WO2012090372A1 - 光学材料用組成物 - Google Patents
光学材料用組成物 Download PDFInfo
- Publication number
- WO2012090372A1 WO2012090372A1 PCT/JP2011/006207 JP2011006207W WO2012090372A1 WO 2012090372 A1 WO2012090372 A1 WO 2012090372A1 JP 2011006207 W JP2011006207 W JP 2011006207W WO 2012090372 A1 WO2012090372 A1 WO 2012090372A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- mercaptomethylthio
- composition
- compound
- benzene
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 57
- 230000003287 optical effect Effects 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- -1 (thio)cyanate compound Chemical class 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 claims abstract description 29
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 28
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 claims abstract description 27
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 24
- 229920006295 polythiol Polymers 0.000 claims abstract description 23
- 229920000582 polyisocyanurate Polymers 0.000 claims abstract description 17
- 239000011495 polyisocyanurate Substances 0.000 claims abstract description 17
- 238000011282 treatment Methods 0.000 claims description 14
- 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 6
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 claims description 6
- LEAAXJONQWQISB-UHFFFAOYSA-N 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1C2C(CN=C=O)CC1C(CN=C=O)C2 LEAAXJONQWQISB-UHFFFAOYSA-N 0.000 claims description 6
- DAUUORKACOSESW-UHFFFAOYSA-N 2-[2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]ethylsulfanylmethyl]propane-1,2,3-trithiol Chemical compound SCCSCCSCCSCC(S)(CS)CS DAUUORKACOSESW-UHFFFAOYSA-N 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 claims description 4
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 claims description 4
- FOLVZNOYNJFEBK-UHFFFAOYSA-N 3,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1C(CN=C=O)C2C(CN=C=O)CC1C2 FOLVZNOYNJFEBK-UHFFFAOYSA-N 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- JSNABGZJVWSNOB-UHFFFAOYSA-N [3-(sulfanylmethyl)phenyl]methanethiol Chemical compound SCC1=CC=CC(CS)=C1 JSNABGZJVWSNOB-UHFFFAOYSA-N 0.000 claims description 4
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- WTSBJMAOQNCZBF-UHFFFAOYSA-N sulfanylmethylsulfanylmethanethiol Chemical compound SCSCS WTSBJMAOQNCZBF-UHFFFAOYSA-N 0.000 claims description 4
- 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 2
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
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- 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 description 4
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- SPAAESPYCDSRIW-UHFFFAOYSA-N 2-(2-sulfanylethyldisulfanyl)ethanethiol Chemical compound SCCSSCCS SPAAESPYCDSRIW-UHFFFAOYSA-N 0.000 description 2
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 2
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- KXCKKUIJCYNZAE-UHFFFAOYSA-N benzene-1,3,5-trithiol Chemical compound SC1=CC(S)=CC(S)=C1 KXCKKUIJCYNZAE-UHFFFAOYSA-N 0.000 description 1
- IAWMCCJYDCXYTC-UHFFFAOYSA-N benzene-1,3-dicarbonyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC(C(=O)N=C=S)=C1 IAWMCCJYDCXYTC-UHFFFAOYSA-N 0.000 description 1
- ZWOASCVFHSYHOB-UHFFFAOYSA-N benzene-1,3-dithiol Chemical compound SC1=CC=CC(S)=C1 ZWOASCVFHSYHOB-UHFFFAOYSA-N 0.000 description 1
- YGWPJZQQKHBXOR-UHFFFAOYSA-N benzene-1,4-dicarbonyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=C(C(=O)N=C=S)C=C1 YGWPJZQQKHBXOR-UHFFFAOYSA-N 0.000 description 1
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NSKYMLWGJWRTQE-UHFFFAOYSA-N bis(2-isocyanatoethyl) benzene-1,2-dicarboxylate Chemical compound O=C=NCCOC(=O)C1=CC=CC=C1C(=O)OCCN=C=O NSKYMLWGJWRTQE-UHFFFAOYSA-N 0.000 description 1
- DZYFUUQMKQBVBY-UHFFFAOYSA-N bis(2-isocyanatoethyl) carbonate Chemical compound O=C=NCCOC(=O)OCCN=C=O DZYFUUQMKQBVBY-UHFFFAOYSA-N 0.000 description 1
- UKMZAJWQLPRXRD-UHFFFAOYSA-N bis(4-isothiocyanato-3-methylphenyl)methanone Chemical compound C1=C(N=C=S)C(C)=CC(C(=O)C=2C=C(C)C(N=C=S)=CC=2)=C1 UKMZAJWQLPRXRD-UHFFFAOYSA-N 0.000 description 1
- QWCNRESNZMCPJW-UHFFFAOYSA-N bis(sulfanylmethylsulfanyl)methylsulfanylmethanethiol Chemical compound SCSC(SCS)SCS QWCNRESNZMCPJW-UHFFFAOYSA-N 0.000 description 1
- OMWQUXGVXQELIX-UHFFFAOYSA-N bitoscanate Chemical compound S=C=NC1=CC=C(N=C=S)C=C1 OMWQUXGVXQELIX-UHFFFAOYSA-N 0.000 description 1
- 229950002418 bitoscanate Drugs 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 210000001217 buttock Anatomy 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- VSARMWHOISBCGR-UHFFFAOYSA-N cyclohexane-1,1-dithiol Chemical compound SC1(S)CCCCC1 VSARMWHOISBCGR-UHFFFAOYSA-N 0.000 description 1
- YKRCKUBKOIVILO-UHFFFAOYSA-N cyclohexane-1,2-dithiol Chemical compound SC1CCCCC1S YKRCKUBKOIVILO-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000004252 dithioacetals Chemical class 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- BGXUHYCDVKDVAI-UHFFFAOYSA-N isocyanato(isocyanatomethylsulfanyl)methane Chemical compound O=C=NCSCN=C=O BGXUHYCDVKDVAI-UHFFFAOYSA-N 0.000 description 1
- ZHWJTCDUSSCFOZ-UHFFFAOYSA-N isocyanato(isocyanatomethylsulfanylmethylsulfanyl)methane Chemical compound O=C=NCSCSCN=C=O ZHWJTCDUSSCFOZ-UHFFFAOYSA-N 0.000 description 1
- CNIQRWPMYHDBNS-UHFFFAOYSA-N isocyanato(isocyanatomethylsulfonyl)methane Chemical compound O=C=NCS(=O)(=O)CN=C=O CNIQRWPMYHDBNS-UHFFFAOYSA-N 0.000 description 1
- OFUBORBAMWUXTI-UHFFFAOYSA-N isocyanato-(isocyanatomethyldisulfanyl)methane Chemical compound O=C=NCSSCN=C=O OFUBORBAMWUXTI-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UKQMUPLYHOXQQR-UHFFFAOYSA-N phenylmethanedithiol Chemical compound SC(S)C1=CC=CC=C1 UKQMUPLYHOXQQR-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- UWHMFGKZAYHMDJ-UHFFFAOYSA-N propane-1,2,3-trithiol Chemical compound SCC(S)CS UWHMFGKZAYHMDJ-UHFFFAOYSA-N 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- HMPSOEYFMTWOFC-UHFFFAOYSA-N propane-2,2-dithiol Chemical compound CC(C)(S)S HMPSOEYFMTWOFC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- FKPZDPMIYDBOJO-UHFFFAOYSA-N sulfanylmethylsulfanyl(sulfanylmethylsulfanylmethylsulfanyl)methanethiol Chemical compound SCSC(SCSCS)S FKPZDPMIYDBOJO-UHFFFAOYSA-N 0.000 description 1
- OOZWJYRXTAYWTJ-UHFFFAOYSA-N sulfanylmethylsulfanyl-[3-[3-(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanyl]propylsulfanylmethylsulfanylmethylsulfanyl]methanethiol Chemical compound SCSCCCSCSCCCSCSCSC(S)SCS OOZWJYRXTAYWTJ-UHFFFAOYSA-N 0.000 description 1
- QMHKMLUVKWZPCH-UHFFFAOYSA-N sulfanylmethylsulfanyl-[3-[3-(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanylmethylsulfanylmethylsulfanyl]propylsulfanyl]methanethiol Chemical compound SCSCCCSCSCSCSCCCSC(S)SCS QMHKMLUVKWZPCH-UHFFFAOYSA-N 0.000 description 1
- QNITWMBGUWZSSI-UHFFFAOYSA-N sulfanylmethylsulfanylmethylsulfanylmethanethiol Chemical compound SCSCSCS QNITWMBGUWZSSI-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- TWXMZYPORGXIFB-UHFFFAOYSA-N thiophene-3,4-dithiol Chemical group SC1=CSC=C1S TWXMZYPORGXIFB-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- NNMVCFPMIBOZCL-UHFFFAOYSA-N toluene 2,4-diisothiocyanate Chemical compound CC1=CC=C(N=C=S)C=C1N=C=S NNMVCFPMIBOZCL-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/52—Polythioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
-
- 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
Definitions
- the present invention relates to a composition for an optical material and the like, and more particularly to an optical material such as a plastic lens, a prism, an optical fiber, an information recording base, and a filter, and particularly suitable for a plastic lens.
- the present invention relates to an optical material made of polyurethane resin having good optical properties by polymerizing a polymerizable composition comprising a polythiol compound and a polyiso (thio) cyanate compound.
- Resin-made optical materials are lighter and harder to break than optical materials made of inorganic materials, and can be dyed. Therefore, in recent years, it has rapidly spread to optical materials such as eyeglass lenses and camera lenses.
- the resin for optical materials has been required to have higher performance. Specifically, higher refractive index, higher Abbe number, lower specific gravity, higher heat resistance, etc. have been demanded. In response to such demands, various resins for optical materials have been developed and used so far.
- the most typical resins include resins obtained by reacting a polythiol compound and a polyiso (thio) cyanate compound as shown in Patent Documents 1 and 2.
- This resin is colorless and transparent, and has excellent properties such as impact properties, dyeability and processability.
- the problem to be solved by the present invention is to provide a composition for optical materials in which the occurrence of polymerization unevenness called striae, particularly the occurrence of striae in a lens having a high frequency and a tight curve, is suppressed.
- the present inventors have found that a polymerization catalyst having a mass ratio of dibutyltin dichloride to monobutyltin trichloride of 97.0 / 3.0 to 100.0 / 0.0 And this subject was solved by the composition for optical materials containing a polythiol compound and a polyiso (thio) cyanate compound, and it came to this invention. That is, the present invention is as follows.
- An optical material composition comprising a polymerization catalyst, a polythiol compound, and a polyiso (thio) cyanate compound.
- composition for optical materials according to ⁇ 1>, wherein the polymerization catalyst has a dibutyltin dichloride content of 97.0% by mass or more and a monobutyltin trichloride content of 3.0% by mass or less. .
- the polythiol compound is 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane, bis (mercaptomethyl) -3,6,9-trithia-1,11-undecanedithiol, penta Selected from the group consisting of erythritol tetrakis (3-mercaptopropionate), bis (mercaptomethyl) sulfide, 1,3-bis (mercaptomethyl) benzene, 1,1,3,3-tetrakis (mercaptomethylthio) propane
- the polyiso (thio) cyanate compound is 2,5-bis (isocyanatomethyl) -bicyclo [2.2.1] heptane, 2,6-bis (isocyanatomethyl) -bicyclo [2.2. 1] Heptane, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, isophorone diisocyanate, 1,3-bis (isocyanatomethyl) benzene and ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylxylylene diisocyanate
- ⁇ 6> The optical material according to ⁇ 5>, wherein an annealing treatment is performed after the polymerization of the optical material composition.
- optical material of the present invention it is possible to provide a composition for optical material that suppresses the occurrence of polymerization unevenness called striae, which is difficult with the prior art, in particular, the occurrence of striae in lenses with high frequency and tight curves. It became.
- the present invention contains a polymerization catalyst having a mass ratio of dibutyltin dichloride and monobutyltin trichloride of 97.0 / 3.0 to 100.0 / 0.0, a polythiol compound, and a polyiso (thio) cyanate compound.
- a polyurethane resin for optical materials is produced by polymerizing the polymerizable composition.
- dibutyltin dichloride is obtained by the reaction of Grignard reagent and tin tetrachloride. However, since the reaction is a sequential reaction, only dibutyltin dichloride cannot be obtained, and monobutyltin trichloride is mixed.
- a purification step for obtaining dibutyltin dichloride is required except for mixed monobutyltin trichloride.
- the technique include purification methods such as distillation, recrystallization, reprecipitation, column separation operation, adsorbent treatment, and ion exchange resin treatment, but distillation is preferred. Distillation may be carried out at normal pressure or reduced pressure, but preferably under reduced pressure, more preferably 0.01 to 100 Torr, still more preferably 0.1 to 50 Torr.
- the distillation temperature is not a problem as long as the product is distilled without decomposition, but is preferably 50 ° C. to 190 ° C., more preferably 100 ° C. to 180 ° C.
- the polymerization catalyst used in the composition for optical material of the present invention dibutyltin dichloride (Bu 2 SnCl 2) and the mass ratio of the monobutyltin trichloride (BuSnCl 3) (Bu 2 SnCl 2 / BuSnCl 3) is 97.0 / 3
- the effect of the present invention can be obtained at 0.0 to 100.0 / 0.0, preferably 99.0 / 1.0 to 100.0 / 0.0, more preferably 99.5 / 0.5 to 100.0 / 0.0.
- the polymerization catalyst used in the composition for optical materials of the present invention preferably has a dibutyltin dichloride content of 97.0% by mass or more and a monobutyltin trichloride content of 3.0% by mass or less.
- the content of dibutyltin dichloride is 99.0% by mass or more and the content of monobutyltin trichloride is 1.0% by mass or less, most preferably the content of dibutyltin dichloride is 99.5% by mass or more and The content of monobutyltin trichloride is 0.5% by mass or less.
- the upper limit of the content of dibutyltin dichloride and the lower limit of the content of monobutyltin trichloride in the polymerization catalyst are not particularly limited, and a polymerization catalyst consisting only of dibutyltin dichloride can be used, but usually the content of dibutyltin dichloride is 99.99 mass% or less, and the content of monobutyltin trichloride is 0.01 mass% or more.
- the amount of the polymerization catalyst added varies depending on the components of the composition, the mixing ratio, and the polymerization curing method, but is not generally determined, but is usually 0.001% by mass or more based on the total amount of the optical material composition. 5% by mass or less, preferably 0.01% by mass or more and 1% by mass or less, and most preferably 0.01% by mass or more and 0.5% by mass or less.
- the addition amount of the polymerization catalyst is more than 5% by mass, the refractive index and heat resistance of the cured product may be lowered and coloring may occur.
- the addition amount of a polymerization catalyst is less than 0.001 mass%, it may not fully harden
- the polythiol compound used in the present invention is not particularly limited as long as it is a compound having two or more thiol groups in one molecule.
- polythiol compound examples include methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6- Hexanedithiol, 1,2,3-propanetrithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2 -Dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl ester) thiomalate, 2,3-dimercapto-1-propanol (2-mercaptoacetate) ), 2,3-dimercapto-1-propanol 3-mer
- Aromatic polythiol compounds containing sulfur atoms in addition to mercapto groups such as benzene, 1,3,5-tris (mercaptoethylthio) benzene, etc., and their nuclear alkylates;
- Heterocyclic compounds containing sulfur atoms in addition to mercapto groups such as 3,4-thiophenedithiol and 2,5-dimercapto-1,3,4-thiadiazole;
- Glycerin di (mercaptoacetate), 2,4-dimercaptophenol, 3,4-dimercapto-2-propanol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto 1,3-butanediol, pentaerythritol tris (3-mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), dipentaerythritol pentakis (3-mercapto) Compounds containing a hydroxy group in addition to a mercapto group such as propionate), hydroxymethyl-tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-mercaptoethylthiobenzene;
- polythiol compound is not limited to the above exemplified compounds.
- Each of the above exemplary compounds may be used alone or in combination of two or more.
- preferred compounds are 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane, bis (mercaptomethyl) -3,6,9-trithia-1,11-undecane.
- the polyiso (thio) cyanate compound used in the present invention is not particularly limited as long as it is a compound having two or more iso (thio) cyanate groups in one molecule.
- the term “iso (thio) cyanate” means “isocyanate or isothiocyanate”.
- polyiso (thio) cyanate compound examples include hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, and 1,3-butadiene.
- Aromatic sulfide polyisocyanate compounds such as 2-isocyanatophenyl-4-isocyanatophenyl sulfide, bis (4-isocyanatophenyl) sulfide, bis (4-isocyanatomethylphenyl) sulfide;
- Aromatic disulfide polyisocyanate compounds such as disulfide, bis (4-methyl-5-isocyanatophenyl) disulfide, bis (4-methoxy-3-isocyanatophenyl) disulfide;
- Aliphatic polyisothiocyanate compounds such as 1,2-diisothiocyanatoethane and 1,6-diisothiocyanatohexane; Alicyclic polyisothiocyanate compounds such as cyclohexanediisothiocyanate; 1,2-di Isothiocyanatobenzene, 1,3-diisothiocyanatobenzene, 1,4-diisothiocyanatobenzene, 2,4-diisothiocyanatotoluene, 2,5-diisothiocyanato-m-xylene, 4, 4'-methylenebis (phenylisothiocyanate), 4,4'-methylenebis (2-methylphenylisothiocyanate), 4,4'-methylenebis (3-methylphenylisothiocyanate), 4,4'-diisothi Oceanatobenzophenone, 4,4'-diisothiocyanato-3,3'-di
- carbonyl polyisothiocyanate such as 1,3-benzenedicarbonyldiisothiocyanate, 1,4-benzenedicarbonyldiisothiocyanate, (2,2-pyridine) -4,4-dicarbonyldiisothiocyanate, etc.
- Isocyanate compounds sulfur-containing aliphatic polyisothiocyanate compounds such as thiobis (3-isothiocyanatopropane), thiobis (2-isothiocyanatoethane), dithiobis (2-isothiocyanatoethane);
- Sulfur-containing aroma such as 1-isothiocyanato-4-[(2-isothiocyanato) sulfonyl] benzene, thiobis (4-isothiocyanatobenzene), sulfonyl (4-isothiocyanatobenzene), dithiobis (4-isothiocyanatobenzene) Group polyisothiocyanate compounds; sulfur-containing alicyclic polyisothiocyanate compounds such as 2,5-diisothiocyanatothiophene and 2,5-diisothiocyanato-1,4-dithiane;
- halogen-substituted products such as chlorine-substituted products and bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products and prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, and burette-modified products.
- Bodies, dimerization or trimerization reaction products and the like can also be used.
- polyiso (thio) cyanate compound is not limited to the above exemplified compounds.
- each of the above exemplary compounds may be used alone or in combination of two or more.
- preferred compounds are 2,5-bis (isocyanatomethyl) -bicyclo [2.2.1] heptane, 2,6-bis (isocyanatomethyl) -bicyclo [2.2.1]. ] Heptane, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, isophorone diisocyanate, 1,3-bis (isocyanatomethyl) benzene and ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylxylylene diisocyanate It is.
- the composition for optical materials of the present invention is a composition mainly comprising a polythiol compound and a polyiso (thio) cyanate compound.
- optional components such as catalysts other than dibutyltin dichloride, internal mold release agents, ultraviolet absorbers, and bluing agents can be added as necessary to further improve the practicality of the resulting material.
- a polyurethane-based lens can be produced by injecting a polythiol compound, a polyiso (thio) cyanate compound and, if necessary, optional components into a lens mold and polymerizing them.
- a benzotriazole-based compound can be mentioned.
- Specific examples of preferred compounds include 2- (2-hydroxy-5-methylphenyl) -2H-benzotriazole, 5-chloro-2- (3,5-di-tert-butyl-2-hydroxyphenyl) -2H.
- release agents include fluorine-based nonionic surfactants, silicon-based nonionic surfactants, phosphate esters, acidic phosphate esters, oxyalkylene-type acidic phosphate esters, alkali metal salts of acidic phosphate esters, and alkalis of oxyalkylene-type acidic phosphate esters.
- Examples include metal salts, metal salts of higher fatty acids, higher fatty acid esters, paraffins, waxes, higher aliphatic amides, higher aliphatic alcohols, polysiloxanes, and aliphatic amine ethylene oxide adducts. May be mixed and used. The addition amount is usually 0.0001 to 5% by mass with respect to the total amount of the optical material composition.
- an active hydrogen compound typified by an amine
- An optical material made of polyurethane resin is usually produced by cast polymerization. Specifically, a polythiol compound and a polyiso (thio) cyanate compound are mixed. This mixed solution (polymerizable composition) is defoamed by an appropriate method as necessary, and then poured into a mold for optical material, and is usually gradually heated from a low temperature to a high temperature for polymerization. Thereafter, the optical material is obtained by demolding.
- the deaeration treatment is performed under reduced pressure before, during or after mixing the compound capable of reacting with some or all of the composition components, the polymerization catalyst, and the additive. Preferably, it is performed under reduced pressure during or after mixing.
- the treatment conditions are 0 to 100 ° C. for 1 minute to 24 hours under a reduced pressure of 0.001 to 50 torr.
- the degree of vacuum is preferably 0.005 to 25 torr, more preferably 0.01 to 10 torr, and the degree of vacuum may be varied within these ranges.
- the deaeration time is preferably 5 minutes to 18 hours, more preferably 10 minutes to 12 hours.
- the temperature at the time of deaeration is preferably 5 ° C. to 80 ° C., more preferably 10 ° C. to 60 ° C., and the temperature may be varied within these ranges.
- renewing the interface of the resin composition by stirring, blowing of gas, vibration by ultrasonic waves or the like is a preferable operation for enhancing the degassing effect.
- the quality of the optical material of the present invention is further improved. It is also preferable from the viewpoint of increasing.
- the composition for optical material subjected to the above reaction and treatment is poured into a glass or metal mold, and after the polymerization and curing reaction is advanced by irradiation with active energy rays such as heating or ultraviolet rays, the composition is removed from the mold. . In this way, an optical material is manufactured.
- the composition for optical material is preferably polymerized and cured by heating to produce an optical material.
- the curing time is usually 0.1 to 200 hours, preferably 1 to 100 hours
- the curing temperature is usually ⁇ 10 ° C. to 160 ° C., preferably ⁇ 10 ° C. to 140 ° C.
- the polymerization can be performed by holding at a predetermined polymerization temperature for a predetermined time, raising the temperature by 0.1 ° C. to 100 ° C./hour, lowering the temperature by 0.1 ° C. to 100 ° C./hour, and combinations thereof.
- the polyurethane-based resin produced by the method of the present invention is lightweight and has excellent impact resistance, and also has a good hue. Therefore, this resin is suitable for applications of optical materials such as lenses and prisms. In particular, the resin is very suitable for use in lenses such as spectacle lenses and camera lenses.
- the optical material is surface-polished, antistatic treatment, for the purpose of improving the antireflection, high hardness, wear resistance, chemical resistance, cloud resistance, or fashionability, if necessary.
- Physical and chemical treatments such as hard coat treatment, non-reflective coat treatment, dyeing treatment, and light control treatment can be performed.
- Striae Ten lenses having a lens diameter of 75 mm and a power of + 10D were prepared and visually observed by the Schlieren method. ⁇ indicates that no striae is observed, ⁇ indicates that 9 striae is not observed, ⁇ indicates that 7 or 8 striae is not observed, and x indicates that no striae is observed. ⁇ or more is acceptable.
- Polymerization curing was performed by the following method.
- Polymerization method A To 52 parts by weight of 1,3-bis (isocyanatomethyl) benzene (hereinafter referred to as Compound X), 0.05 part by weight of a polymerization catalyst comprising dibutyltin dichloride and monobutyltin trichloride, and 0.10 part by weight of dioctyl phosphate are added. The mixture was mixed and dissolved at 10 to 15 ° C. Further, 48 parts by weight of 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane (Compound A) was mixed to obtain a uniform solution.
- Compound X 1,3-bis (isocyanatomethyl) benzene
- This mixed homogeneous liquid was defoamed at 600 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, poured into a 70 mm diameter + 5D mold, and polymerized from 40 ° C. to 130 ° C. over 24 hours. . Thereafter, the mold was removed to obtain an optical material.
- This mixed homogeneous liquid was defoamed at 600 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, poured into a 70 mm diameter + 5D mold, and polymerized from 40 ° C. to 130 ° C. over 24 hours. . Thereafter, the mold was removed to obtain an optical material.
- a polymerization catalyst having a dibutyltin dichloride content of 94.0% by mass and a monobutyltin trichloride content of 6.0% by mass was distilled at 0.1 to 50 Torr and 50 to 200 ° C. for 0.5 to 48 hours. Then, a polymerization catalyst having a monobutyltin trichloride content of 0.4 mass%, 0.9 mass%, and 2.8 mass% was prepared (the content was measured by gas chromatography).
- Example 1 It was cured by the technique of polymerization method A using a polymerization catalyst having a dibutyltin dichloride content of 99.6% by mass and a monobutyltin trichloride content of 0.4% by mass. The result of pulse separation was good and ⁇ . The results are summarized in Table 1.
- Example 2 It was cured by the polymerization method shown in Table 1 using a polymerization catalyst having a dibutyltin dichloride content of 99.6% by mass and a monobutyltin trichloride content of 0.4% by mass. The results are shown in Table 1.
- Example 5 It was cured by the polymerization method shown in Table 1 using a polymerization catalyst having a dibutyltin dichloride content of 99.1% by mass and a monobutyltin trichloride content of 0.9% by mass. The results are shown in Table 1.
- Example 9 It was cured by the polymerization method shown in Table 1 using a polymerization catalyst having a dibutyltin dichloride content of 97.2% by mass and a monobutyltin trichloride content of 2.8% by mass. The results are shown in Table 1.
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Abstract
Description
1,3-ビス(イソシアナトメチル)ベンゼン(以下、化合物Xとする)52重量部に、ジブチルスズジクロライドとモノブチルスズトリクロライドからなる重合触媒0.05重量部、リン酸ジオクチル0.10重量部を、10~15℃にて混合溶解させた。さらに、1,2-ビス[(2-メルカプトエチル)チオ]-3-メルカプトプロパン(化合物A)48重量部を混合し、均一液とした。この混合均一液を600Paにて1時間脱泡を行った後、1μmのPTFEフィルターにて濾過を行い、直径70mm、+5Dのモールドへ注入し、40℃から130℃まで24時間かけて重合させた。その後脱型し、光学材料を得た。
1,3-ビス(イソシアナトメチル)ベンゼン(化合物X)51重量部に、ジブチルスズジクロライドとモノブチルスズトリクロライドからなる重合触媒0.05重量部、リン酸ジオクチル0.10重量部を、10~15℃にて混合溶解させた。さらに、ビス(メルカプトメチル)-3,6,9-トリチア-1,11-ウンデカンジチオール(化合物B)49重量部を混合し、均一液とした。この混合均一液を600Paにて1時間脱泡を行った後、1μmのPTFEフィルターにて濾過を行い、直径70mm、+5Dのモールドへ注入し、40℃から130℃まで24時間かけて重合させた。その後脱型し、光学材料を得た。
2,5-ビス(イソシアナトメチル)-ビシクロ[2.2.1]ヘプタンと2,6-ビス(イソシアナトメチル)-ビシクロ[2.2.1]ヘプタンの混合物(以下、化合物Yとする)50.6重量部に、ジブチルスズジクロライドとモノブチルスズトリクロライドからなる重合触媒0.06重量部、リン酸ジオクチル0.12重量部を、10~15℃にて混合溶解させた。さらに、1,2-ビス[(2-メルカプトエチル)チオ]-3-メルカプトプロパン(化合物A)25.5重量部とペンタエリスリトールテトラキス(メルカプトプロピオネート)(化合物C)23.9重量部を混合し、均一液とした。この混合均一液を600Paにて1時間脱泡を行った後、1μmのPTFEフィルターにて濾過を行い、直径70mm、+5Dのモールドへ注入し、40℃から130℃まで24時間かけて重合させた。その後脱型し、光学材料を得た。
2,5-ビス(イソシアナトメチル)-ビシクロ[2.2.1]ヘプタンと2,6-ビス(イソシアナトメチル)-ビシクロ[2.2.1]ヘプタンの混合物(化合物Y)50.6重量部に、ジブチルスズジクロライドとモノブチルスズトリクロライドからなる重合触媒0.06重量部、リン酸ジオクチル0.12重量部を、10~15℃にて混合溶解させた。さらに、ビス(メルカプトメチル)-3,6,9-トリチア-1,11-ウンデカンジチオール(化合物B)を25.5重量部とペンタエリスリトールテトラキス(メルカプトプロピオネート)(化合物C)23.9重量部を混合し、均一液とした。この混合均一液を600Paにて1時間脱泡を行った後、1μmのPTFEフィルターにて濾過を行い、直径70mm、+5Dのモールドへ注入し、40℃から130℃まで24時間かけて重合させた。その後脱型し、光学材料を得た。
ジブチルスズジクロライドの含有量が94.0質量%で且つモノブチルスズトリクロライドの含有量が6.0質量%の重合触媒を0.1~50Torr、50~200℃で、0.5時間~48時間蒸留して、モノブチルスズトリクロライド含有量が0.4質量%、0.9質量%、2.8質量%の重合触媒を調製した(含有量は、ガスクロマトグラフィーで測定した)。
ジブチルスズジクロライドの含有量が99.6質量%で且つモノブチルスズトリクロライドの含有量が0.4質量%の重合触媒を用い、重合方法Aの手法で硬化させた。脈離の結果は良好であり◎であった。結果を表1にまとめた。
ジブチルスズジクロライドの含有量が99.6質量%で且つモノブチルスズトリクロライドの含有量が0.4質量%の重合触媒を用いて、表1に示す重合方法で硬化させた。結果を表1に示す。
ジブチルスズジクロライドの含有量が99.1質量%で且つモノブチルスズトリクロライドの含有量が0.9質量%の重合触媒を用いて、表1に示す重合方法で硬化させた。結果を表1に示す。
ジブチルスズジクロライドの含有量が97.2質量%で且つモノブチルスズトリクロライドの含有量が2.8質量%の重合触媒を用いて、表1に示す重合方法で硬化させた。結果を表1に示す。
ジブチルスズジクロライドの含有量が94.0質量%で且つモノブチルスズトリクロライドの含有量が6.0質量%の重合触媒を用いて、表1に示す重合方法で硬化させた。結果を表1に示す。
Claims (6)
- ジブチルスズジクロライドとモノブチルスズトリクロライドとの質量比が97.0/3.0~100.0/0.0である重合触媒と、
ポリチオール化合物と、
ポリイソ(チオ)シアナート化合物と
を含有する光学材料用組成物。 - 前記重合触媒は、ジブチルスズジクロライドの含有量が97.0質量%以上で且つモノブチルスズトリクロライドの含有量が3.0質量%以下である請求項1に記載の光学材料用組成物。
- 前記ポリチオール化合物が、1,2-ビス[(2-メルカプトエチル)チオ]-3-メルカプトプロパン、ビス(メルカプトメチル)-3,6,9-トリチア-1,11-ウンデカンジチオール、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)、ビス(メルカプトメチル)スルフィド、1,3-ビス(メルカプトメチル)ベンゼン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンからなる群より選ばれた少なくとも1種の化合物である請求項1記載の光学材料用組成物。
- 前記ポリイソ(チオ)シアナート化合物が、2,5-ビス(イソシアナトメチル)-ビシクロ[2.2.1]ヘプタン、2,6-ビス(イソシアナトメチル)-ビシクロ[2.2.1]ヘプタン、ビス(イソシアナトメチル)シクロヘキサン、ジシクロヘキシルメタンジイソシアナート、イソホロンジイソシアナート、1,3-ビス(イソシアナトメチル)ベンゼン及びα,α,α’,α’-テトラメチルキシリレンジイソシアナートからなる群より選ばれた少なくとも1種の化合物である請求項1記載の光学材料用組成物。
- 請求項1記載の光学材料用組成物を重合することにより得られた光学材料。
- 前記光学材料用組成物の重合後にアニール処理が施されている、請求項5記載の光学材料。
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CN102459389A (zh) * | 2009-06-23 | 2012-05-16 | 卡尔蔡司视觉澳大利亚控股有限公司 | 基于硫代氨基甲酸酯的镜片元件及它们的生产方法 |
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- 2011-11-07 WO PCT/JP2011/006207 patent/WO2012090372A1/ja active Application Filing
- 2011-11-07 BR BR112013016183-3A patent/BR112013016183B1/pt active IP Right Grant
- 2011-11-07 KR KR1020137016579A patent/KR101877590B1/ko active IP Right Grant
- 2011-11-07 JP JP2012550682A patent/JP5842827B2/ja active Active
- 2011-11-07 EP EP11852983.3A patent/EP2660260B1/en active Active
- 2011-11-07 US US13/996,171 patent/US20130267673A1/en not_active Abandoned
- 2011-11-07 CN CN201180063057.0A patent/CN103282399B/zh active Active
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2021060563A1 (ja) * | 2019-09-27 | 2021-04-01 | ホヤ レンズ タイランド リミテッド | 光学部材用重合性組成物、光学部材、及び、着色光学部材 |
JP2021054915A (ja) * | 2019-09-27 | 2021-04-08 | ホヤ レンズ タイランド リミテッドHOYA Lens Thailand Ltd | 光学部材用重合性組成物、光学部材、及び、着色光学部材 |
Also Published As
Publication number | Publication date |
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KR20140004664A (ko) | 2014-01-13 |
US20130267673A1 (en) | 2013-10-10 |
EP2660260B1 (en) | 2018-09-12 |
EP2660260A4 (en) | 2014-06-11 |
JP5842827B2 (ja) | 2016-01-13 |
CN103282399A (zh) | 2013-09-04 |
BR112013016183B1 (pt) | 2020-03-24 |
KR101877590B1 (ko) | 2018-07-12 |
CN103282399B (zh) | 2015-08-19 |
EP2660260A1 (en) | 2013-11-06 |
JPWO2012090372A1 (ja) | 2014-06-05 |
BR112013016183A2 (ja) | 2018-07-17 |
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