Antibacterial composition

Abstract

The present invention relates to an antimicrobial composition comprising a compound of formula 1, said antimicrobial composition having improved thermal stability and antimicrobial activity.

Description

[Technical field]

[0001] The present disclosure relates to antimicrobial compositions comprising compounds.

[0002] This application claims the benefit of the filing dates of Korean Patent Application No. 10-2022-0175181 filed with the Korean Intellectual Property Office on December 14, 2022, and Korean Patent Application No. 10-2023-0140150 filed with the Korean Intellectual Property Office on October 19, 2023, the entire contents of which are incorporated herein by reference. [Background technology]

[0003] In recent years, there has been a demand for high antibacterial properties in a variety of products, such as household goods and hygiene products.

[0004] The required level of antibacterial properties and the requirements for materials to impart antibacterial properties vary depending on the material of the product for which antibacterial properties are required and the final state of use. For example, the nature of the material to impart antibacterial properties and the level of antibacterial properties vary depending on the amount of antibacterial material applied to the product and the materials used in combination.

[0005] Therefore, there is a need to develop antibacterial materials that are suitable for use in a variety of products. Summary of the Invention [Problem to be solved by the invention]

[0006] One embodiment of the present invention relates to an antibacterial composition, and more specifically, an object of the present invention is to provide an antibacterial composition containing a quaternary ammonium compound of a specific structure that has hydrophilic and hydrophobic properties and is advantageous for imparting antibacterial properties.

[0007] Another object of the antibacterial composition according to one embodiment of the present invention is to ensure heat resistance by including a quaternary ammonium compound containing an anion other than a halogen as a counter ion. [Means for solving the problem]

[0008] One embodiment of the present invention provides an antibacterial composition comprising a compound represented by formula 1:

[0009] [ka]

[0010] In the above Chemical Formula 1, L1 and L2 are the same or different and each independently represent a direct bond; a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A is hydrogen or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; n is an integer from 0 to 4, Among R1 to R3, two groups are the same or different and each is independently a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and the remaining group is a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, When n is 2 or more, two or more As are the same or different, X - is a hydroxy-based anion, a carbonate-based anion, a citrate-based anion, a cyanate-based anion, a phosphate-based anion, a benzoate-based anion, a sulfonate-based anion, a borate-based anion, a salicylate-based anion, a sulfonamide-based anion, or a sulfonimide-based anion. Effect of the Invention

[0011] The antibacterial composition of the present invention contains a compound having a quaternary ammonium structure and a specific anion, which provides high heat resistance while at the same time ensuring a high level of antibacterial activity. [Brief description of the drawings]

[0012] [Figure 1] 1 is a 1H-NMR spectroscopic spectrum of a compound according to one embodiment of the present invention. [Diagram 2]1 is a 19F-NMR spectrum of a compound according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] The present invention will be described in detail below.

[0014] <Antibacterial composition> According to one embodiment of the present invention, there is provided an antibacterial composition comprising a compound represented by formula 1:

[0015] [ka]

[0016] In the above Chemical Formula 1, L1 and L2 are the same or different and each independently represent a direct bond; a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A is hydrogen or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; n is an integer from 0 to 4, Among R1 to R3, two groups are the same or different and each is independently a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and the remaining group is a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, When n is 2 or more, two or more As are the same or different, X - is a hydroxy-based anion, a carbonate-based anion, a citrate-based anion, a cyanate-based anion, a phosphate-based anion, a benzoate-based anion, a sulfonate-based anion, a borate-based anion, a salicylate-based anion, a sulfonamide-based anion, or a sulfonimide-based anion.

[0017] According to one embodiment of the present invention, the X -may be an anion selected from trifluoromethanesulfonate, p-toluenesulfonate, tetrafluoroborate, thiocyanate, hexafluorophosphate, salicylate, hydroxybenzoate, carboxyphenolate, trifluoromethylsulfonamidate, trifluoromethanesulfonimidate, bistrifluoromethylsulfonamidate, or bis(trifluoromethyl)sulfonimidate.

[0018] According to one embodiment of the present invention, L1 and L2 may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms.

[0019] According to one embodiment of the present invention, L1 may be a direct bond; a methylene group or an ethylene group.

[0020] According to one embodiment of the present invention, L1 may be a methylene group.

[0021] According to one embodiment of the invention, L1 may be a direct bond.

[0022] According to one embodiment of the present invention, L2 may be a direct bond; a methylene group; or an ethylene group.

[0023] According to one embodiment of the present invention, L2 may be a methylene group.

[0024] According to one embodiment of the invention, L2 may be a direct bond.

[0025] According to one embodiment of the invention, A may be all hydrogen.

[0026] According to one embodiment of the present invention, among R1 to R3, two groups are the same or different and each is independently a methyl group or an ethyl group, and the remaining group may be an unsubstituted alkyl group having 8 to 20 carbon atoms.

[0027] According to one embodiment of the present invention, the formula 1 may be represented by any of the following structures:

[0028] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0029] According to one embodiment of the present invention, the antibacterial composition may have a primary pyrolysis temperature of 200° C. or higher.

[0030] In the present invention, the thermal decomposition temperature can be measured using a thermogravimetric analyzer.

[0031] The first pyrolysis temperature can be defined as an extrapolated intersection point between the baseline of the initial mass and the tangent line of the maximum slope point in the initial mass loss section of a mass loss curve measured by a thermogravimetric analyzer in an N2 atmosphere.

[0032] In the present invention, when the primary thermal decomposition temperature of the antibacterial composition is higher than the primary thermal decomposition temperature of the substance before substitution, it is considered that the heat resistance is increased. However, when the processing and melting process of the polymer using the compound are taken into consideration, it is considered that the antibacterial composition has thermal stability only when the primary thermal decomposition temperature is 200°C or higher.

[0033] As long as the antibacterial composition has a primary pyrolysis temperature of 200° C. or higher, there is no particular upper limit to the temperature, and a higher temperature means better heat resistance.

[0034] As used herein, the primary thermal decomposition temperature is the temperature at which thermal decomposition occurs at the quaternary ammonium group of the compound, and the inventors have determined that the primary thermal decomposition temperature is the temperature at which thermal decomposition occurs at the anion group (i.e., X - ) and discovered that when a quaternary ammonium group is substituted with a specific anion other than a halogen anion, the thermal stability of the quaternary ammonium group increases, and as a result, the thermal decomposition temperature increases. On the other hand, secondary and subsequent thermal decompositions occur in parts other than the quaternary ammonium group, so the primary thermal decomposition experiment is used as the basis, as it is easier to compare the effects under the same conditions.

[0035] Furthermore, as described above, the higher the thermal decomposition temperature of the quaternary ammonium compound (i.e., monomer) substituted with a specific anion, the higher the resistance of the polymer containing the compound to processes in high temperature environments.

[0036] According to one embodiment of the present invention, the antibacterial composition may have a bacterial growth inhibition rate of 70% or more against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi, as measured by the following method 1.

[0037] [Method 1] 0.04 g of the antibacterial composition was added to 20 mL of nutrient broth culture solution inoculated with 3,000±300 CFU / mL of bacterial strain, and the mixture was cultured in a shaking incubator at 37° C. for 24 hours. The culture solution of the experimental group was measured for absorbance at 600 nm wavelength using a UV / Vis spectrophotometer. 20 mL of nutrient broth culture solution inoculated with 3,000±300 CFU / mL of the strain was cultured at 37° C. for 24 hours without adding the antibacterial composition, and the control culture solution was measured for absorbance at a wavelength of 600 nm using a UV / Vis spectrophotometer. The bacterial growth inhibition rate (%) of the test group was calculated from the absorbance of the test group and the absorbance of the control group according to the following Equation 1.

[0038]

number

[0039] According to one embodiment of the present invention, the bacterial growth inhibition rate of the compound by Method 1 may be 50% or more, 60% or more, 70% or more, 80% or more, or 90% or more.

[0040] In the present invention, "having antibacterial properties" means that the bacterial growth inhibition rate (%) is 50% or more, 60% or more, preferably 70% or more, and more preferably 80% or more.

[0041] In the present invention, "having antibacterial properties" means that the bacterial growth inhibition rate (%) according to the above method 1 is 70% or more, preferably 80% or more.

[0042] According to one embodiment of the present invention, the Gram-positive bacterium may be any one selected from the group consisting of Enterococcus faecalis, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecium, and Lactobacillus lactis, but is not limited thereto.

[0043] In this specification, the gram-positive bacteria is a collective term for bacteria that are stained purple by the gram staining method. The cell walls of gram-positive bacteria are composed of multiple layers of peptidoglycan, and after staining with a basic dye such as crystal violet, they retain their purple color even when treated with ethanol without fading.

[0044] The Gram-negative bacterium may be any one selected from the group consisting of Proteus mirabilis, Escherichia coli, Salmonella typhi, Pseudomonas aeruginosa, Vibrio cholerae, and Enterobacter cloacae, but is not limited thereto.

[0045] As used herein, the term "Gram-negative bacteria" refers to bacteria that stain red when stained with the Gram staining method, and have a cell wall that contains a relatively small amount of peptidoglycan compared to Gram-positive bacteria, but instead have an outer membrane made of lipopolysaccharides, lipoproteins, and / or other complex polymeric substances.

[0046] According to one embodiment of the present invention, the fungus may be, but is not limited to, Candida albicans.

[0047] Since the above Gram-positive, Gram-negative, and fungal strains can not only induce various diseases upon contact but also cause secondary infections, it is preferable to use a single antibacterial compound that exhibits antibacterial activity against all of the above Gram-positive, Gram-negative, and fungal strains.

[0048] In the present invention, when a member (layer) is said to be "located on" another member (layer), this includes not only the case where a member (layer) is in contact with the other member, but also the case where another member (layer) exists between two members (layers).

[0049] In the present invention, when a part "comprises" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified to the contrary.

[0050] In the present invention, the term "monomer" refers to a unit compound that can be converted into a polymeric compound by a polymerization reaction, i.e., a monomer, and the structure derived therefrom can be a repeating unit in a polymer or copolymer. Specifically, this means that when the compound is polymerized and bound to a polymer, all or a part of two or more substituents are removed from the structure of the compound, and a radical for binding to other units of the polymer is located in that position. In this case, the compound can be included in a state of being polymerized and bound to the polymer in any order. EXAMPLES

[0051] Hereinafter, the present invention will be described in detail with reference to examples in order to specifically explain the present invention. However, the examples of the present invention can be modified into various other forms, and the scope of the present invention is not to be construed as being limited to the examples described below. The examples of the present invention are provided to more completely explain the present invention to those having average knowledge in the art.

[0052] Synthesis example: Synthesis of a compound. <Synthesis Example 1> The reaction scheme of the present invention is as follows:

[0053] [ka]

[0054] The compound (or antibacterial monomer) having a halogen anion used in the present invention was prepared as described above. A two-necked round-bottom flask-type reactor equipped with a stirrer connected to a condenser and a stirrer was prepared. 50 g of 1-chloromethyl-4-vinyl benzene and 81.3 g of N,N-dimethyldodecyl amine were mixed with acetonitrile (150 mL) and then added to the reactor. The inside of the reactor was replaced with a nitrogen atmosphere, and the temperature was raised to 45° C. and the reaction was carried out with stirring for 24 hours or more. The solution in which the reaction was completed was dropped into hexane to precipitate and purify the reactant. The purification process was carried out two or more times, and the mixture was dried at about 80° C. for 24 hours or more to obtain compound 1. Compound 1 1 For the H-NMR spectrum, see FIG.

[0055] <Synthesis Example 2> Compound 2 was produced in the same manner as in Synthesis Example 1, except that 81.3 g of N,N-dimethyldodecylamine was replaced with 56.7 g of N,N-dimethyloctylamine. Compound 2 was produced in the same manner as Compound 1. 1 The synthesis was confirmed by 1 H-NMR spectrum.

[0056] <Synthesis Example 3> Compound 3 was produced in the same manner as in Synthesis Example 1, except that 81.3 g of N,N-dimethyldodecylamine was replaced with 69.0 g of N,N-dimethyldecylamine. Compound 3 was produced in the same manner as Compound 1. 1 The synthesis was confirmed by 1 H-NMR spectrum.

[0057] <Synthesis Example 4> Compound 4 was produced in the same manner as in Synthesis Example 1, except that 81.3 g of N,N-dimethyldodecylamine was replaced with 105.9 g of N,N-dimethylcetylamine. Compound 4 was produced in the same manner as Compound 1. 1 The synthesis was confirmed by 1 H-NMR spectrum.

[0058] <Synthesis Example 5> Compound 5 was produced in the same manner as in Synthesis Example 1, except that 81.3 g of N,N-dimethyldodecylamine was replaced with 130.6 g of N,N-dimethyl eicosanamine. Compound 5 was produced in the same manner as Compound 1. 1 The synthesis was confirmed by 1 H-NMR spectrum.

[0059] Example: Anion Substitution (Preparation of Antibacterial Composition) <Example 1> Compound 1 (1 g) prepared in Synthesis Example 1 was dissolved in 10 g of water. In another vessel, 0.94 g of sodium trifluoromethyl sulfonate was dissolved in 10 g of water, and then added dropwise to the reactor. The mixture was stirred for 8 hours or more to convert anions from halogen anions (i.e., Cl - ) Trifluoromethylsulfonate anion (CF3SO3 - ) was added to the replacement liquid, and the mixture was allowed to stand for 30 minutes or more to separate the phases. After only the upper ethyl acetate was separated from the separated mixture, magnesium sulfate (MgSO4) was added to remove the remaining water. After filtering the magnesium sulfate in the ethyl acetate solution, the ethyl acetate was removed in a vacuum oven at 40°C to obtain the antibacterial composition of Example 1. As shown in FIG. 2, 19F-NMR (Nuclear Magnetic Resonance, Bruker, Ascend (trademark pending) 500) spectroscopy confirmed that the F element of trifluoromethyl sulfonate was detected, and the anion of Compound 1 in Synthesis Example 1 was Cl. - It was confirmed that the fluorine-containing trifluoromethylsulfonic acid was substituted with trifluoromethylsulfonic acid.

[0060] <Example 2> The antibacterial composition of Example 2 was obtained in the same manner as in Example 1, except that the compound 1 (1g) in Example 1 was replaced with the compound 2 (1g) prepared in Synthesis Example 2. The antibacterial composition of Example 2 was obtained by the same method as in Example 1. 19 The anion substitution was confirmed by F-NMR spectroscopy.

[0061] <Example 3> The antibacterial composition of Example 3 was obtained in the same manner as in Example 1, except that the compound 1 (1g) in Example 1 was replaced with the compound 3 (1g) prepared in Synthesis Example 3. The antibacterial composition of Example 3 was obtained by the same method as in Example 1. 19 The anion substitution was confirmed by F-NMR spectroscopy.

[0062] <Example 4> The antibacterial composition of Example 4 was obtained in the same manner as in Example 1, except that the compound 1 (1g) in Example 1 was replaced with the compound 4 (1g) prepared in Synthesis Example 4. The antibacterial composition of Example 4 was obtained by the same method as in Example 1. 19 The anion substitution was confirmed by F-NMR spectroscopy.

[0063] <Example 5> The antibacterial composition of Example 5 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethyl sulfonate was replaced with 0.60 g of sodium tetrafluoroborate. 19From the F-NMR spectroscopy results, it was confirmed that the F element of tetrafluoroborate was detected, and it was confirmed that the anion of Compound 1 in Synthesis Example 1 was Cl - It was confirmed that the fluorine-containing tetrafluoroboric acid was replaced by tetrafluoroboric acid containing the F element.

[0064] <Example 6> The antibacterial composition of Example 6 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 0.87 g of sodium salicylate. 19 F-NMR spectrum shows Cl - From F - When the F peak was replaced with salicylate, the F peak disappeared. - It was indirectly confirmed that the anion was substituted to salicylic acid.

[0065] <Example 7> The antibacterial composition of Example 7 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 1.65 g of sodium bis(trifluoromethane)sulfonamide. 19 The anion substitution was confirmed by F-NMR spectroscopy.

[0066] <Example 8> The compound of Example 8 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 0.65 g of sodium methane sulfonate. 19 F-NMR spectrum shows Cl - From F -When the methane sulfonate salt was substituted, the F peak disappeared. - It was indirectly confirmed that the anion was substituted to methane sulfonate.

[0067] <Example 9> The antibacterial composition of Example 9 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 0.79 g of sodium benzoate. 19 F-NMR spectrum shows Cl - From F - When the substitution with benzoic acid was confirmed, the F peak disappeared. - It was indirectly confirmed that the anion was substituted from 1 to benzoate.

[0068] <Example 10> The antibacterial composition of Example 10 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 1.41 g of sodium citrate monobasic. 19 F-NMR spectrum shows Cl - From F - When the substitution with dihydrogen citrate (citrate monobasic) was confirmed, the F peak disappeared. - This indirectly confirmed that the anion was replaced by dihydrogen citrate.

[0069] <Example 11> The antibacterial composition of Example 11 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 0.74 g of sodium trifluoroacetate. 19 The anion substitution was confirmed by F-NMR spectroscopy.

[0070] <Example 12> The compound of Example 12 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 1.01 g of potassium hexafluorophosphate. 19 The anion substitution was confirmed by F-NMR spectroscopy.

[0071] <Example 13> The antibacterial composition of Example 13 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 0.53 g of potassium thiocyanate. 19 F-NMR spectrum shows Cl - From F - When the substitution with thiocyanate was confirmed, the F peak disappeared. - It was indirectly confirmed that the anion was replaced by thiocyanate.

[0072] <Example 14> The antibacterial composition of Example 14 was obtained in the same manner as in Example 1, except that 1 g of sodium trifluoromethylsulfonate was replaced with 1.06 g of sodium p-toluenesulfonate. 19 F-NMR spectrum shows Cl - From F- When p-toluenesulfonate was substituted, the F peak disappeared. - It was indirectly confirmed that the anion was substituted with p-toluenesulfonic acid.

[0073] <Comparative Example 1> As in the previous Examples, Compound 1 in Synthesis Example 1, which is a compound that does not undergo anion substitution, was selected as the compound in Comparative Example 1. According to FIG. 19 The F-NMR spectroscopy results confirmed that no F element was detected, and the anion (Cl - ) remains as it is.

[0074] Experimental example. <Experimental Example 1: Primary pyrolysis measurement experiment> In order to test the primary thermal decomposition temperatures of the antibacterial compositions of Examples 1 to 13 and Comparative Example 1, a thermogravimetric analyzer (TGA2, Mettler Toledo) was used.

[0075] In this experiment, the first thermal decomposition temperature was defined as the extrapolated intersection point between the baseline of the initial mass and the tangent line of the maximum slope point in the first mass loss section in the mass loss curve measured by a thermogravimetric analyzer in an N2 atmosphere. In the present invention, when the first thermal decomposition temperature of the antibacterial composition is higher than the first thermal decomposition temperature of the material before anion substitution, it is determined that the heat resistance is increased. The measurement results are shown in Table 1 below.

[0076] <Experimental Example 2: Bacterial growth inhibition rate (%) measurement experiment> In this experiment, the bacterial growth inhibition rate was measured by the following method 1. E. coli was used. The measurement results are shown in Table 1 below.

[0077] [Method 1] 0.04 g of the antibacterial composition was added to 20 mL of nutrient broth culture solution inoculated with 3,000±300 CFU / mL of bacterial strain, and the mixture was cultured in a shaking incubator at 37° C. for 24 hours. The culture solution of the experimental group was measured for absorbance at 600 nm wavelength using a UV / Vis spectrophotometer. 20 mL of nutrient broth culture solution inoculated with 3,000±300 CFU / mL of the strain was cultured at 37° C. for 24 hours without adding the antibacterial composition, and the control culture solution was measured for absorbance at a wavelength of 600 nm using a UV / Vis spectrophotometer. The bacterial growth inhibition rate (%) of the test group was calculated from the absorbance of the test group and the absorbance of the control group according to the following Equation 1.

[0078]

number

[0079] [Table 1]

[0080] According to the description in Table 1, Examples 1 to 14 are antibacterial compositions in which anions other than halogen are substituted, and they exhibited a bacterial growth inhibition rate of 90% or more, maintaining high antibacterial properties, and at the same time, the primary pyrolysis temperature exceeded 200° C. or more, indicating high heat resistance. In contrast, Comparative Example 1, which contained halogen anions, maintained a high level of antibacterial properties, but had a primary pyrolysis temperature below 200° C., indicating low heat resistance.

Claims

1. An antibacterial composition comprising a compound represented by formula 1: 【Chemistry 1】 In the above Chemical Formula 1, L1 and L2 are the same or different and each independently represent a direct bond; a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A is hydrogen; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; n is an integer from 0 to 4, Among R1 to R3, two groups are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and the remaining group is a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, When n is 2 or more, two or more A's are the same or different, X － is a hydroxy-based anion, a carbonate-based anion, a citrate-based anion, a cyanate-based anion, a phosphate-based anion, a benzoate-based anion, a sulfonate-based anion, a borate-based anion, a salicylate-based anion, a sulfonamide-based anion, or a sulfonimide-based anion.

2. The X － is an anion selected from trifluoromethanesulfonate, p-toluenesulfonate, tetrafluoroborate, thiocyanate, hexafluorophosphate, salicylate, hydroxybenzoate, carboxyphenolate, trifluoromethylsulfonamidate, trifluoromethanesulfonimidate, bistrifluoromethylsulfonamidate, or bis(trifluoromethyl)sulfonimidate.

3. The antimicrobial composition of claim 1 , wherein L1 is a direct bond.

4. The antimicrobial composition of claim 1 , wherein L2 is a methylene group.

5. The antimicrobial composition of claim 1 , wherein A is hydrogen.

6. The antibacterial composition according to claim 1, wherein among R1 to R3, two groups are the same or different and each independently represents a methyl group or an ethyl group, and the remaining group is an unsubstituted alkyl group having 8 to 20 carbon atoms.

7. The antimicrobial composition of claim 1, wherein the formula 1 is represented by any of the following structures: 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】

8. 2. The antimicrobial composition of claim 1, wherein the compound has a first thermal decomposition temperature of 200° C. or higher.

9. The antibacterial composition according to claim 1, wherein the compound has a bacterial growth inhibition rate of 70% or more against at least one strain of gram-positive bacteria, gram-negative bacteria, and fungi as measured by the following method 1: [Method 1] 0.04 g of the antibacterial composition was added to 20 mL of Nutrient Broth culture solution inoculated with 3,000±300 CFU / mL of the bacterial strain, and the mixture was cultured in a shaking incubator at 37° C. for 24 hours. The culture solution of the experimental group was measured for absorbance at a wavelength of 600 nm using a UV / Vis spectrophotometer. 20 mL of Nutrient broth culture solution inoculated with 3,000±300 CFU / mL of the strain was cultured at 37° C. for 24 hours without adding the antibacterial composition, and the control culture solution was measured for absorbance at a wavelength of 600 nm using a UV / Vis spectrophotometer. The bacterial growth inhibition rate (%) of the test group was calculated from the absorbance of the test group and the absorbance of the control group according to the following Equation 1. [0010]

10. The antibacterial composition according to claim 9, wherein the Gram-positive bacterium is any one selected from the group consisting of Enterococcus faecalis, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecium, and Lactobacillus lactis.

11. The antibacterial composition according to claim 9, wherein the Gram-negative bacterium is any one selected from the group consisting of Proteus mirabilis, Escherichia coli, Salmonella typhi, Pseudomonas aeruginosa, Vibrio cholerae, and Enterobacter cloacae.

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