TWI572641B - Composition for optical materials - Google Patents
Composition for optical materials Download PDFInfo
- Publication number
- TWI572641B TWI572641B TW102106959A TW102106959A TWI572641B TW I572641 B TWI572641 B TW I572641B TW 102106959 A TW102106959 A TW 102106959A TW 102106959 A TW102106959 A TW 102106959A TW I572641 B TWI572641 B TW I572641B
- Authority
- TW
- Taiwan
- Prior art keywords
- composition
- optical material
- sulfur
- mass
- bis
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 62
- 230000003287 optical effect Effects 0.000 title claims description 60
- 239000000203 mixture Substances 0.000 title claims description 55
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- 239000011593 sulfur Substances 0.000 claims description 55
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 53
- -1 epoxide sulfide compound Chemical class 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 27
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- 239000004593 Epoxy Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 238000007872 degassing Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229920006295 polythiol Polymers 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002685 polymerization catalyst Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- SZPVNHKZNBIEBT-UHFFFAOYSA-N 1,3-di(undecyl)benzene Chemical compound CCCCCCCCCCCC1=CC=CC(CCCCCCCCCCC)=C1 SZPVNHKZNBIEBT-UHFFFAOYSA-N 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 4
- MLGITEWCALEOOJ-UHFFFAOYSA-N 2-(thiiran-2-ylmethylsulfanylmethyl)thiirane Chemical compound C1SC1CSCC1CS1 MLGITEWCALEOOJ-UHFFFAOYSA-N 0.000 description 4
- 229910052684 Cerium Inorganic materials 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- WISUILQECWFZCN-UHFFFAOYSA-N 2-(oxiran-2-ylmethylsulfanylmethyl)oxirane Chemical compound C1OC1CSCC1CO1 WISUILQECWFZCN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- ZXACHZITICPUKS-UHFFFAOYSA-N 2-[(oxiran-2-ylmethyldisulfanyl)methyl]oxirane Chemical compound C1OC1CSSCC1CO1 ZXACHZITICPUKS-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RAMYGXOAMNVWRX-UHFFFAOYSA-N CC1(CO1)SC1(C)CO1 Chemical compound CC1(CO1)SC1(C)CO1 RAMYGXOAMNVWRX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VCVYFPYBCGIWDH-UHFFFAOYSA-K SCC(=O)[O-].[Bi+3].OCC(CO)(CO)CO.SCC(=O)[O-].SCC(=O)[O-] Chemical compound SCC(=O)[O-].[Bi+3].OCC(CO)(CO)CO.SCC(=O)[O-].SCC(=O)[O-] VCVYFPYBCGIWDH-UHFFFAOYSA-K 0.000 description 2
- OPRZTXUAUABOQB-UHFFFAOYSA-K SCCC(=O)[O-].[Bi+3].OCC(CO)(CO)CO.SCCC(=O)[O-].SCCC(=O)[O-] Chemical compound SCCC(=O)[O-].[Bi+3].OCC(CO)(CO)CO.SCCC(=O)[O-].SCCC(=O)[O-] OPRZTXUAUABOQB-UHFFFAOYSA-K 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000006477 desulfuration reaction Methods 0.000 description 2
- 230000023556 desulfurization Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000008434 ginseng Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZSPQVOFATJEJMT-UHFFFAOYSA-N 1,1,3,3-tetraethylthiourea Chemical compound CCN(CC)C(=S)N(CC)CC ZSPQVOFATJEJMT-UHFFFAOYSA-N 0.000 description 1
- JAEZSIYNWDWMMN-UHFFFAOYSA-N 1,1,3-trimethylthiourea Chemical compound CNC(=S)N(C)C JAEZSIYNWDWMMN-UHFFFAOYSA-N 0.000 description 1
- DZUCNDRXUNGSMM-UHFFFAOYSA-N 1,2-di(undecyl)benzene Chemical compound CCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCC DZUCNDRXUNGSMM-UHFFFAOYSA-N 0.000 description 1
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- CVGVPWAGZNTBSN-UHFFFAOYSA-N 1,3-didecylcyclohexane Chemical compound CCCCCCCCCCC1CCCC(CCCCCCCCCC)C1 CVGVPWAGZNTBSN-UHFFFAOYSA-N 0.000 description 1
- LGOIGWKQHKMYNM-UHFFFAOYSA-N 1,4-di(undecyl)benzene Chemical compound CCCCCCCCCCCC1=CC=C(CCCCCCCCCCC)C=C1 LGOIGWKQHKMYNM-UHFFFAOYSA-N 0.000 description 1
- HYXPQIIYXQBMSW-UHFFFAOYSA-N 1,4-di(undecyl)cyclohexane Chemical compound C(CCCCCCCCC)CC1CCC(CC1)CCCCCCCCCCC HYXPQIIYXQBMSW-UHFFFAOYSA-N 0.000 description 1
- ZDOBWFOCGGBPNS-UHFFFAOYSA-N 1,4-didecylcyclohexane Chemical compound CCCCCCCCCCC1CCC(CCCCCCCCCC)CC1 ZDOBWFOCGGBPNS-UHFFFAOYSA-N 0.000 description 1
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 1
- IZNIJEWSKRQQLT-UHFFFAOYSA-N 1-(3-chloropentan-3-yl)-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C(Cl)(CC)CC IZNIJEWSKRQQLT-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
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 1
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 description 1
- NQLQMVQEQFIDQB-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)propane-1,3-dithiol Chemical compound SCCSC(CS)CS NQLQMVQEQFIDQB-UHFFFAOYSA-N 0.000 description 1
- ZSTGYXSSYULQHU-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC(C(C)CC)=C(O)C(N2N=C3C=CC=CC3=N2)=C1 ZSTGYXSSYULQHU-UHFFFAOYSA-N 0.000 description 1
- IFZMWFQDOSRYFG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-octan-3-ylphenol Chemical compound CCCCCC(CC)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IFZMWFQDOSRYFG-UHFFFAOYSA-N 0.000 description 1
- YBIGQANAFDQTNA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-ethoxyphenol Chemical compound OC1=CC(OCC)=CC=C1N1N=C2C=CC=CC2=N1 YBIGQANAFDQTNA-UHFFFAOYSA-N 0.000 description 1
- IYQVQZXLTJHEKZ-UHFFFAOYSA-N 2-(ethylsulfanyl)ethanethiol Chemical compound CCSCCS IYQVQZXLTJHEKZ-UHFFFAOYSA-N 0.000 description 1
- FOBHCEPKFIUKPH-UHFFFAOYSA-N 2-(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)CS FOBHCEPKFIUKPH-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- JRKRMWWBDZSDMT-UHFFFAOYSA-N 2-[(thiiran-2-ylmethyldisulfanyl)methyl]thiirane Chemical compound C1SC1CSSCC1CS1 JRKRMWWBDZSDMT-UHFFFAOYSA-N 0.000 description 1
- GIURVBCWGBRPHD-UHFFFAOYSA-N 2-[[4-(1H-indol-2-ylmethyl)phenyl]methyl]-1H-indole Chemical compound N1C(=CC2=CC=CC=C12)CC1=CC=C(C=C1)CC=1NC2=CC=CC=C2C=1 GIURVBCWGBRPHD-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
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- VKFXRBZSVGYYSA-UHFFFAOYSA-N 3-ethyl-1,1-dimethylthiourea Chemical compound CCNC(=S)N(C)C VKFXRBZSVGYYSA-UHFFFAOYSA-N 0.000 description 1
- IPNDIMIIGZSERC-UHFFFAOYSA-N 4-(2-sulfanylacetyl)oxybutyl 2-sulfanylacetate Chemical compound SCC(=O)OCCCCOC(=O)CS IPNDIMIIGZSERC-UHFFFAOYSA-N 0.000 description 1
- WREGWRFRXHKFGE-UHFFFAOYSA-N 4-(4-sulfanylphenoxy)benzenethiol Chemical compound C1=CC(S)=CC=C1OC1=CC=C(S)C=C1 WREGWRFRXHKFGE-UHFFFAOYSA-N 0.000 description 1
- DIFMOXDTKAEVHX-UHFFFAOYSA-N 4-[2-(4-sulfanylphenyl)propan-2-yl]benzenethiol Chemical compound C=1C=C(S)C=CC=1C(C)(C)C1=CC=C(S)C=C1 DIFMOXDTKAEVHX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- JLLMOYPIVVKFHY-UHFFFAOYSA-N Benzenethiol, 4,4'-thiobis- Chemical compound C1=CC(S)=CC=C1SC1=CC=C(S)C=C1 JLLMOYPIVVKFHY-UHFFFAOYSA-N 0.000 description 1
- DKCSLPYYEPOKQE-UHFFFAOYSA-N C(CC)SC1(CO1)SC1(CO1)SCCC Chemical compound C(CC)SC1(CO1)SC1(CO1)SCCC DKCSLPYYEPOKQE-UHFFFAOYSA-N 0.000 description 1
- LMJCUAOOTWKTEP-UHFFFAOYSA-N CC1(CS1)SC1(C)CS1 Chemical compound CC1(CS1)SC1(C)CS1 LMJCUAOOTWKTEP-UHFFFAOYSA-N 0.000 description 1
- QEUCBMQFJDGQFC-UHFFFAOYSA-N CCCCCCCCCCCC1CCCC(C1)CCCCCCCCCCC Chemical compound CCCCCCCCCCCC1CCCC(C1)CCCCCCCCCCC QEUCBMQFJDGQFC-UHFFFAOYSA-N 0.000 description 1
- INBDPOJZYZJUDA-UHFFFAOYSA-N Ca salt---Methanedithiol Natural products SCS INBDPOJZYZJUDA-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- DMELZFRCCTUALZ-UHFFFAOYSA-N SC=CC(=O)OCCCCOC(C=CS)=O Chemical compound SC=CC(=O)OCCCCOC(C=CS)=O DMELZFRCCTUALZ-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BPFAQZURMHOGLM-UHFFFAOYSA-N [4-[2-[4-(sulfanylmethyl)phenyl]propan-2-yl]phenyl]methanethiol Chemical compound C=1C=C(CS)C=CC=1C(C)(C)C1=CC=C(CS)C=C1 BPFAQZURMHOGLM-UHFFFAOYSA-N 0.000 description 1
- MSILJOYZYPRFDK-UHFFFAOYSA-N [4-[4-(sulfanylmethyl)phenoxy]phenyl]methanethiol Chemical compound C1=CC(CS)=CC=C1OC1=CC=C(CS)C=C1 MSILJOYZYPRFDK-UHFFFAOYSA-N 0.000 description 1
- WMOSGVRFIUEZSX-UHFFFAOYSA-N [4-[4-(sulfanylmethyl)phenyl]sulfanylphenyl]methanethiol Chemical compound C1=CC(CS)=CC=C1SC1=CC=C(CS)C=C1 WMOSGVRFIUEZSX-UHFFFAOYSA-N 0.000 description 1
- MFKFAJJQTUSOTO-UHFFFAOYSA-N [Cl-].[Cl-].C1(=CC=CC=C1)[PH2+]C1=CC=CC=C1.C1(=CC=CC=C1)[PH2+]C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)[PH2+]C1=CC=CC=C1.C1(=CC=CC=C1)[PH2+]C1=CC=CC=C1 MFKFAJJQTUSOTO-UHFFFAOYSA-N 0.000 description 1
- YZSSOZVGPWVMNS-UHFFFAOYSA-N [Cl-].[Cl-].[Cl-].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+] Chemical compound [Cl-].[Cl-].[Cl-].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+] YZSSOZVGPWVMNS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling 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
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- YKRCKUBKOIVILO-UHFFFAOYSA-N cyclohexane-1,2-dithiol Chemical compound SC1CCCCC1S YKRCKUBKOIVILO-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SBOSGIJGEHWBKV-UHFFFAOYSA-L dioctyltin(2+);dichloride Chemical compound CCCCCCCC[Sn](Cl)(Cl)CCCCCCCC SBOSGIJGEHWBKV-UHFFFAOYSA-L 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
- 238000011156 evaluation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- JCWMXAXCPYFCRN-UHFFFAOYSA-N hydrazine;urea Chemical compound NN.NC(N)=O JCWMXAXCPYFCRN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000002601 lanthanoid compounds Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- DWNFDVKTSHVLHQ-UHFFFAOYSA-N methanedithiol Chemical compound S[CH]S DWNFDVKTSHVLHQ-UHFFFAOYSA-N 0.000 description 1
- BXWXUCPVRKLZSJ-UHFFFAOYSA-N methyl piperidine-1-carbodithioate Chemical compound CSC(=S)N1CCCCC1 BXWXUCPVRKLZSJ-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 230000003449 preventive effect Effects 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
- VUTVSWPVTJZPFU-UHFFFAOYSA-N propylsulfanylmethanethiol Chemical compound CCCSCS VUTVSWPVTJZPFU-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940052367 sulfur,colloidal Drugs 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- VJFXTJZJJIZRKP-UHFFFAOYSA-M tetraphenylazanium;bromide Chemical compound [Br-].C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VJFXTJZJJIZRKP-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- INTLMJZQCBRQAT-UHFFFAOYSA-K trichloro(octyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(Cl)Cl INTLMJZQCBRQAT-UHFFFAOYSA-K 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- NVSDADJBGGUCLP-UHFFFAOYSA-N trisulfur Chemical compound S=S=S NVSDADJBGGUCLP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- OBMHSNXMHVKVSA-UHFFFAOYSA-L zinc;n-benzylcarbamodithioate Chemical compound [Zn+2].[S-]C(=S)NCC1=CC=CC=C1.[S-]C(=S)NCC1=CC=CC=C1 OBMHSNXMHVKVSA-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
- C08G75/08—Polythioethers from cyclic thioethers from thiiranes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012047973 | 2012-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201345957A TW201345957A (zh) | 2013-11-16 |
| TWI572641B true TWI572641B (zh) | 2017-03-01 |
Family
ID=49116624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102106959A TWI572641B (zh) | 2012-03-05 | 2013-02-27 | Composition for optical materials |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10025005B2 (enExample) |
| EP (1) | EP2824129B1 (enExample) |
| JP (1) | JP6356061B2 (enExample) |
| KR (1) | KR101979240B1 (enExample) |
| CN (2) | CN104114607A (enExample) |
| BR (1) | BR112014019545B1 (enExample) |
| IN (1) | IN2014DN07804A (enExample) |
| TW (1) | TWI572641B (enExample) |
| WO (1) | WO2013133144A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015069087A (ja) * | 2013-09-30 | 2015-04-13 | 三菱瓦斯化学株式会社 | 高屈折率樹脂製光学レンズの製造方法 |
| TWI656155B (zh) * | 2014-04-14 | 2019-04-11 | 日商三菱瓦斯化學股份有限公司 | Composition for optical material, method for producing the same, and optical material obtained from composition for optical material |
| KR102516520B1 (ko) * | 2015-07-09 | 2023-03-31 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 광학재료용 조성물 및 광학재료 |
| KR101869785B1 (ko) * | 2016-03-24 | 2018-06-22 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 티올 화합물을 함유하는 신규 광학재료용 조성물 |
| JP7726207B2 (ja) * | 2020-05-27 | 2025-08-20 | 三菱瓦斯化学株式会社 | 光学材料用組成物 |
| EP4083109A1 (en) | 2021-04-28 | 2022-11-02 | The Boeing Company | Cure promoter compositions and methods for the same |
| CN118165264A (zh) * | 2024-04-23 | 2024-06-11 | 益丰新材料股份有限公司 | 一种光学材料组合物及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1524289A1 (en) * | 2002-07-08 | 2005-04-20 | Mitsubishi Gas Chemical Company, Inc. | Polymerizable composition, optical material comprising the composition and method for producing the material |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3491660B2 (ja) | 1995-08-16 | 2004-01-26 | 三菱瓦斯化学株式会社 | 新規な直鎖アルキルスルフィド型エピスルフィド化合物 |
| JP3738817B2 (ja) | 1999-04-23 | 2006-01-25 | 三菱瓦斯化学株式会社 | 光学材料用組成物 |
| JP2001002933A (ja) * | 1999-04-23 | 2001-01-09 | Mitsubishi Gas Chem Co Inc | 光学材料用組成物 |
| DE60304935T2 (de) * | 2002-06-04 | 2006-09-21 | Hoya Corp. | Verfahren zur Herstellung von Kunststofflinsen und die hergestellte Kunststofflinse |
| JP2004043526A (ja) * | 2002-07-08 | 2004-02-12 | Mitsubishi Gas Chem Co Inc | 光学材料用組成物 |
| JP4127169B2 (ja) | 2002-09-27 | 2008-07-30 | 三菱瓦斯化学株式会社 | 光学材料の製造方法 |
| JP2004269673A (ja) | 2003-03-07 | 2004-09-30 | Mitsubishi Gas Chem Co Inc | 樹脂用組成物 |
| JP4245515B2 (ja) * | 2004-05-25 | 2009-03-25 | 三井化学株式会社 | エピスルフィド系硫黄原子含有樹脂光学材料の強度低下を抑制する方法 |
| JP5103788B2 (ja) * | 2005-05-19 | 2012-12-19 | 三菱瓦斯化学株式会社 | 樹脂用組成物 |
| TWI482814B (zh) * | 2007-03-16 | 2015-05-01 | Mitsubishi Gas Chemical Co | 光學材料用樹脂組成物及由該組成物得到之光學材料 |
| JP2009242532A (ja) * | 2008-03-31 | 2009-10-22 | Mitsubishi Gas Chem Co Inc | 光学材料用樹脂組成物の製造方法 |
| JP5358792B2 (ja) | 2008-12-26 | 2013-12-04 | 独立行政法人産業技術総合研究所 | 硫黄変性ポリアクリロニトリルシート、その製造方法及びその用途 |
| JP2011231185A (ja) * | 2010-04-26 | 2011-11-17 | Nikon-Essilor Co Ltd | 光学レンズ成形用プレポリマーの製造方法及び光学レンズの製造方法 |
-
2013
- 2013-02-27 TW TW102106959A patent/TWI572641B/zh active
- 2013-03-01 EP EP13758146.8A patent/EP2824129B1/en active Active
- 2013-03-01 JP JP2014503809A patent/JP6356061B2/ja active Active
- 2013-03-01 BR BR112014019545-5A patent/BR112014019545B1/pt active IP Right Grant
- 2013-03-01 CN CN201380009291.4A patent/CN104114607A/zh active Pending
- 2013-03-01 IN IN7804DEN2014 patent/IN2014DN07804A/en unknown
- 2013-03-01 US US14/373,739 patent/US10025005B2/en active Active
- 2013-03-01 WO PCT/JP2013/055619 patent/WO2013133144A1/ja not_active Ceased
- 2013-03-01 KR KR1020147025773A patent/KR101979240B1/ko active Active
- 2013-03-01 CN CN201810188368.3A patent/CN108276579B/zh active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1524289A1 (en) * | 2002-07-08 | 2005-04-20 | Mitsubishi Gas Chemical Company, Inc. | Polymerizable composition, optical material comprising the composition and method for producing the material |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108276579A (zh) | 2018-07-13 |
| KR20140131540A (ko) | 2014-11-13 |
| BR112014019545A8 (pt) | 2017-07-11 |
| KR101979240B1 (ko) | 2019-05-17 |
| US20150028270A1 (en) | 2015-01-29 |
| CN108276579B (zh) | 2021-05-14 |
| BR112014019545A2 (enExample) | 2017-06-20 |
| US10025005B2 (en) | 2018-07-17 |
| WO2013133144A1 (ja) | 2013-09-12 |
| IN2014DN07804A (enExample) | 2015-05-15 |
| JPWO2013133144A1 (ja) | 2015-07-30 |
| EP2824129A1 (en) | 2015-01-14 |
| CN104114607A (zh) | 2014-10-22 |
| EP2824129B1 (en) | 2017-07-12 |
| BR112014019545B1 (pt) | 2021-03-30 |
| EP2824129A4 (en) | 2015-11-18 |
| JP6356061B2 (ja) | 2018-07-11 |
| TW201345957A (zh) | 2013-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI572641B (zh) | Composition for optical materials | |
| JP6468284B2 (ja) | 光学材料用組成物及びその製造方法並びに光学材料用組成物から得られる光学材料 | |
| US9260566B2 (en) | Composition for optical materials, process for production thereof, and optical materials made from the composition | |
| WO2013122068A1 (ja) | 光学材料用重合性組成物、その製造方法、及び光学材料の製造方法 | |
| JP5648636B2 (ja) | 光学材料の製造方法、光学材料および光学レンズ | |
| JP6048013B2 (ja) | 光学材料用重合性組成物の製造方法 | |
| JP6048012B2 (ja) | 光学材料の製造方法 | |
| JP7726207B2 (ja) | 光学材料用組成物 |