EP4288471A1 - Wasserdispergierbare polyisocyanatzusammensetzung, verfahren zur herstellung der zusammensetzung, härtbare zusammensetzung auf wasserbasis, farbe auf wasserbasis und artikel - Google Patents
Wasserdispergierbare polyisocyanatzusammensetzung, verfahren zur herstellung der zusammensetzung, härtbare zusammensetzung auf wasserbasis, farbe auf wasserbasis und artikelInfo
- Publication number
- EP4288471A1 EP4288471A1 EP21923652.8A EP21923652A EP4288471A1 EP 4288471 A1 EP4288471 A1 EP 4288471A1 EP 21923652 A EP21923652 A EP 21923652A EP 4288471 A1 EP4288471 A1 EP 4288471A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- water
- acrylic polymer
- group
- acrylic
- mol
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 95
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 91
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 91
- 239000003973 paint Substances 0.000 title claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 66
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 94
- 239000000178 monomer Substances 0.000 claims abstract description 54
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 26
- 239000002994 raw material Substances 0.000 claims abstract description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 18
- 239000011248 coating agent Substances 0.000 abstract description 16
- 229920000642 polymer Polymers 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 52
- -1 industrial machinery Substances 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 239000000463 material Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920001427 mPEG Polymers 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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- 150000002739 metals Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- 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
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 229940043430 calcium compound Drugs 0.000 description 2
- 150000001674 calcium compounds Chemical class 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- DUDXQIXWPJMPRQ-UHFFFAOYSA-N isocyanatomethylcyclohexane Chemical compound O=C=NCC1CCCCC1 DUDXQIXWPJMPRQ-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
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- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- GNQKHBSIBXSFFD-UHFFFAOYSA-N 1,3-diisocyanatocyclohexane Chemical compound O=C=NC1CCCC(N=C=O)C1 GNQKHBSIBXSFFD-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
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- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
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- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical group C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- GWCTUKHUBWMAMI-GQCTYLIASA-N butyl (e)-but-2-enoate Chemical compound CCCCOC(=O)\C=C\C GWCTUKHUBWMAMI-GQCTYLIASA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- XFWJKVMFIVXPKK-UHFFFAOYSA-N calcium;oxido(oxo)alumane Chemical compound [Ca+2].[O-][Al]=O.[O-][Al]=O XFWJKVMFIVXPKK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006074 cyclodimerization reaction Methods 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 238000006006 cyclotrimerization reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- OGVXYCDTRMDYOG-UHFFFAOYSA-N dibutyl 2-methylidenebutanedioate Chemical compound CCCCOC(=O)CC(=C)C(=O)OCCCC OGVXYCDTRMDYOG-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- HJVKTYVDOZVQPA-UHFFFAOYSA-N ethenoxycyclopentane Chemical compound C=COC1CCCC1 HJVKTYVDOZVQPA-UHFFFAOYSA-N 0.000 description 1
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- IGWTZHMYJZZIGC-UHFFFAOYSA-N ethyl 2,6-diisocyanatohexanoate Chemical compound CCOC(=O)C(N=C=O)CCCCN=C=O IGWTZHMYJZZIGC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 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
- 238000003756 stirring Methods 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 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
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
Definitions
- Embodiments of the present invention relate to a water-dispersible polyisocyanate composition, a method for producing the composition, a water-based curable composition, a water-based paint, and an article.
- Patent Literatures 1 and 2 disclose water-dispersible polyisocyanate compositions containing a polyisocyanate and a nonionic group-containing vinyl polymer. However, even these isocyanate compositions disadvantageously have short pot lives as two-component urethane coatings.
- One aspect of the present invention is directed to providing a water-dispersible polyisocyanate composition that contains a hydrophobic polyisocyanate (A) and an acrylic polymer (B) containing an alkoxy group end-capped polyoxyalkylene group and an isocyanate group, in which the acrylic polymer (B) is a reaction product of an acrylic polymer (b) and a hydrophobic polyisocyanate, the acrylic polymer (b) contains an acrylic polymer (b1) and an acrylic polymer (b2) , the acrylic polymer (b1) is derived from a monomer raw material containing 11 mol%or more and 35 mol%or less of an acrylic monomer (x) having an alkoxy group end-capped polyoxyalkylene group, and the acrylic polymer (b2) is derived from a monomer raw material containing 2 mol%or more and less than 11 mol%of the acrylic monomer (x) .
- the water-dispersible polyisocyanate composition according to an embodiment of the present invention provides a long pot life after mixing two components and excellent appearance of a coating film to be formed and thus can be suitably used in various paints for, for example, interiors and exteriors of automobiles, automobile repairs, plastics, industrial machinery, building materials, and woodworking.
- a water-dispersible polyisocyanate composition contains a hydrophobic polyisocyanate (A) and an acrylic polymer (B) containing an alkoxy group end-capped polyoxyalkylene group and an isocyanate group, in which the acrylic polymer (B) is a reaction product of an acrylic polymer (b) and a hydrophobic polyisocyanate, the acrylic polymer (b) contains an acrylic polymer (bl) and an acrylic polymer (b2) , the acrylic polymer (b1) is derived from a monomer raw material containing 11 mol%or more and 35 mol%or less of an acrylic monomer (x) having an alkoxy group end-capped polyoxyalkylene group, and the acrylic polymer (b2) is derived from a monomer raw material containing 2 mol%or more and less than 11 mol%of the acrylic monomer (x) .
- the hydrophobic polyisocyanate (A) has no hydrophilic group.
- examples of the hydrophobic polyisocyanate (A) include aliphatic diisocyanates, such as 1, 4-tetramethylene diisocyanate, ethyl 2, 6-diisocyanatohexanoate, 1, 6-hexamethylene diisocyanate, 1, 12-dodecamethylene diisocyanate, and 2, 2, 4-or 2, 4, 4-trimethylhexamethylene diisocyanate; aliphatic triisocyanates, such as 1, 3, 6-hexamethylene triisocyanate, 1, 8-diisocyanato-4- (isocyanatomethyl) octane, and 2-isocyanatoethyl (2, 6-diisocyanato) hexanoate; alicyclic diisocyanates, such as 1, 3-bis (isocyanatomethylcyclohexane) , 1, 4-bis (isocyanatomethylcyclohexane
- hydrophobic polyisocyanates (A) aliphatic or alicyclic diisocyanates or triisocyanates, aralkylene diisocyanates, and polyisocyanates derived therefrom are preferred in view of the stability of isocyanate groups in water and the weatherability of a coating film formed from a paint containing the water-dispersible polyisocyanate composition.
- polyisocyanates having three or more functionalities such as isocyanurate-type polyisocyanates, polyisocyanates having a biuret structure, polyisocyanates having a uretdione structure, polyisocyanates having an allophanate structure, and polyisocyanates formed by the reaction of diisocyanates and trihydric or higher polyhydric alcohols, are preferred in order to prepare a water-based curable composition excellent in weatherability and durability.
- a hydrophilic group-containing polyisocyanate may be used in combination with the hydrophobic polyisocyanate (A) as long as the stability of the water-dispersible polyisocyanate composition according to an embodiment of the present invention is not impaired.
- the acrylic polymer (B) has an alkoxy group end-capped polyoxyalkylene group.
- the polyoxyalkylene group can be easily introduced by the use of an acrylic monomer (x) having an alkoxy group end-capped polyoxyalkylene group as the monomer raw material for the acrylic polymer (b) .
- polyoxyalkylene group examples include a polyoxyethylene group, a polyoxypropylene group, a polyoxybutylene group, polyoxyalkylene groups formed by random or block copolymerization of different oxyalkylenes, and polyoxyalkylene groups formed by ring-opening polymerization of dioxolane.
- polyoxyalkylene groups a polyoxyalkylene group containing an oxyethylene unit as an essential structural unit is preferred because water dispersibility is further improved.
- the polyoxyalkylene group preferably has 12 to 30 oxyalkylene group repeat units because the water dispersibility and the pot life are further improved.
- terminal alkoxy group examples include lower alkoxy groups, such as a methoxy group, an ethoxy group, and a butoxy group.
- the acrylic polymer (b) contains the acrylic polymer (b1) and the acrylic polymer (b2) . This provides excellent pot life after mixing two components.
- the monomer raw material for the acrylic polymer (b1) contains 11 mol%or more and 35 mol%or less, preferably 12 mol%or more and 24 mol or less of the acrylic monomer (x) having an alkoxy group end-capped polyoxyalkylene group because a longer pot life is achieved.
- the monomer raw material for the acrylic polymer (b2) contains 2 mol%or more and less than 11 mol%, preferably 5 mol%or more and 10 mol%or less of the acrylic monomer (x) because a longer pot life is achieved.
- acrylic monomer (x) examples include methoxy poly (ethylene glycol) (meth) acrylate, ethoxy poly (ethylene glycol) (meth) acrylate, propoxy poly (ethylene glycol) (meth) acrylate, butoxy poly (ethylene glycol) (meth) acrylate, phenoxy poly (ethylene glycol) (meth) acrylate, methoxy poly (propylene glycol) (meth) acrylate, ethoxy poly (propylene glycol) (meth) acrylate, propoxy poly (propylene glycol) (meth) acrylate, butoxypoly (propylene glycol) (meth) acrylate, phenoxy poly (propylene glycol) (meth) acrylate, methoxy poly (butylene glycol) (meth) acrylate, ethoxy poly (butylene glycol) (meth) acrylate, propoxy poly (butylene glycol) (meth) acrylate, butoxy poly (butylene glycol)
- the acrylic polymer (B) is a reaction product of the acrylic polymer (b) and the hydrophobic polyisocyanate and is easily prepared by introducing an active hydrogen-containing group into the acrylic polymer (b1) and/or the acrylic polymer (b2) andallowingthe acrylicpolymer (b1) and/or the acrylicpolymer (b2) to react with the hydrophobic polyisocyanate.
- the active hydrogen-containing group can be easily introduced into the acrylic polymer by the use of an unsaturated monomer having an active hydrogen-containing group as a monomer raw material for the acrylic polymer (b1) and/or the acrylic polymer (b2) .
- Examples of the unsaturated monomer having an active hydrogen-containing group include hydroxy group-containing unsaturated monomers, carboxy group-containing unsaturated monomers, amino group-containing unsaturated monomers, and active methylene group-containing unsaturated monomers. Hydroxy group-containing unsaturated monomers are preferred. These unsaturated monomers having active hydrogen-containing groups may be used alone or in combination of two or more.
- Examples of such a hydroxy group-containing unsaturated monomer include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxy-n-butyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-n-butyl (meth) acrylate, 3-hydroxy-n-butyl (meth) acrylate, 1, 4-cyclohexanedimethanol mono (meth) acrylate, glycerol mono (meth) acrylate, poly (ethylene glycol) mono (meth) acrylate, poly (propylene glycol) mono (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2- (meth) acryloyloxyethyl 2-hydroxyethyl phthalate, and lactone-modified (meth) acrylate having a terminal hydroxy group.
- These hydroxy group-containing unsaturated monomers may be used alone or in combination of
- an unsaturated monomer containing a hydrophobic group having 4 or more carbon atoms is preferably used because the water dispersibility and the pot life are further improved.
- Examples of the unsaturated monomer containing a hydrophobic group having 4 or more carbon atoms include (meth) acrylates each containing an alkyl group having 4 to 22 carbon atoms, such as n-butyl (meth) acrylate, iso-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, and octadecyl (meth) acrylate; cycloalkyl (meth) acrylates, such as cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, bornyl (meth) acrylate, isobornyl (meth) acrylate, and dicyclopentanyl (meth) acrylate; cycloalkylalkyl (meth) acrylates, such as cyclopentylmethyl (meth)
- acrylic polymers (b1) and (b2) a known and commonly used monomer, such as alkyl (meth) acrylates having 3 or less carbon atoms, e.g., methyl (meth) acrylate, ethyl (meth) acrylate, or n-propyl (meth) acrylate, can be used in combination with the monomer described above.
- alkyl (meth) acrylates having 3 or less carbon atoms e.g., methyl (meth) acrylate, ethyl (meth) acrylate, or n-propyl (meth) acrylate
- the monomer raw material for the acrylic polymer (b1) preferably contains 11 mol%or more and 35 mol%or less of the acrylic monomer (x) because the water dispersibility and the pot life are further improved.
- the monomer raw material for the acrylic polymer (b2) preferably contains 2 mol%or more and less than 11 mol%of the acrylic monomer (x) because the water dispersibility and the pot life are further improved.
- the monomer raw material for each of the acrylic polymers (b1) and (b2) preferably contains 1%to 10%by mass of the monomer having an active hydrogen-containing group because the water dispersibility and the pot life are further improved.
- Each of the acrylic polymers (b1) and (b2) preferably has a hydroxyl value of 5 to 50 mgKOH/g because the water dispersibility and the pot life are further improved.
- the hydroxyl value according to an embodiment of the present invention is defined as a calculated value determined from the raw materials used.
- acrylic polymers (b1) and (b2) Various known and commonly used polymerization methods can be employed for the formation of the acrylic polymers (b1) and (b2) .
- a radical solution polymerization method in an organic solvent is convenient and preferable.
- polymerization initiators can be used.
- examples thereof include azo compounds, such as 2, 2′-azobis (isobutyronitrile) , 2, 2′-azobis (2, 4-dimethylbutyronitrile) , and 2, 2′-azobis (2-methylbutyronitrile) ; and peroxides, such as tert-butyl peroxypivalate, tert-butyl peroxybenzoate, tert-butyl peroxy-2-ethylhexanoate, di-tert-butyl peroxide, cumene hydroperoxide, and diisopropyl peroxycarbonate.
- azo compounds such as 2, 2′-azobis (isobutyronitrile) , 2, 2′-azobis (2, 4-dimethylbutyronitrile) , and 2, 2′-azobis (2-methylbutyronitrile)
- peroxides such as tert-butyl peroxypivalate, tert-butyl peroxybenzo
- any compound that is not reactive with an isocyanate group can be used.
- examples thereof include aliphatic or alicyclichydrocarbon compounds, such as n-hexane, n-heptane, n-octane, cyclohexane, and cyclopentane; aromatic hydrocarbon compounds, such as toluene, xylene, and ethylbenzene; ester compounds, such as ethyl acetate, n-butyl acetate, n-amyl acetate, and ethylene glycol monomethyl ether acetate; ketone compounds, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl n-amyl ketone, and cyclohexanone; poly (alkylene glycol) dialkyl ether compounds, such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene glycol di
- the acrylic polymer (b) contains the acrylic polymers (bi) and (b2) .
- a method for producing the acrylic polymer (b) a method is preferred in which the monomer raw material for the acrylic polymer (b2) is polymerized in the presence of the acrylic polymer (b1) because the water dispersibility and the pot life are further improved.
- Each of the acrylic polymers (b1) and (b2) preferably has a weight-average molecular weight of 5,000 to 100,000 because the water dispersibility and the pot life are further improved.
- the acrylic polymer (b) preferably has a hydroxyl value of 5 to 50 mgKOH/g because the water dispersibility and the pot life are further improved.
- the isocyanate group-containing hydrophobic polyisocyanate (A) is preferably allowed to react with the acrylic polymer (b) in excess of the equivalent weight of the active hydrogen-containing group of the acrylic polymer (b) .
- the equivalent ratio of the isocyanate group to the active hydrogen-containing group is preferably in the range of 10 to 80.
- the water-dispersible polyisocyanate composition according to an embodiment of the present invention contains the hydrophobic polyisocyanate (A) and the acrylic polymer (B) and is easily obtained by the method for producing the acrylic polymer (B) described above.
- the ratio by mass (A/b) of the hydrophobic polyisocyanate (A) to the acrylic polymer (b) is in the range of 0.8 to 6.3 because the water dispersibility and the pot life are further improved.
- the water-dispersible polyisocyanate composition according to an embodiment of the present invention contains the hydrophobic polyisocyanate (A) and the acrylic polymer (B) .
- the ratio by mass (A/B) of the hydrophobic polyisocyanate (A) to the acrylic polymer (B) is preferably in the range of 0.5 to 6 because the water dispersibility and the pot life are further improved.
- a water-based curable composition according to an embodiment of the present invention contains the water-dispersible polyisocyanate composition and a water-based resin (C) having an active hydrogen-containing group reactive with an isocyanate group.
- Examples of the active hydrogen-containing group of the water-based resin (C) include a hydroxy group, a carboxy group, an amino group, an amide group, and active methylene group-containing groups, such as an acetoacetyl group. Among these, a hydroxy group and a carboxy group are preferred.
- Examples of the form of the water-based resin (C) include known and commonly used forms, such as water-soluble forms and water-dispersible forms, e.g., colloidal dispersions and emulsions.
- water-based resin (C) examples include vinyl polymers, such as vinyl acetate-based resins, styrene-butadiene-based resins, styrene-acrylonitrile resins, acrylic resins, fluoroolefin resins, silicone-modified vinyl polymers, and poly (vinyl alcohol) ; synthetic resins other than vinyl polymers, such as polyester resins, polyurethane resins, phenolic resins, melamine resins, epoxy resins, alkyd resins, polyamide resins, polyether resins, and silicone resins; and naturally-occurring polymers, such as animal protein, starch, cellulose derivatives, dextrin, and gum arabic. Among these, vinyl polymers and various synthetic resins other than vinyl polymers are preferred. These water-based resins (C may be used alone or in combination of two or more.
- vinyl polymers such as vinyl acetate-based resins, styrene-butadiene-based resins, styren
- the amount of the active hydrogen-containing group contained in the water-based resin (C) is preferably in the range of 0.1 to 6 mol, more preferably 0.2 to 4 mol, even more preferably 0.4 to 3 mol per 1,000 g of the solid content of the water-based resin in view of the curability of the water-based curable composition according to an embodiment of the present invention and the water resistance of a cured article to be formed.
- the ratio of (1) the amount by mole of the isocyanate groups in the polyisocyanate composition to (2) the total amount by mole of the active hydrogen-containing group in the water-based resin (C) and the blocked active hydrogen-containing group contained in the NCO group-containing vinyl polymer (B) , i.e., (1) / (2) is preferably in the range of 0.1 to 5, more preferably 0.3 to 3, even more preferably 0.5 to 2 in view of the curability of the curable composition and the performance of a cured article formed from the composition.
- the water-based curable composition according to an embodiment of the present invention can be used as a pigment-free clear composition.
- the water-based curable composition according to an embodiment of the present invention can further contain various known and commonly used organic or inorganic pigments and thus can be used as a colored composition.
- the water-based curable composition thus prepared can be used for various applications, such as paints, adhesives, inks, waterproofing materials, sealing agents, impregnation treatment agents for various fibers, e.g., natural fibers, synthetic fibers, and glass fibers, and paper, and surface treatment agents for various fibers, e.g., natural fibers, synthetic fibers, and glass fibers, and paper.
- the water-based curable composition is preferably used for a water-based paint.
- a water-based paint according to an embodiment of the present invention has a long pot life and provides a cured coating film excellent in appearance and so forth.
- the water-based paint according to an embodiment of the present invention can further contain known and commonly used various additives suitable for various applications, such as fillers, leveling agents, thickeners, defoamers, organic solvents, ultraviolet absorbers, antioxidants, and pigment dispersants, as components other than the foregoing water-based curable composition according to an embodiment of the present invention, if necessary.
- various additives suitable for various applications such as fillers, leveling agents, thickeners, defoamers, organic solvents, ultraviolet absorbers, antioxidants, and pigment dispersants, as components other than the foregoing water-based curable composition according to an embodiment of the present invention, if necessary.
- Examples of a base material onto which the water-based paint according to an embodiment of the present invention is applied include various metal basematerials, inorganic base materials, plastic base materials, inorganic fibers, such as paper, synthetic fibers, natural fibers, and glass fibers, cloths, synthetic leathers, natural leathers, and woody base materials.
- metal base materials include metals, such as iron, nickel, aluminum, chromium, zinc, tin, copper, and lead; alloys of various metals described above, such as stainless steel and brass; and various surface-treated metals and alloys in which the foregoing various metals and alloys have been subjected to surface treatment, such as plating or chemical conversion treatment.
- Examples of the inorganic base materials include hardened articles produced from calcium compounds, such as calcium silicate, calcium aluminate, calcium sulfate, and calcium oxide; ceramic materials produced by sintering metal oxides, such as alumina, silica, and zirconia; tiles produced by sintering various clay minerals; and various glasses.
- Typical examples of the hardened articles produced from calcium compounds include hardened articles of cement compositions, such as concrete and mortar, asbestos cement boards and sheets, hardened articles of autoclaved lightweight concrete (ALC) , hardened articles of dolomite plaster, hardened articles of gypsum plaster, and calcium silicate boards.
- plastic base materials include formed articles of thermoplastic resins, such as polystyrene, polycarbonates, poly (methyl methacrylate) , acrylonitrile-butadiene-styrene (ABS) resins, poly (phenylene oxide) , polyurethane, polyethylene, poly (vinyl chloride) , polypropylene, poly (butylene terephthalate) , and poly (ethylene terephthalate) ; and formed articles of various thermosetting resins, such as unsaturated polyester resins, phenolic resins, crosslinked polyurethane, crosslinked acrylic resins, and crosslinked saturated polyester resins.
- thermoplastic resins such as polystyrene, polycarbonates, poly (methyl methacrylate) , acrylonitrile-butadiene-styrene (ABS) resins, poly (phenylene oxide) , polyurethane, polyethylene, poly (vinyl chloride) , polypropylene, poly (butylene terephthal
- Coated base materials in which various base materials as described above have been coated can be used. Moreover, the coated base materials in which the deterioration of coated portions has progressed can also be used.
- the water-based paint according to an embodiment of the present invention is applied to such a base material by a known and commonly used coating method, such as brush coating, roller coating, spray coating, dip coating, coating with a flowcoater, coating with a roll coater and then allowed to stand at room temperature for about 1 to about 10 days or heated in a temperature range of 40°C to 250°C for about 30 seconds to about 2 hours, thereby enabling the formation of a cured coating film excellent in appearance and so forth.
- a known and commonly used coating method such as brush coating, roller coating, spray coating, dip coating, coating with a flowcoater, coating with a roll coater and then allowed to stand at room temperature for about 1 to about 10 days or heated in a temperature range of 40°C to 250°C for about 30 seconds to about 2 hours, thereby enabling the formation of a cured coating film excellent in appearance and so forth.
- ′′PMA′′ propylene glycol monomethyl ether acetate
- methoxy poly (ethylene glycol) methacrylate containing 23 oxyethylene units on average per molecule
- ′′BA′′ butyl acrylate
- ′′2-HEMA′′ 2-hydroxyethyl methacrylate
- ′′P-O′′ rert-butyl per
- the resulting mixture was maintained for 1 hour at 110°C.
- Amixture of 403 parts by mass of ′′MPEGMA-i′′ , 378 parts by mass of BA, 41 parts by mass of 2-HEMA, and 50 parts by mass of P-O was added dropwise thereinto over a period of 2.5 hours.
- the resulting mixture was allowed to react at 110°C for 9 hours to prepare a solution of an acrylic polymer (b-1) containing an acrylic polymer (b1-1) and an acrylic polymer (b2-1) and having a non-volatile content of 50%by mass.
- the acrylic polymer (b-1) had a hydroxyl value of 21.5 mgKOH/g.
- Table 1 presents monomer compositions used for the preparation of the acrylic polymers (b-1) to (b-4) in Synthesis examples 1 to 4.
- Table 2 presents monomer compositions used for the preparation of the acrylic polymers (Rb-1) ⁇ (Rb-3) in Synthesis examples 5 to 7.
- the mixture was heated to 100°C under a nitrogen stream and then allowed to react at the same temperature for 6 hours under stirring to give a water-dispersible polyisocyanate composition (1) having a non-volatile content of 82.5%by mass and an NCO group content of 13.3%by mass.
- Water-dispersible polyisocyanate compositions (2) to (8) were prepared as in Example 1, except that the hydrophobic polyisocyanate (A-i) and the acrylic polymer (b-1) used in Example 1 were changed as given in Tables 3 and 4.
- Comparative Example 1 to 3 Synthesis of Water-Dispersible Polyisocyanate Compositions (Ri) to (R3) )
- Water-dispersible polyisocyanate compositions (Ri) to (R3) were prepared as in Example 1, except that the hydrophobic polyisocyanate (A-i) and the acrylic polymer (b-1) used in Example 1 were changed as given in Table 5.
- Tables 3 and 4 present compositions of the polyisocyanate compositions (1) to (8) prepared in Examples 1 to 8.
- Table 5 presents compositions of the polyisocyanate compositions (Ri) to (R3) prepared in Comparative examples 1 to 3.
- the water-dispersible polyisocyanate composition (1) prepared in Example 1 and a water-based resin ( ′′Burnock WD-551′′ , available from DIC Corporation, non-volatile content: 44%by mass, hydroxyl value of solid content: 100 mgKOH/g) were mixed in such a manner that the ratio by mole of isocyanate groups in the water-dispersible polyisocyanate composition (1) to hydroxy groups in the water-based resin, i.e., (NCO/OH) , was 1.2/1.
- the mixture was diluted with water so as to have a viscosity of 500mPa ⁇ s or less (Brookfield typeviscometer, 25°C, No. 2 rotor, 30 rpm) . Thereby, a water-based curable composition (1) was prepared.
- the viscosity of the water-based curable composition (1) was measured immediately after the preparation and every hour after the preparation.
- the pot life was determined by subtracting 1 hour from the time when the viscosity exceeded 2,000 mPa ⁇ s.
- the pot life was evaluated according to the following evaluation criteria.
- the water-based curable composition (1) was applied onto a glass plate with an applicator to a dry thickness of 30 ⁇ m and dried at 60°C for 2 hours to produce a cured coating film.
- the appearance of the resulting cured coating film was evaluated according to the following evaluation criteria.
- Water-based curable compositions (2) to (8) were prepared in the same manner as in Example 9, except that the water-dispersible polyisocyanate composition (1) used in Example 9 was changed to the water-dispersible polyisocyanate compositions (2) to (8) , and then evaluated similarly.
- Comparative Example 4 to 6 Preparation and Evaluation of Water-Based Curable Compositions (R-i) to (R-3) )
- Water-based curable compositions (R-i) to (R-3) were prepared in the same manner as in Example 9, except that the water-dispersible polyisocyanate composition (1) used in Example 9 was changed to the water-dispersible polyisocyanate compositions (Ri) to (R3) , and then evaluated similarly.
- Tables 6 to 8 present the evaluation results of Examples 9 to 16 and Comparative examples 4 to 6.
- the water-dispersible polyisocyanate composition of Comparative example 1 was an example of a water-dispersible polyisocyanate composition prepared without using the acrylic polymer (b2) , which is an essential raw material in an embodiment of the present invention.
- the water-dispersible polyisocyanate composition of Comparative example 2 was an example of a water-dispersible polyisocyanate composition prepared without using the acrylic polymer (b1) , which is an essential raw material in an embodiment of the present invention. The results indicated that the water-based curable composition prepared by using the water-dispersible polyisocyanate composition of Comparative example 2 provided the coating film having poor appearance.
- the water-dispersible polyisocyanate composition of Comparative example 3 was an example of a water-dispersible polyisocyanate composition prepared by using only one type of acrylic polymer serving as a raw material. The results indicated that the water-based curable composition prepared by using the water-dispersible polyisocyanate composition of Comparative example 3 had a poor pot life.
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