CN110643010B - Isocyanate composition and optical resin prepared from same - Google Patents
Isocyanate composition and optical resin prepared from same Download PDFInfo
- Publication number
- CN110643010B CN110643010B CN201910898633.1A CN201910898633A CN110643010B CN 110643010 B CN110643010 B CN 110643010B CN 201910898633 A CN201910898633 A CN 201910898633A CN 110643010 B CN110643010 B CN 110643010B
- Authority
- CN
- China
- Prior art keywords
- bis
- isocyanate
- mercaptomethylthio
- complexing agent
- diisocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 57
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 51
- 230000003287 optical effect Effects 0.000 title claims abstract description 43
- 239000011347 resin Substances 0.000 title claims abstract description 28
- 229920005989 resin Polymers 0.000 title claims abstract description 28
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 239000008139 complexing agent Substances 0.000 claims abstract description 33
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 28
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 14
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 14
- 239000011651 chromium Substances 0.000 claims abstract description 14
- 229910052742 iron Inorganic materials 0.000 claims abstract description 14
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 14
- 239000011572 manganese Substances 0.000 claims abstract description 14
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 14
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 14
- 239000011591 potassium Substances 0.000 claims abstract description 14
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 14
- 239000011734 sodium Substances 0.000 claims abstract description 14
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 14
- 239000012043 crude product Substances 0.000 claims description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- GNQKHBSIBXSFFD-UHFFFAOYSA-N 1,3-diisocyanatocyclohexane Chemical compound O=C=NC1CCCC(N=C=O)C1 GNQKHBSIBXSFFD-UHFFFAOYSA-N 0.000 claims description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims 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 claims description 2
- 238000003860 storage Methods 0.000 abstract description 11
- -1 isocyanate compound Chemical class 0.000 description 56
- 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 30
- 150000001875 compounds Chemical class 0.000 description 28
- 239000000047 product Substances 0.000 description 17
- 229920006295 polythiol Polymers 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 230000000007 visual effect Effects 0.000 description 8
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 238000006552 photochemical reaction Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- VUTVSWPVTJZPFU-UHFFFAOYSA-N propylsulfanylmethanethiol Chemical compound CCCSCS VUTVSWPVTJZPFU-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RHMKQRWOFRAOHS-UHFFFAOYSA-N (sulfanylmethyldisulfanyl)methanethiol Chemical compound SCSSCS RHMKQRWOFRAOHS-UHFFFAOYSA-N 0.000 description 2
- XLWCIHPMASUXPI-UHFFFAOYSA-N 1,1'-(propane-1,2-diyl)dibenzene Chemical compound C=1C=CC=CC=1C(C)CC1=CC=CC=C1 XLWCIHPMASUXPI-UHFFFAOYSA-N 0.000 description 2
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SPAAESPYCDSRIW-UHFFFAOYSA-N 2-(2-sulfanylethyldisulfanyl)ethanethiol Chemical compound SCCSSCCS SPAAESPYCDSRIW-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010040925 Skin striae Diseases 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- MALTWXYAYKZMJG-UHFFFAOYSA-N [1,2-bis(sulfanylmethylsulfanyl)-2-[1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethylsulfanyl]ethyl]sulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCSC(SCS)C(SCS)SCS MALTWXYAYKZMJG-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
- 239000002390 adhesive tape Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 150000004252 dithioacetals Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- 239000006082 mold release agent Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VRQFYSHDLYCPRC-UHFFFAOYSA-N (ethylsulfanyl)methanethiol Chemical compound CCSCS VRQFYSHDLYCPRC-UHFFFAOYSA-N 0.000 description 1
- CAYNCHQZXZMUEX-UHFFFAOYSA-N (hydroxymethyldisulfanyl)methanol 2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OCSSCO CAYNCHQZXZMUEX-UHFFFAOYSA-N 0.000 description 1
- BXGKVFOHNHSLHH-UHFFFAOYSA-N (hydroxymethyldisulfanyl)methanol 3-sulfanylpropanoic acid Chemical compound OCSSCO.OC(=O)CCS.OC(=O)CCS BXGKVFOHNHSLHH-UHFFFAOYSA-N 0.000 description 1
- CNQBWJAQMONNEC-UHFFFAOYSA-N 1,1,2-tris(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCCC1(CN=C=O)CN=C=O CNQBWJAQMONNEC-UHFFFAOYSA-N 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- PBPRZRZXNXUAEJ-UHFFFAOYSA-N 1,2-bis(sulfanyl)butane-1,3-diol Chemical compound CC(O)C(S)C(O)S PBPRZRZXNXUAEJ-UHFFFAOYSA-N 0.000 description 1
- PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical compound C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- UAFGBPBVGOWZHR-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropyl)benzene Chemical compound O=C=NC(C)CC1=CC=CC(CC(C)N=C=O)=C1 UAFGBPBVGOWZHR-UHFFFAOYSA-N 0.000 description 1
- WNPSAOYKQQUALV-UHFFFAOYSA-N 1,3-bis(sulfanyl)propan-2-ol Chemical compound SCC(O)CS WNPSAOYKQQUALV-UHFFFAOYSA-N 0.000 description 1
- UFUYYOACZGNQGB-UHFFFAOYSA-N 1,3-dithiolan-2-ylmethanethiol Chemical compound SCC1SCCS1 UFUYYOACZGNQGB-UHFFFAOYSA-N 0.000 description 1
- WOCWGASBYDHHMD-UHFFFAOYSA-N 1,3-dithiolan-2-ylsulfanylmethanethiol Chemical compound SCSC1SCCS1 WOCWGASBYDHHMD-UHFFFAOYSA-N 0.000 description 1
- HFLVJACGRATKGE-UHFFFAOYSA-N 1,3-dithiolan-4-ylsulfanylmethanethiol Chemical compound SCSC1CSCS1 HFLVJACGRATKGE-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- JFLJVRLBIZHFSU-UHFFFAOYSA-N 1,4-dithiane-2,5-dithiol Chemical compound SC1CSC(S)CS1 JFLJVRLBIZHFSU-UHFFFAOYSA-N 0.000 description 1
- YPLPXJFDSYXYSF-UHFFFAOYSA-N 1,5,7,11-tetrathiaspiro[5.5]undecane-3,9-dithiol Chemical compound S1CC(S)CSC21SCC(S)CS2 YPLPXJFDSYXYSF-UHFFFAOYSA-N 0.000 description 1
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 1
- PGTWZHXOSWQKCY-UHFFFAOYSA-N 1,8-Octanedithiol Chemical compound SCCCCCCCCS PGTWZHXOSWQKCY-UHFFFAOYSA-N 0.000 description 1
- QOPKHMOZQMJDRR-UHFFFAOYSA-N 1-(isocyanatomethyl)-1-[1-(isocyanatomethyl)cycloheptyl]cycloheptane Chemical compound C1CCCCCC1(CN=C=O)C1(CN=C=O)CCCCCC1 QOPKHMOZQMJDRR-UHFFFAOYSA-N 0.000 description 1
- NPFJINKUEGHANT-UHFFFAOYSA-N 1-[1,3-bis(sulfanyl)propylsulfanyl]propane-1,3-dithiol Chemical compound SCCC(S)SC(S)CCS NPFJINKUEGHANT-UHFFFAOYSA-N 0.000 description 1
- NNCXDEWVRJPDMP-UHFFFAOYSA-N 1-[3-(2-sulfanylethylsulfanyl)phenyl]sulfanylethanol Chemical compound CC(O)SC1=CC=CC(SCCS)=C1 NNCXDEWVRJPDMP-UHFFFAOYSA-N 0.000 description 1
- JEARXBADBBQFGS-UHFFFAOYSA-N 1-methoxypropane-1,2-dithiol Chemical compound COC(S)C(C)S JEARXBADBBQFGS-UHFFFAOYSA-N 0.000 description 1
- DLLOHKQWGFKFLO-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dithiol Chemical compound CC1(S)CCCCC1S DLLOHKQWGFKFLO-UHFFFAOYSA-N 0.000 description 1
- YDFDTKKXMZRNHR-UHFFFAOYSA-N 1-n,3-n-dimethylcyclohexane-1,3-diamine Chemical compound CNC1CCCC(NC)C1 YDFDTKKXMZRNHR-UHFFFAOYSA-N 0.000 description 1
- KMRGAXDRIMOHPO-UHFFFAOYSA-N 2,2-bis(isocyanatomethyl)-1,4-dithiane Chemical compound O=C=NCC1(CN=C=O)CSCCS1 KMRGAXDRIMOHPO-UHFFFAOYSA-N 0.000 description 1
- MTZVWTOVHGKLOX-UHFFFAOYSA-N 2,2-bis(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)(CS)CS MTZVWTOVHGKLOX-UHFFFAOYSA-N 0.000 description 1
- MLHBQCMRBXCFLT-UHFFFAOYSA-N 2,2-bis(sulfanylmethylsulfanyl)ethanethiol Chemical compound SCSC(CS)SCS MLHBQCMRBXCFLT-UHFFFAOYSA-N 0.000 description 1
- LPMUHJBJYVXZTL-UHFFFAOYSA-N 2,3-bis(sulfanyl)propyl 2-[[2-[2,3-bis(sulfanyl)propoxy]-2-oxoethyl]disulfanyl]acetate Chemical compound SCC(S)COC(=O)CSSCC(=O)OCC(S)CS LPMUHJBJYVXZTL-UHFFFAOYSA-N 0.000 description 1
- DSPSCCDARHPVFY-UHFFFAOYSA-N 2,3-bis(sulfanyl)propyl 3-[3-[2,3-bis(sulfanyl)propoxy]-3-oxopropyl]sulfanylpropanoate Chemical compound SCC(S)COC(=O)CCSCCC(=O)OCC(S)CS DSPSCCDARHPVFY-UHFFFAOYSA-N 0.000 description 1
- UQSCGTREKJYHOH-UHFFFAOYSA-N 2,3-bis(sulfanyl)propyl 3-[[3-[2,3-bis(sulfanyl)propoxy]-3-oxopropyl]disulfanyl]propanoate Chemical compound SCC(S)COC(=O)CCSSCCC(=O)OCC(S)CS UQSCGTREKJYHOH-UHFFFAOYSA-N 0.000 description 1
- HLTWSPVMZDUPJH-UHFFFAOYSA-N 2,4-bis(sulfanyl)phenol Chemical compound OC1=CC=C(S)C=C1S HLTWSPVMZDUPJH-UHFFFAOYSA-N 0.000 description 1
- SXASCLUSQYBUFW-UHFFFAOYSA-N 2-(2-hydroxyethyldisulfanyl)ethanol 2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OCCSSCCO SXASCLUSQYBUFW-UHFFFAOYSA-N 0.000 description 1
- YTAFNCWRRKIZAV-UHFFFAOYSA-N 2-(2-hydroxyethyldisulfanyl)ethanol 3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.OCCSSCCO YTAFNCWRRKIZAV-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
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 description 1
- CQFQASKMKKPUKN-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.SCCOCCS CQFQASKMKKPUKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
- RDNOXVONDLWZCI-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanylmethylsulfanyl)ethanethiol Chemical compound SCCSCSCCS RDNOXVONDLWZCI-UHFFFAOYSA-N 0.000 description 1
- HAQZWTGSNCDKTK-UHFFFAOYSA-N 2-(3-sulfanylpropanoyloxy)ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOC(=O)CCS HAQZWTGSNCDKTK-UHFFFAOYSA-N 0.000 description 1
- UREAOTFLSRRYKQ-UHFFFAOYSA-N 2-(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical compound SCSCCSCS UREAOTFLSRRYKQ-UHFFFAOYSA-N 0.000 description 1
- YZIGUJRGKPNSGI-UHFFFAOYSA-N 2-[2,3-bis(2-sulfanylethyl)phenyl]ethanethiol Chemical compound SCCC1=CC=CC(CCS)=C1CCS YZIGUJRGKPNSGI-UHFFFAOYSA-N 0.000 description 1
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- AGLJIHAGINEOIR-UHFFFAOYSA-N [bis[bis(sulfanylmethylsulfanyl)methylsulfanyl]methylsulfanyl-(sulfanylmethylsulfanyl)methyl]sulfanylmethanethiol Chemical compound SCSC(SCS)SC(SC(SCS)SCS)SC(SCS)SCS AGLJIHAGINEOIR-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
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PPQNMKIMOCEJIR-UHFFFAOYSA-N benzene-1,2,3-trithiol Chemical compound SC1=CC=CC(S)=C1S PPQNMKIMOCEJIR-UHFFFAOYSA-N 0.000 description 1
- UKLXGHUHPLLTKD-UHFFFAOYSA-N benzene-1,2,4-trithiol Chemical compound SC1=CC=C(S)C(S)=C1 UKLXGHUHPLLTKD-UHFFFAOYSA-N 0.000 description 1
- KXCKKUIJCYNZAE-UHFFFAOYSA-N benzene-1,3,5-trithiol Chemical compound SC1=CC(S)=CC(S)=C1 KXCKKUIJCYNZAE-UHFFFAOYSA-N 0.000 description 1
- ZWOASCVFHSYHOB-UHFFFAOYSA-N benzene-1,3-dithiol Chemical compound SC1=CC=CC(S)=C1 ZWOASCVFHSYHOB-UHFFFAOYSA-N 0.000 description 1
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QWCNRESNZMCPJW-UHFFFAOYSA-N bis(sulfanylmethylsulfanyl)methylsulfanylmethanethiol Chemical compound SCSC(SCS)SCS QWCNRESNZMCPJW-UHFFFAOYSA-N 0.000 description 1
- QXTVJKYCVXUFLD-UHFFFAOYSA-N butane-1,2,4-trithiol Chemical compound SCCC(S)CS QXTVJKYCVXUFLD-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- YKRCKUBKOIVILO-UHFFFAOYSA-N cyclohexane-1,2-dithiol Chemical compound SC1CCCCC1S YKRCKUBKOIVILO-UHFFFAOYSA-N 0.000 description 1
- FWBXAOOHHILPSR-UHFFFAOYSA-N cyclohexylmethanethiol Chemical compound SCC1CCCCC1 FWBXAOOHHILPSR-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 1
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- IXBUFAUQDFHNGI-UHFFFAOYSA-N methylsulfanylmethanethiol Chemical compound CSCS IXBUFAUQDFHNGI-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229920005749 polyurethane resin Polymers 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
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- OOZWJYRXTAYWTJ-UHFFFAOYSA-N sulfanylmethylsulfanyl-[3-[3-(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanyl]propylsulfanylmethylsulfanylmethylsulfanyl]methanethiol Chemical compound SCSCCCSCSCCCSCSCSC(S)SCS OOZWJYRXTAYWTJ-UHFFFAOYSA-N 0.000 description 1
- WTSBJMAOQNCZBF-UHFFFAOYSA-N sulfanylmethylsulfanylmethanethiol Chemical compound SCSCS WTSBJMAOQNCZBF-UHFFFAOYSA-N 0.000 description 1
- QNITWMBGUWZSSI-UHFFFAOYSA-N sulfanylmethylsulfanylmethylsulfanylmethanethiol Chemical compound SCSCSCS QNITWMBGUWZSSI-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-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
- C08G18/30—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
-
- 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)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses an isocyanate composition and an optical resin prepared by using the composition. In the isocyanate composition, one or more of sodium, potassium, iron, chromium, manganese and nickel are contained in an amount of 1ppm or more and 50ppm or less based on isocyanate; preferably greater than 1ppm and less than or equal to 20ppm, the optical resin prepared has low incidence of optical deformation and cloudiness. Preferably, the isocyanate composition further comprises a complexing agent in an amount that provides excellent storage stability to the isocyanate.
Description
Technical Field
The present invention relates to the field of isocyanates, in particular to isocyanate compositions for optical resins, and also to the field of optical resins (lenses, etc.).
Background
Optical materials are widely used for producing optical elements such as spectacle lenses, windshields for airplanes and automobiles, window glass, lenses, prisms, and the like.
Among the optical resins, polyurethane resin is the most important one, and the resin is obtained by polymerization reaction of polythiol compound and isocyanate compound. Such an optical resin has high refractive index and is excellent in properties such as impact resistance, dyeability and processability. The polyurethane lens has a high refractive index, so that the lens can be made thinner and more attractive, and is a development trend of the later lens. M-xylylene diisocyanate (m-XDI) is a main raw material for polyurethane optical resins.
Among isocyanate compounds, since isocyanate groups have high reactivity, they tend to yellow or self-polymerize during storage, affecting downstream applications, and m-XDI has a benzene ring in the molecule, and is highly reactive, making it difficult to achieve long-term storage.
Representative of the isocyanate compound stabilizers at present are hindered phenols such as 2, 6-di-t-butyl-4-methylphenol (BHT) as isocyanate stabilizers disclosed in US patent No. 3715381, and carbon dioxide and sulfur dioxide as well as in US patent No. 3247236; also patent CN104718215 discloses that acid chlorides as stabilizers for silicon-containing isocyanates improve their storage stability.
However, the above stabilizers have poor stability to m-xylylene diisocyanate (m-XDI), and the isocyanate stabilizers used at present and the stabilizers disclosed in the above patents have difficulty in achieving stable storage of m-XDI at room temperature for more than 1 month.
Korean SKC patent CN108586705a reports that after the xylylene diisocyanate composition is sealed in a container and left at a temperature of 80 ℃ for 6 months, the total amount of materials (e.g., metals) eluted from the container may be within 1ppm, and more than 1ppm may deteriorate isocyanate.
However, even if the metal content is less than 1ppm, long-term storage of m-XDI cannot be achieved. Patents US5302749, US3743115, GB1192859, etc. report that m-XDI is prone to the formation of nylon-1 type polymers leading to haze degradation of the product.
In addition, in the polymerization process of the polyurethane lens, the influence of raw material deterioration often occurs, so that resin polymerization is uneven, the lens is opaque and optically deformed, and the quality of the lens is unqualified.
There is a need to control the raw materials and processes of lens polymerization, primarily isocyanate raw materials, to reduce the occurrence of blushing and optical distortion.
Disclosure of Invention
The invention aims to provide an isocyanate composition and an optical resin prepared by using the composition, and the occurrence rate of optical deformation and cloudiness of an optical resin lens can be reduced by controlling the content of sodium, potassium, iron, chromium, manganese and nickel elements of isocyanate. If the complexing agent is contained in a specific amount, the storage stability of isocyanate and the occurrence of optical deformation and cloudiness of the optical resin lens are excellent.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
the present invention provides an isocyanate composition and an optical resin using the same, wherein an isocyanate compound and a polythiol compound are mixed and polymerized to obtain the optical resin.
An isocyanate composition comprising an isocyanate and a metal element selected from one or more of sodium, potassium, iron, chromium, manganese and nickel, the metal element being contained in an amount of greater than 1ppm by weight and equal to or less than 50ppm by weight, preferably greater than 1ppm by weight and equal to or less than 20ppm by weight, based on the isocyanate.
The industrial production process of isocyanate inevitably contacts with metal materials such as stainless steel, and the like, so that partial metal elements are dissolved out, and the performance of the isocyanate is affected by the too high content of the metal elements, so that the content of the metal elements in the isocyanate is reduced.
The isocyanate used in the present invention is not particularly limited as long as it is a compound having 2 or more isocyanate groups in the molecule. For example, an aromatic ring-containing polyisocyanate compound, an aliphatic polyisocyanate compound, a alicyclic polyisocyanate compound, and the like can be cited.
Examples of the polyisocyanate compound having an aromatic ring include 1, 4-phenylene diisocyanate, methyl-1, 3-phenylene diisocyanate, 1, 3-di (isocyanatomethyl) benzene, mesitylene triisocyanate, 1, 3-di (2-isocyanatopropyl) benzene, 4.4 '-diphenylmethane diisocyanate, 2.4' -diphenylmethane diisocyanate, 1, 5-diisocyanate naphthalene, (3, 3 '-dimethyl-4, 4' -biphenyl) diisocyanate, and the like.
Examples of the aliphatic polyisocyanate compound include hexamethylene diisocyanate, lysine ester triisocyanate, and hexamethylene triisocyanate.
Examples of the polyisocyanate compound having an alicyclic structure include isophorone diisocyanate, di (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, di (isocyanatomethyl) bicycloheptane, tri (isocyanatomethyl) cyclohexane, and di (isocyanatomethyl) 1, 4-dithiane.
The polyisocyanate compounds may be used alone or in combination of 2 or more.
Preferably, the isocyanate according to the invention is selected from one or more of toluene diisocyanate, 4 '-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, 4' -dicyclohexylmethane diisocyanate, m-xylylene diisocyanate (m-XDI), p-xylylene diisocyanate (p-XDI), 1, 3-diisocyanatocyclohexane (m-HXDI), 1, 4-diisocyanatocyclohexane (p-HXDI).
Preferably, the isocyanate composition of the present invention further comprises a complexing agent, wherein the complexing agent is selected from one or more of organic carboxylic acid complexing agent and phosphoric acid complexing agent.
More preferably, the complexing agent comprises one or more of ethylenediamine tetraacetic acid (EDTA), isophthalic acid, tripolyphosphoric acid, dibutyl phosphate.
NCO is easy to form a nylon-1 type polymer in the m-XDI storage process to cause turbidity of a product, and it is found that a metal element in isocyanate and a complexing agent can be cooperated to capture free radicals, so that NCO is prevented from forming the nylon-1 type polymer, and the clarification time of an isocyanate product is prevented from being influenced, so that the isocyanate is stable in long-term storage.
The inventors have surprisingly found that in m-XDI, the presence of a metal element together with a complexing agent improves the storage stability of m-XDI. The complexing agent is used in an amount of greater than 1ppm by weight and less than or equal to 50ppm by weight, preferably greater than 1ppm by weight and less than or equal to 20ppm by weight, based on the weight of isocyanate.
As an alternative technical scheme, in the m-XDI, the metal element and the complexing agent can be the same or different in dosage.
A process for preparing the isocyanate composition of the present invention comprising the steps of: adding an optional complexing agent into the isocyanate crude product, and rectifying to control the content of metal elements and the complexing agent in the isocyanate. For example: adding excessive complexing agent for rectification to obtain isocyanate without metal element; rectifying without adding complexing agent to obtain isocyanate containing only metal elements.
An optical resin is prepared through mixing isocyanate composition with polythiol compound, and polymerizing.
The polythiol compound of the present invention is selected from the group consisting of methyl dithiol, 1, 2-ethanedithiol, 1-propanedithiol, 1, 2-propanedithiol, 1, 3-propanedithiol, 2-propanedithiol, 1, 6-hexanedithiol, 1,2, 3-propanetrithiol, 1-cyclohexanedithiol, 1, 2-cyclohexanedithiol, 2-dimethylpropane-1, 3-dithiol, 3, 4-dimethoxybutane-1, 2-dithiol, 2-methylcyclohexane-2, 3-dithiol, 1-bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl thiomalate), 2, 3-dimercapto-1-propanol (2-mercaptoacetate) 2, 3-dimercapto-1-propanol (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1, 2-dimercaptopropylmethyl ether, 2, 3-dimercaptopropylmethyl ether, 2-bis (mercaptomethyl) -1, 3-propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylol propane bis (2-mercaptoacetate), trimethylol propane bis (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), aliphatic polythiol compounds such as tetrakis (mercaptomethyl) methane;
1, 2-dimercaptobenzene, 1, 3-dimercaptobenzene, 1, 4-dimercaptobenzene, 1, 2-bis (mercaptomethyl) benzene, 1, 3-bis (mercaptomethyl) benzene, 1, 4-bis (mercaptomethyl) benzene, 1, 2-bis (mercaptoethyl) benzene, 1, 3-bis (mercaptoethyl) benzene, 1, 4-bis (mercaptoethyl) benzene, 1,2, 3-trismercaptobenzene, 1,2, 4-trismercaptobenzene, 1,3, 5-trismercaptobenzene, 1,2, 3-tris (mercaptomethyl) benzene, 1,2, 4-tris (mercaptomethyl) benzene, 1,3, 5-tris (mercaptomethyl) benzene, 1,2, 3-tris (mercaptoethyl) benzene, 1,2, 4-tris (mercaptoethyl) benzene, 1,3, 5-tris (mercaptoethyl) benzene, 2, 5-toluene dithiol, 3, 4-dithiol, 1, 3-bis (2, 3-diphenyl) propane, 2-diphenyl-dithiol, 2-diphenyl propane, 2-diphenyl-dithiol, poly (1, 2-diphenyl) propane, poly (mercapto-propane, etc.;
aromatic polythiol compounds having a sulfur atom other than a mercapto group, such as 1, 2-bis (mercaptoethylthio) benzene, 1, 3-bis (mercaptoethylthio) benzene, 1, 4-bis (mercaptoethylthio) benzene, 1,2, 3-tris (mercaptomethylthiothio) benzene, 1,2, 4-tris (mercaptomethylthiothio) benzene, 1,3, 5-tris (mercaptomethylthiothio) benzene, 1,2, 3-tris (mercaptoethylthio) benzene, 1,2, 4-tris (mercaptoethylthio) benzene, 1,3, 5-tris (mercaptoethylthio) benzene, and the like, and alkyls thereof;
bis (mercaptomethyl) sulfide, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) sulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropylthio) methane, 1, 2-bis (mercaptomethylthio) ethane, 1, 2-bis (2-mercaptoethylthio) ethane, 1, 2-bis (3-mercaptopropyl) ethane, 1, 3-bis (mercaptomethylthio) propane, 1, 3-bis (2-mercaptoethylthio) propane, 1, 3-bis (3-mercaptopropylthio) propane, 1,2, 3-tris (mercaptomethylthio) propane 1,2, 3-tris (2-mercaptoethylthio) propane, 1,2, 3-tris (3-mercaptopropylthio) propane, 1, 2-bis [ (2-mercaptoethyl) thio ] -3-mercaptopropane, 4, 8-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane, 4, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane, 5, 7-dimercaptomethyl-1, 11-dimercapto-3, 6, 9-trithiaundecane, bis (mercaptomethyl) -3,6, 9-trithio-1, 11-undecanedithiol, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, aliphatic polythiol compounds having a sulfur atom other than a mercapto group such as tetrakis (3-mercaptopropylthiomethyl) methane, bis (2, 3-dimercaptopropyl) sulfide, bis (1, 3-dimercaptopropyl) sulfide, 2, 5-dimercapto-1, 4-dithiane, 2, 5-dimercaptomethyl-2, 5-dimethyl-1, 4-dithiane, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) disulfide, and esters of mercaptoacetic acid and mercaptopropionic acid thereof;
hydroxymethyl thioether bis (2-mercaptoacetate), hydroxymethyl thioether bis (3-mercaptopropionate), hydroxyethyl thioether bis (2-mercaptoacetate), hydroxyethyl thioether bis (3-mercaptopropionate), hydroxypropyl thioether bis (2-mercaptoacetate), hydroxypropyl thioether bis (3-mercaptopropionate), hydroxymethyl disulfide bis (2-mercaptoacetate), hydroxymethyl disulfide bis (3-mercaptopropionate), hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide bis (3-mercaptopropionate), hydroxypropyl disulfide bis (2-mercaptoacetate), hydroxypropyl disulfide bis (3-mercaptopropionate), 2-mercaptoethyl ether bis (2-mercaptoacetate), 2-mercaptoethyl ether bis (3-mercaptopropionate), 1, 4-dithiane-2, 5-diol bis (2-mercaptoacetate), 1, 4-dithiane-2, 5-diol bis (3-mercaptopropionate), ethylene disulfide bis (2-mercaptoacetate), ethylene disulfide bis (2-mercaptopropionate), diethyl disulfide bis (2-mercaptopropionate), aliphatic polythiol compounds having a sulfur atom and an ester bond in addition to a mercapto group, such as bis (2-mercaptoethyl) 4, 4-dithiodibutyrate, bis (2, 3-dimercaptopropyl) thionodipropionate, bis (2, 3-dimercaptopropyl) dithiodiacetate, and bis (2, 3-dimercaptopropyl) dithiodipropionate;
heterocyclic compounds containing a sulfur atom in addition to a mercapto group, such as 3, 4-thiophenedichiol and 2, 5-dimercapto-1, 3, 4-thiodiazole;
compounds containing a hydroxyl group other than a mercapto group, such as 2-mercaptoethanol, 3-mercapto-1, 2-propanediol, glycerol bis (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2, 4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3, 4-dimercapto-2-propanol, 1, 3-dimercapto-2-propanol, 2, 3-dimercapto-1-propanol, 1, 2-dimercapto-1, 3-butanediol, pentaerythritol tris (3-mercaptopropionate), pentaerythritol mono (3-mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (mercaptoacetate), dipentaerythritol penta (3-mercaptopropionate), hydroxymethyl-tris (mercaptoethylthiomethyl) methane, and 1-hydroxyethylthio-3-mercaptoethylthio benzene;
1, 3-tetra (mercaptomethylthio) propane, 1, 2-tetra (mercaptomethylthio) ethane, 4, 6-bis (mercaptomethylthio) -1, 3-dithiane 1, 5-tetra (mercaptomethylthio) -3-thiapentane, 1, 6-tetra (mercaptomethylthio) -3, 4-dithio-hexane 2, 2-bis (mercaptomethylthio) ethanethiol, 2- (4, 5-dimercapto-2-thiapentyl) -1, 3-dithiolane, 2-bis (mercaptomethyl) -1, 3-dithiolane, 2, 5-bis (4, 4-bis (mercaptomethylthio) -2-thiabutyl) -1, 4-dithiane 2, 2-bis (mercaptomethylthio) -1, 3-propane dithiol, 3-mercaptomethylthio-1, 7-dimercapto-2, 6-dithioheptane, 3, 6-bis (mercaptomethylthio) -1, 9-dimercapto-2, 5, 8-trithianonane, 4, 6-bis (mercaptomethylthio) -1, 9-dimercapto-2, 5, 8-trithianonane, 3-mercaptomethylthio-1, 6-dimercapto-2, 5-dithiohexane, 2- (2, 2-bis (mercaptomethylthio) ethyl) -1, 3-dithiocyclobutane, 1,1,9,9-tetrakis (mercaptomethylthio) -5- (3, 3-bis (mercaptomethylthio) -1-thiopropyl) 3, 7-dithiononane, tris (2, 2-bis (mercaptomethylthio) ethyl) methane, tris (4, 4-bis (mercaptomethylthio) -2-thiobutyl) methane, tetrakis (2, 2-bis (mercaptomethylthio) ethyl) methane, tetrakis (4, 4-bis (mercaptomethylthio) -2-thiobutyl) methane, 3,5,9,11-tetrakis (mercaptomethylthio) -1, 13-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexa (mercaptomethylthio) -1, 19-dimercapto-2,6,8,12,14,18-hexa-nonadecane, 9- (2, 2-bis (mercaptomethylthio) ethyl) -3,5,13,15-tetrakis (mercaptomethylthio) -1, 17-dimercapto-2,6,8,10,12,16-hexaheptadecane, 3,4,8, 9-tetrakis (mercaptomethylthio) -1, 11-dimercapto-2, 5,7, 10-tetrathiaundecane, 3,4,8,9,13,14-hexa (mercaptomethylthio) -1, 16-hexamercapto-3, 6-dimercapto-pentadecane-1, 17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3,4,8, 9-tetrakis (mercaptomethylthio) -1, 11-dimercapto-2, 5,7, 10-tetrathiaundecane, 3,4,8,9,13,14-hexa (mercapto) -1, 16-dimercapto-hexamercapto-3, 3-bis (mercaptomethylthio) -3, 3-dimercapto-pentadecane-6-dimercapto-3-methyltetramercapto-3-6-dimercapto-pentadecane 4- {3, 5-bis (mercaptomethylthio) -7-mercapto-2, 6-dithiaheptylthio } -6-mercaptomethylthio-1, 3-dithiane, 1-bis {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -3, 3-bis (mercaptomethylthio) propane, 1, 3-bis {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -1, 3-bis (mercaptomethylthio) propane, 1- {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -3- {2, 2-bis (mercaptomethylthio) ethyl } -7, 9-bis (mercaptomethylthio) -2,4,6, 10-tetrathiaundecane 1- {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -3- {2- (1, 3-dithiacyclobutyl) } methyl-7, 9-bis (mercaptomethylthio) -2,4,6, 10-tetrathiaundecane, 1, 5-bis {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -3- {2- (1, 3-dithiabutylyl) } methyl-2, 4-dithiapentane, 4, 6-bis [3- {2- (1, 3-dithiabutylyl) } methyl-5-mercapto-2, 4-dithiapentylthio ] -1, 3-dithiane, 4, 6-bis {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -1, 3-dithiane, 4- {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -6- {4- (6-mercaptomethylthio) -1, 3-dithiaalkylthio } -1, 3-dithiane, 3- {2- (1, 3-dithiacyclobutyl) } methyl-7, 9-bis (mercaptomethylthio) -1, 11-dimercapto-2, 4,6, 10-tetrathiaundecane, 9- {2- (1, 3-dithiacyclobutyl) } methyl-3,5,13,15-tetrakis (mercaptomethylthio) -1, 17-dimercapto-2,6,8,10,12,16-hexaheptadecane 3- {2- (1, 3-dithiacyclobutyl) } methyl-7,9,13,15-tetrakis (mercaptomethylthio) -1, 17-dimercapto-2,4,6,10,12,16-hexathiaheptadecane, 3, 7-bis {2- (1, 3-dithiabutylyl) } methyl-1, 9-dimercapto-2, 4,6, 8-tetrathianonane, 4- {3,4,8, 9-tetrakis (mercaptomethylthio) -11-mercapto-2, 5,7, 10-tetrathiaundecyl } -5-mercaptomethylthio-1, 3-dithiacyclopentane, 4, 5-bis {3, 4-bis (mercaptomethylthio) -6-mercapto-2, 5-dithiahexylthio } -1, 3-dithiacyclopentane, 4- {3, 4-bis (mercaptomethylthio) -6-mercapto-2, 5-dithiohexylthio } -5-mercaptomethylthio-1, 3-dithiolane, 4- { 3-bis (mercaptomethylthio) -methyl-5, 6-bis (mercaptomethylthio) -8-mercapto-2, 4, 7-trithiooctyl } -5-mercaptomethylthio-1, 3-dithiolane, 2- [ bis {3, 4-bis (mercaptomethylthio) -6-mercapto-2, 5-dithiohexylthio } methyl ] -1, 3-dithiocyclobutane, 2- {3, 4-bis (mercaptomethylthio) -6-mercapto-2, 5-dithiohexylthio } mercaptomethylthiomethyl-1, 3-dithiocyclobutane 2- {3,4,8, 9-tetra (mercaptomethylthio) -11-mercapto-2, 5,7, 10-tetrathiaundecylthio } mercaptomethylthiomethyl-1, 3-dithio-tane, 2- { 3-bis (mercaptomethylthio) methyl-5, 6-bis (mercaptomethylthio) -8-mercapto-2, 4, 7-trithiooctyl } mercaptomethylthiomethyl-1, 3-dithio-tane, 4, 5-bis [1- {2- (1, 3-dithio-butyl) } -3-mercapto-2-thi-propylthio ] -1, 3-dithio-lane, 4- [1- {2- (1, 3-dithiol-butyl) } -3-mercapto-2-thiiranyl ] -5- {1, 2-bis (mercapto-methylthio) -4-mercapto-3-thiobutanethiol } -1, 3-dithiolane, 2- [ bis {4- (5-mercapto-1, 3-dithiolane) thio ] methyl-1, 3-dithiolane, 4- {4- (5-mercapto-methylthio-1, 3-dithiolane) thio } -5- [1- {2- (1, 3-dithiol-butyl) } -3-mercapto-2-thiiranyl ] -1, 3-dithiolane, their oligomers and the like compounds having a dithioacetal (dithioacetal) or dithioketal (dithioketal) backbone;
tris (mercaptomethylthio) methane, tris (mercaptoethylthio) methane, 1, 5-tetrakis (mercaptomethylthio) -2, 4-dithiolane, bis (4, 4-bis (mercaptomethylthio) -1, 3-dithiobutyl) (mercaptomethylthio) methane, tris (4, 4-bis (mercaptomethylthio) -1, 3-dithiobutyl) methane, 2,4, 6-tris (mercaptomethylthio) -1,3, 5-trithiocyclohexane, 2, 4-bis (mercaptomethylthio) -1,3, 5-trithiocyclohexane, 1, 3-tetrakis (mercaptomethylthio) -2-thiopropane, bis (mercaptomethyl) methylthio-1, 3, 5-trithiocyclohexane tris ((4-mercaptomethyl-2, 5-dithiocyclohexyl-1-yl) methylthio) methane, 2, 4-bis (mercaptomethylthio) -1, 3-dithiolane, 2-mercaptoethylthio-4-mercaptomethyl-1, 3-dithiolane, 2- (2, 3-dimercaptopropylthio) -1, 3-dithiolane, 4-mercaptomethyl-2- (1, 3-dimercapto-2-propylthio) -1, 3-dithiolane, tris (2, 2-bis (mercaptomethylthio) -1-thiaethyl) methane, compounds having a trithio-orthoformate (ortho trithioformate) skeleton such as tris (3, 3-bis (mercaptomethylthio) -2-thiapropyl) methane, tris (4, 4-bis (mercaptomethylthio) -3-thiabutyl) methane, 2,4, 6-tris (3, 3-bis (mercaptomethylthio) -2-thiapropyl) -1,3, 5-trithiocyclohexane, tetrakis (3, 3-bis (mercaptomethylthio) -2-thiapropyl) methane, and oligomers thereof;
compounds having a tetrathiocarbonate skeleton such as 3,3 '-bis (mercaptomethylthio) -1, 5-dimercapto-2, 4-dithiolane, 2' -bis (mercaptomethylthio) -1, 3-dithiolane, 2, 7-bis (mercaptomethyl) -1,4,5,9-tetrathiaspiro [4,4] nonane, 3, 9-dimercapto-1,5,7,11-tetrathiaspiro [5,5] undecane, and oligomers thereof.
However, the polythiol compound is not limited to the above-mentioned compounds. The above-mentioned compounds may be used alone or in combination of 2 or more.
Of the above-mentioned compounds, at least 1 polythiol compound selected from the group consisting of 1, 2-bis [ (2-mercaptoethyl) thio ] -3-mercaptopropane, bis (mercaptomethyl) -3,6, 9-trithia-1, 11-undecanedithiol, pentaerythritol tetrakis (3-mercaptopropionate), 1, 3-tetrakis (mercaptomethylthio) propane and 2-mercaptoethanol is particularly preferably used.
Preferably, the method for producing the optical resin is carried out in the presence of a polymerization catalyst, and the polymerization catalyst is preferably an organotin compound, and examples thereof include dialkyltin halides (dialkyltin halide) such as dibutyltin dichloride and dimethyltin dichloride; tin dialkyldicarboxylates such as dimethyldiacetate, dibutyltin dioctanoate, dibutyltin dilaurate and the like.
In the above-mentioned method for producing an optical resin, various additives such as a chain extender, a crosslinking agent, a light stabilizer, an ultraviolet absorber, an antioxidant, an oil-soluble dye, a filler, and a mold release agent are optionally added according to the purpose.
Optical materials formed from polyurethane-based resins are generally manufactured by injection polymerization. Specifically, a polythiol compound and an isocyanate compound are mixed, and a suitable auxiliary agent is optionally added. When necessary, the mixed solution (polymerizable composition) is defoamed by an appropriate method, and then injected into an injection mold for an optical material, and is usually heated gradually from a low temperature to a high temperature to polymerize. Then, the optical material is obtained by demolding.
A lens made of the optical resin according to the present invention.
The technical scheme of the invention has the following beneficial effects:
according to the invention, the optical resin lens prepared from isocyanate with the content of metal elements (one or more of sodium, potassium, iron, chromium, manganese and nickel) being more than 1ppm and less than or equal to 20ppm has optical deformation and occurrence rate of white turbidity being less than 2%, the content of metal elements (one or more of sodium, potassium, iron, chromium, manganese and nickel) being more than 1ppm and less than or equal to 20ppm, and m-XDI with the content of complexing agent being more than 1ppm and less than or equal to 20ppm can be stably stored for more than 6 months.
According to the invention, the m-HXDI with the content of metal elements (one or more of sodium, potassium, iron, chromium, manganese and nickel elements) being more than 1ppm and less than or equal to 20ppm and the content of complexing agent being more than 1ppm and less than or equal to 20ppm can be stably stored for more than 6 months, the optical deformation and the occurrence rate of white turbidity of the prepared optical resin lens are less than 2%,
the optical material of the present invention is characterized by little optical distortion or cloudiness. That is, the optical material of the present invention is characterized by excellent properties and can be manufactured with good yield.
Detailed Description
The invention will be further illustrated with reference to the following examples, which are not intended to limit the same.
The optical material is prepared by polymerizing a polythiol compound and an isocyanate compound under the action of a catalyst, and necessary components such as an internal mold release agent, a UV absorber and the like are also required to be added. The lens is manufactured by injecting the polymer into a lens mold and polymerizing.
The content of sodium, potassium, iron, chromium, manganese and nickel elements in m-XDI or m-HXDI is determined by ICP-OES analysis;
instrument: thermo Scientific ICAP 7200ICP-OES
The complexing agent is determined by liquid chromatography
Instrument: agilent 1260
Incidence of optical deformation: the optical strain is a phenomenon in which the local refractive index is different from the surrounding normal refractive index due to the difference in resin composition or the like. 100 lenses were visually observed under a high-pressure mercury lamp, and the occurrence of optical strain was calculated by confirming that the lenses having a stripe shape were judged to have optical strain.
Occurrence rate of white turbidity: 100 lenses were visually observed under a high-pressure mercury lamp, and the occurrence of cloudiness was calculated by confirming that the cloudiness was judged as a cloudiness-containing lens.
Polymerization rate: the evaluation was performed using the viscosity after 5 hours as an index, which was 0 hours when the polymerizable composition was prepared.
Viscosity testing was performed using a Brookfiled rotor viscometer.
Example 1
Preparation of m-xylylene diisocyanate (m-XDI)
In a stainless steel reaction kettle, 1360g of m-xylylenediamine is dissolved in 12240g of o-dichlorobenzene, hydrogen chloride gas is introduced at the rate of 1000L/h for salifying reaction, the temperature is controlled to be less than 30 ℃, milky sticky matters are obtained after salifying is finished, the temperature is raised to 150 ℃, phosgene is introduced at the rate of 500L/h for photochemical reaction, and unreacted phosgene is condensed and recovered and then enters an alkaline washing system for destruction. After the reaction liquid is clarified, the photochemical reaction is completed, nitrogen is introduced to expel unreacted phosgene, and the solvent is removed subsequently, so that a crude product of m-xylylene diisocyanate is obtained.
Next, a glass rectifying tower with an inner diameter of 20mm and a length of 1500mm and filled with regular fillers is used for rectifying the obtained crude product of the m-xylylene diisocyanate, 100ppm of complexing agent is added into the crude product of the m-xylylene diisocyanate in advance, the crude product of the m-xylylene diisocyanate is preheated to 120 ℃ by a preheater, then is fed from the middle part of the rectifying tower, the absolute pressure of the tower top is 100pa, the temperature of the tower bottom reboiler is 155 ℃, the temperature of the tower top is 120 ℃, the reflux ratio is controlled to be 10:1, and the product is taken out from the tower top after reaching a stable state. The content of sodium, potassium, iron, chromium, manganese and nickel and the content of complexing agent in the product are analyzed, the initial color number is less than 5hazen, and the product is clear and transparent by visual observation.
The m-XDI product was stored in 1000mL aluminum bottles, protected with nitrogen, stored at 20℃and color numbers were measured every other week to determine visual turbidity.
Lens preparation
52. 52g m-XDI, 0.015g of dibutyltin dichloride as a catalyst, 0.10g of an acid phosphate (Stepan, trade name Zelec UN) and 0.05g of an ultraviolet absorber (co-produced by Kogyo Co., ltd., trade name BioSorb 583) were mixed and dissolved at 25 ℃. Then, 48g of 1, 2-bis [ (2-mercaptoethyl) thio ] -3-mercaptopropane (Beijing Bo chemical industry, mixing them to form a homogeneous solution (polymerizable composition)) was added, and the viscosity after 5 hours was measured to prepare a homogeneous solution for 0 hour.
52. 52g m-XDI, 0.015g of dibutyltin dichloride as a catalyst, 0.10g of an acid phosphate (Stepan, trade name Zelec UN) and 0.05g of an ultraviolet absorber (co-produced by Kogyo Co., ltd., trade name BioSorb 583) were mixed and dissolved at 25 ℃. Then, 48g of 1, 2-bis [ (2-mercaptoethyl) thio ] -3-mercaptopropane was added and mixed to form a homogeneous liquid (polymerizable composition). The homogeneous mixture was deaerated at 600Pa for 1 hour, and then filtered through a 1 μm PTFE (polytetrafluoroethylene) filter. Then, the mixture was injected into an injection mold for lenses, which was composed of a 4D glass mold having a diameter of 75mm and an adhesive tape. The injection mold was placed in an oven and held at 40℃for 2 hours, heated to 50℃for 2 hours over 4 hours, and heated to 60℃for 2 hours over 3 hours. The temperature was raised to 70℃for 2 hours over 3 hours, to 100℃over 3 hours, and then to 130℃for 2 hours over 1 hour. After the polymerization, the injection mold was taken out of the oven, and the lens was obtained by demolding. The resulting lenses were annealed at 120℃for a further 3 hours. 100 lenses were produced in the same manner, and the occurrence rate of striae and the occurrence rate of cloudiness were calculated.
The conditions and results are shown in Table 1.
Examples 2 to 5, comparative examples 1 to 3
And respectively obtaining m-xylylene diisocyanate containing different contents of sodium, potassium, iron, chromium, manganese and nickel and the complexing agent content by changing the pre-added complexing agent amount and controlling the reflux ratio, and analyzing the contents of metal elements and the complexing agent in corresponding products. The initial color number is less than 5hazen, and the color is clear and transparent by visual observation.
The corresponding m-XDI product was stored in 1000mL aluminum bottles, nitrogen-protected, stored at 20℃and color number was measured every other week, and visual turbidity was observed.
In addition, the product properties in the preparation of lenses were separately tested according to the method of example 1.
The conditions and results are shown in Table 1.
TABLE 1 conditions and results for examples 1-5 and comparative examples 1-3
Example 6
m-HXDI preparation
In a stainless steel reaction kettle, 1420g of 1, 3-dimethylamino cyclohexane is dissolved in 12240g of o-dichlorobenzene, hydrogen chloride gas is introduced at the rate of 1000L/h for salifying reaction, the temperature is controlled to be less than 30 ℃, after salifying is finished, milky sticky matter is obtained, the temperature is raised to 150 ℃, phosgene is introduced at the rate of 500L/h for photochemical reaction, and unreacted phosgene is condensed and recovered and then enters an alkaline washing system for destruction. After the reaction liquid is clarified, the photochemical reaction is completed, nitrogen is introduced to expel unreacted phosgene, and the solvent is removed subsequently, so that a crude product of 1, 3-methyl diisocyanate cyclohexane is obtained.
Next, the obtained crude m-xylylene diisocyanate was rectified using a glass rectifying column filled with a regular packing material having an inner diameter of 20mm and a length of 1500mm, 100ppm of a complexing agent was previously added to the crude 1, 3-diisocyanatomethyl cyclohexane, the crude 1, 3-diisocyanatomethyl cyclohexane was preheated to 120 ℃ by a preheater, and then fed from the middle of the rectifying column, the operating pressure of the column top was 100pa, the reboiler temperature of the column bottom was 154 ℃, the temperature of the column top was 115 ℃, the reflux ratio was controlled at 10:1, and after reaching a steady state, the product was recovered from the column top. The content of sodium, potassium, iron, chromium, manganese and nickel and the content of complexing agent in the product are analyzed, the initial color number is less than 5hazen, and the product is clear and transparent by visual observation.
The m-HXDI product was stored in 1000mL aluminum bottles, protected with nitrogen, stored at 20℃and color numbers were measured every other week to determine visual turbidity.
Lens preparation
53.7. 53.7g m-HXDI, 0.075g of dibutyltin dichloride as a catalyst, 0.10g of acid phosphate (Stepan, trade name Zelec UN) and 0.05g of an ultraviolet absorber (co-produced by Co-pharmaceutical Co., ltd., trade name BioSorb 583) were mixed and dissolved at 25 ℃. Further, 48g of 1, 2-bis [ (2-mercaptoethyl) thio ] -3-mercaptopropane (Peking chemical industry) was added and mixed to form a homogeneous liquid (polymerizable composition). The viscosity after 5 hours was measured at 0 hour when a homogeneous solution was prepared.
53.7. 53.7g m-HXDI, 0.075g of dibutyltin dichloride as a catalyst, 0.10g of acid phosphate (Stepan, trade name Zelec UN) and 0.05g of an ultraviolet absorber (co-produced by Co-pharmaceutical Co., ltd., trade name BioSorb 583) were mixed and dissolved at 25 ℃. Further, 48g of 1, 2-bis [ (2-mercaptoethyl) thio ] -3-mercaptopropane (Peking chemical industry) was added and mixed to form a homogeneous liquid (polymerizable composition). The homogeneous mixture was deaerated at 600Pa for 1 hour, and then filtered through a 1 μm PTFE (polytetrafluoroethylene) filter. Then, the mixture was injected into an injection mold for lenses, which was composed of a 4D glass mold having a diameter of 75mm and an adhesive tape. The injection mold was placed in an oven and held at 40℃for 2 hours, heated to 50℃for 2 hours over 4 hours, and heated to 60℃for 2 hours over 3 hours. The temperature was raised to 70℃for 2 hours over 3 hours, to 100℃over 3 hours, and to 130℃over 1 hour for 2 hours. After the polymerization, the injection mold was taken out of the oven, and the lens was obtained by demolding. The resulting lenses were annealed at 120℃for a further 3 hours. 100 lenses were produced in the same manner, and the occurrence rate of striae and the occurrence rate of cloudiness were calculated.
The conditions and results are shown in Table 2.
Examples 7 to 10, comparative examples 4 and 5
And respectively obtaining m-HXDI containing different contents of sodium, potassium, iron, chromium, manganese and nickel and the complexing agent by changing the dosage of the complexing agent added in advance and controlling the proportion of reflux, and analyzing the contents of metal elements and the complexing agent in corresponding products. The initial color number is less than 5hazen, and the color is clear and transparent by visual observation.
The m-HXDI product was stored in 1000mL aluminum bottles, protected with nitrogen, stored at 20℃and color numbers were measured every other week to determine visual turbidity.
In addition, the product properties in the lens preparation were separately tested according to the method of example 6.
The conditions and results are shown in Table 2.
TABLE 2 conditions and results for examples 6-10 and comparative examples 4,5
From the above data, it is found that the occurrence of optical distortion and cloudiness of the lens obtained by using isocyanate having a metal element content of not less than 1ppm and not more than 20ppm is less than 2%. The optical deformation and the occurrence rate of the white turbidity of the lens obtained by isocyanate with higher or lower metal element content are greatly improved.
It is known that the polymerization rate of isocyanate and polythiol has a large influence on the lens resin, and if the polymerization rate is too high, the resin is optically deformed and air bubbles are generated, and if the polymerization rate is too low, the resin is easily caused to be opaque and cloudy. The inventor surprisingly found that the content of sodium, potassium, iron, chromium, manganese and nickel elements in isocyanate has a great influence on the polymerization rate, and the lens resin with good transparency and low incidence of optical deformation and white turbidity can be obtained by controlling the content of sodium, potassium, iron, chromium, manganese and nickel elements in isocyanate to a certain level.
In addition, a certain content of metal element in m-XDI forms a complex with a complexing agent to improve the storage stability.
Claims (3)
1. An isocyanate composition comprising an isocyanate, a metal element and a complexing agent, the metal element being one or more selected from the group consisting of sodium, potassium, iron, chromium, manganese and nickel, the metal element being present in an amount of greater than 1ppm by weight and 20ppm by weight or less based on the isocyanate; the complexing agent comprises ethylenediamine tetraacetic acid and/or isophthalic acid; the isocyanate is selected from one or more of toluene diisocyanate, 4 '-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, 4' -dicyclohexylmethane diisocyanate, terephthalene diisocyanate, 1, 3-diisocyanatocyclohexane and 1, 4-diisocyanatocyclohexane.
2. A process for preparing the isocyanate composition of claim 1 comprising the steps of: adding complexing agent into the isocyanate crude product, rectifying, and controlling the contents of metal elements and complexing agent in the isocyanate.
3. An optical resin prepared from the isocyanate composition of claim 1.
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CN107428897A (en) * | 2015-03-12 | 2017-12-01 | 豪雅镜片泰国有限公司 | Different (sulphur) cyanate compositions and the optical component resin combination using it |
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