JPH0121123B2 - - Google Patents
Info
- Publication number
- JPH0121123B2 JPH0121123B2 JP8269079A JP8269079A JPH0121123B2 JP H0121123 B2 JPH0121123 B2 JP H0121123B2 JP 8269079 A JP8269079 A JP 8269079A JP 8269079 A JP8269079 A JP 8269079A JP H0121123 B2 JPH0121123 B2 JP H0121123B2
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- iodine
- methyl acrylate
- vinylpyrrolidone
- amount
- 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.)
- Expired
Links
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 239000011630 iodine Substances 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- OYVTWDRMQKITTL-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;methyl prop-2-enoate Chemical compound COC(=O)C=C.C=CN1CCCC1=O OYVTWDRMQKITTL-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は殺菌性組成物に関するものである。詳
しくはヨウ素を含む固体状殺菌性組成物に関する
ものである。
従来、ポリビニルピロリドンとヨウ素を含む液
状の組成物が殺菌剤として有用なことは知られて
いる。また、ビニルピロリドンとジビニルベンゼ
ン等のコモノマーの共重合体とヨウ素を含む固体
状の組成物が殺菌剤として有用なことも知られて
いる。
一方、緊急用手術器具や人口臓器のコーテイン
グ用に、固体状殺菌性組成物が必要とされてい
る。この用途には固体であることが必要であり、
従来知られているものでは殺菌性やヨウ素の溶解
性の点で不満足である。
本発明者等は、これらの事情に鑑み鋭意研究し
た結果、本発明に到達した。
すなわち、本発明の要旨は、ビニルピロリドン
とアクリル酸メチルまたはメチルメタクリレート
の共重合体およびヨウ素を含む固体状殺菌性組成
物に存する。
以下に本発明を詳細に説明する。
本発明に係わる組成物の一つの成分である、ビ
ニルピロリドンとアクリル酸メチルまたはメチル
メタクリレートの共重合体中のビニルピロリドン
とアクリル酸メチルまたはメチルメタクリレート
のモル比は、通常10：〜90〜90：10、好ましくは
30：70〜70：30である。ビニルピロリドンの量が
少なすぎると、組成物中に含みうるヨウ素の量が
低下して殺菌性が不十分となるし、またビニルピ
ロリドンの量が多すぎても共重合体の強度が低下
したりするので、何れも好ましくない。また、こ
の共重合体の分子量は、固体としての物性がみた
される範囲であれば、とくに制限はない。
ヨウ素の量は、ビニルピロリドンとアクリル酸
メチルまたはメチルメタクリレートの共重合体中
のビニルピロリドンの量により変化するが、この
共重合体に対し0.1〜10％（重量）、好ましくは
0.5〜５％（重量）である。共重合体中のビニル
ピロリドンの量が多い場合にはヨウ素を多く含む
ことができる。何れにしても、ヨウ素の量は、共
重合体中への溶解度以下である。ヨウ素の量が少
なすぎると殺菌性が不十分となるし、ヨウ素の量
が多すぎても、共重合体への溶解度をこえ、組成
物が不均一となるので好ましくない。
本発明組成物は、勿論その目的の範囲内におい
て、他の成分を含んでいてもさしつかえない。
本発明に係わる組成物は、例えば以下に述べる
ようにして製造することができる。
先ず、ビニルピロリドンとアクリル酸メチルま
たはメチルメタクリレートの共重合体は、常法に
よりビニルピロリドンとアクリル酸メチルまたは
メチルメタクリレートを所定量混合し、ラジカル
開始剤を触媒として、溶液重合、乳化重合や懸濁
重合を行わせることにより、製造することができ
る。低分子量の分画を除きたい場合には、常法に
より溶媒精製を行えばよい。このビニルピロリド
ンとアクリル酸メチルまたはメチルメタクリレー
トの共重合体は、例えばアセトンやメチルエチル
ケトン等のケトン系の溶媒等に可溶性である。
ビニルピロリドンとアクリル酸メチルまたはメ
チルメタクリレートを共重合体とヨウ素を混合す
るには、例えばこの共重合体を前記の様な溶媒に
溶解させ、ヨウ素の溶液を滴下し、混合した後、
例えば水等の貧溶媒を添加すると、目的とする組
成物を沈殿として得ることができる。
得られた組成物は殺菌性があり、緊急用手術器
具や人工臓器のレコーデイング用として有用であ
り、優れた物性を有している。
以下に製造例および応用例を挙げて、本発明を
更に詳細に説明するが、本発明はその要旨を超え
ない限り、以下の実施例により限定を受けるもの
ではない。
製造例 １
ビニルピロリドン（モノマー）50ｇおよびアク
リル酸メチル（モノマー）50ｇを、500mlのアセ
トンに溶解し、重合開始剤（アゾビスイソブチロ
ニトル）１ｇをアセトン10mlに溶解して加え、窒
素気流中で60℃、５時間反応させる。この反応物
を、ｎ−ヘキサン中に滴下して、不溶な共重合体
を彩取する。
この共重合体は、クロロホルム、テトラヒドロ
フランおよびエチルメチルケトンに対して無色透
明に溶け、水、アセトンに対しては不溶であつ
た。
別にヨウ素のエチルアルコール飽和溶液を準備
し、この中に上記のビニルピロリドン−アクリル
酸メチル共重合体を浸漬し、24時間後、水洗、乾
燥する。
元素分析（重量％）
Ｃ Ｈ Ｎ Ｉ
分析値 58.26 7.52 3.99 3.58
製造例 ２〜３
ビニルピロリドン25ｇおよびアクリル酸メチル
75ｇまたはビニルピロリドン75ｇおよびアクリル
酸メチル25ｇを原料とした他は製造例１と同様に
して、殺菌性組成物が得られた。
製造例 ４〜６
製造例１〜３において、アクリル酸メチルをメ
チルメタクリレートに代えた他は同様にして、殺
菌性組成物が得られた。
応用例
殺菌性の試験
製造例１により得られたビニルピロリドン−ア
クリル酸メチル共重合体−ヨウ素組成物0.5ｇを
試験管中のブレイン ハート インフユ−ジヨン
ブロス（Brain heart infusion broth）培地10
mlに加え、スタフイロコツカス アウレス（JC
−１株）またはエシエリシア コリ（JC−２株）
を所定量を加え、37℃で18時間静置培養または振
とう培養した。また、振とう培養したものについ
ては、菌を再接種し、37℃で18時間静置培養し
た。結果は表１に示した。
なお、表中で＋の記号は殺菌効果あり、−の記
号は殺菌効果なしの意味をそれぞれ表わす。
FIELD OF THE INVENTION The present invention relates to fungicidal compositions. More specifically, the present invention relates to a solid antiseptic composition containing iodine. It has been known that liquid compositions containing polyvinylpyrrolidone and iodine are useful as disinfectants. It is also known that solid compositions containing iodine and copolymers of vinylpyrrolidone and comonomers such as divinylbenzene are useful as fungicides. On the other hand, solid germicidal compositions are needed for coating emergency surgical instruments and artificial organs. This application requires a solid state,
Conventionally known products are unsatisfactory in terms of bactericidal properties and iodine solubility. In view of these circumstances, the present inventors conducted extensive research and arrived at the present invention. That is, the gist of the present invention resides in a solid fungicidal composition comprising a copolymer of vinylpyrrolidone and methyl acrylate or methyl methacrylate and iodine. The present invention will be explained in detail below. The molar ratio of vinylpyrrolidone and methyl acrylate or methyl methacrylate in the copolymer of vinylpyrrolidone and methyl acrylate or methyl methacrylate, which is one component of the composition according to the present invention, is usually 10: to 90 to 90: 10, preferably
It is from 30:70 to 70:30. If the amount of vinyl pyrrolidone is too small, the amount of iodine that can be contained in the composition will be reduced, resulting in insufficient bactericidal properties, and if the amount of vinyl pyrrolidone is too large, the strength of the copolymer may be reduced. Therefore, neither is preferable. Further, the molecular weight of this copolymer is not particularly limited as long as the physical properties as a solid are satisfied. The amount of iodine varies depending on the amount of vinylpyrrolidone in the copolymer of vinylpyrrolidone and methyl acrylate or methyl methacrylate, but is preferably 0.1 to 10% (by weight) of the copolymer.
It is 0.5-5% (weight). When the amount of vinylpyrrolidone in the copolymer is large, it can contain a large amount of iodine. In any event, the amount of iodine is below its solubility in the copolymer. If the amount of iodine is too small, the bactericidal properties will be insufficient, and if the amount of iodine is too large, the solubility in the copolymer will be exceeded and the composition will become non-uniform, which is not preferable. The composition of the present invention may of course contain other components within the scope of its purpose. The composition according to the present invention can be produced, for example, as described below. First, a copolymer of vinyl pyrrolidone and methyl acrylate or methyl methacrylate is prepared by mixing a predetermined amount of vinyl pyrrolidone and methyl acrylate or methyl methacrylate using a conventional method, and then carrying out solution polymerization, emulsion polymerization, or suspension using a radical initiator as a catalyst. It can be produced by polymerization. If it is desired to remove low molecular weight fractions, solvent purification may be performed by a conventional method. This copolymer of vinyl pyrrolidone and methyl acrylate or methyl methacrylate is soluble in, for example, ketone solvents such as acetone and methyl ethyl ketone. To mix a copolymer of vinyl pyrrolidone and methyl acrylate or methyl methacrylate with iodine, for example, dissolve this copolymer in the above-mentioned solvent, add a solution of iodine dropwise, and mix.
For example, by adding a poor solvent such as water, the desired composition can be obtained as a precipitate. The resulting composition has sterilizing properties, is useful for recording emergency surgical instruments and artificial organs, and has excellent physical properties. The present invention will be explained in more detail below with reference to production examples and application examples, but the present invention is not limited by the following examples unless it exceeds the gist thereof. Production Example 1 50 g of vinyl pyrrolidone (monomer) and 50 g of methyl acrylate (monomer) were dissolved in 500 ml of acetone, 1 g of polymerization initiator (azobisisobutyronitrile) was dissolved in 10 ml of acetone, and the mixture was dissolved in a nitrogen stream. Incubate at 60°C for 5 hours. This reaction product is dropped into n-hexane to remove the insoluble copolymer. This copolymer was colorless and transparent and soluble in chloroform, tetrahydrofuran and ethyl methyl ketone, and insoluble in water and acetone. Separately, a saturated solution of iodine in ethyl alcohol is prepared, and the above vinylpyrrolidone-methyl acrylate copolymer is immersed in this solution, and after 24 hours, it is washed with water and dried. Elemental analysis (wt%) C H N I analysis value 58.26 7.52 3.99 3.58 Production examples 2-3 Vinylpyrrolidone 25g and methyl acrylate
A bactericidal composition was obtained in the same manner as in Production Example 1, except that 75 g or 75 g of vinylpyrrolidone and 25 g of methyl acrylate were used as raw materials. Production Examples 4 to 6 Antibacterial compositions were obtained in the same manner as in Production Examples 1 to 3, except that methyl acrylate was replaced with methyl methacrylate. Application Example Sterilization Test 0.5 g of the vinylpyrrolidone-methyl acrylate copolymer-iodine composition obtained in Production Example 1 was placed in a test tube of Brain heart infusion broth medium (10 g).
In addition to ml, Staphylococcus aures (JC
-1 strain) or E. coli (JC-2 strain)
A predetermined amount of was added and cultured either statically or with shaking at 37°C for 18 hours. In addition, for those cultured with shaking, the bacteria were re-inoculated and cultured statically at 37°C for 18 hours. The results are shown in Table 1. In addition, in the table, the symbol + means that there is a bactericidal effect, and the symbol - means that there is no bactericidal effect.
【表】【table】
Claims (1)
メチルメタクリレートの共重合体およびヨウ素を
含む固体状殺菌性組成物。1. A solid fungicidal composition containing a copolymer of vinylpyrrolidone and methyl acrylate or methyl methacrylate and iodine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8269079A JPS568057A (en) | 1979-07-02 | 1979-07-02 | Sterilizing composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8269079A JPS568057A (en) | 1979-07-02 | 1979-07-02 | Sterilizing composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS568057A JPS568057A (en) | 1981-01-27 |
| JPH0121123B2 true JPH0121123B2 (en) | 1989-04-19 |
Family
ID=13781405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8269079A Granted JPS568057A (en) | 1979-07-02 | 1979-07-02 | Sterilizing composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS568057A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19843903A1 (en) * | 1998-09-24 | 2000-03-30 | Basf Ag | Solid dosage form for prolonged slow release of e.g. drugs, plant treatment agents or food or feed additives, containing copolymer of N-vinyl-lactam and methyl methacrylate as binder |
| JP5485895B2 (en) * | 2007-09-27 | 2014-05-07 | ビーエーエスエフ ソシエタス・ヨーロピア | Osmotic transfer enhancer |
-
1979
- 1979-07-02 JP JP8269079A patent/JPS568057A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS568057A (en) | 1981-01-27 |
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