JP2005089348A - New microbicide composition - Google Patents
New microbicide composition Download PDFInfo
- Publication number
- JP2005089348A JP2005089348A JP2003322894A JP2003322894A JP2005089348A JP 2005089348 A JP2005089348 A JP 2005089348A JP 2003322894 A JP2003322894 A JP 2003322894A JP 2003322894 A JP2003322894 A JP 2003322894A JP 2005089348 A JP2005089348 A JP 2005089348A
- Authority
- JP
- Japan
- Prior art keywords
- isothiazolin
- iodoacetamide
- benzisothiazolin
- microbicidal
- octyl
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 230000003641 microbiacidal effect Effects 0.000 title claims abstract description 29
- 239000002855 microbicide agent Substances 0.000 title abstract description 4
- 229940124561 microbicide Drugs 0.000 title abstract 3
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 claims abstract description 14
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims abstract description 10
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims abstract description 9
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims abstract description 7
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 claims abstract description 6
- 229940044120 2-n-octyl-4-isothiazolin-3-one Drugs 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- LUYIHWDYPAZCNN-UHFFFAOYSA-N 2-butyl-1,2-benzothiazol-3-one Chemical compound C1=CC=C2C(=O)N(CCCC)SC2=C1 LUYIHWDYPAZCNN-UHFFFAOYSA-N 0.000 claims abstract description 4
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- ZLEUYGBJFPTXLX-UHFFFAOYSA-N C1C=[S+]NC1 Chemical class C1C=[S+]NC1 ZLEUYGBJFPTXLX-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 241000894006 Bacteria Species 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- -1 metal complex salts Chemical class 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 239000004566 building material Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FMNZAHDAULEOSO-UHFFFAOYSA-N 2,2-dibromo-2-nitroethanol Chemical compound OCC(Br)(Br)[N+]([O-])=O FMNZAHDAULEOSO-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- AFSROBHYIMWVTR-UHFFFAOYSA-N 1-(2-bromoacetyl)oxyethyl 2-bromoacetate Chemical compound BrCC(=O)OC(C)OC(=O)CBr AFSROBHYIMWVTR-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- UUIVKBHZENILKB-UHFFFAOYSA-N 2,2-dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N UUIVKBHZENILKB-UHFFFAOYSA-N 0.000 description 1
- WGHAPLWNJPAJDE-UHFFFAOYSA-N 2-(2-bromoacetyl)oxyethyl 2-bromoacetate Chemical compound BrCC(=O)OCCOC(=O)CBr WGHAPLWNJPAJDE-UHFFFAOYSA-N 0.000 description 1
- QYYMDNHUJFIDDQ-UHFFFAOYSA-N 5-chloro-2-methyl-1,2-thiazol-3-one;2-methyl-1,2-thiazol-3-one Chemical compound CN1SC=CC1=O.CN1SC(Cl)=CC1=O QYYMDNHUJFIDDQ-UHFFFAOYSA-N 0.000 description 1
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 238000010953 Ames test Methods 0.000 description 1
- 231100000039 Ames test Toxicity 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000750 industrial fungicide Substances 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000013054 paper strength agent Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
本発明は、諸工業分野において利用されている接着剤、樹脂エマルジョン、インキ、糊剤、塗料、紙、繊維および建材等の水系分散物の微生物汚染を防止し、かつ環境負荷の恐れのない新規な殺微生物組成物に関するものである。 The present invention is a novel material that prevents microbial contamination of aqueous dispersions such as adhesives, resin emulsions, inks, glues, paints, paper, fibers and building materials used in various industrial fields and has no fear of environmental impact. A microbicidal composition.
近年、諸工業分野において利用されている接着剤、樹脂エマルジョン、インキ、糊剤、塗料、紙、繊維および建材等の水系分散物製品およびその製造工程の水系において、その用水や製品に含有されている有機化合物や微量な無機物を栄養源にして、種々の微生物、すなわち細菌、酵母、糸状菌、藻類が増殖して、製品の品質や生産性を著しく低下させるという問題がある。これら問題に対処するため、多種多様な殺菌剤および殺菌組成物が製品等に添加されている。そのような殺菌組成物として、例えば、5―クロロ―2―メチル―4―イソチアゾリン―3−オンと2―メチル―4―イソチアゾリン―3−オンとの混合物(ケミクレア社製9:1混合物商品名:ゾ−ネン−F、ローム&ハ−ス社製3:1混合物商品名:ケ−ソンLX SF25)(特許文献1)またはそれらの金属コンプレックス塩の混合物(ケミクレア社製3:1混合物商品名:ゾ−ネン−C、ローム&ハ−ス社製3:1混合物商品名:ケ−ソンWT)の単独製剤や、それらと、例えば、2−ブロモ−2−ニトロプロパン−1,3−ジオ−ル、2,2−ジブロモ−2−ニトロ−1−エタノ−ル、1,2−ビス(ブロモアセトオキシ)エタン等の有機ブロモ系化合物や更には、メチレンビスチオシアナ−ト、2−(4−チオシアノメチルチオ)ベンゾチアゾ−ル、1,2−ベンズイソチアゾリン−3−オン等との組合せ配合剤が汎用されている(特許文献2および3)。しかしながら、これらはいずれも、エイムズ試験において陽性であり、人体に対して変異原性を示す。更に、2,2−ジブロモ−3−ニトリロプロピオンアミド、2−ブロモ−2−ニトロプロパン−1,3−ジオ−ル、2,2−ジブロモ−2−ニトロ−1−エタノ−ル、1,2−ビス(ブロモアセトオキシ)エタン等の有機ブロモ系化合物や、更には、メチレンビスチオシアナ−ト、2−(4−チオシアノメチルチオ)ベンゾチアゾ−ル等が配合されている組合せ配合剤の場合、いずれも溶剤に希釈されて汎用されているため、水性系分散物の微生物汚染防止のために使用すると、溶剤が揮発性有機化合物(VOC)として大気中に揮散したり、溶剤が水系に流入してCOD(化学酸素要求量)を上昇させ、少なからず環境への負荷を生じさせるという問題があった。
本発明は、上記事情に鑑みてなされたものであり、エイムズ陰性でかつ水性系で長期間に亘り安定した殺微生物効果を発揮できる新規な殺微生物組成物を提供することを目的とするものである。 The present invention has been made in view of the above circumstances, and aims to provide a novel microbicidal composition which is Ames-negative and can exhibit a stable microbicidal effect over a long period of time in an aqueous system. is there.
本発明者らは、新規な殺微生物組成物を開発すべく種々研究を重ねた結果、従来の工業用殺菌剤として用いられていたヨードアセトアミドと、2―メチル―4―イソチアゾリン―3−オン、2−n−オクチル−4−イソチアゾリン−3−オン、1,2−ベンズイソチアゾリン−3−オン、4,5−ジクロロ−2−n−オクチル−4−イソチアゾリン−3−オン、およびN−ブチル−1,2−ベンズイソチアゾリン−3−オンよりなる群から選ばれる1種または2種以上とを配合させることによって、エイムズ陰性でありかつ水性系で長期間に亘り安定した殺微生物効果発揮できる殺微生物組成物を作成できることを見出し、この知見に基づいて本発明をなすに至った。すなわち、本発明は、ヨードアセトアミドと、下記の(1)〜(5)のイソチアゾリン系化合物から選ばれる1種または2種以上とを含有する新規な殺微生物組成物を提供するものである
(1)2−メチル−4−イソチアゾリン−3−オン
(2)2−n−オクチル−4−イソチアゾリン−3−オン
(3)1,2−ベンズイソチアゾリン−3−オン
(4)4,5−ジクロロ−2−n−オクチル−4−イソチアゾリン−3−オン
(5)N−ブチル−1,2−ベンズイソチアゾリン−3−オン
好ましくは、ヨードアセトアミドと、前記イソチアゾリン系化合物全体との配合割合は、重量に基づき10:1から1:10である。
As a result of various studies to develop a novel microbicidal composition, the present inventors have found that iodoacetamide and 2-methyl-4-isothiazolin-3-one, which have been used as conventional industrial fungicides, 2-n-octyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one, and N-butyl- Microbicidal agent that is Ames-negative and can exhibit a stable microbicidal effect over a long period of time in an aqueous system by incorporating one or more selected from the group consisting of 1,2-benzisothiazolin-3-one The present inventors have found that a composition can be prepared and have come to make the present invention based on this finding. That is, the present invention provides a novel microbicidal composition containing iodoacetamide and one or more selected from the following (1) to (5) isothiazoline compounds (1). ) 2-Methyl-4-isothiazolin-3-one (2) 2-n-octyl-4-isothiazolin-3-one (3) 1,2-benzisothiazolin-3-one (4) 4,5-dichloro- 2-n-octyl-4-isothiazolin-3-one (5) N-butyl-1,2-benzisothiazolin-3-one Preferably, the blending ratio of iodoacetamide and the entire isothiazoline-based compound is Based on 10: 1 to 1:10.
本発明の新規な殺微生物組成物は、ヨードアセトアミドと、上記の(1)〜(5)のイソチアゾリン系化合物から選ばれる1種または2種以上とを含有することによって、エイムズ陰性であり、かつ水性系で長期間に亘り安定な殺微生物効果を発揮できる。従って、本発明は、環境負荷の問題のない、長期間に亘り安定な水性殺微生物製剤の調製を可能にする。 The novel microbicidal composition of the present invention is Ames-negative by containing iodoacetamide and one or more selected from the above (1) to (5) isothiazoline compounds, and A stable microbicidal effect can be exhibited over a long period of time in an aqueous system. Therefore, the present invention enables the preparation of an aqueous microbicidal preparation that is stable over a long period of time without the problem of environmental burden.
本発明において用いられるヨードアセトアミド、および上記(1)〜(5)のイソチアゾリン系化合物は、いずれも工業用殺菌剤として広く使用されており、市販品として容易に入手することができる。上記(1)〜(5)のイソチアゾリン系化合物は、単独で用いても、2種以上を組み合わせて用いてもよい。 The iodoacetamide used in the present invention and the isothiazoline compounds (1) to (5) are widely used as industrial disinfectants and can be easily obtained as commercial products. The isothiazoline-based compounds (1) to (5) may be used alone or in combination of two or more.
ヨードアセトアミドと、上記(1)〜(5)のイソチアゾリン系化合物全体との配合割合は、好ましくは、重量に基づき50:1から1:50であり、より好ましくは10:1から1:10であり、さらに好ましくは5:1から1:5である。係る範囲の配合割合を有する場合に特に長期間に亘り安定した防腐効果を発揮できるが、本願発明の目的を達成できる限り、上記範囲に限定されない。 The blending ratio of iodoacetamide and the whole of the isothiazoline compounds (1) to (5) is preferably 50: 1 to 1:50, more preferably 10: 1 to 1:10, based on weight. More preferably 5: 1 to 1: 5. In the case of having such a blending ratio, a stable antiseptic effect can be exhibited particularly for a long period of time, but it is not limited to the above range as long as the object of the present invention can be achieved.
本発明の1つの実施形態において、本発明の殺微生物組成物は水溶液の形態である。用いられる水は、水道水、イオン交換水、蒸留水、工業用水等のいずれでもよく、特に限定されない。本発明の殺微生物組成物水溶液は、殺菌剤を水に溶解させる任意の公知の方法によって調製することができる。例えば、ヨードアセトアミドと、上記の(1)〜(5)のイソチアゾリン系化合物の1種または2種以上とを、界面活性剤無しにまたは界面活性剤と共に水に添加し、混合することによって、本発明の殺微生物組成物水溶液を調製することができる。界面活性剤としては、例えば、アニオン界面活性剤、ノニオン界面活性剤等、任意の界面活性剤を用いることができる。 In one embodiment of the invention, the microbicidal composition of the invention is in the form of an aqueous solution. The water used may be any of tap water, ion exchange water, distilled water, industrial water and the like, and is not particularly limited. The aqueous microbicidal composition solution of the present invention can be prepared by any known method for dissolving a bactericide in water. For example, iodoacetamide and one or more of the isothiazoline compounds (1) to (5) described above are added to water without a surfactant or together with a surfactant and mixed. An aqueous microbicidal composition solution of the invention can be prepared. As the surfactant, for example, any surfactant such as an anionic surfactant and a nonionic surfactant can be used.
本発明の別の実施形態において、本発明の殺微生物組成物は水系分散液の形態である。用いられる水は、前記の水溶液と同様に特に限定されない。本発明の殺微生物組成物分散液は、殺菌剤を水に分散させる任意の公知の方法によって調製することができる。例えば、ヨードアセトアミドと、上記の(1)〜(5)のイソチアゾリン系化合物の1種または2種以上とを、乳化剤、分散剤、填料、粘度調整剤、電解質、および/または界面補強剤等と共に水に添加し、混合し、さらにコロイドミル、ボ−ルミル、サンドミル、ビ−ズミル等の任意の粉砕機で処理することによって、本発明の殺微生物組成物分散液を調製することができる。乳化剤および分散剤としては、例えば、アニオン界面活性剤、ノニオン界面活性剤、カチオン界面活性剤、両性界面活性剤、高分子界面活性剤などの公知の界面活性剤があげられる。填料としては、例えば、珪酸、ベントナイト、酸性白土、クレ−、カオリン、層状粘土鉱物があげられる。粘度調整剤としては、例えば、カルボキシメチルセルロ−スナトリウム塩、ポリビニルピロリドン、ポリビニルアルコ−ル、グアガム、アルギン酸ナトリウム、アラビアガム等があげられる。電解質としては、例えば、塩化ナトリウム、塩化カリウム等の無機化合物、シュウ酸、酒石酸、マレイン酸等の有機化合物があげられる。界面補強剤としては、例えば、ステアリン酸等の高級脂肪酸類、セタノ−ル等の高級アルコ−ル類、炭化水素類等があげられる。 In another embodiment of the invention, the microbicidal composition of the invention is in the form of an aqueous dispersion. The water used is not particularly limited as in the case of the aqueous solution. The microbicidal composition dispersion of the present invention can be prepared by any known method for dispersing a bactericide in water. For example, iodoacetamide and one or more of the isothiazoline compounds (1) to (5) above are used together with an emulsifier, a dispersant, a filler, a viscosity modifier, an electrolyte, and / or an interfacial reinforcing agent. The microbicidal composition dispersion of the present invention can be prepared by adding to water, mixing, and further treating with an optional pulverizer such as a colloid mill, ball mill, sand mill, or bead mill. Examples of emulsifiers and dispersants include known surfactants such as anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, and polymeric surfactants. Examples of the filler include silicic acid, bentonite, acid clay, clay, kaolin, and layered clay mineral. Examples of the viscosity modifier include carboxymethyl cellulose sodium salt, polyvinyl pyrrolidone, polyvinyl alcohol, guar gum, sodium alginate, gum arabic and the like. Examples of the electrolyte include inorganic compounds such as sodium chloride and potassium chloride, and organic compounds such as oxalic acid, tartaric acid, and maleic acid. Examples of the interfacial reinforcing agent include higher fatty acids such as stearic acid, higher alcohols such as cetanol, and hydrocarbons.
本発明の新規殺微生物組成物の使用に際しての添加量は、微生物濃度により異なるが、接着剤、樹脂エマルジョン、インキ、糊剤、塗料、紙、繊維および建材等の諸工業分野において利用されている水系分散物での使用において、20〜500ppm程度であり、この範囲で特に良好な殺微生物効果が得られる。 The amount of addition of the novel microbicidal composition of the present invention varies depending on the microbial concentration, but is used in various industrial fields such as adhesives, resin emulsions, inks, glues, paints, paper, fibers and building materials. When used in an aqueous dispersion, it is about 20 to 500 ppm, and a particularly good microbicidal effect can be obtained in this range.
本発明の殺微生物組成物は、本発明の目的を妨げない限り、必要に応じて、任意の安定剤、緩衝剤等をさらに含有していて差し支えない。 The microbicidal composition of the present invention may further contain an optional stabilizer, buffering agent, etc. as necessary, as long as the object of the present invention is not hindered.
次に本発明を実施例によりさらに詳細に説明するが、本発明はこれら例によってなんら限定されるものではない。 EXAMPLES Next, although an Example demonstrates this invention still in detail, this invention is not limited at all by these examples.
表1に示す配合組成で、ヨードアセトアミドと、指示されたイソチアゾリン系化合物とを水に溶解または分散させて、表1に示す配合組成の殺微生物組成物を調製した(実施例1〜5、比較例1〜6)
各組成物について、以下に示す試験をおこなった。 Each composition was subjected to the following tests.
(1)紙力増強剤における菌増殖防止試験
紙力増強剤100mlに、濃度が50ppm、100ppm、300ppmになるように各殺微生物組成物を添加し、予め腐敗(1ml当り腐敗菌数108)させておいた紙力増強剤1mlを加え、これを32℃の恒温器に保存した。紙力増強剤中の生菌数を経時的に測定した。その結果を表2に示す:
(2)水性塗料における菌増殖防止試験
水性塗料100mlに、濃度が50ppm、100ppm、300ppmになるように各殺微生物組成物を添加し、予め腐敗(1ml当り腐敗菌数108)させておいた水性塗料1mlを加え、これを32℃の恒温器に保存した。水性塗料中の生菌数を経時的に測定した。その結果を表3に示す:
これら結果から明らかであるように、ヨードアセトアミドと、2−メチル−4−イソチアゾリン−3−オン、2−n−オクチル−4−イソチアゾリン−3−オン、1,2−ベンズイソチアゾリン−3−オン、4,5−ジクロロ−2−n−オクチル−4−イソチアゾリン−3−オン、およびN−ブチル−1,2−ベンズイソチアゾリン−3−オンよりなる群から選ばれるイソチアゾリン系化合物とを含有する本発明の殺微生物組成物(実施例1から5)は、水性系において、50から300ppmの濃度範囲で、4週間という長期間に亘り高い殺微生物効果を示すことができた。一方、ヨードアセトアミドのみ含有する組成物(比較例1)では、50および100ppmでは2週間目に既に菌の増殖が認められ、300ppmでも4週間後には菌の顕著な増殖が認められた。また、上記のイソチアゾリン系化合物のみを含有する組成物(比較例2から6)では、1週間後に既に菌の増殖が認められ、2週間後にはブランクとほぼ同程度まで菌が増殖し、ほとんど殺微生物効果を示すことができなかった。 As is apparent from these results, iodoacetamide and 2-methyl-4-isothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one, The present invention contains an isothiazoline compound selected from the group consisting of 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one and N-butyl-1,2-benzisothiazolin-3-one The microbicidal compositions (Examples 1 to 5) in the aqueous system were able to show a high microbicidal effect over a long period of 4 weeks in a concentration range of 50 to 300 ppm in an aqueous system. On the other hand, in the composition containing only iodoacetamide (Comparative Example 1), the growth of bacteria was already observed at 2 weeks at 50 and 100 ppm, and the remarkable growth of bacteria was observed after 4 weeks even at 300 ppm. In addition, in the composition containing only the above isothiazoline-based compound (Comparative Examples 2 to 6), the growth of bacteria was already observed after 1 week, and after 2 weeks, the bacteria grew to almost the same level as the blank, and almost killed. The microbial effect could not be shown.
Claims (2)
(1)2−メチル−4−イソチアゾリン−3−オン
(2)2−n−オクチル−4−イソチアゾリン−3−オン
(3)1,2−ベンズイソチアゾリン−3−オン
(4)4,5−ジクロロ−2−n−オクチル−4−イソチアゾリン−3−オン
(5)N−ブチル−1,2−ベンズイソチアゾリン−3−オン。 Microbicidal composition comprising iodoacetamide and one or more selected from the following (1) to (5) isothiazoline compounds (1) 2-methyl-4-isothiazolin-3-one (2 ) 2-n-octyl-4-isothiazolin-3-one (3) 1,2-benzisothiazolin-3-one (4) 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one ( 5) N-butyl-1,2-benzisothiazolin-3-one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003322894A JP2005089348A (en) | 2003-09-16 | 2003-09-16 | New microbicide composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003322894A JP2005089348A (en) | 2003-09-16 | 2003-09-16 | New microbicide composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2005089348A true JP2005089348A (en) | 2005-04-07 |
Family
ID=34454118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003322894A Pending JP2005089348A (en) | 2003-09-16 | 2003-09-16 | New microbicide composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2005089348A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007031300A (en) * | 2005-07-22 | 2007-02-08 | Taisho Technos Co Ltd | Antiseptic / antifungal method and antiseptic / antifungal composition for aqueous industrial products |
| JP2007031299A (en) * | 2005-07-22 | 2007-02-08 | Taisho Technos Co Ltd | Industrial antiseptic mildew-proofing agent composition |
| EP1772055A1 (en) * | 2005-10-04 | 2007-04-11 | Rohm and Haas France SAS | Synergistic microbicidal compositions comprising a N-alkyl-1,2-benzoisothiazolin-3-one |
| JP2008056644A (en) * | 2006-09-04 | 2008-03-13 | Japan Organo Co Ltd | Water treatment agent |
| WO2008146436A1 (en) * | 2007-05-31 | 2008-12-04 | Chemicrea Inc. | Stable microbiocidal composition |
| WO2020246452A1 (en) | 2019-06-03 | 2020-12-10 | 株式会社ケミクレア | Stable microbicide composition |
-
2003
- 2003-09-16 JP JP2003322894A patent/JP2005089348A/en active Pending
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007031300A (en) * | 2005-07-22 | 2007-02-08 | Taisho Technos Co Ltd | Antiseptic / antifungal method and antiseptic / antifungal composition for aqueous industrial products |
| JP2007031299A (en) * | 2005-07-22 | 2007-02-08 | Taisho Technos Co Ltd | Industrial antiseptic mildew-proofing agent composition |
| KR100870884B1 (en) * | 2005-10-04 | 2008-11-28 | 롬 앤드 하아스 컴패니 | Microbicidal composition |
| AU2006222721B2 (en) * | 2005-10-04 | 2012-04-19 | Rohm And Haas Company | Microbicidal composition |
| EP1772056A3 (en) * | 2005-10-04 | 2007-05-30 | Rohm and Haas Company | Synergistic microbicidal compositions comprising a N-alkyl-1,2-benzoisothiazolin-3-one |
| KR100839816B1 (en) * | 2005-10-04 | 2008-06-19 | 롬 앤드 하아스 컴패니 | Bactericidal composition |
| KR100851543B1 (en) * | 2005-10-04 | 2008-08-11 | 롬 앤드 하아스 컴패니 | Microbicidal composition |
| EP1772055A1 (en) * | 2005-10-04 | 2007-04-11 | Rohm and Haas France SAS | Synergistic microbicidal compositions comprising a N-alkyl-1,2-benzoisothiazolin-3-one |
| US8741940B2 (en) | 2005-10-04 | 2014-06-03 | Rohm And Haas Company | Microbicidal composition |
| KR100873916B1 (en) | 2005-10-04 | 2008-12-12 | 롬 앤드 하아스 컴패니 | Microbicidal composition |
| JP2007099773A (en) * | 2005-10-04 | 2007-04-19 | Rohm & Haas Co | Microbicidal composition |
| JP2011006452A (en) * | 2005-10-04 | 2011-01-13 | Rohm & Haas Co | Microbicidal composition |
| JP2008056644A (en) * | 2006-09-04 | 2008-03-13 | Japan Organo Co Ltd | Water treatment agent |
| JPWO2008146436A1 (en) * | 2007-05-31 | 2010-08-19 | 株式会社ケミクレア | Stable microbicidal composition |
| WO2008146436A1 (en) * | 2007-05-31 | 2008-12-04 | Chemicrea Inc. | Stable microbiocidal composition |
| WO2020246452A1 (en) | 2019-06-03 | 2020-12-10 | 株式会社ケミクレア | Stable microbicide composition |
| KR20220006129A (en) | 2019-06-03 | 2022-01-14 | 가부시키가이샤 케미크레아 | Stable Microbicide Composition |
| CN114173563A (en) * | 2019-06-03 | 2022-03-11 | 株式会社凯美科瑞亚 | Stable Microbicide Composition |
| US12408668B2 (en) | 2019-06-03 | 2025-09-09 | Chemicrea Inc. | Stable microbicide composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5435475B2 (en) | Liquid composition containing histidine silver complex, bactericidal composition, and method for stabilizing histidine silver complex | |
| AU764274B2 (en) | Synergistic antimicrobial combination of 4,5-dichloro-2-N-octyl-4-isothiazolin-3-one and a mixture of a chlorinated isocyanurate and a bromide compound and methods of using same | |
| JP4965783B2 (en) | Antimicrobial mixture comprising 1,3-bis (hydroxymethyl) -5,5-dimethylhydantoin and 1,2-benzisothiazolin-3-one | |
| CN102647902B (en) | Process for bacterial stabilizing of aqueous ground natural calcium carbonate and/or precipitated calcium carbonate and/or dolomite and/or surface-reacted calcium carbonate-comprising mineral preparations | |
| FI107223B (en) | Synergistic combinations of iodine propargyl compounds and 1,2-benzisothiazol-3-one to prevent fungal and bacterial growth in aqueous fluids | |
| JP2020520369A (en) | Biocide-free storage | |
| JP7478445B2 (en) | Stable microbicidal composition | |
| WO2015107934A1 (en) | Antiseptic agent composition | |
| JP2005089348A (en) | New microbicide composition | |
| CA2016384A1 (en) | Bismuth salt stabilizers for 3-isothiazolones | |
| JP2009096754A (en) | Industrial antifungal composition | |
| WO2000067578A1 (en) | Composite bactericidal compositions | |
| CN101252841A (en) | Synergistic silver-containing insecticide compositions | |
| EP1450823B1 (en) | Biocidal mixture of 2-propenal-releasing polymer and isothiazolones | |
| JP5383969B2 (en) | Emulsion formulation composition and method for stabilizing water-soluble disinfectant | |
| JP2001192308A (en) | Industrial disinfectants and preservatives and their disinfection and preservative methods | |
| US8759416B2 (en) | Hindered primary chlorinated amine in a latex formulation | |
| JP4318543B2 (en) | Industrial sterilization composition | |
| JP3194687B2 (en) | Industrial fungicides | |
| JP6858502B2 (en) | Industrial antibacterial, antifungal and anti-algae agents | |
| JPWO2008146436A1 (en) | Stable microbicidal composition | |
| JP4338461B2 (en) | Industrial antibacterial composition | |
| JP4201885B2 (en) | Harmful microorganism eradication agent | |
| JP3876461B2 (en) | Industrial antibacterial agent | |
| JP4684643B2 (en) | Industrial sterilization composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060810 |
|
| A131 | Notification of reasons for refusal |
Effective date: 20090908 Free format text: JAPANESE INTERMEDIATE CODE: A131 |
|
| A02 | Decision of refusal |
Effective date: 20100112 Free format text: JAPANESE INTERMEDIATE CODE: A02 |