DE60315029T2 - Latex-Anstrichzusammensetzungen und Beschichtungen - Google Patents
Latex-Anstrichzusammensetzungen und Beschichtungen Download PDFInfo
- Publication number
- DE60315029T2 DE60315029T2 DE60315029T DE60315029T DE60315029T2 DE 60315029 T2 DE60315029 T2 DE 60315029T2 DE 60315029 T DE60315029 T DE 60315029T DE 60315029 T DE60315029 T DE 60315029T DE 60315029 T2 DE60315029 T2 DE 60315029T2
- Authority
- DE
- Germany
- Prior art keywords
- paint composition
- integer
- fluorine
- acrylic polymer
- units
- 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.)
- Expired - Lifetime
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- 239000003973 paint Substances 0.000 title claims abstract description 124
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 229920000126 latex Polymers 0.000 title claims abstract description 65
- 239000004816 latex Substances 0.000 title claims abstract description 63
- 238000000576 coating method Methods 0.000 title claims abstract description 22
- 239000000654 additive Substances 0.000 claims abstract description 50
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- -1 heptafluoropropanesulfonamido, nonafluorobutanesulfonamido, undecafluoropentanesulfonamido Chemical group 0.000 claims abstract description 39
- 230000000996 additive effect Effects 0.000 claims abstract description 38
- 239000000049 pigment Substances 0.000 claims abstract description 32
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 32
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000002562 thickening agent Substances 0.000 claims abstract description 16
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 13
- 125000005529 alkyleneoxy group Chemical group 0.000 claims abstract description 12
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 11
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims abstract description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 7
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000011248 coating agent Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 10
- FUVKFLJWBHVMHX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FUVKFLJWBHVMHX-UHFFFAOYSA-N 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- FQKBJSUFBIZAKR-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropane-1-sulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F FQKBJSUFBIZAKR-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical group 0.000 claims description 4
- 239000006224 matting agent Substances 0.000 claims description 4
- 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 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 229920001983 poloxamer Polymers 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000013459 approach Methods 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 229920005692 JONCRYL® Polymers 0.000 description 8
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000003801 milling Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229920002125 Sokalan® Polymers 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 6
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- BHFJBHMTEDLICO-UHFFFAOYSA-N Perfluorooctylsulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O BHFJBHMTEDLICO-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 5
- 238000010422 painting Methods 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 229920005604 random copolymer Polymers 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 235000010216 calcium carbonate Nutrition 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 229910052570 clay Inorganic materials 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 235000015096 spirit Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DSRUAYIFDCHEEV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(2-hydroxyethyl)-n-methylbutane-1-sulfonamide Chemical compound OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DSRUAYIFDCHEEV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004851 dishwashing Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010943 off-gassing Methods 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 238000000518 rheometry Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- GFZPUWKGPNHWHD-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-methylbutane-1-sulfonamide Chemical compound CNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GFZPUWKGPNHWHD-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241001522296 Erithacus rubecula Species 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940010698 activated attapulgite Drugs 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 231100000693 bioaccumulation Toxicity 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QZHDEAJFRJCDMF-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-M 0.000 description 1
- VWNAITWBRLKIIS-UHFFFAOYSA-N 1-sulfanylpropane-1,1-diol Chemical compound CCC(O)(O)S VWNAITWBRLKIIS-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- GXLQLZJWDQCAPT-UHFFFAOYSA-N 3-(2-carboxyethenoxy)prop-2-enoic acid Chemical compound OC(=O)C=COC=CC(O)=O GXLQLZJWDQCAPT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910000004 White lead Inorganic materials 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CJDPJFRMHVXWPT-UHFFFAOYSA-N barium sulfide Chemical compound [S-2].[Ba+2] CJDPJFRMHVXWPT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- NKZSPGSOXYXWQA-UHFFFAOYSA-N dioxido(oxo)titanium;lead(2+) Chemical compound [Pb+2].[O-][Ti]([O-])=O NKZSPGSOXYXWQA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical class OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical class OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
-
- 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
- C09D125/00—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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/14—Copolymers of styrene with unsaturated esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D135/00—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 a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D135/06—Copolymers with vinyl aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/183,176 US7041727B2 (en) | 2002-06-25 | 2002-06-25 | Latex paint compositions and coatings |
| US183176 | 2002-06-25 | ||
| PCT/US2003/014831 WO2004000957A1 (en) | 2002-06-25 | 2003-05-13 | Latex paint compositions and coatings |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60315029D1 DE60315029D1 (de) | 2007-08-30 |
| DE60315029T2 true DE60315029T2 (de) | 2008-04-10 |
Family
ID=29735169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60315029T Expired - Lifetime DE60315029T2 (de) | 2002-06-25 | 2003-05-13 | Latex-Anstrichzusammensetzungen und Beschichtungen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7041727B2 (enExample) |
| EP (1) | EP1517969B1 (enExample) |
| JP (1) | JP2005530888A (enExample) |
| CN (1) | CN100509972C (enExample) |
| AT (1) | ATE367422T1 (enExample) |
| AU (1) | AU2003230375A1 (enExample) |
| BR (1) | BR0312055A (enExample) |
| CA (1) | CA2490503C (enExample) |
| DE (1) | DE60315029T2 (enExample) |
| MX (1) | MXPA05000118A (enExample) |
| WO (1) | WO2004000957A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6881782B2 (en) * | 2002-11-06 | 2005-04-19 | 3M Innovative Properties Company | Latex paint compositions and coatings |
| US20050145134A1 (en) * | 2003-12-30 | 2005-07-07 | Petrin Jason T. | Latex paint compositions and coatings |
| US20080280808A1 (en) * | 2004-04-05 | 2008-11-13 | Daikin Industries, Ltd. | Stain Remover Containing Fluoropolymer |
| EP1632464B1 (en) * | 2004-09-02 | 2011-04-13 | 3M Innovative Properties Company | Method for treating porous stone using a fluorochemical composition |
| US7758954B2 (en) * | 2005-08-18 | 2010-07-20 | James Hardie Technology Limited | Coated substrate having one or more cross-linked interfacial zones |
| US7425374B2 (en) * | 2005-12-22 | 2008-09-16 | 3M Innovative Properties Company | Fluorinated surfactants |
| CN101553529B (zh) * | 2006-12-07 | 2012-09-05 | 3M创新有限公司 | 含有氟化硅氧烷的颗粒及其制备和使用方法 |
| US20080153963A1 (en) * | 2006-12-22 | 2008-06-26 | 3M Innovative Properties Company | Method for making a dispersion |
| BRPI0806455A2 (pt) * | 2007-01-05 | 2011-09-06 | Taminco | método para reduzir o teor do composto orgánico volátil de uma formulação de tinta de látex, uso de pelo menos uma n-alquildialcanolamina, e, formulação de tinta de látex |
| WO2008089391A1 (en) * | 2007-01-19 | 2008-07-24 | 3M Innovative Properties Company | Fluorinated surfactants and methods of using the same |
| US20100025038A1 (en) * | 2007-01-19 | 2010-02-04 | Savu Patricia M | Methods of using stable hydrocarbon foams |
| US8501863B2 (en) * | 2007-06-28 | 2013-08-06 | James Hardie Technology Limited | Paint |
| AU2008269996B2 (en) * | 2007-06-29 | 2014-06-12 | James Hardie Technology Limited | Multifunctional primers |
| EP2277959B1 (en) | 2008-09-02 | 2013-10-16 | Celanese International Corporation | Low emission, high scrub VAE latex paints |
| CN101402815B (zh) * | 2008-10-23 | 2011-06-01 | 贝发集团股份有限公司 | 一种用于喷涂细管状竹制品表面的油漆及其喷涂方法 |
| JPWO2010110339A1 (ja) * | 2009-03-25 | 2012-10-04 | ダイキン工業株式会社 | 含フッ素ポリマーから成る界面活性剤 |
| US9000069B1 (en) | 2010-07-02 | 2015-04-07 | The Sherwin-Williams Company | Self-stratifying coatings |
| BR112013015240A2 (pt) | 2010-12-17 | 2016-09-13 | Celanese Int Corp | composições aquosas para revestimento de látex |
| WO2013088187A1 (en) | 2011-12-15 | 2013-06-20 | Celanese Emulsions Gmbh | Polymer dispersions |
| WO2015048797A1 (en) | 2013-09-30 | 2015-04-02 | Certainteed Corporation | Stain repellent and voc eliminating coatings and use thereof |
| US9777170B2 (en) | 2014-02-25 | 2017-10-03 | The Chemours Company Tt, Llc | Fluorinated polymer additives derived using hydrophilic chain transfer agents for architectural coatings |
| US9938431B2 (en) | 2014-09-26 | 2018-04-10 | The Chemours Company Fc, Llc | Use of non-fluorinated or partially fluorinated urethanes in coatings |
| SG11201703320QA (en) | 2014-10-28 | 2017-05-30 | 3M Innovative Properties Co | Spray application system components comprising a repellent surface & methods |
| US10584249B2 (en) | 2015-10-28 | 2020-03-10 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface |
| CN113145341A (zh) | 2015-10-28 | 2021-07-23 | 3M创新有限公司 | 包括拒液表面的喷雾施用系统部件和方法 |
| CN105348936A (zh) * | 2015-11-25 | 2016-02-24 | 三棵树涂料股份有限公司 | 一种疏水型弹性水性乳胶漆及其制备方法 |
| EP3448944A4 (en) | 2016-04-26 | 2019-11-13 | 3M Innovative Properties Company | ARTISTS SUBJECT TO ICE FORMATION WITH A REPELLENT SURFACE COMPRISING SILOXONE MATERIAL |
| CN115181040A (zh) * | 2022-07-25 | 2022-10-14 | 武汉松石科技股份有限公司 | 丙烯酸(n-甲基全氟烷基磺酰胺基)乙酯的精制纯化方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US614955A (en) * | 1898-11-29 | Box-fastener | ||
| US2803615A (en) * | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
| US2915554A (en) * | 1957-07-23 | 1959-12-01 | Minnesota Mining & Mfg | Non-ionic surfactant derivatives of perfluoro alkane-sulfonamides |
| GB1215861A (en) * | 1967-02-09 | 1970-12-16 | Minnesota Mining & Mfg | Cleanable stain-resistant fabrics or fibers and polymers therefor |
| US3822228A (en) * | 1969-11-10 | 1974-07-02 | Air Prod & Chem | Fluorochemical surfactants for latex paints |
| US3787351A (en) * | 1972-02-28 | 1974-01-22 | Minnesota Mining & Mfg | Use of soluble fluoroaliphatic oligomers in resin composite articles |
| US3891591A (en) * | 1973-08-13 | 1975-06-24 | Du Pont | Coating compositions |
| US4208496A (en) * | 1977-02-02 | 1980-06-17 | N L Industries, Inc. | Dust repellent paint |
| US4600441A (en) * | 1985-03-21 | 1986-07-15 | Westinghouse Electric Corp. | Oil and dirt repellent alkyd paint |
| US5006624A (en) * | 1987-05-14 | 1991-04-09 | The Dow Chemical Company | Fluorocarbon containing, reactive polymeric surfactants and coating compositions therefrom |
| US4929666A (en) * | 1987-05-14 | 1990-05-29 | The Dow Chemical Company | Fluorocarbon containing, reactive polymeric surfactants and coating compositions therefrom |
| US5010153A (en) * | 1988-06-03 | 1991-04-23 | Air Products And Chemicals, Inc. | Copolymers of vinyl acetate and fluorine-containing acrylate monomers |
| US5082895A (en) * | 1988-12-30 | 1992-01-21 | Doris Wolff | High solids, large particle size latex compositions |
| AT392478B (de) * | 1989-09-01 | 1991-04-10 | Vianova Kunstharz Ag | Verwendung von acrylatcopolymerisaten als additive fuer waessrige kationische lacksysteme |
| DE69112269T2 (de) * | 1990-05-17 | 1996-03-21 | Nippon Oils & Fats Co Ltd | Ungesättigte Gruppen und Fluor enthaltende Blockcopolymere, Verfahren zur Herstellung davon und Verwendung. |
| US5468812A (en) * | 1991-04-02 | 1995-11-21 | Minnesota Mining And Manufacturing Company | Polymerizable fluorochemical surfactants |
| CA2114706A1 (en) | 1993-03-08 | 1994-09-09 | Edward R. Hauser | Stain-resistant latex paint |
| DE19522476A1 (de) * | 1995-06-21 | 1997-01-02 | Bayer Ag | Fluor enthaltende Dispergierhilfsmittel für wäßrige Lacke |
| US5688884A (en) * | 1995-08-31 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
| US5827919A (en) * | 1995-10-06 | 1998-10-27 | E. I. Du Pont De Nemours And Company | Fluorourethane additives for water-dispersed coating compositions |
| US5948851A (en) * | 1997-11-21 | 1999-09-07 | E. I. Du Pont De Nemours And Company | Coating compositions containing a highly fluorinated polymeric additive |
| JPH11152428A (ja) * | 1997-11-25 | 1999-06-08 | Kansai Paint Co Ltd | 断熱塗装仕上げ方法 |
| DE19836253C1 (de) * | 1998-08-11 | 1999-12-23 | Goldschmidt Ag Th | Endfunktionalisierte Polymethacrylsäureester und deren Verwendung als Dispergiermittel zur Herstellung wäßriger Pigmentpasten |
| AU1440901A (en) | 1999-10-27 | 2001-05-08 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
| AU2001294391A1 (en) | 2000-09-07 | 2002-03-22 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappijk Onderzoek Tno | Coating compositions containing perfluoropolyether surfactants |
-
2002
- 2002-06-25 US US10/183,176 patent/US7041727B2/en not_active Expired - Lifetime
-
2003
- 2003-05-13 MX MXPA05000118A patent/MXPA05000118A/es active IP Right Grant
- 2003-05-13 AU AU2003230375A patent/AU2003230375A1/en not_active Abandoned
- 2003-05-13 AT AT03724552T patent/ATE367422T1/de not_active IP Right Cessation
- 2003-05-13 CN CNB038177447A patent/CN100509972C/zh not_active Expired - Fee Related
- 2003-05-13 WO PCT/US2003/014831 patent/WO2004000957A1/en not_active Ceased
- 2003-05-13 JP JP2004515676A patent/JP2005530888A/ja active Pending
- 2003-05-13 BR BR0312055-4A patent/BR0312055A/pt not_active IP Right Cessation
- 2003-05-13 EP EP03724552A patent/EP1517969B1/en not_active Expired - Lifetime
- 2003-05-13 CA CA2490503A patent/CA2490503C/en not_active Expired - Fee Related
- 2003-05-13 DE DE60315029T patent/DE60315029T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1517969B1 (en) | 2007-07-18 |
| US20030236340A1 (en) | 2003-12-25 |
| CN1671811A (zh) | 2005-09-21 |
| AU2003230375A1 (en) | 2004-01-06 |
| CN100509972C (zh) | 2009-07-08 |
| CA2490503C (en) | 2011-08-16 |
| EP1517969A1 (en) | 2005-03-30 |
| ATE367422T1 (de) | 2007-08-15 |
| US7041727B2 (en) | 2006-05-09 |
| MXPA05000118A (es) | 2005-04-11 |
| DE60315029D1 (de) | 2007-08-30 |
| JP2005530888A (ja) | 2005-10-13 |
| CA2490503A1 (en) | 2003-12-31 |
| WO2004000957A1 (en) | 2003-12-31 |
| BR0312055A (pt) | 2005-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |