JP4320755B2 - Antibacterial / antifungal agent and antibacterial / antifungal resin composition containing the same - Google Patents

Description

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【表２】

【００４８】
【発明の効果】
本発明の抗菌・抗カビ剤は幅広い抗菌・抗カビスペクトルを持ち，優れた抗菌・抗カビ性を示すと同時に，高い耐熱分解性や金属腐食性のない抗菌・抗カビ剤およびその樹脂組成物を提供できる。
この効果により，木材，紙，皮革，プラスチック，セラミック，ガラス，金属などの表面に，本発明の抗菌・抗カビ層を形成することにより，塗料，目地コーキング材，接着剤，タイル，木工品，紙製品，繊維製品，皮革製品や流し台，蛇口などの金属部品，或いはエアコン，電気掃除機，電気洗濯機，冷蔵庫などの電気製品，下駄箱や洗面台などの家具，アルミサッシなどの建築物などに使用し，抗菌・抗カビ性を付与できる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel antibacterial and antifungal agent having a specific ammonium salt structure and molecular weight and an antibacterial / antifungal resin composition containing the same.
[0002]
[Prior art]
Conventionally, inorganic and organic antibacterial agents are known as antibacterial agents. The inorganic system described above is typified by silver, and the organic system is natural products such as chitin, chitosan, hinokitiol, and quaternary ammonium salts typified by benzalkonium chloride (Patent Document 1). An organic compound having a cationic group is represented.
[0003]
On the other hand, as an antifungal agent effective against mold which is a problem in hot and humid climatic conditions in Japan, for example, dialkyldimethylammonium salts having a carbon chain length of 10 to 14 (Patent Document 2) and 2- An antifungal agent effective against a wide range of molds by a combination of (4-thiazolyl) -benzimidazole and a long-chain alkyldimethylbenzylammonium salt is disclosed (Patent Document 3).
[0004]
Such antibacterial and antifungal agents are marketed as various antibacterial or antifungal products that are filled or applied in thermoplastic resins. The thermoplastic resins mentioned above are, for example, polyethylene, polypropylene, polyvinylidene chloride, nylon, polyethylene terephthalate, etc., and are excellent in physical and chemical properties. Therefore, fibers, plastics, films, sheets, adhesives Etc. are used.
[0005]
However, although conventional antibacterial agents are effective against bacteria, they do not show sufficient effects against fungi, and antifungal agents are also effective against fungi but are effective against bacteria. There is a drawback that it does not show sufficient efficacy.
[0006]
In addition, conventional antibacterial agents and antifungal agents cause thermal decomposition when the above-mentioned thermoplastic resin is heat-kneaded and molded with other additives together with other additives, resulting in problems such as reduced effectiveness and coloring. ing.
[0007]
In addition, the above-mentioned anti-fungal agents cannot be used for electrical products having a metal part because the metal is corroded by chloride ions of ammonium salt.
[Patent Document 1]
JP-A-10-95773 [Patent Document 2]
JP-A-11-286405 [Patent Document 3]
Japanese Examined Patent Publication No. 62-3804 [0008]
[Problems to be solved by the invention]
The present invention is intended to solve the above-mentioned problems of the prior art, has both antibacterial and antifungal properties, improves heat resistance so as not to cause thermal decomposition even under high temperature conditions, and further, metal An object is to provide an antibacterial / antifungal agent having no corrosiveness and an antibacterial / antifungal resin composition containing the same.
[0009]
[Means for Solving the Problems]
The present invention is characterized in that an ammonium salt structure comprising an ammonium cation and a fluorine atom-containing counter anion is contained in the molecule, and the molecular weight of the ammonium cation moiety is in the range of 60 to 250 per ammonium nitrogen atom. An antibacterial / antifungal agent, an antibacterial / antifungal resin composition containing the same, and a salt structure comprising three or more ammonium cations and a fluorine atom-containing counter anion in the molecule The problems are solved by an antibacterial / antifungal agent and an antibacterial / antifungal resin composition containing the same.
[0010]
The present invention will be described in more detail. The ammonium salt structure comprising the ammonium cation of the present invention and a fluorine atom-containing counter anion is contained in the molecule, and the molecular weight of the ammonium cation moiety is in the range of 60 to 250 per ammonium nitrogen atom.
[0011]
Preferably, the molecular weight is in the range of 60-200. Particularly preferably, the molecular weight is in the range of 60 to 150.
[0012]
When the molecular weight of the ammonium cation moiety is less than 60, antibacterial or antifungal properties are exhibited, but poor water resistance and long-term stability, and when the molecular weight is greater than 250, antibacterial and antifungal properties are exhibited. The effect is low.
[0013]
The ammonium salt structure comprising an ammonium cation and a fluorine atom-containing counter anion in the present invention is a salt structure comprising an aliphatic, alicyclic, or aromatic ammonium cation and a fluorine atom-containing counter anion. Examples thereof include a salt structure composed of at least one ammonium cation selected from the following ammonium cation group and at least one anion selected from the following anion group.
[0014]
(Ammonium cation group) pyrrolium cation, pyridinium cation, imidazolium cation, pyrazolium cation, benzimidazolium cation, indolium cation, carbazolium cation, quinolinium cation, pyrrolidinium cation, piperidinium cation, Piperazinium cation, alkylammonium cation (including those substituted with a hydrocarbon group having 1 to 10 carbon atoms, hydroxyalkyl, alkoxyalkyl)
Any of them includes N and / or a ring having a hydrocarbon group having 1 to 10 carbon atoms, a hydroxyalkyl group, or an alkoxyalkyl group.
[0015]
(Anion group) BF ₄ , PF ₆ , C _n F _{2n + 1} CO ₂ (where n is an integer of 1 to 4),
C _n F _{2n + 1} SO ₃ (where n is an integer of 1 to 4), (FSO ₂ ) ₂ N,
(CF ₃ SO ₂ ) ₂ N, (C ₂ F ₅ SO ₂ ) ₂ N, (CF ₃ SO ₂ ) ₃ C,
_{CF 3 SO 2 -N-COCF 3} , R-SO 2 -N-SO 2 CF 3 (R is an aliphatic group),
_{ArSO 2 -N-SO 2 CF 3} (Ar is an aromatic group)
[0016]
Particularly preferred anionic species include bis {(trifluoromethyl) sulfonyl} amide anion, 2,2,2-trifluoro-N- (trifluoromethylsulfonyl) acetamide anion, bis {(pentafluoroethyl) sulfonyl} amide anion, Bis {(fluoro) sulfonyl} amide anion, tetrafluoroborate anion, trifluoromethanesulfonate anion, and the like.
[0017]
The above ammonium cations are superior in heat resistance compared to other ammonium cations. In addition, benzalkonium chloride, a quaternary ammonium salt that is a conventional antibacterial agent, is decomposed at a slightly low temperature, whereas the antibacterial / antifungal agent in the present invention has a high decomposition temperature of 250 ° C. or higher. Yes. Therefore, antibacterial and antifungal properties can be imparted without causing thermal decomposition during the thermoplastic resin heat kneading or resin molding.
[0018]
An ammonium salt structure comprising the ammonium cation of the present invention and a fluorine atom-containing counter anion is contained in the molecule, and the molecular weight of the ammonium cation moiety is in the range of 60 to 250 per ammonium nitrogen atom. Antibacterial and antifungal agents can be easily prepared by an ion exchange reaction between a normal ammonium halide and an acid or counter salt containing a counter ion.
[0019]
One of the preferred embodiments of the present invention comprises a salt structure composed of an ammonium cation and a fluorine atom-containing counter anion and three or more salt structures in one molecule obtained by polymerizing a monomer containing a polymerizable functional group. A compound.
[0020]
Examples of the above-mentioned polymerizable functional groups include carbon-carbon unsaturated groups such as vinyl group, acrylic group, methacryl group and allyl group, cyclic alkoxide groups such as epoxy group and oxetane group, isocyanate group, hydroxyl group and carboxyl group. it can.
[0021]
Particularly preferred ammonium cation species include 1-ethyl-3-vinylimidazolium cation, 1-vinyl-3-alkylimidazolium cation, 4-vinyl-1-alkylpyridinium cation, 1-alkyl-3-allylimidazolium cation. , 1- (4-vinylbenzyl) -3-alkylimidazolium cation, 1- (vinyloxyethyl) -3-alkylimidazolium cation, 1-vinylimidazolium cation, 1-allylimidazolium cation, N-allylbenz Examples include imidazolium cation, diallyl-dialkylammonium cation, (meth) acryloyloxyethyl-trimethylammonium, and (meth) acryloylaminopropyl-trimethylammonium. However, alkyl is a C1-C10 alkyl group.
[0022]
Particularly preferred anionic species include bis {(trifluoromethyl) sulfonyl} amide anion, 2,2,2-trifluoro-N- (trifluoromethylsulfonyl) acetamide anion, bis {(pentafluoroethyl) sulfonyl} amide anion, Bis {(fluoro) sulfonyl} amide anion, tetrafluoroborate anion, trifluoromethanesulfonate anion, and the like.
[0023]
Particularly preferred as a monomer having a salt structure composed of an ammonium cation and a fluorine atom-containing counter anion and a polymerizable functional group is 1-ethyl-3-vinylimidazolium {(trifluoromethyl) sulfonyl} amide, 1-vinyl. -3-alkylimidazolium bis {(trifluoromethyl) sulfonyl} amide (wherein alkyl is C1-C10), 1-vinyl-3-alkylimidazolium tetrafluoroborate (wherein alkyl is C1-C10), 4- Vinyl-1-alkylpyridinium bis {(trifluoromethyl) sulfonyl} amide (wherein alkyl is C1-C10), 4-vinyl-1-alkylpyridinium tetrafluoroborate (wherein alkyl is C1-C10), 1- ( 4-vinylbenzyl) -3-alkylimida Rium bis {(trifluoromethyl) sulfonyl} amide (wherein alkyl is C1-C10), 1- (4-vinylbenzyl) -3-alkylimidazolium tetrafluoroborate (wherein alkyl is C1-C10), 1- Glycidyl-3-alkyl-imidazolium bis {(trifluoromethyl) sulfonyl} amide (wherein alkyl is C1-C10), 1-glycidyl-3-alkyl-imidazolium tetrafluoroborate (wherein alkyl is C1-C10) , N-vinylcarbazolium tetrafluoroborate, (meth) acryloyloxyethyl-trimethylammonium tetrafluoroborate, (meth) acryloyloxyethyl-trimethyl bis {(trifluoromethyl) sulfonyl} amide, etc.
[0024]
The main polymerization reaction is carried out by adding a catalyst or a curing agent that accelerates the polymerization reaction of the polymerizable functional group of the monomer and heating to 40 ° C. to 200 ° C. usually. When the polymerizable functional group is a carbon-carbon unsaturated group, the polymerization initiator includes benzoyl peroxide, dicumyl peroxide, di-t-butyl peroxide, 1,1-bis (t-butylperoxy). Peroxides such as cyclohexane and cumene hydroperoxide, azobis compounds such as 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), inorganic systems such as ammonium persulfate An initiator etc. can be mentioned.
The amount of the polymerization initiator used is usually 0.1 to 10%, preferably 1 to 5%, based on the total weight of the polymerizable monomers.
When the polymerizable functional group is an epoxy group, amines, acid anhydrides and carboxylic acids can be used as curing agents, and alkylimidazole derivatives can be used as reaction catalysts.
[0025]
Next, an antibacterial / antifungal agent characterized in that it contains an ammonium salt structure comprising the ammonium cation of the present invention and a fluorine atom-containing counter anion in the molecule, and the molecular weight of the ammonium cation is in the range of 60 to 250. The agent can be mixed with various resins.
[0026]
Examples of the above-mentioned resins include natural resins such as starch and protein cellulose, semi-synthetic resins such as acetyl cellulose, and the following synthetic resins. Synthetic resins include polyolefin resins such as polyethylene and polypropylene, vinyl resins such as polystyrene, polyvinyl chloride, polymethyl methacrylate, and polyacrylonitrile, polyester resins such as polyethylene terephthalate, polybutylene terephthalate, and polyoxybenzoate, and polycaprolactam. Polyamide resins such as polyhexamethylene adipate and poly-m-phenylene isophthalamide, polyphenylene sulfide resins, polycarbonate resins, polysulfone resins such as polysulfone and polyethersulfone, and polyetherketone resins such as polyetheretherketone , Polyimide resin, fluorine resin such as polytetrafluoroethylene, epoxy resin, polyurethane resin, pheno Le resin, can be exemplified such as unsaturated polyester resin, both available commercially. These resins can be kneaded and coated.
[0027]
The antibacterial / antifungal agent of the present invention contains 0.1 to 80% by weight, preferably 1 to 30% by weight, in the antibacterial / antifungal resin composition. If the content is less than 0.1% by weight, the antibacterial / antifungal activity of the composition becomes insufficient. Conversely, if it exceeds 80% by weight, the mechanical properties of the composition may be lowered.
[0028]
The composition of the antibacterial / antifungal agent and resin of the present invention is prepared by blending the antibacterial / antifungal agent and resin pellets or powder to a predetermined concentration with a mixer, and after mixing uniformly, heat melt kneading with an extruder. And a method of mixing in a solvent in which the antibacterial / antifungal agent and the resin are dissolved or / dispersed can be applied.
[0029]
The antibacterial / antifungal agent and the resin composition thereof according to the present invention may contain other additives as necessary, such as stabilizers (antioxidants, ultraviolet absorbers, etc.), lubricants (silica, wax, fatty acid amides, etc.), inorganic fillers. (Glass fiber titanium oxide, calcium carbide, etc.), flame retardant (bromine compound, aluminum hydroxide, etc.), dispersant (surfactant, metal soap, wax, etc.), dye, pigment etc. may be added.
[0030]
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be further described with reference to examples, but the present invention is not limited to the examples.
[0031]
The measuring method in the Example of this invention is shown.
<Antimicrobial Test I-Liquid Medium Test Method>
As a preculture, 1 platinum ear was inoculated into LB liquid medium and shake-cultured for 20 hours. [Escherichia. E. coli (hereinafter abbreviated as E. coli): 30 ° C / Staphylococcus aureus subsp. aureus (hereinafter abbreviated as Staphylococcus): 37 ° C.]
After completion of the pre-culture, 50 μl of the bacterial solution is dispensed with a sterile pipette into the liquid medium to which each sample has been added, and the main culture is performed for 20 hours (E. coli: 30 ° C./Staphylococcus: 37 ° C.). 660 nm was measured. Further, as a comparative example, a shaking culture was similarly performed in a medium without an antibacterial agent, and the absorbance was measured at 660 nm.
Each example was performed at two levels: a sample concentration of 5 μl / ml (indicated as each example No-1) and a sample concentration of 10 μl / ml (indicated as each example No-2).
The above LB liquid medium is dissolved in ion-exchanged water so that the polypeptone is 1.0%, the yeast extract is 0.5%, and the sodium chloride is 0.5%, dispensed into a 5 ml test tube, and then sterilized. .
[0032]
<Antimicrobial Test II-Plate Test Method>
As a preculture, each bacterium was inoculated with 1 platinum ear in an LB liquid medium and shake-cultured for 20 hours. (E. coli: 30 ° C./Staphylococcus: 37 ° C.)
300 μl of each sample was added to the LB plate medium and stretched across the plate. One platinum loop was inoculated into the plate medium from the bacterial solution after completion of the preculture, and stationary culture was performed for 20 hours (E. coli: 30 ° C./Staphylococcus: 37 ° C.).
From each sample, 25% by weight (indicated as Example No-1) and 50% by weight methyl ethyl ketone solution (indicated as Example No-2) were prepared and used.
As a comparative example, static culture was similarly performed in a medium without an antibacterial agent.
LB plate medium Polypeptone 1.0%, Yeast extract 0.5%, Sodium chloride 0.5%, Agar 2.0% Dissolved in ion-exchanged water, sterilized, dispensed 20ml into sterile petri dish, culture A medium was used.
[0033]
<Antimicrobial Test III-Plate-Amplification Test Method>
The film processed in each example was cut, a 4.0 cm × 4.0 cm test piece was prepared, 0.1 ml of the pre-cultured bacterial solution was inoculated on the surface, and a sterilized polyethylene film was coated thereon. The state was preserve | saved at 30 degreeC. After 24 hours, the test piece was washed out with 10 ml of SCDLP liquid medium, 1 ml of the test piece was inoculated into LB plate medium, and cultured for 20 hours (E. coli: 30 ° C./Staphylococcus: 37 ° C.).
As a comparative example, static culture was also performed in the antibacterial additive-free test piece.
Preparation of SCDLP medium Casein peptone 17%, soybean peptone 3.0%, sodium chloride 5.0%, dipotassium hydrogen phosphate 2.5%, glucose 2.5%, lecithin 1.0%, nonionic interface 7.0% of the active agent was dissolved in ion-exchanged water, adjusted to pH 6.8 to 7.2, and sterilized.
[0034]
<Anti-mold test I-plate test method>
One platinum ear was inoculated into a liquid LB liquid medium similar to that used in <Antibacterial Test I-Liquid Medium Test Method> and shake-cultured for 70 hours [Aspergillus niger (hereinafter referred to as “Aspergillus niger”) , Aspergillus), Penicillium funiculosum (hereinafter abbreviated as Penicillium), Gliocladium virens (hereinafter abbreviated as Gliocladium), and Chaetomium globosum (hereinafter abbreviated as Chaetomium). 300 μl of each example sample was added to the same LB plate medium as in <Antimicrobial Test II-Plate Test Method>, and was stretched to one side of the LB plate medium. One platinum loop was inoculated from the bacterial solution after the completion of the preculture, and stationary culture was performed at 30 ° C. for 70 hours.
From each sample, 25% by weight (indicated as Example No-1) and 50% by weight methyl ethyl ketone solution (indicated as Example No-2) were prepared and used.
As a comparative example, static culture was similarly performed in a medium without an antifungal agent.
[0035]
<Anti-mold test II-plate-amplification test method>
The film processed in each example was cut, inoculated with 0.1 ml of the bacterial solution after completion of the pre-culture, and stored at 30 ° C. while covered with a sterilized polyethylene film. After 48 hours, the test piece was washed out with 10 ml of SCDLP liquid medium, 1 ml of the test piece was inoculated into LB medium, and statically cultured at 30 ° C for 70 hours.
As a comparative example, static culture was also carried out in the same manner in the anti-fungal additive-free test piece. Antibacterial test I adjusted in Examples 1 to 10, liquid medium test, antibacterial test II (plate test), antibacterial test III (plate-amplification test method), antifungal test I (plate test method), antifungal test II ( Tables 1 and 2 show the results of the plate-amplification test method.
[0036]
[Example 1]
A synthesis example of 1-ethyl-3-methylimidazolium bis {(trifluoromethyl) sulfonyl} amide (EMI • TFSI) is shown.
Dissolve 37.0 gr (0.45 mol) of 1-methylimidazole in 200 ml of 1,1,1-trichloroethane and add dropwise 98.1 gr (0.9 mol) of bromoethane over 1 hour while stirring at room temperature. The reaction was continued at 50 ° C. for 10 hours with continued stirring. The formed precipitate was separated, washed twice with 100 ml of 1,1,1, -trichloroethane each time, dried in vacuo at 70 ° C. for 2 hours, and white crystalline 1-ethyl-3-methylimidazolium bromide (EMI -Br) 77gr (90%) was obtained.
Next, potassium bis-{(trifluoromethyl) sulfonyl} amide (KTFSI) was dissolved in 100 ml of water at 70 ° C. and stirred at 50 ° C. to obtain 19.1 gr (0.1 mol) of EMI · Br obtained above. ) In 50 ml of water was added dropwise over 10 minutes, and the reaction was further stirred for 30 minutes. The formed oil layer was separated, washed twice with 50 ml of water each time, dried in vacuum at 100 ° C. for 2 hours, and salt 1-ethyl-3-methylimidazolium bis {(trifluoromethyl) sulfonyl} at room temperature. Amide (EMI * TFSI) 33.2gr (yield 85%) was obtained.
The EMI · TFSI synthesized in this example showed excellent heat resistance when the thermal decomposition temperature measured in argon was 350 ° C. or higher.
Table 1 shows the evaluation results of the antibacterial and antifungal tests.
[0037]
[Example 2]
Instead of EMI · Br of Example 1, diallyl-dimethylammonium chloride (DAA · Cl) was used and diallyl-dimethylammonium bis {(trifluoromethyl) sulfonyl} amide (DAA · TFSI) in the same manner as in Example 1. Was synthesized.
Table 1 shows the evaluation results of the antibacterial and antifungal tests.
[0038]
[Example 3]
The reaction was carried out in the same manner as in Example 1 except that lithium trifluoromethylsulfonate (LiSO ₃ CF ₃ ) was used instead of potassium bis-{(trifluoromethyl) sulfonyl} amide (KTFSI) in Example 1. However, water was distilled off from the reaction solution after completion of the reaction under reduced pressure, 5 cc of water and 50 cc of methylene chloride were added, and the product was recovered from the methylene chloride layer to obtain 1-ethyl-3-methylimidazolium trifluoromethyl. Sulfonate (EMI Tf) was obtained.
Table 1 shows the evaluation results of the antibacterial and antifungal tests.
[0039]
[Example 4]
Instead of EMI · Br of Example 1, 1-ethyl-3-vinylimidazolium bromide (EVI · Br) was used and 1-ethyl-3-vinylimidazolium bis {(trifluoro Methyl) sulfonyl} amide (EVI.TFSI) was synthesized.
Table 1 shows the evaluation results of the antibacterial and antifungal tests.
[0040]
[Example 5]
Lithium tetrafluoroborate (LiBF ₄ ) was used instead of lithium trifluoromethylsulfonate (LiSO ₃ CF ₃ ) of Example 3, and 1-ethyl-3-methylimidazolium tetrafluoroborate (EMI BF ₄ ) was obtained.
Table 1 shows the evaluation results of the antibacterial and antifungal tests.
[0041]
[Example 6]
In place of EM · Br in Example 1, methacryloyloxyethyl-trimethylammonium chloride (MOETMA · Cl) was used, and methacryloyloxyethyl-trimethylammonium bis {(trifluoromethyl) sulfonyl} amide was obtained in the same manner as in Example 1. (MOETMA · TFSI) was synthesized.
Table 1 shows the evaluation results of the antibacterial and antifungal tests.
[0042]
[Example 7]
20 g of EVI · TFSI obtained in Example 4 and 0.4 g of benzoyl peroxide were dissolved in 100 cc of dimethylacetamide and polymerized at 120 ° C. for 30 minutes in a nitrogen atmosphere to prepare an EVI · TFSI polymer solution.
Next, this solution was applied to a corona-treated surface of a 100 μm polyester film (Toyobo 5101) and then dried at 100 ° C. for 10 minutes to prepare a coated film (coating thickness, 5 μm).
Table 2 shows the evaluation results of the antibacterial and antifungal tests.
[0043]
[Example 8]
Using MOETMA · TFSI obtained in Example 6 instead of EVI · TFSI in Example 7, the reaction was carried out in the same manner as in Example 7 to prepare a polymer solution of MOETMA · TFSI. Further, the coated film was produced in the same manner as in Example 7.
Table 2 shows the evaluation results of the antibacterial and antifungal tests.
[0044]
[Example 9]
A coating solution (solid content ratio 6: 4) was prepared by dissolving 0.5 gr of EMI · TFSI obtained in Example 1 in 2.5 gr of thermoplastic polyester resin (Toyobo Byron UR-3210 30% methyl ethyl ketone solution). This solution was applied to the surface of a 50 μm polyester film (Toray Miller T type) and then dried at room temperature for 1 minute.
Table 2 shows the evaluation results of the antibacterial and antifungal tests.
[0045]
[Example 10]
Instead of the EMI • TFSI of Example 9, the adhesive solution was prepared using EMI • BF ₄ obtained in Example 5. Further, the coated film was produced in the same manner as in Example 9.
Table 2 shows the evaluation results of the antibacterial and antifungal tests.
[0046]
[Table 1]

[0047]
[Table 2]

[0048]
【The invention's effect】
The antibacterial / antifungal agent of the present invention has a wide antibacterial / antifungal spectrum, exhibits excellent antibacterial / antifungal properties, and at the same time has no high thermal decomposition resistance and metal corrosion resistance and its resin composition Can provide.
By this effect, the antibacterial / antifungal layer of the present invention is formed on the surface of wood, paper, leather, plastic, ceramic, glass, metal, etc., so that the paint, joint caulking material, adhesive, tile, woodwork, Paper products, textile products, leather products, metal parts such as sinks, faucets, etc., or electrical products such as air conditioners, vacuum cleaners, electric washing machines, refrigerators, furniture such as shoe boxes and washbasins, buildings such as aluminum sashes, etc. Can be used for antibacterial and antifungal properties.

Claims (2)

The cationic moiety is selected from 1-ethyl-3-methylimidazolium cation, diallyl-dimethylammonium cation, 1-ethyl-3-vinylimidazolium cation, or methacryloyloxyethyl-trimethylammonium cation;
Anionic portion bis [(trifluoromethyl) sulfonyl] amide anion, a thermoplastic resin product comprising as active ingredient a compound having a trifluoromethyl sulfonate anion quaternary ammonium salt-free structure or selected from tetrafluoroborate anion, Antibacterial and antifungal agent.   A compound having a quaternary ammonium salt structure in which the cation moiety is selected from 1-ethyl-3-vinylimidazolium cation or methacryloyloxyethyl-trimethylammonium cation and the anion moiety is a bis [(trifluoromethyl) sulfonyl] amide anion Antibacterial and antifungal agents for thermoplastic resin products containing polymers as active ingredients.