WO2000054589A1 - Sel de cuivre bis (2-pyridinethiol 1-oxyde) enrobe - Google Patents
Sel de cuivre bis (2-pyridinethiol 1-oxyde) enrobe Download PDFInfo
- Publication number
- WO2000054589A1 WO2000054589A1 PCT/JP2000/001638 JP0001638W WO0054589A1 WO 2000054589 A1 WO2000054589 A1 WO 2000054589A1 JP 0001638 W JP0001638 W JP 0001638W WO 0054589 A1 WO0054589 A1 WO 0054589A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copper salt
- oxide
- bis
- weight
- parts
- Prior art date
Links
- 150000001879 copper Chemical class 0.000 title claims abstract description 130
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 title claims abstract description 57
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 40
- -1 rosins Chemical class 0.000 claims abstract description 34
- 239000011248 coating agent Substances 0.000 claims abstract description 25
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 20
- 239000000194 fatty acid Substances 0.000 claims abstract description 20
- 229930195729 fatty acid Natural products 0.000 claims abstract description 20
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 20
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 15
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 15
- 239000010687 lubricating oil Substances 0.000 claims abstract description 14
- 229920001083 polybutene Polymers 0.000 claims abstract description 14
- 238000000576 coating method Methods 0.000 claims abstract description 7
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 24
- 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 claims description 24
- 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 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 235000011187 glycerol Nutrition 0.000 claims description 18
- 239000012188 paraffin wax Substances 0.000 claims description 15
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 13
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 claims 1
- RIVXBGBFTVRUKA-UHFFFAOYSA-N BSB Chemical compound BSB RIVXBGBFTVRUKA-UHFFFAOYSA-N 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 28
- 230000003373 anti-fouling effect Effects 0.000 abstract description 20
- 230000002411 adverse Effects 0.000 abstract description 4
- 229940099259 vaseline Drugs 0.000 abstract description 2
- 125000005498 phthalate group Chemical class 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
- 239000000203 mixture Substances 0.000 description 21
- 239000010949 copper Substances 0.000 description 15
- 229910052802 copper Inorganic materials 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 12
- 229910052725 zinc Inorganic materials 0.000 description 12
- 239000011701 zinc Substances 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 235000019271 petrolatum Nutrition 0.000 description 8
- 239000000428 dust Substances 0.000 description 7
- 229920001021 polysulfide Polymers 0.000 description 7
- 239000005077 polysulfide Substances 0.000 description 7
- 150000008117 polysulfides Polymers 0.000 description 7
- 239000004264 Petrolatum Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229940066842 petrolatum Drugs 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000010723 turbine oil Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- DWLAVVBOGOXHNH-UHFFFAOYSA-L magnesium;prop-2-enoate Chemical compound [Mg+2].[O-]C(=O)C=C.[O-]C(=O)C=C DWLAVVBOGOXHNH-UHFFFAOYSA-L 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000007794 irritation Effects 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
- 231100000017 mucous membrane irritation Toxicity 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 230000036556 skin irritation Effects 0.000 description 3
- 231100000475 skin irritation Toxicity 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- UGRXGEHQNPBILJ-UHFFFAOYSA-N (2-methoxyphenyl) prop-2-enoate Chemical compound COC1=CC=CC=C1OC(=O)C=C UGRXGEHQNPBILJ-UHFFFAOYSA-N 0.000 description 2
- ZENZJGDPWWLORF-UHFFFAOYSA-N (Z)-9-Octadecenal Natural products CCCCCCCCC=CCCCCCCCC=O ZENZJGDPWWLORF-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- BSVKCDLFPMKDBM-UHFFFAOYSA-L C(C(=C)C)(=O)[O-].C(C)(=O)[O-].[Cu+2] Chemical compound C(C(=C)C)(=O)[O-].C(C)(=O)[O-].[Cu+2] BSVKCDLFPMKDBM-UHFFFAOYSA-L 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- CHONRHACVRVHMK-UHFFFAOYSA-N O(C1=CC=CC=C1)CC(=O)O.C(C=C)(=O)O Chemical compound O(C1=CC=CC=C1)CC(=O)O.C(C=C)(=O)O CHONRHACVRVHMK-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 description 2
- HTNGVPRYUODTIX-UHFFFAOYSA-L copper;2-methylprop-2-enoate;naphthalene-1-carboxylate Chemical compound [Cu+2].CC(=C)C([O-])=O.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 HTNGVPRYUODTIX-UHFFFAOYSA-L 0.000 description 2
- XPLSDXJBKRIVFZ-UHFFFAOYSA-L copper;prop-2-enoate Chemical compound [Cu+2].[O-]C(=O)C=C.[O-]C(=O)C=C XPLSDXJBKRIVFZ-UHFFFAOYSA-L 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000001508 eye Anatomy 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- DZBOAIYHPIPCBP-UHFFFAOYSA-L magnesium;2-methylprop-2-enoate Chemical compound [Mg+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O DZBOAIYHPIPCBP-UHFFFAOYSA-L 0.000 description 2
- GUKBQGHCNPSOJF-UHFFFAOYSA-L magnesium;prop-2-enoate;benzoate Chemical compound [Mg+2].[O-]C(=O)C=C.[O-]C(=O)C1=CC=CC=C1 GUKBQGHCNPSOJF-UHFFFAOYSA-L 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 231100000989 no adverse effect Toxicity 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- MPLUJWVUQCBCBX-UHFFFAOYSA-L zinc;16-methylheptadecanoate Chemical compound [Zn+2].CC(C)CCCCCCCCCCCCCCC([O-])=O.CC(C)CCCCCCCCCCCCCCC([O-])=O MPLUJWVUQCBCBX-UHFFFAOYSA-L 0.000 description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 2
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 2
- NLAUYBDMLQNGCO-UHFFFAOYSA-N (2-methoxyphenyl) 2-methylprop-2-enoate Chemical compound COC1=CC=CC=C1OC(=O)C(C)=C NLAUYBDMLQNGCO-UHFFFAOYSA-N 0.000 description 1
- NCPCSICMICIMCE-UHFFFAOYSA-N (3-methoxyphenyl) 2-methylprop-2-enoate Chemical compound COC1=CC=CC(OC(=O)C(C)=C)=C1 NCPCSICMICIMCE-UHFFFAOYSA-N 0.000 description 1
- MJJURONWODRKDU-UHFFFAOYSA-N (3-methoxyphenyl) prop-2-enoate Chemical compound COC1=CC=CC(OC(=O)C=C)=C1 MJJURONWODRKDU-UHFFFAOYSA-N 0.000 description 1
- WIZMCLXMWBKNKH-UHFFFAOYSA-N (4-methoxyphenyl) 2-methylprop-2-enoate Chemical compound COC1=CC=C(OC(=O)C(C)=C)C=C1 WIZMCLXMWBKNKH-UHFFFAOYSA-N 0.000 description 1
- WFJNXICXEHGDLB-UHFFFAOYSA-N (4-methoxyphenyl) prop-2-enoate Chemical compound COC1=CC=C(OC(=O)C=C)C=C1 WFJNXICXEHGDLB-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- VZSSEIYYXSLLNB-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethyl prop-2-enoate Chemical compound COC1=CC=C(CCOC(=O)C=C)C=C1 VZSSEIYYXSLLNB-UHFFFAOYSA-N 0.000 description 1
- NMGPHUOPSWFUEB-UHFFFAOYSA-N 2-(butylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCCNCCOC(=O)C(C)=C NMGPHUOPSWFUEB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- BMFMTNROJASFBW-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfinyl)acetic acid Chemical compound OC(=O)CS(=O)CC1=CC=CO1 BMFMTNROJASFBW-UHFFFAOYSA-N 0.000 description 1
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- 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
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- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
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- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 1
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- NDOZRESYLDMABN-UHFFFAOYSA-L zinc;2-methylprop-2-enoate;benzoate Chemical compound [Zn+2].CC(=C)C([O-])=O.[O-]C(=O)C1=CC=CC=C1 NDOZRESYLDMABN-UHFFFAOYSA-L 0.000 description 1
- WOQSHHHKBNWSCM-UHFFFAOYSA-L zinc;2-methylprop-2-enoate;propanoate Chemical compound [Zn+2].CCC([O-])=O.CC(=C)C([O-])=O WOQSHHHKBNWSCM-UHFFFAOYSA-L 0.000 description 1
- NZBPBKKXMQWABX-UHFFFAOYSA-L zinc;2-nitronaphthalene-1-carboxylate Chemical compound [Zn+2].C1=CC=C2C(C(=O)[O-])=C([N+]([O-])=O)C=CC2=C1.C1=CC=C2C(C(=O)[O-])=C([N+]([O-])=O)C=CC2=C1 NZBPBKKXMQWABX-UHFFFAOYSA-L 0.000 description 1
- QDVOXCFDSCPLDI-UHFFFAOYSA-L zinc;2-phenoxyacetate Chemical compound [Zn+2].[O-]C(=O)COC1=CC=CC=C1.[O-]C(=O)COC1=CC=CC=C1 QDVOXCFDSCPLDI-UHFFFAOYSA-L 0.000 description 1
- BAPZYNIYMWKFFL-UHFFFAOYSA-L zinc;naphthalene-1-carboxylate;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 BAPZYNIYMWKFFL-UHFFFAOYSA-L 0.000 description 1
- GXTFJSCLUPBSCT-UHFFFAOYSA-L zinc;prop-2-enoate;benzoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C1=CC=CC=C1 GXTFJSCLUPBSCT-UHFFFAOYSA-L 0.000 description 1
- ZMMDDNWOALVYRP-UHFFFAOYSA-L zinc;prop-2-enoate;quinoline-2-carboxylate Chemical compound [Zn+2].[O-]C(=O)C=C.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 ZMMDDNWOALVYRP-UHFFFAOYSA-L 0.000 description 1
- KJROUBUHARNBCN-UHFFFAOYSA-L zinc;propanoate;prop-2-enoate Chemical compound [Zn+2].CCC([O-])=O.[O-]C(=O)C=C KJROUBUHARNBCN-UHFFFAOYSA-L 0.000 description 1
- WNZNEKPFXJXMSK-UHFFFAOYSA-L zinc;quinoline-2-carboxylate Chemical compound [Zn+2].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 WNZNEKPFXJXMSK-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
Definitions
- the present invention relates to an antifouling active ingredient composition for a ship bottom paint that is safe and has an excellent antifouling effect when handling and applying work such as transportation.
- Bis (2-pyridinethiol-1-oxide) copper salt is effective as an industrial bioside, and has recently attracted attention as an antifouling active ingredient replacing organotin.
- the present invention provides a composition containing bis (2-pyridinethiol-1-oxide) copper salt, which is an antifouling component of ship bottom paints, which solves these problems and does not adversely affect the efficacy of the compound.
- the purpose is to:
- the present inventors have made intensive studies to solve the above-mentioned problems of the conventional bis (2-pyridinethiol-1-oxide) copper salt.
- the coated bis (2-pyridine) according to the present invention was obtained.
- Thiol-1-oxoxide) Copper salt was reached. That is, a bis (2-pyridinethiol-1-oxide) copper salt is coated with a specific coating agent.
- the scattering of dust is suppressed, thereby improving the safety and workability for workers, and the bottom paint containing the coated bis (2-pyridinethiol-111-oxide) copper salt is The present inventors have found that this effect is stably exhibited for a long period of time without any adverse effect on the antifouling effect, and that the long-term storage stability is not inferior, and the present invention has been completed.
- the present invention relates to [1]: one kind selected from the group consisting of glycerin, dialkyl phthalate, lubricating oil, acrylic resin, rosin, fatty acid amide, dialkyl polysulfite, polybutene, paraffin and paraserine Or bis (2-pyridinethiol-1-oxide) copper salt coated with a coating agent containing two or more compounds,
- the total amount of the compound represented by the formula (1) is 1 to 40 parts by weight per 100 parts by weight of bis (2-pyridinethiol-l-oxide) copper salt.
- 1-oxide) Copper salt
- BACKGROUND ART Bis (2-pyridinethiol-1-oxide) copper salt is known as a compound having an excellent antifouling property due to its biocidal effect, and is used as an antifouling component in marine paints such as ship bottom paints.
- the copper salt is commercially available, or can be produced, for example, by the method described in USP 2,809,971.
- To coat the bis (2-pyridinethiol-1-oxide) copper salt Contains one or more compounds selected from the group consisting of phosphorus, dialkyl phthalate, lubricating oil, acrylic resin, rosin, fatty acid amide, dialkyl boryl sulfite, polybutene, paraffin, and petrolatum Use a coating.
- glycerin examples include general-purpose glycerin, diglycerin, polyglycerin, and the like, and these may be used as a mixture.
- the alkyl group of the dialkyl phthalate preferably has 1 to 18 carbon atoms. Specific examples include getyl phthalate, dibutyl phthalate, diheptyl phthalate, and octyl phthalate. These may be used as a mixture.
- the lubricating oil include spindle oil, dynamo oil, machine oil, engine oil, turbine oil, and silicon oil, and may be used as a mixture thereof.
- other non-volatile substances for example, higher alcohols such as polyethylene glycol and stearyl alcohol may be used in combination.
- acrylic resin examples include methyl acrylate, ethyl acrylate, n-propynoleactylate, i-propynoleactylate, n-butynoleactylate, i-butynoleactylate, and t-butyl acrylate.
- Homopolymers and copolymers such as acrylamides such as rilamide, dimethylaminoethyl methacrylamide, and dimethylaminopropyl methacrylyl amide, cyanoacrylates, acrolein, cumarone, and indene Polymers. These may be used as a mixture.
- the copolymers of alkyl esterolenoate and alkyl methacrylate (glass transition point: 120 ° C to 50 ° C), the power of acrylic acid and methacrylic acid Is a divalent heavy metal salt such as copper or zinc or —S i (R) 3 (R is a methyl group, ethyl group or other alkyl group having 1 to 18 carbon atoms, or E A self-polishing resin replaced with a toxic chain group) is preferred.
- rosin examples include wood rosin, gum rosin, and towel oil rosin. Of these, wood rosin is preferred. These may be used as a mixture.
- Fatty acid amide compounds include stearic acid amides, amino acids, remitinic acid amides, methylene bis stearamides, ethylene bis stearamides, amide waxes, polyamide waxes, etc. Amide compounds of fatty acids are preferred. These may be used as a mixture.
- the dialkyl polysulfide has the general formula (1)
- R 1 represents an alkyl group having 1 to 20 carbon atoms, and ⁇ represents an integer of 2 to 10).
- Preferred R 1 includes an ethyl group, a propyl group, a t-butyl group, a t-amyl group, a t-octyl group, a t-nonyl group, a t-decyl group and a nonadecyl group.
- Preferred dialkyl polysulfides represented by the general formula (1) include getinolepentasulfide, dipropynoletetrasulfide, di-t-butyl dis / sulfide, and di-t —Octinolepentas / refited, di-t-noninolepentasulfide, di-t-dodecylpentasulfide, dinonadecyltetrasnolefin and the like. Also, these mixtures may be used.
- Dialkyl polysulfides can also be used as a mixture.
- polybutene having an average molecular weight (Mn) of 200 to 1,000 is preferably used.
- Mn average molecular weight
- Specific examples thereof include, for example, LV-5, LV-10, LV-25, and LV-25 manufactured by Nippon Oil Co., Ltd. — 50, LV—100, HV—15, HV—35, HV—50, HV—100, etc. These may be used as a mixture.
- paraffin examples include liquid paraffin, paraffin wax, and chlorinated paraffin, and these may be used as a mixture.
- Vaseline includes white petrolatum, yellow petrolatum, etc., which are used as a mixture. May be used.
- Acrylic resin, rosin and fatty acid amide are provided in a solution by dissolving acryl resin and rosin in an organic solvent to facilitate handling. Preferably.
- an aromatic organic solvent or an aliphatic organic solvent can be used.
- xylene, sorbent naphtha, kerosene and alcohols are preferable, and xylene is most preferable.
- the amount of the above-mentioned active ingredients in the coating agent is also determined as appropriate, but each of the active ingredients used, that is, glycerin, dialkyl phthalate, lubricating oil, acrylic resin, resin, fatty acid amide, dialkyl boryl sulfate
- each of the active ingredients used that is, glycerin, dialkyl phthalate, lubricating oil, acrylic resin, resin, fatty acid amide, dialkyl boryl sulfate
- 1 to 40 parts by weight of tud, polybutene, paraffin and petrolatum are added to 100 parts by weight of bis (2-pyridinthiol-1-oxide) copper salt.
- the total amount of the active ingredients of the coating agent to be used may be 1 to 40 parts by weight based on 100 parts by weight of bis (2-pyridinethiol mono-oxide) copper salt.
- bis (2-pyridinethiol-1-oxide) copper salt does not scatter and does not adversely affect the physical properties of the prepared paint.
- the amount of each used is 100 parts by weight of bis (2-pyridinethiol-one-one-oxide) copper salt.
- a total of 1 to 20 parts by weight is preferably used.
- the active ingredient in the coating agent to be used is an acrylic resin, rosin or fatty acid amide
- an organic solvent solution containing 30 to 50% by weight of an acrylic resin is used in an amount of 5 to 40 parts by weight based on 100 parts by weight of bis (2-pyridinethiol 1-oxide) copper salt.
- rosin 50 to 80 weight parts by weight. /. 5 to 40 parts by weight of the organic solvent solution contained per 100 parts by weight of the above copper salt, using fatty acid amide If so, the fatty acid amide is 10 to 40% by weight, particularly preferably 10 to 30% by weight.
- the paste containing / 0 with respect to 100 parts by weight of the copper salt.
- the total amount of the acrylic resin solution, rosin solution, and fatty acid amide paste of the above contents used is bis (2-pyridinethiol-1-1). Oxide) The amount is preferably 5 to 40 parts by weight based on 100 parts by weight of the copper salt.
- the amount of each used is 1 ⁇ 0 parts by weight of bis (2-pyridinethiol-l-oxide) copper salt. If more than 5 to 40 parts by weight are used, the total amount is preferably 5 to 40 parts by weight.
- the coated bis (2-pyridinethiol-l-oxide) copper salt of the present invention can be prepared, for example, by using various high-speed mixers or kneaders to prepare a predetermined amount of the bis (2-pyridine-thiol-l-l-oxide) copper salt and the coating agent. It is easily obtained by mixing and kneading.
- high-speed mixers include those marketed under the brand names such as "Hyblender”, “Roller Mixer”, “Hisbyda-1", “Hisladja-1”, and "Pagmixer” manufactured by Taiheiyo Kikai Co., Ltd.
- coating means not only that the entire surface of the bis (2-pyridinethiol-1-oxide) copper salt is covered with the coating agent, but also that the copper salt is not scattered as dust. The case where the coating agent is partially adhered to the copper salt surface is also included.
- the coated bis (2-pyridine-1-oxide) copper salt of the present invention is applied to underwater structures such as marine paints such as ship bottom paints, harbor facilities, buoys, submarine bases, headraces of power plants, and aquaculture nets. It is blended in paints and the like.
- Example 2 a bis (2-pyridinethiol-1-oxide) copper salt coated with the compound having an antifouling effect described in the specification was obtained. Table 1 summarizes them.
- ship bottom paint was prepared using the coated bis (2-pyridinethiol-1-oxide) copper salt obtained in Examples 1 to 20 as an antifouling component.
- a paint prepared in the same manner as in the example except that bis (2-pyridinethiol-1-oxide) copper salt not coated at all as an antifouling component was blended was tested.
- the rosin xylene solution described in Table 2 has a rosin component of 60% by weight. / 0, xylene component 4 0% by weight of the solution, Amai Dowa box, the fatty acid Ami de component 2 0 parts by weight%, the paste-like composition containing xylene 8 0 wt%, the resin is a vinyl chloride over isobutyl bi vinyl ether copolymer 50 weight of polymer component. /. 50 weight of xylene component. /. Solution.
- the coated bis (2-pyridinethiol 1-oxide) copper salt of Examples 1 to 20 does not scatter and does not cause irritation, skin irritation or mucous membrane irritation, and the workability is remarkably improved. It was found that the coating was easily eluted with, and became a bis (2-pyridinethiol-l-oxide) copper salt again.
- the paint of the comparative example using bis (2-pyridinethiol-1-oxide) copper salt which is not coated at all is compared with the paint of the example in which the coated copper salt of the present invention is blended. During preparation, dust was scattered violently, and irritation, skin irritation and mucous membrane irritation were felt. In addition, workability was significantly reduced due to poor handling.
- Examples 1 to 20 Coated bis (2-pyridinethiol-11-oxide) hull bottom paint mixed with copper salt was placed in a pressure-resistant glass bottle and left in a 50 ° C constant temperature bath to perform an accelerated deterioration test. After a predetermined date, the sample was taken out and the viscosity at 25 ° C was measured with a streamer viscometer. The results are shown in Table 3.
- Bis (2-pyridinthiol-1-oxide) copper salt Bis (2-pyridinethiol-1-oxide) copper salt coated with the compound by adding 3 parts by weight of serine, 3 parts by weight of di-n-butylphthalate, and 3 parts by weight of turbine oil and stirring and mixing with a Henschel mixer. A composition was obtained.
- a bis (2-pyridinethiol-1-oxide) copper salt coated with the compound was obtained in the same manner as in Example 1 except that 5 parts by weight of glycerin was added as a coating agent.
- Example 2 4 A bis (2-pyridinethiol-1-oxide) copper salt coated with the compound was obtained in the same manner as in Example 1 except that 5 parts by weight of glycerin was added as a coating agent.
- Example 2 4 A bis (2-pyridinethiol-1-oxide) copper salt coated with the compound was obtained in the same manner as in Example 1 except that 5 parts by weight of glycerin was added as a coating agent.
- a bis (2-pyridinthiol-1-oxide) copper salt coated with the compound was obtained in the same manner as in Example 1 except that 5 parts by weight of di-n-butyl phthalate was added as a coating agent.
- a bis (2-pyridinethiol-1-oxide) copper salt coated with the compound was obtained in the same manner as in Example 1 except that 5 parts by weight of turbine oil was added as a coating agent.
- a bis (2-pyridinethiol-l-loxide) copper salt coated with the compound was prepared in the same manner as in Example 1 except that 5 parts by weight of dalyserin and 0.5 part by weight of di-n-butylphthalate were added as a coating agent. Obtained.
- a bis (2-pyridinethiol-111-oxide) copper salt coated with the compound was obtained in the same manner as in Example 1 except that 5 parts by weight of glycerin and 5 parts by weight of turbine oil were added as coating agents.
- Example 2 100 parts by weight of bis (2-viridinethiol-1-oxide), 100 parts by weight of copper salt, 5 parts by weight of polyalkyl polysulfide, 5 parts by weight of polybutene, and 5 parts by weight of petrolatum are added for 1 hour using a Henschel mixer By stirring and mixing, a bis (2-pyridinethiol-1-oxide) copper salt coated with the compound was obtained.
- Example 21 The coated bis (2-pyridinethiol-1-oxide) copper salt obtained in Examples 1 to 28 is different from the bis (2-pyridinethiol-1-oxide) copper salt, which is a needle-like crystal. There was no outbreak. It was also found that the coating was easily eluted in the paint, and again became acicular crystals of bis (2-pyridinethiol-1-oxide) copper salt.
- Examples 21 The coated bis (2-pyridinethiol-11-oxide) copper salt obtained in 1-27 was used as an antifouling component in the composition shown in Table 5 and the coated bis (2-pyridinethiol-11-oxide) obtained in Example 28 was used.
- S (2-pyridinethiol 1-oxide) A ship bottom paint with the composition shown in Table 2 was prepared using copper salt as an antifouling component.
- Table 5 Formulations of ship bottom paints 21 to 27
- the coated bis (2-pyridinethiol-1-oxide) copper salt of Examples 21 to 28 does not scatter, and it is also irritating to inhalation, skin irritation, and mucous membrane irritation. Workability was significantly improved without being twisted. In addition, it was possible to obtain a ship bottom paint that had no adverse effect on the physical properties of the prepared paint and had excellent long-term storage stability.
- Table 6 shows the u results of the efficacy tests described above using a marine paint of Example 2 1 2 8. Table 6 Results of sea immersion test (biofouling area%)
- Copper 3 ⁇ 4 has no scattering properties, is easy to handle, and has excellent safety and workability. Further, the bottom paint containing the bis (2-viridinethiol-1-oxide) copper salt has no adverse effect on the storage stability and the antifouling effect, and the effect is not impaired at all even when coated.
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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Medicinal Preparation (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/700,648 US6544440B1 (en) | 1999-03-17 | 2000-03-17 | Coated bis(2-pyridinethiol-1-oxide) copper salt |
AT00909705T ATE249142T1 (de) | 1999-03-17 | 2000-03-17 | Beschichtetes bis(2-pyridinthiol 1-oxid) kupfersalz |
EP00909705A EP1080640B1 (en) | 1999-03-17 | 2000-03-17 | Coated bis(2-pyridinethiol-1-oxide)copper salt |
JP2000604683A JP4815669B2 (ja) | 1999-03-17 | 2000-03-17 | 被覆されたビス(2−ピリジンチオール−1−オキシド)銅塩 |
DE60005101T DE60005101D1 (de) | 1999-03-17 | 2000-03-17 | Beschichtetes bis(2-pyridinthiol 1-oxid) kupfersalz |
NO20005794A NO327214B1 (no) | 1999-03-17 | 2000-11-16 | Belagt bis(2-pyridintiol-1-oksyd)kobbersalt og anvendelse av bestemte forbindelser til belegging av bis(2-pyridintiol-1-oksyd)kobbersalt. |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7272799 | 1999-03-17 | ||
JP11/72727 | 1999-03-17 | ||
JP11295799 | 1999-04-20 | ||
JP11/112957 | 1999-04-20 | ||
JP11295899 | 1999-04-20 | ||
JP11/112958 | 1999-04-20 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/700,648 A-371-Of-International US6544440B1 (en) | 1999-03-17 | 2000-03-17 | Coated bis(2-pyridinethiol-1-oxide) copper salt |
US10/337,844 Division US6630079B2 (en) | 1999-03-17 | 2003-01-08 | Coated bis (2-pyridinethiol-1-oxide) copper salt |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000054589A1 true WO2000054589A1 (fr) | 2000-09-21 |
Family
ID=27301019
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2000/001638 WO2000054589A1 (fr) | 1999-03-17 | 2000-03-17 | Sel de cuivre bis (2-pyridinethiol 1-oxyde) enrobe |
Country Status (9)
Country | Link |
---|---|
US (2) | US6544440B1 (ja) |
EP (1) | EP1080640B1 (ja) |
JP (1) | JP4815669B2 (ja) |
KR (1) | KR100679497B1 (ja) |
CN (1) | CN1159965C (ja) |
AT (1) | ATE249142T1 (ja) |
DE (1) | DE60005101D1 (ja) |
NO (1) | NO327214B1 (ja) |
WO (1) | WO2000054589A1 (ja) |
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WO2003028452A1 (en) * | 2001-09-28 | 2003-04-10 | Arch Chemicals, Inc. | Non-dusting copper pyrithione dispersion |
WO2004060062A1 (en) | 2002-12-20 | 2004-07-22 | Arch Chemicals, Inc. | Small particle copper pyrithione |
JP2004225024A (ja) * | 2003-01-21 | 2004-08-12 | Api Corporation | 金属ピリチオンの油性分散組成物 |
US7481873B2 (en) | 2002-12-20 | 2009-01-27 | Arch Chemicals, Inc. | Small particle copper pyrithione |
US8980235B2 (en) * | 2003-09-30 | 2015-03-17 | Arch Chemicals, Inc. | Coated metal pyrithione particles for treatment of microorganisms |
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KR100529159B1 (ko) * | 2005-02-22 | 2005-11-17 | 주식회사 코오롱 | 특정 입도 분포를 갖는 피리치온 금속염 및 이를 포함하는도료 조성물 |
US7893047B2 (en) | 2006-03-03 | 2011-02-22 | Arch Chemicals, Inc. | Biocide composition comprising pyrithione and pyrrole derivatives |
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- 2000-03-17 AT AT00909705T patent/ATE249142T1/de not_active IP Right Cessation
- 2000-03-17 KR KR1020007012885A patent/KR100679497B1/ko not_active IP Right Cessation
- 2000-03-17 DE DE60005101T patent/DE60005101D1/de not_active Expired - Lifetime
- 2000-03-17 EP EP00909705A patent/EP1080640B1/en not_active Expired - Lifetime
- 2000-03-17 US US09/700,648 patent/US6544440B1/en not_active Expired - Fee Related
- 2000-03-17 JP JP2000604683A patent/JP4815669B2/ja not_active Expired - Fee Related
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2003
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1429605A4 (en) * | 2001-09-28 | 2007-05-30 | Arch Chem Inc | DISPERSION OF NON-DUSTOUS COPPER PYRITHIONE |
US6627665B2 (en) * | 2001-09-28 | 2003-09-30 | Arch Chemicals, Inc. | Non-dusting copper pyrithione dispersion |
JP4794817B2 (ja) * | 2001-09-28 | 2011-10-19 | アーチ ケミカルズ,インコーポレイテッド | 無粉塵性銅ピリチオン分散系 |
JP2011105753A (ja) * | 2001-09-28 | 2011-06-02 | Arch Chemicals Inc | 無粉塵性銅ピリチオン分散系 |
JP2005504812A (ja) * | 2001-09-28 | 2005-02-17 | アーチ ケミカルズ,インコーポレイテッド | 無粉塵性銅ピリチオン分散系 |
WO2003028452A1 (en) * | 2001-09-28 | 2003-04-10 | Arch Chemicals, Inc. | Non-dusting copper pyrithione dispersion |
JP2011032279A (ja) * | 2002-12-20 | 2011-02-17 | Arch Chemicals Inc | 小粒子銅ピリチオン |
US7481873B2 (en) | 2002-12-20 | 2009-01-27 | Arch Chemicals, Inc. | Small particle copper pyrithione |
JP2006511665A (ja) * | 2002-12-20 | 2006-04-06 | アーチ ケミカルズ,インコーポレイテッド | 小粒子銅ピリチオン |
WO2004060062A1 (en) | 2002-12-20 | 2004-07-22 | Arch Chemicals, Inc. | Small particle copper pyrithione |
JP2014005300A (ja) * | 2002-12-20 | 2014-01-16 | Arch Chemicals Inc | 小粒子銅ピリチオン |
JP4629311B2 (ja) * | 2003-01-21 | 2011-02-09 | 株式会社エーピーアイ コーポレーション | 金属ピリチオンの油性分散組成物 |
JP2004225024A (ja) * | 2003-01-21 | 2004-08-12 | Api Corporation | 金属ピリチオンの油性分散組成物 |
US8980235B2 (en) * | 2003-09-30 | 2015-03-17 | Arch Chemicals, Inc. | Coated metal pyrithione particles for treatment of microorganisms |
Also Published As
Publication number | Publication date |
---|---|
KR20010043679A (ko) | 2001-05-25 |
DE60005101D1 (de) | 2003-10-16 |
US6630079B2 (en) | 2003-10-07 |
CN1159965C (zh) | 2004-08-04 |
NO327214B1 (no) | 2009-05-11 |
ATE249142T1 (de) | 2003-09-15 |
NO20005794D0 (no) | 2000-11-16 |
EP1080640B1 (en) | 2003-09-10 |
CN1296380A (zh) | 2001-05-23 |
US6544440B1 (en) | 2003-04-08 |
US20030124085A1 (en) | 2003-07-03 |
EP1080640A1 (en) | 2001-03-07 |
JP4815669B2 (ja) | 2011-11-16 |
EP1080640A4 (en) | 2002-03-20 |
NO20005794L (no) | 2000-12-14 |
KR100679497B1 (ko) | 2007-02-07 |
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