JP6344632B2 - ウレタン樹脂組成物、コーティング剤及び物品 - Google Patents
ウレタン樹脂組成物、コーティング剤及び物品 Download PDFInfo
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- JP6344632B2 JP6344632B2 JP2018504957A JP2018504957A JP6344632B2 JP 6344632 B2 JP6344632 B2 JP 6344632B2 JP 2018504957 A JP2018504957 A JP 2018504957A JP 2018504957 A JP2018504957 A JP 2018504957A JP 6344632 B2 JP6344632 B2 JP 6344632B2
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- urethane resin
- polyol
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- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims description 112
- 239000011248 coating agent Substances 0.000 title claims description 69
- 239000011342 resin composition Substances 0.000 title claims description 58
- 150000003077 polyols Chemical class 0.000 claims description 99
- 229920005862 polyol Polymers 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 64
- 238000000576 coating method Methods 0.000 claims description 54
- -1 alkylene diol Chemical class 0.000 claims description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 44
- 239000004417 polycarbonate Substances 0.000 claims description 35
- 229920000515 polycarbonate Polymers 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 229920005906 polyester polyol Polymers 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 17
- 239000005056 polyisocyanate Substances 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 124
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 33
- 239000000463 material Substances 0.000 description 28
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 28
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 20
- 239000000049 pigment Substances 0.000 description 20
- 239000004970 Chain extender Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 17
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000001273 butane Substances 0.000 description 13
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 229910000831 Steel Inorganic materials 0.000 description 9
- 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 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000010959 steel Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000007514 bases Chemical class 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
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003009 polyurethane dispersion Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 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 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 2
- QIPOUSKNIMYTRA-UHFFFAOYSA-N [2-hydroxy-3-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)butoxy]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COCCCCOCC(O)COC(=O)C=C QIPOUSKNIMYTRA-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003242 anti bacterial agent Substances 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
- 239000004202 carbamide Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
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- 230000002087 whitening effect Effects 0.000 description 2
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YUIOPHXTILULQC-UHFFFAOYSA-N 1,4-Dithiane-2,5-diol Chemical compound OC1CSC(O)CS1 YUIOPHXTILULQC-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- ROFVGYAMRSGUSQ-UHFFFAOYSA-N 1-(2-bromoethyl)piperazine;hydrobromide Chemical compound Br.BrCCN1CCNCC1 ROFVGYAMRSGUSQ-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Description
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)38.6質量部、1,6−ヘキサンジオール3.9質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリエステルポリオール(1,6−ヘキサンジオールとネオペンチルグリコールとアジピン酸とを反応させて得られるポリエステルポリオール、数平均分子量2000)38.6質量部、1,6−ヘキサンジオール3.9質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリテトラメチレンエーテルグリコール(数平均分子量2000)38.6質量部、1,6−ヘキサンジオール3.9質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン61.5質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)43.4質量部、1,6−ヘキサンジオール0.04質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン61.5質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)43.4質量部、1,6−ヘキサンジオール0.04質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)38.6質量部、1,6−ヘキサンジオール3.9質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン61.5質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)43.4質量部、1,6−ヘキサンジオール0.04質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、ペンタエリスリトールジアクリレート(一般式(1)中のR1は、炭素原子数3のもので、重合性不飽和基を有する原子団を2つ有するものである。)8.2質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)47.8質量部、1,6−ヘキサンジオール2.2質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)38.6質量部、1,6−ヘキサンジオール3.9質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン61.5質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)21.7質量部、ポリテトラメチレンエーテルグリコール(数平均分子量2000)21.7質量部、1,6−ヘキサンジオール0.04質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン61.5質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)43.4質量部、1,6−ヘキサンジオール0.04質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)38.6質量部、1,6−ヘキサンジオール3.9質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン61.5質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)43.4質量部、1,6−ヘキサンジオール0.04質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
加熱装置、攪拌機、温度計及び還流冷却管を備えた2リットル4つ口フラスコに、メチルエチルケトン23.7質量部、1,4−ビス(3−アクリロイロキシ−2−ヒドロキシプロキシ)ブタン(一般式(2)中のR1は炭素原子数2個、R2は炭素原子数4個、R3は炭素原子数2個、重合性不飽和基を有する原子団2個)12.1質量部、ポリカーボネートポリオール(1,6−ヘキサンジオールと1,5−ペンタンジオールとジエチルカーボネートとを反応させて得られるポリカーボネートポリオール、数平均分子量2000)38.6質量部、1,6−ヘキサンジオール3.9質量部、メチルヒドロキノン0.0024質量部、及び、2,6−tert−ブチル−p−クレゾール0.0242質量部を仕込み、攪拌しながら50℃で調整した。
光重合開始剤(1−ヒドロキシ−シクロヘキシル−フェニル−ケトンとベンゾフェノンの混合物)を、実施例及び比較例で得た各ウレタン樹脂組成物に含まれるウレタン樹脂100質量部あたり4質量部混合し、それを、塗膜の膜厚が10μmとなるように、それぞれガラス基材の表面に塗布した。前記塗布物を140℃で5分間乾燥した後、高圧水銀灯(株式会社GSユアサ製)を用いて、400mJ/cm2の紫外線を2パス照射し、前記ガラス基材の表面に塗膜が積層した物品を得た。
光重合開始剤(1−ヒドロキシ−シクロヘキシル−フェニル−ケトンとベンゾフェノンの混合物)を、実施例及び比較例で得た各ウレタン樹脂組成物に含まれるウレタン樹脂100質量部あたり4質量部混合し、それを、塗膜の膜厚が10μmとなるように、それぞれガラス基材の表面に塗布した。前記塗布物を140℃で5分間乾燥した後、高圧水銀灯(株式会社GSユアサ製)を用いて、500mJ/cm2の紫外線を1パス照射することによって、前記ガラス基材の表面に塗膜が積層した物品を得た。
光重合開始剤(1−ヒドロキシ−シクロヘキシル−フェニル−ケトンとベンゾフェノンの混合物)を、実施例及び比較例で得た各ウレタン樹脂組成物に含まれるウレタン樹脂100質量部あたり4質量部混合し、それを、塗膜の膜厚が10μmとなるように、それぞれPETフィルム(150μm)の表面に塗布した。前記塗布物を100℃で30秒間乾燥した後、高圧水銀灯(株式会社GSユアサ製)を用いて、400mJ/cm2の紫外線を2パス照射し、前記PETフィルムの表面に塗膜が積層した物品を得た。
Claims (4)
- 下記一般式(1)で示される2つ以上の重合性不飽和基を有するアルキレンジオール(a1−1)または下記一般式(2)で示される2つ以上の重合性不飽和基を有するオキシアルキレンジオール(a1−2)を含有するポリオール(a1)と、ポリイソシアネート(a2)との反応物であるウレタン樹脂(A)、多官能アクリレート(B)、及び、溶媒(C)を含有するウレタン樹脂組成物であって、
前記ウレタン樹脂(A)及び前記多官能アクリレート(B)の合計中の重合性不飽和結合の割合が2.5〜9.5mmol/gの範囲であり、
前記ウレタン樹脂(A)と前記多官能アクリレート(B)の質量比「多官能アクリレート(B)/ウレタン樹脂(A)」が、0.5〜4の範囲であり、
前記ポリオール(a1)が、さらにポリエステルポリオール、ポリカーボネートポリオール又はポリエーテルポリオールを含むものであることを特徴とするウレタン樹脂組成物。
- 前記多官能アクリレート(B)中の重合性不飽和結合の割合が、4〜12mmol/gの範囲である請求項1記載のウレタン樹脂組成物。
- 請求項1又は2記載のウレタン樹脂組成物からなるコーティング剤。
- 請求項3記載のコーティング剤の塗膜を有する物品。
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KR20200006873A (ko) * | 2018-07-11 | 2020-01-21 | 삼성에스디아이 주식회사 | 점착 필름, 이를 위한 점착제 조성물 및 이를 포함하는 디스플레이 부재 |
KR102210259B1 (ko) | 2018-07-11 | 2021-02-01 | 삼성에스디아이 주식회사 | 점착 필름, 이를 위한 점착제 조성물 및 이를 포함하는 디스플레이 부재 |
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KR102077485B1 (ko) | 2020-02-17 |
TWI740919B (zh) | 2021-10-01 |
WO2017164002A1 (ja) | 2017-09-28 |
JPWO2017164002A1 (ja) | 2018-07-12 |
US20200172656A1 (en) | 2020-06-04 |
TW201802201A (zh) | 2018-01-16 |
US11008417B2 (en) | 2021-05-18 |
KR20180110154A (ko) | 2018-10-08 |
CN108884200B (zh) | 2021-01-26 |
CN108884200A (zh) | 2018-11-23 |
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