhesive strength can be adjusted satisfactorily. That is, it is possible to prevent the molded substrate from moving on the contact surface with the film when the polymerizable composition is cured and shrunk in the curing step. Therefore, the contact surface between the film and the polymerizable composition can be recessed inward.
  • the heat resistance index is preferably 2 mm or more, and more preferably 3 mm or more.
  • the upper limit of the heat resistance index is not particularly limited as long as it does not completely peel off from the glass.
  • the heat resistance index is preferably 15 mm or less, more preferably 10 mm or less, and further preferably 7 mm or less.
  • the specific method of the heat resistance index test in the fourth embodiment is the same as the specific method of the heat resistance index test in the third embodiment.
  • Heat distortion temperature Details of the heat distortion temperature of the film, the preferred range of the glass ball tack test, the measurement method, etc. in the fourth embodiment are described in detail of the heat distortion temperature of the film, the preferred range of the glass ball tack test, the measurement method, etc. in the third embodiment. Is similar to.
  • the film in the fourth embodiment preferably has a storage elastic modulus at 80 ° C. of 3.0 ⁇ 10 10 Pa or more, more preferably 5.0 ⁇ 10 10 Pa or more, and 7.0 ⁇ 10 It is more preferably 10 Pa or more.
  • the film in the fourth embodiment preferably has a storage elastic modulus at 80 ° C. of 40.0 ⁇ 10 10 Pa or less, more preferably 30.0 ⁇ 10 10 Pa or less, and 20.0 ⁇ 10 It is more preferably 10 Pa or less.
  • the specific example of the detailed conditions of the storage elastic modulus measurement test in the fourth embodiment is the same as the specific example of the detailed conditions of the storage elastic modulus measurement test in the third embodiment.
  • the adhesive strength of the adhesive layer is preferably 1.0 N / 10 mm to 10.0 N / 10 mm, preferably 2.0 N / 10 mm to 7.0 N / 10 mm. Is more preferable, and 3.0N / 10mm to 5.0N / 10mm is even more preferable. Adhesive strength is measured according to JIS Z 0237: 2009.
  • the polymerizable composition of the fourth embodiment may be a polymerizable composition containing two or more different monomers for optical materials and a polymerization catalyst.
  • the polymerizable composition in the fourth embodiment preferably has a thickening curve with a slope of 0.4 or more at 25 ° C.
  • the preferred range of the slope of the thickening curve of the polymerizable composition at 25 ° C. in the fourth embodiment, the measurement method and the like are described in detail in the preferred range of the slope of the thickening curve of the polymerizable composition at 25 ° C. in the third embodiment. , The details of the measurement method, etc. are the same.
  • the polymerizable composition of the fourth embodiment contains two or more kinds of monomers for different optical materials and a polymerization catalyst, and the content of the polymerization catalyst with respect to a total of 100 parts by mass of the two or more kinds of monomers for different optical materials is It is preferably 0.010 part by mass to 2.0 parts by mass, and the viscosity measured with a B-type viscosity meter at 25 ° C. and 60 rpm is preferably 10 mPa ⁇ s to 1000 mPa ⁇ s.
  • the isocyanate compound preferably contains at least one selected from the group consisting of an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound and a heterocyclic isocyanate compound.
  • the isocyanate compound does not contain an aromatic isocyanate compound.
  • the monomer for an optical material contains an aromatic isocyanate compound and a polythiol compound having four or more functionalities from the same viewpoint as described above.
  • polythiol compound having two or more mercapto groups Specific examples of the polythiol compound having two or more mercapto groups in the fourth embodiment, preferable embodiments, preferable contents and the like are details of the specific examples of the polythiol compound having two or more mercapto groups in the third embodiment, preferable. It is the same as the details such as an embodiment and a preferable content.
  • Polythiol compound having 3 or more mercapto groups Specific examples of the polythiol compound having three or more mercapto groups in the fourth embodiment, preferable embodiments, preferable contents and the like are details of the specific examples of the polythiol compound having three or more mercapto groups in the third embodiment, preferable. It is the same as the details such as an embodiment and a preferable content.
  • Hydroxythiol compound containing one or more mercapto groups and one or more hydroxyl groups Specific examples, preferred embodiments, preferred contents and the like of the hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups in the fourth embodiment refer to the one or more mercapto groups in the third embodiment. It is the same as the details of the specific example of the hydroxythiol compound having one or more hydroxyl groups, a preferable embodiment, a preferable content and the like.
  • polyol compound containing two or more hydroxyl groups Specific examples, preferred embodiments, preferred contents and the like of the polyol compound having two or more hydroxyl groups in the fourth embodiment are specific examples of the polyol compound having two or more hydroxyl groups in the third embodiment, preferred embodiments. It is the same as the details such as a preferable content.
  • organometallic catalyst (Organometallic catalyst)
  • the details of the specific examples, preferred embodiments, etc. of the organometallic catalyst in the fourth embodiment are the same as the details of the specific examples, preferred embodiments, etc. of the organometallic catalyst in the third embodiment.
  • the polymerizable composition of the fourth embodiment may contain any additive.
  • Optional additives include photochromic compounds, internal mold release agents, brewing agents, UV absorbers and the like. Details of specific examples of the photochromic compound, the internal mold release agent, the bluing agent, and the ultraviolet absorber in the fourth embodiment, preferable embodiments, and the like are described in detail in the photochromic compound, the internal mold release agent, the bluing agent, and the ultraviolet absorption in the third embodiment. The same applies to the details of specific examples of the agent, preferred embodiments, and the like.
  • FIG. 10 is a schematic diagram for explaining a change in the shape of the film in the curing step.
  • the polymerizable composition 120 in the cavity 114 is cured.
  • the polymerizable composition 120 is polymerized by, for example, heating, active energy rays, or the like, and polymerization shrinkage occurs.
  • this polymerization shrinkage occurs most violently, the shape-retaining force for holding the shape of the film (for example, adhesive tape) 113 decreases.
  • the stress associated with the polymerization shrinkage of the polymerizable composition 120 in the cavity 114 causes the intersection of one main surface and the outer peripheral surface and the other main surface and the outer peripheral surface.
  • the shape of the film between the intersections is transformed into a concave curve.
  • the amount of deformation of the film is substantially equal to the amount of polymerization shrinkage of the polymerizable composition 120.
  • the volumetric contraction of the polymerizable composition 120 is made into a concave curve in the shape of the film between the intersection of one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface. Can be absorbed.
  • the side surface of the obtained cured product 130 forms a concave curve. Therefore, the outer diameters of the molded substrates 111 and 112 may be the same as the finished outer diameter dimensions of the plastic lens. This eliminates the waste of the outer peripheral portion of several mm, which has been conventionally scraped by the polishing work. In the case of a lens having a thick outer peripheral portion, the amount of the polymerizable composition can be reduced by more than 10%. In addition, there is an advantage that polishing work becomes unnecessary.
  • the polymerizable composition when the polymerization reaction is carried out, the polymerizable composition is heated to generate the polymerization reaction.
  • the polymerizable composition according to the fourth embodiment promotes the polymerization reaction of the monomer for optical material in the polymerizable composition by generating the reaction heat (that is, the heat due to self-heating) associated with the polymerization reaction in a short time.
  • the reaction heat that is, the heat due to self-heating
  • a specific embodiment a preferred embodiment, a definition of a closed system space and an adiabatic environment, a thermal conductivity and density of an adiabatic material, and polymerization regarding accelerating the polymerization reaction by using the reaction heat associated with the polymerization reaction in the third embodiment. It is the same as the details such as time.
  • the curing step in the fourth embodiment there is an aspect including the step b described as one aspect of the curing step in the third embodiment.
  • the method for producing an optical member according to the fourth embodiment may include an annealing step of annealing the cured polymerizable composition, if necessary.
  • the temperature at which the annealing treatment is performed is usually 50 to 150 ° C, preferably 90 to 140 ° C, and more preferably 100 to 130 ° C.
  • the cured product in the fourth embodiment can be suitably used as an optical member.
  • the optical member in the fourth embodiment may have a thickness of 1 mm to 20 mm or 4 mm to 16 mm.
  • the optical member in the fourth embodiment can be used for a plastic lens, a prism, an optical fiber, an information recording board, a filter, a light emitting diode and the like.
  • the optical member according to the fourth embodiment can be suitably used for a plastic lens, and can be preferably used for a plastic lens for spectacles.
  • the first embodiment will be specifically described with reference to Examples, but the first embodiment is not limited to these Examples.
  • the method for measuring the viscosity in the examples is the same as the above-mentioned method.
  • the following evaluation was performed on the molded product obtained in each Example or Comparative Example.
  • the molded product was projected with an ultra-high pressure mercury lamp (light source model OPM-252HEG: manufactured by Ushio, Inc.), and the transmitted image was visually observed and evaluated according to the following criteria.
  • the obtained polymerizable composition for optical materials was sent to a casting mold (that is, a mold) while being remixed in a static mixer.
  • the viscosity (also referred to as casting viscosity) of the polymerizable composition for an optical material when the liquid was sent to a mold and cast was adjusted to the value shown in Table 1.
  • a 4-curve or 6-curve glass mold (upper mold) having a diameter of 78 mm and a glass mold (upper mold) having a diameter of 78 mm are used while filtering the polymerizable composition for optical materials with a 1 ⁇ m PTFE filter.
  • Examples 2 to 4 Except for changing the polymerization catalyst amount and stirring time of the first mixed solution in the prepolymerization step to the values shown in Table 1 and adjusting the casting viscosity of the polymerizable composition for optical materials to the values shown in Table 1.
  • a molded product (lens) was obtained by the same method as in Example 1.
  • the viscosities of the mixture containing the prepolymer are shown in Table 1. Then, the mixture containing the prepolymer was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a first mixed solution. Pentaerythritol tetrakis (3-mercaptopropionate) [monomer for optical materials] 22.2 parts by mass, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] 23.7% by mass After charging the parts to prepare a mixed solution, the obtained mixed solution was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a second mixed solution.
  • the first mixed solution and the second mixed solution were mixed at 20 ° C. to obtain a polymerizable composition for an optical material.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the value shown in Table 1.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour.
  • the cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • Example 6 to 7 The contents of pentaerythritol tetrakis (3-mercaptopropionate) and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane in the prepolymerization step were changed to the values shown in Table 1 and polymerized for optical materials.
  • a molded product (lens) was obtained by the same method as in Example 5 except that the casting viscosity of the sex composition was adjusted to the values shown in Table 1.
  • Example 8 The cast was placed in a heat insulating container at 25 ° C. and allowed to stand for 3 hours for adiabatic polymerization, and then the cast was taken out from the heat insulating container and released by the same method as in Example 7. I got a body (lens).
  • Example 9 A molded product (lens) was obtained by the same method as in Example 7 except that the cast product was heated from 30 ° C. to 120 ° C. over time without adiabatic polymerization and heat-polymerized over 3 hours.
  • Example 10 to 11 The contents of pentaerythritol tetrakis (3-mercaptopropionate) and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane in the prepolymerization step were changed to the values shown in Table 1 and polymerized for optical materials.
  • a molded product (lens) was obtained by the same method as in Example 5 except that the casting viscosity of the sex composition was adjusted to the values shown in Table 1.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting was not subjected to adiabatic polymerization, and the time was from 10 ° C to 120 ° C. And heat polymerization was carried out over 38 hours. Then, a molded product (lens) was obtained by the same method as in Example 1.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • a preparatory step for preparing a total of 100 parts by mass of two or more different monomers for optical materials and a polymerization catalyst of 0.010 parts by mass to 2.0 parts by mass A part of two or more different monomers for optical materials and at least a part of a polymerization catalyst are mixed, and at least a part of a part of two or more different monomers for optical materials is polymerized to obtain a prepolymer.
  • a prepolymerization step of obtaining a mixture containing a prepolymer, and Optical containing at least two or more different optical material monomers, a prepolymer, and a polymerization catalyst by adding the remainder of two or more different optical material monomers to the mixture containing the prepolymer.
  • a process for producing a polymerizable composition for an optical material for obtaining a polymerizable composition for a material A curing step of obtaining an optical material which is a cured product of a polymerizable composition for an optical material by curing two or more different monomers for an optical material in the polymerizable composition for an optical material.
  • Examples 2 to 4 and Examples 6 to 11 have a viscosity (that is, a casting viscosity) of the polymerizable composition for an optical material at the time of casting of 70 mPa ⁇ s or more. The optics could be suppressed better.
  • Example 12 JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), which is an acidic phosphoric acid ester, 0.03 part by mass, Tinuvin 329 [ultraviolet absorber] 1.5 parts by mass, and m-xylylene diisocyanate [monomer for optical material] 40.
  • a mixed solution was prepared by stirring 7 parts by mass at 25 ° C. for 1 hour to completely dissolve the mixture, and then, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9 was added to the mixed solution.
  • the monomer for optical materials was polymerized while adjusting the viscosity to obtain a first mixed solution containing a prepolymer.
  • the viscosities of the mixture containing the prepolymer are shown in Table 2.
  • a mixed solution was prepared by charging 10 parts by mass of m-xylylene diisocyanate [monomer for optical material] and 0.01 part by mass of 3,5-lutidine [polymerization catalyst]. This mixture was stirred at 25 ° C. for 15 minutes to obtain a second mixture. Then, the first mixed solution and the second mixed solution were mixed at 20 ° C. to obtain a polymerizable composition for an optical material.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the value shown in Table 2.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. Then, a molded product (lens) was obtained by the same method as in Example 1.
  • Example 13 Except for changing the polymerization catalyst amount and stirring time of the first mixed solution in the prepolymerization step to the values shown in Table 2 and adjusting the casting viscosity of the polymerizable composition for optical materials to the values shown in Table 2.
  • a molded product (lens) was obtained by the same method as in Example 12.
  • Example 14 JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), which is an acidic phosphoric acid ester, 0.03 parts by mass, Tinuvin 329 [ultraviolet absorber] 1.5 parts by mass, and m-xylylene diisocyanate [monomer for optical materials] 50.7
  • a mixed solution was prepared by charging parts by mass. The mixture was stirred at 25 ° C. for 1 hour to completely dissolve.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the values shown in Table 2.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • Examples 15 to 19 Polymerization catalyst amount in the prepolymerization step, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trichiaundecane and 4,7-dimercaptomethyl-1,11-dimercapto-3, Changed the content and stirring time of the mixture of 6,9-trichaundecane and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trichiaundecan to the values shown in Table 2.
  • a molded body (lens) was obtained by the same method as in Example 14 except that the casting viscosity of the polymerizable composition for optical materials was adjusted to the values shown in Table 2.
  • Example 20 The cast was placed in a heat insulating container at 25 ° C. and allowed to stand for 3 hours for adiabatic polymerization, and then the cast was taken out from the heat insulating container and released by the same method as in Example 19. I got a body (lens).
  • Example 21 A molded product (lens) was obtained by the same method as in Example 19 except that the cast product was heated from 30 ° C. to 120 ° C. over time without adiabatic polymerization and heat-polymerized over 3 hours.
  • the first mixed solution and the second mixed solution were mixed at 20 ° C. to obtain a polymerizable composition for an optical material.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the values shown in Table 2.
  • the cast material was not subjected to adiabatic polymerization, but was heated from 20 ° C. to 120 ° C. over time, and heat polymerization was carried out over 30 hours. Then, a molded product (lens) was obtained by the same method as in Example 1.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the values shown in Table 2.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • a prepolymerization step of obtaining a mixture containing a prepolymer, and Optical containing at least two or more different optical material monomers, a prepolymer, and a polymerization catalyst by adding the remainder of two or more different optical material monomers to the mixture containing the prepolymer.
  • a process for producing a polymerizable composition for an optical material for obtaining a polymerizable composition for a material A curing step of obtaining an optical material which is a cured product of a polymerizable composition for an optical material by curing two or more different monomers for an optical material in the polymerizable composition for an optical material.
  • Examples 11 to 12 and Examples 14 to 21 have a viscosity (that is, a casting viscosity) of the polymerizable composition for an optical material at the time of casting of 120 mPa ⁇ s or more. , I was able to suppress the optics better.
  • JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), which is an acidic phosphoric acid ester, 0.05 parts by mass, Tinuvin 329 [ultraviolet absorber] 1.5 parts by mass, and m-xylylene diisocyanate [monomer for optical materials] 52 parts by mass.
  • a mixed solution The mixture was stirred at 25 ° C. for 1 hour to completely dissolve.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the value shown in Table 3.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • Example 23 to 25 The content of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane in the prepolymerization step was changed to the value shown in Table 3, and the casting viscosity of the polymerizable composition for optical materials is shown in Table 3.
  • a molded product (lens) was obtained by the same method as in Example 22 except that the value was adjusted.
  • Example 26 The cast was placed in a heat insulating container at 25 ° C. and allowed to stand for 3 hours for adiabatic polymerization, and then the cast was taken out from the heat insulating container and released by the same method as in Example 25. I got a body (lens).
  • Example 27 A molded product (lens) was obtained by the same method as in Example 25 except that the cast product was heated from 30 ° C. to 120 ° C. over time without adiabatic polymerization and heat-polymerized over 3 hours.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the value shown in Table 3.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • a prepolymerization step of obtaining a mixture containing a prepolymer, and Optical containing at least two or more different optical material monomers, a prepolymer, and a polymerization catalyst by adding the remainder of two or more different optical material monomers to the mixture containing the prepolymer.
  • a process for producing a polymerizable composition for an optical material for obtaining a polymerizable composition for a material A curing step of obtaining an optical material which is a cured product of a polymerizable composition for an optical material by curing two or more different monomers for an optical material in the polymerizable composition for an optical material.
  • Example 28 Dicyclohexylmethane diisocyanate [monomer for optical material] 58.9 parts by mass, Tinuvin329 [ultraviolet absorber] 1.5 parts by mass, Mitsui Chemicals Co., Ltd.
  • MR internal mold release agent internal mold release agent 0.1 parts by mass A mixed solution was prepared in. The mixture was stirred at 25 ° C. for 1 hour to completely dissolve.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the value shown in Table 4.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 3 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 130 ° C. for 2 hours. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • a preparatory step for preparing a total of 100 parts by mass of two or more different monomers for optical materials and a polymerization catalyst of 0.010 parts by mass to 2.0 parts by mass A part of two or more different monomers for optical materials and at least a part of a polymerization catalyst are mixed, and at least a part of a part of two or more different monomers for optical materials is polymerized to obtain a prepolymer.
  • a process for producing a polymerizable composition for an optical material for obtaining a polymerizable composition for a material A curing step of obtaining an optical material which is a cured product of a polymerizable composition for an optical material by curing two or more different monomers for an optical material in the polymerizable composition for an optical material.
  • Example 29 1,3-Bis (isocyanismethyl) cyclohexane [monomer for optical material] 48 parts by mass, Tinuvin329 [ultraviolet absorber] 1.5 parts by mass, JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.) 0.18 parts by mass A mixed solution was prepared in. The mixture was stirred at 25 ° C. for 1 hour to completely dissolve. Then, 4.0 parts by mass of pentaerythritol tetrakis (2-mercaptoacetate) and 3.9 parts by mass of 2,5-bis (mercaptomethyl) -1,4-dithiane were added to this mixed solution, and 25 parts by mass was charged.
  • the mixture was stirred at ° C. for 5 minutes to obtain a uniform solution. Further, 0.1 part by mass of 3,5-lutidine [polymerization catalyst] was added to the obtained uniform solution, and the mixture was stirred at 40 ° C. for 3 hours to polymerize the monomer for optical material while adjusting the viscosity. A mixture containing the polymer was obtained. The viscosities of the mixture containing the prepolymer are shown in Table 5. Then, the mixture containing the prepolymer was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a first mixed solution.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • a process for producing a polymerizable composition for an optical material for obtaining a polymerizable composition for a material A curing step of obtaining an optical material which is a cured product of a polymerizable composition for an optical material by curing two or more different monomers for an optical material in the polymerizable composition for an optical material.
  • Examples 101 to 103 In the prepolymerization step, the isocyanate and thiol [monomer for optical material] shown in Table 6 are used in the amounts shown in Table 6, and 3,5-lutidine [polymerization catalyst] is used in the amounts shown in Table 6 to MR.
  • the internal mold release agent [release agent] was used in the amount shown in Table 6, and the amount of the monomer for the optical material added in the polymerizable composition for the optical material was adjusted as shown in Table 7, and the polymerization time was adjusted.
  • a molded body (lens) was obtained by the same method as in Example 5 except that the method was changed as shown in Table 6. The evaluation of the pulse is shown in Table 6.
  • Examples 104 to 105 In the prepolymerization step, the isocyanate and thiol [monomer for optical material] shown in Table 6 are used in the amounts shown in Table 6, and 3,5-lutidine [polymerization catalyst] is used in the amounts shown in Table 6, JP. -506H [mold release agent] was used in the amount shown in Table 6, and the amount of the monomer for the optical material added in the polymerizable composition for the optical material was adjusted as shown in Table 7, and the polymerization time and method were adjusted. A molded product (lens) was obtained in the same manner as in Example 22 except that the above was changed as shown in Table 6. The evaluation of the pulse is shown in Table 6.
  • Example 106 A mixed solution was prepared by charging 1.5 parts by mass of Tinuvin 329 [ultraviolet absorber] and 48.9 parts by mass of m-xylylene diisocyanate [monomer for optical material]. The mixture was stirred at 25 ° C. for 1 hour to completely dissolve. Then, 10.1 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] was added to this mixed solution, and the mixture was stirred at 25 ° C. for 5 minutes to prepare a uniform solution. did.
  • a mixed solution was prepared by charging 37.9 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 3.1 parts by mass of m-xylylene diisocyanate [monomer for optical material]. This was stirred at 25 ° C. for 5 minutes to give a uniform solution. Further, 0.005 parts by mass of 3,5-lutidine [polymerization catalyst] was added to the obtained uniform solution, and the mixture was stirred at 40 ° C. for 1 hour to polymerize the monomer for optical material while adjusting the viscosity. A mixture containing the polymer was obtained. The viscosities of the mixture containing the prepolymer are shown in Table 6.
  • This mixed solution was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a second mixed solution. Then, the first mixed solution and the second mixed solution were mixed at 20 ° C. to obtain a polymerizable composition for an optical material.
  • the liquid was sent to a casting mold by the same method as in Example 1, and the casting viscosity was adjusted to the value shown in Table 6.
  • the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for adiabatic polymerization. Then, the cast material was taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. The cured molded product was released from the mold mold and further subjected to annealing treatment at 120 ° C. for 2 hours to obtain a molded product (lens).
  • the evaluation of the pulse is shown in Table 6.
  • Example 107 to Example 108 In the prepolymerization step, the isocyanate and thiol [monomer for optical material] shown in Table 6 are used in the amounts shown in Table 6, and 3,5-lutidine [polymerization catalyst] is used in the amounts shown in Table 6, JP. -506H [mold release agent] was used in the amount shown in Table 6, and the amount of the monomer for the optical material added in the polymerizable composition for the optical material was adjusted as shown in Table 7, and the polymerization time and method were adjusted. A molded product (lens) was obtained in the same manner as in Example 14 except that the above was changed as shown in Table 6. The evaluation of the pulse is shown in Table 6.
  • the molded product was projected with an ultra-high pressure mercury lamp (light source model OPM-252HEG: manufactured by Ushio, Inc.), and the transmitted image was visually observed and evaluated according to the following criteria.
  • the monomer for optical material was polymerized while adjusting the viscosity to obtain a mixture containing a prepolymer. Then, the mixture containing the prepolymer was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a first raw material composition.
  • the viscosity Va of the first raw material composition is shown in Table 8.
  • a portion was charged, and the mixture was stirred at 25 ° C. for 15 minutes to prepare a uniform solution.
  • This mixed solution was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a second raw material composition.
  • the viscosity Vb of the second raw material composition is shown in Table 8.
  • the first raw material composition was placed in the first tank, and the second raw material composition was placed in the second tank. Using a gear pump, each composition was fed to a power mixer at the flow rates shown in Table 8. Next, after applying a shearing force to the first raw material composition and the second raw material composition sent by using a power mixer at the rotation speeds shown in Table 8, the filtration accuracy shown in Table 8 is obtained. It was passed through a capsule filter (manufactured by F-tech Inc.). The polymerizable composition for optical materials after passing through the filter is sent to a stirring tank and stirred in the stirring tank at the rotation speeds shown in Table 8 to obtain the polymerizable composition for optical materials.
  • a capsule filter manufactured by F-tech Inc.
  • the polymerization reaction was carried out by any of the following methods. -The mold after casting was placed in a heat insulating container at 25 ° C. and allowed to stand for 2 hours for heat insulating polymerization. Then, the cast material is taken out from the heat insulating container and further subjected to heat polymerization at 120 ° C. for 1 hour. -Using an oven, heat the cast mold from 30 ° C to 70 ° C over 1.5 hours, then heat from 70 ° C to 120 ° C over 0.5 hours, then heat the temperature for 1 hour. Heat polymerization is performed while maintaining the temperature at 120 ° C.
  • the mold was naturally cooled, the cured molded product was released from the mold, and further annealed at 120 ° C. for 2 hours to obtain a molded product (lens).
  • a raw material composition preparation step for preparing a second raw material composition for preparing a second raw material composition
  • a shearing step for producing a polymerizable composition for an optical material by applying a shearing force to the first raw material composition and the second raw material composition and polymerization for an optical material.
  • Examples using a curing step of curing a polymerizable composition for an optical material by polymerizing different monomers for an optical material and a method for producing an optical material including the above are excellent in evaluation of pulse and the optical material. I was able to suppress the U-shaped polymerization in.
  • the method for measuring the viscosity in the examples is the same as the above-mentioned method.
  • the method of the heat resistance index test in the examples is the same as the above-mentioned method.
  • the method for measuring the heat distortion temperature in the examples is the same as the above-mentioned method.
  • the method for measuring the storage elastic modulus in the examples is the same as the above-mentioned method.
  • the method of the glass ball tack test in the examples is the same as the above-mentioned method.
  • the method for measuring the adhesive strength in the examples is the same as the above-mentioned method.
  • the cured product (that is, the lens) obtained in each Example or Comparative Example was evaluated as follows. [Edge smoothness] The smoothness of the outer peripheral surface of the cured product was visually confirmed. The case where the outer peripheral surface has no unevenness with a depth of 1 mm or more was defined as A, and the case where the outer peripheral surface had irregularities with a depth of 1 mm or more was defined as B.
  • protrude It was visually confirmed whether or not the intersection of one main surface and the outer peripheral surface of the cured product and the intersection of the other main surface and the outer peripheral surface contained a protrusion substantially parallel to the outer peripheral surface. The case where the protrusion was confirmed was designated as A, and the case where the protrusion was not confirmed was designated as B.
  • the films used in this example are as follows. A: SLIONTEC # 6261 (manufactured by Maxell Co., Ltd.) B: Mending tape # 810 (manufactured by 3M Japan Ltd.) C: SLIONTEC 6263-73 (manufactured by Maxell Co., Ltd.) Details of each film are shown in Table 9.
  • Example 301 Mitsui Chemicals, Inc.
  • MR internal mold release agent 0.1 parts by mass
  • Tinuvin 329 0.1 parts by mass
  • 2,5 (6) -bis (isocyanatomethyl) -bicyclo -[2.2.1] -Heptane 50.6 parts by mass was charged to prepare a mixed solution. The mixture was stirred at 25 ° C. for 1 hour to completely dissolve.
  • Polymerization was carried out to obtain a mixture containing a prepolymer. Then, the mixture containing the prepolymer was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a first mixed solution. Pentaerythritol tetrakis (3-mercaptopropionate) [monomer for optical materials] 20.8 parts by mass, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical materials] 22.2% by mass After charging the parts to prepare a mixed solution, the obtained mixed solution was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a second mixed solution. Then, the first mixed solution and the second mixed solution were mixed at 20 ° C. to obtain a polymerizable composition. The obtained polymerizable composition had a thickening curve slope of 4.6822 at 25 ° C.
  • the films shown in Table 9 are attached to the outer peripheral surfaces of two mold substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two mold substrates and the film for casting. A mold was made.
  • the obtained polymerizable composition was remixed in a static mixer to form a 4-curve glass mold (upper mold) having a diameter of 80 mm and a 4-curve glass mold (lower mold) having a diameter of 80 mm. It was injected at a rate of 6 g / sec into the above space having a center thickness of 10 mm.
  • the viscosity (also referred to as casting viscosity) of the polymerizable composition when the liquid was sent to the mold and cast was adjusted to the value shown in Table 9.
  • the cast material was heated in an oven at the temperature and time shown in Table 9 to carry out polymerization.
  • the cured product was released from the mold and further annealed at 120 ° C. for 2 hours to obtain a cured product (lens).
  • Example 302 A lens was obtained in the same manner as in Example 301, except that the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for the curing time shown in Table 9 for heat insulating polymerization. The maximum curing temperature is shown in Table 9.
  • Example 303 JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.), which is an acidic phosphoric acid ester, 0.05 parts by mass, Tinuvin329 [ultraviolet absorber] 1.5 parts by mass, and m-xylylene diisocyanate [monomer for optical material] 52.0
  • a mixed solution was prepared by charging parts by mass. The mixture was stirred at 25 ° C. for 1 hour to completely dissolve. Then, 12.0 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane [monomer for optical material] was added to this mixed solution, and the mixture was stirred at 25 ° C. for 5 minutes to prepare a uniform solution.
  • the polymer catalysts shown in Table 9 are added to the obtained uniform solution so as to have the total amount shown in Table 9, and the mixture is stirred at 40 ° C. for 3 hours to prepare a monomer for an optical material while adjusting the viscosity. Polymerization was carried out to obtain a mixture containing a prepolymer. The viscosities of the mixture containing the prepolymer are shown in Table 9. Then, the mixture containing the prepolymer was degassed at 400 Pa and 25 ° C. for 1 hour to obtain a first mixed solution.
  • Example 304 A lens was obtained in the same manner as in Example 303, except that the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for the curing time shown in Table 9 for heat insulating polymerization. The maximum curing temperature is shown in Table 9.
  • Example 305 A lens was obtained in the same manner as in Example 303, except that JP-506H was charged in an amount of 0.1 parts by mass and the polymerization catalyst was charged in a total amount shown in Table 9. The maximum curing temperature is shown in Table 9. The obtained polymerizable composition had an inclination of the thickening curve of 0.9010 at 25 ° C.
  • the viscosity of the polymerizable composition measured at 40 ° C. and 60 rpm with a B-type viscometer when the temperature of the polymerizable composition reached 40 ° C. after the start of polymerization. It was 164 mPa ⁇ s.
  • Example 301 A lens was obtained in the same manner as in Example 301, except that the film was changed to the film shown in Table 9. The maximum curing temperature is shown in Table 9.
  • Example 302 A lens was obtained in the same manner as in Example 302, except that the film was changed to the film shown in Table 9. The maximum curing temperature is shown in Table 9.
  • the obtained solution was defoamed at 400 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, and then sent to a casting mold by the same method as in Example 301, and the casting viscosity is shown in Table 9. Adjusted to the value.
  • the cast material was heated in an oven at the temperature and time shown in Table 9 to carry out polymerization.
  • the cured product was released from the mold and further annealed at 120 ° C. for 2 hours to obtain a cured product (lens).
  • the maximum curing temperature is shown in Table 9.
  • the film comprises an injection step of injecting the polymerizable composition into the space and a curing step of curing the polymerizable composition injected into the space to obtain a cured product, and the film is attached to glass.
  • the film has a thermal deformation temperature of 70 ° C. or higher and a curing time of 10 hours or less in the curing step.
  • Comparative Examples 304 to 306 using a film that does not completely peel off from the glass when attached to glass and subjected to a heat resistance index test at 85 ° C. are inferior in the evaluation of edge smoothness, and the outer peripheral surface is smooth. It was not possible to manufacture a certain optical member.
  • the method for measuring the viscosity in the examples is the same as the above-mentioned method.
  • the method of the heat resistance index test in the examples is the same as the above-mentioned method.
  • the method for measuring the heat distortion temperature in the examples is the same as the above-mentioned method.
  • the method for measuring the storage elastic modulus in the examples is the same as the above-mentioned method.
  • the method of the glass ball tack test in the examples is the same as the above-mentioned method.
  • the method for measuring the adhesive strength in the examples is the same as the above-mentioned method.
  • the cured product (that is, the lens) obtained in each Example or Comparative Example was evaluated as follows. [Edge smoothness] The smoothness of the outer peripheral surface of the cured product was visually confirmed. In the cured product, the shape between the intersection of one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface is a concave curve, and the outer peripheral surface has no unevenness with a depth of 1 mm or more. year, In the cured product, the shape between the intersection of one main surface and the outer peripheral surface and the intersection of the other main surface and the outer peripheral surface is not a concave curve, or the outer peripheral surface has irregularities with a depth of 1 mm or more. Was set to B.
  • protrude It was visually confirmed whether or not the intersection of one main surface and the outer peripheral surface of the cured product and the intersection of the other main surface and the outer peripheral surface contained a protrusion substantially parallel to the outer peripheral surface. The case where the protrusion was confirmed was designated as A, and the case where the protrusion was not confirmed was designated as B.
  • the films used in this example are as follows.
  • D Cellotape (registered trademark) NO29NEW (manufactured by Nitto Denko KK)
  • Example 401 Mitsui Chemicals, Inc.
  • MR internal mold release agent 0.1 parts by mass
  • Tinuvin 329 0.1 parts by mass
  • 2,5 (6) -bis (isocyanatomethyl) -bicyclo -[2.2.1] -Heptane 50.6 parts by mass was charged to prepare a mixed solution. The mixture was stirred at 25 ° C. for 1 hour to completely dissolve.
  • the films shown in Table 10 are attached to the outer peripheral surfaces of two mold substrates arranged so as to face each other at predetermined intervals to form a space surrounded by the two mold substrates and the film for casting. A mold was made.
  • the obtained polymerizable composition was remixed in a static mixer to form a 4-curve glass mold (upper mold) having a diameter of 80 mm and a 4-curve glass mold (lower mold) having a diameter of 80 mm. It was injected at a rate of 6 g / sec into the above space having a center thickness of 10 mm.
  • the viscosity (also referred to as casting viscosity) of the polymerizable composition when the liquid was sent to the mold and cast was adjusted to the value shown in Table 10.
  • the cast product was heated in an oven at the temperature and time shown in Table 10 to carry out polymerization.
  • the cured product was released from the mold and further annealed at 120 ° C. for 2 hours to obtain a cured product (lens).
  • Example 402 A lens was obtained in the same manner as in Example 401, except that the cast material was placed in a heat insulating container at 25 ° C. and allowed to stand for the curing time shown in Table 10 for heat insulating polymerization. The maximum curing temperature is shown in Table 10.
  • the viscosity of the polymerizable composition measured at 40 ° C. and 60 rpm with a B-type viscometer when the temperature of the polymerizable composition reached 40 ° C. after the start of polymerization. It was 164 mPa ⁇ s.
  • Example 403 to Example 405 Comparative Example 402
  • a lens was obtained in the same manner as in Example 402, except that the film was changed to the film shown in Table 10.
  • the maximum curing temperature is shown in Table 10.
  • Example 401 A lens was obtained in the same manner as in Example 401, except that the film was changed to the film shown in Table 10.
  • the film comprises an injection step of injecting the polymerizable composition into the space and a curing step of curing the polymerizable composition injected into the space to obtain a cured product, and the film is attached to glass.
  • the heat resistance index test is performed at 85 ° C., the heat resistance index is 1 mm or more (except when it is completely peeled off from the glass), the film has a thermal deformation temperature of 120 ° C. or less, and the curing step.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • Casting Or Compression Moulding Of Plastics Or The Like (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Ce procédé de production d'un matériau optique utilise un total de 100 parties en masse de deux ou plus de deux monomères différents pour un matériau optique et de 0,010 à 2,0 parties en masse d'un catalyseur de polymérisation en tant que matières premières pour produire un matériau optique. Le procédé comprend : une étape de préparation destinée à préparer un total de 100 parties en masse de deux ou plus de deux monomères différents pour un matériau optique et de 0,010 à 2,0 parties en masse d'un catalyseur de polymérisation ; et une étape de pré-polymérisation consistant à mélanger une partie des deux ou plus de deux monomères différents pour un matériau optique et au moins une partie du catalyseur de polymérisation, et de polymérisation d'au moins une partie de la partie des deux ou plus de deux monomères différents pour un matériau optique de manière à obtenir un prépolymère, ce qui permet d'obtenir un mélange contenant le prépolymère.
PCT/JP2021/042848 2020-11-24 2021-11-22 Procédé de production de matériau optique, composition polymérisable pour matériau optique, système de production de matériau optique, procédé de production d'élément optique, film de production d'élément optique, moule de production d'élément optique et produit durci WO2022113955A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202180078034.0A CN116529048A (zh) 2020-11-24 2021-11-22 光学材料的制造方法、光学材料用聚合性组合物、光学材料制造系统、光学构件的制造方法、光学构件制造用膜、光学构件制造用模具及固化物
JP2022565339A JPWO2022113955A1 (fr) 2020-11-24 2021-11-22

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
JP2020-194660 2020-11-24
JP2020194660 2020-11-24
JP2021-084856 2021-05-19
JP2021084856 2021-05-19
JP2021-122743 2021-07-27
JP2021122743 2021-07-27
JP2021124696 2021-07-29
JP2021124697 2021-07-29
JP2021-124696 2021-07-29
JP2021-124697 2021-07-29

Publications (1)

Publication Number Publication Date
WO2022113955A1 true WO2022113955A1 (fr) 2022-06-02

Family

ID=81754608

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/042848 WO2022113955A1 (fr) 2020-11-24 2021-11-22 Procédé de production de matériau optique, composition polymérisable pour matériau optique, système de production de matériau optique, procédé de production d'élément optique, film de production d'élément optique, moule de production d'élément optique et produit durci

Country Status (2)

Country Link
JP (1) JPWO2022113955A1 (fr)
WO (1) WO2022113955A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014047334A (ja) * 2012-09-04 2014-03-17 Mitsubishi Gas Chemical Co Inc 光学材料用重合性組成物の製造方法
WO2014080750A1 (fr) * 2012-11-21 2014-05-30 三井化学株式会社 Procédé de production d'une résine polyuréthane

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014047334A (ja) * 2012-09-04 2014-03-17 Mitsubishi Gas Chemical Co Inc 光学材料用重合性組成物の製造方法
WO2014080750A1 (fr) * 2012-11-21 2014-05-30 三井化学株式会社 Procédé de production d'une résine polyuréthane

Also Published As

Publication number Publication date
JPWO2022113955A1 (fr) 2022-06-02

Similar Documents

Publication Publication Date Title
JP7141528B2 (ja) 光学材料用重合性組成物、光学材料用重合性プレポリマー組成物、硬化物及び光学材料の製造方法
WO2021153632A1 (fr) Composition polymérisable pour matériau optique, composition de prépolymère polymérisable pour matériau optique, objet durci, et procédé de fabrication de matériau optique
WO2021182526A1 (fr) Composition polymérisable pour matériau optique, composition polymérisable de prépolymère pour matériau optique, objet durci et procédé de production de matériau optique
JP6872086B1 (ja) 重合触媒の使用条件設定方法、重合条件設定方法、光学材料の製造方法
WO2022113955A1 (fr) Procédé de production de matériau optique, composition polymérisable pour matériau optique, système de production de matériau optique, procédé de production d'élément optique, film de production d'élément optique, moule de production d'élément optique et produit durci
WO2023120606A1 (fr) Procédé de fabrication d'un élément optique et produit durci
CN116529048A (zh) 光学材料的制造方法、光学材料用聚合性组合物、光学材料制造系统、光学构件的制造方法、光学构件制造用膜、光学构件制造用模具及固化物
WO2023163191A1 (fr) Méthode de production d'élément optique et élément optique
WO2023145685A1 (fr) Procédé de production de matériau optique
WO2024096030A1 (fr) Méthode de production d'élément optique et élément d'isolation thermique
JP2023094404A (ja) 光学材料用重合性組成物、光学材料用重合性プレポリマー組成物、硬化物及び光学材料の製造方法
CN118556196A (zh) 光学构件的制造方法及光学构件

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21897928

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022565339

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 202180078034.0

Country of ref document: CN

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21897928

Country of ref document: EP

Kind code of ref document: A1