JP2021529239A - 電着可能なコーティング組成物 - Google Patents
電着可能なコーティング組成物 Download PDFInfo
- Publication number
- JP2021529239A JP2021529239A JP2020572776A JP2020572776A JP2021529239A JP 2021529239 A JP2021529239 A JP 2021529239A JP 2020572776 A JP2020572776 A JP 2020572776A JP 2020572776 A JP2020572776 A JP 2020572776A JP 2021529239 A JP2021529239 A JP 2021529239A
- Authority
- JP
- Japan
- Prior art keywords
- group
- epoxy resin
- resin dispersion
- aqueous resin
- carbamate functional
- 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
- 239000008199 coating composition Substances 0.000 title claims description 27
- 229920005989 resin Polymers 0.000 claims abstract description 229
- 239000011347 resin Substances 0.000 claims abstract description 229
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 186
- 239000003822 epoxy resin Substances 0.000 claims abstract description 177
- 239000006185 dispersion Substances 0.000 claims abstract description 171
- 238000000576 coating method Methods 0.000 claims abstract description 100
- 239000011248 coating agent Substances 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 60
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 52
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 32
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 100
- 239000000758 substrate Substances 0.000 claims description 79
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 68
- 239000003795 chemical substances by application Substances 0.000 claims description 58
- -1 alkyl radical Chemical class 0.000 claims description 53
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 50
- 239000004593 Epoxy Substances 0.000 claims description 41
- 239000007787 solid Substances 0.000 claims description 39
- 238000005260 corrosion Methods 0.000 claims description 38
- 230000007797 corrosion Effects 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 125000003700 epoxy group Chemical group 0.000 claims description 33
- 125000000524 functional group Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 230000007062 hydrolysis Effects 0.000 claims description 31
- 238000006460 hydrolysis reaction Methods 0.000 claims description 31
- 150000005840 aryl radicals Chemical class 0.000 claims description 28
- 239000005056 polyisocyanate Substances 0.000 claims description 28
- 229920001228 polyisocyanate Polymers 0.000 claims description 28
- 229920001002 functional polymer Polymers 0.000 claims description 26
- 238000010998 test method Methods 0.000 claims description 26
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 23
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 238000013112 stability test Methods 0.000 claims description 15
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 229920003180 amino resin Polymers 0.000 claims description 11
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229920001568 phenolic resin Polymers 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 6
- 238000000151 deposition Methods 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 6
- 230000000052 comparative effect Effects 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 238000010586 diagram Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 119
- 239000010410 layer Substances 0.000 description 66
- 229920000642 polymer Polymers 0.000 description 43
- 239000000049 pigment Substances 0.000 description 23
- 239000002585 base Substances 0.000 description 22
- 235000011007 phosphoric acid Nutrition 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000004070 electrodeposition Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229910052804 chromium Inorganic materials 0.000 description 17
- 239000011651 chromium Substances 0.000 description 17
- 239000003086 colorant Substances 0.000 description 17
- 150000002431 hydrogen Chemical class 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 16
- 239000003112 inhibitor Substances 0.000 description 16
- 239000003973 paint Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 239000002105 nanoparticle Substances 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 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 13
- 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 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 239000011247 coating layer Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 230000000670 limiting effect Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229910000547 2024-T3 aluminium alloy Inorganic materials 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 238000007654 immersion Methods 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 239000002981 blocking agent Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000010959 steel Substances 0.000 description 7
- 238000000108 ultra-filtration Methods 0.000 description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 5
- BSBQJOWZSCCENI-UHFFFAOYSA-N 3-hydroxypropyl carbamate Chemical compound NC(=O)OCCCO BSBQJOWZSCCENI-UHFFFAOYSA-N 0.000 description 5
- 229910000838 Al alloy Inorganic materials 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000008399 tap water Substances 0.000 description 4
- 235000020679 tap water Nutrition 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- 229910000165 zinc phosphate Inorganic materials 0.000 description 4
- 0 CC(COc1ccc([C@@](*)(c(cc2)ccc2OC)I)cc1)OC(NC1CC(C)(CNC(O*OC(*)=O)=O)CC(C)(C)C1)=O Chemical compound CC(COc1ccc([C@@](*)(c(cc2)ccc2OC)I)cc1)OC(NC1CC(C)(CNC(O*OC(*)=O)=O)CC(C)(C)C1)=O 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 229960004217 benzyl alcohol Drugs 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 239000002828 fuel tank Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000002365 multiple layer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical group NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical group [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- 206010073306 Exposure to radiation Diseases 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910018286 SbF 6 Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910001297 Zn alloy Inorganic materials 0.000 description 2
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 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
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
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- 150000003852 triazoles Chemical class 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229940048102 triphosphoric acid Drugs 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- KHADWTWCQJVOQO-UHFFFAOYSA-N zinc;oxido-(oxido(dioxo)chromio)oxy-dioxochromium Chemical compound [Zn+2].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KHADWTWCQJVOQO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
Description
(式中、R1およびR2はそれぞれ、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、または別のホスホエステル基を表す)に示されるように、炭素原子とホスホエステル基の酸素との間の共有結合を指す。本明細書で使用する場合、用語「ホスホエステル基」は、アルキルラジカルまたはアリールラジカルに共有結合した酸素原子を指し、酸素原子はまた、二重結合によって別の酸素原子に結合しているリン原子にも共有結合している。例えば、上記の構造において、R1またはR2がO−Rである場合、R1またはR2はホスホエステル基であると見なされ、式中、Rはアルキルラジカルまたはアリールラジカルである。リン原子は、ホスホエステル結合を含む3つのホスホエステル基を含んでもよいことが理解されよう。
(式中、R1およびR2はそれぞれ独立して、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、またはホスホエステル基を表す)にしたがってもよい。この構造による複数の末端基は、リン酸化エポキシ樹脂上に存在してもよい。例えば、リン酸化エポキシ樹脂は、ホスホエステル結合によって樹脂に共有結合したリン原子を含む少なくとも2つの末端基を含み得る。ホスホエステル結合によって樹脂に共有結合したリン原子を含む2つの末端基を有するリン酸化エポキシ樹脂は、構造:
(式中、R1、R2、R3およびR4は、それぞれ独立して、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、またはホスホエステル基を表し、Rは、リン酸化エポキシ樹脂の残部を表す)にしたがってもよい。リン酸化エポキシ樹脂の残部は、エポキシ官能性ポリマーの残部または残基を含んでもよい。本明細書で使用する場合、R基に関する用語「エポキシ官能性ポリマーの残部または残基」は、エポキシ官能性ポリマーのポリマー骨格および分子構造に示されていないその上に存在する任意の置換基を指す。リン酸化エポキシ樹脂の残部および/またはエポキシ官能性ポリマーの残部もしくは残基は、脂肪族、芳香族、環状、非環式、脂環式または複素環式であってもよい。R1、R2、R3またはR4がヒドロキシルである場合、Rx基は、別のエポキシ含有ポリマーのエポキシド官能基とさらに反応する可能性のあるリン酸基を含み、その結果、リン酸化エポキシ樹脂はポリマー骨格に存在するリン原子で鎖延長されることを理解されたい。さらに、2つのリン酸基が存在し、それぞれがエポキシ含有ポリマーのエポキシド官能基と反応する場合、亜リン酸からの分枝が発生する可能性がある。
(式中、Rは有機ラジカル、例えば合計1〜30個、例えば6〜18個の炭素を有する有機ラジカルである)の有機ホスホン酸である。Rは、脂肪族、芳香族、または脂肪族/芳香族の混合物であってもよく、非置換炭化水素または置換炭化水素であってもよい。
(式中、RおよびR’はそれぞれ独立して水素または有機ラジカルである)の有機ホスフィン酸である。このようなラジカルの例は、合計1〜30個、例えば6〜18個の炭素を有するラジカルである。ホスフィン酸の有機成分(R、R’)は、脂肪族、芳香族、または脂肪族/芳香族の混合物であることができる。RおよびR’は、非置換炭化水素または置換炭化水素であることができる。
(式中、R1は、リン酸化エポキシ樹脂の残部を含み、必要に応じてカルバメート官能基をリン酸化エポキシ樹脂のポリマー骨格に結合する別の有機連結基をさらに含んでもよく、R2は、水素、アルキルラジカル、またはアリールラジカルを含む)を有するリン酸化エポキシ樹脂上の官能基を指す。カルバメートは、ペンダント基、末端基、または複数のカルバメート基が存在する場合はそれらの組み合わせであってもよい。有機連結基は、エポキシ樹脂骨格とカルバメート官能基を結合することができる。カルバメート官能基、およびカルバメート官能基をエポキシ樹脂骨格に結合する有機連結基を含む部分の特定の非限定的な例は、構造:
(式中、Rはリン酸化エポキシ樹脂の残部を表し、R5は、二価の、置換または非置換の有機基、例えば、アルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)であってもよい。カルバメート官能基およびカルバメート官能基をエポキシ樹脂骨格に結合する有機連結基を含む部分の別の特定の非限定的な例は、構造:
(式中、Rはリン酸化エポキシ樹脂の残部を表す)であってもよい。
(式中、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表し、R5は、二価の、置換または非置換の有機基、例えばアルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)を含む少なくとも1つの構成単位Aを含んでもよい。例えば、リン酸化エポキシ樹脂は、構造:
(式中、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表す)を含む少なくとも1つの構成単位Aを含んでもよい。例えば、R1およびR2はそれぞれ独立して、水素、メチル、エチル、プロピル、ブチル、またはフェニル基を表してもよい。さらに、芳香環を置換してもよい。
(式中、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表す)を含む少なくとも1つの構成単位Bをさらに含んでもよい。例えば、R1およびR2はそれぞれ独立して、水素、メチル、エチル、プロピル、ブチル、またはフェニル基を表してもよい。さらに、芳香環を置換してもよい。
(式中、mは1〜2,000であり、nは0〜2,000であり、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表し、R3およびR4はそれぞれ独立して、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、またはホスホエステル基を表し、R5は、二価の、置換または非置換の有機基、例えばアルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)を含んでもよい。例えば、リン酸化エポキシ樹脂は、構造:
(式中、mは1〜2,000であり、nは0〜2,000であり、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表し、R3およびR4はそれぞれ独立して、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、またはホスホエステル基を表す)を含んでもよい。例えば、R1およびR2はそれぞれ独立して、水素、メチル、エチル、プロピル、ブチル、またはフェニル基を表してもよい。さらに、芳香環を置換してもよい。構造は、カルバメート官能性ブロックおよびヒドロキシル官能性ブロックを含むブロックポリマーを示しているが、ポリマーは、ランダム重合体セグメントおよび重合生成物も含んでもよい。
(式中、各R5は、二価の、置換または非置換の有機基、例えば、アルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)を含んでもよい。例えば、カルバメート官能性オリゴマーは、3つ以上のカルバメート官能基を含んでもよく、そして構造:
を含んでもよい。
態様
炭素−リン結合によって、またはホスホエステル結合によって樹脂に共有結合したリン原子を含む少なくとも1つの末端基と、
少なくとも1つのカルバメート官能基と、を含む、リン酸化エポキシ樹脂。
態様2
末端基は、リン酸塩、有機リン酸塩、ホスホン酸塩、有機ホスホン酸塩、ホスフィン酸塩、有機ホスフィン酸塩、またはそれらの組み合わせを含む、態様1のリン酸化エポキシ樹脂。
態様3
リン酸化エポキシ樹脂は、炭素−リン結合によって、またはホスホエステル結合によって樹脂に共有結合したリン原子を含むペンダント基を実質的に含まない、態様1または2のいずれか一つに記載のリン酸化エポキシ樹脂。
態様4
リン酸化エポキシ樹脂の末端基は、構造:
(式中、R1およびR2はそれぞれ独立して、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、またはホスホエステル基を表す)を含む、態様1〜3のいずれか一つに記載のリン酸化エポキシ樹脂。
態様5
リン酸化エポキシ樹脂は、カルバメート官能基を含む少なくとも1つのペンダント基を含み、ペンダント基は、構造:
(式中、Rはリン酸化エポキシ樹脂の残部を表し、R5は、二価の、置換または非置換の有機基、例えば、アルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)を含む、態様1〜4のいずれか一つに記載のリン酸化エポキシ樹脂。
態様6
リン酸化エポキシ樹脂は、構造:
(式中、R1、R2、R3およびR4は、それぞれ独立して、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、またはホスホエステル基を表し、Rは、少なくとも1つのカルバメート官能基を含むエポキシ官能性ポリマーの残基を表す)を含む、態様1〜5のいずれか一つに記載のリン酸化エポキシ樹脂。
態様7
リン酸化エポキシ樹脂は、構造:
(式中、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表し、R5は、二価の、置換または非置換の有機基、例えばアルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)を含む少なくとも1つの構成単位Aを含む、態様1〜6のいずれか一つに記載のリン酸化エポキシ樹脂。
態様8
リン酸化エポキシ樹脂は、構造:
(式中、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表す)を含む少なくとも1つの構成単位Bをさらに含む、態様1〜7のいずれか一つに記載のリン酸化エポキシ樹脂。
態様9
構成単位Aの構成単位Bに対する比は1:20〜20:1である、態様8に記載のリン酸化エポキシ樹脂。
態様10
リン酸化エポキシ樹脂は、構造:
(式中、mは1〜2,000であり、nは0〜2,000であり、R1およびR2はそれぞれ独立して、水素、アルキルラジカルまたはアリールラジカルを表し、R3およびR4はそれぞれ独立して、水素、ヒドロキシル、アルキルラジカル、アリールラジカル、またはホスホエステル基を表し、R5は、二価の、置換または非置換の有機基、例えばアルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)を含む、態様1〜7のいずれか一つに記載のエポキシ樹脂。
態様11
(a)態様1〜10のいずれか一つに記載のリン酸化エポキシ樹脂と、
(b)硬化剤と、を含む、水性樹脂分散体。
態様12
硬化剤は、カルバメート官能基と反応する少なくとも2つの官能基を含む、態様11に記載の水性樹脂分散体。
態様13
硬化剤は、アミノプラスト樹脂、フェノプラスト樹脂、ブロック化ポリイソシアネート、またはそれらの組み合わせを含む、態様11または12のいずれか一つに記載の水性樹脂分散体。
態様14
硬化剤は高分子量の揮発性基を含む、態様11〜13のいずれか一つに記載の水性樹脂分散体。
態様15
高分子量の揮発性基は、水性樹脂分散体の樹脂固形分の総重量に対して、5重量%〜50重量%、例えば7重量%〜45重量%、例えば9重量%〜40重量%、例えば11重量%〜35重量%、例えば13重量%〜30重量%の水性樹脂分散体の樹脂固形分を含む、態様17に記載の水性樹脂分散体。
態様16
樹脂分散体は、金属含有触媒を実質的に含まない、態様11〜15のいずれか一つに記載の水性樹脂分散体。
態様17
少なくとも2つのカルバメート基を含むカルバメート官能性オリゴマーをさらに含む、態様11〜16のいずれか一つに記載の水性樹脂分散体。
態様18
カルバメート官能性オリゴマーは、構造:
(式中、R5は、二価の、置換または非置換の有機基、例えば、アルキレン基、シクロアルキレン基、アリーレン基、シクロアリーレン基、またはそれらの組み合わせを含む)を含む、態様17に記載の水性樹脂分散体。
態様19
方法は、
少なくとも1つの末端エポキシド官能基および少なくとも1つのペンダントヒドロキシル官能基を含むエポキシ樹脂を、イソシアナト官能基およびカルバメート官能基を含む分子と反応させることであって、ペンダントヒドロキシル官能基およびイソシアナト官能基は、反応してウレタン結合を形成し、それによって分子がエポキシ樹脂に組み込まれてカルバメート官能性エポキシ樹脂を形成する、反応させることと、
カルバメート官能性エポキシ樹脂を、リン酸、ホスホン酸、ホスフィン酸、またはそれらの組み合わせとさらに反応させることであって、カルバメート官能性エポキシ樹脂の少なくとも1つの末端エポキシド官能基は、リン酸またはホスホン酸の酸基と反応し、それによって、リン酸、ホスホン酸、および/またはホスフィン酸は、カルバメート官能性エポキシ樹脂に組み込まれ、リン酸化されたカルバメート官能性エポキシ樹脂を形成する、さらに反応させることと、
を含む、態様1〜10のいずれか一つに記載のリン酸化エポキシ樹脂を製造する方法。
態様20
リン酸化カルバメート官能性エポキシ樹脂は塩基で中和される、態様19に記載の方法。
態様21
態様11〜18のいずれか一つに記載の水性樹脂分散体を基材上に電気泳動的に堆積させて基材上にコーティングを形成することを含む、基材をコーティングする方法。
態様22
コーティングされた基材は、態様11〜18のいずれか一つに記載の樹脂分散体で少なくとも部分的にコーティングされる、コーティングされた基材。
態様23
(a)エポキシ樹脂と、
(b)少なくとも2つのカルバメート官能基を含むカルバメート官能性オリゴマーと、を含む、水性樹脂分散体。
態様24
カルバメート官能性オリゴマーは、構造:
を含む、態様23に記載の水性樹脂分散体。
態様25
硬化剤をさらに含む、態様23または24に記載の水性樹脂分散体。
カルバメート官能性オリゴマー(ヒドロキシプロピルカルバメートで完全にキャップされたヘキサメチレンジイソシアネート三量体)を作製するための反応の概略的および一般的な手順を、以下のように実行した。
実施例3A:ヒドロキシル官能性リン酸化エポキシ樹脂と実施例2のカルバメート官能性オリゴマーとの水性樹脂分散体を作製する一般的な手順を、以下のように実行した。
カルバメート官能性分子、ヒドロキシプロピルカルバメートでハーフキャップされたイソホロンジイソシアネートを作製するための反応の概略的および一般的な手順を、以下のように実行した。
実施例5−カルバメート官能性リン酸化エポキシ樹脂の水性樹脂分散体の調製
実施例7A:カルバメート官能性リン酸化エポキシ樹脂と実施例2のカルバメート官能性オリゴマーとの水性樹脂分散体を作製する一般的な手順を、以下のように実行した。
実施例9A:高分子量の揮発性基を含むButyl CELLOSOLVE修飾硬化剤を用いてヒドロキシル官能性リン酸化エポキシ樹脂の水性樹脂分散体を作製する一般的な手順を、以下のように実行した。
実施例10A:高分子量の揮発性基を含むButyl CELLOSOLVE修飾硬化剤を用いてカルバメート官能性リン酸化エポキシ樹脂を作製する一般的な手順を、以下のように実行した。
結果の概要
Claims (35)
- 炭素−リン結合によって、またはホスホエステル結合によって樹脂に共有結合したリン原子を含む少なくとも1つの末端基と、
少なくとも1つのカルバメート官能基と、
を含む、リン酸化エポキシ樹脂。 - 構成単位Aの構成単位Bに対する比は1:20〜20:1である、請求項4に記載のリン酸化エポキシ樹脂。
- (a)
(i)炭素−リン結合によって、またはホスホエステル結合によって樹脂に共有結合するリン原子を含む少なくとも1つの末端基と、
(ii)少なくとも1つのカルバメート官能基と、を含む、リン酸化エポキシ樹脂と、
(b)硬化剤と、を含む、水性樹脂分散体。 - 前記末端基は、リン酸塩、有機リン酸塩、ホスホン酸塩、有機ホスホン酸塩、ホスフィン酸塩、有機ホスフィン酸塩、またはそれらの組み合わせを含む、請求項6に記載の水性樹脂分散体。
- 前記リン酸化エポキシ樹脂は、炭素−リン結合によって、またはホスホエステル結合によって樹脂に共有結合したリン原子を含むペンダント基が実質的にない、請求項6に記載の水性樹脂分散体。
- 構成単位Aの構成単位Bに対する比は1:20〜20:1である、請求項13に記載の水性樹脂分散体。
- 前記硬化剤は、カルバメート官能基と反応する少なくとも2つの官能基を含む、請求項6に記載の水性樹脂分散体。
- 前記硬化剤は、アミノプラスト樹脂、フェノプラスト樹脂、ブロック化ポリイソシアネート、またはそれらの組み合わせを含む、請求項6に記載の水性樹脂分散体。
- 前記硬化剤は高分子量の揮発性基を含む、請求項6に記載の水性樹脂分散体。
- 前記高分子量の揮発性基は、樹脂固形分の総重量に対して、5重量%〜50重量%の前記水性樹脂分散体の前記樹脂固形分を含む、請求項18に記載の水性樹脂分散体。
- 前記水性樹脂分散体は、金属含有触媒を実質的に含まない、請求項6に記載の水性樹脂分散体。
- 少なくとも2つのカルバメート官能基を含むカルバメート官能性オリゴマーをさらに含む、請求項6に記載の水性樹脂分散体。
- 少なくとも1つの末端エポキシド官能基および少なくとも1つのペンダントヒドロキシル官能基を含むエポキシ樹脂を、イソシアナト官能基およびカルバメート官能基を含む分子と反応させることであって、前記ペンダントヒドロキシル官能基およびイソシアナト官能基は、反応してウレタン結合を形成し、それによって前記分子が前記エポキシ樹脂に組み込まれてカルバメート官能性エポキシ樹脂を形成する、反応させることと、
前記カルバメート官能性エポキシ樹脂を、リン酸、ホスホン酸、ホスフィン酸、またはそれらの組み合わせとさらに反応させることであって、前記カルバメート官能性エポキシ樹脂のうちの前記少なくとも1つの末端エポキシド官能基は、前記リン酸またはホスホン酸の酸基と反応し、それによって、前記リン酸および/または前記ホスホン酸は、前記カルバメート官能性エポキシ樹脂に組み込まれ、少なくとも1つのカルバメート官能基を含む前記リン酸化エポキシ樹脂を形成する、さらに反応させることと、
を含む、請求項1に記載のリン酸化エポキシ樹脂を製造する方法。 - 少なくとも1つのカルバメート官能基を含む前記リン酸化エポキシ樹脂は、塩基で中和されている、請求項23に記載の方法。
- 基材をコーティングする方法であって、請求項6に記載の水性樹脂分散体を前記基材上に電気泳動的に堆積させて前記基材上にコーティングを形成することを含む、方法。
- 請求項6に記載の水性樹脂分散体から堆積された前記コーティングは、ダブルアセトン擦りつけ試験方法に従って少なくとも25回のダブルアセトン擦りつけに耐えることによって測定されるように、250°Fのベーク温度で60分以内に硬化する、請求項25に記載の方法。
- 請求項6に記載の水性樹脂分散体から堆積された前記コーティングは、加水分解安定性試験方法によって測定されるように、加水分解に安定である、請求項25に記載の方法。
- 前記水性樹脂分散体は、カルバメート官能性オリゴマーをさらに含み、糸状腐食試験方法に従って測定されるように、前記水性樹脂分散体から堆積された前記コーティングは、前記カルバメート官能性オリゴマーを含まない比較コーティング組成物と比較する場合、糸状腐食の長さが減少することを示す、請求項25に記載の方法。
- 請求項6に記載の水性樹脂分散体で少なくとも部分的にコーティングされている、コーティングされた基材。
- 請求項6に記載の水性樹脂分散体で少なくとも部分的にコーティングされた、部品。
- 請求項30に記載の部品を備える、ビークル。
- 前記ビークルは、航空宇宙ビークルを含む、請求項31に記載のビークル。
- 請求項6に記載の水性樹脂分散体で少なくとも部分的にコーティングされた、ビークル。
- 前記ビークルは、航空宇宙ビークルを含む、請求項33に記載のビークル。
- (a)リン酸化エポキシ樹脂と、
(b)少なくとも2つのカルバメート官能基を含むカルバメート官能性オリゴマーと、
を含む、水性樹脂分散体。
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CN112771127A (zh) | 2021-05-07 |
CA3104528A1 (en) | 2020-01-02 |
JP7372270B2 (ja) | 2023-10-31 |
US10947408B2 (en) | 2021-03-16 |
US20210284864A1 (en) | 2021-09-16 |
WO2020006188A1 (en) | 2020-01-02 |
AU2019291855A1 (en) | 2021-01-21 |
EP3814437A1 (en) | 2021-05-05 |
KR20210027375A (ko) | 2021-03-10 |
US20200002566A1 (en) | 2020-01-02 |
CN112771127B (zh) | 2022-12-27 |
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