CA2717609C - Polymer dispersions containing phosphorous polymers and emulsifiers - Google Patents
Polymer dispersions containing phosphorous polymers and emulsifiers Download PDFInfo
- Publication number
- CA2717609C CA2717609C CA2717609A CA2717609A CA2717609C CA 2717609 C CA2717609 C CA 2717609C CA 2717609 A CA2717609 A CA 2717609A CA 2717609 A CA2717609 A CA 2717609A CA 2717609 C CA2717609 C CA 2717609C
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- CA
- Canada
- Prior art keywords
- monomers
- meth
- polymer
- emulsion polymerization
- ethylenically unsaturated
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 134
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 41
- 239000006185 dispersion Substances 0.000 title abstract description 47
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 title description 10
- 239000000178 monomer Substances 0.000 claims abstract description 237
- 238000000576 coating method Methods 0.000 claims abstract description 153
- 239000004815 dispersion polymer Substances 0.000 claims abstract description 122
- 239000011248 coating agent Substances 0.000 claims abstract description 99
- 238000007720 emulsion polymerization reaction Methods 0.000 claims abstract description 82
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 62
- 150000002148 esters Chemical class 0.000 claims abstract description 62
- 239000000049 pigment Substances 0.000 claims abstract description 46
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 41
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 31
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000012855 volatile organic compound Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 238000009826 distribution Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 143
- -1 vinyl halides Chemical class 0.000 claims description 121
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 103
- 239000000463 material Substances 0.000 claims description 79
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 55
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 52
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 42
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 34
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 25
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000003926 acrylamides Chemical class 0.000 claims description 20
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 18
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 13
- 150000002825 nitriles Chemical class 0.000 claims description 11
- 150000008064 anhydrides Chemical class 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 6
- 239000011256 inorganic filler Substances 0.000 claims description 5
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 5
- 239000001023 inorganic pigment Substances 0.000 claims description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 4
- 150000001298 alcohols Chemical class 0.000 abstract description 12
- 238000005299 abrasion Methods 0.000 abstract description 11
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 238000005498 polishing Methods 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 133
- 238000006116 polymerization reaction Methods 0.000 description 82
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 34
- 238000003756 stirring Methods 0.000 description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 31
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 30
- 238000007792 addition Methods 0.000 description 29
- 238000000034 method Methods 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 23
- 239000000945 filler Substances 0.000 description 20
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 20
- 239000004971 Cross linker Substances 0.000 description 16
- 239000003973 paint Substances 0.000 description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 15
- 229910021529 ammonia Inorganic materials 0.000 description 15
- VSVCAMGKPRPGQR-UHFFFAOYSA-N propan-2-one;sulfurous acid Chemical compound CC(C)=O.OS(O)=O VSVCAMGKPRPGQR-UHFFFAOYSA-N 0.000 description 15
- 239000002562 thickening agent Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 13
- FDENMIUNZYEPDD-UHFFFAOYSA-L disodium [2-[4-(10-methylundecyl)-2-sulfonatooxyphenoxy]phenyl] sulfate Chemical compound [Na+].[Na+].CC(C)CCCCCCCCCc1ccc(Oc2ccccc2OS([O-])(=O)=O)c(OS([O-])(=O)=O)c1 FDENMIUNZYEPDD-UHFFFAOYSA-L 0.000 description 13
- 239000011734 sodium Substances 0.000 description 11
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 150000001735 carboxylic acids Chemical class 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000003172 aldehyde group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000005690 diesters Chemical class 0.000 description 8
- 125000000468 ketone group Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 7
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 7
- 239000013530 defoamer Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000004816 latex Substances 0.000 description 7
- 229920000126 latex Polymers 0.000 description 7
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 7
- 239000005022 packaging material Substances 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 235000016213 coffee Nutrition 0.000 description 6
- 235000013353 coffee beverage Nutrition 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 238000007046 ethoxylation reaction Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229930194542 Keto Natural products 0.000 description 5
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical class O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000006224 matting agent Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000005201 scrubbing Methods 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- 239000004408 titanium dioxide Substances 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
- 239000004908 Emulsion polymer Substances 0.000 description 4
- 240000002989 Euphorbia neriifolia Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 244000269722 Thea sinensis Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000003140 primary amides Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000006468 Thea sinensis Nutrition 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 235000020279 black tea Nutrition 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 235000010216 calcium carbonate Nutrition 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
- 239000000084 colloidal system Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 235000010460 mustard Nutrition 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
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
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- 239000012966 redox initiator Substances 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
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- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 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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- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical class OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- 235000021537 Beetroot Nutrition 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
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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
- C09D143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/02—Homopolymers or copolymers of monomers containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08153095.8 | 2008-03-20 | ||
| EP08153095 | 2008-03-20 | ||
| PCT/EP2009/053326 WO2009115607A1 (de) | 2008-03-20 | 2009-03-20 | Polymerdispersionen enthaltend phosphorhaltige polymere und emulgatoren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2717609A1 CA2717609A1 (en) | 2009-09-24 |
| CA2717609C true CA2717609C (en) | 2016-11-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2717609A Expired - Fee Related CA2717609C (en) | 2008-03-20 | 2009-03-20 | Polymer dispersions containing phosphorous polymers and emulsifiers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8293825B2 (https=) |
| EP (1) | EP2257579B1 (https=) |
| JP (1) | JP2011515527A (https=) |
| KR (1) | KR101574365B1 (https=) |
| CN (1) | CN102037034B (https=) |
| AU (1) | AU2009227048B2 (https=) |
| CA (1) | CA2717609C (https=) |
| ES (1) | ES2636995T3 (https=) |
| PT (1) | PT2257579T (https=) |
| WO (1) | WO2009115607A1 (https=) |
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| US9950306B2 (en) * | 2011-07-14 | 2018-04-24 | Basf Se | Process for producing water-absorbing polymer particles with high free swell rate |
| MX366946B (es) | 2012-04-18 | 2019-07-31 | Swimc Llc | Composiciones de revestimiento a base de agua con nivel bajo de contenido organico volatil adecuadas para proteger sustratos que contienen metal que incluyen envases de alimentos y bebidas. |
| BR112015015088A2 (pt) * | 2013-01-16 | 2017-07-11 | Rohm & Haas | composição de revestimento |
| CN104448956A (zh) * | 2013-09-25 | 2015-03-25 | 刘立先 | 一种净化空气、吸收、分解甲醛有害气体的硅藻泥涂覆材料 |
| CN104558431B (zh) | 2013-10-28 | 2018-05-18 | 广东华润涂料有限公司 | 水性胶乳以及包含该水性胶乳的无机颜料颗粒的分散体 |
| JP2015214674A (ja) | 2014-04-15 | 2015-12-03 | 株式会社リコー | インクジェット記録用インク、インク収容容器、インクジェット記録装置、記録物 |
| AU2014402271B2 (en) | 2014-07-28 | 2018-11-29 | Dow Global Technologies Llc | Poly(vinyl acetate) dispersion, and paint formulation comprising thereof |
| US10639672B2 (en) * | 2015-01-29 | 2020-05-05 | Kansai Paint Co., Ltd. | Method for forming multilayer coating film |
| CA2918266C (en) * | 2015-02-16 | 2023-03-28 | Rohm And Haas Company | Acid suppressible rheology modifier stabilized with phosphoric acid ester surfactant |
| TW201700506A (zh) * | 2015-06-19 | 2017-01-01 | 羅門哈斯公司 | 磷酸官能化塗料組合物 |
| US10597550B2 (en) * | 2015-11-24 | 2020-03-24 | Dow Global Technologies Llc | Aqueous polymer dispersion and process of making the same |
| US10125287B2 (en) * | 2016-06-30 | 2018-11-13 | The Sherwin-Williams Company | Pigment complexes for water borne coating compositions |
| PL3548545T3 (pl) * | 2016-12-05 | 2021-06-14 | Rohm And Haas Company | Sposób wytwarzania granulowanej mieszanki polimerów |
| EP3555219B1 (en) * | 2016-12-19 | 2022-07-27 | Dow Global Technologies LLC | Aqueous coating composition |
| EP3385350A1 (en) * | 2017-04-07 | 2018-10-10 | Arkema France | Aqueous dispersions with high stability for adhesives and sealants |
| CN111094444B (zh) | 2017-09-25 | 2022-06-03 | 陶氏环球技术有限责任公司 | 水性聚合物组合物 |
| WO2019091889A1 (de) | 2017-11-10 | 2019-05-16 | Basf Se | Wässrige polymerdispersionen |
| US11884846B2 (en) * | 2018-04-20 | 2024-01-30 | Basf Se | Adhesive composition having a gel content based on cross-linking via keto groups or aldehyde groups |
| US11193039B2 (en) | 2018-07-16 | 2021-12-07 | Ppg Industries Ohio, Inc. | Stain resistant coating compositions |
| CN113590002B (zh) * | 2020-04-30 | 2024-04-16 | 京东方科技集团股份有限公司 | 笔迹形成方法、笔迹形成装置及电子设备 |
| CN116134056B (zh) * | 2020-07-20 | 2025-02-25 | 巴斯夫欧洲公司 | 适合作为水性涂料组合物中的粘合剂的成膜共聚物的水性聚合物胶乳 |
| WO2022161998A1 (en) | 2021-01-26 | 2022-08-04 | Basf Se | Aqueous polymer latex |
| WO2025128643A1 (en) * | 2023-12-13 | 2025-06-19 | Arkema Inc. | Coating compositions with improved performance |
| CN118108905B (zh) * | 2024-03-06 | 2025-01-21 | 深圳市研一新材料有限责任公司 | 电极浆料添加剂及其制备方法和应用 |
| CN119614278B (zh) * | 2024-11-29 | 2025-09-23 | 中科红基(广东)科技有限公司 | 一种高耐磨润滑油组合物及其制备方法 |
| CN121130856B (zh) * | 2025-11-18 | 2026-02-17 | 西安金沃泰环保科技有限公司 | 一种高效磷去除吸附树脂及其制备方法 |
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| GB1329126A (en) | 1969-12-11 | 1973-09-05 | Mitsubishi Rayon Co | Acrylic fibre and a method for manufacturing the same |
| JPS5033767B1 (https=) | 1971-03-11 | 1975-11-04 | ||
| DE2722097C3 (de) | 1977-05-16 | 1981-09-17 | Basf Ag, 6700 Ludwigshafen | (Meth)acryloxy-alkylpropanale, Verfahren zu dessen Herstellung und Verwendung derselben |
| US4226007A (en) * | 1979-03-16 | 1980-10-07 | Signode Corporation | Sealless strap connection |
| US4269749A (en) * | 1979-04-30 | 1981-05-26 | The Dow Chemical Company | Method of imparting salt and/or mechanical stability to aqueous polymer microsuspensions |
| US5385960A (en) | 1991-12-03 | 1995-01-31 | Rohm And Haas Company | Process for controlling adsorption of polymeric latex on titanium dioxide |
| DE4219384A1 (de) | 1992-06-13 | 1993-12-23 | Basf Ag | Bei Raumtemperatur mit Hydroxylaminen oder Oximethern vernetzbare Dispersion oder Lösung |
| DE19824087A1 (de) | 1998-05-29 | 1999-12-02 | Basf Ag | Phosphat- oder Phosphonatgruppen enthaltende Bindemittel für den Korrosionsschutz |
| WO2001074909A2 (en) | 2000-03-31 | 2001-10-11 | Rhodia, Inc. | Polymerizable compounds and uses thereof |
| US6485786B2 (en) | 2000-04-26 | 2002-11-26 | Rohm And Haas Company | Aqueous stain-blocking coating composition |
| DE60228035D1 (de) | 2001-10-01 | 2008-09-18 | Rohm & Haas | Beschichtungszusammensetzung auf Basis eines bimodalen Emulsionscopolymeren, Verfahren zur Fleckenbeseitigung, Deckkraftverbesserung, Blockneigungsreduzierung und Verbesserung der Scherstabilität |
| FI20030684A7 (fi) * | 2003-05-07 | 2004-11-15 | Targetor Oy | Menetelmä ja järjestelmä tiedon käsittelemiseksi |
| US7332046B2 (en) * | 2003-09-26 | 2008-02-19 | Eastman Chemical Company | Methods of blocking stains on a substrate to be painted, and composites suitable for use in such methods |
| US7820754B2 (en) | 2004-03-10 | 2010-10-26 | Cray Valley S.A. | Aqueous polymer dispersion for barrier coating |
| FR2867478B1 (fr) * | 2004-03-10 | 2006-04-28 | Cray Valley Sa | Dispersion aqueuse de polymere pour revetement barriere |
| DE602005004303T2 (de) * | 2004-08-26 | 2009-01-02 | Lubrizol Advanced Materials, Inc., Cleveland | Beschichtungszusammensetzungen mit verbesserter stabilität |
| EP1762601A1 (en) | 2005-09-12 | 2007-03-14 | Basf Aktiengesellschaft | Method to increase resistance against stain penetration of aqueous coating compositions |
| NZ553410A (en) * | 2006-03-02 | 2008-06-30 | Rohm & Haas | Scrub and stain-resistant copolymer coating composition |
| KR20090097933A (ko) * | 2006-12-15 | 2009-09-16 | 바스프 에스이 | 고분지형 폴리카르보네이트를 함유하는 중합체 분산액 |
| JP4792052B2 (ja) * | 2007-04-30 | 2011-10-12 | ローム アンド ハース カンパニー | 水性コポリマー分散体およびコーティング組成物 |
| EP1997839A1 (en) * | 2007-05-07 | 2008-12-03 | Rhodia Opérations | Polymer and use thereof |
| EP2235077B2 (en) * | 2007-12-20 | 2017-06-21 | Lubrizol Advanced Materials, Inc. | Use of a waterborne composition as a waterborne coating with improved early water blushing and chemical resistance |
| WO2009109622A1 (de) | 2008-03-06 | 2009-09-11 | Basf Se | Polyurethandispersion, die wenigstens ein hochverzweigtes polymer enthält |
-
2009
- 2009-03-20 US US12/922,983 patent/US8293825B2/en not_active Expired - Fee Related
- 2009-03-20 CA CA2717609A patent/CA2717609C/en not_active Expired - Fee Related
- 2009-03-20 CN CN2009801181389A patent/CN102037034B/zh not_active Expired - Fee Related
- 2009-03-20 KR KR1020107023336A patent/KR101574365B1/ko not_active Expired - Fee Related
- 2009-03-20 WO PCT/EP2009/053326 patent/WO2009115607A1/de not_active Ceased
- 2009-03-20 AU AU2009227048A patent/AU2009227048B2/en not_active Ceased
- 2009-03-20 JP JP2011500238A patent/JP2011515527A/ja active Pending
- 2009-03-20 EP EP09721936.4A patent/EP2257579B1/de not_active Revoked
- 2009-03-20 PT PT97219364T patent/PT2257579T/pt unknown
- 2009-03-20 ES ES09721936.4T patent/ES2636995T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2636995T3 (es) | 2017-10-10 |
| EP2257579B1 (de) | 2017-05-10 |
| CN102037034A (zh) | 2011-04-27 |
| CA2717609A1 (en) | 2009-09-24 |
| WO2009115607A1 (de) | 2009-09-24 |
| AU2009227048B2 (en) | 2014-07-17 |
| KR20100126527A (ko) | 2010-12-01 |
| US20110009540A1 (en) | 2011-01-13 |
| AU2009227048A1 (en) | 2009-09-24 |
| EP2257579A1 (de) | 2010-12-08 |
| US8293825B2 (en) | 2012-10-23 |
| JP2011515527A (ja) | 2011-05-19 |
| PT2257579T (pt) | 2017-08-14 |
| KR101574365B1 (ko) | 2015-12-03 |
| CN102037034B (zh) | 2013-06-19 |
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