CN109627419B - 用于塑料光学镜片的多硫醇组合物 - Google Patents
用于塑料光学镜片的多硫醇组合物 Download PDFInfo
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- CN109627419B CN109627419B CN201811625363.9A CN201811625363A CN109627419B CN 109627419 B CN109627419 B CN 109627419B CN 201811625363 A CN201811625363 A CN 201811625363A CN 109627419 B CN109627419 B CN 109627419B
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- polythiol
- compound
- polythiol compound
- hydrogen
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- 150000001875 compounds Chemical class 0.000 claims abstract description 154
- 125000000524 functional group Chemical group 0.000 claims abstract description 54
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 47
- 229920002578 polythiourethane polymer Polymers 0.000 claims abstract description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 5
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- 239000002685 polymerization catalyst Substances 0.000 claims description 4
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
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- 239000010452 phosphate Substances 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
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- NZARHKBYDXFVPP-UHFFFAOYSA-N tetrathiolane Chemical compound C1SSSS1 NZARHKBYDXFVPP-UHFFFAOYSA-N 0.000 description 2
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- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
- RHNNQENFSNOGAM-UHFFFAOYSA-N 1,8-diisocyanato-4-(isocyanatomethyl)octane Chemical compound O=C=NCCCCC(CN=C=O)CCCN=C=O RHNNQENFSNOGAM-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- GNDOBZLRZOCGAS-JTQLQIEISA-N 2-isocyanatoethyl (2s)-2,6-diisocyanatohexanoate Chemical compound O=C=NCCCC[C@H](N=C=O)C(=O)OCCN=C=O GNDOBZLRZOCGAS-JTQLQIEISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
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- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
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- 150000001845 chromium compounds Chemical class 0.000 description 1
- RPBPCPJJHKASGQ-UHFFFAOYSA-K chromium(3+);octanoate Chemical compound [Cr+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O RPBPCPJJHKASGQ-UHFFFAOYSA-K 0.000 description 1
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- CKEIYLXUHITGSQ-UHFFFAOYSA-N cyclohexyl-dodecyl-diethylazanium Chemical class CCCCCCCCCCCC[N+](CC)(CC)C1CCCCC1 CKEIYLXUHITGSQ-UHFFFAOYSA-N 0.000 description 1
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- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 1
- XWKIXFQOFAVHQI-UHFFFAOYSA-N disodium;sulfide;pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[S-2] XWKIXFQOFAVHQI-UHFFFAOYSA-N 0.000 description 1
- DGJUONISEWDPFO-UHFFFAOYSA-N dodecyl(triethyl)azanium Chemical class CCCCCCCCCCCC[N+](CC)(CC)CC DGJUONISEWDPFO-UHFFFAOYSA-N 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical class CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
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- 229940079101 sodium sulfide Drugs 0.000 description 1
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- ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 1
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- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- 229910009112 xH2O Inorganic materials 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- 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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
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- C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- 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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
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- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
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| KR102564990B1 (ko) * | 2020-12-01 | 2023-08-07 | 에스케이씨 주식회사 | 폴리티올 조성물 및 이를 포함하는 중합성 조성물 |
| CN116601200A (zh) * | 2020-11-27 | 2023-08-15 | Skc株式会社 | 多硫醇组合物、光学组合物和光学产品 |
| US20240002336A1 (en) * | 2020-11-27 | 2024-01-04 | Skc Co., Ltd. | Polythiol composition, optical composition, and optical product |
| KR102707088B1 (ko) * | 2020-11-27 | 2024-09-19 | 에스케이피유코어 주식회사 | 폴리티올 조성물, 광학 조성물 및 광학 제품 |
| GB2615967B (en) * | 2020-11-27 | 2024-09-11 | Sk Pucore Co Ltd | Polythiol composition, optical composition and optical product |
| CN114605605B (zh) * | 2022-03-08 | 2023-03-24 | 益丰新材料股份有限公司 | 一种含有多硫醇组合物的光学材料组合物 |
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| DE68918356T2 (de) * | 1988-07-14 | 1995-05-11 | Mitsui Toatsu Chemicals, Inc., Tokio/Tokyo | Linse, ein Kunstharz mit hohem Brechungsindex enthaltend und Verfahren zur Herstellung der Linse. |
| FR2649711B1 (fr) * | 1989-07-13 | 1993-01-22 | Essilor Int | Compositions de polymeres a base de polythiourethanes pour la fabrication de verres organiques |
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| US5608115A (en) | 1994-01-26 | 1997-03-04 | Mitsui Toatsu Chemicals, Inc. | Polythiol useful for preparing sulfur-containing urethane-based resin and process for producing the same |
| JPH09194558A (ja) | 1996-01-23 | 1997-07-29 | Mitsui Toatsu Chem Inc | 含硫ウレタン系プラスチックレンズ |
| US5942158A (en) * | 1998-03-09 | 1999-08-24 | Ppg Industries Ohio, Inc. | One-component optical resin composition |
| JP3974404B2 (ja) * | 2002-01-15 | 2007-09-12 | 三井化学株式会社 | ポリチオール、その製造方法、これを含有する重合性組成物、並びに樹脂及びレンズ |
| EP1878758B1 (en) * | 2005-04-11 | 2013-06-05 | Mitsui Chemicals, Inc. | Polythiourethane polymerizable composition and method for producing optical resin by using same |
| CN101421232A (zh) * | 2006-04-19 | 2009-04-29 | 三井化学株式会社 | 光学材料用(多)硫醇化合物的制造方法及含有该化合物的聚合性组合物 |
| WO2007131145A1 (en) * | 2006-05-05 | 2007-11-15 | Ppg Industries Ohio, Inc. | Compositions and articles prepared from thioether functional oligomeric polythiols |
| KR101400358B1 (ko) * | 2012-05-23 | 2014-05-27 | 주식회사 케이오씨솔루션 | 신규한 폴리티올 화합물의 제조방법 및 이를 포함하는 광학재료용 중합성 조성물 |
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| TW201506083A (zh) * | 2013-06-18 | 2015-02-16 | Mitsubishi Gas Chemical Co | 光學材料用組成物 |
| CN106458876B (zh) * | 2014-06-09 | 2018-06-05 | 可奥熙搜路司有限公司 | 新的硫醇化合物和包含其的聚合性组合物 |
| KR20170091723A (ko) * | 2015-02-02 | 2017-08-09 | 미쯔이가가꾸가부시끼가이샤 | 광학 재료용 중합성 조성물, 광학 재료 및 그 용도 |
| CA2975582A1 (en) * | 2015-02-05 | 2016-08-11 | Sekisui Chemical Co., Ltd. | Interlayer film for laminated glass, and laminated glass |
| US10526533B2 (en) * | 2015-03-10 | 2020-01-07 | Tokuyama Corporation | Process for producing a photochromic cured body |
| JP6335392B2 (ja) * | 2015-06-24 | 2018-05-30 | 三井化学株式会社 | ペンタエリスリトールメルカプトカルボン酸エステルの製造方法、重合性組成物、樹脂、光学材料およびレンズ |
| KR101831892B1 (ko) * | 2016-06-30 | 2018-02-26 | 에스케이씨 주식회사 | 폴리티오우레탄계 광학 재료용 중합성 조성물 |
| WO2018012803A1 (ko) * | 2016-07-14 | 2018-01-18 | 에스케이씨 주식회사 | 광학 재료용 방향족 폴리티올 화합물 |
| JP6632493B2 (ja) * | 2016-08-05 | 2020-01-22 | ホヤ レンズ タイランド リミテッドHOYA Lens Thailand Ltd | ポリチオール化合物の製造方法、硬化性組成物の製造方法、および硬化物の製造方法 |
| JP6633990B2 (ja) * | 2016-08-08 | 2020-01-22 | ホヤ レンズ タイランド リミテッドHOYA Lens Thailand Ltd | ポリチオール化合物の製造方法、硬化性組成物の製造方法、および硬化物の製造方法 |
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| US20190225755A1 (en) | 2019-07-25 |
| US10435512B2 (en) | 2019-10-08 |
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| TW201932449A (zh) | 2019-08-16 |
| JP2019128596A (ja) | 2019-08-01 |
| KR101894921B1 (ko) | 2018-09-04 |
| TWI675821B (zh) | 2019-11-01 |
| EP3514187B1 (en) | 2020-07-29 |
| JP6700444B2 (ja) | 2020-05-27 |
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