JP5842827B2 - 光学材料用組成物 - Google Patents
光学材料用組成物 Download PDFInfo
- Publication number
- JP5842827B2 JP5842827B2 JP2012550682A JP2012550682A JP5842827B2 JP 5842827 B2 JP5842827 B2 JP 5842827B2 JP 2012550682 A JP2012550682 A JP 2012550682A JP 2012550682 A JP2012550682 A JP 2012550682A JP 5842827 B2 JP5842827 B2 JP 5842827B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- mercaptomethylthio
- isocyanatomethyl
- composition
- compound
- 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.)
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- 239000000463 material Substances 0.000 title claims description 55
- 230000003287 optical effect Effects 0.000 title claims description 55
- 239000000203 mixture Substances 0.000 title claims description 44
- -1 (thio) cyanate compound Chemical class 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 60
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 claims description 27
- 239000002685 polymerization catalyst Substances 0.000 claims description 26
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- 229920006295 polythiol Polymers 0.000 claims description 22
- 229920000582 polyisocyanurate Polymers 0.000 claims description 16
- 239000011495 polyisocyanurate Substances 0.000 claims description 16
- 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 7
- 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 7
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-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
- 238000000137 annealing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 206010040925 Skin striae Diseases 0.000 description 11
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 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
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 3
- RHMKQRWOFRAOHS-UHFFFAOYSA-N (sulfanylmethyldisulfanyl)methanethiol Chemical compound SCSSCS RHMKQRWOFRAOHS-UHFFFAOYSA-N 0.000 description 2
- OAWJNGTVHKRBAT-UHFFFAOYSA-N 1,1-bis(isocyanatomethylsulfanyl)ethane Chemical compound O=C=NCSC(C)SCN=C=O OAWJNGTVHKRBAT-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000003490 Thiodipropionic acid Substances 0.000 description 2
- VDKDFKRKAPXHBH-UHFFFAOYSA-N [3-(2-sulfanylpropanoyloxy)-2,2-bis(2-sulfanylpropanoyloxymethyl)propyl] 2-sulfanylpropanoate Chemical compound CC(S)C(=O)OCC(COC(=O)C(C)S)(COC(=O)C(C)S)COC(=O)C(C)S VDKDFKRKAPXHBH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000004662 dithiols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 2
- INBDPOJZYZJUDA-UHFFFAOYSA-N methanedithiol Chemical compound SCS INBDPOJZYZJUDA-UHFFFAOYSA-N 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- VUTVSWPVTJZPFU-UHFFFAOYSA-N propylsulfanylmethanethiol Chemical compound CCCSCS VUTVSWPVTJZPFU-UHFFFAOYSA-N 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 2
- 235000019303 thiodipropionic acid Nutrition 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 2
- CAYNCHQZXZMUEX-UHFFFAOYSA-N (hydroxymethyldisulfanyl)methanol 2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OCSSCO CAYNCHQZXZMUEX-UHFFFAOYSA-N 0.000 description 1
- BXGKVFOHNHSLHH-UHFFFAOYSA-N (hydroxymethyldisulfanyl)methanol 3-sulfanylpropanoic acid Chemical compound OCSSCO.OC(=O)CCS.OC(=O)CCS BXGKVFOHNHSLHH-UHFFFAOYSA-N 0.000 description 1
- XVNGTGZGWDPIRR-UHFFFAOYSA-N 1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCS XVNGTGZGWDPIRR-UHFFFAOYSA-N 0.000 description 1
- WGBYQYHKMIWESB-UHFFFAOYSA-N 1,2,3-tris(2-isocyanatoethylsulfanyl)propane Chemical compound O=C=NCCSCC(SCCN=C=O)CSCCN=C=O WGBYQYHKMIWESB-UHFFFAOYSA-N 0.000 description 1
- LTKBJFRCZZYLJY-UHFFFAOYSA-N 1,2,3-tris(isocyanatomethylsulfanyl)propane Chemical compound O=C=NCSCC(SCN=C=O)CSCN=C=O LTKBJFRCZZYLJY-UHFFFAOYSA-N 0.000 description 1
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 description 1
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- VODRFGZSOKHZDQ-UHFFFAOYSA-N 1,2-bis(3-isocyanatopropyl)benzene Chemical compound O=C=NCCCC1=CC=CC=C1CCCN=C=O VODRFGZSOKHZDQ-UHFFFAOYSA-N 0.000 description 1
- YCFNKSOIDNKUIO-UHFFFAOYSA-N 1,2-bis(4-isocyanatobutyl)benzene Chemical compound O=C=NCCCCC1=CC=CC=C1CCCCN=C=O YCFNKSOIDNKUIO-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
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- PBPRZRZXNXUAEJ-UHFFFAOYSA-N 1,2-bis(sulfanyl)butane-1,3-diol Chemical compound CC(O)C(S)C(O)S PBPRZRZXNXUAEJ-UHFFFAOYSA-N 0.000 description 1
- PIDUEESSWOVGNT-UHFFFAOYSA-N 1,2-diethyl-3,4-diisocyanatobenzene Chemical compound CCC1=CC=C(N=C=O)C(N=C=O)=C1CC PIDUEESSWOVGNT-UHFFFAOYSA-N 0.000 description 1
- MMJDYWRDMVPQPF-UHFFFAOYSA-N 1,2-diisocyanato-3,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(N=C=O)C(N=C=O)=C1C(C)C MMJDYWRDMVPQPF-UHFFFAOYSA-N 0.000 description 1
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- HMDXXHVBUMKDQL-UHFFFAOYSA-N 1,2-diisocyanato-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(N=C=O)=C1N=C=O HMDXXHVBUMKDQL-UHFFFAOYSA-N 0.000 description 1
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- WOCWGASBYDHHMD-UHFFFAOYSA-N 1,3-dithiolan-2-ylsulfanylmethanethiol Chemical compound SCSC1SCCS1 WOCWGASBYDHHMD-UHFFFAOYSA-N 0.000 description 1
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- JFLJVRLBIZHFSU-UHFFFAOYSA-N 1,4-dithiane-2,5-dithiol Chemical compound SC1CSC(S)CS1 JFLJVRLBIZHFSU-UHFFFAOYSA-N 0.000 description 1
- YPLPXJFDSYXYSF-UHFFFAOYSA-N 1,5,7,11-tetrathiaspiro[5.5]undecane-3,9-dithiol Chemical compound S1CC(S)CSC21SCC(S)CS2 YPLPXJFDSYXYSF-UHFFFAOYSA-N 0.000 description 1
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-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
- VZZPYUKWXDLMGI-UHFFFAOYSA-N 1,6-diisothiocyanatohexane Chemical compound S=C=NCCCCCCN=C=S VZZPYUKWXDLMGI-UHFFFAOYSA-N 0.000 description 1
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- 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
- 239000012964 benzotriazole Substances 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-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
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical group CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 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
- 239000000539 dimer Substances 0.000 description 1
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000004252 dithioacetals 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
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 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
- 239000001294 propane Substances 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
- 239000000758 substrate Substances 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
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- TWXMZYPORGXIFB-UHFFFAOYSA-N thiophene-3,4-dithiol Chemical compound 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
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 (5)
- ジブチルスズジクロライドの含有量が97.0質量%以上99.99%以下で且つモノブチルスズトリクロライドの含有量が0.01質量%以上3.0質量%以下である重合触媒と、
ポリチオール化合物と、
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。 - 前記ポリイソ(チオ)シアナート化合物が1,3−ビス(イソシアナトメチル)ベンゼン又は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]ヘプタンの混合物である請求項1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。
- 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4記載の光学材料。
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KR101827033B1 (ko) * | 2010-11-17 | 2018-02-07 | 미츠비시 가스 가가쿠 가부시키가이샤 | 광학 재료용 조성물 |
TWI699389B (zh) | 2014-07-18 | 2020-07-21 | 日商三菱瓦斯化學股份有限公司 | 聚硫醇組成物及其製造方法 |
KR20190079956A (ko) * | 2017-12-28 | 2019-07-08 | 에스케이씨 주식회사 | 광학 재료용 중합성 조성물 |
KR102345703B1 (ko) * | 2018-03-29 | 2021-12-31 | 호야 렌즈 타일랜드 리미티드 | 중합성 조성물의 제조 방법 |
CN108794781B (zh) * | 2018-06-22 | 2019-11-22 | 苏州大学 | 一种透明可卷曲折叠聚硅氧烷膜及其制备与自修复方法 |
WO2020004532A1 (ja) * | 2018-06-29 | 2020-01-02 | 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および光学部材 |
KR102553438B1 (ko) * | 2018-07-30 | 2023-07-10 | 미쓰이 가가쿠 가부시키가이샤 | 에피설파이드계 고굴절 광학재료용 조성물과 광학재료의 제조방법 |
JP7296754B2 (ja) * | 2019-03-28 | 2023-06-23 | 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、及び眼鏡レンズ |
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 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009226742A (ja) * | 2008-03-24 | 2009-10-08 | Seiko Epson Corp | プラスチックレンズの製造方法 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2560042A (en) * | 1949-06-08 | 1951-07-10 | Firestone Tire & Rubber Co | Preparation of butyltin chlorides |
JPS60199016A (ja) | 1984-03-23 | 1985-10-08 | Mitsui Toatsu Chem Inc | チオカルバミン酸s―アルキルエステル系レンズ用樹脂の製造方法 |
JP2703753B2 (ja) | 1988-12-22 | 1998-01-26 | 三井東圧化学株式会社 | レンズ及びその製造方法 |
JP3491164B2 (ja) * | 1992-06-26 | 2004-01-26 | 株式会社ニコン | 反射防止性プラスチックレンズ |
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 |
JP3279848B2 (ja) * | 1993-12-20 | 2002-04-30 | 三井化学株式会社 | 高速重合性樹脂組成物およびレンズ |
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 |
JP3438318B2 (ja) | 1994-04-22 | 2003-08-18 | 旭化成株式会社 | タイヤ用ゴム組成物 |
JP3422079B2 (ja) | 1994-06-01 | 2003-06-30 | チッソ株式会社 | 多分岐脂肪族−芳香族ポリエステルポリオールの製造法 |
JPH08198958A (ja) | 1995-01-24 | 1996-08-06 | Toray Ind Inc | ポリブチレンテレフタレート系ポリマーの製造方法 |
JPH08208794A (ja) * | 1995-02-03 | 1996-08-13 | Mitsui Toatsu Chem Inc | 含硫ウレタン系プラスチックレンズの製造方法 |
US5736609A (en) * | 1995-06-30 | 1998-04-07 | Mitsui Toatsu Chemicals, Inc. | Sulfur-containing urethane-based resin composition, its resin, and optical element and lens comprising resin |
JP4206815B2 (ja) * | 2003-05-14 | 2009-01-14 | 三菱瓦斯化学株式会社 | 光学材料の製造方法 |
JP4291190B2 (ja) * | 2004-03-26 | 2009-07-08 | 三井化学株式会社 | 高屈折率・高耐候性樹脂及びその製造方法 |
JP4961103B2 (ja) * | 2004-08-27 | 2012-06-27 | Hoya株式会社 | プラスチックレンズの製造方法及びプラスチックレンズ |
EP1743898A1 (en) | 2005-07-12 | 2007-01-17 | Arkema Vlissingen B.V. | Process for the preparation of monoalkyl tin trihalides and dialkyl tin dihalides |
CN101291907A (zh) | 2005-10-31 | 2008-10-22 | 三井化学株式会社 | 季戊四醇巯基羧酸酯的制备方法、由该方法得到的季戊四醇巯基羧酸酯及其用途 |
CN104211623A (zh) | 2006-04-19 | 2014-12-17 | 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 |
CN102516487B (zh) * | 2006-10-16 | 2015-07-08 | 三井化学株式会社 | 光学材料用树脂的制造方法 |
JP5340937B2 (ja) | 2007-07-25 | 2013-11-13 | Hoya株式会社 | プラスチックレンズの製造方法 |
US7867577B2 (en) * | 2008-05-15 | 2011-01-11 | Essilor International (Compagnie Generale D'optique) | Sulfur modified silanes for the elaboration of high refractive index materials |
US8304507B2 (en) * | 2008-06-30 | 2012-11-06 | Mitsui Chemicals, Inc. | Polymerizable composition for polythiourethane optical material, polythiourethane optical material obtained from the polymerizable composition, and polymerization catalyst for polythiourethane optical material |
WO2010148424A1 (en) * | 2009-06-23 | 2010-12-29 | Carl Zeiss Vision Australia Holdings Limited | Thiourethane-based lens elements and processes for their production |
KR101827033B1 (ko) * | 2010-11-17 | 2018-02-07 | 미츠비시 가스 가가쿠 가부시키가이샤 | 광학 재료용 조성물 |
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EP2660260A1 (en) | 2013-11-06 |
US20130267673A1 (en) | 2013-10-10 |
KR101877590B1 (ko) | 2018-07-12 |
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WO2012090372A1 (ja) | 2012-07-05 |
CN103282399B (zh) | 2015-08-19 |
JPWO2012090372A1 (ja) | 2014-06-05 |
BR112013016183A2 (ja) | 2018-07-17 |
EP2660260A4 (en) | 2014-06-11 |
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BR112013016183B1 (pt) | 2020-03-24 |
CN103282399A (zh) | 2013-09-04 |
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