NO320324B1 - Polymerer og monomerer og anvendelse derav samt fremgangsmate for fremstilling av polymerer og begroingshindrende maling inneholdende polymerer - Google Patents
Polymerer og monomerer og anvendelse derav samt fremgangsmate for fremstilling av polymerer og begroingshindrende maling inneholdende polymerer Download PDFInfo
- Publication number
- NO320324B1 NO320324B1 NO20021491A NO20021491A NO320324B1 NO 320324 B1 NO320324 B1 NO 320324B1 NO 20021491 A NO20021491 A NO 20021491A NO 20021491 A NO20021491 A NO 20021491A NO 320324 B1 NO320324 B1 NO 320324B1
- Authority
- NO
- Norway
- Prior art keywords
- acrylate
- meth
- chloride
- substituted
- alcohol
- Prior art date
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- 239000000178 monomer Substances 0.000 title claims abstract description 73
- 229920000642 polymer Polymers 0.000 title claims abstract description 65
- 230000003373 anti-fouling effect Effects 0.000 title claims abstract description 34
- 239000003973 paint Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 10
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract description 7
- -1 triethylsilyl Chemical group 0.000 claims description 1014
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 238000005498 polishing Methods 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 claims description 3
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000012512 characterization method Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 512
- 235000019441 ethanol Nutrition 0.000 description 187
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 119
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 111
- 239000011230 binding agent Substances 0.000 description 22
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 10
- 239000000049 pigment Substances 0.000 description 10
- FPCPOLLWTJARLO-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)acetic acid Chemical compound CC(=C)C(=O)OCC(O)=O FPCPOLLWTJARLO-UHFFFAOYSA-N 0.000 description 9
- SBWOBTUYQXLKSS-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propanoic acid Chemical compound CC(=C)C(=O)OCCC(O)=O SBWOBTUYQXLKSS-UHFFFAOYSA-N 0.000 description 9
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 8
- JYSWMLAADBQAQX-UHFFFAOYSA-N 2-prop-2-enoyloxyacetic acid Chemical compound OC(=O)COC(=O)C=C JYSWMLAADBQAQX-UHFFFAOYSA-N 0.000 description 8
- FWGJQLNEEMJIRO-UHFFFAOYSA-N 5-(2-methylprop-2-enoyloxy)pentanoic acid Chemical compound CC(=C)C(=O)OCCCCC(O)=O FWGJQLNEEMJIRO-UHFFFAOYSA-N 0.000 description 8
- WCPPBOCOQZELQO-UHFFFAOYSA-N 5-prop-2-enoyloxypentanoic acid Chemical compound OC(=O)CCCCOC(=O)C=C WCPPBOCOQZELQO-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229960004419 dimethyl fumarate Drugs 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- DTJGMNVTTPUVFY-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butanoic acid Chemical compound CC(=C)C(=O)OCCCC(O)=O DTJGMNVTTPUVFY-UHFFFAOYSA-N 0.000 description 6
- HEMYIEDNNZJZSV-UHFFFAOYSA-N 4-prop-2-enoyloxybutanoic acid Chemical compound OC(=O)CCCOC(=O)C=C HEMYIEDNNZJZSV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 6
- 229960003750 ethyl chloride Drugs 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- 239000005751 Copper oxide Substances 0.000 description 3
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 3
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 229910000431 copper oxide Inorganic materials 0.000 description 3
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000013535 sea water Substances 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- VYBIZBGDHYRFBW-OWBHPGMISA-N (Z)-2-methyl-3-[4-oxo-4-(3-phenylpropanoyloxy)butyl]but-2-enedioic acid Chemical compound OC(=O)C(/C)=C(C(O)=O)/CCCC(=O)OC(=O)CCC1=CC=CC=C1 VYBIZBGDHYRFBW-OWBHPGMISA-N 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CLMOTGBOOYXUAE-UHFFFAOYSA-N 1,4-dichloro-1,1-diphenylbutane-2,3-dione Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)C(=O)CCl)C1=CC=CC=C1 CLMOTGBOOYXUAE-UHFFFAOYSA-N 0.000 description 2
- YAJOYOBJPNAYHH-UHFFFAOYSA-N 1,4-dichloro-1-phenylbutane-2,3-dione Chemical compound ClCC(=O)C(=O)C(Cl)C1=CC=CC=C1 YAJOYOBJPNAYHH-UHFFFAOYSA-N 0.000 description 2
- HVSHJFFGLQTUHX-UHFFFAOYSA-N 1,5-dichloro-1,1-diphenylpentane-2,3-dione Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)C(=O)CCCl)C1=CC=CC=C1 HVSHJFFGLQTUHX-UHFFFAOYSA-N 0.000 description 2
- NHBPTRUUPJUTNG-UHFFFAOYSA-N 1,5-dichloro-1-phenylpentane-2,3-dione Chemical compound ClCCC(=O)C(=O)C(Cl)C1=CC=CC=C1 NHBPTRUUPJUTNG-UHFFFAOYSA-N 0.000 description 2
- PVQXKWYRDXIWFJ-UHFFFAOYSA-N 1,6-dichloro-1,1-diphenylhexane-2,3-dione Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)C(=O)CCCCl)C1=CC=CC=C1 PVQXKWYRDXIWFJ-UHFFFAOYSA-N 0.000 description 2
- QKQQEWDWKPZVKC-UHFFFAOYSA-N 1,6-dichloro-1-phenylhexane-2,3-dione Chemical compound ClCCCC(=O)C(=O)C(Cl)C1=CC=CC=C1 QKQQEWDWKPZVKC-UHFFFAOYSA-N 0.000 description 2
- JFESQDALZVWHCT-UHFFFAOYSA-N 1,7-dichloro-1,1-diphenylheptane-2,3-dione Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)C(=O)CCCCCl)C1=CC=CC=C1 JFESQDALZVWHCT-UHFFFAOYSA-N 0.000 description 2
- CKFKRNPRPGNLLV-UHFFFAOYSA-N 1,7-dichloro-1-phenylheptane-2,3-dione Chemical compound ClCCCCC(=O)C(=O)C(Cl)C1=CC=CC=C1 CKFKRNPRPGNLLV-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- MWTFOYVPAQSMKR-UHFFFAOYSA-N 1-chloro-4-(4-methoxyphenyl)butane-2,3-dione Chemical compound COC1=CC=C(CC(=O)C(=O)CCl)C=C1 MWTFOYVPAQSMKR-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
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- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
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- 239000011667 zinc carbonate Substances 0.000 description 1
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- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C09D143/04—Homopolymers or copolymers of monomers containing silicon
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Adhesive Tapes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20021491A NO320324B1 (no) | 2002-03-26 | 2002-03-26 | Polymerer og monomerer og anvendelse derav samt fremgangsmate for fremstilling av polymerer og begroingshindrende maling inneholdende polymerer |
| AU2003225433A AU2003225433A1 (en) | 2002-03-26 | 2003-03-20 | Film-forming polymer and antifouling paint |
| PT03745039T PT1487928E (pt) | 2002-03-26 | 2003-03-20 | Polímero que forma filmes e tinta antivegetativa |
| PCT/NO2003/000095 WO2003080747A1 (en) | 2002-03-26 | 2003-03-20 | Film-forming polymer and antifouling paint |
| JP2003578484A JP4468702B2 (ja) | 2002-03-26 | 2003-03-20 | 皮膜形成性ポリマーと防汚塗料 |
| EP03745039A EP1487928B1 (de) | 2002-03-26 | 2003-03-20 | Filmbildendes polymer und bewuchsverhindernder anstrichstoff |
| DE60322853T DE60322853D1 (de) | 2002-03-26 | 2003-03-20 | Filmbildendes polymer und bewuchsverhindernder anstrichstoff |
| AT03745039T ATE404642T1 (de) | 2002-03-26 | 2003-03-20 | Filmbildendes polymer und bewuchsverhindernder anstrichstoff |
| KR1020047015466A KR101015264B1 (ko) | 2002-03-26 | 2003-03-20 | 필름 형성 폴리머 및 방오 페인트 |
| CNB038069261A CN100519671C (zh) | 2002-03-26 | 2003-03-20 | 成膜聚合物和防污漆 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20021491A NO320324B1 (no) | 2002-03-26 | 2002-03-26 | Polymerer og monomerer og anvendelse derav samt fremgangsmate for fremstilling av polymerer og begroingshindrende maling inneholdende polymerer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20021491D0 NO20021491D0 (no) | 2002-03-26 |
| NO20021491L NO20021491L (no) | 2003-09-29 |
| NO320324B1 true NO320324B1 (no) | 2005-11-21 |
Family
ID=19913471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20021491A NO320324B1 (no) | 2002-03-26 | 2002-03-26 | Polymerer og monomerer og anvendelse derav samt fremgangsmate for fremstilling av polymerer og begroingshindrende maling inneholdende polymerer |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1487928B1 (de) |
| JP (1) | JP4468702B2 (de) |
| KR (1) | KR101015264B1 (de) |
| CN (1) | CN100519671C (de) |
| AT (1) | ATE404642T1 (de) |
| AU (1) | AU2003225433A1 (de) |
| DE (1) | DE60322853D1 (de) |
| NO (1) | NO320324B1 (de) |
| PT (1) | PT1487928E (de) |
| WO (1) | WO2003080747A1 (de) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009076722A1 (en) * | 2007-12-19 | 2009-06-25 | The University Of Melbourne | Method of protecting a surface from biological fouling |
| NO328788B1 (no) | 2008-03-14 | 2010-05-18 | Jotun As | Bindemiddel til lufttørkende maling |
| US20100135949A1 (en) * | 2008-12-01 | 2010-06-03 | Becton, Dickinson And Company | Antimicrobial compositions |
| EP2348077B1 (de) | 2010-01-26 | 2013-04-03 | Jotun A/S | Fäulnisverhindernde Zusammensetzung |
| US20130136716A1 (en) | 2010-06-04 | 2013-05-30 | Jotun A/S | Antifouling coating |
| US9352119B2 (en) | 2012-05-15 | 2016-05-31 | Becton, Dickinson And Company | Blood control IV catheter with antimicrobial properties |
| US9579486B2 (en) | 2012-08-22 | 2017-02-28 | Becton, Dickinson And Company | Blood control IV catheter with antimicrobial properties |
| EP2708594A1 (de) | 2012-09-18 | 2014-03-19 | Jotun A/S | Reinigungsverfahren |
| EP2725073B1 (de) | 2012-10-23 | 2016-08-03 | Jotun A/S | Fäulnisverhindernde Beschichtungszusammensetzung |
| WO2014064048A1 (en) | 2012-10-23 | 2014-05-01 | Jotun A/S | Antifouling coating composition |
| CN104955828A (zh) | 2012-12-19 | 2015-09-30 | 佐敦集团 | 甲硅烷基酯共聚物 |
| US9750928B2 (en) | 2013-02-13 | 2017-09-05 | Becton, Dickinson And Company | Blood control IV catheter with stationary septum activator |
| US9695323B2 (en) | 2013-02-13 | 2017-07-04 | Becton, Dickinson And Company | UV curable solventless antimicrobial compositions |
| EP2902453A1 (de) | 2014-01-31 | 2015-08-05 | Jotun A/S | Fäulnisverhindernde Zusammensetzung |
| EP2902452A1 (de) | 2014-01-31 | 2015-08-05 | Jotun A/S | Fäulnisverhindernde Zusammensetzung |
| US9675793B2 (en) | 2014-04-23 | 2017-06-13 | Becton, Dickinson And Company | Catheter tubing with extraluminal antimicrobial coating |
| US10376686B2 (en) | 2014-04-23 | 2019-08-13 | Becton, Dickinson And Company | Antimicrobial caps for medical connectors |
| US9789279B2 (en) | 2014-04-23 | 2017-10-17 | Becton, Dickinson And Company | Antimicrobial obturator for use with vascular access devices |
| US10232088B2 (en) | 2014-07-08 | 2019-03-19 | Becton, Dickinson And Company | Antimicrobial coating forming kink resistant feature on a vascular access device |
| KR102626623B1 (ko) | 2015-04-09 | 2024-01-17 | 요툰 에이/에스 | 방오성 조성물 |
| US10954395B2 (en) | 2015-07-13 | 2021-03-23 | Jotun A/S | Antifouling composition |
| US10493244B2 (en) | 2015-10-28 | 2019-12-03 | Becton, Dickinson And Company | Extension tubing strain relief |
| CN106221344A (zh) * | 2016-07-28 | 2016-12-14 | 江苏昌悦重工科技有限公司 | 一种耐腐蚀光伏箱 |
| JP7178167B2 (ja) | 2016-11-11 | 2022-11-25 | ヨトゥン アーエス | 防汚組成物 |
| CN110139903B (zh) | 2016-11-11 | 2022-01-28 | 汉伯公司 | 包含新型碳基可水解聚合物的防污涂料组合物 |
| EP4234643B1 (de) | 2016-11-11 | 2025-02-12 | Jotun A/S | Antifouling-zusammensetzung |
| CN108070055B (zh) * | 2016-11-11 | 2022-10-04 | 佐敦公司 | 防污组合物 |
| SG11201906534XA (en) | 2017-01-19 | 2019-08-27 | Jotun As | Antifouling composition |
| EP3845617B1 (de) * | 2018-08-29 | 2022-10-05 | Nitto Kasei Co., Ltd. | Bewuchshemmende beschichtungsmaterialzusammensetzung |
| DE102018129419A1 (de) * | 2018-11-22 | 2020-05-28 | Johannes Gutenberg-Universität Mainz | Acrylat-Copolymer für galenische Anwendungen |
| JP7747338B2 (ja) * | 2020-11-10 | 2025-10-01 | 日東化成株式会社 | 防汚塗料組成物 |
| JP7588835B2 (ja) * | 2021-02-24 | 2024-11-25 | 日東化成株式会社 | 防汚塗料組成物 |
| CN117015579B (zh) * | 2021-03-02 | 2025-09-30 | 日东化成株式会社 | 防污涂料组合物 |
| CN116940644A (zh) * | 2021-03-02 | 2023-10-24 | 日东化成株式会社 | 防污涂料组合物 |
| EP4328276A4 (de) * | 2021-05-12 | 2024-11-20 | Nitto Kasei Co., Ltd. | Fäulnisverhindernde beschichtungszusammensetzung |
| KR102473773B1 (ko) | 2021-05-17 | 2022-12-02 | 한국신발피혁연구원 | 해수 저항성이 우수한 방오점착테이프용 아크릴 점착제 조성물 |
| KR20240134194A (ko) * | 2022-01-26 | 2024-09-06 | 닛토 가세이 가부시끼 가이샤 | 방오 도료 조성물 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5847066A (ja) * | 1981-09-16 | 1983-03-18 | Nippon Oil & Fats Co Ltd | 防汚塗料 |
| JPS63215780A (ja) * | 1987-03-04 | 1988-09-08 | Dainippon Ink & Chem Inc | 防汚塗料用樹脂 |
| JP2514217B2 (ja) * | 1987-12-04 | 1996-07-10 | 東芝シリコーン株式会社 | 防汚コ―ティング材 |
| EP0617096B1 (de) * | 1993-03-25 | 1998-01-28 | Dai Nippon Toryo Co., Ltd. | Antifäulnisfarbe |
| JP2790021B2 (ja) * | 1993-09-30 | 1998-08-27 | 日本油脂株式会社 | 塗料組成物 |
| JPH0820778A (ja) * | 1994-07-06 | 1996-01-23 | Kawasaki Steel Corp | コークス炉の炉壁補修用仮炉蓋 |
| MY115462A (en) * | 1995-06-01 | 2003-06-30 | Chugoku Marine Paints | Antifouling coating composition, coating film formed from said antifouling coating composition, antifouling method using said antifouling coating composition and hull or underwater structure coated with said coating film |
| NO952329D0 (no) * | 1995-06-13 | 1995-06-13 | Jotun As | Polymerer for grohemmende maling og fremgangsmåte for fremstilling derav |
| PL200670B1 (pl) * | 1998-12-28 | 2009-01-30 | Chugoku Marine Paints | Kopolimer sililo(met)akrylanowy, sposób jego wytwarzania, przeciwporostowa kompozycja do malowania zawierająca kopolimer sililo(met)akrylanowy oraz jej zastosowanie |
| US6992120B2 (en) * | 2001-11-13 | 2006-01-31 | Arkema Inc. | Coating compositions |
| NO327258B1 (no) * | 1999-07-27 | 2009-05-25 | Ishikawajima Harima Heavy Ind | Polyesterharpiks for anvendelse i en grohemmende maling samt grohemmende maling omfattende polyesterharpiksen |
| US6498264B2 (en) * | 2001-03-06 | 2002-12-24 | Shin-Etsu Chemical Co., Ltd. | Silyl (meth)acrylates having bulky substituent group and preparation thereof |
| DE60216129T2 (de) * | 2001-09-21 | 2007-03-15 | Sigma Coatings B.V. | Verfahren zur herstellung von organosilylkarboxylatmonomeren, und deren verwendung als anwuchsverhindernde überzüge |
| EP1295888A1 (de) * | 2001-09-21 | 2003-03-26 | Sigma Coatings B.V. | Verfahren zur Herstellung von trialkylsilylierten Karboxylatmonomeren, diese trialkylsilylierten Karboxylatmonomere, und deren Verwendung als anwuchsverhindernder Überzug |
-
2002
- 2002-03-26 NO NO20021491A patent/NO320324B1/no not_active IP Right Cessation
-
2003
- 2003-03-20 KR KR1020047015466A patent/KR101015264B1/ko not_active Expired - Fee Related
- 2003-03-20 DE DE60322853T patent/DE60322853D1/de not_active Expired - Lifetime
- 2003-03-20 CN CNB038069261A patent/CN100519671C/zh not_active Expired - Fee Related
- 2003-03-20 AT AT03745039T patent/ATE404642T1/de not_active IP Right Cessation
- 2003-03-20 PT PT03745039T patent/PT1487928E/pt unknown
- 2003-03-20 EP EP03745039A patent/EP1487928B1/de not_active Expired - Lifetime
- 2003-03-20 AU AU2003225433A patent/AU2003225433A1/en not_active Abandoned
- 2003-03-20 WO PCT/NO2003/000095 patent/WO2003080747A1/en not_active Ceased
- 2003-03-20 JP JP2003578484A patent/JP4468702B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE404642T1 (de) | 2008-08-15 |
| WO2003080747A1 (en) | 2003-10-02 |
| JP2005520912A (ja) | 2005-07-14 |
| JP4468702B2 (ja) | 2010-05-26 |
| KR101015264B1 (ko) | 2011-02-18 |
| KR20050016323A (ko) | 2005-02-21 |
| NO20021491D0 (no) | 2002-03-26 |
| CN1643085A (zh) | 2005-07-20 |
| PT1487928E (pt) | 2008-11-14 |
| CN100519671C (zh) | 2009-07-29 |
| DE60322853D1 (de) | 2008-09-25 |
| AU2003225433A1 (en) | 2003-10-08 |
| EP1487928B1 (de) | 2008-08-13 |
| EP1487928A1 (de) | 2004-12-22 |
| NO20021491L (no) | 2003-09-29 |
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Legal Events
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| MM1K | Lapsed by not paying the annual fees |