AU2009227048B2 - Polymer dispersions containing phosphorous polymers and emulsifiers - Google Patents
Polymer dispersions containing phosphorous polymers and emulsifiers Download PDFInfo
- Publication number
- AU2009227048B2 AU2009227048B2 AU2009227048A AU2009227048A AU2009227048B2 AU 2009227048 B2 AU2009227048 B2 AU 2009227048B2 AU 2009227048 A AU2009227048 A AU 2009227048A AU 2009227048 A AU2009227048 A AU 2009227048A AU 2009227048 B2 AU2009227048 B2 AU 2009227048B2
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- Australia
- Prior art keywords
- monomers
- polymer
- meth
- emulsion polymerization
- ethylenically unsaturated
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 115
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 40
- 239000006185 dispersion Substances 0.000 title description 45
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 title description 10
- 239000000178 monomer Substances 0.000 claims abstract description 154
- 239000004815 dispersion polymer Substances 0.000 claims abstract description 119
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000007720 emulsion polymerization reaction Methods 0.000 claims abstract description 57
- 150000002148 esters Chemical class 0.000 claims abstract description 51
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 30
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 24
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000576 coating method Methods 0.000 claims description 142
- 239000000203 mixture Substances 0.000 claims description 128
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 103
- 239000011248 coating agent Substances 0.000 claims description 95
- 239000000463 material Substances 0.000 claims description 77
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 40
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 35
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000012855 volatile organic compound Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001735 carboxylic acids Chemical class 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 10
- 150000003140 primary amides Chemical class 0.000 claims description 8
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 7
- 150000003926 acrylamides Chemical class 0.000 claims description 5
- 239000001023 inorganic pigment Substances 0.000 claims description 5
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 133
- -1 alkyl phosphate Chemical compound 0.000 description 105
- 238000006116 polymerization reaction Methods 0.000 description 84
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 70
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000000049 pigment Substances 0.000 description 41
- 238000003756 stirring Methods 0.000 description 32
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- 238000007792 addition Methods 0.000 description 30
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 23
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 22
- 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 19
- 239000000945 filler Substances 0.000 description 18
- 239000004971 Cross linker Substances 0.000 description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 16
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 16
- 239000003973 paint Substances 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 15
- 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 15
- VSVCAMGKPRPGQR-UHFFFAOYSA-N propan-2-one;sulfurous acid Chemical compound CC(C)=O.OS(O)=O VSVCAMGKPRPGQR-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 239000002562 thickening agent Substances 0.000 description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 13
- 150000001298 alcohols Chemical class 0.000 description 12
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 12
- 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
- 238000005299 abrasion Methods 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
- 238000004132 cross linking Methods 0.000 description 9
- 238000009826 distribution 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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000000468 ketone group Chemical group 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000013530 defoamer Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
- 239000002253 acid Substances 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
- 239000003795 chemical substances by application Substances 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
- 239000000839 emulsion Substances 0.000 description 6
- 238000007046 ethoxylation reaction Methods 0.000 description 6
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 6
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 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
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 5
- 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
- 150000001768 cations Chemical class 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
- 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
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000005022 packaging material Substances 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 230000008569 process Effects 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 229910000366 copper(II) sulfate Inorganic materials 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
- 239000006224 matting agent 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 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
- 239000011575 calcium Substances 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
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 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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- 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
- 150000002825 nitriles Chemical class 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
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
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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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- 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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- VPJDULFXCAQHRC-UHFFFAOYSA-N prop-2-enylurea Chemical compound NC(=O)NCC=C VPJDULFXCAQHRC-UHFFFAOYSA-N 0.000 description 1
- DQJSKCFIYCTPBV-UHFFFAOYSA-N propan-2-yl n-(propan-2-yloxycarbonylamino)peroxycarbamate Chemical compound CC(C)OC(=O)NOONC(=O)OC(C)C DQJSKCFIYCTPBV-UHFFFAOYSA-N 0.000 description 1
- HMPSOEYFMTWOFC-UHFFFAOYSA-N propane-2,2-dithiol Chemical compound CC(C)(S)S HMPSOEYFMTWOFC-UHFFFAOYSA-N 0.000 description 1
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- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 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
- 229950006389 thiodiglycol Drugs 0.000 description 1
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- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- 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
-
- 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 | 2008-03-20 | ||
| EP08153095.8 | 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 |
|---|---|
| AU2009227048A1 AU2009227048A1 (en) | 2009-09-24 |
| AU2009227048B2 true AU2009227048B2 (en) | 2014-07-17 |
Family
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Family Applications (1)
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|---|---|---|---|
| AU2009227048A Ceased AU2009227048B2 (en) | 2008-03-20 | 2009-03-20 | Polymer dispersions containing phosphorous polymers and emulsifiers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8293825B2 (enExample) |
| EP (1) | EP2257579B1 (enExample) |
| JP (1) | JP2011515527A (enExample) |
| KR (1) | KR101574365B1 (enExample) |
| CN (1) | CN102037034B (enExample) |
| AU (1) | AU2009227048B2 (enExample) |
| CA (1) | CA2717609C (enExample) |
| ES (1) | ES2636995T3 (enExample) |
| PT (1) | PT2257579T (enExample) |
| WO (1) | WO2009115607A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9950306B2 (en) * | 2011-07-14 | 2018-04-24 | Basf Se | Process for producing water-absorbing polymer particles with high free swell rate |
| CN104334474B (zh) | 2012-04-18 | 2017-10-31 | 威士伯采购公司 | 适合用于保护含金属基材包括食物和饮料包装体的低voc水基涂料组合物 |
| CN104884551B (zh) * | 2013-01-16 | 2017-05-24 | 罗门哈斯公司 | 具有颜料和吸附性乙酸乙烯酯粘合剂的涂层组合物 |
| 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 |
| US10167393B2 (en) | 2014-07-28 | 2019-01-01 | Dow Global Technologies Llc | Poly(vinyl acetate) dispersion, and a paint formulation comprising thereof |
| WO2016121238A1 (ja) * | 2015-01-29 | 2016-08-04 | 関西ペイント株式会社 | 複層塗膜形成方法 |
| 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 |
| BR112018009310B1 (pt) * | 2015-11-24 | 2023-02-07 | Rohm And Haas Company | Dispersão aquosa de polímero, composição aquosa de revestimento, e, método para melhorar o bloqueio de taninos de um revestimento |
| US9657184B1 (en) * | 2016-06-30 | 2017-05-23 | The Sherwin-Williams Company | Water borne coating compositions and polymers therefor |
| AU2017371704A1 (en) * | 2016-12-05 | 2019-07-04 | Rohm And Haas Company | Method for producing a granular polymer blend |
| KR102623074B1 (ko) * | 2016-12-19 | 2024-01-10 | 다우 글로벌 테크놀로지스 엘엘씨 | 수성 코팅 조성물 |
| EP3385350A1 (en) * | 2017-04-07 | 2018-10-10 | Arkema France | Aqueous dispersions with high stability for adhesives and sealants |
| US11365314B2 (en) | 2017-09-25 | 2022-06-21 | Dow Global Technologies Llc | Aqueous polymer composition |
| CN111315832B (zh) * | 2017-11-10 | 2025-06-17 | 巴斯夫欧洲公司 | 水性聚合物分散体 |
| CN112004878A (zh) * | 2018-04-20 | 2020-11-27 | 巴斯夫欧洲公司 | 具有基于通过酮基或醛基的交联的凝胶含量的粘合剂组合物 |
| 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 |
| KR20230041759A (ko) * | 2020-07-20 | 2023-03-24 | 바스프 에스이 | 수계 코팅 조성물에서 결합제로서 적합한 필름-형성 공중합체의 수성 중합체 라텍스 |
| US20240425628A1 (en) | 2021-01-26 | 2024-12-26 | 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 |
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| WO2005030495A2 (en) * | 2003-09-26 | 2005-04-07 | Eastman Chemical Company | Methods of blocking stains on a substrate to be painted, and composites suitable for use in such methods |
| WO2005097853A1 (fr) * | 2004-03-10 | 2005-10-20 | Cray Valleys.A. | Dispersion aqueuse de polymere pour revetement barriere |
| WO2008135403A1 (en) * | 2007-05-07 | 2008-11-13 | Rhodia Operations | Polymer and use thereof |
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| US5385960A (en) | 1991-12-03 | 1995-01-31 | Rohm And Haas Company | Process for controlling adsorption of polymeric latex on titanium dioxide |
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| MXPA01003663A (es) | 2000-04-26 | 2002-06-04 | Rohm & Haas | Composicion acuosa de revestimiento bloqueador de manchas. |
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| US7820754B2 (en) | 2004-03-10 | 2010-10-26 | Cray Valley S.A. | Aqueous polymer dispersion for barrier coating |
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| WO2009109622A1 (de) | 2008-03-06 | 2009-09-11 | Basf Se | Polyurethandispersion, die wenigstens ein hochverzweigtes polymer enthält |
-
2009
- 2009-03-20 AU AU2009227048A patent/AU2009227048B2/en not_active Ceased
- 2009-03-20 JP JP2011500238A patent/JP2011515527A/ja active Pending
- 2009-03-20 WO PCT/EP2009/053326 patent/WO2009115607A1/de not_active Ceased
- 2009-03-20 PT PT97219364T patent/PT2257579T/pt unknown
- 2009-03-20 KR KR1020107023336A patent/KR101574365B1/ko 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 EP EP09721936.4A patent/EP2257579B1/de not_active Revoked
- 2009-03-20 ES ES09721936.4T patent/ES2636995T3/es active Active
- 2009-03-20 US US12/922,983 patent/US8293825B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005030495A2 (en) * | 2003-09-26 | 2005-04-07 | Eastman Chemical Company | Methods of blocking stains on a substrate to be painted, and composites suitable for use in such methods |
| WO2005097853A1 (fr) * | 2004-03-10 | 2005-10-20 | Cray Valleys.A. | Dispersion aqueuse de polymere pour revetement barriere |
| WO2008135403A1 (en) * | 2007-05-07 | 2008-11-13 | Rhodia Operations | Polymer and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102037034B (zh) | 2013-06-19 |
| WO2009115607A1 (de) | 2009-09-24 |
| KR20100126527A (ko) | 2010-12-01 |
| CA2717609A1 (en) | 2009-09-24 |
| US20110009540A1 (en) | 2011-01-13 |
| PT2257579T (pt) | 2017-08-14 |
| ES2636995T3 (es) | 2017-10-10 |
| AU2009227048A1 (en) | 2009-09-24 |
| CN102037034A (zh) | 2011-04-27 |
| CA2717609C (en) | 2016-11-29 |
| EP2257579A1 (de) | 2010-12-08 |
| KR101574365B1 (ko) | 2015-12-03 |
| EP2257579B1 (de) | 2017-05-10 |
| JP2011515527A (ja) | 2011-05-19 |
| US8293825B2 (en) | 2012-10-23 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |