Bactericidal and preservative composition

Abstract

The invention relates to a composition for antibiosis, sterilization and preservation and a product containing the same, and the composition is used for protecting the quality of products in various industrial fields from being damaged by microorganisms. Comprising a family care product group such as a clothes cleaning agent, a dish cleaning agent and a living space cleaning agent, a personal care product group such as a shampoo, a shower gel, a wet tissue and a cleaning product, and a cosmetic product group such as a face cream and an emulsion. The composition for antibiosis and preservation of the present invention comprises a compound represented by chemical formula 1, a compound represented by chemical formula 2, a compound represented by chemical formula 3 or a compound represented by chemical formula 4, so that the problems of harm to human bodies, skin irritation and the like can be solved, and at the same time, the antibacterial ability can be improved. Furthermore, the hair care cosmetic composition for preventing dandruff or the antifungal composition of the present invention, comprising the compound represented by chemical formula 1, has an effect of controlling dandruff fungi, and has a synergistic effect when the compound represented by chemical formula 1 is used together with an expensive dandruff fungus therapeutic agent such as piroctone olamine salt, zinc pyrithione or clomidazole. Moreover, the antiviral composition comprising the compound represented by chemical formula 1 according to the present invention can effectively control microorganisms such as viruses, and thus can be used as an eco-friendly epidemic prevention composition for controlling viruses.

Description

Technical Field

[0001] The present invention relates to an antibacterial, sterilizing and preservative composition and a product containing the same. The composition is used to protect the quality of products in various industrial fields from microbial damage, including household care products such as laundry detergents, dishwashing detergents, and living space cleaners, personal care products such as shampoos, shower gels, wet wipes, and cleaning products, and cosmetic products such as creams and lotions.

[0002] Also, the present invention relates to a hair care cosmetic composition for preventing dandruff and an antiviral composition for removing dandruff fungus. Background Art

[0003] All products containing water must use antimicrobial agents because they are prone to the growth of microorganisms. Antimicrobial agents are agents that inhibit the growth of bacteria or kill bacteria.

[0004] In particular, cleaning products containing large amounts of water must contain preservatives to prevent microbial growth and spoilage, as well as antimicrobial agents to eliminate microorganisms that could be a source of contamination, in order to maintain their quality over time. Antimicrobial agents are essential because these products have a very long shelf life, are highly likely to come into contact with microorganisms during use and storage, contain various carbon and nitrogen sources, and require high levels of water for microbial growth.

[0005] The harmful effects of antimicrobials on the human body have recently become a matter of debate. However, when products do not use antimicrobials or have weak antimicrobial properties, not only are there high risks of product deterioration and the spread of infectious pathogens, but they can also cause skin problems and diseases caused by microbial metabolism. Therefore, the use of antimicrobials is unavoidable.

[0006] Toxic chemicals such as isothiazolinone, including methylisothiazolinone, chloromethylisothiazolinone, and 1,2-benzisothiazol-3(2H)-one, are still used for the preservation of clothing and dishes, in cleaning and fragrance products for living spaces, wet wipes, shampoos, and cosmetics (face creams, lipsticks, etc.).

[0007] Isothiazolinones, toxic chemicals widely used because they are affordable and potent, are facing increasing regulation due to their potential carcinogenicity.

[0008] In recent years, South Korea has been strengthening regulations for each product group due to the potential impact of antimicrobials on public health. While these efforts are accelerating, with initiatives such as classifying wipes as other hygiene products under the Hygiene Products Management Act and the Ministry of Food and Drug Safety notifying the public of ingredients that can be used in kitchen cleaners, the use of these highly safe and effective antimicrobials is shrinking due to inappropriate use.

[0009] On the other hand, in the complexities of modern society, environmental pollution and stress affect the normal shedding of the skin, hair, and scalp, leading to scalp disorders such as dandruff and itching. Dandruff is a condition caused by the breakdown of the bonds between keratinocytes on the scalp, resulting in the shedding of dead skin cells. While not life-threatening, dandruff and itching can affect people's daily lives, affecting their image and causing a loss of self-confidence.

[0010] Dandruff is the most common scalp skin disease. Malassezia fungi are one of the causes of dandruff and are commonly referred to as dandruff fungi. Within the genus Malassezia, species such as Malassezia furfur, Malassezia restricta, and Malassezia globosa are known to be primarily associated with dandruff. Furthermore, various studies worldwide have shown that Malassezia fungi are the dominant species on the scalps of dandruff patients, and reports indicate that the presence of Malassezia increases with symptom severity.

[0011] These shampoos, hair conditioners, hair growth enhancers, etc. that are used to prevent excessive dandruff all contain formulas such as exfoliating solvents, anti-seborrheic agents, and antiseptics. In addition, anti-inflammatory and antipruritic agents are also added to prevent inflammation from worsening. Currently, compounds such as piroctone olamine, pyrithione zinc, and climbazole that are known to be effective for treating dandruff are expensive and are rarely added to cosmetic formulations such as shampoos.

[0012] Meanwhile, various viral prevention products are widely used, and the increasing variety of preventative substances, as they are used in everyday life, necessitates more effective and safer preventative measures. The need to prevent not only bacteria but also viruses such as foot-and-mouth disease and coronaviruses, which are cyclical and increasingly frequent, necessitates the development of substances that are safer than existing preventative substances and the development of preventative agents that utilize substances with broad-spectrum viral protection and relatively low toxicity.

[0013] Among the commercially available products currently approved by the Ministry of Environment, quaternary ammonium salts such as n-alkyldimethylethylbenzyl ammonium chloride, alkylbenzyldimethylammonium chloride (1:1) and benzalkonium chloride are prohibited from use on the human body or items that come into direct contact with the human body, and cannot be used to disinfect food or food containers. Most of these epidemic prevention products are advised not to come into direct contact or be sprayed on humans or livestock, but in reality, avoiding contact is impossible, so there is a need to develop substances that are recognized as safe as possible.

[0014] Therefore, we are committed to developing a sterilizing and preservative agent that can be safely used in cosmetics, sanitary products and daily chemical products, using substances that are non-toxic to the human body and are recognized as environmentally safe, while also having excellent antibacterial and antiviral properties. Summary of the Invention

[0015] Technical issues

[0016] The inventors of the present invention discovered that the compound represented by Chemical Formula 1 has an antibacterial effect during research and development of a method for controlling microorganisms by other means without using existing antibacterial agents that harm the human body in various ways.

[0017] It was also found that when the compound represented by Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4 is mixed with the compound represented by Chemical Formula 1, the microbial control material can be easily mixed into the product dosage form, and compared with the use of each compound alone, a synergistic effect of antibacterial, bactericidal and preservative effects can be provided. It also has the effect of offsetting the reduction in antibacterial, bactericidal and preservative functions caused by the ionicity of the product substrate. Therefore, it is determined that microorganisms can be controlled more effectively, thereby completing the present invention.

[0018] Furthermore, the inventors of the present invention have discovered that the compound represented by Chemical Formula 1 can effectively kill strains of the genus Malassezia, which is a dandruff fungus, and when the compound represented by Chemical Formula 1 is mixed with piroctone olamine, zinc pyrithione, or climbazole, compared with using the compound represented by Chemical Formula 1 alone, it exhibits a synergistic effect in the bactericidal effect against strains of the genus Malassezia, and when applied to hair care cosmetics, the amount of piroctone olamine, zinc pyrithione, and climbazole can be reduced, thereby completing the present invention.

[0019] Furthermore, the inventors of the present invention discovered that the compound represented by Chemical Formula 1 has an antiviral effect in addition to an antibacterial effect during the process of researching and developing a method for controlling viruses by other means without using existing antiviral agents that harm the human body in various ways, thereby completing the present invention.

[0020] Therefore, the present invention aims to develop a bactericidal preservative with antibacterial and antiviral properties.

[0021] Technical Solution

[0022] In order to solve the above-mentioned problems, the present invention discloses the following solutions.

[0023] Specifically, the present invention provides a composition for antibacterial and preservation, comprising a compound as shown in Chemical Formula 1.

[0024] The present invention provides a composition for antibacterial and preservation, comprising: (a) a compound as shown in Chemical Formula 1; and (b) any one of the compounds shown in Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4.

[0025] The present invention provides a product comprising the antibacterial and preservation composition.

[0026] The present invention provides an antibacterial method, comprising the step of treating bacteria using the antibacterial and preservation composition.

[0027] The present invention provides a hair care cosmetic composition for preventing dandruff, comprising a compound as shown in Chemical Formula 1.

[0028] The present invention provides a hair care cosmetic composition for preventing dandruff, comprising: a compound as shown in Chemical Formula 1; and any one compound selected from the group consisting of piroctone olamine, pyrithione zinc, and climbazole.

[0029] The present invention provides an antifungal composition targeting Malassezia sp. strains and comprising a compound as shown in Chemical Formula 1.

[0030] The present invention provides a hair care cosmetic in various dosage forms, comprising the hair care cosmetic composition for preventing dandruff or the composition for antifungal use.

[0031] The present invention provides a method for sterilizing dandruff fungi, comprising the step of treating dandruff fungi using the hair care cosmetic composition for preventing dandruff or the antifungal composition.

[0032] The present invention provides an antiviral composition comprising a compound as shown in Chemical Formula 1.

[0033] The present invention provides an antiviral method, comprising the step of treating viruses with an antiviral composition.

[0034] The antibacterial and preservation composition, the antidandruff composition, and the antiviral composition using the compound represented by Chemical Formula 1 of the present invention exhibit broad microbial control capabilities and have the advantage of being able to solve problems such as harm to the human body and skin irritation caused by preservatives.

[0035] Effects of the Invention

[0036] The synergistic effect of antimicrobial activity can be exhibited by combining the components invented by the present inventors.

[0037] Furthermore, when the antibacterial and preservation composition invented by the present inventors is included in various products such as cosmetics, sanitary products, and daily chemical products, it can contribute to emulsification and solubilization due to the properties of the surfactant and exhibit excellent antibacterial activity and a broad antibacterial spectrum.

[0038] Furthermore, the antibacterial and preservation composition of the present invention can exhibit a wide range of applications because it achieves a wide range of efficacy in anionic and nonionic surfactant-based compositions and cationic surfactant-based compositions.

[0039] Furthermore, the hair care cosmetic composition for preventing dandruff or the antifungal composition of the present invention has an effect of controlling dandruff fungi, and when the compound represented by Chemical Formula 1 is used together with expensive dandruff fungal therapeutic agents such as piroctone olamine, pyrithione zinc, or climbazole, a synergistic effect is achieved, and the amount of these expensive therapeutic agents used can be reduced by more than 50%.

[0040] Furthermore, the antiviral composition of the present invention can effectively control microorganisms such as viruses, and thus can be used as an environmentally friendly and epidemic prevention composition for controlling viruses.

[0041] The effects of the present invention are not limited to the above-mentioned effects, and various effects can be included within the scope that is obvious to those skilled in the art based on the following description. DETAILED DESCRIPTION

[0042] Hereinafter, this specification will be described in more detail.

[0043] The following is a detailed description. On the other hand, each description and embodiment disclosed herein can also be applied to each other description and embodiment. That is, all combinations of the various factors disclosed herein fall within the scope of the present invention. Furthermore, the scope of the present invention should not be considered limited by the following detailed description.

[0044] The expressions such as “including” and the like used in this specification should be understood as open-ended terms implying the possibility of including other embodiments, unless otherwise stated in a sentence or article including the expression.

[0045] The terms or words used in the description of the present invention and the scope of the invention claims should not be interpreted as limited to the conventional meaning or dictionary meaning, and should be interpreted as the meaning and concept that conforms to the technical idea of ​​the present invention based on the principle that the inventor can appropriately define the concept of the term to describe his own invention in the best way.

[0046] Composition for antibacterial and preservation

[0047] The present invention provides a composition for antibacterial and preservation, comprising a compound as shown in Chemical Formula 1.

[0048] Chemical formula 1:

[0049]

[0050] In the chemical formula 1, R1 is a substituted or unsubstituted C7 to C 17 Alkyl, or substituted or unsubstituted C7 to C 17 Alkenyl.

[0051] Furthermore, in the chemical formula 1, R1 is a linear or branched C7 to C 17 Alkyl, linear or branched C7 to C 17 Alkenyl, or C7 to C 17 Hydroxyalkyl.

[0052] More specifically, R1 is a linear or branched C 10-14 Alkyl, linear or branched C 10-14 Alkenyl or C 10-14 Hydroxyalkyl.

[0053] In the present invention, the composition for antibacterial and preservation comprises the compound shown in Chemical Formula 1 as an effective ingredient.

[0054] In the present invention, "active ingredient" refers to an ingredient that can exert the desired activity alone or together with an inactive carrier.

[0055] The present invention provides a composition for antibacterial and preservation, comprising: (a) a compound as shown in Chemical Formula 1; and (b) any one of the compounds shown in Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4.

[0056] Chemical formula 1:

[0057]

[0058] Chemical formula 2:

[0059]

[0060] Chemical formula 3:

[0061]

[0062] Chemical formula 4:

[0063]

[0064] In the chemical formula 1,

[0065] R1 is substituted or unsubstituted C7 to C 17 Alkyl, or substituted or unsubstituted C7 to C 17 alkenyl,

[0066] In the chemical formula 2,

[0067] L1 is -(CH=CH)-, -(CH2) l -, -C(=O)- or -O-,

[0068] R2 is -H, -C(=O)-CH3, -C(=O)H, -OH, -O - Na + 、-(CH2) m -OH, -CH(CH3)-CH2-C(CH3)2-CH3, or substituted or unsubstituted C1 to C6 alkyl,

[0069] R3, R4 and R5 are each independently -H, -OH, C1 to C3 alkoxy, =O, -O - Na + , or a substituted or unsubstituted C1 to C6 alkyl group,

[0070] X and Y are each independently -CH-, -O- or -NR a ,

[0071] R a is -OH,

[0072] Z is NH2-CH2-CH2-OH or does not exist (Null),

[0073] represents a single bond or a double bond,

[0074] K, l, and m are each independently an integer from 1 to 4.

[0075] In the chemical formula 3,

[0076] R6 is -H, substituted or unsubstituted C2 to C 18 Alkyl, or substituted or unsubstituted C2 to C 18 alkenyl,

[0077] L2 is -(CH2) o-, -O- or -C(=O)-,

[0078] R7 is -NHCH-, -N- or C(=O)CHNH-,

[0079] R8 is -OH, COOH, -COOCH3, -COOCH2CH3, -(CH2)4NH- or

[0080] R9 is -H, -(CH2)4NH2 or -(CH2)3C(NH)2NH2,

[0081] A is -H or does not exist (Null),

[0082] n is an integer from 1 to 99,

[0083] o is an integer from 1 to 3,

[0084] In the chemical formula 4,

[0085] L3 is -(CH2) p -, -O-, -C(=O)- or -OC(=O)-,

[0086] R 10 is substituted or unsubstituted C2 to C 10 Alkyl, -OH or -O - Na + ,

[0087] R 11 is one or more selected from -CH2-CHOH-CH 2- , hydroxyl, unsubstituted C1 to C3 alkyl and carboxyl substituted or unsubstituted -(CH2) q -, substituted or unsubstituted -(CH2) r -N(R b )-(CH2) s -, or unsubstituted phenylene (-C6H4-),

[0088] R 12 -OH, -COOH, C1 to C3 alkoxy or -COO - Na + ,

[0089] R b -(CH2) t -N[(CH2) u -CO2-)]2,

[0090] p, q, r, s, t, and u are each independently an integer from 1 to 3.

[0091] In the present invention, the term "composition for antibacterial and preservation" may refer to a preservative composition, which may include all additives that can be used to prevent the composition to which they are added from deteriorating, corrupting, changing color and chemical changes, and may also include functional antibiotics that inhibit the growth of microorganisms such as bacteria, molds, yeasts, etc., to prevent the development of corruptive microorganisms or have a bactericidal effect.

[0092] In the present invention, the above-mentioned composition for antibacterial and preservation may have an antibacterial or antifungal effect on bacteria or fungi, but is not limited thereto.

[0093] In the present invention, the term "antibacterial" refers to the effect of inhibiting or controlling the growth and proliferation of bacteria.

[0094] In the present invention, the term "antifungal" refers to the effect of inhibiting or controlling the growth and proliferation of fungi.

[0095] In the present invention, the composition for antibacterial and preservation may have antibacterial activity against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, methicillin-resistant Staphylococcus aureus, Bacillus subtilis, Vibrio parahaemolyticus, Salmonella typhimurium, Listeria monocytogenes or Shigella flexneri, or antifungal activity against Candida albicans, Aspergillus niger or Aspergillus brasiliensis, but is not limited thereto.

[0096] In the present invention, compounds represented by Chemical Formula 1 or Chemical Formulas 2 to 4 are preservative compounds. The term "preservative" refers to chemical substances added to industrially produced and distributed processed foods, beverages, cosmetics, pharmaceuticals, sanitary products, daily chemical products, and the like to control the quality of these products. These substances are used to prevent microbial spoilage or degradation of chemical components, leading to quality loss or deterioration. Specifically, because they exhibit antimicrobial activity against at least one of bacteria, molds, and yeasts, they are intended to be used as antimicrobial and / or antibacterial and / or antifungal agents.

[0097] In the present invention, the antibacterial and preservative composition can be used to control at least one microorganism selected from the group consisting of Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, methicillin-resistant Staphylococcus aureus, Bacillus subtilis, Vibrio parahaemolyticus, Salmonella typhimurium, Listeria monocytogenes, Shigella flexneri, Candida albicans, Aspergillus niger and Aspergillus brasiliensis, but is not limited thereto.

[0098] Specifically, the antibacterial and preservative composition can be used to control at least one microorganism selected from the group consisting of Escherichia Coli, Staphylococcus Aureus, Pseudomonas Aeruginosa, Aspergillus brasiliensis, and Candida albicans.

[0099] In the present invention, the weight ratio of the compound represented by Chemical Formula 1 to any one of the compounds represented by Chemical Formula 2, Chemical Formula 3, or Chemical Formula 4 may be 0.01:9.99 to 9.99:0.01. Specifically, the weight ratio of the compound represented by Chemical Formula 1 to any one of the compounds represented by Chemical Formula 2, Chemical Formula 3, or Chemical Formula 4 may be 2:8, 4:6, 5:5, 7:3, and / or 8:2, but is not limited thereto.

[0100] Specifically, the content of the compound represented by Chemical Formula 1 and any one of the compounds represented by Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4 is within the above range, thereby having the advantage of improving the microbial control effect.

[0101] In the present invention, 3,3′-(dodecylimino)bispropane-1,2-diol as the compound represented by Chemical Formula 1 has the following chemical formula.

[0102] Chemical formula 1-1:

[0103]

[0104] Specifically, the compound represented by Chemical Formula 1-1 is a surfactant compound having excellent emulsification and solubilization effects, and is mixed with any one of the compounds represented by Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4 to form an antibacterial composition, thereby inhibiting bacteria such as Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, methicillin-resistant Staphylococcus aureus, Bacillus subtilis, Vibrio parahaemolyticus, Salmonella typhimurium, Listeria monocytogenes, Shigella flexneri, Candida albicans, Aspergillus niger, etc. niger) and Aspergillus brasiliensis, and thus can exhibit antibacterial and antifungal properties, and have the advantage of being applicable to various products in liquid and solid forms such as cosmetics, hygiene products, and daily chemical products.

[0105] In the present invention, the compound represented by Chemical Formula 2 may be one or more selected from the group consisting of o-Methoxycinnamaldehyde, 4-Methoxycinnamaldehyde, raspberry ketone, 3-phenyl-1-propanol, hydroxyacetophenone, sodium benzoate, phenoxyethanol, tropolone, piroctone olamine, and sodium dehydroacetate, but is not limited thereto.

[0106] Specifically, the structure of o-Methoxycinnamaldehyde is The structure of 4-Methoxycinnamaldehyde is The structure of raspberry ketone is The structure of 3-phenyl-1-propanol is The structure of 4-Hydroxyacetophenone is The structure of sodium benzoate is The structure of phenoxyethanol is The structure of Tropolone is The structure of Piroctone Olamine is The structure of sodium dehydroacetate is

[0107] In the present invention, the compound represented by Chemical Formula 3 may be one or more selected from the group consisting of lauroyl arginine methyl ester, lauroyl lysine methylester, lauroyl arginine ethyl ester, iodopropynyl butylcarbamate, polylysine, lauroyl lysine, and caprylhydroxamic acid, but is not limited thereto.

[0108] Specifically, the structure of lauroyl arginine methyl ester is The structure of lauroyl lysinemethyl ester is The structure of lauroyl arginine ethyl ester is IodopropynylButylcarbamate The structure of polylysine is The structure of Lauroyl Lysine is The structure of Caprylhydroxamic Acid is

[0109] In the present invention, the compound represented by Chemical Formula 4 may be one or more selected from the group consisting of hexane-1,2-diol, octane-1,2-diol, decane-1,2-diol, ethylhexylglycerin, glyceryl monocaprylate, octyl glycerin, hexyl glycerin, levulinic acid, citric acid, sodium anisate, disodium EDTA, and tetrasodium EDTA, but is not limited thereto.

[0110] Specifically, the structure of Hexane-1,2-diol is The structure of Octane-1,2-diol is The structure of Decane-1,2-diol is The structure of ethylhexylglycerin is The structure of Glyceryl monoCaprylate is The structure of Octyl glycerin is The structure of Hexyl glycerin is The structure of levulinic acid is The structure of citric acid is The structure of Sodium Anisate is The structure of Disodium EDTA is The structure of Tetrasodium EDTA is

[0111] Compared with using any one of the compounds represented by Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4 alone, using the compound represented by Chemical Formula 1 together as a component of the antibacterial and preservative composition can inhibit the growth of microorganisms such as bacteria, molds, and yeasts, thereby preventing the development of spoilage microorganisms and exhibiting a synergistic effect by improving the bactericidal effect.

[0112] Products comprising compositions for antibacterial and preservation purposes

[0113] The present invention provides a product comprising the above composition for antibacterial and preservation.

[0114] In the present invention, the above-mentioned products may be cosmetics, sanitary products or daily chemical products, but are not limited thereto.

[0115] In the present invention, the term "cosmetics" refers to an article that is applied to the human body by smearing, rubbing or spraying or similar methods, and is used to enhance charm and brighten the appearance by cleaning and beautifying the human body, or to maintain or promote the health of the skin and hair, and its effect on the human body is minimal.

[0116] In the present invention, the term "hygienic products" refers to products that require special hygiene supervision to ensure health and hygiene.

[0117] In the present invention, the term "daily chemical products" refers to chemical products used in daily living spaces such as homes, offices, and public facilities, which may cause exposure of chemical substances to humans or the environment.

[0118] In the present invention, the cosmetics can be prepared according to cosmetic methods in any dosage form commonly prepared in the art, and can be prepared as any of the following: solutions, suspensions, emulsions, pastes, gels, creams, pressed powders, loose powders, liquid foundations, stick foundations, sprays, soaps, cleansers, body washes, shampoos, and conditioners, but are not limited thereto. More specifically, the cosmetics can be prepared in the form of toners, nourishing lotions, creams, nourishing creams, massage creams, lipsticks, pressed powders, essences, eye creams, makeup removers, cleansers, makeup removers, sheet masks, or sprays.

[0119] In the present invention, according to the Sanitary Products Management Act, the sanitary products may be selected from the group consisting of dishwashing detergents, dishwasher detergents, and wet wipes, but are not limited thereto.

[0120] In the present invention, according to the relevant laws on the safety management of daily chemical products and biocides, the above-mentioned daily chemical products can be selected from the group consisting of clothing detergents, living space cleaners, deodorizers, air purifiers, room fragrances, hair fragrances, fabric softeners, multi-functional cleaning products, bactericidal products, antibacterial products, disinfectant products and sterilizers, but are not limited thereto.

[0121] In the present invention, the content of the antibacterial and preservation composition can be 0.01 weight percent to 10 weight percent relative to the cosmetics, sanitary products or daily chemical products, but is not limited thereto.

[0122] Specifically, the product can be selected from the group consisting of liquid detergent compositions for clothing, kitchen detergent compositions, wet wipe stock compositions, shampoo stock compositions, cosmetic cream stock compositions, and cosmetic powder compositions, but is not limited thereto.

[0123] When the product comprising the composition for antibacterial and preservation is a liquid detergent composition for clothing, a kitchen detergent composition, a wet wipe stock solution composition, a shampoo stock solution composition, a cosmetic cream stock solution composition or a cosmetic powder composition, the composition comprises a 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1-1 or a 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1-1 and o-methoxycinnamaldehyde, 4-methoxycinnamaldehyde, raspberry ketone, 3-phenyl-1-propanol, hydroxyacetophenone, sodium benzoate, phenoxyethanol, tropolone, piroctone olamine salt as shown in Chemical Formula 2. The invention discloses an antibacterial and preservative composition comprising any one of a compound selected from the group consisting of hydroxybenzoic acid, hydroxybenzoic acid sulfoxide, hydroxybenzoic acid sulfoxide, hydroxybenzoic acid sulfoxide and sodium dehydroacetate, which can effectively control Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa), Aspergillus brasiliensis (A. brasiliensis) and Candida albicans (C. albicans).

[0124] Furthermore, when the product comprising the composition for antibacterial and preservation is a liquid detergent composition for clothing, a kitchen detergent composition, a wet wipe stock solution composition, a shampoo stock solution composition, a cosmetic cream stock solution composition, or a cosmetic pressed powder composition, the product comprises a 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1-1 and lauroyl arginine methyl ester, lauroyl lysine methyl ester, lauroyl arginine ethyl ester, iodopropynyl butylcarbamate, polylysine, lauroyl lysine, and caprylhydroxamic acid as shown in Chemical Formula 3. A composition for antibacterial and preservation containing any one of the compounds of Acid) can effectively control Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa), Aspergillus brasiliensis (A. brasiliensis) and Candida albicans (C. albicans).

[0125] Furthermore, when the product comprising the composition for antibacterial and preservation is a liquid detergent composition for clothing, a kitchen detergent composition, a wet wipe stock solution composition, a shampoo stock solution composition, a cosmetic cream stock solution composition, or a cosmetic powder composition, the product comprises a 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1-1 and hexane-1,2-diol (Hexane-1,2-diol), octane-1,2-diol, decane-1,2-diol (Decane-1,2-diol), ethylhexylglycerin, glyceryl monocaprylate, octyl glycerin, hexylglycerin, levulinic acid, citric acid, sodium anisate, disodium edetate (Disodium edetate), and the like as shown in Chemical Formula 4. The invention discloses an antibacterial and preservative composition comprising any one of tetrasodium EDTA and tetrasodium EDTA, which can effectively control Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa), Aspergillus brasiliensis (A. brasiliensis) and Candida albicans (C. albicans).

[0126] Antibacterial methods

[0127] The present invention provides an antibacterial method, which comprises the step of treating bacteria with the antibacterial and preservation composition.

[0128] The method for treating bacteria with the antibacterial and preservation composition can be appropriately used according to conventional methods known to those skilled in the art in various fields where antibacterial treatment is required. The treatment amount of the antibacterial and preservation composition can be appropriately determined according to the intended use.

[0129] Unless otherwise contradictory, matters mentioned in the composition for antibacterial and preservation, the product comprising the composition for antibacterial and preservation, and the antibacterial method of the present invention are equally applicable.

[0130] Hair care cosmetic composition for preventing dandruff

[0131] The present invention provides a hair care cosmetic composition for preventing dandruff, comprising a compound as shown in Chemical Formula 1.

[0132] Chemical formula 1:

[0133]

[0134] In the chemical formula 1, R1 is a substituted or unsubstituted C7 to C 17 Alkyl, or substituted or unsubstituted C7 to C 17 Alkenyl.

[0135] Furthermore, in the chemical formula 1, R1 is a linear or branched C7 to C 17 Alkyl, linear or branched C7 to C 17 Alkenyl, or C7 to C 17 Hydroxyalkyl.

[0136] More specifically, R1 is a linear or branched C 10-14 Alkyl, linear or branched C 10-14 Alkenyl or C 10-14 Hydroxyalkyl.

[0137] In the present invention, the hair care cosmetic composition for preventing dandruff comprises the compound represented by Chemical Formula 1 as an effective ingredient.

[0138] In the present invention, the alkyl length of the compound as shown in Chemical Formula 1 can be C 7-17 There are many options, specifically 3,3'-(dodecylimino)bispropane-1,2-diol, which has the following chemical formula.

[0139] Chemical formula 1-1:

[0140]

[0141] (In the compound shown in Chemical Formula 1-1, R1 in Chemical Formula 1 is C 11 alkyl.)

[0142] In the present invention, the cosmetic composition may further include a compound as shown in Chemical Formula 5.

[0143] Chemical formula 5:

[0144] R 13 -L4·W

[0145] In the chemical formula 5,

[0146] L4 is -Zn or

[0147] R 13 is CH3-C(CH3)2-CH2-CH(CH3)-CH2-,

[0148] W is NH2-CH2-CH2-OH, Or does not exist (Null).

[0149] Specifically, in the compound shown in Chemical Formula 5, L4 is R 13 It is CH3-C(CH3)2-CH2-CH(CH3)-CH2-, and W is NH2-CH2-CH2-OH.

[0150] In the compound shown in Chemical Formula 5, L4 is -Zn, R 13 for W is

[0151] In the compound shown in Chemical Formula 5, L4 is R 13 for W does not exist (Null).

[0152] In the present invention, the compound represented by Chemical Formula 5 may be any one or more selected from the group consisting of piroctone olamine, zinc pyrithione, and climbazole, but is not limited thereto.

[0153] Specifically, the structure of Piroctone olamine is The structure of Zinc Pyrithione is The structure of Climbazole is

[0154] In the present invention, the cosmetic composition may further comprise any one compound selected from the group consisting of piroctone olamine, pyrithione zinc and climbazole.

[0155] The compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 5 may be included in the hair care cosmetic composition in a weight ratio of 9:1 to 1:9.

[0156] The compound represented by Chemical Formula 1 and any one compound selected from the group consisting of piroctone olamine, pyrithione zinc, and climbazole can be included in the hair care cosmetic composition in a weight ratio of 9:1 to 1:9. From the perspective of controlling dandruff fungi, the weight ratio can be 7:3 to 1:9. From an economic perspective, the weight ratio can be 9:1 to 5:5.

[0157] The cosmetic composition has a bactericidal effect on Malassezia sp. strains, specifically, one or more fungi selected from the group consisting of Malassezia furfur, Malassezia restricta, Malassezia globosa, Malassezia sympodialis, Malassezia slooffiae, Malassezia achydermatis, and Malassezia obtusa. Furthermore, the cosmetic composition can be applied to Malassezia sp. strains without limitation.

[0158] Compared with using the compound represented by Chemical Formula 1 alone, when the cosmetic composition is prepared by mixing the compound with any one compound selected from the group consisting of piroctone olamine, pyrithione zinc, and climbazole, a synergistic effect is exhibited in killing Malassezia sp. strains, which are dandruff fungi. Moreover, even if the compound represented by Chemical Formula 1 replaces 50% or more, specifically 70% to 80% of expensive dandruff fungal therapeutic agents such as piroctone olamine, pyrithione zinc, or climbazole, the Malassezia sp. strain can be killed with the same or better effect.

[0159] Composition for antifungal use

[0160] The present invention provides an antifungal composition targeting Malassezia sp. strains and comprising a compound as shown in Chemical Formula 1.

[0161] The compound represented by Chemical Formula 1 is as described above.

[0162] In the present invention, the antifungal composition may further comprise the compound shown in Chemical Formula 5, specifically, any one compound selected from the group consisting of piroctone olamine, pyrithione zinc, and climbazole.

[0163] From the perspective of controlling dandruff fungi, the weight ratio of the compound shown in Chemical Formula 1 to the compound shown in Chemical Formula 5, specifically, the compound shown in Chemical Formula 1 to any one compound selected from the group consisting of piroctone olamine, pyrithione zinc and climbazole, can be 7:3 to 1:9. From an economic perspective, the weight ratio can be 9:1 to 5:5.

[0164] The antifungal composition has a bactericidal effect on Malassezia sp. strains, specifically, one or more fungi selected from the group consisting of Malassezia furfur, Malassezia restricta, Malassezia globosa, Malassezia sympodialis, Malassezia slooffiae, Malassezia achydermatis, and Malassezia obtusa. Furthermore, the composition can be applied to Malassezia sp. strains without limitation.

[0165] Compared with using the compound represented by Chemical Formula 1 alone, when the antifungal composition is prepared by mixing the compound with any one compound selected from the group consisting of piroctone olamine, pyrithione zinc and climbazole, a synergistic effect is exhibited in killing Malassezia sp. strains, which are dandruff fungi. Moreover, even if the compound represented by Chemical Formula 1 replaces 50% or more, specifically 70% to 80% of expensive dandruff fungal therapeutic agents such as piroctone olamine, pyrithione zinc or climbazole, the Malassezia sp. strain can be killed with the same or better effect.

[0166] Hair care cosmetics

[0167] The present invention provides a hair care cosmetic comprising a hair care cosmetic composition for preventing dandruff or a composition for antifungal use.

[0168] The hair care cosmetic has an antidandruff effect and an antifungal effect on dandruff fungi.

[0169] In the present invention, the term "cosmetics" refers to an article that is applied to the human body by smearing, rubbing or spraying or similar methods, and is used to enhance charm and brighten the appearance by cleaning and beautifying the human body, or to maintain or promote the health of the skin and hair, and its effect on the human body is minimal.

[0170] In the present invention, the cosmetic can be prepared according to the cosmetic method in any dosage form commonly prepared in the art. The hair care cosmetic can be prepared in the form of any one selected from the group consisting of a hair tonic, a hair cream, a hair mask, a hair milk, a hair essence, a hair nutrient, a shampoo, a hair conditioner, a hair conditioner, a hair spray, a hair gel, a hair cream, a hair oil, a hair wax, a hair bleach, and a hair dye.

[0171] The content of the anti-dandruff hair care cosmetic composition or the anti-fungal composition can be 0.01 to 2.0 weight percent relative to the hair care cosmetic. Even at a relatively low content, it can still have excellent bactericidal activity against Malassezia sp. strains. The anti-dandruff hair care cosmetic composition or the anti-fungal composition comprises the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 5, specifically piroctone olamine, pyrithione zinc, or climbazole.

[0172] From the perspective of controlling dandruff fungi, the weight ratio of the compound shown in Chemical Formula 1 to the compound shown in Chemical Formula 5, specifically, the compound shown in Chemical Formula 1 to any one compound selected from the group consisting of piroctone olamine, pyrithione zinc and climbazole, can be 7:3 to 1:9. From an economic perspective, the weight ratio can be 9:1 to 5:5.

[0173] Compared with a cosmetic dosage form such as a shampoo containing a hair care cosmetic composition for preventing dandruff or an antifungal composition containing the compound as shown in Chemical Formula 1 alone or any one compound selected from the group consisting of piroctone olamine, pyrithione zinc and climbazole alone, when both are contained, Malassezia sp. strains can be effectively controlled at a lower dosage (concentration).

[0174] How to kill dandruff fungus

[0175] The present invention provides a method for sterilizing dandruff fungi, comprising the step of applying a hair care cosmetic composition for preventing dandruff or a composition for antifungal use to an individual.

[0176] The sterilization method of the present invention comprises the step of applying the hair care cosmetic composition for preventing dandruff or the composition for antifungal use to an individual.

[0177] The dandruff fungus is a strain of the genus Malassezia sp., specifically, it can be one or more selected from the group consisting of Malassezia furfur, Malassezia restricta, Malassezia globosa, Malassezia sympodialis, Malassezia slooffiae, Malassezia pachydermatis and Malassezia obtusa. In addition, it can be applied to strains of the genus Malassezia sp. without limitation.

[0178] Since the composition has a strong bactericidal effect on the Malassezia sp. strain, the composition can be administered to an individual to sterilize and control dandruff fungus.

[0179] In the present invention, the term "application" refers to contacting the antidandruff hair care cosmetic composition or antifungal composition with an individual's scalp or hair by any suitable method, thereby allowing the ingredients in the composition to act on the dandruff fungus and exert a fungicidal effect. The amount of the antidandruff hair care cosmetic composition or antifungal composition applied can be appropriately determined according to the intended use.

[0180] The subjects to which the hair care cosmetic composition for preventing dandruff or the antifungal composition of the present invention can be applied include, but are not limited to, mammals including humans, and examples thereof may include cows, pigs, horses, rabbits, mice, and humans.

[0181] Furthermore, the dosage of the hair care cosmetic composition for preventing dandruff or the antifungal composition of the present invention can be appropriately adjusted according to individual differences such as age and the degree of lesions and the dosage form. By applying an appropriate amount to the scalp once or more per day, it can be used for one week to several months.

[0182] The matters mentioned in the hair care cosmetic composition for preventing dandruff, the composition for antifungal use or the hair care cosmetic comprising these compositions, and the sterilization method of the present invention also apply unless they contradict each other.

[0183] Composition for antiviral use

[0184] The present invention provides an antiviral composition comprising a compound as shown in Chemical Formula 1.

[0185] Chemical formula 1:

[0186]

[0187] In the chemical formula 1,

[0188] R1 is substituted or unsubstituted C7 to C 17 Alkyl, or substituted or unsubstituted C7 to C 17 Alkenyl.

[0189] In the present invention, the antiviral composition comprises the compound represented by Chemical Formula 1 as an effective ingredient.

[0190] In the present invention, the term "antiviral" refers to the ability to reduce, prevent, inhibit or eliminate the proliferation, growth or survival of viruses, or to reduce, inhibit or eliminate the activity of viruses.

[0191] The "composition for use against viruses" of the present invention has the effect of reducing, preventing, inhibiting or eliminating the proliferation, growth or survival of viruses, or reducing, inhibiting or eliminating the activity of viruses.

[0192] In the present invention, the compound represented by Chemical Formula 1 may be 3,3'-(dodecylimino)bispropane-1,2-diol, the structural formula of which is represented by Chemical Formula 1-1, and is a nonionic surfactant.

[0193] Chemical formula 1-1:

[0194]

[0195] (In the compound shown in Chemical Formula 1-1, R1 in Chemical Formula 1 is C 11 alkyl.)

[0196] The antiviral composition can be diluted with water or other liquids to form a 0.1-5% (w / v) aqueous solution for use, and can also exert an antiviral effect when diluted to a 0.1-5% (w / v) aqueous solution for use.

[0197] The antiviral composition of the present invention has an antiviral or virucidal effect on viruses.

[0198] The virus can be one or more selected from the group consisting of coronavirus, influenza virus, norovirus, rotavirus, respiratory syncytial virus, avian influenza virus, foot-and-mouth disease virus and African swine fever virus.

[0199] Specifically, the antiviral composition is characterized in that it can effectively control various viruses such as norovirus, rotavirus, coronavirus (Human coronavirus 229E, OC43), influenza virus (Human influenza virus A, B, C), influenza A virus subtype H1N1 (Influenza A virus subtype, H1N1), respiratory syncytial virus (RSV) that causes respiratory tract infection, and avian influenza virus (AIV) that is transmitted to livestock and animals, especially highly pathogenic avian influenza virus (HPAIV (H5N1)), foot-and-mouth disease virus (Picornaviridae Aphthovirus), African swine fever virus (ASFV), etc.

[0200] In the present invention, the antiviral composition can also be used as an environmentally friendly epidemic prevention composition. In the present invention, the term "epidemic prevention" refers to preventing the occurrence or spread of infectious diseases in advance.

[0201] Antiviral methods

[0202] The present invention provides an antiviral method, comprising the step of treating viruses with the antiviral composition.

[0203] The method for treating viruses using the antiviral composition can be appropriately used according to conventional methods known to those skilled in the art in various fields requiring antiviral efficacy. The treatment amount of the antiviral composition can be appropriately determined according to the purpose of use.

[0204] Unless otherwise contradictory, the matters mentioned in the antiviral composition and antiviral method of the present invention are also applicable. DETAILED DESCRIPTION

[0205] Hereinafter, the present invention will be evaluated by applying it to various products with reference to preferred embodiments so that those skilled in the art can easily implement it. However, the present invention can be implemented in various forms and is not limited to the embodiments described below.

[0206] Test A: Antibacterial Effects of Compounds Represented by Chemical Formula 1 and Chemical Formula 2

[0207] Examples 1 to 10: Preparation of antibacterial and preservation compositions using the compounds shown in Chemical Formula 1 and Chemical Formula 2

[0208] Example 1.

[0209] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the o-methoxycinnamaldehyde compound shown in Chemical Formula 2 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0210] Example 2.

[0211] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the 4-methoxycinnamaldehyde compound shown in Chemical Formula 2 were mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0212] Example 3.

[0213] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the raspberry ketone compound shown in Chemical Formula 2 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0214] Example 4.

[0215] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the 3-phenyl-1-propanol compound shown in Chemical Formula 2 are mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0216] Example 5.

[0217] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the hydroxyacetophenone compound shown in Chemical Formula 2 are mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0218] Example 6.

[0219] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the sodium benzoate compound shown in Chemical Formula 2 are mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0220] Example 7.

[0221] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the phenoxyethanol compound shown in Chemical Formula 2 are mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0222] Example 8.

[0223] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the tropolone compound shown in Chemical Formula 2 were mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0224] Example 9.

[0225] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the piroctone olamine salt compound shown in Chemical Formula 2 are mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0226] Example 10.

[0227] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the sodium dehydroacetate compound shown in Chemical Formula 2 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0228] Comparative Examples 1 to 11: Preparation of an antibacterial and preservation composition using a compound as shown in Chemical Formula 1 or Chemical Formula 2.

[0229] A 3,3′-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 is used.

[0230] Comparative Example 2.

[0231] An o-methoxycinnamaldehyde compound as shown in Chemical Formula 2 is used.

[0232] Comparative Example 3.

[0233] A 4-methoxycinnamaldehyde compound as shown in Chemical Formula 2 is used.

[0234] Comparative Example 4.

[0235] A raspberry ketone compound as shown in Chemical Formula 2 is used.

[0236] Comparative Example 5.

[0237] A 3-phenyl-1-propanol compound as shown in Chemical Formula 2 was used.

[0238] Comparative Example 6.

[0239] A hydroxyacetophenone compound as shown in Chemical Formula 2 is used.

[0240] Comparative Example 7.

[0241] A sodium benzoate compound as shown in Chemical Formula 2 is used.

[0242] Comparative Example 8.

[0243] A phenoxyethanol compound as shown in Chemical Formula 2 is used.

[0244] Comparative Example 9.

[0245] The tropolone compound shown in Chemical Formula 2 is used.

[0246] Comparative Example 10.

[0247] The piroctone olamine salt compound shown in Chemical Formula 2 is used.

[0248] Comparative Example 11.

[0249] A sodium dehydroacetate compound as shown in Chemical Formula 2 is used.

[0250] Preparation Examples and Comparative Examples

[0251] The components used in the following preparation examples and comparative examples were purchased from Sigma-Aldrich Korea and TCI, among others. The antimicrobial and preservation compositions of the examples were prepared by combining the 3,3'-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with the compound represented by Chemical Formula 2 in a weight ratio of 8:2. These compositions were then used to prepare preparation examples of cosmetics, sanitary products, or daily chemical products. Comparative examples of cosmetics, sanitary products, or daily chemical products were then prepared using the antimicrobial and preservation compositions of the comparative examples containing only the compounds of Chemical Formula 1 or Chemical Formula 2.

[0252] Preparation Examples 1 to 10: Liquid detergent compositions for clothing

[0253] Preparation Example 1.

[0254] A liquid laundry detergent composition was prepared, comprising 6 weight percent of laureth-7, 3 weight percent of alkylbenzene sulfonate, 5 weight percent of sodium laureth-2 sulfate, 0.3 weight percent of protease, 0.3 weight percent of lipase, 1 weight percent of coconut fatty acid soap, 2 weight percent of salt, 0.2 weight percent of fragrance, 81.7 weight percent of purified water, and 0.5 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0255] Preparation Examples 2 to 10.

[0256] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, and 10 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the liquid laundry detergent compositions of Preparation Examples 2, 3, 4, 5, 6, 7, 8, 9, and 10 were prepared in sequence by the same method as in Preparation Example 1.

[0257] Preparation Examples 11-20: Kitchen Cleaner Compositions

[0258] Preparation Example 11.

[0259] A kitchen cleaning composition was prepared, comprising 5 weight percent of sodium laureth-2 sulfate, 4 weight percent of α-olefin sulfonate, 2 weight percent of amine oxide, 2 weight percent of alkyl glycoside, 2 weight percent of alkylbenzene sulfonate, 2 weight percent of glycerin, 0.2 weight percent of fragrance, 82.5 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0260] Preparation Examples 12-20.

[0261] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, and 10 were used instead of the antibacterial and preservation composition prepared according to Example 1, and the kitchen cleaning compositions of Preparation Examples 12, 13, 14, 15, 16, 17, 18, 19, and 20 were prepared in sequence by the same method as Preparation Example 11.

[0262] Preparation Examples 21-30: Wet Wipes Stock Liquid Composition

[0263] Preparation Example 21.

[0264] A wet wipe stock solution composition was prepared, comprising 1 weight percent of a natural extract, 98.7 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0265] Preparation Examples 22-30.

[0266] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, and 10 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the wet wipes stock solutions of Preparation Examples 22, 23, 24, 25, 26, 27, 28, 29, and 30 were prepared in sequence by the same method as Preparation Example 21.

[0267] Preparation Examples 31-40: Shampoo Stock Composition

[0268] Preparation Example 31.

[0269] A shampoo stock composition was prepared, comprising 0.05 weight percent of disodium EDTA, 0.1 weight percent of panthenol, 1 weight percent of glycerin, 1 weight percent of tocopheryl acetate, 0.5 weight percent of polyquaternium-7, 8 weight percent of sodium laureth sulfate, 5 weight percent of cocamidopropyl betaine, 2 weight percent of sodium cocoyl sarcosinate, 0.5 weight percent of polyquaternium-10, 1 weight percent of fragrance, 80.55 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservative composition prepared according to Example 1.

[0270] Preparation Examples 32-40.

[0271] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, and 10 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the shampoo stock solutions of Preparation Examples 32, 33, 34, 35, 36, 37, 38, 39, and 40 were prepared in sequence by the same method as Preparation Example 31.

[0272] Preparation Examples 41-50: Cosmetic Cream Stock Composition

[0273] Preparation Example 41.

[0274] A facial cream stock solution composition was prepared, comprising 2.5 weight percent of cetearyl alcohol, 1.5 weight percent of glyceryl stearate, 5.0 weight percent of tricaprylin, 1.2 weight percent of polysorbate 60, 0.5 weight percent of sorbitan stearate, 5.0 weight percent of squalane, 3.0 weight percent of liquid paraffin, 3.0 weight percent of cyclomethicone, 0.2 weight percent of δ-tocopherol, 4.0 weight percent of glycerol, 2.0 weight percent of 1,3-butylene glycol, 0.2 weight percent of xanthan gum, 0.05 weight percent of disodium ethylenediaminetetraacetic acid (EDTA-2Na), 0.1 weight percent of fragrance, 71.55 weight percent of purified water, and 0.2 weight percent of the composition for antibacterial and preservation prepared according to Example 1.

[0275] Preparation Examples 42-50.

[0276] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, and 10 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the cream stock solutions of Preparation Examples 42, 43, 44, 45, 46, 47, 48, 49, and 50 were prepared in sequence by the same method as Preparation Example 41.

[0277] Preparation Examples 51-60: Cosmetic Pressed Powder (Solid Makeup) Compositions

[0278] Preparation Example 51.

[0279] A pressed powder (solid makeup) composition was prepared, comprising 25 weight percent of spherical powder (Silica-HDI), 10 weight percent of calcium aluminum borosilicate, 20 weight percent of an oily adhesive silicone oil (dimethicone), 0.2 weight percent of a fragrance, 5 weight percent of a pigment, 20 weight percent of ethanol, 19.4 weight percent of plate-like talc (Talc JA 46R), and 0.4 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0280] Preparation Examples 52-60.

[0281] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, and 10 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the pressed powder (solid makeup) compositions of Preparation Examples 52, 53, 54, 55, 56, 57, 58, 59, and 60 were prepared in sequence by the same method as Preparation Example 51.

[0282] Preparation of Comparative Examples 1 to 11: Liquid detergent compositions for clothing

[0283] Preparation of Comparative Example 1.

[0284] A liquid detergent composition for laundry was prepared, comprising 6 weight percent of laureth-7, 3 weight percent of alkylbenzene sulfonate, 5 weight percent of sodium laureth-2 sulfate, 0.3 weight percent of protease, 0.3 weight percent of lipase, 1 weight percent of coconut fatty acid soap, 2 weight percent of salt, 0.2 weight percent of fragrance, 81.7 weight percent of purified water, and 0.5 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0285] Preparation of Comparative Examples 2 to 11.

[0286] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were used instead of the antibacterial and preservation compositions prepared according to Comparative Example 1, and the liquid laundry detergent compositions of Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were prepared in sequence by the same method as that for Comparative Example 1.

[0287] Preparation of Comparative Examples 12 to 22: Kitchen Cleaner Compositions

[0288] Preparation of Comparative Example 12.

[0289] A kitchen cleaning composition was prepared, comprising 5 weight percent of sodium laureth-2 sulfate, 4 weight percent of α-olefin sulfonate, 2 weight percent of amine oxide, 2 weight percent of alkyl glycoside, 2 weight percent of alkylbenzene sulfonate, 2 weight percent of glycerin, 0.2 weight percent of fragrance, 82.5 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0290] Preparation of Comparative Examples 13 to 22.

[0291] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the kitchen cleaning compositions of Comparative Examples 13, 14, 15, 16, 17, 18, 19, 20, 21, and 22 were prepared in sequence by the same method as that for preparing Comparative Example 12.

[0292] Preparation of Comparative Examples 23 to 33: Wet Wipes Stock Liquid Composition

[0293] Preparation of Comparative Example 23.

[0294] A wet wipe stock solution composition was prepared, comprising 1 weight percent of a natural extract, 98.7 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0295] Preparation of Comparative Examples 24 to 33.

[0296] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were used instead of the composition for antibacterial and preservation prepared according to Comparative Example 1, and the wet wipes stock solutions of Comparative Examples 24, 25, 26, 27, 28, 29, 30, 31, 32, and 33 were prepared in sequence by the same method as that for preparing Comparative Example 23.

[0297] Preparation of Comparative Examples 34-44: Shampoo Stock Liquid Composition

[0298] Preparation of Comparative Example 34.

[0299] A shampoo stock composition was prepared, comprising 0.05 weight percent of disodium EDTA, 0.1 weight percent of panthenol, 1 weight percent of glycerin, 1 weight percent of tocopheryl acetate, 0.5 weight percent of polyquaternium-7, 8 weight percent of sodium laureth sulfate, 5 weight percent of cocamidopropyl betaine, 2 weight percent of sodium cocoyl sarcosinate, 0.5 weight percent of polyquaternium-10, 1 weight percent of fragrance, 80.55 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0300] Preparation of Comparative Examples 35 to 44.

[0301] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the shampoo stock solutions of Comparative Examples 35, 36, 37, 38, 39, 40, 41, 42, 43, and 44 were prepared in sequence by the same method as that for preparing Comparative Example 34.

[0302] Preparation of Comparative Examples 45-55: Cosmetic Cream Stock Solution Composition

[0303] Preparation of Comparative Example 45.

[0304] A facial cream stock composition is prepared, which includes 2.5 weight percent of cetearyl alcohol, 1.5 weight percent of glyceryl stearate, 5.0 weight percent of tricaprylin, 1.2 weight percent of polysorbate 60, 0.5 weight percent of sorbitan stearate, 5.0 weight percent of squalane, 3.0 weight percent of liquid paraffin, 3.0 weight percent of cyclomethicone, 0.2 weight percent of δ-tocopherol, 4.0 weight percent of glycerol, 2.0 weight percent of 1,3-butylene glycol, 0.2 weight percent of xanthan gum, 0.05 weight percent of disodium ethylenediaminetetraacetic acid (EDTA-2Na), 0.1 weight percent of fragrance, 71.55 weight percent of purified water, and 0.2 weight percent of the composition for antibacterial and preservation prepared according to Comparative Example 1.

[0305] Preparation of Comparative Examples 46 to 55.

[0306] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were used instead of the antibacterial and preservation compositions prepared according to Comparative Example 1, and the cream stock solutions of Comparative Examples 46, 47, 48, 49, 50, 51, 52, 53, 54, and 55 were prepared in sequence by the same method as that for preparing Comparative Example 45.

[0307] Preparation of Comparative Examples 56-66: Cosmetic Pressed Powder (Solid Makeup) Compositions

[0308] Preparation of Comparative Example 56.

[0309] A pressed powder (solid makeup) composition was prepared, comprising 25 weight percent of spherical powder (Silica-HDI), 10 weight percent of calcium aluminum borosilicate, 20 weight percent of an oily adhesive silicone oil (dimethicone), 0.2 weight percent of a fragrance, 5 weight percent of a pigment, 20 weight percent of ethanol, 19.4 weight percent of plate-like talc (Talc JA 46R), and 0.4 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0310] Preparation of Comparative Examples 57 to 66.

[0311] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were used instead of the antibacterial and preservation compositions prepared according to Comparative Example 1, and the pressed powder (solid makeup) compositions of Comparative Examples 57, 58, 59, 60, 61, 62, 63, 64, 65, and 66 were prepared in sequence by the same method as that for preparing Comparative Example 56.

[0312] Experimental example

[0313] Antibacterial tests against bacteria, filamentous fungi, and yeasts were performed using a disc diffusion method for the compound represented by Chemical Formula 1, each antibacterial and preservation composition prepared according to the components of the above Examples and Comparative Examples, and each cosmetic, sanitary product, and daily chemical product composition prepared according to the Preparation Examples and Comparative Examples. The methods are as follows.

[0314] Experimental Example 1: Evaluation of antibacterial effect by disc diffusion method

[0315] (1) Paper diffusion method

[0316] Pseudomonas aeruginosa, Staphylococcus aureus, and Escherichia coli were cultured in tryptic soy broth, and Candida albicans was cultured in Sabouraud dextrose broth. Aspergillus brasiliensis was subcultured in potato dextrose agar (PDA) and spores were collected using sterile saline to prepare bacterial suspensions. 200 μL of each prepared bacterial suspension was added to 4 mm thick tryptic soy agar (TSA) and potato dextrose agar (PDA) media and evenly spread using a spreader. Allow the culture medium with the bacterial solution to dry for 5 minutes.

[0317] After inoculating each paper disc with 50 μL of the compound 3,3'-(dodecylimino)bispropane-1,2-diol (chemical formula 1), the discs were gently pressed onto the dry culture medium using a sterilized rod or ring. A gap of approximately 20 to 30 mm was left between each disc. The solid culture medium with the discs was placed in an incubator, and bacteria (Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa) were cultured at 35±2°C for 24 to 48 hours, Candida albicans at 25°C for 24 to 48 hours, and Aspergillus brasiliensis at 24°C for 48 to 72 hours. The clear zone (in millimeters) where growth inhibition occurs was then measured. In the experiment, the disc diffusion method was repeated three times.

[0318] (2) Antibacterial test results

[0319] The results confirmed that treatment with 3,3'-(dodecylimino)bispropane-1,2-diol inhibited the growth of bacteria such as Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), and Pseudomonas aeruginosa (P. aeruginosa), as well as fungi such as Candida albicans (C. albicans) and Aspergillus brasiliensis. This suggests that 3,3'-(dodecylimino)bispropane-1,2-diol has antibacterial effects not only against bacteria but also against fungi such as filamentous fungi and yeasts.

[0320] Table 1:

[0321]

[0322] Experimental Example 2: Antibacterial test of the composition for antibacterial and preservation

[0323] The antibacterial power of the test solution is determined by the liquid culture medium dilution method (broth dilution method). A test solution is used in which the treatment concentration is diluted to a maximum concentration of 5% and a minimum concentration of 0.0001%. The test solution and the strain are cultured together to confirm the turbidity of the test tube. In this case, the concentration of the test solution in the test tube in which no bacterial growth is observed in the test tube treated with the test solution at different concentrations is set as the minimum inhibitory concentration (MIC) compared to the turbidity observed in the test tube in which the strain is only inoculated in the culture medium without treating the test solution. After performing the first test as above, a second test is performed by further subdividing the treatment concentration of the test solution to obtain the correct minimum inhibitory concentration (MIC).

[0324] (1) Pre-culture of test bacteria

[0325] Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa were inoculated into Tryptic Soy Broth and cultured at 35±2°C for 16-24 hours. Candida albicans was inoculated into Sabouraud Dextrose Broth and cultured at 25°C for 24-48 hours. Aspergillus brasiliensis was spread onto potato dextrose agar and cultured at 25±1°C for 7 days. Sterile saline was then dispensed onto the solid culture medium where the bacteria had grown, and spores were scraped off with a spreader and diluted in sterile saline.

[0326] (2) Preparation of test solution

[0327] The antibacterial and preservation compositions of Examples 1 to 10 were dissolved in dipropylene glycol to serve as test solutions.

[0328] Comparative Examples 1 to 11 were used as comparative solutions.

[0329] (3) Mixed strains and compositions for antibacterial and preservation (test solutions)

[0330] After adding liquid culture medium to the test tube, the test solution was diluted to a treatment concentration ranging from a maximum concentration of 5% to a minimum concentration of 0.0001%. Tryptic Soy Broth was used as a liquid culture medium for E. coli, S. aureus, and P. aeruginosa (bacteria), and Sabouraud Dextrose Broth was used as a liquid culture medium for Candida albicans and A. brasiliensis (fungi).

[0331] (4) Inoculation of test bacterial solution

[0332] Inoculate Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), and Pseudomonas aeruginosa (P. aeruginosa) to a concentration of 1×10 5 CFU / mL. Incubate the test tubes treated with the test solution at 35±2°C for 16 to 24 hours. Inoculate Candida albicans and Aspergillus brasiliensis to a concentration of 1×10 4 CFU / mL. After treatment with the test solution, Candida albicans (C. albicans) was cultured at 25°C for 24-48 hours, and Aspergillus brasiliensis (A. brasiliensis) was cultured at 25°C for 46-50 hours. A culture tube without bacterial solution was used as a negative control, and a tube inoculated with only bacterial solution without the test solution was used as a growth control. Furthermore, to confirm the antimicrobial activity of dipropylene glycol, the solvent, the MIC of the test bacteria against the solvent was determined using the same test conditions as the sample.

[0333] (5) Antibacterial test results of the composition used for antibacterial and preservation

[0334] The test results are shown in Tables 2 and 3. Evaluation of the test results shows that the antibacterial and preservation composition of the present invention effectively inhibits bacteria, fungi, and yeasts.

[0335] Table 2-3: Antibacterial test results of the composition used for antibacterial and preservation

[0336] Table 2 shows the antibacterial test results of the composition for antibacterial and preservation prepared according to the examples against bacteria, filamentous fungi and yeasts. Table 3 shows the antibacterial test results of the composition for antibacterial and preservation prepared according to the comparative examples against bacteria, filamentous fungi and yeasts, which are expressed as minimum inhibitory concentration (MIC).

[0337] Referring to Tables 2 and 3, the antibacterial and preservation compositions prepared according to all examples of the present invention exhibited excellent antibacterial effects against bacteria, filamentous fungi, and yeasts, compared to the comparative examples using only the compounds in Table 3. In particular, it was confirmed that the antibacterial and preservation composition comprising a combination of the compound of Chemical Formula 1 and the compound of Chemical Formula 2 at a ratio of 8:2 was the most effective in controlling bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), and Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis), and yeast (Candida albicans (C. albicans)).

[0338] Table 2:

[0339]

[0340]

[0341] Table 3:

[0342]

[0343]

[0344] Experimental Example 3: Antibacterial Test of Compositions of Cosmetics, Sanitary Products, and Daily Chemical Products

[0345] (1) Antibacterial test method

[0346] The experiment was conducted in accordance with the Korean Industrial Standard Cosmetics-Microbiology-Evaluation of Cosmetic Preservative Power (KS M ISO 1930:2014). The specific experimental methods are as follows.

[0347] Bacterial solutions of Pseudomonas aeruginosa, Staphylococcus aureus, and Escherichia coli, and fungal solutions of Candida albicans and Aspergillus brasiliensis were prepared.

[0348] The liquid detergent composition for clothing, the kitchen detergent composition, the wet wipe stock solution composition, the shampoo stock solution composition, the cosmetic face cream stock solution composition, and the cosmetic powder composition prepared in the preparation examples and the comparative preparation examples were respectively divided into five sample bottles for preparation. Each of the bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)) as well as Candida albicans (C. albicans) and Aspergillus brasiliensis (A. brasiliensis) were then inoculated. Sample bottles inoculated only with the bacterial liquid without the formulation composition served as a preservative-untreated control group.

[0349] The samples were sorted by date, with the start date of the inoculation experiment designated as Day 0 (Day-0), 24 hours after inoculation as Day 1 (Day-1), and 7 days after inoculation as Day 7 (Day-7). Each sample was then inoculated onto Tryptic Soy Agar (TSA) and Potato Dextrose Agar (PDA). Bacteria (E. coli, S. aureus, Pseudomonas aeruginosa) were cultured in an incubator at 35±2°C for 24-48 hours, yeast (C. albicans) at 25°C for 24-48 hours, and mold (A. brasiliensis) at 24°C for 48-72 hours. The presence of bacteria was then determined.

[0350] (2) Antibacterial test results of cosmetics, sanitary products, and daily chemical product compositions

[0351] Table 4-5: Antibacterial test results of liquid detergent compositions for laundry

[0352] Tables 4 to 15 below show the antibacterial efficacy of the compositions for antimicrobial and preservative use, including the Examples and Comparative Examples, for cosmetics, hygiene products, and daily chemical products. After applying the Examples and Comparative Examples to bacteria, filamentous fungi, and yeasts, the residual bacterial count after 7 days is expressed in CFU / mL. If the residual bacterial count is too high to be counted, it is expressed as TNTC (too-numerous-to-count).

[0353] Table 4 below shows the antibacterial test results of the liquid laundry detergent compositions of Preparation Examples 1 to 10 against bacteria, filamentous fungi, and yeasts, and Table 5 shows the antibacterial test results of the liquid laundry detergent compositions of Comparative Examples 1 to 11 against bacteria, filamentous fungi, and yeasts.

[0354] Referring to Table 4, it was confirmed that the liquid detergent compositions for clothing of Preparation Examples 1 to 10 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0355] Furthermore, it was confirmed that the liquid laundry detergent compositions of Preparation Examples 1 to 10 containing both Chemical Formula 1 and Chemical Formula 2 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the liquid laundry detergent compositions of Preparation Examples 1 to 11 containing only Chemical Formula 1 or Chemical Formula 2.

[0356] Table 4:

[0357]

[0358] Table 5:

[0359]

[0360] Table 6-7: Antibacterial test results of kitchen detergent compositions

[0361] Table 6 below shows the antibacterial test results of the kitchen cleaning compositions of Preparation Examples 11 to 20 against bacteria, filamentous fungi, and yeasts, and Table 7 shows the antibacterial test results of the kitchen cleaning compositions of Comparative Preparation Examples 12 to 22 against bacteria, filamentous fungi, and yeasts.

[0362] Referring to Table 6, it was confirmed that the kitchen cleaning compositions of Preparation Examples 11 to 20 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0363] Furthermore, it was confirmed that the kitchen cleaning compositions of Preparation Examples 11 to 20 containing both Chemical Formula 1 and Chemical Formula 2 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the kitchen cleaning compositions of Preparation Examples 12 to 22 containing only Chemical Formula 1 or Chemical Formula 2.

[0364] Table 6:

[0365]

[0366] Table 7:

[0367]

[0368] Table 8-9 : Antibacterial test results of wet wipes stock solution composition

[0369] Table 8 below shows the antibacterial test results of the wet wipes stock solutions of Preparation Examples 21 to 30 against bacteria, filamentous fungi, and yeasts, and Table 9 shows the antibacterial test results of the wet wipes stock solutions of Preparation Examples 23 to 33 against bacteria, filamentous fungi, and yeasts.

[0370] Referring to Table 8, it was confirmed that the wet wipes stock solution compositions of Preparation Examples 21 to 30 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0371] Furthermore, it has been confirmed that the wet wipes stock solution compositions of Preparation Examples 21 to 30 containing both Chemical Formula 1 and Chemical Formula 2 have excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the wet wipes stock solution compositions of Preparation Examples 23 to 33 containing only Chemical Formula 1 or Chemical Formula 2.

[0372] Table 8:

[0373]

[0374] Table 9:

[0375]

[0376] Table 10-11: Antibacterial test results of shampoo stock solution composition

[0377] Table 10 below shows the antibacterial test results of the shampoo stock solutions of Preparation Examples 31 to 40 against bacteria, filamentous fungi, and yeasts, and Table 11 shows the antibacterial test results of the shampoo stock solutions of Comparative Examples 34 to 44 against bacteria, filamentous fungi, and yeasts.

[0378] Referring to Table 10, it was confirmed that the shampoo concentrate compositions of Preparation Examples 31 to 40 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0379] Furthermore, it was confirmed that the shampoo stock solution compositions of Preparation Examples 31 to 40 containing both Chemical Formula 1 and Chemical Formula 2 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the shampoo stock solution compositions of Preparation Examples 34 to 44 containing only Chemical Formula 1 or Chemical Formula 2.

[0380] Table 10:

[0381]

[0382] Table 11:

[0383]

[0384]

[0385] Table 12-13: Antibacterial test results of cosmetic cream stock solution composition

[0386] Table 12 below shows the antibacterial test results of the cosmetic facial cream stock solution compositions of Preparation Examples 41 to 50 against bacteria, filamentous fungi, and yeasts, and Table 13 shows the antibacterial test results of the cosmetic facial cream stock solution compositions of Preparation Examples 45 to 55 against bacteria, filamentous fungi, and yeasts.

[0387] Referring to Table 12, it was confirmed that the cosmetic facial cream stock solution compositions of Preparation Examples 41 to 50 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0388] Furthermore, it was confirmed that the cosmetic cream stock solution compositions of Preparation Examples 41 to 50 containing both Chemical Formula 1 and Chemical Formula 2 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the cosmetic cream stock solution compositions of Preparation Examples 45 to 55 containing only Chemical Formula 1 or Chemical Formula 2.

[0389] Table 12:

[0390]

[0391] Table 13:

[0392]

[0393]

[0394] Table 14-15: Antibacterial test results of cosmetic powder compositions

[0395] Table 14 below shows the antibacterial test results of the cosmetic powder compositions of Preparation Examples 51 to 60 against bacteria, filamentous fungi, and yeasts, and Table 15 shows the antibacterial test results of the cosmetic powder compositions of Comparative Examples 56 to 66 against bacteria, filamentous fungi, and yeasts.

[0396] Referring to Table 14, it was confirmed that the cosmetic powder compositions of Preparation Examples 51 to 60 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0397] Furthermore, it was confirmed that the cosmetic powder compositions of Preparation Examples 51 to 60 containing both Chemical Formula 1 and Chemical Formula 2 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the cosmetic powder compositions of Preparation Examples 56 to 66 containing only Chemical Formula 1 or Chemical Formula 2.

[0398] Table 14:

[0399]

[0400] Table 15:

[0401]

[0402]

[0403] Test B: Antibacterial Effects of Compounds Represented in Chemical Formula 1 and Chemical Formula 3

[0404] Examples 1 to 7: Preparation of antibacterial and preservation compositions using the compounds shown in Chemical Formula 1 and Chemical Formula 3

[0405] Example 1.

[0406] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the lauroyl arginine methyl ester compound shown in Chemical Formula 3 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0407] Example 2.

[0408] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the lauroyl lysine methyl ester compound shown in Chemical Formula 3 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0409] Example 3.

[0410] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the lauroyl arginine ethyl ester compound shown in Chemical Formula 3 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0411] Example 4.

[0412] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the iodopropynyl butylcarbamate compound shown in Chemical Formula 3 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0413] Example 5.

[0414] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the polylysine compound shown in Chemical Formula 3 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0415] Example 6.

[0416] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the lauroyl lysine compound shown in Chemical Formula 3 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0417] Example 7.

[0418] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the octanoylhydroxamic acid compound shown in Chemical Formula 3 are mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0419] Comparative Examples 1 to 8: Comparative Example 1: Preparation of an antibacterial and preservation composition using a compound as shown in Chemical Formula 1 or Chemical Formula 3.

[0420] A 3,3′-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 is used.

[0421] Comparative Example 2.

[0422] The lauroyl arginine methyl ester compound shown in Chemical Formula 3 is used.

[0423] Comparative Example 3.

[0424] The lauroyl lysine methyl ester compound shown in Chemical Formula 3 is used.

[0425] Comparative Example 4.

[0426] The lauroyl arginine ethyl ester compound shown in Chemical Formula 3 is used.

[0427] Comparative Example 5.

[0428] The iodopropynyl butylcarbamate compound shown in Chemical Formula 3 is used.

[0429] Comparative Example 6.

[0430] A polylysine compound as shown in Chemical Formula 3 is used.

[0431] Comparative Example 7.

[0432] The lauroyl lysine compound shown in Chemical Formula 3 is used.

[0433] Comparative Example 8.

[0434] An octanoylhydroxamic acid compound as shown in Chemical Formula 3 is used.

[0435] Preparation Examples and Comparative Examples

[0436] The components used in the following preparation examples and comparative examples were purchased from Sigma-Aldrich Korea and TCI, among others. The antimicrobial and preservation compositions of the examples were prepared by combining the 3,3'-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with the compound represented by Chemical Formula 3 in a weight ratio of 8:2. These compositions were then used to prepare preparation examples of cosmetics, sanitary products, or daily chemical products. Comparative examples of cosmetics, sanitary products, or daily chemical products were then prepared using the comparative examples of antimicrobial and preservation compositions containing only the compound represented by Chemical Formula 1 or Chemical Formula 3.

[0437] Preparation Examples 1 to 7: Liquid detergent compositions for clothing

[0438] Preparation Example 1.

[0439] A liquid laundry detergent composition was prepared, comprising 6 weight percent of laureth-7, 3 weight percent of alkylbenzene sulfonate, 5 weight percent of sodium laureth-2 sulfate, 0.3 weight percent of protease, 0.3 weight percent of lipase, 1 weight percent of coconut fatty acid soap, 2 weight percent of salt, 0.2 weight percent of fragrance, 81.7 weight percent of purified water, and 0.5 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0440] Preparation Examples 2 to 7.

[0441] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, and 7 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the liquid detergent compositions for clothing of Preparation Examples 2, 3, 4, 5, 6, and 7 were prepared in sequence by the same method as in Preparation Example 1.

[0442] Preparation Examples 8-14: Kitchen Cleaner Compositions

[0443] Preparation Example 8.

[0444] A kitchen cleaning composition was prepared, comprising 5 weight percent of sodium laureth-2 sulfate, 4 weight percent of α-olefin sulfonate, 2 weight percent of amine oxide, 2 weight percent of alkyl glycoside, 2 weight percent of alkylbenzene sulfonate, 2 weight percent of glycerin, 0.2 weight percent of fragrance, 82.5 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0445] Preparation Examples 9 to 14.

[0446] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, and 7 were used instead of the antibacterial and preservation composition prepared according to Example 1, and the kitchen cleaning compositions of Preparation Examples 9, 10, 11, 12, 13, and 14 were prepared in sequence by the same method as Preparation Example 8.

[0447] Preparation Examples 15-21: Wet Wipes Stock Composition

[0448] Preparation Example 15.

[0449] A wet wipe stock solution composition was prepared, comprising 1 weight percent of a natural extract, 98.7 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0450] Preparation Examples 16-21.

[0451] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, and 7 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the wet wipes stock solutions of Preparation Examples 16, 17, 18, 19, 20, and 21 were prepared in sequence by the same method as Preparation Example 15.

[0452] Preparation Examples 22-28: Shampoo Stock Composition

[0453] Preparation Example 22.

[0454] A shampoo stock composition was prepared, comprising 0.05 weight percent of disodium EDTA, 0.1 weight percent of panthenol, 1 weight percent of glycerin, 1 weight percent of tocopheryl acetate, 0.5 weight percent of polyquaternium-7, 8 weight percent of sodium laureth sulfate, 5 weight percent of cocamidopropyl betaine, 2 weight percent of sodium cocoyl sarcosinate, 0.5 weight percent of polyquaternium-10, 1 weight percent of fragrance, 80.55 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservative composition prepared according to Example 1.

[0455] Preparation Examples 23-28.

[0456] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, and 7 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the shampoo stock solutions of Preparation Examples 23, 24, 25, 26, 27, and 28 were prepared in sequence by the same method as Preparation Example 22.

[0457] Preparation Examples 29-35: Cosmetic Cream Stock Composition

[0458] Preparation Example 29.

[0459] A facial cream stock solution composition was prepared, comprising 2.5 weight percent of cetearyl alcohol, 1.5 weight percent of glyceryl stearate, 5.0 weight percent of tricaprylin, 1.2 weight percent of polysorbate 60, 0.5 weight percent of sorbitan stearate, 5.0 weight percent of squalane, 3.0 weight percent of liquid paraffin, 3.0 weight percent of cyclomethicone, 0.2 weight percent of δ-tocopherol, 4.0 weight percent of glycerol, 2.0 weight percent of 1,3-butylene glycol, 0.2 weight percent of xanthan gum, 0.05 weight percent of disodium ethylenediaminetetraacetic acid (EDTA-2Na), 0.1 weight percent of fragrance, 71.55 weight percent of purified water, and 0.2 weight percent of the composition for antibacterial and preservation prepared according to Example 1.

[0460] Preparation Examples 30-35.

[0461] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, and 7 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the cream stock solutions of Preparation Examples 30, 31, 32, 33, 34, and 35 were prepared in sequence by the same method as Preparation Example 29.

[0462] Preparation Examples 36-42: Cosmetic Pressed Powder (Solid Makeup) Compositions

[0463] Preparation Example 36.

[0464] A pressed powder (solid makeup) composition was prepared, comprising 25 weight percent of spherical powder (Silica-HDI), 10 weight percent of calcium aluminum borosilicate, 20 weight percent of an oily adhesive silicone oil (dimethicone), 0.2 weight percent of a fragrance, 5 weight percent of a pigment, 20 weight percent of ethanol, 19.4 weight percent of plate-like talc (Talc JA 46R), and 0.4 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0465] Preparation Examples 37-42.

[0466] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, and 7 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the pressed powder (solid makeup) compositions of Preparation Examples 37, 38, 39, 40, 41, and 42 were prepared in sequence by the same method as Preparation Example 36.

[0467] Preparation of Comparative Examples 1 to 8: Liquid Cleanser Compositions for Clothes

[0468] Preparation of Comparative Example 1.

[0469] A liquid detergent composition for laundry was prepared, comprising 6 weight percent of laureth-7, 3 weight percent of alkylbenzene sulfonate, 5 weight percent of sodium laureth-2 sulfate, 0.3 weight percent of protease, 0.3 weight percent of lipase, 1 weight percent of coconut fatty acid soap, 2 weight percent of salt, 0.2 weight percent of fragrance, 81.7 weight percent of purified water, and 0.5 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0470] Preparation of Comparative Examples 2 to 8.

[0471] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, and 8 were used instead of the antibacterial and preservation compositions prepared according to Comparative Example 1, and the liquid laundry detergent compositions of Comparative Examples 2, 3, 4, 5, 6, 7, and 8 were prepared in sequence by the same method as that of Comparative Example 1.

[0472] Preparation of Comparative Examples 9 to 16: Kitchen Cleaner Compositions

[0473] Preparation of Comparative Example 9.

[0474] A kitchen cleaning composition was prepared, comprising 5 weight percent of sodium laureth-2 sulfate, 4 weight percent of α-olefin sulfonate, 2 weight percent of amine oxide, 2 weight percent of alkyl glycoside, 2 weight percent of alkylbenzene sulfonate, 2 weight percent of glycerin, 0.2 weight percent of fragrance, 82.5 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0475] Preparation of Comparative Examples 10 to 16.

[0476] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, and 8 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the kitchen cleaning compositions of Comparative Examples 10, 11, 12, 13, 14, 15, and 16 were prepared in sequence by the same method as that for Comparative Example 9.

[0477] Preparation of Comparative Examples 17 to 24: Wet Wipes Stock Composition

[0478] Preparation of Comparative Example 17.

[0479] A wet wipe stock solution composition was prepared, comprising 1 weight percent of a natural extract, 98.7 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0480] Preparation of Comparative Examples 18 to 24.

[0481] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, and 8 were used instead of the antibacterial and preservation compositions prepared according to Comparative Example 1, and the wet wipe stock solutions of Comparative Examples 18, 19, 20, 21, 22, 23, and 24 were prepared in sequence by the same method as that of Comparative Example 17.

[0482] Preparation of Comparative Examples 25 to 32: Shampoo Stock Compositions

[0483] Preparation of Comparative Example 25.

[0484] A shampoo stock composition was prepared, comprising 0.05 weight percent of disodium EDTA, 0.1 weight percent of panthenol, 1 weight percent of glycerin, 1 weight percent of tocopheryl acetate, 0.5 weight percent of polyquaternium-7, 8 weight percent of sodium laureth sulfate, 5 weight percent of cocamidopropyl betaine, 2 weight percent of sodium cocoyl sarcosinate, 0.5 weight percent of polyquaternium-10, 1 weight percent of fragrance, 80.55 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0485] Preparation of Comparative Examples 26 to 32.

[0486] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, and 8 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the shampoo stock solutions of Comparative Examples 26, 27, 28, 29, 30, 31, and 32 were prepared in sequence by the same method as that for Comparative Example 25.

[0487] Preparation of Comparative Examples 33-40: Cosmetic Cream Stock Solution Composition

[0488] Preparation of Comparative Example 33.

[0489] A facial cream stock composition is prepared, which includes 2.5 weight percent of cetearyl alcohol, 1.5 weight percent of glyceryl stearate, 5.0 weight percent of tricaprylin, 1.2 weight percent of polysorbate 60, 0.5 weight percent of sorbitan stearate, 5.0 weight percent of squalane, 3.0 weight percent of liquid paraffin, 3.0 weight percent of cyclomethicone, 0.2 weight percent of δ-tocopherol, 4.0 weight percent of glycerol, 2.0 weight percent of 1,3-butylene glycol, 0.2 weight percent of xanthan gum, 0.05 weight percent of disodium ethylenediaminetetraacetic acid (EDTA-2Na), 0.1 weight percent of fragrance, 71.55 weight percent of purified water, and 0.2 weight percent of the composition for antibacterial and preservation prepared according to Comparative Example 1.

[0490] Preparation of Comparative Examples 34 to 40.

[0491] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, and 8 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the cream stock solutions of Comparative Examples 34, 35, 36, 37, 38, 39, and 40 were prepared in sequence by the same method as that for preparing Comparative Example 33.

[0492] Preparation of Comparative Examples 41 to 48: Cosmetic Pressed Powder (Solid Makeup) Compositions

[0493] Preparation of Comparative Example 41.

[0494] A pressed powder (solid makeup) composition was prepared, comprising 25 weight percent of spherical powder (Silica-HDI), 10 weight percent of calcium aluminum borosilicate, 20 weight percent of an oily adhesive silicone oil (dimethicone), 0.2 weight percent of a fragrance, 5 weight percent of a pigment, 20 weight percent of ethanol, 19.4 weight percent of plate-like talc (Talc JA 46R), and 0.4 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0495] Preparation of Comparative Examples 42 to 48.

[0496] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, and 8 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the pressed powder (solid makeup) compositions of Comparative Examples 42, 43, 44, 45, 46, 47, and 48 were prepared in sequence by the same method as that for Comparative Example 41.

[0497] Experimental example

[0498] Using the compounds represented by Chemical Formula 1 and Chemical Formula 3, each composition for antibacterial and preservation prepared according to the components of the above-mentioned Examples and Comparative Examples, and each cosmetic, sanitary product, and daily chemical product composition prepared according to the Preparation Examples and Comparative Examples were tested for antibacterial effects on bacteria, filamentous fungi, and yeasts, and the methods are as follows.

[0499] Experimental Example 1: Antibacterial test of the composition for antibacterial and preservation

[0500] The antibacterial test was conducted by the same method as the antibacterial test of the aforementioned composition for antibacterial and preservation.

[0501] The test results are shown in Tables 16 and 17. It can be seen from the test results that the antibacterial and preservation composition of the present invention effectively controls bacteria, filamentous fungi, and yeasts.

[0502] Table 16-17: Antibacterial test results of the composition used for antibacterial and preservation

[0503] Table 16 shows the antibacterial test results of the composition for antibacterial and preservation prepared according to the examples against bacteria, filamentous fungi, and yeasts. Table 17 shows the antibacterial test results of the composition for antibacterial and preservation prepared according to the comparative examples against bacteria, filamentous fungi, and yeasts, which are expressed as minimum inhibitory concentration (MIC).

[0504] Referring to Tables 16 and 17, the antibacterial and preservation compositions prepared according to all examples of the present invention exhibited excellent antibacterial effects against bacteria, filamentous fungi, and yeasts, compared to the comparative example using only the compounds in Table 17. In particular, it was confirmed that the antibacterial and preservation composition comprising the compounds of Chemical Formula 1 and Chemical Formula 3, in a ratio of 8:2, was the most effective in controlling bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), and Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis), and yeast (Candida albicans (C. albicans)).

[0505] Table 16:

[0506]

[0507] Table 17:

[0508]

[0509]

[0510] Experimental Example 2: Antibacterial Test of Compositions of Cosmetics, Sanitary Products, and Daily Chemical Products

[0511] (1) Antibacterial test method

[0512] The antibacterial test was conducted by the same method as the antibacterial test of the aforementioned cosmetics, sanitary products, and daily chemical product compositions.

[0513] (2) Antibacterial test results of cosmetics, sanitary products, and daily chemical product compositions

[0514] Table 18-19: Antibacterial test results of liquid laundry detergent compositions

[0515] Tables 18 to 29 below show the antibacterial efficacy of the compositions for cosmetics, hygiene products, and daily chemical products, including the preparation examples and comparative examples of the antibacterial and preservative compositions of the Examples and Comparative Examples. After application of the Preparation Examples and Comparative Examples to bacteria, filamentous fungi, and yeasts, the residual bacterial count after 7 days is expressed in CFU / mL. If the residual bacterial count is too high to be counted, it is expressed as TNTC (too-numerous-to-count).

[0516] Table 18 below shows the antibacterial test results of the liquid detergent compositions for laundry of Preparation Examples 1 to 7 against bacteria, filamentous fungi, and yeasts, and Table 19 shows the antibacterial test results of the liquid detergent compositions for laundry of Comparative Examples 1 to 8 against bacteria, filamentous fungi, and yeasts.

[0517] Referring to Table 18, it was confirmed that the liquid detergent compositions for clothing of Preparation Examples 1 to 7 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0518] Furthermore, it was confirmed that the liquid laundry detergent compositions of Preparation Examples 1 to 7 containing both Chemical Formula 1 and Chemical Formula 3 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the liquid laundry detergent compositions of Preparation Examples 1 to 8 containing only Chemical Formula 1 or Chemical Formula 3.

[0519] Table 18:

[0520]

[0521] Table 19:

[0522]

[0523]

[0524] Table 20-21: Antibacterial test results of kitchen cleaning composition

[0525] Table 20 below shows the antibacterial test results of the kitchen detergent compositions of Preparation Examples 8 to 14 against bacteria, filamentous fungi, and yeasts, and Table 21 shows the antibacterial test results of the kitchen detergent compositions of Comparative Preparation Examples 9 to 16 against bacteria, filamentous fungi, and yeasts.

[0526] Referring to Table 20, it was confirmed that the kitchen cleaner compositions of Preparation Examples 8 to 14 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0527] Furthermore, it was confirmed that the kitchen cleaning compositions of Preparation Examples 8 to 14 containing both Chemical Formula 1 and Chemical Formula 3 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the kitchen cleaning compositions of Preparation Examples 9 to 16 containing only Chemical Formula 1 or Chemical Formula 3.

[0528] Table 20:

[0529]

[0530] Table 21:

[0531]

[0532]

[0533] Table 22-23: Antibacterial test results of wet wipes stock solution composition

[0534] Table 22 below shows the antibacterial test results of the wet wipes stock solution compositions of Preparation Examples 15 to 21 against bacteria, filamentous fungi, and yeasts, and Table 23 shows the antibacterial test results of the wet wipes stock solution compositions of Preparation Comparative Examples 17 to 24 against bacteria, filamentous fungi, and yeasts.

[0535] Referring to Table 22, it was confirmed that the wet wipes stock solution compositions of Preparation Examples 15 to 21 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0536] Furthermore, it has been confirmed that compared with the wet wipe stock solution compositions of Preparation Examples 17 to 24 containing only Chemical Formula 1 or Chemical Formula 3, the wet wipe stock solution compositions of Preparation Examples 15 to 21 containing both Chemical Formula 1 and Chemical Formula 3 have excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0537] Table 22:

[0538]

[0539] Table 23:

[0540]

[0541]

[0542] Table 24-25: Antibacterial test results of shampoo stock solution composition

[0543] Table 24 below shows the antibacterial test results of the shampoo stock solutions of Preparation Examples 22 to 28 against bacteria, filamentous fungi, and yeasts, and Table 25 shows the antibacterial test results of the shampoo stock solutions of Preparation Examples 25 to 32 against bacteria, filamentous fungi, and yeasts.

[0544] Referring to Table 24, it was confirmed that the shampoo concentrate compositions of Preparation Examples 22 to 28 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0545] Furthermore, it was confirmed that the shampoo stock solution compositions of Preparation Examples 22 to 28 containing both Chemical Formula 1 and Chemical Formula 3 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the shampoo stock solution compositions of Preparation Examples 25 to 32 containing only Chemical Formula 1 or Chemical Formula 3.

[0546] Table 24:

[0547]

[0548] Table 25:

[0549]

[0550]

[0551] Table 26-27: Antibacterial test results of cosmetic cream stock solution composition

[0552] Table 26 below shows the antibacterial test results of the cosmetic facial cream stock solution compositions of Preparation Examples 29 to 35 against bacteria, filamentous fungi, and yeasts, and Table 27 shows the antibacterial test results of the cosmetic facial cream stock solution compositions of Preparation Examples 33 to 40 against bacteria, filamentous fungi, and yeasts.

[0553] Referring to Table 26, it was confirmed that the cosmetic facial cream stock solution compositions of Preparation Examples 29 to 35 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0554] Furthermore, it was confirmed that the cosmetic cream stock solution compositions of Preparation Examples 29 to 35 containing both Chemical Formula 1 and Chemical Formula 3 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the cosmetic cream stock solution compositions of Preparation Examples 33 to 40 containing only Chemical Formula 1 or Chemical Formula 3.

[0555] Table 26:

[0556]

[0557] Table 27:

[0558]

[0559] Table 28-29: Antibacterial test results of cosmetic powder compositions

[0560] Table 28 below shows the antibacterial test results of the cosmetic powder compositions of Preparation Examples 36 to 42 against bacteria, filamentous fungi, and yeasts, and Table 29 shows the antibacterial test results of the cosmetic powder compositions of Comparative Examples 41 to 48 against bacteria, filamentous fungi, and yeasts.

[0561] Referring to Table 28, it was confirmed that the cosmetic powder compositions of Preparation Examples 36 to 42 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0562] Furthermore, it was confirmed that the cosmetic powder compositions of Preparation Examples 36 to 42 containing both Chemical Formula 1 and Chemical Formula 3 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the cosmetic powder compositions of Preparation Examples 41 to 48 containing only Chemical Formula 1 or Chemical Formula 3.

[0563] Table 28:

[0564]

[0565] Table 29:

[0566]

[0567] Test C: Antibacterial Effects of Compounds Represented by Chemical Formula 1 and Chemical Formula 4

[0568] Examples 1 to 12: Preparation of antibacterial and preservation compositions using the compounds shown in Chemical Formula 1 and Chemical Formula 4

[0569] Example 1.

[0570] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the hexane-1,2-diol compound shown in Chemical Formula 4 were mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0571] Example 2.

[0572] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the octane-1,2-diol compound shown in Chemical Formula 4 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0573] Example 3.

[0574] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the decane-1,2-diol compound shown in Chemical Formula 4 are mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0575] Example 4.

[0576] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the ethylhexylglycerol compound shown in Chemical Formula 4 were mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0577] Example 5.

[0578] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the monocaprylic glycerol compound shown in Chemical Formula 4 were mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0579] Example 6.

[0580] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the octylglycerol compound shown in Chemical Formula 4 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0581] Example 7.

[0582] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the hexylglycerol compound shown in Chemical Formula 4 were mixed at weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0583] Example 8.

[0584] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the levulinic acid compound shown in Chemical Formula 4 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0585] Example 9.

[0586] 3,3'-(dodecylimino)bispropane-1,2-diol as shown in Chemical Formula 1 and a citric acid compound as shown in Chemical Formula 4 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0587] Example 10.

[0588] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the sodium anisate compound shown in Chemical Formula 4 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0589] Example 11.

[0590] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the disodium ethylenediaminetetraacetic acid compound shown in Chemical Formula 4 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0591] Example 12.

[0592] The 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the tetrasodium ethylenediaminetetraacetic acid compound shown in Chemical Formula 4 are mixed in weight ratios of 2:8, 5:5, and 8:2 to prepare a composition for antibacterial and preservation.

[0593] Comparative Examples 1 to 13: Preparation of antibacterial and preservation compositions using the compound shown in Chemical Formula 1 or Chemical Formula 4. Comparative Example 1.

[0594] A 3,3′-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 is used.

[0595] Comparative Example 2.

[0596] A hexane-1,2-diol compound as shown in Chemical Formula 4 is used.

[0597] Comparative Example 3.

[0598] An octane-1,2-diol compound as shown in Chemical Formula 4 is used.

[0599] Comparative Example 4.

[0600] A decane-1,2-diol compound as shown in Chemical Formula 4 is used.

[0601] Comparative Example 5.

[0602] An ethylhexylglycerin compound as shown in Chemical Formula 4 was used.

[0603] Comparative Example 6.

[0604] The monocaprylic acid glyceryl compound shown in Chemical Formula 4 is used.

[0605] Comparative Example 7.

[0606] An octylglycerol compound as shown in Chemical Formula 4 is used.

[0607] Comparative Example 8.

[0608] A hexylglycerol compound as shown in Chemical Formula 4 is used.

[0609] Comparative Example 9.

[0610] A levulinic acid compound as shown in Chemical Formula 4 is used.

[0611] Comparative Example 10.

[0612] A citric acid compound as shown in Chemical Formula 4 is used.

[0613] Comparative Example 11.

[0614] A sodium anisate compound as shown in Chemical Formula 4 is used.

[0615] Comparative Example 12.

[0616] A disodium ethylenediaminetetraacetic acid compound as shown in Chemical Formula 4 is used.

[0617] Comparative Example 13.

[0618] A tetrasodium ethylenediaminetetraacetic acid compound as shown in Chemical Formula 4 is used.

[0619] Preparation Examples and Comparative Examples

[0620] The components used in the following preparation examples and comparative examples were purchased from Sigma-Aldrich Korea and TCI, among others. The antimicrobial and preservation compositions of the examples were prepared by combining the 3,3'-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with the compound represented by Chemical Formula 4 in a weight ratio of 8:2. These compositions were then used to prepare preparation examples of cosmetics, sanitary products, or daily chemical products. Comparative examples of cosmetics, sanitary products, or daily chemical products were then prepared using the antimicrobial and preservation compositions of the comparative examples containing only the compounds of Chemical Formula 1 or Chemical Formula 4.

[0621] Preparation Examples 1 to 12: Liquid detergent compositions for clothing

[0622] Preparation Example 1.

[0623] A liquid laundry detergent composition was prepared, comprising 6 weight percent of laureth-7, 3 weight percent of alkylbenzene sulfonate, 5 weight percent of sodium laureth-2 sulfate, 0.3 weight percent of protease, 0.3 weight percent of lipase, 1 weight percent of coconut fatty acid soap, 2 weight percent of salt, 0.2 weight percent of fragrance, 81.7 weight percent of purified water, and 0.5 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0624] Preparation Examples 2 to 12.

[0625] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the liquid laundry detergent compositions of Preparation Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were prepared in sequence by the same method as in Preparation Example 1.

[0626] Preparation Examples 13-24: Kitchen Cleaner Compositions

[0627] Preparation Example 13.

[0628] A kitchen cleaning composition was prepared, comprising 5 weight percent of sodium laureth-2 sulfate, 4 weight percent of α-olefin sulfonate, 2 weight percent of amine oxide, 2 weight percent of alkyl glycoside, 2 weight percent of alkylbenzene sulfonate, 2 weight percent of glycerin, 0.2 weight percent of fragrance, 82.5 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0629] Preparation Examples 14-24.

[0630] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were used instead of the antibacterial and preservation composition prepared according to Example 1, and the kitchen cleaning compositions of Preparation Examples 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, and 24 were prepared in sequence by the same method as Preparation Example 13.

[0631] Preparation Examples 25-36: Wet Wipes Stock Composition

[0632] Preparation Example 25.

[0633] A wet wipe stock solution composition was prepared, comprising 1 weight percent of a natural extract, 98.7 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0634] Preparation Examples 26-36.

[0635] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the wet wipes stock solutions of Preparation Examples 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, and 36 were prepared in sequence by the same method as Preparation Example 25.

[0636] Preparation Examples 37-48: Shampoo Stock Composition

[0637] Preparation Example 37.

[0638] A shampoo stock composition was prepared, comprising 0.05 weight percent of disodium EDTA, 0.1 weight percent of panthenol, 1 weight percent of glycerin, 1 weight percent of tocopheryl acetate, 0.5 weight percent of polyquaternium-7, 8 weight percent of sodium laureth sulfate, 5 weight percent of cocamidopropyl betaine, 2 weight percent of sodium cocoyl sarcosinate, 0.5 weight percent of polyquaternium-10, 1 weight percent of fragrance, 80.55 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservative composition prepared according to Example 1.

[0639] Preparation Examples 38-48.

[0640] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the shampoo stock solutions of Preparation Examples 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, and 48 were prepared in sequence by the same method as Preparation Example 37.

[0641] Preparation Examples 49-60: Cosmetic Cream Stock Solution Composition

[0642] Preparation Example 49.

[0643] A facial cream stock solution composition was prepared, comprising 2.5 weight percent of cetearyl alcohol, 1.5 weight percent of glyceryl stearate, 5.0 weight percent of tricaprylin, 1.2 weight percent of polysorbate 60, 0.5 weight percent of sorbitan stearate, 5.0 weight percent of squalane, 3.0 weight percent of liquid paraffin, 3.0 weight percent of cyclomethicone, 0.2 weight percent of δ-tocopherol, 4.0 weight percent of glycerol, 2.0 weight percent of 1,3-butylene glycol, 0.2 weight percent of xanthan gum, 0.05 weight percent of disodium ethylenediaminetetraacetic acid (EDTA-2Na), 0.1 weight percent of fragrance, 71.55 weight percent of purified water, and 0.2 weight percent of the composition for antibacterial and preservation prepared according to Example 1.

[0644] Preparation Examples 50-60.

[0645] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the cream stock solutions of Preparation Examples 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, and 60 were prepared in sequence by the same method as Preparation Example 49.

[0646] Preparation Examples 61-72: Cosmetic Pressed Powder (Solid Makeup) Compositions

[0647] Preparation Example 61.

[0648] A pressed powder (solid makeup) composition was prepared, comprising 25 weight percent of spherical powder (Silica-HDI), 10 weight percent of calcium aluminum borosilicate, 20 weight percent of an oily adhesive silicone oil (dimethicone), 0.2 weight percent of a fragrance, 5 weight percent of a pigment, 20 weight percent of ethanol, 19.4 weight percent of plate-like talc (Talc JA46R), and 0.4 weight percent of the antibacterial and preservation composition prepared according to Example 1.

[0649] Preparation Examples 62-72.

[0650] The antibacterial and preservation compositions prepared according to Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were used instead of the antibacterial and preservation compositions prepared according to Example 1, and the pressed powder (solid makeup) compositions of Preparation Examples 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, and 72 were prepared in sequence by the same method as Preparation Example 61.

[0651] Preparation of Comparative Examples 1 to 13: Liquid Cleanser Compositions for Clothes

[0652] Preparation of Comparative Example 1.

[0653] A liquid detergent composition for laundry was prepared, comprising 6 weight percent of laureth-7, 3 weight percent of alkylbenzene sulfonate, 5 weight percent of sodium laureth-2 sulfate, 0.3 weight percent of protease, 0.3 weight percent of lipase, 1 weight percent of coconut fatty acid soap, 2 weight percent of salt, 0.2 weight percent of fragrance, 81.7 weight percent of purified water, and 0.5 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0654] Preparation of Comparative Examples 2 to 13.

[0655] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13 were used instead of the antibacterial and preservation compositions prepared according to Comparative Example 1, and the liquid laundry detergent compositions of Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13 were prepared in sequence by the same method as that for Comparative Example 1.

[0656] Preparation of Comparative Examples 14 to 26: Kitchen Cleaner Compositions

[0657] Preparation of Comparative Example 14.

[0658] A kitchen cleaning composition was prepared, comprising 5 weight percent of sodium laureth-2 sulfate, 4 weight percent of α-olefin sulfonate, 2 weight percent of amine oxide, 2 weight percent of alkyl glycoside, 2 weight percent of alkylbenzene sulfonate, 2 weight percent of glycerin, 0.2 weight percent of fragrance, 82.5 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0659] Preparation of Comparative Examples 15 to 26.

[0660] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the kitchen cleaning compositions of Comparative Examples 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, and 26 were prepared in sequence by the same method as that for preparing Comparative Example 14.

[0661] Preparation of Comparative Examples 27 to 39: Wet Wipes Stock Liquid Composition

[0662] Preparation of Comparative Example 27.

[0663] A wet wipe stock solution composition was prepared, comprising 1 weight percent of a natural extract, 98.7 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0664] Preparation of Comparative Examples 28 to 39.

[0665] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13 were used instead of the composition for antibacterial and preservation prepared according to Comparative Example 1, and the wet wipes stock solutions of Comparative Examples 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, and 39 were prepared in sequence by the same method as that for Comparative Example 27.

[0666] Preparation of Comparative Examples 40-52: Shampoo Stock Liquid Composition

[0667] Preparation of Comparative Example 40.

[0668] A shampoo stock composition was prepared, comprising 0.05 weight percent of disodium EDTA, 0.1 weight percent of panthenol, 1 weight percent of glycerin, 1 weight percent of tocopheryl acetate, 0.5 weight percent of polyquaternium-7, 8 weight percent of sodium laureth sulfate, 5 weight percent of cocamidopropyl betaine, 2 weight percent of sodium cocoyl sarcosinate, 0.5 weight percent of polyquaternium-10, 1 weight percent of fragrance, 80.55 weight percent of purified water, and 0.3 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0669] Preparation of Comparative Examples 41 to 52.

[0670] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13 were used instead of the antibacterial and preservation composition prepared according to Comparative Example 1, and the shampoo stock solutions of Comparative Examples 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, and 52 were prepared in sequence by the same method as that for Comparative Example 40.

[0671] Preparation of Comparative Examples 53-65: Cosmetic Cream Stock Solution Composition

[0672] Preparation of Comparative Example 53.

[0673] A facial cream stock composition is prepared, which includes 2.5 weight percent of cetearyl alcohol, 1.5 weight percent of glyceryl stearate, 5.0 weight percent of tricaprylin, 1.2 weight percent of polysorbate 60, 0.5 weight percent of sorbitan stearate, 5.0 weight percent of squalane, 3.0 weight percent of liquid paraffin, 3.0 weight percent of cyclomethicone, 0.2 weight percent of δ-tocopherol, 4.0 weight percent of glycerol, 2.0 weight percent of 1,3-butylene glycol, 0.2 weight percent of xanthan gum, 0.05 weight percent of disodium ethylenediaminetetraacetic acid (EDTA-2Na), 0.1 weight percent of fragrance, 71.55 weight percent of purified water, and 0.2 weight percent of the composition for antibacterial and preservation prepared according to Comparative Example 1.

[0674] Preparation of Comparative Examples 54 to 65.

[0675] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13 were used instead of the antibacterial and preservation compositions prepared according to Comparative Example 1, and the cream stock solutions of Comparative Examples 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, and 65 were prepared in sequence by the same method as that for preparing Comparative Example 53.

[0676] Preparation of Comparative Examples 66-78: Cosmetic Pressed Powder (Solid Makeup) Compositions

[0677] Preparation of Comparative Example 66.

[0678] A pressed powder (solid makeup) composition was prepared, comprising 25 weight percent of spherical powder (Silica-HDI), 10 weight percent of calcium aluminum borosilicate, 20 weight percent of an oily adhesive silicone oil (dimethicone), 0.2 weight percent of a fragrance, 5 weight percent of a pigment, 20 weight percent of ethanol, 19.4 weight percent of plate-like talc (Talc JA 46R), and 0.4 weight percent of the antibacterial and preservation composition prepared according to Comparative Example 1.

[0679] Preparation of Comparative Examples 67 to 78.

[0680] The antibacterial and preservation compositions prepared according to Comparative Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, and 13 were used instead of the composition for antibacterial and preservation prepared according to Comparative Example 1, and the pressed powder (solid makeup) compositions of Comparative Examples 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, and 78 were prepared in sequence by the same method as that for preparing Comparative Example 66.

[0681] Experimental example

[0682] Using the compounds represented by Chemical Formula 1 and Chemical Formula 4, each composition for antibacterial and preservation prepared according to the components of the above-mentioned Examples and Comparative Examples, and each cosmetic, sanitary product, and daily chemical product composition prepared according to the Preparation Examples and Comparative Examples were tested for antibacterial effects on bacteria, filamentous fungi, and yeasts, and the methods are as follows.

[0683] Experimental Example 1: Antibacterial test of the composition for antibacterial and preservation

[0684] The antibacterial test was conducted by the same method as the antibacterial test of the aforementioned composition for antibacterial and preservation.

[0685] The test results are shown in Tables 30 and 31. It can be seen from the test results that the antibacterial and preservation composition of the present invention effectively controls bacteria, filamentous fungi, and yeasts.

[0686] Table 30-31: Antibacterial test results of the composition used for antibacterial and preservation

[0687] Table 30 shows the antibacterial test results of the composition for antibacterial and preservation prepared according to the examples against bacteria, filamentous fungi, and yeasts. Table 31 shows the antibacterial test results of the composition for antibacterial and preservation prepared according to the comparative examples against bacteria, filamentous fungi, and yeasts, which are expressed as minimum inhibitory concentration (MIC).

[0688] Referring to Tables 30 and 31, the antibacterial and preservation compositions prepared according to all examples of the present invention exhibited excellent antibacterial effects against bacteria, filamentous fungi, and yeasts, compared to the comparative example using only the compounds in Table 31. In particular, it was confirmed that the antibacterial and preservation composition comprising a combination of the compound of Chemical Formula 1 and the compound of Chemical Formula 4 at a ratio of 8:2 was the most effective in controlling bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), and Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis), and yeast (Candida albicans (C. albicans)).

[0689] Table 30:

[0690]

[0691]

[0692] Table 31:

[0693]

[0694]

[0695] Experimental Example 2: Antibacterial Test of Compositions of Cosmetics, Sanitary Products, and Daily Chemical Products

[0696] (1) Antibacterial test method

[0697] The antibacterial test was conducted by the same method as the antibacterial test of the aforementioned cosmetics, sanitary products, and daily chemical product compositions.

[0698] (2) Antibacterial test results of cosmetics, sanitary products, and daily chemical product compositions

[0699] Table 32-33: Antibacterial test results of liquid laundry detergent compositions

[0700] Tables 32 to 43 below show the antibacterial efficacy of the compositions for cosmetics, hygiene products, and daily chemical products, including the preparation examples and comparative examples of the antibacterial and preservative compositions of the Examples and Comparative Examples. After application of the Preparation Examples and Comparative Examples to bacteria, filamentous fungi, and yeasts, the residual bacterial count after 7 days is expressed in CFU / mL. If the residual bacterial count is too high to be counted, it is expressed as TNTC (too-numerous-to-count).

[0701] Table 32 below shows the antibacterial test results of the liquid detergent compositions for clothing of Preparation Examples 1 to 12 against bacteria, filamentous fungi, and yeasts, and Table 33 shows the antibacterial test results of the liquid detergent compositions for clothing of Comparative Examples 1 to 13 against bacteria, filamentous fungi, and yeasts.

[0702] Referring to Table 32, it was confirmed that the liquid detergent compositions for clothing of Preparation Examples 1 to 12 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0703] Furthermore, it was confirmed that the liquid laundry detergent compositions of Preparation Examples 1 to 12 containing both Chemical Formula 1 and Chemical Formula 4 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the liquid laundry detergent compositions of Preparation Examples 1 to 13 containing only Chemical Formula 1 or Chemical Formula 4.

[0704] Table 32:

[0705]

[0706] Table 33:

[0707]

[0708] Table 34-35: Antibacterial test results of kitchen cleaner compositions

[0709] Table 34 below shows the antibacterial test results of the kitchen detergent compositions of Preparation Examples 13 to 24 against bacteria, filamentous fungi, and yeasts, and Table 35 shows the antibacterial test results of the kitchen detergent compositions of Comparative Examples 14 to 26 against bacteria, filamentous fungi, and yeasts.

[0710] Referring to Table 34, it was confirmed that the kitchen cleaner compositions of Preparation Examples 13 to 24 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0711] Furthermore, it was confirmed that the kitchen cleaning compositions of Preparation Examples 13 to 24, which contain both Chemical Formula 1 and Chemical Formula 4, had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the kitchen cleaning compositions of Preparation Examples 14 to 26, which contain only Chemical Formula 1 or Chemical Formula 4.

[0712] Table 34:

[0713]

[0714]

[0715] Table 35:

[0716]

[0717] Table 36-37: Antibacterial test results of wet wipes stock solution composition

[0718] Table 36 below shows the antibacterial test results of the wet wipes stock solutions of Preparation Examples 25 to 36 against bacteria, filamentous fungi, and yeasts, and Table 37 shows the antibacterial test results of the wet wipes stock solutions of Preparation Examples 27 to 39 against bacteria, filamentous fungi, and yeasts.

[0719] Referring to Table 36, it was confirmed that the wet wipes stock solution compositions of Preparation Examples 25 to 36 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0720] Furthermore, it has been confirmed that compared with the wet wipe stock solution compositions of Preparation Examples 27 to Preparation Examples 39 containing only Chemical Formula 1 or Chemical Formula 4, the wet wipe stock solution compositions of Preparation Examples 25 to Preparation Examples 36 containing both Chemical Formula 1 and Chemical Formula 4 have excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0721] Table 36:

[0722]

[0723] Table 37:

[0724]

[0725] Table 38-39: Antibacterial test results of shampoo stock solution composition

[0726] Table 38 below shows the antibacterial test results of the shampoo concentrate compositions of Preparation Examples 37 to 48 against bacteria, filamentous fungi, and yeasts, and Table 39 shows the antibacterial test results of the shampoo concentrate compositions of Preparation Examples 40 to 52 against bacteria, filamentous fungi, and yeasts.

[0727] Referring to Table 38, it was confirmed that the shampoo concentrate compositions of Preparation Examples 37 to 48 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0728] Furthermore, it was confirmed that the shampoo stock solution compositions of Preparation Examples 37 to 48 containing both Chemical Formula 1 and Chemical Formula 4 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the shampoo stock solution compositions of Preparation Examples 40 to 52 containing only Chemical Formula 1 or Chemical Formula 4.

[0729] Table 38:

[0730]

[0731] Table 39:

[0732]

[0733]

[0734] Table 40-41: Antibacterial test results of cosmetic cream stock solution composition

[0735] Table 40 below shows the antibacterial test results of the cosmetic facial cream stock solutions of Preparation Examples 49 to 60 against bacteria, filamentous fungi, and yeasts, and Table 41 shows the antibacterial test results of the cosmetic facial cream stock solutions of Preparation Examples 53 to 65 against bacteria, filamentous fungi, and yeasts.

[0736] Referring to Table 40, it was confirmed that the cosmetic facial cream stock solution compositions of Preparation Examples 49 to 60 can effectively control all bacteria used in the antibacterial test (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)).

[0737] Furthermore, it was confirmed that the cosmetic cream stock solution compositions of Preparation Examples 49 to 60 containing both Chemical Formula 1 and Chemical Formula 4 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the cosmetic cream stock solution compositions of Preparation Examples 53 to 65 containing only Chemical Formula 1 or Chemical Formula 4.

[0738] Table 40:

[0739]

[0740] Table 41:

[0741]

[0742]

[0743] Table 42-43: Antibacterial test results of cosmetic powder compositions

[0744] Table 42 below shows the antibacterial test results of the cosmetic powder compositions of Preparation Examples 61 to 72 against bacteria, filamentous fungi, and yeasts, and Table 43 shows the antibacterial test results of the cosmetic powder compositions of Comparative Examples 66 to 78 against bacteria, filamentous fungi, and yeasts.

[0745] Referring to Table 42, it was confirmed that the cosmetic powder compositions of Preparation Examples 61 to 72 can effectively control all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) used in the antibacterial test.

[0746] Furthermore, it was confirmed that the cosmetic powder compositions of Preparation Examples 61 to 72 containing both Chemical Formula 1 and Chemical Formula 4 had excellent antibacterial effects on all bacteria (Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa)), filamentous fungi (Aspergillus brasiliensis (A. brasiliensis)), and yeast (Candida albicans (C. albicans)) compared to the cosmetic powder compositions of Preparation Examples 66 to 78 containing only Chemical Formula 1 or Chemical Formula 4.

[0747] Table 42:

[0748]

[0749] Table 43:

[0750]

[0751]

[0752] Test D: Anti-dandruff fungal effect

[0753] Experimental Example 1: Preparation of a hair care (antifungal) composition for preventing dandruff using Chemical Formula 1 and a piroctone olamine salt compound and evaluation of bactericidal activity

[0754] 1-1. Preparation of a hair care (antifungal) composition for preventing dandruff

[0755] A hair care (antifungal) composition for preventing dandruff was prepared by mixing a 3,3′-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 with a piroctone olamine (PO) compound at different mixing ratios.

[0756] 1-2. Evaluation of bactericidal activity

[0757] (1) Pre-culture of test bacteria

[0758] The dandruff fungi Malassezia furfur, Malassezia restricta, and Malassezia globosa, which were tested as strains, were inoculated into Leeming & Notman broth and cultured at 30±2°C for 72 to 96 hours.

[0759] (2) Preparation of test solution

[0760] The hair care (antifungal) composition for preventing dandruff prepared above was dissolved in dimethyl sulfoxide (DMSO) to prepare a test solution.

[0761] (3) Mixed bacterial strains and hair care (antifungal) composition for preventing dandruff (test solution)

[0762] After adding liquid culture medium to the test tube, the test solution was diluted to a treatment concentration ranging from a maximum of 5% to a minimum of 0.0001%. Leeming & Notman broth was used as the liquid culture medium to culture Malassezia furfur, Malassezia restricta, and Malassezia globosa.

[0763] (4) Inoculation of test bacterial solution

[0764] Inoculate Malassezia furfur, Malassezia restricta, and Malassezia globosa to a concentration of 1 × 10 5 CFU / mL. Test tubes treated with the test solution were incubated at 30±2°C for 72-96 hours. A culture tube without bacterial solution was used as a negative control, and a tube inoculated with bacterial solution alone without the test solution was used as a growth control. Furthermore, to confirm the antimicrobial activity of the solvent, dimethyl sulfoxide (DMSO), the MIC of the test bacteria against the solvent was determined using the same test conditions as the sample.

[0765] The bactericidal effect of the test solution was measured using the broth dilution method. The treatment concentration of the test solution was diluted to a maximum concentration of 5% and a minimum concentration of 0.0001% for use. After the test solution was incubated with the strain, the turbidity of the test tube was checked. At this time, the concentration of the test solution in the test tube where no bacterial growth was observed among the test tubes treated with different concentrations of the test solution was determined as the minimum inhibitory concentration (MIC), relative to the turbidity observed in the test tube in which the test solution was not treated on the culture medium but only inoculated with the strain. After completing the above-mentioned first test, a second test was performed to further fine-tune the treatment concentration of the test solution to obtain an accurate minimum inhibitory concentration (MIC).

[0766] (5) Results of bactericidal tests on hair care (antifungal) compositions for preventing dandruff

[0767] The test results are shown in Tables 44 to 46.

[0768] Table 44 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which were prepared by mixing 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with piroctone olamine (PO) at different mixing ratios, on Malassezia furfur.

[0769] Table 44:

[0770]

[0771] The results showed that the fungicidal effect was minimal when the compound of Chemical Formula 1 was used alone, but was enhanced when the compound of Chemical Formula 1 was mixed with piroctone olamine (PO) at a lower ratio. When the 3,3'-(dodecylimino)bispropane-1,2-diol compound of Chemical Formula 1 was mixed with piroctone olamine (PO) at a ratio of 8:2 to 1:9, the fungicidal effect against Malassezia furfur was relatively high.

[0772] Table 45 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which were prepared by mixing 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with piroctone olamine (PO) at different mixing ratios, on Malassezia restricta.

[0773] Table 45:

[0774]

[0775] The results showed that when the compound of Chemical Formula 1 was used alone, the bactericidal effect was minimal. However, when the mixing ratio of the compound of Chemical Formula 1 was reduced and piroctone olamine (PO) was added, the bactericidal effect was enhanced. When the 3,3'-(dodecylimino)bispropane-1,2-diol compound of Chemical Formula 1 was mixed with piroctone olamine (PO) in a ratio of 9:1 to 1:9, the bactericidal effect against Malassezia restricta was relatively high.

[0776] Table 46 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which were prepared by blending 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 and piroctone olamine (PO) at different mixing ratios, on Malassezia globosa.

[0777] Table 46:

[0778]

[0779]

[0780] The results showed that the fungicidal effect was minimal when the compound of Chemical Formula 1 was used alone, but was enhanced when the compound of Chemical Formula 1 was mixed with piroctone olamine (PO) at a lower ratio. When the 3,3'-(dodecylimino)bispropane-1,2-diol compound of Chemical Formula 1 was mixed with piroctone olamine (PO) at a ratio of 9:1 to 1:9, the fungicidal effect against Malassezia globosa was relatively high.

[0781] The test results show that the hair care (antifungal) composition for preventing dandruff using the compound of Chemical Formula 1 and piroctone olamine (PO) of the present invention effectively controls Malassezia furfur, Malassezia restricta, and Malassezia globosa, which are dandruff fungi, even if the content of piroctone olamine (PO) in the total weight of the composition is reduced and the content of the compound of Chemical Formula 1 is increased.

[0782] Experimental Example 2: Preparation of a hair care (antifungal) composition for preventing dandruff using Chemical Formula 1 and a zinc pyrithione compound and evaluation of the bactericidal effect

[0783] 2-1. Preparation of a hair care (antifungal) composition for preventing dandruff

[0784] A hair care (antifungal) composition for preventing dandruff was prepared by mixing a 3,3′-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 with a zinc pyrithione (ZPT) compound at different mixing ratios.

[0785] 2-2. Evaluation of bactericidal activity

[0786] The bactericidal activity was evaluated by the same method as in Experimental Example 1-2.

[0787] The test results are shown in Tables 47 to 49.

[0788] Table 47 shows the fungicidal effects of hair care (antifungal) compositions for preventing dandruff, which contain 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 and zinc pyrithione (ZPT) at different mixing ratios, on Malassezia furfur.

[0789] Table 47:

[0790]

[0791] The results showed that the fungicidal effect was minimal when the compound of Chemical Formula 1 was used alone, but was enhanced when the compound of Chemical Formula 1 was mixed with zinc pyrithione (ZPT) in a ratio of 8:2 to 1:9. A relatively high fungicidal effect against Malassezia furfur was observed when the compound of Chemical Formula 1, 3,3'-(dodecylimino)bispropane-1,2-diol, was mixed with zinc pyrithione (ZPT).

[0792] Table 48 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which contain 3,3'-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 and zinc pyrithione (ZPT) at different mixing ratios, on Malassezia restricta.

[0793] Table 48:

[0794]

[0795] The results showed that the fungicidal effect was minimal when the compound of Chemical Formula 1 was used alone, but was enhanced when the compound of Chemical Formula 1 was mixed with zinc pyrithione (ZPT) at a ratio of 9:1 to 1:9. A relatively high fungicidal effect against Malassezia restricta was observed when the compound of Chemical Formula 1, 3,3'-(dodecylimino)bispropane-1,2-diol, was mixed with zinc pyrithione (ZPT).

[0796] Table 49 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which contain 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 and zinc pyrithione (ZPT) at different mixing ratios, on Malassezia globosa.

[0797] Table 49:

[0798]

[0799] The results showed that the fungicidal effect was minimal when the compound of Chemical Formula 1 was used alone, but was enhanced when the compound of Chemical Formula 1 was mixed with zinc pyrithione (ZPT) at a ratio of 9:1 to 1:9. A relatively high fungicidal effect against Malassezia globosa was observed when the compound of Chemical Formula 1, 3,3'-(dodecylimino)bispropane-1,2-diol, was mixed with zinc pyrithione (ZPT).

[0800] The test results show that the hair care (antifungal) composition for preventing dandruff using the compound of Chemical Formula 1 and zinc pyrithione (ZPT) of the present invention effectively controls dandruff fungi such as Malassezia furfur, Malassezia restricta, and Malassezia globosa, even when the content of zinc pyrithione (ZPT) in the total weight of the composition is reduced and the content of the compound of Chemical Formula 1 is increased.

[0801] Experimental Example 3: Preparation of a hair care (antifungal) composition for preventing dandruff using Chemical Formula 1 and a climbazole (CB) compound and evaluation of the bactericidal effect

[0802] 3-1. Preparation of a hair care (antifungal) composition for preventing dandruff

[0803] A hair care (antifungal) composition for preventing dandruff was prepared by mixing 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with climbazole (CB) at different mixing ratios.

[0804] 3-2. Evaluation of bactericidal activity

[0805] The bactericidal activity was evaluated by the same method as in Experimental Example 1-2.

[0806] The test results are shown in Tables 50 to 52.

[0807] Table 50 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which were prepared by blending 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with climbazole (CB) at different mixing ratios, on Malassezia furfur.

[0808] Table 50:

[0809]

[0810] The results showed that the fungicidal effect was minimal when the compound of Chemical Formula 1 was used alone, but was enhanced when the compound of Chemical Formula 1 was mixed with climbazole (CB) at a lower ratio. When the 3,3'-(dodecylimino)bispropane-1,2-diol compound of Chemical Formula 1 was mixed with climbazole (CB) at a ratio of 9:1 to 1:9, the fungicidal effect against Malassezia furfur was relatively high.

[0811] Table 51 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which were prepared by mixing 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with climbazole (CB) at different mixing ratios, on Malassezia restricta.

[0812] Table 51:

[0813]

[0814] The results showed that the fungicidal effect was minimal when the compound of Chemical Formula 1 was used alone, but was enhanced when the compound of Chemical Formula 1 was mixed with climbazole (CB) at a ratio of 9:1 to 1:9. When the 3,3'-(dodecylimino)bispropane-1,2-diol compound of Chemical Formula 1 was mixed with climbazole (CB) at a ratio of 9:1 to 1:9, the fungicidal effect against Malassezia restricta was relatively high.

[0815] Table 52 shows the bactericidal effects of hair care (antifungal) compositions for preventing dandruff, which were prepared by blending 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 with climbazole (CB) at different mixing ratios, on Malassezia globosa.

[0816] Table 52:

[0817]

[0818] The results showed that the compound of Chemical Formula 1 had the lowest bactericidal effect when used alone, but the bactericidal effect was enhanced when the compound of Chemical Formula 1 was mixed with climbazole (CB) at a lower mixing ratio. In particular, when the 3,3'-(dodecylimino)bispropane-1,2-diol compound of Chemical Formula 1 was mixed with climbazole (CB) at a ratio of 8:2 to 1:9, the bactericidal effect against Malassezia globosa was relatively high.

[0819] The test results show that the hair care (antifungal) composition for preventing dandruff using the compound of Chemical Formula 1 and climbazole (CB) of the present invention effectively controls dandruff fungi such as Malassezia furfur, Malassezia restricta, and Malassezia aglobos, even when the content of climbazole (CB) in the total weight of the composition is reduced and the content of the compound of Chemical Formula 1 is increased.

[0820] Experimental Example 4: Evaluation of the Bactericidal Effect of a Shampoo Composition Containing a Hair Care (Antifungal) Composition for Preventing Dandruff 4-1: Preparation of Shampoo Composition

[0821] A shampoo composition was prepared by adding 32 weight percent of sodium laureth sulfate, 17 weight percent of cocamidopropyl betaine, 7 weight percent of coco-glucoside, 0.3 weight percent of dimethicone, 0.3 weight percent of polyquaternium-10, 0.3 weight percent of tetrasodium EDTA, 42.6 weight percent of purified water, and 0.5 weight percent of the hair care (antifungal) composition for preventing dandruff prepared according to Experimental Example 1.

[0822] As the hair care (antifungal) composition for preventing dandruff prepared according to Experimental Example 1, a hair care (antifungal) composition for preventing dandruff containing solely the 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1, a hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 and piroctone olamine (PO) compound in a ratio of 5:5, a hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 and piroctone olamine (PO) in a ratio of 2:8, and a hair care (antifungal) composition for preventing dandruff containing solely piroctone olamine (PO) were used.

[0823] The amounts of the ingredients used in the preparation of the shampoo composition are shown in Table 53.

[0824] Table 53:

[0825] Element Weight percentage Sodium Laureth Sulfate 32 Cocamidopropyl Betaine 17 Coco-Glucoside 7 Dimethicone 0.3 Polyquaternium-10 0.3 Tetrasodium EDTA 0.3 purified water 42.6 Hair care (antifungal) composition for preventing dandruff 0.5 total 100

[0826] 4-2. Evaluation of bactericidal activity of shampoo compositions

[0827] All test solutions, test strain suspensions, reagents, and water were placed in a constant temperature water bath at 20°C ± 1°C. A shampoo composition formulation comprising a hair care (antifungal) composition for preventing dandruff was placed in a sterile test tube, and the test strain suspension was added and immediately mixed.

[0828] The shampoo composition was placed in contact with the test strain suspension at 20±1°C for 3 min±10 s, 5 min±10 s, 10 min±10 s, and 15 min±10 s, respectively, and then diluted with a neutralizer. 1 mL of this dilution was added to each of two Petri dishes. Aseptically dispense approximately 15 mL of sterilized Leeming & Notman agar preparative medium stored at 45±1°C, taking care not to adhere to the Petri dish lid. Gently swirl and tilt the dish side to side to thoroughly mix with the medium, and then cool to solidify.

[0829] To prevent the formation of spreading colonies, add 4-5 mL of sterilized Leeming & Notman agar medium and cover. After cooling and solidifying, invert the plate and incubate at 30±2°C for 72-96 hours. Verify the presence of bacteria in each plate to confirm the effectiveness of the treatment in eliminating dandruff fungi.

[0830] Thus, a shampoo composition formulation containing a hair care (antifungal) composition for preventing dandruff was brought into contact with Malassezia furfur, a dandruff fungus, for 3, 5, 10, and 15 minutes, and a bactericidal experiment was conducted. The presence or absence of Malassezia furfur was indicated by O and X. If Malassezia furfur was not eliminated and remained, it was indicated as O, and if Malassezia furfur was completely eliminated, it was indicated as X.

[0831] (1) Shampoo composition formulation using chemical formula 1 and piroctone olamine salt compound

[0832] The test results are shown in Tables 54 to 56.

[0833] Table 54 shows the bactericidal effect of a shampoo composition using a hair care (antifungal) composition for preventing dandruff containing a 3,3′-(dodecylimino)bispropane-1,2-diol compound or a piroctone olamine (PO) compound on Malassezia furfur.

[0834] Table 54:

[0835]

[0836]

[0837] The results confirmed that the shampoo composition formulations prepared using the hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and the piroctone olamine (PO) compound at a ratio of 5:5 or 2:8, and the hair care (antifungal) composition for preventing dandruff containing the piroctone olamine (PO) compound alone, eliminated Malassezia furfur within 3 minutes, and therefore had excellent bactericidal effect on Malassezia furfur, compared to the shampoo composition formulations prepared using the hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 alone.

[0838] Therefore, it has been confirmed that even if the expensive piroctone olamine salt (PO) compound is not used alone, but the 3,3'-(dodecylimino)bispropane-1,2-diol compound and piroctone olamine salt (PO) are mixed and used as shown in Chemical Formula 1, it still has an excellent bactericidal effect on Malassezia furfur, which is a dandruff fungus. Therefore, 50% of the piroctone olamine salt can be replaced by the compound of Chemical Formula 1 to eliminate the dandruff fungus.

[0839] (2) Shampoo composition formulation using Chemical Formula 1 and zinc pyrithione compound

[0840] Table 55 shows the bactericidal effect on Malassezia furfur using a shampoo composition containing a 3,3′-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 or zinc pyrithione (ZPT) for preventing dandruff (antifungal) composition.

[0841] Table 55:

[0842]

[0843] The results confirmed that the shampoo composition formulation prepared using the hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and zinc pyrithione (ZPT) at a ratio of 5:5 and the hair care (antifungal) composition for preventing dandruff containing zinc pyrithione (ZPT) alone eliminated Malassezia furfur within 3 minutes, compared to the shampoo composition formulation prepared using the hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 alone, and thus had excellent bactericidal activity against Malassezia furfur.

[0844] Therefore, it was confirmed that even if expensive zinc pyrithione (ZPT) is not used alone, but a mixture of 3,3'-(dodecylimino)bispropane-1,2-diol compound as shown in Chemical Formula 1 and zinc pyrithione (ZPT) is used, it still has an excellent bactericidal effect on Malassezia furfur, which is a dandruff fungus. Therefore, 50% of zinc pyrithione (ZPT) can be replaced by the compound of Chemical Formula 1 to eliminate dandruff fungus.

[0845] (3) Shampoo composition formulation using Chemical Formula 1 and a climbazole compound

[0846] Table 56 shows the bactericidal effect on Malassezia furfur using a shampoo composition containing a 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 or climbazole (CB) for preventing dandruff (antifungal) composition.

[0847] Table 56:

[0848]

[0849] The results confirmed that the shampoo composition formulations prepared using the hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 and climbazole (CB) at a ratio of 5:5 or 2:8, and the hair care (antifungal) composition for preventing dandruff containing climbazole (CB) alone, eliminated Malassezia furfur within 3 minutes, and thus had excellent bactericidal effect on Malassezia furfur, as compared to the shampoo composition formulations prepared using the hair care (antifungal) composition for preventing dandruff containing the 3,3'-(dodecylimino)bispropane-1,2-diol compound shown in Chemical Formula 1 alone.

[0850] Therefore, it was confirmed that even if the expensive climbazole (CB) compound is not used alone, but a mixture of the 3,3'-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 and climbazole (CB) is used, it still has an excellent bactericidal effect against Malassezia furfur, which is a dandruff fungus. Therefore, 50% of climbazole (CB) can be replaced by the compound of Chemical Formula 1 to eliminate dandruff fungus.

[0851] Experimental Example 5: Evaluation of the bactericidal effect of shampoo compositions according to the content of the hair care (antifungal) composition for preventing dandruff

[0852] 5-1. Preparation of shampoo composition

[0853] A shampoo composition formulation was prepared by the same method as in Experimental Example 4-1, comprising a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1, piroctone olamine (PO), zinc pyrithione (ZPT), and climbazole (CB) at 0.2 weight percent, 0.3 weight percent, 0.4 weight percent, 0.5 weight percent, 0.6 weight percent, and 0.7 weight percent, respectively, or a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1 and piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) at a ratio of 5:5.

[0854] Specifically, based on 100 weight percent of the shampoo composition, 32 weight percent of sodium laureth sulfate, 17 weight percent of cocamidopropyl betaine, 7 weight percent of coco-glucoside, 0.3 weight percent of dimethicone, 0.3 weight percent of polyquaternium-10, and 0.3 weight percent of tetrasodium EDTA were added to the shampoo composition of Experimental Example 4. Without changing these components, 0.2 weight percent, 0.3 weight percent, 0.4 weight percent, 0.5 weight percent, 0.6 weight percent, and 0.7 weight percent of a hair care (antifungal) composition for preventing dandruff were added, respectively, and the remainder was supplemented with purified water to prepare a shampoo composition of 100 weight percent.

[0855] Then, the prepared shampoo composition formulation was contacted with Malassezia furfur, Malassezia restricta, and Malassezia globosa, which are dandruff fungi, for a fixed contact time of 3 minutes, and the bactericidal effect was measured according to the addition ratio (in weight percentage).

[0856] 5-2. Evaluation of bactericidal activity of shampoo compositions

[0857] (1) Evaluation of bactericidal activity against Malassezia furfur

[0858] As shown in Experimental Example 4-2 above, a shampoo composition formulation containing a hair care (antifungal) composition for preventing dandruff was briefly brought into contact with Malassezia furfur, a dandruff fungus, for 3 minutes to conduct a bactericidal experiment, and the presence or absence of Malassezia furfur was indicated by O and X. If Malassezia furfur was not eliminated and remained, it was indicated as O, and if Malassezia furfur was completely eliminated, it was indicated as X.

[0859] Table 57 shows the results of evaluating the fungicidal effect of shampoo composition formulations on Malassezia furfur, a dandruff fungus, which were prepared by changing the content of a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1, piroctone olamine (PO), zinc pyrithione (ZPT), and climbazole (CB), respectively, and a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1 and piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) at a ratio of 5:5.

[0860] Table 57:

[0861]

[0862] The results confirmed that as the content of the anti-dandruff hair care (antifungal) composition in the shampoo composition increased, its bactericidal activity against Malassezia furfur increased. In particular, shampoo compositions containing the compound of Chemical Formula 1 and piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) at a weight ratio of 5:5 had overall superior bactericidal activity against Malassezia furfur compared to shampoo compositions containing the compound of Chemical Formula 1, piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) alone.

[0863] Therefore, it was confirmed that Malassezia furfur, which is a dandruff fungus, can be eliminated by mixing the compound of Chemical Formula 1 with piroctone olamine (PO), zinc pyrithione (ZPT) or climbazole (CB) compounds at a weight ratio of 5:5, instead of using expensive piroctone olamine (PO), zinc pyrithione (ZPT) or climbazole (CB) alone.

[0864] (2) Evaluation of bactericidal activity against Malassezia restricta

[0865] As shown in Experimental Example 4-2 above, a shampoo composition formulation containing a hair care (antifungal) composition for preventing dandruff was briefly exposed to Malassezia restricta, a dandruff fungus, for 3 minutes to conduct a bactericidal experiment. The presence or absence of Malassezia restricta was indicated by O and X. If Malassezia restricta was not eliminated and remained, it was indicated as O, and if Malassezia restricta was completely eliminated, it was indicated as X.

[0866] Table 58 shows the results of evaluating the fungicidal effect of shampoo composition formulations on Malassezia restricta, a dandruff fungus, which were prepared by changing the content of a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1, piroctone olamine (PO), zinc pyrithione (ZPT), and climbazole (CB), respectively, and a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1 and piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) at a ratio of 5:5.

[0867] Table 58:

[0868]

[0869] The results confirmed that as the content of the anti-dandruff hair care (antifungal) composition in the shampoo composition increased, its bactericidal activity against Malassezia restricta increased. In particular, shampoo compositions containing the compound of Chemical Formula 1 and piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) at a weight ratio of 5:5 showed overall superior bactericidal activity against Malassezia restricta compared to shampoo compositions containing the compound of Chemical Formula 1, piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) alone.

[0870] Therefore, it was confirmed that Malassezia restricta, which is a dandruff fungus, can be eliminated by mixing the compound of Chemical Formula 1 with piroctone olamine (PO), pyrithione zinc (ZPT) or climbazole (CB) compound at a weight ratio of 5:5, instead of using expensive piroctone olamine (PO), pyrithione zinc (ZPT) or climbazole (CB) alone.

[0871] (3) Evaluation of bactericidal activity against Malassezia globosa

[0872] As shown in Experimental Example 4-2 above, a shampoo composition formulation containing a hair care (antifungal) composition for preventing dandruff was briefly brought into contact with Malassezia globosa, a dandruff fungus, for 3 minutes to conduct a bactericidal experiment. The presence or absence of Malassezia globosa was indicated by O and X. If Malassezia globosa was not eliminated and remained, it was indicated as O, and if Malassezia globosa was completely eliminated, it was indicated as X.

[0873] Table 59 shows the results of evaluating the bactericidal effect of shampoo composition formulations on Malassezia globosa, a dandruff fungus, which were prepared by changing the content of a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1, piroctone olamine (PO), zinc pyrithione (ZPT), and climbazole (CB), respectively, and a hair care (antifungal) composition for preventing dandruff comprising the compound of Chemical Formula 1 and piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB).

[0874] Table 59:

[0875]

[0876]

[0877] The results confirmed that as the content of the anti-dandruff hair care (antifungal) composition in the shampoo composition increased, its bactericidal activity against Malassezia globosa increased. In particular, compared with shampoo compositions containing the compound of Chemical Formula 1, piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) alone, shampoo compositions containing the compound of Chemical Formula 1 and piroctone olamine (PO), zinc pyrithione (ZPT), or climbazole (CB) at a weight ratio of 5:5 had overall superior bactericidal activity against Malassezia globosa.

[0878] Therefore, it was confirmed that Malassezia globosa, which is a dandruff fungus, can be eliminated by mixing the compound of Chemical Formula 1 with piroctone olamine (PO), zinc pyrithione (ZPT) or climbazole (CB) in a weight ratio of 5:5, instead of using expensive piroctone olamine (PO), zinc pyrithione (ZPT) or climbazole (CB) alone.

[0879] In summary, the present invention confirms that the compound shown in Chemical Formula 1 can effectively eliminate dandruff fungi. In addition, compared with using the compound shown in Chemical Formula 1 alone, when the compound shown in Chemical Formula 1 is mixed with piroctone olamine, pyrithione zinc, or a climbazole compound, there is a synergistic effect in controlling dandruff fungi, and Malassezia sp. strains can be effectively controlled at lower dosages. Therefore, the advantage of the present invention is that the dosage of the compound shown in Chemical Formula 1 and piroctone olamine, pyrithione zinc, or a climbazole compound can be reduced.

[0880] At the same time, in the present invention, even if more than 50% of piroctone olamine, zinc pyrithione, or climbazole is replaced by the compound of Chemical Formula 1 in a hair care composition such as a shampoo, the same effect as using 100% of piroctone olamine, zinc pyrithione, or climbazole can be exhibited. Moreover, since the compound of Chemical Formula 1 can be prepared at a lower cost, dandruff fungi can be controlled very economically.

[0881] Test E: Antiviral Effect

[0882] Example

[0883] Example 1.

[0884] 2 g of the 3,3′-(dodecylimino)bispropane-1,2-diol compound represented by Chemical Formula 1 was diluted in 1 L of water for use.

[0885] Comparative Example

[0886] Comparative Example 1.

[0887] 2 g of a mixture obtained by mixing n-alkyldimethylethylbenzyl ammonium chloride and alkylbenzyldimethylammonium chloride at a weight ratio (w / w) of 1:1 was diluted in 1 L of water for use.

[0888] Comparative Example 2.

[0889] 2 g of alkylbenzyldimethylammonium chloride (benzalkonium chloride) was diluted in 1 L of water for use.

[0890] Experimental example

[0891] Experimental Example 1. Evaluation of the antiviral effect on coronavirus (Human coronavirus 229E)

[0892] (1) Experimental methods

[0893] After the viral genome enters and replicates in a host cell, it becomes a new virus. These viruses then leave the host cell and invade new host cells to continue replicating. During this process, the host cell that produced the virus dies, and the traces of cell death, called plaques, are used as a unit of viral quantification.

[0894] Using the liquid samples of Example 1 and Comparative Examples 1 and 2 diluted in water, an antiviral test against coronavirus was carried out using the ASTM E1052 method.

[0895] A specific amount of virus is prepared and inoculated into a sample. Sample-exposed and non-exposed virus are diluted 10-fold in a series. The virus prepared at each dilution factor is inoculated into HCT-8 (human colon adenocarcinoma) host cells. The virus undergoes an adsorption (infection) process, enabling it to effectively penetrate host cells through host cell surface receptors. Using a solid culture medium prevents indiscriminate infection of host cells and effectively forms plaques.

[0896] After incubating infected host cells in solid culture medium for a specified period of time, the cells are fixed and then stained with a dye that stains only active cells. The number of plaques is quantified. The quantitative unit is the plaque forming unit (PFU), which is calculated by multiplying the number of plaques by the dilution factor. Antiviral activity is calculated as the log reduction of the sample exposed to the virus (test group) relative to the sample not exposed to the virus (control group). Effectiveness is considered when the log reduction reaches 4 or more and 99.99% or more.

[0897] Table 60:

[0898]

[0899] (2) Experimental results

[0900] The liquid samples of Example 1, Comparative Example 1, and Comparative Example 2 were diluted with water and then treated. The results showed that compared with the sample non-contact virus (control group), the plaque forming units in the liquid samples of all Examples 1, Comparative Example 1, and Comparative Example 2 were significantly reduced, indicating that they have the ability to control coronaviruses. In particular, the sample treatment of Example 1 showed excellent coronavirus control ability, and compared with the quaternary ammonium disinfectants of Comparative Examples 1 and Comparative Examples 2, its coronavirus control effect was significantly better. The test was repeated three times to confirm its reproducibility.

[0901] The quaternary ammonium salt disinfectants in Comparative Examples 1 and 2 are the most common commercially available cationic surfactant viral disinfectants. Cationic surfactants are known to have pulmonary adsorption issues and adverse effects on the respiratory system. In contrast, the compound represented by Chemical Formula 1 in Example 1 is non-ionic and is not adsorbed by the human body but is excreted, making it safe for the human body.

[0902] Table 61:

[0903]

[0904]

[0905] Experimental Example 2. Evaluation of the antiviral effect against influenza A virus (H1N1)

[0906] (1) Experimental methods

[0907] The samples were tested for antiviral activity against influenza A (H1N1) virus using the plaque reduction test method based on ASTM E1052. The plaque reduction test method is a method that directly quantifies the inhibition of a test substance against infectious virus by counting plaques isolated from cell culture. Despite the continuous development of virus quantification methods and technologies, the plaque assay remains the gold standard for determining the concentration of infectious lytic virus. The virus continues its replication-lysis-infection cycle in infected cells, destroying surrounding cells and forming increasingly visible areas. The destroyed cell areas at this time are called plaques, and visible plaques usually form within 2 to 14 days, depending on the virus proliferation and host cell type. At this time, a monolayer of cells (MDCK cells) infected with influenza virus is covered with an overlay culture medium to prevent indiscriminate spread of the virus infection through mechanical or convective flow of the liquid culture medium during the virus proliferation process. The formation of viral plaques can be observed (a fixed overlay technique is used to confirm whether the plaques have decreased).

[0908] Plaque quantification was measured in plaque-forming units (PFUs), calculated as in Experimental Example 1 by multiplying the number of plaques by the dilution factor. Antiviral activity was calculated as the log reduction of the virus-exposed sample (test group) relative to the non-virus-exposed sample (control group). Effectiveness was considered when the log reduction reached 4 or higher and reached 99.99% or higher.

[0909] (2) Experimental results

[0910] Liquid samples from Example 1, Comparative Example 1, and Comparative Example 2 were diluted with water and then treated. Results showed that compared to samples not exposed to the virus (control group), plaque-forming units in all of the liquid samples from Example 1, Comparative Example 1, and Comparative Example 2 were significantly reduced, demonstrating their ability to control influenza A (H1N1) virus. In particular, the sample treatment from Example 1 demonstrated excellent control of influenza A (H1N1) virus, particularly compared to the quaternary ammonium disinfectants used in Comparative Examples 1 and 2. The test was repeated three times to confirm its reproducibility.

[0911] Table 62:

[0912]

[0913] Experimental Example 3. Evaluation of the antiviral effect on avian influenza virus

[0914] (1) Experimental methods

[0915] 200 PFU / well of avian influenza virus were inoculated into a pre-prepared 6-well plate. After 1 hour, all viral inoculum was removed. After washing the cells (MDCK cells) with serum-free medium, the test substance (sample) was aliquoted and incubated in a 37°C, CO2 incubator for 1 hour. To observe normal plaque formation, the test substance treatment time was set within 2 hours. The experiment was repeated twice, and a negative control group (virus only) was set up without test substance treatment.

[0916] After treatment with the test substance, the test substance solution was removed from the plate. 3 mL of agar medium prepared with 4% FBSDMEM:3% agarose (1:1) was slowly dispensed onto the sides of the plate. After the agar solidified, the plate was incubated at 37°C in a CO2 incubator for 3 days. The cells in each well were stained with crystal violet solution and allowed to stand at room temperature for at least 6 hours. The stain and agar were then removed, and the plate was washed with water. After the plate was thoroughly dried at room temperature, the plaques in each well were observed and counted. The quantitative unit is plaque forming unit (PFU), calculated by multiplying the number of plaques by the dilution factor. Antiviral activity was calculated as the log reduction of the sample exposed to the virus (test group) relative to the sample not exposed to the virus (control group). Effectiveness was considered when the log reduction reached 4 or higher and reached 99.99%.

[0917] (2) Experimental results

[0918] Liquid samples from Example 1, Comparative Example 1, and Comparative Example 2 were diluted with water and then treated. Results showed that compared to samples not exposed to the virus (control group), plaque-forming units were significantly reduced in all Examples and Comparative Examples, demonstrating their ability to control influenza viruses. In particular, the sample treated with Example 1 demonstrated excellent control of avian influenza viruses, particularly compared to the quaternary ammonium disinfectants used in Comparative Examples 1 and 2. The test was repeated three times to confirm its reproducibility.

[0919] Table 63:

[0920]

[0921] Although the preferred embodiments of the present invention have been described in detail above, the scope of protection of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic ideas of the present invention as defined in the appended claims also fall within the scope of protection of the present invention.

Claims

1. A composition for antibacterial and preservation, comprising a compound as shown in Chemical Formula 1, characterized in that: Chemical formula 1: In the chemical formula 1, R1 is substituted or unsubstituted C7 to C 17 Alkyl, or substituted or unsubstituted C7 to C 17 Alkenyl.

2. The composition for antibacterial and preservation according to claim 1, characterized in that Contains any one of the compounds shown in the following Chemical Formula 2, Chemical Formula 3 or Chemical Formula 4: Chemical formula 2: Chemical formula 3: Chemical formula 4: In the chemical formula 2, L1 is -(CH=CH)-, -(CH2) l -, -C(=O)- or -O-, R2 is -H, -C(=O)-CH3, -C(=O)H, -OH, -O - Na + 、-(CH2) m -OH, -CH(CH3)-CH2-C(CH3)2-CH3, or substituted or unsubstituted C1 to C6 alkyl, R3, R4 and R5 are each independently -H, -OH, C1 to C3 alkoxy, =O, -O - Na + , or a substituted or unsubstituted C1 to C6 alkyl group, X and Y are each independently -CH-, -O- or -NR a , R a is -OH, Z is NH2-CH2-CH2-OH or does not exist, represents a single bond or a double bond, K, l, and m are each independently an integer from 1 to 4, In the chemical formula 3, R6 is -H, substituted or unsubstituted C2 to C 18 Alkyl, or substituted or unsubstituted C2 to C 18 alkenyl, L2 is -(CH2) o -, -O- or -C(=O)-, R7 is -NHCH-, -N- or C(=O)CHNH-, R8 is -OH, COOH, -COOCH3, -COOCH2CH3, -(CH2)4NH- or R9 is -H, -(CH2)4NH2 or -(CH2)3C(NH)2NH2, A is -H or does not exist, n is an integer from 1 to 99, o is an integer from 1 to 3, In the chemical formula 4, L3 is -(CH2) p -, -O-, -C(=O)- or -OC(=O)-, R 10 is substituted or unsubstituted C2 to C 10 Alkyl, -OH or -O - Na + , R 11 is one or more selected from -CH2-CHOH-CH 2- , hydroxyl, unsubstituted C1 to C3 alkyl and carboxyl substituted or unsubstituted -(CH2) q -, substituted or unsubstituted -(CH2) r -N(R b )-(CH2) s -, or unsubstituted phenylene (-C6H4-), R 12 -OH, -COOH, C1 to C3 alkoxy or -COO - Na + , R b -(CH2) t -N[(CH2) u -CO2-)]2, p, q, r, s, t, and u are each independently an integer from 1 to 3.

3. The composition for antibacterial and preservation according to claim 1, characterized in that The composition for antibacterial and preservation has antibacterial or antifungal effects on bacteria or fungi.

4. The composition for antibacterial and preservation according to claim 1, characterized in that The antibacterial and preservation composition is used to control at least one microorganism selected from the group consisting of Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, methicillin-resistant Staphylococcus aureus, Bacillus subtilis, Vibrio parahaemolyticus, Salmonella typhimurium, Listeria monocytogenes, Shigella flexneri, Candida albicans, Aspergillus niger and Aspergillus brasiliensis.

5. The composition for antibacterial and preservation according to claim 2, characterized in that The weight ratio of the compound represented by Chemical Formula 1 to any one of the compounds represented by Chemical Formula 2, Chemical Formula 3, or Chemical Formula 4 is 0.01:9.99 to 9.99:0.

01.

6. The composition for antibacterial and preservation according to claim 1, characterized in that The compound shown in Chemical Formula 1 is 3,3′-(dodecylimino)bispropane-1,2-diol.

7. The composition for antibacterial and preservation according to claim 2, characterized in that The compound shown in Chemical Formula 2 is one or more selected from the group consisting of o-methoxycinnamaldehyde, 4-methoxycinnamaldehyde, raspberry ketone, 3-phenyl-1-propanol, hydroxyacetophenone, sodium benzoate, phenoxyethanol, tropolone, piroctone olamine and sodium dehydroacetate.

8. The composition for antibacterial and preservation according to claim 2, characterized in that The compound represented by Chemical Formula 3 is one or more selected from the group consisting of lauroyl arginine methyl ester, lauroyl lysine methyl ester, lauroyl arginine ethyl ester, iodopropynyl butylcarbamate, polylysine, lauroyl lysine and octanoyl hydroxamic acid.

9. The composition for antibacterial and preservation according to claim 2, characterized in that The compound represented by Chemical Formula 4 is one or more selected from the group consisting of hexane-1,2-diol, octane-1,2-diol, decane-1,2-diol, ethylhexylglycerin, monocaprylin, caprylylglycerin, hexylglycerin, levulinic acid, citric acid, sodium anisate, disodium edetate, and tetrasodium edetate.

10. A product, characterized in that The invention comprises the composition for antibacterial and preservation according to claim 1 or 2.

11. The product according to claim 10, characterized in that The product is a cosmetic, a hygiene product or a daily chemical product.

12. The product according to claim 11, characterized in that The cosmetic is made into any one selected from the group consisting of solution, suspension, emulsion, paste, gel, cream, pressed powder, loose powder, liquid foundation, foundation stick, spray, soap, facial cleanser, shower gel, shampoo and hair conditioner.

13. The product according to claim 11, characterized in that The sanitary product is selected from the group consisting of dishwashing detergent, dishwasher detergent and wet wipes.

14. The product according to claim 11, characterized in that The daily chemical product is selected from the group consisting of laundry detergents, living space cleaners, deodorizers, air purifiers, room fragrances, hair fragrances, fabric softeners, multi-functional cleaning products, bactericidal products, antibacterial products, disinfectant products and sterilizers.

15. The product according to claim 11, characterized in that Relative to cosmetics, sanitary products or daily chemical products, the content of the antibacterial and preservation composition is 0.01 weight percent to 10 weight percent.

16. An antibacterial method, characterized in that: The method comprises the step of treating bacteria using the antibacterial and preservation composition according to claim 1 or 2.

17. A hair care cosmetic composition for preventing dandruff, comprising the compound shown in Chemical Formula 1, characterized in that: Chemical formula 1: In the chemical formula 1, R1 is a linear or branched C7 to C 17 Alkyl, linear or branched C7 to C 17 Alkenyl, or C7 to C 17 Hydroxyalkyl.

18. The hair care cosmetic composition for preventing dandruff according to claim 17, characterized in that: It also contains a compound as shown in the following chemical formula 5, Chemical formula 5: R 13 -L4·W In the chemical formula 5, L4 is -Zn or R 13 is CH3-C(CH3)2-CH2-CH(CH3)-CH2-, W is NH2-CH2-CH2-OH, Or does not exist.

19. The hair care cosmetic composition for preventing dandruff according to claim 18, characterized in that: The weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 5 is 9:1 to 1:

9.

20. The hair care cosmetic composition for preventing dandruff according to claim 17, characterized in that The cosmetic composition has a bactericidal effect on Malassezia strains.

21. The hair care cosmetic composition for preventing dandruff according to claim 17, wherein The hair care cosmetic composition for preventing dandruff has a bactericidal effect on one or more fungi selected from the group consisting of Malassezia furfur, Malassezia restricta, Malassezia globosa, Malassezia slophidia, Malassezia pachydermatis and Malassezia obtusiformis.

22. The hair care cosmetic composition for preventing dandruff according to claim 17, wherein The compound shown in Chemical Formula 1 is 3,3′-(dodecylimino)bispropane-1,2-diol.

23. A composition for antifungal use, targeting Malassezia strains, comprising a compound as shown in Chemical Formula 1, characterized in that: Chemical formula 1: In the chemical formula 1, R1 is a straight or branched C7 to C 17 Alkyl, linear or branched C7 to C 17 Alkenyl, or C7 to C 17 Hydroxyalkyl.

24. The antifungal composition according to claim 23, characterized in that It also contains the compound shown in Chemical Formula 5.

25. The antifungal composition according to claim 23, characterized in that The antifungal composition has a bactericidal effect on one or more fungi selected from the group consisting of Malassezia furfur, Malassezia restricta, Malassezia globosa, Malassezia slophidia, Malassezia pachydermatis and Malassezia obtusiformis.

26. A hair care cosmetic, characterized in that: Comprising the composition according to any one of claims 17 to 25.

27. The hair care cosmetic according to claim 26, characterized in that The content of the composition is 0.01 weight percent to 2.0 weight percent relative to the hair care cosmetic.

28. The hair care cosmetic according to claim 26, characterized in that The hair care cosmetic is made into any one selected from the group consisting of hair nourishment, hair cream, hair mask, hair milk, hair essence, hair nutrition agent, shampoo, hair conditioner, hair conditioner, hair spray, hair gel, hair cream, hair oil, hair wax, hair bleach and hair dye.

29. A method for sterilizing dandruff fungi, characterized in that: Comprising the step of treating dandruff fungus using a composition according to any one of claims 17 to 25.

30. An antiviral composition comprising the compound shown in Chemical Formula 1 as an active ingredient, characterized in that: Chemical formula 1: In the chemical formula 1, R1 is substituted or unsubstituted C7 to C 17 Alkyl, or substituted or unsubstituted C7 to C 17 Alkenyl.

31. The antiviral composition according to claim 30, characterized in that The compound shown in Chemical Formula 1 is 3,3′-(dodecylimino)bispropane-1,2-diol.

32. The antiviral composition according to claim 30, characterized in that The antiviral composition is diluted into a 0.1-5% (w / v) aqueous solution for use.

33. The antiviral composition according to claim 30, characterized in that The virus is one or more selected from the group consisting of coronavirus, influenza virus, norovirus, rotavirus, respiratory syncytial virus, avian influenza virus, foot-and-mouth disease virus and African swine fever virus.

34. An antiviral method, characterized in that: The method comprises the step of treating viruses using the antiviral composition according to claim 30.

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