JPWO2010035641A1 - 水性塗料組成物 - Google Patents
水性塗料組成物 Download PDFInfo
- Publication number
- JPWO2010035641A1 JPWO2010035641A1 JP2010530809A JP2010530809A JPWO2010035641A1 JP WO2010035641 A1 JPWO2010035641 A1 JP WO2010035641A1 JP 2010530809 A JP2010530809 A JP 2010530809A JP 2010530809 A JP2010530809 A JP 2010530809A JP WO2010035641 A1 JPWO2010035641 A1 JP WO2010035641A1
- Authority
- JP
- Japan
- Prior art keywords
- compound
- water
- polyamine resin
- coating composition
- resin
- 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.)
- Granted
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 28
- 239000000203 mixture Substances 0.000 title claims description 15
- 239000003973 paint Substances 0.000 title claims description 15
- 229920005989 resin Polymers 0.000 claims abstract description 130
- 239000011347 resin Substances 0.000 claims abstract description 130
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 229920000768 polyamine Polymers 0.000 claims abstract description 120
- 239000008199 coating composition Substances 0.000 claims abstract description 56
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract 2
- 238000000576 coating method Methods 0.000 claims description 80
- 239000011248 coating agent Substances 0.000 claims description 79
- 239000004593 Epoxy Substances 0.000 claims description 25
- 239000000839 emulsion Substances 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000003995 emulsifying agent Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000002075 main ingredient Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 description 24
- -1 Solvesso 100 Substances 0.000 description 22
- 239000003822 epoxy resin Substances 0.000 description 22
- 229920000647 polyepoxide Polymers 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 150000003141 primary amines Chemical group 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000004925 Acrylic resin Substances 0.000 description 12
- 229920000178 Acrylic resin Polymers 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000003335 secondary amines Chemical group 0.000 description 12
- 238000006386 neutralization reaction Methods 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 6
- 125000004386 diacrylate group Chemical group 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 208000034189 Sclerosis Diseases 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical class C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012875 nonionic emulsifier Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 239000012874 anionic emulsifier Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 238000002715 modification method Methods 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- LBDSQNRQXIKAGX-UHFFFAOYSA-N (2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OCC(C)COC(=O)C=C LBDSQNRQXIKAGX-UHFFFAOYSA-N 0.000 description 1
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RHNJVKIVSXGYBD-UHFFFAOYSA-N 10-prop-2-enoyloxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC(=O)C=C RHNJVKIVSXGYBD-UHFFFAOYSA-N 0.000 description 1
- OMVSWZDEEGIJJI-UHFFFAOYSA-N 2,2,4-Trimethyl-1,3-pentadienol diisobutyrate Chemical compound CC(C)C(=O)OC(C(C)C)C(C)(C)COC(=O)C(C)C OMVSWZDEEGIJJI-UHFFFAOYSA-N 0.000 description 1
- AIHWKCKFGYDSSD-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol 2-methylprop-2-enoic acid prop-2-enoic acid Chemical compound C(C=C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(O)C(CO)(CO)CO AIHWKCKFGYDSSD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JEJIWKKGUFJLAF-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(C)(CO)CO JEJIWKKGUFJLAF-UHFFFAOYSA-N 0.000 description 1
- XZWQPQHCWPXUMF-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(C)(CO)CO XZWQPQHCWPXUMF-UHFFFAOYSA-N 0.000 description 1
- KANYKVYWMZPGSL-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(C)(CO)CO KANYKVYWMZPGSL-UHFFFAOYSA-N 0.000 description 1
- RGADKZXRWFOTFV-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(C)(CO)CO RGADKZXRWFOTFV-UHFFFAOYSA-N 0.000 description 1
- OWDBMKZHFCSOOL-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)propoxy]propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(C)COC(C)COC(=O)C(C)=C OWDBMKZHFCSOOL-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- JMWGZSWSTCGVLX-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid Chemical class CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO JMWGZSWSTCGVLX-UHFFFAOYSA-N 0.000 description 1
- CVUYSVSDCCHRNV-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO CVUYSVSDCCHRNV-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- UPTHZKIDNHJFKQ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane-1,2,3-triol Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(O)CO UPTHZKIDNHJFKQ-UHFFFAOYSA-N 0.000 description 1
- VPJOGDPLXNTKAZ-UHFFFAOYSA-N 2-methylpropanoic acid;2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)=O.CC(C)C(O)C(C)(C)CO VPJOGDPLXNTKAZ-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本発明の水性塗料組成物は、分子内に1つ以上の第1アミン基および/または第2アミン基を有する水溶性または水分散型のポリアミン樹脂(A)と、分子内に1つ以上の(メタ)アクリロイル基を有する化合物(B)とを含み、ポリアミン樹脂(A)と化合物(B)との反応により硬化し、塗膜を得ることができる。
本発明の水性塗料組成物に用いられるポリアミン樹脂(A)は、1つ以上の第1アミン基および/または第2アミン基を有し、かつ水溶性または水分散型の樹脂であれば任意の適切な樹脂が採用され得る。このような樹脂としては、例えば、脂肪族ポリアミン樹脂、芳香族ポリアミン樹脂、脂環族ポリアミン樹脂が挙げられる。
本発明の水性塗料組成物に用いられる化合物(B)は、分子内に1以上の(メタ)アクリロイル基を有する。
本発明の水性塗料組成物は、任意の適切な被塗物に塗装し得る。代表的には、鉄の表面である。
実施例および比較例で得られた塗料を25℃下で塗装および乾燥(24時間)したガラス板を目視にて、塗膜のつや、透明性、ブツ・ハジキ等の塗膜異常を評価した。
つや ○:つやの高いもの
△:半つや程度のもの
×:つやのないもの
透明性 ○:全く、またはほとんど濁りのないもの
△:やや濁りのあるもの
×:濁りの大きいもの
塗膜異常 ○:全く、またはほとんどブツ・ハジキのないもの
△:少しブツ・ハジキのあるもの
×:全面にブツ・ハジキのあるもの
(硬化性)
実施例および比較例で得られた塗料を25℃下および5℃下でガラス板に塗装および乾燥(24時間)して塗膜を得た後、当該塗膜をそれぞれ塗装時および乾燥時と同様の温度下において、メチルエチルケトン(MEK)を含ませたガーゼにてこすり、ガラス素地が露出するまでの往復回数を測定した。なお、表中における「>200」の表記は、200往復してもなおガラス素地が露出しなかったことを意味する。また、露出するまでの往復回数が100回以上の塗膜が合格である。
(防食性)
実施例で得られた塗料をサンドブラスト板に200g/m2となるよう、刷毛で塗布し、20℃で7日間乾燥させることにより、試験片を得た。当該試験片に対し、JIS K 5600 7−7に定めるサイクル腐食試験を実施し、120サイクル後の塗膜状態を下記基準に基づいて確認した。
試験片の表面に対する塗膜に生じた錆面積の割合
◎:0.05%未満
○:0.05%以上0.1%未満
△:0.1%以上0.3%未満
×:0.3%以上
撹拌機、冷却器、窒素導入管及び温度計を備えた反応槽に、ビスフェノールAとエピクロルヒドリンとから合成したエポキシ当量188のエポキシ樹脂702部、ビスフェノールA269部、ダイマー酸108部、メチルイソブチルケトン(以下「MIBK」という。)190部を仕込み、ベンジルジメチルアミン1部存在下、エポキシ当量1270になるまで117℃で反応させた。その後、アミノエチルエタノールアミンのケチミン化合物(73質量%MIBK溶液)255部を加え、117℃で1時間反応させた。その後、MIBKで不揮発分75%になるまで希釈し、数平均分子量2400、アミン当量1184のエポキシ系ポリアミン樹脂を得た。
製造例1で得たエポキシ系ポリアミン樹脂に、酢酸を加え、中和率20.0%(樹脂のアミン基に対する中和率)となるようにし、イオン交換水を加え希釈した。その後、固形分が40質量%となるまで減圧下でMIBK及び水の混合物を除去し、エマルションIを調製した。
撹拌機、冷却器、窒素導入管、温度計及び滴下ロートを備えた反応槽に、MIBK670部を仕込み110℃に昇温した。この反応槽に、滴下ロートを用い、スチレン540部、アクリル酸n−ブチル400部、グリシジルメタアクリレート140部、MIBK100部及びt−ブチルパーオクトエート20部とからなる溶液を3時間かけて滴下した。滴下終了後30分間にわたり110℃で保持した後、t−ブチルパーオクトエート2部とMIBK50部とからなる溶液を30分間で滴下した。この滴下終了後、さらに1時間、110℃にて反応を継続させ、エポキシ基を含む不揮発分60%のアクリル樹脂ワニスを得た。得られたワニス1920部に、アミノエチルエタノールアミンのケチミン化合物(73質量%MIBK溶液)255部を加え、117℃で1時間反応させ、数平均分子量10000、アミン当量1184のアクリル系ポリアミン樹脂を得た。
製造例3で得たアクリル系ポリアミン樹脂に、酢酸を加え、中和率20.0%(樹脂のアミン基に対する中和率)となるようにし、イオン交換水を加え希釈した。その後、固形分が40質量%となるまで減圧下でMIBK及び水の混合物を除去し、エマルションIIを調製した。
撹拌機、冷却器、窒素導入管及び温度計を備えた反応槽に、ビスフェノールAとエピクロルヒドリンとから合成したエポキシ当量188のエポキシ樹脂742部、ビスフェノールA336部、MIBK190部を仕込み、ベンジルジメチルアミン1部存在下、エポキシ当量1270になるまで117℃で反応させた。その後、ジエチレントリアミンのケチミン化合物(73質量%MIBK溶液)350部を加え、117℃で1時間反応させた。その後、イオン交換水27部、ネオデカン酸グリシジルエステル(カージュラE10−P)188部を仕込み、100℃で2時間反応させた。その後、MIBKで不揮発分75%になるまで希釈し、数平均分子量2600、アミン当量947のエポキシ系ポリアミン樹脂を得た。
製造例5で得たエポキシ系ポリアミン樹脂に、酢酸を加え、中和率20.0%(樹脂のカチオン性基に対する中和率)となるようにし、イオン交換水を加え希釈した。その後、固形分が40質量%となるまで減圧下でMIBK及び水の混合物を除去し、エマルションIIIを調製した。
ポリアミン樹脂(A)として製造例2で得られたエマルションI2960部に、ディスパーで撹拌しながら、ジプロピレングリコールn−ブチルエーテル(DPnB)118部を加えた後、さらに、ディスパー撹拌しながら、化合物(B)としてエトキシ化トリメチロールプロパントリアクリレート(EO20mol)(新中村化学社製 商品名「AT−20E」)392部を加え、10分間撹拌し、クリヤー塗料を得た。得られた塗料を25℃および5℃の環境下で、6milのアプリケーターにてガラス板に塗装し、塗装時と同じ環境下で24時間乾燥させて塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表2に示す。
化合物(B)をエトキシ化トリメチロールプロパントリアクリレート(EO20mol)392部に代えて、表1に示す化合物(B)を表2に示す含有量で用いた以外は、実施例1と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表2に示す。
ポリアミン樹脂(A)をエマルションIに代えて、製造例4で得られたエマルションIIを用いた以外は、実施例10と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表2に示す。
イオン交換水159部、ニューコール740(日本乳化剤社製、ノニオン系乳化剤)16部をディスパーにて攪拌し、均一に溶解させ乳化剤水溶液を調整した。その後、化合物(B)であるエトキシ化トリメチロールプロパントリアクリレート(EO3mol)143部を加え、ディスパーにて10分攪拌し粗分散させた。さらに超音波ホモジナイザーにて平均粒子径350nmになるまで分散し、化合物(B)の乳化物を得た。
ポリアミン樹脂(A)として製造例6で得られたエマルションIII2367部に、ディスパーで撹拌しながら、ジプロピレングリコールn−ブチルエーテル(DPnB)118部を加えた後、さらに、ディスパー撹拌しながら、先に得られた化合物(B)の乳化物318部(化合物(B)の含有量143部)を加え、10分間撹拌し、クリヤー塗料を得た。得られた塗料については、実施例1と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表2に示す。
水道水100部、DISPERBYK−190(ビックケミー社製 顔料分散剤)34部、BYK−019(ビックケミー社製 消泡剤)2部、炭酸カルシウム170部、酸化チタン185部、カルシウム系防錆顔料2部からなる顔料分散組成物を、ディスパーにて30分間分散した。次いで、ポリアミン樹脂(A)として製造例2で得られたエマルションI450部、DPnB18部、アデカノールUH−420(アデカ社製 会合型増粘剤)10部を加えて混合し、主剤塗料液とした。さらに、ディスパーで攪拌しながら、化合物(B)としてプロポキシ化ビスフェノールAジアクリレート(PO4mol)41部をDPnB41部に溶解させたものを加え、10分間撹拌し、エナメル塗料を得た。得られた塗料を25℃および5℃の環境下で、6milのアプリケーターにてガラス板に塗装し、塗装時と同じ環境下で24時間乾燥させて塗膜を得た。その後、得られた塗膜の塗膜状態、硬化性および防食性を評価した。結果を表3に示す。
プロポキシ化ビスフェノールAジアクリレート(PO4mol)41部に代えて、エトキシ化グリセリントリアクリレート(EO9mol)(新中村化学社製 商品名「A−GLY−9E」、化合物(B)No.6)33部を用いた以外は、実施例13と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態、硬化性および防食性を評価した。結果を表3に示す。
ポリアミン樹脂(A)として製造例2で得られたエマルションI450部に代えて、製造例4で得られたエマルションII450部を用いた以外は、実施例13と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態、硬化性および防食性を評価した。結果を表3に示す。
化合物(B)を用いなかった以外は、実施例1と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表4に示す。
化合物(B)に代えて、分子量4200、粘度30,000mPa・s、官能基数2のウレタンアクリレート(UA−W2 新中村化学工業社製)2100部を用いた以外は、実施例1と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表4に示す。
化合物(B)に代えて、分子量562、粘度6600mPa・s、官能基数6のジペンタエリスリトールヘキサアクリレート94部を用いた以外は、実施例1と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表4に示す。
化合物(B)に代えて、分子量510,粘度100,000mPa・s、アクリロイル基数2のビスフェノール型エポキシ樹脂(リポキシVR−77 昭和高分子社製)255部を用いた以外は、実施例1と同様にして、塗膜を得た。その後、得られた塗膜の塗膜状態および硬化性を評価した。結果を表4に示す。
アデカレジンEM−101−50(アデカ社製水性エポキシ樹脂エマルジョン;エポキシ等量1000、固形分50%)1000部、DPnB50部を混合し、主剤塗料液とした。
次に、硬化剤としてサンマイドWH−900(エアープロダクツ社製 変性脂肪族ポリアミン、不揮発分60% アミン価220)200部を主剤塗料液に加え、ディスパー攪拌により混合した。得られた塗料を25℃および5℃の環境下で、6milのアプリケーターにてガラス板に塗装し、塗装時と同じ環境下で24時間乾燥させて塗膜を得た。得られた塗膜の硬化性を評価したところ、25℃における硬化性は良好(耐MEK>200回)であり、5℃においては全く硬化していなかった(MEKにて容易に溶けた)。
Claims (10)
- 分子内に1つ以上の第1アミン基および/または第2アミン基を有する水溶性または水分散型のポリアミン樹脂(A)と、
分子内に1つ以上の(メタ)アクリロイル基を有する化合物(B)とを含み、
該ポリアミン樹脂(A)のアミン当量が100〜3000であり、
該化合物(B)の25℃における粘度が3000mPa・s以下である、
水性塗料組成物。 - 前記水性塗料組成物が2液型水性塗料組成物であり、
主剤塗料液が前記ポリアミン樹脂(A)を含み、硬化剤が前記化合物(B)を含む、請求項1に記載の水性塗料組成物。 - 前記ポリアミン樹脂(A)が、アクリル系ポリアミン樹脂またはエポキシ系ポリアミン樹脂である、請求項1または2に記載の水性塗料組成物。
- 前記化合物(B)の分子量が、150以上2000以下である、請求項1から3のいずれかに記載の水性塗料組成物。
- 前記化合物(B)が水溶性化合物であり、かつ前記ポリアミン樹脂(A)が水分散型樹脂である、請求項1から4のいずれかに記載の水性塗料組成物。
- 前記化合物(B)が、自己乳化性化合物である、請求項1から4のいずれかに記載の水性塗料組成物。
- 前記化合物(B)が、前記ポリアミン樹脂(A)により乳化または分散されている、請求項1から4のいずれかに記載の水性塗料組成物。
- 前記化合物(B)が、水溶性化合物および非水溶性化合物の混合物である、請求項1から4のいずれかに記載の水性塗料組成物。
- 前記化合物(B)が、乳化物である、請求項1から4のいずれかに記載の水性塗料組成物。
- 前記硬化剤が、乳化剤をさらに含む、請求項2から4のいずれかに記載の水性塗料組成物。
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JP5821271B2 (ja) * | 2011-05-18 | 2015-11-24 | 三菱レイヨン株式会社 | 活性エネルギー線硬化性含水被覆塗料 |
US8881181B1 (en) | 2012-05-04 | 2014-11-04 | Kabam, Inc. | Establishing a social application layer |
CN102702811A (zh) * | 2012-06-01 | 2012-10-03 | 安徽省金盾涂料有限责任公司 | 水性涂料组合物 |
EP2727968A1 (en) | 2012-11-06 | 2014-05-07 | ALLNEX AUSTRIA GmbH | Multifunctional primary amine, process for its preparation, and use thereof |
JP6106209B2 (ja) * | 2015-05-26 | 2017-03-29 | 日本ペイント株式会社 | 自然乾燥型水性塗料組成物 |
DE112016002028B4 (de) * | 2016-02-12 | 2019-04-25 | Nippon Paint Marine Coatings Co., Ltd. | Korrosionsschutzfarbzusammensetzung, Beschichtungsfilm sowie Schiff und Offshore-Struktur |
CN106002091B (zh) * | 2016-06-03 | 2017-12-01 | 南京钢铁股份有限公司 | 一种压平机垫铁的制作方法 |
CN105969169A (zh) * | 2016-06-30 | 2016-09-28 | 广州中海环保科技有限公司 | 一种天然环保涂料 |
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CN102165027A (zh) | 2011-08-24 |
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