KR101571275B1 - 중합성 조성물, 광학 재료 및 그 제조 방법 - Google Patents
중합성 조성물, 광학 재료 및 그 제조 방법 Download PDFInfo
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- KR101571275B1 KR101571275B1 KR1020157011250A KR20157011250A KR101571275B1 KR 101571275 B1 KR101571275 B1 KR 101571275B1 KR 1020157011250 A KR1020157011250 A KR 1020157011250A KR 20157011250 A KR20157011250 A KR 20157011250A KR 101571275 B1 KR101571275 B1 KR 101571275B1
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- South Korea
- Prior art keywords
- bis
- polymerizable composition
- compound
- mercaptopropionate
- lens
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 239000000463 material Substances 0.000 title claims description 32
- 230000003287 optical effect Effects 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title description 9
- -1 alicyclic isocyanate compound Chemical class 0.000 claims abstract description 205
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 79
- 239000003054 catalyst Substances 0.000 claims abstract description 72
- 239000012948 isocyanate Substances 0.000 claims abstract description 48
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 50
- 239000004033 plastic Substances 0.000 claims description 31
- 229920003023 plastic Polymers 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 238000005266 casting Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 7
- YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 claims description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- BODVSESPBZOELC-UHFFFAOYSA-N 2-(2-phenylethyl)-1h-imidazole Chemical compound N=1C=CNC=1CCC1=CC=CC=C1 BODVSESPBZOELC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 5
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 claims description 4
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 claims description 4
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 claims description 4
- QNSUVMHSJGIMDL-UHFFFAOYSA-N [6-(sulfanylmethylsulfanyl)-1,3-dithian-4-yl]sulfanylmethanethiol Chemical compound SCSC1CC(SCS)SCS1 QNSUVMHSJGIMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QNITWMBGUWZSSI-UHFFFAOYSA-N sulfanylmethylsulfanylmethylsulfanylmethanethiol Chemical compound SCSCSCS QNITWMBGUWZSSI-UHFFFAOYSA-N 0.000 claims description 4
- MTZVWTOVHGKLOX-UHFFFAOYSA-N 2,2-bis(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)(CS)CS MTZVWTOVHGKLOX-UHFFFAOYSA-N 0.000 claims description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
- AVEHHJFINMFELH-UHFFFAOYSA-N 1-(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical compound SCSC(C)SCS AVEHHJFINMFELH-UHFFFAOYSA-N 0.000 claims description 2
- DGPOVPJSXNLHJO-UHFFFAOYSA-N 2,3-bis(sulfanyl)propyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(S)CS DGPOVPJSXNLHJO-UHFFFAOYSA-N 0.000 claims description 2
- WXDDGAZCUPULGL-UHFFFAOYSA-N 2,3-bis(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSCC(SCS)CSCS WXDDGAZCUPULGL-UHFFFAOYSA-N 0.000 claims description 2
- YZRWBFPKXNRWHS-UHFFFAOYSA-N 2-(sulfanylmethylsulfanyl)ethanethiol Chemical compound SCCSCS YZRWBFPKXNRWHS-UHFFFAOYSA-N 0.000 claims description 2
- QTEWPHJCEXIMRJ-UHFFFAOYSA-N 2-[2,3-bis(2-sulfanylethylsulfanyl)propylsulfanyl]ethanethiol Chemical compound SCCSCC(SCCS)CSCCS QTEWPHJCEXIMRJ-UHFFFAOYSA-N 0.000 claims description 2
- MXTOXODEXBYZFX-UHFFFAOYSA-N 2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]ethanethiol Chemical compound SCCSCCSCCS MXTOXODEXBYZFX-UHFFFAOYSA-N 0.000 claims description 2
- KIVDBXVDNQFFFL-UHFFFAOYSA-N 2-[3-(2-sulfanylethylsulfanyl)-2,2-bis(2-sulfanylethylsulfanylmethyl)propyl]sulfanylethanethiol Chemical compound SCCSCC(CSCCS)(CSCCS)CSCCS KIVDBXVDNQFFFL-UHFFFAOYSA-N 0.000 claims description 2
- SQTMWMRJFVGAOW-UHFFFAOYSA-N 3-[2,3-bis(sulfanyl)propylsulfanyl]propane-1,2-dithiol Chemical compound SCC(S)CSCC(S)CS SQTMWMRJFVGAOW-UHFFFAOYSA-N 0.000 claims description 2
- SWTBZQOYIMBDQQ-UHFFFAOYSA-N OCSCO.OC(=O)CCS.OC(=O)CCS Chemical compound OCSCO.OC(=O)CCS.OC(=O)CCS SWTBZQOYIMBDQQ-UHFFFAOYSA-N 0.000 claims description 2
- OKFFYKLCPLSDRT-UHFFFAOYSA-N SCC(=O)O.SCC(=O)O.OCSCO Chemical compound SCC(=O)O.SCC(=O)O.OCSCO OKFFYKLCPLSDRT-UHFFFAOYSA-N 0.000 claims description 2
- HSXLFQVUYYYRDH-UHFFFAOYSA-N SCCC(=O)O.SCC(=O)O.SCC(=O)O.SCC(=O)O.SCC(=O)O.OCC(CO)(CO)CO Chemical compound SCCC(=O)O.SCC(=O)O.SCC(=O)O.SCC(=O)O.SCC(=O)O.OCC(CO)(CO)CO HSXLFQVUYYYRDH-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- OLKXZFMYPZDPLQ-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-(3-sulfanylpropanoyloxy)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CO)(CO)COC(=O)CCS OLKXZFMYPZDPLQ-UHFFFAOYSA-N 0.000 claims description 2
- OCCLJFJGIDIZKK-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(3-sulfanylpropanoyloxy)-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CO)(COC(=O)CCS)COC(=O)CCS OCCLJFJGIDIZKK-UHFFFAOYSA-N 0.000 claims description 2
- PSTJFHCNZDHXGK-UHFFFAOYSA-N [4-(2-sulfanylacetyl)oxycyclohexyl] 2-sulfanylacetate Chemical compound SCC(=O)OC1CCC(OC(=O)CS)CC1 PSTJFHCNZDHXGK-UHFFFAOYSA-N 0.000 claims description 2
- ZXYNIDHBHXSPSU-UHFFFAOYSA-N [4-hydroxy-3,3-bis(hydroxymethyl)butyl] 2-sulfanylacetate Chemical compound OCC(CO)(CO)CCOC(=O)CS ZXYNIDHBHXSPSU-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- WTSBJMAOQNCZBF-UHFFFAOYSA-N sulfanylmethylsulfanylmethanethiol Chemical compound SCSCS WTSBJMAOQNCZBF-UHFFFAOYSA-N 0.000 claims description 2
- HBFBFJVRBIGLND-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)(CO)CO HBFBFJVRBIGLND-UHFFFAOYSA-N 0.000 claims 1
- XYHKMRNYSMEEDT-UHFFFAOYSA-N 2-[3-(2-sulfanylethylsulfanyl)propylsulfanyl]ethanethiol Chemical compound SCCSCCCSCCS XYHKMRNYSMEEDT-UHFFFAOYSA-N 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- ZQLOVEFZBNCMLV-UHFFFAOYSA-N 3,3-bis(sulfanyl)propanoic acid Chemical compound OC(=O)CC(S)S ZQLOVEFZBNCMLV-UHFFFAOYSA-N 0.000 claims 1
- FYOKDASBYGFLNH-UHFFFAOYSA-N 3,4-bis(isothiocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2(CN=C=S)C(CN=C=S)CC1C2 FYOKDASBYGFLNH-UHFFFAOYSA-N 0.000 claims 1
- XBNYMYZLSBMANG-UHFFFAOYSA-N 3-(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSCCCSCS XBNYMYZLSBMANG-UHFFFAOYSA-N 0.000 claims 1
- JPOGHRQRPDMXMQ-UHFFFAOYSA-N OCCSCCO.SCCC(=O)O Chemical compound OCCSCCO.SCCC(=O)O JPOGHRQRPDMXMQ-UHFFFAOYSA-N 0.000 claims 1
- NYBRUVZLACHFDJ-UHFFFAOYSA-N SCCC(=O)O.SCC(=O)O.SCC(=O)O.SCC(CO)O Chemical compound SCCC(=O)O.SCC(=O)O.SCC(=O)O.SCC(CO)O NYBRUVZLACHFDJ-UHFFFAOYSA-N 0.000 claims 1
- FRGKKTITADJNOE-UHFFFAOYSA-N sulfanyloxyethane Chemical compound CCOS FRGKKTITADJNOE-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 57
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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- 238000011156 evaluation Methods 0.000 description 15
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- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical class CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
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- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- C—CHEMISTRY; METALLURGY
- 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
- C08G18/20—Heterocyclic amines; 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
-
- 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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
-
- 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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
-
- 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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C2202/00—Generic optical aspects applicable to one or more of the subgroups of G02C7/00
- G02C2202/16—Laminated or compound lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Ophthalmology & Optometry (AREA)
- General Health & Medical Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Eyeglasses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| JP2012251913 | 2012-11-16 | ||
| JPJP-P-2012-251913 | 2012-11-16 | ||
| PCT/JP2013/080936 WO2014077369A1 (ja) | 2012-11-16 | 2013-11-15 | 重合性組成物、光学材料およびその製造方法 |
Publications (2)
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| KR20150065793A KR20150065793A (ko) | 2015-06-15 |
| KR101571275B1 true KR101571275B1 (ko) | 2015-11-23 |
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| US (1) | US9778397B2 (https=) |
| EP (1) | EP2921511B1 (https=) |
| JP (1) | JP5646790B2 (https=) |
| KR (1) | KR101571275B1 (https=) |
| CN (1) | CN104755520B (https=) |
| IN (1) | IN2015DN03767A (https=) |
| WO (1) | WO2014077369A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9944029B2 (en) | 2014-02-20 | 2018-04-17 | Mitsui Chemicals, Inc. | Process for producing optical material |
| US10663625B2 (en) * | 2014-04-24 | 2020-05-26 | Hoya Lens Thailand Ltd. | Spectacle lens |
| US10544283B2 (en) | 2015-03-12 | 2020-01-28 | Hoya Lens Thailand Ltd. | Iso(thio)cyanate composition, and resin composition including same for optical member |
| WO2016170059A1 (en) * | 2015-04-21 | 2016-10-27 | Covestro Deutschland Ag | Polyisocyanurate polymers and process for the production of polyisocyanurate polymers |
| WO2017111142A1 (ja) * | 2015-12-22 | 2017-06-29 | ホヤ レンズ タイランド リミテッド | 光学部材、光学部材管理システム、及び光学部材の製造方法 |
| WO2018003060A1 (ja) * | 2016-06-30 | 2018-01-04 | ホヤ レンズ タイランド リミテッド | 硬化物の製造方法、硬化物および眼鏡レンズ基材 |
| JPWO2018003058A1 (ja) * | 2016-06-30 | 2019-01-17 | ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ | 硬化物の製造方法、硬化物および眼鏡レンズ基材 |
| TWI615415B (zh) * | 2016-09-13 | 2018-02-21 | 奇美實業股份有限公司 | 光學材料用樹脂組成物、光學材料用樹脂及其所形成的光學透鏡 |
| BR112019004133B1 (pt) * | 2016-09-30 | 2022-10-25 | Mitsui Chemicals, Inc | Composição polimerizável para material ótico e produto moldado |
| CN109906240B (zh) | 2016-10-31 | 2021-08-24 | 三井化学株式会社 | 光学材料用聚合性组合物、光学材料及其制造方法 |
| KR101893558B1 (ko) * | 2017-02-03 | 2018-08-30 | 에스케이씨 주식회사 | 플라스틱 렌즈용 중합성 조성물 |
| ES2905949T3 (es) * | 2017-09-29 | 2022-04-12 | Fund Cidetec | Politiouretanos reticulados inyectables, reprocesables, reparables e intrínsecamente reciclables |
| CN108440734A (zh) * | 2018-03-07 | 2018-08-24 | 上海伟星光学有限公司 | 一种聚氨酯镜片及其短流程固化方法 |
| CN111868099B (zh) * | 2018-03-27 | 2022-12-16 | 三井化学株式会社 | 聚合条件设定方法、光学材料的制造方法 |
| US12135472B2 (en) | 2019-04-19 | 2024-11-05 | Mitsui Chemicals, Inc. | Optical material, polymerizable composition for optical material, cured product, optical material, plastic lens, method of producing optical material, and method of using optical material |
| WO2020213717A1 (ja) * | 2019-04-19 | 2020-10-22 | 三井化学株式会社 | 光学材料 |
| KR102150590B1 (ko) * | 2019-06-20 | 2020-09-01 | 에스케이씨 주식회사 | 중합성 조성물 및 이를 이용한 광학 재료 |
| CN116874734A (zh) | 2020-01-27 | 2023-10-13 | 三井化学株式会社 | 光学材料用聚合性组合物、光学材料用聚合性预聚物组合物、固化物及光学材料的制造方法 |
| CN113557254B (zh) | 2020-01-27 | 2023-01-17 | 三井化学株式会社 | 光学材料用聚合性组合物、光学材料用聚合性预聚物组合物、固化物及光学材料的制造方法 |
| CN112661930B (zh) * | 2020-11-27 | 2022-08-05 | 万华化学集团股份有限公司 | 一种苯二亚甲基二异氰酸酯组合物及光学树脂 |
| US12583963B2 (en) | 2021-05-28 | 2026-03-24 | Sk Pucore Co., Ltd. | Polymerizable composition and optical material using the same |
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| KR100191067B1 (ko) | 1994-04-08 | 1999-06-15 | 사또 아끼오 | 우레탄계 플라스틱렌즈용조성물 및 상기 우레탄계 플라스틱렌즈의 제조방법 |
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| JP2950862B2 (ja) | 1989-08-29 | 1999-09-20 | 三井化学株式会社 | チオカルバミン酸ｓ―アルキルエステル系レンズおよびその製造方法 |
| JP2695599B2 (ja) * | 1993-09-29 | 1997-12-24 | ホーヤ株式会社 | ポリウレタンレンズの製造方法 |
| JP3220614B2 (ja) | 1994-04-08 | 2001-10-22 | 三井化学株式会社 | ウレタン系プラスチックレンズ用組成物、それよりなるプラスチックレンズおよびその製造方法 |
| JP3872155B2 (ja) | 1997-02-19 | 2007-01-24 | 住友精化株式会社 | 硬化性組成物およびそれからなる光学材料 |
| JP2001131257A (ja) * | 1999-11-09 | 2001-05-15 | Mitsubishi Gas Chem Co Inc | 樹脂用組成物 |
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| JP3562579B2 (ja) * | 2000-10-13 | 2004-09-08 | 三菱瓦斯化学株式会社 | 光学材料用組成物 |
| JP2002234997A (ja) * | 2001-02-09 | 2002-08-23 | Seiko Epson Corp | ポリウレタンレンズ成形用内部離型剤及びそれを用いたポリウレタンレンズ |
| JP4702508B2 (ja) * | 2001-07-18 | 2011-06-15 | 三菱瓦斯化学株式会社 | 樹脂の製造方法 |
| JP4393831B2 (ja) * | 2003-09-22 | 2010-01-06 | Ｈｏｙａ株式会社 | プラスチックレンズの製造方法 |
| JP2005163008A (ja) * | 2003-11-12 | 2005-06-23 | Seiko Epson Corp | 含硫黄光学材料用樹脂の製造方法、含硫黄光学材料用樹脂及び含硫黄プラスチックレンズ |
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| JP2005345684A (ja) * | 2004-06-02 | 2005-12-15 | Mitsui Chemicals Inc | 硫黄原子含有樹脂からなる光学材料 |
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| JP4716249B2 (ja) | 2005-03-24 | 2011-07-06 | 三菱瓦斯化学株式会社 | 重合性組成物 |
| KR101029908B1 (ko) * | 2006-05-05 | 2011-04-18 | 피피지 인더스트리즈 오하이오 인코포레이티드 | 싸이오에터 작용성 올리고머성 폴리싸이올로부터 제조된 조성물 및 제품 |
| JP5254793B2 (ja) | 2006-08-23 | 2013-08-07 | 昭和電工株式会社 | チオウレタン化合物および感光性樹脂組成物 |
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| JP2009169391A (ja) | 2007-12-17 | 2009-07-30 | Seiko Epson Corp | 光学物品の製造方法および製造装置 |
| JP5488859B2 (ja) * | 2008-08-05 | 2014-05-14 | 東海カーボン株式会社 | 顔料分散感光性樹脂組成物 |
| CN101613450B (zh) * | 2009-07-16 | 2011-11-30 | 烟台德邦科技有限公司 | 一种弹性光学树脂材料及其制备方法 |
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2013
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- 2013-11-15 CN CN201380057315.3A patent/CN104755520B/zh active Active
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- 2013-11-15 EP EP13854323.6A patent/EP2921511B1/en active Active
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100191067B1 (ko) | 1994-04-08 | 1999-06-15 | 사또 아끼오 | 우레탄계 플라스틱렌즈용조성물 및 상기 우레탄계 플라스틱렌즈의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014077369A1 (ja) | 2014-05-22 |
| EP2921511A1 (en) | 2015-09-23 |
| CN104755520B (zh) | 2018-10-09 |
| JP5646790B2 (ja) | 2014-12-24 |
| KR20150065793A (ko) | 2015-06-15 |
| US9778397B2 (en) | 2017-10-03 |
| CN104755520A (zh) | 2015-07-01 |
| IN2015DN03767A (https=) | 2015-10-02 |
| US20150331147A1 (en) | 2015-11-19 |
| JPWO2014077369A1 (ja) | 2017-01-05 |
| EP2921511A4 (en) | 2015-11-25 |
| EP2921511B1 (en) | 2017-11-01 |
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