JP6381474B2 - 硬化性ポリウレタン樹脂組成物および硬化物 - Google Patents
硬化性ポリウレタン樹脂組成物および硬化物 Download PDFInfo
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- JP6381474B2 JP6381474B2 JP2015071669A JP2015071669A JP6381474B2 JP 6381474 B2 JP6381474 B2 JP 6381474B2 JP 2015071669 A JP2015071669 A JP 2015071669A JP 2015071669 A JP2015071669 A JP 2015071669A JP 6381474 B2 JP6381474 B2 JP 6381474B2
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- mass
- meth
- acrylate
- polyol
- pentamethylene diisocyanate
- Prior art date
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- 229920005749 polyurethane resin Polymers 0.000 title claims description 72
- 239000011342 resin composition Substances 0.000 title claims description 65
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 99
- 229920005862 polyol Polymers 0.000 claims description 97
- 150000003077 polyols Chemical class 0.000 claims description 85
- 239000005056 polyisocyanate Substances 0.000 claims description 84
- 229920001228 polyisocyanate Polymers 0.000 claims description 84
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
- 229910052801 chlorine Inorganic materials 0.000 claims description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 37
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 103
- -1 isocyanate compound Chemical class 0.000 description 98
- 239000000203 mixture Substances 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 52
- 238000004519 manufacturing process Methods 0.000 description 41
- 238000004821 distillation Methods 0.000 description 30
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 28
- 239000003999 initiator Substances 0.000 description 25
- 239000012948 isocyanate Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 24
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- 238000003860 storage Methods 0.000 description 21
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 13
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229940059574 pentaerithrityl Drugs 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 9
- 229920000193 polymethacrylate Polymers 0.000 description 9
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 8
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- 239000007787 solid Substances 0.000 description 8
- 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 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 description 7
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- 229920000909 polytetrahydrofuran Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002009 diols Chemical class 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 150000003839 salts Chemical class 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 229920001610 polycaprolactone Polymers 0.000 description 5
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
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- 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 3
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- KWYLNOQTLCTWCF-UHFFFAOYSA-L copper oct-2-enoate Chemical compound [Cu+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O KWYLNOQTLCTWCF-UHFFFAOYSA-L 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
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- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
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- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
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- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
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- 239000000806 elastomer Substances 0.000 description 1
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- 239000012634 fragment Substances 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- MAWWBGJQKJTVHJ-UHFFFAOYSA-M hexadecanoate;triethyl(2-hydroxypropyl)azanium Chemical compound CC[N+](CC)(CC)CC(C)O.CCCCCCCCCCCCCCCC([O-])=O MAWWBGJQKJTVHJ-UHFFFAOYSA-M 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- PPHNBXJJZWRPEN-UHFFFAOYSA-M hexanoate;2-hydroxyethyl-(2-hydroxypropyl)-dimethylazanium Chemical compound CCCCCC([O-])=O.CC(O)C[N+](C)(C)CCO PPHNBXJJZWRPEN-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- NFMHSPWHNQRFNR-UHFFFAOYSA-N hyponitrous acid Chemical class ON=NO NFMHSPWHNQRFNR-UHFFFAOYSA-N 0.000 description 1
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- 238000007641 inkjet printing Methods 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
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- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- 150000002611 lead compounds Chemical class 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
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- 239000004973 liquid crystal related substance Substances 0.000 description 1
- ZADRSPBLAQBZEC-UHFFFAOYSA-N lithium;pentane-2,4-dione Chemical compound [Li].CC(=O)CC(C)=O ZADRSPBLAQBZEC-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
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- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- ODYNBECIRXXOGG-UHFFFAOYSA-N n-butylbutan-1-amine;hydron;chloride Chemical compound [Cl-].CCCC[NH2+]CCCC ODYNBECIRXXOGG-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
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- ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
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- 150000001451 organic peroxides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- OXQKEKGBFMQTML-BIVRFLNRSA-N perseitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-BIVRFLNRSA-N 0.000 description 1
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- PWGIEBRSWMQVCO-UHFFFAOYSA-N phosphono prop-2-enoate Chemical compound OP(O)(=O)OC(=O)C=C PWGIEBRSWMQVCO-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002984 plastic foam Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- YMPPRYJBYFNJTO-UHFFFAOYSA-M sodium;diethoxy-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Na+].CCOP([O-])(=S)OCC YMPPRYJBYFNJTO-UHFFFAOYSA-M 0.000 description 1
- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003606 tin 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
- SBUXRMKDJWEXRL-ZWKOTPCHSA-N trans-body Chemical compound O=C([C@@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ZWKOTPCHSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BXJWDOYMROEHEN-UHFFFAOYSA-N tributylstibane Chemical compound CCCC[Sb](CCCC)CCCC BXJWDOYMROEHEN-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
- 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
- 239000013638 trimer Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
ペンタメチレンジイソシアネートの純度は、後述する製造例1で得られたペンタメチレンジイソシアネート(a)を用い、以下のGC分析条件下で得られたクロマトグラムの面積値から検量線を作成し、ペンタメチレンジイソシアネートの純度を算出した。
カラム;UADX−30(フロンティア・ラボ社製)0.25mmφ×30m、膜厚0.15μm
オーブン温度;50℃で5分間保持、50℃から200℃まで、10℃/minで昇温、200℃から350℃まで、20℃/minで昇温、350℃で7.5分間保持
注入口温度;250℃
検出器温度;250℃
He流量 ; 1.2mL/min
注入モード ; スプリット
検出方法;FID
<塩素濃度(単位:ppm>
試料を200mg秤量し、Ar/O2気流中、900℃の燃焼炉にて燃焼分解した。発生したガスを吸収液に吸収させ、イオンクロマトグラフ法にて塩素濃度を定量した。
装置:イオンクロマトグラフICS−1500(サーモフィッシャーサイエンティフィック製)
<式(1)で示される化合物の濃度(単位:ppm)>
以下の装置および条件にてGC分析を行い、式(1)で示される化合物の面積比率を、式(1)で示される化合物の濃度とした。
カラム;DB−5MS+DG(アジレント・テクノロジー社製)0.25mmφ×30m、膜厚0.25μm
オーブン温度;40℃で5分間保持、40℃から220℃まで、10℃/minで昇温
注入口温度;200℃
検出器温度;250℃
検出方法:FID
He流量 ; 4mL/min
注入モード ; スプリット
スプリット比:50/1
<イソシアネート基の反応率(単位:%)>
イソシアネート基の反応率は、電位差滴定装置を用いて、JIS K−1603−1(2007年)に準拠したトルエン/ジブチルアミン・塩酸法によりイソシアネート含有率を測定し、以下の式より算出した。
<イソシアネートモノマーの濃度(単位:質量%)>
後述する製造例1で得られたペンタメチレンジイソシアネート(a)または市販のヘキサメチレンジイソシアネートを標準物質として用い、ジベンジルアミンによりラベル化させ、以下のHPLC分析条件下で得られたクロマトグラムの面積値から作成した検量線により、未反応のイソシアネートモノマー(ペンタメチレンジイソシアネート、ヘキサメチレンジイソシアネート)の濃度を算出した。
装置;Prominence(島津製作所社製)
1) ポンプ LC−20AT
2) デガッサ DGU−20A3
3) オートサンプラ SIL−20A
4) カラム恒温槽 COT−20A
5) 検出器 SPD−20A
カラム;SHISEIDO SILICA SG−120
カラム温度;40℃
溶離液;n−ヘキサン/メタノール/1,2−ジクロロエタン=90/5/5(体積比)
流量;0.2mL/min
検出方法;UV 225nm
<イソシアネート基含有率(単位:質量%)>
イソシアネート基含有率は、電位差滴定装置を用いて、JIS K−1603−1(2007年)に準拠したトルエン/ジブチルアミン・塩酸法による測定結果に基いて算出した。
東機産業社製のE型粘度計TV−30を用いて、25℃における粘度を測定した。
製造例1(ペンタメチレンジイソシアネート(a)の製造)
国際公開パンフレットWO2012/121291号の明細書における実施例1と同様の操作にて、99.9質量%のペンタメチレンジイソシアネート(a)(以後PDI(a)と略する場合がある。)を得た。
PDI(a)を以下のGC−MS分析条件で測定した結果、MSスペクトルのフラグメントイオンとしてm/z:55、68、85、112にピークを持ち、148、150の強度比が約3対1であり、1原子中に塩素原子を1つ持つ化合物が検出され、式(1)で表される化合物と推定した。
装置;Q1000GC K9(日本電子社製)
イオン化法;EI、CI
カラム;DB−5MS+DG(アジレント・テクノロジー社製)0.25mmφ×30m、膜厚0.25μm
オーブン温度;40℃で5分間保持、40℃から220℃まで、10℃/minで昇温
注入口温度;200℃
検出器温度;250℃
He流量 ; 4mL/min
注入モード ; スプリット
スプリット比;50/1
イオン源温度;200℃
イオン化電流;200μA
製造例2(ペンタメチレンジイソシアネート(b)の製造)
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率35〜80%の留分を採取した。得られたペンタメチレンジイソシアネート(b)の純度は99.9質量%、塩素濃度は14ppm、式(1)で示される化合物の濃度は24ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率13〜80%の留分を採取した。得られたペンタメチレンジイソシアネート(c)の純度は99.8質量%、塩素濃度は477ppm、式(1)で示される化合物の濃度は1103ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率20〜70%の留分を採取した。得られたペンタメチレンジイソシアネート(c)の純度は99.9質量%、塩素濃度は8ppm、式(1)で示される化合物の濃度は31ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率20〜88%の留分を採取した。得られたペンタメチレンジイソシアネート(e)の純度は99.9質量%、塩素濃度は511ppm、式(1)で示される化合物の濃度は386ppmであった。
製造例6(ペンタメチレンジイソシアネート(f)の製造)
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率35〜70%の留分を採取した。得られたペンタメチレンジイソシアネート(f)の純度は99.9質量%、塩素濃度は7ppm、式(1)で示される化合物の濃度は28ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率13〜88%の留分を採取した。得られたペンタメチレンジイソシアネート(g)の純度は99.8質量%、塩素濃度は562ppm、式(1)で示される化合物の濃度は1037ppmであった。
合成例1(ポリイソシアネート組成物(a)の合成)
撹拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、PDI(a)を500質量部、イソブチルアルコール(以後IBAと略する場合がある)を0.5質量部、2,6−ジ(tert−ブチル)−4−メチルフェノール(以後BHTと略する場合がある)を0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部装入し、80℃で2時間ウレタン化反応を行った。
表2に記載のポリイソシアネート化合物を用いた以外は、合成例1と同様の操作にてポリイソシアネート組成物(b)〜(g)を得た。なお、合成例5および7においては、塩化ベンゾイルの配合量を、0.003質量部から0.15質量部に変更した。
撹拌機、温度計、還流管、および、窒素導入管を備えた4つ口フラスコに、ヘキサメチレンジイソシアネート(商品名:タケネート700、三井化学製、以後HDIと略する場合がある)を500質量部、イソブチルアルコールを0.4質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部装入し、80℃で2時間ウレタン化反応を行った。
実施例1(硬化性ポリウレタン樹脂組成物(A)の製造)
撹拌機、温度計、還流管、および、乾燥空気導入管を備えた5つ口フラスコに、PDI(a)を100質量部、アロニックスM305(ペンタエリスリトールトリアクリレート(55〜63%)と、ペンタエリスリトールテトラアクリレート(37〜43%)との混合物、東亞合成社製)を664.5質量部、ハイドロキノンメチルエーテル(以後、MEHQと略する場合がある)を0.5質量部、酢酸エチルを143.4質量部仕込み、65℃で2時間反応させた。その後、ジブチルスズジラウレートを0.1質量部添加し、さらに3時間反応させ、イソシアネート基含有率が0.1%以下となった時点でイソプロパノールを47.8質量部添加し、硬化性ポリウレタン樹脂組成物(A)を得た。硬化性ポリウレタン樹脂組成物(A)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
撹拌機、温度計、還流管、および、乾燥空気導入管を備えた5つ口フラスコに、合成例1で得られたポリイソシアネート組成物(a)を100質量部、アロニックスM305を249.9質量部、2−ヒドロキシエチルアクリレート(以後、HEAと略する場合がある)を11.9質量部、MEHQを0.5質量部、酢酸エチルを116.3質量部、仕込み、65℃で2時間反応させた。その後、ジブチルスズジラウレートを0.1質量部添加し、さらに3時間反応させ、イソシアネート基含有率が0.1%以下となった時点でイソプロパノールを38.8質量部添加し、硬化性ポリウレタン樹脂組成物(B)を得た。硬化性ポリウレタン樹脂組成物(B)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
撹拌機、温度計、還流管、および、乾燥空気導入管を備えた5つ口フラスコに、PDI(a)を100質量部、アロニックスM403(ジペンタエリスリトールペンタアクリレート(50〜60%)と、ジペンタエリスリトールヘキサアクリレート(40〜50%)との混合物、東亞合成社製)を747.6質量部、MEHQを0.5質量部、酢酸エチルを159質量部仕込み、65℃で2時間反応させた。その後、ジブチルスズジラウレートを0.1質量部添加し、さらに3時間反応させ、イソシアネート基含有率が0.1%以下となった時点でイソプロパノールを53質量部添加し、硬化性ポリウレタン樹脂組成物(C)を得た。硬化性ポリウレタン樹脂組成物(C)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
撹拌機、温度計、還流管、窒素導入管、および、乾燥空気導入管を備えた5つ口フラスコに、PDI(a)を100質量部、トリメチロールプロパンを29質量部、酢酸エチルを64.5質量部挿入し、75℃で4時間反応させ、イソシアネート基含有率が所定の値に達した後、60℃まで冷却した。次いで、MEHQを0.1質量部、HEAを79.1質量部添加し、65℃で2時間反応させた。その後、ジブチルスズジラウレートを0.1質量部添加し、さらに3時間反応させ、イソシアネート基含有率が0.1%以下となった時点でイソプロパノールを21.5質量部添加し、硬化性ポリウレタン樹脂組成物(D)を得た。硬化性ポリウレタン樹脂組成物(D)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
撹拌機、温度計、還流管、窒素導入管、および、乾燥空気導入管を備えた5つ口フラスコに、PDI(a)を100質量部、プラクセル205(PCL205、ポリカプロラクトンジオール、分子量530、ダイセル社製)を85.9質量部、プラクセル303(PCL305、ポリカプロラクトントリオール、分子量550、ダイセル社製)を48.6質量部酢酸エチルを34.9質量部挿入し、75℃で4時間反応させ、イソシアネート基含有率が所定の値に達した後、65℃まで冷却した。次いで、MEHQを0.1質量部、HEAを99.7質量部、質量部添加し、65℃で2時間反応させた。その後、ジブチルスズジラウレートを0.1質量部添加し、さらに3時間反応させ、イソシアネート基含有率が0.1%以下となった時点でイソプロパノールを11.6量部添加し、硬化性ポリウレタン樹脂組成物(E)を得た。硬化性ポリウレタン樹脂組成物(E)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
プラクセル205(PCL205、ポリカプロラクトンジオール、分子量530、ダイセル社製)に代えて、UH−50(ETERNACOLL UH−50、ポリカーボネートジオール、分子量500、宇部興産社製)またはPTG−650(ポリテトラメチレンエーテルグリコール、分子量650、保土ヶ谷化学社製)を用い、また、各成分の配合量を表3に記載の通りとした以外は、実施例5と同様の操作にて硬化性ポリウレタン樹脂組成物(F)〜(G)を得た。硬化性ポリウレタン樹脂組成物(F)〜(G)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
表3に記載のポリイソシアネートを使用した以外は、実施例1と同様の操作にて硬化性ポリウレタン樹脂組成物(H)〜(M)を得た。硬化性ポリウレタン樹脂組成物(H)〜(M)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
表3に記載のポリイソシアネートを使用した以外は、実施例2と同様の操作にて硬化性ポリウレタン樹脂組成物(N)〜(S)を得た。硬化性ポリウレタン樹脂組成物(N)〜(S)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った後、粘度を測定し、粘度増加率を算出した。
ヘキサメチレンジイソシアネート(商品名:タケネート700、三井化学製、塩素濃度201ppm)を使用した以外は、実施例1と同様の操作にて硬化性ポリウレタン樹脂組成物(T)を得た。硬化性ポリウレタン樹脂組成物(T)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った。貯蔵安定性試験後の硬化性ポリウレタン樹脂組成物(T)は白濁し粘度を測定することができなかった。
表3に記載のポリイソシアネートを使用した以外は、実施例2と同様の操作にて硬化性ポリウレタン樹脂組成物(U)を得た。硬化性ポリウレタン樹脂組成物(U)の粘度を測定し、初期粘度とした。その後、1℃の冷蔵庫で一か月間貯蔵安定性試験を行った。貯蔵安定性試験後の硬化性ポリウレタン樹脂組成物(U)は固化し粘度を測定することができなかった。
実施例20〜38および比較例3〜4(ポリウレタン樹脂(A)〜(U)の製造)
表3に記載の硬化性ポリウレタン樹脂組成物と、硬化性ポリウレタン樹脂組成物の固形分に対し5重量%の光重合開始剤(商品名:Irgacure184、BASFジャパン社製)、さらに混合液の粘度が30〜50mPa・sとなるようにイソプロパノールを添加後、23℃で90秒間撹拌した。次いで、この混合液をポリカーボネート板(商品名:PC1600、タキロン社製)に塗布し、60℃で5分間加温し、紫外線照射量900mJ/cm2にて硬化させ、厚みが15μmのポリウレタン樹脂(A)〜(U)を得た。
各実施例および各比較例で得られたポリウレタン樹脂の耐擦傷性を、以下の方法で測定した。その結果を表4に示す。
ポリウレタン樹脂の光沢を測定した後、スチールウール(番手:♯0000、日本スチールウール社製)に1kg荷重を加えポリウレタン樹脂の表面を10往復させた。その後ポリウレタン樹脂の光沢を測定し、光沢保持率を算出した。
TMP:トリメチロールプロパン
PCL205:プラクセル205、ポリカプロラクトンジオール、分子量530、ダイセル社製
UH−50:ETERNACOLL UH−50、ポリカーボネートジオール、分子量500、宇部興産社製
PTG−650:ポリテトラメチレンエーテルグリコール、分子量650、保土ヶ谷化学社製
PCL303:プラクセル303、ポリカプロラクトントリオール、分子量550、ダイセル社製
アロニックスM305:ペンタエリスリトールトリアクリレート(55〜63%)と、ペンタエリスリトールテトラアクリレート(37〜43%)との混合物、東亞合成社製
HEA:2−ヒドロキシエチルアクリレート
アロニックスM403:ジペンタエリスリトールペンタアクリレート(50〜60%)と、ジペンタエリスリトールヘキサアクリレート(40〜50%)との混合物、東亞合成社製
MEHQ:ハイドロキノンメチルエーテル
Claims (4)
- 少なくとも、ペンタメチレンジイソシアネートおよび/またはその誘導体を含むポリイソシアネートと、エチレン性不飽和基およびヒドロキシル基を含有するヒドロキシル基含有不飽和化合物とを反応させることにより得られ、および/または、
少なくとも、前記ポリイソシアネートと、ポリオールと、前記ヒドロキシル基含有不飽和化合物とを反応させることにより得られ、
エチレン性不飽和基を含むウレタン樹脂を含有することを特徴とする、硬化性ポリウレタン樹脂組成物。 - 前記ポリイソシアネートの塩素濃度が、10ppm以上500ppm以下であることを特徴とする、請求項1に記載の硬化性ポリウレタン樹脂組成物。
- 請求項1〜3のいずれか一項に記載の硬化性ポリウレタン樹脂組成物を、活性エネルギー線の照射により、硬化させることにより得られることを特徴とする、硬化物。
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