JP2015522678A - 水性複合結合剤およびアルキド系の、コーティング剤のための使用 - Google Patents
水性複合結合剤およびアルキド系の、コーティング剤のための使用 Download PDFInfo
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- JP2015522678A JP2015522678A JP2015519004A JP2015519004A JP2015522678A JP 2015522678 A JP2015522678 A JP 2015522678A JP 2015519004 A JP2015519004 A JP 2015519004A JP 2015519004 A JP2015519004 A JP 2015519004A JP 2015522678 A JP2015522678 A JP 2015522678A
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- Prior art keywords
- aqueous
- alkyd
- acrylate
- meth
- emulsion
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- 229920000180 alkyd Polymers 0.000 title claims abstract description 116
- 239000011230 binding agent Substances 0.000 title claims abstract description 43
- 239000002131 composite material Substances 0.000 title claims abstract description 37
- 238000000576 coating method Methods 0.000 title claims description 26
- 239000004815 dispersion polymer Substances 0.000 claims abstract description 62
- 239000000839 emulsion Substances 0.000 claims abstract description 46
- 239000011248 coating agent Substances 0.000 claims abstract description 40
- 239000006185 dispersion Substances 0.000 claims abstract description 26
- 239000003973 paint Substances 0.000 claims abstract description 22
- 229920002635 polyurethane Polymers 0.000 claims abstract description 22
- 239000004814 polyurethane Substances 0.000 claims abstract description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 78
- 239000000178 monomer Substances 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 41
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 35
- 238000006116 polymerization reaction Methods 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 23
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 238000004332 deodorization Methods 0.000 claims description 12
- 238000011161 development Methods 0.000 claims description 11
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 6
- 230000009477 glass transition Effects 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 239000001023 inorganic pigment Substances 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- -1 acetoacetoxyethyl Chemical group 0.000 description 100
- 125000000217 alkyl group Chemical group 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 20
- 239000003995 emulsifying agent Substances 0.000 description 19
- 239000000049 pigment Substances 0.000 description 18
- 238000001035 drying Methods 0.000 description 14
- 150000002763 monocarboxylic acids Chemical class 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000004132 cross linking Methods 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- 239000003431 cross linking reagent Substances 0.000 description 11
- 150000001991 dicarboxylic acids Chemical class 0.000 description 11
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- 229920002554 vinyl polymer Polymers 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 125000000468 ketone group Chemical group 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 125000003172 aldehyde group Chemical group 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000003926 acrylamides Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 4
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- NTMMCWJNQNKACG-KBKUWGQMSA-N UDP-N-acetyl-alpha-D-muramoyl-L-alanine Chemical compound CC(=O)N[C@@H]1[C@@H](O[C@H](C)C(=O)N[C@@H](C)C(O)=O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 NTMMCWJNQNKACG-KBKUWGQMSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000006224 matting agent Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000003136 n-heptyl 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])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 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 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
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- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 2
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- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
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- 239000004435 Oxo alcohol Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WEAYWASEBDOLRG-UHFFFAOYSA-N pentane-1,2,5-triol Chemical compound OCCCC(O)CO WEAYWASEBDOLRG-UHFFFAOYSA-N 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 1
- AKRQMTFHUVDMIL-UHFFFAOYSA-N tetrakis(prop-2-enyl)silane Chemical compound C=CC[Si](CC=C)(CC=C)CC=C AKRQMTFHUVDMIL-UHFFFAOYSA-N 0.000 description 1
- KWXLCDNSEHTOCB-UHFFFAOYSA-J tetrasodium;1,1-diphosphonatoethanol Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P(=O)([O-])C(O)(C)P([O-])([O-])=O KWXLCDNSEHTOCB-UHFFFAOYSA-J 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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- 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AQZSPJRLCJSOED-UHFFFAOYSA-M trimethyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(C)C AQZSPJRLCJSOED-UHFFFAOYSA-M 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
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- 150000003672 ureas Chemical class 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- 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
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- 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
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
- C09D133/12—Homopolymers or copolymers of methyl methacrylate
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- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
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- 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
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Abstract
Description
(a)少なくとも1種のα,β−エチレン性不飽和モノマー(M)
(b)および場合により、少なくとも1種のさらなるモノマー(M1)をラジカル乳化重合させてポリマー(P)にし、
(c)場合により、続いて化学的脱臭をして、
(d)5000〜40000Daの重量平均分子量を有する、少なくとも1種の水溶性アルキド樹脂または少なくとも1種の水性アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンもしくは分散液を、
i.MとM1との重合、および場合により、室温での前記化学的脱臭に続いて、
ii.MとM1との重合に続いて、後撹拌時間0〜2時間で、
または
iii.前記化学的脱臭に続いて、後撹拌時間0〜2時間で、
のいずれかで添加し、
ここで、iiもしくはiiiによる添加での温度が、60〜99℃、好ましくは70〜95℃、特に80〜90℃であることを特徴とする、前記アルキド樹脂または前記アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンもしくは分散液の添加を行うことにより得られるものである。
・以下に記載の、少なくとも1種の本発明による複合結合剤または水性アルキド系、
・場合により、少なくとも1種の無機充填剤および/または無機顔料、
・一般的な助剤、および
・100質量%になるまでの水
を含む水性組成物の形態のコーティング剤である。
アクリレート残留モノマーの量が同時に(別の複合化方法と比べて)減少した場合のコーティング剤(塗装剤)、特に、アクリレート分散液をベースとする光沢着色剤の光沢度の上昇。
n−ブチルアクリレート、メチルメタクリレート;
n−ブチルアクリレート、メチルメタクリレート、スチレン;
n−ブチルアクリレート、スチレン、ブチル(メタ)アクリレート;
n−ブチルアクリレート、エチルヘキシルアクリレート、スチレン
n−ブチルアクリレート、スチレン
n−ブチルアクリレート、n−ブチル(メタ)アクリレート、メチルメタクリレート。
Maphos 24T(C10H21O(CH2CH2O)4−P(=O)(OH2))および
Maphos 10T((2―エチルヘキシル)ホスフェート)が好ましく、両方ともBASF BTCのものである。
固体含有量の測定
内径約5cmのアルミニウムるつぼ内の、決められた量の水性結合剤(約1g)を、乾燥棚内で140℃にて恒量になるまで乾燥させるという方法で、固体含有量(FG)を一般的に測定した。2つの別個の測定を実施した。例に示される値は、それぞれ両方の測定結果の平均値を表している。
水希釈性アルキド樹脂WorleeSol(登録商標)61Eを、あらかじめ25質量%アンモニア水溶液および完全脱塩(VE)水で固体含有量40%およびpH値約8に調整した。
計量供給装置および温度調整器を備える重合容器に以下:
を装入して、撹拌して85℃に加熱した。次に、この温度を維持しながら、供給3の10%を供給して5分撹拌した。その後、供給1を180分で計量供給し、同時に供給3の残量を195分で計量供給した。
例4の通りであるが、供給2として:WorleeSol(登録商標)E150W 395g。
例4の通りであるが、供給2として:WorleeSol(登録商標)E280W 416g。
振り子硬度
試験するコーティングを、エリクセンフィルムアプリケーター(300μm、湿式)で、38×7cmのガラス板にナイフコーティングにより塗布した。室温で乾燥させた後、前記ガラス板の三箇所で3つの測定値を振り子測定した。測定は、ケーニッヒ(DIN EN ISO1522)に準拠して行った。
光開始剤を有するポリマー分散液(PD)の配合
撹拌機に、室温にてポリマー分散液(PD)100gを装入して、撹拌しながら、次に、それぞれポリマー分散液の固体含有量に対して1質量%もしくは2質量%のEsacure(登録商標)TZM(Lehmann&Voss&Co.社、ドイツ)(ベンゾフェノンと4−メチルベンゾフェノンとの混合物)を添加して、15分間、後撹拌した。
Claims (17)
- 水性ポリマー分散液(PD)と光開始剤0.01〜5質量%とを含む水性複合結合剤であって、
前記水性ポリマー分散液(PD)が、
(a)少なくとも1種のα,β−エチレン性不飽和モノマー(M)
(b)および場合により、少なくとも1種のさらなるモノマー(M1)をラジカル乳化重合させてポリマー(P)にし、
(c)場合により、続いて化学的脱臭をして、
(d)5000〜40000Daの重量平均分子量を有する、少なくとも1種の水溶性アルキド樹脂または少なくとも1種の水性アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンもしくは分散液を、
i.MとM1との重合、および場合により、室温での前記化学的脱臭に直接続いて、
ii.MとM1との重合に続いて、後撹拌時間0〜2時間で、または
iii.前記化学的脱臭に続いて、後撹拌時間0〜2時間で
のいずれかで添加し、
ここで、iiもしくはiiiによる添加の温度が、60〜99℃、好ましくは70〜95℃、特に80〜90℃であることを特徴とする、前記アルキド樹脂または前記アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンもしくは分散液の添加を行うことにより得られる前記水性複合結合剤。 - 前記光開始剤が、室温(23℃)に冷却された前記ポリマー分散液(PD)に添加されることを特徴とする、請求項1に記載の水性複合結合剤。
- 前記主モノマーM1が、
n−ブチルアクリレート、メチルメタクリレート;
n−ブチルアクリレート、メチルメタクリレート、スチレン;
n−ブチルアクリレート、スチレン、ブチル(メタ)アクリレート;
n−ブチルアクリレート、エチルヘキシルアクリレート、スチレン、
n−ブチルアクリレート、スチレン、または
n−ブチルアクリレート、n−ブチル(メタ)アクリレート、メチルメタクリレート
の群から選択されることを特徴とする、請求項1または2に記載の水性複合結合剤。 - 請求項3に記載のモノマーM1と組み合わされるモノマーM2として、アクリル酸、メタクリル酸、アクリルアミド、メタクリルアミド、アセトアセトキシエチルメタクリレート(AAEM)、2−ウレイドメタクリレート(UMA)またはBisomer(登録商標)またはその混合物が使用されることを特徴とする、請求項1から3までのいずれか1項に記載の水性複合結合剤。
- 前記ポリマー分散液(PD)が、少なくとも1種の水溶性アルキド樹脂または水性アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンを、前記複合結合剤の総質量に対して5〜60質量%(固体)含むことを特徴とする、請求項1から4までのいずれか1項に記載の水性複合結合剤。
- 前記アクリレートアルキドポリマー分散液(PD)のアクリレート部分のガラス転移温度Tgが、50℃未満であるが、20℃よりも大きいことを特徴とする、請求項1から5までのいずれか1項に記載の水性複合結合剤。
- 少なくとも1種の水溶性アルキド樹脂または水性アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンもしくは分散液、および光開始剤0.01〜5質量%を含む水性アルキド系。
- ・請求項1から6までのいずれか1項に記載の、少なくとも1種の複合結合剤、
・場合により、少なくとも1種の無機充填剤および/または無機顔料、
・一般的な助剤、ならびに
・100質量%になるまでの水
を含む、水性組成物の形態のコーティング剤。 - ・請求項7に記載の、少なくとも1種の水性アルキド系、
・場合により、少なくとも1種の無機充填剤および/または無機顔料、
・一般的な助剤、ならびに
・100質量%になるまでの水
を含む、水性組成物の形態のコーティング剤。 - 塗装剤であることを特徴とする、請求項8または9に記載のコーティング剤。
- 水性複合結合剤の製造方法であって、
(a)少なくとも1種のα,β−エチレン性不飽和モノマー(M)
(b)および場合により、少なくとも1種のさらなるモノマー(M1)をラジカル乳化重合させてポリマー(P)にし、
(c)場合により、続いて化学的脱臭をして、
(d)5000〜40000Daの重量平均分子量を有する、少なくとも1種の水溶性アルキド樹脂または少なくとも1種の水性アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンを、
i.MとM1との重合、および場合により、室温での前記化学的脱臭に直接続いて、
ii.MとM1との重合に続いて、後撹拌時間0〜2時間で、または
iii.前記化学的脱臭に続いて、後撹拌時間0〜2時間で
のいずれかで添加し、
ここで、iiもしくはiiiによる添加の温度が、60〜99℃、好ましくは70〜95℃、特に80〜90℃であることを特徴とする、前記アルキド樹脂または前記アルキドエマルジョンもしくはポリウレタンアルキドエマルジョンもしくは分散液の添加により水性ポリマー分散液(PD)を製造し、ならびに光開始剤0.01〜5質量%を添加することによる水性複合結合剤の製造方法。 - 請求項1から6までのいずれか1項に記載の水性複合結合剤の、塗装剤における結合剤としての使用。
- 請求項7に記載の水性アルキド系の、塗装剤における使用。
- 前記塗装剤が、クリア塗料または着色塗料であることを特徴とする、請求項12または13に記載の水性複合結合剤または水性アルキド系の使用。
- 前記塗装剤が、高光沢クリア塗料または高光沢着色塗料であることを特徴とする、請求項12または13に記載の水性複合結合剤または水性アルキド系の使用。
- 請求項1から6のいずれか1項に記載の水性複合結合剤をベースとするコーティングの早期硬度発現を高めるための方法。
- 請求項7に記載の水性アルキド系をベースとするコーティングの早期硬度発現を高めるための方法。
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- 2013-06-21 EP EP13732874.6A patent/EP2870208A1/de not_active Withdrawn
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- 2013-06-21 JP JP2015519004A patent/JP2015522678A/ja active Pending
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- 2013-06-21 WO PCT/EP2013/063035 patent/WO2014005862A1/de active Application Filing
- 2013-06-21 AU AU2013286181A patent/AU2013286181B2/en not_active Ceased
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AU2013286181A1 (en) | 2015-01-29 |
US20150126639A1 (en) | 2015-05-07 |
WO2014005862A1 (de) | 2014-01-09 |
EP2870208A1 (de) | 2015-05-13 |
ZA201500804B (en) | 2017-01-25 |
US9567484B2 (en) | 2017-02-14 |
CN104428378A (zh) | 2015-03-18 |
RU2015103810A (ru) | 2016-08-27 |
BR112015000169A2 (pt) | 2017-06-27 |
AU2013286181B2 (en) | 2017-02-16 |
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