JP6258876B2 - キレート官能性を有するコーティング組成物 - Google Patents
キレート官能性を有するコーティング組成物 Download PDFInfo
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- JP6258876B2 JP6258876B2 JP2014560939A JP2014560939A JP6258876B2 JP 6258876 B2 JP6258876 B2 JP 6258876B2 JP 2014560939 A JP2014560939 A JP 2014560939A JP 2014560939 A JP2014560939 A JP 2014560939A JP 6258876 B2 JP6258876 B2 JP 6258876B2
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- 239000008199 coating composition Substances 0.000 title claims description 51
- 239000000178 monomer Substances 0.000 claims description 160
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- 239000013522 chelant Substances 0.000 claims description 61
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- -1 kayanite Inorganic materials 0.000 claims description 38
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- 239000003125 aqueous solvent Substances 0.000 claims description 19
- 150000001768 cations Chemical class 0.000 claims description 19
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 18
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 17
- OUDSFQBUEBFSPS-UHFFFAOYSA-N ethylenediaminetriacetic acid Chemical compound OC(=O)CNCCN(CC(O)=O)CC(O)=O OUDSFQBUEBFSPS-UHFFFAOYSA-N 0.000 claims description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
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- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 claims description 10
- PQHYOGIRXOKOEJ-UHFFFAOYSA-N 2-(1,2-dicarboxyethylamino)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)NC(C(O)=O)CC(O)=O PQHYOGIRXOKOEJ-UHFFFAOYSA-N 0.000 claims description 10
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
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- 125000003700 epoxy group Chemical group 0.000 claims description 7
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 7
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 5
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- 229960000892 attapulgite Drugs 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 claims description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052863 mullite Inorganic materials 0.000 claims description 4
- 229910052625 palygorskite Inorganic materials 0.000 claims description 4
- 229910052851 sillimanite Inorganic materials 0.000 claims description 4
- 229940071182 stannate Drugs 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 239000004408 titanium dioxide Substances 0.000 claims description 4
- VAELQCZFRATZQB-UHFFFAOYSA-N calcium copper silicate Chemical compound [Ca+2].[Cu+2].[O-][Si]([O-])([O-])[O-] VAELQCZFRATZQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- OGDYVWQEAVKKDI-UHFFFAOYSA-N chromium(3+);oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Cr+3].[Cr+3] OGDYVWQEAVKKDI-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- 239000010445 mica Substances 0.000 claims description 3
- 229910052618 mica group Inorganic materials 0.000 claims description 3
- 239000010434 nepheline Substances 0.000 claims description 3
- 229910052664 nepheline Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000010435 syenite Substances 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical class [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 44
- 239000003973 paint Substances 0.000 description 42
- 238000009472 formulation Methods 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 20
- 229910010413 TiO 2 Inorganic materials 0.000 description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 18
- 229910010272 inorganic material Inorganic materials 0.000 description 17
- 239000011147 inorganic material Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 14
- 239000008367 deionised water Substances 0.000 description 13
- 229910021641 deionized water Inorganic materials 0.000 description 13
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
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- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 9
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 9
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- 150000002148 esters Chemical class 0.000 description 6
- PEOHLVWFSVQRLK-UHFFFAOYSA-N ethenylcarbamic acid Chemical compound OC(=O)NC=C PEOHLVWFSVQRLK-UHFFFAOYSA-N 0.000 description 6
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
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- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- VOOQRJIZEJHBGL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.CCCCOC(=O)C(C)=C VOOQRJIZEJHBGL-UHFFFAOYSA-N 0.000 description 1
- YWDYRRUFQXZJBG-UHFFFAOYSA-N butyl prop-2-enoate;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.CCCCOC(=O)C=C YWDYRRUFQXZJBG-UHFFFAOYSA-N 0.000 description 1
- AQCDIIAORKRFCD-UHFFFAOYSA-N cadmium selenide Chemical compound [Cd]=[Se] AQCDIIAORKRFCD-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- ZZBBCSFCMKWYQR-UHFFFAOYSA-N copper;dioxido(oxo)silane Chemical compound [Cu+2].[O-][Si]([O-])=O ZZBBCSFCMKWYQR-UHFFFAOYSA-N 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical group C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- ISXDVFNOXYQPIA-UHFFFAOYSA-N dibutyl pentanedioate Chemical compound CCCCOC(=O)CCCC(=O)OCCCC ISXDVFNOXYQPIA-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- QKXBVVVYILIRDO-UHFFFAOYSA-N diethyl 1h-pyrrole-3,4-dicarboxylate Chemical compound CCOC(=O)C1=CNC=C1C(=O)OCC QKXBVVVYILIRDO-UHFFFAOYSA-N 0.000 description 1
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- BNMYXGKEMMVHOX-UHFFFAOYSA-N dimethyl butanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCC(=O)OC.COC(=O)CCCC(=O)OC BNMYXGKEMMVHOX-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- FSCIDASGDAWVED-UHFFFAOYSA-N dimethyl hexanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC.COC(=O)CCCCC(=O)OC FSCIDASGDAWVED-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- MGLUUYLPGOWCNW-UHFFFAOYSA-M dimethyl(diphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C)(C)C1=CC=CC=C1 MGLUUYLPGOWCNW-UHFFFAOYSA-M 0.000 description 1
- JMPVESVJOFYWTB-UHFFFAOYSA-N dipropan-2-yl carbonate Chemical compound CC(C)OC(=O)OC(C)C JMPVESVJOFYWTB-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 229910052571 earthenware Inorganic materials 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- SENKOTRUJLHKFM-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCOC(=O)C(C)=C SENKOTRUJLHKFM-UHFFFAOYSA-N 0.000 description 1
- YGTXYHBZYODOKK-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;phosphoric acid Chemical compound OP(O)(O)=O.CCOC(=O)C(C)=C YGTXYHBZYODOKK-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 229910001448 ferrous ion Inorganic materials 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940079826 hydrogen sulfite Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZNZRNJQUEOMPOP-UHFFFAOYSA-N methyl(triphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](OC=1C=CC=CC=1)(C)OC1=CC=CC=C1 ZNZRNJQUEOMPOP-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- AMBKPYJJYUKNFI-UHFFFAOYSA-N methylsulfanylethene Chemical compound CSC=C AMBKPYJJYUKNFI-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005787 opaque polymer Polymers 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical group CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical group CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
Description
X1、X2、X3及びX4は、各々独立して、水素又は一価カチオンであり、R3は、水素又は重合性モノマーから誘導される単位であり、
*は、アミノカルボン酸基が、重合性モノマーから誘導される単位、又は、エチレン性不飽和のモノマーから誘導される単位でキレートポリマーに結合する位置である。
X1、X2、X3及びX4は、独立して、各々水素又は一価カチオンであり、R3は、水素又は重合性モノマーから誘導される単位であり、
*は、アミノカルボン酸基が、重合性モノマーから誘導される単位、又は、エチレン性不飽和のモノマーから誘導される単位でキレートポリマーに結合する位置である。
イミノ二酢酸(IDA)又はその塩は、例えば、以下の一般構造を有する。
温度計、凝縮器及びスターラを備える適切な反応器内での初期リアクタチャージを、窒素雰囲気生成下で85〜86℃まで加熱する一方、表2に記載の供給A〜Mを調製した。85℃で、供給C及びリンスを一度に反応器に加え、温度を80〜85℃に合わせた後、供給Dのケトルチャージを行った。2分以内に、3℃〜5℃の温度上昇によって重合の開始が合図され、反応混合物の外観(色及び不透明度)に変化が現れた。発熱が止まったとき、残留モノマー混合物、供給A、及び同時供給触媒液、供給F、が、約85℃で125分間をかけて反応器に徐々に加えられた。同時に、供給Bは、約85℃で60分間かけて、同時に反応器に加えられた。供給Bの終了の後60分後に、供給Bを収容する容器にすすぎを行い、そのすすぎ液はリアクタに加えられた。すすぎの後、供給Eは、供給Bの残りに供給され、同時にリアクタに供給された。この供給が終了した後、リアクタ内容物は85℃で15分間静置された。次いでリアクタは60℃に冷却された後、供給Gのショットを添加して追跡し、その後、供給H及びIのショットを加えた。2回目の追跡では、15分後に、25分間かけて、第2のレドックスペア、供給J及びKを徐々に供給した。追跡の後、リアクタの内容物は、40℃に冷却された。供給Lが、10分間かけてリアクタに加えられた。次いで供給Lが、20分間かけて反応器に加えられ、ラテックスのpHを8.0に調整した。この後に、供給Mの添加が数分間続いた。次いで、リアクタの内容物は、100メッシュ及び325メッシュの篩に通され、固形物、pH、粘性及び粒径の特性評価を行った。
GMA−IDAモノマーを4.0重量%加えた以外は、実施例1と同様に、実施例2のアクリル分散物を調製した。ただし、ポリマーは、表2に記載されるモノマーの比率を有するモノマーエマルジョンを用いて調製された。
GMA−IDAモノマーを加えなかった以外は、実施例1と同様に、比較例Aのアクリル分散物を調製した。ポリマーは、表2に記載されるモノマーの比率を有するモノマーエマルジョンを用いて調製された。
GMA−IDAモノマーを加えた以外は、比較例Aと同様に、比較例Bのアクリル分散物を調製した。その代わりに、2.0%のPEMを用いた。ポリマーは、表2に記載されるモノマーの比率を有するモノマーエマルジョンを用いて調製された。
脱イオン水(545g)、Disponil FES−993界面活性剤(82.5g(30%アクティブ))、Ba(456g)、EA(570g)、MMA(802.75g)、PEM(38g(65%アクティブ))、メタアクリル酸(4.75g)、UMA(57g(50%アクティブ))及びn−DDM(2.38g)を混合して、第1のモノマーエマルジョン(ME1)を調製した。脱イオン水(25g)、Disponil FES−993界面活性剤(アクティブ30%、2.6g)、BA(20g)及びMMA(80g)を混合して、第2のモノマーエマルジョン(ME2)を調製した。
前述の5つのサンプルポリマーの各々を、水性不透明コーティング配合物に配合し、その後、色相強度、粘度及び凍結/融解強度等の特性に関してペイント塗料としての性能を評価した。下記のように、水性コーティング配合物はバインダとしてポリマーを含んでおり、0gm/LVOCの半光沢塗料であった。
1.比較するそれぞれの塗料は、2.00oz/ガロン又は他の所望のレベルのレベルで、所望の着色剤で着色された。
2.容器を手で振動させて、着色剤が塗料に確実に沈殿するようにした。
3.サンプルを、機械式振とう機に5分間置いた。
4.厚い(3ミルのバードフィルムアプリケータ又はそれ以上)の着色塗料のドローダウンが生成され、制御条件(75°F/50%RH)の下で、1日間乾燥させた。
5.Y−反射率(R)を、塗料ドローダウンの3つの領域で測定し、平均数を報告した。
色合い強度(TS)は、以下の方程式を用いて算出した。
TS=[(R2)/(1−R2)2]x[(1−R1)2/(R1)]×100
式中、R1は標準を表し、R2は試験された塗料を表す。本実施例では、R1は比較例Aの反射率(63.46)であり、これは、比較例Aが「標準」として用いられたことを意味するものである。
また、凍結融解挙動に関して、以下の凍結/融解試験方法によって、半光沢塗料配合物を以下のように評価した。0.5パイントの金属コンテナの75%を特定のサンプル配合物で満たすことにより、試料を調製した。初期粘度を、Brookfield KU−1粘度計を用いたクレブス単位(KU値)で測定した。次いで容器を密閉し、0°F(−18℃)のフリーザ内に16時間(h)配置した。容器を取り出し、雰囲気条件で8h融解させた。水性コーティングを手でこそげ取り、外観について、1〜5のスケールで評価したが、評価5は、コーティングは滑らかでクリーム状、評価3は、コーティングが使えたがもはや滑らかでなくクリーム状、評価1は、コーティングが非常に高い粗粒状を示した、とした。次いで、コーティングのKU粘度を測定し記録した。結果を、下記の表7に示す。KUOは、KU値の初期粘度のことである。
また、半光沢塗料配合物に対して、一晩静置している間の塗料配合物の粘度の変化を解析する以下の方法により、粘度安定性の評価も行った。0.5パイントの金属コンテナの75%を特定のサンプル配合物で満たすことにより、試料を調製した。初期粘度を、Brookfield KU−1粘度計を用いたクレブス単位(KU値)で測定した。次いで容器を密閉し、雰囲気温度(20〜25℃)の部屋の中に16時間放置した。容器を開け、それぞれの塗料配合物を手でこそげ取り、外観について、1〜5のスケールで評価したが、評価5は、コーティングは滑らかでクリーム状、評価3は、コーティングが使えたがもはや滑らかでなくクリーム状、評価1は、コーティングが非常に高い粗粒状を示した、とした。一晩通した塗料KU粘度(KU O/N)を、Brookfield KU−1粘度計を用いて測定し、記録した。結果を、下記の表8に示した。KUOは、初期粘度のことであり、KU O/Nは、一晩の粘度のことであり、ともにクレブス単位である。「デルタKU」は、一晩の粘度の変化を示し、単純にシールをしただけで未使用の場合の塗料配合物の粘度の変化は好ましくないので、デルタKUは、最小の値が好適である。
Claims (6)
- 水性不透明コーティング配合物であって、
(A)水性溶媒と、
(B)二酸化チタン、酸化亜鉛、スズ酸コバルト(II)、セレン化カドミウム、硫化カドミウム、カルシウムケイ酸銅、酸化クロム(III)水和物、タルク、炭酸カルシウム、霞石閃長岩、硫酸バリウム、カオリン水和物、ムライト、パイロフィライト、カヤナイト、シリマナイト、アタパルジャイト、マイカ、及びこれらの組合せから成る群より選択される、無機顔料と、
(C)キレートポリマーのラテックス粒子と
を含み、前記キレートポリマーは、
(1)1種以上のアミノカルボン酸化合物又はその塩と、
(2)ビニル基、アリル基の一方又はその双方と、任意のエポキシ基とを含む1種以上の重合性モノマーと、
(3)1種以上のエチレン性不飽和モノマーと
に由来する重合単位を含み、
前記(C)(1)1種以上のアミノカルボン酸化合物又はその塩の重合単位は、以下の構造の少なくとも1つのアミノカルボン酸基を有するものを含み、
X 1 、X 2 、X 3 及びX 4 は、各々独立して、水素及び一価カチオンから成る群より選択されるものであり、
前記一価カチオンはNa + 、K + 、及びNH 4 + から成る群より選択されるものであり、
R 3 は、水素及び重合性モノマーから誘導される単位から成る群より選択されるものであり、
*は、アミノカルボン酸基が、重合性モノマーから誘導される単位、又は、エチレン性不飽和のモノマーから誘導される単位において、キレートポリマーに結合して重合単位を形成する位置であり、
前記(C)(2)ビニル基、アリル基の一方又は両方、及び任意のエポキシ基を含む1種以上の重合性モノマーに由来する単位は、以下の構造の1つ以上を有し、
前記キレートポリマーの前記単位(C)(3)を誘導する前記1種類以上のエチレン性不飽和モノマーが、1又は複数の炭素−炭素二重結合を有するカルボン酸、1又は複数の炭素−炭素二重結合を有するカルボン酸エステル、マレイン酸、スチレン、1又は複数の炭素−炭素二重結合を有するスルホン酸並びにそれらの組合せから成る群より選択されるものである、
水性不透明コーティング配合物。 - (C)(1)1種以上のアミノカルボン酸化合物又はその塩は、イミノ二酢酸、イミノジコハク酸、エチレンジアミントリ酢酸、エチレンジアミン二コハク酸、及びそれらの塩から成る群より選択される請求項1に記載の水性不透明コーティング配合物。
- (C)(2)1種以上の重合性モノマーは、メタクリル酸グリシジル、アリルグリシジルエーテル、ビニルベンジルクロライド、臭化アリル、及びそれらの誘導体から成る群より選択される請求項1に記載の水性不透明コーティング配合物。
- (C)キレートポリマーは、(3)1種以上のエチレン性不飽和モノマーと;(1)1種以上のアミノカルボン酸化合物又はその塩と(2)ビニル基、アリル基の一方又は両方と任意のエポキシ基とを含む1種以上の重合性モノマーとの反応生成物と;に由来する重合単位を含む請求項1に記載の水性不透明コーティング配合物。
- 水性不透明コーティング配合物の全重量に基づき、
(A)1重量%〜95重量%の水性溶媒と、
(B)0.1重量%〜85重量%の無機顔料と、
(C)5重量%〜80重量%のキレートポリマーと
を含む請求項1に記載の水性不透明コーティング配合物。 - 表面を有する基材を被覆するための不透明膜を提供する方法であって、請求項1に記載の水性不透明コーティング配合物を基材の表面に塗布することを含む方法。
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