KR20240042929A - Anti-bacterial compound - Google Patents

Abstract

The antibacterial compound according to an exemplary embodiment of the present application is represented by Formula 1, and the antibacterial compound can improve the heat resistance of the antibacterial compound by configuring a specific anion other than halogen as an anion of a quaternary ammonium compound.

Description

Antibacterial compound {ANTI-BACTERIAL COMPOUND}

This application relates to antibacterial compounds.

Recently, high antibacterial properties are being required for various products such as household goods and hygiene products.

Depending on the material of the product requiring antibacterial properties or the final state of use, the degree of antibacterial properties required and the requirements for materials to provide antibacterial properties are different. For example, depending on the amount of antibacterial material applied to the product or the material used together, the nature of the material for imparting antibacterial properties or the degree of antibacterial property are different.

However, when introducing antibacterial agents that inhibit bacterial growth into the resin, select antibacterial ingredients that exhibit excellent bacterial growth inhibition properties, are harmless to the human body, are economical, and do not deteriorate the basic properties of the polymer resin. Therefore, it was not that easy to introduce.

Accordingly, there is a need to develop antibacterial materials suitable for application to various products.

Republic of Korea Patent Publication No. 10-0752150

This application seeks to provide an antibacterial compound.

An exemplary embodiment of the present application provides an antibacterial compound represented by the following formula (1).

[Formula 1]

In Formula 1,

At least one of R1 to R3 is an alkyl group having 4 to 16 carbon atoms, and the others are each independently an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxy group,

R4 is an alkyl group having 1 to 6 carbon atoms,

X ^-is a borate -based anion, sulfonate -based anion, sulfate -based anion, salicilate anion, male -based anion, phosphate -based anion, tartrate -based anion, vanillate -based anion , or an acetate-based anion.

In addition, another embodiment of the present application provides a product containing the antibacterial compound or manufactured therefrom.

The antibacterial compound according to an exemplary embodiment of the present application can improve the heat resistance of the antibacterial compound by configuring a specific anion other than halogen as an anion of a quaternary ammonium compound.

In addition, the antibacterial compound according to an exemplary embodiment of the present application has excellent heat resistance and has the characteristic of maintaining antibacterial activity even after a high temperature process.

Figure 1 is a diagram showing the ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of antibacterial compound 3 prepared in Example 1 as an exemplary embodiment of the present invention.
Figure 2 is a diagram showing the ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of antibacterial compound 4 prepared in Example 2 as an exemplary embodiment of the present invention.
Figure 3 is a diagram showing the ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of antibacterial compound 6 prepared in Example 4 as an exemplary embodiment of the present invention.
Figure 4 is a diagram showing the ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of antibacterial compound 8 prepared in Example 6 as an exemplary embodiment of the present invention.
Figure 5 is a diagram showing the ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of antibacterial compound 14 prepared in Example 12, as an exemplary embodiment of the present invention.

Hereinafter, this specification will be described in more detail.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components unless specifically stated to the contrary.

The antibacterial mechanism of antibacterial substances varies depending on the target germ or bacteria, but antibacterial activity is possible through destruction of cell membranes by hydrophobic functional groups or cationic groups. Therefore, in order to increase the antibacterial effect, the structure is designed in such a way that hydrophobic functional groups and cations exist together. However, when the antibacterial material is decomposed due to external stimuli such as heat, and its structure changes or decomposes, the antibacterial activity of the antibacterial material decreases.

Therefore, the present application seeks to provide an antibacterial material that improves resistance to external stimuli such as high temperature and thus maintains antibacterial activity even after a high temperature process.

The antibacterial compound according to an exemplary embodiment of the present application is represented by the following formula (1).

[Formula 1]

In Formula 1,

At least one of R1 to R3 is an alkyl group having 4 to 16 carbon atoms, and the others are each independently an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxy group,

R4 is an alkyl group having 1 to 6 carbon atoms,

X ^-is a borate -based anion, sulfonate -based anion, sulfate -based anion, salicilate anion, male -based anion, phosphate -based anion, tartrate -based anion, vanillate -based anion , or an acetate-based anion.

In an exemplary embodiment of the present application, one of R1 to R3 in Formula 1 is an alkyl group having 4 to 16 carbon atoms, and the other two are alkyl groups having 1 to 12 carbon atoms substituted with a hydroxy group.

In an exemplary embodiment of the present application, one of R1 to R3 in Formula 1 is an alkyl group having 4 to 16 carbon atoms, the other is an alkyl group having 1 to 12 carbon atoms substituted with a hydroxy group, and the other is an alkyl group having 1 to 12 carbon atoms. It is an alkyl group of

In an exemplary embodiment of the present application, R1 in Formula 1 may be an alkyl group having 8 to 16 carbon atoms.

In an exemplary embodiment of the present application, R1 in Formula 1 may be a straight-chain alkyl group having 8 to 16 carbon atoms.

In an exemplary embodiment of the present application, R1 in Formula 1 may be a straight-chain alkyl group having 10 to 16 carbon atoms.

In an exemplary embodiment of the present application, R1 in Formula 1 may be a straight-chain alkyl group having 8 carbon atoms.

In an exemplary embodiment of the present application, R1 in Formula 1 may be a straight-chain alkyl group having 10 carbon atoms.

In an exemplary embodiment of the present application, R1 in Formula 1 may be a straight-chain alkyl group having 12 carbon atoms.

In an exemplary embodiment of the present application, R1 in Formula 1 may be a straight-chain alkyl group having 14 carbon atoms.

In an exemplary embodiment of the present application, R1 in Formula 1 may be a straight-chain alkyl group having 16 carbon atoms.

In an exemplary embodiment of the present application, when R1 in Formula 1 is an alkyl group having more than 16 carbon atoms, it is not preferable because the movement of the alkyl group is slowed and the size is too large, which may reduce the antibacterial activity.

In an exemplary embodiment of the present application, R2 and R3 in Formula 1 may each independently be an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxy group.

In an exemplary embodiment of the present application, R2 and R3 in Formula 1 may each independently be an alkyl group having 1 to 8 carbon atoms unsubstituted or substituted with a hydroxy group.

In an exemplary embodiment of the present application, R2 and R3 in Formula 1 may each independently be an alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with a hydroxy group.

In an exemplary embodiment of the present application, R2 and R3 of Formula 1 may each independently be a straight-chain alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with a hydroxy group.

In an exemplary embodiment of the present application, R2 and R3 in Formula 1 may each independently be a straight-chain alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with a hydroxy group.

In an exemplary embodiment of the present application, at least one of R2 and R3 of Formula 1 may be an alkyl group having 1 to 5 carbon atoms.

In an exemplary embodiment of the present application, at least one of R2 and R3 of Formula 1 may be a straight-chain alkyl group having 1 to 5 carbon atoms.

In an exemplary embodiment of the present application, at least one of R2 and R3 of Formula 1 may be a straight-chain alkyl group having 1 to 3 carbon atoms.

In an exemplary embodiment of the present application, at least one of R2 and R3 of Formula 1 may be a methyl group.

In an exemplary embodiment of the present application, any one of R2 and R3 in Formula 1 may be an alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with a hydroxy group.

In an exemplary embodiment of the present application, any one of R2 and R3 in Formula 1 may be an alkyl group having 1 to 5 carbon atoms substituted with a hydroxy group.

In an exemplary embodiment of the present application, either R2 and R3 of Formula 1 may be an alkyl group having 1 to 5 carbon atoms.

In an exemplary embodiment of the present application, R2 in Formula 1 may be an alkyl group having 1 to 12 carbon atoms.

In an exemplary embodiment of the present application, R3 in Formula 1 may be an alkyl group having 1 to 12 carbon atoms that is unsubstituted or substituted with a hydroxy group.

In an exemplary embodiment of the present application, R4 in Formula 1 may be a straight-chain alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present application, R4 in Formula 1 may be a straight-chain alkyl group having 1 to 4 carbon atoms.

In an exemplary embodiment of the present application, R4 in Formula 1 may be a methyl group.

In an exemplary embodiment of the present application, the antibacterial compound may be any one of the following compounds.

In the above compounds, X ^- is as defined in Formula 1.

In ^an exemplary embodiment of the present application, Anion, hydroxyphenylsulfonate anion, methylsulfate anion, salicylate anion, maleate anion, phosphate anion, hexafluorophosphate anion, tart It may be a tartrate anion, a vanillate anion, a syringate anion, a thiocyanate anion, or a trifluoroacetate anion.

^In addition, in order to further improve the heat resistance properties of the antibacterial compound, More preferably, it is a fluorophosphate (hexafluorophosphate) anion.

In an exemplary embodiment of the present application, most of X ^- in Formula 1 is an anion having a lower basicity than a conventional halogen anion. When the basicity decreases, charge transfer from anions to cations decreases and binding energy increases, thereby improving the heat resistance of the antibacterial compound.

In an exemplary embodiment of the present application, the thermal decomposition temperature of the antibacterial compound may be 170°C or higher, 190°C or higher, and may be 200°C or higher. The upper limit of the thermal decomposition temperature of the antibacterial compound is not particularly limited, but may be 350°C or lower and 340°C or lower. If the thermal decomposition temperature of the antibacterial compound is less than 170°C, it is undesirable because the antibacterial compound may be decomposed during drying and processing and the antibacterial properties may not be maintained.

The thermal decomposition temperature can be measured using TGA (Thermogravimetric Analyzer, TA Instrument, DISCOVERY TGA 550 W/MFC & AUTO). More specifically, in the present application, under temperature conditions where the temperature is increased from 50°C to 600°C at a rate of 10°C/min, the first temperature decrease section of the mass loss curve was set as the pyrolysis temperature.

In an exemplary embodiment of the present application, the antibacterial compound may have a bacterial growth inhibition rate of 80% or more against at least one strain of Gram-positive bacteria, Gram-negative bacteria, and mold bacteria, as measured by Method 1 below.

[Method 1]

After adding 0.02 g of the antibacterial compound to 20 mL of Nutrient broth culture medium inoculated with 3,000 CFU/mL of the strain, the culture solution of the experimental group was cultured in a shaking incubator at a temperature of 37°C for 24 hours and subjected to UV/Vis spectroscopy. Measure the absorbance at a wavelength of 600 nm using a spectrophotometer,

The control culture solution was cultured for 24 hours at a temperature of 37°C without adding the antibacterial compound to 20 mL of Nutrient broth culture medium inoculated with 3,000 CFU/mL of the strain, and the absorbance at 600 nm was measured using a UV/Vis spectrophotometer. Measure and

Calculate the bacterial growth inhibition rate (%) based on the absorbance of the experimental group and the absorbance of the control group according to Equation 1 below,

[Equation 1]

Bacterial growth inhibition rate (%) = (1 - A _s /A ₀ ) × 100

In Equation 1 above,

A _s is the absorbance of the culture solution of the experimental group, and A ₀ is the absorbance of the culture solution of the control group.

In an exemplary embodiment of the present application, the antibacterial compound may have a bacterial growth inhibition rate of 80% or more, and 85% or more, as measured by Method 1 for at least one strain of Gram-positive bacteria, Gram-negative bacteria, and mold bacteria. and may be more than 90%. The higher the bacterial growth inhibition rate, the better the antibacterial activity. The upper limit is not limited, but may be, for example, 100% or less.

In an exemplary embodiment of the present application, the Gram-positive bacteria are a general term for bacteria that stain purple when stained with Gram staining. The cell walls of Gram-positive bacteria are composed of several layers of peptidoglycan, so basic dyes such as crystal violet are used. Even if treated with ethanol after dyeing, the color remains purple without discoloration.

In an exemplary embodiment of the present application, the Gram-positive bacteria include Enterococcus faecalis, Staphylococcus aureus , Streptococcus pneumoniae , Streptococcus pyogene , and Enterococcus faecium. ) and Lactobacillus lactis .

In an exemplary embodiment of the present application, the Gram-negative bacteria are a general term for bacteria that stain red when stained with Gram staining. Instead of having a cell wall with a relatively small amount of peptidoglycan compared to Gram-positive bacteria, the Gram-negative bacteria have lipopolysaccharide. , has an outer membrane composed of lipoproteins and/or other complex polymers.

In an exemplary embodiment of the present application, the Gram-negative bacteria include Proteus mirabilis, Escherichia coli , Salmonella typhi , Pseudomonas aeruginosa , Vibrio cholerae , and Enterobacter. It may be any one selected from Enterobacter cloacae .

In an exemplary embodiment of the present application, the fungus may be Candida albicans or the like, but is not limited thereto.

Since the Gram-positive bacteria, Gram-negative bacteria, and mold strains can not only cause various diseases upon contact, but also cause secondary infections, a single antibacterial compound is used to exhibit antibacterial properties against all of the Gram-positive bacteria, Gram-negative bacteria, and mold. It is desirable.

Another embodiment of the present application provides a product containing or manufactured from the antibacterial compound. The product is not particularly limited as long as it requires antibacterial properties. According to one example, the product may be used in the form of a copolymer such as a copolymer with a (meth)acrylic resin, a copolymer with polyvinyl chloride, a copolymer with polylactic acid (PLA), and a copolymer with urethane. Alternatively, it may be a product containing at least one of the above copolymers, such as sanitary products, antibacterial films, diapers, etc. The copolymer is preferably an acrylate- or methacrylate-based copolymer. As a copolymerization method, a known copolymerization method may be applied.

Hereinafter, in order to explain the present application in detail, examples will be given in detail. However, the embodiments according to the present application may be modified into various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more completely explain the present application to those with average knowledge in the art.

<Example>

<Comparative Example 1> Preparation of antibacterial compound 1

After adding 130 ml of ethanol, 0.131 mol of methyldiethanolamine, and 0.144 mol of chlorodecane to a 250 ml flask, the reaction was carried out by stirring for 24 hours using a magnetic bar at 65°C. After 24 hours, the reaction solution was precipitated by placing it in 800 ml of diethyl ether solution, then the reaction product was filtered using a vacuum filter, and the remaining diethyl ether was completely removed in a vacuum oven to produce the final composite, as shown in Table 1 below. Antibacterial compound 1 was obtained.

<Comparative Example 2> Preparation of antibacterial compound 2

Antibacterial compound 2 of Table 1 below was obtained by manufacturing in the same manner as Comparative Example 1, except that bromododecane was used instead of chlorodecane in the manufacturing method of Comparative Example 1.

<Example 1> Preparation of antibacterial compound 3

Antibacterial compound 2 was prepared in the same manner as in Comparative Example 2.

1 g of the prepared antibacterial compound 2 was dissolved in 10 g of water. The aqueous solution was added dropwise to a mixed solution of 1 g of sodium tetrafluoroborate and 10 g of water and stirred for 8 hours. Ethyl acetate was added to the mixed solution, and the organic solvent was extracted in a phase-separated state. After concentrating the extracted solvent, MgSO ₄ was added to remove the remaining water. After re-concentrating the filtered organic solvent and drying it in a vacuum oven for 24 hours, the final composite, antibacterial compound 3 in Table 1 below, was prepared.

The ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of the prepared antibacterial compound 3 is shown in Figure 1 below.

<Example 2> Preparation of antibacterial compound 4

Antibacterial compound 4 of Table 1 below was prepared in the same manner as in Example 1, except that sodium trifluoromethanesufonate was used instead of sodium tetrafluoroborate.

The ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of the prepared antibacterial compound 4 is shown in Figure 2 below.

<Example 3> Preparation of antibacterial compound 5

In the manufacturing method of Example 1, the antibacterial compound 1 of Comparative Example 1 was used instead of the antibacterial compound 2, and sodium methanesulfonate was used instead of sodium tetrafluoroborate, and the antibacterial compounds of Table 1 below were prepared in the same manner as in Example 1. Compound 5 was prepared.

The synthesis of antibacterial compound 5 prepared above was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) similarly to antibacterial compounds 3 and 4 described above.

<Example 4> Preparation of antibacterial compound 6

Antibacterial compound 6 of Table 1 below was prepared in the same manner as in Example 1, except that sodium toluenesulfonate was used instead of sodium tetrafluoroborate in the preparation method of Example 1.

The ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of the prepared antibacterial compound 6 is shown in Figure 3 below.

<Example 5> Preparation of antibacterial compound 7

Antibacterial compound 7 of Table 1 below was prepared in the same manner as in Example 1, except that sodium methylsulfate was used instead of sodium tetrafluoroborate in the preparation method of Example 1.

The synthesis of antibacterial compound 7 prepared above was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) similarly to antibacterial compounds 3 and 4 described above.

<Example 6> Preparation of antibacterial compound 8

Antibacterial compound 8 of Table 1 below was prepared in the same manner as in Example 1, except that sodium salicylate was used instead of sodium tetrafluoroborate in the manufacturing method of Example 1.

The ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of the prepared antibacterial compound 8 is shown in Figure 4 below.

<Example 7> Preparation of antibacterial compound 9

Antibacterial compound 9 of Table 1 below was prepared in the same manner as in Example 1, except that sodium maleate was used instead of sodium tetrafluoroborate in the preparation method of Example 1.

The synthesis of the prepared antibacterial compound 9 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

<Example 8> Preparation of antibacterial compound 10

In the manufacturing method of Example 1, the antibacterial compound 1 of Comparative Example 1 was used instead of the antibacterial compound 2, and sodium phosphate was used instead of sodium tetrafluoroborate, and the antibacterial compounds of Table 1 below were prepared in the same manner as in Example 1. Compound 10 was prepared.

The synthesis of the prepared antibacterial compound 10 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

<Example 9> Preparation of antibacterial compound 11

Antibacterial compound 11-1 was obtained in the same manner as in Comparative Example 1, except that bromotetradecane was used instead of chlorodecane.

[Antibacterial compound 11-1]

The antibacterial compounds of Table 1 below were prepared in the same manner as in Example 1, except that in the preparation method of Example 1, the antibacterial compound 11-1 was used instead of the antibacterial compound 2, and sodium tartrate was used instead of sodium tetrafluoroborate. 11 was prepared.

The synthesis of the prepared antibacterial compound 11 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

<Example 10> Preparation of antibacterial compound 12

The antibacterial compounds of Table 1 below were prepared in the same manner as in Example 1, except that the antibacterial compound 1 of Comparative Example 1 was used instead of the antibacterial compound 2 in the manufacturing method of Example 1, and sodium vanillate was used instead of sodium tetrafluoroborate. Compound 12 was prepared.

The synthesis of the prepared antibacterial compound 12 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

<Example 11> Preparation of antibacterial compound 13

Antibacterial compound 13 of Table 1 below was prepared in the same manner as in Example 1, except that sodium syringate was used instead of sodium tetrafluoroborate in the preparation method of Example 1.

The synthesis of the prepared antibacterial compound 13 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

<Example 12> Preparation of antibacterial compound 14

Except that in the manufacturing method of Example 1, antibacterial compound 1 of Comparative Example 1 was used instead of antibacterial compound 2, and potassium hexafluorophosphate was used instead of sodium tetrafluoroborate, the antibacterial compounds of Table 1 below were prepared in the same manner as in Example 1. Compound 14 was prepared.

The ¹ H-NMR spectrum ((CD ₃ ) ₂ SO) of the prepared antibacterial compound 14 is shown in Figure 5 below.

<Example 13> Preparation of antibacterial compound 15

In the manufacturing method of Example 1, the antibacterial compound 1 of Comparative Example 1 was used instead of the antibacterial compound 2, and potassium thiocyanate was used instead of sodium tetrafluoroborate, and the antibacterial properties of Table 1 below were prepared in the same manner as in Example 1. Compound 15 was prepared.

The synthesis of the prepared antibacterial compound 15 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

<Example 14> Preparation of antibacterial compound 16

Except that in the preparation method of Example 1, antibacterial compound 1 of Comparative Example 1 was used instead of antibacterial compound 2, and sodium trifluoroacetate was used instead of sodium tetrafluoroborate, the antibacterial compounds of Table 1 below were prepared in the same manner as in Example 1. Compound 16 was prepared.

The synthesis of the prepared antibacterial compound 16 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

<Example 15> Preparation of antibacterial compound 17

Antibacterial compound 17 of Table 1 below was prepared in the same manner as in Example 1, except that sodium 4-hydroxybenzenesulfonate dihydrate was used instead of sodium tetrafluoroborate in the preparation method of Example 1.

The synthesis of the prepared antibacterial compound 17 was confirmed by ¹ H-NMR spectrum ((CD ₃ ) ₂ SO), similar to the antibacterial compounds 3 and 4 described above.

[Table 1]

<Experimental Example 1> Measurement of thermal decomposition temperature of antibacterial compounds

The thermal decomposition temperatures of the antibacterial compounds prepared in the above Examples and Comparative Examples were measured and shown in Table 2 below. The thermal decomposition temperature was measured using TGA (Thermogravimetric Analyzer, TA Instrument, DISCOVERY TGA 550 W/MFC & AUTO). More specifically, under temperature conditions where the temperature was increased from 50°C to 600°C at a rate of 10°C/min, the first temperature decrease section of the mass loss curve was set as the thermal decomposition temperature.

<Experimental Example 2> Measurement of bacterial growth inhibition rate of antibacterial compounds

After adding 0.02 g of the antibacterial compound prepared in the above Example or Comparative Example to 20 mL of Nutrient broth culture medium inoculated with 3,000 CFU/mL of Escherichia coli strain, the mixture was incubated for 24 hours at a temperature of 37°C in a shaking incubator. The absorbance of the culture solution of the experimental group incubated for a period of time was measured using a UV/Vis spectrophotometer at a wavelength of 600 nm,

In 20 mL of Nutrient broth culture medium inoculated with 3,000 CFU/mL of Escherichia coli strain, the control culture solution incubated for 24 hours at a temperature of 37°C without adding the antibacterial compound was cultured using a UV/Vis spectrophotometer. Measure the absorbance at a wavelength of 600 nm,

The bacterial growth inhibition rate (%) was calculated from the absorbance of the experimental group and the control group according to Equation 1 below, and the results are shown in Table 2 below.

[Equation 1]

Bacterial growth inhibition rate (%) = (1 - A _s /A ₀ ) × 100

In Equation 1 above,

A _s is the absorbance of the culture solution of the experimental group, and A ₀ is the absorbance of the culture solution of the control group.

[Table 2]

As shown in the above results, the antibacterial compound according to an exemplary embodiment of the present application can improve the heat resistance of the antibacterial compound by configuring a specific anion other than halogen as an anion of the quaternary ammonium compound.

In addition, the antibacterial compound according to an exemplary embodiment of the present application has excellent heat resistance and has the characteristic of maintaining antibacterial activity even after a high temperature process.

Claims (10)

Antibacterial compound represented by the following formula (1):
[Formula 1]

In Formula 1,
At least one of R1 to R3 is an alkyl group having 4 to 16 carbon atoms, and the others are each independently an alkyl group having 1 to 12 carbon atoms unsubstituted or substituted with a hydroxy group,
R4 is an alkyl group having 1 to 6 carbon atoms,
X ^-is a borate -based anion, sulfonate -based anion, sulfate -based anion, salicilate anion, male -based anion, phosphate -based anion, tartrate -based anion, vanillate -based anion , or an acetate-based anion. The antibacterial compound according to claim 1, wherein one of R1 to R3 is an alkyl group having 4 to 16 carbon atoms, and the other two are alkyl groups having 1 to 12 carbon atoms substituted with a hydroxy group. The antibacterial compound according to claim 1, wherein one of R1 to R3 is an alkyl group having 4 to 16 carbon atoms, the other is an alkyl group having 1 to 12 carbon atoms substituted with a hydroxy group, and the other is an alkyl group having 1 to 12 carbon atoms. . The antibacterial compound according to claim 1, wherein the antibacterial compound is any one of the following compounds:

In the above compounds, X ^- is as defined in Formula 1. The method of claim 1, ^wherein the An antibacterial compound that is an ate anion, a phosphate anion, a hexafluorophosphate anion, a tartrate anion, a vanillate anion, a syringate anion, a thiocyanate anion, or a trifluoroacetate anion. The antibacterial compound according to claim 1, wherein the thermal decomposition temperature of the antibacterial compound is 170°C or higher. The antibacterial compound according to claim 1, wherein the antibacterial compound has a bacterial growth inhibition rate of 80% or more for at least one strain of Gram-positive bacteria, Gram-negative bacteria, and mold bacteria, as measured by Method 1 below:
[Method 1]
After adding 0.02 g of the antibacterial compound to 20 mL of Nutrient broth culture medium inoculated with 3,000 CFU/mL of the strain, the culture solution of the experimental group was cultured in a shaking incubator at a temperature of 37°C for 24 hours and subjected to UV/Vis spectroscopy. Measure the absorbance at a wavelength of 600 nm using a spectrophotometer,
The control culture solution was cultured for 24 hours at a temperature of 37°C without adding the antibacterial compound to 20 mL of Nutrient broth culture medium inoculated with 3,000 CFU/mL of the strain, and the absorbance at 600 nm was measured using a UV/Vis spectrophotometer. Measure and
Calculate the bacterial growth inhibition rate (%) based on the absorbance of the experimental group and the absorbance of the control group according to Equation 1 below,
[Equation 1]
Bacterial growth inhibition rate (%) = (1 - A _s /A ₀ ) × 100
In Equation 1 above,
A _s is the absorbance of the culture solution of the experimental group, and A ₀ is the absorbance of the culture solution of the control group. The method of claim 7, wherein the Gram-positive bacteria are Enterococcus faecalis, Staphylococcus aureus , Streptococcus pneumoniae , Streptococcus pyogene , Enterococcus faecium , and Lactobacillus. An antibacterial compound selected from Lactobacillus lactis . The method of claim 7, wherein the Gram-negative bacteria are Proteus mirabilis, Escherichia coli , Salmonella typhi , Pseudomonas aeruginosa , Vibrio cholerae , and Enterobacter . cloacae ). An antibacterial compound selected from among. A product comprising or prepared from the antibacterial compound according to any one of claims 1 to 9.