JP2008222696A - Antimicrobial deodorant composition and manufacturing method of antimicrobial deodorant - Google Patents

Antimicrobial deodorant composition and manufacturing method of antimicrobial deodorant Download PDF

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JP2008222696A
JP2008222696A JP2007099853A JP2007099853A JP2008222696A JP 2008222696 A JP2008222696 A JP 2008222696A JP 2007099853 A JP2007099853 A JP 2007099853A JP 2007099853 A JP2007099853 A JP 2007099853A JP 2008222696 A JP2008222696 A JP 2008222696A
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antimicrobial deodorant
odor
deodorizing
antibacterial agent
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Motoshi Yoshida
茂斗志 吉田
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MORUTETSUKU KK
NPO KANKYO BISEIBUTSU SAIGAI T
NPO KANKYO BISEIBUTSU SAIGAI TAISAKU KYOKAI
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MORUTETSUKU KK
NPO KANKYO BISEIBUTSU SAIGAI T
NPO KANKYO BISEIBUTSU SAIGAI TAISAKU KYOKAI
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Abstract

<P>PROBLEM TO BE SOLVED: To provide an antimicrobial deodorant composition which has a function of preventing, decomposing and removing low-molecular-weight odor that has penetrated a target over many years or odor in a deep part of the target and a function of decomposing and removing odor deposited on a construction material etc. that has been burnt down and prevents odor production by microbial proteolysis, and to provide a manufacturing method thereof. <P>SOLUTION: The antimicrobial deodorant composition includes a silicone resin showing a permeability and a residual efficacy, diodomethyl-P-trisulfone, a quaternary ammonium salt, 2-phenoxyethanol and ethanol and/or isopropyl alcohol as essential antimicrobial deodorant components, wherein the amount of ethanol and/or isopropyl alcohol among the essential antimicrobial deodorant components is ≥50 wt.%. The manufacturing method of the antimicrobial deodorant includes diluting the antimicrobial deodorant composition so that the content of the antimicrobial deodorant components reaches 0.01-2 wt.%. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は消臭抗菌効果吸着性に優れ、その結果住宅・設備及び生活必需品に良好な耐久性のある防臭効果を賦与する、防臭抗菌剤に関するものである。  The present invention relates to a deodorizing and antibacterial agent which is excellent in adsorptivity to deodorizing and antibacterial effects and as a result imparts a durable and deodorizing effect to houses, facilities and daily necessities.

技術背景Technical background

従来より消臭剤としては、アルキルトリメチルアンモニュウムクロライドと2−フェノキシエタノール付加物等が知られている(例えば、特許文献1)
特開平9−168717公報
Conventionally, alkyltrimethylammonium chloride and 2-phenoxyethanol adduct are known as deodorants (for example, Patent Document 1).
JP-A-9-168717

これら公知の消臭剤を用いた組成物は、現況の浮遊している異臭に対しては即効的に分解消臭する事はできるが、多年に亘り浸透した低分子系の悪臭や動物性の異臭と微生物類、なかでもカビや放線菌による深部の臭気、及び建材等の焼失時に付着した異臭は、従来の消臭剤では解決できなかった。  Compositions using these known deodorants can quickly resolve the odors that are currently floating, but they have low molecular weight malodors and animal-related odors that have permeated for many years. Off-flavors and microorganisms, especially deep odors caused by mold and actinomycetes, and off-flavors attached when building materials are burned out cannot be solved by conventional deodorants.

本発明者は、上記問題に着目し、浸透性及び残効性のある柔軟性物質に消臭殺菌効果のある抗菌剤を合理的に配合することにより深部に残留する異臭分子を消去すると共に異臭分子の付着防止を賦与できることを見だし本発明を成すに至った。  The present inventor has paid attention to the above-mentioned problem and erases the off-flavor molecules remaining in the deep part by rationally adding an antibacterial agent having a deodorizing and bactericidal effect to a flexible material having penetrability and residual effect. The inventors have found that the prevention of adhesion of molecules can be imparted, and have reached the present invention.

即ち本発明の、柔軟性物質は珪素樹脂(シリコーン)で消臭殺菌効果のあるジョードメチル−P−トリスルホンに公知の消臭剤を配合することを特徴とする防臭抗菌剤を提供するものである。  That is, the flexible substance of the present invention provides a deodorizing antibacterial agent characterized in that a known deodorant is blended with Jodomethyl-P-trisulfone which is a silicon resin (silicone) and has a deodorizing and sterilizing effect. is there.

本発明防臭抗菌剤は、対象物を選ばず、深部に凝縮された悪臭を分解して、再び吸着することを防止することで従来の消臭剤に比して長期間有効なため、特に公共の場に於ける不快臭の防止や浄化槽設備等、日常手入れの及ばない場所でも環境浄化を賦与する。  Since the deodorizing antibacterial agent of the present invention is effective for a long period of time compared to conventional deodorants by decomposing bad odors condensed in the deep part and preventing re-adsorption, regardless of the object, it is particularly public. Environmental cleansing is provided even in places where daily care is not possible, such as prevention of unpleasant odors and septic tank facilities.

以下、本発明の構成について詳述する。本発明に於いて用いられる珪素樹脂は撥水性と柔軟性があるものでレベリング効果があればよく、有機溶媒でもある2−フェノキシエタノール、エタノール及び/又は、イソプロピルアルコールによって溶解された、ジョードメチル−P−トリスルホンの分子によって通気性のある保護層が形成され脱臭性と防臭性を同時に得ることができる。乳化剤としても有効なアルキルトリメチルアンモニュウム塩と、親水性溶媒のエタノール及び/又はイソプロピルアルコールとによって希釈及び水性化された防臭抗菌剤を得ることができる。  Hereinafter, the configuration of the present invention will be described in detail. The silicon resin used in the present invention has water repellency and flexibility and needs only to have a leveling effect, and is dissolved in 2-methyloxyethanol, ethanol and / or isopropyl alcohol, which is an organic solvent, Joodomethyl-P -A protective layer having air permeability is formed by the molecules of trisulfone, and deodorizing properties and deodorizing properties can be obtained simultaneously. It is possible to obtain a deodorizing antibacterial agent diluted and made aqueous with an alkyltrimethylammonium salt which is also effective as an emulsifier and a hydrophilic solvent ethanol and / or isopropyl alcohol.

本発明においては、珪素樹脂(シリコーン)、アルキルトリメチルアンモニュウム塩、2−フェノキシエタノール、ジョードメチル−P−トリスルホンの必須防臭抗菌剤化合物を全重量のそれぞれ0.2〜30%未満とし、水性可能配合量のエタノール、又はイソプロピルアルコールの配合量を50重量%以上とした防臭抗菌剤組成物、並びに前記防臭抗菌剤組成物中の乾燥成分重量が好ましくは0.001〜2重量%となる防臭抗菌剤。  In the present invention, the essential deodorant antibacterial compound of silicon resin (silicone), alkyltrimethylammonium salt, 2-phenoxyethanol, and jodomethyl-P-trisulfone is 0.2 to less than 30% of the total weight, respectively, and water-based formulation Deodorant antibacterial agent composition in which the amount of ethanol or isopropyl alcohol is 50% by weight or more, and the deodorant antibacterial agent in which the dry component weight in the deodorant antibacterial agent composition is preferably 0.001 to 2% by weight .

珪素樹脂(シリコーン)は、有機溶剤により溶解されたもので、ジメチルシリコーン、ポリオキシアルキレンで常温にて撥水性を示すもので、必須防臭抗菌成分中の配合割合は、0.5〜20重量%、特に2〜10重量%の範囲が好ましい。配合割合が0.5%未満の場合は吸着性が希薄となり耐久性が乏しくなり、20重量%を超えると保護層の通気性を損なう恐れがある。  Silicone resin (silicone) is dissolved in an organic solvent and is water-repellent at room temperature with dimethylsilicone and polyoxyalkylene. The blending ratio in the essential deodorant antibacterial component is 0.5 to 20% by weight. In particular, the range of 2 to 10% by weight is preferable. When the blending ratio is less than 0.5%, the adsorptivity becomes dilute and the durability becomes poor, and when it exceeds 20% by weight, the air permeability of the protective layer may be impaired.

ジョードメチル−P−トリスルホンは、抗菌剤として知られているが、表面乾燥の促進性と低分子系の異臭の消去に効果がある。必須成分の防臭効果と通気性の作用を示す成分である。該ジョードメチル−P−トリスルホンの必須防臭抗菌成分中の配合割合は、0.2〜10重量%で、好ましくは0.5〜5重量%である。0.2重量%未満では、保護層の通気性に関する分子が希薄となる。10重量%以上になると保護層の吸着性を損なう恐れがある。  Joodomethyl-P-trisulfone is known as an antibacterial agent, but is effective in promoting surface drying and eliminating low-molecular odors. It is a component that exhibits the deodorizing effect and breathability of essential components. The blending ratio of the jodomethyl-P-trisulfone in the essential deodorant antibacterial component is 0.2 to 10% by weight, preferably 0.5 to 5% by weight. If it is less than 0.2% by weight, the molecules relating to the air permeability of the protective layer are diluted. If it is 10% by weight or more, the adsorbability of the protective layer may be impaired.

アルキルトリメチルアンモニュウム塩の必須防臭抗菌成分中の配合割合は、1〜25重量%である。好ましくは5〜10重量%で1重量%未満の場合には、所望とする乳化性を失う恐れがある。25重量%を超えた場合には、界面活性剤特有の刺激臭が発生する恐れがあるので好ましくない。  The blending ratio of the alkyltrimethylammonium salt in the essential deodorant antibacterial component is 1 to 25% by weight. When the amount is preferably 5 to 10% by weight and less than 1% by weight, the desired emulsifiability may be lost. If it exceeds 25% by weight, an irritating odor peculiar to the surfactant may be generated, which is not preferable.

2−フェノキシエタノールは、該防臭抗菌剤のジョードメチル−P−トリスルホンの溶媒剤として作用し、且つ必須防臭成分と共に防臭作用を示す成分である。該2−フェノキシエタノールの必須防臭抗菌成分中の配合割合は1〜30重量%、好ましくは5〜10重量%で、1重量%未満の場合には、溶媒としての作用を示さない。30重量%を超えると粘度が増幅し、乾燥性が著しく悪くなり防臭効果の吸着性が失われるので好ましくない。  2-Phenoxyethanol is a component that acts as a solvent agent for the deodorizing antibacterial agent Jodomethyl-P-trisulfone, and exhibits a deodorizing action together with an essential deodorizing component. The blending ratio of the 2-phenoxyethanol in the essential deodorant antibacterial component is 1 to 30% by weight, preferably 5 to 10% by weight, and when it is less than 1% by weight, it does not act as a solvent. If it exceeds 30% by weight, the viscosity is amplified, the drying property is remarkably deteriorated, and the adsorptive property of the deodorizing effect is lost.

エタノール及び/又はイソプロピルアルコールは前記珪素樹脂(シリコーン)、ジョードメチル−P−トリスルホン及びトリメチルアンモニュウム塩及び2−フェノキシエタノールの溶媒として作用し、且つこれら必須成分と共に消臭成分と共に消臭や芳香作用を示す成分である。該エタノール及び/又はイソプロピルアルコールの必須防臭抗菌成分中の配合割合は、50重量%以上、好ましくは50〜80重量%である。  Ethanol and / or isopropyl alcohol acts as a solvent for the silicon resin (silicone), jodomethyl-P-trisulfone, trimethylammonium salt, and 2-phenoxyethanol, and together with these essential components, deodorant and fragrance action together with deodorant components. It is a component shown. The blending ratio of the ethanol and / or isopropyl alcohol in the essential deodorant antibacterial component is 50% by weight or more, preferably 50 to 80% by weight.

本発明の防臭抗菌剤組成物においては、前記防臭抗菌剤組成物においては、前記必須防臭抗菌成分の他に、例えば低毒性の防カビ剤、サイアベンダソール(TBZ)、N−ハロメチルチオ系(プリベントールA4−S)などを抗菌補助剤として含有させることもでき、その配合割合は、必須防臭抗菌成分10重量部に対して0.5重量部以下であることが好ましい。  In the deodorant antibacterial agent composition of the present invention, in the deodorant antibacterial agent composition, in addition to the essential deodorant antibacterial component, for example, a low-toxic antifungal agent, siabendazole (TBZ), N-halomethylthio type ( Preventol A4-S) or the like can also be contained as an antibacterial auxiliary agent, and the blending ratio thereof is preferably 0.5 parts by weight or less with respect to 10 parts by weight of the essential deodorant antibacterial component.

本発明の防臭抗菌剤組成物を防臭抗菌剤として使用するには、前記必須防臭抗菌剤成分の含有割合が、0.05〜25重量%含有されるように、水又はエタノール及び/イソプロピルアルコールの混合物で希釈するのが好ましい。0.05重量%未満の場合は、所望の防臭抗菌効果が得られない恐れがあり、25重量%を超える場合には、深部の特に低分子系の悪臭を閉じこめる恐れがあるので好ましくない。  In order to use the deodorant antibacterial composition of the present invention as a deodorant antibacterial agent, water or ethanol and / or isopropyl alcohol is used so that the content of the essential deodorant antibacterial component is 0.05 to 25% by weight. It is preferred to dilute with the mixture. If the amount is less than 0.05% by weight, the desired deodorizing and antibacterial effect may not be obtained. If the amount exceeds 25% by weight, a deep low-molecular odor may be trapped, which is not preferable.

本発明の防臭抗菌剤組成物を用いて防臭抗菌剤を調整するには、まずエタノール及び/又はイソプロピルアルコールに他の必須防臭抗菌成分を好ましくは前記配合割合となるように混合攪拌して防臭抗菌成分を得、次いで得られた防臭抗菌成分の含有割合が、0.05〜25重量%になるように、使用前若しくは使用時に水又はエタノール及び/又はイソプロピルアルコールによって希釈する方法により得ることができる。  In order to prepare a deodorant antibacterial agent using the deodorant antibacterial agent composition of the present invention, first, ethanol and / or isopropyl alcohol are mixed and stirred with other essential deodorant antibacterial components preferably in the above-mentioned blending ratio, and the deodorant antibacterial agent is prepared. It can be obtained by a method of obtaining components and then diluting with water or ethanol and / or isopropyl alcohol before use or at the time of use so that the content of the obtained deodorant antibacterial component is 0.05 to 25% by weight. .

本発明の防臭抗菌剤組成物は、トイレの壁面や床面、生ゴミや産業廃棄物の設備、車両等に付着した複合的汚染の悪臭や魚等の生物の容器などに付着した生臭に対して有効に作用し、ついで一定期間付着を防止することができる。この際、防臭を目的とする個所は汚れ等を通常のクリーニングで清掃した後1mにつき50〜100mlになるよう噴霧又は刷毛で塗布すればよく、2回以上に分けて使用するのが好ましい。The deodorant antibacterial agent composition of the present invention is suitable for the bad smell of complex pollution attached to toilet walls and floors, garbage and industrial waste facilities, vehicles, etc. and raw odors attached to biological containers such as fish. Effective, and then can prevent adhesion for a certain period of time. At this time, the portion intended for deodorization may be applied by spraying or brushing so as to be 50 to 100 ml per 1 m 2 after dirt or the like is cleaned by ordinary cleaning, and is preferably used in two or more times.

発明の効果The invention's effect

本発明の防臭抗菌剤組成物は、初期の消臭効果に加えて微生物の発育阻止、特にバチルス属(グラム陽性桿菌)などの発育を阻止しアンモニアの生成などを抑え腐敗臭とは違う低分子系の異臭を防止して、公衆トイレによくみられる不快臭を長期間阻止する。人や他の環境に対する悪影響を最小限に軽減することができる。又、本発明の製造方法では、このような防臭抗菌剤組成物を基本とする防臭抗菌剤を容易に得ることができる。しかも得られた防臭抗菌剤は混合及び噴霧等の簡便な方法により使用することができる。  The deodorant antibacterial agent composition of the present invention has a low molecular weight that is different from a spoiled odor by preventing the growth of microorganisms, in particular, the growth of Bacillus (Gram-positive gonococci) in addition to the initial deodorizing effect, and suppressing the production of ammonia Prevents the odor of the system and prevents the unpleasant odor common in public toilets for a long time. The adverse effects on people and other environments can be reduced to a minimum. Moreover, in the manufacturing method of this invention, the deodorizing antibacterial agent based on such a deodorizing antibacterial agent composition can be obtained easily. Moreover, the obtained deodorant antibacterial agent can be used by a simple method such as mixing and spraying.

以下本発明を実施例及び比較例により更に詳細に説明するが、本発明はこれらに限定されるものではない。  EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention further in detail, this invention is not limited to these.

エタノール50重量部、イソプロピルアルコール20重量部、モノアルキルアンモニュウム塩15重量部、2−フェノキシエタノール7.5重量部、珪素樹脂(シリコーン)(信越化学株式会社製 KF96)5重量部、ジョードメチル−P−トリスルホン2.5重量部とを混合攪拌して防臭抗菌成分を調整した。次いで得られた防臭抗菌成分をイソプロピルアルコール400重量部に希釈混合した。得られた防臭抗菌剤について、以下の(イ)〜(ロ)の試験を行った。
尚、評価はトイレに関しては、試験当日は監督者ら5名、経過検査は男女の各10名に任意に入場、匂いを嗅いでもらい評価した。
50 parts by weight of ethanol, 20 parts by weight of isopropyl alcohol, 15 parts by weight of a monoalkyl ammonium salt, 7.5 parts by weight of 2-phenoxyethanol, 5 parts by weight of silicon resin (silicone) (KF96 manufactured by Shin-Etsu Chemical Co., Ltd.), Jodomethyl-P- A deodorizing and antibacterial component was prepared by mixing and stirring 2.5 parts by weight of trisulfone. Subsequently, the obtained deodorizing antibacterial component was diluted and mixed with 400 parts by weight of isopropyl alcohol. About the obtained deodorizing antibacterial agent, the following tests (a) to (b) were performed.
As for the evaluation of toilets, 5 supervisors and 10 followers were selected on the day of the test, and 10 men and women were allowed to enter and smell the scent.

(イ)東京都中央区の地下街の公衆トイレを通常の清掃後、前記防臭抗菌剤を1m当たり70mlを2回に分けて噴霧し乾燥させた。通常の清掃では消臭し得なかった臭いは、アルコール臭の消滅と同時に消臭された。以後10日、30日、180日後にも従来の臭いは発生していず、爽やかな状態である。(B) Chuo-ku, Tokyo of After the usual cleaning the public toilets of the underground mall, the deodorant antibacterial agent was sprayed separately 1m 2 per 70ml to 2 times dry. The odor that could not be removed by normal cleaning was removed at the same time as the disappearance of the alcohol odor. After 10 days, 30 days, and 180 days later, the conventional odor is not generated and it is in a refreshing state.

(ロ)東京都渋谷区で6月、改装に伴う仮設トイレ10個に対して、仮設時に設置床面を始め内部に前記防臭抗菌剤を70mlを2回に分け噴霧乾燥させた。12月の点検時に臭いの発生はなかった。  (B) In June in Shibuya-ku, Tokyo, 10 temporary toilets for refurbishment were spray-dried in two portions of 70 ml of the deodorizing antibacterial agent in the interior including the installation floor during temporary installation. There was no odor at the December inspection.

珪素樹脂(シリコーン)を水性化に調整した商品TSF4440(東芝シリコーン株式会社製)に代えた以外は、実施例1と同様に防臭抗菌剤を調整し、また希釈をイソプロピルアルコールに代えて水の量を4,900重量部とした防臭抗菌剤を調整し(イ)〜(ロ)の試験を行った。実際にそれぞれの当事者に匂いを嗅いでもらうことにより評価した。  The amount of water was changed by adjusting the deodorizing antibacterial agent in the same manner as in Example 1, except that the product TSF4440 (manufactured by Toshiba Silicone Co., Ltd.), which was adjusted to water-based silicon resin (silicone), was used. A deodorizing antibacterial agent was adjusted to 4,900 parts by weight, and tests (a) to (b) were conducted. The evaluation was performed by having each party actually smell the scent.

(イ)21年間生存した日本猫の雄が10年間使用したカーペットは、健康体であった生存中の臭いは前記(0002)の消臭剤で充分効果があったが、死亡1ヶ月前よりの病臭には効果はなかった。
本発明による防臭抗菌剤を該カーペットの表面に70ml/1m噴霧し24時間乾燥した後は複合した悪臭は消滅復元しカーペットは再生した。
(I) The carpet used for 10 years by a Japanese cat male who survived for 21 years was a healthy body, and the odor during survival was sufficiently effective with the deodorant of (0002) above, but since 1 month before his death There was no effect on the disease odor.
After spraying 70 ml / 1 m 2 of the deodorizing antibacterial agent according to the present invention on the carpet surface and drying it for 24 hours, the composite malodor disappeared and the carpet was regenerated.

(ロ)東京都下及び埼玉県のスーパー銭湯の木造トイレに使用するため、市販の消臭剤や(0002)の消臭剤では即効性はあるものの雨天が連続したりして悪臭が滞留し、壁面や床面に付着してしまったものは、消臭できなかった。
前記の防臭抗菌剤を木造の壁面や床面に刷毛、ローラーで塗布した結果、30日間後も臭いの付着を防止していた。
(B) Because it is used in wooden public toilets under the Tokyo Metropolitan and Saitama prefectures, commercial deodorants and (0002) deodorizers have immediate effects, but rainy weather continues and stinks accumulate. Those that adhered to the wall or floor could not be deodorized.
As a result of applying the deodorizing antibacterial agent to a wooden wall surface or floor surface with a brush or a roller, odor adhesion was prevented even after 30 days.

比較例1Comparative Example 1

茨城県において、RC構造の3階建ての2階部分が失火により損害を受けた。消失により低分子系の悪臭が壁面及び天井のスラブに焼き付いた。全体を水洗いした後、内1室に実施例1と同様の防臭抗菌剤を調整し70ml/1m、噴霧乾燥させた。一方他の1室にジョードメチル−P−トリスルホンを用いない以外は同様の防臭抗菌剤を70ml/1m噴霧乾燥させた。乾燥後ジョードメチル−P−トリスルホンを用いた例では7日後も悪臭はなかった。一方用いなかった室は乾燥後悪臭の残留があった。In Ibaraki Prefecture, the second floor of the three-story RC structure was damaged by a misfire. Due to the disappearance, a low molecular odor was burned onto the wall and ceiling slabs. After the whole was washed with water, the same deodorizing and antibacterial agent as in Example 1 was prepared in one chamber and spray-dried at 70 ml / 1 m 2 . On the other hand, the same deodorizing antibacterial agent was spray-dried at 70 ml / 1 m 2 except that Jodomethyl-P-trisulfone was not used in the other chamber. In the example using Joodomethyl-P-trisulfone after drying, there was no odor after 7 days. On the other hand, the room which was not used had a bad odor residue after drying.

Claims (2)

珪素樹脂(シリコーン)とジョードメチル−P−トリスルホンとモノアルキルアンモニュウム塩と、2−フェノキシエタノールを必須防臭成分として含み、必須成分中のエタノール及び/又はイソプロピルアルコールの配合量を50重量%以上としたことを特長とする防臭抗菌剤組成物。  Silicone resin (silicone), jodomethyl-P-trisulfone, monoalkylammonium salt, and 2-phenoxyethanol are included as essential deodorizing components, and the blending amount of ethanol and / or isopropyl alcohol in the essential components is 50% by weight or more. A deodorant antibacterial composition characterized by that. 珪素樹脂(シリコーン)とジョードメチル−P−トリスルホンとモノアルキルアンモニュウム塩と、2−フェノキシエタノールにエタノール及び/又はイソプロピルアルコールの含有量が50重量%以上となるように溶解して防臭抗菌剤成分を得、該防臭抗菌剤成分含有量が0.01〜2.0重量%になるように希釈することを特長とする防臭抗菌剤の製造法。  Deodorizing antibacterial agent component by dissolving silicon resin (silicone), jodomethyl-P-trisulfone, monoalkylammonium salt, and 2-phenoxyethanol so that the content of ethanol and / or isopropyl alcohol is 50% by weight or more. A method for producing a deodorizing antibacterial agent, characterized in that the deodorizing antibacterial agent component content is diluted to 0.01 to 2.0% by weight.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010004971A (en) * 2008-06-25 2010-01-14 Kao Corp Method for suppressing malodor generated from waste, drain outlet and the like
WO2020252530A1 (en) * 2019-06-18 2020-12-24 Animal Control Technologies (Australia) Pty Ltd Formulations and methods for controlling invasive amphibians

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JPH04103501A (en) * 1990-08-22 1992-04-06 Mirudou Sangyo Kk Mildew-proofing fungicidal composition and mildew-proofing fungicidal paint composition
JPH09168717A (en) * 1995-12-20 1997-06-30 Mirudou Sangyo Kk Deodorant composition and preparation of deodorant
JPH10218702A (en) * 1997-02-06 1998-08-18 Morutetsuku:Kk Antimicrobial and antimould composition having formaldehyde-removing activity and removal of formaldehyde
JP2000186001A (en) * 1998-12-22 2000-07-04 Morutetsuku:Kk Antimicrobial/fungicidal composition

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Publication number Priority date Publication date Assignee Title
JPH04103501A (en) * 1990-08-22 1992-04-06 Mirudou Sangyo Kk Mildew-proofing fungicidal composition and mildew-proofing fungicidal paint composition
JPH09168717A (en) * 1995-12-20 1997-06-30 Mirudou Sangyo Kk Deodorant composition and preparation of deodorant
JPH10218702A (en) * 1997-02-06 1998-08-18 Morutetsuku:Kk Antimicrobial and antimould composition having formaldehyde-removing activity and removal of formaldehyde
JP2000186001A (en) * 1998-12-22 2000-07-04 Morutetsuku:Kk Antimicrobial/fungicidal composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010004971A (en) * 2008-06-25 2010-01-14 Kao Corp Method for suppressing malodor generated from waste, drain outlet and the like
WO2020252530A1 (en) * 2019-06-18 2020-12-24 Animal Control Technologies (Australia) Pty Ltd Formulations and methods for controlling invasive amphibians

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