JPH11335213A - Antimicrobial, antimicrobial resin composition and article having antimicrobial activity - Google Patents
Antimicrobial, antimicrobial resin composition and article having antimicrobial activityInfo
- Publication number
- JPH11335213A JPH11335213A JP11033659A JP3365999A JPH11335213A JP H11335213 A JPH11335213 A JP H11335213A JP 11033659 A JP11033659 A JP 11033659A JP 3365999 A JP3365999 A JP 3365999A JP H11335213 A JPH11335213 A JP H11335213A
- Authority
- JP
- Japan
- Prior art keywords
- tetramethyl
- antimicrobial
- antibacterial
- piperidyl
- resin composition
- 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
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Hydrogenated Pyridines (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は抗菌剤に関し、特に
安全性、透明性及び耐候性に優れる抗菌剤に関する。
又、本発明は上記抗菌剤を用いた樹脂組成物、更にはそ
の樹脂組成物を用いた物品に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antibacterial agent, and more particularly to an antibacterial agent having excellent safety, transparency and weather resistance.
The present invention also relates to a resin composition using the above antibacterial agent, and further to an article using the resin composition.
【０００２】[0002]
【従来の技術】従来、抗菌剤は無機系と有機系のものに
大別される。無機系の抗菌剤は、樹脂、合成繊維或いは
塗料等に添加して使用した場合、得られる製品の耐熱性
及び耐候性が良好ではあるが、得られる製品の透明性及
び機械的強度等の物性を劣化させるという問題点があ
る。又、無機系の抗菌剤の安全性については、該抗菌剤
が銀等の金属イオンを含有しているので、今後の大量消
費による銀等の金属の蓄積に起因する生態系への影響が
問題となっている。2. Description of the Related Art Conventionally, antibacterial agents are roughly classified into inorganic and organic ones. When an inorganic antibacterial agent is used by adding it to a resin, synthetic fiber, paint, or the like, the resulting product has good heat resistance and weather resistance, but the obtained product has properties such as transparency and mechanical strength. Is deteriorated. In addition, regarding the safety of inorganic antibacterial agents, since the antibacterial agents contain metal ions such as silver, the effect on ecosystems due to the accumulation of silver and other metals due to future mass consumption is a problem. It has become.
【０００３】有機系の抗菌剤は、樹脂、合成繊維或いは
塗料等に添加して使用する場合、得られる製品の機械的
強度は良好ではあるが、該製品の耐熱性や耐候性に欠点
があり、使用する抗菌剤の種類によっては得られる製品
に透明性の問題が生じる。When an organic antibacterial agent is used by adding it to a resin, synthetic fiber, paint or the like, the resulting product has good mechanical strength, but has a defect in heat resistance and weather resistance of the product. Depending on the type of antibacterial agent used, the resulting product has a problem of transparency.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、上記の問題
点を克服し、樹脂や合成繊維等に添加して使用した場
合、得られる製品に優れた透明性、安全性、耐候性及び
耐劣化性を与えることができる抗菌剤を提供することを
目的とする。DISCLOSURE OF THE INVENTION The present invention overcomes the above-mentioned problems, and when used in addition to resins, synthetic fibers, and the like, provides excellent transparency, safety, weatherability, and resistance to products. An object of the present invention is to provide an antibacterial agent capable of imparting deterioration.
【０００５】[0005]
【課題を解決するための手段】上記目的は以下の本発明
によって達成される。即ち、本発明は、２，２，６，６
−テトラメチル−４−ピペリジン誘導体からなることを
特徴とする抗菌剤、該抗菌剤を含む抗菌性樹脂組成物、
及び該抗菌性樹脂組成物からなる抗菌性物品を提供す
る。本発明者は、鋭意研究を重ねた結果、２，２，６，
６−テトラメチル−４−ピペリジン誘導体が、該誘導体
を樹脂や合成繊維に添加した場合、これらの樹脂や合成
繊維等に安定した抗菌性、優れた透明性、安全性、耐候
性及び耐劣化性を付与することを見い出し、本発明を完
成するに至った。The above object is achieved by the present invention described below. That is, the present invention relates to 2,2,6,6
-An antimicrobial agent comprising a tetramethyl-4-piperidine derivative, an antimicrobial resin composition containing the antimicrobial agent,
And an antibacterial article comprising the antibacterial resin composition. The present inventors have conducted intensive studies and found that 2,2,6,
When the 6-tetramethyl-4-piperidine derivative is added to a resin or a synthetic fiber, the derivative has a stable antibacterial property, excellent transparency, safety, weather resistance and deterioration resistance to the resin or the synthetic fiber. Has been found, and the present invention has been completed.
【０００６】[0006]
【発明の実施の形態】次に好ましい実施態様を挙げて本
発明を更に詳細に説明する。本発明で使用される２，
２，６，６−テトラメチル−４−ピペリジン誘導体は、
分子中に以下の構造を有する化合物である。Next, the present invention will be described in more detail with reference to preferred embodiments. 2, used in the present invention
The 2,6,6-tetramethyl-4-piperidine derivative is
It is a compound having the following structure in the molecule.
【０００７】 （式中、Ｒは水素原子又はアルキル基である。）[0007] (In the formula, R is a hydrogen atom or an alkyl group.)
【０００８】本発明で使用される２，２，６，６−テト
ラメチル−４−ピペリジン誘導体としては公知の化合物
が使用できるが、下記（ａ）〜（ｅ）の化合物が特に好
ましい。 （ａ）ビス（２，２，６，６−テトラメチル−４−ピペ
リジル）セバケート As the 2,2,6,6-tetramethyl-4-piperidine derivative used in the present invention, known compounds can be used, but the following compounds (a) to (e) are particularly preferred. (A) bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate
【０００９】（ｂ）ポリ［｛６−（１，１，３，３−テ
トラメチルブチル）アミノ−１，３，５−トリアジン−
２，４−ジイル｝｛（２，２，６，６，−テトラメチル
−４−ピペリジル）イミノ｝ヘキサメチレン｛（２，
２，６，６−テトラメチル−４−ピペリジル）イミ
ノ｝］ (B) poly [{6- (1,1,3,3-tetramethylbutyl) amino-1,3,5-triazine-
2,4-diyl {(2,2,6,6-tetramethyl-4-piperidyl) imino {hexamethylene} (2
2,6,6-tetramethyl-4-piperidyl) imino}]
【００１０】（ｃ）１，２，３，４−ブタンテトラカル
ボン酸と２，２，６，６−テトラメチル−４−ピペリジ
ノール及び３，９−ビス（２−ヒドロキシ−１，１−ジ
メチルエチル）−２，４，８，１０−テトラオキサスピ
ロ〔５．５〕ウンデカンとの混合エステル化物 (C) 1,2,3,4-butanetetracarboxylic acid and 2,2,6,6-tetramethyl-4-piperidinol and 3,9-bis (2-hydroxy-1,1-dimethylethyl) ) -2,4,8,10-Tetraoxaspiro [5.5] undecane mixed esterified product
【００１１】（ｄ）テトラキス（１，２，２，６，６−
ペンタメチル−４−ピペリジル）−１，２，３，４−ブ
タンテトラカルボキシラート (D) tetrakis (1,2,2,6,6-
(Pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate
【００１２】（ｅ）テトラキス（２，２，６，６−テト
ラメチル−４−ピペリジル）−１，２，３，４−ブタン
テトラカルボキシラート 上記化合物の内（ａ）及び（ｂ）はポリオレフィン等、
衛生協議会でのポジティブリストに記載されており、食
品容器及び包装用途への使用が認められていることから
特に安全性に優れている。これらの化合物は単独でも２
種以上組み合わせても使用することができる。(E) Tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate Of the above compounds (a) and (b) are polyolefins,
It is listed on the Positive List at the Sanitation Council and is particularly safe because it is approved for use in food containers and packaging. These compounds alone or
A combination of more than one species can be used.
【００１３】本発明で使用される２，２，６，６−テト
ラメチル−４−ピペリジン誘導体は、融点又は軟化点が
８０〜１３５℃であり、樹脂への分散性に優れ、透明性
が高い抗菌性樹脂組成物を提供することができる。The 2,2,6,6-tetramethyl-4-piperidine derivative used in the present invention has a melting point or softening point of 80 to 135 ° C., is excellent in dispersibility in a resin, and has high transparency. An antimicrobial resin composition can be provided.
【００１４】本発明で使用される２，２，６，６−テト
ラメチル−４−ピペリジン誘導体は、特に樹脂に対し
て、耐候性及び耐劣化性を付与されることが知られてお
り、従来の有機抗菌剤より優れた抗菌性樹脂組成物を提
供することができる。It is known that the 2,2,6,6-tetramethyl-4-piperidine derivative used in the present invention imparts weather resistance and deterioration resistance particularly to resins. It is possible to provide an antibacterial resin composition which is more excellent than the organic antibacterial agent.
【００１５】本発明の抗菌剤の抗菌性は、以下の機構に
より発現されるものと推測する。即ち２，２，６，６−
テトラメチル−４−ピペリジン構造から第四級アンモニ
ウム塩を形成し、菌に対して細胞膜・細胞壁の損傷、酵
素タンパク質の変性・呼吸阻害を引き起こして抗菌性を
示すものと考えられる。It is presumed that the antibacterial property of the antibacterial agent of the present invention is exhibited by the following mechanism. That is, 2,2,6,6-
It is thought that quaternary ammonium salts are formed from the tetramethyl-4-piperidine structure, causing damage to cell membranes and cell walls, denaturation of enzyme proteins, and inhibition of respiration for bacteria, thereby exhibiting antibacterial properties.
【００１６】本発明の抗菌性樹脂組成物で使用される樹
脂としては特に限定されず、例えば、ポリエチレン樹
脂、ポリプロピレン樹脂、ポリエステル樹脂、ポリスチ
レン樹脂、ポリ塩化ビニル樹脂、ポリウレタン樹脂、ポ
リアクリル樹脂、ポリアミド樹脂、ポリビニルアルコー
ル樹脂、セルロース樹脂等が挙げられる。The resin used in the antibacterial resin composition of the present invention is not particularly limited. Examples thereof include polyethylene resin, polypropylene resin, polyester resin, polystyrene resin, polyvinyl chloride resin, polyurethane resin, polyacryl resin, and polyamide. Resin, polyvinyl alcohol resin, cellulose resin, and the like.
【００１７】本発明の抗菌性樹脂組成物で使用される
２，２，６，６−テトラメチル−４−ピペリジン誘導体
の添加量は特に限定されないが、樹脂１００重量部に対
して０．０５〜５重量部が好ましい。２，２，６，６−
テトラメチル−４−ピペリジン誘導体の添加量が０．０
５重量部未満になると、得られる樹脂組成物の抗菌効果
が低くなり、例えば、ビス（２，２，６，６−テトラメ
チル−４−ピペリジル）セバケートではグラム陰性細菌
に対する抗菌効果が認めにくくなる。又、２，２，６，
６−テトラメチル−４−ピペリジン誘導体の添加量が５
重量部を越えると、得られる樹脂組成物の物性に悪影響
を及ぼすおそれがある。The amount of the 2,2,6,6-tetramethyl-4-piperidine derivative used in the antimicrobial resin composition of the present invention is not particularly limited, but is preferably 0.05 to 100 parts by weight of the resin. 5 parts by weight are preferred. 2,2,6,6-
When the addition amount of the tetramethyl-4-piperidine derivative is 0.0
When the amount is less than 5 parts by weight, the antibacterial effect of the obtained resin composition becomes low. For example, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate does not easily show the antibacterial effect against Gram-negative bacteria. . Also, 2, 2, 6,
The amount of the 6-tetramethyl-4-piperidine derivative added is 5
If the amount exceeds the weight part, physical properties of the obtained resin composition may be adversely affected.
【００１８】本発明の抗菌性樹脂組成物には本発明の効
果を損なわない範囲で顔料、添加剤、他の抗菌剤等を加
えることができる。本発明の抗菌性を有する物品は、本
発明の上記抗菌性樹脂組成物からなるものであれば特に
限定されないが、例として以下の物品が挙げられる。The antibacterial resin composition of the present invention may contain pigments, additives, other antibacterial agents and the like as long as the effects of the present invention are not impaired. The antibacterial article of the present invention is not particularly limited as long as it is made of the above antibacterial resin composition of the present invention, and examples include the following articles.
【００１９】（１）抗菌性成形品 本発明の抗菌性樹脂組成物を射出成形、押出成形、ブロ
ー成形等により成形した物品であり、より具体的には食
品容器、ごみ箱、文具、電気器具のハウジング、化粧品
容器、車両内装部品、台所用品、浴用製品、衣装収納製
品等が挙げられる。(1) Antibacterial molded article An antibacterial resin composition of the present invention is an article formed by injection molding, extrusion molding, blow molding, or the like. More specifically, it is used for food containers, garbage boxes, stationery, and electric appliances. Housings, cosmetic containers, vehicle interior parts, kitchenware, bath products, costume storage products, and the like.
【００２０】（２）抗菌性繊維 本発明の抗菌性樹脂組成物を紡糸等により繊維化した物
品であり、更にはそれを織布又は不織布としたものであ
る。より具体的には衣服やカーペット等が挙げられる。 （３）抗菌性塗料 本発明の抗菌性樹脂組成物を、溶剤に溶解又は分散して
塗料とする。(2) Antimicrobial fiber An article obtained by fiberizing the antimicrobial resin composition of the present invention by spinning or the like, and further comprising a woven or nonwoven fabric. More specifically, clothes, carpets and the like are mentioned. (3) Antibacterial paint The antibacterial resin composition of the present invention is dissolved or dispersed in a solvent to form a paint.
【００２１】[0021]
【実施例】以下に実施例及び比較例を挙げて本発明を詳
しく説明する。尚、文中部とあるのは特に断りのない限
り重量基準である。本実施例で使用する抗菌剤を以下に
示す。The present invention will be described in detail below with reference to examples and comparative examples. It should be noted that the parts in the text are based on weight unless otherwise specified. The antibacterial agents used in this example are shown below.
【００２２】抗菌剤ａ：ビス（２，２，６，６−テトラ
メチル−４−ピペリジル）セバケート（ＣＡＳＮｏ．５
２８２９−０７−９） 抗菌剤ｂ：ポリ［｛６−（１，１，３，３−テトラメチ
ルブチル）アミノ−１，３，５−トリアジン−２，４−
ジイル｝｛（２，２，６，６，−テトラメチル−４−ピ
ペリジル）イミノ｝ヘキサメチレン｛（２，２，６，６
−テトラメチル−４−ピペリジル）イミノ｝］（ＣＡＳ
Ｎｏ．７１８７８−１９−８） 抗菌剤ｃ：１，２，３，４−ブタンテトラカルボン酸と
２，２，６，６−テトラメチル−４−ピペリジノール及
び３，９−ビス（２−ヒドロキシ−１，１−ジメチルエ
チル）−２，４，８，１０−テトラオキサスピロ〔５．
５〕ウンデカンとの混合エステル化物（ＣＡＳＮｏ．１
１９５２４−４７−９） 抗菌剤ｄ：テトラキス（１，２，２，６，６−ペンタメ
チル−４−ピペリジル）−１，２，３，４−ブタンテト
ラカルボキシラート（ＣＡＳＮｏ．９１２７４−８９−
４） 抗菌剤ｅ：テトラキス（２，２，６，６−テトラメチル
−４−ピペリジル）−１，２，３，４−ブタンテトラカ
ルボキシラート（ＣＡＳＮｏ．６４０２２−６１−３）Antibacterial agent a: bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate (CAS No. 5)
2829-07-9) Antibacterial agent b: poly [{6- (1,1,3,3-tetramethylbutyl) amino-1,3,5-triazine-2,4-
Diyl {(2,2,6,6-tetramethyl-4-piperidyl) imino} hexamethylene} (2,2,6,6
-Tetramethyl-4-piperidyl) imino}] (CAS
No. 71878-19-8) Antimicrobial agent c: 1,2,3,4-butanetetracarboxylic acid and 2,2,6,6-tetramethyl-4-piperidinol and 3,9-bis (2-hydroxy-1,2 1-dimethylethyl) -2,4,8,10-tetraoxaspiro [5.
5] Mixed esterified product with undecane (CAS No. 1)
19524-47-9) Antibacterial agent d: tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate (CAS No. 91274-89-)
4) Antibacterial agent e: tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate (CAS No.64022-61-3)
【００２３】実施例１ ニュートリエントブロス液体培地で３７℃で１６時間前
培養した菌液を２００倍に希釈して接種菌液とした。接
種菌液に抗菌剤ａを５００ｐｐｍ添加し、これを滅菌Ｌ
字管に５ｍｌ採り、３７℃で２４時間培養した培養液に
ついて、寒天平板希釈法により生菌数を測定した（シェ
イクフラスコ法）。大腸菌（Escherichia coli）及び
黄色ブドウ球菌（Staphylococcus aureus）について試
験した。結果を表１に示す。Example 1 A bacterial solution precultured in a nutrient broth liquid medium at 37 ° C. for 16 hours was diluted 200-fold to obtain an inoculated bacterial solution. Add 500 ppm of antimicrobial agent a to the inoculated bacterial solution, and sterilize L
A 5 ml aliquot was placed in a tube and cultured for 24 hours at 37 ° C., and the viable cell count was measured by the agar plate dilution method (shake flask method). Escherichia coli and Staphylococcus aureus were tested. Table 1 shows the results.
【００２４】実施例２〜５ 抗菌剤ａの代りに各々抗菌剤ｂ〜ｅを使用する以外は実
施例１と同様に試験した。結果を表１に示す。 比較例１ 抗菌剤を添加しないで実施例１と同様に試験した。結果
を表１に示す。Examples 2 to 5 Tests were conducted in the same manner as in Example 1 except that antimicrobial agents be used instead of antimicrobial agent a. Table 1 shows the results. Comparative Example 1 A test was performed in the same manner as in Example 1 without adding an antibacterial agent. Table 1 shows the results.
【００２５】[0025]
【表１】表１：結果（実施例１〜５及び比較例１） Table 1: Results (Examples 1 to 5 and Comparative Example 1)
【００２６】実施例６ 低密度ポリエチレン樹脂１００部と抗菌剤ａ０．３部と
を加熱混練後成形し、透明な試料フィルムを得た。抗菌
性は、実施例１の抗菌剤ａを５００ｐｐｍ添加する代り
に試料フィルム１．０ｇを添加する以外は実施例１と同
様に試験した。又、耐候性をＪＩＳ Ｋ７１１３に従
い、各試料フィルムを２号ダンベルサイズに打ち抜き、
これらをサンシャインウェザーオーメーターにて５００
時間暴露させた。暴露後の試験片の破断伸度を引張試験
機にて測定した。以上の結果を表２に示す。Example 6 100 parts of a low-density polyethylene resin and 0.3 part of an antibacterial agent a were kneaded by heating and then molded to obtain a transparent sample film. The antibacterial property was tested in the same manner as in Example 1 except that 1.0 g of the sample film was added instead of adding 500 ppm of the antibacterial agent a of Example 1. Also, in accordance with JIS K7113, each sample film was punched into a No. 2 dumbbell size,
These are 500 with a sunshine weather o meter
Exposure for hours. The elongation at break of the test piece after the exposure was measured by a tensile tester. Table 2 shows the above results.
【００２７】実施例７〜１０ 抗菌剤ａの代りに各々抗菌剤ｂ〜ｅを使用する以外は実
施例６と同様に試験した。結果を表２に示す。 比較例２ 抗菌剤を添加しないで実施例６と同様に試験した。結果
を表２に示す。Examples 7 to 10 Tests were conducted in the same manner as in Example 6 except that antimicrobial agents be used instead of antimicrobial agent a. Table 2 shows the results. Comparative Example 2 A test was performed in the same manner as in Example 6 without adding an antibacterial agent. Table 2 shows the results.
【００２８】[0028]
【表２】表２：結果（実施例６〜１０及び比較例２） Table 2: Results (Examples 6 to 10 and Comparative Example 2)
【００２９】実施例１１ ポリプロピレン樹脂１００部と抗菌剤ａ０．５部とを加
熱混練後成形し、透明な５ｃｍ×５ｃｍの試料プレート
を得た。ニュートリエントブロス液体培地で３７℃で１
６時間前培養した菌液をリン酸緩衝液で希釈し、接種菌
液とした。滅菌処理した試料プレート表面の対角に４カ
所及び中心に１カ所接種菌液を各０．１ｍｌ滴下し、滅
菌シャーレ中で３７℃で相対湿度９０％以上で２４時間
培養したのち、リン酸緩衝液で菌を洗い出し、寒天平板
希釈法で生菌数を測定した（ドロップ法）。大腸菌（Es
cherichia coli）及び黄色ブドウ球菌（Staphylococcu
s aureus）について試験した。結果を表３に示す。Example 11 100 parts of a polypropylene resin and 0.5 part of an antimicrobial agent a were kneaded by heating and then molded to obtain a transparent 5 cm × 5 cm sample plate. Nutrient broth liquid medium at 37 ° C
The bacterial solution pre-cultured for 6 hours was diluted with a phosphate buffer to obtain an inoculated bacterial solution. 0.1 ml each of the inoculated bacterial solution was dropped at four locations and one location at the center on the diagonal of the surface of the sterilized sample plate, and cultured in a sterilized petri dish at 37 ° C. at a relative humidity of 90% or more for 24 hours. The bacteria were washed out with the liquid, and the number of viable bacteria was measured by an agar plate dilution method (drop method). Escherichia coli (Es
cherichia coli) and Staphylococcus
s aureus). Table 3 shows the results.
【００３０】実施例１２〜１５ 抗菌剤ａの代りに各々抗菌剤ｂ〜ｅを使用する以外は実
施例１１と同様に試験した。結果を表３に示す。 比較例３ 抗菌剤を添加しないで実施例１１と同様に試験した。結
果を表３に示す。Examples 12 to 15 Tests were performed in the same manner as in Example 11 except that antimicrobial agents be used instead of antimicrobial agent a. Table 3 shows the results. Comparative Example 3 A test was performed in the same manner as in Example 11 without adding an antibacterial agent. Table 3 shows the results.
【００３１】[0031]
【表３】表３：結果（実施例１１〜１５及び比較例３） Table 3: Results (Examples 11 to 15 and Comparative Example 3)
【００３２】実施例１６ 飽和ポリエステル１００部と抗菌剤ａ０．３部とを加熱
混練後紡糸し、透明な試料繊維を得た。ニュートリエン
トブロス液体培地で３７℃で１６時間前培養後希釈した
菌液０．２ｍｌを滅菌バイアル瓶中の試料繊維０．４ｇ
に接種する。３７℃で１８時間培養後、生理食塩水で洗
い出し、寒天平板希釈法で生菌数を測定した。黄色ブド
ウ球菌（Staphylococcus aureus）及び肺炎桿菌（Kleb
siellapneumoniae）について試験した。結果を表４に示
す。Example 16 100 parts of a saturated polyester and 0.3 part of an antibacterial agent a were kneaded under heating and spun to obtain a transparent sample fiber. 0.2 ml of the diluted bacterial solution after pre-cultured in a nutrient broth liquid medium at 37 ° C. for 16 hours, 0.4 g of the sample fiber in a sterilized vial
Inoculate. After culturing at 37 ° C. for 18 hours, the cells were washed out with physiological saline and the viable cell count was measured by an agar plate dilution method. Staphylococcus aureus and Kleb
siellapneumoniae). Table 4 shows the results.
【００３３】実施例１７〜２０ 抗菌剤ａの代りに各々抗菌剤ｂ〜ｅを使用する以外は実
施例１６と同様に試験した。結果を表４に示す。Examples 17 to 20 Tests were conducted in the same manner as in Example 16 except that antimicrobial agents be used instead of antimicrobial agent a. Table 4 shows the results.
【００３４】比較例４ 飽和ポリエステルを加熱混練後紡糸し、透明な試料繊維
を得た。ニュートリエントブロス液体培地で３７℃で１
６時間前培養後希釈した菌液０．２ｍｌを滅菌バイアル
瓶中の試料繊維０．４ｇに接種する。接種直後の試料を
生理食塩水で洗い出し、寒天平板希釈法で生菌数を測定
し初期値とした。又、接種後別途３７℃で１８時間培養
し、生理食塩水で洗い出し、寒天平板希釈法で生菌数を
測定した。黄色ブドウ球菌（Staphylococcus aureus）
及び肺炎桿菌（Klebsiella pneumoniae）について試
験した。結果を表４に示す。Comparative Example 4 A saturated polyester was spun after heating and kneading to obtain a transparent sample fiber. Nutrient broth liquid medium at 37 ° C
0.2 ml of the diluted bacterial solution after 6 hours of preculture is inoculated into 0.4 g of the sample fiber in a sterile vial. The sample immediately after the inoculation was washed out with physiological saline, and the number of viable cells was measured by an agar plate dilution method to obtain an initial value. After inoculation, the cells were separately cultured at 37 ° C. for 18 hours, washed with physiological saline, and the viable cell count was measured by an agar plate dilution method. Staphylococcus aureus
And Klebsiella pneumoniae. Table 4 shows the results.
【００３５】[0035]
【表４】表４：結果（実施例１６〜２０及び比較例４） Table 4: Results (Examples 16 to 20 and Comparative Example 4)
【００３６】実施例２１ 実施例６の樹脂組成物を加熱混練し、次いで押出成形し
て食品用トレーを得た。このものは抗菌性を有すること
が確認された。Example 21 The resin composition of Example 6 was heated and kneaded, and then extruded to obtain a food tray. This was confirmed to have antibacterial properties.
【００３７】[0037]
【発明の効果】本発明の抗菌剤は上述のように、優れた
抗菌性を発現しつつ、安全性、透明性、耐熱性、耐候
性、耐劣化性に優れており、又、該抗菌剤を用いた樹脂
組成物、更にはその樹脂組成物を用いた物品も同様に優
れた上記特性を有する。As described above, the antibacterial agent of the present invention exhibits excellent antibacterial properties, as well as excellent safety, transparency, heat resistance, weather resistance, and deterioration resistance. A resin composition using the same, and an article using the resin composition also have the above excellent properties.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｄ 211/46 Ｃ０７Ｄ 211/46 493/10 493/10 Ｃ Ｃ０８Ｇ 73/00 Ｃ０８Ｇ 73/00 Ｃ０８Ｋ 5/3435 Ｃ０８Ｋ 5/3435 Ｃ０８Ｌ 101/00 Ｃ０８Ｌ 101/00 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 Identification code FI C07D 211/46 C07D 211/46 493/10 493/10 C C08G 73/00 C08G 73/00 C08K 5/3435 C08K 5/3435 C08L 101/00 C08L 101/00
Claims (4)
ペリジン誘導体からなることを特徴とする抗菌剤。1. An antibacterial agent comprising a 2,2,6,6-tetramethyl-4-piperidine derivative.
ペリジン誘導体が、（ａ）ビス（２，２，６，６−テト
ラメチル−４−ピペリジル）セバケート、（ｂ）ポリ
［｛６−（１，１，３，３−テトラメチルブチル）アミ
ノ−１，３，５−トリアジン−２，４−ジイル｝
｛（２，２，６，６，−テトラメチル−４−ピペリジ
ル）イミノ｝ヘキサメチレン｛（２，２，６，６−テト
ラメチル−４−ピペリジル）イミノ｝］、（ｃ）１，
２，３，４−ブタンテトラカルボン酸と２，２，６，６
−テトラメチル−４−ピペリジノール及び３，９−ビス
（２−ヒドロキシ−１，１−ジメチルエチル）−２，
４，８，１０−テトラオキサスピロ〔５．５〕ウンデカ
ンとの混合エステル化物、（ｄ）テトラキス（１，２，
２，６，６−ペンタメチル−４−ピペリジル）−１，
２，３，４−ブタンテトラカルボキシラート及び（ｅ）
テトラキス（２，２，６，６−テトラメチル−４−ピペ
リジル）−１，２，３，４−ブタンテトラカルボキシラ
ートの群から選ばれた少なくとも１種の化合物である請
求項１に記載の抗菌剤。2. The 2,2,6,6-tetramethyl-4-piperidine derivative comprises (a) bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate and (b) poly [｛ 6- (1,1,3,3-tetramethylbutyl) amino-1,3,5-triazine-2,4-diyl
{(2,2,6,6-tetramethyl-4-piperidyl) imino} hexamethylene {(2,2,6,6-tetramethyl-4-piperidyl) imino}], (c) 1,
2,3,4-butanetetracarboxylic acid and 2,2,6,6
-Tetramethyl-4-piperidinol and 3,9-bis (2-hydroxy-1,1-dimethylethyl) -2,
Mixed esterified product with 4,8,10-tetraoxaspiro [5.5] undecane, (d) tetrakis (1,2,2
2,6,6-pentamethyl-4-piperidyl) -1,
2,3,4-butanetetracarboxylate and (e)
The antibacterial according to claim 1, wherein the antibacterial is at least one compound selected from the group consisting of tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate. Agent.
からなること特徴とする抗菌性樹脂組成物。3. An antibacterial resin composition comprising the antibacterial agent according to claim 1 and a resin.
と特徴とする抗菌性を有する物品。4. An article having antibacterial properties, comprising the antibacterial resin composition according to claim 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03365999A JP3716965B2 (en) | 1998-03-24 | 1999-02-12 | Antibacterial agent |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10-76209 | 1998-03-24 | ||
| JP7620998 | 1998-03-24 | ||
| JP03365999A JP3716965B2 (en) | 1998-03-24 | 1999-02-12 | Antibacterial agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11335213A true JPH11335213A (en) | 1999-12-07 |
| JP3716965B2 JP3716965B2 (en) | 2005-11-16 |
Family
ID=26372393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP03365999A Expired - Fee Related JP3716965B2 (en) | 1998-03-24 | 1999-02-12 | Antibacterial agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3716965B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008526779A (en) * | 2005-01-03 | 2008-07-24 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | A method for converting normal and commercially important polymers into durable and refillable antimicrobial polymeric materials. |
| JP2008214396A (en) * | 2007-02-28 | 2008-09-18 | Dainichiseika Color & Chem Mfg Co Ltd | Polymer-bonded anti-bacterial agent and use of the same |
-
1999
- 1999-02-12 JP JP03365999A patent/JP3716965B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008526779A (en) * | 2005-01-03 | 2008-07-24 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | A method for converting normal and commercially important polymers into durable and refillable antimicrobial polymeric materials. |
| JP2008214396A (en) * | 2007-02-28 | 2008-09-18 | Dainichiseika Color & Chem Mfg Co Ltd | Polymer-bonded anti-bacterial agent and use of the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3716965B2 (en) | 2005-11-16 |
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