JP2001097806A - Antibacterial agent and antibacterial composition using the same - Google Patents
Antibacterial agent and antibacterial composition using the sameInfo
- Publication number
- JP2001097806A JP2001097806A JP28162899A JP28162899A JP2001097806A JP 2001097806 A JP2001097806 A JP 2001097806A JP 28162899 A JP28162899 A JP 28162899A JP 28162899 A JP28162899 A JP 28162899A JP 2001097806 A JP2001097806 A JP 2001097806A
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- JP
- Japan
- Prior art keywords
- antibacterial
- antibacterial agent
- agent
- polymer
- present
- 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.)
- Pending
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は抗菌剤及び抗菌性組
成物に関し、さらに詳しくは、細菌、黴（かび）等の有
害微生物に対して殺菌性、抗菌性を示す２−ビニルイミ
ダゾール重合体を有効成分とする抗菌剤及びそれを用い
た抗菌性組成物に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antibacterial agent and an antibacterial composition, and more particularly, to a 2-vinylimidazole polymer having bactericidal and antibacterial properties against harmful microorganisms such as bacteria and fungi. The present invention relates to an antibacterial agent as an active ingredient and an antibacterial composition using the same.
【０００２】[0002]
【従来の技術】従来より種々の抗菌剤が提案されてい
る。例えば、無機系抗菌剤においては、銀、銅、亜鉛な
どの金属又はその化合物は殺菌性を有することが知られ
ていることから、銀、銅、亜鉛などの金属又はその化合
物をゼオライト、セラミックス、ガラス、活性炭などの
担体に担持して用いていた。また、有機系抗菌剤とし
て、合成樹脂にこのような金属粉末を分散したもの、金
属を吸着したキレート樹脂を使用するもの（特公昭６３
−１１０７６号公報）、Ｎ−長鎖アシルアミノ酸の金属
塩を用いるもの（特開平３−１８１４０３号公報）など
も知られている。2. Description of the Related Art Various antibacterial agents have been proposed. For example, in inorganic antibacterial agents, metals such as silver, copper, and zinc or compounds thereof are known to have bactericidal properties, so that metals such as silver, copper, and zinc or compounds thereof are zeolites, ceramics, It was used by supporting it on a carrier such as glass or activated carbon. Further, as an organic antibacterial agent, a product obtained by dispersing such a metal powder in a synthetic resin or a product using a chelate resin adsorbing a metal (Japanese Patent Publication No. Sho 63)
Japanese Unexamined Patent Publication (Kokai) No. -11076) and those using metal salts of N-long-chain acylamino acids (Japanese Patent Laid-Open No. 3-181403) are also known.
【０００３】しかしながら、無機系抗菌剤を液状で用い
る場合、液体に添加してもすぐに担持した金属やその化
合物が分離してしまい、抗菌剤としての効果が十分に持
続させることが困難であった。また、合成樹脂に金属粉
末を分散したものやキレート樹脂を使用するものは、こ
れを塗料などに利用する際に、樹脂の穴が塞がれてその
効果が低くなり、また水などに対する分散性も不十分な
ものであった。さらにＮ−長鎖アシルアミノ酸の金属塩
を用いるものは、溶解性を高めるためにアンモニア水な
どの溶媒を必要とし、このため作業環境の悪化を招いて
しまうことがあった。However, when an inorganic antibacterial agent is used in a liquid form, even if it is added to a liquid, the supported metal or its compound is immediately separated, and it is difficult to sufficiently maintain the effect as an antibacterial agent. Was. In addition, in the case of using synthetic resin in which metal powder is dispersed or using chelate resin, when this is used in paints, the holes in the resin are closed and the effect is reduced, and dispersibility in water etc. Was also inadequate. Further, those using a metal salt of an N-long-chain acylamino acid require a solvent such as aqueous ammonia in order to enhance the solubility, which may lead to deterioration of the working environment.
【０００４】さらに低分子の有機化合物を用いた抗菌剤
も知られているが、その揮発性のため、効力に持続性が
乏しく、また樹脂などに添加した際、分散性が十分なも
のとはいえなかった。[0004] Further, antibacterial agents using low-molecular organic compounds are also known. However, their volatility makes them less effective in persistence and, when added to resins and the like, disperses sufficiently. I couldn't say it.
【０００５】このように従来の抗菌剤は水などの液体に
対する溶解性、分散性や担持物質の安定性の点で十分な
ものとはいえず、そのためにその抗菌作用が良好で、長
期に渡りその作用を継続できる抗菌剤が望まれていた。As described above, the conventional antibacterial agents are not sufficient in terms of solubility, dispersibility and stability of a carrier substance in liquids such as water, and therefore have a good antibacterial effect, and have a long term antibacterial effect. An antibacterial agent that can continue its action has been desired.
【０００６】[0006]
【発明が解決しようとする課題】本発明の目的は、この
ような状況と背景において、抗菌剤としての作用が良好
かつ持続する高分子化合物系の剤を提供することにあ
る。さらに、その剤型についても種々の成分、器材との
組み合わせが可能な剤及びこの剤を用いた抗菌性組成物
を提供することも本発明の目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a polymer compound-based agent which has good and long-lasting action as an antibacterial agent in such a situation and background. Furthermore, it is an object of the present invention to provide an agent which can be combined with various components and equipments, and an antibacterial composition using the agent.
【０００７】[0007]
【課題を解決するための手段】本発明者は、上記の課題
について、種々検討した結果、１）２−ビニルイミダゾ
ール重合体を有効成分とした抗菌剤が、アンモニア水な
どの作業環境を悪化させる溶媒を使用することなく、水
などの溶媒に可溶あるいは分散が容易であり、良好な抗
菌性を示すこと、２）架橋剤によりその物性を変えるこ
とで水などの溶媒に対する溶解性、分散性を制御でき
る、３）金属イオンを結合させることもできることで、
抗菌スペクトルを広くでき、また抗菌作用を増強でき
る、４）高分子化合物であるため、揮発性がなく、樹脂
に添加した時の分散性や、紙又は繊維に含浸させる場合
の浸透性にも優れている、といった種々の事実を見い出
し、本発明を完成させるに至った。As a result of various studies on the above problems, the present inventor has found that: 1) an antibacterial agent containing a 2-vinylimidazole polymer as an active ingredient deteriorates the working environment such as aqueous ammonia; It can be easily dissolved or dispersed in a solvent such as water without using a solvent, and exhibits good antibacterial properties. 2) Solubility and dispersibility in a solvent such as water by changing its physical properties with a crosslinking agent. 3) By being able to bind metal ions,
Can broaden the antibacterial spectrum and enhance the antibacterial action. 4) Because it is a polymer compound, it has no volatility, and has excellent dispersibility when added to resin and permeability when impregnated into paper or fiber. And found the fact that the present invention was completed.
【０００８】すなわち本発明は、２−ビニルイミダゾー
ル重合体を有効成分とする抗菌剤及びそれを用いた抗菌
性組成物に関する。That is, the present invention relates to an antibacterial agent containing a 2-vinylimidazole polymer as an active ingredient and an antibacterial composition using the same.
【０００９】以下に本発明をさらに詳細に説明する。Hereinafter, the present invention will be described in more detail.
【００１０】本発明の抗菌剤は、２−ビニルイミダゾー
ル重合体を有効成分とする。The antibacterial agent of the present invention contains a 2-vinylimidazole polymer as an active ingredient.
【００１１】ここで、有効成分とは抗菌作用を有する成
分を意味している。また、本発明の抗菌剤は液状、固体
状など種々の剤型をとることができるため、用いる剤型
に応じて分散剤、安定化剤、固化剤などの添加剤、溶剤
を含んでいてもよい。例えば、分散剤として界面活性剤
などを、安定化剤として紫外線の吸収作用を示す化合物
などを、また固化剤としてポリエチレングリコールなど
を用いることができる。Here, the active ingredient means a component having an antibacterial action. Further, since the antibacterial agent of the present invention can be in various forms such as liquid and solid, it may contain additives such as a dispersant, a stabilizer, and a solidifying agent, and a solvent depending on the form used. Good. For example, a surfactant or the like can be used as a dispersant, a compound having an ultraviolet absorbing effect as a stabilizer, and polyethylene glycol or the like can be used as a solidifying agent.
【００１２】また本発明の抗菌剤は有効成分として２−
ビニルイミダゾール重合体を単独で用いることができる
が、他のポリマーと混合したり、あるいは他のモノマー
と共重合したものであってもよく、また、２−ビニルイ
ミダゾール重合体の前駆体となる重合体よりその一部が
２−ビニルイミダゾール重合体へと変換して得られるよ
うな共重合体様のものであってもよい。The antibacterial agent of the present invention comprises 2-
The vinylimidazole polymer can be used alone, but may be mixed with another polymer or copolymerized with another monomer, or may be used as a precursor of a 2-vinylimidazole polymer. A copolymer-like material obtained by converting a part of the coalesced product into a 2-vinylimidazole polymer may be used.
【００１３】さらにその分子量としては特に制限はない
が、粘度により操作性が影響されることを考慮して、重
量平均分子量で１０００〜１００００００が好ましく、
さらに５０００〜５０００００が好ましい。The molecular weight is not particularly limited, but is preferably 1,000 to 1,000,000 in terms of weight average molecular weight in consideration of operability being affected by viscosity.
Further, 5,000 to 500,000 is preferable.
【００１４】本発明の抗菌剤中の有効成分である２−ビ
ニルイミダゾール重合体の製造方法は公知の方法を用い
ればよいが、通常２−ビニルイミダゾリン重合体より脱
水素するなどして得ることができる。The method for producing the 2-vinylimidazole polymer, which is the active ingredient in the antibacterial agent of the present invention, may be a known method, but is usually obtained by dehydrogenation from the 2-vinylimidazoline polymer. it can.
【００１５】この２−ビニルイミダゾール重合体の原料
となる２−ビニルイミダゾリン重合体は、アクリロニト
リル重合体とエチレンジアミンなどのジアミンとを反応
させることによって得られるが、アクリロニトリル重合
体としては、アクリロニトリルと他のモノマーとの共重
合体も原料とすることができる。A 2-vinylimidazoline polymer, which is a raw material of the 2-vinylimidazole polymer, is obtained by reacting an acrylonitrile polymer with a diamine such as ethylenediamine. A copolymer with a monomer can also be used as a raw material.
【００１６】アクリロニトリルと他のモノマーとの共重
合体をアクリロニトリル重合体の原料とする場合、共重
合体の単位を形成しうるモノマーとしては、塩化ビニ
ル、臭化ビニル、弗化ビニル等のハロゲン化ビニル類；
塩化ビニリデン等のハロゲン化ビニリデン類；アクリル
酸、メタクリル酸、イタコン酸、無水マレイン酸等の不
飽和カルボン酸、及びこれらの塩類、（メタ）アクリル
酸メチル、（メタ）アクリル酸エチル等の（メタ）アク
リル酸エステル類；（メタ）アクリルアミド及びそのア
ルキル置換体、メチルビニルケトン、メチルイソプロペ
ニルケトン等の不飽和ケトン類；酢酸ビニル、安息香酸
ビニル等のビニルエステル類；メチルビニルエーテル、
エチルビニルエーテル等のビニルエーテル類；ビニルス
ルホン酸、（メタ）アリルスルホン酸、ｐ−スチレンス
ルホン酸、２−アクリルアミド−２−メチルプロパンス
ルホン酸、（メタ）アクリロイルオキシエチルスルホン
酸等の不飽和スルホン酸、及びこれらの塩類、スチレ
ン、α−メチルスチレン、クロロスチレン等のスチレン
類、及びそのアルキル又はハロゲン置換体、アリルアル
コール及びそのエステル又はエーテル類、ビニルピリジ
ン、ビニルピリミジン、１−ビニルイミダゾール、ビニ
ルイミダゾリン、ジメチルアミノエチルメタクリレー
ト、ビニルベンジルジメチルアミン等の塩基性ビニル化
合物などが例示される。これらは予めアクリロニトリル
と共重合される。When a copolymer of acrylonitrile and another monomer is used as a raw material of the acrylonitrile polymer, the monomer capable of forming a unit of the copolymer includes halogenated compounds such as vinyl chloride, vinyl bromide and vinyl fluoride. Vinyls;
Halogenated vinylidenes such as vinylidene chloride; unsaturated carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, and maleic anhydride, and salts thereof; (meth) methyl such as methyl (meth) acrylate and ethyl (meth) acrylate; A) acrylates; (meth) acrylamide and its alkyl-substituted products, unsaturated ketones such as methyl vinyl ketone and methyl isopropenyl ketone; vinyl esters such as vinyl acetate and vinyl benzoate; methyl vinyl ether;
Vinyl ethers such as ethyl vinyl ether; unsaturated sulfonic acids such as vinyl sulfonic acid, (meth) allyl sulfonic acid, p-styrene sulfonic acid, 2-acrylamido-2-methylpropane sulfonic acid and (meth) acryloyloxyethyl sulfonic acid; And salts thereof, styrene, α-methylstyrene, styrenes such as chlorostyrene, and alkyl or halogen substituted products thereof, allyl alcohol and its esters or ethers, vinylpyridine, vinylpyrimidine, 1-vinylimidazole, vinylimidazoline, Basic vinyl compounds such as dimethylaminoethyl methacrylate and vinylbenzyldimethylamine are exemplified. These are previously copolymerized with acrylonitrile.
【００１７】本発明の抗菌剤中に有効成分として含まれ
る２−ビニルイミダゾール重合体としては、架橋した重
合体も好ましく用いることができる。例えば、溶剤に対
する溶解性がよいものの抗菌剤としての効果の持続性が
劣る時、あるいは粘度が不足した時などは、架橋するこ
とにより、溶解性を低下させ、粘度を上げることができ
る。架橋する方法としては架橋剤を使用するのが一般的
である。架橋剤としてはアミンと反応し架橋構造を形成
しうる官能基を有する化合物が使用できるし、２−ビニ
ルイミダゾールと共重合したモノマーの官能基と反応し
うる官能基を有する化合物も使用できる。アミンと反応
し架橋構造を形成しうる化合物を例示すると、アジピン
酸などのカルボン酸、アジポイルクロリドのような酸ハ
ロゲン化物、グリオキザールのようなアルデヒド、１，
４−ジクロロブタンのようなハロゲン化物、エポキシ化
合物、イソシアネートなどが使用でき、通常、多官能化
合物が使用される。架橋化合物は共有結合を形成するも
のだけではなく、イオン結合を形成するものも使用でき
る。分子中の架橋密度については、所望する粘度、溶解
性、樹脂強度により選ぶことができる。As the 2-vinylimidazole polymer contained as an active ingredient in the antibacterial agent of the present invention, a crosslinked polymer can be preferably used. For example, when the solubility in a solvent is good but the persistence of the effect as an antibacterial agent is poor, or when the viscosity is insufficient, the solubility can be reduced and the viscosity can be increased by crosslinking. As a method of crosslinking, a crosslinking agent is generally used. As the crosslinking agent, a compound having a functional group capable of forming a crosslinked structure by reacting with an amine can be used, and a compound having a functional group capable of reacting with a functional group of a monomer copolymerized with 2-vinylimidazole can also be used. Examples of the compound capable of forming a crosslinked structure by reacting with an amine include carboxylic acids such as adipic acid, acid halides such as adipoyl chloride, aldehydes such as glyoxal,
A halide such as 4-dichlorobutane, an epoxy compound, an isocyanate, or the like can be used, and usually, a polyfunctional compound is used. As the crosslinking compound, not only those forming a covalent bond but also those forming an ionic bond can be used. The crosslink density in the molecule can be selected depending on the desired viscosity, solubility, and resin strength.
【００１８】本発明の抗菌剤中に有効成分として含まれ
る２−ビニルイミダゾール重合体はアミンの形で使用す
ることもできるし、アミン塩の形で使用することもでき
る。アミン塩の形で使用する場合、塩の種類としては硫
酸塩、塩酸塩、リン酸塩、酢酸塩などの無機酸、有機酸
の塩が使用できる。The 2-vinylimidazole polymer contained as an active ingredient in the antibacterial agent of the present invention can be used in the form of an amine or an amine salt. When used in the form of an amine salt, salts of inorganic acids and organic acids such as sulfate, hydrochloride, phosphate and acetate can be used as the kind of salt.
【００１９】また本発明の抗菌剤中に有効成分として含
まれる２−ビニルイミダゾール重合体は、その抗菌活性
を高めたり、溶解性を変えるために、金属イオンのイミ
ダゾール錯体として使用することもできる。ここで金属
イオンとしてはアミンに配位し得るものならば特に制限
はなく、例えば銀、カドミウム、コバルト、銅、鉄、水
銀、マンガン、ニッケル、鉛、亜鉛、カルシウム、ゲル
マニウム、マグネシウム、白金、タリウム、金、ビスマ
スなどが挙げられ、その中でも銅、銀、亜鉛が抗菌活性
が高く好ましく用いられる。これらの金属イオンは、一
種単独にて用いるだけでなく、二種以上を用いて２−ビ
ニルイミダゾール重合体の金属錯体としてもよい。The 2-vinylimidazole polymer contained as an active ingredient in the antibacterial agent of the present invention can also be used as a metal ion imidazole complex in order to enhance its antibacterial activity and change its solubility. Here, the metal ion is not particularly limited as long as it can coordinate to the amine.Examples include silver, cadmium, cobalt, copper, iron, mercury, manganese, nickel, lead, zinc, calcium, germanium, magnesium, platinum, and thallium. , Gold, bismuth and the like. Among them, copper, silver and zinc are preferably used because of their high antibacterial activity. These metal ions may be used alone or in combination of two or more to form a metal complex of a 2-vinylimidazole polymer.
【００２０】金属錯体の製造方法としては特に制限はな
く、例えば、２−ビニルイミダゾール重合体を製造する
際の原料に添加したり、また、生成した２−ビニルイミ
ダゾール重合体に金属イオンを添加することによっても
製造できる。ここで金属イオンの原料としては２−ビニ
ルイミダゾール重合体の金属錯体を製造できるものであ
れば特に制限はなく用いることができ、例えば酢酸など
の有機酸の塩、塩酸、硫酸、硝酸などの無機酸の塩、あ
るいは金属の酸化物などが挙げられる。The method for producing the metal complex is not particularly limited. For example, the metal complex may be added to a raw material for producing a 2-vinylimidazole polymer, or a metal ion may be added to the produced 2-vinylimidazole polymer. It can also be manufactured by: The raw material of the metal ion can be used without any particular limitation as long as it can produce a metal complex of a 2-vinylimidazole polymer. For example, salts of organic acids such as acetic acid, inorganic salts such as hydrochloric acid, sulfuric acid, and nitric acid can be used. Acid salts, metal oxides and the like can be mentioned.
【００２１】本発明の抗菌剤は、黴などの菌類、藻類、
細菌類などに対する抗菌性があり、種々の用途に使用す
ることができる。例えば、直接水などに添加して、水
槽、プール、風呂、クーラントなどに発生し得る菌類な
どを殺菌、殺藻することができる。また織物、メリヤ
ス、網、糸、紐、索、綱などの繊維、紙、皮革、砂、セ
ラミックス、ガラスなどに塗布あるいは含浸させること
により、抗菌性を持たせた種々の製品とすることができ
る。特に繊維、紙のような含浸性のよいものに適用する
ことで容易に本発明の抗菌剤を含む組成物とすることが
でき、例えば紙おむつなどの商品とすることでその衛生
管理が容易となり好ましい。さらに樹脂、塗料、接着剤
などに添加して、抗菌性樹脂の製造や、抗菌性を有した
塗料、接着剤による種々の材料への抗菌性の付与など種
々の用途に使用できる。The antibacterial agent of the present invention includes fungi such as molds, algae,
It has antibacterial properties against bacteria and the like, and can be used for various applications. For example, it can be added directly to water or the like to sterilize and algae fungi or the like that can be generated in a water tank, pool, bath, coolant, or the like. In addition, various products having antibacterial properties can be obtained by applying or impregnating textiles, knits, nets, yarns, strings, cords, ropes, and other fibers, paper, leather, sand, ceramics, glass, and the like. . In particular, the composition containing the antibacterial agent of the present invention can be easily obtained by applying to a material having good impregnating property such as fiber and paper. . Further, it can be added to resins, paints, adhesives and the like to be used for various purposes such as production of antibacterial resins and imparting antibacterial properties to various materials by paints and adhesives having antibacterial properties.
【００２２】本発明の抗菌剤を含ませる器材に対し、そ
の表面部分のみならず内部まで含浸させることもでき、
これらは具体的な用途に応じて適宜選択すればよい。ま
たその抗菌力を高めたり、抗菌スペクトルを広げるため
に、既存の殺菌剤、抗菌剤と併用することもできる。The device containing the antibacterial agent of the present invention can be impregnated not only on the surface but also inside.
These may be appropriately selected according to the specific application. In addition, it can be used in combination with existing bactericides and antibacterial agents in order to enhance its antibacterial activity and broaden the antibacterial spectrum.
【００２３】さらに、本発明の抗菌剤の具体的な使用量
はそれぞれの用途に応じて異なるため一概には言えない
が、原則的にはそれぞれの用途における一般的な使用方
法と大幅に異なることはない。ただし本発明の抗菌剤
は、その優れた機能、効果のゆえに従来にない使用が期
待でき、また他の抗菌剤による同程度の効果の達成に対
して使用量の削減が可能であることは言うまでもない。Furthermore, although the specific amount of the antibacterial agent of the present invention varies depending on the intended use, it cannot be specified unconditionally. There is no. However, the antibacterial agent of the present invention can be expected to be used unconventionally because of its excellent functions and effects, and it is needless to say that the use amount can be reduced in order to achieve the same effect by other antibacterial agents. No.
【００２４】[0024]
【実施例】以下、本発明を実施例にて説明するが、本発
明はこれらに限定されるものではない。EXAMPLES Hereinafter, the present invention will be described with reference to Examples, but the present invention is not limited thereto.
【００２５】なお、表記を簡潔にするため以下の略記号
を使用し、説明する。The following abbreviations will be used for simplicity of the description.
【００２６】ＰＶＩ：２−ビニルイミダゾリン重合体 ＰＶＩＺ：２−ビニルイミダゾール重合体 ＥＤＡ：エチレンジアミン ＰＡＮ：ポリアクリロニトリル かび抵抗性試験は以下に示した方法によって実施した。PVI: 2-vinylimidazoline polymer PVIZ: 2-vinylimidazole polymer EDA: ethylenediamine PAN: polyacrylonitrile The mold resistance test was carried out by the following method.
【００２７】ＪＩＳ−Ｚ２９１１を参考にして実施し
た。すなわち抗菌剤を含む溶液を５ｃｍ×５ｃｍに切っ
たろ紙（東洋濾紙製、５Ｃ）を添加して含浸させた。つ
いでこのろ紙を、培地（グルコース−ペプトン寒天培
地：日本製薬製、ＧＰ，商品名「ダイゴ」）の入ったシ
ャーレに置き、かび胞子懸濁液をまんべんなく振り掛け
た。これを湿式、２８±１℃にて培養し、菌糸の発育状
況を観察した。The measurement was carried out with reference to JIS-Z2911. That is, the solution containing the antibacterial agent was impregnated by adding filter paper (5C, manufactured by Toyo Roshi Kaisha) cut to 5 cm × 5 cm. Then, the filter paper was placed on a petri dish containing a medium (glucose-peptone agar medium: GP, manufactured by Nippon Pharmaceutical Co., Ltd., trade name "Digo"), and the mold spore suspension was sprinkled evenly. This was cultured at 28 ± 1 ° C. in a wet condition, and the state of mycelial growth was observed.
【００２８】実施例１ ガラス製フラスコにＰＡＮ（試薬、アルドリッチ製、重
量平均分子量８６０００）１０ｇ、酢酸１ｇ、１−プロ
パノール３０ｇ、ＥＤＡ２６．８ｇを入れ、混合し、９
５℃で９時間反応させた。反応液は粘度の高い黄色の均
一溶液になった。これに１，３−ジメチルイミダゾリジ
ノン１００ｇを加え、減圧下、ＥＤＡと１−プロパノー
ルを留去し、ＰＶＩの１，３−ジメチルイミダゾリジノ
ン溶液とした。水を除いたラネー型ニッケル３ｇをこれ
に加え、窒素気流下１６０℃に加熱すると、水素の発生
が見られた。この脱水素反応を１６０℃で６時間実施し
た後、反応液を冷却し、ニッケル触媒をろ過して除いた
後、アセトン中に注ぐと黄色粉体が析出した。これを乾
燥すると、１５．３ｇのＰＶＩＺが得られた。Example 1 A glass flask was charged with 10 g of PAN (reagent, manufactured by Aldrich, weight average molecular weight: 86,000), 1 g of acetic acid, 30 g of 1-propanol, and 26.8 g of EDA, and mixed.
The reaction was performed at 5 ° C. for 9 hours. The reaction liquid became a high-viscosity yellow homogeneous solution. 100 g of 1,3-dimethylimidazolidinone was added thereto, and EDA and 1-propanol were distilled off under reduced pressure to obtain a 1,3-dimethylimidazolidinone solution of PVI. When 3 g of Raney-type nickel excluding water was added thereto and heated to 160 ° C. in a nitrogen stream, generation of hydrogen was observed. After performing this dehydrogenation reaction at 160 ° C. for 6 hours, the reaction solution was cooled, the nickel catalyst was removed by filtration, and the mixture was poured into acetone to deposit yellow powder. When this was dried, 15.3 g of PVIZ was obtained.
【００２９】次にろ紙にこの５重量％のＰＶＩＺ水溶液
を含浸させた後、乾燥させ、かび抵抗性試験を実施し
た。その結果、１ヶ月後においてもろ紙及び周辺にかび
の生育は見られなかった。Next, the filter paper was impregnated with this 5% by weight aqueous solution of PVIZ, dried, and subjected to a mold resistance test. As a result, no mold growth was observed on the filter paper and the surroundings after one month.
【００３０】実施例２ 実施例１で得られたＰＶＩＺ２ｇを５０ｍｌのメタノー
ルに溶解し、これに０．５ｇの塩化亜鉛を溶かしたメタ
ノール５０ｍｌに添加した。メタノールを減圧下、留去
し、ＰＶＩＺの亜鉛錯体を合成した。Example 2 2 g of PVIZ obtained in Example 1 was dissolved in 50 ml of methanol, and 0.5 g of zinc chloride was dissolved in 50 ml of methanol. Methanol was distilled off under reduced pressure to synthesize a zinc complex of PVIZ.
【００３１】ろ紙にＰＶＩＺの亜鉛錯体の５重量％の水
溶液を含浸させた後、乾燥させ、かび抵抗性試験を実施
した。その結果、１ヶ月後においてもろ紙及び周辺にか
びの生育は見られなかった。The filter paper was impregnated with a 5% by weight aqueous solution of a zinc complex of PVIZ, dried, and subjected to a mold resistance test. As a result, no mold growth was observed on the filter paper and the surroundings after one month.
【００３２】比較例１ ろ紙に蒸留水を含浸させ、かび抵抗性試験を実施した。
その結果、５日目にはろ紙の１／３を越える面積にかび
の生育が見られた。Comparative Example 1 A filter paper was impregnated with distilled water, and a mold resistance test was performed.
As a result, on the fifth day, mold growth was observed in an area exceeding one third of the filter paper.
【００３３】比較例２ ガラス製フラスコにＰＡＮ（試薬、アルドリッチ製、重
量平均分子量８万６千）１０ｇ、酢酸１ｇ、１−プロパ
ノール３０ｇ、ＥＤＡ２６．８ｇを入れ、混合し、９５
℃で９時間反応させた。反応液は粘度の高い黄色の均一
溶液になった。これをアセトン中に注ぎ、乾燥させると
淡黄色のＰＶＩ粉末が得られた。Comparative Example 2 10 g of PAN (reagent, manufactured by Aldrich, weight average molecular weight: 86,000), 1 g of acetic acid, 30 g of 1-propanol, and 26.8 g of EDA were put into a glass flask, and mixed.
The reaction was performed at 9 ° C. for 9 hours. The reaction liquid became a high-viscosity yellow homogeneous solution. This was poured into acetone and dried to give a pale yellow PVI powder.
【００３４】ろ紙にこのＰＶＩの５重量％の水溶液を含
浸させた後、乾燥させ、かび抵抗性試験を実施した。そ
の結果、２週間までは、紙及び周辺にかびの生育は見ら
れなかったが、１ヶ月後にはろ紙の１／３にかびの生育
が見られた。The filter paper was impregnated with a 5% by weight aqueous solution of PVI, dried, and subjected to a mold resistance test. As a result, no mold growth was observed on the paper and the surroundings until two weeks, but one month later, mold growth was observed on 1/3 of the filter paper.
【００３５】[0035]
【発明の効果】本発明の抗菌剤は抗菌効果が良好かつ持
続し、さらに溶液に対して分散性が高く、そのまま溶液
にして添加して使用することができる。さらに、本発明
の抗菌剤を種々の器材に含ませ抗菌性を有する組成物と
することができ、多くの用途に用いることができ、極め
て有意義である。The antibacterial agent of the present invention has a good and long-lasting antibacterial effect, has a high dispersibility in a solution, and can be used by adding it as a solution as it is. Furthermore, the antibacterial agent of the present invention can be incorporated into various devices to form a composition having antibacterial properties, and can be used for many purposes, which is extremely significant.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ａ０１Ｎ 43/50 Ａ０１Ｎ 43/50 Ｚ ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) A01N 43/50 A01N 43/50 Z
Claims (3)
とすることを特徴とする抗菌剤。An antibacterial agent comprising a 2-vinylimidazole polymer as an active ingredient.
及び銀からなる群より選ばれる１以上の金属との錯体で
あることを特徴とする請求項１に記載の抗菌剤。2. The antibacterial agent according to claim 1, wherein the 2-vinylimidazole polymer is a complex with one or more metals selected from the group consisting of zinc, copper and silver.
材に含ませてなることを特徴とする抗菌性組成物。3. An antibacterial composition comprising the antibacterial agent according to claim 1 or 2 in a device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28162899A JP2001097806A (en) | 1999-10-01 | 1999-10-01 | Antibacterial agent and antibacterial composition using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28162899A JP2001097806A (en) | 1999-10-01 | 1999-10-01 | Antibacterial agent and antibacterial composition using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001097806A true JP2001097806A (en) | 2001-04-10 |
Family
ID=17641773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28162899A Pending JP2001097806A (en) | 1999-10-01 | 1999-10-01 | Antibacterial agent and antibacterial composition using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001097806A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005298507A (en) * | 2004-04-08 | 2005-10-27 | Rohm & Haas Co | Antibacterial composition, method for producing the same and use thereof |
| JP2007106763A (en) * | 2005-10-07 | 2007-04-26 | Rohm & Haas Co | Method for disinfecting or sanitizing surface |
| JP2007177152A (en) * | 2005-12-28 | 2007-07-12 | Hokkaido Univ | Composite material film and method for producing the same, porous laminate and method for producing hydrogen carbonate ion |
| US7335613B2 (en) | 2004-04-08 | 2008-02-26 | Rohm And Haas Company | Fiber substrate with antibacterial finish and methods of making and using the same |
| US7846856B2 (en) | 2005-07-07 | 2010-12-07 | Rohm And Haas Company | Method of making a fiber containing an antimicrobial composition |
| US7927379B2 (en) * | 2009-03-11 | 2011-04-19 | Rohm And Haas Company | Method for fabric treatment at low pH |
-
1999
- 1999-10-01 JP JP28162899A patent/JP2001097806A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005298507A (en) * | 2004-04-08 | 2005-10-27 | Rohm & Haas Co | Antibacterial composition, method for producing the same and use thereof |
| US7335613B2 (en) | 2004-04-08 | 2008-02-26 | Rohm And Haas Company | Fiber substrate with antibacterial finish and methods of making and using the same |
| US7390774B2 (en) | 2004-04-08 | 2008-06-24 | Rohm And Haas Company | Antibacterial composition and methods of making and using the same |
| JP2010260874A (en) * | 2004-04-08 | 2010-11-18 | Rohm & Haas Co | Antibacterial composition, and method for producing and using the same |
| US7846856B2 (en) | 2005-07-07 | 2010-12-07 | Rohm And Haas Company | Method of making a fiber containing an antimicrobial composition |
| JP2007106763A (en) * | 2005-10-07 | 2007-04-26 | Rohm & Haas Co | Method for disinfecting or sanitizing surface |
| JP2007177152A (en) * | 2005-12-28 | 2007-07-12 | Hokkaido Univ | Composite material film and method for producing the same, porous laminate and method for producing hydrogen carbonate ion |
| US7927379B2 (en) * | 2009-03-11 | 2011-04-19 | Rohm And Haas Company | Method for fabric treatment at low pH |
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