WO2015056984A1 - Antibacterial composition and antibacterial surface treatment method using same - Google Patents

Abstract

The present application relates to an antibacterial composition and an antibacterial surface treatment method using the antibacterial composition.

Description

Antibacterial composition and surface antibacterial treatment method using the same

The present application relates to an antimicrobial composition and a surface antimicrobial treatment method using the antimicrobial composition.

Recently, with increasing interest in health, in various fields such as textiles, portable electronic devices, building materials, home appliances, filters, packaging materials, food manufacturing equipment, pharmaceutical manufacturing equipment, medical equipment, the composition having antimicrobial, so-called antibacterial Compositions are widely used. Originally, antimicrobial agents aim to create a difficult environment in which bacteria cannot grow by inhibiting the growth of bacteria rather than killing them. The antimicrobial agent contained in such an antimicrobial composition is excellent in safety, antibacterial action is maintained for a long time, and should be excellent in heat resistance.

The antimicrobial agent is largely divided into two types: organic antimicrobial agent and inorganic antimicrobial agent. Due to its characteristics, the antimicrobial agent is classified into an elution type and a contact type. Elute.

Metal materials commonly used as antibacterial agents in the market include silver (for example, silver nitrate, silver sulfadiazine, etc.). Since silver has a property of minimally expressing bacterial resistance, an antimicrobial composition containing silver or a silver compound It is used for this various use. For example, US Pat. No. 2,791,518 (Stokes et al.) Describes a method for producing antimicrobial products using silver nitrate, barium nitrate and the like. However, these metal antimicrobial agents have a problem in adhesion when coated on fibers, and may be applied to the surfaces of fibers or polymers in the form of zeolites or titanium phosphate compounds, but the adhesion characteristics thereof are limited. In addition, these raw materials are not only expensive, but are generally not stable to light and leave stains on the skin upon contact, and are consumed when used for a long time. In addition, the organic antimicrobial agent is difficult to control the dissolution rate and due to the toxicity of the eluted organic antimicrobial to the human body is limited in use and expensive. Overall, the development of antimicrobial substances is still slow, and further, methods of utilizing these antimicrobial substances in fibers or films have not been properly developed.

On the other hand, viologen-based compounds are widely used as electron transfer mediators in the development of materials such as battery electrodes and transistors because of their redox properties. By utilizing these redox properties, a compound called methylbiogen (1,1'-dimethyl-4,4'-bipyridylium) is known to be involved in plant growth and is used on a large scale as a herbicide under the trade name Paraquat [Environmental Health Perspectives, 1984, Vol. 55, pp. 37-46]. Although these biologen-based compounds showed various properties as herbicides, they have not been properly reported as antimicrobial agents for inhibiting microbial growth, and have not been reported as surface antimicrobial agents on the surface of fibers or polymers. In general, a biologen-based compound is an alkyl group, in particular, methylbiogen having a methyl group is mainly used, and a biologen-based compound having a substituent having 2 or more carbon atoms is also used, but the characteristics thereof are not significantly different. In addition, while alkylbiogen has the physical properties of redox, there is little chemical reactivity, and therefore, reaction or surface treatment using alkylbiogen is not possible.

Accordingly, the present application is to provide an antimicrobial composition and a surface antimicrobial treatment method using the antimicrobial composition.

However, the problem to be solved by the present application is not limited to the above-mentioned problem, and other problems not mentioned will be clearly understood by those skilled in the art from the following description.

A first aspect of the present application provides an antimicrobial composition comprising an alkyl-biogen derivative compound represented by the following general formula (1):

[Formula 1]

;

In formula 1, R ¹ and R ² are, each independently, is to include respective substituted C _1-10 linear or branched alkyl group by a X ¹ and X ^2, X ¹ and X ² are, each independently, -NH ₂ , -NR ³ H, -NR ³ R ⁴ , -COOH, -SO ₃ H, -SO ₂ H, and -PR ³ R ⁴ , wherein R ³ and Each R ⁴ is independently a C _1-10 alkyl group.

The second aspect of the present application provides a surface antibacterial treatment method comprising applying to the substrate the antimicrobial composition comprising the alkyl-biogen derivative compound represented by the formula (1).

According to this application, the antimicrobial composition and coating composition containing an alkyl-biogen derivative compound excellent in antibacterial performance can be manufactured. The coating composition according to the present invention can be applied to various substrates such as fiber, plastic, paper, glass, polymer film, metal film, and can be used in various fields because the coating method is simple.

In particular, according to the present invention, a combination of the redox properties of biologens and the bioactive properties of polyamines is combined in one molecule to produce a new concept of antimicrobial composition, which is very different from those of biologen and also very different from polyamine. can do. Alkyl-biogen derivative compounds according to the present invention not only show excellent antimicrobial effect but also retain activity to kill strains.

1 is a photograph showing that the growth of the strain is inhibited when the antimicrobial composition prepared according to an embodiment of the present application is treated at various concentrations.

Figure 2 is a photograph showing the antimicrobial activity when the antimicrobial composition prepared according to an embodiment of the present application to the strain at various concentrations.

Figure 3 is a graph measuring the size of the region showing the antimicrobial activity when the antimicrobial composition prepared according to an embodiment of the present application to the strain at various concentrations.

Figure 4 is a photograph showing the antimicrobial activity of the antimicrobial activity of the antimicrobial composition prepared according to an embodiment of the present application and the methyl biologen.

Figure 5a is a photograph showing the antimicrobial degree to Staphylococcus aureus of the coating composition prepared according to an embodiment of the present application.

Figure 5b is a photograph showing the antimicrobial degree against pneumococcal of the coating composition prepared according to an embodiment of the present application.

Figure 6a is a photograph showing the antimicrobial degree against Staphylococcus aureus of the coating composition prepared according to an embodiment of the present application.

Figure 6b is a photograph showing the antimicrobial degree against pneumococcal of the coating composition prepared according to an embodiment of the present application.

Figure 7a is a photograph showing the antimicrobial activity against Staphylococcus aureus of the coating composition prepared according to an embodiment of the present application.

Figure 7b is a photograph showing the antimicrobial activity against E. coli of the coating composition prepared according to an embodiment of the present application.

Hereinafter, exemplary embodiments of the present disclosure will be described in detail with reference to the accompanying drawings so that those skilled in the art may easily implement the present disclosure. As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention. In the drawings, parts irrelevant to the description are omitted for simplicity of explanation, and like reference numerals designate like parts throughout the specification.

Throughout this specification, when a portion is "connected" to another portion, this includes not only "directly connected" but also "electrically connected" with another element in between. do.

Throughout this specification, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

Throughout this specification, when a part is said to "include" a certain component, it means that it can further include other components, without excluding the other components unless specifically stated otherwise.

As used throughout this specification, the terms "about", "substantially" and the like are used at, or in the sense of, numerical values when a manufacturing and material tolerance inherent in the stated meanings is indicated, Accurate or absolute figures are used to assist in the prevention of unfair use by unscrupulous infringers.

As used throughout this specification, the term "step to" or "step of" does not mean "step for."

Throughout this specification, the term "combination (s) thereof" included in the representation of a makushi form refers to one or more mixtures or combinations selected from the group consisting of the components described in the representation of makushi form, It means to include one or more selected from the group consisting of the above components.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B."

Throughout this specification, the term "alkyl group" may include linear or branched, saturated or unsaturated C _1-20 or C _1-10 alkyl groups, respectively, for example methyl, ethyl, propyl, butyl , Pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosanyl, or all possible isomers thereof It may be included, but may not be limited thereto.

Hereinafter, embodiments of the present disclosure have been described in detail, but the present disclosure may not be limited thereto.

A first aspect of the present application provides an antimicrobial composition comprising an alkyl-biogen derivative compound represented by the following general formula (1):

[Formula 1]

;

In Formula 1,

R ¹ and R ² are, each independently, is to include a C _1-10 alkyl group, each substituted, linear or branched, by a X ¹ and X ^2, X ¹ and X ² are, each independently, -NH ₂ , —NR ³ H, —NR ³ R ⁴ , —COOH, —SO ₃ H, —SO ₂ H, and —PR ³ R ⁴ , wherein R ³ and Each R ⁴ is independently a C _1-10 alkyl group.

According to the present application, among the viologen derivative compounds mainly used as herbicides in the past, substituted alkyl-biogen derivative compounds are not only suitable as antibacterial agents, but also have the activity of killing the strain by reacting with the protein of the strain, and in particular, By placing an amine group at both or one end of the alkyl-biogen group, new antimicrobial properties can be expressed beyond the redox characteristics of the existing alkyl-biogen. In particular, materials having amine groups at both ends have special bioactive properties, because polyamines belonging to a group of substances collectively called polyamines (PAs) play an important role in the growth and killing of organisms. Polyamines are so widely distributed in vivo that they can be used during cellular transcription, RNA modification, protein translation, membrane stabilization, and modulation of cell signaling. Involved [Proceedings of National Academy of Sciences: PNAS, 2013, vol 109, 6343-6347]. According to the present application, a new concept of antimicrobial composition can be prepared by combining the redox properties of biologen and the bioactive properties of polyamine in one molecule, which are very different from those of biologen and also very different from polyamine. have. Alkyl-biogen derivative compounds according to the present invention not only show excellent antimicrobial effect but also retain activity to kill strains.

Alkyl-biogen derivative compounds according to the present application, although there are some antimicrobial differences depending on the size of the alkyl group substituted by X ¹ and X ² , but does not differ significantly. The antimicrobial composition of the present application may include an alkyl-biogen derivative compound having a C _1-10 alkyl group. In addition, a carboxyl group, a sulfate group, a phosphate group, etc. may be used instead of the amine group substituted with the C _1-10 alkyl group, and although the characteristics show lower antimicrobial properties than the viologen derivative compound having an amine group, it may be used as a meaningful antimicrobial substance. Can be.

In one embodiment of the present application, the alkyl-biogen derivative compound is a positively charged material of +2, may be combined with one or more of various anions to form a complex, but may not be limited thereto. At this time, the anion is not particularly limited.

In an exemplary embodiment, R ¹ and R ² are each independently a C _1-20 or C _1-10 linear or branched alkyl group each substituted by X ¹ or X ² , and are selected from X ¹ or X ² . It may include one selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, hepyl, octyl, nonyl, decyl, and isomers thereof each substituted by However, this may not be limited. Alternatively, R ¹ and R ² may include one or more carbon-carbon double bonds. In addition, R ¹ and R ² may be the same or different.

In an exemplary embodiment, the alkyl-biogen derivative compounds according to the present disclosure, the substituents X ¹ and X ² at both ends may be the same or different.

In an exemplary embodiment, R ³ and R ⁴ is each independently a C _1-20 or C _1-10 linear or branched alkyl group, which is methyl, ethyl, propyl, butyl, pentyl, hexyl, hepyl, octyl, nonyl, It may include, but is not limited to, those selected from the group consisting of decyl groups, and isomers thereof. For example, R ³ and R ⁴ may be the same or different.

In one embodiment of the present application, the antimicrobial composition comprises water; C _1-5 alcohols such as methanol, ethanol, propanol, butanol or pentanol and the like; Tetrahydrofuran; Acetone; Dimethylformamide; And it may be to include a solvent selected from the group consisting of, but may not be limited thereto.

In one embodiment of the present application, the alkyl-biogen derivative compound, R ¹ and R ² are both trimethylene group [-CH ₂ -CH ₂ -CH _2- ], X ¹ and X ² are the same , -NH ₂ , -NHCH ₃ , -COOH, and may have a substituent selected from the group consisting of -SO ₃ H, but may not be limited thereto.

In one embodiment of the present application, the concentration of the alkyl-biogen derivative compound may be about 10 M or less, but may not be limited thereto. The concentration of the compound may be, for example, about 0.1 nM to about 10 M, about 0.1 nM to about 5 M, about 0.1 nM to about 1 M, about 0.1 nM to about 0.5 M, about 0.1 nM to about 0.1 M, About 0.1 nM to about 50 mM, about 0.1 nM to about 10 mM, about 0.1 nM to about 1 mM, about 0.1 nM to about 0.1 mM, about 0.1 nM to about 50 μM, about 0.1 nM to about 10 μM, about 0.1 nM to about 1 μM, about 0.1 nM to about 0.1 μM, about 0.1 nM to about 50 nM, about 0.1 nM to about 10 nM, about 0.1 nM to about 1 nM, about 1 nM to about 10 M, about 10 nM to About 10 M, about 50 nM to about 10 M, about 0.1 μM to about 10 M, about 1 μM to about 10 M, about 10 μM to about 10 M, about 50 μM to about 10 M, about 0.1 mM to about 10 M, about 1 mM to about 10 M, about 10 mM to about 10 M, about 50 mM to about 10 M, about 0.1 M to about 10 M, about 0.5 M to about 10 M, about 1 M to about 10 M, Or about 5 M to about 10 M, but may not be limited thereto.

In one embodiment of the present application, the strain to be applied of the antimicrobial composition is not particularly limited. For example, the antimicrobial composition may include Pseudomonas aeruginosa, Staphylococcus aureus, Klebsiella pneumoniae, Klebsiella sp., E. coli, and Bacillus sp. Bacillus sp.), Streptococcus mutans, Candida albicans, Aspergillus niger, Micrococcus sp., Staphylococcus sp., May have an antimicrobial activity against a strain selected from the group consisting of Enterobacter sp., Vibrio sp., Edwardsiella sp., And combinations thereof. However, this may not be limited. For example, the antimicrobial composition has antimicrobial activity against that comprising a strain selected from the group consisting of Pseudomonas aeruginosa, Staphylococcus aureus, Klebsiella pneumoniae, and combinations thereof. It may be, but may not be limited thereto.

A second aspect of the present application provides a surface antimicrobial treatment method comprising applying to the substrate an antimicrobial composition according to the first aspect of the present application comprising an alkyl-biogen derivative compound represented by the following general formula:

[Formula 1]

;

In Formula 1,

R ¹ , R ² , X ¹ and X ² are as defined in the first aspect herein above.

Conventional antimicrobial materials are limited in their application to the contact type rather than the elution type. However, since the compounds of Formula 1 according to the present invention have amine groups at both ends, they are disposed on the surface of various substrates or materials such as plastics, fibers, or polymers through nucleophilic reactions using the same [Royal Society of Chemistry: RSC Advances, 2013, vol. 3, 2509-2519], and can be stably fixed to the oxide or chalcogenide surface through a process such as self-assembly adsorption. At this time, if a variety of substrates or materials such as polymers, fibers, plastics that can be applied to the nucleophilic reaction can be disposed stably on the surface of the antimicrobial composition according to the present application, if the nucleophilic reaction is very slow or difficult By blending well with the base material or the raw material of the material can be expressed through the injection molding process antibacterial properties.

In one embodiment of the present application, the antimicrobial composition comprises water; C _1-5 alcohols such as methanol, ethanol, propanol, butanol or pentanol and the like; Tetrahydrofuran; Acetone; Dimethylformamide; And it may be to include a solvent selected from the group consisting of, but may not be limited thereto.

Applying the antimicrobial composition to a substrate may be to apply the surface of the substrate by immersing the substrate in the antimicrobial composition. In this case, the coating may be performed only on one surface of the substrate, or may be performed on both surfaces. When only one surface of the substrate is to be applied, but may be performed by applying a masking material such as paraffin on the other surface and the substrate coated on one surface of the paraffin in the solution, but may not be limited thereto. The masking material application may be carried out through conventional methods known using materials commonly used in the art in addition to paraffin.

In one embodiment of the present application, the above description is not particularly limited. For example, the substrate is polyethylene terephthalate (PET), polyethylene sulfone (PES), polyethylene naphthalate (PEN), polyester (polyester), polycarbonate (PC), polymethyl methacrylate (PMMA), poly Mead (PI), ethylene vinyl acetate (EVA), polycaprolactame, polycaprolactone, polylactic acid, polyglycolic acid, polyurethane, poly (3) -Hydroxybutylate-co-3-hydroxyvalate (poly (3-hydroxybutyrate-co-3-hydroxyvalerate: PHBV), nylon (nylon), polyvinylchloride (PVC), polyacrylate , Polylysine, polysaccharide, polypeptide, polynucleotide, polyethylene oxide, polyphosphazene, amorphospolye Lenterephthalate (APET), polypropylene terephthalate (PPT), polyethylene terephthalate glycerol (PETG), polycyclohexylenedimethylene terephthalate (PCTG), modified triacetylcellulose (TAC), polyarylate (PAR), Polydimethylsiloxane (PDMS), silicone resins, fluorine resins, modified epoxy resins, Teflon, and copolymers thereof; cotton; fiberglass; indium tin compound (ITO) films; and metal films The composition according to the present disclosure may be used without particular limitation in the type and application method of the substrate.

In an exemplary embodiment, when the antimicrobial composition includes water as a solvent, applying the antimicrobial composition to the substrate may be performed at a temperature of about 100 ° C. or less, but may not be limited thereto. For example, when using a solvent other than water, the coating temperature may be an appropriate temperature below the boiling point of the solvent used, but may not be limited thereto.

In an exemplary embodiment, the thickness at which the antimicrobial composition is applied to the substrate is not particularly limited. For example, the thickness of the coating film of the antimicrobial composition may be the thickness of a single molecule layer, or may be about 1 μm or less or about 100 nm or less, but may not be limited thereto.

In the second aspect of the present application, detailed descriptions of portions overlapping with the first aspect of the present application are omitted, but the descriptions of the first aspect of the present application may be equally applied even if the description is omitted in the second aspect of the present application. Can be.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the following Examples are only provided to help understanding of the present application, and the contents of the present application are not limited to the following Examples.

EXAMPLE

Example 1

Di- (3-aminopropyl) -biogen (hereafter DAPV) was dissolved in water to a concentration of 1 nM, 1 μM, 1 mM, 1 M, respectively. After mixing 20 μl of the DAPV solution in each agar plate at different concentrations, Pseudomonas aeruginosa strains were plated on the various concentrations of DAPV-treated agar plates and incubated at 37 ° C. for 16 hours. The experimental result is shown in FIG.

As shown in FIG. 1, the strain was cultured when the concentration of DAPV was 1 nM, but it was confirmed that the strain was not cultured in the agar plate mixed with DAPV at a concentration of 1 μM or more, whereby the DAPV had antibacterial activity. I could see that this is.

Example 2

1,1'-bis (3-carboxypropyl) -4,4'-bipyridine-1,1'-dium (HOOC-CH ₂ -CH ₂ -CH ₂ -N ⁺ C ₅ H ₄ -N ⁺ C ₅ H ₄ -CH ₂ -CH ₂ -CH ₂ -COOH (hereinafter referred to as DCPV) was dissolved in water to a concentration of 1 nM, 1 μM, 1 mM, and 1 M, respectively. After mixing by μl, Pseudomonas aeruginosa strains were plated on the DCPV treated agar plates of various concentrations and incubated at 37 ° C. for 16 hours.

As a result of the culture, the strain was cultured when the concentration of DCPV was 1 nM, but it was confirmed that the strain was not cultured in the agar plate mixed with DCPV at a concentration of 1 μM or more, whereby the DCPV has antibacterial activity Could.

Example 3

1,1'-bis (3-sulfopropyl) -4,4'-bipyridine-1,1'-dium (HO ₃ S-CH ₂ -CH ₂ -CH ₂ -N ⁺ C ₅ H ₄ -N ⁺ C ₅ H ₄ -CH ₂ -CH ₂ -CH ₂ -SO ₃ H (hereinafter referred to as DSPV) was dissolved in water to a concentration of 1 nM, 1 μM, 1 mM, and 1 M, respectively. After mixing 20 μl of each concentration, Pseudomonas aeruginosa strains were plated on the DSPV-treated agar plates of various concentrations and incubated at 37 ° C. for 16 hours.

As a result of the culture, the strain was cultured when the concentration of DSPV was 1 nM, but it was confirmed that the strain was not cultured in the agar plate mixed with DSPV at a concentration of 1 μM or more, whereby the DSPV had antibacterial activity. Could.

Example 4

1,1'-bis (3- (methylamino) propyl) -4,4'-bipyridine-1,1'-dium (CH ₃ NH-CH ₂ -CH ₂ -CH ₂ -N ⁺ C ₅ H ₄ -N ⁺ C ₅ H ₄ -CH ₂ -CH ₂ -CH ₂ -NHCH ₃ (hereinafter DMAPV) were dissolved in water to 1 nM, 1 μM, 1 mM, 1 M concentration, respectively. After 20 μl of the solution was mixed at each concentration, Pseudomonas aeruginosa strains were plated on the DMAPV-treated agar plates of various concentrations and incubated at 37 ° C. for 16 hours.

As a result of the culture, the strain was cultured when the concentration of DMAPV was 1 nM, but it was confirmed that the strain was not cultured in the agar plate mixed with DMAPV at a concentration of 1 μM or more, whereby the DMAPV had antibacterial activity. Could.

Example 5

Pseudomonas aeruginosa strains were incubated for 16 hours at a temperature of 37 ℃. Di- (3-aminopropyl) -biogen (DAPV) was dissolved in water to 1 nM, 1 μM, 1 mM, 1 M concentration, respectively. After absorbing 20 μl of the DAPV solution by concentration into paper discs having a diameter of 1 cm, the paper discs having absorbed the DAPV solution were placed on the cultured strains.

The experimental results are shown in FIG. 2, and the diameters of the regions in which strain culture is suppressed are measured and shown in FIG. 3.

As shown in Figures 2 and 3, it was shown that even when the concentration of DAPV is nM level, strain culture is suppressed, and as the concentration is higher, the region where the strain culture is suppressed becomes wider.

Example 6

Di- (3-aminopropyl) -biogen (DAPV) was dissolved in water to a concentration of 1 nm, 1 μM and 1 mM, respectively, and methyl biogen was also added to concentrations of 1 nM, 1 μM and 1 mM, respectively. Dissolved in water. After absorbing 20 μl of the DAPV solution and the methyl viologen solution into the paper disc each having a diameter of 1 cm by concentration, the paper disc was placed on a plate. Here, Pseudomonas aeruginosa strains were plated and incubated at 37 ° C. for 16 hours. The experimental results are shown in FIG. 4.

As shown in FIG. 4, even when the concentration of 1 nM DAPV was observed to inhibit the strain culture in the vicinity (B), the higher the concentration was confirmed that the culture inhibition region is wider, but treated with methyl biogen In one case, antimicrobial activity could not be confirmed, and even if the concentration was increased, no significant difference was observed (A).

Example 7

Di- (3-aminopropyl) -biogen (DAPV) was dissolved in water to prepare a 1 wt% DAPV solution. The DAPV solution was heated to 40 ° C., and then the PET film was immersed therein. At this time, 20 minutes after the PET film was immersed in the DAPV solution, the immersed PET film was taken out to measure the contact angle (Phoenicx 150, SEO Co.).

As a result, the initial contact angle of the PET film before dipping was 85 degrees (°), while the contact angle of the PET film immersed in the DAPV solution for 20 minutes was measured at 34 degrees, and the PET film immersed in the DAPV solution showed strong immersion. And it was found. This is the result of DAPV binding to the PET surface through aminolysis, demonstrating that the PET was successfully surface modified.

Experimental Example 1: Using a polyester fabric Antimicrobiality Measurement

For the measurement of antimicrobial activity, polyester fabric was used as a standard cloth and DAPV was treated according to Example 7, followed by strain 1 (Staphylococcus aureus ATC 6538; Staphylococcus aureus) and strain 2 (Klebsiella pneumoniae ATCC 4352; pneumococcal). Was inoculated and the antimicrobial activity was measured as follows using the measurement method of KS K0639: 2011. At this time, the control group was inoculated with the strain to the polyester fabric treated nothing and maintained under the same conditions for 18 hours. The results are shown in Table 1 below, and FIGS. 5A and 5B.

TABLE 1

As shown in Table 1 and Figures 5a and 5b, the control group treated with nothing increased the number of bacteria after 18 hours, but in the sample to which DAPV was applied, the strains were killed so that the number of bacteria significantly decreased to 99.9% in both strain 1 and strain 2. I could confirm that. This result is due to the bactericidal and antimicrobial action of alkyl-biogen as described above.

Experimental Example 2: Using Cotton Fabric Antimicrobiality Measurement

For antimicrobial determination, cotton fabric was used as a standard cloth and DAPV was treated according to Example 7, followed by strain 1 (Staphylococcus aureus ATC 6538; Staphylococcus aureus) and strain 2 (Klebsiella pneumoniae ATCC 4352; Pneumococcal) and the antimicrobial activity was measured as follows using the measurement method of KS K0639: 2011. At this time, the control group was inoculated with the strain to cotton treated nothing and maintained under the same conditions for 18 hours. The results are shown in Table 2 below, and FIGS. 6A and 6B.

TABLE 2

As shown in Table 2 and FIGS. 6A and 6B, the control group treated with nothing increased the bacterial count after 18 hours, but in the sample to which DAPV was applied, the strains were killed and the bacterial counts were significantly reduced by 99.9% in both strain 1 and strain 2. I could confirm that. This result is due to the bactericidal and antimicrobial action of alkyl-biogen as described above.

Experimental Example 3: Antibacterial Activity

For the determination of antimicrobial activity, Stomacher 400 POLY-BAG was used as a standard film and DAPV was treated according to Example 7, followed by strain 1 (Staphylococcus aureus ATC 6538; Staphylococcus aureus) and strain 2 (Escherichia coli ATCC 8739; Escherichia coli). ) Was inoculated and the antimicrobial activity (JIS Z 2801: 2010, adhesion film method) was measured as follows. At this time, the test solution was incubated for 24 hours at a temperature of 35 ± 1 ℃, 90% relative humidity and then the number of bacteria per 1 cm ² was measured, the control group was inoculated strain on Stomacher 400 POLY-BAG film that did not process anything And incubated at the same conditions for 24 hours. The results are shown in Table 3 below, and FIGS. 7A and 7B.

TABLE 3

As shown in Table 3 and FIGS. 7A and 7B, the control group treated with nothing increased the number of bacteria after 24 hours, but it was confirmed that the strains in the sample to which DAPV was applied decreased significantly to 0.63 per cm ² . The antimicrobial activity value is 2.0 log or more, indicating that there is an antimicrobial effect, and in the case of DAPV-treated samples, strains 1 and 2 show 4.5 and 6.3, respectively, as described above. It can be confirmed that the action is excellent.

Example 8

Di- (3-aminopropyl) -biogen (DAPV) was dissolved in water to prepare a 1 wt% solution. The DAPV solution was heated to 40 ° C., and then the surface thereof was modified by immersing the glass slide coated with alumina. At this time, 20 minutes after the glass slide was immersed in the DAPV solution, the immersed glass slide was taken out to measure the contact angle. As a result, the initial contact angle of the alumina-coated glass slide before surface modification was 10 degrees, while the contact angle of the surface-modified glass slide was immersed in DAPV solution for 20 minutes to measure 39 degrees. The water contact angle of the surface-modified glass slide after immersion is similar to that of the alkyl-biogen, indicating that alkyl-biogen is present on the glass slide surface.

Example 9

Di- (3-aminopropyl) -biogen (DAPV) was dissolved in water to prepare a 1 wt% solution. The DAPV solution was heated to 40 ° C., and then the surface was modified by immersing a Tin-doped Indiumoxide (ITO) slide therein. At this time, 20 minutes after the ITO slide was immersed in the DAPV solution, the immersed ITO slide was taken out to measure the contact angle. As a result, the initial contact angle of the ITO slide before surface modification was 20 degrees, while the contact angle of the surface modified ITO slide was immersed in DAPV solution for 20 minutes and measured at 39 degrees. The water contact angle of the surface-modified ITO slide after immersion is similar to that of the alkyl-biogen, indicating that alkyl-biogen is present on the surface of the ITO slide.

Example 11

A coating film was formed on the polystyrene film using a spray gun by dissolving a water-based paint (product name: MultiPlus Multi-Aqueous Water Paint, Noropaint) to contain 1 wt% of di- (3-aminopropyl) -biogen (DAPV). . The coating film was inoculated with strain 1 (Staphylococcus aureus ATC 6538; Staphylococcus aureus) and strain 2 (Klebsiella pneumoniae ATCC 4352; pneumococci) and the antimicrobial activity (JIS Z 2801: 2010, adhesion film method) was measured as follows. At this time, the test bacteria were incubated for 24 hours at a temperature of 35 ± 1 ° C. and 90% relative humidity, and the number of bacteria was measured per 1 cm ² , and the control group was inoculated with the strain to the aqueous paint coating without treatment for 24 hours. Incubated under the same conditions. The results are shown in Table 4 below.

TABLE 4

As shown in Table 4, the control group treated with nothing increased the number of bacteria after 24 hours, but in the paint coating sample to which DAPV was applied, it was confirmed that the strains significantly decreased to 0.63 per cm ² . When the antimicrobial activity value is 2.0 log or more, the antimicrobial effect is shown. In the case of DAPV-treated samples, strains 1 and 2 show 4.5 and 6.3, respectively. When applied, it can be confirmed that the bactericidal and antimicrobial effect is excellent.

The foregoing description is for the purpose of illustration, and Those skilled in the art will understand that the present invention can be easily modified in other specific forms without changing the technical spirit or essential features of the present application. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined form.

The scope of the present application is indicated by the following claims rather than the above description, and all changes or modifications derived from the meaning and scope of the claims and their equivalents are included in the scope of the present application. Should be interpreted as

Claims (8)

1. An antimicrobial composition comprising an alkyl-biogen derivative compound represented by Formula 1 below:

   [Formula 1]

   

   ;

   In Formula 1,

   R ¹ and R ² each independently include a linear or branched C _1-10 alkyl group each substituted by X ¹ and X ² ,

   X ¹ and X ² are each independently selected from the group consisting of —NH ₂ , —NR ³ H, —NR ³ R ⁴ , —COOH, —SO ₃ H, —SO ₂ H, and —PR ³ R ⁴ Wherein R ³ and Each R ⁴ is independently a C _1-10 alkyl group.
2. The method of claim 1,

   Wherein the antimicrobial composition comprises a solvent selected from the group consisting of water, C _1-5 alcohol, tetrahydrofuran, acetone, dimethylformamide, and combinations thereof.
3. The method of claim 1,

   The antimicrobial composition of which the density | concentration of the said alkyl- biologen derivative compound is 10 M or less.
4. The method of claim 1,

   The antimicrobial composition includes Pseudomonas aeruginosa, Staphylococcus aureus, Klebsiella pneumoniae, Klebsiella sp., E. coli, Bacillus sp. , Streptococcus mutans, Candida albicans, Aspergillus niger, Micrococcus sp., Staphylococcus sp., Enterobacter sp. An antimicrobial composition having antimicrobial activity against a strain selected from the group consisting of Enterobacter sp.), Vibrio sp., Edwardsiella sp., And combinations thereof.
5. The method of claim 4, wherein

   The antimicrobial composition has an antimicrobial activity against those comprising a strain selected from the group consisting of Pseudomonas aeruginosa, Staphylococcus aureus, Klebsiella pneumoniae, and combinations thereof. Composition.
6. Applying an antimicrobial composition according to claim 1 comprising an alkyl-biogen derivative compound represented by the following formula (1) to a substrate:

   Including, surface antibacterial treatment method:

   [Formula 1]

   

   ;

   In Formula 1,

   R ¹ , R ² , X ¹ and X ² are as defined in claim 1.
7. The method of claim 6,

   And wherein said antimicrobial composition comprises a solvent selected from the group consisting of water, C _1-5 alcohol, tetrahydrofuran, acetone, dimethylformamide, and combinations thereof.
8. The method of claim 6,

   The substrate is polyethylene terephthalate (PET), polyethylene sulfone (PES), polyethylene naphthalate (PEN), polycarbonate (PC), polymethyl methacrylate (PMMA), polyimide (PI), ethylene vinyl acetate (EVA ), Polycaprolactame, polycaprolactone, polylactic acid, polyglycolic acid, polyurethane, poly (3-hydroxybutylate-co-3- Poly (3-hydroxybutyrate-co-3-hydroxyvalerate (PHBV), nylon (nylon), polyvinylchloride (PVC), polyacrylate, polylysine, polysaccharide (polysaccharide), polypeptide (polypeptide), polynucleotide (polynucleotide), polyethylene oxide (polyethylene oxide), polyphosphazene (polyphosphazene), amorphous polyethylene terephthalate (APET), polypro Lenterephthalate (PPT), polyethylene terephthalateglycerol (PETG), polycyclohexylenedimethylene terephthalate (PCTG), modified triacetylcellulose (TAC), polyarylate (PAR), polyetherimide (PEI), poly A surface comprising one selected from the group consisting of dimethylsiloxane (PDMS), silicone resins, fluorine resins, modified epoxy resins, Teflon, and copolymers thereof; cotton; fiberglass; and metal films Antibacterial treatment method.

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