JPH01153604A - Slime controller for petroleum fuel - Google Patents

Slime controller for petroleum fuel

Info

Publication number
JPH01153604A
JPH01153604A JP62312075A JP31207587A JPH01153604A JP H01153604 A JPH01153604 A JP H01153604A JP 62312075 A JP62312075 A JP 62312075A JP 31207587 A JP31207587 A JP 31207587A JP H01153604 A JPH01153604 A JP H01153604A
Authority
JP
Japan
Prior art keywords
slime
fuel
compound
heavy oil
growth
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
Application number
JP62312075A
Other languages
Japanese (ja)
Other versions
JP2605764B2 (en
Inventor
Shigefumi Arai
重文 新井
Akio Furuhata
降旗 昭夫
Takeshi Nakajima
健 中島
Yasushi Nakaida
中井田 靖
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
Dainippon Ink and Chemicals Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dainippon Ink and Chemicals Co Ltd filed Critical Dainippon Ink and Chemicals Co Ltd
Priority to JP62312075A priority Critical patent/JP2605764B2/en
Publication of JPH01153604A publication Critical patent/JPH01153604A/en
Application granted granted Critical
Publication of JP2605764B2 publication Critical patent/JP2605764B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

PURPOSE:To obtain the title controller containing 2-n-octyl-4-isothiazolone and 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine showing inhibitory effects on growth of molds, main part of slime. CONSTITUTION:A slime controller containing 2-n-octyl-4-isothiazolone and 2,3,5,6- tatrachloro-4-(methylsulfonyl)pyridine as active ingredients, having extremely inhibitory effects on growth of molds, main part of slime, not changing qualities of fuel, readily soluble in fuel, soluble in water at the interface of water base. The blending ratio of the two compounds is 0.1-5, preferably 0.2-1pt.wt. of the latter based on 1pt.wt. of the former. The content ratio of the active ingredients is about 1-30wt.%, preferably 10-30wt.%. The amount of the controller added to heavy oil, gasoline, kerosine, jet fuel, etc. is 50-10,000ppm, especially about 100-5,000ppm.

Description

【発明の詳細な説明】 〈産業上の利用分野〉   〜 本発明は、エンジン、発電機、がイラー等に使用される
石油系燃料中に発生するスライムを防除する為のスライ
ム防除薬剤に関する。
DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a slime control agent for controlling slime generated in petroleum fuel used in engines, generators, blowers, etc.

〈従来の技術及び問題点〉 カビ、バクテリア、酵母、放線菌等は、水分、栄養素の
存在と、適当な温度、−条件がそろうと増殖し産業上微
生物汚染、腐敗、劣化、変色、濁シ、沈澱、悪臭等の原
因となる。そしてそれらが原因となってさまざまなトラ
ブルが発生する為゛その防除薬剤が使用されている。
<Prior art and problems> Molds, bacteria, yeast, actinomycetes, etc. proliferate in the presence of moisture, nutrients, and appropriate temperature, resulting in industrial microbial contamination, rot, deterioration, discoloration, and cloudiness. , causing precipitation, bad odor, etc. And because they cause various problems, pesticides are used to prevent them.

A重油、軽油、航空機燃料、ガソリン等の燃料は、タン
ク貯蔵される為タンク呼吸、結篇現象によシ水が混入す
る。特に油層と水層の界面にカビ、バクテリア、酵母、
放線菌等の微生物が発生し。
Fuels such as A-heavy oil, light oil, aviation fuel, and gasoline are stored in tanks, so water gets mixed in due to tank breathing and coalescence phenomena. Especially at the interface between the oil layer and the water layer, mold, bacteria, yeast, etc.
Microorganisms such as actinomycetes occur.

これらの微生物と系中のスラッジとが集合したものをス
ライムと称している。スライムが発生するとタンク、配
管等に付着したり浮遊したシして、燃料の濾過工程で目
詰t、bを生じ、配管中の流れが悪くなったシする。一
般にA重油では、アスファルテン及びパラフィン系スラ
ッジによるトラブルもあるが、これらの沈降は比較的遅
く、また分散している為、遠心分離機能を具備した濾過
機を通す事によシ除去されている。一方、微生物が主体
でおるスライムは、形状も大きく、粘着性もある為急激
表フィルター〇目詰fシを起こし、エンジン、発電機の
運転が不能となシ船舶等の航行上危険である。その為従
来一部の船舶ではスライム防除薬剤が使用されているが
、一部のカビ、酵母等には全くスライム防除効果を示さ
ない。従来から使用されていた薬剤としては例虻ば次の
薬剤が挙げられる。メチレンビスチオシアネート、ベン
ザルコニウムクロライド、1,2−ペンツインチアゾリ
ン−3−オン、非イオン及びカチオン系界面活性剤等。
The aggregate of these microorganisms and the sludge in the system is called slime. When slime is generated, it adheres to or floats in tanks, piping, etc., causing clogging (t, b) during the fuel filtration process, and impairing the flow in the piping. In general, heavy oil A has problems due to asphaltene and paraffinic sludge, but since these settle relatively slowly and are dispersed, they are removed by passing through a filter equipped with a centrifugal separation function. On the other hand, slime, which is mainly made up of microorganisms, is large in size and sticky, so it can rapidly clog filters, making it impossible to operate engines and generators, and is dangerous to ships. For this reason, some ships have conventionally used slime control agents, but they do not show any slime control effect on some molds, yeasts, etc. Examples of conventionally used drugs include the following drugs. Methylene bisthiocyanate, benzalkonium chloride, 1,2-pentwinthiazolin-3-one, nonionic and cationic surfactants, etc.

これらの薬剤は、従来製紙用及び冷却水のスライムコン
トロール剤として使用されていたが(1)バクテリアに
は効果があるがカビに対しては効果が弱い、(2)培地
上での効果はあるがへ重油に溶解しにくい、(3)A重
油−水系界面での効果は弱い、(4)メチレンビスチオ
シアネートは生物に対する毒性がきわめて強い等の問題
点がある。
These agents have traditionally been used as slime control agents for papermaking and cooling water, but (1) they are effective against bacteria but weak against mold, and (2) they are effective on culture media. Methylene bisthiocyanate has problems such as being difficult to dissolve in heavy oil, (3) having a weak effect at the A heavy oil-water interface, and (4) methylene bisthiocyanate being extremely toxic to living organisms.

〈問題を解決する為の手段〉 本発明者らは、前記の問題点について鋭意研究した結果
、スライムの主体が糸状菌であシ、油層界面の水系の−
が弱酸性であること、更にこれら糸状菌について研究し
たところ、これら糸状菌が、クラドスホリウム属、ペニ
シリウム属、アスペルギルス属等とキャンプイタ属の酵
母からなる各種微生物の集合体であることを見い出し、
こうした菌類に燃料及び界面の水系中で低い濃度(10
0〜200 ppm程度)で著しい生育抑制効果を有し
かつ、燃料を変質させず、燃料中に容易に溶解し界面の
水系にも水溶化できる薬剤について研究した結果、本発
明を完成するに至った。
<Means for solving the problem> As a result of intensive research into the above-mentioned problems, the present inventors found that the main body of slime is filamentous fungi, and that the slime is mainly composed of filamentous fungi.
Furthermore, upon researching these filamentous fungi, we discovered that they were a collection of various microorganisms consisting of yeasts of the genus Cladosphorium, Penicillium, Aspergillus, etc., and yeasts of the genus Campita.
These fungi are present at low concentrations (10
As a result of research into a drug that has a significant growth-inhibiting effect at a concentration of about 0 to 200 ppm), does not alter the quality of the fuel, is easily dissolved in the fuel, and is also water-soluble in the aqueous system at the interface, the present invention was completed. Ta.

即ち、本発明は、2−n−オクチル−4−イソチアゾロ
ン(化合物Aと称す)と2.3,5.6−テトラクロロ
−4−(メチルスルホニルヒリジン(化合物Bと称す)
を有効成分として含有してなる石油系燃料用スライム防
除薬剤を提供するものである。
That is, the present invention provides 2-n-octyl-4-isothiazolone (referred to as compound A) and 2,3,5,6-tetrachloro-4-(methylsulfonylhyridine (referred to as compound B)).
An object of the present invention is to provide a slime control agent for petroleum-based fuel, which contains as an active ingredient.

〈構成〉 本発明の有効成分である化合物A及びBは、水不溶かつ
有機溶媒に可溶のもので、必髪に応じて溶剤、界面活性
剤等を添加して用いられる。
<Structure> Compounds A and B, which are the active ingredients of the present invention, are insoluble in water and soluble in organic solvents, and are used by adding a solvent, a surfactant, etc. according to the needs of the hair.

溶剤としては、グリコール系溶剤、例えばエチレングリ
コール、ジエチレングリコール、ジエチレングリコール
、アルコール系溶剤、例えばメタノール、エタノール、
鵬σ、キシレン、レクロヘキサノン、トルエン、THF
、プチルセロンルグ、オレイルアルコール等が用いられ
る。界面活性剤は、非イオン系もしくは陰イオン系のも
のが好ましく用いられ、非イオン系界面活性剤としては
ポリオキシエチレン系例えばポリオキシエチレンスチレ
ン化フェノール、ポリオキシエチレンフェニルエーテル
、ポリオキシエチレンアルキルエーテルなどや多価アル
コールエステル系例えばンルビタン脂肪酸エステルなど
が挙げられる。陰イオン系界面活性剤としては、アルキ
ルアリールスルホン酸塩系が好ましく例えばアルキルベ
ンゼンスルホン酸ナトリウム等が挙けられる。
As the solvent, glycol solvents such as ethylene glycol, diethylene glycol, diethylene glycol, alcohol solvents such as methanol, ethanol,
Peng σ, xylene, leclohexanone, toluene, THF
, butylseronrug, oleyl alcohol, etc. are used. Nonionic or anionic surfactants are preferably used, and examples of nonionic surfactants include polyoxyethylene surfactants such as polyoxyethylene styrenated phenol, polyoxyethylene phenyl ether, and polyoxyethylene alkyl ether. and polyhydric alcohol esters such as nrubitan fatty acid ester. The anionic surfactant is preferably an alkylaryl sulfonate salt, such as sodium alkylbenzene sulfonate.

化合物Aと化合物Bとの混合割合は、燃料によシ多少異
なるが、通常化合物A1部(重量部以下同じ)に対して
化合物80.1〜5部、好ましくは0.2〜1部である
The mixing ratio of compound A and compound B varies somewhat depending on the fuel, but is usually 80.1 to 5 parts, preferably 0.2 to 1 part, of the compound to 1 part of compound A (same parts by weight). .

本発明防除薬剤の有効成分の含有割合は、剤型や使用目
的によって異なるが一般的には約1〜30重量%、好ま
しくは10〜30重量%とするのが望ましい。その時溶
剤は、60〜98重量%界面活性剤は1〜10重量%程
度とするのが好ましい。
The content of the active ingredient in the pesticidal agent of the present invention varies depending on the dosage form and purpose of use, but it is generally about 1 to 30% by weight, preferably 10 to 30% by weight. At this time, it is preferable that the amount of the solvent is 60 to 98% by weight, and the amount of surfactant is about 1 to 10% by weight.

本発明防除薬剤は声調整緩衡剤、凍結防止剤、香料、消
泡剤他の工業用殺菌剤等を添加して使用することもでき
る。他の工業用殺菌剤としては、ハロダン化フェノール
、テトラクロロインフタロニトリル、ショートメチル−
p −) 1)ルスルホン、4−10ロフェニル−3−
ヨードグロパギルホル? −A/ 、 3−ヨードj−
2−7’口/4’ギルブチルカーバメイト、N−ジメチ
ル−N−フェニル−(N / −フルオロソクロロメチ
ルチオ)スルファミド、2−プロモー2−ニトロ−1,
3−fロパンジオール、1.2−ペンツインチアゾリン
−3−オン、2−(4゜−チオシアノメチルチオ)ベン
ゾチアゾール、2−メトキシカルボニルアミノペンツイ
ミダゾール、5−クロル−2−メチル−4−インチアゾ
リン−3−オン、2−メチル−4−インチアゾリン−3
−オン等を挙は得るが、これらの例示に限定されるもの
ではない。
The pesticidal agent of the present invention may be used with the addition of a voice control buffer, an antifreeze agent, a fragrance, an antifoaming agent, and other industrial fungicides. Other industrial fungicides include halodanated phenols, tetrachloroinphthalonitrile, short methyl
p-) 1) Lusulfone, 4-10 Lophenyl-3-
Iodoglopa gilhor? -A/, 3-iodoj-
2-7'/4' Gylbutylcarbamate, N-dimethyl-N-phenyl-(N/-fluorosochloromethylthio)sulfamide, 2-promo 2-nitro-1,
3-f lopanediol, 1,2-pentzithiazolin-3-one, 2-(4°-thiocyanomethylthio)benzothiazole, 2-methoxycarbonylaminopenzimidazole, 5-chloro-2-methyl-4-inthiazoline -3-one, 2-methyl-4-inthiazoline-3
-on, etc., but the present invention is not limited to these examples.

石油系燃料とは、重油、軽油、ガソリン、灯油、ジェッ
ト燃料等である。
Petroleum-based fuels include heavy oil, light oil, gasoline, kerosene, and jet fuel.

本発明の防除薬剤の石油系燃料への添加量は、燃料の種
類にもよるが、好ましくは50〜110000pp 、
特に100〜5000 ppmである。
The amount of the pest control agent of the present invention added to petroleum fuel depends on the type of fuel, but is preferably 50 to 110,000 pp.
In particular, it is 100 to 5000 ppm.

本発明の薬剤は、化合物Aの単剤と化合物Bの単剤を各
々別々にへ重油等の燃料に添加するか、化合物Aを燃料
に添加した後、化合物Bを添加、もしくは化合物Bを燃
料に添加した後化合物Bを添加、もしくは、化合物Aと
化合物Bを混合したものをA重油に添加してもよい。
The drug of the present invention can be prepared by adding a single agent of compound A and a single agent of compound B to fuel such as heavy oil separately, or by adding compound B after adding compound A to fuel, or by adding compound B to fuel such as compound B. Compound B may be added after the addition of compound B to heavy oil A, or a mixture of compound A and compound B may be added to heavy oil A.

く効果〉 本発明のスライム防除薬剤は、各種燃料に容易に溶解混
合でき、しかも低い濃度で優れたスライム発生防止効果
を有するもので、化合物A及びBの併用によって燃料が
変質したシネ安定となって化学的反応を起こすこともな
いし、又、人体への影響(毒性)が強くなることもない
といった優れたものである。
Effectiveness> The slime control agent of the present invention can be easily dissolved and mixed with various fuels and has an excellent slime generation prevention effect even at low concentrations. It is an excellent product, as it does not cause any chemical reactions, nor does it have any strong effects (toxicity) on the human body.

以下に、実施例をもって本発明の詳細な説明する。文中
特に断わシのない限シ「部」及び「饅」実施例1及び対
照例1〜2 上記の配合に従って、実施例1として化合物Bを混合溶
剤(シクロヘキサノン、ジメチルホルムアミド)に溶解
した後、さらに化合物A、−(ネロール−N −100
(松本油脂製薬(株)製非イオン系界面活性剤)を添加
溶解しスライム防除薬剤とした。
Hereinafter, the present invention will be explained in detail with reference to examples. Example 1 and Comparative Examples 1 to 2 Unless otherwise specified, Compound B was dissolved in a mixed solvent (cyclohexanone, dimethylformamide) as Example 1 according to the above formulation, and then Furthermore, compound A, -(nerol-N-100
(Nonionic surfactant manufactured by Matsumoto Yushi Pharmaceutical Co., Ltd.) was added and dissolved to prepare a slime control agent.

同様に混合溶剤に各々化合物A、Bを単独とした上記配
合を対照例1及び2のスライム防除薬剤とした。
Similarly, the slime control agents of Control Examples 1 and 2 were prepared by using the above-mentioned formulations in which each of Compounds A and B was used alone in a mixed solvent.

試験例1(抗菌力試験) 殺菌水で希釈した薬液を調製し、その希釈液1dを50
℃に冷した培地(馬鈴薯煎汁寒天)49ゴと混合して直
径9傭の殺菌シャーレに入れ、所定濃度の薬液含有寒天
平板を調製した。予め斜面培地で28℃、7日間培養し
た供試菌(A重油スライムから分離されたもの)の胞子
懸濁液を調製し、さらに滅菌した直径5簡のペーパー・
ディスクを各胞子懸濁液に含浸して平板上に置いた。こ
れらのシャーレを28℃、7日間培養して黴の生育の有
無を調査し、各画の生育を完全に阻止する最低薬剤濃度
(最低生育阻止濃度)を求めた。その結果は表1に示す
通シで本発明の化合物人と化合物Bとの混合物からなる
薬剤が相乗的防菌効果F−1〜Y−3は以下の黴、及び
酵母を示す。
Test example 1 (antibacterial activity test) Prepare a drug solution diluted with sterile water, and add 1 d of the diluted solution to 50%
The mixture was mixed with 49° C.-cooled culture medium (potato decoction agar) and placed in a sterilized Petri dish with a diameter of 9° C. to prepare an agar plate containing a drug solution at a predetermined concentration. A spore suspension of the test bacteria (separated from A heavy oil slime) was prepared in advance by culturing on a slant medium at 28°C for 7 days, and then a sterilized paper with a diameter of 5 pieces was prepared.
A disk was impregnated with each spore suspension and placed on a plate. These Petri dishes were cultured at 28° C. for 7 days to examine the presence or absence of mold growth, and the lowest drug concentration that completely inhibited the growth of each plot (minimum growth-inhibiting concentration) was determined. The results are shown in Table 1, and the drug consisting of a mixture of the compound of the present invention and compound B has a synergistic antibacterial effect on the following molds and yeasts F-1 to Y-3.

F −1: Cladosporium Ip。F-1: Cladosporium Ip.

(クラドスポリウム エスピー) F −2: Penicillium 1ips(ペニ
シリウム エスピー) F−3:Aspergillus  Ips(アスペル
ギルス エスピー) F−4: Fusarium  1Ip6(フザリウム
 エスピー) F −5: Psnicillium l1pa(ペニ
シリウム エスピー) Y −1: Candi da lIp。
(Cladosporium sp.) F-2: Penicillium 1ips (Penicillium sp.) F-3: Aspergillus Ips (Aspergillus sp.) F-4: Fusarium 1Ip6 (Fusarium sp.) F-5: Psnicillium l1pa (Penicillium sp.) Rium SP) Y-1: Candi da lIp.

(キャンディダ エスピー) Y−2: Candida  ap。(Candida SP) Y-2: Candida ap.

(キャンディダ エスピー) Y−3:Torulopsis  ljp。(Candida SP) Y-3: Torulopsis ljp.

(トルロプシス エスピー) A重油中での薬剤のスライム防除効果を確認する為、胞
子の発芽を抑制する予防効果と既に発生している菌体に
直接作用し菌を死滅させる殺菌効果の実験を行なった。
(Torulopsis sp.) In order to confirm the slime control effect of the drug in heavy oil A, we conducted experiments on the preventive effect of suppressing the germination of spores and the bactericidal effect of directly acting on already generated bacterial cells to kill them. .

試験(例2(胞子懸濁液接種法) 試験方法 無機塩液体培地10dを418mの試験管に
入れ所定量の実施例、対照 例の薬剤を添加したA重油を9.51rLl加えた。次
に斜面培養したものよシ 菌の胞子を採取し、A重油に分散さ せ0.5 +nlを接種した。25℃±2℃で30日間
静置培養し、A重油−水 層の界面にスライムが発生するかど うか検討した。
Test (Example 2 (Spore suspension inoculation method) Test method 10 d of inorganic salt liquid medium was placed in a 418 m test tube, and 9.51 rLl of heavy oil A containing the prescribed amount of the drugs of Examples and Controls was added. Next, The spores of the fungus that had been cultured on the slope were collected, dispersed in heavy oil A, and inoculated with 0.5 + nl.Still cultured at 25°C ± 2°C for 30 days, and slime was generated at the interface of the heavy oil A-water layer. I considered whether or not to do so.

判定基準 m:スライムの発生なし 十ニスライムの発生少ない 丑ニスライムの発生多い 市販薬剤の有効成分 A:有機非金属化合物 B:カチオン系界面活性剤 試験例3(菌叢接種法) 試験方法 接種には6菌の菌叢(カビ:3m×3ms度
の大きさ)、酵母は/白金 耳を接種する。
Judgment Criteria M: No slime generation (10) Low slime generation (Ushii) High slime generation Active ingredient of commercially available drug A: Organic non-metallic compound B: Cationic surfactant Test Example 3 (Bacterial flora inoculation method) Test method For inoculation A bacterial colony of 6 bacteria (mold: 3 m x 3 ms in size) and a loopful of yeast were inoculated.

その他の条件は胞子懸濁液接種法と ′)発明の薬剤が、100〜250 ppm程度の低い
濃度においてもA重油中でのスライム発生防除効果に優
れることを各画の胞子発芽の抑制による予防効果及び既
に発生している菌を死滅させる殺菌効果のあることから
確認した。
The other conditions are the spore suspension inoculation method and ') prevention by suppressing spore germination in each image, which shows that the drug of the invention has an excellent slime generation control effect in heavy oil A even at a low concentration of about 100 to 250 ppm. It was confirmed because of its effectiveness and its bactericidal effect, which kills existing bacteria.

代理人 弁理士  高 橋 勝 利Agent Patent Attorney Katsutoshi Takahashi

Claims (1)

【特許請求の範囲】[Claims] 2−n−オクチル−4−イソチアゾロンと2,3,5,
6−テトラクロロ−4−(メチルスルホニル)ピリジン
を有効成分として含有してなる石油系燃料用スライム防
除薬剤。
2-n-octyl-4-isothiazolone and 2,3,5,
A slime control agent for petroleum fuel containing 6-tetrachloro-4-(methylsulfonyl)pyridine as an active ingredient.
JP62312075A 1987-12-11 1987-12-11 Slime control chemicals for petroleum fuels Expired - Lifetime JP2605764B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP62312075A JP2605764B2 (en) 1987-12-11 1987-12-11 Slime control chemicals for petroleum fuels

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Application Number Priority Date Filing Date Title
JP62312075A JP2605764B2 (en) 1987-12-11 1987-12-11 Slime control chemicals for petroleum fuels

Publications (2)

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JPH01153604A true JPH01153604A (en) 1989-06-15
JP2605764B2 JP2605764B2 (en) 1997-04-30

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0390394A2 (en) * 1989-03-31 1990-10-03 Zeneca Limited Composition and use
JPH0671287A (en) * 1992-08-27 1994-03-15 Shikoku Chem Corp Bulking canceling agent for activated sludge
EP0608911A1 (en) * 1989-11-03 1994-08-03 Rohm And Haas Company Synergistic microbicidal combinations
JPH0892012A (en) * 1994-09-26 1996-04-09 Senkawa:Kk Antimicrobial composition
JP2003063916A (en) * 2001-08-29 2003-03-05 Shinto Fine Co Ltd Antibacterial composition for industrial use and antibacterial treatment method
JP2013507506A (en) * 2009-10-14 2013-03-04 パロックス リミテッド Liquid fuel protection
JP2017156089A (en) * 2016-02-29 2017-09-07 株式会社日立ハイテクノロジーズ Electrolyte analyzer

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0390394A2 (en) * 1989-03-31 1990-10-03 Zeneca Limited Composition and use
EP0608911A1 (en) * 1989-11-03 1994-08-03 Rohm And Haas Company Synergistic microbicidal combinations
JPH0671287A (en) * 1992-08-27 1994-03-15 Shikoku Chem Corp Bulking canceling agent for activated sludge
JPH0892012A (en) * 1994-09-26 1996-04-09 Senkawa:Kk Antimicrobial composition
JP2003063916A (en) * 2001-08-29 2003-03-05 Shinto Fine Co Ltd Antibacterial composition for industrial use and antibacterial treatment method
JP2013507506A (en) * 2009-10-14 2013-03-04 パロックス リミテッド Liquid fuel protection
JP2017156089A (en) * 2016-02-29 2017-09-07 株式会社日立ハイテクノロジーズ Electrolyte analyzer

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