KR100417985B1 - 안경용 플라스틱 렌즈 - Google Patents
안경용 플라스틱 렌즈 Download PDFInfo
- Publication number
- KR100417985B1 KR100417985B1 KR10-2001-0013147A KR20010013147A KR100417985B1 KR 100417985 B1 KR100417985 B1 KR 100417985B1 KR 20010013147 A KR20010013147 A KR 20010013147A KR 100417985 B1 KR100417985 B1 KR 100417985B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- polyisocyanate compound
- bis
- sulfur
- plastic lens
- Prior art date
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- 239000004033 plastic Substances 0.000 title claims abstract description 46
- 229920003023 plastic Polymers 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 167
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 76
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 76
- 229920006295 polythiol Polymers 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 239000011593 sulfur Substances 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 20
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 17
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 15
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 13
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- VTJSCVKZQYZWHT-UHFFFAOYSA-N CC1SCCSC1.N=C=O Chemical compound CC1SCCSC1.N=C=O VTJSCVKZQYZWHT-UHFFFAOYSA-N 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 7
- MLGITEWCALEOOJ-UHFFFAOYSA-N 2-(thiiran-2-ylmethylsulfanylmethyl)thiirane Chemical compound C1SC1CSCC1CS1 MLGITEWCALEOOJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910010272 inorganic material Inorganic materials 0.000 claims description 3
- 239000011147 inorganic material Substances 0.000 claims description 3
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000003377 silicon compounds Chemical class 0.000 claims 1
- -1 isocyanate compound Chemical class 0.000 description 23
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- RGDDNZPCGLMOMQ-UHFFFAOYSA-N [2-(sulfanylmethyl)-1,4-dithian-2-yl]methanethiol Chemical compound SCC1(CS)CSCCS1 RGDDNZPCGLMOMQ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 4
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- SKGVGRLWZVRZDC-UHFFFAOYSA-N butyl 2-sulfanylacetate Chemical compound CCCCOC(=O)CS SKGVGRLWZVRZDC-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 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 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 4
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 3
- GWAOOGWHPITOEY-UHFFFAOYSA-N 1,5,2,4-dioxadithiane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCO1 GWAOOGWHPITOEY-UHFFFAOYSA-N 0.000 description 3
- AOSATGCSEIIZPL-FMQUCBEESA-N 1-methyl-4-[(e)-4-(4-methylphenyl)hex-3-en-3-yl]benzene Chemical compound C=1C=C(C)C=CC=1C(/CC)=C(\CC)C1=CC=C(C)C=C1 AOSATGCSEIIZPL-FMQUCBEESA-N 0.000 description 3
- SYCHYZZAONZCBB-UHFFFAOYSA-N 2-[2,2-bis(sulfanyl)ethylsulfanyl]ethane-1,1-dithiol Chemical compound SC(S)CSCC(S)S SYCHYZZAONZCBB-UHFFFAOYSA-N 0.000 description 3
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OKFFYKLCPLSDRT-UHFFFAOYSA-N SCC(=O)O.SCC(=O)O.OCSCO Chemical compound SCC(=O)O.SCC(=O)O.OCSCO OKFFYKLCPLSDRT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003490 Thiodipropionic acid Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- INBDPOJZYZJUDA-UHFFFAOYSA-N methanedithiol Chemical compound SCS INBDPOJZYZJUDA-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 150000003553 thiiranes Chemical class 0.000 description 2
- 235000019303 thiodipropionic acid Nutrition 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- BXGKVFOHNHSLHH-UHFFFAOYSA-N (hydroxymethyldisulfanyl)methanol 3-sulfanylpropanoic acid Chemical compound OCSSCO.OC(=O)CCS.OC(=O)CCS BXGKVFOHNHSLHH-UHFFFAOYSA-N 0.000 description 1
- RHMKQRWOFRAOHS-UHFFFAOYSA-N (sulfanylmethyldisulfanyl)methanethiol Chemical compound SCSSCS RHMKQRWOFRAOHS-UHFFFAOYSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical group C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- ALLXFCXWOBUHLB-UHFFFAOYSA-N 1,4-dithiane-2,5-diol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OC1CSC(O)CS1 ALLXFCXWOBUHLB-UHFFFAOYSA-N 0.000 description 1
- JFLJVRLBIZHFSU-UHFFFAOYSA-N 1,4-dithiane-2,5-dithiol Chemical compound SC1CSC(S)CS1 JFLJVRLBIZHFSU-UHFFFAOYSA-N 0.000 description 1
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 1
- FTMOZBNCMQDACZ-UHFFFAOYSA-N 1-(2-sulfanylethylsulfanyl)propane-1,3-dithiol Chemical compound SCCSC(S)CCS FTMOZBNCMQDACZ-UHFFFAOYSA-N 0.000 description 1
- JEARXBADBBQFGS-UHFFFAOYSA-N 1-methoxypropane-1,2-dithiol Chemical compound COC(S)C(C)S JEARXBADBBQFGS-UHFFFAOYSA-N 0.000 description 1
- DLLOHKQWGFKFLO-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dithiol Chemical compound CC1(S)CCCCC1S DLLOHKQWGFKFLO-UHFFFAOYSA-N 0.000 description 1
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 description 1
- WKTIINJWBLIZPI-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OC(=O)CS.OC(=O)CS.OCC(CO)(CO)CO WKTIINJWBLIZPI-UHFFFAOYSA-N 0.000 description 1
- MTZVWTOVHGKLOX-UHFFFAOYSA-N 2,2-bis(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)(CS)CS MTZVWTOVHGKLOX-UHFFFAOYSA-N 0.000 description 1
- SGLYOTGYKDFSSC-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-dithiol Chemical compound SCC(C)(C)CS SGLYOTGYKDFSSC-UHFFFAOYSA-N 0.000 description 1
- VRVKQSIMDPCNDA-UHFFFAOYSA-N 2,3-bis(sulfanyl)-2-(2-sulfanylethyl)butanedioic acid Chemical compound OC(=O)C(S)C(S)(C(O)=O)CCS VRVKQSIMDPCNDA-UHFFFAOYSA-N 0.000 description 1
- HWJPXZLPHCUAAZ-UHFFFAOYSA-N 2,3-bis(sulfanyl)propan-1-ol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OCC(S)CS HWJPXZLPHCUAAZ-UHFFFAOYSA-N 0.000 description 1
- WXDDGAZCUPULGL-UHFFFAOYSA-N 2,3-bis(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSCC(SCS)CSCS WXDDGAZCUPULGL-UHFFFAOYSA-N 0.000 description 1
- SDMYZIQYGCCLHR-UHFFFAOYSA-N 2,5-bis(thiiran-2-ylmethylsulfanylmethyl)-1,4-dithiane Chemical compound C1SC1CSCC(SC1)CSC1CSCC1CS1 SDMYZIQYGCCLHR-UHFFFAOYSA-N 0.000 description 1
- ZDJGRSRMDJBKAU-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OCCOCCO ZDJGRSRMDJBKAU-UHFFFAOYSA-N 0.000 description 1
- SXASCLUSQYBUFW-UHFFFAOYSA-N 2-(2-hydroxyethyldisulfanyl)ethanol 2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OCCSSCCO SXASCLUSQYBUFW-UHFFFAOYSA-N 0.000 description 1
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 description 1
- CQFQASKMKKPUKN-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.SCCOCCS CQFQASKMKKPUKN-UHFFFAOYSA-N 0.000 description 1
- SPAAESPYCDSRIW-UHFFFAOYSA-N 2-(2-sulfanylethyldisulfanyl)ethanethiol Chemical compound SCCSSCCS SPAAESPYCDSRIW-UHFFFAOYSA-N 0.000 description 1
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
- RDNOXVONDLWZCI-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanylmethylsulfanyl)ethanethiol Chemical compound SCCSCSCCS RDNOXVONDLWZCI-UHFFFAOYSA-N 0.000 description 1
- HAQZWTGSNCDKTK-UHFFFAOYSA-N 2-(3-sulfanylpropanoyloxy)ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOC(=O)CCS HAQZWTGSNCDKTK-UHFFFAOYSA-N 0.000 description 1
- UREAOTFLSRRYKQ-UHFFFAOYSA-N 2-(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical compound SCSCCSCS UREAOTFLSRRYKQ-UHFFFAOYSA-N 0.000 description 1
- LOSJLAVLYJUGJO-UHFFFAOYSA-N 2-[1,3-bis(sulfanyl)propan-2-ylsulfanyl]propane-1,3-dithiol Chemical compound SCC(CS)SC(CS)CS LOSJLAVLYJUGJO-UHFFFAOYSA-N 0.000 description 1
- QTEWPHJCEXIMRJ-UHFFFAOYSA-N 2-[2,3-bis(2-sulfanylethylsulfanyl)propylsulfanyl]ethanethiol Chemical compound SCCSCC(SCCS)CSCCS QTEWPHJCEXIMRJ-UHFFFAOYSA-N 0.000 description 1
- ZQLHFUHXRDOCBC-UHFFFAOYSA-N 2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOC(=O)CCS ZQLHFUHXRDOCBC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- XYHKMRNYSMEEDT-UHFFFAOYSA-N 2-[3-(2-sulfanylethylsulfanyl)propylsulfanyl]ethanethiol Chemical compound SCCSCCCSCCS XYHKMRNYSMEEDT-UHFFFAOYSA-N 0.000 description 1
- XWBDFXFFZGDSQD-UHFFFAOYSA-N 2-[4-(2-sulfanylethylsulfanyl)-3,3-bis(2-sulfanylethylsulfanylmethyl)butyl]sulfanylethanethiol Chemical compound C(CSCCS)C(CSCCS)(CSCCS)CSCCS XWBDFXFFZGDSQD-UHFFFAOYSA-N 0.000 description 1
- WQKFQBSUWRZIAR-UHFFFAOYSA-N 2-[[4-(thiiran-2-ylmethylsulfanylmethyl)cyclohexyl]methylsulfanylmethyl]thiirane Chemical compound C1SC1CSCC(CC1)CCC1CSCC1CS1 WQKFQBSUWRZIAR-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- OEHCVHLWJWZUGM-UHFFFAOYSA-N 2-sulfanylacetic acid;2-(2-sulfanylethoxy)ethanethiol Chemical compound OC(=O)CS.OC(=O)CS.SCCOCCS OEHCVHLWJWZUGM-UHFFFAOYSA-N 0.000 description 1
- KOCAIQHVJFBWHC-UHFFFAOYSA-N 3,4-dimethoxybutane-1,2-dithiol Chemical compound COCC(OC)C(S)CS KOCAIQHVJFBWHC-UHFFFAOYSA-N 0.000 description 1
- RSQCPZJFYJBZDV-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCCSCCS RSQCPZJFYJBZDV-UHFFFAOYSA-N 0.000 description 1
- AHHJYDXYFRLFQC-UHFFFAOYSA-N 3-(3-hydroxypropylsulfanyl)propan-1-ol 3-sulfanylpropanoic acid Chemical compound SCCC(=O)O.SCCC(=O)O.OCCCSCCCO AHHJYDXYFRLFQC-UHFFFAOYSA-N 0.000 description 1
- KTJKAUMRBSAQLR-UHFFFAOYSA-N 3-(3-sulfanylpropyldisulfanyl)propane-1-thiol Chemical compound SCCCSSCCCS KTJKAUMRBSAQLR-UHFFFAOYSA-N 0.000 description 1
- GZWIBBZCQMNKPK-UHFFFAOYSA-N 3-(3-sulfanylpropylsulfanyl)propane-1-thiol Chemical compound SCCCSCCCS GZWIBBZCQMNKPK-UHFFFAOYSA-N 0.000 description 1
- XBNYMYZLSBMANG-UHFFFAOYSA-N 3-(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSCCCSCS XBNYMYZLSBMANG-UHFFFAOYSA-N 0.000 description 1
- DUYICINCNBSZMH-UHFFFAOYSA-N 3-[2,3-bis(3-sulfanylpropylsulfanyl)propylsulfanyl]propane-1-thiol Chemical compound SCCCSCC(SCCCS)CSCCCS DUYICINCNBSZMH-UHFFFAOYSA-N 0.000 description 1
- SQTMWMRJFVGAOW-UHFFFAOYSA-N 3-[2,3-bis(sulfanyl)propylsulfanyl]propane-1,2-dithiol Chemical compound SCC(S)CSCC(S)CS SQTMWMRJFVGAOW-UHFFFAOYSA-N 0.000 description 1
- DVHQXOQBURNXCE-UHFFFAOYSA-N 3-[4-(3-sulfanylpropylsulfanyl)-3,3-bis(3-sulfanylpropylsulfanylmethyl)butyl]sulfanylpropane-1-thiol Chemical compound C(CS)CSCCC(CSCCCS)(CSCCCS)CSCCCS DVHQXOQBURNXCE-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- QDNHFLDYNJTWKV-UHFFFAOYSA-N 3-methoxypropane-1,2-dithiol Chemical compound COCC(S)CS QDNHFLDYNJTWKV-UHFFFAOYSA-N 0.000 description 1
- DWKUCGVJAUKGCG-UHFFFAOYSA-N 3-propylsulfanylpropane-1-thiol Chemical compound CCCSCCCS DWKUCGVJAUKGCG-UHFFFAOYSA-N 0.000 description 1
- XKCYYVCNDLSTRW-UPHRSURJSA-N C(\C=C/C(=O)OCCS)(=S)OCCS Chemical compound C(\C=C/C(=O)OCCS)(=S)OCCS XKCYYVCNDLSTRW-UPHRSURJSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- SWTBZQOYIMBDQQ-UHFFFAOYSA-N OCSCO.OC(=O)CCS.OC(=O)CCS Chemical compound OCSCO.OC(=O)CCS.OC(=O)CCS SWTBZQOYIMBDQQ-UHFFFAOYSA-N 0.000 description 1
- OHPMECDFYMJRGR-UHFFFAOYSA-N SCC(=O)O.SCC(=O)O.OCCCSCCCO Chemical compound SCC(=O)O.SCC(=O)O.OCCCSCCCO OHPMECDFYMJRGR-UHFFFAOYSA-N 0.000 description 1
- MKZWJDSFUIZNMG-UHFFFAOYSA-N SCC(=O)O.SCC(=O)O.OCCCSSCCCO Chemical compound SCC(=O)O.SCC(=O)O.OCCCSSCCCO MKZWJDSFUIZNMG-UHFFFAOYSA-N 0.000 description 1
- PGILEVNTXKHSHZ-UHFFFAOYSA-N SCC(=O)O.SCC(=O)O.S(CCO)CCO Chemical compound SCC(=O)O.SCC(=O)O.S(CCO)CCO PGILEVNTXKHSHZ-UHFFFAOYSA-N 0.000 description 1
- GNTSCFPBDDEJHN-UHFFFAOYSA-N SCCC(=O)O.SCCC(=O)O.OCCCSSCCCO Chemical compound SCCC(=O)O.SCCC(=O)O.OCCCSSCCCO GNTSCFPBDDEJHN-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/775—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur sulfur
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- G02B1/041—Lenses
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
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Abstract
Description
폴리이소시아네이트 화합물(중량부) | 폴리티올화합물(중량부) | 배합비(-SH/-NCO)(몰비) | 에피티오기함유화합물(중량부) | 외관 | 굴절률 | 아베수 | 내열성℃ | 인장강도kgf | 줄무늬 | ||
실시예 | 1 | DIMB4.35 | BMMD15.65 | 3.5 | BEPS80.0 | 무색투명 | 1.699 | 36 | 90 | 40 | ○ |
2 | DIMB5.16 | MMDS/BMMD7.91/11.93 | 3.0 | BEPS75.0 | 무색투명 | 1.699 | 36 | 92 | 40 | ○ | |
3 | BIMD9.30 | BMMD25.70 | 3.0 | BEPS65.0 | 무색투명 | 1.700 | 36 | 90 | 53 | ○ | |
4 | HMDI6.48 | MMDS/BMMD15.7/7.82 | 3.0 | BEPS70.0 | 무색투명 | 1.691 | 36 | 85 | 44 | ○ | |
5 | BIMD12.22 | BMMD20.28 | 1.80 | BEPS67.50 | 무색투명 | 1.697 | 36 | 89 | 53 | ○ | |
6 | BIMD13.64 | BMMD18.861 | 1.50 | BEPS67.50 | 무색투명 | 1.696 | 36 | 92 | 56 | ○ | |
7 | BIMD15.10 | BMMD17.40 | 1.25 | BEPS67.50 | 무색투명 | 1.695 | 36 | 96 | 60 | ○ | |
8 | BIMD/DIMB6.88/4.10 | BMMD19.02 | 1.80 | BEPS70.00 | 무색투명 | 1.694 | 36 | 89 | 49 | ○ | |
9 | BIMD/DIMB7.00/4.18 | BMMD18.82 | 1.75 | BEPS70.00 | 무색투명 | 1.694 | 36 | 92 | 54 | ○ | |
10 | BIMD/DIMB8.93/3.43 | BMMD17.64 | 1.50 | BEPS70.00 | 무색투명 | 1.694 | 36 | 95 | 51 | ○ | |
비교예 | 1 | XDI 20.0 | BTG 5.00 | 0.16 | BEPS75.0 | 경화하지않음(다갈색화한 액체) | |||||
2 | XDI 20.0 | DMES 5.00 | 0.31 | BEPS75.0 | 경화하지않음(백탁불투명젤리상) | ||||||
3 | IPDI 15.0 | BTG 5.00 | 0.25 | BEPS80.0 | 경화하지않음(다갈색화한 액체) | ||||||
4 | XDI 20.0 | DMTMP20.0 | 1.08 | BEPS60.0 | 황색연질고무 | ||||||
5 | - | DMES/HEMA6.00/1.00 | - | BEPS93.0 | 무색투명 | 1.700 | 36 | 90 | 25 | ○ |
Claims (24)
- 에피티오기 함유 화합물(a)과, 폴리티올 화합물(b)과, 폴리이소시아네이트 화합물(c)을 중합하는 공정을 포함하는 안경용 플라스틱 렌즈에 적합한 재료를 제조하는 방법에 있어서,폴리이소시아네이트 화합물(c)이 유황을 함유하지 않는 폴리이소시아네이트 화합물(co)인 경우에, -SH 및 -NCO 기의 몰 양에 근거하여 계산된 폴리이소시아네이트 화합물(c)에 대한 폴리티올 화합물(b)의 비율이 최소한 2.0이고, 에피티오기 함유 화합물(a)은 비스(β-에피티오프로필)술피드이며,폴리이소시아네이트 화합물(c)이 유황을 함유하는 폴리이소시아네이트 화합물(cs)의 경우에, -SH 및 -NCO 기의 몰 양에 근거하여 계산된 폴리이소시아네이트 화합물(c)에 대한 폴리티올 화합물(b)의 비율이 최소한 1.2인 것을 특징으로 하는 안경용 플라스틱 렌즈 재료의 제조 방법.
- 삭제
- 제1항에 있어서,상기 황 무함유 폴리이소시아네이트 화합물(co)이 디(이소시아네이트메틸)비시클로헵탄과 디시클로헥실메탄 디이소시아네이트로 부터 선택된 적어도 1종인 것을 특징으로 하는 제조 방법.
- 제1항에 있어서,상기 황 함유 폴리이소시아네이트 화합물(cs)이 비스(이소시아네이트메틸)-1,4-디티안인 것을 특징으로 하는 제조 방법.
- 제1항에 있어서,상기 폴리이소시아네이트 화합물(c)이 디(이소시아네이트메틸)비시클로헵탄, 비스(이소시아네이트메틸)-1,4-디티안 및 디시클로헥실메탄 디이소시아네이트로 부터 선택되는 것을 특징으로 하는 제조 방법.
- 제1항에 있어서,상기 폴리이소시아네이트 화합물(c)이 비스(이소시아네이트메틸)-1,4-디티안과, 디(이소시아네이트메틸)비시클로헵탄과 디시클로헥실메탄 디이소시아네이트로부터 선택된 적어도 1종의 다른 폴리이소시아네이트 화합물의 혼합물인 것을 특징으로 하는 제조 방법.
- 제1항에 있어서,상기 폴리티올 화합물(b)이 비스메르캅토메틸-1,4-디티안과 (4-메르캅토메틸 -2,5-디티아닐)메틸 디술피드로 부터 선택된 적어도 1종인 것을 특징으로 하는 제조 방법.
- 제1항에 있어서,상기 에피티오기를 갖는 화합물(a)이 비스(β-에피티오프로필)술피드인 것을 특징으로하는 제조 방법.
- 제1항에 있어서,다음 일반식(1)으로 된 촉매를 첨가하는 것을 특징으로 하는 제조 방법.(식 중 R는 1∼4의 탄소원자를 갖는 알킬기를 나타낸다)
- 제9항에 있어서,상기 식(1)의 촉매가 테트라메틸디아세톡시-디스타녹산, 테트라에틸디아세톡시-디스타녹산, 테트라프로필디아세톡시-디스타녹산 및 테트라부틸디아세톡시-디스타녹산으로부터 선택된 적어도 1종인 것을 특징으로 하는 제조 방법.
- 촉매의 존재하에서, 에피티오기 함유 화합물(a)과, 폴리티올 화합물(b)과, 폴리이소시아네이트 화합물(c)을 중합하는 공정을 포함하는 안경용 플라스틱 렌즈에 적합한 재료를 제조하는 방법에 있어서,폴리이소시아네이트 화합물(c)이 유황을 함유하지 않는 폴리이소시아네이트 화합물(co)의 경우에, -SH 및 -NCO 기의 몰 양에 근거하여 계산된 폴리이소시아네이트 화합물(c)에 대한 폴리티올 화합물(b)의 비율이 최소한 2.0이고,폴리이소시아네이트 화합물(c)이 유황을 함유하는 폴리이소시아네이트 화합물(cs)의 경우에, -SH 및 -NCO 기의 몰 양에 근거하여 계산된 폴리이소시아네이트 화합물(c)에 대한 폴리티올 화합물(b)의 비율이 최소한 1.2이며, 상기 촉매는 다음 일반식(1)로 표시되는 것을 특징으로 하는 안경용 플라스틱 렌즈 재료의 제조 방법.(식 중 R는 1∼4의 탄소원자를 갖는 알킬기를 나타낸다)
- 제11항에 있어서,상기 촉매는 테트라메틸디아세톡시-디스타녹산, 테트라에틸디아세톡시-디스타녹산, 테트라프로필디아세톡시-디스타녹산과 테트라부틸디아세톡시-디스타녹산으로부터 선택된 적어도 1종인 것을 특징으로하는 제조 방법.
- 청구항 1항의 제조방법에 따라 얻어진 재료로 제조된 안경용 플라스틱렌즈.
- 제13항에 있어서,유기규소 화합물로 이루어진 경화피막으로 코팅된 것을 특징으로 하는 안경용 플라스틱렌즈.
- 제14항에 있어서,상기 경화피막(Hard film)은 무기물질로 이루어진 반사방지막으로 더 코팅된 것을 특징으로 하는 안경용 플라스틱렌즈.
- 제15항에 있어서,상기 반사방지막은 불소코팅 규소화합물로 이루어진 발수막으로 더 코팅된 것을 특징으로 하는 안경용 플라스틱렌즈.
- 제13항 내지 제16항 중 어느 항에 있어서,굴절률이 1.65∼1.76인 것을 특징으로하는 안경용 플라스틱렌즈.
- 에피티오기 함유 화합물(a)과, 폴리티올 화합물(b)과, 황 무함유 폴리이소시 아네이트 화합물(co)을 중합하는 공정을 포함하는 안경용 플라스틱렌즈에 적합한 물질을 제조하는 방법에 있어서,-SH 및 -NCO 기의 몰 양에 근거하여 계산된 황 무함유 폴리이소시아네이트 화합물(co)에 대한 폴리티올 화합물(b)의 비율이 최소한 2.0이며, 60∼85 중량%의 에피티오기 함유 화합물(a)과, 15∼40 중량%의 폴리티올 화합물(b) 및 황 무함유 폴리이소시아네이트 화합물(co)이 사용되는 것을 특징으로하는 제조 방법.
- 제18항에 있어서,상기 황 무함유 폴리이소시아네이트 화합물(co)이 디(이소시아네이트메틸)비시클로헵탄과 디시클로헥실메탄 디이소시아네이트로 부터 선택된 적어도 1종인 것을 특징으로 하는 제조 방법.
- 제18항에 있어서,상기 폴리티올 화합물(b)이 비스메르캅토메틸-1,4-디티안과 (4-메르캅토메틸 -2,5-디티아닐)메틸디술피드로 부터 선택된 적어도 1종인 것을 특징으로 하는 제조 방법.
- 제18항에 있어서,상기 에피티오기를 갖는 화합물(a)이 비스(β-에피티오프로필)술피드인 것을 특징으로하는 제조 방법.
- 제18항에 있어서,다음 일반식(1)으로 된 촉매를 첨가하는 것을 특징으로 하는 제조 방법.(식 중 R는 1∼4의 탄소원자를 갖는 알킬기를 나타낸다)
- 청구항 18항의 제조방법에 따라 얻어진 재료로 제조된 안경용 플라스틱 렌즈.
- 제23항에 있어서,굴절률이 1.65∼1.76인 것을 특징으로 하는 안경용 플라스틱 렌즈.
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KR20200106729A (ko) | 2019-03-05 | 2020-09-15 | 주식회사 케이오씨솔루션 | 광학렌즈용 내부이형제 조성물 및 이를 포함하는 에폭시 아크릴계 광학렌즈용 조성물 |
KR20200113612A (ko) | 2019-03-26 | 2020-10-07 | 주식회사 케이오씨솔루션 | 에피설파이드계 고굴절 광학재료용 조성물과 이를 이용한 광학재료의 제조방법 |
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KR20210105224A (ko) | 2020-02-18 | 2021-08-26 | 주식회사 케이오씨솔루션 | 에피설파이드계 광학재료의 내광성 및 열안정성 개선을 위한 조성물과 이를 이용한 광학재료용 조성물 및 광학재료의 제조방법 |
KR20210105219A (ko) | 2020-02-18 | 2021-08-26 | 주식회사 케이오씨솔루션 | 광학재료용 에피설파이드 화합물, 이를 포함하는 고굴절 광학재료용 조성물 및 광학재료의 제조방법 |
KR20210106823A (ko) | 2020-02-21 | 2021-08-31 | 주식회사 케이오씨솔루션 | 에피설파이드계 광학재료의 내광성 및 열안정성 개선을 위한 조성물과 이를 이용한 광학재료용 조성물 및 광학재료의 제조방법 |
KR20210107444A (ko) | 2020-02-24 | 2021-09-01 | 주식회사 케이오씨솔루션 | 내광성이 향상된 에피설파이드계 고굴절 광학재료용 조성물 및 광학재료의 제조방법 |
KR20210117080A (ko) | 2020-03-18 | 2021-09-28 | 주식회사 엠엘텍 | 에피설파이드계 광학재료용 중합조절제와 이를 포함하는 광학재료용 조성물 및 광학재료의 제조방법 |
KR20210130547A (ko) | 2020-04-22 | 2021-11-01 | 주식회사 엠엘텍 | 광학재료용 에폭시 화합물의 제조방법 및 이를 이용한 광학재료용 에피설파이드 화합물과 고굴절 광학재료의 제조방법 |
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CA2337955C (en) | 2006-07-25 |
HU222786B1 (hu) | 2003-10-28 |
EP1134242B1 (en) | 2004-09-01 |
HK1036462A1 (en) | 2002-01-04 |
KR20010092329A (ko) | 2001-10-24 |
AU744901B2 (en) | 2002-03-07 |
AU2491001A (en) | 2001-10-11 |
PL346442A1 (en) | 2001-09-24 |
DE60105212D1 (de) | 2004-10-07 |
CA2337955A1 (en) | 2001-09-15 |
CN1313513A (zh) | 2001-09-19 |
US6743886B2 (en) | 2004-06-01 |
US20040220370A1 (en) | 2004-11-04 |
EP1134242A2 (en) | 2001-09-19 |
TWI232225B (en) | 2005-05-11 |
ATE275160T1 (de) | 2004-09-15 |
EP1134242A3 (en) | 2002-03-20 |
DE60105212T2 (de) | 2005-01-13 |
HUP0101105A3 (en) | 2002-12-28 |
HUP0101105A2 (en) | 2002-08-28 |
US7091301B2 (en) | 2006-08-15 |
CN1155841C (zh) | 2004-06-30 |
US20010030734A1 (en) | 2001-10-18 |
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