JPH08119878A - Antimicrobial agent and its production - Google Patents
Antimicrobial agent and its productionInfo
- Publication number
- JPH08119878A JPH08119878A JP28004794A JP28004794A JPH08119878A JP H08119878 A JPH08119878 A JP H08119878A JP 28004794 A JP28004794 A JP 28004794A JP 28004794 A JP28004794 A JP 28004794A JP H08119878 A JPH08119878 A JP H08119878A
- Authority
- JP
- Japan
- Prior art keywords
- antimicrobial agent
- salt
- cationic
- anionic surfactant
- fatty acid
- 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
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、カチオン性殺菌剤の高
い殺菌力の発現を可能とする、カチオン性殺菌剤とアニ
オン性界面活性剤との複合塩からなる殺菌剤及びその製
造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a bactericidal agent comprising a complex salt of a cationic bactericidal agent and an anionic surfactant, which enables the cationic bactericidal agent to exhibit high bactericidal activity, and a method for producing the same.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来よ
り、歯磨、洗口剤等の口腔用組成物に歯垢形成を抑制さ
せるため塩化セチルピリジニウム、塩化ベンゼトニウム
等のカチオン性殺菌剤を配合することが知られている。2. Description of the Related Art Conventionally, a cationic bactericide such as cetylpyridinium chloride or benzethonium chloride is blended with oral compositions such as toothpaste and mouthwash in order to suppress plaque formation. It is known.
【０００３】しかしながら、口腔用組成物には通常アニ
オン性界面活性剤が配合されているため、カチオン性殺
菌剤はアニオン性界面活性剤と静電気相互作用により複
合塩を形成して失活し、また非イオン性界面活性剤とは
その可溶化作用により殺菌力が著しく抑制される。一
方、非イオン性界面活性剤の中でポリオキシエチレン・
ポリオキシプロピレンのブロックコポリマ−は塩化セチ
ルピリジニウム等のカチオン性殺菌剤を失活させにくい
ことが知られている（特開平４−２０２１２１号公報）
が、この種の非イオン性界面活性剤は疎水基が小さく、
香料等の可溶化量が小さいため、配合量を増加しなけれ
ばならないし、またＨＬＢを連続的に変化させた製品が
ないため口腔用組成物を調製する際に制限され、しかも
泡立ち性も著しく悪いという問題点がある。However, since an oral composition usually contains an anionic surfactant, the cationic bactericide is deactivated by forming a complex salt with the anionic surfactant by electrostatic interaction. The bactericidal effect of the nonionic surfactant is remarkably suppressed by its solubilizing action. On the other hand, among nonionic surfactants, polyoxyethylene
It is known that block copolymers of polyoxypropylene are unlikely to deactivate cationic bactericides such as cetylpyridinium chloride (Japanese Patent Laid-Open No. 4-202121).
However, this type of nonionic surfactant has a small hydrophobic group,
Since the solubilizing amount of perfume and the like is small, the blending amount has to be increased, and since there is no product in which HLB is continuously changed, it is limited when preparing an oral composition, and the foaming property is also remarkable. There is a problem that it is bad.
【０００４】また、アニオン性界面活性剤の中でカチオ
ン性殺菌剤の殺菌力を効果的に発揮させる実用性のある
技術はほとんどない。In addition, there are few practical techniques for effectively exhibiting the bactericidal activity of the cationic bactericide among the anionic surfactants.
【０００５】本発明は、上記事情に鑑みなされたもの
で、口腔用組成物などに配合した場合にもカチオン性殺
菌剤の殺菌効果を有効に発揮させることができる殺菌剤
及びその製造方法を提供することを目的とする。The present invention has been made in view of the above circumstances, and provides a bactericidal agent capable of effectively exerting the bactericidal effect of a cationic bactericidal agent even when incorporated into an oral composition or the like, and a method for producing the same. The purpose is to do.
【０００６】[0006]
【課題を解決するための手段及び作用】本発明者は、上
記目的を達成するため鋭意検討を行った結果、カチオン
性殺菌剤と、脂肪酸塩、アルキル基の炭素数が８以下の
アルキル硫酸塩及びポリオキシエチレンアルキルエーテ
ル硫酸塩から選ばれるアニオン性界面活性剤とを反応さ
せることにより得られる複合塩が、口腔用組成物などに
配合した場合、アニオン性界面活性剤やノニオン性界面
活性剤が存在していても失活することがなく、カチオン
性殺菌剤の高い殺菌作用を有効に発揮させることを知見
し、本発明をなすに至った。Means and Actions for Solving the Problems As a result of intensive studies to achieve the above-mentioned object, the present inventor has found that a cationic bactericide, a fatty acid salt, and an alkylsulfate having an alkyl group with 8 or less carbon atoms are used. And, a complex salt obtained by reacting with an anionic surfactant selected from polyoxyethylene alkyl ether sulfates, when compounded into an oral composition or the like, an anionic surfactant or a nonionic surfactant is The present invention has been accomplished by finding that the cationic bactericidal agent does not deactivate even if it is present and effectively exerts a high bactericidal action.
【０００７】従って、本発明は、（１）カチオン性殺菌
剤と、脂肪酸塩、アルキル基の炭素数が８以下のアルキ
ル硫酸塩及びポリオキシエチレンアルキルエーテル硫酸
塩から選ばれるアニオン性界面活性剤との複合塩からな
ることを特徴とする殺菌剤、（２）カチオン性殺菌剤
と、脂肪酸塩、アルキル基の炭素数が８以下のアルキル
硫酸塩及びポリオキシエチレンアルキルエ−テル硫酸塩
から選ばれるアニオン性界面活性剤とを反応させて、こ
れらの複合塩を得ることを特徴とする殺菌剤の製造方法
を提供する。Therefore, the present invention provides (1) a cationic bactericide and an anionic surfactant selected from fatty acid salts, alkyl sulfates having an alkyl group having 8 or less carbon atoms, and polyoxyethylene alkyl ether sulfates. Selected from the group consisting of (2) a cationic bactericide, a fatty acid salt, an alkyl sulfate having an alkyl group having 8 or less carbon atoms, and a polyoxyethylene alkyl ether sulfate. Provided is a method for producing a bactericide, which comprises reacting with an anionic surfactant to obtain a complex salt thereof.
【０００８】以下、本発明につき更に詳しく説明する
と、本発明の殺菌剤は、上述したように、カチオン性殺
菌剤と、脂肪酸塩、アルキル硫酸塩及びポリオキシエチ
レンアルキルエーテル硫酸塩との複合塩からなるもので
ある。The present invention will be described in more detail below. The bactericide of the present invention comprises, as described above, a complex salt of a cationic bactericide, a fatty acid salt, an alkyl sulfate and a polyoxyethylene alkyl ether sulfate. It will be.
【０００９】この場合、カチオン性殺菌剤としては、塩
化セチルピリジニウム、塩化ベンゼトニウム、塩化ベン
ザルコニウム、クロルヘキシジン塩酸塩及びグルコン酸
塩、アルキル基の炭素数が８〜１８の塩化アルキルベン
ジルジメチルアンモニウム、アルキル基の炭素数が８〜
２２の塩化アルキルジメチルアンモニウム等が挙げられ
る。In this case, as the cationic bactericide, cetylpyridinium chloride, benzethonium chloride, benzalkonium chloride, chlorhexidine hydrochloride and gluconate, alkylbenzyldimethylammonium chloride having 8 to 18 carbon atoms in the alkyl group, alkyl The number of carbon atoms in the group is 8 to
Alkyldimethylammonium chloride of 22 and the like can be mentioned.
【００１０】次に、脂肪酸塩としては、アルキル基の炭
素数が８〜２２、より好ましくは１２〜１８の飽和又は
不飽和脂肪酸のナトリウム塩、カリウム塩、トリエタノ
−ルアミン塩等の水溶性塩が挙げられ、この脂肪酸は直
鎖であっても分岐鎖であってもよい。Next, as the fatty acid salt, water-soluble salts such as sodium salt, potassium salt, and triethanolamine salt of saturated or unsaturated fatty acid having an alkyl group having 8 to 22 carbon atoms, more preferably 12 to 18 carbon atoms. The fatty acids may be linear or branched.
【００１１】なお、この脂肪酸塩以外に−ＣＯＯＨ基又
はその塩を有する界面活性剤、例えば、ココイルサルコ
シンナトリウム、ラウロイルサルコシンナトリウム、及
びミリストイルサルコシンナトリウム等のＮ−アシルア
ミノ酸塩、カルボキシル化ポリ（オキシエチレン）
（３）ドデシルエ−テル、カルボキシル化ポリ（オキシ
エチレン）（３）ラウリルエ−テルナトリウム塩等のエ
−テルカルボン酸塩、ラウリルジメチルアミノ酢酸ベタ
イン、ヤシ油脂肪酸、アミドプロピルジメチルアミノ酢
酸ベタイン等の酢酸ベタイン及びコ−ル酸塩なども脂肪
酸塩と同様の効果を有する。In addition to the fatty acid salt, a surfactant having a --COOH group or a salt thereof, for example, N-acyl amino acid salts such as cocoyl sarcosine sodium, lauroyl sarcosine sodium, and myristoyl sarcosine sodium, carboxylated poly (oxyethylene). )
(3) Dodecyl ether, carboxylated poly (oxyethylene) (3) Ether carboxylate such as sodium lauryl ether, betaine lauryl dimethylamino acetic acid, coconut oil fatty acid, betaine acetate such as amidopropyl dimethyl amino acetic acid betaine Also, cholate and the like have the same effect as the fatty acid salt.
【００１２】アルキル硫酸塩としては、アルキル基の炭
素数が８以下、より好ましくは６〜８のナトリウム塩、
カリウム塩等の水溶性塩が挙げられる。炭素数が１０以
上ではカチオン性殺菌剤の殺菌力は顕著に低下する。As the alkyl sulfate, a sodium salt having an alkyl group having 8 or less carbon atoms, more preferably 6 to 8,
Water-soluble salts such as potassium salts may be mentioned. When the carbon number is 10 or more, the bactericidal activity of the cationic bactericide is remarkably reduced.
【００１３】ポリオキシエチレンアルキルエ−テル硫酸
塩としては、エチレンオキシド付加モル数が２〜６で、
アルキル基の炭素数が８〜１２であるナトリウム塩、カ
リウム塩等の水溶性塩が挙げられる。The polyoxyethylene alkyl ether sulfate has an ethylene oxide addition mole number of 2 to 6,
Examples thereof include water-soluble salts such as sodium salts and potassium salts in which the alkyl group has 8 to 12 carbon atoms.
【００１４】本発明の上記殺菌剤を得る方法としては、
カチオン性殺菌剤と上記アニオン性界面活性剤とを好ま
しくは１：１のモル比で反応させる。この場合、溶媒と
してはエタノール又はエタノール／水の混合溶媒を用
い、冷却器をつけたナス型フラスコ中で８０〜９０℃の
温度において１〜３時間反応を行なうことが好ましい。The method for obtaining the above-mentioned bactericide of the present invention includes:
The cationic bactericide and the anionic surfactant are reacted preferably in a molar ratio of 1: 1. In this case, it is preferable to use ethanol or a mixed solvent of ethanol / water as the solvent and carry out the reaction at a temperature of 80 to 90 ° C. for 1 to 3 hours in an eggplant type flask equipped with a condenser.
【００１５】本発明のカチオン性殺菌剤／アニオン性界
面活性剤複合塩は、水又はエタノール等の有機溶剤に溶
解又は分散させて使用することができ、特に歯磨、洗口
剤などの口腔用組成物に配合して用いることができ、高
い殺菌効果を与えることができるものである。この場
合、アニオン性界面活性剤やノニオン性界面活性剤が存
在していても本発明殺菌剤が失活することもなく、複合
塩形成に用いたアニオン性界面活性剤の過剰量に可溶化
させた状態でも高い殺菌作用を呈する。The cationic bactericidal / anionic surfactant complex salt of the present invention can be used by dissolving or dispersing it in water or an organic solvent such as ethanol, and in particular, oral compositions such as toothpaste and mouthwash. It can be used by being blended with a product and can give a high bactericidal effect. In this case, even if an anionic surfactant or a nonionic surfactant is present, the bactericide of the present invention is not deactivated, and is solubilized in an excessive amount of the anionic surfactant used for forming the complex salt. It exhibits a high bactericidal action even in a standing condition.
【００１６】[0016]
【発明の効果】本発明によれば、口腔用組成物などに配
合されても失活し難く、カチオン性殺菌剤の殺菌効果を
有効に発揮する殺菌剤が提供される。INDUSTRIAL APPLICABILITY According to the present invention, there is provided a bactericide which is hard to deactivate even when incorporated into an oral composition and the like, and which effectively exhibits the bactericidal effect of a cationic bactericide.
【００１７】[0017]
【実施例】以下、実施例と比較例を示し、本発明を具体
的に説明するが、本発明は下記の実施例に制限されるも
のではない。EXAMPLES The present invention will be described below in detail with reference to examples and comparative examples, but the present invention is not limited to the following examples.
【００１８】［実施例・比較例Ｉ］表１に示したカチオ
ン性殺菌剤とアニオン性界面活性剤との複合塩を調製し
た。調製方法は、塩化セチルピリジニウムとラウリン酸
ナトリウムとの反応を例にとると、下記の通りである。
まず、５００ｍｌのナス型フラスコに１７．９ｇの塩化
セチルピリジニウムと、それと等モルになるラウリン酸
ナトリウム１．１２ｇ及び２５０ｍｌのエタノ−ルを入
れて混合溶解し、還流冷却器を付け、８０〜９０℃の温
浴中で２時間加熱して反応させ、生成したＮａＣｌを濾
別した。その濾液を室温で１日放置した。生じたＮａＣ
ｌを濾別し、濾液からエタノ−ルを留去し、固形分（複
合塩）を得た。更に、その固形分にエタノ−ルを加えて
再結晶し、目的の複合塩を得た。[Examples / Comparative Example I] Composite salts of the cationic bactericide and anionic surfactant shown in Table 1 were prepared. The preparation method is as follows, taking the reaction of cetylpyridinium chloride and sodium laurate as an example.
First, 17.9 g of cetylpyridinium chloride, 1.12 g of sodium laurate and equimolar amount of 1.12 g of sodium laurate and 250 ml of ethanol were put in a 500 ml eggplant-shaped flask, and they were mixed and dissolved. The mixture was heated for 2 hours in a warm bath at 0 ° C. to cause reaction, and the produced NaCl was filtered off. The filtrate was left at room temperature for 1 day. Generated NaC
l was filtered off and ethanol was distilled off from the filtrate to obtain a solid content (composite salt). Further, ethanol was added to the solid content and recrystallization was performed to obtain a target complex salt.
【００１９】次に、調製した複合塩溶液（１０％エタノ
−ル）６ｍｌにエシェリキア・コリ（Ｅｓｃｈｅｒｉｃ
ｈｉａ ｃｏｌｉ）Ｕ５／４１の菌液６０μｌを加え、
室温で１分間反応させたのち、ＬＰＳ（滅菌生理食塩水
に１％Ｔｗｅｅｎ８０，０．１％レシチンを混合したも
の）を加え、反応を停止したものを試料とした。次い
で、ＴＨＢ培地９ｍｌを分注した試験管（２０ｍｌ）に
上記試料１ｍｌを加えてよく混ぜた。さらに、そこから
１ｍｌを取り、２管目に移し、以後同様にして６管目ま
で希釈を行った。対照（塩化セチルピリジニウム）につ
いても同様に８管目まで希釈を行った。次に、希釈され
た試験管から１ｍｌと所定量のＳＣＤＬＰ寒天培地をシ
ャ−レにまき、混釈して３７℃で２４時間培養後、菌数
を測定し、肉眼で菌の発育が認められない試料の最小濃
度をＭＩＣとした。Next, 6 ml of the prepared complex salt solution (10% ethanol) was added to Escherichia coli (Escheric).
hia coli) Add 60 μl of U5 / 41 bacterial solution,
After reacting for 1 minute at room temperature, LPS (sterile physiological saline mixed with 1% Tween80, 0.1% lecithin) was added, and the reaction was stopped to give a sample. Next, 1 ml of the above sample was added to a test tube (20 ml) into which 9 ml of THB medium was dispensed and mixed well. Further, 1 ml was taken from the tube, transferred to the second tube, and then diluted to the sixth tube in the same manner. Similarly, the control (cetylpyridinium chloride) was diluted to the 8th tube. Next, 1 ml of the diluted test tube and a predetermined amount of SCDLP agar medium were spread on a dish, and the mixture was poured and cultured at 37 ° C. for 24 hours. Then, the number of bacteria was measured, and the growth of the bacteria was visually recognized. The minimum concentration of the sample that did not exist was taken as the MIC.
【００２０】その結果を表１に示す。The results are shown in Table 1.
【００２１】[0021]
【表１】 [Table 1]
【００２２】＊石鹸チップの化学組成は下記の通りであ
る。 オクタン酸ナトリウム １．９（％） デカン酸ナトリウム １．９ ラウリン酸ナトリウム １８．０ ミリスチン酸ナトリウム ５．７ パルミチン酸ナトリウム ３０．８ ステアリン酸ナトリウム ４．０ オレイン酸ナトリウム ３２．５ ラウリン酸 １．０ パルミチン酸 ４．０ エチレンジアミン四酢酸ナトリウム ０．０２５ ヒドロキシエタンジホスホン酸 ０．２５* The chemical composition of the soap chips is as follows. Sodium octanoate 1.9 (%) Sodium decanoate 1.9 Sodium laurate 18.0 Sodium myristate 5.7 Sodium palmitate 30.8 Sodium stearate 4.0 Sodium oleate 32.5 Laurate 1.0 Palmitic acid 4.0 Sodium ethylenediaminetetraacetate 0.025 Hydroxyethanediphosphonic acid 0.25
【００２３】ＣＰＣ：塩化セチルピリジニウム ＡＳ：アルキル硫酸塩 Ｒ−ＳＯ3Ｎａ Ｓｏａｐ：脂肪酸塩 Ｒ−ＣＯＯＮａ ＡＥＳ：ポリオキシエチレンアルキル硫酸エーテル塩
（ナトリウム塩） ＬＡＳ：直鎖アルキルベンゼンスルホン酸塩（ナトリウ
ム塩）CPC: cetylpyridinium chloride AS: alkyl sulfate R-SO 3 Na Soap: fatty acid salt R-COONA AES: polyoxyethylene alkyl sulfate ether salt (sodium salt) LAS: linear alkylbenzene sulfonate (sodium salt)
【００２４】表１の結果より、複合塩に用いられるアニ
オン性界面活性剤は、アルキル硫酸塩ではアルキル基の
炭素数８以下であれば殺菌力は低下せず、炭素数１０以
上になると殺菌力は大きく低下した。また、炭素数１２
の直鎖アルキルベンゼンスルホン酸ナトリウムの殺菌力
は不良であり、炭素数１２〜１８の脂肪酸塩及び石鹸チ
ップ、炭素数１２のポリオキシエチレンアルキルエ−テ
ル硫酸塩では良好な殺菌力を有していることが知見され
た。また、炭素数１２の脂肪酸塩とカチオン性殺菌剤と
して塩化セチルピリジニウム、塩化ベンゼトニウム、塩
化ベンザルコニウム、クロルヘキシジン塩酸塩とをそれ
ぞれ用いて調製した複合塩は、いずれも良好な殺菌力を
有していることが知見された。From the results shown in Table 1, the anionic surfactant used in the complex salt does not show a decrease in bactericidal activity when the alkyl group has 8 or less carbon atoms in the alkyl group, and a bactericidal activity when the carbon number is 10 or more. Fell significantly. Also, carbon number 12
The straight-chain sodium sodium alkylbenzene sulfonate has poor bactericidal activity, and fatty acid salts having 12 to 18 carbon atoms, soap chips, and polyoxyethylene alkyl ether sulfate having 12 carbon atoms have good bactericidal activity. It was discovered. Further, the complex salts prepared by using a fatty acid salt having 12 carbon atoms and cetylpyridinium chloride, benzethonium chloride, benzalkonium chloride, and chlorhexidine hydrochloride as cationic bactericides each have good bactericidal activity. It was discovered that
【００２５】［実施例・比較例ＩＩ］表２に示すカチオ
ン性殺菌剤と界面活性剤とを上記と同様の方法で反応さ
せて得た複合塩を使用し、表２の処方の練歯磨を調製
し、そのＭＩＣ及びＭＢＣを評価した。結果を表２に併
記する。[Examples / Comparative Example II] A toothpaste having a formulation shown in Table 2 was prepared by using a complex salt obtained by reacting a cationic bactericide shown in Table 2 with a surfactant in the same manner as described above. It was prepared and its MIC and MBC were evaluated. The results are also shown in Table 2.
【００２６】ＭＩＣ測定法 各練歯磨を滅菌水でそれぞれ８段階まで倍々希釈し、９
６穴ウェルプレ−トの各穴に０．１ｍｌずつ入れ、そこ
に６％濃度のＴＨＢ培地０．１ｍｌを添加し、さらに前
培養したエシェリキア・コリ Ｕ５／４１を５倍希釈し
た菌液０．０１ｍｌを加えてよく混和し、３７℃で２４
時間培養後、菌数を測定し、肉眼的に菌の発育の認めら
れない試料の最小濃度をＭＩＣとした。 MIC measurement method Each toothpaste is diluted with sterilized water by 8 times to obtain 9 dilutions.
0.1 ml was put in each well of a 6-well plate, 0.1 ml of 6% concentration of THB medium was added thereto, and 0.01 ml of bacterial solution obtained by diluting pre-cultured Escherichia coli U5 / 41 5-fold Add well and mix well, and mix at 37 ℃ for 24 hours.
After culturing for a period of time, the number of bacteria was measured, and the minimum concentration of the sample in which the growth of bacteria was not visually recognized was defined as MIC.
【００２７】ＭＢＣ測定法 各歯磨を滅菌水でそれぞれ８段階まで倍々希釈し、９６
穴ウェルプレ−トの各穴に０．１ｍｌずつ入れ、そこに
６％濃度のＴＨＢ培地０．１ｍｌを添加し、更に前培養
したエシェリキア・コリ Ｕ５／４１を５倍希釈した菌
液０．０１ｍｌを加えてよく混和し、３７℃で２４時間
培養後、その培養液の１白金耳をＳＣＤＬＰ寒天平板に
塗抹し、更に３７℃で２４時間培養後、菌数を測定し、
肉眼的に菌の発育が認められない試料の最小濃度をＭＢ
Ｃとした。 MBC measurement method Each dentifrice is double-diluted with sterilized water up to 8 steps, and 96
0.1 ml was placed in each well of the well plate, 0.1 ml of 6% concentration of THB medium was added thereto, and 0.01 ml of the bacterial solution obtained by diluting the precultured Escherichia coli U5 / 41 by 5 times was added. In addition, mix well and after culturing at 37 ° C for 24 hours, 1 platinum loop of the culture solution is smeared on an SCDLP agar plate, and after further culturing at 37 ° C for 24 hours, the number of bacteria is measured,
MB is the minimum concentration of the sample in which bacterial growth is not visually recognized.
It was set to C.
【００２８】[0028]
【表２】 [Table 2]
【００２９】表２の結果から、本発明の複合塩を含む練
歯磨（Ｎｏ．１〜３）は、比較例（Ｎｏ．４）及び対照
歯磨（Ｎｏ．５）に比べ高い殺菌力を有することが認め
られた。From the results shown in Table 2, the toothpaste (No. 1 to 3) containing the complex salt of the present invention has a higher bactericidal activity than the comparative example (No. 4) and the control toothpaste (No. 5). Was recognized.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ６１Ｋ 47/08 Ｊ 47/12 Ｊ 47/20 Ｊ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display area A61K 47/08 J 47/12 J 47/20 J
Claims (2)
ル基の炭素数が８以下のアルキル硫酸塩及びポリオキシ
エチレンアルキルエーテル硫酸塩から選ばれるアニオン
性界面活性剤との複合塩からなることを特徴とする殺菌
剤。1. A composite salt of a cationic bactericide and an anionic surfactant selected from fatty acid salts, alkyl sulfates having an alkyl group having 8 or less carbon atoms, and polyoxyethylene alkyl ether sulfates. Characteristic fungicide.
ル基の炭素数が８以下のアルキル硫酸塩及びポリオキシ
エチレンアルキルエ−テル硫酸塩から選ばれるアニオン
性界面活性剤とを反応させて、これらの複合塩を得るこ
とを特徴とする殺菌剤の製造方法。2. A cationic bactericide is reacted with an anionic surfactant selected from a fatty acid salt, an alkyl sulfate having an alkyl group having 8 or less carbon atoms, and a polyoxyethylene alkyl ether sulfate, A method for producing a bactericide, which comprises obtaining these complex salts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28004794A JPH08119878A (en) | 1994-10-19 | 1994-10-19 | Antimicrobial agent and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28004794A JPH08119878A (en) | 1994-10-19 | 1994-10-19 | Antimicrobial agent and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08119878A true JPH08119878A (en) | 1996-05-14 |
Family
ID=17619561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28004794A Pending JPH08119878A (en) | 1994-10-19 | 1994-10-19 | Antimicrobial agent and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08119878A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998056253A1 (en) * | 1997-06-13 | 1998-12-17 | Avecia Limited | Biocidal organic acid salts of a polymeric biguanide |
| US7863458B2 (en) | 2002-03-01 | 2011-01-04 | Merck Patent Gmbh | Halogen-free ionic liquids |
| US8460689B2 (en) | 2009-05-08 | 2013-06-11 | 3M Innovative Properties Company | Oral care method and kit |
| US11684069B2 (en) | 2013-09-13 | 2023-06-27 | 3M Innovative Properties Company | Cationic antiseptic compositions |
-
1994
- 1994-10-19 JP JP28004794A patent/JPH08119878A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998056253A1 (en) * | 1997-06-13 | 1998-12-17 | Avecia Limited | Biocidal organic acid salts of a polymeric biguanide |
| US7863458B2 (en) | 2002-03-01 | 2011-01-04 | Merck Patent Gmbh | Halogen-free ionic liquids |
| US8460689B2 (en) | 2009-05-08 | 2013-06-11 | 3M Innovative Properties Company | Oral care method and kit |
| US9468614B2 (en) | 2009-05-08 | 2016-10-18 | 3M Innovative Properties Company | Oral care method and kit |
| US11684069B2 (en) | 2013-09-13 | 2023-06-27 | 3M Innovative Properties Company | Cationic antiseptic compositions |
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