JPH02292202A - Industrial bactericide and sterilization - Google Patents
Industrial bactericide and sterilizationInfo
- Publication number
- JPH02292202A JPH02292202A JP11317389A JP11317389A JPH02292202A JP H02292202 A JPH02292202 A JP H02292202A JP 11317389 A JP11317389 A JP 11317389A JP 11317389 A JP11317389 A JP 11317389A JP H02292202 A JPH02292202 A JP H02292202A
- Authority
- JP
- Japan
- Prior art keywords
- organic solvent
- maleic anhydride
- water
- industrial
- formula
- 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
- 230000001954 sterilising effect Effects 0.000 title claims description 5
- 238000004659 sterilization and disinfection Methods 0.000 title claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 18
- 239000003899 bactericide agent Substances 0.000 title abstract description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 244000005700 microbiome Species 0.000 claims abstract description 6
- 150000003951 lactams Chemical group 0.000 claims abstract description 3
- 239000000645 desinfectant Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000000750 industrial fungicide Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 abstract description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000498 cooling water Substances 0.000 abstract description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 2
- 230000002265 prevention Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 21
- 238000009472 formulation Methods 0.000 description 19
- 230000000694 effects Effects 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- FJLHLDBEZKTSOK-UHFFFAOYSA-N n-ethyl-n-methylformamide Chemical compound CCN(C)C=O FJLHLDBEZKTSOK-UHFFFAOYSA-N 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- DSVGICPKBRQDDX-UHFFFAOYSA-N 1,3-diacetoxypropane Chemical compound CC(=O)OCCCOC(C)=O DSVGICPKBRQDDX-UHFFFAOYSA-N 0.000 description 1
- XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- ZWUWDFWEMWMTHX-UHFFFAOYSA-N 2-methoxybutyl acetate Chemical compound CCC(OC)COC(C)=O ZWUWDFWEMWMTHX-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- -1 diacetquinmethane Chemical compound 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940079920 digestives acid preparations Drugs 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- ZHCJUZJGMJDUKJ-UHFFFAOYSA-M ethyl(phosphonatooxy)mercury;hydron Chemical compound CC[Hg+].OP(O)([O-])=O ZHCJUZJGMJDUKJ-UHFFFAOYSA-M 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
（イ）産業上の利用分野
この発明は、工業用殺菌剤に関する。さらに詳しくは、
紙パルブ工業の抄紙工程水、各種工業用の冷却水、など
の水系における微生物障害を防止するために有用な製剤
に関する。DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application This invention relates to an industrial disinfectant. For more details,
This invention relates to a formulation useful for preventing microbial damage in water systems such as papermaking process water in the pulp and paper industry and cooling water for various industrial uses.
（口）従来の技術
従来から紙パルプ工業における抄紙工程水や各種工業に
おける冷却水中に、細菌や真閑によるスライムが発生し
、生産品の品質低下や生産効率のを、適宜界面活性剤や
アルコール等を用いて、ｌＯ〜５０％程度の水溶液剤や
乳剤とした製剤を開示している。(Ex) Conventional technology Slime caused by bacteria and manganese has been generated in the papermaking process water in the pulp and paper industry and in the cooling water in various industries. The patent discloses formulations in the form of aqueous solutions or emulsions of about 10 to 50% using the same methods.
また、この公報においては、マイレン酸と無水マイレン
酸との殺菌効果は同等であることが示されている。Furthermore, this publication indicates that the bactericidal effects of maleic acid and maleic anhydride are equivalent.
しかしながら、上記公報に開示された聾様や製剤による
殺菌効果は充分満足できるものではなかった。However, the bactericidal effect of the deaf-like formulations disclosed in the above-mentioned publication was not fully satisfactory.
この発明はかかる状況下なされたものである。This invention was made under such circumstances.
（二）課題を解決するための手段
かくしてこの発明によれば、実質的に無水の非プロトン
性親水性有機溶媒中に無水マレイン酸を溶解調製してな
る工業用殺菌剤が提供される。(2) Means for Solving the Problems According to the present invention, there is provided an industrial disinfectant prepared by dissolving maleic anhydride in a substantially anhydrous aprotic hydrophilic organic solvent.
この発明の工業用殺菌剤は、それ自体、製剤として著し
く安定なものであって長期間保存、貯蔵（例えば１年）
した後においても安定な殺菌効果を示すものである。そ
して、さらに、この殺菌剤は、直接水系に添加すること
により、無水マイレン酸粉末の直接添加や而記公報に開
示された水性低下などの損失を与えることが知られてい
る。The industrial fungicide of this invention is itself extremely stable as a formulation and can be stored and stored for a long period of time (for example, one year).
It shows a stable bactericidal effect even after treatment. Furthermore, it is known that when this bactericide is directly added to an aqueous system, it causes losses such as direct addition of maleic anhydride powder and a decrease in aqueous properties as disclosed in the publication.
これらの微生物による障害を防止するため、多くの殺菌
剤が使用されてきた。古くは、エチルリン酸水銀や酢酸
フエニル水銀等の有機水銀化合物、ペンタクロ口フェノ
ールやトリクロロフェノール等の塩素化フェノール化合
物などが使用されていた。しかしこれらの薬剤は人体や
魚介類に対する毒性が強く、環境汚染をひき起こすため
使用が規制されるようになり、最近では比較的低毒性の
塩素化イソシアヌール酸、次亜塩素酸ナトリウム、メチ
レンビスチオシアネート、５−クロロ−２−メチル−４
−イソチアゾリンー３−オン、２−ブロモー２一二トロ
ブロバンー１，３−ジオール等が工業用殺菌剤として汎
用されている。Many disinfectants have been used to prevent damage caused by these microorganisms. In the old days, organic mercury compounds such as ethylmercury phosphate and phenylmercury acetate, and chlorinated phenol compounds such as pentachlorophenol and trichlorophenol were used. However, these drugs are highly toxic to humans and fish and shellfish, and cause environmental pollution, so their use has become regulated. Thiocyanate, 5-chloro-2-methyl-4
-Isothiazolin-3-one, 2-bromo-2-ditrobroban-1,3-diol, and the like are commonly used as industrial fungicides.
そして、同様な目的のために、ごく最近、マレイン酸ま
たはその無水物を殺菌剤として用いる提案がなされてい
る（特開昭６４−５０８０３号公報）。Recently, it has been proposed to use maleic acid or its anhydride as a disinfectant for the same purpose (Japanese Patent Application Laid-open No. 50803/1983).
（ハ）発明が解決しようとする課題
上記特開昭６４−５０８０３号公報は、マレイン酸や無
水マレイン酸を、直接添加する態様並びにこれら製剤の
直接盛加時に比して著しく優れた殺菌効果を奏するもの
である。(c) Problems to be Solved by the Invention The above-mentioned Japanese Patent Application Laid-Open No. 64-50803 discloses a mode in which maleic acid or maleic anhydride is added directly, and a bactericidal effect significantly superior to that in the direct addition of these preparations. It is something to play.
ことにかかる優れた段菌効果は、マイレン酸使用時にお
いては発運されず無水マイレン酸固育の効果であり、従
来技術からして意外な効果といえるものである。In particular, this excellent sterilizing effect is due to the effect of solidification of maleic anhydride, which is not carried out when maleic acid is used, and can be said to be an unexpected effect considering the conventional technology.
かかる効果が発揮される理由は明らかではないが、■上
記特定の有機溶媒が、従来の製剤に比して無水マイレン
酸を加水分解することなく安定に溶解保持すると共に、
■水系への添加時に水と無水マイレン酸との直接接触を
抑制しつつ水系内へ効率良く分散させるよう作用するた
め無水マイレン酸がその加水分解が抑制された状態で水
系中の微生物と接触し、それにより、直接添加時や従来
製剤に比して優れた殺菌効果が奏されていると考えられ
る。Although the reason for this effect is not clear, (1) the above-mentioned specific organic solvent stably dissolves and retains maleic anhydride without hydrolyzing it, compared to conventional formulations;
■When added to an aqueous system, maleic anhydride acts to suppress direct contact between water and maleic anhydride while efficiently dispersing it into the aqueous system, so that maleic anhydride comes into contact with microorganisms in the aqueous system while its hydrolysis is suppressed. It is thought that this results in a superior bactericidal effect compared to direct addition or conventional formulations.
この発明に用いる非プロトン性浅水性有機溶媒とては、
下式（Ｉ）〜（ＩＩ［）から選ばれる有機溶媒を用いる
のが適している。The aprotic shallow water organic solvent used in this invention is:
It is suitable to use an organic solvent selected from the following formulas (I) to (II[).
Ｒｌ （Ｘ）Ｒ！ （Ｙ）Ｒ３ ・・・・・・
（Ｉ）（式中、Ｒ１及びＲ３は各々、Ｃ Ｉ−４のアル
キル基、Ｒ２はＣ ＋−ｓのアルキレン基：Ｘ及びＹは
各々、基一ｏ− −ｃｏｏ一又ｉ１−０−又は−０−
）、／
、Ｒ２
（式中、Ｒｌ，Ｒ３は前記定義と同一、Ｒ４は水素原子
又はＣ＋−ａのアルキル基；但し、Ｒ４はＲ１又は、Ｒ
２と結合してラクタム環を構成してもよい）、及び
Ｒ４
（式中、Ｒ４は前記定義と同一、ＺはＣ１−，のアルキ
レン基又は基−０−）
上記式（１）で示される有機溶媒としては、例えば、ジ
エチレングリコールジメチルエーテル、ジエチレングリ
コールジエチルエーテル、１．２−ノメトキシエタン、
２−エトキシエチルアセテート、■，２−ジエトキシエ
タン、２−メトキシエチルアセテート、３−メトキンブ
チルアセテート、２−メトキシブ口ピルアセテート、２
−エトキンブ口ビルアセテート、３−エトキンブチルア
セテート、ジアセトキンメタン、１．２−ジアセトキシ
エタン、１．３−ジアセトキシプロパン、１．４−ジア
セトキシブタン、■，５−ジアセトキシペンクン、１．
６−ジアセトキシヘキサン、エチレングリコールジブロ
ピオン酸エステル等が挙げられる。Rl (X)R! (Y)R3...
(I) (wherein R1 and R3 are each a C I-4 alkyl group, R2 is a C +-s alkylene group; -0-
), / , R2 (wherein Rl and R3 are the same as defined above, R4 is a hydrogen atom or a C+-a alkyl group; however, R4 is R1 or R
(may be combined with 2 to form a lactam ring), and R4 (wherein R4 is the same as the above definition, Z is C1-, an alkylene group or group -0-) represented by the above formula (1) Examples of organic solvents include diethylene glycol dimethyl ether, diethylene glycol diethyl ether, 1,2-nomethoxyethane,
2-Ethoxyethyl acetate, ■,2-diethoxyethane, 2-methoxyethyl acetate, 3-methoxybutyl acetate, 2-methoxybutyl acetate, 2
-Etquinbuvir acetate, 3-ethquinbutyl acetate, diacetquinmethane, 1,2-diacetoxyethane, 1,3-diacetoxypropane, 1,4-diacetoxybutane, ■,5-diacetoxypenkun , 1.
Examples include 6-diacetoxyhexane and ethylene glycol dibropionic acid ester.
上記式（ｎ）で示される有機溶媒としては、ＮＮ−ジメ
チルホルムアミド、Ｎ−メチルーＮ−エチルホルムアミ
ド、Ｎ，Ｎ−ジエチルホルムアミド、Ｎ，Ｎ−ジメチル
アセトアミド、Ｎ−メチル−２−ビロリドン、Ｎ一エチ
ル−２−ピロリドン等が挙げられる。Examples of the organic solvent represented by the above formula (n) include NN-dimethylformamide, N-methyl-N-ethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and N-methyl-N-ethylformamide. Examples include ethyl-2-pyrrolidone.
また、上記式（ＩＩＩ）で示される有機溶媒としては、
エチレンカーボネート、プロピレンカーボネート、γ−
プチロラクトン、δ−バレロラクトン等が挙げられる。Further, as the organic solvent represented by the above formula (III),
Ethylene carbonate, propylene carbonate, γ-
Examples include petirolactone and δ-valerolactone.
上記式（Ｉ）−（ＩＩＩ）で示される有機溶媒は、各々
混合して用いられても良い。The organic solvents represented by the above formulas (I) to (III) may be used in combination.
これらの有機溶媒のうち、製剤安定性の点で特に、３−
メトキシブチルアセテート、エチレンカーボネート、プ
ロピレンカーボネート及びγ−プチロラクトンを用いる
のが好ましい。Among these organic solvents, 3-
Preference is given to using methoxybutyl acetate, ethylene carbonate, propylene carbonate and γ-butyrolactone.
この発明においてかかる有機溶媒としては、実質的に無
水のものが用いられる。ここで実質的に無水とは、上記
有機溶剤の市販品中に不可避的に含まれる微量の水分や
製剤時に大気中から不可避的に混入しうる微量の水分等
の存在を許容するが、意図的に水が添加されていないこ
とを意味する。In this invention, a substantially anhydrous organic solvent is used. Here, "substantially anhydrous" refers to the presence of trace amounts of water that are unavoidably contained in commercially available organic solvents and trace amounts of water that may be unavoidably mixed in from the atmosphere during formulation; This means that no water is added to the .
ここで、水が有意に添加された有機溶媒を用いると、製
剤安定性が低下し、実使用上の殺菌効果の低下を招くた
め適さない。Here, if an organic solvent to which water is significantly added is used, it is not suitable because the stability of the formulation decreases and the bactericidal effect in practical use decreases.
この発明の工業殺菌剤は、無水マレイン酸を上記有機溶
媒に直接添加混合して溶解させることにより調製するこ
とができる。従って有機溶媒の使用量は無水マレイン酸
を溶解するに足る量とされ、通常、製剤中の無水マレイ
ン酸の濃度が約５〜５０重量％、好ましくはｌＯ〜４０
重量％となるように調整される。この量が多すぎると、
長時間保存時に無水マレイン酸か固体として折出するお
それがあり、製剤安定性上好ましくない。The industrial disinfectant of the present invention can be prepared by directly adding and mixing maleic anhydride to the above-mentioned organic solvent to dissolve it. Therefore, the amount of organic solvent used is sufficient to dissolve maleic anhydride, and the concentration of maleic anhydride in the preparation is usually about 5 to 50% by weight, preferably 10 to 40% by weight.
% by weight. If this amount is too large,
Maleic anhydride may be precipitated as a solid during long-term storage, which is unfavorable in terms of formulation stability.
このようにして得られるこの発明の殺菌剤は、それ事態
、製剤安定性が優れた有用なものであるが、前述のごと
くこれを微生物が繁殖した水系に直接添加することによ
り、従来の無水マレイン酸製剤使用時に比して、著しく
高い殺菌効果を発現する。従って、この発明は、上記工
業用殺菌剤を水系に直接添加することからなる工業用殺
菌方法をも提供するものである。The disinfectant of the present invention obtained in this way is useful as it has excellent formulation stability, but as mentioned above, by directly adding it to the aqueous system in which microorganisms have grown, it is possible to It exhibits a significantly higher bactericidal effect than when using acid preparations. Accordingly, the present invention also provides an industrial sterilization method comprising directly adding the above-mentioned industrial sterilizer to an aqueous system.
この際の適切な添加量は、対象系の微生物の繁殖状況、
水質、温度等によっても異なるが、通常、対象系中に対
し、１〜２００ｐｐｍ （無水マレイン酸量）とするの
が適している。この際、上記製剤自体の水分散性が優れ
ているので流通系においては連続少量添加で濃度調整を
行っても衝撃添加で行ってもよい。The appropriate amount to add at this time depends on the growth status of microorganisms in the target system.
Although it varies depending on water quality, temperature, etc., it is usually suitable to set the amount to 1 to 200 ppm (amount of maleic anhydride) in the target system. At this time, since the above formulation itself has excellent water dispersibility, in a distribution system, the concentration may be adjusted by continuous small amount addition or by impact addition.
なお、この発明の製剤において、その効果と阻害しない
他の有機溶媒や他の殺菌剤等の第三成分が少量混合され
ていてもよい。In addition, in the preparation of this invention, a small amount of a third component such as another organic solvent or another fungicide that does not interfere with the effect may be mixed.
（ホ）実施例
実施例ｌ
無水マレイン酸（日本触媒化学製）を各溶媒に溶解して
無水マレイン酸溶液を調製した。ついて、これらを５０
℃の恒温漕内に静置し、経日的に無水マレイン酸（ Ｍ
Ａ ）の残存率（Ｗ％）をＨＰＬＣで定量した。組成
及び結果を表−１に示す。(e) Examples Example 1 Maleic anhydride (manufactured by Nippon Shokubai Chemical) was dissolved in each solvent to prepare a maleic anhydride solution. Then, 50 of these
Maleic anhydride (M
The residual rate (W%) of A) was quantified by HPLC. The composition and results are shown in Table-1.
（以下余白）
表−１
表一！ 続き
（以下余白）
＊ＤＢＥ’ ：ノベインックエステル
構造式： ＣＨｓ Ｃ−０−（ＣＨＪｔ−．０−Ｃ−
ＣＩ−］１１１
表一ｌに示されるように、水及び種々の現水性有機溶媒
で調製した無水マレイン酸製剤のうち、特定の親水性有
機溶媒を用いたこの発明の製剤においては、３０日後に
おいても無水マレイン酸が９４％以上残存していること
が分かる。ここで５０℃で３０日放置は、実用環境下に
おける約１年程度の放置条件に相当するため、上記高い
残存率はこの発明の製剤の著しく優れた製剤安定性を示
すものである。中でも、ＤＢＥ，エチレンカーボネート
、プロピレンカーボネート及びγ−プチロラクトン使用
時には、３０日後においても無水マレイン酸の減少が全
く認められず、とくに優れていることが分かる。(Margins below) Table-1 Table 1! Continued (blank below) *DBE': Noveinic ester structural formula: CHs C-0-(CHJt-.0-C-
CI-]111 As shown in Table 1, among the maleic anhydride formulations prepared with water and various aqueous organic solvents, the formulation of this invention using a specific hydrophilic organic solvent showed It can also be seen that 94% or more of maleic anhydride remains. Here, 30 days of standing at 50°C corresponds to about 1 year of standing in a practical environment, so the above-mentioned high survival rate indicates the extremely excellent stability of the formulation of the present invention. Among these, when DBE, ethylene carbonate, propylene carbonate, and γ-butyrolactone were used, no decrease in maleic anhydride was observed even after 30 days, indicating that they were particularly excellent.
なお、比較例に示す各製剤のほとんどは、１日以内に無
水マレイン酸成分が消失して無水マレイン酸としての効
果を全く期待できず、また最も安定性の高いトリブロビ
レングリコールモノメチルエーテル（比較例Ｎｏ．４）
においても３０日後において無水マレイン酸がほとんど
残存していないことが判る。In addition, in most of the formulations shown in the comparative examples, the maleic anhydride component disappears within one day and no effect as maleic anhydride can be expected. Example No. 4)
It can be seen that almost no maleic anhydride remained after 30 days.
実施例２
実施例と同様にして、表２及び表３に示す組成の無水マ
レイン酸製剤（実施例ＡＩ−ＡＩＯ、比較例Ｂｌ−８７
）を作製した。Example 2 Maleic anhydride preparations having the compositions shown in Tables 2 and 3 (Example AI-AIO, Comparative Example Bl-87) were prepared in the same manner as in Example.
) was created.
（以下余白） 表−２ 実施例 表 比較例 （以下余白） 上記各製剤を用いて、殺菌試験を行った。(Margin below) Table-2 Example table Comparative example (Margin below) A sterilization test was conducted using each of the above formulations.
（試験方法）某製紙工場の新聞紙抄造機より採取した生
菌数３．５ＸｌＯ’／ｄを含む白水（ ｐ Ｈ４．８，
シュードモナス属アルカリゲネス属菌主体）をビーカー
に５０１１ｙ＋２とり３０℃の恒温漕内で撹拌する。(Test method) White water (pH 4.8,
5011y+2 (mainly Pseudomonas and Alcaligenes) was placed in a beaker and stirred in a constant temperature bath at 30°C.
ここへ、表２−３の製剤物を約２ｃｍ角のテフロンシ一
トに所定量（活性成分当り１０〜１００ｐｐｍ）化学天
秤で精秤したものを直接投入する。A predetermined amount (10 to 100 ppm of active ingredient) of the formulation shown in Table 2-3 was accurately weighed using a chemical balance into a approximately 2 cm square Teflon sheet and then directly charged therein.
投入後、経時的に菌数を測定した結果を表−４に示す。Table 4 shows the results of measuring the number of bacteria over time after the injection.
なお、これらの供試薬剤は調製７日後（室温）に供試し
た。Note that these test drugs were tested 7 days after preparation (at room temperature).
（以下余白）
表−４
（考察）
表−４から明らかな様に、本願発明の製剤品が優れた殺
菌効力を示したのに対し、水・アルコール・グリコール
類で製剤したものやマレイン酸では、本願発明品の５〜
１０倍の濃度においてら充分な効力は得られなかった。(Margins below) Table 4 (Discussion) As is clear from Table 4, the formulation of the present invention showed excellent bactericidal efficacy, whereas those formulated with water, alcohol, glycols, and maleic acid did not. , 5 to 5 of the claimed invention
Sufficient efficacy was not obtained even at 10 times the concentration.
さらに無水マレイン酸をそのまま添加した場合と比較し
ても本願発明品は低濃度で有効である。これは、溶媒効
果によって無水マレイン酸の水添加時に加水分解が抑制
されつつ迅速に系中に分散されることや、菌に対する浸
透力が向上した為と考えられる。Furthermore, compared to the case where maleic anhydride is added as is, the product of the present invention is effective at a low concentration. This is thought to be because maleic anhydride is rapidly dispersed into the system while its hydrolysis is suppressed when water is added due to the solvent effect, and because the permeability to bacteria is improved.
なお、Ａ− １−Ａ− １ ０の各製剤品を５０゜Ｃで
１ヶ月静置後、同様に試験したところ、ほぼ同等の殺菌
効果が得られた。In addition, when each of the formulations of A-1-A-10 was allowed to stand at 50°C for one month and then tested in the same manner, almost the same bactericidal effect was obtained.
（比較試験例）
供試薬剤の１％水溶液を調製したものを約３０分後に供
試する以外は全て試験例−２と同ように行った。(Comparative Test Example) All tests were carried out in the same manner as Test Example 2, except that a 1% aqueous solution of the test drug was prepared and tested after about 30 minutes.
（以下余白）
表−５
（考察）表−５から明らかな様に、いずれの薬剤も原液
添加をした場合に比較して著しく効力は低下し、マレイ
ン酸と同程度の効力しか得られなかった。１％水溶液調
製後無水マレイン酸か加水分解してマレイン酸になって
から供試されたものと考えられる。(Left below) Table 5 (Discussion) As is clear from Table 5, the efficacy of all drugs was significantly lower than when the undiluted solution was added, and only the same efficacy as maleic acid was obtained. . It is believed that after preparing a 1% aqueous solution, maleic anhydride was hydrolyzed to form maleic acid before being tested.
（へ）発明の効果
この発明の殺菌剤によれば、無水マイレン酸直接添加時
や従来の無水マレイン酸製剤添加時に比して、著しく高
い殺菌効果が発現され、しかもその効果は製剤の長期間
放置後においても同様に発現される。従ってその実用的
価値は著しく高いものである。(f) Effects of the Invention According to the bactericidal agent of the present invention, a significantly higher bactericidal effect is expressed than when maleic anhydride is added directly or when conventional maleic anhydride preparations are added, and the effect remains for a long period of time. It is expressed in the same way even after being left alone. Therefore, its practical value is extremely high.
また、かかる殺菌剤においては、対象水系中に亜硫酸イ
オンのごとき還元性イオンが含有されている場合、通常
の汎用性工業用殺菌剤ではその殺菌効果が低減されてし
まうのに対し、このような低減が生じず安定な萌記殺菌
効果が発現されることら見出されているため、上記効果
とも相俟ってその有用性は極めて大なるものである。In addition, with such disinfectants, if reducing ions such as sulfite ions are contained in the target water system, the bactericidal effect of ordinary general-purpose industrial disinfectants is reduced. It has been found that a stable bactericidal effect is exhibited without any reduction, and in combination with the above-mentioned effects, its usefulness is extremely great.
Claims (3)
無水マレイン酸を溶解調製してなる工業用殺菌剤。(1) An industrial disinfectant prepared by dissolving maleic anhydride in a substantially anhydrous aprotic hydrophilic organic solvent.
（III）から選ばれる有機溶媒： Ｒ＿１−（Ｘ）−Ｒ＿２−（Ｙ）−Ｒ＿３……（ I ）
（式中、Ｒ＿１及びＲ＿３は各々、Ｃ＿１＿−＿４のア
ルキル基、Ｒ＿２はＣ＿１＿−＿６のアルキレン基；Ｘ
及びＹは各々、基−Ｏ−、−ＣＯＯ−又は−Ｏ−Ｒ＿２
−Ｏ−）、▲数式、化学式、表等があります▼……（I
I） （式中、Ｒ＿１、Ｒ＿２は前記定義と同一、Ｒ＿４は水
素原子又はＣ＿１＿−＿４のアルキル基：但し、Ｒ＿４
はＲ＿１又はＲ＿３と結合してラクタム環を構成しても
よい）、及び ▲数式、化学式、表等があります▼ （式中、Ｒ＿４は前記定義と同一、ＺはＣ＿１＿−＿４
のアルキレン基又は基−Ｏ−） である請求項１記載の工業用殺菌剤。(2) The aprotic hydrophilic organic solvent has the following formula (I) ~
Organic solvent selected from (III): R_1-(X)-R_2-(Y)-R_3...(I)
(In the formula, R_1 and R_3 are each an alkyl group of C_1_-_4, R_2 is an alkylene group of C_1_-_6;
and Y are each a group -O-, -COO- or -O-R_2
-O-), ▲Mathematical formulas, chemical formulas, tables, etc.▼……(I
I) (In the formula, R_1 and R_2 are the same as the above definitions, R_4 is a hydrogen atom or an alkyl group of C_1_-_4: However, R_4
may be combined with R_1 or R_3 to form a lactam ring), and ▲ mathematical formulas, chemical formulas, tables, etc. ▼ (wherein R_4 is the same as the above definition, Z is C_1_-_4
The industrial fungicide according to claim 1, which is an alkylene group or a group -O-).
該水系中に存在する微生物の殺菌処理を行うことを特徴
とする工業用殺菌方法。(3) An industrial sterilization method comprising directly adding the industrial sterilizer of claim 1 to a water system to sterilize microorganisms present in the water system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11317389A JP2661745B2 (en) | 1989-05-02 | 1989-05-02 | Industrial disinfectant and disinfection method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11317389A JP2661745B2 (en) | 1989-05-02 | 1989-05-02 | Industrial disinfectant and disinfection method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02292202A true JPH02292202A (en) | 1990-12-03 |
| JP2661745B2 JP2661745B2 (en) | 1997-10-08 |
Family
ID=14605408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11317389A Expired - Lifetime JP2661745B2 (en) | 1989-05-02 | 1989-05-02 | Industrial disinfectant and disinfection method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2661745B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5122301A (en) * | 1991-09-09 | 1992-06-16 | Great Lakes Chemical Corp. | Antimicrobial compositions containing propylene carbonate and/or ethylene carbonate as the carrier solvent |
| WO2001082694A1 (en) * | 2000-04-28 | 2001-11-08 | Ecolab Inc. | Antimicrobial composition |
| EP1767091A3 (en) * | 2005-09-21 | 2007-08-22 | Clariant Produkte (Deutschland) GmbH | Biocidal compositions |
-
1989
- 1989-05-02 JP JP11317389A patent/JP2661745B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5122301A (en) * | 1991-09-09 | 1992-06-16 | Great Lakes Chemical Corp. | Antimicrobial compositions containing propylene carbonate and/or ethylene carbonate as the carrier solvent |
| WO1993005032A1 (en) * | 1991-09-09 | 1993-03-18 | Great Lakes Chemical Corporation | Antimicrobial compositions containing propylene carbonate and/or ethylene carbonate as the carrier solvent |
| WO2001082694A1 (en) * | 2000-04-28 | 2001-11-08 | Ecolab Inc. | Antimicrobial composition |
| EP1767091A3 (en) * | 2005-09-21 | 2007-08-22 | Clariant Produkte (Deutschland) GmbH | Biocidal compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2661745B2 (en) | 1997-10-08 |
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