JP2012232913A - Bactericide composition and sterilization method - Google Patents
Bactericide composition and sterilization method Download PDFInfo
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本発明は、主に食品工場等の床、壁、器具、設備等の殺菌に用いる殺菌剤組成物およびこれを用いた殺菌方法に関する。 The present invention mainly relates to a disinfectant composition used for disinfecting floors, walls, appliances, facilities and the like of food factories and the like, and a disinfection method using the same.
食品工場、飲食店等の厨房、スーパー内の加工作業場などの食品を取り扱う現場では、衛生上の観点から床、壁、器具、設備等の殺菌を行う必要があり、従来からアルコール、塩素系化合物、過酸化物、カチオン界面活性剤、両性界面活性剤、ビグアナイド化合物等、様々な殺菌剤が用いられている。その中でもジデシルジメチルアンモニウムクロライドやポリヘキサメチレンビグアナイド塩酸塩は、殺菌効果および安全性の点から頻繁に利用されている殺菌剤である。 In the field of handling food such as food factories, kitchens of restaurants, processing shops in supermarkets, it is necessary to sterilize floors, walls, appliances, equipment, etc. from the viewpoint of hygiene. Various bactericides such as peroxides, cationic surfactants, amphoteric surfactants and biguanide compounds are used. Among them, didecyldimethylammonium chloride and polyhexamethylene biguanide hydrochloride are bactericides that are frequently used from the viewpoint of bactericidal effect and safety.
しかしながら、近年、第四級アンモニウム塩やビグアナイド系殺菌剤の使用を重ねるうちに、これら殺菌剤に対し抵抗性を有する微生物（以下、薬剤抵抗性菌とも称する）が発生し、殺菌が不十分となる問題が生じている。ジデシルジメチルアンモニウムクロライドやポリヘキサメチレンビグアナイド塩酸塩に対する薬剤抵抗性菌としては、例えば、非特許文献１に記載されるように、Pseudomonas属やSerratia属の菌が知られている。これら薬剤抵抗性菌に対しては、その発生を予防する手段として使用薬剤を定期的に変更する等の対策が採られているが、作業性およびコストの点から敬遠される傾向にある。また、薬剤抵抗性菌の存在が確認された場合には、次亜塩素酸ナトリウム等の塩素系殺菌剤による処理が行われているが、塩素系殺菌剤は金属腐食性が強く、設備や装置に与える影響が大きい上、臭いが残留する等の問題があり、やはり敬遠される傾向にある。さらに、ジデシルジメチルアンモニウムクロライドは使用後にぬめりが残り易く、ポリヘキサメチレンビグアナイド塩酸塩は使用後にべたつきが残り易い傾向がある。 However, in recent years, while using quaternary ammonium salts and biguanide fungicides repeatedly, microorganisms having resistance to these fungicides (hereinafter also referred to as drug-resistant bacteria) have been generated, and sterilization is insufficient. Has arisen. As drug-resistant bacteria against didecyldimethylammonium chloride and polyhexamethylene biguanide hydrochloride, for example, as described in Non-Patent Document 1, bacteria of the genus Pseudomonas and Serratia are known. For these drug-resistant bacteria, measures such as periodically changing the used drug are taken as means for preventing the occurrence thereof, but they tend to be avoided from the viewpoint of workability and cost. When the presence of drug-resistant bacteria is confirmed, treatment with a chlorine-based disinfectant such as sodium hypochlorite is carried out. In addition, there is a problem that the odor remains, and there is a tendency to be avoided. Further, didecyldimethylammonium chloride tends to remain slimy after use, and polyhexamethylene biguanide hydrochloride tends to remain sticky after use.
上記のような背景から、カビなどの真菌類や一般細菌に加え、薬剤抵抗性菌に対しても殺菌効果を有し、継続的に使用しても薬剤抵抗性菌が発生し難く、使用後のぬめりやべたつきが改善された殺菌剤組成物が望まれている。 From the above background, in addition to fungi such as molds and general bacteria, it also has a bactericidal effect against drug-resistant bacteria, and drug-resistant bacteria are unlikely to occur even after continuous use. There is a demand for a fungicide composition with improved sliminess and stickiness.
本発明の目的は、真菌類、一般細菌に対して殺菌効果を有すると共に、ジデシルジメチルアンモニウムクロライドなどの第四級アンモニウム塩に対し抵抗性を有する微生物やポリヘキサメチレンビグアナイド塩酸塩などのビグアナイド系殺菌剤に対し抵抗性を有する微生物に対しても殺菌効果を有し、それ自体に対する薬剤抵抗性菌が発生し難い殺菌剤組成物を提供することにある。 The object of the present invention is a microorganism having a bactericidal effect on fungi and general bacteria and having resistance to quaternary ammonium salts such as didecyldimethylammonium chloride and biguanides such as polyhexamethylene biguanide hydrochloride An object of the present invention is to provide a bactericide composition which has a bactericidal effect against microorganisms having resistance to bactericides and hardly generates drug-resistant bacteria against itself.
本発明者らは、鋭意検討の結果、下記式（Ｉ）の化合物およびトリエタノールアミンを含有する組成物が上記課題を解決することを見出し、本発明を完成させるに至った。 As a result of intensive studies, the present inventors have found that a composition containing a compound of the following formula (I) and triethanolamine solves the above problems, and has completed the present invention.
すなわち本発明は、式（Ｉ）の化合物およびトリエタノールアミンを含有する殺菌剤組成物を提供する：
［式中、Ｒ１は炭素数１〜３の飽和直鎖アルキル基、Ｒ２は炭素数８〜１２の飽和直鎖アルキル基、Ｘ−はハロゲンイオン、Ｙは炭素数８〜１２の飽和直鎖アルキレン基を表す］。
Thus, the present invention provides a fungicide composition comprising a compound of formula (I) and triethanolamine:
[Wherein R 1 is a saturated linear alkyl group having 1 to 3 carbon atoms, R 2 is a saturated linear alkyl group having 8 to 12 carbon atoms, X − is a halogen ion, and Y is a saturated straight chain alkyl group having 8 to 12 carbon atoms. Represents a chain alkylene group].
また、本発明は、上記殺菌剤組成物を殺菌対象物と接触させることを特徴とする殺菌方法も提供する。 Moreover, this invention also provides the sterilization method characterized by making the said disinfectant composition contact with a sterilization target object.
本発明の殺菌剤組成物は、カビなどの真菌類や一般細菌への殺菌効果に加え、第四級アンモニウム塩および／またはビグアナイド系殺菌剤に抵抗性を有する薬剤抵抗性菌に対しても優れた殺菌効果を有し、長期間継続的に使用した場合でも、該組成物自体に対する薬剤抵抗性菌が発生し難く、かつ、使用後のぬめりやべたつきも改善されたものである。 The fungicide composition of the present invention is excellent against drug-resistant bacteria having resistance to quaternary ammonium salts and / or biguanide fungicides, in addition to fungicidal effects on fungi such as molds and general bacteria. Even when used continuously for a long period of time, drug-resistant bacteria are hardly generated against the composition itself, and slimming and stickiness after use are improved.
本発明の殺菌剤組成物の構成成分である式（Ｉ）の化合物において、Ｒ１はメチル基、エチル基またはプロピル基のいずれかであり、メチル基またはエチル基が好ましく、メチル基がより好ましい。Ｒ２は炭素数８〜１０の飽和直鎖アルキル基が好ましく、デシル基がより好ましい。Ｘ−はハロゲンイオンであり、塩素イオンまたは臭素イオンが好ましく、塩素イオンがより好ましい。Ｙは炭素数１０〜１２の飽和直鎖アルキル基が好ましく、デシレン基がより好ましい。 In the compound of formula (I) which is a constituent of the fungicide composition of the present invention, R 1 is any one of a methyl group, an ethyl group and a propyl group, preferably a methyl group or an ethyl group, more preferably a methyl group. . R 2 is preferably a saturated linear alkyl group having 8 to 10 carbon atoms, and more preferably a decyl group. X − represents a halogen ion, preferably a chlorine ion or a bromine ion, and more preferably a chlorine ion. Y is preferably a saturated linear alkyl group having 10 to 12 carbon atoms, and more preferably a decylene group.
式（Ｉ）の化合物の具体例としては、１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジブロミド、１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジクロライド、１，１２−ジ（３−デシル−２−メチルイミダゾリウム）ドデカンジブロミド、１，１２−ジ（３−デシル−２−メチルイミダゾリウム）ドデカンジクロライド、１，１０−ジ（３−オクチル−２−メチルイミダゾリウム）デカンジブロミド、１，１０−ジ（３−オクチル−２−メチルイミダゾリウム）デカンジクロライド、１，１２−ジ（３−オクチル−２−メチルイミダゾリウム）ドデカンジブロミド、１，１２−ジ（３−オクチル−２−メチルイミダゾリウム）ドデカンジクロライド等が例示される。これらの中で１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジブロミド、１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジクロライド、１，１２−ジ（３−デシル−２−メチルイミダゾリウム）ドデカンジブロミド、１，１２−ジ（３−デシル−２−メチルイミダゾリウム）ドデカンジクロライド、１，１２−ジ（３−オクチル−２−メチルイミダゾリウム）ドデカンジブロミド、１，１２−ジ（３−オクチル−２−メチルイミダゾリウム）ドデカンジクロライドが一般細菌に対する殺菌効果の点で好ましく、１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジブロミド、１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジクロライド、１，１２−ジ（３−デシル−２−メチルイミダゾリウム）ドデカンジクロライド、１，１２−ジ（３−オクチル−２−メチルイミダゾリウム）ドデカンジクロライドが他の殺菌成分との混合性の点でより好ましく、１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジクロライドが薬剤抵抗性菌に対する殺菌効果および水への溶解性の点でさらに好ましい。 Specific examples of the compound of formula (I) include 1,10-di (3-decyl-2-methylimidazolium) decane dibromide, 1,10-di (3-decyl-2-methylimidazolium) decane dichloride. 1,12-di (3-decyl-2-methylimidazolium) dodecane dibromide, 1,12-di (3-decyl-2-methylimidazolium) dodecane dichloride, 1,10-di (3-octyl- 2-methylimidazolium) decane dibromide, 1,10-di (3-octyl-2-methylimidazolium) decane dichloride, 1,12-di (3-octyl-2-methylimidazolium) dodecane dibromide, 1, , 12-di (3-octyl-2-methylimidazolium) dodecane dichloride and the like. Among these, 1,10-di (3-decyl-2-methylimidazolium) decane dibromide, 1,10-di (3-decyl-2-methylimidazolium) decane dichloride, 1,12-di (3 -Decyl-2-methylimidazolium) dodecane dibromide, 1,12-di (3-decyl-2-methylimidazolium) dodecane dichloride, 1,12-di (3-octyl-2-methylimidazolium) dodecandi Bromide and 1,12-di (3-octyl-2-methylimidazolium) dodecane dichloride are preferred in terms of bactericidal effect on general bacteria, and 1,10-di (3-decyl-2-methylimidazolium) decanedibromide 1,10-di (3-decyl-2-methylimidazolium) decane dichloride, 1,12-di (3-decyl-2-methyl) Imidazolium) dodecane dichloride and 1,12-di (3-octyl-2-methylimidazolium) dodecane dichloride are more preferable in terms of miscibility with other bactericidal components, and 1,10-di (3-decyl-2). -Methylimidazolium) decane dichloride is more preferable in terms of bactericidal effect against drug-resistant bacteria and solubility in water.
本発明の殺菌剤組成物における式（Ｉ）の化合物の割合は特に限定されないが、本発明の殺菌剤組成物が水溶液の形態である場合、該殺菌剤組成物における式（Ｉ）の化合物の割合は、０．００１〜５０重量％が好ましく、０．００５〜３０重量％がより好ましく、０．０１５〜９重量％がさらに好ましい。式（Ｉ）の化合物の割合が０．００１重量％未満の場合、第四級アンモニウム塩および／またはビグアナイド系殺菌剤に対し抵抗性を有する薬剤抵抗性菌に対する発育阻止効果が低下する傾向があり、５０重量％を超える場合、組成物の粘度が上昇し、取り扱い難くなる傾向がある。 The proportion of the compound of formula (I) in the fungicide composition of the present invention is not particularly limited, but when the fungicide composition of the present invention is in the form of an aqueous solution, the ratio of the compound of formula (I) in the fungicide composition The proportion is preferably 0.001 to 50% by weight, more preferably 0.005 to 30% by weight, and still more preferably 0.015 to 9% by weight. When the proportion of the compound of formula (I) is less than 0.001% by weight, the growth inhibitory effect on drug-resistant bacteria having resistance to quaternary ammonium salts and / or biguanide fungicides tends to decrease. When the amount exceeds 50% by weight, the viscosity of the composition increases and it tends to be difficult to handle.
本発明の殺菌剤組成物におけるトリエタノールアミンの割合は特に限定されないが、式（Ｉ）の化合物１重量部に対し、０．００２５〜２４．５重量部が好ましく、０．００５〜５重量部がより好ましく、０．０１〜１．５重量部がさらに好ましい。トリエタノールアミンの割合が０．００２５重量部未満の場合、殺菌効果が不十分となる傾向、殺菌剤組成物を水溶液の形態とした場合の低温条件における安定性が低下する傾向、後述する他の殺菌成分や他の添加剤を配合した際に水溶液の白濁等を生じる傾向、および金属腐蝕抑制効果が十分に得られない傾向がある。一方、トリエタノールアミンの割合が２４．５重量部を超える場合、殺菌剤組成物を水溶液の形態とした場合の該組成物のｐＨが過度に上昇し、金属腐食性が高くなる傾向がある。 Although the ratio of triethanolamine in the fungicidal composition of the present invention is not particularly limited, 0.0025 to 24.5 parts by weight is preferable with respect to 1 part by weight of the compound of formula (I), and 0.005 to 5 parts by weight. Is more preferable, and 0.01-1.5 weight part is further more preferable. When the proportion of triethanolamine is less than 0.0025 parts by weight, the bactericidal effect tends to be insufficient, the stability at low temperature conditions when the bactericidal composition is in the form of an aqueous solution, When a sterilizing component or other additive is blended, the aqueous solution tends to become cloudy and the metal corrosion inhibiting effect tends not to be sufficiently obtained. On the other hand, when the proportion of triethanolamine exceeds 24.5 parts by weight, the pH of the composition when the bactericidal composition is in the form of an aqueous solution tends to increase excessively, and the metal corrosivity tends to increase.
本発明の殺菌剤組成物が水溶液の形態である場合、該殺菌剤組成物のｐＨは特に限定されないが、ｐＨ７〜１２が好ましく、ｐＨ７．５〜１１がより好ましく、ｐＨ７．７〜９．５がさらに好ましく、ｐＨ８〜９．４が特に好ましい。 When the disinfectant composition of the present invention is in the form of an aqueous solution, the pH of the disinfectant composition is not particularly limited, but is preferably pH 7-12, more preferably pH 7.5-11, and pH 7.7-9.5. Is more preferable, and pH 8 to 9.4 is particularly preferable.
水溶液の形態の本発明の殺菌剤組成物は、トリエタノールアミンの割合が式（Ｉ）の化合物１重量部に対し０．００２５〜２４．５重量部の範囲であれば、ｐＨが７〜１２の範囲となるものであるが、所望により、アルカリ剤を用いてｐＨを調整してもよい。本発明の殺菌剤組成物に適用可能なアルカリ剤としては、配合することによって析出や白濁等の変化が発生しないものであればよく、例えば水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム、セスキ炭酸ナトリウム、メタケイ酸ナトリウム、セスキケイ酸ナトリウム、オルソケイ酸ナトリウム、オルソリン酸ナトリウム、ピロリン酸ナトリウム、トリポリリン酸ナトリウム、テトラリン酸ナトリウム、ヘキサメタリン酸ナトリウム等が例示される。これらアルカリ剤の中で、水酸化ナトリウムおよび水酸化カリウムが水溶液として保管する際の組成物の安定性の点で好ましい。また、これらアルカリ剤は２種以上を併用してもよい。 The fungicide composition of the present invention in the form of an aqueous solution has a pH of 7 to 12 if the proportion of triethanolamine is in the range of 0.0025 to 24.5 parts by weight with respect to 1 part by weight of the compound of formula (I). However, if desired, the pH may be adjusted using an alkaline agent. The alkali agent applicable to the fungicide composition of the present invention is not particularly limited as long as it does not cause changes such as precipitation and cloudiness when blended. For example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate , Potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium sesquicarbonate, sodium metasilicate, sodium sesquisilicate, sodium orthosilicate, sodium orthophosphate, sodium pyrophosphate, sodium tripolyphosphate, sodium tetraphosphate, sodium hexametaphosphate, etc. Is done. Among these alkali agents, sodium hydroxide and potassium hydroxide are preferable in terms of stability of the composition when stored as an aqueous solution. Two or more of these alkali agents may be used in combination.
また、本発明の殺菌剤組成物には、他の殺菌成分を配合してもよい。本発明の殺菌剤組成物に配合可能な他の殺菌成分としては、ジデシルジメチルアンモニウムクロライド、ベンザルコニウムクロライド等の第四級アンモニウム塩、ポリヘキサメチレンビグアナイド塩酸塩、グルコン酸クロルヘキシジン等のビグアナイド系殺菌剤、ヨウ素グリシン複合体等の有機ヨード系殺菌剤等が例示される。これら他の殺菌成分の中でもビグアナイド系殺菌剤が芽胞菌に対する殺菌効果の点で好ましく、ビグアナイド系殺菌剤の中でもポリヘキサメチレンビグアナイド塩酸塩が特に好ましい。これら他の殺菌成分は２種以上を用いてもよい。 Moreover, you may mix | blend another disinfection component with the disinfectant composition of this invention. Other bactericidal components that can be blended in the bactericidal composition of the present invention include quaternary ammonium salts such as didecyldimethylammonium chloride and benzalkonium chloride, biguanides such as polyhexamethylene biguanide hydrochloride and chlorhexidine gluconate. Examples include bactericides and organic iodine bactericides such as iodine glycine complex. Among these other bactericidal components, a biguanide type bactericidal agent is preferable in terms of bactericidal effect against spore bacteria, and among biguanide type bactericides, polyhexamethylene biguanide hydrochloride is particularly preferable. Two or more kinds of these other sterilizing components may be used.
本発明の殺菌剤組成物に他の殺菌成分を配合する際の割合は、式（Ｉ）の化合物１重量部に対し、０．５〜４０重量部が好ましく、０．７〜１０重量部がより好ましく、１〜５重量部がさらに好ましい。他の殺菌成分の割合が０．５重量部未満の場合、当該他の殺菌成分による殺菌効果が十分に発揮されない傾向があり、４０重量部を超える場合、水溶液として保管する間に白濁等を生じる傾向がある。 The proportion when the other bactericidal component is blended with the bactericide composition of the present invention is preferably 0.5 to 40 parts by weight, and 0.7 to 10 parts by weight with respect to 1 part by weight of the compound of formula (I). More preferred is 1 to 5 parts by weight. When the proportion of other sterilizing components is less than 0.5 parts by weight, the sterilizing effect due to the other sterilizing components tends not to be sufficiently exerted. When the proportion exceeds 40 parts by weight, white turbidity occurs during storage as an aqueous solution. Tend.
本発明の殺菌剤組成物には必要により、さらに他の添加剤を配合することができる。配合可能な他の添加剤としては、例えば、エタノール、着色料、香料等が挙げられる。本発明の殺菌剤組成物におけるこれら他の添加剤の割合は、通常、５重量％以下である。 If necessary, the disinfectant composition of the present invention can further contain other additives. Examples of other additives that can be blended include ethanol, coloring agents, and fragrances. The ratio of these other additives in the fungicide composition of the present invention is usually 5% by weight or less.
本発明の殺菌剤組成物は、錠剤や粉末等の固形の形態、またはペーストやゼリー状等の半固形の形態で提供されてもよく、水溶液の形態で提供されてもよい。本発明の殺菌剤組成物が固形または半固形の形態で提供される場合には、通常、該組成物を水に溶解させ、水溶液の形態として殺菌対象物に適用することができる。本発明の殺菌剤組成物が水溶液の形態で提供される場合には、該水溶液をそのまま、またはさらに希釈した水溶液を殺菌対象物に適用することができる。 The disinfectant composition of the present invention may be provided in a solid form such as a tablet or powder, or a semi-solid form such as a paste or jelly, or may be provided in the form of an aqueous solution. When the disinfectant composition of the present invention is provided in a solid or semi-solid form, the composition can usually be dissolved in water and applied to an object to be sterilized in the form of an aqueous solution. When the bactericidal composition of the present invention is provided in the form of an aqueous solution, the aqueous solution can be applied to the sterilization target as it is or after further dilution.
本発明の殺菌剤組成物の調製方法は特に限定されないが、例えば、固形の殺菌剤組成物であれば、必要な成分を、所望により賦形剤等と共に、単に混合することによって得ることができ、さらに造粒、打錠等の一般的な製剤工程を経て得ることもできる。半固形の殺菌剤組成物であれば、必要な成分および水を結合剤やゲル化剤等と混合することによって得ることができ、水溶液の形態の殺菌剤組成物であれば、必要な成分を水に均一に溶解させることによって、あるいは調製された上記固形または半固形の殺菌剤組成物を水に溶解させることによって得ることができる。 The method for preparing the bactericidal composition of the present invention is not particularly limited. For example, in the case of a solid bactericidal composition, it can be obtained by simply mixing necessary components together with an excipient or the like as desired. Furthermore, it can also be obtained through general preparation steps such as granulation and tableting. If it is a semi-solid disinfectant composition, it can be obtained by mixing the necessary components and water with a binder, gelling agent, etc. If it is a disinfectant composition in the form of an aqueous solution, the necessary components can be obtained. It can be obtained by uniformly dissolving in water or by dissolving the prepared solid or semi-solid fungicide composition in water.
本発明の殺菌剤組成物のｐＨを調整する場合、該ｐＨ調整を行う段階は特に限定されないが、通常は、調製された水溶液の形態の殺菌剤組成物にアルカリ剤を添加すればよい。あるいは、水溶液の形態の殺菌剤組成物を所望のｐＨ範囲に調整し得るアルカリ剤の量を事前に決定しておき、殺菌剤組成物を調製する際に、当該量のアルカリ剤を必要な成分と共に水に均一に溶解させてもよいし、当該量のアルカリ剤を固形もしくは半固形の殺菌剤組成物に配合することによりｐＨ調整を行ってもよい。 When adjusting the pH of the disinfectant composition of the present invention, the stage of adjusting the pH is not particularly limited, but usually an alkali agent may be added to the prepared disinfectant composition in the form of an aqueous solution. Alternatively, the amount of the alkaline agent that can adjust the bactericidal composition in the form of an aqueous solution to a desired pH range is determined in advance, and when preparing the bactericidal composition, the amount of the alkaline agent is a necessary component. In addition, it may be dissolved uniformly in water, or the pH may be adjusted by blending the amount of the alkaline agent in a solid or semisolid fungicide composition.
固形または半固形の形態で提供される本発明の殺菌剤組成物の例としては、式（Ｉ）の化合物を１〜９９重量％およびトリエタノールアミンを０．０００１〜５重量％含有するもの、式（Ｉ）の化合物を３〜５０重量％およびトリエタノールアミンを０．００５〜３重量％含有するもの、式（Ｉ）の化合物を５〜１５重量％およびトリエタノールアミンを０．００１〜１重量％含有するものが挙げられる。さらに他の殺菌成分を含む本発明の殺菌剤組成物の例としては、式（Ｉ）の化合物を１〜９８重量％、トリエタノールアミンを０．０００１〜５重量％およびビグアナイド系殺菌剤を１〜９８重量％含有するもの、式（Ｉ）の化合物を３〜５０重量％、トリエタノールアミンを０．００５〜３重量％およびビグアナイド系殺菌剤を３〜５０重量％含有するもの、式（Ｉ）の化合物を５〜１５重量％、トリエタノールアミンを０．００１〜１重量％およびビグアナイド系殺菌剤を５〜１５重量％含有するものが挙げられる。 Examples of the fungicide composition of the present invention provided in solid or semi-solid form include 1 to 99% by weight of the compound of formula (I) and 0.0001 to 5% by weight of triethanolamine, A compound containing 3 to 50% by weight of the compound of the formula (I) and 0.005 to 3% by weight of triethanolamine, 5 to 15% by weight of the compound of the formula (I) and 0.001 to 1 of triethanolamine. What contains weight% is mentioned. Furthermore, examples of the bactericidal composition of the present invention containing other bactericidal components include 1 to 98% by weight of the compound of formula (I), 0.0001 to 5% by weight of triethanolamine and 1 of the biguanide type bactericide. ˜98% by weight, 3 to 50% by weight of compound of formula (I), 0.005 to 3% by weight of triethanolamine and 3 to 50% by weight of biguanide fungicide, ) Containing 5 to 15 wt%, triethanolamine 0.001 to 1 wt% and biguanide fungicide 5 to 15 wt%.
水溶液の形態で提供される本発明の殺菌剤組成物の例としては、式（Ｉ）の化合物を０．００１〜５０重量％およびトリエタノールアミンを０．０７５〜５０重量％含有する水溶液からなるもの、式（Ｉ）の化合物を１〜２０重量％およびトリエタノールアミンを０．０９〜０．３重量％含有する水溶液からなるもの、式（Ｉ）の化合物を３〜９重量％およびトリエタノールアミンを０．１〜０．２５重量％含有する水溶液からなるものが挙げられ、式（Ｉ）の化合物を１〜２０重量％およびトリエタノールアミンを０．０９〜０．３重量％含有する水溶液からなるものが好ましく、式（Ｉ）の化合物を３〜９重量％およびトリエタノールアミンを０．１〜０．２５重量％含有する水溶液からなるものが特に好ましい。さらに他の殺菌成分を含む本発明の殺菌剤組成物の例としては、式（Ｉ）の化合物を０．００１〜５０重量％、トリエタノールアミンを０．０７５〜９９重量％およびビグアナイド系殺菌剤を０．０００５〜３０重量％含有する水溶液からなるもの、式（Ｉ）の化合物を１〜２０重量％、トリエタノールアミンを０．０９〜９８重量％およびビグアナイド系殺菌剤を１〜２０重量％含有する水溶液からなるもの、式（Ｉ）の化合物を３〜９重量％、トリエタノールアミンを１〜９３重量％およびビグアナイド系殺菌剤を４〜１６重量％含有する水溶液からなるものが挙げられ、式（Ｉ）の化合物を１〜２０重量％、トリエタノールアミンを０．０９〜９８重量％およびビグアナイド系殺菌剤を１〜２０重量％含有する水溶液からなるものが好ましく、式（Ｉ）の化合物を３〜９重量％、トリエタノールアミンを１〜９３重量％およびビグアナイド系殺菌剤を４〜１６重量％含有する水溶液からなるものがより好ましく、式（Ｉ）の化合物を３〜９重量％、トリエタノールアミンを１〜９３重量％およびポリヘキサメチレンビグアナイド塩酸塩を４〜１６重量％含有する水溶液からなるものが特に好ましい。 An example of the fungicide composition of the present invention provided in the form of an aqueous solution comprises an aqueous solution containing 0.001 to 50% by weight of the compound of formula (I) and 0.075 to 50% by weight of triethanolamine. Consisting of an aqueous solution containing 1-20% by weight of the compound of formula (I) and 0.09-0.3% by weight of triethanolamine, 3-9% by weight of the compound of formula (I) and triethanol Examples include an aqueous solution containing 0.1 to 0.25% by weight of an amine, and an aqueous solution containing 1 to 20% by weight of a compound of formula (I) and 0.09 to 0.3% by weight of triethanolamine. Those consisting of an aqueous solution containing 3 to 9% by weight of the compound of the formula (I) and 0.1 to 0.25% by weight of triethanolamine are particularly preferred. Furthermore, examples of the fungicide composition of the present invention containing other fungicide components include 0.001 to 50% by weight of the compound of formula (I), 0.075 to 99% by weight of triethanolamine and a biguanide fungicide. 1 to 20% by weight of a compound of formula (I), 0.09 to 98% by weight of triethanolamine and 1 to 20% by weight of a biguanide fungicide And an aqueous solution containing 3 to 9% by weight of the compound of formula (I), 1 to 93% by weight of triethanolamine and 4 to 16% by weight of a biguanide fungicide, Preferred is an aqueous solution containing 1 to 20% by weight of the compound of formula (I), 0.09 to 98% by weight of triethanolamine and 1 to 20% by weight of a biguanide fungicide. More preferred is an aqueous solution containing 3 to 9% by weight of the compound of formula (I), 1 to 93% by weight of triethanolamine and 4 to 16% by weight of a biguanide fungicide, Particularly preferred is an aqueous solution containing 3 to 9% by weight of the compound, 1 to 93% by weight of triethanolamine and 4 to 16% by weight of polyhexamethylene biguanide hydrochloride.
また、水溶液の形態の本発明の殺菌剤組成物は、使用者の目的に応じて、さらに水を加えて希釈液として用いることもできるが、希釈液として用いる場合でも式（Ｉ）の化合物の割合が０．００１〜５０重量％となるように希釈するのが好ましい。例えば、式（Ｉ）の化合物を０．００１〜０．２５重量％およびトリエタノールアミンを０．０００４〜０．２５重量％含有する水溶液、式（Ｉ）の化合物を０．００５〜０．１重量％およびトリエタノールアミンを０．０００５〜０．００１５重量％含有する水溶液、式（Ｉ）の化合物を０．０１５〜０．０４５重量％およびトリエタノールアミンを０．０００６〜０．００１重量％含有する水溶液として用いることができ、式（Ｉ）の化合物を０．００５〜０．１重量％およびトリエタノールアミンを０．０００５〜０．００１５重量％含有する水溶液として用いることが好ましく、式（Ｉ）の化合物を０．０１５〜０．０４５重量％およびトリエタノールアミンを０．０００６〜０．００１重量％含有する水溶液として用いることが特に好ましい。さらに他の殺菌成分を含む場合には、例えば、式（Ｉ）の化合物を０．００１〜０．２５重量％、トリエタノールアミンを０．０００４〜０．５重量％およびビグアナイド系殺菌剤を０．０００５〜０．１５重量％含有する水溶液、式（Ｉ）の化合物を０．００５〜０．１重量％、トリエタノールアミンを０．０００５〜０．４５重量％およびビグアナイド系殺菌剤を０．００５〜０．１重量％含有する水溶液、式（Ｉ）の化合物を０．０１５〜０．０４５重量％、トリエタノールアミンを０．００５〜０．４重量％およびビグアナイド系殺菌剤を０．０２〜０．０８重量％含有する水溶液として用いることができ、式（Ｉ）の化合物を０．００５〜０．１重量％、トリエタノールアミンを０．０００５〜０．４５重量％およびビグアナイド系殺菌剤を０．００５〜０．１重量％含有する水溶液として用いることが好ましく、式（Ｉ）の化合物を０．０１５〜０．０４５重量％、トリエタノールアミンを０．００５〜０．４重量％およびビグアナイド系殺菌剤を０．０２〜０．０８重量％含有する水溶液として用いることがより好ましく、式（Ｉ）の化合物を０．０１５〜０．０４５重量％、トリエタノールアミンを０．００５〜０．４重量％およびポリヘキサメチレンビグアナイド塩酸塩を０．０２〜０．０８重量％含有する水溶液として用いることが特に好ましい。 Further, the fungicidal composition of the present invention in the form of an aqueous solution can be used as a diluent by further adding water depending on the purpose of the user, but even when used as a diluent, the compound of the formula (I) It is preferable to dilute the ratio to be 0.001 to 50% by weight. For example, an aqueous solution containing 0.001 to 0.25 wt% of the compound of formula (I) and 0.0004 to 0.25 wt% of triethanolamine, 0.005 to 0.1 of the compound of formula (I) % Aqueous solution containing 0.0005 to 0.0015% by weight of triethanolamine, 0.015 to 0.045% by weight of the compound of formula (I) and 0.0006 to 0.001% by weight of triethanolamine It can be used as an aqueous solution containing, and is preferably used as an aqueous solution containing 0.005 to 0.1% by weight of the compound of formula (I) and 0.0005 to 0.0015% by weight of triethanolamine. Specially used as an aqueous solution containing 0.015 to 0.045% by weight of the compound of I) and 0.0006 to 0.001% by weight of triethanolamine. Preferred. When other sterilizing components are further included, for example, 0.001 to 0.25% by weight of the compound of the formula (I), 0.0004 to 0.5% by weight of triethanolamine, and 0 An aqueous solution containing 0.005 to 0.15% by weight, 0.005 to 0.1% by weight of the compound of formula (I), 0.0005 to 0.45% by weight of triethanolamine and 0.005% of a biguanide fungicide. An aqueous solution containing 005 to 0.1% by weight, 0.015 to 0.045% by weight of the compound of formula (I), 0.005 to 0.4% by weight of triethanolamine and 0.02 of a biguanide fungicide. Can be used as an aqueous solution containing ˜0.08% by weight, 0.005-0.1% by weight of the compound of formula (I), 0.0005-0.45% by weight of triethanolamine and biguanide It is preferably used as an aqueous solution containing 0.005 to 0.1% by weight of a disinfectant, 0.015 to 0.045% by weight of the compound of formula (I), and 0.005 to 0.4% by weight of triethanolamine. % And a biguanide fungicide is preferably used as an aqueous solution containing 0.02 to 0.08% by weight, 0.015 to 0.045% by weight of the compound of the formula (I), 0.005% of triethanolamine It is particularly preferred to use as an aqueous solution containing .about.0.4 wt% and polyhexamethylene biguanide hydrochloride 0.02 to 0.08 wt%.
本発明の殺菌剤組成物は、通常、水溶液の形態で殺菌対象物と接触させることによって殺菌を行うことができる。接触方法は特に限定されず、散布、噴霧、浸漬、拭き取り等の一般的な方法で実施することができる。 The disinfectant composition of the present invention can usually be sterilized by bringing it into contact with an object to be sterilized in the form of an aqueous solution. A contact method is not specifically limited, It can implement by general methods, such as dispersion | spreading, spraying, immersion, and wiping.
本発明の殺菌剤組成物を殺菌対象物と接触させる際の接触時間は特に限定されず、有効成分の濃度により、適宜定めればよいが、常温で作用させる場合には通常３０秒〜１０分間、好ましくは１〜５分間で十分な殺菌効果が得られる。 The contact time when the bactericidal composition of the present invention is brought into contact with the object to be sterilized is not particularly limited, and may be appropriately determined depending on the concentration of the active ingredient, but is usually 30 seconds to 10 minutes when acting at normal temperature. Preferably, a sufficient bactericidal effect is obtained in 1 to 5 minutes.
半固形または水溶液の形態の本発明の殺菌剤組成物の調製に用いる水は、イオン交換水、蒸留水等の精製水、水道水および地下水、伏流水等の天然水のいずれであってもよいが、塩素や金属イオンの含有量が少ない点で精製水が好ましい。 The water used for the preparation of the disinfectant composition of the present invention in the form of a semi-solid or aqueous solution may be any of purified water such as ion-exchanged water and distilled water, natural water such as tap water and underground water, and underground water. However, purified water is preferable in terms of low content of chlorine and metal ions.
本発明の殺菌剤組成物は、食品工場、病院、畜舎、ホテル、レストラン、学校、店舗等の床や壁を殺菌する設備用ないし食品取扱設備用殺菌剤組成物として有用である。また、食品工場等で使用される食品製造・加工機器や器具等の食品用途の対象の殺菌にも有用である。食品製造・加工機器としては、各種の攪拌機、混合機、ホモジナイザー、自動カッター等が挙げられる。器具としては、まな板、包丁、食器、食品用容器、布巾等が挙げられる。 The disinfectant composition of the present invention is useful as a disinfectant composition for facilities for sterilizing floors and walls of food factories, hospitals, barns, hotels, restaurants, schools, stores, etc. or for food handling facilities. It is also useful for sterilization of food applications such as food production / processing equipment and utensils used in food factories. Examples of food production / processing equipment include various stirrers, mixers, homogenizers, and automatic cutters. Examples of instruments include cutting boards, kitchen knives, tableware, food containers, and cloths.
本発明の殺菌剤組成物は、カビなどの真菌類や一般細菌への殺菌効果に加え、第四級アンモニウム塩および／またはビグアナイド系殺菌剤に対し抵抗性を有する微生物、例えば、ジデシルジメチルアンモニウムクロライド（ＤＤＡＣ）および／またはポリヘキサメチレンビグアナイド塩酸塩（ＰＨＭＢ）に対し抵抗性を有する微生物に対して殺菌力を発揮するものであり、かかる微生物が存在する対象に対して使用する殺菌剤組成物として特に有用である。 The fungicide composition of the present invention is a microorganism having resistance to quaternary ammonium salts and / or biguanide fungicides, for example, didecyldimethylammonium ammonium, in addition to fungicidal effects on fungi such as molds and general bacteria. Disinfectant composition that exerts bactericidal activity against microorganisms having resistance to chloride (DDAC) and / or polyhexamethylene biguanide hydrochloride (PHMB), and is used for a subject in which such microorganisms exist As particularly useful.
また、本発明の殺菌剤組成物は、第四級アンモニウム塩および／またはビグアナイド系殺菌剤と比較して、長期間にわたって使用しても当該組成物に対し抵抗性を有する微生物が発生し難いものである。したがって、第四級アンモニウム塩および／またはビグアナイド系殺菌剤の使用によって当該薬剤に対する抵抗性を有する微生物が発生し得る対象に対して使用する殺菌剤組成物としても有用である。 In addition, the fungicide composition of the present invention is less susceptible to the generation of microorganisms having resistance to the composition even when used over a long period of time, compared to quaternary ammonium salts and / or biguanide fungicides. It is. Therefore, it is also useful as a bactericidal composition used for a subject where a microorganism having resistance to the drug can be generated by using a quaternary ammonium salt and / or a biguanide fungicide.
第四級アンモニウム塩および／またはビグアナイド系殺菌剤に対し抵抗性を有する微生物の例としては、Pseudomonas属の微生物、およびSerratia属の微生物、例えばSerratia marcescens、Serratia liquefaciens等が挙げられる。 Examples of microorganisms having resistance to quaternary ammonium salts and / or biguanide fungicides include microorganisms belonging to the genus Pseudomonas and microorganisms belonging to the genus Serratia such as Serratia marcescens and Serratia liquefaciens.
本発明の殺菌剤組成物は、連続または継続して使用するための組成物として適するものである。具体的には、本発明の殺菌剤組成物は、長期間にわたり連続または継続して使用しても当該組成物に対して抵抗性を有する微生物が発生し難いものであり、同一の対象に対して繰り返し使用する場合に、該組成物に対し抵抗性を有する微生物の発生が、第四級アンモニウム塩および／またはビグアナイド系殺菌剤を該対象に対し同様にして繰り返し使用した場合と比較して少ないことを特徴とする。ここで、「同一の対象に対して繰り返し使用」とは、同一の対象に対し、または、対象の微生物種が特定されている場合には同一の微生物種に対し、同一の組成物を複数回（例えば、２回、３回、４回、５回、６回、７回、８回もしくはそれ以上）使用することをいう。また、「連続して使用」とは、例えば（組成物Ａ、組成物Ａ、組成物Ａ・・・）のように、同じ組成物を２回以上続けて使用することをいう。「継続して使用」とは、同じ組成物を２回以上続けては使用しないが、間で別の組成物を使用して、同一の対象に対しての使用を継続することをいい、例えば（組成物Ａ、組成物Ｂ、組成物Ｃ、組成物Ａ、組成物Ｄ、・・・）の場合、組成物Ａは連続してではなく、継続して使用されているといえる。 The disinfectant composition of the present invention is suitable as a composition for continuous or continuous use. Specifically, the disinfectant composition of the present invention is resistant to the generation of microorganisms having resistance to the composition even when used continuously or continuously over a long period of time. When used repeatedly, the generation of microorganisms having resistance to the composition is less than when the quaternary ammonium salt and / or biguanide fungicide are used repeatedly on the subject in the same manner. It is characterized by that. Here, “repeated use for the same target” means that the same composition is applied multiple times to the same target or to the same microbial species when the target microbial species is specified. (For example, 2, 3, 4, 5, 6, 7, 8, or more). Further, “use continuously” means that the same composition is continuously used twice or more like (Composition A, Composition A, Composition A...). “Continuous use” means that the same composition is not used more than once, but another composition is used in between, and the use on the same subject is continued. In the case of (Composition A, Composition B, Composition C, Composition A, Composition D,...), It can be said that the composition A is used continuously, not continuously.
以下、実施例により本発明をさらに説明する。尚、以下の各試験において、表中の「＋」は菌の増殖が確認されたことを示し、「−」は菌の増殖が確認されなかったことを表す。 Hereinafter, the present invention will be further described by examples. In each of the following tests, “+” in the table indicates that the growth of the bacteria was confirmed, and “−” indicates that the growth of the bacteria was not confirmed.
試験例１
下記に示す供試菌i〜viiiを１０６ｃｆｕ／ｍｌとなるように生理食塩水で希釈した菌液０．０３ｍｌ（供試菌iiiおよびviiiは０．１ｍｌ）と、薬剤濃度が１．２５〜３２０ｐｐｍのＰＨＭＢ水溶液３ｍｌ（供試菌iiiおよびviiiは１０ｍｌ）とを混合した後、２５℃で５分間保持した。感作時間経過後、再度攪拌した後、各混合物から１白金耳を取り、ＢＨＩブイヨン培地１０ｍｌ（供試菌viiiのみＳＣＤＬＰ培地１０ｍｌ）に接種し、３０℃で４８時間培養した（供試菌iiのみ１２０時間培養）。菌未接種のＢＨＩブイヨン培地（供試菌viiiのみ菌未接種のＳＣＤＬＰ培地）を基準とし、目視で培地の濁りを比較して、ＰＨＭＢの各供試菌に対する殺菌効果を確認した。結果を表１に示す。
ＰＨＭＢ：ポリヘキサメチレンビグアナイド塩酸塩
ＢＨＩ：ブレインハートインフュージョン
ＳＣＤＬＰ：Soybean-Casein Digest Broth with Lecithin & Polysorbate 80
供試菌i ：Ｐｓｅｕｄｏｍｏｎａｓ ａｅｒｕｇｉｎｏｓａ ＮＢＲＣ１３７３６
供試菌ii ：Ａｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒ ＡＴＣＣ１６４０４
供試菌iii ：Ｂａｃｉｌｌｕｓ ｃｅｒｅｕｓ ＮＢＲＣ１５３０５
供試菌iv ：Ｓｅｒｒａｔｉａ ｍａｒｃｅｓｃｅｎｓ（食品工場分離菌１）
供試菌v ：Ｓｅｒｒａｔｉａ ｌｉｑｕｅｆａｃｉｅｎｓ（食品工場分離菌２）
供試菌vi ：Ｓｅｒｒａｔｉａ ｍａｒｃｅｓｃｅｎｓ（食品工場分離菌３）
供試菌vii ：Ｓｅｒｒａｔｉａ ｍａｒｃｅｓｃｅｎｓ（食品工場分離菌４）
供試菌viii：Ｂａｃｉｌｌｕｓ ｓｕｂｔｉｌｉｓ ＩＦＯ１３７１９
Test example 1
0.03 ml of a bacterial solution obtained by diluting the following test bacteria i to viii with physiological saline so as to be 10 6 cfu / ml (test bacteria iii and viii are 0.1 ml), and the drug concentration is 1.25 After mixing 3 ml of a ~ 320 ppm PHMB aqueous solution (test bacteria iii and viii were 10 ml), the mixture was kept at 25 ° C for 5 minutes. After the sensitization time, after stirring again, 1 platinum loop was taken from each mixture, inoculated into 10 ml of BHI broth medium (10 ml of SCDLP medium only for test bacteria viii) and cultured at 30 ° C. for 48 hours (test bacteria ii Only for 120 hours). Based on the BHI broth medium not inoculated with bacteria (SCDLP medium in which only test bacteria viii were not inoculated), the turbidity of the medium was visually compared to confirm the bactericidal effect of PHMB on each test bacteria. The results are shown in Table 1.
PHMB: Polyhexamethylene biguanide hydrochloride BHI: Brain Heart Infusion SCDLP: Soybean-Casein Digest Broth with Lecithin & Polysorbate 80
Test bacteria i: Pseudomonas aeruginosa NBRC13736
Test bacteria ii: Aspergillus niger ATCC 16404
Test bacteria iii: Bacillus cereus NBRC15305
Test bacteria iv: Serratia marcescens (Food factory isolate 1)
Test bacteria v: Serratia liquidfaciens (Food factory isolate 2)
Test bacteria vi: Serratia marcescens (Food factory isolate 3)
Test bacteria vii: Serratia marcescens (Food factory isolate 4)
Test bacteria viii: Bacillus subtilis IFO13719
試験例２
試験例１で用いた供試菌i〜viiを用い、薬剤をＤＤＡＣに変更し、試験例１と同様の方法でＤＤＡＣの各供試菌に対する殺菌効果を確認した。結果を表２に示す。
ＤＤＡＣ：ジデシルジメチルアンモニウムクロライド
Test example 2
Using the test bacteria i to vii used in Test Example 1, the drug was changed to DDAC, and the bactericidal effect of each DDAC on the test bacteria was confirmed by the same method as Test Example 1. The results are shown in Table 2.
DDAC: Didecyldimethylammonium chloride
試験例３
式（Ｉ）の化合物〔１，１０−ジ（３−デシル−２−メチルイミダゾリウム）デカンジクロライド〕およびＰＨＭＢを下記配合比で含有する水溶液を調製し、３時間後の外観変化を確認した。結果を表３に示す。
Test example 3
An aqueous solution containing the compound of formula (I) [1,10-di (3-decyl-2-methylimidazolium) decane dichloride] and PHMB at the following blending ratio was prepared, and the appearance change after 3 hours was confirmed. The results are shown in Table 3.
実施例１〜６及び比較例１〜１３
殺菌力試験１（カビ）
下記に示す供試菌の胞子懸濁液を１０６ｃｆｕ／ｍｌとなるように生理食塩水で希釈した菌液０．０３ｍｌと、表４に示す殺菌剤組成物を殺菌剤組成物濃度が０．１〜０．３重量％となるように希釈した水溶液３ｍｌとを混合した後、２５℃で５分間保持した。感作時間経過後、再度攪拌した後、各混合物から１白金耳を取り、ＢＨＩブイヨン培地１０ｍｌに接種し、３０℃で１２０時間培養した。菌未接種のＢＨＩブイヨン培地を基準とし、目視で培地の濁りを比較して、殺菌剤組成物の殺菌効果を判定した。
供試菌ii：Ａｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒ ＡＴＣＣ１６４０４
Examples 1-6 and Comparative Examples 1-13
Bactericidal test 1 (mold)
0.03 ml of a bacterial solution obtained by diluting a spore suspension of the test bacteria shown below with physiological saline so as to be 10 6 cfu / ml, and the fungicide composition shown in Table 4 with a fungicide composition concentration of 0 The mixture was mixed with 3 ml of an aqueous solution diluted to 0.1 to 0.3% by weight and then kept at 25 ° C. for 5 minutes. After the sensitization time had elapsed, the mixture was stirred again, one platinum loop was taken from each mixture, inoculated into 10 ml of BHI broth medium, and cultured at 30 ° C. for 120 hours. The sterilization effect of the bactericidal composition was determined by comparing the turbidity of the medium visually with reference to a BHI broth medium not inoculated with bacteria.
Test bacteria ii: Aspergillus niger ATCC 16404
結果を表５に示す。本発明の殺菌剤組成物は、比較例の組成物に比べてカビに対する殺菌力が優れていた。 The results are shown in Table 5. The fungicidal composition of the present invention was superior in fungicidal power against molds as compared with the composition of the comparative example.
殺菌力試験２（芽胞菌）
下記に示す供試菌の芽胞懸濁液を１０６ｃｆｕ／ｍｌとなるように生理食塩水で希釈した菌液０．１ｍｌと、表４に示す殺菌剤組成物を殺菌剤組成物濃度が０．１〜０．３重量％となるように希釈した水溶液１０ｍｌとを混合した後、２５℃で５分間保持した。感作時間経過後再度攪拌した後、各混合物から１白金耳を取り、ＢＨＩブイヨン培地１０ｍｌに接種し、３０℃で４８時間培養した。菌未接種のＢＨＩブイヨン培地を基準とし、目視で培地の濁りを比較して、各菌体に対する殺菌剤組成物の殺菌効果を判定した。
供試菌iii：Ｂａｃｉｌｌｕｓ ｃｅｒｅｕｓ ＮＢＲＣ１５３０５
Bactericidal test 2 (spore fungus)
0.1 ml of a bacterial solution obtained by diluting the spore suspension of the test bacteria shown below with physiological saline so as to be 10 6 cfu / ml, and the fungicide composition shown in Table 4 with a fungicide composition concentration of 0 The mixture was mixed with 10 ml of an aqueous solution diluted to 0.1 to 0.3% by weight and then kept at 25 ° C. for 5 minutes. After stirring for the sensitization time, 1 platinum loop was taken from each mixture, inoculated into 10 ml of BHI broth medium, and cultured at 30 ° C. for 48 hours. Based on the BHI broth medium that had not been inoculated with bacteria, the turbidity of the medium was visually compared to determine the bactericidal effect of the bactericide composition on each cell.
Test bacteria iii: Bacillus cereus NBRC15305
結果を表６に示す。本発明の殺菌剤組成物は、比較例の組成物に比べ芽胞菌に対する殺菌力が優れていた。 The results are shown in Table 6. The bactericidal composition of the present invention was superior in bactericidal power against spore bacteria compared to the composition of the comparative example.
殺菌力試験３（薬剤抵抗性菌）
食品工場から分離された下記供試菌をＢＨＩブイヨン培地で３０℃にて、２４時間培養し、１０６ｃｆｕ／ｍｌとなるように生理食塩水で希釈した菌液０．０３ｍｌと、実施例１〜５で用いた殺菌剤組成物および表７に示す殺菌剤組成物を殺菌剤組成物濃度が０．０２５〜０．１重量％となるように希釈した水溶液３ｍｌとを混合した後、２５℃で５分間保持した。感作時間経過後再度攪拌した後、各混合物から１白金耳を取り、ＢＨＩブイヨン培地１０ｍｌに接種し、３０℃で４８時間培養した。菌未接種のＢＨＩブイヨン培地を基準とし、目視で培地の濁りを比較して、各菌体に対する殺菌剤組成物の殺菌効果を判定した。
供試菌iv：Ｓｅｒｒａｔｉａ ｍａｒｃｅｓｃｅｎｓ（食品工場分離菌１）
Bactericidal test 3 (drug-resistant bacteria)
The following test bacteria isolated from a food factory were cultured in a BHI broth medium at 30 ° C. for 24 hours, and 0.03 ml of a bacterial solution diluted with physiological saline to 10 6 cfu / ml, Example 1 After mixing the bactericidal composition used in -5 and the bactericidal composition shown in Table 7 with 3 ml of an aqueous solution diluted so that the bactericidal composition concentration is 0.025 to 0.1 wt%, For 5 minutes. After stirring for the sensitization time, 1 platinum loop was taken from each mixture, inoculated into 10 ml of BHI broth medium, and cultured at 30 ° C. for 48 hours. Based on the BHI broth medium that had not been inoculated with bacteria, the turbidity of the medium was visually compared to determine the bactericidal effect of the bactericide composition on each cell.
Test bacteria iv: Serratia marcescens (Food factory isolate 1)
結果を表８に示す。本発明の殺菌剤組成物は、比較例の組成物に比べ薬剤抵抗性菌に対する殺菌力が優れていた。 The results are shown in Table 8. The bactericidal composition of the present invention was superior in bactericidal power against drug-resistant bacteria as compared with the composition of the comparative example.
殺菌力試験４（薬剤抵抗性菌）
食品工場から分離された下記供試菌をＢＨＩブイヨン培地で３０℃にて、２４時間前培養し、１０６ｃｆｕ／ｍｌとなるように生理食塩水で希釈した菌液０．０３ｍｌと、実施例１〜５で用いた殺菌剤組成物および表７に示す殺菌剤組成物を殺菌剤組成物濃度が０．０８〜１．３３重量％となるように希釈した水溶液３ｍｌとを混合した後、２５℃で１分間保持した。感作時間経過後再度攪拌した後、各混合物から１白金耳を取り、ＢＨＩブイヨン培地１０ｍｌに接種し、３０℃で１２０時間本培養した。菌未接種のＢＨＩブイヨン培地を基準とし、目視で培地の濁りを比較して、各菌体に対する殺菌剤組成物の殺菌効果を判定した。
供試菌v：Ｓｅｒｒａｔｉａ ｌｉｑｕｅｆａｃｉｅｎｓ（食品工場分離菌２）
Bactericidal test 4 (drug-resistant bacteria)
The following test bacteria isolated from food factories were pre-cultured in BHI broth medium at 30 ° C. for 24 hours and diluted with physiological saline to a concentration of 10 6 cfu / ml. After mixing the bactericidal composition used in 1-5 and the bactericidal composition shown in Table 7 with 3 ml of an aqueous solution diluted so that the bactericidal composition concentration is 0.08 to 1.33% by weight, 25 Hold for 1 minute at ° C. After the sensitization time, the mixture was stirred again, one platinum loop was taken from each mixture, inoculated into 10 ml of BHI broth medium, and main cultured at 30 ° C. for 120 hours. Based on the BHI broth medium that had not been inoculated with bacteria, the turbidity of the medium was visually compared to determine the bactericidal effect of the bactericide composition on each cell.
Test bacteria v: Serratia liquidfaciens (Food factory isolate 2)
結果を表９に示す。本発明の殺菌剤組成物は、比較例の組成物に比べ薬剤抵抗性菌に対する殺菌力が優れていた。 The results are shown in Table 9. The bactericidal composition of the present invention was superior in bactericidal power against drug-resistant bacteria as compared with the composition of the comparative example.
薬剤耐性化抑制試験
日本化学療法学会標準法（微量液体希釈法）に準じ、最小発育阻止濃度（ＭＩＣ）の測定を連続的に実施した。実施例１および比較例１３の組成物を滅菌水で希釈し、組成物濃度０．００７〜１．７９２重量％の薬液を調製し、指定濃度の２倍濃度に調整したニュートリエントブロス培地（栄研化学株式会社製、普通ブイヨン培地‘栄研’Ｅ−ＭＣ３５）を薬液と同量添加し、撹拌後、マイクロタイタープレート（９６ウェル）に１５０μｌ／ウェルずつ分注した。次に食品工場から分離された下記供試菌をＮＢ培地にて３０℃で２０時間培養した菌液を１０７ｃｆｕ／ｍｌとなるように生理食塩水で希釈した後、上記で作製した培地注入済みのマイクロタイタープレートに７．５μｌ／ウェルずつ接種した。これを３０℃の恒温器内で４８時間培養し、目視にて菌の生育の有無を確認し、ＭＩＣを測定した。さらに生育が確認されたウェルの中で薬剤濃度が最大であったウェルから菌液を採取し、１０７ｃｆｕ／ｍｌとなるように生理食塩水で希釈した菌液を用いて、上記と同様にして再度ＭＩＣを測定した。この操作を繰り返し、ＭＩＣの測定を合計８回行い、ＭＩＣの変化を確認した。
供試菌vi：Ｓｅｒｒａｔｉａ ｍａｒｃｅｓｃｅｎｓ（食品工場分離菌３）
供試菌vii：Ｓｅｒｒａｔｉａ ｍａｒｃｅｓｃｅｎｓ（食品工場分離菌４）
Anti-drug resistance inhibition test According to the standard method of the Japanese Society of Chemotherapy (micro liquid dilution method), the minimum inhibitory concentration (MIC) was continuously measured. The composition of Example 1 and Comparative Example 13 was diluted with sterilized water to prepare a chemical solution having a composition concentration of 0.007 to 1.792% by weight and adjusted to a nutrient broth medium (Eiwa) adjusted to twice the designated concentration. A normal bouillon medium “Eiken” E-MC35) manufactured by Ken Chemical Co., Ltd. was added in the same amount as the chemical solution, and after stirring, it was dispensed at 150 μl / well into a microtiter plate (96 well). Next, a bacterial solution obtained by culturing the following test bacteria isolated from a food factory in NB medium at 30 ° C. for 20 hours was diluted with physiological saline to 10 7 cfu / ml, and then the medium injection prepared above was injected. 7.5 μl / well was inoculated into the finished microtiter plate. This was cultured in a thermostat at 30 ° C. for 48 hours, and the presence or absence of bacterial growth was visually confirmed, and the MIC was measured. Further, among the wells in which growth was confirmed, the bacterial solution was collected from the well with the highest drug concentration, and the bacterial solution diluted with physiological saline so as to be 10 7 cfu / ml was used in the same manner as described above. The MIC was measured again. This operation was repeated, and the MIC was measured a total of 8 times to confirm the change in MIC.
Test bacteria vi: Serratia marcescens (Food factory isolate 3)
Test bacteria vii: Serratia marcescens (Food factory isolate 4)
結果を表１０および１１に示す。実施例１は、８回目の試験でもＭＩＣが０．０５６重量％（供試菌vi）および０．０２８重量％（供試菌vii）と低く、薬剤抵抗性菌が発生し難いことが確認された。 The results are shown in Tables 10 and 11. In Example 1, the MIC was as low as 0.056% by weight (test bacteria vi) and 0.028% by weight (test bacteria vii) even in the eighth test, and it was confirmed that drug-resistant bacteria were hardly generated. It was.
金属腐食性試験
実施例１，５及び比較例１２，１３に示す各製剤の０．３％水溶液６０ｍｌを７０ｍｌ容の蓋付ガラス瓶に入れ、その中に銅製ピース（縦５０ｍｍ×横３０ｍｍ×厚さ１ｍｍ）を浸漬し、２５℃の恒温器内で１ヶ月間保存した。保存後の銅製ピースを目視により外観観察し、下記基準で腐食性を判定した。尚、薬剤水溶液の代わりに水道水を用いて、同様に保存した銅製ピースを対照とした。
○：対照より腐食が少ない △：対照と同等 ×：対照に比べ腐食が多い
Metal Corrosion Test 60 ml of a 0.3% aqueous solution of each formulation shown in Examples 1 and 5 and Comparative Examples 12 and 13 was placed in a 70 ml glass bottle with a lid, and a copper piece (length 50 mm × width 30 mm × thickness) 1 mm) and was stored in a thermostat at 25 ° C. for 1 month. The appearance of the copper pieces after storage was visually observed, and the corrosivity was determined according to the following criteria. In addition, the copper piece preserve | saved similarly using the tap water instead of chemical | medical-agent aqueous solution was made into the control | contrast.
○: Less corrosion than control △: Equivalent to control ×: More corrosion than control
結果を表１２に示す。実施例１の薬剤で処理したピースは、処理前のピースと同等の外観が保持されており、対照に比べ明らかに腐食が抑制されていた。実施例５の薬剤で処理したピースは、わずかに退色が見られるものの、錆や変色の発生は確認されなかった。比較例１２の薬剤で処理したピースは、ピース全体が変色しており、対照よりも腐食が進行していた。比較例１３の薬剤で処理したピースは、明らかに退色しており、対照と同程度の外観であった。 The results are shown in Table 12. The piece treated with the chemical of Example 1 maintained the same appearance as the piece before treatment, and the corrosion was clearly suppressed as compared with the control. The piece treated with the chemical of Example 5 was slightly discolored, but no rust or discoloration was observed. In the piece treated with the chemical of Comparative Example 12, the entire piece was discolored and was more corroded than the control. The piece treated with the drug of Comparative Example 13 was clearly faded and looked similar to the control.
Claims (13)
［式中、Ｒ１は炭素数１〜３の飽和直鎖アルキル基、Ｒ２は炭素数８〜１２の飽和直鎖アルキル基、Ｘ−はハロゲンイオン、Ｙは炭素数８〜１２の飽和直鎖アルキレン基を表す］。 Bactericidal composition comprising a compound of formula (I) and triethanolamine:
[Wherein R 1 is a saturated linear alkyl group having 1 to 3 carbon atoms, R 2 is a saturated linear alkyl group having 8 to 12 carbon atoms, X − is a halogen ion, and Y is a saturated straight chain alkyl group having 8 to 12 carbon atoms. Represents a chain alkylene group].
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| JP2014043440A (en) * | 2012-07-31 | 2014-03-13 | Ueno Fine Chem Ind Ltd | Solid bactericide composition, and sterilization method |
| CN104923002A (en) * | 2015-06-15 | 2015-09-23 | 临沂大学 | Preparation method and application of air purification agent special for haze prevention window screen |
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| WO1994008972A1 (en) * | 1992-10-20 | 1994-04-28 | Zeneca Limited | Oligomeric heterocyclic salts and their use as antimicrobial agents in swimming pools and spas |
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| JP2014043440A (en) * | 2012-07-31 | 2014-03-13 | Ueno Fine Chem Ind Ltd | Solid bactericide composition, and sterilization method |
| CN104923002A (en) * | 2015-06-15 | 2015-09-23 | 临沂大学 | Preparation method and application of air purification agent special for haze prevention window screen |
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