NO303583B1 - Grohemmende belegningsmiddel - Google Patents
Grohemmende belegningsmiddel Download PDFInfo
- Publication number
- NO303583B1 NO303583B1 NO922455A NO922455A NO303583B1 NO 303583 B1 NO303583 B1 NO 303583B1 NO 922455 A NO922455 A NO 922455A NO 922455 A NO922455 A NO 922455A NO 303583 B1 NO303583 B1 NO 303583B1
- Authority
- NO
- Norway
- Prior art keywords
- mol
- quaternary ammonium
- coating agent
- weight
- polymer
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims description 26
- 238000000576 coating method Methods 0.000 title description 7
- 239000003146 anticoagulant agent Substances 0.000 title 1
- 229940127219 anticoagulant drug Drugs 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 88
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000011230 binding agent Substances 0.000 claims abstract description 24
- 230000003115 biocidal effect Effects 0.000 claims abstract description 18
- 230000003373 anti-fouling effect Effects 0.000 claims abstract description 13
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims abstract description 12
- 239000003139 biocide Substances 0.000 claims abstract description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 32
- 229920001577 copolymer Polymers 0.000 claims description 23
- 239000000049 pigment Substances 0.000 claims description 16
- 239000013535 sea water Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 5
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical group OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000008199 coating composition Substances 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 65
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 46
- 238000000034 method Methods 0.000 description 38
- 239000000178 monomer Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- -1 amine salts Chemical class 0.000 description 34
- 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 28
- 238000006243 chemical reaction Methods 0.000 description 27
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 26
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 21
- 239000003973 paint Substances 0.000 description 18
- 150000003839 salts Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- JIXRLXQGMYKCND-UHFFFAOYSA-M 2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate;triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C JIXRLXQGMYKCND-UHFFFAOYSA-M 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 7
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000003459 sulfonic acid esters Chemical class 0.000 description 6
- 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 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003495 polar organic solvent Substances 0.000 description 5
- 238000005498 polishing Methods 0.000 description 5
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000008054 sulfonate salts Chemical class 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical group [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920001002 functional polymer Polymers 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- VEAZEPMQWHPHAG-UHFFFAOYSA-N n,n,n',n'-tetramethylbutane-1,4-diamine Chemical compound CN(C)CCCCN(C)C VEAZEPMQWHPHAG-UHFFFAOYSA-N 0.000 description 2
- 230000002572 peristaltic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- WYMJGAFESNKTEC-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;copper(1+) Chemical compound [Cu+].NC(=S)SCCSC(N)=S WYMJGAFESNKTEC-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- GIPMCZGVJZPZBS-UHFFFAOYSA-M 2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate;trimethyl(tetradecyl)azanium Chemical compound [O-]S(=O)(=O)CC(C)(C)NC(=O)C=C.CCCCCCCCCCCCCC[N+](C)(C)C GIPMCZGVJZPZBS-UHFFFAOYSA-M 0.000 description 1
- XBACSBFKXGHTIS-UHFFFAOYSA-N 2-methyl-5-sulfopent-2-enoic acid Chemical compound OC(=O)C(C)=CCCS(O)(=O)=O XBACSBFKXGHTIS-UHFFFAOYSA-N 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- OYTWCZMDLBCQKN-UHFFFAOYSA-M 2-phenylethenesulfonate;triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC.[O-]S(=O)(=O)C=CC1=CC=CC=C1 OYTWCZMDLBCQKN-UHFFFAOYSA-M 0.000 description 1
- IYPBILGFFAROLA-UHFFFAOYSA-N 2-phenylethenesulfonate;trimethylazanium Chemical compound C[NH+](C)C.[O-]S(=O)(=O)C=CC1=CC=CC=C1 IYPBILGFFAROLA-UHFFFAOYSA-N 0.000 description 1
- ONWRSBMOCIQLRK-UHFFFAOYSA-N 2-phenylethenesulfonyl chloride Chemical compound ClS(=O)(=O)C=CC1=CC=CC=C1 ONWRSBMOCIQLRK-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- GLODRNIBKLRUOM-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound C[N+](C)(C)CCCO.[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C GLODRNIBKLRUOM-UHFFFAOYSA-M 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-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
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- CWADHCVBLDPPBO-UHFFFAOYSA-N dimethyl(9-phenylnonyl)azanium;2-phenylethenesulfonate Chemical compound [O-]S(=O)(=O)C=CC1=CC=CC=C1.C[NH+](C)CCCCCCCCCC1=CC=CC=C1 CWADHCVBLDPPBO-UHFFFAOYSA-N 0.000 description 1
- MYJQCRXZEKMIRC-UHFFFAOYSA-N dimethyl(9-phenylnonyl)azanium;bromide Chemical compound [Br-].C[NH+](C)CCCCCCCCCC1=CC=CC=C1 MYJQCRXZEKMIRC-UHFFFAOYSA-N 0.000 description 1
- VVMDCRAXALUEOO-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;2-phenylethenesulfonate Chemical compound [O-]S(=O)(=O)C=CC1=CC=CC=C1.CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC VVMDCRAXALUEOO-UHFFFAOYSA-M 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- WIBQZDXLMHDYMQ-UHFFFAOYSA-N dodecyl-dimethyl-octylazanium Chemical compound CCCCCCCCCCCC[N+](C)(C)CCCCCCCC WIBQZDXLMHDYMQ-UHFFFAOYSA-N 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- HDHLIWCXDDZUFH-UHFFFAOYSA-N irgarol 1051 Chemical class CC(C)(C)NC1=NC(SC)=NC(NC2CC2)=N1 HDHLIWCXDDZUFH-UHFFFAOYSA-N 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- OUVMSFWEIBCLSB-UHFFFAOYSA-N methyl 2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound COS(=O)(=O)CC(C)(C)NC(=O)C=C OUVMSFWEIBCLSB-UHFFFAOYSA-N 0.000 description 1
- FSMDHYUPDKNFEI-UHFFFAOYSA-N methyl 2-phenylethenesulfonate Chemical compound COS(=O)(=O)C=CC1=CC=CC=C1 FSMDHYUPDKNFEI-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- RAJUSMULYYBNSJ-UHFFFAOYSA-N prop-1-ene-1-sulfonic acid Chemical compound CC=CS(O)(=O)=O RAJUSMULYYBNSJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229920006250 telechelic polymer Polymers 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- QYWVQMLYIXYLRE-SEYXRHQNSA-N trimethyl-[(z)-octadec-9-enyl]azanium Chemical compound CCCCCCCC\C=C/CCCCCCCC[N+](C)(C)C QYWVQMLYIXYLRE-SEYXRHQNSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1668—Vinyl-type polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Paints Or Removers (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Windings For Motors And Generators (AREA)
- Mobile Radio Communication Systems (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Engine Equipment That Uses Special Cycles (AREA)
- Waveguide Aerials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898929111A GB8929111D0 (en) | 1989-12-22 | 1989-12-22 | Coating compositions |
| GB909026392A GB9026392D0 (en) | 1990-12-05 | 1990-12-05 | Coating compositions |
| PCT/GB1990/002019 WO1991009915A1 (en) | 1989-12-22 | 1990-12-21 | Anti-fouling coating compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO922455D0 NO922455D0 (no) | 1992-06-19 |
| NO922455L NO922455L (no) | 1992-06-19 |
| NO303583B1 true NO303583B1 (no) | 1998-08-03 |
Family
ID=26296426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO922455A NO303583B1 (no) | 1989-12-22 | 1992-06-19 | Grohemmende belegningsmiddel |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5302192A (es) |
| EP (1) | EP0506782B1 (es) |
| JP (1) | JP2994749B2 (es) |
| KR (1) | KR100193215B1 (es) |
| AT (1) | ATE141317T1 (es) |
| BR (1) | BR9007943A (es) |
| DE (1) | DE69028116T2 (es) |
| DK (1) | DK0506782T3 (es) |
| ES (1) | ES2091909T3 (es) |
| GR (1) | GR3021554T3 (es) |
| NO (1) | NO303583B1 (es) |
| PT (1) | PT96346B (es) |
| SG (1) | SG45228A1 (es) |
| WO (1) | WO1991009915A1 (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5518992A (en) * | 1994-08-05 | 1996-05-21 | University Of Central Florida | Photocatalytic surfacing agents for inhibiting algae growth |
| GB9515720D0 (en) * | 1995-08-01 | 1995-10-04 | Zeneca Ltd | Bacterial coating compositions |
| US6110452A (en) * | 1995-09-29 | 2000-08-29 | Buckman Laboratories International Inc | Methods and compositions for controlling biofouling using polyglycol fatty acid esters |
| SG50827A1 (en) * | 1996-05-13 | 1998-07-20 | Lubrizol Corp | Sulfonate containing copolymers as mist suppressants in soluble oil (water-based) metal working fluids |
| US6242526B1 (en) * | 1997-01-28 | 2001-06-05 | Stepan Company | Antimicrobial polymer latexes derived from unsaturated quaternary ammonium compounds and antimicrobial coatings, sealants, adhesives and elastomers produced from such latexes |
| US20020161108A1 (en) * | 2000-03-09 | 2002-10-31 | Stepan Company, A Corporation Of The State Of Delaware | Emulsion polymerization process utilizing ethylenically unsaturated amine salts of sulfonic, phosphoric and carboxylic acids |
| US7423167B2 (en) * | 1997-01-28 | 2008-09-09 | Stepan Company | Ethylenically unsaturated amine salts of sulfonic, phosphoric and carboxylic acids |
| DE69821337T2 (de) * | 1997-01-28 | 2004-12-02 | Stepan Co., Northfield | Emulsionspolymerisationsverfahren unter verwendung von ethylenisch ungesättigten aminsalzen von sulfonsäure,phosphorsäure und carbonsäure |
| US5880067A (en) * | 1997-05-20 | 1999-03-09 | University Of Central Florida | Photocatalytic surfacing agents with varying oxides for inhibiting algae growth |
| US6020291A (en) * | 1997-11-21 | 2000-02-01 | The Lubrizol Corporation | Branched sulfonate containing copolymers as mist suppressants in soluble oil (water-based) metal working fluids |
| GB9801747D0 (en) | 1998-01-27 | 1998-03-25 | Courtaulds Coatings Holdings | Antifouling coatings |
| NZ512945A (en) | 1999-01-20 | 2003-08-29 | Akzo Nobel Nv | Antifouling paint |
| WO2000077103A1 (en) * | 1999-06-11 | 2000-12-21 | J.C. Hempel's Skibsfarve-Fabrik A/S | Self-polishing marine antifouling paint composition containing blocked acid functional co-polymers and fibres |
| DE19928859A1 (de) * | 1999-06-24 | 2001-02-01 | Lurgi Zimmer Ag | Verfahren zur Reinigung von Ventilen oder Leitungen |
| US20020051754A1 (en) * | 2000-04-13 | 2002-05-02 | Schroeder Joseph D. | Anti-microbial packaging polymer and its method of use |
| EP1299483B1 (en) * | 2000-07-06 | 2005-08-24 | Akzo Nobel Coatings International B.V. | Antifouling paint |
| KR100386417B1 (ko) * | 2000-08-31 | 2003-06-02 | 주식회사 내비켐 | 해조류의 추출물을 이용한 환경 친화적인 방오제 |
| KR100386416B1 (ko) * | 2000-08-31 | 2003-06-02 | 주식회사 내비켐 | 해조류의 수용성 대사산물을 이용한 환경 친화적인방오제 |
| PL211454B1 (pl) | 2002-08-09 | 2012-05-31 | Akzo Nobel Coatings Int Bv | Polimer nierozpuszczalny w wodzie morskiej, sposób wytwarzania takiego polimeru oraz przeciwporostowa kompozycja powłokowa |
| BRPI0507364B1 (pt) | 2004-02-03 | 2016-07-05 | Akzo Nobel Coatings Int Bv | composiççao de revestimento antiincrustante e uso de uma composição de revestimento antiincrustante |
| CN1965002B (zh) * | 2004-05-12 | 2010-05-05 | 佳能株式会社 | 具有磺酸基或磺酸酯基和酰胺基的聚合物和生产它的方法 |
| US20070258940A1 (en) * | 2006-05-04 | 2007-11-08 | Willard Charlson Hamilton | Hydrophilic fouling-release coatings and uses thereof |
| CN101970529B (zh) * | 2008-02-13 | 2014-02-19 | 乔顿有限公司 | 防污组合物 |
| US9045651B2 (en) | 2010-06-22 | 2015-06-02 | University Of Florida Research Foundation, Inc. | Antifouling surfaces, methods of manufacture thereof and articles comprising the same |
| US9580608B1 (en) * | 2014-08-08 | 2017-02-28 | Sandia Corporation | Switchable antifouling coatings and uses thereof |
| MX2017005298A (es) * | 2014-10-28 | 2017-07-28 | Akzo Nobel Coatings Int Bv | Composicion de recubrimiento de control de incrustaciones que comprende un polimero que contiene grupos de ester de sililo y un polimero que comprende grupos de amonio cuaternario/sulfonato de fosfonio. |
| WO2016148649A1 (en) | 2015-03-16 | 2016-09-22 | Agency For Science, Technology And Research | Functionalized quaternary ammonium halides and use thereof |
| WO2019216413A1 (ja) * | 2018-05-11 | 2019-11-14 | 中国塗料株式会社 | 防汚塗料組成物、防汚塗膜、防汚塗膜付き基材及び防汚方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281452A (en) * | 1963-12-23 | 1966-10-25 | Coastal Interchemical Company | Polycyano quaternary ammonium compounds |
| US3288555A (en) * | 1965-02-05 | 1966-11-29 | Continental Oil Co | Method of inhibiting corrosion |
| GB1482252A (en) * | 1975-11-05 | 1977-08-10 | Lubrizol Corp | Salts of acrylamidoalkanesulphonic acids and polymers thereof |
| GB8700398D0 (en) * | 1986-01-22 | 1987-02-11 | Ici Plc | Compositions for surface treatment |
| FR2606021B1 (fr) * | 1986-10-30 | 1989-08-25 | Provence Universite | Liants pour peintures resistant aux salissures marines et leur procede de preparation |
| US4818797A (en) * | 1987-01-10 | 1989-04-04 | Daicel Chemical Industries, Ltd. | Polyacrylate derivative |
-
1990
- 1990-12-21 DE DE69028116T patent/DE69028116T2/de not_active Expired - Fee Related
- 1990-12-21 PT PT96346A patent/PT96346B/pt not_active IP Right Cessation
- 1990-12-21 AT AT91901604T patent/ATE141317T1/de not_active IP Right Cessation
- 1990-12-21 JP JP3501866A patent/JP2994749B2/ja not_active Expired - Fee Related
- 1990-12-21 US US07/916,158 patent/US5302192A/en not_active Expired - Lifetime
- 1990-12-21 SG SG1996001737A patent/SG45228A1/en unknown
- 1990-12-21 BR BR909007943A patent/BR9007943A/pt not_active IP Right Cessation
- 1990-12-21 EP EP91901604A patent/EP0506782B1/en not_active Expired - Lifetime
- 1990-12-21 ES ES91901604T patent/ES2091909T3/es not_active Expired - Lifetime
- 1990-12-21 WO PCT/GB1990/002019 patent/WO1991009915A1/en active IP Right Grant
- 1990-12-21 DK DK91901604.8T patent/DK0506782T3/da active
-
1992
- 1992-06-19 NO NO922455A patent/NO303583B1/no unknown
- 1992-06-20 KR KR1019920701487A patent/KR100193215B1/ko not_active IP Right Cessation
-
1996
- 1996-11-06 GR GR960402928T patent/GR3021554T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0506782T3 (da) | 1996-10-14 |
| SG45228A1 (en) | 1998-01-16 |
| DE69028116T2 (de) | 1997-02-13 |
| JP2994749B2 (ja) | 1999-12-27 |
| NO922455D0 (no) | 1992-06-19 |
| PT96346B (pt) | 1998-06-30 |
| BR9007943A (pt) | 1992-10-06 |
| NO922455L (no) | 1992-06-19 |
| ATE141317T1 (de) | 1996-08-15 |
| GR3021554T3 (en) | 1997-02-28 |
| EP0506782A1 (en) | 1992-10-07 |
| JPH05504365A (ja) | 1993-07-08 |
| KR927003741A (ko) | 1992-12-18 |
| US5302192A (en) | 1994-04-12 |
| PT96346A (pt) | 1991-10-15 |
| DE69028116D1 (de) | 1996-09-19 |
| EP0506782B1 (en) | 1996-08-14 |
| KR100193215B1 (ko) | 1999-06-15 |
| ES2091909T3 (es) | 1996-11-16 |
| WO1991009915A1 (en) | 1991-07-11 |
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