WO2017026352A1 - 硬化性組成物及びその硬化物 - Google Patents

硬化性組成物及びその硬化物 Download PDF

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Publication number
WO2017026352A1
WO2017026352A1 PCT/JP2016/072818 JP2016072818W WO2017026352A1 WO 2017026352 A1 WO2017026352 A1 WO 2017026352A1 JP 2016072818 W JP2016072818 W JP 2016072818W WO 2017026352 A1 WO2017026352 A1 WO 2017026352A1
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WIPO (PCT)
Prior art keywords
curable composition
compound
curable
mold
weight
Prior art date
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Ceased
Application number
PCT/JP2016/072818
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English (en)
French (fr)
Japanese (ja)
Inventor
藤川武
福井貞之
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daicel Corp
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Daicel Corp
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Filing date
Publication date
Application filed by Daicel Corp filed Critical Daicel Corp
Priority to US15/751,951 priority Critical patent/US10988569B2/en
Priority to EP20184748.0A priority patent/EP3738739B1/en
Priority to EP16835049.4A priority patent/EP3336122B1/en
Priority to KR1020187004897A priority patent/KR20180039085A/ko
Priority to CN201680046146.7A priority patent/CN107922586B/zh
Publication of WO2017026352A1 publication Critical patent/WO2017026352A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • B29C33/00—Moulds or cores; Details thereof or accessories therefor
    • B29C33/42—Moulds or cores; Details thereof or accessories therefor characterised by the shape of the moulding surface, e.g. ribs or grooves
    • 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
    • B29C39/003—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor characterised by the choice of material
    • 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
    • B29C39/22—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
    • B29C39/36—Removing moulded 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
    • B29C39/38—Heating or cooling
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00009—Production of simple or compound lenses
    • B29D11/00278—Lenticular sheets
    • B29D11/00307—Producing lens wafers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00009—Production of simple or compound lenses
    • B29D11/0048—Moulds for lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2063/00—Use of EP, i.e. epoxy resins or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/24—Condition, form or state of moulded material or of the material to be shaped crosslinked or vulcanised
    • 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
    • B29L2011/0016—Lenses

Definitions

  • a silicone mold that is excellent in shape transferability and releasability and is transparent and can be used for a photocurable composition is widely used.
  • the present invention also provides the method for producing the optical component described above, wherein in step 1, the bottom portion is filled with the curable composition, and then the filled curable composition is defoamed.
  • a curable composition for producing an optical component by molding using a silicone mold which contains a curable compound and a cationic polymerization initiator, and the alicyclic epoxy compound (A) as the curable compound And the oxetane compound (B), the content of the oxetane compound (B) being 10 to 45% by weight of the total amount of the curable compound contained in the curable composition, and the total amount of the curable compound contained in the curable composition 90% by weight or more of the curable composition is a compound in which the SP value at 25 ° C. of Fedors is 9.0 (cal / cm 3 ) 1/2 or more.
  • the molecular weight of the oxetane compound (B) (in the case where the curable composition contains two or more compounds as the oxetane compound (B), 90% by weight or more thereof) has a molecular weight of 100 to 800.
  • the curable compound further contains a glycidyl ether-based epoxy compound (C), and the alicyclic epoxy compound (A), the oxetane compound (B), and the glycidyl ether-based epoxy compound (C).
  • the curable composition according to any one of [1] to [8], wherein the sum is 70% by weight or more of the total amount of the curable compound contained in the curable composition.
  • hydrocarbon group optionally containing an oxygen atom or a halogen atom in R 1 to R 18 at least one hydrogen atom in the above hydrocarbon group is substituted with a group having an oxygen atom or a group having a halogen atom.
  • the group etc. can be mentioned.
  • the group having an oxygen atom include hydroxyl group; hydroperoxy group; C 1-10 alkoxy group such as methoxy, ethoxy, propoxy, isopropyloxy, butoxy, isobutyloxy group; C 2-10 such as allyloxy group.
  • the SP value of component (A) and the curable composition of the present invention contain two or more compounds as component (A), they are 90% by weight or more (preferably 95% by weight or more, particularly preferably 99% or more).
  • the SP value of the compound is preferably 9.0 or more, for example 9.0 to 15, preferably 9.2 to 15, particularly preferably 9.5 to 15, and most preferably 9.6. ⁇ 14. Since the component (A) having the SP value in the above range hardly infiltrates into the silicone mold, when the curable composition containing the component (A) having the SP value in the above range is used, the silicone mold of the curable composition is used. Swelling can be suppressed, the durability of the silicone mold can be improved, and the number of service life can be increased.
  • the monovalent hydrocarbon group includes various substituents [for example, halogen atom, oxo group, hydroxyl group, substituted oxy group (for example, alkoxy group, aryloxy group, aralkyloxy group, acyloxy group, etc.), carboxyl group Substituted oxycarbonyl groups (alkoxycarbonyl groups, aryloxycarbonyl groups, aralkyloxycarbonyl groups, etc.), substituted or unsubstituted carbamoyl groups, cyano groups, nitro groups, substituted or unsubstituted amino groups, sulfo groups, heterocyclic groups, etc. ] May be included.
  • the hydroxyl group or carboxyl group may be protected with a protective group commonly used in the field of organic synthesis.
  • the molecular weight of component (B) and the curable composition of the present invention contain two or more compounds as component (B), it is 90% by weight or more (preferably 95% by weight or more, particularly preferably
  • the molecular weight of the compound of 99% by weight or more is, for example, 100 or more (for example, 100 to 800), and the upper limit of the molecular weight is preferably 700, particularly preferably 500, most preferably 300, and particularly preferably 200.
  • the curable composition containing the component (B) having a molecular weight in the above range is excellent in shape transferability and handleability.
  • the molecular weight exceeds the above range, the viscosity tends to increase and the handleability tends to decrease, and when the molecular weight falls below the above range, the shape transferability tends to decrease.
  • the curable composition of the present invention may further contain one or more glycidyl ether epoxy compounds (hereinafter sometimes referred to as “component (C)”) as the curable compound. It is preferable at the point which can improve the sclerosis
  • a sulfonium salt compound in that a cured product having excellent curability can be formed.
  • the cation moiety of the sulfonium salt compound include (4-hydroxyphenyl) methylbenzylsulfonium ion, triphenylsulfonium ion, diphenyl [4- (phenylthio) phenyl] sulfonium ion, and 4- (4-biphenylylthio) phenyl.
  • arylsulfonium ions such as -4-biphenylylphenylsulfonium ion and tri-p-tolylsulfonium ion (particularly, triarylsulfonium ion).
  • Y represents a phenyl group or a biphenylyl group.
  • Phf represents at least one hydrogen atom
  • BF 4 ⁇ [(Rf) k PF 6-k] - (Rf: alkyl group in which at least 80% are substituted with fluorine atoms of the hydrogen atom, k: 0 ⁇ 5 an integer), AsF 6 -, SbF 6 - and the like, etc. -, SbF 5 OH it can.
  • the thermal cationic polymerization initiator is a compound that generates an acid by heat treatment and initiates a curing reaction of the curable compound contained in the curable composition, and a cationic part that absorbs heat and a source of the acid It consists of an anion part.
  • a thermal cationic polymerization initiator can be used individually by 1 type or in combination of 2 or more types.
  • the content of the surface modifier (when two or more types are contained, the total amount thereof) is, for example, 0.01 to 3 parts by weight with respect to the total amount (100 parts by weight) of the curable compound contained in the curable composition.
  • the amount is preferably 0.03 to 2 parts by weight, particularly preferably 0.1 to 1 part by weight.
  • the total amount of the curable compound contained in the curable composition of the present invention is a compound having an SP value of 9.0 or more. Therefore, the content of the compound having an SP value of less than 9.0 in the total amount of the curable compound contained in the curable composition of the present invention is 10% by weight or less, preferably 5% by weight or less, particularly preferably 1 % By weight or less.
  • the compound having an SP value of 9.5 or more is 50% by weight or more (for example, 50 to 80% by weight, preferably 55 to 80% by weight) of the total amount of the curable compound contained in the curable composition.
  • the average SP value of all curable compounds contained in the curable composition of the present invention is, for example, 9.55 or more, and preferably 10.00 or more.
  • the upper limit of the average SP value is, for example, 10.50, preferably 10.30, particularly preferably 10.10.
  • the average SP value is below the above range, it becomes difficult to suppress the swelling of the silicone mold by the curable composition, and it tends to be difficult to improve the durability of the silicone mold.
  • the average SP value exceeds the above range, the viscosity of the curable composition becomes too high, and it tends to be difficult to suppress foaming.
  • the silicone mold Since the curable composition of the present invention contains the curable compound having the above SP value in the above range, the silicone mold hardly infiltrates into the silicone mold and suppresses the swelling of the silicone mold due to the infiltration of the curable composition. The shape of the mold can be maintained, and the durability of the mold can be improved.
  • the viscosity (at 25 ° C., shear rate 20 (1 / s)) of the curable composition of the present invention is, for example, 100 to 1000 mPa ⁇ s, and the upper limit of the viscosity is preferably 500 mPa ⁇ s, particularly preferably. 400 mPa ⁇ s, most preferably 350 mPa ⁇ s, and the lower limit of the viscosity is preferably 130 mPa ⁇ s, particularly preferably 150 mPa ⁇ s, and most preferably 170 mPa ⁇ s.
  • the cured product of the present invention is obtained by curing the above curable composition. Curing is performed, for example, by subjecting the curable composition to light irradiation and / or heat treatment.
  • the cured product of the present invention is excellent in transparency, and the transmittance of light having a wavelength of 400 nm is, for example, 80% or more, preferably 85% or more, and more preferably 90% or more.
  • the cured product of the present invention is excellent in heat resistance, and can maintain excellent transparency even after being subjected to a heat resistance test.
  • the transmittance of light having a wavelength of 400 nm after being subjected to the heat resistance test described in the embodiment three times continuously is, for example, 90% or more of the transmittance of light having a wavelength of 400 nm before being subjected to the heat resistance test. , Preferably 95% or more, particularly preferably 98% or more. That is, the reduction rate (or yellowing rate) of light having a wavelength of 400 nm due to the heat resistance test is, for example, 10% or less, preferably 5% or less, and more preferably 1% or less. .
  • the optical component of the present invention comprises the above cured product.
  • the optical components of the present invention include optical components [flash lenses, light diffusion lenses, imaging lenses, etc. used in portable electronic devices (smartphones, tablet terminals, etc.), in-vehicle electronic devices, various sensors (infrared sensors, etc.), etc. Or a lens such as a sensor lens (especially a Fresnel lens), a prism or the like].
  • the material of the mold examples include metal, glass, plastic, silicone, and the like.
  • a material for the bottom of the mold among others, it has transparency, so it can be used for molding a photocurable composition, and it is a silicone mold (for example, polydimethyl) because it has excellent shape transferability and releasability. Silicone molds made from siloxane are preferred.
  • the said curable composition is used in this invention, since the swelling of the silicone mold by a curable composition can be suppressed, a silicone mold can be used repeatedly and an optical component is manufactured at low cost. be able to.
  • the silicone mold can be produced, for example, by pouring a silicone resin into a mold having the shape of a desired optical component and curing it.
  • the optical device of the present invention is a device provided with the above optical component.
  • the optical device include portable electronic devices such as mobile phones, smartphones, tablet PCs, infrared sensors, near infrared sensors, millimeter wave radars, LED spot illumination devices, near infrared LED illumination devices, mirror monitors, In-vehicle electronic devices such as a meter panel, a head-mounted display (projection type) combiner, and a head-up display combiner
  • the obtained bicyclohexyl-3,3′-diene (243 g) and ethyl acetate (730 g) were charged into a reactor, and nitrogen was blown into the gas phase portion, and the temperature in the reaction system was controlled to 37.5 ° C. Then, 274 g of 30 wt% peracetic acid in ethyl acetate (water content: 0.41 wt%) was added dropwise over about 3 hours. After completion of the dropwise addition, the reaction was terminated by aging at 40 ° C. for 1 hour.
  • Silicone resin (trade name “KE-1606”, manufactured by Shin-Etsu Chemical Co., Ltd.) is mixed with a curing agent (trade name “CAT-RG”, manufactured by Shin-Etsu Chemical Co., Ltd.), and then the above mold is set. It was poured into the mold and cured by holding at 60 ° C. for 24 hours and at 150 ° C. for 1 hour to prepare a silicone mold (bottom). Subsequently, a support (10 mm ⁇ 10 mm glass substrate) was prepared, and an adhesive (trade name “Cemedine 8000”, manufactured by Cemedine Co., Ltd.) was applied on the support to a thickness of 1.0 mm to obtain. The silicone mold (bottom part) was bonded together, heated at 80 ° C. for 2 hours to cure the adhesive, and a silicone mold (bottom part) fixed to the support was produced. Moreover, the silicone mold (lid part) fixed to the support body was produced by the same method as the bottom part, except that a mold having a flat surface was used.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Mechanical Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Epoxy Resins (AREA)
  • Polyethers (AREA)
PCT/JP2016/072818 2015-08-13 2016-08-03 硬化性組成物及びその硬化物 Ceased WO2017026352A1 (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US15/751,951 US10988569B2 (en) 2015-08-13 2016-08-03 Curable composition and cured product from same
EP20184748.0A EP3738739B1 (en) 2015-08-13 2016-08-03 Curable composition and cured product from same
EP16835049.4A EP3336122B1 (en) 2015-08-13 2016-08-03 Curable composition and cured product from same
KR1020187004897A KR20180039085A (ko) 2015-08-13 2016-08-03 경화성 조성물 및 그의 경화물
CN201680046146.7A CN107922586B (zh) 2015-08-13 2016-08-03 固化性组合物及其固化物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015159894A JP6286396B2 (ja) 2015-08-13 2015-08-13 硬化性組成物及びその硬化物
JP2015-159894 2015-08-13

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Publication Number Publication Date
WO2017026352A1 true WO2017026352A1 (ja) 2017-02-16

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PCT/JP2016/072818 Ceased WO2017026352A1 (ja) 2015-08-13 2016-08-03 硬化性組成物及びその硬化物

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US (1) US10988569B2 (enExample)
EP (2) EP3336122B1 (enExample)
JP (1) JP6286396B2 (enExample)
KR (1) KR20180039085A (enExample)
CN (1) CN107922586B (enExample)
TW (1) TWI705882B (enExample)
WO (1) WO2017026352A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110869819A (zh) * 2017-07-11 2020-03-06 株式会社大赛璐 菲涅耳透镜及其制造方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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JP6204420B2 (ja) * 2015-08-07 2017-09-27 株式会社ダイセル 硬化性組成物、及びそれを用いた光学素子
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