KR101285301B1 - Antibacterial coating compound and composition comprising the same - Google Patents

Abstract

The present invention relates to an antimicrobial coating compound comprising a dopamine derivative including a catechol group having a coating power and a quaternary ammonium salt having an aliphatic alkyl chain as an active ingredient. This has an excellent advantage.

Description

Antibacterial coating compound and composition comprising the same

The present invention provides an antimicrobial coating compound comprising a dopamine derivative including a catechol group having a coating power and a quaternary ammonium salt having an aliphatic alkyl chain as an active ingredient, a method for preparing the same, and an antimicrobial coating composition comprising an antimicrobial coating compound. It is about.

In general, electronic products such as interior and exterior materials of glass or buildings, mobile phones, monitors, cameras, air conditioners, etc. are easily messed up in use, and are mainly contaminated by dust, saliva, fingerprints, grease, tobacco smoke, and bacteria.

Recently, in order to compensate for such problems, the surface of the interior or exterior materials of the glass or building, electronic products, etc. is often coated during the manufacture or distribution of the products.

In the case of the existing surface coating, a pretreatment process using a plasma, a primer, or the like, which is a surface treatment for activating the surface, is required. When the silane treatment with a primer on the surface is hydrolyzed at low pH conditions, the surface is activated to increase the binding force. However, this pretreatment process is not only cumbersome as the process is increased when developing various coating materials, but also has the disadvantage of adding process cost. In addition, the existing coating material has a problem that the coating power is lost due to the release of antimicrobial material under time, harsh conditions (60 ℃, 24h storage) occurs.

Accordingly, an object of the present invention is to provide an antimicrobial coating compound and a method for producing the same, and an antimicrobial coating composition having excellent coating power on various surfaces.

In addition, an object of the present invention is to provide an antimicrobial coating compound and a coating method using the same that can be easily coated without the need for pretreatment by plasma or primer.

In addition, an object of the present invention is to provide an antimicrobial coating compound and a coating method using the same, which is excellent in antimicrobial activity as well as excellent in the fixing force of the antimicrobial material.

In order to achieve the above object, the present invention provides an antimicrobial coating compound of Formula 1 comprising a dopamine derivative including a catechol group and a quaternary ammonium salt having an aliphatic alkyl chain as an active ingredient.

[Formula 1]

Wherein m is an integer from 1 to 6 and n is an integer from 2 to 20.

The present invention also provides an antimicrobial coating compound in which a dopamine derivative having a catechol group and a quaternary ammonium salt are combined in a molar ratio of 1: 1.

In addition, the present invention is Escherichia coli, Salmonella paratyphi (Salmonella paratyphi), Klebsilla pneumoniae, Proteus vulgaris, Vibrio cholerae (Vibrio cholerae) and Shigella flexneri ), Shigella dysenteriae provides an antimicrobial coating compound having antimicrobial activity against at least one Gram-negative bacterium selected from the group consisting of.

In addition, the present invention is Bacillus subtilis (Bacillus subtilis), Bacillus anthracis (Bacillus anthracis), Mycobacterium smegmatis, Mycobacterium tuberculosis (Mycobacterium tuberculosis), Mycobacterium Kansashi ( It provides an antimicrobial coating compound having antimicrobial activity against at least one Gram-positive bacteria selected from the group consisting of Mycobacterium kansasii), Staphylococcus aureus and Streptococcus pyogenes.

In addition, the present invention is one or more fungi selected from the group consisting of fungi, Aspergillus niger, penicillium, penicillium, Cladosporium, Arternaria and Fusarium It provides an antimicrobial coating compound having antimicrobial activity against.

The present invention also provides an antimicrobial coating compound having antimicrobial activity against at least one bacterium selected from the group consisting of Gram-positive bacteria, Gram-negative bacteria and fungi after storage at a temperature of -70 ° C to 100 ° C.

The present invention also provides an antimicrobial coating compound having antimicrobial activity against at least one bacterium selected from the group consisting of Gram-positive bacteria, Gram-negative bacteria and fungi after storage at 100% humidity.

In addition, the present invention comprises the step 1 to obtain a dopamine derivative compound by reacting a catechol group-containing dopamine compound and an acyl halide compound in a solvent; And a step 2 of reacting the obtained dopamine derivative with a quaternary ammonium salt in a solvent.

In another aspect, the present invention provides a method for deep coating the antimicrobial coating compound containing a dopamine derivative containing a catechol group in an aqueous solution or an organic solvent for 20 to 28 hours at room temperature.

In another aspect, the present invention provides a coating method for deep coating the antimicrobial coating compound on a metal substrate such as Si, Ti or Au substrate, a universal polymer film such as PP, PET, PVC, PDMS or PS.

In another aspect, the present invention provides a coating method characterized in that the NaIO ₄ further added to the aqueous solution.

The present invention also provides a coating method wherein the organic solvent is ethanol, methanol, toluene, methylene chloride (MC), dimethylformamide (DMF) or tetrahydrofuran (THF).

The present invention also provides an antimicrobial coating composition comprising the antimicrobial coating compound mentioned above.

The antimicrobial coating compound according to the present invention includes a quaternary ammonium salt as an active ingredient in a dopamine derivative having a catechol group having a coating power, and thus has an excellent antibacterial activity. That is, the antimicrobial coating compound of the present invention has excellent antimicrobial activity, and has antimicrobial activity against fungi as well as gram positive bacteria and gram negative bacteria.

The antimicrobial coating compound of the present invention has the advantage of being able to coat a metal or polymer film surface through a dip coating method very easily in wet conditions. In other words, the antimicrobial coating compound of the present invention can be coated with a simple coating manufacturing process through crosslinking of catechol groups, and can also be immobilized with antimicrobial substances, causing parasitic diseases in various electronic products such as interior and exterior materials of buildings, mobile phones, and air conditioners. It has the effect of showing very good antimicrobial activity and biofilm formation inhibiting function against Gram-positive bacteria, Gram-negative bacteria and fungi.

1 is a view showing a state of the antimicrobial coating film is coated with the antimicrobial coating compound of the present invention.
Figure 2 is a graph showing the ¹ H NMR analysis of the antimicrobial coating compound according to an embodiment of the present invention.
Figure 3 is a graph showing the results measured by ATR-IR surface coated with an antimicrobial coating compound according to an embodiment of the present invention.
Figure 4 is a graph showing the results of measuring the surface coated with the antimicrobial coating compound according to an embodiment of the present invention by XPS.
Figure 5 is a photograph showing the antimicrobial test results for E. coli of the surface coated with the antimicrobial coating compound according to an embodiment of the present invention.
Figure 6 is a photograph showing the results of the antimicrobial test against Staphylococcus aureus on the surface coated with the antimicrobial coating compound according to an embodiment of the present invention.
Figure 7 is a photograph showing the results of the antimicrobial test for Salmonella (Salmonella) on the surface of the PVC film coated with the antimicrobial coating compound according to an embodiment of the present invention.
Figure 8 is a photograph showing the antimicrobial activity test results for E. coli (E. coli) on the surface of the PVC film coated with an antimicrobial coating compound according to an embodiment of the present invention.
Figure 9 is a photograph showing the antimicrobial activity test results for S. aureus (Straphylococcus aureus) on the surface of the PVC film coated with an antimicrobial coating compound according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail with the drawings.

The antimicrobial coating compound of the present invention is composed of a dopamine derivative including a catechol group and a quaternary ammonium salt having an aliphatic alkyl chain having 2 to 20 carbon atoms as an active ingredient, as shown in Formula 1 below.

[Formula 1]

Wherein m is an integer from 1 to 6 and n is an integer from 2 to 20.

The component of the antimicrobial coating compound of this invention is demonstrated concretely.

The dopamine derivative including the catechol group of the present invention is obtained by reacting a bromoacyl halide compound of formula (3) with dopamine (3,4-dihydroxyphenethylamine), which is a catecholamine of formula (2).

[Formula 2]

(3)

In the formula, m represents an integer of 1 to 6.

The compound of Formula 3 applied to the dopamine derivative compound of the present invention may be used without particular limitation as long as it is a bromoacyl halide-based compound, 3-bromopropionyl chloride, 4-bromopropionyl chloride, 4- Bromobutyroyl chloride, 5-Bromovaleroyl chloride or 6-bromohexanoyl chloride may be preferably used, with particular preference. For example, 4-bromobutyroyl chloride may be used.

The quaternary ammonium salt, which is an antimicrobial active ingredient of the antimicrobial coating compound of the present invention, may be used without particular limitation as long as it is a quaternary ammonium salt having an aliphatic alkyl chain having 2 to 20 carbon atoms, but preferably C ₂ -C ₁₆ Quaternary ammonium salts with alkyl chains can be used. Among these quaternary ammonium salts, specifically, N, N'-dimethylethylamine, N, N'-dimethylbutylamine, N, N'-dimethylhexyl Amine (N, N'-Dimethylhexylamine), N, N'-dimethylheptylamine, N, N'-dimethyloctylamine, N, N'-dimethylnonylamine (N, N-Dimethylnonylamine), N, N'-dimethyldecylamine, N, N'-dimethylundecylamine, N, N'-dimethyldodecyl Amine (N, N'-Dimethyldodecylamine), N, N'-dimethyltetradecylamine or N, N'-dimethylhexadecylamine (N, N-Dimethylhexadecylamine) may be more preferably used. have.

In the antimicrobial coating compound of the present invention, the dopamine derivative and the quaternary ammonium salt compound are preferably combined in a molar ratio of 1: 1.

Next, the manufacturing method of the antimicrobial coating compound of this invention is demonstrated.

Method for producing an antimicrobial coating compound of the present invention step 1 to obtain a dopamine derivative compound by reacting a dopamine compound and an acyl halide compound in a solvent; And reacting the obtained dopamine derivative with the quaternary ammonium salt in a solvent. The solvent that can be used in step 1 of the above method is not particularly limited as long as it is a nonpolar solvent, but tetrahydrofuran (THF) may be particularly preferably used. After stirring for 4-6 hours at a temperature of 0 ~ 5 ℃ for the reaction of step 1, it is preferable to stir at room temperature for 20 to 48 hours, preferably 22 to 24 hours. For the reaction of step 2 of the above method, as the solvent, any solvent capable of dissolving the dopamine derivative may be used without particular limitation, but methanol may be particularly preferably used. It is preferable to stir for 20 to 72 hours, preferably 22 to 24 hours at a temperature of 50 ~ 90 ℃, preferably 70 ~ 80 ℃ for the reaction of step 2.

Next, the coating method using the antimicrobial coating compound of the present invention

All. 1 is a view showing a state of a coating film coated with an antimicrobial coating compound of the present invention. According to Figure 1, the antimicrobial coating compound of the present invention can be seen that the dopamine derivative portion having a coating power to the coating substrate is adhered tightly through crosslinking. Coating using the antimicrobial coating compound of the present invention has the advantage that does not have to go through a cumbersome process such as a pretreatment process using a plasma or primer required in the conventional antimicrobial coating process.

Dopamine-containing antimicrobial coating compound containing a catechol group having a coating power is dip under basic conditions in an aqueous solution or an organic solvent such as ethanol, methanol, toluene, MC, DMF or THF for 20 to 28 hours at room temperature. Through the coating process, the catechol group-containing dopamine derivative component is cross-linked to form a coating. The quaternary ammonium salt, an active ingredient with antimicrobial activity contained in the antimicrobial coating compound coated on the coated substrate, is immobilized on the coated surface and is well immobilized even under harsh conditions (60 ° C, 100% humidity, 24h storage). Antimicrobial properties can be exhibited without release of the substance.

The present invention has been described in detail with respect to the coating by the dip coating method, it is also possible to coat by a general coating method such as spin coating or spray coating.

The antimicrobial coating compound according to the present invention has excellent coating power, and can be coated on various surfaces without being limited whether the surface properties of the coating substrate are a metal or a polymer film. As a preferred coating substrate, the metal surface may be Si, Ti or Au, and the polymer film may be polypropylene (PP), polyethylene terephthalate (PET), polyvinyl chloride (PVC), polystyrene (PS) or polydimethylsiloxane. (PDMS).

Meanwhile, according to the present invention, the antimicrobial coating compound may be prepared as an antimicrobial coating composition together with a functional material having an antibacterial function, an infrared absorption function, an ultraviolet absorption function, an antistatic function, a hydrophilic function or a water repellent function, and the like.

Hereinafter, the present invention will be described in detail with examples. The embodiments described below are intended to help the understanding of the present invention, but the scope of the present invention is not limited thereto.

EXAMPLES Preparation of Antimicrobial Coating Compound

5 g of dopamine was dissolved in 35 ml of THF. 2.63 g of TEA (triethylamine) was added to the gastric solution, and 15 ml of THF (tetrahydrofuran) and 4.89 g of 4-bromobutyroyl chloride were dissolved in a dropping funnel. The mixture was slowly added under 1 ° C. for 1 hour, and then stirred for 5 hours, followed by stirring at room temperature for 24 hours. Thereafter, to remove salt, it was filtered, and the remaining solution except for the solution caused by precipitation of the filtered solution in hexane was removed and dried in a dry oven. After drying, the precipitate was reprecipitated using methylene chloride (MC) and dried. After drying, the obtained product was dissolved in methanol, and N, N'-dimethyldecylamine (N, N'-Dimethyldecylamine) was added thereto, and the mixture was stirred at 80 ° C for 24 hours. Thereafter, the precipitate was precipitated using hexane, and then hexane was removed, dried in a dry oven, dissolved in methylene chloride, and then methylene chloride was removed to obtain a compound of Chemical Formula 4 below. The reaction of the examples is shown by the following chemical scheme.

[Formula 4]

[Chemical Reaction Formula]

The compound of Chemical Formula 4 obtained in this Example was subjected to structural analysis through 1H NMR, and the results are shown in FIG. 2.

Test Example 1 Coating Test

In order to evaluate the coating properties of the antimicrobial coating compound according to the present invention was carried out the following experiment.

(1) Dip coating in aqueous solution

The antimicrobial coating compound sample obtained in the example was dissolved at 50 mg / ml in an aqueous solution solvent. The metal surface of Si, Ti and Au and PDMS, PET, PVC, PS, and PP, which were universal polymer films, were added to the solution, and stored in a basic condition of pH 8.5 or above at room temperature for 24 hours for deep coating. At this time, it is possible to add the oxidizing agent NaIO ₄ in order to shorten the coating time in an amount of 2 to 10 equivalents to 1 equivalent of the antimicrobial coating compound sample, 2 equivalents was added in this test.

First, in order to confirm the coating on the metal surface and the surface of the polymer film, the contact angle was measured, and the coating was determined based on the change of the contact angle. The results are shown in Table 1 below. The result of measuring the contact angle of the uncoated surface (indicated by Bare), the sample obtained from the dopamine derivative produced in step 1, and the contact angle of the coated surface using the sample obtained in Example Comparing the values, it was found that the contact angles of the bare and coated states varied. In the case of coating, it was confirmed that the contact angle became large on the metal surface and the contact angle decreased on the general-purpose polymer film.

On the other hand, the coating thickness of the surface coated in the same manner as above was measured using an ellipsometer (Elipsometer). As a result, the difference of the thickness of the coated surface was confirmed using the uncoated Bare state and the sample obtained in the Example, and the results are shown in Table 2. According to Table 2, it can be seen that the coating thickness became thicker after the addition of NaIO ₄ used to shorten the coating time.

Si surface Ti surface Au surface Example NaIO ₄ Ex 87.39 59.15 56.96 After NaIO ₄ 109.78 990.77 689.82

In addition, the coated Si metal surface was measured by ATR-IR through the same method as above, and the functional groups of the surface were confirmed. The results are shown in FIG. 3. Aromatic (aromatic) appears in the range according to FIG. 3, when using the samples obtained in Examples measured by the coated surface, 2800cm ^-1 The alkyl chain and 3000-3500cm ^-1 in the sample in the range of functional groups Confirmed.

Finally, XPS was measured for surface analysis of the coated surface through the same method as above, and the results are shown in FIG. 4. According to Figure 4, the surface analysis confirmed the elements such as C (1s) at 284-285 eV, O (1s) at 531 eV and N (1s) at 399 eV.

(2) Dip Coating Process in Organic Solvent State

The antimicrobial coating compound sample obtained in the example was dissolved at 50 mg / ml in methanol as an organic solvent. At this time, the ratio of the organic solvent and the aqueous solution was adjusted in various ways. In this solution, a metal surface of Si, Ti, and Au was added and stored at room temperature for 24 hours for deep coating. The contact angle of the coated surface was measured and the results are shown in Table 3 below. When coated, it was found that the contact angle became large on the metal surface and the contact angle decreased on the general-purpose polymer film.

(3) Dip coating process under harsh conditions (-70 ℃, 60 ℃, and 100 ℃)

The antimicrobial coating compound sample obtained in the example was dissolved in an aqueous solution at 50 mg / ml. The Si metal surface was placed in this solution and stored for 24 hours under harsh conditions of -70 ° C, 60 ° C, and 100 ° C, and then dip coated. The results are shown in Table 4. It was confirmed that there was no significant change in contact angle even under harsh conditions, and it was confirmed that the coating material could be immobilized even under severe conditions.

Test Example 2 Antimicrobial Effect Test

In order to evaluate the practicality of the antimicrobial properties of the antimicrobial coating composition according to the present invention, the following experiment was conducted.

(1) Experiment on solid agar plate

To test the antimicrobial effects on various bacteria, representative Gram positive and Gram negative test microorganisms were selected. The selected microorganisms were selected as Escherichia coli, Salmonella paratyphi as Gram-negative bacteria, and Staphylococcus aureus as Gram-positive bacteria. Agar Plate Smear Mathod, which can be measured visually by counting the antimicrobial activity in cultured colonies, and a typical antimicrobial screening system that observes the inhibition zone that appears around the surface of a coated metal or universal polymer film The antimicrobial activity on solid LB, NB and MRS agar plates, respectively, was determined according to the strain. Specifically, the experiment was performed as follows.

(1) Agar plate smearing method test on NB agar plate of Salmonella

Antimicrobial tests on NB agar plates were performed on Salmonella, representative of Gram-negative bacteria. A single colony of Salmonella was inoculated into 5 ml NB liquid medium and incubated overnight in a 37 ° C. shaking incubator with stirring at 150 rpm. 50ul of the cultured cell suspension was inoculated in 5ml of liquid NB medium. 100 ul of this solution was inoculated in 900 ul of peptone water to repeat this method to dilute the final strain to 10 ² . A universal PVC and PS film, dip-coated with the sample obtained in this example at a concentration of 50 mg / ml, was placed on a plate, and a solid NB agar plate was formed thereon. 100 ul of diluted cell culture was then plated onto NB agar plates and incubated overnight in a 37 ° C. incubator.

As a result, colonies did not grow at all on the coated PVC and PS film surfaces in the above examples, but numerous colonies were observed on the uncoated surfaces. The results are shown in Table 5. According to Table 5, it can be seen that when coated with the sample obtained in the embodiment of the present invention there is no change in antimicrobial properties even under severe conditions.

PVC surface PS surface Severe conditions (60 ℃, 100% humidity, 24h storage) Control Example Control Example Control Example Log ₁₀ CFU
(ml) 3.5 0 3.69 0 3.51 0 Bacteria Kill
(%) - 100 - 100 - 100

(2) Test of agar plate smearing method on LB agar plate of E. coli

Antimicrobial tests on LB agar plates were also performed on the Escherichia coli, a representative Gram-negative bacterium. Proceed as in Salmonella method above.

As a result, the same result was found. That is, colonies did not grow at all on the surface coated with the sample obtained in the example, but numerous colonies were observed on the uncoated surface. The results are shown in FIG. 5 and Table 6. According to Table 6, it can be seen that when coated with the sample obtained in the embodiment of the present invention there is no change in antimicrobial properties even under severe conditions.

PVC surface PS surface Severe conditions (60 ℃, 100% humidity, 24h storage) Control Example Control Example Control Example Log ₁₀ CFU
(ml) 3.78 0 3.36 0 3.54 0 Bacteria Kill
(%) - 100 - 100 - 100

(3) Staphylococcus aureus (S. aureus )of MRS  Agar plate smearing method test on agar plate

Single colonies of S. aureus were inoculated into 5 ml MRS liquid medium and incubated overnight in a 37 ° C. incubator. 50ul of the cultured cell suspension was inoculated in 5ml of liquid MRS medium. This procedure was repeated, inoculating 100 ul of this solution in 900 ul of peptone water to dilute the final strain to 10 ² . General purpose PVC and PS films were dip-coated with the sample obtained in this example at a concentration of 50 mg / ml, and a solid MRS agar plate was formed thereon. 100 ul of diluted cell culture was then plated onto MRS agar plates and incubated overnight in a 37 ° C. incubator.

In the case of Staphylococcus aureus, numerous colonies were observed in the film that was not coated with the sample obtained in the example, but the surface coated with the sample obtained in the example showed that the colony of Staphylococcus aureus Didn't grow at all The results are shown in FIG. 6 and Table 7. According to Table 7, it can be seen that when coated with the sample obtained in the embodiment of the present invention there is no change in antimicrobial properties even under severe conditions.

PVC surface PS surface Severe conditions (60 ℃, 100% humidity, 24h storage) Control Example Control Example Control Example Log ₁₀ CFU
(ml) 3.88 0 3.43 0 3.79 0 Bacteria Kill
(%) - 100 - 100 - 100

(4) Salmonella ( Salmonella )of NB  Restraining band on agar plate ( inhibition  zone test

Single colonies of Salmonella were inoculated into 5 ml NB liquid medium and incubated overnight in a 37 ° C. incubator. 50ul of the cultured cell suspension was inoculated in 5ml of dissolved solid NB medium. The sample obtained in the above example was placed on a solid NB plate at a concentration of 50 mg / ml so that the coated PVC surface was in contact with the strain. The inoculated strained solid NB medium was then plated so as to be entirely covered thereon and incubated overnight in a 37 ° C. incubator.

As a result, it was confirmed that all strains were grown on the surface which was not coated with the sample obtained in the example, but the surface coated with the sample obtained in the example was relatively suppressed by the naked eye because growth of the strain was suppressed. A clear transparent inhibition zone was formed. The results are shown in Fig.

(5) Inhibition zone test on LB agar plate of E. coli

Antimicrobial testing on LB agar plates was also performed on E. coli. Proceed as in Salmonella method above. As a result, it was confirmed that all strains were grown on the PVC surface which was not coated with the sample obtained in the example, but the surface coated with the sample obtained in the example was inhibited from the growth of the strain, so that the growth was not possible. ) Formed small. The results are shown in Fig.

(6) Inhibition zone test on MRS agar plate of S. aureus

Single colonies of S. aureus were inoculated into 5 ml MRS liquid medium and incubated overnight in a 37 ° C. incubator. 50ul of the cultured cell suspension was inoculated in 5ml of dissolved solid MRS medium. The sample obtained in this example was placed on a solid MRS plate with the coated side of the PVC film dip-coated at a concentration of 50 mg / ml contacting the strain. The inoculated strained solid MRS medium was then plated so as to be entirely covered thereon and incubated overnight in a 37 ° C. incubator. As a result, it was confirmed that all strains were grown on the surface which was not coated with the sample obtained in the example, but the surface coated with the sample obtained in the example did not grow because the growth of the strain was inhibited and thus a transparent inhibition zone was created. It was formed small. The results are shown in FIG.

Claims (22)

An antimicrobial coating compound of formula 1 consisting of a dopamine derivative having a catechol group and a quaternary ammonium salt having an aliphatic alkyl chain.
[Formula 1]

Wherein m is an integer from 1 to 6 and n is an integer from 2 to 20. The method of claim 1,
Dopamine derivative having a catechol group is an antimicrobial coating compound, characterized in that consisting of dopamine and acyl halide-based compounds. The method of claim 2,
The acyl halide compounds include 3-bromopropionyl chloride, 4-bromobutyroyl chloride, 5-bromo valeroyl chloride, and 5-bromoleroyl chloride. 6-Bromo hexanoyl chloride (6-Bromohexanoyl chloride) is an antimicrobial coating compound, characterized in that any one compound selected from the group consisting of. The method of claim 1,
The quaternary ammonium salt is an antimicrobial coating compound, characterized in that the quaternary ammonium salt having an alkyl chain in the C ₂ -C ₁₆ range. The method of claim 1,
The quaternary ammonium salts include N, N'-dimethylethylamine, N, N'-dimethylbutylamine, N, N'-dimethylhexylamine (N , N'-Dimethylhexylamine), N, N'-dimethylheptylamine, N, N'-dimethyloctylamine, N, N'-dimethylnonylamine (N, N-Dimethylnonylamine), N, N'-Dimethyldecylamine, N, N'-Dimethylundecylamine, N, N'-Dimethyldodecylamine, Any one selected from the group consisting of N, N'-Dimethyldodecylamine, N, N'-Dimethyltetradecylamine, and N, N'-dimethylhexadecylamine Antimicrobial coating compound, characterized in that the compound. The method of claim 1,
Dopamine (Dopamine) derivative having a catechol group and the quaternary ammonium salt is an antimicrobial coating compound, characterized in that combined in a molar ratio of 1: 1. The antimicrobial coating compound according to any one of claims 1 to 6 is Escherichia coli, Salmonella paratyphi, Klebsilla pneumoniae, Proteus vulgaris, An antimicrobial coating compound characterized by having antimicrobial activity against at least one Gram-negative bacterium selected from the group consisting of Vibrio cholerae, Shigella flexneri, and Shigella dysenteriae. The antimicrobial coating compound according to any one of claims 1 to 6 is Bacillus subtilis, Bacillus anthracis, Mycobacterium smegmatis, Mycobacterium two One or more Gram-positive bacteria selected from the group consisting of Mycobacterium tuberculosis, Mycobacterium kansasii, Staphylococcus aureus, and Streptococcus pyogenes Antimicrobial coating compound, characterized in that it has an antimicrobial activity against. The antimicrobial coating compound according to any one of claims 1 to 6 is selected from fungi, Aspergillus niger, penicillium, Cladosporium, Arternaria and An antimicrobial coating compound characterized by having antimicrobial activity against one or more fungi selected from the group consisting of Fusarium. The antimicrobial coating compound according to any one of claims 1 to 6 has an antimicrobial activity against at least one bacterium selected from the group consisting of Gram-positive bacteria, Gram-negative bacteria and fungi even after storage at a temperature of -70 ° C to 100 ° C. Antimicrobial coating compound, characterized in that having a. The antimicrobial coating compound according to any one of claims 1 to 6, characterized in that it has an antimicrobial activity against one or more bacteria selected from the group consisting of Gram-positive bacteria, Gram-negative bacteria and fungi even after storage at 100% humidity. Antibacterial coating compound. In the method for producing an antimicrobial coating compound according to any one of claims 1 to 6,
Step 1, reacting the catechol group-containing dopamine compound and the acyl halide compound in a solvent to obtain a dopamine derivative compound; And
Method for producing an antimicrobial coating compound comprising the step 2 of reacting the obtained dopamine derivatives with a quaternary ammonium salt having an aliphatic alkyl chain in a solvent. The method of claim 12,
The solvent of step 1 is a method for producing an antimicrobial coating compound, characterized in that tetrahydrofuran. The method of claim 12,
Step 1 is a method for producing an antimicrobial coating compound, characterized in that the reaction for 4 to 6 hours at a temperature of 0 ~ 5 ℃, the reaction for 20 to 48 hours at room temperature. The method of claim 12,
The solvent of step 2 is a method for producing an antimicrobial coating compound, characterized in that methanol. The method of claim 12,
Step 2 is a method for producing an antimicrobial coating compound, characterized in that the reaction for 22 to 72 hours at a temperature of 70 ~ 80 ℃. A method for coating an antimicrobial coating compound, characterized in that the antimicrobial coating compound according to any one of claims 1 to 6 is dissolved in an aqueous solution or an organic solvent, followed by dip coating for 20 to 28 hours at room temperature. 18. The method of claim 17,
The substrate is a coating method, characterized in that the Si, Ti or Au substrate. 18. The method of claim 17,
The substrate is a coating method, characterized in that the universal polymer film PP, PET, PVC, PDMS or PS. 18. The method of claim 17,
Coating method characterized by further adding NaIO ₄ to the aqueous solution. 18. The method of claim 17,
The organic solvent is ethanol, methanol, toluene, chloromethane (MC), dimethylformamide (DMF) or tetrahydrofuran (THF). An antimicrobial coating composition comprising an antimicrobial coating compound according to any one of claims 1 to 6.

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