JPS63316702A - Antimicrobial agent - Google Patents
Antimicrobial agentInfo
- Publication number
- JPS63316702A JPS63316702A JP15136587A JP15136587A JPS63316702A JP S63316702 A JPS63316702 A JP S63316702A JP 15136587 A JP15136587 A JP 15136587A JP 15136587 A JP15136587 A JP 15136587A JP S63316702 A JPS63316702 A JP S63316702A
- Authority
- JP
- Japan
- Prior art keywords
- antimicrobial agent
- compound
- formula
- complex compound
- water systems
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004599 antimicrobial Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 150000001450 anions Chemical group 0.000 claims abstract description 5
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical compound O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 15
- 244000005700 microbiome Species 0.000 abstract description 10
- 238000000576 coating method Methods 0.000 abstract description 8
- 239000011248 coating agent Substances 0.000 abstract description 7
- 239000000243 solution Substances 0.000 abstract description 7
- 230000002265 prevention Effects 0.000 abstract description 5
- 229920001131 Pulp (paper) Polymers 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract description 3
- 239000008235 industrial water Substances 0.000 abstract description 3
- 229920000126 latex Polymers 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 239000006185 dispersion Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000005555 metalworking Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000001457 metallic cations Chemical group 0.000 abstract 1
- 230000001473 noxious effect Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 24
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 16
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 239000012530 fluid Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- UGQRORUKXRJCIS-UHFFFAOYSA-N magnesium 5-chloro-2-methyl-1,2-thiazol-3-one dinitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O.CN1SC(Cl)=CC1=O UGQRORUKXRJCIS-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 241000233866 Fungi Species 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- -1 Salt compounds Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- OVQPFRKYCXCKNG-UHFFFAOYSA-N 1,1-dibromo-1-nitropropan-2-ol Chemical compound CC(O)C(Br)(Br)[N+]([O-])=O OVQPFRKYCXCKNG-UHFFFAOYSA-N 0.000 description 1
- FMNZAHDAULEOSO-UHFFFAOYSA-N 2,2-dibromo-2-nitroethanol Chemical group OCC(Br)(Br)[N+]([O-])=O FMNZAHDAULEOSO-UHFFFAOYSA-N 0.000 description 1
- KIPMDPDAFINLIV-UHFFFAOYSA-N 2-nitroethanol Chemical compound OCC[N+]([O-])=O KIPMDPDAFINLIV-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000013055 pulp slurry Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は一般式（Ｉ）で表わされるイソチアゾロン錯化
合物又はインチアゾロン誘導体錯化合物と一般式（ＩＩ
）で表わされるジブロモニトロアルコール化合物とを含
有し、両者の相乗効果を利用する新規な防菌剤に関する
。本防菌剤は、特に紙パルプ製造に関係ある工業用水系
において好適に使用される。Detailed Description of the Invention (Industrial Application Field) The present invention relates to an isothiazolone complex compound or an inthiazolone derivative complex compound represented by the general formula (I) and an inthiazolone derivative complex compound represented by the general formula (II).
) and a dibromonitroalcohol compound represented by the following, and which utilizes the synergistic effect of both. This antibacterial agent is particularly suitable for use in industrial water systems related to paper pulp production.
（従来技術及び問題点）
従来、紙パルプ工業分野における抄紙工程からの廃水、
各種産業分野における循環冷却水等種々の用水系にあっ
ては、また、工業用水を使用して作る水性塗料、紙用塗
工液、ラテックス、捺染糊、皮革などにあっては、それ
らに有害な微生物が増繁殖しやすく、これが生産性や品
質の低下の原因となっている。(Prior art and problems) Conventionally, wastewater from the papermaking process in the pulp and paper industry,
In various water systems such as circulating cooling water in various industrial fields, and in water-based paints, paper coating fluids, latex, printing pastes, leather, etc. made using industrial water, it is harmful to them. microorganisms are likely to multiply, which causes a decline in productivity and quality.
特に、紙パルブ工業分野における用水系では、最近、糸
状菌及び酵母類の増繁殖によりスライムが発生し、バル
ブスラリーが流れる水路、とりわけスラリ＝が接する壁
面の粗い場所やチェスト、フローボックス、輸送パイプ
、その他パルプスラリーの流速が小さくなって淀むよう
な場所において、スライムが付着形成される。このスラ
イムは、しばしば脱離し、紙切れや紙パルプ製品汚染の
原因となっているほか、微生物の繁殖による種々の障害
を発生させている。In particular, in water systems in the pulp and paper industry, slime has recently been generated due to the multiplication of filamentous fungi and yeasts. , and other places where the flow rate of the pulp slurry is low and stagnates, slime is formed. This slime often detaches and causes contamination of paper pieces and pulp and paper products, as well as various problems caused by the growth of microorganisms.
このような障害発生は、高速マシンを使用する際には特
に大きな問題となり、著しい生産性低下及び経済的損失
を招来している。The occurrence of such failures becomes a particularly serious problem when high-speed machines are used, resulting in a significant decrease in productivity and economic loss.
更に、金属加工油剤の冷却用循環用水系においても、微
生物が増繁殖し加工油剤の冷却性能や乳化性を阻害した
り、また、悪臭が発生し作業環境の悪化をさせ公衆衛生
上好ましくない現象をひきおこしている。Furthermore, in the circulating water system for cooling metal processing fluids, microorganisms multiply and multiply, impairing the cooling performance and emulsifying properties of processing fluids, and producing bad odors, deteriorating the working environment, which is an undesirable phenomenon in terms of public health. is causing the
有害微生物の繁殖によるその他の障害は、水性塗料、紙
用塗工液、高分子ラテックス、製紙用パルプ、糊、皮革
、金属加工油剤などの工業用製品にもみられる。Other problems caused by the growth of harmful microorganisms occur in industrial products such as water-based paints, paper coatings, polymer latex, paper pulp, glues, leather, and metalworking fluids.
ところで、前記用水系、又は、前記工業用製品における
有害微生物の発生を抑制し、ないしは防除する薬剤とし
ては、これまで例えば有機金属化合物類、有機塩素化合
物類、有機硫黄化合物類、第４級アンモニウム塩化合物
類などが使用されてきたが、これらの化合物類は人体に
対し毒性を有し、また、悪臭や異臭を発し、更には発泡
などの好まし・くない現象を生じる。加えて、これらの
防除剤含有水系は、これを一般河用や海等に反流した場
合には魚介類に対し悪影響を与え環境保全上問題を生じ
る。By the way, as agents for suppressing or controlling the occurrence of harmful microorganisms in the water system or industrial products, for example, organic metal compounds, organic chlorine compounds, organic sulfur compounds, and quaternary ammonium compounds have been used. Salt compounds and the like have been used, but these compounds are toxic to the human body, emit foul odors and foreign odors, and even cause undesirable phenomena such as foaming. In addition, when water systems containing these pesticides are discharged back into rivers, the sea, etc., they have a negative impact on fish and shellfish, causing problems in terms of environmental conservation.
（発明の目的、構成及び効果）
本発明者等は、防菌剤について上記したような欠点を除
去すべく、鋭意研究を重ねた結果、本発明を完成するに
至った。(Object, structure, and effect of the invention) The present inventors have completed the present invention as a result of extensive research in order to eliminate the above-mentioned drawbacks of antibacterial agents.
即ち、本発明は下記の防菌剤である。That is, the present invention is the following antibacterial agent.
一般式
（式中、Ｒ１は水素原子又は置換若しくは非置換の一価
炭化水素基、Ｒ２及びＲ３は同−若しくは、 異なり
で水素原子又はハロゲン原子、Ｍは金属カチオン又はア
ンモニウム、Ｘは錯化合物を形成するアニオン、ａは１
又は２、ｂはアニオンＸがカチオンＭの原子価を満足す
る整数を示す。）で表わされるインチアゾロン錯化合物
又はイソチアゾロン誘導体錯化合物と、
一般式
％式％（）
（式中、Ｒは水素原子、置換し得るアルキル基を表わす
。）で表わされるジブロモニトロアルコール化合物とを
（１：１０）〜（１０： １）の重量割合で含有するこ
とを特徴とする防菌剤。General formula (wherein R1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, R2 and R3 are the same or different and are hydrogen atoms or halogen atoms, M is a metal cation or ammonium, and X is a complex compound) anion to form, a is 1
Alternatively, 2 and b represent an integer such that the anion X satisfies the valence of the cation M. ) and a dibromonitroalcohol compound represented by the general formula % () (wherein R represents a hydrogen atom or a substitutable alkyl group). :10) to (10:1) in a weight ratio.
一般式（１）で表わされる化合物は特公昭５４−２３９
６８号公報に記載されている殺菌剤であり、また、一般
式（ｎ）で表わされる化合物は特公昭４０−８９１７号
公報に記載されている殺菌剤である。The compound represented by the general formula (1) is
The compound represented by the general formula (n) is a fungicide described in Japanese Patent Publication No. 40-8917.
これら各々の殺菌剤は、成る種類の微生物に効果が限定
されるなど殺菌効果が不十分であり、また、効果の持続
性にも欠けるなど防菌剤としては満足すべきものではな
い。Each of these bactericidal agents is not satisfactory as a bactericidal agent, as the bactericidal effect is limited to certain types of microorganisms, and the bactericidal effect is insufficient, and the duration of the effect is also lacking.
本発明の防菌剤は、構成成分個別からは到底予測するこ
とができない、極めて優れた防菌作用を発揮し、また、
有害微生物である糸状菌、細菌、酵母類等に対してその
種類に係わりなく広い適用範囲を有する。The antibacterial agent of the present invention exhibits an extremely excellent antibacterial effect that cannot be predicted from the individual constituent components, and
It has a wide range of applications regardless of the type of harmful microorganisms such as filamentous fungi, bacteria, and yeast.
本発明における一般式（Ｉ）の化合物としては、例えば
５−クロロ−２−メチル−３−インチアゾロンマグネシ
ウムナイトレート、２−メチル−３−インチアゾロンマ
グネシウムナイトレート、２−オクチル−４−クロロ−
３−インチアゾロンカルシウムクロライド等があげられ
る。Examples of the compound of general formula (I) in the present invention include 5-chloro-2-methyl-3-inchazolone magnesium nitrate, 2-methyl-3-inchazolone magnesium nitrate, and 2-octyl-4-inchazolone magnesium nitrate. Chloro
Examples include 3-inchazolone calcium chloride.
一般式（ＩＩ）の化合物としては、２．２−ジブロモ−
２−二トロエタノール、２，２−ジブロモ−２−ニトロ
−１−メチルエタノール等があげられる。As the compound of general formula (II), 2,2-dibromo-
Examples include 2-nitroethanol, 2,2-dibromo-2-nitro-1-methylethanol, and the like.
上記したインチアゾロン錯化合物又はインチアゾロン誘
導体錯化合物や、ジブロモニトロアルコール化合物は、
いずれも使用に際しては１種のみに限定されるものでは
なく、２種以上を併用してもよい。The above-mentioned inthiazolone complex compound or intiazolone derivative complex compound and dibromonitroalcohol compound are
The use of any of them is not limited to only one type, and two or more types may be used in combination.
本発明で最も好ましい組成は、一方の成分が５−クロロ
−２−メチル−３−インチアゾロンマグネシウムナイト
レートと２−メチル−３−インチアゾロンマグネシウム
ナイトレートとの３：１（重量）混合物で、他方の成分
が２．２−ジブロモ−２−二トロエタノールである。The most preferred composition of the present invention is a 3:1 (by weight) mixture in which one component is 5-chloro-2-methyl-3-inchazolone magnesium nitrate and 2-methyl-3-inchazolone magnesium nitrate. The other component is 2,2-dibromo-2-nitroethanol.
一般式（Ｉ）の化合物と一般式（ｎ）の化合物との配合
割合（重量）は（１：１０）〜（１０：１）、好ましく
は（１：５）〜（５： １）である。The compounding ratio (weight) of the compound of general formula (I) and the compound of general formula (n) is (1:10) to (10:1), preferably (1:5) to (5:1). .
いずれか一方が少なすぎても満足できる効果を得ること
ができない。If either one of them is too small, a satisfactory effect cannot be obtained.
本発明の防菌剤は、基本的には上記した２成分を均一に
混合することにより調製されるが、一般的には水溶液、
溶剤溶液、乳化分散液等として使用に供される。The antibacterial agent of the present invention is basically prepared by uniformly mixing the two components described above, but is generally prepared as an aqueous solution,
It can be used as a solvent solution, emulsified dispersion, etc.
ここで使用することのできる溶剤としては、アルコール
系溶剤、ケトン系溶剤、エーテル系溶剤、炭化水素系溶
剤等が、また乳化分散剤としては、アニオン系界面活性
剤、ノニオン系界面活性剤等が例示される。また、本発
明の防菌剤は任意の担体に担持して使用してもよく、使
用態様に特に制限はなく種々の方法を採用することがで
きる。Solvents that can be used here include alcohol solvents, ketone solvents, ether solvents, hydrocarbon solvents, etc. Emulsifying dispersants include anionic surfactants, nonionic surfactants, etc. Illustrated. Furthermore, the antibacterial agent of the present invention may be used by being supported on any carrier, and there are no particular restrictions on the mode of use, and various methods can be adopted.
この防菌剤の使用に際しての添加量は、微生物濃度によ
っても異なるが、一般的に紙パルブ工業等の分野におけ
る用水系の場合は０．０１〜１１００ｐｐ （インチ
アゾロン錯化合物等及びジブロモニトロアルコール化合
物の合計量基準）、水性塗料、糊、皮革等の分野の場合
は１〜５００ｐｐｍ（同上）であり、この程度で良好な
殺菌効果が得られる。The amount added when using this antibacterial agent varies depending on the microbial concentration, but in general, for water systems in fields such as the pulp and paper industry, it is 0.01 to 1100 pp (for intiazolone complex compounds, etc. and dibromonitroalcohol compounds). In the field of water-based paints, glues, leather, etc., it is 1 to 500 ppm (same as above), and a good bactericidal effect can be obtained at this level.
本発明の防菌剤に、この発明の目的を阻害しない範囲で
安定剤、界面活性剤等を添加することは何ら差支えない
。There is no problem in adding stabilizers, surfactants, etc. to the antibacterial agent of the present invention as long as they do not impede the purpose of the present invention.
（実施例及び比較例）
下記の各側で示す処方によって防菌剤をそれぞれ調製し
た。各例中の部は重量部を意味する。(Examples and Comparative Examples) Antibacterial agents were prepared according to the formulations shown on each side below. Parts in each example mean parts by weight.
実施例１
５−クロロ−２−メチル−３−イソチアゾロンマグネシ
ウムナイトレートと２−メチル−３−インチアゾロンマ
グネシウムナイトレートとの３：１ （重量）混合物
５部ジエチレングリコール
８５部実施例２
５−クロロ−２−メチル−３−イソチアゾロンマグネシ
ウムナイトレートと２−メチル−３−インチアゾロンマ
グネシウムナイトレートとの３：１ （重量）混合物
５部ジエチレングリコール
８５部実施例３
２−オクチル−４−クロロ−３−インチアゾロンカルシ
ウム（ｎ）クロライド ５部ジエチレングリコー
ル ８５部実施例４
２−オクチル−４−クロロ−３−インチアゾロンカルシ
ウム（ｎ）クロライド ５部ジエチレングリコー
ル ８５部比較例１
５−クロロ−２−メチル−３−イソチアゾロンマグネシ
ウムナイトレートと２−メチル−３−インチアゾロンマ
グネシウムナイトレートとの３：１ （重量）混合物
１５部ジエチレングリコール
８５部比較例２
２−オクチル−４−クロロ−３−インチアゾロンカルシ
ウム（Ｉ［）クロライド １５部ジエチレングリコ
ール ８５部比較例３
ジエチレングリコール ８５部比較例４
ジエチレングリコール ８５部（効果試験
）
上記実施例１〜４及び比較例１〜４で調製した防菌剤に
ついて下記のような試験方法により、菌増殖防止作用及
びスライム発生防止作用を調べた。Example 1 3:1 (by weight) mixture of 5-chloro-2-methyl-3-isothiazolone magnesium nitrate and 2-methyl-3-inchazolone magnesium nitrate
5-part diethylene glycol
85 parts Example 2 3:1 (by weight) mixture of 5-chloro-2-methyl-3-isothiazolone magnesium nitrate and 2-methyl-3-inchazolone magnesium nitrate
5-part diethylene glycol
85 parts Example 3 2-octyl-4-chloro-3-inchazolone calcium (n) chloride 5 parts diethylene glycol 85 parts Example 4 2-octyl-4-chloro-3-inchazolone calcium (n) chloride 5 Part diethylene glycol 85 parts Comparative Example 1 3:1 (by weight) mixture of 5-chloro-2-methyl-3-isothiazolone magnesium nitrate and 2-methyl-3-inchazolone magnesium nitrate
15 parts diethylene glycol
85 parts Comparative Example 2 2-Octyl-4-chloro-3-inchazolone calcium (I[) chloride 15 parts Diethylene glycol 85 parts Comparative Example 3 Diethylene glycol 85 parts Comparative Example 4 Diethylene glycol 85 parts (Efficacy test) Above Examples 1 to The antibacterial agents prepared in Example No. 4 and Comparative Examples 1 to 4 were examined for their antibacterial effects and slime generation effects using the following test methods.
試験例１
〔抄紙工程後の排水における菌増殖防止及びスライム発
生防止試験〕
ビットに１日のうち２時間、３回にわたり、水中濃度が
２０ｐｐｍになるように７日間添加して、白水中の微生
物の菌数を測定した。Test Example 1 [Bacterial growth prevention and slime generation prevention test in wastewater after papermaking process] Microorganisms in white water were added to bits for 2 hours, 3 times a day, for 7 days so that the water concentration was 20 ppm. The number of bacteria was measured.
試験方法は白水試料を滅菌水で希釈し、この一定量をシ
ャーレに採り、溶解したワックスマン寒天培地を注入し
、混和し、平板状に固化させた。恒温器内（３２℃）で
２日間培養後発生する微生物コロニーをコロニー計数器
にて測定した。また、抄造時の紙切れの回数も測定し、
防菌効果を確認した。その結果を下記の第１表に示す。The test method involved diluting a white water sample with sterilized water, placing a certain amount of this in a Petri dish, pouring dissolved Waxman agar medium into it, mixing it, and solidifying it into a flat plate. After culturing in a thermostatic chamber (32° C.) for 2 days, microbial colonies generated were measured using a colony counter. We also measured the number of paper breaks during papermaking.
The antibacterial effect was confirmed. The results are shown in Table 1 below.
第１表
上記第１表の結果から、本発明の防菌剤（実施例１〜４
）は、製紙工場の排水において優れた菌増殖防止作用と
スライム発生防止作用を有することがわかる。Table 1 From the results in Table 1 above, the antibacterial agent of the present invention (Examples 1 to 4)
) was found to have excellent anti-bacterial growth and slime generation prevention effects in wastewater from paper mills.
試験例２
〔製紙用塗工液における菌増殖防止試験〕ｐＨ１０，０
の澱粉系塗工液にブイヨン液体培地及び予め腐敗させた
塗工液を加えて撹拌し、３００ｐｐｍ濃度になるように
調整した防菌剤を添加した。Test Example 2 [Bacterial growth prevention test in papermaking coating solution] pH 10.0
A bouillon liquid medium and a previously spoiled coating solution were added to the starch-based coating solution, stirred, and an antibacterial agent adjusted to a concentration of 300 ppm was added.
これを３２℃の恒温器に５日間保存した後、各塗工液中
の生菌数を測定した。その結果を下記の第２表に示す。After storing this in a thermostat at 32° C. for 5 days, the number of viable bacteria in each coating solution was measured. The results are shown in Table 2 below.
第２表
上記第２表の結果から本発明の防菌剤（実施例１〜４）
は製紙用塗工液において優れた菌増殖防止作用を有する
ことがわかる。Table 2 From the results in Table 2 above, the antibacterial agent of the present invention (Examples 1 to 4)
It can be seen that it has an excellent anti-microbial growth effect in papermaking coating solutions.
Claims (1)
） （式中、Ｒ＾１は水素原子又は置換若しくは非置換の一
価炭化水素基、Ｒ＾２及びＲ＾３は同一若しくは異なり
て水素原子又はハロゲン原子、Ｍは金属カチオン又はア
ンモニウム、Ｘは錯化合物を形成するアニオン、ａは１
又は２、ｂはアニオンＸがカチオンＭの原子価を満足す
る整数を示す。）で表わされるイソチアゾロン錯化合物
又はイソチアゾロン誘導体錯化合物と、 一般式 ▲数式、化学式、表等があります▼・・・・・・（II） （式中、Ｒは水素原子、置換し得るアルキル基を示す。 ）で表わされるジブロモニトロアルコール化合物とを、
（１：１０）〜（１０：１）の重量割合で含有すること
を特徴とする防菌剤。[Claims] General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・( I
) (In the formula, R^1 is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, R^2 and R^3 are the same or different and are hydrogen atoms or halogen atoms, M is a metal cation or ammonium, and X is Anion forming a complex compound, a is 1
Alternatively, 2 and b represent an integer such that the anion X satisfies the valence of the cation M. ) isothiazolone complex compound or isothiazolone derivative complex compound represented by general formula▲mathematical formula, chemical formula, table, etc.▼・・・・・・(II) ) and a dibromonitroalcohol compound represented by
An antibacterial agent characterized in that it is contained in a weight ratio of (1:10) to (10:1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62151365A JPH0647524B2 (en) | 1987-06-19 | 1987-06-19 | Industrial antibacterial agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62151365A JPH0647524B2 (en) | 1987-06-19 | 1987-06-19 | Industrial antibacterial agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63316702A true JPS63316702A (en) | 1988-12-26 |
| JPH0647524B2 JPH0647524B2 (en) | 1994-06-22 |
Family
ID=15516949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62151365A Expired - Lifetime JPH0647524B2 (en) | 1987-06-19 | 1987-06-19 | Industrial antibacterial agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0647524B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02784A (en) * | 1988-10-08 | 1990-01-05 | Katayama Chem Works Co Ltd | Isothiazolone composition and use thereof |
| JPH02134302A (en) * | 1988-09-30 | 1990-05-23 | Union Carbide Chem & Plast Co Inc | Antibacterial composition and its usage |
| EP0608914A1 (en) * | 1989-11-03 | 1994-08-03 | Rohm And Haas Company | Synergistic microbicidal combinations |
| US5591759A (en) * | 1989-05-17 | 1997-01-07 | Katayama Chemical, Inc. | Aqueous isothiazolone formulation |
| JP2001261509A (en) * | 2000-03-17 | 2001-09-26 | Kurita Water Ind Ltd | Industrial antimicrobial agent composition and industrial antimicrobial method |
| JP2006001850A (en) * | 2004-06-16 | 2006-01-05 | Permachem Asia Ltd | Aqueous preservative |
| JP2006151885A (en) * | 2004-11-30 | 2006-06-15 | Nagase Chemtex Corp | Aqueous antimicrobial preparation |
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| JPS54140726A (en) * | 1978-04-24 | 1979-11-01 | Somar Mfg | Slime controlling agent in paper pulp industry |
| JPS5573603A (en) * | 1978-11-30 | 1980-06-03 | Kumiai Chem Ind Co Ltd | Antibacterial agent for destroying algae |
| JPS5618904A (en) * | 1979-07-25 | 1981-02-23 | Kumiai Chem Ind Co Ltd | Antimicrobial and algicidal agent |
| JPS5699401A (en) * | 1980-10-24 | 1981-08-10 | Kumiai Chem Ind Co Ltd | Stable liquid microbicidal and algicidal preparation |
| JPS584682A (en) * | 1981-06-27 | 1983-01-11 | Mitsubishi Heavy Ind Ltd | Trunk device for underwater operation |
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| JPS5978109A (en) * | 1982-09-23 | 1984-05-04 | ロ−ム・アンド・ハ−ス・コンパニ− | Solid microbicidal composition and use |
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| JPS6054281A (en) * | 1983-09-02 | 1985-03-28 | Hitachi Ltd | Manufacture of build-up welded flange |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02134302A (en) * | 1988-09-30 | 1990-05-23 | Union Carbide Chem & Plast Co Inc | Antibacterial composition and its usage |
| JPH02784A (en) * | 1988-10-08 | 1990-01-05 | Katayama Chem Works Co Ltd | Isothiazolone composition and use thereof |
| US5591759A (en) * | 1989-05-17 | 1997-01-07 | Katayama Chemical, Inc. | Aqueous isothiazolone formulation |
| EP0608914A1 (en) * | 1989-11-03 | 1994-08-03 | Rohm And Haas Company | Synergistic microbicidal combinations |
| JP2001261509A (en) * | 2000-03-17 | 2001-09-26 | Kurita Water Ind Ltd | Industrial antimicrobial agent composition and industrial antimicrobial method |
| JP4552165B2 (en) * | 2000-03-17 | 2010-09-29 | 栗田工業株式会社 | Industrial antibacterial agent composition and industrial antibacterial method |
| JP2006001850A (en) * | 2004-06-16 | 2006-01-05 | Permachem Asia Ltd | Aqueous preservative |
| JP2006151885A (en) * | 2004-11-30 | 2006-06-15 | Nagase Chemtex Corp | Aqueous antimicrobial preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0647524B2 (en) | 1994-06-22 |
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