CN109575217A - 光学材料用聚合性组合物 - Google Patents
光学材料用聚合性组合物 Download PDFInfo
- Publication number
- CN109575217A CN109575217A CN201811490099.2A CN201811490099A CN109575217A CN 109575217 A CN109575217 A CN 109575217A CN 201811490099 A CN201811490099 A CN 201811490099A CN 109575217 A CN109575217 A CN 109575217A
- Authority
- CN
- China
- Prior art keywords
- polymerizable composition
- mentioned
- diisocyanate
- poly
- bis
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 125
- 239000000463 material Substances 0.000 title claims abstract description 30
- 230000003287 optical effect Effects 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 229920002578 polythiourethane polymer Polymers 0.000 claims abstract description 22
- -1 poly-thiol compound Chemical class 0.000 claims description 94
- 239000005056 polyisocyanate Substances 0.000 claims description 51
- 229920001228 polyisocyanate Polymers 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 230000008859 change Effects 0.000 claims description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002366 halogen compounds Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 17
- 239000011521 glass Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000012948 isocyanate Substances 0.000 description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 241000534944 Thia Species 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 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 6
- 239000001294 propane Substances 0.000 description 6
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 229930192474 thiophene Natural products 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 3
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N dimethyl monosulfide Natural products CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- QOKSGFNBBSSNAL-UHFFFAOYSA-N 1,2-diisocyanato-3,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(N=C=O)=C1C QOKSGFNBBSSNAL-UHFFFAOYSA-N 0.000 description 2
- LUYHWJKHJNFYGV-UHFFFAOYSA-N 1,2-diisocyanato-3-phenylbenzene Chemical compound O=C=NC1=CC=CC(C=2C=CC=CC=2)=C1N=C=O LUYHWJKHJNFYGV-UHFFFAOYSA-N 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AXIWPQKLPMINAT-UHFFFAOYSA-N 1-ethyl-2,3-diisocyanatobenzene Chemical compound CCC1=CC=CC(N=C=O)=C1N=C=O AXIWPQKLPMINAT-UHFFFAOYSA-N 0.000 description 2
- QLOQTKGUQKAAAB-UHFFFAOYSA-N 1-isocyanato-2-(2-isocyanatoethoxy)ethane Chemical class O=C=NCCOCCN=C=O QLOQTKGUQKAAAB-UHFFFAOYSA-N 0.000 description 2
- QUVLJNYSCQAYLV-UHFFFAOYSA-N 1-isocyanato-2-(2-isocyanatoethylsulfanyl)ethane Chemical compound O=C=NCCSCCN=C=O QUVLJNYSCQAYLV-UHFFFAOYSA-N 0.000 description 2
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 2
- VSSFYDMUTATOHG-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)-3-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropane-1-thiol Chemical compound SCCSC(CS)CSCC(CS)SCCS VSSFYDMUTATOHG-UHFFFAOYSA-N 0.000 description 2
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 2
- QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-UHFFFAOYSA-N 0.000 description 2
- NTRMNYKTDJIULH-UHFFFAOYSA-N 3-[2,3-bis(sulfanyl)propyldisulfanyl]propane-1,2-dithiol Chemical compound SCC(S)CSSCC(S)CS NTRMNYKTDJIULH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NPBTYNRGLVLCSG-UHFFFAOYSA-N N=C=O.C1CCCCC1C(C)(C)C1CCCCC1 Chemical class N=C=O.C1CCCCC1C(C)(C)C1CCCCC1 NPBTYNRGLVLCSG-UHFFFAOYSA-N 0.000 description 2
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical compound N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 description 2
- OQSSNGKVNWXYOE-UHFFFAOYSA-N N=C=O.N=C=O.CCC(C)CC(C)(C)C Chemical compound N=C=O.N=C=O.CCC(C)CC(C)(C)C OQSSNGKVNWXYOE-UHFFFAOYSA-N 0.000 description 2
- MFWSSBVVMCUQFC-UHFFFAOYSA-N N=C=O.N=C=O.CCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCC(C)(C)C MFWSSBVVMCUQFC-UHFFFAOYSA-N 0.000 description 2
- LRNAHSCPGKWOIY-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=CC=C1 LRNAHSCPGKWOIY-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- PLOWAKQTEHQOFB-UHFFFAOYSA-L di(propan-2-yl)tin(2+);dichloride Chemical compound CC(C)[Sn](Cl)(Cl)C(C)C PLOWAKQTEHQOFB-UHFFFAOYSA-L 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- CTRHCENQKGMZLE-UHFFFAOYSA-L dipropyltin(2+);dichloride Chemical compound CCC[Sn](Cl)(Cl)CCC CTRHCENQKGMZLE-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940093495 ethanethiol Drugs 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- VCAVAURZPNANDQ-UHFFFAOYSA-N ethyl-hexadecyl-dimethylazanium Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)CC VCAVAURZPNANDQ-UHFFFAOYSA-N 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- CNIQRWPMYHDBNS-UHFFFAOYSA-N isocyanato(isocyanatomethylsulfonyl)methane Chemical class O=C=NCS(=O)(=O)CN=C=O CNIQRWPMYHDBNS-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical class CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- SQTMWMRJFVGAOW-OLQVQODUSA-N (2s)-3-[(2r)-2,3-bis(sulfanyl)propyl]sulfanylpropane-1,2-dithiol Chemical compound SC[C@H](S)CSC[C@H](S)CS SQTMWMRJFVGAOW-OLQVQODUSA-N 0.000 description 1
- GHXPTDPKJYFMOE-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCCC1CN=C=O GHXPTDPKJYFMOE-UHFFFAOYSA-N 0.000 description 1
- WZROIUBWZBSCSE-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)naphthalene Chemical compound C1=CC=CC2=C(CN=C=O)C(CN=C=O)=CC=C21 WZROIUBWZBSCSE-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
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-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
- 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
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- VFTVILNYPYJIGL-UHFFFAOYSA-N 1,3-diisocyanato-2-(2-isocyanatoethylsulfanyl)propane Chemical compound O=C=NCCSC(CN=C=O)CN=C=O VFTVILNYPYJIGL-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- UTYQUKHNHPEPDA-UHFFFAOYSA-N 1-(isocyanatomethyl)naphthalene Chemical class C1=CC=C2C(CN=C=O)=CC=CC2=C1 UTYQUKHNHPEPDA-UHFFFAOYSA-N 0.000 description 1
- KDELCQKJXHQDEX-UHFFFAOYSA-N 1-isocyanato-3-(3-isocyanatopropyldisulfanyl)propane Chemical compound O=C=NCCCSSCCCN=C=O KDELCQKJXHQDEX-UHFFFAOYSA-N 0.000 description 1
- CPWFHLLBKVXEBO-UHFFFAOYSA-N 1-isocyanato-3-(3-isocyanatopropylsulfanyl)propane Chemical compound O=C=NCCCSCCCN=C=O CPWFHLLBKVXEBO-UHFFFAOYSA-N 0.000 description 1
- DCQWACSEFXBOCJ-UHFFFAOYSA-N 1-isocyanato-6-(6-isocyanatohexylsulfanyl)hexane Chemical compound O=C=NCCCCCCSCCCCCCN=C=O DCQWACSEFXBOCJ-UHFFFAOYSA-N 0.000 description 1
- GVEDOIATHPCYGS-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)benzene Chemical group CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 GVEDOIATHPCYGS-UHFFFAOYSA-N 0.000 description 1
- GZCWLCBFPRFLKL-UHFFFAOYSA-N 1-prop-2-ynoxypropan-2-ol Chemical compound CC(O)COCC#C GZCWLCBFPRFLKL-UHFFFAOYSA-N 0.000 description 1
- RRPZHYWZRCTYBG-UHFFFAOYSA-N 18,18-dimethylnonadecan-1-amine Chemical class CC(C)(C)CCCCCCCCCCCCCCCCCN RRPZHYWZRCTYBG-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- YRHRHYSCLREHLE-UHFFFAOYSA-N 2,5-bis(isocyanatomethyl)-1,4-dithiane Chemical compound O=C=NCC1CSC(CN=C=O)CS1 YRHRHYSCLREHLE-UHFFFAOYSA-N 0.000 description 1
- BVLMYSAVQJGHAN-UHFFFAOYSA-N 2,5-bis(isocyanatomethyl)thiolane Chemical compound O=C=NCC1CCC(CN=C=O)S1 BVLMYSAVQJGHAN-UHFFFAOYSA-N 0.000 description 1
- YWROYNZKLNPZHR-UHFFFAOYSA-N 2,5-diisocyanatothiolane Chemical compound O=C=NC1CCC(N=C=O)S1 YWROYNZKLNPZHR-UHFFFAOYSA-N 0.000 description 1
- HKJDFSNCHROEEB-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)-3-[2-[2-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylethylsulfanyl]ethylsulfanyl]propane-1-thiol Chemical compound SCCSC(CS)CSCCSCCSCC(CS)SCCS HKJDFSNCHROEEB-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
- HORKBEXCKBOYSL-UHFFFAOYSA-N 2-[2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C1=C(CC(O)=O)N2C=CC=CC2=N1 HORKBEXCKBOYSL-UHFFFAOYSA-N 0.000 description 1
- OUHMFOSYPWFSKI-UHFFFAOYSA-N 2-[3-ethylsulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylethanethiol Chemical compound SCCSC(CSCC)CSCCS OUHMFOSYPWFSKI-UHFFFAOYSA-N 0.000 description 1
- VHBSECWYEFJRNV-UHFFFAOYSA-N 2-hydroxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1O.OC(=O)C1=CC=CC=C1O VHBSECWYEFJRNV-UHFFFAOYSA-N 0.000 description 1
- UKTZJXRJZBVHKL-UHFFFAOYSA-N 2h-benzotriazole Chemical class C1=CC=C2NN=NC2=C1.C1=CC=C2NN=NC2=C1 UKTZJXRJZBVHKL-UHFFFAOYSA-N 0.000 description 1
- TVLKIWFNAPTXLZ-UHFFFAOYSA-N 3,4-bis(isocyanatomethyl)thiolane Chemical compound O=C=NCC1CSCC1CN=C=O TVLKIWFNAPTXLZ-UHFFFAOYSA-N 0.000 description 1
- OCGYTRZLSMAPQC-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[1-sulfanyl-3-(2-sulfanylethylsulfanyl)propan-2-yl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SC(CS)CSCCS OCGYTRZLSMAPQC-UHFFFAOYSA-N 0.000 description 1
- NXYWIOFCVGCOCB-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SCC(CS)SCCS NXYWIOFCVGCOCB-UHFFFAOYSA-N 0.000 description 1
- HVSHOSLRLPSHOC-UHFFFAOYSA-N 3-(isocyanatomethyl)-7-thiabicyclo[4.1.0]hepta-2,4-diene Chemical compound N(=C=O)CC1=CC2C(C=C1)S2 HVSHOSLRLPSHOC-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
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 1
- CUVNZIBIDCGPQO-UHFFFAOYSA-N 4,5-bis(isocyanatomethyl)-2-methyl-1,3-dithiolane Chemical compound CC1SC(CN=C=O)C(CN=C=O)S1 CUVNZIBIDCGPQO-UHFFFAOYSA-N 0.000 description 1
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
- 102000013563 Acid Phosphatase Human genes 0.000 description 1
- 108010051457 Acid Phosphatase Proteins 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001614291 Anoplistes Species 0.000 description 1
- NCDMKVXZKAYJND-UHFFFAOYSA-N C(#N)C(C(=O)O)=C.C(#N)OC(C=C)=O Chemical class C(#N)C(C(=O)O)=C.C(#N)OC(C=C)=O NCDMKVXZKAYJND-UHFFFAOYSA-N 0.000 description 1
- XWBPZZRBPWENDC-UHFFFAOYSA-N C1=CC=C2NN=NC2=C1.CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 Chemical compound C1=CC=C2NN=NC2=C1.CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 XWBPZZRBPWENDC-UHFFFAOYSA-N 0.000 description 1
- JRANNTKZJNTXAU-UHFFFAOYSA-N CC1=C(C)C(C)=CC=C1.N=C=O.N=C=O.N=C=O Chemical compound CC1=C(C)C(C)=CC=C1.N=C=O.N=C=O.N=C=O JRANNTKZJNTXAU-UHFFFAOYSA-N 0.000 description 1
- MAMABHFMIUQTIY-UHFFFAOYSA-N CC1=CC=CC=C1.N=C=O.N=C=O.N=C=O Chemical compound CC1=CC=CC=C1.N=C=O.N=C=O.N=C=O MAMABHFMIUQTIY-UHFFFAOYSA-N 0.000 description 1
- KGZTXQAXSYNZKH-UHFFFAOYSA-N CCCCCCSCCCCCC.N=C=O Chemical compound CCCCCCSCCCCCC.N=C=O KGZTXQAXSYNZKH-UHFFFAOYSA-N 0.000 description 1
- PIVUWIOJBWFYAY-UHFFFAOYSA-N CCCCN(CCCCCCCCCCCC(CC)CC)C1CCCCC1 Chemical class CCCCN(CCCCCCCCCCCC(CC)CC)C1CCCCC1 PIVUWIOJBWFYAY-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000143243 Idaea flaveolaria Species 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- KOGDGTHGWFBMAY-UHFFFAOYSA-N N(=C=O)C1=C(C=CC=C1)C=CC1=C(C=CC=C1)N=C=O.N(=C=O)C1=C(C=CC=C1)C=C Chemical compound N(=C=O)C1=C(C=CC=C1)C=CC1=C(C=CC=C1)N=C=O.N(=C=O)C1=C(C=CC=C1)C=C KOGDGTHGWFBMAY-UHFFFAOYSA-N 0.000 description 1
- VRGMTXBMKXPNAO-UHFFFAOYSA-N N(=C=O)CC1SCSC1CN=C=O.N(=C=O)CC1SCSC1CN=C=O Chemical group N(=C=O)CC1SCSC1CN=C=O.N(=C=O)CC1SCSC1CN=C=O VRGMTXBMKXPNAO-UHFFFAOYSA-N 0.000 description 1
- AWLKTWKMOGKXGB-UHFFFAOYSA-N N(=C=O)CC=1SC(=CC1)CN=C=O.N(=C=O)CC=1SC(=CC1)CN=C=O Chemical compound N(=C=O)CC=1SC(=CC1)CN=C=O.N(=C=O)CC=1SC(=CC1)CN=C=O AWLKTWKMOGKXGB-UHFFFAOYSA-N 0.000 description 1
- SRDASPSTEGVGCM-UHFFFAOYSA-N N(=C=O)CCC1=C(C=CC=C1)CCN=C=O.N(=C=O)CCC1=CC=CC=C1 Chemical compound N(=C=O)CCC1=C(C=CC=C1)CCN=C=O.N(=C=O)CCC1=CC=CC=C1 SRDASPSTEGVGCM-UHFFFAOYSA-N 0.000 description 1
- PJCMAYITBZEGIL-UHFFFAOYSA-N N(=C=O)CCCC1=C(C=CC=C1)CCCN=C=O.C1=CC=CC=C1 Chemical compound N(=C=O)CCCC1=C(C=CC=C1)CCCN=C=O.C1=CC=CC=C1 PJCMAYITBZEGIL-UHFFFAOYSA-N 0.000 description 1
- JRZRDZSJNBVTTC-UHFFFAOYSA-N N(=C=O)CCCCC1=C(C=CC=C1)CCCCN=C=O.C1=CC=CC=C1 Chemical compound N(=C=O)CCCCC1=C(C=CC=C1)CCCCN=C=O.C1=CC=CC=C1 JRZRDZSJNBVTTC-UHFFFAOYSA-N 0.000 description 1
- XDMAIOVMEPCKAN-UHFFFAOYSA-N N(=C=O)CCSC(C)SCCN=C=O.CC Chemical compound N(=C=O)CCSC(C)SCCN=C=O.CC XDMAIOVMEPCKAN-UHFFFAOYSA-N 0.000 description 1
- FNUBGCHUEZWCDJ-UHFFFAOYSA-N N(=C=O)CCSCSCCN=C=O.C Chemical compound N(=C=O)CCSCSCCN=C=O.C FNUBGCHUEZWCDJ-UHFFFAOYSA-N 0.000 description 1
- ABNCWGFUMOXXOC-UHFFFAOYSA-N N(=C=O)CSC(C)SCN=C=O.CC Chemical compound N(=C=O)CSC(C)SCN=C=O.CC ABNCWGFUMOXXOC-UHFFFAOYSA-N 0.000 description 1
- RGIWGMTVJSICJZ-UHFFFAOYSA-N N(=C=O)CSCSCN=C=O.C Chemical compound N(=C=O)CSCSCN=C=O.C RGIWGMTVJSICJZ-UHFFFAOYSA-N 0.000 description 1
- XOMPUFACNHSNPC-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=CC=C1C Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1C XOMPUFACNHSNPC-UHFFFAOYSA-N 0.000 description 1
- BVZHBDFDJFWYQL-UHFFFAOYSA-N OC1C(C(C(C=C1)(CC1=CC=CC=C1)O)(O)O)(O)O Chemical compound OC1C(C(C(C=C1)(CC1=CC=CC=C1)O)(O)O)(O)O BVZHBDFDJFWYQL-UHFFFAOYSA-N 0.000 description 1
- AQFDQKHIHPQLBK-UHFFFAOYSA-N S-[2,3-bis(sulfanyl)propanoyl] 2,3-bis(sulfanyl)propanethioate Chemical compound SC(C(=O)SC(C(CS)S)=O)CS AQFDQKHIHPQLBK-UHFFFAOYSA-N 0.000 description 1
- JHXCBYAWHFDMGZ-UHFFFAOYSA-N S-[2,3-bis(sulfanyl)propanoylsulfanyl] 2,3-bis(sulfanyl)propanethioate Chemical compound SC(C(=O)SSC(C(CS)S)=O)CS JHXCBYAWHFDMGZ-UHFFFAOYSA-N 0.000 description 1
- SVTFOXIMEXFJBV-UHFFFAOYSA-N SCC(CS)(CS)CS.SCC Chemical compound SCC(CS)(CS)CS.SCC SVTFOXIMEXFJBV-UHFFFAOYSA-N 0.000 description 1
- FXEJHPSZPFKSQT-UHFFFAOYSA-N SCCSC(CSCCSCC(CS)SCCS)CS.CC Chemical compound SCCSC(CSCCSCC(CS)SCCS)CS.CC FXEJHPSZPFKSQT-UHFFFAOYSA-N 0.000 description 1
- CBFQFIHSZZFFSZ-UHFFFAOYSA-N SCSC(C(SCS)SCS)SCS.CC Chemical compound SCSC(C(SCS)SCS)SCS.CC CBFQFIHSZZFFSZ-UHFFFAOYSA-N 0.000 description 1
- UHLAIIZSHUXCBW-UHFFFAOYSA-N SCSC(CC(SCS)SCS)SCS.CCC Chemical compound SCSC(CC(SCS)SCS)SCS.CCC UHLAIIZSHUXCBW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 1
- COYTVZAYDAIHDK-UHFFFAOYSA-N [5-(sulfanylmethyl)-1,4-dithian-2-yl]methanethiol Chemical compound SCC1CSC(CS)CS1 COYTVZAYDAIHDK-UHFFFAOYSA-N 0.000 description 1
- SWJBITNFDYHWBU-UHFFFAOYSA-N [I].[I] Chemical compound [I].[I] SWJBITNFDYHWBU-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- VWPUAXALDFFXJW-UHFFFAOYSA-N benzenehexol Chemical compound OC1=C(O)C(O)=C(O)C(O)=C1O VWPUAXALDFFXJW-UHFFFAOYSA-N 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-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
- MPBRYMWMMKKRGC-UHFFFAOYSA-M carbocyanin DBTC Chemical compound [Br-].C1=CC=CC2=C([N+](=C(C=C(C)C=C3N(C4=C5C=CC=CC5=CC=C4S3)CC)S3)CC)C3=CC=C21 MPBRYMWMMKKRGC-UHFFFAOYSA-M 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- YFAXVVMIXZAKSR-UHFFFAOYSA-L dichloro(diethyl)stannane Chemical compound CC[Sn](Cl)(Cl)CC YFAXVVMIXZAKSR-UHFFFAOYSA-L 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- QPOIJJUKCPCQIV-UHFFFAOYSA-N diphenylmethanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 QPOIJJUKCPCQIV-UHFFFAOYSA-N 0.000 description 1
- PEGCFRJASNUIPX-UHFFFAOYSA-L ditert-butyltin(2+);dichloride Chemical compound CC(C)(C)[Sn](Cl)(Cl)C(C)(C)C PEGCFRJASNUIPX-UHFFFAOYSA-L 0.000 description 1
- DGJUONISEWDPFO-UHFFFAOYSA-N dodecyl(triethyl)azanium Chemical class CCCCCCCCCCCC[N+](CC)(CC)CC DGJUONISEWDPFO-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- KFGJUQRJVQDJHL-UHFFFAOYSA-N ethanethiol Chemical compound CCS.CCS KFGJUQRJVQDJHL-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- IVTWEBSTMUFDIA-UHFFFAOYSA-N heptadecane-1,17-dithiol Chemical compound SCCCCCCCCCCCCCCCCCS IVTWEBSTMUFDIA-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- IXBUFAUQDFHNGI-UHFFFAOYSA-N methylsulfanylmethanethiol Chemical group CSCS IXBUFAUQDFHNGI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical class C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- RWLIDRPIMIEHGZ-UHFFFAOYSA-N octadecane-1,18-dithiol Chemical compound SCCCCCCCCCCCCCCCCCCS RWLIDRPIMIEHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000002370 organoaluminium group Chemical group 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- ICNCMCHAPLUNBG-UHFFFAOYSA-N propyl carbamodithioate Chemical compound CCCSC(N)=S ICNCMCHAPLUNBG-UHFFFAOYSA-N 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C08G18/28—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
- 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
- C08G18/08—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
- C08G18/28—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
-
- 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
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6453—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having sulfur
-
- 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
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
-
- 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
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
-
- 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
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/757—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
-
- 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
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
-
- 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
- C08L75/04—Polyurethanes
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
实施方案涉及一种光学材料用聚合性组合物及由此获得的聚硫氨酯类化合物,上述聚硫氨酯类化合物的脉理及气泡发生率低,因此具有优异的外观。
Description
技术领域
实施方案涉及一种聚硫氨酯(polythiourethane)类光学材料用聚合性组合物及由此获得的聚硫氨酯类化合物,该聚硫氨酯类化合物的脉理及气泡发生率低,因此具有优异的外观。
背景技术
相比由玻璃等无机材料构成的光学材料,利用塑料的光学材料轻量、不易碎、染色性优秀,因此各种树脂的塑料材料作为眼镜镜片、相机镜片等的光学材料被广泛应用。随着近年来对更高性能及便利性的需求增加,对具有高透明性、高折射率、低比重、高耐热性、高耐冲击性等特性的光学材料的研究正在持续。
广泛应用的光学材料的实例,可以提及聚硫醇化合物(polythiol compound)和聚异氰酸酯化合物(polyisocyanate compound)聚合后得到的聚硫氨酯类化合物。但是,聚硫醇化合物和聚异氰酸酯化合物进行反应,由此制备聚硫氨酯类光学材料时,根据聚硫醇化合物和聚异氰酸酯化合物的种类、以及催化剂的种类及含量,反应性会发生变化,因此制备的聚硫氨酯类光学材料存在如下问题,即聚硫氨酯类光学材料因发生脉理及/或者气泡等存在外观缺陷。
作为解决方案,韩国公告专利第10-1704951号公开了一种聚氨酯树脂组合物(polyurethane resin composition)的制备方法,通过添加醇化合物,使得羟基相对于异氰酸酯基的比率为10乃至20mol%。
现有技术文献
专利文献
专利文献1:韩国公告专利第10-1704951号
发明要解决的课题
但是,上述韩国公告专利对脉理或气泡的改善并不充分,存在产量低的问题。
因此,实施方案期望提供一种可以制造塑料镜片的聚合性组合物,由于不受聚异氰酸酯、聚硫醇及催化剂的种类的约束,且不发生脉理及/或者气泡,所以可以使外观优异。
发明内容
一个实施方案提供一种聚合性组合物,其包含1~5种聚异氰酸酯化合物、1~5种聚硫醇化合物及由以下化学式1表示的催化剂,
由以下数学式1计算的R为9.5乃至19.5的实数,
[数学式1]
在上述数学式1中,
n是聚异氰酸酯化合物的种类数,
Ni是i聚异氰酸酯化合物的NCO的含量(重量%),
mi是i聚异氰酸酯化合物的官能团数,
Wi是i聚异氰酸酯化合物的投入量(g),
oi是i聚异氰酸酯化合物的重均分子量(g/mol),
l是聚硫醇化合物的种类数,
Sj是j聚硫醇化合物的当量重量(equivalent weight,g/eq)
uj是j聚硫醇化合物的官能团数,
Vj是j聚硫醇化合物的投入量(g),
tj是j聚硫醇化合物的重均分子量(g/mol),
Q是
[化学式1]
在上述化学式1中,
E是卤素化合物,
F是碳数为1乃至30的脂肪烃(aliphatic hydrocarbon)、或者碳数为6乃至30的芳香烃(aromatic hydrocarbon),
h及g各自独立地为1乃至4的整数,
h+g是4,
K是以聚异氰酸酯化合物和聚硫醇化合物的总投入量100为基准时由上述化学式1表示的化合物的添加量,
D是上述聚合性组合物的随时间变化的粘度变化率,是从以下数学式2导出的值,
[数学式2]
ln y=ln G+D×x
在上述数学式2中,
x是从制备组合物后到测量粘度为止所经过的时间(小时),为5乃至24,
y是x小时后10℃下的上述聚合性组合物的粘度(cps),
G是10℃下的上述聚合性组合物的初期粘度(cps)。
另一个实施方案提供一种由上述聚合性组合物获得的聚硫氨酯类化合物。
又一个实施方案提供一种由上述聚硫氨酯类化合物模塑而成的光学材料。
发明效果
由于实施方案的聚合性组合物不受聚异氰酸酯、聚硫醇及催化剂的种类的约束,且不发生脉理及/或者气泡,所以可制备出外观优异的塑料镜片。具体地,根据聚异氰酸酯、聚硫醇及催化剂等原料种类的不同,所制备的塑料镜片的外观、可加工性、数值稳定性等会有所不同,通过调整原料的种类及其含量,使得通过上述数学式1计算的R满足特定的数值范围,从而可提供一种如上所述的特性被综合考虑的聚合性组合物。
具体实施方式
一个实施方案提供一种聚合性组合物,其包含1~5种聚异氰酸酯化合物、1~5种聚硫醇化合物及由以下化学式1表示的催化剂,
由以下数学式1计算的R为9.5乃至19.5的实数,
[数学式1]
在上述数学式1中,
n是聚异氰酸酯化合物的种类数,
Ni是i聚异氰酸酯化合物的NCO的含量(重量%),
mi是i聚异氰酸酯化合物的官能团数,
Wi是i聚异氰酸酯化合物的投入量(g),
oi是i聚异氰酸酯化合物的重均分子量(g/mol),
l是聚硫醇化合物的种类数,
Sj是j聚硫醇化合物的当量重量(equivalent weight,g/eq)
uj是j聚硫醇化合物的官能团数,
Vj是j聚硫醇化合物的投入量(g),
tj是j聚硫醇化合物的重均分子量(g/mol),
Q是
[化学式1]
在上述化学式1中,
E是卤素化合物,
F是碳数为1乃至30的脂肪烃(aliphatic hydrocarbon)、或者碳数为6乃至30的芳香烃(aromatic hydrocarbon),
h及g各自独立地为1乃至4的整数,
h+g是4,
K是以聚异氰酸酯化合物和聚硫醇化合物的总投入量100为基准时由上述化学式1表示的化合物的添加量,
D是上述聚合性组合物的随时间变化的粘度变化率,是从以下数学式2导出的值,
[数学式2]
ln y=ln G+D×x
在上述数学式2中,
x是从制备组合物后到测量粘度为止所经过的时间(小时),为5乃至24,
y是x小时后10℃下的上述聚合性组合物的粘度(cps),
G是10℃下的上述聚合性组合物的初期粘度(cps)。
例如,当上述聚合性组合物包含第一聚异氰酸酯及第二聚异氰酸酯两种聚异氰酸酯时,在上述数学式1中,n是2,W1是第一聚异氰酸酯的使用量(g),W2是第二聚异氰酸酯的使用量(g),并且可按照相同的方式代入其他参数。
在上述聚合性组合物中,由上述数学式1计算的R可以是9.5乃至19.5的实数。具体地,在上述聚合性组合物中,由上述数学式1计算的R可以是9.5乃至19的实数、9.8乃至19的实数、9.8乃至18.5的实数、或者9.8乃至18的实数。当上述R为9.5以上时,由于聚异氰酸酯和聚硫醇之间的反应性太慢,所以可以防止在聚合末期因反应不均衡所引起的脉理及气泡发生率增加的情况和产量下降的问题。另外,当上述R为19.5以下时,由于反应性太快,所以可以防止在聚合初期因反应不均衡所引起的脉理及气泡发生率增加的情况和产量下降的问题。因此,优选上述R在上述范围内的聚合性组合物,从而使得制造出来的塑料镜片中存在脉理或气泡的可能性最小化,防止外观缺陷,并且使产量最大化。
上述A可以是80乃至120的实数,上述B可以是80乃至115的实数。具体地,上述A可以是82乃至117的实数、86乃至112的实数、或90乃至105的实数,上述B可以是82乃至114的实数、85乃至112的实数、或87乃至110的实数。
当上述A和B在上述范围内时,在聚合及固化过程中可提高尺寸稳定性,更有利于提高耐热性和抑制裂缝(crack)的发生。
上述D可以是0.08乃至0.25的实数、0.09乃至0.24的实数、或0.10乃至0.23的实数。当上述D在上述范围内时,聚合性组合物的均匀聚合是可能的,因此具有抑制气泡及脉理的出现、改善外观及可加工性的效果。
上述E可以是从由氟(F)、氯(Cl)、溴(Br)及碘(I)构成的群中选择的一种以上。具体地,上述E可以是氯。
上述F可以是碳数为1乃至10的烷基。具体地,上述F可以是甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基。
上述聚合性组合物包含1~5种聚异氰酸酯化合物、1~5种聚硫醇化合物及由上述化学式1表示的催化剂。具体地,上述聚合性组合物可包含1~3种聚异氰酸酯、1~4种聚硫醇及由上述化学式1表示的催化剂,或者包含1~2种聚异氰酸酯、1~2种聚硫醇及由上述化学式1表示的催化剂。
另外,上述聚合性组合物可包含1~3种聚异氰酸酯及1~4种聚硫醇。
聚异氰酸酯化合物
上述聚异氰酸酯化合物可以使用通常用于合成聚硫氨酯的。例如,可以包含选自由异佛尔酮二异氰酸酯(isophorone diisocyanate)、二环己基甲烷-4,4-二异氰酸酯(dicyclohexylmethane-4,4-diisocyanate)、六亚甲基二异氰酸酯(hexamethylenediisocyanate)、2,2-二甲基戊烷二异氰酸酯(2,2-dimethylpentane diisocyanate)、2,2,4-三甲基己烷二异氰酸酯(2,2,4-trimethylhexane diisocyanate)、丁烯二异氰酸酯(butene diisocyanate)、1,3-丁二烯-1,4-二异氰酸酯(1,3-butadiene-1,4-diisocyanate)、2,4,4-三甲基六亚甲基二异氰酸酯(2,4,4-trimethylhexamethylenediisocyanate)、1,6,11-十一烷三异氰酸酯(1,6,11-undecane triisocyanate)、1,3,6-六亚甲基三异氰酸酯(1,3,6-hexamethylene triisocyanate)、1,8-二异氰酸基-4-异氰酸基甲基辛烷(1,8-diisocyanato-4-isocyanatomethyloctane)、二(异氰酸基乙基)碳酸酯(bis(isocyanatoethyl)carbonate)、二(异氰酸基乙基)醚(bis(isocyanatoethyl)ether)等脂肪族异氰酸酯化合物;异佛尔酮二异氰酸酯(isophorone diisocyanate)、1,2-二(异氰酸基甲基)环己烷(1,2-bis(isocyanatomethyl)cyclohexane)、1,3-二(异氰酸基甲基)环己烷(1,3-bis(isocyanatomethyl)cyclohexane)、1,4-二(异氰酸基甲基)环己烷(1,4-bis(isocyanatomethyl)cyclohexane)、二环己基甲烷二异氰酸酯(dicyclohexylmethanediisocyanate)、环己烷二异氰酸酯(cyclohexane diisocyanate)、甲基环己烷二异氰酸酯(methylcyclohexane diisocyanate)、二环己基二甲基甲烷异氰酸酯(dicyclohexyldimethylmethane isocyanate)、2,2-二甲基二环己基甲烷异氰酸酯(2,2-dimethyldicyclohexylmethane isocyanate)、原冰片烷二异氰酸酯(norbornanediisocyanate)等脂环族异氰酸酯化合物;二(异氰酸基甲基)苯(bis(isocyanatomethyl)benzene)、二(异氰酸基乙基)苯(bis(isocyanatoethyl)benzene)、二(异氰酸基丙基)苯(bis(isocyanatopropyl)benzene)、二(异氰酸基丁基)苯(bis(isocyanatobutyl)benzene)、二(异氰酸基甲基)萘(bis(isocyanatomethyl)naphthalene)、二(异氰酸基甲基)二苯醚(bis(isocyanatomethyl)diphenyl ether)、亚苯基二异氰酸酯(phenylenediisocyanate)、乙基亚苯基二异氰酸酯(ethylphenylenediisocyanate)、异丙基亚苯基二异氰酸酯(isopropylphenylene diisocyanate)、二甲基亚苯基二异氰酸酯(dimethylphenylene diisocyanate)、二乙基亚苯基二异氰酸酯(diethylphenylenediisocyanate)、二异丙基亚苯基二异氰酸酯(diisopropylphenylene diisocyanate)、三甲基苯三异氰酸酯(trimethylbenzene triisocyanate)、苯三异氰酸酯(benzenetriisocyanate)、联苯二异氰酸酯(biphenyl diisocyanate)、甲苯胺二异氰酸酯(toluidine diisocyanate)、4,4-二苯基甲烷二异氰酸酯(4,4-diphenylmethanediisocyanate)、3,3-二甲基二苯基甲烷-4,4-二异氰酸酯(3,3-dimethyldiphenylmethane-4,4-diisocyanate)、联苄-4,4-二异氰酸酯(bibenzyl-4,4-diisocyanate)、二(异氰酸基苯基)乙烯(bis(isocyanatophenyl)ethylene)、3,3-二甲氧基联苯-4,4-二异氰酸酯(3,3-dimethoxybiphenyl-4,4-diisocyanate)、六羟基苯二异氰酸酯(hexahydrobenzene diisocyanate)、六羟基二苯基甲烷-4,4-二异氰酸酯(hexahydrodiphenylmethane-4,4-diisocyanate)、邻二甲苯二异氰酸酯(o-xylenediisocyanate)、间二甲苯二异氰酸酯(m-xylene diisocyanate)、对二甲苯二异氰酸酯(p-xylene diisocyanate)、甲苯二异氰酸酯(toluene diisocyanate)等芳香族异氰酸酯化合物;二(异氰酸基乙基)硫化物(bis(isocyanatoethyl)sulfide)、二(异氰酸基丙基)硫化物(bis(isocyanatopropyl)sulfide)、二(异氰酸基己基)硫化物(bis(isocyanate hexyl)sulfide)、二(异氰酸基甲基)砜(bis(isocyanatomethyl)sulfone)、二(异氰酸基甲基)二硫化物(bis(isocyanatomethyl)disulfide)、二(异氰酸基丙基)二硫化物(bis(isocyanatopropyl)disulfide)、二(异氰酸基甲基硫代)甲烷(bis(isocyanato methylthio)methane)、二(异氰酸基乙基硫代)甲烷(bis(isocyanato ethyl thio)methane)、二(异氰酸基乙基硫代)乙烷(bis(isocyanato ethyl thio)ethane)、二(异氰酸基甲基硫代)乙烷(bis(isocyanato methyl thio)ethane)、1,5-二异氰酸基-2-异氰酸基甲基-3-硫戊烷(1,5-diisocyanato-2-isocyanatomethyl-3-thiapentane)等含硫(sulfur-containing)脂肪族异氰酸酯化合物;二苯硫-2,4-二异氰酸酯(diphenyl sulfide-2,4-diisocyanate)、二苯硫-4,4-二异氰酸酯(diphenyl sulfide-4,4-diisocyanate)、3,3-二甲氧基-4,4-二异氰酸基二苄基硫醚(3,3-dimethoxy-4,4-diisocyanate dibenzylthioether)、二(4-异氰酸基甲苯)硫化物(bis(4-isocyanatomethylbenzene)sulfide)、4,4-甲氧基苯硫代乙二醇-3,3-二异氰酸酯(4,4-methoxybenzenethio ethylene glycol-3,3-diisocyanate)、二苯基二硫化物-4,4-二异氰酸酯(diphenyl disulfide-4,4-diisocyanate)、2,2-二甲基二苯基二硫化物-5,5-二异氰酸酯(2,2-dimethyl diphenyldisulfide-5,5-diisocyanate)、3,3-二甲基二苯基二硫化物-5,5-二异氰酸酯(3,3-dimethyl diphenyl disulfide-5,5-diisocyanate)、3,3-二甲基二苯基二硫化物-6,6-二异氰酸酯(3,3-dimethyl diphenyldisulfide-6,6-diisocyanate)、4,4-二甲基二苯基二硫化物-5,5-二异氰酸酯(4,4-dimethyldiphenyl disulfide-5,5-diisocyanate)、3,3-二甲氧基二苯基二硫化物-4,4-二异氰酸酯(3,3-dimethoxydiphenyl disulfide-4,4-diisocyanate)、4,4-二甲氧基二苯基二硫化物-3,3-二异氰酸酯(4,4-Dimethoxydiphenyldisulfide-3,3-diisocyanate)等含硫芳香族异氰酸酯化合物;及2,5-二异氰酸基噻吩(2,5-diisocyanate thiophene)、2,5-二(异氰酸基甲基)噻吩(2,5-bis(isocyanatomethyl)thiophene)、2,5-二异氰酸基四氢噻吩(2,5-diisocyanato tetrahydrothiophene)、2,5-二(异氰酸基甲基)四氢噻吩(2,5-bis(isocyanatomethyl)tetrahydrothiophene)、3,4-二(异氰酸基甲基)四氢噻吩(3,4-bis(isocyanatomethyl)tetrahydrothiophene)、2,5-二异氰酸基-1,4-二噻烷(2,5-diisocyanate-1,4-dithiane)、2,5-双(异氰酸基甲基)-1,4-二噻烷(2,5-bis(isocyanatomethyl)-1,4-dithiane)、4,5-二异氰酸基-1,3-二硫戊环(4,5-diisocyanate-1,3-dithiolane)、4,5-二(异氰酸基甲基)-1,3-二硫戊环(4,5-bis(isocyanatomethyl)-1,3-dithiolane)、4,5-二(异氰酸基甲基)-2-甲基-1,3-二硫戊环(4,5-bis(isocyanatomethyl)-2-methyl-1,3-dithiolane)等含硫杂环异氰酸酯化合物构成的群的一种以上。具体地,上述聚异氰酸酯化合物可以是选自由异佛尔酮二异氰酸酯(isophorone diisocyanate)、原冰片烷二异氰酸酯(norbornane diisocyanate)、间二甲苯二异氰酸酯(m-xylene diisocyanate)、甲苯二异氰酸酯(toluene diisocyanate)、六亚甲基二异氰酸酯(hexamethylene diisocyanate)及环己烷二异氰酸酯(cyclohexanediisocyanate)构成的群的1~5种。
上述聚异氰酸酯化合物的种类数(n)可以是1乃至5。具体地,上述聚异氰酸酯化合物的种类数(n)可以是1乃至3、或1乃至2。
上述聚异氰酸酯化合物的NCO含量(Ni)可通过ISO 14896“Plastics-Polyurethane raw materials-Determination of isocyanate content”中指定的方法来求得。
上述聚异氰酸酯化合物的官能团数(mi)可以是2或3。
上述聚异氰酸酯化合物的重均分子量(oi)可以是100乃至900g/mol、或150乃至800g/mol。
聚硫醇化合物
上述聚硫醇化合物可以使用通常用于合成聚硫氨酯的。例如,可以包含选自由二(2-(2-巯基乙基硫代)-3-巯基丙基)硫化物(bis(2-(2-mercaptoethylthio)-3-mercaptopropyl)sulfide)、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷(4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane)、2,3-二(2-巯基乙基硫代)丙烷-1-硫醇(2,3-bis(2-mercaptoethylthio)propane-1-thiol)、2,2-二(巯基甲基)-1,3-丙烷二硫醇(2,2-bis(mercapto methyl)-1,3-propane dithiol)、二(2-巯基乙基)硫化物(bis(2-mercapto ethyl)sulfide)、四(巯基甲基)甲烷(tetrakis(mercapto methyl)methane)、2-(2-巯基乙基硫代)丙烷-1,3-二硫醇(2-(2-mercapto ethyl thio)propane-1,3-dithiol)、2-(2,3-二(2-巯基乙基硫代)丙基硫代)乙烷硫醇(2-(2,3-bis(2-mercaptoethyl thio)propyl thio)ethane thiol)、二(2,3-二巯基丙基)硫化物(bis(2,3-dimercaptopropanyl)sulfide)、二(2,3-二巯基丙基)二硫化物(bis(2,3-dimercaptopropanyl)disulfide)、1,2-二(2-巯基乙基硫代)-3-巯基丙烷(1,2-bis(2-mercaptoethylthio)-3-mercaptopropane)、1,2-二(2-(2-巯基乙基硫代)-3-巯基丙基硫代)乙烷(1,2-bis(2-(2-mercapto ethyl thio)-3-mercapto propyl thio)ethane)、2-(2-巯基乙基硫代)-3-2-巯基-3-[3-巯基-2-(2-巯基乙基硫代)-丙基硫代]丙基硫代-丙烷-1-硫醇(2-(2-mercapto ethyl thio)-3-2-mercapto-3-[3-mercapto-2-(2-mercaptoethyl thio)-propyl thio]propyl thio-propane-1-thiol)、2,2-二-(3-巯基-丙酰氧甲基)-丁酯(2,2-bis-(3-mercapto-propionyl oxymethyl)-butyl ester)、2-(2-巯基乙基硫代)-3-(2-(2-[3-巯基-2-(2-巯基乙基硫代)-丙基硫代]乙基硫代)乙基硫代)丙烷-1-硫醇(2-(2-mercapto ethyl thio)-3-(2-(2-[3-mercapto-2-(2-mercapto ethyl thio)-propyl thio]ethyl thio)ethyl thio)propane-1-thiol)、(4R,11S)-4,11-二(巯基甲基)-3,6,9,12-四硫代四癸烷-1,14-二硫醇((4R,11S)-4,11-bis(mercapto methyl)-3,6,9,12-tetra thia tetra decane-1,14-dithiol)、(S)-3-((R-2,3-二巯基丙基)硫代)丙烷-1,2-二硫醇((S)-3-((R-2,3-dimercapto propyl)thio)propane-1,2-dithiol)、(4R,14R)-4,14-二(巯基甲基)-3,6,9,12,15-五硫代庚烷-1,17-二硫醇((4R,14R)-4,14-bis(mercapto methyl)-3,6,9,12,15-penta thia heptane-1,17-dithiol)、(S)-3-((R-3-巯基-2-((2-巯基乙基)硫代)丙基)硫代)丙基)硫代)-2-((2-巯基乙基)硫代)丙烷-1-硫醇((S)-3-((R-3-mercapto-2-((2-mercapto ethyl)thio)propyl)thio)propyl)thio)-2-((2-mercapto ethyl)thio)propane-1-thiol)、3,3'-二硫代二(丙烷-1,2-二硫醇)(3,3'-dithio bis(propane-1,2-dithiol))、(7R,11S)-7,11-二(巯基甲基)-3,6,9,12,15-五硫杂十七烷-1,17-二硫醇((7R,11S)-7,11-bis(mercapto methyl)-3,6,9,12,15-pentathia heptadecane-1,17-dithiol)、(7R,12S)-7,12-二(巯基甲基)-3,6,9,10,13,16-六硫杂十八烷-1,18-二硫醇((7R,12S)-7,12-bis(mercapto methyl)-3,6,9,10,13,16-hexathia octadecane-1,18-dithiol)、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷(5,7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷(4,7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷(4,8-dimercapto methyl-1,11-dimercapto-3,6,9-trithiaundecane)、季戊四醇四(3-巯基丙酸酯)(pentaerythritol tetrakis(3-mercaptopropionate))、三羟甲基丙烷三(3-巯基丙酸酯)(trimethylolpropane tris(3-mercaptopropionate))、季戊四醇四(2-巯基乙酸酯)(pentaerythritol tetrakis(2-mercaptoacetate))、二季戊四醇-醚-六(3-巯基丙酸酯)(bis-pentaerythritol-ether-hexakis(3-mercaptopropionate))、1,1,3,3-四(巯基甲基硫代)丙烷(1,1,3,3-tetrakis(mercapto methyl thio)propane)、1,1,2,2-四(巯基甲基硫代)乙烷(1,1,2,2-tetrakis(mercapto methyl thio)ethane)、4,6-二(巯基甲基硫代)-1,3-二噻烷(4,6-bis(mercapto methyl thio)-1,3-dithiane)、1,4-二噻烷-2,5-二甲硫醇(1,4-dithiane-2,5-dimethanethiol)及2-(2,2-二(巯基二甲基硫代)乙基)-1,3-二噻烷2-(2,2-bis(mercaptodimethylthio)ethyl)-1,3-dithiane)构成的群的一种以上。具体地,上述聚硫醇化合物可以是选自由4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷(4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane)、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷(4,8-dimercapto methyl-1,11-dimercapto-3,6,9-trithiaundecane)、季戊四醇四(3-巯基丙酸酯)(pentaerythritol tetrakis(3-mercaptopropionate))、季戊四醇四(2-巯基乙酸酯)(pentaerythritol tetrakis(2-mercaptoacetate))及1,4-二噻烷-2,5-二甲硫醇(1,4-dithiane-2,5-dimethanethiol)构成的群的1~5种。
上述聚硫醇化合物的种类数(l)可以是1乃至5、1乃至3、2或3。
可以通过容量滴定法来测量上述聚硫醇化合物的每单位分子量的当量重量(equivalent weight,g/eq)(Sj),上述容量滴定法利用硫醇(thiol)和碘(iodine)的氧化还原反应。
上述聚硫醇化合物的官能团数(uj)可以是2乃至6的整数、或2乃至4的整数。
上述聚硫醇化合物的重均分子量(tj)可以是100乃至1,000g/mol、或200乃至800g/mol。
上述聚合性组合物可包含摩尔比为0.5乃至1.5:1的聚硫醇化合物和异氰酸酯化合物。具体地,上述聚合性组合物可包含摩尔比为0.8乃至1.2:1的聚硫醇化合物和异氰酸酯化合物。
上述催化剂可以是由上述化学式1表示的化合物。具体地,上述催化剂可以是选自由二氯化二丁基锡(dibutyl tin dichloride)、二氯化二甲基锡(dimethyl tindichloride)、二氯化二乙基锡(diethyl tin dichloride)、二氯化二丙基锡(dipropyltin dichloride)、二氯化二异丙基锡(di-isopropyl tin dichloride)和二氯化二叔丁基锡(di-tertbutyl tin dichloride)构成的群的一种以上。
在10℃下放置24小时后,上述聚合性组合物的粘度可以是1,000cps(centipoise)以上。具体地,在10℃下放置24小时后,上述聚合性组合物的粘度可以是1,000乃至10,000cps、或1,500乃至10,000cps。在10℃下放置24小时后,当上述聚合性组合物的粘度在上述范围内时,可以防止因组合物的反应性太快使得可加工性变差、或者上述组合物的反应性太慢而使得产率降低的问题。
将上述聚合性组合物制备成直径为75mm、厚度为10mm的试片时,气泡发生率为0乃至10%,脉理发生率为0乃至8%。具体地,将上述聚合性组合物制备成直径为75mm、厚度为10mm的试片时,气泡发生率为0乃至8%、或0乃至5%,脉理发生率为0乃至7%、或0乃至5%。
添加剂
根据需要,上述聚合性组合物还可以包含内部脱模剂、紫外线吸收剂、聚合起始剂、热稳定剂、上蓝剂(blueing agent)、扩链剂、交联剂、光稳定剂、抗氧化剂、填充剂等添加剂。
上述内部脱模剂,例如可以包含选自由具有全氟烷基(perfluoroalkyl group)、羟烷基(hydroxyalkyl group)、或磷酸酯基(phosphate ester group)的氟系列非离子界面活性剂;具有二甲基聚硅氧烷基(dimethylpolysiloxane group)、羟烷基(hydroxyalkylgroup)、或磷酸酯基(phosphate ester group)的硅胶系列非离子界面活性剂;三甲基十六烷基铵盐(trimethylcetyl ammonium salt)、三甲基十八烷基(trimethylstearylammonium salt)、二甲基乙基十六烷基铵盐(dimethylethylcetyl ammonium salt)、三乙基十二烷基铵盐(triethyldodecyl ammonium salt)、三辛基甲基铵盐(trioctylmethylammonium salt)、二乙基环己基十二烷基铵盐(diethylcyclohexadodecyl ammoniumsalt)等烷基季铵盐(alkyl quaternary ammonium salts);以及酸性磷酸酯构成的群的一种以上。
上述紫外线吸收剂,例如,可以提及苯甲酮(benzophenone)类、苯并三唑(benzotriazole)类、水杨酸(salicylate)类、氰基丙烯酸酯(cyanoacrylate)类、草酰替苯胺(oxanilide)类等。
上述聚合起始剂,例如,可以提及胺类、磷类、有机锡类、有机铜类、有机镓、有机锆、有机铁类、有机锌和有机铝等。
上述热稳定剂,例如,可以提及金属脂肪酸盐类、磷类、铅类、有机锡类等。
上述上蓝剂对可见光区域中的橙色至黄色的波域具有吸收带,并具有对由树脂制成的光学材料的色相进行调整的功能。上述上蓝剂,具体可包含表现出蓝色至紫色的物质,但并不限定于此。此外,上述上蓝剂可提及染料、荧光增白剂、荧光颜料、无机颜料等,但是可以配合所要制造的光学部件要求的物理性质、树脂色相等适当选择。上述上蓝剂可以分别单独使用或者组合两种以上来使用。从对聚合性组合物的溶解性的观点以及所获得的光学材料的透明性的观点来看,上述上蓝剂优选染料。关于上述染料,从吸收波长的观点来看,具体可以是极大吸收波长为520~600nm的染料,更加具体地,可以是极大吸收波长为540~580nm的染料。此外,从化合物结构的观点来看,上述染料优选蒽醌(anthraquinone)类染料。上蓝剂的添加方法并没有特别限定,可以事先添加至单体(monomer)系列中。具体地,上述上蓝剂的添加方法可使用如下多种方法:溶解于单体中的方法;或者,制造出含有高浓度上蓝剂的母液(master solution),并用使用上述母液的单体或者其他添加剂稀释后添加的方法等。
聚硫氨酯类化合物
另一个实施方案提供一种由如上所述的聚合性组合物获得的聚硫氨酯类化合物。
上述聚硫氨酯类化合物是通过聚合(及固化)聚硫醇化合物和聚异氰酸酯化合物来制备。在上述聚合反应中,SH基/NCO基的反应摩尔比可以是0.5乃至3.0,具体地,可以是0.6乃至2.0、或0.8乃至1.3。在上述范围内时,可提高光学材料要求的折射率、耐热性等特性及均势(balance)。
光学材料
再一个实施方案提供一种由如上所述的聚硫氨酯类化合物模塑而成的光学材料。具体地,上述光学材料可以由固化上述聚合性组合物后所获得的成型体构成。另外,上述光学材料可以通过聚合及模塑聚合性组合物(聚硫醇化合物+聚异氰酸酯化合物+催化剂)来制备。
首先,在减压下对上述聚合性组合物进行脱气(degassing)后,注入到光学材料成形用模具中。像这样的脱气及模具内的注入,例如可以在5~40℃或者10~30℃下进行。注入到模具中后,通常从低温逐渐加热至高温来进行聚合。上述聚合反应的温度,例如,可以是30~150℃,具体地,可以是40~130℃。另外,为了调节反应速度,可以添加通常用于制备聚硫氨酯的反应催化剂,其具体种类如前所述。
此后,将聚硫氨酯类光学材料从模具分离。
通过更换制造过程中所使用的模具的模,上述光学材料可以被制成各种形状。具体地,可以是眼镜镜片、相机镜片、发光二极管(LED)等形态。上述光学材料,例如,可以是光学镜片,具体地,可以是塑料光学镜片。
上述光学材料对546nm的光的折射率为1.55乃至1.70,阿贝数可以是25乃至50。具体地,上述光学材料对546nm的光的折射率为1.58乃至1.68,阿贝数可以是30乃至45。
[实施例]
以下,根据下述实施例,更加详细地进行说明。但是,下述实施例仅仅是为了例示本发明而已,本发明的范围并不限定于这些实施例。
在以下实施例和比较例中使用的聚异氰酸酯及聚硫醇如下表1和2所示。
【表1】
【表2】
-催化剂1:DMTC,二氯化二甲基锡
-催化剂2:DBTC,二氯化二丁基锡
实施例1.
将聚异氰酸酯、聚硫醇和催化剂按照下面表3中所示的组成来混合,以聚异氰酸酯和聚硫醇的总100重量份为基准,混合1.0重量份的紫外线稳定剂2-(2-羟基-5-叔辛基苯基)苯并三唑(2-(2-hydroxy-5-tert-octylphenyl)benzotriazole)及0.2重量份的内部脱模剂UN(酸性磷酸烷基酯(phosphoric alkyl ester)脱模剂,Stepan公司),由此制备聚合性组合物。
实施例2~9及比较例1~3.
除了将聚异氰酸酯、聚硫醇和催化剂按照下面表3中所示的组成来混合之外,用和实施例1相同的方法来制备聚合性组合物。
【表3】
实验例:确认物理性质
将上述实施例1~9及比较例1~3的聚合性组合物作为对象,测量10℃下的粘度变化、由此获得的塑料镜片的脉理及气泡发生率、折射率及阿贝数。测量结果如下表4所示。
(1)测量粘度
将上述实施例1~9及比较例1~3的聚合性组合物在10℃及2torr下进行1小时的脱气后,用3μm的聚四氟乙烯过滤器(teflon filter)进行过滤。对过滤后的聚合性组合物利用非接触式粘度计(EMS-1000,日本京都电子公司)测量10℃下的粘度变化,测量持续24小时,再用以下数学式2计算随时间的粘度变化率。
[数学式2]
ln y=ln G+D×x
(2)脉理发生率
用和上述项目(1)相同的方法将过滤后的聚合性组合物注入到用胶带组装的玻璃铸模中。然后将上述铸模在10℃下放置5小时后,以5℃/分钟的速度从10℃升温至120℃,在120℃下进行20小时的聚合。接着,在玻璃铸模中固化的直径为75mm、厚度为10mm的试片在130℃下进一步固化4小时之后,使成形体(塑料镜片)从玻璃铸模中脱模。
使汞灯光透过塑料镜片,并将透射光投影至白板上,查看是否具有明暗差,由此判断是否具有脉理。制备100枚塑料镜片来评价脉理发生率。
(3)气泡发生率
在汞灯下用肉眼观察用和上述项目(2)相同的方法制备的塑料镜片,观察是否发生微细气泡。制备100枚塑料镜片来评价气泡发生率。
(4)折射率及阿贝数
在20℃下使用阿贝折射仪DR-M4(ATAGO公司制造)并用E-line(nE),来测量用和上述项目(2)相同的方法制备的塑料镜片的折射率和阿贝数。
具体地,测量对546nm的光的折射率。
【表4】
如上述表4所示,实施例1~9的聚合性组合物的R是9.5乃至19.5,由此制备的塑料镜片的脉理及气泡发生率低,从而具有优异的外观。与此相反,由于比较例1~3的聚合性组合物的R不满足上述范围,所以由此制备的塑料镜片的脉理及气泡发生率高,从而存在外观缺陷。
Claims (13)
1.一种聚合性组合物,其包含1~5种聚异氰酸酯化合物、1~5种聚硫醇化合物及由以下化学式1表示的催化剂,
由以下数学式1计算的R为9.5乃至19.5的实数,
[数学式1]
在上述数学式1中,
n是聚异氰酸酯化合物的种类数,
Ni是i聚异氰酸酯化合物的NCO的含量(重量%),
mi是i聚异氰酸酯化合物的官能团数,
Wi是i聚异氰酸酯化合物的投入量(g),
oi是i聚异氰酸酯化合物的重均分子量(g/mol),
l是聚硫醇化合物的种类数,
Sj是j聚硫醇化合物的当量重量(equivalent weight,g/eq)
uj是j聚硫醇化合物的官能团数,
Vj是j聚硫醇化合物的投入量(g),
tj是j聚硫醇化合物的重均分子量(g/mol),
Q是
[化学式1]
在上述化学式1中,
E是卤素化合物,
F是碳数为1乃至30的脂肪烃、或碳数为6乃至30的芳香烃,
h及g各自独立地为1乃至4的整数,
h+g是4,
K是以聚异氰酸酯化合物和聚硫醇化合物的总投入量100为基准时由上述化学式1表示的化合物的添加量,
D是上述聚合性组合物的随时间变化的粘度变化率,是从以下数学式2导出的值,
[数学式2]
ln y=ln G+D×x
在上述数学式2中,
x是从制备组合物后到测量粘度为止所经过的时间(小时),为5乃至24,
y是x小时后10℃下的上述聚合性组合物的粘度(cps),
G是10℃下的上述聚合性组合物的初期粘度(cps)。
2.如权利要求1所述的聚合性组合物,其特征在于,
上述A是80乃至120的实数,
上述B是80乃至115的实数。
3.如权利要求1所述的聚合性组合物,其特征在于,
上述D是0.08乃至0.25的实数。
4.如权利要求1所述的聚合性组合物,其特征在于,
上述R是9.8乃至18的实数。
5.如权利要求1所述的聚合性组合物,其特征在于,
上述E是从由氟(F)、氯(Cl)、溴(Br)及碘(I)构成的群中选择的一种以上。
6.如权利要求1所述的聚合性组合物,其特征在于,
上述F是具有碳数为1乃至10的烷基。
7.如权利要求6所述的聚合性组合物,其特征在于,
上述F是甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基。
8.如权利要求1所述的聚合性组合物,其特征在于,
在10℃下放置24小时后,上述聚合性组合物的粘度为1,000cps(centipoise)以上。
9.如权利要求1所述的聚合性组合物,其特征在于,
将上述聚合性组合物制备成直径为75mm、厚度为10mm的试片时,气泡发生率为0乃至10%,脉理发生率为0乃至8%。
10.如权利要求1所述的聚合性组合物,其特征在于,
上述聚合性组合物包含1~3种聚异氰酸酯及1~4种聚硫醇。
11.一种聚硫氨酯类化合物,由权利要求1~10中任一项所述的聚合性组合物来制备。
12.一种光学材料,由权利要求11的聚硫氨酯类化合物模塑而成。
13.如权利要求12所述的光学材料,其特征在于,
上述光学材料对546nm的光的折射率为1.55乃至1.70,阿贝数为25乃至45。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020170182078A KR20190079956A (ko) | 2017-12-28 | 2017-12-28 | 광학 재료용 중합성 조성물 |
KR10-2017-0182078 | 2017-12-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109575217A true CN109575217A (zh) | 2019-04-05 |
CN109575217B CN109575217B (zh) | 2021-05-11 |
Family
ID=65199275
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811490099.2A Active CN109575217B (zh) | 2017-12-28 | 2018-12-06 | 光学材料用聚合性组合物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10759895B2 (zh) |
EP (1) | EP3505547B1 (zh) |
JP (1) | JP6957445B2 (zh) |
KR (1) | KR20190079956A (zh) |
CN (1) | CN109575217B (zh) |
TW (1) | TWI691519B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115403737A (zh) * | 2021-05-28 | 2022-11-29 | Skc株式会社 | 聚合性组合物及使用其的光学材料 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021202197A1 (en) * | 2020-03-30 | 2021-10-07 | Ppg Industries Ohio, Inc. | Method of preparing low haze polymer compositions for use in high refractive index optical materials |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001353734A (ja) * | 2000-06-16 | 2001-12-25 | Seiko Epson Corp | プラスチックレンズの製造方法およびプラスチックレンズ製造用粘着テープ |
WO2004108844A2 (en) * | 2003-06-04 | 2004-12-16 | Basf Corporation | Dual radiation/thermal cured coating composition |
CN101516947A (zh) * | 2006-09-26 | 2009-08-26 | 洛克泰特(R&D)有限公司 | 新型加合物和使用它们的可固化组合物 |
CN103108918A (zh) * | 2011-03-02 | 2013-05-15 | 可奥熙搜路司有限公司 | 利用通用聚异氰酸酯化合物的硫代氨基甲酸乙酯系光学材料用树脂的制备方法和树脂组合物及制备的光学材料 |
WO2013146481A1 (ja) * | 2012-03-27 | 2013-10-03 | Hoya株式会社 | プラスチックレンズの製造方法 |
EP2660260A1 (en) * | 2010-12-27 | 2013-11-06 | Mitsubishi Gas Chemical Company, Inc. | Composition for optical material |
EP2891672A1 (en) * | 2012-08-29 | 2015-07-08 | KOC Solution Co. Ltd. | Method for manufacturing thiourethane-based optical material |
US20150226379A1 (en) * | 2012-10-24 | 2015-08-13 | Daewoo Shipbuilding & Marine Engineering Co., Ltd. | Liquefied gas treatment method for vessel |
CN105960425A (zh) * | 2014-02-06 | 2016-09-21 | 三井化学株式会社 | 光学材料用聚合性组合物和光学材料 |
WO2016153061A1 (ja) * | 2015-03-25 | 2016-09-29 | ホヤ レンズ タイランド リミテッド | 重合性組成物、光学部材、プラスチックレンズ、及び眼鏡レンズ |
US20160304701A1 (en) * | 2013-12-13 | 2016-10-20 | Mitsui Chemicals, Inc. | Polymerizable composition for optical materials |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9464154B2 (en) | 2012-11-21 | 2016-10-11 | Mitsui Chemicals, Inc. | Process for producing polyurethane resin |
KR101996981B1 (ko) * | 2017-10-18 | 2019-07-05 | 에스케이씨 주식회사 | 플라스틱 렌즈용 중합성 조성물 |
-
2017
- 2017-12-28 KR KR1020170182078A patent/KR20190079956A/ko active Search and Examination
-
2018
- 2018-12-06 CN CN201811490099.2A patent/CN109575217B/zh active Active
- 2018-12-20 TW TW107146157A patent/TWI691519B/zh active
- 2018-12-24 EP EP18215872.5A patent/EP3505547B1/en active Active
- 2018-12-25 JP JP2018241026A patent/JP6957445B2/ja active Active
- 2018-12-26 US US16/232,746 patent/US10759895B2/en active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001353734A (ja) * | 2000-06-16 | 2001-12-25 | Seiko Epson Corp | プラスチックレンズの製造方法およびプラスチックレンズ製造用粘着テープ |
WO2004108844A2 (en) * | 2003-06-04 | 2004-12-16 | Basf Corporation | Dual radiation/thermal cured coating composition |
CN101516947A (zh) * | 2006-09-26 | 2009-08-26 | 洛克泰特(R&D)有限公司 | 新型加合物和使用它们的可固化组合物 |
EP2660260A1 (en) * | 2010-12-27 | 2013-11-06 | Mitsubishi Gas Chemical Company, Inc. | Composition for optical material |
CN103108918A (zh) * | 2011-03-02 | 2013-05-15 | 可奥熙搜路司有限公司 | 利用通用聚异氰酸酯化合物的硫代氨基甲酸乙酯系光学材料用树脂的制备方法和树脂组合物及制备的光学材料 |
WO2013146481A1 (ja) * | 2012-03-27 | 2013-10-03 | Hoya株式会社 | プラスチックレンズの製造方法 |
EP2891672A1 (en) * | 2012-08-29 | 2015-07-08 | KOC Solution Co. Ltd. | Method for manufacturing thiourethane-based optical material |
US20150226379A1 (en) * | 2012-10-24 | 2015-08-13 | Daewoo Shipbuilding & Marine Engineering Co., Ltd. | Liquefied gas treatment method for vessel |
US20160304701A1 (en) * | 2013-12-13 | 2016-10-20 | Mitsui Chemicals, Inc. | Polymerizable composition for optical materials |
CN105960425A (zh) * | 2014-02-06 | 2016-09-21 | 三井化学株式会社 | 光学材料用聚合性组合物和光学材料 |
WO2016153061A1 (ja) * | 2015-03-25 | 2016-09-29 | ホヤ レンズ タイランド リミテッド | 重合性組成物、光学部材、プラスチックレンズ、及び眼鏡レンズ |
Non-Patent Citations (1)
Title |
---|
高长有: "含硫高折光指数光学塑料的分子设计 ", 《材料研究学报》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115403737A (zh) * | 2021-05-28 | 2022-11-29 | Skc株式会社 | 聚合性组合物及使用其的光学材料 |
CN115403737B (zh) * | 2021-05-28 | 2024-07-09 | 爱思开核心聚氨酯有限公司 | 聚合性组合物及使用其的光学材料 |
Also Published As
Publication number | Publication date |
---|---|
US10759895B2 (en) | 2020-09-01 |
TW201932503A (zh) | 2019-08-16 |
KR20190079956A (ko) | 2019-07-08 |
US20190202968A1 (en) | 2019-07-04 |
EP3505547A1 (en) | 2019-07-03 |
JP6957445B2 (ja) | 2021-11-02 |
JP2019119861A (ja) | 2019-07-22 |
EP3505547B1 (en) | 2024-06-26 |
TWI691519B (zh) | 2020-04-21 |
CN109575217B (zh) | 2021-05-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6077146B2 (ja) | ウレタン系光学材料用樹脂の製造方法、樹脂組成物、及び製造された光学材料 | |
JP5315426B2 (ja) | 光学材料用樹脂の製造方法 | |
JP4496121B2 (ja) | 色相に優れた硫黄原子含有透明樹脂の製造方法 | |
CN104662012B (zh) | 环硫化物化合物的保管方法和利用上述环硫化物化合物的硫代环氧类光学材料的制备方法 | |
JP5842827B2 (ja) | 光学材料用組成物 | |
JP3995427B2 (ja) | 新規なポリチオールを含有する重合性組成物、及びそれを重合させてなる樹脂、並びにレンズ | |
CN104321308A (zh) | 新聚硫醇化合物的制造方法及包括此的光学材料用聚合性组合物 | |
KR101802479B1 (ko) | 고리개환을 통해 사슬연장된 폴리티올화합물과 그 제조 방법 및 이를 이용한 우레탄계 광학재료용 수지 조성물 | |
JP2016175905A (ja) | 光学材料用ポリチオール化合物の製造方法及びそれを用いたウレタン系光学材料の製造方法 | |
JP2019065185A (ja) | 光学部材用樹脂の製造方法、光学部材用樹脂、眼鏡レンズ及び眼鏡 | |
CN109575217A (zh) | 光学材料用聚合性组合物 | |
US7396900B2 (en) | Thiourethane-based optical material | |
CN104039860A (zh) | 硫代环氧基系光学材料用聚合性合成物与硫代环氧基系光学材料制造方法 | |
KR20130085914A (ko) | 티오에폭시계 중합성 조성물과 티오에폭시계 광학재료의 제조방법 | |
KR20130081253A (ko) | 티오에폭시 화합물, 폴리이소시아네이트 화합물 및 폴리티올 화합물을 포함하는 고굴절 광학렌즈용 공중합체 조성물과 광학렌즈의 제조방법 | |
JP4684427B2 (ja) | 新規なポリチオール | |
JP4326455B2 (ja) | 高耐熱性樹脂用ポリチオール | |
KR102150592B1 (ko) | 광학 재료용 중합성 조성물 | |
KR20140001808A (ko) | 티오우레탄계 광학재료의 제조방법 | |
JP2005325183A (ja) | 高屈折率チオウレタン系光学材料 | |
JP4417089B2 (ja) | 高屈折率・高耐熱性透明樹脂用組成物 | |
JP3974404B2 (ja) | ポリチオール、その製造方法、これを含有する重合性組成物、並びに樹脂及びレンズ | |
CN112543776A (zh) | 可聚合组合物及由其制备的光学材料 | |
JP2005154692A (ja) | 高屈折率透明樹脂用組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240205 Address after: 255 Longyan Road, Ulsan South District, South Korea Patentee after: Aisikai Core Polyurethane Co.,Ltd. Country or region after: Republic of Korea Address before: Chang'an Road 309 Pan Street 84, Chang'an District, Shuiyuan City, Gyeonggi Road, Korea Patentee before: SKC Co.,Ltd. Country or region before: Republic of Korea |
|
TR01 | Transfer of patent right |