JP2021092776A - ジイソシアネート組成物および光学レンズの製造方法 - Google Patents
ジイソシアネート組成物および光学レンズの製造方法 Download PDFInfo
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- JP2021092776A JP2021092776A JP2020202276A JP2020202276A JP2021092776A JP 2021092776 A JP2021092776 A JP 2021092776A JP 2020202276 A JP2020202276 A JP 2020202276A JP 2020202276 A JP2020202276 A JP 2020202276A JP 2021092776 A JP2021092776 A JP 2021092776A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- diisocyanate
- diamine hydrochloride
- diamine
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 250
- 125000005442 diisocyanate group Chemical group 0.000 title claims abstract description 131
- 238000000034 method Methods 0.000 title claims abstract description 65
- 230000003287 optical effect Effects 0.000 title claims abstract description 55
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims abstract description 125
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 119
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract description 58
- 150000004985 diamines Chemical class 0.000 claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims description 119
- 238000004821 distillation Methods 0.000 claims description 36
- 150000002500 ions Chemical class 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 15
- 238000002834 transmittance Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 11
- 150000003553 thiiranes Chemical class 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 31
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 24
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 13
- 239000012948 isocyanate Substances 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 10
- 150000002513 isocyanates Chemical class 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 9
- 239000007787 solid Substances 0.000 abstract description 9
- 150000001412 amines Chemical class 0.000 abstract description 7
- 239000004033 plastic Substances 0.000 abstract description 5
- 239000012467 final product Substances 0.000 abstract description 3
- 239000010419 fine particle Substances 0.000 abstract description 3
- 238000013019 agitation Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 86
- 239000003960 organic solvent Substances 0.000 description 58
- 238000003756 stirring Methods 0.000 description 33
- -1 amine hydrochloride Chemical class 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000001816 cooling Methods 0.000 description 15
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 14
- 239000003990 capacitor Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 150000003573 thiols Chemical class 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000007790 solid phase Substances 0.000 description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 8
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000006839 xylylene group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 5
- FHKVBKRABWGIMY-UHFFFAOYSA-M benzyl(trimethyl)azanium;methyl carbonate Chemical compound COC([O-])=O.C[N+](C)(C)CC1=CC=CC=C1 FHKVBKRABWGIMY-UHFFFAOYSA-M 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000005587 bubbling Effects 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 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 5
- 238000005259 measurement Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000013557 residual solvent Substances 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- PSNBALLUTKSQPQ-UHFFFAOYSA-N ethylbenzene;isocyanic acid Chemical compound N=C=O.CCC1=CC=CC=C1 PSNBALLUTKSQPQ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- XKXKKCYHCIGWJG-UHFFFAOYSA-N (2-chloro-1-isocyanatoethyl)benzene Chemical compound O=C=NC(CCl)C1=CC=CC=C1 XKXKKCYHCIGWJG-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- GRJWOKACBGZOKT-UHFFFAOYSA-N 1,3-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC(CCl)=C1 GRJWOKACBGZOKT-UHFFFAOYSA-N 0.000 description 2
- MTZVWTOVHGKLOX-UHFFFAOYSA-N 2,2-bis(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)(CS)CS MTZVWTOVHGKLOX-UHFFFAOYSA-N 0.000 description 2
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 2
- NQLQMVQEQFIDQB-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)propane-1,3-dithiol Chemical compound SCCSC(CS)CS NQLQMVQEQFIDQB-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- LADVLFVCTCHOAI-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.CC1=CC=CC=C1 LADVLFVCTCHOAI-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000005068 thioepoxy group Chemical group S(O*)* 0.000 description 2
- STQMMGQDGYHHII-UHFFFAOYSA-N xi-1-(Propylthio)-1-propanethiol Chemical compound CCCSC(S)CC STQMMGQDGYHHII-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- KPLNSCKRXRCEIQ-TXEJJXNPSA-N (2r)-2-(2-sulfanylethylsulfanyl)-3-[2-[(2s)-3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylethylsulfanyl]propane-1-thiol Chemical compound SCCS[C@@H](CS)CSCCSC[C@@H](CS)SCCS KPLNSCKRXRCEIQ-TXEJJXNPSA-N 0.000 description 1
- 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
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BTMPBHHAYWOBBL-UHFFFAOYSA-N 1-(aminomethylsulfanyl)ethylsulfanylmethanamine Chemical compound NCSC(C)SCN BTMPBHHAYWOBBL-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- JJSCUXAFAJEQGB-UHFFFAOYSA-N 1-isocyanatoethylbenzene Chemical compound O=C=NC(C)C1=CC=CC=C1 JJSCUXAFAJEQGB-UHFFFAOYSA-N 0.000 description 1
- MOFBDJIQKHNGPG-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,1-diamine Chemical compound CCC(C)CC(C)(C)C(N)N MOFBDJIQKHNGPG-UHFFFAOYSA-N 0.000 description 1
- WBIGZXWZARXXBI-UHFFFAOYSA-N 2,2-dimethylpentane-1,1-diamine Chemical compound CCCC(C)(C)C(N)N WBIGZXWZARXXBI-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- JONTXEXBTWSUKE-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)ethanamine Chemical compound NCCSCCN JONTXEXBTWSUKE-UHFFFAOYSA-N 0.000 description 1
- KJNRRILYMLFXMY-UHFFFAOYSA-N 2-(2-aminoethylsulfanylmethylsulfanyl)ethanamine Chemical compound NCCSCSCCN KJNRRILYMLFXMY-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
- BXOMQXHMKABUEI-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)-3-[4-[2-[4-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propoxy]phenyl]propan-2-yl]phenoxy]propane-1-thiol Chemical compound C=1C=C(OCC(CS)SCCS)C=CC=1C(C)(C)C1=CC=C(OCC(CS)SCCS)C=C1 BXOMQXHMKABUEI-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- NZHJAPBLGJCOFV-UHFFFAOYSA-N 2-[1-(2-aminoethylsulfanyl)ethylsulfanyl]ethanamine Chemical compound NCCSC(C)SCCN NZHJAPBLGJCOFV-UHFFFAOYSA-N 0.000 description 1
- QTEWPHJCEXIMRJ-UHFFFAOYSA-N 2-[2,3-bis(2-sulfanylethylsulfanyl)propylsulfanyl]ethanethiol Chemical compound SCCSCC(SCCS)CSCCS QTEWPHJCEXIMRJ-UHFFFAOYSA-N 0.000 description 1
- VYZPXGMSAOCYOL-UHFFFAOYSA-N 2-[2-(2-aminoethyl)phenyl]ethanamine Chemical compound NCCC1=CC=CC=C1CCN VYZPXGMSAOCYOL-UHFFFAOYSA-N 0.000 description 1
- SLQDZZGEPQYECP-UHFFFAOYSA-N 2-[2-(thiiran-2-ylmethylsulfanyl)ethylsulfanylmethyl]thiirane Chemical compound C1SC1CSCCSCC1CS1 SLQDZZGEPQYECP-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
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- C07C265/00—Derivatives of isocyanic acid
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- 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
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Abstract
Description
一実現例によるジイソシアネート組成物の調製方法は、(1)ジアミン組成物を塩酸水溶液と反応させてジアミン塩酸塩組成物を得る段階と、(2)前記ジアミン塩酸塩組成物をトリホスゲンと反応させてジイソシアネート組成物を得る段階とを含み、前記ジイソシアネート組成物がCIE色座標による0.1〜2.0のb*値を有する。
以下、各段階別に具体的に説明する。
まず、ジアミンを塩酸水溶液と反応させ、ジアミン塩酸塩組成物を得る。
このようなジアミン塩酸塩の調製過程において、ジアミンの高い反応性およびpHによる温度および湿度に起因して容易に変質されることによって、ジアミン塩酸塩組成物のCIE色座標によるb*値が上昇し得る。特に、一定のレベル以上のb*値を有するジアミン塩酸塩組成物を利用して、ジイソシアネート組成物を調製する場合、色およびヘイズが低下し、最終的な光学レンズの脈理、透過率、黄色度および屈折率にも影響を与え得る。また、変色したジイソシアネート組成物を無色透明に変化させるために数回の蒸留を実施する場合、収率の損失に起因する経済性の低下を引き起こし得る。
次に、前記ジアミン塩酸塩組成物をトリホスゲンと反応させてジイソシアネート組成物を得る。この際、前記ジアミン塩酸塩組成物とトリホスゲンとの反応は、第2有機溶媒中で行われ得る。
前記反応により得られた結果物は、分離、脱気、ろ過、蒸留などをさらに経ても良い。
このようなジアミン塩酸塩組成物およびトリホスゲンを利用して調製されたジイソシアネート組成物は、色とヘイズが改善され得る。
前記ジアミン塩酸塩組成物およびトリホスゲンからジイソシアネート組成物を得る段階は、(aa)反応器内で前記ジアミン塩酸塩組成物をトリホスゲンと第2有機溶媒中で反応させて反応溶液を得る段階と、(ab)前記反応溶液の色および透明度を測定する段階と、(ac)前記反応溶液からジイソシアネート組成物を得る段階とを含み得る。
前記実現例で調製されたジイソシアネート組成物を他の成分と組み合わせることにより、光学材料用組成物を調製し得る。すなわち、前記光学材料用組成物は、前記実現例により調製されたジイソシアネート組成物、およびチオールまたはエピスルフィドを含む。前記光学材料用組成物を用いて光学材料、具体的には、光学レンズを製造し得る。例えば、前記光学材料用組成物を混合してモールドで加熱硬化することにより、光学レンズを製造し得る。以下で説明する光学レンズの製造方法や特性は、光学レンズの他にも、前記実現例によるジイソシアネート組成物を利用して実現し得る様々な光学材料の製造方法や特性として理解するべきである。
以下において、より具体的な実施例を例示するが、これらに限定されない。
<段階1:ジアミン塩酸塩組成物の調製>
反応器に、下記表2のようなFeイオン含有量を有する35%の塩酸水溶液1009.4g(9.46mol)を投入して撹拌しながら、反応器内部の温度を15℃に冷却した。反応器の温度を60℃に維持しながらm−XDA600.0g(4.4mol)を1時間かけて投入した。投入完了後、反応器内部の温度を10℃に冷却して1時間撹拌した後、テトラヒドロフラン(THF)1320.0gを追加投入し、反応器内部の温度を−5℃に冷却して1時間さらに撹拌した。反応完了後、フィルターを用いる真空ろ過により、m−XDA・2HClを含有するジアミン塩酸塩組成物を分離し、ろ過されたテトラヒドロフランは再利用するために回収した。分離されたジアミン塩酸塩組成物を90℃および0.5torrで真空乾燥して残留溶媒および水分を除去した。
反応器Aに、前の段階で調製したジアミン塩酸塩組成物800gおよびODCB3550gを投入して撹拌しながら、約125℃にて加熱した。反応器Bに、トリホスゲン(BTMC)950gおよびODCB800gを入れて約60℃にて撹拌溶解し、析出されないように125℃の温度を維持しながら、反応器Aに24時間かけて滴下した。
<段階1:ジアミン塩酸塩組成物の調製>
1番反応器に、下記表2のようなFeイオン含有量を有する35%の塩酸水溶液1009.4g(9.46mol)を投入して撹拌しながら、1番反応器内部の温度を15℃に冷却した。1番反応器の温度を50℃に維持しながらH6XDA627.0g(4.4mol)を1時間かけて投入した。投入完了後、1番反応器内部の温度を10℃に冷却して1時間撹拌した後、ジエチルエーテル2640.0gが投入されている2番反応器内部の温度を−5℃に冷却した後、0℃以下にて1番反応器内の混合物を2番反応器にゆっくり滴下した。
反応器Aに、前の段階で調製したジアミン塩酸塩組成物823gおよびODCB3550gを投入して撹拌しながら、約125℃にて加熱した。反応器Bに、トリホスゲン(BTMC)950gおよびODCB800gを入れて約60℃にて撹拌溶解し、析出されないように125℃の温度を維持しながら、反応器Aに24時間かけて滴下した。滴下終了後、3時間〜4時間の撹拌を行った。反応終了後、125℃にて窒素ガスを溶媒内部に吹き込んでバブリングしながら脱気した。以降、10℃まで冷却した後、セライトを用いて残存固形分をろ過した。有機溶媒(ODCB)の除去および蒸留工程を行い、H6XDIを含有するジイソシアネート組成物を得た。この際、有機溶媒の除去は、0.5torr以下の圧力および60℃の温度にて8時間行った。また、蒸留は、120℃の温度および0.5torr以下の圧力で10時間行った。
<段階1:ジアミン塩酸塩組成物の調製>
反応器に、下記表2のようなFeイオン含有量を有する35%の塩酸水溶液1009.4g(9.46mol)を投入して撹拌しながら、反応器内部の温度を15℃に冷却した。反応器の温度を50℃以下に維持しながらHDA490.1g(4.4mol)を1時間かけて投入した。投入完了後、反応器内部の温度を10℃に冷却して1時間撹拌した後、テトラヒドロフラン1320.0gをさらに投入して反応器内部の温度を−5℃に冷却して1時間さらに撹拌した。反応完了後、フィルターを用いる真空ろ過により、HDA・2HClを含有するジアミン塩酸塩組成物を分離し、ろ過されたテトラヒドロフランは再利用するために回収した。その後、分離されたジアミン塩酸塩組成物を90℃および0.5torrで真空乾燥して残留溶媒および水分を除去した。
反応器Aに、前の段階で調製したジアミン塩酸塩組成物723gおよびODCB3550gを投入して撹拌しながら、約125℃にて加熱した。反応器Bに、トリホスゲン(BTMC)950gおよびODCB800gを入れて約60℃にて撹拌溶解し、析出されないように125℃の温度を維持しながら、反応器Aに24時間かけて滴下した。滴下終了後、3時間〜4時間の撹拌を行った。反応終了後、125℃にて窒素ガスを溶媒内部に吹き込んでバブリングしながら脱気した。以降、10℃まで冷却した後、セライトを用いて残存固形分をろ過して、HDIを含有するジイソシアネート組成物を得た。その際、ジイソシアネート組成物内の有機溶媒の除去および蒸留工程を行った。この際、有機溶媒の除去は、0.5torr以下の圧力および60℃の温度にて8時間行った。また、蒸留は、120℃の温度および0.5torr以下の圧力で10時間行った。
<段階1:ジアミン塩酸塩組成物の調製>
1番反応器に、下記表2のようなFeイオン含有量を有する35%の塩酸水溶液1009.4g(9.46mol)を投入して撹拌しながら、1番反応器内部の温度を15℃に冷却した。1番反応器の温度を50℃以下に維持しながらIPDA812.0g(4.4mol)を1時間かけて投入した。投入完了後、1番反応器内部の温度を10℃に冷却して1時間撹拌した後、ジエチルエーテル2640.0gが投入されている2番反応器内部の温度を−5℃に冷却した後、0℃以下にて1番反応器内の混合物を2番反応器にゆっくり滴下した。完了後、フィルターを用いる真空ろ過により、IPDA・2HClを含有するジアミン塩酸塩組成物を分離し、ろ過されたジエチルエーテルは再利用するために回収した。その後、分離されたジアミン塩酸塩組成物を90℃および0.5torrで真空乾燥して残留溶媒および水分を除去した。
反応器Aに、前の段階で調製したジアミン塩酸塩組成物984gおよびODCB3550gを投入して撹拌しながら、約125℃にて加熱した。反応器Bに、トリホスゲン(BTMC)950gおよびODCB800gを入れて約60℃にて撹拌溶解し、析出されないように125℃の温度を維持しながら、反応器Aに24時間かけて滴下した。滴下終了後、3時間〜4時間の撹拌を行った。反応終了後、125℃にて窒素ガスを溶媒内部に吹き込んでバブリングしながら脱気した。以降、10℃まで冷却した後、セライトを用いて残存固形分をろ過して、IPDIを含有するジイソシアネート組成物を得た。その後、ジイソシアネート組成物内の有機溶媒の除去および蒸留工程を行った。この際、有機溶媒の除去は、0.5torr以下の圧力および60℃の温度にて8時間行った。また、蒸留は、120℃の温度および0.5torr以下の圧力で10時間行った。
実施例5の段階1の手順を繰り返すが、下記表2のようなFeイオン含有量を有する35%の塩酸水溶液を用いてジアミン塩酸塩組成物を調製した後、実施例5の段階2の手順によりジイソシアネート組成物を調製した。
実施例6の段階1の手順を繰り返すが、下記表2のようなFeイオン含有量を有する35%の塩酸水溶液を用いてジアミン塩酸塩組成物を調製した後、実施例5の段階2の手順によりジイソシアネート組成物を調製した。
実施例7の段階1の手順を繰り返すが、下記表2のようなFeイオン含有量を有する35%の塩酸水溶液を用いてジアミン塩酸塩組成物を調製した後、実施例5の段階2の手順によりジイソシアネート組成物を調製した。
下記表1に記載のように、実施例または比較例で調製したジイソシアネート組成物(主成分:m−XDI、H6XDI、HDI、またはIPDI)、ポリチオールとして5,7−ジメルカプトメチル−1,11−ジメルカプト−3,6−トリチアウンデカン(BET)、および添加剤としてスズ系触媒などを均一に混合し、600Paで1時間脱泡して重合性組成物を調製した。
前記実施例および比較例を以下のように評価した。
色差計(Colormate、SCINCO社)を利用して、液状サンプルの場合、厚さ10mmの石英セルに満たし、固体サンプルの場合、有機溶媒(ODCB)に8重量%で溶解してb*値を測定した。b*値が低いほど色が良好である。
アッベ屈折計DR−M4(ATAGO社)を利用して、20℃にて固相屈折率(nd20)を測定した。
半径16mmおよび高さ45mmの円柱状で光学レンズを作製し、高さ方向に光を透過して黄色度および透過率を測定した。黄色度は、測定結果のxとyの値に基づいて、以下の式により算出した。
Y.I=(234x+106y)/y
直径75mm、−2.00D、−8.00Dのレンズを製造し、マーキュリーランプ光源を製造済みのレンズに透過させ、透過光を白色板に投影して明暗差の有無により脈理発生の有無を判断した。
−分析装置:ICP−OES(Inductively Coupled Plasma-Optical Emission Spectrometer)
−装置仕様:Agilent社730ES
−光源:Axially viewed Plasma system
−検出器:167nm〜785nm波長CCD(charge coupled device)検出器
−試料前処理:液相試料の場合、試料2gを水18gに1時間超音波処理した後に水層のみ採取しており、固相試料の場合、試料0.2gを水19.8gに溶解した溶液を調製した。
その結果を下記の表に示した。
T−2:第2タンク
T−3:第3タンク、
R−1:反応器
D−1:第1蒸留器
D−2:第2蒸留器
C−1:第1コンデンサ
C−2:第2コンデンサ
C−3:第3コンデンサ
S−1:第1スクラバー
S−2:第2スクラバー
G−1:透視窓
V−1:溶媒回収器
Claims (10)
- (1)ジアミン組成物を塩酸水溶液と反応させてジアミン塩酸塩組成物を得る段階と、
(2)前記ジアミン塩酸塩組成物をトリホスゲンと反応させてジイソシアネート組成物を得る段階とを含み、
前記ジイソシアネート組成物がCIE色座標による0.1〜2.0のb*値を有する、ジイソシアネート組成物の調製方法。 - 前記塩酸水溶液内のFeイオンの含有量が0.5ppm以下である、請求項1に記載のジイソシアネート組成物の調製方法。
- 前記ジアミン塩酸塩組成物が水に8重量%の濃度で溶解する際に、CIE色座標による1.5以下のb*値を有する、請求項1に記載のジイソシアネート組成物の調製方法。
- 前記ジアミン塩酸塩組成物のCIE色座標によるb*値は、
5.7以下の極性を有する5℃以下の溶媒を用いた洗浄によって調節される、請求項3に記載のジイソシアネート組成物の調製方法。 - 前記段階(2)の前に、前記ジアミン塩酸塩組成物のCIE色座標によるb*値を測定する段階をさらに含む、請求項1に記載のジイソシアネート組成物の調製方法。
- 前記ジイソシアネート組成物が、前記ジアミン塩酸塩組成物と前記トリホスゲンとの反応後に蒸留して得られたものであり、
前記蒸留が、100℃〜130℃の温度および2torr以下の圧力条件におけるジイソシアネート蒸留を含む、請求項1に記載のジイソシアネート組成物の調製方法。 - (1)ジアミン組成物を塩酸水溶液と反応させて、ジアミン塩酸塩組成物を得る段階と、
(2)前記ジアミン塩酸塩組成物をトリホスゲンと反応させて、ジイソシアネート組成物を得る段階と、
(3)前記ジイソシアネート組成物をチオールまたはエピスルフィドと混合して、モールドで重合および硬化させる段階とを含み、
前記ジイソシアネート組成物が、CIE色座標による0.1〜2.0のb*値を有する、光学レンズの製造方法。 - 前記光学レンズが、90%以上の透過率および20以下の黄色度(Y.I)を有する、請求項7に記載の光学レンズの製造方法。
- CIE色座標によるb*値が0.1〜2.0である、ジイソシアネート組成物。
- 前記ジイソシアネート組成物内のFeイオンの含有量が0.2ppm以下であり、
前記ジイソシアネート組成物が、キシリレンジイソシアネートを99.9重量%以上で含む、請求項9に記載のジイソシアネート組成物。
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