JPS6339563B2 - - Google Patents
Info
- Publication number
- JPS6339563B2 JPS6339563B2 JP5890984A JP5890984A JPS6339563B2 JP S6339563 B2 JPS6339563 B2 JP S6339563B2 JP 5890984 A JP5890984 A JP 5890984A JP 5890984 A JP5890984 A JP 5890984A JP S6339563 B2 JPS6339563 B2 JP S6339563B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- polymer
- bacteria
- compound
- group
- 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
- 230000000844 anti-bacterial effect Effects 0.000 claims description 12
- -1 polymethylene group Polymers 0.000 claims description 8
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 239000003899 bactericide agent Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 19
- 241000894006 Bacteria Species 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000645 desinfectant Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 244000063299 Bacillus subtilis Species 0.000 description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 241000588915 Klebsiella aerogenes Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229940006460 bromide ion Drugs 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000000710 polymer precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、ある種の水溶性の重合体（ポリカチ
オン）を有効成分とする殺菌剤に関するものであ
る。さらに詳しくいえば、主鎖に第４級アンモニ
ウム塩構造およびハイドロキノン構造を含むポリ
カチオンを有効成分とする殺菌剤に関するもので
ある。
低分子性の第４級アンモニウム塩化合物には殺
菌作用があることが知られており、現在、殺菌、
消毒剤として利用されているが、さらに高い抗菌
作用を持つ殺菌剤の開発が望まれている。第４級
アンモニウム塩化合物の細菌に対する作用機序
は、細菌の細胞表面への静電的作用および疎水性
相互作用による吸着とそれにつづく細胞内への拡
散の結果として、細胞膜の破壊を生じ、細菌を死
滅させるという過程が考えられている。したがつ
て、より高い殺菌活性を得るには、殺菌剤につい
て最適な電荷密度、電荷間距離および疎水性が得
られるように化学構造を変化させる必要がある。
しかし、低分子性の第４級アンモニウム塩化合物
では、この様な自由な分子設計が困難であるた
め、殺菌活性の向上にはおのずから限界がある。
本発明者は、これら従来の低分子性の第４級ア
ンモニウム塩化合物を用いた抗菌剤の欠点を改良
すべく研究を重ねた結果、
一般式（）
（式中のＲはポリメチレン基あるいはキシリレ
ン基、Ｙは塩素、臭素または
The present invention relates to a disinfectant containing a certain kind of water-soluble polymer (polycation) as an active ingredient. More specifically, it relates to a disinfectant whose active ingredient is a polycation containing a quaternary ammonium salt structure and a hydroquinone structure in its main chain. Low-molecular-weight quaternary ammonium salt compounds are known to have bactericidal effects, and are currently used for bactericidal and
Although it is used as a disinfectant, there is a desire to develop a disinfectant with even higher antibacterial effects. The mechanism of action of quaternary ammonium salt compounds on bacteria is that they adsorb to the bacterial cell surface through electrostatic and hydrophobic interactions, followed by diffusion into the cell, resulting in destruction of the cell membrane and The process of killing off is considered. Therefore, to obtain higher fungicidal activity, it is necessary to change the chemical structure of the fungicide to obtain optimal charge density, intercharge distance, and hydrophobicity.
However, with low-molecular-weight quaternary ammonium salt compounds, such free molecular design is difficult, so there is a natural limit to the improvement of bactericidal activity. As a result of repeated research to improve the drawbacks of these conventional antibacterial agents using low-molecular-weight quaternary ammonium salt compounds, the present inventors found that the general formula () (R in the formula is a polymethylene group or xylylene group, Y is chlorine, bromine or
【式】X-は塩素
あるいは臭素イオン、ｎは４〜125の整数であ
る。）
で示される循環単位からなる重合体が電荷密度、
疎水性など自由に構造を変えられ、しかも低分子
性の一般式（）
で示されるモデル化合物よりも高い抗菌活性を持
つ事実を見い出し、この知見に基づいて本発明を
成すに至つた。
一般式（）で示される重合体は、分子量約
2000〜50000、分解点約210℃を有する既知の化合
物（特公昭58−34495号公報）であり、一般式
（）
で示されるハイドロキノン化合物と、一般式
（）
Ｘ−Ｒ−Ｘ …()
（式中のＲはポリメチレン基あるいはキシリレ
ン基を表わし、Ｘは塩素あるいは臭素原子を表わ
す）
で示されるハライドとの重付加反応から容易に合
成できる。
本重合体を殺菌、消毒剤として使用するには、
水または無機塩水溶液（例えば、生理食塩水）に
溶し、所定時間、細菌と接触させるだけでその効
果を示す。この性質は、本重合体を石けん、シヤ
ンプーなどの洗剤へ混入させることにより、皮
膚、髪、衣類、ガラス、プラスチツク（例えば、
食器、玩具）などの消毒、殺菌に使用できる。ま
た、重合体の特徴を生し、抗菌作用のある乳化剤
としても利用可能である。
本発明の殺菌財は、エシエリア コリ
（Escherichia coli）、アエロバクター アエロジ
エネス（Aerobacter aerogenes）、シユードモナ
ス アエルギノサ（Pseudomonas aeruginosa）
などのグラム陰性菌よりも、バチルスズブテイリ
ス（Bacillus subtilis）、スタフイロコツカス
アウレス（Staphyrococcus aureus）などのグラ
ム陽性菌に対し、抗菌活性が高いこと、一般式
（）の低分子モデル化合物に比較してより高い
抗菌活性を持つことおよび水に対し高い溶解性を
持つことから、水洗により容易に除去できること
などの特徴を持つている。
次に実施例により本発明をさらに詳細に説明す
る。
参考例 １
１，６―ジブロモヘキサン（5.067×10-3mol）
と一般式（）の化合物（5.067×10-3mol）に２
mlのジメチルスルホキシドを入れ、50〜70℃、３
時間加熱する。反応終了後、溶媒を留去し、残基
をエチルエーテルで洗浄し、重合体〔一般式
（）でＲがヘキサメチレン基、X-が臭素イオ
ン，ｎが４〜20〕を得た。この重合体は、軟化点
が約200℃、還元粘度が0.249（ポリマー濃度＝
0.233ｇ／dl、H2O）であつた。
参考例 ２
パラ―キシリレンジクロリド1.7511ｇと2.2440
ｇの一般式（）の化合物に10mlのジメチルスル
ホキシドを入れ、50℃、２時間反応させる。反応
終了後、メタノールを加え、析出しているポリマ
ーを溶し、ベンゼン中へ再沈殿させることにより
重合体〔一般式（）でＲがパラ―キシリレン
基、X-が塩素イオン，ｎが10〜125〕を定量的に
得た。この重合物は、軟化点210℃、還元粘度が
2.93（ポリマー濃度＝0.306ｇ／dl，H2O）であつ
た。
実施例 １
寒天培地に所定の濃度（1ppm〜1000ppm）の
参考例１で得られた重合体と試供菌としてバチル
ス ズブチイリス（Bacillus subtilis）あるいは
スタフイロコツカス アウレウス
（Staphylococus aureus）を入れ、37℃で48時間
培養し、コロニーの発生を目で確認する方法によ
り、重合体の抗菌活性を評価した。20ppm以上の
参考例１の重合体の存在は、上記の菌の生育を完
全に防止できた。他の菌、エシエリア コリ
（Escherichia coli）、アエロバクター アエロジ
エネス（Aerobacter aerogenes）、シユードモナ
ス アエルギノサ（Pseudomonas aeruginosa）
に対し、それぞれ、100ppm，100ppm，330ppm
以上の濃度でその生育を完全に防止できた。
実施例 ２
実施例１と同様の方法を用い、参考例２から得
られた重合体の抗菌活性を調べた結果、この重合
体は、バチルス ズブチルス（Bacillus
subtilis）、スタフイロコツカス アウレウス
（Staphylococcus aureus）、バチルス ズブテイ
リス（Bacillius subtilis）、エシエリア コリ
（Escherichia coli）、アエロバクター アエロジ
エネス（Aerobacter aerogenes）、シユードモナ
ス アエルギノサ（Pseudomonas aeruginosa）、
に対し、それぞれ、66ppm、10ppm、100ppm、
100ppm、330ppm以上の濃度でその生育を完全に
防止できた。
実施例 ３
一般式（）の低分子モデルと参考例１および
２から得られた重合体との抗菌活性を比較するた
めに、滅菌水中にこれら化合物と試供菌（この場
合は、Staphylococcus aureus）を入れ、１時間
接触後の生存菌数を求めた。1ppm濃度の参考例
１および２から得られた重合体は、生存菌数がゼ
ロであるのに対し、一般式（）の低分子性の第
４級アンモニウム塩化合物は、初期菌数の0.1％
の菌の生存が見られた。また、同様の条件下で、
一般式（）の化合物を用いて生存菌数を完全に
ゼロにするには、5ppmの濃度を必要とした。[Formula] X - is a chlorine or bromide ion, and n is an integer from 4 to 125. ) The polymer consisting of circulating units has a charge density,
General formula () whose structure can be freely changed such as hydrophobicity and is low molecular weight. The present inventors have discovered the fact that the compound has higher antibacterial activity than the model compound shown in , and based on this knowledge, the present invention has been completed. The polymer represented by the general formula () has a molecular weight of approximately
2,000 to 50,000 and a decomposition point of approximately 210°C (Japanese Patent Publication No. 58-34495), and has the general formula () Polyaddition between a hydroquinone compound represented by the following and a halide represented by the general formula () It can be easily synthesized by reaction. To use this polymer as a sterilizing and disinfecting agent,
It exhibits its effects simply by dissolving it in water or an aqueous inorganic salt solution (eg, physiological saline) and contacting it with bacteria for a predetermined period of time. This property can be applied to skin, hair, clothing, glass, plastics (e.g., by mixing this polymer into detergents such as soap and shampoo).
It can be used to disinfect and sterilize things (tableware, toys), etc. It can also be used as an emulsifier that exhibits the characteristics of polymers and has antibacterial effects. The fungicidal property of the present invention can be applied to Escherichia coli, Aerobacter aerogenes, Pseudomonas aeruginosa.
Gram-negative bacteria such as Bacillus subtilis, Staphylococcus
It has high antibacterial activity against Gram-positive bacteria such as Staphyrococcus aureus, has higher antibacterial activity than the low-molecular-weight model compound of general formula (), and has high solubility in water. It has the characteristics that it can be easily removed by washing with water. Next, the present invention will be explained in more detail with reference to Examples. Reference example 1 1,6-dibromohexane (5.067×10 -3 mol)
and 2 to the compound of general formula () (5.067×10 -3 mol)
Add ml of dimethyl sulfoxide and heat at 50-70℃ for 3
Heat for an hour. After the reaction was completed, the solvent was distilled off and the residue was washed with ethyl ether to obtain a polymer [in the general formula (), R is a hexamethylene group, X - is a bromide ion, and n is 4 to 20]. This polymer has a softening point of approximately 200℃ and a reduced viscosity of 0.249 (polymer concentration =
0.233 g/dl, H 2 O). Reference example 2 Para-xylylene dichloride 1.7511g and 2.2440
Add 10 ml of dimethyl sulfoxide to the compound of general formula () in g, and react at 50°C for 2 hours. After the reaction is complete, methanol is added to dissolve the precipitated polymer, and reprecipitation is carried out in benzene to form a polymer [in the general formula (), R is a para-xylylene group, X - is a chlorine ion, and n is 10~ 125] was obtained quantitatively. This polymer has a softening point of 210℃ and a reduced viscosity of
2.93 (polymer concentration = 0.306 g/dl, H 2 O). Example 1 The polymer obtained in Reference Example 1 at a predetermined concentration (1 ppm to 1000 ppm) and Bacillus subtilis or Staphylococcus aureus as a sample bacteria were added to an agar medium and incubated at 37°C. The antibacterial activity of the polymer was evaluated by culturing for 48 hours and visually confirming the development of colonies. The presence of the polymer of Reference Example 1 at 20 ppm or more was able to completely prevent the growth of the above bacteria. Other bacteria, Escherichia coli, Aerobacter aerogenes, Pseudomonas aeruginosa
100ppm, 100ppm, 330ppm respectively
At the above concentration, its growth could be completely prevented. Example 2 As a result of examining the antibacterial activity of the polymer obtained from Reference Example 2 using the same method as Example 1, it was found that this polymer
subtilis), Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Aerobacter aerogenes, Pseudomonas aeruginosa,
66ppm, 10ppm, 100ppm, respectively.
Its growth could be completely prevented at concentrations of 100ppm and 330ppm or higher. Example 3 In order to compare the antibacterial activity of the low molecular model of general formula () and the polymers obtained from Reference Examples 1 and 2, these compounds and a sample bacteria (in this case, Staphylococcus aureus) were added to sterile water. The number of viable bacteria was determined after 1 hour of contact. The polymers obtained from Reference Examples 1 and 2 at a concentration of 1 ppm had zero viable bacteria, whereas the low molecular weight quaternary ammonium salt compound of general formula () had a viable bacterial count of 0.1% of the initial bacterial count.
Survival of bacteria was observed. Also, under similar conditions,
Using the compound of general formula (), a concentration of 5 ppm was required to completely reduce the number of viable bacteria to zero.
Claims (1)
ン基、Ｙは塩素、臭素または
【式】X-は塩素 あるいは臭素イオン、ｎは４〜125の整数であ
る。） で示される循環単位からなるポリカチオンを有効
成分とする殺菌剤。 ２ 一般式中のＲがヘキサメチレン基である特許
請求の範囲第１項記載の殺菌剤。 ３ 一般式中のＲがパラ―キシリレン基である特
許請求の範囲第１項記載の殺菌剤。[Claims] 1. General formula (In the formula, R is a polymethylene group or xylylene group, Y is chlorine or bromine, or [Formula] A bactericide as an active ingredient. 2. The fungicide according to claim 1, wherein R in the general formula is a hexamethylene group. 3. The fungicide according to claim 1, wherein R in the general formula is a para-xylylene group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5890984A JPS60202802A (en) | 1984-03-26 | 1984-03-26 | Fungicide comprising polycation having hydroquinone structure as active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5890984A JPS60202802A (en) | 1984-03-26 | 1984-03-26 | Fungicide comprising polycation having hydroquinone structure as active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60202802A JPS60202802A (en) | 1985-10-14 |
| JPS6339563B2 true JPS6339563B2 (en) | 1988-08-05 |
Family
ID=13097937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5890984A Granted JPS60202802A (en) | 1984-03-26 | 1984-03-26 | Fungicide comprising polycation having hydroquinone structure as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60202802A (en) |
-
1984
- 1984-03-26 JP JP5890984A patent/JPS60202802A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60202802A (en) | 1985-10-14 |
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