Antibacterial composition

By designing quaternary ammonium cationic compounds containing both hydrophilic and hydrophobic functional groups, the problem of insufficient activity of existing antibacterial materials against a variety of bacteria has been solved, achieving highly efficient antibacterial effects against Gram-positive bacteria, Gram-negative bacteria, and fungi, while maintaining stable antibacterial properties even with uneven concentrations.

CN117355215BActive Publication Date: 2026-07-31LG CHEM LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
LG CHEM LTD
Filing Date
2022-09-28
Publication Date
2026-07-31

AI Technical Summary

Technical Problem

Existing antibacterial materials are difficult to simultaneously meet the requirements for highly efficient antibacterial activity against Gram-positive bacteria, Gram-negative bacteria, and fungi, and their antibacterial properties are easily affected by uneven concentration.

Method used

An antibacterial composition comprising a quaternary ammonium cation compound with a specific structure was developed. This compound has both hydrophilic and hydrophobic functional groups and disrupts bacterial cell structure through electrostatic adsorption and hydrophobic interactions, exhibiting highly efficient antibacterial activity.

Benefits of technology

This antimicrobial composition exhibits 80% or higher antimicrobial activity against Gram-positive bacteria, Gram-negative bacteria, and fungi, and maintains its antimicrobial properties within the predicted range even when concentrations are uneven, providing safe and excellent antimicrobial effects.

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Abstract

One embodiment of the present application relates to an antibacterial composition comprising a compound represented by Formula 1 and having an antibacterial activity of 80% or more as measured by Method 1.
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Description

Technical Field

[0001] This invention relates to antibacterial compositions.

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2021-0141414, filed on October 21, 2021, and Korean Patent Application No. 10-2022-0118143, filed on September 19, 2022, the entire contents of which are incorporated herein by reference. Background Technology

[0003] Recently, various products, such as household products and hygiene products, require high antibacterial properties.

[0004] Depending on the materials used in the product or its final use, the required degree of antimicrobial properties and the material requirements for imparting those properties will vary. For example, the properties and degree of antimicrobial properties of the material used to impart antimicrobial properties will differ depending on the intended use of the antimicrobial material in the product or the materials used in conjunction with it.

[0005] Therefore, it is necessary to develop antimicrobial materials suitable for use in various products. Summary of the Invention

[0006] Technical issues

[0007] One embodiment of the present invention provides an antimicrobial composition that is advantageous in imparting antimicrobial properties by having both hydrophilic and hydrophobic properties.

[0008] Technical solution

[0009] One embodiment of the present invention provides an antimicrobial composition comprising a compound represented by Formula 1 and having 80% or higher antimicrobial activity against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi, as measured by Method 1:

[0010] [Formula 1]

[0011]

[0012] in,

[0013] L1 and L2 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0014] A is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0015] n is an integer from 0 to 4.

[0016] R1 and R2 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and at least one of R1 and R2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0017] R3 is an alkyl group having 4 to 20 carbon atoms.

[0018] Where n is 2 or greater, two or more A's are the same or different from each other, and

[0019] [Method 1]

[0020] After placing 25 mL of broth-type medium (nutrient broth, BDDIF CO., 8 g / L) inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.015 g of the antibacterial composition was added and the mixture was suspended (vortexed). The thoroughly mixed solution was then incubated in a shaking water bath maintained at 35°C for 16 hours.

[0021] After diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer, and the measured absorbance was compared with that of the solution cultured without the addition of the antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation.

[0022] Antibacterial activity (%) = (1-A) 样品 / A 参照 )×100

[0023] A 样品 =Absorbance of the culture medium solution cultured with the addition of an antibacterial composition

[0024] A 参照 =Absorbance of the culture medium solution cultured without the addition of antimicrobial composition

[0025] Beneficial effects

[0026] Since the antimicrobial compositions according to some embodiments of the present invention simultaneously contain both hydrophilic and hydrophobic functional groups, they are advantageous for imparting antimicrobial properties. Furthermore, by controlling the antimicrobial properties within a specific range, they can provide safe and excellent antimicrobial properties.

[0027] Since the antimicrobial composition according to some embodiments of the present invention exhibits almost no variation in antimicrobial activity depending on the application, it can still exhibit antimicrobial properties within the predicted range even when concentration inconsistencies occur unintentionally when applied as a product.

[0028] Antimicrobial compositions according to some embodiments of the present invention may exhibit 80% or higher antimicrobial properties against specific bacteria. Detailed Implementation

[0029] The present invention will be described in detail below.

[0030] <Antibacterial Composition>

[0031] One embodiment of the present invention provides an antimicrobial composition comprising a compound represented by Formula 1 and having 80% or higher antimicrobial activity against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi, as measured by Method 1:

[0032] [Formula 1]

[0033]

[0034] in,

[0035] L1 and L2 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0036] A is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0037] n is an integer from 0 to 4.

[0038] R1 and R2 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and at least one of R1 and R2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0039] R3 is an alkyl group having 4 to 20 carbon atoms.

[0040] Where n is 2 or greater, two or more A's are the same or different from each other, and

[0041] [Method 1]

[0042] After placing 25 mL of broth-type medium (nutrient broth, BDDIF CO., 8 g / L) inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.015 g of the antibacterial composition was added and the mixture was suspended (vortexed). The thoroughly mixed solution was then incubated in a shaking water bath maintained at 35°C for 16 hours.

[0043] After diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer. The measured absorbance was compared with that of the solution cultured without the antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation:

[0044] Antibacterial activity (%) = (1-A) 样品 / A 参照 )×100

[0045] A 样品 =Absorbance of the culture medium solution cultured with the addition of an antibacterial composition

[0046] A 参照 =Absorbance of the culture medium solution cultured without the addition of antimicrobial composition

[0047] According to one embodiment of the invention, hydrogen can be deuterium as an isotope. 2 H) or tritium ( 3 H) and protium ( 1 The concept of H).

[0048] According to one embodiment of the present invention, A is hydrogen or methyl.

[0049] According to one embodiment of the present invention, A is entirely composed of hydrogen.

[0050] According to one embodiment of the invention, at least one of R1 and R2 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0051] According to one embodiment of the invention, at least one of R1 and R2 is an unsubstituted alkyl group having 1 to 4 carbon atoms, i.e., each is independently methyl, ethyl, propyl, or butyl.

[0052] According to one embodiment of the invention, R3 is an unsubstituted alkyl group having 4 to 20 carbon atoms.

[0053] According to one embodiment of the invention, R3 is a substituted or unsubstituted alkyl group having 4 to 16 carbon atoms.

[0054] According to one embodiment of the invention, R3 is an unsubstituted alkyl group having 4 to 16 carbon atoms.

[0055] According to one embodiment of the invention, R1 to R3 may not be simultaneously methyl or ethyl. In other words, when R1 and R2 are the same or different from each other and are independently methyl or ethyl, R3 may be an alkyl group having 4 to 16 carbon atoms.

[0056] According to one embodiment of the invention, R1 to R3 may not simultaneously be substituted or unsubstituted alkyl groups having 4 to 16 carbon atoms. In other words, when at least two groups of R1 to R3 are the same or different from each other and are each independently an alkyl group having 4 to 16 carbon atoms, the remaining group (specifically, R1 or R2) may be methyl or ethyl.

[0057] In other words, when R1 to R3 meet the above conditions, the compound (quaternary ammonium cation) represented by Formula 1 can electrostatically adsorb onto the anionic sites on the cell surface of at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi. Simultaneously, the compound can physicochemically disrupt the cell's surface layer structure through hydrophobic interactions, leading to effective killing. Therefore, the antibacterial activity measured by the aforementioned method 1 can be improved and reach a certain level or higher.

[0058] When R1 to R3 do not meet the above conditions, in particular when R1 to R3 are simultaneously methyl or ethyl, or simultaneously substituted or unsubstituted alkyl groups having 4 to 16 carbon atoms, the quaternary ammonium cations formed therefrom are insufficient to cause hydrophobic interactions until cell death, and therefore the antibacterial activity measured by the aforementioned method 1 may be reduced.

[0059] According to one embodiment of the invention, L1 and L2 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted alkylene group having 4 to 16 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0060] According to one embodiment of the invention, L1 and L2 may be the same as or different from each other, and each is independently a direct bond, or a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms.

[0061] According to one embodiment of the present invention, L1 is a direct bond.

[0062] According to one embodiment of the invention, L2 is an unsubstituted alkylene group having 1 to 4 carbon atoms.

[0063] According to one embodiment of the present invention, L2 is methylene or ethylene.

[0064] According to one embodiment of the present invention, L2 is methylene.

[0065] According to one embodiment of the present invention, the compound represented by Formula 1 above is selected from any of the following structures:

[0066]

[0067]

[0068] According to one embodiment of the present invention, the antibacterial activity of the antibacterial composition according to method 1 above can be 80% or higher, 85% or higher, 90% or higher, 93% or higher, 95% or higher, 97% or higher, 98% or higher, or 99% or higher.

[0069] According to one embodiment of the present invention, the antibacterial reduction rate (also known as antibacterial activity) can be evaluated in the same manner as in Method 1 above, except that the amount of the added antibacterial composition is changed.

[0070] For example, the antibacterial reduction rate can be evaluated in the same manner as in Method 1 above, except that 0.005g of antibacterial composition (Method 2 below), 0.01g of antibacterial composition (Method 3 below), or 0.02g of antibacterial composition (Method 4 below) can be added instead of 0.015g of antibacterial composition.

[0071] One embodiment of the present invention may include an antimicrobial composition comprising a compound represented by Formula 1 above and having 50% or more of antimicrobial activity against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi, as measured by Method 2 below:

[0072] [Method 2]

[0073] After placing 25 mL of broth-type medium (nutrient broth, BDDIFCO., 8 g / L) inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.005 g of antibacterial composition was added and the mixture was suspended (vortexed). The well-mixed solution was then incubated in a shaking water bath at 35°C for 16 hours.

[0074] In addition, after diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer, and the measured absorbance was compared with that of the solution cultured without the addition of the antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation:

[0075] Antibacterial activity (%) = (1-A) 样品 / A 参照 )×100

[0076] A 样品 =Absorbance of the culture medium solution cultured with the addition of an antibacterial composition

[0077] A 参照 =Absorbance of the culture medium solution cultured without the addition of antimicrobial composition

[0078] According to one embodiment of the present invention, the antibacterial activity of the antibacterial composition according to method 2 above can be 50% or higher, 55% or higher, or 60% or higher.

[0079] One embodiment of the present invention may include an antimicrobial composition comprising a compound represented by Formula 1 above and having 70% or higher antimicrobial activity against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi, as measured by method 3 below:

[0080] [Method 3]

[0081] After placing 25 mL of broth-type medium (nutrient broth, BDDIFCO., 8 g / L) inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.01 g of antimicrobial composition was added and the mixture was suspended (vortexed). The well-mixed solution was then incubated in a shaking water bath at 35°C for 16 hours.

[0082] In addition, after diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer, and the measured absorbance was compared with that of the solution cultured without the addition of the antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation:

[0083] Antibacterial activity (%) = (1-A) 样品 / A 参照 )×100

[0084] A 样品 =Absorbance of the culture medium solution cultured with the addition of an antibacterial composition

[0085] A 参照 =Absorbance of the culture medium solution cultured without the addition of antimicrobial composition

[0086] According to one embodiment of the present invention, the antibacterial activity of the antibacterial composition according to method 3 above can be 70% or higher, 75% or higher, or 80% or higher.

[0087] One embodiment of the present invention may include an antimicrobial composition comprising a compound represented by Formula 1 above and having 90% or higher antimicrobial activity against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi, as measured by method 4 below:

[0088] [Method 4]

[0089] After placing 25 mL of broth-type medium (nutrient broth, BD DIFCO., 8 g / L) inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.02 g of antimicrobial composition was added and the mixture was suspended (vortexed). The well-mixed solution was then incubated in a shaking water bath at 35°C for 16 hours.

[0090] In addition, after diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer, and the measured absorbance was compared with that of the solution cultured without the addition of the antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation:

[0091] Antibacterial activity (%) = (1-A) 样品 / A 参照 )×100

[0092] A 样品 =Absorbance of the culture medium solution cultured with the addition of an antibacterial composition

[0093] A 参照 =Absorbance of the culture medium solution cultured without the addition of antimicrobial composition

[0094] According to one embodiment of the present invention, the antibacterial activity of the antibacterial composition according to method 4 above can be 90% or higher, 95% or higher, or 99% or higher.

[0095] In one embodiment of the present invention, "having antibacterial properties" means that the antibacterial activity (%) is at least 50%, at least 70% or higher, preferably 80% or higher, more preferably 90% or higher, even more preferably 95% or higher, or most preferably 99% or higher.

[0096] In one embodiment of the present invention, "having antibacterial properties" means that the antibacterial activity (%) of the method 1 described above is 80% or higher, preferably 90% or higher, more preferably 95% or higher, or most preferably 99% or higher.

[0097] In one embodiment of the present invention, "having antibacterial properties" means that the antibacterial activity (%) obtained by method 2 above is 50% or higher, preferably 55% or higher, or most preferably 60% or higher.

[0098] In one embodiment of the present invention, according to one embodiment, "having antibacterial properties" means that the antibacterial composition has an antibacterial activity (%) of 70% or higher by method 3 above, preferably 75% or higher, or most preferably 80% or higher.

[0099] In one embodiment of the present invention, "having antibacterial properties" means that the antibacterial activity (%) obtained by method 4 above is 90% or higher, preferably 95% or higher, or most preferably 99% or higher.

[0100] According to one embodiment of the invention, the antimicrobial composition has 80% or more of the antimicrobial activity as measured by method 1 above against at least one strain selected from Gram-positive bacteria, Gram-negative bacteria and fungi.

[0101] In antimicrobial compositions with antimicrobial activity, Gram-positive bacteria, Gram-negative bacteria, and fungal strains can cause various diseases and secondary infections upon contact. Therefore, it is preferable to use an antimicrobial agent that exhibits antimicrobial properties against all Gram-positive bacteria, Gram-negative bacteria, and fungi.

[0102] [Method 1]

[0103] After placing 25 mL of broth-type medium (nutrient broth, BDDIF CO., 8 g / L) inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.015 g of the antibacterial composition was added and the mixture was suspended (vortexed). The thoroughly mixed solution was then incubated in a shaking water bath maintained at 35°C for 16 hours.

[0104] After diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer. The measured absorbance was compared with that of the solution cultured without the antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation:

[0105] Antibacterial activity (%) = (1-A) 样品 / A 参照 )×100

[0106] A 样品 =Absorbance of the culture medium solution cultured with the addition of an antibacterial composition

[0107] A 参照 =Absorbance of the culture medium solution cultured without the addition of antimicrobial composition

[0108] When the antimicrobial activity of the antimicrobial composition according to one embodiment of the present invention was evaluated by method 1 above, only cases where the antimicrobial activity was 90% or higher were observed. Therefore, it was determined that the antimicrobial composition according to one embodiment of the present invention has excellent antimicrobial activity.

[0109] According to one embodiment of the present invention, the Gram-positive bacteria may be selected from any of the following: Enterococcus faecalis, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenesis, Enterococcus faecium, and Lactobacillus lactis, but are not limited thereto.

[0110] Gram-negative bacteria can be selected from any of the following: Proteus mirabilis, Escherichia coli, Salmonella typhi, Pseudomonas aeruginosa, Vibrio cholerae, and Enterobacter cloacae, but are not limited thereto.

[0111] According to one embodiment of the invention, the fungus may be Candida albicans, but is not limited thereto.

[0112] <Preparation Method>

[0113] One embodiment of the present invention provides a method for preparing a compound represented by Formula 1.

[0114] According to one embodiment of the present invention, a method for preparing a compound represented by Formula 1 is provided, wherein the method comprises reacting acetonitrile, a compound represented by Formula 11, and a trialkylamine compound:

[0115] [Formula 1]

[0116] as well as

[0117] [Equation 11]

[0118]

[0119] in,

[0120] L1 and L2 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0121] A is hydrogen or an alkyl group having 1 to 3 carbon atoms.

[0122] n is an integer from 0 to 4.

[0123] R1 and R2 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and at least one of R1 and R2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0124] R3 is an alkyl group having 4 to 20 carbon atoms, and

[0125] Hal is a halogen group.

[0126] When n is 2 or greater, two or more A's are either the same or different from each other.

[0127] In this regard, L1, L2, R1 to R3, A and n can be applied to the foregoing content of the antimicrobial composition.

[0128] According to one embodiment of the invention, the trialkylamine compound is represented by NR1R2R3. In this respect, R1 to R3 are defined as in Formula 1 above.

[0129] Antibacterial resin

[0130] According to one embodiment of the present invention, the antibacterial resin may be a polymer derived from repeating units of one or more compounds represented by Formula 1 above contained in the aforementioned antibacterial composition.

[0131] According to one embodiment of the present invention, the antibacterial resin may be a homopolymer or copolymer derived from repeating units of one or more compounds represented by Formula 1 above.

[0132] According to one embodiment of the invention, in addition to repeating units derived from one or more compounds represented by Formula 1 above, the antibacterial resin may also contain repeating units derived from other compounds.

[0133] Other examples of compounds include, but are not limited to, styrene and acrylonitrile.

[0134] Copolymers can be alternating copolymers, random copolymers, block copolymers, or graft copolymers.

[0135] In one embodiment of the invention, the term "on" used to specify the position of one component (layer) relative to another component (layer) includes both the case where one component (layer) is adjacent to another component and the case where there are any other components (layers) between the two components (layers).

[0136] In one embodiment of the invention, when a component is referred to as "comprising" a constituent element, unless otherwise specifically described, this means that it may also include other constituent elements without excluding other constituent elements.

[0137] The present invention will be described in detail below with reference to embodiments thereof. However, embodiments of the invention may be modified in various other forms, and the scope of the invention should not be construed as limited to the embodiments described below. Embodiments of the invention are provided to illustrate the invention more fully to those skilled in the art.

[0138] Invention Embodiments

[0139] <Synthesis example>

[0140] The reaction scheme of the present invention is as follows.

[0141]

[0142] In the above reaction scheme, R1 and R2 are each independently an alkyl group having 1 to 4 carbon atoms, and R3 is an alkyl group having 1 to 20 carbon atoms.

[0143] Synthesis Example 1: Synthesis of Compound A

[0144]

[0145] After adding 50 mL of acetonitrile (ACN) to a two-necked round-bottom flask and replacing it with nitrogen, 20 g of 4-vinylbenzyl chloride (1.0 equivalent) and 18.6 g of N,N-diethylbutane-1-amine (1.1 equivalent) were added, and the mixture was reacted overnight with stirring at 45 °C. After drying the organic solvent under vacuum, hexane was added and the mixture was stirred for 1 hour. The resulting solid was washed with hexane and filtered to obtain compound A.

[0146] [MS-H] + =246

[0147] Synthesis Example 2: Synthesis of Compound B

[0148]

[0149] Compound B was obtained using the same method as in Synthesis Example 1, except that N-butyl-N-ethylbutane-1-amine was used instead of N,N-diethylbutane-1-amine.

[0150] [MS-H] + =274

[0151] Synthesis Example 3: Synthesis of Compound C

[0152]

[0153] Compound C was obtained using the same method as in Synthesis Example 1, except that N-methyl-N-octyloctane-1-amine was used instead of N,N-diethylbutane-1-amine.

[0154] [MS-H] + =372

[0155] Synthesis Example 4: Synthesis of Compound D

[0156]

[0157] Compound D was obtained using the same method as in Synthesis Example 1, except that N-decyl-N-methyldecane-1-amine was used instead of N,N-diethylbutane-1-amine.

[0158] [MS-H] + =428

[0159] Comparative Synthesis Example 1: Comparative Synthesis of Compound 1

[0160]

[0161] Comparative compound 1 was obtained using the same method as in Synthesis Example 1, except that triethylamine was used instead of N,N-diethylbutane-1-amine.

[0162] [MS-H] + =218

[0163] <Example>

[0164] Example 1

[0165] The antimicrobial activity of the antimicrobial composition containing compound A was measured according to Method 1 below, and is shown in Table 1. Proteus mirabilis (ATCC29906) bacteria were used in this regard.

[0166] [Method 1]

[0167] After placing 25 mL of broth-type medium (nutrient broth, BDDIFCO., 8 g / L) inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.015 g of antimicrobial composition was added and the mixture was suspended (vortexed). The well-mixed solution was then incubated in a shaking water bath at 35°C for 16 hours.

[0168] After diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance (λ = 600 nm) was measured using a UV / Vis spectrophotometer. The measured absorbance was compared with that of the solution cultured without the antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation:

[0169] Antibacterial activity (%) = (1-A) 样品 / A 参照 )×100

[0170] A 样品 =Absorbance of the culture medium solution cultured with the addition of an antibacterial composition

[0171] A 参照 =Absorbance of the culture medium solution cultured without the addition of antimicrobial composition

[0172] Examples 2 to 4 and Comparative Example 1

[0173] The antimicrobial activities were measured in the same manner as in Example 1 above, except that antimicrobial compositions containing compounds B to D and comparative compound 1 were used independently instead of the antimicrobial composition containing compound A. The results of the antimicrobial activity measurements are shown in Table 1 below.

[0174] [Table 1]

[0175]

[0176] However, the reference is a sample in which no antimicrobial composition was added. In Table 1, methods 2 to 4 are the same as method 1, except that the amount of antimicrobial composition added as described in Table 1 is different from each other.

[0177] According to Table 1, when comparing the antimicrobial activities measured according to method 4 above, all antimicrobial compositions of Examples 1 to 4 had an antimicrobial activity of 99.9%, but the antimicrobial composition of Comparative Example 1 had an antimicrobial activity of 14.3%, indicating that the antimicrobial activity of the antimicrobial composition containing Comparative Compound 1 was significantly lower than that of the antimicrobial compositions containing Compounds A to D.

Claims

1. The antimicrobial use of an antimicrobial composition against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and fungi, said antimicrobial composition comprising one or more compounds represented by Formula 1, wherein said antimicrobial composition has 80% or more of antimicrobial activity as measured by Method 1: [Formula 1] in, L1 and L2 may be the same as or different from each other, and each is independently a direct bond, an alkylene group having 1 to 4 carbon atoms, or an aryl group having 6 to 30 carbon atoms. A is hydrogen or an alkyl group having 1 to 3 carbon atoms. n is an integer from 0 to 4. R1 and R2 are identical to each other, and each is independently ethyl, propyl, or butyl; and R3 is an alkyl group having 4 to 16 carbon atoms; or Two groups in R1 to R3 are identical to each other and are each an alkyl group having 4 to 16 carbon atoms, and the remaining group is either methyl or ethyl. Where n is 2 or greater, two or more A's are the same or different from each other; and [Method 1] After placing 25 mL of broth-type medium inoculated with 3,000 CFU / mL bacteria into a 50 mL conical tube, 0.015 g of the described antibacterial composition was added and the mixture was suspended. The thoroughly mixed solution was then incubated in a shaking water bath maintained at 35°C for 16 hours. After diluting the cultured solution to 1 / 5 using 1X PBS buffer, the absorbance at 600 nm was measured using a UV / Vis spectrophotometer. The measured absorbance was compared with that of the solution cultured without the added antimicrobial composition to calculate the antimicrobial activity as the rate of inhibition reduction using the following equation: A 样品 = absorbance of the culture medium solution incubated with the addition of the antimicrobial composition A 参照 = absorbance of the culture medium solution incubated without the addition of the antimicrobial composition.

2. The antibacterial use according to claim 1, wherein the antibacterial activity is 90% or higher.

3. The antimicrobial use according to claim 1, wherein the Gram-positive bacteria is selected from any one of the following: Enterococcus faecalis, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecium, and Lactobacillus.

4. The antimicrobial use according to claim 1, wherein the Gram-negative bacteria is selected from any one of the following: Proteus mirabilis, Escherichia coli, Salmonella typhi, Pseudomonas aeruginosa, Vibrio cholerae, and Enterobacter cloacae.

5. The antibacterial use according to claim 1, wherein L1 is a direct bond.

6. The antibacterial use according to claim 1, wherein L2 is methylene.

7. The antibacterial use according to claim 1, wherein the compound represented by formula 1 above is selected from any of the following structures: 。