JP2021091672A - ジアミン組成物、およびジイソシアネート組成物の調製方法 - Google Patents
ジアミン組成物、およびジイソシアネート組成物の調製方法 Download PDFInfo
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- JP2021091672A JP2021091672A JP2020199067A JP2020199067A JP2021091672A JP 2021091672 A JP2021091672 A JP 2021091672A JP 2020199067 A JP2020199067 A JP 2020199067A JP 2020199067 A JP2020199067 A JP 2020199067A JP 2021091672 A JP2021091672 A JP 2021091672A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- diamine
- diisocyanate
- methyl group
- ppm
- 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 440
- 125000005442 diisocyanate group Chemical group 0.000 title claims abstract description 178
- 150000004985 diamines Chemical class 0.000 title claims abstract description 168
- 238000002360 preparation method Methods 0.000 title abstract description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 145
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims abstract description 119
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 113
- 238000000034 method Methods 0.000 claims abstract description 64
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract description 64
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 50
- 238000006243 chemical reaction Methods 0.000 claims description 142
- 238000004821 distillation Methods 0.000 claims description 57
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 claims description 51
- 239000000126 substance Substances 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 claims description 12
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 claims description 3
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 description 121
- 239000000243 solution Substances 0.000 description 94
- 239000000463 material Substances 0.000 description 59
- 239000003960 organic solvent Substances 0.000 description 57
- -1 alicyclic isocyanate Chemical class 0.000 description 34
- 239000007789 gas Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 24
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 23
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 21
- 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 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 14
- 239000003990 capacitor Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 150000003573 thiols Chemical class 0.000 description 13
- 238000002834 transmittance Methods 0.000 description 13
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 12
- 229920002578 polythiourethane polymer Polymers 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 150000003553 thiiranes Chemical class 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 150000002513 isocyanates Chemical class 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 210000003462 vein Anatomy 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 238000005381 potential energy Methods 0.000 description 9
- 238000004383 yellowing Methods 0.000 description 9
- 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 8
- 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 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- 239000007790 solid phase Substances 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 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 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 229910052742 iron Inorganic materials 0.000 description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical group CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 125000006839 xylylene group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- JCUQBSLBFAVVOS-UHFFFAOYSA-N 1-(isocyanatomethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CN=C=O)=C1 JCUQBSLBFAVVOS-UHFFFAOYSA-N 0.000 description 4
- XSHSGUNSTVQOQE-UHFFFAOYSA-N 2-isocyanato-2-phenylacetonitrile Chemical compound C1(=CC=CC=C1)C(C#N)N=C=O XSHSGUNSTVQOQE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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
- 229910000831 Steel Inorganic materials 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000003860 storage 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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-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
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-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
- 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 3
- 230000005587 bubbling Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000007613 environmental effect Effects 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
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical group C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000010349 pulsation Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007858 starting material Substances 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
- 238000003828 vacuum filtration Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VNHPWTGETWKSLP-UHFFFAOYSA-N 1-(isocyanatomethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CN=C=O VNHPWTGETWKSLP-UHFFFAOYSA-N 0.000 description 2
- KNYDWDHLGFMGCO-UHFFFAOYSA-N 1-(isocyanatomethyl)-4-methylbenzene Chemical compound CC1=CC=C(CN=C=O)C=C1 KNYDWDHLGFMGCO-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-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
- 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
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004132 cross linking 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
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 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
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- 239000007924 injection Substances 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
- 239000007788 liquid 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
- 239000010452 phosphate Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 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
- XKXKKCYHCIGWJG-UHFFFAOYSA-N (2-chloro-1-isocyanatoethyl)benzene Chemical compound O=C=NC(CCl)C1=CC=CC=C1 XKXKKCYHCIGWJG-UHFFFAOYSA-N 0.000 description 1
- 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
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
-
- 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
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Abstract
Description
実現例によるジアミン組成物は、ジアミン;および10ppm〜2000ppmの含有量でメチル基を有するベンジルモノアミンを含む。
本発明の実現例により、前記のように組成が制御されたジアミン組成物を用いて、ジイソシアネート組成物を調製し得る。
まず、ジアミン組成物を塩酸水溶液と反応させ、ジアミン塩酸塩組成物を得る(第1段階)。
前記実現例によると、出発物質としてCIE色座標によるb*値が調節されたジアミン組成物を利用するので、これにより得られたジアミン塩酸塩組成物のb*値も調節され得る。例えば、前記実現例による方法で調製されたジアミン塩酸塩組成物は、水に8重量%の濃度で溶解時にCIE色座標によるb*値が1.5以下、1.2以下、1.0以下、または0.8以下であり得る。具体的に、前記CIE色座標によるb*値は、0.01〜1.2、0.1〜1.2、0.1〜1.0、0.1〜0.8、または0.2〜1.0であり得る。
前記ジアミン塩酸塩組成物およびトリホスゲンを用いてジイソシアネート組成物を得る(第2段階)。具体的に、前記ジアミン塩酸塩組成物からホスゲン化反応によりジイソシアネート組成物を得る。
前記反応により得られた反応結果物は、分離、脱気、ろ過、および蒸留をさらに経ても良い。
実現例によると、ジイソシアネート組成物内でメチル基を有するベンジルイソシアネートの含有量は、5ppm〜200ppmであり得る。
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を他の成分と組み合わせることにより、光学材料用重合性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。
本発明の一実現例による光学材料は、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が重合されたポリチオウレタンを含む光学材料として、前記ジイソシアネート組成物内でメチル基を有するベンジルイソシアネートの含有量が5ppm〜200ppm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。
<第1段階:ジアミン塩酸塩組成物の調製>
メタキシリレンジアミン(m−XDA)600g(4.4mol)に3−メチルベンジルアミンを添加してジアミン組成物内で前記3−メチルベンジルアミンの濃度が10ppmに調節されたジアミン組成物を準備した。
反応器Aに、前記調製したm−XDA塩酸塩組成物800gおよびオルトジクロロベンゼン(ODCB)3550gを投入して撹拌しながら、反応器の内部温度を約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、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。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。その後、有機溶媒(ODCB)を除去して、m−XDIを下記蒸留条件で蒸留して精製した。前記有機溶媒の除去(1次蒸留)は、0.5torr以下の圧力、60℃の温度にて8時間行っており、m−XDIの蒸留(2次蒸留)は、0.1torr以下の圧力、120℃の温度にて10時間行い、m−XDI組成物を得た。
4,8−ビス(メルカプトメチル)−3,6,9−トリチアウンデカン−1,11−ジチオール49.3重量部、前記調製したm−XDI組成物50.7重量部、ジブチルスズクロリド0.01重量部、リン酸エステル離型剤(Zelec UN(登録商標)、Stepan社)0.1重量部を均一に混合して、600Paで1時間脱泡した後、3μmテフロンフィルターにろ過して、ガラスモールドとテープにより製作されたモールドに注入した。前記モールドを25℃にて8時間維持した後、130℃まで8時間かけて一定の速度でゆっくり昇温し、130℃にて2時間重合した。成形物をモールドから離型した後、120℃にて2時間さらに硬化して光学レンズ(光学材料)を得た。
3−メチルベンジルアミンの投入濃度を下記表1のように調節したことを除いては、実施例1−1と同様の方法により、m−XDI組成物および光学レンズを得た。
3−メチルベンジルアミンの投入濃度を下記表1のように調節したことを除いては、実施例1−1と同様の方法により、m−XDI組成物および光学レンズを得た。
前記実施例および比較例を以下のように評価した。
硬化されたレンズを暗所にてプロジェクターに照射して、レンズの曇りや不透明物質の有無を目視で確認した。
白濁無し:レンズの曇りや不透明物質がない場合
白濁有り:レンズの曇りや不透明物質がある場合
米国FDAの試験基準に基づいて、常温20℃にて直径80mm、厚さ1.2mmの平板で製造された試験片に、127cmの高さにて軽い鋼球から重い鋼球まで順に落下させて破壊される重さの位置エネルギーで耐衝撃性を測定した。
Ep=mgh=0.016×9.8×1.27=0.2(J)
計算例−2)韓国産業安全基準67g、127cm基準のときの位置エネルギー(Ep)は、
Ep=mgh=0.067×9.8×1.27=0.83(J)
<段階1:ジアミン塩酸塩組成物の調製>
まず、m−XDAを含むジアミン組成物を準備し、そのCIE色座標によるb*値を測定して、b*値が3.0を超える場合、100℃〜130℃および0.1torr〜1torrの条件で蒸留して、b*値が0.01〜3.0の範囲になるように調節した。反応器に35%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、前記準備したジアミン組成物600.0g(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。残留溶媒および水分を除去するために、分離したジアミン塩酸塩組成物内の残留溶媒および水分を90℃にて除去し、0.1Torrで真空乾燥を行った。
前の段階で得たジアミン塩酸塩組成物800gおよびオルトジクロロベンゼン(ODCB)3550gを反応器Aに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℃の温度を維持して、反応器Aに24時間かけて滴下した。滴下終了後、4時間の撹拌を行い、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。その後、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、有機溶媒(ODCB)の除去および蒸留工程を行い、m−XDI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、60℃の温度にて8時間行っており、また、蒸留は0.1torr以下の圧力、120℃の温度にて10時間行った。
4,8−ビス(メルカプトメチル)−3,6,9−トリチアウンデカン−1,11−ジチオール49.3重量部、前記実施例または比較例で調製したm−XDI組成物50.7重量部、ジブチルスズクロリド0.01重量部、リン酸エステル離型剤(Zelec UN、Stepan社)0.1重量部を均一に混合して、600Paで1時間脱泡した後、3μmテフロンフィルターにろ過して、ガラスモールドとテープにより製作されたモールドに注入した。前記モールドを25℃にて8時間維持した後、130℃まで8時間かけて一定の速度でゆっくり昇温し、130℃にて2時間重合した。成形物をモールドから離型した後、120℃にて2時間さらに硬化して、光学レンズを得た。
前記実施例および比較例に対する評価方法は以下の通りである。
蒸留収率は、トリホスゲンとの反応に投入されたジアミン塩酸塩組成物の量から算出された理論的ジイソシアネート組成物の生成量に対する、蒸留後のジイソシアネート組成物の収得量を測定して算出した。
ジイソシアネート組成物内のジイソシアネート含有量を、ガスクロマトグラフィー(GC)により測定した(機器:Agilent社の6890/7890、キャリアガス:He、注入温度250℃、オーブン温度40℃〜320℃、カラム:HP−1、Wax、30m、検出器:FID、300℃)
直径75mm、−2.00D、−8.00Dのレンズを製造して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で脈理発生の有無を判断した。
光学レンズを暗所にてプロジェクターに照射して、光学レンズの曇りや不透明物質の有無を目視で確認した。
半径16mmおよび高さ45mmの円柱状に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、下記数学式により算出した。
[数1]
Y.I=(234x+106y)/y
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 (14)
- ジアミン;および
10ppm〜2000ppmの含有量でメチル基を有するベンジルモノアミンを含む、ジアミン組成物。 - 前記組成物の総重量を基準に前記ジアミンを99重量%以上〜100重量%未満の量で含み、
前記ジアミンが、オルトキシリレンジアミン(o−XDA)、メタキシリレンジアミン(m−XDA)、およびパラキシリレンジアミン(p−XDA)からなる群より選択された1種以上を含む、請求項1に記載のジアミン組成物。 - 前記メタキシリレンジアミン(m−XDA)を、前記組成物の総重量を基準に99.5重量%以上〜100重量%未満の量で含む、請求項3に記載のジアミン組成物。
- 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、
前記ジアミン塩酸塩組成物およびトリホスゲンを用いてジイソシアネート組成物を得る段階とを含み、
前記ジアミン組成物が、ジアミン;および10ppm〜2000ppmの含有量でメチル基を有するベンジルモノアミンを含む、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、メチル基を有するベンジルモノアミン塩酸塩を含み、
前記メチル基を有するベンジルモノアミン塩酸塩が、前記トリホスゲンとの反応によりメチル基を有するベンジルイソシアネートが生成され、
前記メチル基を有するベンジルイソシアネートが、前記ジイソシアネート組成物内に5ppm〜200ppmの量で含まれ、
前記メチル基を有するベンジルモノアミンの含有量に対する、前記メチル基を有するベンジルイソシアネートの生成比が0.05〜0.9である、請求項5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とトリホスゲンとの反応後に得た反応結果物を蒸留する段階をさらに含み、
前記蒸留が、前記反応結果物を40℃〜60℃にて2時間〜8時間の1次蒸留と、
100℃〜120℃にて2時間〜10時間の2次蒸留とを含む、請求項6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および前記トリホスゲンが1:1〜5の当量比で反応に投入され、
前記ジアミン塩酸塩組成物とトリホスゲンとの反応が110℃〜160℃の温度にて行われる、請求項5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を得た後、前記ジアミン塩酸塩組成物を処理する段階をさらに含み、
前記処理済みのジアミン塩酸塩組成物が前記トリホスゲンと反応して、前記ジイソシアネート組成物が調製される、請求項5に記載のジイソシアネート組成物の調製方法。 - 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、
前記ジアミン塩酸塩組成物およびトリホスゲンを用いてジイソシアネート組成物を得る段階とを含み、
前記ジアミン組成物が、CIE色座標による0.01〜3.0のb*値を有する、ジイソシアネート組成物の調製方法。 - 前記ジイソシアネート組成物の調製方法は、前記ジアミン塩酸塩組成物を得る段階の前に、
前記ジアミン組成物のCIE色座標によるb*値を測定する段階と、
前記b*値を0.01〜3.0に調節する段階とをさらに含む、請求項10に記載のジイソシアネート組成物の調製方法。 - 前記b*値の調節は、前記ジアミン組成物を1回以上蒸留することを含み、
前記ジアミン組成物の蒸留は、100℃〜130℃の温度および0.1tоrr〜1tоrrの圧力条件で行われ、
前記ジアミン組成物がCIE色座標による0.01〜1.0のb*値を有する、請求項11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は、水に8重量%の濃度で溶解する際、CIE色座標による1.2以下のb*値を有し、
前記ジイソシアネート組成物は、CIE色座標による0.01〜2.0のb*値を有する、請求項10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は、前記ジアミン塩酸塩組成物をトリホスゲンと反応させた後、蒸留して得られたものであり、前記蒸留は、100℃〜130℃の温度および2tоrr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10に記載のジイソシアネート組成物の調製方法。
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