CN103068229A - 二溴丙二酰胺组合物及其作为杀生物剂的用途 - Google Patents
二溴丙二酰胺组合物及其作为杀生物剂的用途 Download PDFInfo
- Publication number
- CN103068229A CN103068229A CN201180038883XA CN201180038883A CN103068229A CN 103068229 A CN103068229 A CN 103068229A CN 201180038883X A CN201180038883X A CN 201180038883XA CN 201180038883 A CN201180038883 A CN 201180038883A CN 103068229 A CN103068229 A CN 103068229A
- Authority
- CN
- China
- Prior art keywords
- silver
- copper
- water
- metal
- dibromomalonamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- SWHQVMGRXIYDSF-UHFFFAOYSA-N 2,2-dibromopropanediamide Chemical group NC(=O)C(Br)(Br)C(N)=O SWHQVMGRXIYDSF-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000003139 biocide Substances 0.000 title description 21
- 239000010949 copper Substances 0.000 claims abstract description 25
- 239000004332 silver Substances 0.000 claims abstract description 24
- 229910052709 silver Inorganic materials 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052802 copper Inorganic materials 0.000 claims abstract description 22
- 230000003115 biocidal effect Effects 0.000 claims abstract description 21
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 23
- -1 silver hexafluoroantimonate Chemical compound 0.000 claims description 14
- 239000012530 fluid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 230000000813 microbial effect Effects 0.000 claims description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 5
- 238000005555 metalworking Methods 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 108010082714 Silver Proteins Proteins 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 239000003570 air Substances 0.000 claims description 3
- 238000010276 construction Methods 0.000 claims description 3
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims description 3
- 238000004851 dishwashing Methods 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000446 fuel Substances 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 239000011499 joint compound Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- 239000002351 wastewater Substances 0.000 claims description 3
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 claims description 2
- HGXIBFSXZZKKRV-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;silver;hydrate Chemical compound O.[Ag].[Ag].[Ag].OC(=O)CC(O)(C(O)=O)CC(O)=O HGXIBFSXZZKKRV-UHFFFAOYSA-N 0.000 claims description 2
- RYKLZUPYJFFNRR-UHFFFAOYSA-N 3-hydroxypiperidin-2-one Chemical compound OC1CCCNC1=O RYKLZUPYJFFNRR-UHFFFAOYSA-N 0.000 claims description 2
- RILOPSTZZRJOQI-UHFFFAOYSA-N 4-cyclohexylbutanoic acid;silver Chemical compound [Ag].OC(=O)CCCC1CCCCC1 RILOPSTZZRJOQI-UHFFFAOYSA-N 0.000 claims description 2
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 claims description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 2
- 239000005750 Copper hydroxide Substances 0.000 claims description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000005751 Copper oxide Substances 0.000 claims description 2
- 239000005752 Copper oxychloride Substances 0.000 claims description 2
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 claims description 2
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 2
- 229910021612 Silver iodide Inorganic materials 0.000 claims description 2
- YRXWPCFZBSHSAU-UHFFFAOYSA-N [Ag].[Ag].[Te] Chemical compound [Ag].[Ag].[Te] YRXWPCFZBSHSAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052946 acanthite Inorganic materials 0.000 claims description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 2
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 claims description 2
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940116318 copper carbonate Drugs 0.000 claims description 2
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 2
- 229910000431 copper oxide Inorganic materials 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 2
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 claims description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 2
- GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 claims description 2
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 2
- HZXGNBMOOYOYIS-PAMPIZDHSA-L copper;(z)-1,1,1,5,5,5-hexafluoro-4-oxopent-2-en-2-olate Chemical compound [Cu+2].FC(F)(F)C(/[O-])=C/C(=O)C(F)(F)F.FC(F)(F)C(/[O-])=C/C(=O)C(F)(F)F HZXGNBMOOYOYIS-PAMPIZDHSA-L 0.000 claims description 2
- OCUCCJIRFHNWBP-UHFFFAOYSA-L copper;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Cu+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O OCUCCJIRFHNWBP-UHFFFAOYSA-L 0.000 claims description 2
- MAUZTCHAIPUZJB-UHFFFAOYSA-L copper;2,3-dihydroxybutanedioate;hydrate Chemical compound O.[Cu+2].[O-]C(=O)C(O)C(O)C([O-])=O MAUZTCHAIPUZJB-UHFFFAOYSA-L 0.000 claims description 2
- FGUOYHAMMRMUQO-UHFFFAOYSA-L copper;4-cyclohexylbutanoate Chemical compound [Cu+2].[O-]C(=O)CCCC1CCCCC1.[O-]C(=O)CCCC1CCCCC1 FGUOYHAMMRMUQO-UHFFFAOYSA-L 0.000 claims description 2
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 claims description 2
- VUWZDHZJZQTKAY-UHFFFAOYSA-L copper;benzenethiolate Chemical compound [Cu+2].[S-]C1=CC=CC=C1.[S-]C1=CC=CC=C1 VUWZDHZJZQTKAY-UHFFFAOYSA-L 0.000 claims description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 2
- NOHDJXFJXJZYGO-UHFFFAOYSA-L copper;diformate;hydrate Chemical compound O.[Cu+2].[O-]C=O.[O-]C=O NOHDJXFJXJZYGO-UHFFFAOYSA-L 0.000 claims description 2
- IKUPISAYGBGQDT-UHFFFAOYSA-N copper;dioxido(dioxo)molybdenum Chemical compound [Cu+2].[O-][Mo]([O-])(=O)=O IKUPISAYGBGQDT-UHFFFAOYSA-N 0.000 claims description 2
- NHELIHXBJRANPL-UHFFFAOYSA-L copper;diperchlorate;hexahydrate Chemical compound O.O.O.O.O.O.[Cu+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O NHELIHXBJRANPL-UHFFFAOYSA-L 0.000 claims description 2
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 claims description 2
- AYNQPTYHFBBKFC-UHFFFAOYSA-N copper;methanolate Chemical compound [Cu+2].[O-]C.[O-]C AYNQPTYHFBBKFC-UHFFFAOYSA-N 0.000 claims description 2
- JNRBLFVQPTZFAG-UHFFFAOYSA-L copper;selenite Chemical compound [Cu+2].[O-][Se]([O-])=O JNRBLFVQPTZFAG-UHFFFAOYSA-L 0.000 claims description 2
- PXZSJEBZWADSIY-UHFFFAOYSA-J dicopper;phosphonato phosphate;hydrate Chemical compound O.[Cu+2].[Cu+2].[O-]P([O-])(=O)OP([O-])([O-])=O PXZSJEBZWADSIY-UHFFFAOYSA-J 0.000 claims description 2
- OLVPAOFJQTWZMY-UHFFFAOYSA-L diiodocopper;methylsulfanylmethane Chemical compound CSC.I[Cu]I OLVPAOFJQTWZMY-UHFFFAOYSA-L 0.000 claims description 2
- XQMCHJBJXIEXTM-UHFFFAOYSA-L diiodocopper;trimethyl phosphite Chemical compound I[Cu]I.COP(OC)OC XQMCHJBJXIEXTM-UHFFFAOYSA-L 0.000 claims description 2
- QEKREONBSFPWTQ-UHFFFAOYSA-N disilver dioxido(dioxo)tungsten Chemical compound [Ag+].[Ag+].[O-][W]([O-])(=O)=O QEKREONBSFPWTQ-UHFFFAOYSA-N 0.000 claims description 2
- OJKANDGLELGDHV-UHFFFAOYSA-N disilver;dioxido(dioxo)chromium Chemical compound [Ag+].[Ag+].[O-][Cr]([O-])(=O)=O OJKANDGLELGDHV-UHFFFAOYSA-N 0.000 claims description 2
- KDSXXMBJKHQCAA-UHFFFAOYSA-N disilver;selenium(2-) Chemical compound [Se-2].[Ag+].[Ag+] KDSXXMBJKHQCAA-UHFFFAOYSA-N 0.000 claims description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
- LYKNMRJOZGSSPV-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC(C)=CC=N1 LYKNMRJOZGSSPV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- IRPLSAGFWHCJIQ-UHFFFAOYSA-N selanylidenecopper Chemical compound [Se]=[Cu] IRPLSAGFWHCJIQ-UHFFFAOYSA-N 0.000 claims description 2
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 2
- 229940071536 silver acetate Drugs 0.000 claims description 2
- IMGNYAPMSDUASV-UHFFFAOYSA-K silver arsenate Chemical compound [Ag+].[Ag+].[Ag+].[O-][As]([O-])([O-])=O IMGNYAPMSDUASV-UHFFFAOYSA-K 0.000 claims description 2
- XQLMNMQWVCXIKR-UHFFFAOYSA-M silver bromate Chemical compound [Ag+].[O-]Br(=O)=O XQLMNMQWVCXIKR-UHFFFAOYSA-M 0.000 claims description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 claims description 2
- 229910001958 silver carbonate Inorganic materials 0.000 claims description 2
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 claims description 2
- SDLBJIZEEMKQKY-UHFFFAOYSA-M silver chlorate Chemical compound [Ag+].[O-]Cl(=O)=O SDLBJIZEEMKQKY-UHFFFAOYSA-M 0.000 claims description 2
- 229940096017 silver fluoride Drugs 0.000 claims description 2
- WSJGGGWTGNKDJU-UHFFFAOYSA-N silver hydrofluoride Chemical compound F.[Ag] WSJGGGWTGNKDJU-UHFFFAOYSA-N 0.000 claims description 2
- YSVXTGDPTJIEIX-UHFFFAOYSA-M silver iodate Chemical compound [Ag+].[O-]I(=O)=O YSVXTGDPTJIEIX-UHFFFAOYSA-M 0.000 claims description 2
- 229940045105 silver iodide Drugs 0.000 claims description 2
- MHLYOTJKDAAHGI-UHFFFAOYSA-N silver molybdate Chemical compound [Ag+].[Ag+].[O-][Mo]([O-])(=O)=O MHLYOTJKDAAHGI-UHFFFAOYSA-N 0.000 claims description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 2
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 claims description 2
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 claims description 2
- 229910001923 silver oxide Inorganic materials 0.000 claims description 2
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 claims description 2
- 229910000161 silver phosphate Inorganic materials 0.000 claims description 2
- 229940019931 silver phosphate Drugs 0.000 claims description 2
- 229960003600 silver sulfadiazine Drugs 0.000 claims description 2
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 claims description 2
- 229910000367 silver sulfate Inorganic materials 0.000 claims description 2
- 229940056910 silver sulfide Drugs 0.000 claims description 2
- XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 claims description 2
- WYCFMBAHFPUBDS-UHFFFAOYSA-L silver sulfite Chemical compound [Ag+].[Ag+].[O-]S([O-])=O WYCFMBAHFPUBDS-UHFFFAOYSA-L 0.000 claims description 2
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 claims description 2
- RHUVFRWZKMEWNS-UHFFFAOYSA-M silver thiocyanate Chemical compound [Ag+].[S-]C#N RHUVFRWZKMEWNS-UHFFFAOYSA-M 0.000 claims description 2
- UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 claims description 2
- CHACQUSVOVNARW-LNKPDPKZSA-M silver;(z)-4-oxopent-2-en-2-olate Chemical compound [Ag+].C\C([O-])=C\C(C)=O CHACQUSVOVNARW-LNKPDPKZSA-M 0.000 claims description 2
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 claims description 2
- XAYJXAUUXJTOSI-UHFFFAOYSA-M silver;2,2,3,3,3-pentafluoropropanoate Chemical compound [Ag+].[O-]C(=O)C(F)(F)C(F)(F)F XAYJXAUUXJTOSI-UHFFFAOYSA-M 0.000 claims description 2
- GPNIJXACCBKBEP-UHFFFAOYSA-M silver;2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound [Ag+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)F GPNIJXACCBKBEP-UHFFFAOYSA-M 0.000 claims description 2
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 claims description 2
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 claims description 2
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 claims description 2
- DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 claims description 2
- IXFNJWPLHOWEPT-UHFFFAOYSA-M silver;perchlorate;hydrate Chemical compound O.[Ag+].[O-]Cl(=O)(=O)=O IXFNJWPLHOWEPT-UHFFFAOYSA-M 0.000 claims description 2
- GJGOWHNOGHVUJK-UHFFFAOYSA-M silver;pyridine-2-carboxylate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=N1 GJGOWHNOGHVUJK-UHFFFAOYSA-M 0.000 claims description 2
- 230000009182 swimming Effects 0.000 claims description 2
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 claims description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 claims 1
- HSSAUTCKFNBPAS-UHFFFAOYSA-N CCCC[Cu] Chemical compound CCCC[Cu] HSSAUTCKFNBPAS-UHFFFAOYSA-N 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 239000004816 latex Substances 0.000 claims 1
- 229920000126 latex Polymers 0.000 claims 1
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 claims 1
- 244000005700 microbiome Species 0.000 abstract description 18
- 238000002474 experimental method Methods 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 230000009036 growth inhibition Effects 0.000 description 8
- 238000003556 assay Methods 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000003643 water by type Substances 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011885 synergistic combination Substances 0.000 description 3
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 description 2
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- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
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- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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Abstract
一种生物杀灭性组合物，其包含2,2-二溴丙二酰胺和选自银、铜及其混合物的金属，及其用于控制水和含水体系中微生物的用途。
Description
相关申请的交叉引用
本申请要求2010年8月9日提交的美国临时专利申请第61/371,906号为优先权，该申请通过引用全文纳入本文。
技术领域
本发明涉及生物杀灭性组合物及其用于控制水和含水体系中微生物的方法。所述组合物包含2,2-二溴丙二酰胺和选自银、铜及其混合物的金属。
背景技术
水体系给藻类、细菌、病毒和真菌（其中一些为致病性）提供了肥沃的滋生地。这些微生物污染源会导致多种问题，包括如泥泞绿水(green water)的不美观，如真菌、细菌或病毒感染的严重健康危险，以及包括设备堵塞腐蚀和热传递减弱的机械问题。
杀生物剂常被用于消毒和控制水和含水体系中微生物的生长。然而，并非所有杀生物剂都可以有效抵制大范围的微生物和/或温度，而且一些杀生物剂与其他化学处理添加剂不相容。另外，一些杀生物剂不能在足够长的时间段实现微生物的控制。
虽然可以通过使用大量杀生物剂克服某些上述缺点，但该措施会产生自身问题，包括增加成本，增加废物，以及增加杀生物剂干扰所处理介质所需性质的可能性。另外，即便使用大量杀生物剂，因为对某种微生物的低抑制活性或微生物对这些化合物的耐抗性，许多商业化杀生物化合物仍无法给予有效控制。
提供给出如下一种或多种优势的用于水体系处理的杀生物剂组合物将成为本领域的重大进步：低浓度时功效加强，与物理条件和处理介质中其他添加剂的相容性，抵抗广谱微生物的效力，和/或既能短期又能长期控制微生物的能力。
发明概要
一方面，本发明提供一种生物杀灭性组合物。所述组合物可用于控制水或含水体系中的微生物。所述组合物包含：2,2-二溴丙二酰胺和选自银、铜及其混合物的金属。
另一方面，本发明提供一种控制水或含水体系中微生物的方法。所述方法包括利用本文所述的有效剂量的生物杀灭性组合物处理所述体系。
发明内容
如上提及，本发明提供一种生物杀灭性组合物及其用于控制微生物的方法。所述组合物包含：2,2-二溴丙二酰胺和选自银、铜及其混合物的金属。惊喜地发现，2,2-二溴丙二酰胺和本文所述金属以某重量比组合在用于控制水或含水介质中微生物时具有协同作用。也就是组合物质会产生比基于它们各自性能预想的增强的生物杀灭特性。所述协同作用可以减少实现所需生物杀灭性能的所述材料用量，从而减少工业过程水中微生物生长导致的问题，同时可能降低环境影响和材料成本。
为达到本说明书的目的，“微生物”的意思包括但不限于细菌、真菌、藻类和病毒。术语“控制”应宽泛地理解为包括但不限于以下意思：抑制微生物的生长或繁殖，杀死微生物，消毒和/或防腐。一些优选实施方式中，“控制”指抑制微生物的生长或繁殖。另一些实施方式中，“控制”指杀死微生物。
术语“2,2-二溴丙二酰胺”、“二溴丙二酰胺”和“DBMAL”指化学式如下的化合物：
本发明的一些实施方式中，2,2-二溴丙二酰胺和金属的重量比在约1000:1到约1:100之间，或者在约800:1到约1:1之间。2,2-二溴丙二酰胺为商业购得和/或由本领域技术人员利用熟知技术容易制得。
某一实施方式中，本发明组合物包含2,2-二溴丙二酰胺和银。所述银以能与微生物细胞组分发生反应的离子或非离子形式存在。优选所述银从无机或有机源中或由银离子电解产生获得。包括但不限于以下一种或多种示例：醋酸银，乙酰丙酮酸银，砷酸银，苯甲酸银，溴酸银，溴化银，碳酸银，氯酸银，氯化银，铬酸银，柠檬酸银水合物，氰酸银，环己烷丁酸银，氟化银，七氟丁酸银，六氟锑酸银，六氟砷酸银，六氟磷酸银，氟氢化银，碘酸银，碘化银，乳酸银，偏矾酸银，甲烷磺酸银，六亚甲基四胺银，钼酸银，硝酸银，亚硝酸银，氧化银，五氟丙酸银，高氯酸银水合物，一水高氯酸银，高氯酸银，磷酸银，酞菁银，吡啶甲酸银，银蛋白，蛋白银，对甲苯磺酸银，硒化银，磺胺嘧啶银，硫酸银，硫化银，亚硫酸银，碲化银，四氟硼酸银，硫氰酸银，三氟乙酸银，三氟甲烷磺酸银或钨酸银。优选来源为硝酸银。所述银也可以从设计为控制银释放的制剂中获得。银的控释制剂的示例包括基于有机聚合物，沸石，玻璃，磷酸钙，二氧化钛和氧化锌的制剂。这些制剂可以采用上面提及的多种无机或有机银形式。
一些实施方式中，2,2-二溴丙二酰胺和银的重量比在约800:1至约1:1之间，或者在约800:1至约6:1之间，或者在约800:1至约12.5:1之间，或者在约400:1至约6:1之间。
一些实施方式中，本发明组合物包含2,2-二溴丙二酰胺和铜。所述铜以能与微生物细胞组分发生反应的离子或非离子形式存在。优选所述铜从无机或有机源中或由铜离子电解产生获得。包括但不限于以下一种或多种示例：醋酸铜，乙酰丙酮酸铜，溴化铜，碳酸铜，氯化铜，亚铬酸铜，氰化铜，环己烷丁酸铜，D-葡糖酸铜，氟化铜，甲酸铜水合物，六氟乙酰丙酮酸铜水合物，氢氧化铜，碘化铜，碘化铜二甲基硫醚络合物，碘化铜亚磷酸三甲酯络合物，甲醇铜，钼酸铜，硝酸铜，氧化铜，氧氯化铜，六水高氯酸铜，焦磷酸铜水合物，硒化铜，亚硒酸铜，硫酸铜，硫化铜，酒石酸铜水合物，碲化铜，硫氰酸铜，噻吩-2-羧酸铜，苯硫酚铜(copperthiophenolate)，三氟乙酰丙酮酸铜，1-丁基硫醇铜，2-乙基己酸铜，3-甲基水杨酸铜或三氟甲烷磺酸铜。优选来源为硫酸铜。所述铜也可以从设计为控制铜释放的制剂中获得。铜的控释制剂的示例包括基于有机聚合物，沸石，玻璃，磷酸钙，二氧化钛和氧化锌的制剂。这些制剂可以采用上面提及的多种无机或有机铜形式。
一些实施方式中，2,2-二溴丙二酰胺和铜的重量比在约100:1至约1:1之间，或者在约70:1至约1:1之间，或者在约40:1至约1:1之间，或者在约32:1至约1:1之间，或者在约16:1至1:1或16:1至2:1之间。
上述比例基于组合物中的金属量，虽然所述金属可能如以无机或有机化合物形式递送(deliver)。
本发明组合物可用于控制多种水或含水体系中的微生物。所述体系的示例包括但不限于：油漆和涂料，水性乳液，乳胶，粘合剂，油墨，颜料分散液，家用和工业清洁剂，去污剂，餐具去污剂，矿物浆料，聚合物乳液，嵌缝胶和粘合剂，胶带连接化合物，消毒剂，杀菌剂，金属加工液，建筑产品，个人护理产品，纺织液如纺丝油剂(spin finish)，工业过程水(如油田水，纸浆水，冷却水)，油田功能液如钻井泥浆和压裂液，燃料，空气洗涤剂，废水，压载水，过滤体系，及泳池和温泉水。优选水体系为金属加工液，个人护理产品，家用和工业清洁剂，工业过程水，及油漆和涂料。特别优选为工业过程水，油漆和涂料，金属加工液和纺织液如纺丝油剂。
本领域普通技术人员通过适当实验即可确定任何特定应用中实现微生物控制应使用的组合物的有效剂量。以实例说明，通常合适的活性物浓度(2,2-二溴丙二酰胺和金属的总浓度)为至少约0.001重量百分比，或者至少约0.01重量百分比，该重量百分比基于包含生物杀灭性组合物的水或含水体系的总重量。一些实施方式中，活性物浓度的合适上限值约为5重量百分比或以下，或者1重量百分比，或者0.1重量百分比，该重量百分比基于水或含水体系的总重量。
所述组合物的组分可以各自加到水或含水体系中，或预混合后加入。本领域普通技术人员可容易确定加入的适当方法。所述组合物可在体系中与其他添加剂一起使用，所述添加剂例如但不限于表面活性剂，离子/非离子聚合物，水垢和腐蚀抑制剂，除氧剂，和/或附加的杀生物剂。
以下实施例是对本发明的说明，但并不旨在限制本发明范围。除非另外说明，比例、百分比、份，及本文中使用的类似表述均基于重量。
实施例
实施例中给予的结果采用生长抑制检测获得。各检测细节提供如下。
生长抑制检测。实施例中使用的生长抑制检测测量微生物菌群的生长(或其缺失)抑制。生长抑制可以是杀死细胞(因此不再生长)，杀死大部分细胞致使重新生长需要一段延迟期，或不杀死但抑制生长(停滞)的结果。不管作用机理如何，杀生物剂(或杀生物剂的组合)的影响可以根据群体尺寸随时间的增加测得。
所述检测是在稀释的矿物盐培养基中测量一种或多种杀生物剂阻止细菌菌群生长的功效。所述培养基包含以下组分(mg/l)：FeCl3.6H2O(1);CaCl2.2H2O(10);MgSO4.7H2O(22.5);(NH4)2SO4(40);KH2PO4(10);K2HPO4(25.5);酵母提取物(10);和葡萄糖(100)。将所有组分加到去离子水中，然后调节培养基pH至7.5。过滤除菌后，按100μl等量置入灭菌的微量滴定板孔中。然后在微量滴定板中加入2,2-二溴丙二酰胺(“DBMAL”)和/或“杀生物剂B”的稀释液。按以下所述方式配制活性物的组合后，每个孔中接种100μl含每毫升约1×106个细胞的绿脓假单胞菌(Pseudomonas aeruginosa)、肺炎克雷伯氏菌(Klebsiella pneumoniae)、金黄色葡萄球菌(Staphylococcusaureus)和枯草芽孢杆菌(Bacillus subtilis)混合物的细胞悬浮液。每个孔中培养基的最终总体积为300μl。当按本文中所述方法配制活性物，如表1所示，各活性物的浓度在25ppm到0.195ppm之间。所得基质可以测定8个浓度的各活性物和64种按比例(以活性物计)的活性物组合。
表1.基于微量滴定板协同检测的显示各活性物浓度的模板。所述比例基于各活性物的重量(ppm)。
对照样(未显示)含不加入杀生物剂的培养基。
配制好微量滴定板后，立刻测量每个孔在580nm处的光密度(OD)读数，然后将板置于37°C孵育24小时。孵育之后，温和晃动板，然后采集OD580值。T24时的OD580值减去T0时的OD580值，以确定生长(或缺失)总量。这些值被用以计算由于存在各杀生物剂和各64种组合而导致的生长抑制的百分比。90%生长抑制(I90)值被作为利用以下方程计算协同指数(SI)的阈值：
协同指数=MDBMAL/CDBMAL+MB/CB
其中，
CDBMAL：单独使用时抑制至少90%细菌生长所需的DBMAL浓度；
CB：单独使用时抑制至少90%细菌生长所需的杀生物剂(B)浓度；
MDBMAL：与杀生物剂(B)组合使用时抑制至少90%细菌生长所需的DBMAL浓度；
MB：与DBMAL组合使用时抑制至少90%细菌生长所需的杀生物剂(B)浓度。
SI值说明如下：
SI<1：协同组合
SI=1：叠加组合
SI>1：拮抗组合
以下实施例中，测得溶液中杀生物剂含量为毫克每升溶液(mg/l)。因为溶液密度约为1.00，mg/l测量值与重量相对应，可以表述为百万分之一份(ppm)。因此这两个单位在实施例中可互换使用。
对银(Ag)和铜(Cu)进行评估。对于各金属，进行两个独立的实验以确定各金属与DBMAL组合使用时是否检测到有协同作用。以下部分为实验结果。
实施例1
DBMAL和银
实验1
尽管Ag以AgNO3形式加到细胞悬浮液中，所指浓度针对Ag而言，以mg/l表示。单独测定DBMAL和Ag，选定比例为1:64到64:1(DBMAL比Ag)。DBMAL和Ag的I90值分别为12.5mg/l和0.063mg/l。后续实验中，Ag的I90值为0.125ppm。两个研究中均检测到一些协同组合。表2含协同组合的比例和协同指数。
表2
由表可以看出，宽比例范围内两活性物表现出SI值<1，表明存在协同效应。
实验2
如表3所示，表2所列结果(实验1)是可重复的，且显示的抑制方式与实验1得到的非常相似。
表3
实施例2
DBMAL和铜
表6显示DBMAL、Cu和其组合的抑制生长检测结果。为了实现至少90%所测试生物的生长抑制，需要0.78mg/l Cu，如前所测，需要12.5mg/lDBMAL以实现相同功效。两活性物浓度低于I90浓度时，发现效果呈协同性。数据列于表4。
表4
实验2
该实验中，得到与实验1相似的结果(见表5)。
表5
实施例3
表10显示对DBMAL和锌(Zn)的检测结果。这些物质间未检测到协同作用。
虽然以上根据优选实施方式对本发明进行说明，但是可在本专利申请说明书的精神和范围内对本发明进行修改。因此本申请旨在覆盖采用本文公开的普遍原理对本发明的任何变更，使用或调整。本申请还旨在覆盖本专利申请说明书中属于本领域已知或常规做法的内容及本发明相关的和落入以下权利要求限定的内容。
Claims (9)
1.一种生物杀灭性组合物，其包含：2,2-二溴丙二酰胺和选自银、铜及其混合物的金属。
2.如权利要求1所述的组合物，其特征在于，2,2-二溴丙二酰胺和所述金属的重量比在约1000:1至约1:100之间。
3.如权利要求1和2中任一项所述的组合物，其特征在于，所述金属包括银，且2,2-二溴丙二酰胺和所述金属的重量比在约800:1至约1:1之间。
4.如权利要求1和2中任一项所述的组合物，其特征在于，所述金属包括铜，且2,2-二溴丙二酰胺和所述金属的重量比在约100:1至约1:1之间。
5.如权利要求1至3中任一项所述的组合物，其特征在于，所述金属为银，且所述银从无机或有机源中获得，所述无机或有机源选自：醋酸银，乙酰丙酮酸银，砷酸银，苯甲酸银，溴酸银，溴化银，碳酸银，氯酸银，氯化银，铬酸银，柠檬酸银水合物，氰酸银，环己烷丁酸银，氟化银，七氟丁酸银，六氟锑酸银，六氟砷酸银，六氟磷酸银，氟氢化银，碘酸银，碘化银，乳酸银，偏矾酸银，甲烷磺酸银，六亚甲基四胺银，钼酸银，硝酸银，亚硝酸银，氧化银，五氟丙酸银，高氯酸银水合物，一水高氯酸银，高氯酸银，磷酸银，酞菁银，吡啶甲酸银，银蛋白，蛋白银，对甲苯磺酸银，硒化银，磺胺嘧啶银，硫酸银，硫化银，亚硫酸银，碲化银，四氟硼酸银，硫氰酸银，三氟乙酸银，三氟甲烷磺酸银和钨酸银。
6.如权利要求1、2或4中任一项所述的组合物，其特征在于，所述金属为铜，且所述铜从无机或有机源中获得，所述无机或有机源选自：醋酸铜，乙酰丙酮酸铜，溴化铜，碳酸铜，氯化铜，亚铬酸铜，氰化铜，环己烷丁酸铜，D-葡糖酸铜，氟化铜，甲酸铜水合物，六氟乙酰丙酮酸铜水合物，氢氧化铜，碘化铜，碘化铜二甲基硫醚络合物，碘化铜亚磷酸三甲酯络合物，甲醇铜，钼酸铜，硝酸铜，氧化铜，氧氯化铜，六水高氯酸铜，焦磷酸铜水合物，硒化铜，亚硒酸铜，硫酸铜，硫化铜，酒石酸铜水合物，碲化铜，硫氰酸铜，噻吩-2-羧酸铜，苯硫酚铜，三氟乙酰丙酮酸铜，1-丁基硫醇铜，2-乙基己酸铜，3-甲基水杨酸铜或三氟甲烷磺酸铜。
7.如权利要求1至6中任一项所述的组合物，所述组合物为：油漆，涂料，水性乳液，乳胶，粘合剂，油墨，颜料分散液，家用或工业清洁剂，去污剂，餐具去污剂，矿物浆料，聚合物乳液，嵌缝胶，粘合剂，胶带连接化合物，消毒剂，杀菌剂，金属加工液，建筑产品，个人护理产品，纺织液，纺丝油剂，工业过程水，油田功能液，燃料，空气洗涤剂，废水，压载水，过滤体系，泳池或温泉水。
8.一种控制水或含水体系中微生物生长的方法，所述方法包括采用有效剂量的权利要求1至6中任一项所述的组合物处理所述水或含水体系。
9.如权利要求8所述的方法，其特征在于，所述水或含水体系为油漆，涂料，水性乳液，乳胶，粘合剂，油墨，颜料分散液，家用或工业清洁剂，去污剂，餐具去污剂，矿物浆料，聚合物乳液，嵌缝胶，粘合剂，胶带连接化合物，消毒剂，杀菌剂，金属加工液，建筑产品，个人护理产品，纺织液，纺丝油剂，工业过程水，油田功能液，燃料，空气洗涤剂，废水，压载水，过滤体系，泳池或温泉水。
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| WO2012021340A1 (en) | 2012-02-16 |
| RU2013110233A (ru) | 2014-09-20 |
| MX2013001526A (es) | 2013-03-18 |
| EP2582238A1 (en) | 2013-04-24 |
| US9060511B2 (en) | 2015-06-23 |
| EP2582238B1 (en) | 2014-06-04 |
| JP2013533311A (ja) | 2013-08-22 |
| CN103068229B (zh) | 2015-05-20 |
| US20130142886A1 (en) | 2013-06-06 |
| RU2568745C2 (ru) | 2015-11-20 |
| BR112013001746A2 (pt) | 2016-05-31 |
| JP5739533B2 (ja) | 2015-06-24 |
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