KR101976473B1 - Anti-bacterial coating composition - Google Patents

Abstract

(여기서, n은 2 내지 100의 정수이며, R₁은 탄소수 1 내지 5의 알킬기, 탄소수 2 내지 5의 알케닐기 및 탄소수 2 내지 5의 알키닐기로 이루어진 군으로부터 선택되며, R₂는 수소, -OH, 할로겐기 및 -NH₂로 이루어진 군으로부터 선택된다.)The present invention relates to an antimicrobial coating composition. An antimicrobial coating composition according to an embodiment of the present invention is a coating composition for forming a coating layer on a plastic substrate, wherein the coating composition is a carbazole compound represented by the following formula (1): Binder resin; Organic solvents: Antimicrobial coating compositions comprising inorganic particles and natural oils:
[Chemical Formula 1]

(Wherein n is an integer of 2 to 100, R ₁ is selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms, and R ₂ is hydrogen, It is selected from the group consisting of OH, halogen, and -NH _2.)

Description

ANTI-BACTERIAL COATING COMPOSITION [0001]

The present invention relates to an antimicrobial coating composition. More particularly, the present invention relates to an antimicrobial coating composition for enhancing antimicrobial activity and physical properties of a plastic substrate by coating the surface of the plastic substrate.

In general, plastic materials have various excellent features not found in other materials, such as light weight but hard and easy to process. This feature has been extended to various fields in order to respond to social demands such as production rationalization and energy saving. On the other hand, plastics have such merits, but they have problems such as low surface hardness, poor weatherability, weak chemical resistance and solvent resistance, which easily cause discoloration or cracking in the outdoors, It is a big obstacle and its usage is often limited.

Among various uses of plastic materials, particularly when used as a packaging material, a certain level of physical properties that do not cause changes in external impacts is required in order to prevent the storage of the articles stored in the packaging material and the damage during distribution, In view of the increasing interest in the antimicrobial effect, antimicrobial activity is required.

More specifically, an antimicrobial film formed of a plastic material as a base material and having an antimicrobial layer formed on one side thereof is widely used as a packaging material.

Therefore, many experiments and studies have been conducted on an antibacterial film that can be used as a packaging material. However, in order to produce the antibacterial film, it is necessary to directly mix the film resin and the antibacterial material and to inject the antibacterial film. It is not practiced with economic problems because it needs to be reformed. That is, many packaging materials or packaging methods have been developed for the antibacterial packaging, but the commercialization of the packaging materials has not yet been realized, and the production of the expensive packaging material and the antibacterial packaging material are not properly implemented in the packaging system.

The antimicrobial material should have a chemically stable structure and safety must be ensured even when it is synthesized. In addition, when the antimicrobial material is mixed with a film resin such as polyethylene or polypropylene based on a petroleum compound, it is difficult to mix the material with another material that facilitates further mixing. In addition, when the antimicrobial agent is directly mixed with the adhesive or when the antimicrobial agent is mixed with the adhesive material or when the adhesive is mixed with the adhesive agent, the degree of polymerization of the adhesive agent is excessively excessive so that the proper mixing of the antimicrobial agent is not possible. Rather, it is unlikely to spread. When the antimicrobial substance and the polymer are thermally polymerized, the antimicrobial substance may be lost due to high temperature during the process, or an excessive cost is required.

Korean Patent Publication No. 1999-0054327 and Korean Patent Publication No. 2001-0077332 disclose patents relating to antimicrobial films for packaging. However, they have a problem that the antimicrobial activity for a short period of time is recognized but the antimicrobial activity for a long time is not maintained. There is a problem in stability by producing a film including an antimicrobial substance capable of affecting the human body.

Therefore, it is urgently required to develop an antimicrobial coating composition that exhibits antimicrobial activity, is stable, and can complement the physical properties of a plastic material.

KR 10-1999-0054327 A KR 10-2001-0077332 A

An object of the present invention is to provide an antimicrobial coating composition which exhibits antimicrobial activity by forming a coating layer on one side or both sides of a plastic substrate.

Another object of the present invention is to provide a packaging material having improved physical properties by forming a coating layer on a plastic substrate using the antimicrobial coating composition.

In order to achieve the above object, the present invention provides a coating composition for forming a coating layer on a plastic substrate according to an embodiment of the present invention, wherein the coating composition is a carbazole compound represented by the following formula (1): Binder resin: organic solvent; An antimicrobial coating composition comprising an inorganic particle and a natural oil:

[Chemical Formula 1]

(Wherein n is an integer of 2 to 100, R ₁ is selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms, and R ₂ is hydrogen, It is selected from the group consisting of OH, halogen, and -NH _2.)

Wherein the antimicrobial coating composition comprises 100 parts by weight of a binder resin, 10 to 15 parts by weight of a carbazole-based compound; 15 to 40 parts by weight of an organic solvent; 2 to 5 parts by weight of inorganic particles; And 1 to 3 parts by weight of a natural oil, and the carbazole compound and the organic solvent may be contained in a ratio of 1: 1 to 1: 4.

The natural oils include ally isothiocyanate, cinnamaldehyde, garlic oil, rosemary oil, jojoba oil, and carrot seed oil. ≪ / RTI >

The organic solvent may be selected from the group consisting of an alcohol solvent, a halogen-containing hydrocarbon solvent, a ketone solvent, a cellosolve solvent and an amide solvent.

A plastic substrate according to another embodiment of the present invention; And a coating layer formed on one side or both sides of the plastic substrate, wherein the coating layer is formed with a thickness of 10 to 20 mm according to the above-described antimicrobial coating composition.

Hereinafter, the present invention will be described in more detail.

The anti-bacterial of the present invention includes the case of being described as an antibacterial agent, which means blocking and suppressing the propagation of microorganisms such as bacteria, bacteria and ticks which cause asthma, eczema and rhinitis.

An antimicrobial coating composition according to an embodiment of the present invention is a coating composition for forming a coating layer on a plastic substrate, wherein the coating composition is a carbazole compound represented by the following formula (1): Binder resin: organic solvent; Inorganic particles and natural oils:

[Chemical Formula 1]

(Wherein n is an integer of 2 to 100, R ₁ is selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms, and R ₂ is hydrogen, It is selected from the group consisting of OH, halogen, and -NH _2.)

Preferably, the carbazole-based compound represented by the formula (1) is a compound represented by the following formula (2) or (3)

(2)

(3)

(Wherein, n and R ₁ are the same as the formula (I).)

R ₁ is selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms, preferably an ethylene group or a propylene group.

The carbazole-based compound represented by the formula (1) preferably has a number average molecular weight (Mn) of 2,000 to 5,000, but is not limited to the examples.

The antimicrobial coating composition is used for forming a coating layer on one side or both sides of a plastic substrate. The antimicrobial coating composition comprises 100 parts by weight of a binder resin, 10 to 15 parts by weight of a carbazole-based compound; 15 to 40 parts by weight of an organic solvent; 2 to 5 parts by weight of inorganic particles; And 1 to 3 parts by weight of natural oils. Preferably 100 parts by weight of the binder resin with respect to the weight of the whole composition; 12 parts by weight of a carbazole-based compound; 24 parts by weight of an organic solvent; 5 parts by weight of inorganic particles; And 2.5 parts by weight of natural oil.

When the natural oil is contained in an amount of less than 1 part by weight, the antibacterial effect is lowered. When the natural oil is contained in an amount of more than 3 parts by weight, there is a problem that the adhesion strength between the plastic substrate and the coating layer Occurs.

The carbazole compound and the organic solvent may be contained in a weight ratio of 1: 1 to 1: 4. More specifically, when the carbazole-based compound is contained in an amount exceeding 1: 1 as compared with the organic solvent, a yellowing phenomenon may occur when a coating layer is formed on a plastic substrate. The carbazole- When the content is less than 1: 4 as compared with the organic solvent, the antibacterial effect is lowered.

The organic solvent may be selected from the group consisting of an alcohol solvent, a halogen-containing hydrocarbon solvent, a ketone solvent, a cellosolve solvent, and an amide solvent. Specific examples thereof include tetrahydrofurfuryl alcohol, Furfuryl alcohol, and isopropylideneglycerol.

More specifically, the organic solvent is used for dissolving the carbazole-based compound and for facilitating dissolution between the binder resin, the inorganic particles and the natural oil. Any of the organic solvents described in the above examples may be used, but is preferably a cyclic alcohol, Tetrahydrofurfuryl alcohol, Furfuryl alcohol, and Isopropylideneglycerol may be selected from the group consisting of Tetrahydrofurfuryl alcohol, Furfuryl alcohol and Isopropylideneglycerol.

The binder resin is used for improving the adhesive strength when a coating layer is formed on one side or both sides of a plastic substrate using an antimicrobial coating composition. Specifically, the binder resin is composed of polyolefin, polystyrene, polycarbonate, polyurethane, polysulfone and polyacrylate , And in particular, polyacrylate, but not limited to the above examples.

The inorganic particles are selected from the group consisting of silica particles, alumina particles, zirconium oxide particles, titanium oxide particles, antimony oxide particles, and combinations thereof, and more specifically silica particles or alumina particles, but not limited thereto.

Since the inorganic particles provide a function of suppressing the shrinkage rate of the coating layer by coating the inorganic particles with the binder resin, the inorganic particles can improve the physical properties when forming the coating layer on one side or both sides of the plastic substrate. Therefore, in order to maximize the effect of improving the physical properties, the average particle size of the inorganic particles is 100 to 200 占 퐉, specifically 130 to 150 占 퐉, and the present invention is not limited to the above examples. The inorganic particles are added to suppress the shrinkage of the coating layer. When the average particle size is less than 100 탆, the effect of suppressing the shrinkage is insufficient. When the average particle size is more than 200 탆, formation of the transparent coating layer may be hindered.

The natural oil is a composition for further improving the antimicrobial function of the antimicrobial coating composition and specifically includes ally isothiocyanate, cinnamaldehyde, garlic oil, rosemary oil, Jojoba oil and carrot seed oil, and is preferably jojoba oil or carrot seed oil, but is not limited to the above examples.

The plastic substrate may be at least one selected from the group consisting of polyethylene (PE), polypropylene (PP), polyamide (PA), polycarbonate (PC), polystyrene (PS), polyethylene terephthalate (PET), ethylene vinyl acetate PVC), in particular polyethylene (PE) or polypropylene (PP), but not limited to the above example.

A plastic substrate 100 according to another embodiment of the present invention; And an antimicrobial coating layer 200 formed on one side or both sides of the plastic substrate. The antimicrobial coating layer 200 is a packaging material having the above-described antimicrobial coating composition formed to a thickness of 10 to 20 mm.

More specifically, the antimicrobial coating layer (200) comprises a plastic substrate (100) and an antimicrobial coating layer (200) formed on one side of the plastic substrate, wherein the antimicrobial coating layer (200) Binder resin; Organic solvents: may be formed from an antimicrobial coating composition comprising inorganic particles and natural oils:

[Chemical Formula 1]

(Wherein n is an integer of 2 to 100, R ₁ is selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms, and R ₂ is hydrogen, It is selected from the group consisting of OH, halogen, and -NH _2.)

The carbazole-based compound represented by the formula (1) has a number average molecular weight (Mn) of 2,000 to 5,000, but is not limited thereto.

The antimicrobial coating layer 200 is formed of an antimicrobial coating composition and is formed as a transparent coating layer having a thickness of 10 to 20 mm, and more specifically, a thickness of 13 to 15 mm. When the thickness of the coating layer is less than 10 mm, there is a problem that the antibacterial function is lowered, and when the thickness exceeds 20 mm, there is a problem that the economical efficiency is lowered.

The packaging material may be used for packaging a product based on a plastic substrate, and is usable without limitation as long as a person skilled in the art can easily select and use the packaging material.

The antimicrobial coating composition according to the present invention can prevent and inhibit the growth of microorganisms such as bacteria, bacteria, mites and the like by forming a coating layer on one side or both sides of the plastic substrate and can continuously inhibit microbial propagation for 1 to 3 months Blocking and suppression.

In addition, the antimicrobial coating composition according to the present invention can improve the physical properties of the plastic substrate by forming a coating layer on one side or both sides of the plastic substrate, thereby facilitating the storage and movement of the inside when used as a packaging material.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a laminated structure of a packaging material according to an embodiment of the present invention. FIG.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

[Preparation Example 1: Preparation of antimicrobial coating composition]

Example 1 Example 2 Example 3 Example 4 Example 5 Carbazole-based compound 12 15 10 12 12 Polyacrylate 100 100 100 100 100 Tetrahydroperryl rile alcohol 24 15 40 - 24 Furfuryl alcohol - - - 24 - Silica particles 5 5 5 5 5 Carrot seed oil 2.5 2.5 2.5 2.5 - Jojoba oil - - - - 2.5

(Unit: parts by weight)

Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Carbazole-based compound 20 12 12 12 Polyacrylate 100 100 100 100 Tetrahydroperryl rile alcohol 10 - 24 24 Methanol - 24 - - Silica particles 5 5 5 - Silica particles
(Average particle size 50 탆) - - - 5 Carrot seed oil 2.5 2.5 - 2.5 Castor oil - - 2.5 -

(Unit: parts by weight)

The carbazole-based compounds shown in Table 1 and Table 2 are compounds represented by the following Formula 4, and the average particle size of the silica particles is 135 탆:

[Chemical Formula 4]

(Wherein n is an integer of 2 to 100)

[Preparation Example 2: Preparation of a packaging material in which a coating layer was formed]

On one side of the polyethylene (PE) substrate, a coating layer was formed to a thickness of 13 mm using the coating compositions of Examples 1 to 5 and Comparative Examples 1 to 4.

[Experimental Example 1: Antibacterial Experiments of Examples and Comparative Examples]

E. coli was inoculated into the packaging material formed with the coating composition of Example 1 and Comparative Examples 1 to 3, and the concentration of bacteria was measured after 24 hours.

Initial concentration (CFU / mL) After 24 hours concentration (CFU / mL) Antibacterial activity (log) Bacterial reduction rate (%) Example 1 1.00 × 10 ⁵ <2 5.82 99.99 Comparative Example 1 1.00 × 10 ⁵ 3.32 × 10 ³ - - Comparative Example 2 1.00 × 10 ⁵ 8.10ⅹ10 ² - - Comparative Example 3 1.00 × 10 ⁵ 5.62 × 10 ² - -

(CFU is a conceptual representation of the number of bacteria)

As shown in Table 3, in Example 1, the concentration of E. coli decreased after 24 hours and the bacterial reduction rate was 99.99%. On the other hand, in Comparative Examples 1 to 3, the concentration of E. coli was partially reduced, Respectively.

[Experimental Example 2: Physical Properties Tests of Examples and Comparative Examples]

1) Pencil Hardness

Using a pencil hardness meter, the maximum hardness without a groove was observed after three reciprocations at an angle of 45 degrees under the load of 750 g according to the measurement standard JIS K5400.

2) Transmittance and haze

The transmittance and haze were measured using a spectrophotometer (instrument: COH-400).

3) Bending test

Each package was sandwiched between cylindrical ellipses of various diameters and the minimum diameter at which cracks did not occur was measured.

Pencil Hardness (750gf) Transmittance (%) Haze (%) Flex test (Φ, mm) Example 1 3H 93.2 0.4 6 Example 2 3H 90.2 0.6 6 Example 3 3H 91 0.7 6 Example 4 3H 91.4 0.5 6 Example 5 3H 92.3 0.5 6 Comparative Example 4 H 92.3 0.4 3

According to Table 4, although Examples 1 to 5 according to one embodiment of the present invention were found to be superior in physical property evaluation results, in Comparative Example 4, it was confirmed that the hardness and flexure test were inferior to those in Examples 1 to 5 Respectively.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, Of the right.

100: plastic substrate
200: Antimicrobial coating layer

Claims (5)

A coating composition for forming a coating layer on a plastic substrate,
Wherein the coating composition is a carbazole-based compound represented by the following formula (1);
Binder resin;
Organic solvent:
Inorganic particles and
Containing natural oils
Antimicrobial coating composition.
[Chemical Formula 1]

(Wherein n is an integer of 2 to 100, R ₁ is selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms, and R ₂ is hydrogen, It is selected from the group consisting of OH, halogen, and -NH _2.) The method according to claim 1,
Wherein the antimicrobial coating composition comprises 100 parts by weight of a binder resin, 10 to 15 parts by weight of a carbazole-based compound; 15 to 40 parts by weight of an organic solvent; 2 to 5 parts by weight of inorganic particles; And 1 to 3 parts by weight of a natural oil,
Wherein the carbazole compound and the organic solvent are contained in a weight ratio of 1: 1 to 1: 4. The method according to claim 1,
The natural oils include ally isothiocyanate, cinnamaldehyde, garlic oil, rosemary oil, jojoba oil, and carrot seed oil. Selected from the group consisting of
Antimicrobial coating composition. The method according to claim 1,
The organic solvent is selected from the group consisting of an alcohol solvent, a halogen-containing hydrocarbon solvent, a ketone solvent, a cellosolve solvent and an amide solvent
Antimicrobial coating composition. Plastic substrates; And
And a coating layer formed on one or both sides of the plastic substrate,
Wherein the coating layer is formed by forming the antimicrobial coating composition according to claim 1 in a thickness of 10 to 20 mm
Packing material.

Images