Optimal composite antibacterial composition with ensured safety and effectiveness

A synergistic antibacterial composition of DDAC and Si-QAC with silicone oil addresses the limitations of existing agents by providing long-lasting efficacy against multi-drug resistant bacteria and fungi while ensuring safety and environmental sustainability.

WO2026034926A1PCT designated stage Publication Date: 2026-02-12R2ELAB INC
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Patent Information

Application Number
PCT/KR2025/011581
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-11-12
Filing Date
2025-08-04
Publication Date
2026-02-12

AI Technical Summary

Technical Problem

Existing antibacterial agents face limitations such as limited effectiveness against multi-drug resistant bacteria and fungi, short-term activity, and environmental concerns, particularly benzalkonium chloride (BAK) leading to resistant bacteria and health risks.

Method used

A complex antibacterial composition comprising didecyldimethylammonium chloride (DDAC) and 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride (Si-QAC) with silicone oil as a base, providing synergistic bactericidal effects and long-lasting antibacterial properties.

Benefits of technology

The composition effectively inhibits a wide range of multi-drug resistant bacteria and fungi, maintaining antibacterial activity after washing, and is safe for human use, reducing the risk of skin and eye irritation.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention relates to an antibacterial composition. The antibacterial composition according to an embodiment of the present invention has an antibacterial effect against multidrug-resistant strains and is harmless to animals or humans, and comprises: a first antibacterial compound; a second antibacterial compound mixed with the first antibacterial compound to exhibit an antibacterial effect against the strains together with the first antibacterial compound; and a carrier compound supporting the first antibacterial compound and the second antibacterial compound to sustain antibacterial activity, wherein the first antibacterial compound is didecyldimethylammonium chloride (DDAC), and the second antibacterial compound is 3-(trimethoxysilyl)propyldimethyloctadecyl ammonium chloride (Si-QAC).
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Description

Optimal complex antibacterial composition with guaranteed safety and effectiveness

[0001] The present invention relates to a complex antibacterial composition with secured safety and effectiveness, and is an antibacterial composition having an antibacterial effect against multi-drug resistant bacteria and fungi, and having a maximized antibacterial effect using a quaternary ammonium compound as an active ingredient that provides excellent antibacterial properties when applied to sanitary products, wet tissues, etc.

[0002] With rising standards of living and growing concern for health and cleanliness, the development of antibacterial agents to suppress odors and infections caused by microbial growth is essential. Antibacterial agents are already incorporated into filters in air conditioners, air purifiers, and refrigerators. Antibacterial fibers are also recognized as essential in the medical field, including bedding products like shoes, socks, comforters, and blankets, as well as in doctor and nurse uniforms, hospital bed mattresses, and bandages.

[0003] Antibacterial agents currently in development and use include metals, aromatic halogen compounds, quaternary ammonium compounds, phenylamides, natural polymer compounds, and phenolic compounds. However, existing antibacterial agents have limitations, such as limited antibacterial activity against specific microorganisms or short-term effectiveness. Therefore, the development of antibacterial ingredients that maintain long-term antibacterial activity while remaining harmless to the human body is necessary.

[0004] In particular, the spread of multidrug-resistant organisms has emerged as a significant global problem in hospital-acquired infections, posing a serious challenge to healthcare systems. Low- and intermediate-level disinfectants are widely used for surface cleaning and disinfection in healthcare settings to prevent environmental transmission. Furthermore, growing concerns about the environmental impact of biocidal disinfectants are driving the need for effective yet environmentally safe antimicrobials.

[0005] Environmental contamination in healthcare settings is strongly associated with the development of nosocomial infections caused by major pathogens such as methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococci (VRE), Clostridium difficile, carbapenem-resistant carbapenemase-producing Enterobacteriaceae (CR CPE), and Acinetobacter baumannii. Among these pathogens, multidrug-resistant organisms are considered a particularly critical problem because they are associated with severe infections in patients with serious underlying medical conditions. Hand hygiene and environmental management are essential measures to prevent cross-infection in healthcare settings. The importance of hygiene and environmental management has been further highlighted during recent outbreaks of emerging infectious diseases such as severe acute respiratory syndrome (SARS), Middle East respiratory syndrome (MERS), and COVID-19.

[0006] Patients and visitors in healthcare settings are at high risk of exposure to pathogens and infections from contaminated surfaces, due to frequent contact between patients and healthcare professionals, shared medical equipment, and inadequate hand hygiene. Maintaining physical cleanliness of the environment is fundamental to environmental infection control. While completely eliminating microorganisms from surfaces is challenging, ongoing management efforts are essential to minimize the risk of cross-contamination.

[0007] Low- and medium-level disinfectants, such as quaternary ammonium compounds, ethyl or isopropyl alcohol, chlorine-releasing agents, and fortified hydrogen peroxide (3% concentration), are commonly used in hospital disinfection. Unlike flammable substances like alcohol, corrosive substances like chlorine-releasing agents, expensive products like hydrogen peroxide, and highly toxic disinfectants like chlorine, quaternary ammonium compound disinfectants can be widely used in hospital settings.

[0008] Benzalkonium chloride (BAK), a quaternary ammonium compound, has recently been widely used in cleaning agents, coatings, and various consumer products. However, due to environmental concerns, its use is strictly regulated by law (Ministry of Environment Notice No. 2024-89). Furthermore, increased environmental exposure to BAK has led to the emergence of resistant bacteria, posing a significant risk to human health and the ecosystem. Consequently, there is growing interest in the development and application of disinfectants that offer superior antibacterial effects while remaining safe for humans.

[0009] The invention is proposed to solve the above-mentioned problem, and provides an antibacterial composition using a preservative that is harmless to the human body and has antibacterial properties.

[0010] In addition, it is to provide products such as sanitary products to which the above antibacterial composition is applied.

[0011] Other objects and advantages of the present invention will become more apparent from the detailed description, claims and drawings below.

[0012] According to one embodiment of the present invention for achieving the above-described problem, an antibacterial composition has an antibacterial effect against multi-drug resistant strains and is harmless to animals or humans, and comprises a first antibacterial compound, a second antibacterial compound that is mixed with the first antibacterial compound and exhibits an antibacterial effect against the strain together with the first antibacterial compound, and a base compound that supports the first antibacterial compound and the second antibacterial compound to maintain antibacterial activity, wherein the first antibacterial compound is didecyldimethylammonium chloride (DDAC), and the second antibacterial compound is 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride (Si-QAC).

[0013] In the antibacterial composition according to an exemplary embodiment of the present invention, the first antibacterial compound, didecyldimethylammonium chloride, is adsorbed to the cell wall of the strain when in contact with the strain, thereby having a bactericidal effect against the strain.

[0014] In the antibacterial composition according to an exemplary embodiment of the present invention, the second antibacterial compound, 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride, has an antibacterial effect against the strain by damaging the cell wall or cell membrane of the strain when in contact with the strain.

[0015] In an antibacterial composition according to an exemplary embodiment of the present invention, the base compound is silicone oil or polyether-modified silicone oil.

[0016] An antibacterial composition according to an exemplary embodiment of the present invention may include 0.005 wt% to 0.8 wt% of the first antibacterial compound, 0.25 wt% to 4 wt% of the second antibacterial compound, 0.15 wt% to 1.5 wt% of the base compound, and the remainder of purified water, based on 100 wt% of the total composition of the antibacterial composition.

[0017] An antibacterial composition according to an exemplary embodiment of the present invention has an antibacterial effect against Escherichia coli, Klebsiella, Pseudomonas aeruginosa, Acinetobacter, Streptococcus, Staphylococcus aureus, Enterococcus, mold, Clostridium, Bacillus, Mycobacterium or Mycobacterium avium.

[0018] An antibacterial composition according to an exemplary embodiment of the present invention has excellent antibacterial durability, making it suitable for preventing nosocomial infections in hospitals and infectious diseases in multi-use facilities. When applied to textile fabrics or clothing, the antibacterial property can be maintained even after washing, and is effective in producing antibacterial filters and antibacterial protective clothing.

[0019] An antibacterial composition according to an exemplary embodiment of the present invention may not cause skin irritation, corrosion or skin hypersensitivity symptoms in animals.

[0020] An antibacterial composition according to an exemplary embodiment of the present invention may not cause eye irritation or serious eye damage to an animal.

[0021] According to an exemplary embodiment of the present invention, the antibacterial composition harmless to animals may include 0.1 wt% to 0.4 wt% of the first antibacterial compound, 0.5 wt% to 2 wt% of the second antibacterial compound, 0.3 wt% to 0.7% of the base compound, and the remainder of purified water, based on 100 wt% of the total composition of the antibacterial composition.

[0022] A product according to another embodiment of the present invention for achieving the above-described problem may include an antibacterial composition according to the above-described embodiment.

[0023] A product according to an exemplary embodiment of the present invention is a hygiene product or a household chemical product.

[0024] In a product according to an exemplary embodiment of the present invention, the sanitary product is selected from the group consisting of dishwashing detergent, dishwashing detergent, and wet tissue.

[0025] The present invention relates to an antibacterial composition, which has an antibacterial effect against multi-drug resistant bacteria and fungi, and which provides excellent antibacterial properties when applied to sanitary products, wet tissues, etc., and an antibacterial composition with a maximized antibacterial effect using a quaternary ammonium compound as an active ingredient can be provided.

[0026] Figure 1 is an excerpt of the information on toxicity from the material safety data sheet of Manufacturing Example 1 manufactured according to an embodiment of the present invention.

[0027] Figure 2 is an excerpt of the information on toxicity from the material safety data sheet of Manufacturing Example 2 manufactured according to an embodiment of the present invention.

[0028] The advantages and features of the present invention, and the methods for achieving them, will become clear with reference to the embodiments described in detail below together with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below, but may be implemented in various different forms. These embodiments are provided only to ensure that the disclosure of the present invention is complete and to fully inform those skilled in the art of the scope of the invention, and the present invention is defined only by the scope of the claims. Specific details for implementing the present invention will be described in detail with reference to the attached drawings. Regardless of the drawings, the same reference numerals refer to the same components, and "and / or" includes each and all combinations of one or more of the mentioned items.

[0029] The terminology used herein is for the purpose of describing embodiments and is not intended to limit the present invention. In this specification, singular forms also include plural forms, unless specifically stated otherwise. As used herein, the terms "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components in addition to the components mentioned.

[0030] Unless otherwise defined, all terms (including technical and scientific terms) used herein may be used in their common sense to those of ordinary skill in the art to which the present invention pertains. Furthermore, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0031] Hereinafter, an antibacterial composition according to an embodiment of the present invention and a product using the same will be described.

[0032] First, an antibacterial composition according to one embodiment of the present invention has an antibacterial effect against multi-drug resistant strains and is harmless to animals or humans. The antibacterial composition may include a first antibacterial compound, a second antibacterial compound that is mixed with the first antibacterial compound and exhibits an antibacterial effect against the strain together with the first antibacterial compound, and a base compound that supports the first antibacterial compound and the second antibacterial compound to maintain antibacterial activity.

[0033] Here, the first antibacterial compound and the second antibacterial compound may be mainly quaternary ammonium compounds. Here, the first antibacterial compound is didecyldimethylammonium chloride (DDAC), and the second antibacterial compound is 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride (Si-QAC).

[0034] The first antibacterial compound, didecyldimethylammonium chloride (DDAC), is a quaternary ammonium compound, and is characterized by being adsorbed to the cell wall of the strain when in contact with the strain, thereby having a bactericidal effect against the strain.

[0035] Meanwhile, 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride (Si-QAC), a second antibacterial compound that is mixed with the first antibacterial compound and exhibits a synergistic effect (antibacterial activity, bactericidal activity) with the first antibacterial compound in the antibacterial composition, can be characterized by having an antibacterial activity against the strain by damaging the surface of the strain when in contact with the strain.

[0036] An antibacterial composition according to an embodiment of the present invention may include a carrier compound that supports a first antibacterial compound and a second antibacterial compound. The carrier compound may form a carrier for the first antibacterial compound and the second antibacterial compound.

[0037] For this purpose, the base compound is a silicone oil, and may be selected from the group consisting of epoxy-modified silicone oil, amino-modified silicone oil, carboxy-modified silicone oil, polyether-modified silicone oil, and alkyl-modified silicone oil.

[0038] While the embodiments of the present invention have been described above, the present invention is not limited to the above embodiments, but can be manufactured in various different forms. Those skilled in the art will understand that the present invention can be implemented in other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood to be illustrative in all respects and not restrictive.

[0039] The content of each component of the antibacterial composition according to one embodiment of the present invention is as follows. That is, the antibacterial composition may include 0.005 wt% to 0.8 wt% of the first antibacterial compound, 0.25 wt% to 4 wt% of the second antibacterial compound, 0.15 wt% to 1.5 wt% of the base compound, and the remainder of purified water, based on 100 wt% of the total composition of the antibacterial composition.

[0040] In the antibacterial composition, the content of the first antibacterial compound is 0.005 wt% to 0.8 wt%. When the content of the first antibacterial compound is less than 0.005 wt%, the content of the first antibacterial compound in the antibacterial composition is minimal, and thus the antibacterial and sterilizing effects of the antibacterial composition may be reduced. When the content of the first antibacterial compound exceeds 0.8 wt%, the toxicity of the antibacterial composition may be enhanced, and thus the antibacterial effect of the antibacterial composition may be reduced. In the antibacterial composition, the content of the second antibacterial compound is 0.25 wt% to 4 wt%. When the content of the second antibacterial compound is less than 0.25 wt%, the content of the second antibacterial compound in the antibacterial composition is minimal, and thus the antibacterial effect of the antibacterial composition may be reduced. When the content of the second antibacterial compound exceeds 4 wt%, the toxicity of the antibacterial composition as a whole may be enhanced, and thus the antibacterial effect may be reduced.

[0041] In the antibacterial composition, the content of the base compound is 0.15 wt% to 1.5 wt%. When the content of the base compound is less than 0.15 wt%, the carrier formed by the base compound may have difficulty sufficiently supporting the first antibacterial compound and the second antibacterial compound. When the content of the base compound exceeds 1.5 wt%, the carrier may be included in the antibacterial composition more than necessary, and the viscosity of the antibacterial composition may increase, which may cause processing difficulties when applying the antibacterial composition to a product (e.g., wet tissue, etc.).

[0042] Preferably, the antibacterial composition may include 0.05 wt% to 0.8 wt% of the first antibacterial compound, 0.25 wt% to 4 wt% of the second antibacterial compound, 0.15 wt% to 1.5 wt% of the base compound, and the remainder of purified water, based on 100 wt% of the total composition.

[0043] The antibacterial composition of the present invention is harmless to animals, and for this purpose, it may preferably include 0.1 wt% to 0.4 wt% of the first antibacterial compound, 0.5 wt% to 2 wt% of the second antibacterial compound, 0.3 wt% to 0.7% of the base compound, and the remainder of purified water, based on 100 wt% of the total composition of the antibacterial composition.

[0044] The antibacterial composition according to an embodiment of the present invention is characterized by having an antibacterial effect against Escherichia coli, Klebsiella, Pseudomonas aeruginosa, Acinetobacter, Streptococcus, Staphylococcus aureus, Enterococcus, mold, Clostridium, Bacillus, Mycobacterium, which is a pathogen of tuberculosis, Bacillus cereus, and Mycobacterium avium complex.

[0045] In addition, the antibacterial composition according to an embodiment of the present invention may have a time-dependent bactericidal effect against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Enterococcus faecium.

[0046] The present invention provides a product comprising the antibacterial composition. In the present invention, the product comprises a product treated with the antibacterial composition, and may be, but is not limited to, a cosmetic, a hygiene product, or a household chemical product.

[0047] In the present invention, the cosmetic refers to an article that is applied to the human body, rubbed, sprayed, or used in a similar manner to cleanse or beautify the human body, add charm, brighten the appearance, or maintain or improve the health of the skin or hair, and has a mild effect on the human body.

[0048] In the present invention, the sanitary products refer to products that require special sanitary management to ensure health and hygiene.

[0049] In the present invention, the above-mentioned household chemical product refers to a chemical product used in everyday living spaces such as hospitals, homes, offices, and multi-use facilities, which has the potential to cause exposure of people or the environment to chemical substances.

[0050] In the present invention, products containing the antibacterial composition include products coated with the antibacterial composition, and include, but are not limited to, various fabrics, special paper, filters, covers, curtains, cases, clothing, protective clothing, and protective equipment.

[0051] In the present invention, the cosmetic may be manufactured in any formulation commonly manufactured in the art according to the Cosmetics Act, and may be formulated as any one selected from the group consisting of a solution, a suspension, an emulsion, a paste, a gel, a cream, a pact, a powder, an emulsion foundation, a wax foundation, a spray, a soap, a facial cleansing, a body cleansing, a hair shampoo, and a hair rinse, but is not limited thereto. More specifically, the cosmetic may be manufactured in the form of a flexible toner, a nourishing toner, a cream, a nourishing cream, a massage cream, a lipstick, a pact, an essence, an eye cream, a cleansing cream, a cleansing foam, a cleansing water, a pack, or a spray.

[0052] In the present invention, the sanitary product may be selected from the group consisting of dishwashing detergent, dishwashing detergent, and wet tissue according to the Sanitary Product Management Act, but is not limited thereto.

[0053] In the present invention, the household chemical product may be selected from the group consisting of laundry detergent, residential space cleaner, deodorizer, air cleaner, indoor air freshener, fragrance, fabric softener, multi-purpose cleaning product, sterilizing product, antibacterial product, disinfectant product, and bactericide according to the Act on Safety Management of Household Chemical Products and Biocides, and includes, but is not limited to, an antibacterial coating agent for professional use in multi-use facilities, an antibacterial coating agent for consumer use, a product exclusively for preventing mold, and an antibacterial coating product for pet supplies.

[0054] Hereinafter, the present invention will be described in more detail through examples. These examples are intended solely to illustrate the present invention, and it will be apparent to those skilled in the art that the scope of the present invention is not limited by these examples.

[0055]

[0056] [Experimental Example: Materials and Methods - Multidrug-Resistant Strains and Pathogenic Strain Library]

[0057] The experiments conducted for this invention were approved by the Institutional Review Board (IRB) of Seoul St. Mary's Hospital (Approval Number: KC24EIDI0125). Prior consent was not required for this experiment. A total of 188 multidrug-resistant bacterial and fungal strains were constructed into a multidrug-resistant strain library. This library comprised strains isolated from clinical and environmental sources at a tertiary university hospital, as well as strains obtained from the Korea Center for Clinical Trials (KCTC) and the National Center for Clinical Pathogens (NCCP).

[0058] Most bacterial strains were cultured on tryptic soy agar or tryptic soy broth (TSA or TSB, BD Korea, Seoul) in an incubator at 35°C. Streptococcus and Listeria strains were inoculated onto blood agar (BAP, Deoksan, Korea) and incubated for 24 h in a 5% CO2 incubator. Legionella was cultured on BCYE agar (MBcell, Seoul, Korea), and fungi and Candida were cultured on Sabouraud dextrose agar (SDA, BD Korea, Seoul) for more than 48 h. Clostridium was cultured anaerobically in Reinforced Clostridial Medium (BD Korea, Seoul) under restricted air conditions at 35°C in a CO2 incubator for more than 1 week. After confirming endospore formation, the cultures were resuspended in distilled water (DW) for the experiment. Bacillus was cultured on nutrient agar (NA, BD Korea, Seoul) at 35°C for more than one week. After confirming endospore formation, the culture was resuspended in distilled water (DW) for experimental procedures. Mycobacterium was cultured on 7H10 agar (BD Korea, Seoul) in an incubator at 35°C for more than 14 days before use in the experiments.

[0059]

[0060] [Experimental Results-1: Rapid Antibacterial Evaluation of Antibacterial Wet Wipes Against Multidrug-Resistant and Pathogenic Strains]

[0061] 1) Experiment preparation

[0062] Three commercially available antibacterial wipes were selected for the present invention and research: A (DDAC 0.31 wt%, Si-QAC 0.45 wt%), B (DDAC 0.5 wt%, BAK 0.9 wt%), and C (BAK 0.63 wt%).

[0063] Here, DDAC is didecyldimethylammonium chloride, Si-QAC is 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride, and BAK is benzalkonium chloride.

[0064] After culturing the bacterial strains in 3 ml of TSB or BAP, BCYE agar for 24 hours, the suspension was resuspended in McFarland 0.5 standard (1x10 8 CFU / ml, measured at 600 nm using a spectrophotometer. The adjusted suspension was diluted 100-fold in 0.85% NaCl to a final concentration of 1x10 6 It was made into CFU / ml.

[0065] For experimental purposes, each wipe was divided into eighths to ensure that the same amount of disinfectant was applied to the surface. As a positive control, a 20 mg / ml stock solution of didecyldimethylammonium chloride (DDAC, Merk Korea, Seoul) was prepared, and 10 μl (0.2 mg) of this stock solution was used. A 48-well plate was prepared and configured with a negative control well, wells wiped with three antibacterial wipes, and wells containing 10 μl of DDAC. Each well was inoculated with 120 μl of the diluted bacterial suspension. Three μl samples were collected at 5, 15, 30, and 1 hour after inoculation and spread onto square tryptic soy agar (TSA, BD Korea, Seoul) plates. The plates were then incubated for 24 h, and bacterial growth was visually assessed.

[0066]

[0067] 2) Results

[0068] The rapid antibacterial activity of three commercially available antibacterial wipes was evaluated. At 15 minutes, no statistically significant difference was observed between wipes A and C (P=0.0823). In contrast, significant differences were observed between wipes A and B (P<0.0001) and between wipes B and C (P<0.0001). At 30 minutes, no significant difference was observed between wipes A and C (P=0.3160). However, significant differences were observed between wipes A and B (P<0.0001) and between wipes B and C (P<0.0001). After 1 hour, no significant difference was observed between wipes A and C (P=0.8234). In contrast, significant differences were observed between wipes A and B (P<0.0001) and between wipes B and C (P<0.0001). Overall, wet wipes A and C showed comparable antibacterial effects, except for wet wipe B.

[0069] When evaluating the Gram-negative strain Escherichia coli, wet tissue A showed 99% antibacterial efficacy against 46% (n=6 / 13) of the strains at 15 minutes and 61% (n=8 / 13) of the strains after 1 hour.

[0070] Against Klebsiella strains, wet tissue A showed 99% antibacterial efficacy against 69% (n=9 / 13) of the strains at 15 minutes, and 100% (n=13 / 13) of the strains at 1 hour. After 1 hour of exposure to wet tissue B, 99% antibacterial efficacy was observed against 15% (n=2 / 13) of the Escherichia coli strains, and 54% (n=7 / 13) of the Klebsiella strains. Wet tissue C showed 99% bactericidal efficacy against both Escherichia coli and Klebsiella strains, with 92% (n=12 / 13) of the strains after 5 minutes.

[0071] Against Pseudomonas aeruginosa strains, wet wipe A showed 99% bactericidal efficacy against 50% (n=5 / 10) of the strains at 15 minutes and against 70% (n=7 / 10) of the strains at 1 hour. Against Pseudomonas aeruginosa strains, wet wipe A showed 99% antibacterial efficacy against 50% (n=5 / 10) of the strains at 15 minutes and against 70% (n=7 / 10) of the strains at 1 hour. For wet wipe B, 99% antibacterial efficacy was observed against only 50% (n=5 / 10) of the strains at 1 hour for both strains. Wet tissue C achieved 99% antibacterial efficacy against 60% (n=6 / 10) of the strains at 15 minutes, increasing to 70% (n=7 / 10) after 1 hour.

[0072] Against Acinetobacter strains, wet wipe C showed 99% antibacterial efficacy against 100% (n=10 / 10) of the strains after 5 minutes. Wet wipe A showed 99% antibacterial efficacy against 90% (n=9 / 10) of the strains at 15 minutes, and against 100% (n=10 / 10) of the strains after 1 hour. Wet wipe B showed 99% antibacterial efficacy against only 50% (n=5 / 10) of the strains at 1 hour for both strains.

[0073] Against the Gram-positive strain Streptococcus, wet wipes A and C showed 99% antibacterial efficacy against 100% (n=11 / 11) of the strains after 5 minutes. In contrast, wet wipe B showed 99% antibacterial efficacy against 82% (n=9 / 11) of the strains.

[0074] Against Staphylococcus aureus strains, wet wipe A achieved 99% antibacterial efficacy against 93% (n=14 / 15) of the strains at 5 minutes. Wet wipe C showed 99% antibacterial efficacy against 100% (n=11 / 11) of the strains at 5 minutes. In contrast, wet wipe B showed 99% antibacterial efficacy against 47% (n=7 / 15) of the strains at 15 minutes, which increased to 67% (n=10 / 15) after 1 hour.

[0075] Against Enterococcus strains, wet wipe A showed 99% antibacterial efficacy against 94% (n=15 / 16) of the strains at 15 minutes, and 100% (n=16 / 16) of the strains after 1 hour. Wet wipe C showed 99% antibacterial efficacy against 100% (n=16 / 16) of the strains after 5 minutes. In contrast, wet wipe B achieved 99% antibacterial efficacy against only 31% (n=5 / 16) of the strains at 1 hour.

[0076] Analysis of the antibacterial efficacy of wet wipes A and C against fungi revealed that wet wipe A showed significantly higher efficacy than wet wipe C at 15 minutes (P=0.0043), 30 minutes (P=0.0029), and 1 hour (P=0.0388). Specifically, wet wipe A achieved 99% antibacterial efficacy against 37% (n=10 / 27) of strains at 15 minutes, which increased to 82% (n=22 / 27) after 1 hour. On the other hand, wet wipe C showed 99% antibacterial efficacy against 30% (n=8 / 27) of strains at 15 minutes, and was effective against 67% (n=18 / 27) of strains after 1 hour.

[0077] In particular, wet wipe A exhibited excellent antibacterial efficacy against spore-forming Clostridium and Bacillus, as well as Mycobacterium, the pathogen of tuberculosis. Meanwhile, Bacillus cereus showed no antibacterial efficacy with wet wipe B or C within 30 minutes, and Mycobacterium avium did not show antibacterial efficacy with these wipes for up to 1 hour.

[0078]

[0079] [Experimental Results-2: Evaluation of Minimum Inhibitory Concentrations for Quaternary Ammonium Compounds]

[0080] 1) Experiment preparation

[0081] Minimum inhibitory concentrations (MICs) were determined using the culture microdilution method according to guidelines established by the Clinical and Laboratory Standards Institute (CLSI). Disinfectant resistance testing was performed on 175 strains selected from a multidrug-resistant strain library. The culture protocol for these strains was consistent with that used for rapid bactericidal testing.

[0082] Stock solutions of quaternary ammonium compounds were prepared at a concentration of 20,000 μg / ml for DDAC and 53,000 μg / ml for benzalkonium chloride (BAK, Merk Korea, Seoul). A dilution series from 1 to 128 μg / ml was then prepared. 100 μl of each disinfectant concentration was added to a 96-well plate. The bacterial suspension was diluted 100-fold to obtain a concentration of 1 x 10 6 After adjusting to , 100 μl of this dilution was added to each well. The plates were incubated at 37°C for 24 h. Disinfectants and bacterial suspensions were diluted using Mueller-Hinton medium (MHB, BD Korea, Seoul). After incubation, the MIC was visually assessed. The MIC for each bacterial strain 50 The values ​​were determined and the MIC differences in resistance between the two disinfectants were compared.50 was defined as the concentration at which 50% of strains within a particular species were inhibited.

[0083]

[0084] 2) Results

[0085] Quantitative analysis of the minimum inhibitory concentrations (MICs) of DDAC and BAK revealed that the MIC values ​​of DDAC were generally two to three times lower than those of BAK. In particular, DDAC consistently showed lower MIC values ​​than BAK against Gram-negative bacteria, with the difference often reaching threefold.

[0086] According to the compared MIC50 values, the MIC for Escherichia coli was 4 μg / mL for DDAC and 32 μg / mL for BAK; the MIC for Klebsiella was 8 μg / mL for DDAC and 32 μg / mL for BAK; the MIC for Pseudomonas aeruginosa was 8 μg / mL for DDAC and 64 μg / mL for BAK; and the MIC for Acinetobacter baumannii was 4 μg / mL for DDAC and 16 μg / mL for BAK. In the case of Gram-positive bacteria, the MIC value for DDAC was similar to or slightly lower than that for BAK. Comparing the MIC50 values, the MIC for Staphylococcus aureus was 2 μg / mL for both DDAC and BAK, the MIC for Enterococcus was 2 μg / mL for DDAC and 4 μg / mL for BAK, and the MIC for S. epidermidis was 2 μg / mL for both DDAC and BAK.

[0087] The MIC for Streptococcus was also 2 μg / mL for both DDAC and BAK, and the MIC for Listeria monocytogenes was 2 μg / mL for DDAC and 4 μg / mL for BAK. In the case of fungi, DDAC showed a lower MIC value than BAK, and similar to the results for Gram-negative bacteria, the difference was approximately 2-fold. As a result of analyzing the MIC50 values, the MIC for Aspergillus was 2 μg / mL for DDAC and 8 μg / mL for BAK, the MIC for Fusarium and Mucorales was 4 μg / mL for DDAC and 16 μg / mL for BAK, and the MIC for Candida was 2 μg / mL for DDAC and 8 μg / mL for BAK.

[0088]

[0089] [Experimental Results-3: Time Sterilization Test of Quaternary Ammonium Compounds]

[0090] 1) Experiment preparation

[0091] Based on the rapid sterilization results for multidrug-resistant strains, two strains each of representative Gram-negative and Gram-positive bacteria, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Enterococcus faecium, were selected.

[0092] The strain was cultured in 3 ml of TSB for 24 h, then inoculated into McF 0.5 (1x10 6, spectrophotometer 600 nm) were diluted in TSCS (tryptone chloride solution) medium. When QAC was used alone, DDAC stock solution with a concentration of 20,000 μg / ml was prepared and inoculated to a final concentration of 1 / 2 MIC. SI-QAC was first coated on a 6-well plate and then dried before use. In the case of combination therapy, the wells were first coated with SI-QAC, dried, and then 10 μl of DDAC was added to a final concentration of 1 / 2 MIC to form the combination. 1 ml of the diluted bacterial suspension was inoculated into each well of the prepared 6-well plate according to each treatment. 100 μl samples were collected at 15, 30, 1, 2, and 3 hours during incubation in a 37°C incubator, and the remaining disinfectant was neutralized before use. Neutralization was performed by membrane filtration using Amicon Ultra 0.5 ml (100 kJ, Millipore, Merk Korea, Seoul), and the dilution used was TSCS (21). The neutralized samples were serially diluted in PBS, and 10 μl of each dilution was plated on square TSA agar plates. After 24 h of incubation, the number of viable cells was determined.

[0093]

[0094] 2) Results

[0095] For Escherichia coli, the selected strains were CRE (CV_BS_EC1) and non-CRE (CV_BS_EC7). For Pseudomonas aeruginosa, the selected strains were CRE (CV_BS_P29) and non-CRE (CV_BS_P34). For Staphylococcus aureus, the selected strains were MRSA (CV_BS_S48) and VISA (CV_BS_S60). Finally, for Enterococcus faecium, the selected strains were VSE (CV_BS_EF63) and VRE (CV_BS_EF65).

[0096] Time-kill curve tests against Escherichia coli showed that for the CRE strain (CV_BS_EC1), the log10 value at 0 h decreased from 6.24 to 6.26 after 3 h with DDAC, 5.15 with Si-QAC, and 4.23 with the DDAC and Si-QAC combination therapy (DDAC + Si-QAC), reflecting a 2-log reduction. For the non-CRE strain (CV_BS_EC7), the log10 value at 0 h decreased from 6.23 to 3.00 with DDAC, 5.06 with Si-QAC, and 3.18 with DDAC + Si-QAC after 3 h, reflecting a 3-log reduction.

[0097] In the time-kill curve test against Pseudomonas aeruginosa, for the CRE strain (CV_BS_P29), the log10 value at 0 h decreased from 6.27 to 5.36 with DDAC, 5.65 with Si-QAC, and 5.19 with DDAC + Si-QAC after 3 h, corresponding to a 1-log reduction. For the non-CRE strain (CV_BS_P34), the log10 value at 0 h decreased from 6.63 to 4.58 with DDAC, 5.11 with Si-QAC, and 4.40 with DDAC + Si-QAC after 3 h, corresponding to a 2-log reduction.

[0098] The time-kill curve test results for Staphylococcus aureus showed that for the MRSA strain (CV_BS_S48), the log10 value at 0 h decreased from 6.94 to 4.29 with DDAC, 2.02 with Si-QAC, and 1.00 with DDAC + Si-QAC after 3 h, reflecting a reduction of more than 5 logs. For the VISA strain (CV_BS_S60), the log10 value at 0 h decreased from 6.27 to 4.13 with DDAC, 3.52 with Si-QAC, and 3.15 with DDAC + Si-QAC after 3 h, reflecting a reduction of approximately 3 logs.

[0099] Time-kill curve tests against Enterococcus faecium showed that for the VSE strain (CV_BS_EF63), the log10 value decreased from 6.76 at 0 h to 6.90 with DDAC, and to 2.00 after 3 h with Si-QAC and DDAC + Si-QAC, representing a reduction of approximately 4 logs. Similarly, for the VRE strain (CV_BS_EF65), the log10 value decreased from 6.99 at 0 h to 3.90 with DDAC, and to 2.00 after 3 h with Si-QAC and DDAC + Si-QAC, also reflecting a reduction of approximately 4 logs.

[0100]

[0101] [Experimental Results-4: Antibacterial Durability Test]

[0102] After preparing antibacterial compositions as shown in Table 1 below, the antibacterial persistence of each antibacterial composition was evaluated. In other words, the antibacterial persistence by the carrier, which is a base compound, was tested.

[0103] Each antibacterial composition manufactured according to the manufacturing example in Table 1 below was inoculated with strain 1 (Staphylococuus aureus) and strain 2 (Escherichia coli) and cultured, and the results are shown in Table 2 below.

[0104]

[0105]

[0106] Material Example (content wt%) Comparative Example (content wt%) 123133DDAC0.310.310.310.310.310.31Si-QAC0.50.50.50.50.50.5Polyether modified silicone oil0.150.71.5-0.12

[0107] Strain 1 Strain 2 Viscosity aba b Example 199.999.999.999.9○299.999.999.999.9○399.999.999.999.9○ Comparative Example 199.90.5x10 6 99.90.7x10 6○299.90.3x10 5 99.90.6x10 5 ○399.999.999.999.9◎

[0108] Here, a: strain 1x10 6 24 hours after CFU / ml inoculation

[0109] b: 24 hours after the first inoculation, 1x10 strains were added to the same medium. 6 24 hours after CFU / ml inoculation

[0110] ○: Soft viscosity / ◎: Strong viscosity

[0111] As can be seen from the above comparison, when the base compound is added in the examples of the present invention, the antibacterial effect is sustained, and the viscosity is not strong, so the processability is also excellent.

[0112]

[0113] In addition, in order to confirm the coating durability of the antibacterial composition of Example 2 manufactured according to the manufacturing example of Table 1, the substrate coated with the antibacterial composition was treated with a wet tissue once, five times, and ten times, touched 10 times, 50 times, and 100 times, wiped with alcohol once, five times, and ten times, and treated under harsh conditions to confirm whether the antibacterial power against strain 1 (Staphylococuus aureus) was maintained (Table 3).

[0114]

[0115] Classification antibacterial activity value * (Strain 1) Example 2 Wet tissue 1 time 5.6 (99.9%)**Wet tissue 5 times 5.6 (99.9%)**Wet tissue 10 times 5.6 (99.9%)**Hand touch 10 times 5.6 (99.9%)**Hand touch 50 times 4.1 (99.9%)**Hand touch 100 times 5.6 (99.9%)**Alcohol 1 time 5.6 (99.9%)**Alcohol 5 times 4.3 (99.9%)**Alcohol 10 times 5.6 (99.9%)**Harsh treatment 5.6 (99.9%)**

[0116] * If the antibacterial activity value is ≥2.0, there is an antibacterial effect.

[0117] ** % calculation = (1-10-(Log10reduction))X100

[0118] As a result, it was found that the example compound of the present invention maintained the coating for a long period of time and had excellent antibacterial properties.

[0119]

[0120] [Experimental Results-5: Risk Assessment]

[0121] For the antibacterial composition according to the present invention, Manufacturing Examples 1 and 2 for product application were manufactured. The implementation aspects of each Manufacturing Example are shown in Table 3. In addition, after manufacturing each Manufacturing Example, a risk assessment was conducted for each Manufacturing Example. The results of the risk assessment for each Manufacturing Example are shown in Table 4, Figures 1 and 2 below. Figure 1 is an excerpt of the information on toxicity from the Material Safety Data Sheet of Manufacturing Example 1, and Figure 2 is an excerpt of the information on toxicity from the Material Safety Data Sheet of Manufacturing Example 2.

[0122]

[0123] Materials used Manufacturing example 1 Manufacturing example 2 Purified water 96.69 97.15 Didecyldimethylammonium chloride 0.18 0.43 -(Trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride 2.0 0.5 Polyether-modified silicone oil 0.6 3 0.7

[0124] Hazard assessment items Manufacturing example 1 Manufacturing example 2 Inhalation toxicity Results of acute inhalation toxicity test using male rats, lethal dose > 5 mg / L, category 5 / unclassified - Oral toxicity Results of acute oral toxicity test using female rats, lethal dose > 2000 mg / kg bw Results of acute oral toxicity test using female rats, lethal dose > 2000 mg / kg bw Dermal toxicity Results of acute dermal toxicity test using female rats, GHS category 5 / unclassified Results of acute dermal toxicity test using female rats, GHS category 5 / unclassified Skin irritation and corrosion Results of skin irritation and corrosion test using rabbits, no irritation and corrosion Results of skin irritation and corrosion test using rabbits, no irritation and corrosion Eye irritation and serious eye damage Results of eye irritation and serious eye damage test using rabbits, no eye irritation Eye irritation using rabbits And serious eye damage test results, no eye irritation. Skin sensitization. Skin sensitization test using male guinea pigs, evaluated as a non-sensitizing substance classified as very weak. Skin sensitization test using male guinea pigs, evaluated as a non-sensitizing substance classified as very weak.

[0125] As can be seen from Table 4, Figures 1 and 2 above, the antibacterial composition of the present invention was found to be harmless to animals in various risk assessment items as a result of animal testing. Therefore, it can be indirectly determined that a product using the antibacterial composition of the present invention will be harmless even if used on the human body. In other words, it can be seen that the antibacterial composition of the present invention is a material that has excellent antibacterial effects while being harmless to humans and animals. Therefore, it has the potential to be widely applied to sanitary products, household chemical products, wet tissues, etc.

Claims

1. In an antibacterial composition that has an antibacterial effect against multidrug-resistant strains and is harmless to animals, The first antibacterial compound, A second antibacterial compound that is mixed with the first antibacterial compound and exhibits an antibacterial effect against the strain together with the first antibacterial compound, A base compound that supports the first antibacterial compound and the second antibacterial compound to maintain antibacterial activity, The above first antibacterial compound is a quaternary ammonium compound, The second antibacterial compound is an organosilane-quaternary ammonium compound, The above-described compound is an antibacterial composition containing silicone oil.

2. In paragraph 1, The first antibacterial compound is didecyldimethylammonium chloride (DDAC), The second antibacterial compound is an antibacterial composition comprising 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride (Si-QAC).

3. In paragraph 2, An antibacterial composition characterized in that the first antibacterial compound, didecyldimethylammonium chloride, is adsorbed to the cell wall of the strain when in contact with the strain and has a bactericidal effect against the strain.

4. In paragraph 2, An antibacterial composition characterized in that the second antibacterial compound, 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride, has antibacterial activity against the strain by damaging the cell wall or cell membrane of the strain when it comes into contact with the strain.

5. In paragraph 1, An antibacterial composition characterized in that the above silicone oil is a polyether modified silicone oil.

6. In paragraph 1, The above antibacterial composition is, for 100 wt% of the total composition of the above antibacterial composition, An antibacterial composition comprising 0.005 wt% to 0.8 wt% of the first antibacterial compound, 0.25 wt% to 4 wt% of the second antibacterial compound, 0.15 wt% to 1.5 wt% of the base compound, and the remainder of purified water.

7. In paragraph 1, The above antibacterial composition is characterized in that it has an antibacterial effect against Escherichia coli, Klebsiella, Pseudomonas aeruginosa, Acinetobacter, Streptococcus, Staphylococcus aureus, Enterococcus, mold, Clostridium, Bacillus, Mycobacterium or Mycobacterium avium complex.

8. In paragraph 1, An antibacterial composition characterized in that the above antibacterial composition does not cause skin irritation, corrosion, or skin hypersensitivity symptoms in animals.

9. In paragraph 1, An antibacterial composition characterized in that the above antibacterial composition does not cause eye irritation or serious eye damage to animals.

10. A product containing an antibacterial composition according to paragraph 1.

11. In paragraph 10, The above product is characterized as being a sanitary product or a household chemical product.

12. In paragraph 11, The above household chemical product is a product selected from the group consisting of antibacterial coating agents for professional use in multi-use facilities, antibacterial coating agents for consumer use, products for mold prevention, and antibacterial coating products for pet supplies.

13. In paragraph 10, The above product is a product selected from the group consisting of fabrics, special paper, filters, covers, curtains, cases and clothing coated with an antibacterial composition.

14. In paragraph 10, The above product is a product selected from the group consisting of protective clothing and protective equipment coated with an antibacterial composition.

Citation Information

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