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JP6008382B2 - Industrial antibacterial composition - Google Patents

Industrial antibacterial composition Download PDF

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JP6008382B2
JP6008382B2 JP2012057492A JP2012057492A JP6008382B2 JP 6008382 B2 JP6008382 B2 JP 6008382B2 JP 2012057492 A JP2012057492 A JP 2012057492A JP 2012057492 A JP2012057492 A JP 2012057492A JP 6008382 B2 JP6008382 B2 JP 6008382B2
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isothiazolone
antibacterial composition
formula
antibacterial
industrial antibacterial
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JP2013189404A (en
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義晃 加藤
加藤  義晃
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SC Environmental Science Co Ltd
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Description


一般式(II)

Figure 0006008382
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)

Formula (II)
Figure 0006008382
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)

ポリマーエマルションは重合停止剤として還元剤を用いることが一般的であり、過剰に還元剤が添加されるため組成物中に還元剤が残存する場合が一般的である。このポリマーエマルション以外の水系組成物においても漂白、脱色、酸化防止の目的で還元剤が添加される事例は数多く存在する。 In the polymer emulsion, a reducing agent is generally used as a polymerization terminator, and since the reducing agent is excessively added, the reducing agent generally remains in the composition. Even in aqueous compositions other than this polymer emulsion, there are many cases where a reducing agent is added for the purpose of bleaching, decoloring and oxidation prevention.

ポリマーエマルションをはじめとする水系組成物は細菌や真菌などの微生物による腐敗や汚染を受けやすく、これを回避するために一般的には抗菌剤の添加が必須となっている。工業的に使用される水系組成物の抗菌剤としては、2−ブロモー2−ニトロプロパン−1,3−ジオールや2,2−ジブロモ−2−ニトロエタノールなどのブロモニトロ化合物や、1,2−ベンズ−3−イソチアゾロンや5−クロロ−2−メチル−3(2H)−イソチアゾロン、2−メチル−3(2H)−イソチアゾロン、2−n−オクチル−3(2H)−イソチアゾロンなどのイソチアゾロン化合物や、メチレンビスチオジアネートや2−(4−チオシアノメチルチオ)ベンゾチアゾールなどのチオシアネート化合物などが使用されている。 Aqueous compositions such as polymer emulsions are susceptible to spoilage and contamination by microorganisms such as bacteria and fungi, and in general, the addition of antibacterial agents is essential to avoid this. Antibacterial agents for aqueous compositions used industrially include bromonitro compounds such as 2-bromo-2-nitropropane-1,3-diol and 2,2-dibromo-2-nitroethanol, and 1,2-benz Isothiazolone compounds such as -3-isothiazolone, 5-chloro-2-methyl-3 (2H) -isothiazolone, 2-methyl-3 (2H) -isothiazolone, 2-n-octyl-3 (2H) -isothiazolone, methylene Thiocyanate compounds such as bisthiodianate and 2- (4-thiocyanomethylthio) benzothiazole are used.

しかしながらこれら工業用の水系組成物に使用される抗菌剤は還元剤や還元性物質による影響を受けやすく、比較的短期間で分解することから必要以上に抗菌剤の添加濃度を高める必要があり、より添加濃度が少なくてすみ、かつより長期にわたる抗菌性能を発揮する工業用抗菌組成物が望まれている。 However, antibacterial agents used in these industrial water-based compositions are susceptible to the effects of reducing agents and reducing substances, and it is necessary to increase the concentration of the antibacterial agent more than necessary because it decomposes in a relatively short period of time. There is a demand for an industrial antibacterial composition that requires less additive concentration and exhibits antibacterial performance over a longer period of time.

亜鉛ピリチオン複合化合物についてはWO2009/144929号公報(特許文献1)やWO2009/44523号公報(特許文献2)、特開2006−335757(特許文献3)に開示されているが、これらの亜鉛ピリチオン複合体が還元剤や還元性物質の存在下で抗菌活性を保持することについてはなんら記載がない。 Zinc pyrithione complex compounds are disclosed in WO2009 / 144929 (patent document 1), WO2009 / 44523 (patent document 2), and JP-A 2006-335757 (patent document 3). There is no mention that the body retains antibacterial activity in the presence of reducing agents and reducing substances.


一般式(II)

Figure 0006008382
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)

Formula (II)
Figure 0006008382
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)

WO2009/144929WO2009 / 144929 WO2009/44523WO2009 / 44523 特開2006−335757JP 2006-335757 A

本発明が解決しようとする課題は、ポリマーエマルションをはじめとする還元剤や還元性物質を含有する水系組成物を、細菌や真菌等の微生物汚染から少量の添加により長期間にわたって保護することが可能な工業用抗菌組成物を提供することにある。 The problem to be solved by the present invention is that it is possible to protect a water-based composition containing a reducing agent including a polymer emulsion and a reducing substance from microbial contamination such as bacteria and fungi over a long period of time by adding a small amount. It is providing the antibacterial composition for industrial use.


一般式(II)

Figure 0006008382
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)

Formula (II)
Figure 0006008382
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)

上記組成物を用いることにより、還元剤や還元性物質を含有するポリマーエマルションや水系組成物に対して細菌や真菌等の微生物による腐敗から少量の添加により長期間にわたって保護することが可能となる。 By using the above composition, it becomes possible to protect a polymer emulsion or aqueous composition containing a reducing agent or a reducing substance from spoilage by microorganisms such as bacteria and fungi over a long period of time by adding a small amount.


一般式(II)

Figure 0006008382
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)

Formula (II)
Figure 0006008382
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)

本発明の抗菌組成物の対象微生物は、細菌、糸状菌、酵母、藻など広範囲にわたり、本発明の工業用抗菌組成物はかかる広範囲の微生物に対してそれらを防除剤として優れた効果を発揮する。とくに対象物中に重合停止剤として還元剤が含まれるポリマーエマルションや、漂白、脱色、酸化防止の目的で還元剤が添加される水系組成物における有害微生物の防除に有効である他、ポリ塩化ビニルやポリオレフィンなどのプラスチックや、アクリルやウレタンなどのエマルション塗料やエナメルやアルキドなどの油性塗料に添加することによる抗菌効果の付与、得られた抗菌組成物の希釈液に木材を浸漬したり表面処理することによる抗菌効果の付与も可能である。 The target microorganism of the antibacterial composition of the present invention covers a wide range of bacteria, filamentous fungi, yeast, algae and the like, and the industrial antibacterial composition of the present invention exhibits an excellent effect as a control agent against such a wide range of microorganisms. . In particular, it is effective for controlling harmful microorganisms in polymer emulsions containing a reducing agent as a polymerization terminator in the object and aqueous compositions to which a reducing agent is added for the purpose of bleaching, decoloring, and oxidation prevention. Add antibacterial effect by adding it to plastics such as polyolefin, emulsion paints such as acrylic and urethane, and oil paints such as enamel and alkyd, and immerse and surface-treat wood in the diluted solution of the obtained antibacterial composition It is also possible to impart an antibacterial effect.

本発明で使用する一般式(I)で示される亜鉛ピリチオン複合化合物は、WO09/144929に従って調製することが可能である。また「HYBRICIDE(登録商標)−89」としてKOLON LIFE SCIENCE社から市販されているものを使用しても良い。一般式(II)で示されるイソチアゾロン化合物は、1,2−ベンズ−3−イソチアゾロン、N−メチル−1,2−ベンズ−3−イソチアゾロン、N−エチル−1,2−ベンズ−3−イソチアゾロン、N−n−ブチル−1,2−ベンズ−3−イソチアゾロン、2−エチル−3−イソチアゾロン、2−n−ブチル−3−イソチアゾロン、2−n−オクチル−3−イソチアゾロン、5−クロロ−2−n−オクチル−3−イソチアゾロン、4,5−ジクロロ−2−n−オクチル−3−イソチアゾロンなどが挙げられる。これらのうち、1,2−ベンズ−3−イソチアゾロンは例えば、「PROXEL(登録商標) PRESS PASTE」としてARCH CHEMICALS社から市販されているものや、ドイツ特許第3150629号明細書等に記載の方法またはそれに準じる方法によって調製することが可能であり、N−n−ブチル−1,2−ベンズ−3−イソチアゾロンは例えば、「VANQUISH(登録商標)100」としてARCH CHEMICALS社から市販されているものが利用可能であり、2−n−オクチル−3−イソチアゾロンは例えば、「ZONEN(登録商標) O/100」としてケミクレア社から市販されているものが利用可能であり、4,5−ジクロロ−2−n−オクチル−3−イソチアゾロンは例えば、「KATHON(登録商標) 287T」としてROHM AND HAAS社から市販されているものが利用可能である。本発明の抗菌組成物における一般式(I)で示される亜鉛ピリチオン複合化合物と、一般式(II)で示されるイソチアゾロン化合物の含有率はとくに制限を受けないが、好ましくはそれぞれ0.1重量%以上、より好ましくは1重量%以上である。 The zinc pyrithione complex compound represented by the general formula (I) used in the present invention can be prepared according to WO09 / 144929. Moreover, you may use what is marketed from KOLON LIFE SCIENCE as "HYBRICIDE (trademark) -89". The isothiazolone compound represented by the general formula (II) includes 1,2-benz-3-isothiazolone, N-methyl-1,2-benz-3-isothiazolone, N-ethyl-1,2-benz-3-isothiazolone, Nn-butyl-1,2-benz-3-isothiazolone, 2-ethyl-3-isothiazolone, 2-n-butyl-3-isothiazolone, 2-n-octyl-3-isothiazolone, 5-chloro-2- Examples thereof include n-octyl-3-isothiazolone and 4,5-dichloro-2-n-octyl-3-isothiazolone. Among these, for example, 1,2-benz-3-isothiazolone is commercially available from ARCH CHEMICALS as “PROXEL (registered trademark) PRES PASTE”, the method described in German Patent No. 3150629, or the like. The Nn-butyl-1,2-benz-3-isothiazolone is commercially available from ARCH CHEMICALS as “VANQUISH (registered trademark) 100”, for example. 2-n-octyl-3-isothiazolone, for example, commercially available from Chemicrea as “ZONEN® O / 100” can be used, and 4,5-dichloro-2-n -Octyl-3-isothiazolone is exemplified by “KATHON (Registered trademark) 287T "commercially available from ROHM AND HAAS can be used. The contents of the zinc pyrithione complex compound represented by the general formula (I) and the isothiazolone compound represented by the general formula (II) in the antibacterial composition of the present invention are not particularly limited, but preferably 0.1% by weight, respectively. As mentioned above, More preferably, it is 1 weight% or more.

本発明の抗菌組成物に配合可能な溶媒としては、水の他、エタノールやイソプロパノール等の一価アルコール類、エチレングリコール、ジエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール等のグリコール系溶剤およびその誘導体、グリセリン、ジグリセリン等のグリセリン系溶剤およびその誘導体を使用することができる。これら有機溶媒は、単独で使用してもよく、2種類以上を併用することも可能である。亜鉛ピリチオン複合化合物、イソチアゾロン化合物の溶媒に対する溶解性を考慮すると水を主溶媒として、後述する界面活性剤を用いて湿式粉砕した分散懸濁製剤とするのが好ましい。 Solvents that can be blended in the antibacterial composition of the present invention include water, monohydric alcohols such as ethanol and isopropanol, glycol solvents such as ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, and dipropylene glycol, and derivatives thereof. Glycerin solvents such as glycerin and diglycerin and their derivatives can be used. These organic solvents may be used alone or in combination of two or more. In consideration of the solubility of the zinc pyrithione complex compound and the isothiazolone compound in the solvent, it is preferable to prepare a dispersion suspension preparation which is wet-pulverized using water as a main solvent and a surfactant described later.

界面活性剤としては、例えばポリオキシアルキレンアルキルエーテル、ポリオキシアルキレンアリルフェニルエーテル、グリセリン脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシアルキレンソルビタン脂肪酸エステル、ポリオキシアルキレン硬化ヒマシ油等のノニオン界面活性剤や、アルキルサルフェート塩、アルキルエーテルサルフェート塩、アルキルスルホサクシネート塩、アルキルスルホネート塩、アルキルアリルスルホネート塩、脂肪酸アミドスルホネート塩、アルキルホスフェート塩、アルキルエーテルホスフェート塩、ナフタレンスルホン酸ホルムアルデヒド縮合物塩等のアニオン界面活性剤や、アルキルアミン塩、アルキルアンモニウム塩等のカチオン界面活性剤や、グリシン型、ベタイン型、イミダゾリン型等の両性界面活性剤を使用することができる。これら界面活性剤は単独で使用してもよく、2種類以上を組み合わせて使用することも可能である。これらのうちとくにノニオン界面活性剤、アニオン界面活性剤が好ましい。 Examples of the surfactant include nonionic surfactants such as polyoxyalkylene alkyl ether, polyoxyalkylene allyl phenyl ether, glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, polyoxyalkylene hydrogenated castor oil, and alkyl Anionic surfactants such as sulfate salts, alkyl ether sulfate salts, alkyl sulfosuccinate salts, alkyl sulfonate salts, alkyl allyl sulfonate salts, fatty acid amide sulfonate salts, alkyl phosphate salts, alkyl ether phosphate salts, naphthalene sulfonic acid formaldehyde condensate salts And cationic surfactants such as alkylamine salts and alkylammonium salts, glycine type, betaine type, imidazoline type, etc. It can be used sex surfactant. These surfactants may be used alone or in combination of two or more. Of these, nonionic surfactants and anionic surfactants are particularly preferable.

pH調整剤としては、コハク酸やクエン酸、酒石酸等の有機酸やそれらの塩、リン酸やポリリン酸、ホウ酸等の無機酸やそれらの塩等が使用可能であり、消泡剤としては、鉱油系、シリコーン系、ポリエーテル系等が使用可能であり、金属封鎖剤としては、エチレンジアミン四酢酸、1−ヒドロキシエチリデン−1,1−ジホスホン酸、ニトリロ三酢酸やそれらの塩等が使用可能であり、粘度調整剤としてはキサンタンガム、カルボキシメチルセルロース、ヒドロキシエチルセルロース、アラビアガム等が使用可能であり、防錆剤としては、ベンゾトリアゾール、ジシクロヘキシルアンモニウム亜硝酸塩等が使用可能であり、他の抗菌組成物としては、メチレンビスチオシアネート、2−(4−チオシアノメチルチオ)ベンズイミダゾール、2−ブロモーニトロプロパン−1,3−ジオール、2,2−ジブロモ−2−ニトロエタノール、3−ヨード−2−プロピニルブチルカーバメート、2,3,3−トリヨードアリルアルコール、ジヨードメチル−p−トリルスルホン、ベンズイミダゾールカルバミン酸メチル、2−(4−チアゾリル)ベンズイミダゾール、2,3,5,6−テトラクロロ−4−(メチルスルホニル)ピリジン、銅ピリチオン、o−フェニルフェノール、イソプロピルメチルフェノール、パラクロロメタキシレノール、p−オキシ安息香酸アルキルエステル等が使用可能である。 As pH adjusters, organic acids such as succinic acid, citric acid, tartaric acid and their salts, inorganic acids such as phosphoric acid, polyphosphoric acid, boric acid and their salts can be used, and as antifoaming agents , Mineral oils, silicones, polyethers, etc. can be used, and sequestering agents such as ethylenediaminetetraacetic acid, 1-hydroxyethylidene-1,1-diphosphonic acid, nitrilotriacetic acid and their salts can be used As the viscosity modifier, xanthan gum, carboxymethyl cellulose, hydroxyethyl cellulose, gum arabic, etc. can be used, and as the anticorrosive agent, benzotriazole, dicyclohexylammonium nitrite, etc. can be used, and other antibacterial compositions As methylene bis thiocyanate, 2- (4-thiocyanomethylthio) benzimidazole, -Bromo-nitropropane-1,3-diol, 2,2-dibromo-2-nitroethanol, 3-iodo-2-propynylbutylcarbamate, 2,3,3-triiodoallyl alcohol, diiodomethyl-p-tolylsulfone , Methyl benzimidazole carbamate, 2- (4-thiazolyl) benzimidazole, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, copper pyrithione, o-phenylphenol, isopropylmethylphenol, parachloro Metaxylenol, p-oxybenzoic acid alkyl ester, and the like can be used.

以下、実施例および比較例により本発明を具体的に説明するが、本発明はこれらの実施例によって限定されるものではない。
(抗菌組成物実施例)
下記、表1及び表2に従って抗菌組成物を調製した。なお、表1及び表2に示す配合はすべて重量%を表す。ミルベースとして示した配合物をビーズミルにより湿式粉砕・分散した後、レットダウンとして示した配合物と混合することで、組成物中の有効成分濃度が20重量%となる抗菌組成物を得た。
EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention concretely, this invention is not limited by these Examples.
(Antimicrobial composition example)
Antibacterial compositions were prepared according to Table 1 and Table 2 below. In addition, all the formulations shown in Table 1 and Table 2 represent% by weight. The formulation shown as a mill base was wet-ground and dispersed by a bead mill, and then mixed with the formulation shown as a letdown to obtain an antibacterial composition having an active ingredient concentration of 20% by weight in the composition.

Figure 0006008382
Figure 0006008382

Figure 0006008382
Figure 0006008382

(デンプンスラリーに対する抗菌性試験)
溶性デンプン(和光純薬工業社)の10重量%スラリーに亜硫酸ナトリウムを終濃度79mg/L(亜硫酸イオンとして50mg/L)となるように添加したものに、各抗菌組成物を所定濃度添加した後、あらかじめ腐敗させた同品(細菌生菌数;2.0×10CFU/mL、真菌生菌数;1.0×10CFU/mL)を2%接種した。これらを密封静置条件で30℃にて培養し、チオグリコール酸寒天培地もしくはポテトデキストロース寒天培地を用いる平板混釈法によって経時的な生菌数を測定し、抗菌効果を判定した。なお、生菌数測定後、腐敗品を1週間毎に2%接種した。これらの試験結果を表3に示した。また表4には対象物に亜硫酸ナトリウムを添加せずに同じように行った抗菌性試験の結果を示した。これらの結果から本実施例の抗菌組成物は良好な抗菌性能を示すことがわかる。
(Antimicrobial test for starch slurry)
After adding each antibacterial composition to a 10% by weight slurry of soluble starch (Wako Pure Chemical Industries, Ltd.) to which sodium sulfite has been added to a final concentration of 79 mg / L (50 mg / L as sulfite ion) 2% inoculated in advance with the same spoiled product (viable bacterial count; 2.0 × 10 7 CFU / mL, viable fungal count; 1.0 × 10 3 CFU / mL). These were cultured at 30 ° C. under sealed static conditions, and the number of viable bacteria over time was measured by a plate pour method using thioglycolic acid agar medium or potato dextrose agar medium, and the antibacterial effect was judged. After measuring the number of viable bacteria, 2% of the spoiled product was inoculated every week. These test results are shown in Table 3. Table 4 shows the results of an antibacterial test conducted in the same manner without adding sodium sulfite to the object. From these results, it can be seen that the antibacterial composition of this example exhibits good antibacterial performance.

Figure 0006008382
0;細菌および/または真菌の生菌数が10CFU/mL未満
1;細菌および/または真菌の生菌数が10以上10CFU/mL未満
2;細菌および/または真菌の生菌数が10以上10CFU/mL未満
3;細菌および/または真菌の生菌数が10CFU/mL以上
Figure 0006008382
0: Viable count of bacteria and / or fungi is less than 10 2 CFU / mL 1; Viable count of bacteria and / or fungi is 10 2 or more and less than 10 4 CFU / mL 2; Viable count of bacteria and / or fungi Is 10 4 or more and less than 10 6 CFU / mL3; the viable count of bacteria and / or fungi is 10 6 CFU / mL or more

Figure 0006008382
0;細菌および/または真菌の生菌数が10CFU/mL未満
1;細菌および/または真菌の生菌数が10以上10CFU/mL未満
2;細菌および/または真菌の生菌数が10以上10CFU/mL未満
3;細菌および/または真菌の生菌数が10CFU/mL以上
Figure 0006008382
0: Viable count of bacteria and / or fungi is less than 10 2 CFU / mL 1; Viable count of bacteria and / or fungi is 10 2 or more and less than 10 4 CFU / mL 2; Viable count of bacteria and / or fungi Is 10 4 or more and less than 10 6 CFU / mL3; the viable count of bacteria and / or fungi is 10 6 CFU / mL or more

(ポリマーエマルションに対する抗菌性試験)
某社から入手したポリ酢酸ビニルエマルションに亜硫酸ナトリウムを終濃度79mg/L(亜硫酸イオンとして50mg/L)となるように添加したものに、各抗菌組成物を所定濃度添加した後、あらかじめ腐敗させた同品(細菌生菌数;6.0×10CFU/mL)を2%接種した。これらを密封静置条件で30℃にて培養し、チオグリコール酸寒天培地を用いる平板混釈法によって経時的な生菌数を測定し、抗菌効果を判定した。なお、生菌数測定後、腐敗品を1週間毎に2%接種した。これらの試験結果を表5に示した。本実施例の抗菌組成物は良好な抗菌性能を示すことがわかる。
(Antimicrobial test for polymer emulsion)
To the polyvinyl acetate emulsion obtained from a company, sodium sulfite was added to a final concentration of 79 mg / L (50 mg / L as sulfite ion), and after adding each antibacterial composition to a predetermined concentration, 2% of the product (viable bacterial count: 6.0 × 10 6 CFU / mL) was inoculated. These were cultured at 30 ° C. under sealed static conditions, and the number of viable bacteria over time was measured by a plate pour method using a thioglycolic acid agar medium to determine the antibacterial effect. After measuring the number of viable bacteria, 2% of the spoiled product was inoculated every week. The test results are shown in Table 5. It can be seen that the antibacterial composition of this example exhibits good antibacterial performance.

Figure 0006008382
0;細菌の生菌数が10CFU/mL未満
1;細菌の生菌数が10以上10CFU/mL未満
2;細菌の生菌数が10以上10CFU/mL未満
3;細菌の生菌数が10CFU/mL以上
Figure 0006008382
0; Viable bacterial count of less than 10 2 CFU / mL 1; Viable bacterial count of 10 2 or more and less than 10 4 CFU / mL 2; Viable bacterial count of 10 4 or more and less than 10 6 CFU / mL 3; Viable bacteria count of 10 6 CFU / mL or more

一般式(II)

Figure 0006008382
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
Formula (II)
Figure 0006008382
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)

Claims (3)

一般式(I)で示される酸化亜鉛・亜鉛ピリチオン複合化合物と、一般式(II)で示されるイソチアゾロン化合物を必須成分として含有し、還元剤濃度が亜硫酸イオンとして50mg/L以上含有する水系組成物に添加することを特徴とする工業用抗菌組成物

一般式(I)
xZnO・ZnPy
(式中xは0<x≦1を満足する正数、Pyは2−ピリジルチオ−N−オキシド基を示す。)

一般式(II)
Figure 0006008382
(式中、Rは水素または炭素数2以上8以下のアルキル基を示し、X、Yは水素もしくはハロゲン、または互いに結合して芳香族環を形成しても良い)
An aqueous composition containing a zinc oxide / zinc pyrithione complex compound represented by general formula (I) and an isothiazolone compound represented by general formula (II) as essential components, and a reducing agent concentration of 50 mg / L or more as sulfite ion Industrial antibacterial composition characterized by being added to

Formula (I)
xZnO · ZnPy 2
(In the formula, x represents a positive number satisfying 0 <x ≦ 1, and Py represents a 2-pyridylthio-N-oxide group.)

Formula (II)
Figure 0006008382
(Wherein R represents hydrogen or an alkyl group having 2 to 8 carbon atoms, and X and Y may form hydrogen or halogen, or may combine with each other to form an aromatic ring)
請求項1に記載の工業用抗菌組成物を、還元剤濃度が亜硫酸イオンとして50mg/L以上含有する水系組成物に添加する方法。
A method of adding the industrial antibacterial composition according to claim 1 to an aqueous composition containing a reducing agent concentration of 50 mg / L or more as sulfite ion.
一般式(II)で示されるイソチアゾロン化合物が、1,2−ベンズ−3−イソチアゾロンであることを特徴とする請求項1に記載の工業用抗菌組成物。 The industrial antibacterial composition according to claim 1, wherein the isothiazolone compound represented by the general formula (II) is 1,2-benz-3-isothiazolone.
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