JPH0621043B2 - Industrial water-based antibacterial agent - Google Patents
Industrial water-based antibacterial agentInfo
- Publication number
- JPH0621043B2 JPH0621043B2 JP61115038A JP11503886A JPH0621043B2 JP H0621043 B2 JPH0621043 B2 JP H0621043B2 JP 61115038 A JP61115038 A JP 61115038A JP 11503886 A JP11503886 A JP 11503886A JP H0621043 B2 JPH0621043 B2 JP H0621043B2
- Authority
- JP
- Japan
- Prior art keywords
- antibacterial agent
- present
- antibacterial
- inhibitory concentration
- component
- 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.)
- Expired - Fee Related
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は工業用水系抗菌剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an industrial aqueous antibacterial agent.
［従来の技術］ 工業用冷却用水系においては、ズーグレア状細菌、藻
類、糸状菌等によるスライム障害が引き起こされる場合
が多い。その結果、熱効率の低下や通水の悪化をもたら
すばかりでなく、機器、配管等の局部腐食発生の原因と
もなっている。また、紙パルプ用水系においては、細
菌、糸状菌、酵母類によるスライム障害が主に抄紙工程
で発生する。スライムはパイプスラリーの異物として混
入すると、製品の品質を低下させるばかりでなく、紙切
れを生じ抄紙機の連続運転を阻害する要因となり生産効
率を大幅に低下させる。[Prior Art] In industrial cooling water systems, slime disorders are often caused by zooglare-like bacteria, algae, filamentous fungi and the like. As a result, not only does the thermal efficiency decrease and water flow deteriorates, but it also causes local corrosion of equipment, piping, and the like. Further, in the water system for paper pulp, slime disorders due to bacteria, filamentous fungi, and yeasts mainly occur in the papermaking process. If slime is mixed in as foreign matter in the pipe slurry, not only the quality of the product is deteriorated, but also paper breakage is caused and the continuous operation of the paper machine is hindered, so that the production efficiency is significantly decreased.
こうしたスライム障害を防止するには、上記のようなス
ライム構成菌を破壊又は成長阻害する必要がある。この
ため従来より抗菌剤として、イソチアゾロン系化合物が
単独で、又は他の殺菌剤との併用での使用が各種提案さ
れている（特公昭４６−４１９９号公報、特開昭６０−
８４２０３号公報等）。In order to prevent such slime disorders, it is necessary to destroy or inhibit the growth of the above slime-forming bacteria. For this reason, conventionally, various proposals have been made for the use of isothiazolone compounds alone or in combination with other fungicides as an antibacterial agent (Japanese Patent Publication No. 46-4199, JP-A 60-).
84203, etc.).
［発明が解決しようとする課題］ しかしながら、従来の提案方法によっては必ずしもスラ
イム障害を十分に防止することはできなかった。特にイ
ソチアゾロン系化合物は、長期的に使用するとスライム
構成菌に耐性がつきやすく、抵抗性のある細菌が優先し
やすいということが知られている。更に、近年は処理コ
スト低下の意味で、より効力の高い抗菌剤が要求されて
いる。[Problems to be Solved by the Invention] However, slime disorders cannot always be sufficiently prevented by the conventional proposed methods. In particular, isothiazolone compounds are known to be resistant to slime-constituting bacteria when used over a long period of time, and resistant bacteria are preferred. Further, in recent years, antibacterial agents having higher efficacy have been demanded in order to reduce processing costs.
本発明は、抗菌効力が大きく、スライム構成菌の耐性が
つきにくい抗菌剤を提供することを目的とするものであ
る。It is an object of the present invention to provide an antibacterial agent having a large antibacterial effect and being resistant to slime-constituting bacteria.
［課題を解決するための手段］ 本発明者らは前記従来方法の問題点を克服するために鋭
意研究を行なった結果本発明を完成したものであって、
特定のイソシアゾロン系化合物と特定の殺菌剤とを組み
合わせることにより、両成分から予想されるより大きな
相乗効果を得るとともにスライム構成菌の耐性防止に成
功して、本発明を完成するに至った。[Means for Solving the Problems] The present inventors have completed the present invention as a result of intensive studies to overcome the problems of the conventional methods.
By combining a specific isociazolone compound and a specific fungicide, a greater synergistic effect expected from both components was obtained, and the resistance of slime-constituting bacteria was successfully prevented, thus completing the present invention.
すなわち、本発明は、（Ａ）４,５−ジクロロ−２−オ
クチルイソチアゾリン−３−オンに対して、（Ｂ）２,
２−ジブロモ−３−ニトリロプロピオンアミド、１,３
−ジブロモ−５,５−ジメチルヒダントイン及びヘキサ
ブロモジメチルスルホンからなる臭素含有化合物群から
選ばれる少なくとも１種を組み合わせたことを特徴とす
る工業用水系抗菌剤を提供するものである。That is, the present invention relates to (A) 4,5-dichloro-2-octylisothiazolin-3-one and (B) 2,
2-dibromo-3-nitrilopropionamide, 1,3
-An industrial aqueous antibacterial agent characterized by combining at least one selected from the group of bromine-containing compounds consisting of dibromo-5,5-dimethylhydantoin and hexabromodimethylsulfone.
本発明において、（Ａ）成分４,５−ジクロロ−２−オ
クチルイソチアゾリン−３−オンと（Ｂ）成分として用
いる臭素含有化合物との配合割合は特に制限されない
が、通常１０：１〜１：２００程度である。本発明に用
いる両成分の最適配合割合は、実施例に示す方法で選択
することができる。すなわち、それぞれの組み合わせに
おいて配合割合を変えた溶液を用意して、各配合溶液に
おける最小増殖阻止濃度を求め、両成分の添加量の総計
が最も低いものを好適な配合割合として選択することが
できる。In the present invention, the mixing ratio of the component (A) 4,5-dichloro-2-octylisothiazolin-3-one and the bromine-containing compound used as the component (B) is not particularly limited, but is usually 10: 1 to 1: 200. It is a degree. The optimum blending ratio of both components used in the present invention can be selected by the method shown in Examples. That is, it is possible to prepare a solution having a different mixing ratio in each combination, obtain the minimum growth inhibitory concentration in each mixing solution, and select the one having the lowest total addition amount of both components as a suitable mixing ratio. .
本発明抗菌剤の使用法は従来と同様、被処理用水系に添
加すればよく、（Ａ）成分、（Ｂ）成分を予め用水中に
所定濃度となるように配合し、十分混合してから被処理
用水系に添加してもよいし、各成分を別々に用水中に所
定濃度となるように被処理用水系へ添加してもよい。The use of the antibacterial agent of the present invention may be carried out by adding it to the water system to be treated as in the conventional method. The components (A) and (B) are preliminarily blended in the water to a predetermined concentration and sufficiently mixed. It may be added to the water system to be treated, or each component may be separately added to the water system to be treated so as to have a predetermined concentration in the water.
本発明抗菌剤の添加濃度は被処理用水系の状態によって
も異なるが、通常、用水中に０．５〜５００mg／ｌを使
用することができる。The addition concentration of the antibacterial agent of the present invention varies depending on the condition of the water system to be treated, but usually 0.5 to 500 mg / l can be used in the water.
本発明抗菌剤は、粉末のまま、又は、界面活性剤を用い
て乳化状態として、若しくは、溶媒に溶かして溶液とし
て用水に添加することができる。The antibacterial agent of the present invention can be added to water as a powder, in an emulsified state by using a surfactant, or as a solution by being dissolved in a solvent.
溶液とする場合は、本発明抗菌剤の溶媒として、水又は
アルコール類、アセトン、ジメチルスルホキシド、エチ
レングリコールエーテル等の有機溶媒を使用することが
できる。特に本発明抗菌剤の（Ａ）成分は水への溶解性
が悪いので、有機溶媒溶液にして添加するのが分散性の
点で望ましい。In the case of forming a solution, water or an organic solvent such as alcohols, acetone, dimethyl sulfoxide, ethylene glycol ether or the like can be used as the solvent of the antibacterial agent of the present invention. In particular, since the component (A) of the antibacterial agent of the present invention has poor solubility in water, it is desirable to add it as an organic solvent solution in terms of dispersibility.
本発明抗菌剤は、開放及び密閉型冷却用水系や紙パルプ
用水系に、特に好適に使用することができる。The antibacterial agent of the present invention can be particularly preferably used in open and closed cooling water systems and paper pulp water systems.
［作用］ 本発明においては（Ａ）成分の有する抗菌性と（Ｂ）成
分の有する抗菌性とが相乗作用により増幅し、各成分を
単独で用いた場合よりもはるかに強力な抗菌性を揮発す
ることができる。[Action] In the present invention, the antibacterial property of the component (A) and the antibacterial property of the component (B) are amplified by a synergistic effect, and voluntarily elicit a much stronger antibacterial property than when each component is used alone. can do.
以下に実施例により本発明をさらに詳細に説明する。Hereinafter, the present invention will be described in more detail with reference to Examples.
［実施例］ Ｐｓ．ａｅｒｇｉｎｏｓａ（緑膿菌）を用いて最小増殖
阻止濃度（ＭｌＣ24）を求めた。[Example] Ps. The minimum growth inhibitory concentration (MlC 24 ) was determined using aerginosa (Pseudomonas aeruginosa).
試験条件はpH７のペプトン−酵母エキスをベースとする
液体培地（ペプトン１ｇ／ｌ、酵母エキス１ｇ／ｌを含
む）に前記菌を１０6個／mlとなるように接種し、本発
明の抗菌剤を所定割合となるように添加し、３０℃で２
４時間振盪培養した。The test conditions are as follows: A peptone-yeast extract-based liquid medium having a pH of 7 (containing 1 g / l of peptone and 1 g / l of yeast extract) was inoculated with the above-mentioned bacteria at 10 6 cells / ml, and the antibacterial agent of the present invention was inoculated. At a predetermined ratio, and add 2 at 30 ° C.
The cells were shake-cultured for 4 hours.
まず、４,５−ジクロロ−２−オクチルイソチアゾリン
−３−オン単独及び３種のＢ成分の各臭素含有化合物単
独溶液の最小増殖阻止濃度を求め、４,５−ジクロロ−
２−オクチルイソチアゾリン−３−オンの最小増殖阻止
濃度と各臭素含有化合物の最小増殖阻止濃度の比率に対
応して両成分の配合比率を変えた５種の溶液を各臭素含
有化合物毎に調製して、それぞれの溶液について、最小
増殖阻止濃度を求めて、図にプロットした。First, the minimum growth inhibitory concentrations of 4,5-dichloro-2-octylisothiazolin-3-one alone and solutions of each of the three bromine-containing compounds of B component alone were determined, and 4,5-dichloro-
Five kinds of solutions were prepared for each bromine-containing compound by changing the compounding ratio of both components corresponding to the ratio of the minimum growth-inhibitory concentration of 2-octylisothiazolin-3-one and the minimum growth-inhibitory concentration of each bromine-containing compound. Then, the minimum growth inhibitory concentration was determined for each solution and plotted in the figure.
結果を第１〜３図に示す。The results are shown in FIGS.
第１図は、４,５−ジクロロ−２−オクチルイソチアゾ
リン−３−オンと２,２−ジブロモ−３−ニトリロプロ
ピオンアミドと組み合わせた場合の図であり、それぞれ
単独成分の最小増殖阻止濃度は、１mg／ｌ及び５mg／ｌ
であり、この濃度を縦軸及び横軸の最大尺度として取
り、この尺度に対応して配合比率を変えた溶液５種を調
製して、各混合溶液の最小増殖阻止濃度をそれぞれの配
合比率を示す斜線の上にプロットした。FIG. 1 is a diagram in the case where 4,5-dichloro-2-octylisothiazolin-3-one and 2,2-dibromo-3-nitrilopropionamide are combined, and the minimum inhibitory concentration of each individual component is: 1 mg / l and 5 mg / l
This concentration is taken as the maximum scale on the vertical and horizontal axes, and 5 kinds of solutions with different blending ratios are prepared according to this scale, and the minimum growth inhibitory concentration of each mixed solution is determined by the respective blending ratios. Plotted above the diagonal line shown.
第２図は４,５−ジクロロ−２−オクチルイソチアゾリ
ン−３−オンと１,３−ジブロモ−５,５−ジメチルヒダ
ントインと組み合わせた場合の図であり、それぞれ単独
成分の最小増殖阻止濃度は、１mg／ｌ及び５０mg／ｌで
あり、この濃度を縦軸及び横軸の最大尺度として取り、
この尺度に対応して配合比率を変えた溶液５種を調製し
て、各混合溶液の最小増殖阻止濃度をそれぞれの配合比
率を示す斜線の上にプロットした。FIG. 2 is a diagram in the case where 4,5-dichloro-2-octylisothiazolin-3-one and 1,3-dibromo-5,5-dimethylhydantoin were combined, and the minimum inhibitory concentration of each single component was: 1 mg / l and 50 mg / l, taking this concentration as the maximum scale of the vertical and horizontal axes,
Five kinds of solutions having different blending ratios were prepared in accordance with this scale, and the minimum growth inhibitory concentration of each mixed solution was plotted on the diagonal line showing each blending ratio.
第３図は４,５−ジクロロ−２−オクチルイソチアゾリ
ン−３−オンヘキサブロモジメチルスルホンと組み合わ
せた場合の図であり、それぞれ単独成分の最小増殖阻止
濃度は、１mg／ｌ及び２０mg／ｌであり、この濃度を縦
軸及び横軸の最大尺度として取り、この尺度に対応して
配合比率を変えた溶液５種を調製して、各混合溶液の最
小増殖阻止濃度をそれぞれの配合比率を示す斜線の上に
プロットした。FIG. 3 is a diagram when combined with 4,5-dichloro-2-octylisothiazolin-3-one hexabromodimethyl sulfone, and the minimum inhibitory concentrations of the individual components were 1 mg / l and 20 mg / l, respectively. , Take this concentration as the maximum scale of the vertical and horizontal axes, prepare 5 kinds of solutions with different blending ratios corresponding to this scale, and show the minimum growth inhibitory concentration of each mixed solution with diagonal lines showing the respective blending ratios. Plotted above.
本発明抗菌剤溶液は各成分を単独で用いる場合に比べ
て、併用により格段優れた相乗的に大きい抗菌力を発揮
することがわかる。It can be seen that the antibacterial agent solution of the present invention exerts a significantly superior synergistic antibacterial effect when used in combination as compared with the case where each component is used alone.
［発明の効果］ 本発明の抗菌剤は相乗効果により優れた抗菌活性を有す
る。その結果、処理効率の向上を処理コストの低減が実
現される。[Effect of the Invention] The antibacterial agent of the present invention has excellent antibacterial activity due to the synergistic effect. As a result, improvement in processing efficiency and reduction in processing cost are realized.
さらに、複数の抗菌剤の使用により、抗菌スペクトルが
各成分単独使用時に比べて広くなったり、また、耐性が
つきにくくなり、長期的な使用が可能となるという利点
が得られる。Furthermore, the use of a plurality of antibacterial agents has the advantages that the antibacterial spectrum is broader than that when each component is used alone, and that resistance is less likely to occur, enabling long-term use.
【図面の簡単な説明】 第１図は、臭素含有化合物として、２,２−ジブロモ−
３−ニトリロプロピオンアミドを使用した場合の抗菌試
験の最小増殖阻止濃度を示す図である。 第２図は、臭素含有化合物として、１,３−ジブロモ−
５,５−ジメチルヒダントインを使用した場合の抗菌試
験の最小増殖阻止濃度を示す図である。 第３図は、臭素含有化合物として、ヘキサブロモジメチ
ルスルホンを使用した場合の抗菌試験の最小増殖阻止濃
度を示す図である。BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 shows 2,2-dibromo- as a bromine-containing compound.
It is a figure which shows the minimum growth inhibitory concentration of an antibacterial test when 3-nitrilopropionamide is used. FIG. 2 shows 1,3-dibromo- as a bromine-containing compound.
It is a figure which shows the minimum growth inhibitory concentration of an antibacterial test when 5,5-dimethyl hydantoin is used. FIG. 3 is a diagram showing the minimum growth inhibitory concentration in an antibacterial test when hexabromodimethyl sulfone is used as the bromine-containing compound.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 (Ａ０１Ｎ 43/80 37:34） ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display location (A01N 43/80 37:34)
Claims (1)
ゾリン−３−オンに対して、２,２−ジブロモ−３−ニ
トリロプロピオンアミド、１,３−ジブロモ−５,５−ジ
メチルヒダントイン及びヘキサブロモジメチルスルホン
からなる臭素含有化合物群から選ばれる少なくとも１種
を組み合わせたことを特徴とする工業用水系抗菌剤。1. With respect to 4,5-dichloro-2-octylisothiazolin-3-one, 2,2-dibromo-3-nitrilopropionamide, 1,3-dibromo-5,5-dimethylhydantoin and hexabromo. An industrial aqueous antibacterial agent characterized by combining at least one selected from the group of bromine-containing compounds consisting of dimethyl sulfone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61115038A JPH0621043B2 (en) | 1986-05-20 | 1986-05-20 | Industrial water-based antibacterial agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61115038A JPH0621043B2 (en) | 1986-05-20 | 1986-05-20 | Industrial water-based antibacterial agent |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5279083A Division JPH0780729B2 (en) | 1993-10-12 | 1993-10-12 | Industrial water-based antibacterial agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62270506A JPS62270506A (en) | 1987-11-24 |
| JPH0621043B2 true JPH0621043B2 (en) | 1994-03-23 |
Family
ID=14652658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61115038A Expired - Fee Related JPH0621043B2 (en) | 1986-05-20 | 1986-05-20 | Industrial water-based antibacterial agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0621043B2 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4964892A (en) * | 1988-12-22 | 1990-10-23 | Rohm And Haas Company | Synergistic microbicidal combinations containing 2-N-octyl-3-isothiazolone and certain commercial biocides |
| JPH0749362B2 (en) * | 1989-03-30 | 1995-05-31 | ソマール株式会社 | Antibacterial agent |
| ZA908425B (en) * | 1989-11-03 | 1991-07-31 | Rohm & Haas | Synergistic microbicidal combinations |
| US5468759A (en) * | 1991-12-19 | 1995-11-21 | Rohm And Haas Company | Synergistic microbicidal combinations containing 4,5-dichloro-2-octyl-3-isothiazolone and certain commercial biocides |
| US5142058A (en) * | 1990-12-14 | 1992-08-25 | Rohm And Haas Company | Halogen-containing organic stabilizers for 3-isothiazolones |
| US5158596A (en) * | 1991-02-15 | 1992-10-27 | Rohm And Haas Company | Synergistic antialgal compositions comprising diphenylethers and certain commercial biocides, methods of controlling algae, and coating compositions comprising the antialgal compositions |
| JP2679937B2 (en) * | 1993-07-20 | 1997-11-19 | 株式会社片山化学工業研究所 | Industrial sterilizer / bacteriostat |
| US6069142A (en) * | 1998-12-23 | 2000-05-30 | Calgon Corporation | Synergistic antimicrobial combination of 4,5-dichloro-2-N-octyl-4-isothiazolin-3-one and a mixture of a chlorinated isocyanurate and a bromide compound and methods of using same |
| US20030228341A1 (en) * | 2000-01-18 | 2003-12-11 | Howarth Jonathan N. | Microbiological control in aqueous systems |
| CN113367143A (en) * | 2021-06-10 | 2021-09-10 | 浙江先拓环保科技有限公司 | Sewage antibacterial agent and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929562A (en) * | 1975-03-03 | 1975-12-30 | Betz Laboratories | Synergistic compositions containing 2,2-dibromo-3-nitriloproprionamide and their use |
| JPS54140726A (en) * | 1978-04-24 | 1979-11-01 | Somar Mfg | Slime controlling agent in paper pulp industry |
| US4265899A (en) * | 1978-05-30 | 1981-05-05 | Rohm And Haas Company | Cosmetic formulation comprising 3-isothiazolones |
| JPS6054281A (en) * | 1983-09-02 | 1985-03-28 | Hitachi Ltd | Manufacture of build-up welded flange |
| JPS6183105A (en) * | 1984-09-28 | 1986-04-26 | Kurita Water Ind Ltd | Antibacterial agent |
-
1986
- 1986-05-20 JP JP61115038A patent/JPH0621043B2/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929562A (en) * | 1975-03-03 | 1975-12-30 | Betz Laboratories | Synergistic compositions containing 2,2-dibromo-3-nitriloproprionamide and their use |
| JPS54140726A (en) * | 1978-04-24 | 1979-11-01 | Somar Mfg | Slime controlling agent in paper pulp industry |
| US4265899A (en) * | 1978-05-30 | 1981-05-05 | Rohm And Haas Company | Cosmetic formulation comprising 3-isothiazolones |
| JPS6054281A (en) * | 1983-09-02 | 1985-03-28 | Hitachi Ltd | Manufacture of build-up welded flange |
| JPS6183105A (en) * | 1984-09-28 | 1986-04-26 | Kurita Water Ind Ltd | Antibacterial agent |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62270506A (en) | 1987-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5980758A (en) | Method and composition for inhibiting growth of microorganisms including peracetic acid and a non-oxidizing biocide | |
| US4295932A (en) | Synergistic blend of biocides | |
| US4725587A (en) | Biocidal compositions and use thereof containing a synergistic mixture of 2-bromo-2-nitropropane-1,3-diol and tri-n-butyl tetradecyl phosphonium chloride | |
| US5494588A (en) | Method and composition for inhibiting growth of microorganisms including peracetic acid and a second organic biocide | |
| US4732905A (en) | Biocidal compositions and use thereof containing a synergistic mixture of 2-bromo-2-nitropropane-1,3-diol and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one | |
| US5368749A (en) | Synergistic activity of glutaraldehyde in the presence of oxidants | |
| JPH0621043B2 (en) | Industrial water-based antibacterial agent | |
| US4753961A (en) | Biocidal compositions and use thereof containing a synergistic mixture of 2-bromo-2-nitropropane-1,3-diol and tetradecyl dimethyl sulfonium methosulfate | |
| DE69806558T2 (en) | Stabilization of 3-isothiazolone solutions | |
| US4732911A (en) | Biocidal compositions and use thereof containing a synergistic mixture of 2-bromo-2-nitropropane-1,3-diol and bis (tri n-butyl tin) oxide | |
| US5416109A (en) | Method and composition for controlling the growth of microorganisms | |
| CN104054748A (en) | Sterilization algicide suitable for industrial water system and application of sterilization algicide | |
| EP0562739B1 (en) | Control of slime formation in industrial process waters | |
| US4650808A (en) | Synergistic compositions containing hydroxypropyl methanethiolsulfonate and methods of using same | |
| AU641293B2 (en) | Synergistic microbiocidal composition of 2-(decylthio) ethaneamine and 1,2-dibromo-2,4-dicyanobutane | |
| JP4288058B2 (en) | Microbicide composition | |
| DE1271314B (en) | Synergistic microbiocidal agent to combat microorganisms in industrial water systems | |
| JPH0780729B2 (en) | Industrial water-based antibacterial agent | |
| JPS6084203A (en) | Antimicrobial agent | |
| EP0266828B1 (en) | Control of biofouling with certain alkylthioalkylamines | |
| US5015660A (en) | Microbicidal/microbistatic composition for industrial use and method of using same | |
| JPH06256107A (en) | Microorganism-controlling agent and controlling method | |
| EP0743002B1 (en) | Bacterial inhibiting compositions and their use | |
| JPH08188504A (en) | Microbe controlling agent and microbe controlling | |
| JPH0242007A (en) | Industrial germicide and microbicide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |