JP6612438B2 - キシリレンジイソシアネート組成物、樹脂および重合性組成物 - Google Patents
キシリレンジイソシアネート組成物、樹脂および重合性組成物 Download PDFInfo
- Publication number
- JP6612438B2 JP6612438B2 JP2018512021A JP2018512021A JP6612438B2 JP 6612438 B2 JP6612438 B2 JP 6612438B2 JP 2018512021 A JP2018512021 A JP 2018512021A JP 2018512021 A JP2018512021 A JP 2018512021A JP 6612438 B2 JP6612438 B2 JP 6612438B2
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- JP
- Japan
- Prior art keywords
- xylylene diisocyanate
- less
- resin
- polyol
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 121
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 title claims description 117
- 229920005989 resin Polymers 0.000 title claims description 87
- 239000011347 resin Substances 0.000 title claims description 87
- 229920005862 polyol Polymers 0.000 claims description 102
- 150000003077 polyols Chemical class 0.000 claims description 88
- 229920006295 polythiol Polymers 0.000 claims description 57
- XKXKKCYHCIGWJG-UHFFFAOYSA-N (2-chloro-1-isocyanatoethyl)benzene Chemical compound O=C=NC(CCl)C1=CC=CC=C1 XKXKKCYHCIGWJG-UHFFFAOYSA-N 0.000 claims description 40
- 230000003287 optical effect Effects 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- -1 poly (thio) urethane Polymers 0.000 description 94
- 238000006243 chemical reaction Methods 0.000 description 69
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- 239000005056 polyisocyanate Substances 0.000 description 45
- 229920001228 polyisocyanate Polymers 0.000 description 45
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000012948 isocyanate Substances 0.000 description 35
- 150000002513 isocyanates Chemical class 0.000 description 35
- 238000000034 method Methods 0.000 description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 24
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 22
- 229920003023 plastic Polymers 0.000 description 22
- 239000004033 plastic Substances 0.000 description 22
- 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
- 238000002360 preparation method Methods 0.000 description 21
- 239000012442 inert solvent Substances 0.000 description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 238000004821 distillation Methods 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 description 15
- 229920002554 vinyl polymer Polymers 0.000 description 15
- 238000002156 mixing Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000006082 mold release agent Substances 0.000 description 8
- 229920005906 polyester polyol Polymers 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 238000004383 yellowing Methods 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- OCGYTRZLSMAPQC-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[1-sulfanyl-3-(2-sulfanylethylsulfanyl)propan-2-yl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SC(CS)CSCCS OCGYTRZLSMAPQC-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 208000020329 Zika virus infectious disease Diseases 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- 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 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- 238000012662 bulk polymerization Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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 3
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 3
- 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
- NXYWIOFCVGCOCB-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SCC(CS)SCCS NXYWIOFCVGCOCB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000004593 Epoxy Substances 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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
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- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-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
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- TWXMZYPORGXIFB-UHFFFAOYSA-N thiophene-3,4-dithiol Chemical compound SC1=CSC=C1S TWXMZYPORGXIFB-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 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
- 238000012546 transfer Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/02—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms
- C07C265/06—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C265/08—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/773—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur halogens
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
数平均分子量は、水酸基当量および平均官能基数から求めることができ、平均官能基数は、次式(2)から求めることができる(以下同様。)。
また、とりわけ、本発明の樹脂を光学材料として製造する場合における、ポリオール成分および/またはポリチオール成分の水酸基価は、例えば、280mgKOH/g以上、好ましくは、400mgKOH/gであり、例えば、1240mgKOH/g以下、好ましくは、940mgKOH/g以下であり、数平均分子量は、例えば、90以上、好ましくは、100以上であり、例えば、1000以下、好ましくは、800以下であり、平均官能基数は、例えば、2を超過し、好ましくは、2.5以上であり、通常、5.0以下、好ましくは、4.0未満である。
1.測定方法
(キシリレンジアミンのアミン転化率)
キシリレンジアミンの塩酸塩の合成反応終了後の反応液(スラリー)中に残存する未反応のキシリレンジアミン(以下、残存アミンとする。)を中和滴定して、残存アミンのモル数を得た。これと、仕込んだキシリレンジアミン(以下、仕込みアミンとする。)のモル数とから、下記式(3)によりキシリレンジアミンのアミン転化率を算出した。
(キシリレンジイソシアネート組成物中のクロロメチルベンジルイソシアネートの生成率および含有割合)
まず、純度99モル%のクロロメチルベンジルイソシアネートを標準物質として用い、以下のガスクロマトグラフ分析条件で得られたガスクロマトグラフの面積値から検量線を作成した。
装置;GC−2014(SHIMADZU社製)
カラム;DB−1、内径0.53mm×長さ60m×膜厚1.5μm(J&W社製)
オーブン温度;130℃から220℃まで、3℃/minで昇温、220℃到達後10℃/minで300℃まで昇温。
スプリット比;スプリットなし(全量注入)
注入口温度;280℃
検出器温度;300℃
キャリアガス;N2
キャリアガス流量;8ml/min
検出方法;FID
(キシリレンジイソシアネートの純度)
最終的に得られたキシリレンジイソシアネート組成物を上記と同様にガスクロマトグラフィーにて分析して、キシリレンジイソシアネートのモル数を得た。これを質量に換算し、キシリレンジイソシアネート組成物の質量で割ることにより、キシリレンジイソシアネート組成物中のキシリレンジイソシアネートの含有割合(純度)を算出した。
(キシリレンジアミンの塩酸塩の塩酸塩転化率)
キシリレンジアミンの塩酸塩と、ホスゲンとの反応後に濾過し、得られた反応濾過液残渣を中和滴定し、残存したキシリレンジアミンの塩酸塩(以下、残存塩酸塩とする。)のモル数を得た。これと、仕込んだ塩酸塩(以下、仕込み塩酸塩とする。)のモル数とから、下記式(4)により転化率を算出した。
(キシリレンジアミンの塩酸塩の粘度の測定)
キシリレンジアミンの塩酸塩の合成反応終了後の反応液(スラリー)を容器に計り取り、測定温度120℃に昇温した。120℃に到達したときに、BROOKFIELD製LVT型粘度計のNO.2ローターにて粘度を測定し、指示値に係数を掛けて粘度を算出した。
(キシリレンジアミンの塩酸塩の平均粒子径(数平均値)の測定)
キシリレンジアミンの塩酸塩の合成反応終了後の反応液(スラリー)を少量抜き取り、アセトニトリル溶媒中で(株)島津製作所製レーザー回析式粒度分布測定装置SALD−2100にて測定した。測定された粒子径は、全粒子径の数平均値である。
(キシリレンジイソシアネート組成物中のクロロメチルベンジルイソシアネートの含有割合)
キシリレンジイソシアネート組成物をクロロホルムに溶解後、当該溶液を上記と同様にガスクロマトグラフィーでクロロメチルベンジルイソシアネートのモル数を得て、これを質量に換算し、キシリレンジイソシアネート組成物の質量で割って、キシリレンジイソシアネート組成物中のクロロメチルベンジルイソシアネートの含有割合を算出した。
(樹脂のイエローインデックスの値(Y.I.値)の算出)
樹脂を、それぞれ、厚さ9mm、直径75mmの円形平板プラスチックレンズとして作成し、MINOLTA社製色彩色差計CT−210を用いて色度座標x、yを測定した。測定結果であるxとyの値を元に下記式(5)によりY.I.を算出した。
(樹脂比重の測定)
アルキメデス法により測定した。
(樹脂の光学特性の測定)
屈折計KPR−20(カルニュー光学工業社製)を用い、20℃で、波長546.1nm(水銀e線)での屈折率(ne)およびアッベ数(νe)をそれぞれ測定した。
(樹脂の染色性の評価方法)
純水3000gに、「FSP Red E−A」(双葉産業株式会社社製、染料)2.3g、「FSP Yellow P−E」(双葉産業株式会社社製、染料)1.5g、「FSP Blue AUL−S」(双葉産業株式会社社製、染料)6.0g、「ニッカサンソルト#7000」(日華化学株式会社社製、染色分散剤)6.0g、「DK−CN」(大和化学工業社製、染色助剤)6.0gを添加し、染料分散液を調製した。厚さ9mmの樹脂を80℃にて30分間これに浸漬して、染色した。染色された樹脂の638nm、567nmおよび452nmそれぞれにおける光透過率(%)を測定した。
(樹脂の耐熱性の評価方法)
TMAペネートレーション法(荷重:50g、ピン先直径:0.5mm、昇温速度:10℃/min)により、熱機械分析装置TMA−60(島津製作所社製)を用いて、ガラス転移温度(Tg)を測定した。ガラス転移温度を耐熱性の指標とした。
2.キシリレンジイソシアネート組成物の調製
(調製例1)
還流冷却管、撹拌翼、温度計、塩化水素ガス導入管、ホスゲン導入管、原料槽、原料装入ポンプを備えた、圧力調節器付きのオートクレーブ(反応器)を用いた。反応器において、撹拌翼の径(D1)/反応器の内径(D2)の値は0.7であり、槽径(D)/槽長(L)値は0.59であり、反応器の内容積は2m3であった。この反応器内に、不活性溶媒としてオルトジクロロベンゼン846kgを仕込み、原料槽にm−キシリレンジアミン136.2kg(1.0kモル)、および、オルトジクロロベンゼン621kgを仕込んだ(全アミン濃度8.5重量%)。
(調製例2〜8)
精留塔の塔頂還流比を変化させることにより、所定量のメタクロロメチルベンジルイソシアネートを含むキシリレンジイソシアネート組成物を得た。
XDI:キシリレンジイソシアネート
CBI:クロロメチルベンジルイソシアネート
3.樹脂(プラスチックレンズ)の製造
(実施例1)
十分に乾燥させたフラスコに、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート100質量ppmとを含有した、調製例1で得たキシリレンジイソシアネート組成物36.4g、ジブチル錫ジクロライド0.001g、ゼレックUN(商品名、酸性リン酸エステル、内部離型剤、Stepan社製)0.07g、バイオソーブ583(商品名、紫外線吸収剤、堺化学工業社製)0.05gを秤量し、25℃で1時間攪拌して混合溶解させポリイソシアネート成分を調製した。その後、このポリイソシアネート成分に1,2−ビス[(2−メルカプトエチル)チオ]−3−メルカプトプロパン33.6gを装入混合して混合液(重合性組成物)を調製した。
(実施例2)
実施例1で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート200質量ppmとを含有した、調製例2で得たキシリレンジイソシアネート組成物を用いた他は、実施例1と同様にして樹脂(プラスチックレンズ)を製造した。
(実施例3)
実施例1で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート400質量ppmとを含有した、調製例3で得たキシリレンジイソシアネート組成物を用いた他は、実施例1と同様にして樹脂(プラスチックレンズ)を製造した。
(実施例4)
実施例1で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート500質量ppmとを含有した、調製例4で得たキシリレンジイソシアネート組成物を用いた他は、実施例1と同様にして樹脂(プラスチックレンズ)を製造した。
(実施例5)
十分に乾燥させたフラスコに、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート100質量ppmとを含有した、調製例1で得たキシリレンジイソシアネート組成物50.7g、ジブチル錫ジクロライド0.01g、ゼレックUN(商品名、酸性リン酸エステル、内部離型剤、Stepan社製)0.1g、バイオソーブ583(商品名、紫外線吸収剤、堺化学工業社製)0.05gを秤量し、25℃で1時間攪拌して混合溶解させポリイソシアネート成分を調製した。その後、このポリイソシアネート成分に4,8−ジメルカプトメチル−1,11−ジメルカプト−3,6,9−トリチアウンデカンを主成分とするポリチオール49.3gを装入混合して混合液(重合性組成物)を調製した。
(実施例6)
実施例5で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート200質量ppmとを含有した、調製例2で得たキシリレンジイソシアネート組成物を用いた他は、実施例5と同様にして樹脂(プラスチックレンズ)を製造した。
(実施例7)
実施例5で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート400質量ppmとを含有した、調製例3で得たキシリレンジイソシアネート組成物を用いた他は、実施例5と同様にして樹脂(プラスチックレンズ)を製造した。
(実施例8)
実施例5で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート500質量ppmとを含有した、調製例4で得たキシリレンジイソシアネート組成物を用いた他は、実施例5と同様にして樹脂(プラスチックレンズ)を製造した。
(比較例1)
m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート0.1質量ppmとを含有した、調製例5で得たキシリレンジイソシアネート組成物36.4g、ジブチル錫ジクロライド0.001g、ゼレックUN(商品名、酸性リン酸エステル、内部離型剤、Stepan社製)0.07g、バイオソーブ583(商品名、紫外線吸収剤、堺化学工業社製)0.05gを秤量し、25℃で1時間撹拌したが、溶解せず樹脂(プラスチックレンズ)が製造できなかった。
(比較例2)
実施例1で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート700質量ppmとを含有した、調製例6で得たキシリレンジイソシアネート組成物を用いた他は、実施例1と同様にして樹脂(プラスチックレンズ)を製造した。
(比較例3)
m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート0.1質量ppmとを含有した、調製例5で得たキシリレンジイソシアネート組成物5.7g、ジブチル錫ジクロライド0.001g、ゼレックUN(商品名、酸性リン酸エステル、内部離型剤、Stepan社製)0.07g、バイオソーブ583(商品名、紫外線吸収剤、堺化学工業社製)0.05gを秤量し、25℃で1時間攪拌したが、溶解せず樹脂(プラスチックレンズ)が製造できなかった。
(比較例4)
実施例5で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート700質量ppmとを含有した、調製例6で得たキシリレンジイソシアネート組成物を用いた他は、実施例5と同様にして樹脂(プラスチックレンズ)を製造した。
XDI:キシリレンジイソシアネート
CBI:クロロメチルベンジルイソシアネート
(実施例9)
十分に乾燥させたフラスコに、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート32質量ppmとを含有した、調製例7で得たキシリレンジイソシアネート組成物35.5g、ジブチル錫ジクロライド0.007g、ゼレックUN(商品名、酸性リン酸エステル、内部離型剤、Stepan社製)0.07g、バイオソーブ583(商品名、紫外線吸収剤、堺化学工業社製)0.035gを秤量し、25℃で1時間攪拌して混合溶解させポリイソシアネート成分を調製した。その後、このポリイソシアネート成分に5,7−ジメルカプトメチルー1,11−ジメルカプト−3,6,9−トリチアウンデカンと、4,7−ジメルカプトメチルー1,11−ジメルカプト−3,6,9−トリチアウンデカンと、4,8−ジメルカプトメチルー1,11−ジメルカプト−3,6,9−トリチアウンデカンとの混合物34.5gを装入混合して混合液(重合性組成物)を調製した。
(実施例10)
実施例9で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート200質量ppmとを含有した、調製例2で得たキシリレンジイソシアネート組成物を用いた他は、実施例9と同様にして樹脂(プラスチックレンズ)を製造した。
(比較例5)
実施例9で用いたキシリレンジイソシアネート組成物に代えて、m−キシリレンジイソシアネートと、メタクロロメチルベンジルイソシアネート1800質量ppmとを含有した、調製例8で得たキシリレンジイソシアネート組成物を用いた他は、実施例9と同様にして樹脂(プラスチックレンズ)を製造した。
XDI:キシリレンジイソシアネート
CBI:クロロメチルベンジルイソシアネート
なお、上記発明は、本発明の例示の実施形態として提供したが、これは単なる例示に過ぎず、限定的に解釈してはならない。当該技術分野の当業者によって明らかな本発明の変形例は、後記請求の範囲に含まれる。
Claims (6)
- キシリレンジイソシアネートと、クロロメチルベンジルイソシアネートとを含み、
前記クロロメチルベンジルイソシアネートが、0.2ppm以上500ppm以下含有されていることを特徴とする、キシリレンジイソシアネート組成物。 - 光学材料の製造に用いられることを特徴とする、請求項1に記載のキシリレンジイソシアネート組成物。
- 請求項1に記載のキシリレンジイソシアネート組成物と、
ポリオール成分および/またはポリチオール成分と
の反応生成物であることを特徴とする、樹脂。 - 光学材料であることを特徴とする、請求項3に記載の樹脂。
- 光学レンズであることを特徴とする、請求項4に記載の樹脂。
- 請求項1に記載のキシリレンジイソシアネート組成物と、
ポリオール成分および/またはポリチオール成分と
を含むことを特徴とする、重合性組成物。
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2017
- 2017-04-11 WO PCT/JP2017/014828 patent/WO2017179575A1/ja active Application Filing
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- 2017-04-11 KR KR1020187026028A patent/KR102107329B1/ko active IP Right Grant
- 2017-04-11 KR KR1020207009291A patent/KR20200037445A/ko not_active Application Discontinuation
- 2017-04-11 CN CN201780015098.XA patent/CN108779066A/zh active Pending
- 2017-04-11 EP EP17782388.7A patent/EP3444236B1/en active Active
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KR20180104330A (ko) | 2018-09-20 |
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WO2017179575A1 (ja) | 2017-10-19 |
JPWO2017179575A1 (ja) | 2018-12-27 |
US20190106529A1 (en) | 2019-04-11 |
KR102107329B1 (ko) | 2020-05-06 |
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