JPWO2015133493A1 - ポリイソシアヌレート組成物およびその製造方法 - Google Patents
ポリイソシアヌレート組成物およびその製造方法 Download PDFInfo
- Publication number
- JPWO2015133493A1 JPWO2015133493A1 JP2016506513A JP2016506513A JPWO2015133493A1 JP WO2015133493 A1 JPWO2015133493 A1 JP WO2015133493A1 JP 2016506513 A JP2016506513 A JP 2016506513A JP 2016506513 A JP2016506513 A JP 2016506513A JP WO2015133493 A1 JPWO2015133493 A1 JP WO2015133493A1
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- polyisocyanurate composition
- xylylene diisocyanate
- mass
- producing
- 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 81
- 229920000582 polyisocyanurate Polymers 0.000 title claims abstract description 68
- 239000011495 polyisocyanurate Substances 0.000 title claims abstract description 68
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 36
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 129
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 11
- 150000008301 phosphite esters Chemical class 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 5
- 239000003426 co-catalyst Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 27
- 229920005862 polyol Polymers 0.000 description 27
- 150000003077 polyols Chemical class 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- -1 dinonylphenyl Chemical group 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000001879 gelation Methods 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 12
- 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 11
- 229920005749 polyurethane resin Polymers 0.000 description 11
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 10
- 125000000565 sulfonamide group Chemical group 0.000 description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 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 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229920005906 polyester polyol Polymers 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 6
- XZZWOTQMUOIIFX-UHFFFAOYSA-N 1-(2-diphenoxyphosphanyloxypropoxy)propan-2-yl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC(C)COCC(C)OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 XZZWOTQMUOIIFX-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 235000019437 butane-1,3-diol Nutrition 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 150000005622 tetraalkylammonium hydroxides Chemical group 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000002649 leather substitute Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-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
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 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
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- HLFNUPJVFUAPLD-UHFFFAOYSA-M 2-ethylhexanoate;2-hydroxypropyl(trimethyl)azanium Chemical compound CC(O)C[N+](C)(C)C.CCCCC(CC)C([O-])=O HLFNUPJVFUAPLD-UHFFFAOYSA-M 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 2
- HWNJNAUJFVQJRV-UHFFFAOYSA-N 3,7-dimethyloct-7-ene-1,6-diol Chemical compound OCCC(C)CCC(O)C(C)=C HWNJNAUJFVQJRV-UHFFFAOYSA-N 0.000 description 2
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-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
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002334 Spandex Polymers 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
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- 235000011187 glycerol Nutrition 0.000 description 2
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- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
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- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- NQISDOIAJWWPGA-UHFFFAOYSA-N triethyl(3-hydroxypropyl)azanium Chemical compound CC[N+](CC)(CC)CCCO NQISDOIAJWWPGA-UHFFFAOYSA-N 0.000 description 1
- GZBUMTPCIKCWFW-UHFFFAOYSA-N triethylcholine Chemical compound CC[N+](CC)(CC)CCO GZBUMTPCIKCWFW-UHFFFAOYSA-N 0.000 description 1
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- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3885—Phosphate compounds
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- 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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- C08G18/701—Compounds forming isocyanates or isothiocyanates in situ
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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Abstract
Description
<反応率(%)・反応速度>
イソシアネート基濃度(JIS K−1556に準拠した方法)を測定し、その減少率を求めることにより、イソシアヌレート化反応における反応率を求めた。
<ゲル化>
イソシアヌレート化反応後の反応液を目視で観察し、ゲル化の有無について評価した。
温度計、撹拌装置、窒素導入管および冷却管が装着された反応器において、窒素雰囲気下、m−キシリレンジイソシアネート(三井化学社製、XDI)100質量部と、2,6−ジ(tert-ブチル)−4−メチルフェノール(別名:ジブチルヒドロキシトルエン、BHT、ヒンダードフェノール系酸化防止剤) 0.02質量部と、テトラフェニル・ジプロピレングリコール・ジホスファイト(商品名JPP−100、城北化学工業社製、有機亜リン酸エステル、助触媒) 0.05質量部とを混合した後、この混合液に、イソシアヌレート化触媒として、トリメチルベンジルアンモニウムのハイドロオキサイド(40%メタノール溶液)を、0.02質量部配合し、反応開始温度50℃で200分間反応させた。反応中の到達最高温度は、57℃であった。
イソシアヌレート化触媒として、トリメチルベンジルアンモニウムのハイドロオキサイド(40%メタノール溶液)に代えて、テトラブチルアンモニウムのハイドロオキサイド(37%メタノール溶液)を0.02質量部配合し、また、反応時間を300分に変更した以外は、実施例1と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、56℃であった。この反応における反応率は、21.7%であり、反応速度は速く、反応液にゲル化は確認されなかった。
温度計、撹拌装置、窒素導入管および冷却管が装着された反応機において、窒素雰囲気下、m−キシリレンジイソシアネート(三井化学社製、XDI)100質量部と、2,6−ジ(tert-ブチル)−4−メチルフェノール(別名:ジブチルヒドロキシトルエン、BHT、ヒンダードフェノール系酸化防止剤) 0.02質量部と、テトラフェニル・ジプロピレングリコール・ジホスファイト(有機亜リン酸エステル、助触媒) 0.05質量とを混合した後、この混合液に1,3−ブタンジオール 2質量部を加え、混合液を70℃に昇温した。
反応開始温度を60℃とした以外は、実施例2と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、74℃であった。この反応における反応率は、25.8%であり、反応速度は速く、反応液にゲル化は確認されなかった。
テトラブチルアンモニウムのハイドロオキサイド(37%メタノール溶液)の配合量を0.04質量部とし、また、反応開始温度を70℃とし、反応時間を320分に変更した以外は、実施例2と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、79℃であった。この反応における反応率は、33.5%であり、反応速度は速く、反応液にゲル化は確認されなかった。
テトラフェニル・ジプロピレングリコール・ジホスファイト(商品名JPP−100、城北化学工業社製、有機亜リン酸エステル、助触媒)0.05質量部に代えて、トリデシルホスファイト(商品名JP−310、城北化学工業社製、有機亜リン酸エステル、助触媒)0.05質量部を配合した以外は、実施例4と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、76℃であった。この反応における反応率は、30.0%であり、反応速度は速く、反応液にゲル化は確認されなかった。
テトラフェニル・ジプロピレングリコール・ジホスファイト(商品名JPP−100、城北化学工業社製、有機亜リン酸エステル、助触媒)を配合しなかった以外は、実施例4と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、75℃であった。この反応における反応率は、25.1%であり、反応速度は速く、反応液にゲル化は確認されなかった。
反応開始温度を80℃とし、反応時間を200分に変更した以外は、実施例2と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、90℃であった。この反応における反応率は、35.1%であり、反応速度は速く、反応液にゲル化は確認されなかったが、翌日に白濁物が確認された。
イソシアヌレート化触媒として、トリメチルベンジルアンモニウムのハイドロオキサイド(40%メタノール溶液)に代えて、TAP(化薬アクゾ社製、2,4,6−トリス(ジメチルアミノメチル)フェノール)を固形分として0.05質量部配合し、また、反応時間を300分に変更した以外は、実施例1と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、52℃であった。この反応における反応率は、16.9%であり、反応速度はやや遅く、反応液にゲル化は確認されなかった。
イソシアヌレート化触媒として、トリメチルベンジルアンモニウムのハイドロオキサイド(40%メタノール溶液)に代えて、DABCO−TMR(N−(2−ヒドロキシプロピル)−N,N,N−トリメチルアンモニウム−2−エチルヘキサノエート、エアープロダクツ社製)を固形分として0.02質量部配合し、また、反応時間を300分に変更した以外は、実施例1と同様にして、ポリイソシアヌレート組成物を得た。反応中の到達最高温度は、55℃であった。この反応における反応率は、19.7%であり、反応速度はやや遅く、反応液にわずかにゲル化が確認された。
イソシアヌレート化触媒として、トリメチルベンジルアンモニウムのハイドロオキサイド(40%メタノール溶液)に代えて、ナフテン酸のマグネシウム塩(マグネシウム含有量2%、59%ミネラルスピリット溶液)を固形分として0.2質量部配合し、また、反応開始温度を70℃に変更した以外は、実施例1と同様に反応させたが、7時間経過しても十分な量のポリイソシアヌレート組成物を得ることができなかった。反応中の到達最高温度は、73℃であった。なお、この反応における反応率は、1.1%であった。
XDI:m−キシリレンジイソシアネート(三井化学社製)
1,3−BG:1,3−ブタンジオール
TMB:トリメチルベンジルアンモニウムのハイドロオキサイド(40%メタノール溶液)
TBAOH:テトラブチルアンモニウムのハイドロオキサイド(37%メタノール溶液)
TAP:2,4,6−トリス(ジメチルアミノメチル)フェノール、化薬アクゾ社製
Naph.Mg:ナフテン酸のマグネシウム塩
DABCO−TMR:N−(2−ヒドロキシプロピル)−N,N,N−トリメチルアンモニウム−2−エチルヘキサノエート、エアープロダクツ社製
JPP−100:テトラフェニル・ジプロピレングリコール・ジホスファイト、城北化学工業社製、有機亜リン酸エステル、助触媒
JP−310:トリデシルホスファイト、城北化学工業社製、有機亜リン酸エステル、助触媒
各実施例において示すように、テトラアルキルアンモニウムのハイドロオキサイドをイソシアヌレート化触媒として用いると、ゲル化を抑制するとともに、優れた反応率でキシリレンジイソシアネートをイソシアヌレート化することができる。
Claims (6)
- キシリレンジイソシアネートをイソシアヌレート化触媒の存在下においてイソシアヌレート化反応させるポリイソシアヌレート組成物の製造方法であって、
前記イソシアヌレート化触媒が、4級アンモニウムのハイドロオキサイドであることを特徴とする、ポリイソシアヌレート組成物の製造方法。 - 前記イソシアヌレート化触媒が、テトラアルキルアンモニウムのハイドロオキサイド、および/または、トリアルキルヒドロキシアルキルアンモニウムのハイドロオキサイドであることを特徴とする、請求項1に記載のポリイソシアヌレート組成物の製造方法。
- 前記イソシアヌレート化反応における反応温度が、60℃以上80℃以下であることを特徴とする、請求項1に記載のポリイソシアヌレート組成物の製造方法。
- イソシアヌレート化反応において、助触媒として有機亜リン酸エステルを配合することを特徴とする、請求項1に記載のポリイソシアヌレート組成物の製造方法。
- 前記助触媒が、脂肪族有機亜リン酸エステルであることを特徴とする、請求項4に記載のポリイソシアヌレート組成物の製造方法。
- 請求項1に記載のポリイソシアヌレート組成物の製造方法により得られることを特徴とする、ポリイソシアヌレート組成物。
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