JP2015214698A - 水性エポキシ樹脂分散液 - Google Patents
水性エポキシ樹脂分散液 Download PDFInfo
- Publication number
- JP2015214698A JP2015214698A JP2015114982A JP2015114982A JP2015214698A JP 2015214698 A JP2015214698 A JP 2015214698A JP 2015114982 A JP2015114982 A JP 2015114982A JP 2015114982 A JP2015114982 A JP 2015114982A JP 2015214698 A JP2015214698 A JP 2015214698A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- water
- epoxy
- dispersible
- 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.)
- Pending
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 80
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 79
- 239000006185 dispersion Substances 0.000 title abstract description 16
- -1 fatty acid ester Chemical class 0.000 claims abstract description 39
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 32
- 229920005862 polyol Polymers 0.000 claims abstract description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 29
- 239000000194 fatty acid Substances 0.000 claims abstract description 29
- 229930195729 fatty acid Natural products 0.000 claims abstract description 29
- 238000000576 coating method Methods 0.000 claims abstract description 27
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 18
- 239000011248 coating agent Substances 0.000 claims abstract description 18
- 229920000570 polyether Polymers 0.000 claims abstract description 18
- 150000003077 polyols Chemical class 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000004567 concrete Substances 0.000 claims abstract description 4
- 239000004593 Epoxy Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000004665 fatty acids Chemical class 0.000 claims description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 235000011187 glycerol Nutrition 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 4
- 125000006353 oxyethylene group Chemical group 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 229920003180 amino resin Polymers 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 18
- 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 16
- 239000008199 coating composition Substances 0.000 description 11
- 150000002118 epoxides Chemical group 0.000 description 11
- 235000019445 benzyl alcohol Nutrition 0.000 description 6
- 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 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 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
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000009408 flooring Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- OUQGOXCIUOCDNN-UHFFFAOYSA-N Glycidyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC1CO1 OUQGOXCIUOCDNN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- TXXACRDXEHKXKD-UHFFFAOYSA-M benzyl(trimethyl)phosphanium;chloride Chemical compound [Cl-].C[P+](C)(C)CC1=CC=CC=C1 TXXACRDXEHKXKD-UHFFFAOYSA-M 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 1
- KBWLNCUTNDKMPN-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) hexanedioate Chemical compound C1OC1COC(=O)CCCCC(=O)OCC1CO1 KBWLNCUTNDKMPN-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- PVAONLSZTBKFKM-UHFFFAOYSA-N diphenylmethanediol Chemical compound C=1C=CC=CC=1C(O)(O)C1=CC=CC=C1 PVAONLSZTBKFKM-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000011396 hydraulic cement Substances 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- CZKVZZHFMXVDHP-UHFFFAOYSA-N oxiran-2-ylmethyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC1CO1 CZKVZZHFMXVDHP-UHFFFAOYSA-N 0.000 description 1
- NVLOXZZIKJPCPA-UHFFFAOYSA-N oxiran-2-ylmethyl pentanoate Chemical compound CCCCC(=O)OCC1CO1 NVLOXZZIKJPCPA-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins
- C03C17/326—Epoxy resins
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/20—Materials for coating a single layer on glass
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/70—Properties of coatings
- C03C2217/78—Coatings specially designed to be durable, e.g. scratch-resistant
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2218/00—Methods for coating glass
- C03C2218/30—Aspects of methods for coating glass not covered above
- C03C2218/32—After-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/54—Aqueous solutions or dispersions
Abstract
【解決手段】水分散性エポキシ樹脂Eであって、脂肪族ポリエーテルポリオールAと、1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂Bと、Bと同一であってもBと異なっていてもよい、1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂B’と、エポキシ官能性脂肪酸エステルDと、芳香族ポリオールCとに由来する構成成分を含む、水分散性エポキシ樹脂、その調製方法及びその使用方法に関する。
【選択図】なし
Description
少なくとも20%の質量分率のオキシエチレン基を含み、かつ好ましくは0.2kg/mol〜20kg/molの数平均モル質量Mnを有するポリオキシアルキレンエーテルグリコールである、脂肪族ポリエーテルポリオールAと、
好ましくはポリエーテル構造を有し、更に該ポリオール構造が、1,2,3−トリヒドロキシプロパンに由来する部位と、芳香族ジヒドロキシ化合物に由来する部位とを有する、1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂Bと、
Bと同一であってもBと異なっていてもよく、好ましくはポリエーテル構造を有し、更に該ポリオール構造が、1,2,3−トリヒドロキシプロパンに由来する部位と、芳香族ジヒドロキシ化合物に由来する部位とを有する、1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂B’と、
1個〜10個の炭素原子を有する少なくとも一価の脂肪族アルコールD1と、6個〜30個の炭素原子を有する単官能性脂肪酸D2とのエステルであり、アルコール及び脂肪酸の少なくとも一方がその分子中にエポキシ基を有する、エポキシ官能性脂肪酸エステルDと、
5個〜20個の炭素原子と少なくとも2つのヒドロキシル基とを有する芳香族化合物である、芳香族ポリオールCと、
に由来する構成成分を含む。
実施例1.1
3kg/molの重量平均モル質量Mwを有する1500gのポリエチレングリコール、及び5.41mol/kgのエポキシ基の固有物質量(185g/molのエポキシ当量に相当する)を有する、ビスフェノールAをベースとする185gのポリグリシジルエーテルを合わせて100℃に加熱した。1,4−ジオキサンで5重量%に希釈した9gのBF3−ジエチルエーテラートを、撹拌しながら添加した。反応混合物を130℃に加熱し、反応が終了するまでこの温度で維持し、反応の終了は規定値へのエポキシ基の固有物質量の減少によって示した。OH基の数とエポキシド基の数との比は1:1であり、反応生成物のエポキシ基の固有物質量は2.8mmol/kg(およそ360000g/molのエポキシ当量)であった。
別の行程では、4kg/molの重量平均モル質量Mwを有する300gのポリエチレングリコール、及び5.03mol/kgのエポキシ基の固有物質量(199g/molの「エポキシ当量」に相当する)を有する、ポリオキシプロピレングリコールをベースとする34.4gのポリグリシジルエーテルを合わせて100℃に加熱し、10mlのメチルイソブチルケトンで希釈した0.7gのBF3−ジエチルエーテラートを、撹拌しながら添加した。反応混合物を130℃に加熱し、反応が終了するまでこの温度で維持し、反応の終了は規定値へのエポキシ基の固有物質量の減少によって示した。OH基の数とエポキシド基の数との比は1:1.15であり、エポキシ基の固有物質量は6.7mmol/kg(およそ150000g/molのエポキシ当量に相当する)であった。
2400gのビスフェノールAのジグリシジルエーテル、実施例1.1の乳化剤の400gの水溶液(濃度50%)、及び725gのビスフェノールAを混合させ、85℃に加熱した。減圧下で水を留去した後、1.6gのトリフェニルホスフィンを添加し、混合物を撹拌しながら150℃に加熱した。1時間後、195gのエポキシ化ダイズ油を、更なる1gのトリフェニルホスフィンとともに添加した。反応を更に2時間続けた後、600gの冷たい完全に脱イオン化させた水を強力撹拌しながら徐々に添加した。容器温度を70℃に降下させ、その後、218gの完全に脱イオン化させた水を更に3度、60℃で撹拌しながら添加した。次に、得られる白濁分散液を室温まで冷却させ、更に1400gの完全に脱イオン化させた水を添加した。
以下の処方に従って透明なコーティング組成物を調製した:
実施例2の樹脂分散液、比較のために、3%のベンジルアルコールと7%のメトキシプロパノールとを含有する、欧州特許第0272595号の実施例IV−1に従って調製した樹脂分散液を各々50g、それぞれ25.3g及び19.4gの、エポキシ樹脂と脂肪族アミンとの商業用付加物硬化剤((商標)Beckopox VEH 2188/55WA、Cytec Austria GmbH)と混合させた。粘度は、両方の系について、完全に脱イオン化させた水の添加によって830mPa・sに適合させた。ポットライフはいずれの場合も3時間であることが確認された。
Claims (12)
- 水分散性エポキシ樹脂Eであって、脂肪族ポリエーテルポリオールAと、1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂Bと、Bと同一であってもBと異なっていてもよい、1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂B’と、エポキシ官能性脂肪酸エステルDと、芳香族ポリオールCとに由来する構成成分を含む水分散性エポキシ樹脂。
- 請求項1に記載の水分散性エポキシ樹脂Eであって、前記脂肪族ポリエーテルポリオールAが、少なくとも20%の質量分率のオキシエチレン基を含みかつ0.2kg/mol〜20kg/molの数平均モル質量Mnを有するポリオキシアルキレンエーテルグリコールである請求項1に記載の水分散性エポキシ樹脂。
- 請求項1に記載の水分散性エポキシ樹脂Eであって、前記エポキシ樹脂Bが、1分子当たり少なくとも2つのエポキシド基を有し、かつポリエーテル構造を有し、更に該ポリエーテル構造が、1,2,3−トリヒドロキシプロパンに由来する部位と、芳香族ジヒドロキシ化合物に由来する部位とを有する請求項1に記載の水分散性エポキシ樹脂。
- 請求項1に記載の水分散性エポキシ樹脂Eであって、前記エポキシ樹脂B’が、1分子当たり少なくとも2つのエポキシド基を有し、かつBと同一であってもBと異なっていてもよく、ポリエーテル構造を有し、更に該ポリエーテル構造が、1,2,3−トリヒドロキシプロパンに由来する部位と、芳香族ジヒドロキシ化合物に由来する部位とを有する請求項1に記載の水分散性エポキシ樹脂。
- 請求項1に記載の水分散性エポキシ樹脂Eであって、前記エポキシ官能性脂肪酸エステルDが、1個〜10個の炭素原子を有する少なくとも一価の脂肪族アルコールD1と、6個〜30個の炭素原子を有する単官能性脂肪酸D2とのエステルであり、該アルコールD1及び該脂肪酸D2の少なくとも一方がその分子中にエポキシ基を有する請求項1に記載の水分散性エポキシ樹脂。
- 請求項1に記載の水分散性エポキシ樹脂Eであって、前記芳香族ポリオールCが、5個〜20個の炭素原子と少なくとも2つのヒドロキシル基とを有する芳香族化合物である請求項1に記載の水分散性エポキシ樹脂。
- 請求項1に記載の水分散性エポキシ樹脂Eであって、エポキシ官能性脂肪酸エステルDの量が、0.5%〜20%の質量分率に相当するように選ばれ、該質量分率が、該組成物中の成分Dの質量mDと樹脂Eの質量mEとの比mD/mEである請求項1に記載の水分散性エポキシ樹脂。
- 請求項1に記載の水分散性エポキシ樹脂Eの製造方法であって、
第1の工程において、好ましくは酸性触媒の存在下で、脂肪族ポリエーテルポリオールAと、1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂Bとを反応させることであって、付加物ABを形成するよう反応させること、
その後、この付加物ABを、前進反応における第2の工程において、更なるエポキシ樹脂B’、エポキシ官能性脂肪酸エステルD及び芳香族ポリオールCと反応させること、
を含む請求項1に記載の水分散性エポキシ樹脂Eを製造する方法。 - 前記第1の工程中、該縮合反応に使用される、前記脂肪族ポリオールA中のOH基の数と、前記エポキシ化合物Bのエポキシ基の数との比が、1:0.85〜1:3.5となり、かつ前記縮合生成物のエポキシ基の固有物質量が0.002mol/kg〜5mol/kgとなるように、前記脂肪族ポリエーテルポリオールA及び1分子当たり少なくとも2つのエポキシド基を有するエポキシ樹脂Bの分量を選ぶ請求項8に記載の方法。
- 該反応混合物中に存在する前記エポキシ基の少なくとも90%が消費されるまで、前記付加物AB、更なるエポキシ樹脂B’及び芳香族ポリオールCを初めに前記第2の工程において触媒の存在下で反応させ、その後、成分D及び任意に更なる触媒を添加し、該反応を完了させる請求項8に記載の方法。
- Dの少なくとも5%である一部が未反応のまま残るように、Dの量を選ぶ請求項8に記載の方法。
- 請求項1に記載の水分散性エポキシ樹脂Eの使用方法であって、
塩基性硬化剤である多官能性アミン、アミンとエポキシ樹脂との付加物、マンニッヒ塩基及びポリアミドアミン;又はポリカルボン酸及びその無水物並びに多官能性フェノールである酸性硬化剤;並びに、アミノプラスト樹脂及びフェノプラスト樹脂である、エーテル結合若しくはイミン結合を形成する硬化剤からなる群より選択される1種以上の硬化剤を混和させる工程と、
刷毛塗、噴霧、浸漬及びロール塗、並びに塗工用ブレード又は塗工用ワイヤによる塗布からなる群より選択される方法によって、金属、木材、ガラス、コンクリート、プラスチック、セラミック等の基板上に、形成した該混合物を堆積させる工程と、
該塗布した塗膜を加熱により硬化させる工程と、
を含む請求項1に記載の水分散性エポキシ樹脂Eの使用方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09176892A EP2325221A1 (en) | 2009-11-24 | 2009-11-24 | Aqueous epoxy resin dispersions |
EP09176892.9 | 2009-11-24 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012540388A Division JP5925125B2 (ja) | 2009-11-24 | 2010-11-22 | 水性エポキシ樹脂分散液 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016241844A Division JP6576902B2 (ja) | 2009-11-24 | 2016-12-14 | 水性エポキシ樹脂分散液 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2015214698A true JP2015214698A (ja) | 2015-12-03 |
Family
ID=41692799
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012540388A Active JP5925125B2 (ja) | 2009-11-24 | 2010-11-22 | 水性エポキシ樹脂分散液 |
JP2015114982A Pending JP2015214698A (ja) | 2009-11-24 | 2015-06-05 | 水性エポキシ樹脂分散液 |
JP2016241844A Active JP6576902B2 (ja) | 2009-11-24 | 2016-12-14 | 水性エポキシ樹脂分散液 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012540388A Active JP5925125B2 (ja) | 2009-11-24 | 2010-11-22 | 水性エポキシ樹脂分散液 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016241844A Active JP6576902B2 (ja) | 2009-11-24 | 2016-12-14 | 水性エポキシ樹脂分散液 |
Country Status (9)
Country | Link |
---|---|
US (2) | US9346910B2 (ja) |
EP (2) | EP2325221A1 (ja) |
JP (3) | JP5925125B2 (ja) |
KR (1) | KR101829641B1 (ja) |
CN (1) | CN102666634B (ja) |
ES (1) | ES2457234T3 (ja) |
PL (1) | PL2504373T3 (ja) |
SI (1) | SI2504373T1 (ja) |
WO (1) | WO2011064176A1 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2325221A1 (en) * | 2009-11-24 | 2011-05-25 | Cytec Surface Specialties Austria GmbH | Aqueous epoxy resin dispersions |
US9303131B2 (en) | 2012-02-15 | 2016-04-05 | Dow Global Technologies Llc | Premolding article from thermoset and thermoplastic polymer dispersions |
EP2814875A1 (en) | 2012-02-15 | 2014-12-24 | Dow Global Technologies LLC | Pre-molding article from thermoset polymer dispersions |
EP2639272A1 (en) | 2012-03-13 | 2013-09-18 | Cytec Surface Specialties, S.A. | Active energy ray curable aqueous emulsions |
ITMI20131149A1 (it) * | 2013-07-09 | 2015-01-10 | Renner Italia S P A | Composizione preservante per legno |
DE102015012172A1 (de) * | 2015-09-23 | 2017-03-23 | Universität Kassel | Thermisch aktivierbare, schnellhärtende Klebstoffbeschichtung |
BR112019003697B1 (pt) | 2016-08-25 | 2022-12-20 | Stepan Company | Composição de polímero de poliéster-epóxido, revestimento, elastômero, elastômero microcelular, adeviso, selante e processos para preparar uma composição de polímero de poliéster-epóxido |
MX2019010466A (es) | 2017-03-02 | 2019-12-16 | Stepan Co | Composiciones de polimeros de poliester-epoxido modificados con isocianato. |
EP3601406B1 (en) * | 2017-03-31 | 2021-04-14 | Stepan Company | Polyether-epoxide polymer compositions |
CN107236416B (zh) * | 2017-06-21 | 2019-09-27 | 浙江伟星实业发展股份有限公司 | 一种拉头涂料及其涂布工艺 |
US20210009844A1 (en) * | 2018-02-19 | 2021-01-14 | Arkema Inc. | Coalescing agents for waterborne coatings |
US10450478B1 (en) * | 2018-10-23 | 2019-10-22 | Chang Chun Plastics Co., Ltd. | Epoxy resin, aqueous dispersion and water-borne epoxy coating composition comprising the same |
CA3123246A1 (en) | 2018-12-19 | 2020-06-25 | Stepan Company | One-component adhesive compositions |
KR102293684B1 (ko) * | 2020-03-06 | 2021-08-26 | 주식회사 케이씨씨 | 수용성 에폭시 수지, 이의 제조방법 및 이를 포함하는 수성 프라이머 조성물 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5184825A (en) * | 1974-12-12 | 1976-07-24 | Ciba Geigy | Mizudekishakukanona netsukokaseihifukusoseibutsu no seizohoho |
JPS5365326A (en) * | 1976-11-22 | 1978-06-10 | Ciba Geigy Ag | Waterrdilutable and heattcurable coating composition and method of making same |
JPS63168425A (ja) * | 1986-12-20 | 1988-07-12 | ヘキスト・アクチエンゲゼルシャフト | 安定なエポキシ樹脂水性分散物、その製造方法およびその用途 |
JPH0238443A (ja) * | 1988-06-15 | 1990-02-07 | Hoechst Ag | エポキシ樹脂の安定な水性分散物、その製造方法およびその用途 |
JPH10510870A (ja) * | 1994-12-21 | 1998-10-20 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | エポキシ官能性ポリエーテル |
JP2004359746A (ja) * | 2003-06-03 | 2004-12-24 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物及びエポキシ樹脂エマルジョン |
JP2013511613A (ja) * | 2009-11-24 | 2013-04-04 | サイテク オーストリア ゲーエムベーハー | 水性エポキシ樹脂分散液 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3425976A (en) * | 1965-08-18 | 1969-02-04 | Union Carbide Corp | Anti-fogging film comprising vinyl chloride polymer,glycerol monostearate and incompatible plasticizer |
US3447940A (en) * | 1967-12-04 | 1969-06-03 | Pillsbury Co | Paint composition containing polysaccharides |
US3654201A (en) * | 1970-01-19 | 1972-04-04 | Celanese Coatings Co | Polymeric dispersions stabilized by vinyl oxazoline polymers |
US3806478A (en) * | 1970-04-20 | 1974-04-23 | Celanese Coatings Co | Polymeric dispersions stabilized by cellulosic precursors |
US3669728A (en) * | 1970-06-22 | 1972-06-13 | Ppg Industries Inc | Method for providing opaque,microcellular,film coatings on substrates and the resultant product |
DE4128487A1 (de) * | 1991-08-28 | 1993-03-04 | Hoechst Ag | Verfahren zur herstellung von waessrigen epoxidharz-dispersionen |
DE19536381A1 (de) * | 1995-09-29 | 1997-04-03 | Hoechst Ag | Reaktivverdünner-haltige Epoxid- und Epoxid-Polyacrylat-Dispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
US6207228B1 (en) * | 1998-04-21 | 2001-03-27 | Vincent G. Hundt | Concurrent fragmentation and impregnation machine and processing |
JP3499837B2 (ja) * | 2001-03-13 | 2004-02-23 | 住友ベークライト株式会社 | プリプレグの製造方法 |
DE10128889A1 (de) | 2001-06-15 | 2002-12-19 | Solutia Austria Gmbh Werndorf | Wasserverdünnbare Aminhärter für wäßrige Zweikomponenten-Epoxidharz-Systeme |
DE102004049717A1 (de) * | 2004-10-11 | 2006-04-13 | Henkel Kgaa | Alterungsbeständige Beschichtungen und Klebeverbunde |
US7390858B2 (en) | 2005-10-18 | 2008-06-24 | Valspar Sourcing, Inc. | Coating compositions and methods |
US20090149591A1 (en) * | 2007-12-07 | 2009-06-11 | Yong Yang | Paint Compositions With Low- or Zero-VOC Coalescence Aids and Nano-Particle Pigments |
PL2285754T3 (pl) * | 2008-06-13 | 2018-12-31 | Benjamin Moore & Co. | Wodne kompozycje powłokowe z minimalną emisją związków lotnych |
US20120165428A1 (en) * | 2010-12-23 | 2012-06-28 | Columbia Insurance Company | Polymer for Extending the Open Time of Waterborne Architectural Coatings |
-
2009
- 2009-11-24 EP EP09176892A patent/EP2325221A1/en not_active Withdrawn
-
2010
- 2010-11-22 ES ES10784293.2T patent/ES2457234T3/es active Active
- 2010-11-22 CN CN201080053088.3A patent/CN102666634B/zh active Active
- 2010-11-22 PL PL10784293T patent/PL2504373T3/pl unknown
- 2010-11-22 US US13/510,987 patent/US9346910B2/en active Active
- 2010-11-22 JP JP2012540388A patent/JP5925125B2/ja active Active
- 2010-11-22 KR KR1020127016401A patent/KR101829641B1/ko active IP Right Grant
- 2010-11-22 WO PCT/EP2010/067960 patent/WO2011064176A1/en active Application Filing
- 2010-11-22 EP EP10784293.2A patent/EP2504373B1/en active Active
- 2010-11-22 SI SI201030551T patent/SI2504373T1/sl unknown
-
2015
- 2015-06-05 JP JP2015114982A patent/JP2015214698A/ja active Pending
-
2016
- 2016-04-25 US US15/137,039 patent/US9938428B2/en active Active
- 2016-12-14 JP JP2016241844A patent/JP6576902B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5184825A (en) * | 1974-12-12 | 1976-07-24 | Ciba Geigy | Mizudekishakukanona netsukokaseihifukusoseibutsu no seizohoho |
JPS5365326A (en) * | 1976-11-22 | 1978-06-10 | Ciba Geigy Ag | Waterrdilutable and heattcurable coating composition and method of making same |
JPS63168425A (ja) * | 1986-12-20 | 1988-07-12 | ヘキスト・アクチエンゲゼルシャフト | 安定なエポキシ樹脂水性分散物、その製造方法およびその用途 |
JPH0238443A (ja) * | 1988-06-15 | 1990-02-07 | Hoechst Ag | エポキシ樹脂の安定な水性分散物、その製造方法およびその用途 |
JPH10510870A (ja) * | 1994-12-21 | 1998-10-20 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | エポキシ官能性ポリエーテル |
JP2004359746A (ja) * | 2003-06-03 | 2004-12-24 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物及びエポキシ樹脂エマルジョン |
JP2013511613A (ja) * | 2009-11-24 | 2013-04-04 | サイテク オーストリア ゲーエムベーハー | 水性エポキシ樹脂分散液 |
Also Published As
Publication number | Publication date |
---|---|
CN102666634B (zh) | 2015-03-25 |
JP6576902B2 (ja) | 2019-09-18 |
JP2013511613A (ja) | 2013-04-04 |
US20120308729A1 (en) | 2012-12-06 |
PL2504373T3 (pl) | 2014-06-30 |
US9346910B2 (en) | 2016-05-24 |
EP2504373A1 (en) | 2012-10-03 |
SI2504373T1 (sl) | 2014-04-30 |
ES2457234T3 (es) | 2014-04-25 |
KR20120117994A (ko) | 2012-10-25 |
EP2325221A1 (en) | 2011-05-25 |
EP2504373B1 (en) | 2014-01-08 |
JP2017115138A (ja) | 2017-06-29 |
WO2011064176A1 (en) | 2011-06-03 |
JP5925125B2 (ja) | 2016-05-25 |
US20160237304A1 (en) | 2016-08-18 |
US9938428B2 (en) | 2018-04-10 |
CN102666634A (zh) | 2012-09-12 |
KR101829641B1 (ko) | 2018-03-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6576902B2 (ja) | 水性エポキシ樹脂分散液 | |
US4886845A (en) | Stable aqueous epoxy resin dispersion, process for the preparation thereof and use thereof | |
JP5951008B2 (ja) | 硬化性樹脂系のための水性アミン硬化剤 | |
CN106164125B (zh) | 在低voc应用中用作环氧树脂的固化剂的基于呋喃的胺 | |
JPH06298910A (ja) | エポキシ樹脂水性分散物のための硬化剤 | |
JP7369621B2 (ja) | 腐食防止のための水性コーティング組成物 | |
US5523336A (en) | Aqueous, one-component coating composition and use thereof in processes for repair lacquer coating of plastic substrates | |
CA2119170A1 (en) | Polyol/epoxy adducts for use as emulsifier for liquid epoxy resins | |
JPH09111099A (ja) | 可使時間の終了がわかる水希釈性エポキシ樹脂系のための乳化剤系 | |
TWI503341B (zh) | 羥基官能聚酯樹脂 | |
JP2003026990A (ja) | コーティング組成物およびその硬化膜 | |
US20220290001A1 (en) | Self-emulsifying epoxy composition and the coating composition prepared from the same | |
CN115803358A (zh) | 环氧-胺加合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160526 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160614 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160914 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20161111 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20170214 |