JP6250138B2 - イソシアヌレート組成物 - Google Patents
イソシアヌレート組成物 Download PDFInfo
- Publication number
- JP6250138B2 JP6250138B2 JP2016506515A JP2016506515A JP6250138B2 JP 6250138 B2 JP6250138 B2 JP 6250138B2 JP 2016506515 A JP2016506515 A JP 2016506515A JP 2016506515 A JP2016506515 A JP 2016506515A JP 6250138 B2 JP6250138 B2 JP 6250138B2
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- Japan
- Prior art keywords
- isocyanurate
- mass
- less
- composition
- reaction
- 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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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 title claims description 175
- 239000000203 mixture Substances 0.000 title claims description 131
- -1 xylylene isocyanurate derivatives Chemical class 0.000 claims description 34
- 239000012948 isocyanate Substances 0.000 claims description 10
- 150000002513 isocyanates Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 description 68
- 229920005862 polyol Polymers 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 37
- 150000003077 polyols Chemical class 0.000 description 35
- 229920005749 polyurethane resin Polymers 0.000 description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 30
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 29
- 239000005056 polyisocyanate Substances 0.000 description 25
- 229920001228 polyisocyanate Polymers 0.000 description 25
- 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 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- 238000002156 mixing Methods 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- 238000001035 drying Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- 238000004821 distillation Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 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 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000000565 sulfonamide group Chemical group 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 150000008301 phosphite esters Chemical class 0.000 description 3
- 229920000582 polyisocyanurate Polymers 0.000 description 3
- 239000011495 polyisocyanurate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- 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 2
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-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
- 239000004480 active ingredient Substances 0.000 description 2
- 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 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
- 238000007865 diluting Methods 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000002649 leather substitute Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VSLDMOKTYQLSAZ-UHFFFAOYSA-N tetrabutylphosphanium;hydrofluoride Chemical compound F.CCCC[P+](CCCC)(CCCC)CCCC VSLDMOKTYQLSAZ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- QMTFKWDCWOTPGJ-KVVVOXFISA-N (z)-octadec-9-enoic acid;tin Chemical compound [Sn].CCCCCCCC\C=C/CCCCCCCC(O)=O QMTFKWDCWOTPGJ-KVVVOXFISA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LFEXGBPVZBXATF-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(S(N)(=O)=O)=C1C LFEXGBPVZBXATF-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
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- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-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
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Images
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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Description
<イソシアヌレート組成物の蒸留収率>
イソシアヌレート組成物の蒸留収率は、反応混合液(蒸留前液)およびイソシアヌレート組成物(蒸留後液)の質量をそれぞれ測定し、下記式により反応混合液の質量に対するイソシアヌレート組成物の質量の割合を算出することにより求めた。
<イソシアネート基濃度(質量%)、および、イソシアネート基の転化率(反応率)(質量%)>
仕込み液、反応混合液およびイソシアヌレート組成物のイソシアネート基濃度を、JIS K−1556(2006年)のn−ジブチルアミン法に準拠してそれぞれ測定した。
なお、イソシアネート基の転化率が、イソシアヌレート転化率である。
<イソシアヌレート一核体の含有割合(一核体含有率)(質量%)>
イソシアヌレート組成物のサンプルをゲルパーミエーションクロマトグラフィ(GPC)測定し、得られたクロマトグラム(チャート)において、ポリスチレン換算分子量400〜1000の間をピークトップとするピークの面積の、全ピークの面積に対する面積率から、3分子体面積率を求め、その3分子体面積率が、イソシアヌレート組成物の総量に対する、イソシアヌレート一核体の含有割合(一核体含有率)に相当するとした。
(1)分析装置 : Alliance(Waters)
(2)ポンプ : Alliance 2695(Waters)
(3)検出器 : 2414型示差屈折検出器(Waters)
(4)溶離液 : Tetrahydrofuran
(5)分離カラム :Plgel GUARD + Plgel 5μmMixed−C×3本(50×7.5mm,300×7.5mm)
メーカー ; Polymer Laboratories
品番 ; PL1110−6500
(6)測定温度 : 40℃
(7)流速 : 1mL/min
(8)サンプル注入量 : 100μL
(9)解析装置 : EMPOWERデータ処理装置(Waters)
・システム補正
(1)標準物質名 : Polystyrene
(2)検量線作成方法 : 分子量の異なるTOSOH社製 TSKstandard Polystyreneを用い、リテンションタイム(保持時間)と分子量とのグラフを作成。
(3)注入量、注入濃度 : 100μL、 1mg/mL
なお、実施例3のイソシアヌレート組成物のゲルパーミエーションクロマトグラムを図1に示す。
<粘度>
コーンプレート粘度計(モデル:CV−1S、コーン:100Pコーン(角度:2.0°、直径:14.5mm)、東亜工業社製)を用いて、JIS K5600−2−3(2014年)のコーン・プレート粘度計法に準拠して、特定の温度(60℃、80℃、100℃)での粘度を測定した。測定時のコーンプレートの回転数は、粘度が高くなるのに合わせて、750rpm、375rpm、188rpm、94rpm、75rpmと順次変更した。
<イソシアヌレート組成物の製造>
実施例1
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、窒素雰囲気下、1,3−キシリレンジイソシアネート(三井化学社製、m−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(安定剤))0.025phr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(JPP−100(商品名、城北化学工業社製)、有機亜リン酸エステル、助触媒)0.05phrとを仕込んだ後、この仕込み液に、イソシアヌレート化触媒として、テトラブチルアンモニウムのハイドロオキサイド(TBAOH)の37質量%メタノール溶液0.016phr(有効成分(触媒)100%換算:0.006phr)を配合し、反応開始温度60℃で反応させた。その後、反応中に、テトラブチルアンモニウムのハイドロオキサイド(TBAOH)の37質量%メタノール溶液0.0024phr(有効成分(触媒)100%換算:0.009phr)を追加して、反応開始から120分で反応を終了させ、反応混合液を得た。反応中の到達最高温度は、68℃であった。なお、仕込み液のイソシアネート基濃度は、44.7質量%であり、反応混合液のイソシアネート基濃度は、40.8質量%であった。
表1〜3に示す処方および製造条件に変更したこと以外は、実施例1と同様にして、イソシアヌレート誘導体からなるイソシアヌレート組成物を得た。
m−XDI:1,3−キシリレンジイソシアネート(三井化学社製)
p−XDI:1,4−キシリレンジイソシアネート(三井化学社製)
TBAOH:テトラブチルアンモニウムのハイドロオキサイドの37質量%メタノール溶液
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(芳香族有機亜リン酸エステル、城北化学工業社製、商品名)
BHT:2,6−ジ(tert−ブチル)−4−メチルフェノール(ヒンダードフェノール系酸化防止剤(安定剤))
Irg1076:イルガノックス1076(ヒンダードフェノール系酸化防止剤(安定剤)、チバ・ジャパン社製、商品名)
比較例4
市販のキシリレンジイソシアネートのトリメチロールプロパン変性体(商品名:D−110N、NCO基含有率:11.5重量%、固形分75重量%、溶剤:酢酸エチル、粘度(25℃):500mPa・s、三井化学社製)をそのまま用いた。
市販の1,6−ヘキサメチレンジイソシアネートのイソシアヌレート誘導体(商品名:D−170N、NCO基含有率:20.7重量%、固形分100重量%、粘度(25℃):200mPa・s、三井化学社製)をそのまま用いた。
市販のビス(イソシアナトメチル)シクロヘキサンのイソシアヌレート誘導体(商品名:D−127N、NCO基含有率:13.5重量%、固形分75重量%、溶剤:酢酸エチル、粘度(25℃):40mPa・s、三井化学社製)をそのまま用いた。
<評価>
(塗工溶液の調製)
各実施例および各比較例で得られたイソシアヌレート組成物と、アクリルポリオール(三井化学社製、商品名:オレスターQ666、以下、Q666と略する。)とを、イソシアヌレート組成物中のイソシアネート基に対するアクリルポリオール中の水酸基の当量比(NCO/OH)が1.0となる割合で配合し、シンナー(酢酸エチル/プロピレングリコールモノメチルエーテルアセテート/酢酸ブチルを重量比1:1:1で混合したもの)で、固形分50質量%になるように希釈した後に、23℃で5分間攪拌した。さらに、10分間超音波処理することにより、脱泡して、塗工溶液を得た。
(ウレタン皮膜の作製)
上記方法により得られた塗工溶液を、ポリメチルメタクリレート(PMMA)板上に乾燥膜厚が40μmになるように、また、ガラス板上に乾燥膜厚が100μmになるようにそれぞれ塗工した。23℃で2時間乾燥後に、80℃で30分熱処理した。その後、23℃、相対湿度55%で7日間熟成することにより、PMMA板上およびガラス板上にウレタン皮膜をそれぞれ得た。
<物性評価>
各実施例および各比較例の塗工溶液およびウレタン皮膜を用いて、下記の物性についてそれぞれ評価した。
(指触乾燥時間)
アプリケータ―を用いて100μmの厚み(乾燥前厚み)になるように塗工溶液をガラス板上に塗工した。塗工後、23℃、相対湿度30%の条件下で、指で触った時にタックがなくなるまでの時間を測定した。
(硬化乾燥時間)
アプリケータ―を用いて100μmの厚み(乾燥前厚み)になるように塗工溶液をガラス板上に塗工した。塗工後、23℃、相対湿度30%の条件下で、指を強く押し付けた時に指紋の跡がつかなくなるまでの時間を測定した。
(フィルム状態の相溶性の評価)
ガラス板上に塗工したウレタン皮膜のヘイズを、ヘイズメーター(日本電色工業社製、NDH2000)にて評価した。
(耐候性の評価)
促進耐候性試験機(デューパネル光コントロールウェザーメーター、スガ試験機社製)にて、PMMA板上に塗工したウレタン皮膜を、昼間(60℃×相対湿度10%×4時間×光照射)、夜間(50℃×相対湿度95%×4時間×光照射なし)のサイクルで600時間処理した。光沢度を光沢度計(日本電色工業社製、VG2000)にて評価し、初期の光沢度を100としたときの光沢保持率(600時間後)を算出した。
D−110N:キシリレンジイソシアネートのトリメチロールプロパン変性体(NCO基含有率:11.5重量%、固形分75重量%、溶剤:酢酸エチル、粘度(25℃):500mPa・s、三井化学社製)
D−170N:1,6−ヘキサメチレンジイソシアネートのイソシアヌレート誘導体(NCO基含有率:20.7重量%、固形分100重量%、粘度(25℃):200mPa・s、三井化学社製)
D−127N:ビス(イソシアナトメチル)シクロヘキサンのイソシアヌレート誘導体(NCO基含有率:13.5重量%、固形分75重量%、溶剤:酢酸エチル、粘度(25℃):40mPa・s、三井化学社製)
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、後記特許請求の範囲に含まれる。
Claims (3)
- 1,3−キシリレンジイソシアネートのイソシアヌレート誘導体から本質的になり、100℃における粘度が、600mPa・s以上20000mPa・s以下であり、
イソシアヌレート一核体の含有割合が、前記イソシアヌレート組成物の総量に対して、30質量%以上85質量%以下である
ことを特徴とする、イソシアヌレート組成物。 - 前記100℃における粘度が、1500mPa・s以上12000mPa・s以下であることを特徴とする、請求項1に記載のイソシアヌレート組成物。
- 前記イソシアヌレート一核体の含有割合が、前記イソシアヌレート組成物の総量に対して、40質量%以上70質量%以下であることを特徴とする、請求項1または2に記載のイソシアヌレート組成物。
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