JP5415371B2 - 光学レンズ用光硬化型樹脂組成物およびそれを用いた光学レンズ - Google Patents
光学レンズ用光硬化型樹脂組成物およびそれを用いた光学レンズ Download PDFInfo
- Publication number
- JP5415371B2 JP5415371B2 JP2010158039A JP2010158039A JP5415371B2 JP 5415371 B2 JP5415371 B2 JP 5415371B2 JP 2010158039 A JP2010158039 A JP 2010158039A JP 2010158039 A JP2010158039 A JP 2010158039A JP 5415371 B2 JP5415371 B2 JP 5415371B2
- Authority
- JP
- Japan
- Prior art keywords
- component
- resin composition
- photocurable resin
- epoxy resin
- optical lens
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000011342 resin composition Substances 0.000 title claims description 57
- 230000003287 optical effect Effects 0.000 title claims description 53
- 239000003822 epoxy resin Substances 0.000 claims description 42
- 229920000647 polyepoxide Polymers 0.000 claims description 42
- -1 oxetane compound Chemical class 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- 239000003999 initiator Substances 0.000 claims description 21
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 9
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims description 7
- 125000005409 triarylsulfonium group Chemical group 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 238000001723 curing Methods 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 10
- 229920003023 plastic Polymers 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 150000002921 oxetanes Chemical class 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012778 molding material Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- MQOOPAYPXFMXGW-UHFFFAOYSA-N 1-(3-ethyloxetan-3-yl)-4-[(3-ethyloxetan-3-yl)methoxy]-3,3-dimethylbutan-2-ol Chemical compound C1OCC1(CC)CC(O)C(C)(C)COCC1(CC)COC1 MQOOPAYPXFMXGW-UHFFFAOYSA-N 0.000 description 1
- ZVVZJRGGIIJWBL-UHFFFAOYSA-N 1-(3-ethyloxetan-3-yl)-5-[(3-ethyloxetan-3-yl)methoxy]pentan-2-ol Chemical compound C1OCC1(CC)CC(O)CCCOCC1(CC)COC1 ZVVZJRGGIIJWBL-UHFFFAOYSA-N 0.000 description 1
- ALADOYDDKFXPNF-UHFFFAOYSA-N 1-[(3-ethyloxetan-3-yl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CCC1(COC1)CN2C(=O)NC(=O)NC2=O ALADOYDDKFXPNF-UHFFFAOYSA-N 0.000 description 1
- MKNOYISMZFDLQP-UHFFFAOYSA-N 3-[1-[2-(oxetan-3-yl)butoxy]butan-2-yl]oxetane Chemical compound C1OCC1C(CC)COCC(CC)C1COC1 MKNOYISMZFDLQP-UHFFFAOYSA-N 0.000 description 1
- WWJKCARUHXVBFE-UHFFFAOYSA-N 3-ethyl-1-(3-ethyloxetan-3-yl)-3-[(3-ethyloxetan-3-yl)methoxymethyl]heptan-2-ol Chemical compound C1OCC1(CC)CC(O)C(CC)(CCCC)COCC1(CC)COC1 WWJKCARUHXVBFE-UHFFFAOYSA-N 0.000 description 1
- YJCMPXJZAZXTTN-UHFFFAOYSA-N 3-ethyl-3-[[2-[(3-ethyloxetan-3-yl)methoxy]phenoxy]methyl]oxetane Chemical compound C=1C=CC=C(OCC2(CC)COC2)C=1OCC1(CC)COC1 YJCMPXJZAZXTTN-UHFFFAOYSA-N 0.000 description 1
- FHFOJGCIXOUQMZ-UHFFFAOYSA-N 3-ethyl-3-[[3-[(3-ethyloxetan-3-yl)methoxy]phenoxy]methyl]oxetane Chemical compound C=1C=CC(OCC2(CC)COC2)=CC=1OCC1(CC)COC1 FHFOJGCIXOUQMZ-UHFFFAOYSA-N 0.000 description 1
- YHPAMUSAWICJEZ-UHFFFAOYSA-N 3-ethyl-3-[[6-[(3-ethyloxetan-3-yl)methoxy]-2,2,3,3,4,4,5,5-octafluorohexoxy]methyl]oxetane Chemical compound C1OCC1(CC)COCC(F)(F)C(F)(F)C(F)(F)C(F)(F)COCC1(CC)COC1 YHPAMUSAWICJEZ-UHFFFAOYSA-N 0.000 description 1
- VOLHPVISRZJKBP-UHFFFAOYSA-N 3-ethyl-3-[[7-[(3-ethyloxetan-3-yl)methoxy]naphthalen-2-yl]oxymethyl]oxetane Chemical compound C=1C=C2C=CC(OCC3(CC)COC3)=CC2=CC=1OCC1(CC)COC1 VOLHPVISRZJKBP-UHFFFAOYSA-N 0.000 description 1
- CZCMFVCUVXQGJN-UHFFFAOYSA-N C(C)C1(COC1)COC1=C(C=CC=C1)C1=C(C=CC=C1)OCC1(COC1)CC.C(C)C1(COC1)COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC1(COC1)CC Chemical group C(C)C1(COC1)COC1=C(C=CC=C1)C1=C(C=CC=C1)OCC1(COC1)CC.C(C)C1(COC1)COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC1(COC1)CC CZCMFVCUVXQGJN-UHFFFAOYSA-N 0.000 description 1
- SOPOOVUSFZRKMF-UHFFFAOYSA-N C(C)C1(COC1)COC1=CC=C(C=C1)OCC1(COC1)CC.C(C)C1(COC1)COCCCCO Chemical compound C(C)C1(COC1)COC1=CC=C(C=C1)OCC1(COC1)CC.C(C)C1(COC1)COCCCCO SOPOOVUSFZRKMF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 229920006352 transparent thermoplastic Polymers 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/105—Onium compounds
-
- 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
- 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
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1525—Four-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyethers (AREA)
- Epoxy Resins (AREA)
Description
(A)1分子中に2個以上のエポキシ基を有し、脂環式骨格及び/又はビスフェノール骨格を有する、室温で液状のエポキシ樹脂。
(B)下記の一般式(1)で表されるオキセタン化合物。
(A)1分子中に2個以上のエポキシ基を有し、脂環式骨格及び/又はビスフェノール骨格を有する、室温で液状のエポキシ樹脂。
(B)下記の一般式(1)で表されるオキセタン化合物。
脂環式エポキシ樹脂(ダイセル化学社製、セロキサイド2021P、室温で液状を示す)
水添ビスフェノールA型液状エポキシ樹脂(エポキシ価:205g/eq.、)
ビスフェノールA型液状エポキシ樹脂(エポキシ価:185g/eq.、粘度10000mPa・s、)
ビスフェノールF型エポキシ樹脂(エポキシ価:159g/eq.、粘度1240mPa・s)
前記一般式(1)中、n=4で示されるオキセタン化合物
3−メチル−3−ヒドロキシメチルオキセタン
ビス(3−エチル−3−オキセタニルメチル)エーテル
3−エチル−3−フェノキシメチルオキセタン
下記の構造式(2)で表されるアニオン成分とカチオン成分とからなる、トリアリールスルホニウム塩系光重合開始剤
下記の構造式(3)で表されるアニオン成分とカチオン成分とからなる、トリアリールスルホニウム塩系光重合開始剤
下記の構造式(4)で表されるアニオン成分とカチオン成分とからなる、トリアリールスルホニウム塩系光重合開始剤
上記各成分を、後記の表1〜表4に示す割合で配合した後、加熱溶融混合することにより、実験例および比較例の光硬化型樹脂組成物を調製した。なお、比較例1は、実験例1と対比するために設けたものであり、後記の表1および表3に示すように、比較例1における各成分の配合組成は、オキセタン化合物の種類が異なること以外は、実験例1と同じである。後記の表1〜表4に示すように、他の比較例も、その番号と同じ番号の実験例と対比するために設けたものである。なお、光重合開始剤(b)を用いた実験例を実施例(実験例6を実施例1、実験例11を実施例2)とする。
光硬化型樹脂組成物(液状樹脂)を1×1.5×0.5cmの透明成型型に流し込み、UVを16000mJ照射し硬化させた後、型から外し150℃で1時間の加熱処理を行った。このようにして得られた成形物(硬化物)の表面を、グラインダーにより研磨し、屈折率計(アタゴ社製)を用いて、上記成形物(硬化物)の25℃での屈折率を測定した。
光源に水銀ランプ(浜松ホトニクス社製、LC−8、365nmでの照度が30mW/cm2になるよう設定)を用いたUVレオメーター(Rheologica社製、15mmφのアルミ製パラレルプレート使用)によるゲルタイムを測定し、硬化性の評価を行った。上記UVレオメーターによるゲルタイムは、上記各光硬化型樹脂組成物の粘弾性を25℃で測定した際の弾性項(G′)の105Pa到達時間とした。
5gに計量した光硬化型樹脂組成物(液状樹脂)をアルミシャーレにとり、これを、25℃,60%の恒温恒湿槽に入れて30分間放置した。そして、恒温恒湿槽に入れる前(槽投入前)と、恒温恒湿槽に入れて放置した後(槽放置後)との樹脂組成物中の水分量(含有率)を、カールフィッシャー容量滴定方式自動水分量測定装置(KF−07型、三菱化学社製)により測定した。また、この測定値より、恒温恒湿槽に放置したことによる水分量増加率(吸水率)を算出した。
Claims (3)
- エポキシ樹脂、オキセタン化合物および光重合開始剤が含有されている光硬化型樹脂組成物であって、エポキシ樹脂として下記の(A)成分が含有され、かつ、オキセタン化合物として下記の(B)成分が含有され、光重合開始剤として下記の(C)成分が含有され、樹脂組成物中の全樹脂量100重量%に対して、(A)成分が60〜95重量%、上記(B)成分が5〜40重量%の範囲であり、全樹脂量100重量部に対し、(C)成分の割合が0.05〜5重量部の範囲であることを特徴とする光学レンズ用光硬化型樹脂組成物。
(A)1分子中に2個以上のエポキシ基を有し、脂環式骨格及び/又はビスフェノール骨格を有する、室温で液状のエポキシ樹脂。
(B)下記の一般式(1)で表されるオキセタン化合物。
- 上記(A)成分のエポキシ樹脂が、脂環式エポキシ樹脂を必須とする請求項1記載の光学レンズ用光硬化型樹脂組成物。
- 請求項1または2記載の光学レンズ用光硬化型樹脂組成物の硬化体からなり、屈折率1.50以上であることを特徴とする光学レンズ。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010158039A JP5415371B2 (ja) | 2010-07-12 | 2010-07-12 | 光学レンズ用光硬化型樹脂組成物およびそれを用いた光学レンズ |
SG2011050200A SG177843A1 (en) | 2010-07-12 | 2011-07-11 | Photocurable resin composition and optical component using the same |
US13/179,703 US8575227B2 (en) | 2010-07-12 | 2011-07-11 | Photocurable resin composition and optical component using the same |
TW100124643A TWI506083B (zh) | 2010-07-12 | 2011-07-12 | 光硬化樹脂組合物及使用其之光學元件 |
CN201110201260.1A CN102344544B (zh) | 2010-07-12 | 2011-07-12 | 光固化性树脂组合物及利用其的光学部件 |
KR1020110068991A KR20120006460A (ko) | 2010-07-12 | 2011-07-12 | 광 경화형 수지 조성물 및 그것을 사용한 광학 부품 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010158039A JP5415371B2 (ja) | 2010-07-12 | 2010-07-12 | 光学レンズ用光硬化型樹脂組成物およびそれを用いた光学レンズ |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012021044A JP2012021044A (ja) | 2012-02-02 |
JP5415371B2 true JP5415371B2 (ja) | 2014-02-12 |
Family
ID=45439040
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010158039A Active JP5415371B2 (ja) | 2010-07-12 | 2010-07-12 | 光学レンズ用光硬化型樹脂組成物およびそれを用いた光学レンズ |
Country Status (6)
Country | Link |
---|---|
US (1) | US8575227B2 (ja) |
JP (1) | JP5415371B2 (ja) |
KR (1) | KR20120006460A (ja) |
CN (1) | CN102344544B (ja) |
SG (1) | SG177843A1 (ja) |
TW (1) | TWI506083B (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6001668B2 (ja) | 2012-08-31 | 2016-10-05 | 株式会社ダイセル | 硬化性組成物及びその硬化物、光学部材、並びに光学装置 |
WO2014042328A1 (ko) * | 2012-09-13 | 2014-03-20 | 제일모직 주식회사 | 광경화 조성물, 이를 포함하는 장벽층 및 이를 포함하는 봉지화된 장치 |
JP2014224205A (ja) * | 2013-05-17 | 2014-12-04 | 日東電工株式会社 | 光学部品用光硬化型樹脂組成物およびそれを用いた光学部品、並びに光学部品の製法 |
JP6698717B2 (ja) * | 2018-02-05 | 2020-05-27 | 株式会社ダイセル | 硬化性組成物及びその硬化物 |
CN108485184B (zh) * | 2018-02-11 | 2020-11-24 | 东莞爱的合成材料科技有限公司 | 一种可用于临床医学的耐高温透明光敏树脂及其制备方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4350832B2 (ja) * | 1999-04-19 | 2009-10-21 | Jsr株式会社 | 立体造形用光硬化性樹脂組成物およびこれを硬化してなる造形物 |
JP2004051556A (ja) * | 2002-07-19 | 2004-02-19 | Mitsubishi Chemicals Corp | オキセタン誘導体の製造方法 |
JP4589211B2 (ja) * | 2005-09-20 | 2010-12-01 | 日東電工株式会社 | 光学用紫外線硬化型液状樹脂組成物 |
EP2030972A4 (en) | 2006-06-06 | 2010-05-26 | Ube Industries | 3-ETHYLOXETHANE HAVING A HYDROXY GROUP AND METHOD OF PRODUCING THE SAME |
JP5280615B2 (ja) * | 2006-06-16 | 2013-09-04 | シーメット株式会社 | 光学的立体造形用樹脂組成物 |
JP3926380B1 (ja) | 2006-12-07 | 2007-06-06 | マイルストーン株式会社 | 撮像レンズ |
JP5210645B2 (ja) * | 2008-01-25 | 2013-06-12 | シーメット株式会社 | 光学的立体造形用樹脂組成物 |
JP5102671B2 (ja) * | 2008-03-25 | 2012-12-19 | 株式会社日本触媒 | 硬化性樹脂組成物、その硬化物、光学部材及び光学ユニット |
TWI427117B (zh) | 2008-05-30 | 2014-02-21 | Nitto Denko Corp | 光學元件用樹脂組成物、使用其之光學元件及光學鏡片之製造方法 |
JP5070131B2 (ja) * | 2008-05-30 | 2012-11-07 | 日東電工株式会社 | 光学部品用樹脂組成物およびそれを用いた光学部品 |
JP5350324B2 (ja) | 2009-06-18 | 2013-11-27 | 日東電工株式会社 | 光硬化型樹脂組成物およびそれを用いた光学部品 |
EP2264081B1 (en) | 2009-06-18 | 2012-08-22 | Nitto Denko Corporation | Photocurable resin composition and optical component using the same |
JP5447097B2 (ja) * | 2010-03-31 | 2014-03-19 | Dic株式会社 | カチオン重合性組成物、それを含むコーティング剤及び接着剤ならびにそれらを用いて得られる塗装物及び積層体 |
-
2010
- 2010-07-12 JP JP2010158039A patent/JP5415371B2/ja active Active
-
2011
- 2011-07-11 SG SG2011050200A patent/SG177843A1/en unknown
- 2011-07-11 US US13/179,703 patent/US8575227B2/en not_active Expired - Fee Related
- 2011-07-12 KR KR1020110068991A patent/KR20120006460A/ko not_active Application Discontinuation
- 2011-07-12 CN CN201110201260.1A patent/CN102344544B/zh not_active Expired - Fee Related
- 2011-07-12 TW TW100124643A patent/TWI506083B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CN102344544A (zh) | 2012-02-08 |
TW201213431A (en) | 2012-04-01 |
US8575227B2 (en) | 2013-11-05 |
SG177843A1 (en) | 2012-02-28 |
JP2012021044A (ja) | 2012-02-02 |
TWI506083B (zh) | 2015-11-01 |
CN102344544B (zh) | 2015-04-01 |
KR20120006460A (ko) | 2012-01-18 |
US20120010320A1 (en) | 2012-01-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2014185180A1 (ja) | 光学部品用光硬化型樹脂組成物およびそれを用いた光学部品、並びに光学部品の製法 | |
JP5329299B2 (ja) | 光学レンズ | |
JP5415371B2 (ja) | 光学レンズ用光硬化型樹脂組成物およびそれを用いた光学レンズ | |
KR20090124998A (ko) | 광학 부품용 수지 조성물, 이를 이용한 광학 부품 및 광학 렌즈의 제조 방법 | |
JP5415370B2 (ja) | 光硬化型樹脂組成物およびそれを用いた光学部品 | |
JP5070131B2 (ja) | 光学部品用樹脂組成物およびそれを用いた光学部品 | |
JP5405377B2 (ja) | 光学レンズ用光硬化型樹脂組成物およびそれを用いた光学レンズ | |
JP6418672B2 (ja) | 光学部品用樹脂組成物およびそれを用いた光学部品 | |
JP5184336B2 (ja) | 紫外線硬化型樹脂組成物およびそれを用いて得られる光学レンズ | |
JP2016050230A (ja) | 光学用感光性樹脂組成物およびそれを用いた光学材料 | |
WO2022100753A1 (zh) | 光固化组合物、光学膜及其制备方法和光学产品 | |
JP5306315B2 (ja) | 光硬化性樹脂組成物および光学材料 | |
TWI518131B (zh) | 光硬化性樹脂組合物及光學材料 | |
WO2021049443A1 (ja) | 紫外線硬化性樹脂組成物、硬化物及び光学レンズ | |
JP2009288598A (ja) | 光学レンズの製法およびそれにより得られた光学レンズ | |
JP6418673B2 (ja) | 光学部品用樹脂組成物およびそれを用いた光学部品 | |
TWI516517B (zh) | 光硬化樹脂組合物及使用其之光學元件 | |
WO2018096967A1 (ja) | 脂環式エポキシ化合物を含むインプリント成形用光重合性組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20121126 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130510 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130514 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20130711 Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130711 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130813 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20131010 Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131010 |
|
TRDD | Decision of grant or rejection written | ||
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131113 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5415371 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |