JP5563556B2 - 汎用顔料ペースト用のペースト樹脂 - Google Patents
汎用顔料ペースト用のペースト樹脂 Download PDFInfo
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- JP5563556B2 JP5563556B2 JP2011504451A JP2011504451A JP5563556B2 JP 5563556 B2 JP5563556 B2 JP 5563556B2 JP 2011504451 A JP2011504451 A JP 2011504451A JP 2011504451 A JP2011504451 A JP 2011504451A JP 5563556 B2 JP5563556 B2 JP 5563556B2
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- Prior art keywords
- resin
- paste
- paint
- pigment
- acid
- 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.)
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- 239000000049 pigment Substances 0.000 title claims abstract description 88
- 229920005989 resin Polymers 0.000 title claims abstract description 53
- 239000011347 resin Substances 0.000 title claims abstract description 53
- 239000003973 paint Substances 0.000 claims abstract description 90
- 229920000180 alkyd Polymers 0.000 claims abstract description 47
- 239000000178 monomer Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 13
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- -1 polyethylene groups Polymers 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000004925 Acrylic resin Substances 0.000 claims description 15
- 229920000178 Acrylic resin Polymers 0.000 claims description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000011230 binding agent Substances 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 13
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000012860 organic pigment Substances 0.000 claims description 7
- 239000001023 inorganic pigment Substances 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 238000006266 etherification reaction Methods 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000007519 polyprotic acids Polymers 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 238000004040 coloring Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 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 6
- 239000000654 additive Substances 0.000 description 6
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002600 sunflower oil Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 235000006693 Cassia laevigata Nutrition 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 229920000263 Rubber seed oil Polymers 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 241000522641 Senna Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000011324 bead Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 2
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- 235000021388 linseed oil Nutrition 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005474 octanoate group Chemical group 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
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- 239000011541 reaction mixture Substances 0.000 description 2
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- 229940124513 senna glycoside Drugs 0.000 description 2
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- 125000001302 tertiary amino group Chemical group 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
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- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
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- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L33/04—Homopolymers or copolymers of esters
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
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- 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
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- 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
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Description
2000g/モルのモル質量を有する929gのモノメトキシポリエチレングリコールと、71gのテトラヒドロフタル酸無水物とを、触媒として1gのトリエチルアミンの存在下で150℃まで、26.5mg/gの一定の酸価に達するまで反応させることによって、付加物を調製した。
270gのジメチルアミノエチルメタクリレート、50gのブチルアクリレート、及び230gの2-エチルヘキシルアクリレートの混合物と、各々1モルのヒドロキシエチルメタクリレート、トルイレンジイソシアネート及び750g/モルのモル質量の乾燥ポリエチレングリコールモノメチルエーテルを反応させることによって調製された450gの付加物とを、5時間かけて200gのイソプロパノールに溶解した20gのtert−アミルペルオクトエートと同時に、還流条件において窒素ブランケット下で攪拌しながら330gのイソプロパノールに添加した。添加が完了した後1時間この混合物を攪拌し、その後、さらに20gの触媒溶液を添加した。反応が停止し、残渣モノマー濃度が0.3%より低くなったら、減圧下およそ110℃での蒸留によって溶媒を除去した。その後、反応容器に窒素を流し、反応塊を周囲温度まで冷却させた。
600gの実施例1のアルキド樹脂、及び400gの実施例2のアクリル樹脂を、両方とも樹脂ケトル(resin kettle)に充填した後、混合し、80℃で1時間、均質混合物が得られるまで攪拌した。攪拌は続けたまま加熱を止め、次に、30分かけて1222gの水を添加し、その後、ケトルを周囲温度まで冷却させた。約45%の固形分の質量分率を有する粉砕樹脂の半粘性の透明な溶液が得られた。
4.1 溶媒系白色アルキド塗料
303gの溶媒系アルキド樹脂((登録商標)Vialkyd AS 6172/55 SD60(Cytec Surface Specialties Austria GmbH)、(登録商標)Shellsol D60(低質量分率(0.1%未満)の芳香族化合物を有する、C10−〜C12−パラフィン及び−ナフテンの混合物)に溶解した、57%の油含有量を有する、ダイズ油をベースとしたアルキド樹脂)、さらに67gの(登録商標)Shellsol D60、及び268gの白色二酸化チタン顔料((登録商標)Kronos 2190(Kronos Titan GmbH))を混合し、室温において30分間ビーズミルで粉砕した後、さらに303gの(登録商標)Vialkyd AS 6172/55 SD60、6.7gの皮張り防止剤(オキシムをベースとした(登録商標)Additol XL 297/100(Cytec Surface Specialties Austria GmbH))、各々16.8gの(登録商標)Octa−Soligen Cobalt 1、(登録商標)Octa−Soligen Calcium 2及び(登録商標)Octa−Soligen Zirconium 6の乾燥剤混合物(金属オクトエート乾燥剤(Borchers GmbH)、数値は、(登録商標)Shellsol D60を溶媒として用いた溶液中の金属オクトエートの質量分率(%)を表す)、並びに1.9gの流展添加剤(flow and leveling additive)(ポリエーテル変性シリコーンをベースとした(登録商標)Additol VXL 4930(Cytec Surface Specialties Austria GmbH))の混合物を用いてレットダウンさせた。得られた白色塗料(およそ1000g)は、上記と同様に測定した場合542mPa・sの粘度を有していた。
395gの水系アルキド樹脂((登録商標)Resydrol AY 586w/38WA、アクリル変性アルキド樹脂(Cytec Surface Specialties Austria GmbH))、及び254gの白色二酸化チタン顔料(親水性処理済の(登録商標)Kronos 2059(Kronos Titan GmbH))、21.5gの組合せ乾燥剤((登録商標)Additol VXW 4940、脱イオン水で50%強度まで希釈された、Co、Ba及びZr化合物をベースとした乾燥剤のエマルジョン(Cytec Surface Specialties Austria GmbH))、1.45gの脱泡剤(液体炭化水素ベース、(登録商標)Additol VXW 6211(Cytec Surface Specialties Austria GmbH))及び5.35gの流展添加剤(ポリエーテル変性シリコーンをベースとした(登録商標)Additol XW 329(Cytec Surface Specialties Austria GmbH))を混合し、室温において30分間ビーズミルで粉砕した後、さらに268gの(登録商標)Resydrol AY 586w/38WA、5.35gの(登録商標)Additol XL 297(上記参照)、24.4gの脱イオン水、及び7.3gの25%強度のアンモニア水溶液の混合物を用いてレットダウンさせた。得られた白色塗料(およそ1000g)は、上記と同様に測定した場合949mPa・sの粘度、及び10%強度の水分散液に関して求めた場合8.5〜9.0のpHを有していた。
実施例3の本発明によるペースト樹脂から下記のように有色顔料ペーストを調製した(構成成分の質量(g))。
(2)液体炭化水素をベースとした脱泡剤添加剤((登録商標)Additol VXW 6211(Cytec Surface Specialties Austria GmbH))
(3)(登録商標)Hostaperm yellow H3G(Pigment Yellow 154)
(4)(登録商標)Hostaperm red E3B(Pigment Violet 19)
(5)(登録商標)Hostaperm violet RL spec(Pigment Violet 23)
(6)(登録商標)Hostaperm Green GG01
顔料(登録商標)Hostaperm yellow H3G(Pigment Yellow 154)、(登録商標)Hostaperm red E3B(Pigment Violet 19)、(登録商標)Hostaperm violet RL spec(Pigment Violet 23)、及び(登録商標)Hostaperm Green GG01を用いた種々の色の、商業用の水系顔料ペースト((登録商標)Colanyl(Clariant International Ltd.))及び溶媒系顔料ペースト((登録商標)Hostatint(idem))と、商業用グレードのものと同じ顔料から成るが、実施例3のペースト樹脂を用いた実施例5の顔料ペーストとを、実施例4.1の溶媒系白色アルキド塗料及び実施例4.2の水系白色アルキド塗料から着色塗料を調製することによって比較した。
7.1 比較用アクリル樹脂
250gのジメチルアミノエチルメタクリレート、650gのn−ブチルアクリレート、及び100gのヒドロキシエチルアクリレートの混合物を、70gのメトキシプロパノールに溶解した20gのアゾビス−イソバレロニトリルの溶液と共に8時間かけて、85℃に維持された160gのメトキシプロパノールを充填したガラス容器に添加し、容器の内容物を窒素ブランケット下で攪拌した。添加の完了後、反応混合物をもう2時間攪拌し、さらに1g量の同じラジカル開始剤を添加し、10gのメトキシプロパノールに溶解させ、反応混合物をもう2時間攪拌した。その後、さらに20gのメトキシプロパノールを添加して、混合物を室温まで冷却させた。
129gの実施例7.1のアクリル樹脂溶液をガラス容器に移し、減圧下140℃における蒸留によって溶媒メトキシプロパノールを除去した。次に、容器に窒素を流し、100℃未満に冷却後、133gの実施例1のアルキド樹脂を添加し、80℃で1時間アクリル樹脂と十分に混合させた。加熱を止めることによって、及び313gの完全な脱イオン水を30分かけて添加することによって、攪拌しながら混合物を冷却させた。その後、容器及びその内容物を周囲温度にまで冷却させた。約45%の固形分の質量分率を有する、樹脂と水との不均質混合物が得られた。
30.1gの実施例7.2の混合物のサンプルを、均質化直後且つ相分離前に取り出し、27.7gの脱イオン水、0.2gのイソチアゾリノンベースの防腐剤((登録商標)Additol VXW 6372(Cytec Surface Specialties Austria GmbH))、液体炭化水素をベースとした2gの脱泡剤((登録商標)Additol VXW 6211(Cytec Surface Specialties Austria GmbH))、及び40gのキナクリドンレッド顔料(Pigment Violet 19、(登録商標)Hostaperm Red E3B(Clariant Deutschland GmbH))と混合させた。この混合物を室温(21℃)において30分間ビーズミルで均質化させた。
5gの実施例7.3の顔料ペーストを152gの実施例4.1の溶媒系白色アルキド塗料に添加することによって着色塗料を作製した。ガラスパネル(10cm×15cm)上において150μmの湿潤膜強度でアプリケータフレーム(BYK-Gardner製のPA−2056)を用いてこれらの塗料から調製し、24時間室温(21℃)で乾燥させた塗膜に関して、光沢及び色の濃さを測定した。結果を表4にまとめる。光沢は室温(21℃)及び50%相対湿度でBYK製のmicro−triglossメータを用いて測定し、最大の着色力を示す「1」〜低着色力を示す「5」で色の濃さを評価した。
Claims (9)
- 水希釈性アルキド樹脂(B)と塩基性アクリルコポリマー樹脂(A)との混合物であるペースト樹脂(AB)であって、該塩基性アクリルコポリマー樹脂(A)が、少なくとも1つの共重合性オレフィン性不飽和をそれぞれ有する少なくとも3種類のビニルモノマーのコポリマーであり、該ビニルモノマーが、少なくとも1つのアミノ基含有ビニル型モノマー(A1)、アルキル基中に1個〜13個の炭素原子を有する直鎖状又は分岐状アルキル(メタ)アクリレートから成る群から選択される少なくとも1つのモノマー(A2)、及びポリエーテルグリコールに由来する部位を有する少なくとも1つの親水性ビニルモノマー(A3)を含み、該ポリエーテルグリコールが、ポリエチレングリコール、又はオキシアルキレン基の全質量中のオキシエチレン基の質量分率が少なくとも60%であるエチレングリコールとプロピレングリコールとの混合エーテルであり、前記ポリエーテルグリコールのヒドロキシル基の1つが、エーテル基に転化し、オレフィン性不飽和モノカルボン酸によるエステル化によって、又はオレフィン性不飽和アルコールによるエーテル化によって、又はヒドロキシアルキル(メタ)アクリレートとジイソシアネートとの付加物による反応を介したウレタン形成によって、他のヒドロキシル基が消費され、
前記水希釈性アルキド樹脂(B)が、0.2mg/g〜5mg/gの酸価を有する、アルキド樹脂(Ba)と、ポリオキシエチレングリコールのC 1 −〜C 4 −モノアルキルエーテル(Bb1)、又はエチレングリコールとプロピレングリコールとの混合エーテルのC 1 −〜C 4 −モノアルキルエーテル(Bb2)、又はそれらの混合物と、脂環式ジカルボン酸の無水物(Bb3)との付加物(Bb)との縮合生成物をベースとし、前記水希釈性アルキド樹脂(B)中、Bb1及びBb2の物質量の合計と、Bb3の物質量との比率が、0.95モル:1.05モル〜1.05モル:0.95モルであり、構成成分(A)及び構成成分(B)が、45%〜75%のAと、55%〜25%のBとの質量比で混合される、ペースト樹脂(AB)。 - モノマー(A1)の質量分率が15%〜40%であり、モノマー(A2)の質量分率が15%〜45%であり、モノマー(A3)の質量分率が30%〜60%である、請求項1に記載のペースト樹脂(AB)。
- 前記モノマー(A3)が、ポリエチレングリコールモノエーテルと、トルイレンジイソシアネートと、ヒドロキシエチルメタクリレートとの反応生成物である、請求項1に記載のペースト樹脂(AB)。
- 前記アルキド樹脂(Ba)が、1分子当たり2つ以上のヒドロキシル基を有する1つ又は複数のポリオール(Ba1)と、1つ又は複数の多塩基酸(Ba2)と、1つ又は複数のトリグリセリド油(Ba4)を代わりに用いてもよく又はこれと一緒に混合されていてもよい1つ又は複数の脂肪酸(Ba3)との共縮合によって生成される、請求項1に記載のペースト樹脂(AB)。
- 請求項1に記載のペースト樹脂(AB)と、無機顔料及び有機顔料から成る群から選択される少なくとも1つの顔料とを含む、顔料ペースト。
- 請求項1に記載のペースト樹脂を使用する方法であって、前記ペースト樹脂(AB)を少なくとも1つの顔料と混合すること、混合物を剪断下で均質化することであって、顔料ペーストを形成する、均質化すること、及び前記顔料ペーストと、有機塗料バインダを含む無着色塗料又は白色塗料とを混合することを含む、ペースト樹脂を使用する方法。
- 前記塗料バインダが、アルキド樹脂、アクリル樹脂、アクリル変性アルキド樹脂、ウレタンアルキド、及びウレタン変性アクリル樹脂から成る群から選択される、請求項6に記載の方法。
- 前記塗料が水系塗料である、請求項6に記載の方法。
- 前記塗料が溶媒系塗料である、請求項6に記載の方法。
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JP2008007718A (ja) * | 2006-06-30 | 2008-01-17 | Toyobo Co Ltd | アルキッド樹脂、水系アルキッド塗料用樹脂組成物およびそれらの製造方法 |
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Also Published As
Publication number | Publication date |
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US20110028636A1 (en) | 2011-02-03 |
ATE547478T1 (de) | 2012-03-15 |
EP2297246B1 (en) | 2012-02-29 |
US9469775B2 (en) | 2016-10-18 |
EP2110410A1 (en) | 2009-10-21 |
AU2009237639B2 (en) | 2014-12-18 |
NZ588610A (en) | 2011-07-29 |
CN102015890B (zh) | 2012-12-26 |
EP2297246A1 (en) | 2011-03-23 |
RU2010146466A (ru) | 2012-05-27 |
ZA201008159B (en) | 2011-07-27 |
CA2720957C (en) | 2015-11-24 |
JP2011521016A (ja) | 2011-07-21 |
RU2484113C2 (ru) | 2013-06-10 |
CA2720957A1 (en) | 2009-10-22 |
BRPI0910646B1 (pt) | 2019-10-15 |
CN102015890A (zh) | 2011-04-13 |
US20140107277A1 (en) | 2014-04-17 |
MX2010011427A (es) | 2011-01-20 |
WO2009127668A1 (en) | 2009-10-22 |
ES2382196T3 (es) | 2012-06-06 |
KR101566674B1 (ko) | 2015-11-06 |
KR20110008232A (ko) | 2011-01-26 |
BRPI0910646A2 (pt) | 2015-09-22 |
AU2009237639A1 (en) | 2009-10-22 |
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