JP5991814B2 - 水性照射硬化性ポリウレタン組成物 - Google Patents
水性照射硬化性ポリウレタン組成物 Download PDFInfo
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- JP5991814B2 JP5991814B2 JP2011512082A JP2011512082A JP5991814B2 JP 5991814 B2 JP5991814 B2 JP 5991814B2 JP 2011512082 A JP2011512082 A JP 2011512082A JP 2011512082 A JP2011512082 A JP 2011512082A JP 5991814 B2 JP5991814 B2 JP 5991814B2
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- Prior art keywords
- polyurethane
- compounds
- compound
- ethylenically unsaturated
- curable composition
- Prior art date
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 97
- 239000004814 polyurethane Substances 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 230000005855 radiation Effects 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 25
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 14
- 239000012736 aqueous medium Substances 0.000 claims abstract description 9
- 150000002433 hydrophilic molecules Chemical class 0.000 claims abstract description 9
- -1 diacrylate ester compounds Chemical class 0.000 claims description 67
- 229920005862 polyol Polymers 0.000 claims description 40
- 238000000576 coating method Methods 0.000 claims description 31
- 239000011248 coating agent Substances 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Chemical class 0.000 claims description 9
- 230000003472 neutralizing effect Effects 0.000 claims description 8
- 229920000768 polyamine Polymers 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920002873 Polyethylenimine Chemical class 0.000 claims description 4
- WRAGBEWQGHCDDU-UHFFFAOYSA-M C([O-])([O-])=O.[NH4+].[Zr+] Chemical compound C([O-])([O-])=O.[NH4+].[Zr+] WRAGBEWQGHCDDU-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000004970 Chain extender Substances 0.000 abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 10
- 239000001257 hydrogen Substances 0.000 abstract description 10
- 239000006185 dispersion Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 16
- 238000011109 contamination Methods 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 15
- 150000002513 isocyanates Chemical class 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
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- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 229920003009 polyurethane dispersion Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 125000000129 anionic group Chemical group 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
- 238000009835 boiling Methods 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 239000011362 coarse particle Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000006748 scratching Methods 0.000 description 4
- 230000002393 scratching effect Effects 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 230000004931 aggregating effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000015220 hamburgers Nutrition 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical group CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- 235000014443 Pyrus communis Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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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 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229920005628 alkoxylated polyol Polymers 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical class C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
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- 239000012467 final product Substances 0.000 description 2
- 238000004442 gravimetric analysis Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- AULUDJRRNHDTJI-UHFFFAOYSA-N 1,1,3,3-tetramethylcyclohexane Chemical group CC1(C)CCCC(C)(C)C1 AULUDJRRNHDTJI-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
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- 229940043375 1,5-pentanediol Drugs 0.000 description 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 1
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- AREWWPRVYOZSFA-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;propane-1,2,3-triol Chemical compound OCC(O)CO.OCC(CO)(CO)CO AREWWPRVYOZSFA-UHFFFAOYSA-N 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
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- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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Description
−少なくとも1種のポリイソシアネート化合物(Ai)、イソシアネート基と反応することができる少なくとも2個の反応性基を含有する少なくとも1種のエチレン性不飽和化合物(Aii)、イソシアネート基と反応することができる少なくとも1個の反応性基を含有し、および直接に、または中和剤との反応により塩を形成した後、当該ポリウレタンプレポリマーを水性媒質中で分散性にすることができる少なくとも1種の親水性化合物(Aiii)、イソシアネート基と反応することができ、連鎖延長をもたらす少なくとも1種の活性水素含有連鎖延長剤(Avii)、および任意に、1種または2種以上のポリオール(Avi)の反応から得られる少なくとも1種の高分子量エチレン性不飽和ポリウレタン(A);
−ポリウレタン(A)とは相違しており、少なくとも1種のポリイソシアネート化合物(Bi)、イソシアネート基と反応することができる少なくとも2個の反応性基を含有する少なくとも1種のエチレン性不飽和化合物(Bii)、イソシアネート基と反応することができる少なくとも1個の反応性基を含有し、直接に、または中和剤との反応により塩を形成した後、当該ポリウレタンプレポリマーを水性媒質中で分散性にすることができる少なくとも1種の親水性化合物(Biii)、イソシアネート基と反応することができる基本的に1個の反応性基を含有する少なくとも1種のエチレン性不飽和化合物(Biv)、および任意に、1種または2種以上のポリオール(Bvi)および/または1種または2種以上の活性水素含有連鎖延長剤(Bvii)の反応から得られる少なくとも1種の低分子量エチレン性不飽和ポリウレタン(B);
を含んでいる。
−化合物(Ai)、(Aii)、(Aiii)および場合により、化合物(Avi)の反応を含むポリウレタンプレポリマーを形成する第一工程;
−化合物(Aiii)によって提供される親水性基をアニオン性塩に変換する中和剤との反応を含む任意の第二工程;
−第一工程または第二工程後、得られたポリウレタンプレポリマーを水性媒質中に分散させることを含む工程;
−エチレン性不飽和ポリウレタンプレポリマーを少なくとも1種の活性水素含有連鎖延長剤(Avii)と反応させる工程;
を含む方法によって得られる。
−化合物(Bi)、(Bii)、(Biii)および場合により、化合物(Bvi)の反応を含む第一工程;
−第一工程後に得られたプレポリマーを、イソシアネート基と反応することができる基本的に1個の反応性基を含有する少なくとも1種のエチレン性不飽和化合物(Biv)と反応させる第二工程;
−化合物(Biii)によって提供される親水性基をアニオン性塩に変換する中和剤との反応を含む任意の第三工程;
−第二工程または第三工程後に得られたポリウレタンプレポリマーを水性媒質中に分散させることを含む第四工程;
−エチレン性不飽和ポリウレタンを少なくとも1種の活性水素含有連鎖延長剤(Bvii)と反応させる任意の工程;
を含む方法によって得られる。
(例)
機械的攪拌機を備えた反応器に、上記とおりのポリウレタン分散液A1 400gを周辺温度で装入し、次いで上記とおりのポリウレタン分散液B1 600gを均一混合物が得られるまで低せん断下にゆっくり添加した。この混合物のMFFTは6℃であった。
表2および表3に記載のとおりにして得られたポリウレタンを表4に記載の組成物とともに使用する以外は、例1を再現した。
ポリウレタンA1およびポリウレタンB1の両方を含む組成物の代わりに、ポリウレタン分散液A2およびB2のみをそれぞれ使用する以外は例1を再現した。
組成物をポリイソシアネート5%ベイハイダー(Bayhydur)(登録商標)3100と組合わせて使用する以外は例1〜8および比較例9Rおよび10Rを再現した。この組合せは最高8時間の可使時間を有していた。
Claims (15)
- 水性照射硬化性組成物であって、
−少なくとも1種のポリイソシアネート化合物(Ai)、イソシアネート基と反応することができる少なくとも2個の反応性基を含有する少なくとも1種のエチレン性不飽和化合物(Aii)、イソシアネート基と反応することができる少なくとも1個の反応性基を含有し、および直接に、または中和剤との反応により塩を形成した後、当該ポリウレタンプレポリマーを水性媒質中で分散性にすることができる少なくとも1種の親水性化合物(Aiii)、イソシアネート基と反応することができ、連鎖延長をもたらす少なくとも1種のポリアミン(Avii)の反応から得られる少なくとも1種のエチレン性不飽和ポリウレタン(A);ポリウレタン(A)とは相違しており、少なくとも1種のポリイソシアネート化合物(Bi)、イソシアネート基と反応することができる少なくとも2個の反応性基を含有する少なくとも1種のエチレン性不飽和化合物(Bii)、イソシアネート基と反応することができる少なくとも1個の反応性基を含有し、および直接に、または中和剤との反応により塩を形成した後、当該ポリウレタンプレポリマーを水性媒質中で分散性にすることができる少なくとも1種の親水性化合物(Biii)、イソシアネート基と反応することができる基本的に1個の反応性基を含有する少なくとも1種のエチレン性不飽和化合物(Biv)の反応から得られる少なくとも1種のエチレン性不飽和ポリウレタン(B)、ここで前記ポリウレタン(A)は、重量平均分子量が100000ダルトンより大きく、g当たり少なくとも0.5 meqの重合性エチレン性不飽和基を含有し、および
前記ポリウレタン(B)は重量平均分子量が100000ダルトン以下である、
を含み、ポリウレタン(A)10〜90重量%およびポリウレタン(B)10〜90重量%をポリウレタン(A)およびポリウレタン(B)の総重量に基づき含む水性照射硬化性組成物。 - ポリウレタン(A)が化合物(Ai)、(Aii)、(Aiii)、(Avii)および1種または2種以上のポリオール(Avi)の反応により得られる、および/またはポリウレタン(B)が化合物(Bi)、(Bii)、(Biii)、(Biv)および1種または2種以上のポリオール(Bvi)および/または1種または2種以上のポリアミン(Bvii)の反応により得られる請求項1に記載の水性照射硬化性組成物。
- ポリウレタン(B)が1000〜100000ダルトンの重量平均分子量を有する、請求項1または2に記載の水性照射硬化性組成物。
- ポリウレタン(B)がポリウレタン(B)のg当たり少なくとも3meqの重合性エチレン性不飽和基を含有する、請求項1〜3のいずれかに記載の水性照射硬化性組成物。
- ASTM D2354に従い、高くて40℃の最低皮膜形成温度を示す、請求項1〜4のいずれかに記載の水性照射硬化性組成物。
- ポリイソシアネート化合物(Ai)および(Bi)が脂肪族および環状脂肪族ポリイソシアネート化合物から選択される、請求項1〜5のいずれかに記載の水性照射硬化性組成物。
- 親水性化合物(Aiii)および(Biii)が一般式(HO)xR(COOH)y(式中、Rは炭素原子1〜12個を有する直鎖状または分枝鎖状炭化水素残基を表し、およびxおよびyは独立して、1〜3の整数である)で表されるヒドロキシカルボン酸化合物から選択される、請求項1〜6のいずれかに記載の水性照射硬化性組成物。
- エチレン性不飽和化合物(Aii)および(Bii)がジグリシジル化合物と(メト)アクリル酸との反応生成物から選択される、請求項1〜7のいずれかに記載の水性照射硬化性組成物。
- エチレン性不飽和化合物(Aii)および(Bii)がビスフェノールAジグリシジルエーテルのジアクリレートエステル化合物から選択される、請求項8に記載の水性照射硬化性組成物。
- エチレン性不飽和化合物(Biv)が脂肪族および/または芳香族ポリオール化合物の1個の残留平均ヒドロキシル残基を有する(メト)アクリル酸化合物によるエステル化生成物から選択される、請求項1〜9のいずれかに記載の水性照射硬化性組成物。
- ポリアミン(Avii)が60個までの炭素原子を有するポリアミン化合物から選択する、請求項1〜10のいずれかに記載の水性照射硬化性組成物。
- ポリウレタン(A)およびポリウレタン(B)の総重量に基づき1〜50重量%の量のエチレン性不飽和化合物(C)を含む、請求項11に記載の水性照射硬化性組成物。
- コーティングを有する物品の製造方法であって、前記物品を請求項1〜12のいずれかに記載の水性照射硬化性組成物でコーティングする工程を含む物品の製造方法。
- ポリウレタン(A)、ポリウレタン(B)および/または外部化合物中に存在する反応官能性基の存在に基づき、水性照射硬化性組成物を追加の架橋反応に付す、請求項13に記載の方法。
- (ブロックド)ポリイソシアネート化合物、ポリアジリジン化合物、ポリカルボジイミド化合物、ジルコニウムアンモニウムカーボネートのような金属塩化合物、ポリエポキシド化合物およびポリアルコキシシラン化合物から選択される追加の外部架橋剤が水性照射硬化性組成物に添加される、請求項13に記載の方法。
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CN111647348B (zh) * | 2020-05-19 | 2021-06-15 | 广东职业技术学院 | 一种含有生物质多孔碳的低温紫外光固化粉末涂料及其制备方法 |
EP3923072A1 (en) | 2020-06-08 | 2021-12-15 | Joanneum Research Forschungsgesellschaft mbH | A method of preparing an embossed structure, embossed structure and use thereof |
CA3157689A1 (en) | 2021-04-30 | 2022-10-30 | Amrad Manufacturing, Llc | Hard start kit for multiple replacement applications |
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JPS63108020A (ja) * | 1986-06-12 | 1988-05-12 | Toyobo Co Ltd | 放射線硬化型樹脂 |
DE4342384A1 (de) | 1993-12-11 | 1995-06-14 | Hoechst Ag | Wasserverdünnbare Zweikomponenten-Überzugsmasse |
JPH08259888A (ja) * | 1995-03-24 | 1996-10-08 | Dainippon Ink & Chem Inc | 活性エネルギー線硬化性水分散体 |
JPH09279017A (ja) * | 1996-04-16 | 1997-10-28 | Dainippon Ink & Chem Inc | 活性エネルギー線硬化型水性ポリウレタン樹脂組成物 |
DE19619636A1 (de) * | 1996-05-15 | 1997-11-20 | Basf Ag | Latent vernetzende wässerige Polyurethandispersionen |
JPH10251360A (ja) * | 1997-03-14 | 1998-09-22 | Dainippon Ink & Chem Inc | 活性エネルギー線硬化性水性ポリウレタン組成物 |
DE10226932A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Strahlenhärtende Beschichtungsmittel |
EP1845143A1 (en) * | 2006-04-14 | 2007-10-17 | Cytec Surface Specialties, S.A. | Aqueous radiation curable polyurethane compositions |
EP2130846A1 (en) * | 2008-06-06 | 2009-12-09 | Cytec Surface Specialties, S.A. | Aqueous radiation curable polyurethane compositions |
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KR20160075855A (ko) | 2016-06-29 |
CN102046688B (zh) | 2013-03-27 |
JP2011523674A (ja) | 2011-08-18 |
KR20180019785A (ko) | 2018-02-26 |
TWI526462B (zh) | 2016-03-21 |
KR101831447B1 (ko) | 2018-02-22 |
EP2288638B1 (en) | 2012-03-07 |
CN103131163A (zh) | 2013-06-05 |
US8853318B2 (en) | 2014-10-07 |
JP2015163696A (ja) | 2015-09-10 |
TW201006857A (en) | 2010-02-16 |
US20140371387A1 (en) | 2014-12-18 |
BRPI0912160A2 (pt) | 2015-10-13 |
BRPI0912160B1 (pt) | 2019-07-30 |
CN102046688A (zh) | 2011-05-04 |
KR20110034589A (ko) | 2011-04-05 |
WO2009147092A1 (en) | 2009-12-10 |
CA2723464C (en) | 2016-01-05 |
US20110086180A1 (en) | 2011-04-14 |
JP2017043769A (ja) | 2017-03-02 |
EP2130846A1 (en) | 2009-12-09 |
EP2288638A1 (en) | 2011-03-02 |
CA2723464A1 (en) | 2009-12-10 |
ATE548404T1 (de) | 2012-03-15 |
ES2380312T3 (es) | 2012-05-10 |
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