KR20240061133A - Antimicrobial composition for use in cosmetics, daily necessities and hand cleaner - Google Patents

Abstract

The present invention provides an antibacterial composition consisting of a first antibacterial ingredient, a second antibacterial ingredient and sapienic acid stabilizer, an antioxidant, and a carrier. The antibacterial composition of the present invention, which consists of sapienic acid and lauric acid as the first antibacterial ingredients and C12-C18 monolaurate as the second antibacterial ingredient and sapienic acid stabilizer, is used in skin care to eradicate bacteria living in the human body and products for human use. It can be used as an antibacterial composition in products, household goods, and cosmetics.

Description

Antimicrobial composition for use in cosmetics, daily necessities and hand cleaner}

The present invention relates to an antibacterial composition for cosmetics, household goods, and hand sanitizers. More specifically, it provides an antibacterial composition consisting of an antibacterial ingredient, a sapienic acid stabilizer, an antioxidant, and a carrier.

Various bacteria that cause disease live on human skin and oral cavity. Bacteria such as Staphylococcus aureus, Corynebacterium xerosis and Propionibacterium acnes on the skin, Porphyromonas gingivalis and Staphylococcus aureus in the mouth. Gram positive and negative bacteria such as Streptococcus mutans, Fusobacterium nucleatum and Actinomyces viscosus live here.

In addition, bacteria such as Nocardia asteroides and Pseudomonas aeruginosa, spore-forming bacteria such as Bacillus subtilis and Bacillus cereus, and yeast are found around us. There are various bacteria that can enter the human body and cause disease, such as Candida albicans.

A good way to kill or inhibit the growth of bacteria living in the human body is to add antibacterial ingredients to products used on the human body, such as cosmetics, household goods, and healthcare products. To this end, various antibacterial ingredients, such as solids such as silica, solid particles loaded with antibacterial ingredients, polymers, organic compounds, organometallic salts, and essence oils extracted from plants, have been developed with patented technology and are being used in products for human use. However, these ingredients are not secreted within the human body or produced during metabolism, so they cannot be considered human-friendly antibacterial agents. Considering human toxicity, it is desirable that antibacterial agents be made of ingredients that have antibacterial properties among substances produced within the human body.

Considering its toxicity to the human body, free fatty acid, the main component of sebum, may be the optimal ingredient for an antibacterial composition. Sebum secreted from the sebaceous glands is well known as the body's defense system that fights off bacteria living in the human body. Sebum has a very complex composition consisting of neutral fat (mono-, di-, tri-glyceride), fatty acid (free fatty acid), wax ester, ceramide, cholesterol, cholesterol ester, squalene, and tocophenol. It is a collection of lipids. It has been reported in the literature that there are more than 200 types of free fatty acids (hereinafter referred to as fatty acids) produced by hydrolysis of neutral fat. Among these complex sebum components, fatty acids with low molecular weight and high fluidity play an important role in fighting bacteria.

Looking at the prior art of using the ingredients that make up sebum as a cosmetic raw material and antibacterial agent, Korean Patent No. 10-2152850 shows that the two methylene groups of glycerin are hydroxy, acetyl, and methoxy. A mono glyceride in which a (methoxy), ethoxy, butoxy, or pentoxy group is connected to the other methylene group and a C1 to C22 saturated and unsaturated fatty acid is used in cosmetics. A technique for using the composition is disclosed. Here, monoglyceride was used as a cosmetic composition to promote differentiation of skin keratinocytes, improve skin dryness, and prevent atopic dermatitis, rather than as an antibacterial agent.

In Korean Patent No. 10-2061111, a C12 fatty acid ester composition consisting of glyceryl monolaurate and erythorbyl laurate or ascorbyl laurate, which are substances that do not exist in the human body, is used to kill gram-positive and negative bacteria for cosmetics and food. It was used as an antibacterial agent for extermination.

Meanwhile, US patent US 2020/0360260 discloses a technology for using a composition with an antibacterial effect against Staphylococcus aureus and Malassezia (Malassezis spp.), a dandruff-causing bacterium, as an anti-dandruff agent. Biphenol 0.01-10% and sapienic acid, sphingosine, dihydrosphingosine, phytosphingosine, 6-hydroxy phytosphingosine (6 The antibacterial composition of this technology, which consists of 0.01-10% of at least one lipid selected from -hydroxy phytosphigosine and palmitoleic acid, is characterized by the absence of C8-C18 saturated fatty acids.

However, biphenol extracted from Magnolia is not a human secretion, and various sphingosine substances such as disphingosine are strictly speaking components of ceramide contained in sebum, so they are not direct human secretions. In the human body, sphingosine does not exist in a free state, but exists in sebum in the form of ceramide with a fatty acid linked to its amino group.

In US patent US 2022/0151969, a composition consisting of at least one component selected from C4-C22 saturated and unsaturated fatty acids and their esters and metal salts is used as an antibacterial agent. However, short chain and medium chain fatty acids below C8 used in this technology are toxic to the human body due to their high acidity, and are fatty acids that rarely exist in the human body.

In addition, various technologies for using sebum components as antibacterial agents are disclosed in domestic and foreign patents, but most of the conventional antibacterial compositions used in the human body contain synthetic compounds and ingredients extracted from plants whose toxicity to humans has not been confirmed. Although some antibacterial agents are composed solely of sebum components, the germs to which they are applied are mainly limited to bacteria, rather than a wide range of germs including bacteria, mold, and yeast. Also, as some antibacterial agents try to faithfully imitate sebum, they contain excessive amounts of unnecessary ingredients, which can actually be harmful to health.

Sebum has a very complex composition as numerous substances are produced through the catalytic action of various enzymes such as elongation enzymes, desaturation enzymes, and hydrolytic enzymes present in the sebaceous glands, but the key ingredients that play a role in killing bacteria include sapienic acid. It is only a very small number of fatty acids. The remaining saturated and unsaturated fatty acids were produced by indiscriminate decomposition from neutral fats by hydrolytic enzymes and were not biosynthesized for any special purpose. Excessive secretion of unsaturated fatty acids in sebum, including oleic acid, linoleic acid, and linolenic acid, can cause inflammation and acne due to rancidity.

Accordingly, the present inventor came up with the present invention to develop and provide a human-friendly antibacterial composition that has antibacterial properties against a wide range of germs, including bacteria, mold, and yeast, and consists only of key ingredients with the greatest antibacterial properties among sebum components.

Korean Patent No. 10-2152850 Korean Patent No. 10-2061111 US Patent US 2020/0360260 US Patent US 2022/0151969

The purpose of the present invention is to develop and provide an antibacterial composition that is friendly to the human body as it consists only of ingredients secreted by the human body.

In order to achieve the above object, the present invention provides an antibacterial composition consisting of a first antibacterial component composed of sapienic acid and lauric acid, a second antibacterial component composed of C12-C18 monoglyceride, a sapienic acid stabilizer, an antioxidant, and a carrier. I want to do it.

All components of the composition consist only of nutrients secreted by the human body or necessary for the human body, and the composition includes common Staphylococcus aureus, antibiotic-resistant Staphylococcus aureus, Staphylococcus epidermidis, Propionibacterium acnes, and Porphyromonas gingivalis. It is an antibacterial composition that has bactericidal properties against bacteria, mold, and yeast commonly found on human skin and oral cavity, such as S., Fusobacterium nucleatum, Nocadia asteroides, Bacillus candida, and Candida albicans.

The antibacterial composition of the present invention consists only of nutritional ingredients secreted by the human body or necessary for the human body, and can be widely used in commercial products for use in the human body, such as cosmetics and household goods.

The antibacterial composition is composed of fatty acids with the highest antibacterial properties against bacteria, mold, and yeast among saturated and unsaturated fatty acids of medium chain or higher, and can effectively eradicate bacteria living in the human body. It can also be used as a preservative to prevent commercial products for human use from spoiling.

Figure 1 is a death curve of Staphylococcus aureus and Propionibacterium acnes coexisting bacteria.
Figure 2 is a death curve of Porphyromonas gingivalis and Puzobacterium nucleatum coexisting bacteria.

Since the present invention can be modified in various ways and can have various embodiments, specific embodiments will be illustrated in the drawings and described in detail in the detailed description. However, this is not intended to limit the scope of the present invention to only specific embodiments, and should be understood to include all transformations, equivalents, and substitutes included in the spirit and technical scope of the present invention. In describing the present invention, if it is determined that a detailed description of related known technologies may obscure the gist of the present invention, the detailed description will be omitted.

The terms used in this application are only used to describe specific embodiments and are not intended to limit the invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this application, terms such as “comprise” or “have” are intended to designate the presence of features, numbers, steps, operations, components, parts, or combinations thereof described in the specification, but are not intended to indicate the presence of one or more other features. It should be understood that this does not exclude in advance the possibility of the existence or addition of elements, numbers, steps, operations, components, parts, or combinations thereof.

Terms such as first, second, etc. may be used to describe various components, but the components should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another.

Hereinafter, the present invention will be described in detail.

Fatty acids are substances that have both hydrophilic and lipophilic groups and can dissolve both hydrophilic and lipophilic substances at the same time. The mechanism by which bacteria are killed or their growth is stopped by fatty acids is, first of all, the lysis of bacteria due to the amphoteric properties of fatty acids.

In other words, the fatty acid has the properties of a solvent, so the bacteria are dissolved or their shape is changed and their activity stops.

Fatty acids that enter the bacterial cells replace the fatty acids that make up the double lipid layer of the cell membrane and become components of the double lipid layer. At this time, if the molecular movement of the fatty acids that are part of the double lipid layer is very active, the gap between them and neighboring fatty acids widens, and as a result, the components in the cytoplasm necessary for life are leaked out of the cell, causing the bacteria to die.

In bacteria in which this mechanism operates, unsaturated fatty acids with a bent linear carbon double bond rather than saturated fatty acids with a linear carbon chain effectively lower the density of the lipid layer, allowing cytoplasmic contents to easily leak out, resulting in greater antibacterial properties.

For this reason, among unsaturated fatty acids, linear cis fatty acids have better antibacterial properties than linear trans fatty acids.

Another mechanism is the chemical reaction between the synthase of adenosine triphosphate (ATP), which produces energy for bacteria, and the electron carrier required for ATP production, and fatty acids. If fatty acids combine with ATP synthase and electron carriers and ATP cannot be produced, the bacteria die or their growth stops.

Fatty acids in sebum are involved in the death and inhibition of proliferation of bacteria living in the human body through various mechanisms. According to GC analysis, more than 200 types of fatty acids alone are detected in sebum, which is composed of lipids such as neutral fats, fatty acids, wax esters, and ceramides.

The composition is complex as it contains fatty acids with various carbon numbers (2-26), double bonds (0-5), and connected functional groups (hydroxyl group, acetyl group, ketone group, nitrogen- and sulfur-containing group, etc.). do. Among them, the content of C18 saturated fatty acids (stearic acid) and unsaturated fatty acids (C18:1 oleic acid, C18:2 linoleic acid, C18:3 linolenic acid) without a functional group peaks, and as the carbon number increases or decreases, the content decreases rapidly. Fatty acids above C22 and fatty acids below C12 are so small that they can be ignored. (Here, C18:1 in parentheses means that the number of carbons is 18 and the number of double bonds is 1.) The amounts of fatty acids above C22 and below C12 are so small that they can be ignored.

Therefore, the components that play a key role in the human body's defense system are C12 to C22 fatty acids, and as can be seen in the comparative examples described later, according to the inventor's careful investigation, among these, saturated fatty acids are C12 lauric acid, and unsaturated fatty acids are C16 fatty acids. :1 Sapienic acid has the best antibacterial properties against bacteria living in the human body.

The reason why C12 lauric acid has the greatest antibacterial properties among saturated fatty acids is because the strengths of hydrophilic and lipophilic properties are balanced. If the carbon number is 12 or more, the lipophilicity increases but the hydrophilicity decreases. Conversely, if the carbon number is 12 or less, the hydrophilicity increases but the lipophilicity decreases, and the antibacterial effect decreases.

In the case of unsaturated fatty acids, molecular motion is more active than saturated fatty acids and the boiling point is lower, so C16:1 sapienic acid, which is liquid at room temperature, has the greatest antibacterial activity. Sapienic acid, which has a cis-type double bond connected to the 6th carbon from the carboxyl group, is a fatty acid whose name is derived from Homo sapiens, modern humans, because it is the only animal among animals secreted only by human skin.

Although the seed oil of some plants contains this fatty acid, its content and seed production are so low that it must be mass-produced by biological or chemical methods using enzymes for industrial use.

In the present invention, we intend to use it as an antibacterial ingredient by manufacturing it using a new chemical method that has never been used before. Specifically, 6-octadecenoic acid, which, like sapienic acid, contains a double bond at the 6th carbon from the carboxyl group, is used as a raw material to produce 1-undecene or 4-tetradecenoic acid under an olefin metathesis catalyst. Sapienoic acid is produced by cross-metathesis with (4-tetradecenoic acid).

Cross-metathesis reaction is a reaction in which two methylene groups connected to both sides of a double bond of one substance are exchanged with two methylene groups of another substance to create a new substance. If the two reactants are petroselinic acid and 1-undecene, by cross-metathesis, sapienic acid, whose official name is 6-hexadecenoic acid, 6-heptenoic acid, and 1-tridecene (1 -tridecene), and 10-docosene are produced. The by-products of this reaction, 6-heptenoic acid and 10-dococene, contain the alkene group needed to produce sapienic acid, so if they are separated and recovered, they can be reused as raw materials for metathesis.

If 4-tetradecenoic acid is selected instead of 1-undecene and metathesized with petroleum acid, sapienic acid and by-products such as 4-decenedioic acid, 4-hexadecenoic acid and 10-doco are produced. Sen is created. By-products 4-decenedioic acid and 10-dococene can be separated and reused as raw materials.

Petrocellic acid is contained in about 76% of parsley seed oil, and more than 50% in the seed oils of various plants such as lettuce, coriander, pine needle water parsley, palsoni, and fence, making it a raw material that can be easily obtained from nature. 4-Tetradecenoic acid is contained in approximately 10-15% of the seeds of various plants of the genus Ginger, which are widely found in Korea, and also contains 5-10% in the seeds of Quercus genus trees.

Sapienoic acid can be produced more effectively by first metathesising petroleum acid and 4-tetradecenoic acid obtained from these plants with ethylene rather than directly cross-metathesizing them. When petroleum acid is metathesized with ethylene, 6-heptenoic acid and 1-tridecene are produced as products, and when 4-tetradecenoic acid is metathesized with ethylene, only 4-pentenoic acid and 1-undecene are produced. Sapienoic acid can be obtained by separating them from each other and then metathesising 6-heptenoic acid and 1-undecene. The only by-products of this reaction are ethylene and 6-hexadecene, which are discharged as gas, making it very easy to separate sapienic acid with high purity. 6-Hexadecene produced as a by-product can be used again as a raw material for sapienic acid production.

The present invention implements an antibacterial composition composed of a first antibacterial ingredient composed of sapienic acid and lauric acid prepared as described above, a sapienic acid stabilizer with antibacterial properties, an antioxidant, and a carrier.

Here, the first antibacterial ingredient refers to a mixture composed of sapienic acid and lauric acid in an appropriate ratio. Lauric acid is more antibacterial than sapienic acid against bacteria living on the skin, such as Fusobacterium nucleatum, which causes stomatitis, cavities, and gingivitis, and is also the causative agent of colon cancer, and Propionibacterium acnes, a bacteria that causes acne. This is big.

On the other hand, Porphyromonas gingivalis, an oral bacterium that causes periodontitis, Nocardia asteroids, an ambient bacterium that infiltrates the lungs and skin and causes disease, Bacillus cereus, a spore-forming bacterium that causes food poisoning, and methicillin, an antibiotic. Sapienic acid has greater antibacterial activity than lauric acid against resistant Staphylococcus aureus.

The reason for this difference is that the antibacterial mechanisms of fatty acids are different depending on the type of bacteria. In other words, due to the antibacterial mechanism of fatty acids, there are groups of bacteria for which the antibacterial effect of saturated fatty acids is greater and groups of bacteria for which the antibacterial effect of unsaturated fatty acids is greater.

The antibacterial ingredient of the present invention is composed of two ingredients with the highest antibacterial properties among saturated fatty acids and unsaturated fatty acids secreted by the human body. At this time, the appropriate weight ratio of sapienic acid and lauric acid to the total weight of antibacterial ingredients is 5:95 to 95:5. When antibacterial ingredients are contained in this ratio, they can effectively eradicate bacteria living in the human body.

The second antibacterial ingredient and sapienic acid stabilizer constituting the antibacterial composition of the present invention is an ingredient that can simultaneously perform an antibacterial action against bacteria and a function of stabilizing sapienic acid, an unsaturated fatty acid.

Unsaturated fatty acids containing carbon double bonds are chemically unstable compared to saturated fatty acids, so they can be easily converted to other substances through oxidation and addition reactions. When exposed to the atmosphere for a long time, the allylic hydrogen bonded to the carbons on both sides of the double bond breaks off into radical hydrogen, and an autooxidation reaction occurs, resulting in oxidation of unsaturated fatty acids. Additionally, impurities may cause an addition reaction to the double bond and convert it into a saturated fatty acid.

Therefore, in order to prevent sapienic acid, one of the antibacterial ingredients of the present invention, from being easily deteriorated by chemical reactions, it is necessary to stabilize the double bond of sapienic acid to reduce the reactivity.

The optimal sebum components to use for this purpose are C12-C18 monoglycerides. Monoglyceride is a fatty acid ester in which one fatty acid is linked to glycerol, and although the amount is very small, it is found in the human body and in sebum. Sapienoic acid is chemically stabilized by the interaction of the two -OH groups contained in its glycerol group and the double bond.

Meanwhile, monoglycerides containing one saturated fatty acid, in addition to the stabilizing function of sapienic acid, have similar or even better antibacterial properties against bacteria living in the human body compared to saturated fatty acids with the same carbon number in terms of antibacterial properties. many.

For example, the minimum growth inhibitory concentration (MIC) of lauric acid for Staphylococcus aureus is 500 ㎍/㎖, while the MIC of glycerol monolaurate is 31.3 ㎍/㎖, which means that glycerol is more effective than when lauric acid exists alone. Antibacterial properties are greater when it is a monolaurate linked to.

Staphylococcus epidermidis that lives on the skin contains glycerol monolaurate (MIC 31.3 ㎍/㎖) rather than lauric acid (MIC 500 ㎍/㎖), and lauric acid (MIC 31.3 ㎍/㎖) is more effective against Candida alcanbis, a fungus that infects the entire body. Glycerol monolaurate (MIC 31.3 μg/ml) has a smaller MIC than MIC 500 μg/ml), so it can inhibit bacterial growth with a smaller amount.

Therefore, monoglyceride used for the purpose of stabilizing sapienic acid actually acts as an antibacterial ingredient.

In the present invention, monoglycerides suitable as the second antibacterial ingredient and sapienic acid stabilizer are glycerol monolaurate, glycerol monomyristate, glycerol monopalmitate, and glycerol monostearate in which one C12-C18 saturated fatty acid is linked to glycerol. .

Monoglycerides below C12 can be toxic to the human body, and monoglycerides above C18 have low antibacterial properties and are less effective in stabilizing sapienic acid. Therefore, one or a mixture of two or more of the above C12-C18 monoglycerides can be used as the second antibacterial ingredient and sapienic acid stabilizer of the present invention.

The antibacterial performance of the composition consisting of lauric acid, sapienic acid and C12-C18 monoglyceride has a wide range of antibacterial properties against bacteria, mold and yeast. Representative bacteria include skin-inhabiting bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, and Propionibacterium acnes, and oral bacteria such as Porphyromonas gingivalis, Steroptococcus mutan, Fusobacterium nucleatum, and mucous actinomycetes. It has excellent antibacterial properties against intestinal bacteria such as gas gangrene and Escherichia coli, ambient bacteria such as Pseudomonas aeruginosa and Nocardia asteroides, Bacillus subtilis and Bacillus cereus as spore-forming bacteria, and Candida alcanbis as yeast.

The antioxidant constituting the antibacterial composition of the present invention is an ingredient that serves to remove oxygen radicals so that the first antibacterial ingredient and the second antibacterial ingredient and sapienic acid stabilizer described above are not oxidized.

When oxygen entering from the air and ultraviolet rays generate active oxygen, not only unsaturated fatty acids but also saturated fatty acids and monoglycerides can be oxidized. Therefore, an antioxidant with excellent active oxygen removal ability is essential to preserve the antibacterial composition for a long time.

Among the ingredients secreted by the human body or required as nutrients, substances with antioxidant power include tocopherol, methionine, taurine, glutathione, and cysteine, and one or two or more of these can be selected to form the human-friendly antibacterial composition of the present invention. Can be used as an antioxidant.

The carrier constituting the antibacterial composition of the present invention is a component that controls the concentration of the antibacterial composition and functions as a solvent to dissolve solid components. The first antibacterial ingredient, the second antibacterial ingredient and sapienic acid stabilizer, and the antioxidant, which are the components of the present invention, are all solid at room temperature except sapienic acid, so a solvent is needed to convert them into a liquid state to maximize efficacy.

The solvent used for this purpose is a carrier, and by controlling its concentration, the concentration of each component of the antibacterial composition is also controlled.

The carrier of the present invention may be one or a mixture of two or more of methyl laurate, ethyl laurate, methyl myristate, ethyl myristate, and ethanol, which are liquid at room temperature.

Among these, ethanol is suitable for use as a carrier for mouthwash and hand sanitizer that require quick drying and low viscosity.

As such, the antibacterial composition of the present invention, which consists of the first antibacterial ingredient, the second antibacterial ingredient and sapienic acid stabilizer, antioxidant and carrier, is used in the form of skin care, skin lotion, shampoo, toothpaste, mouthwash and hand sanitizer, etc. It can also be used as an antibacterial agent against living bacteria and as a preservative to prevent products for human use from spoiling.

Because the causes of atopic dermatitis are diverse, a standard treatment has not yet been developed. It is known that the secretion of sapienic acid in the body of a person suffering from this disease is very low, so bacteria such as Staphylococcus aureus become active, causing secondary diseases such as itching.

The antibacterial composition of the present invention, which contains sapienic acid as an antibacterial ingredient, is used in skin care products to prevent secondary diseases, making it possible to effectively supply antibacterial ingredients to the skin of patients with low sapienic acid secretion due to atopic dermatitis.

Skin care products for this purpose may additionally contain various ingredients that are beneficial to the skin. For example, moisturizers, whitening agents, emollients and nutrients. The amounts of the first antibacterial ingredient, the second antibacterial ingredient and sapienic acid stabilizer, antioxidant, and carrier of this antibacterial composition in these skin care products are 0.001~5%, 0.001~5%, and 0.1~5%, respectively, based on the weight of the skin care product. Can be used including 5% and 0~60%.

Skin lotion, a basic cosmetic product, does not have much different ingredients from the skin care products above. That is, the antibacterial composition of the present invention can be applied within a concentration range similar to that of the above skin care products. At this time, in order to meet the viscosity standards of skin lotion, one or a mixture of two or more of methyl laurate, ethyl laurate, methyl myristate, ethyl myristate and ethanol can be used within the range of 0 to 40% as the carrier.

Commonly used liquid shampoos contain surfactants such as fatty acid metal salts as their main ingredients. Here, various functional substances such as foaming agents, hair conditioners, thickeners, opacifiers, fragrances, and preservatives are added. If the antibacterial composition of the present invention is added to shampoo, it can eradicate both bacteria living on the head and bacteria that spoil the shampoo.

At this time, the appropriate content is 0.001 to 3% of the first antibacterial ingredient, 0.001 to 3% of the second antibacterial ingredient and sapienic acid stabilizer, and 0.1 to 3% of the antioxidant based on the total weight of the shampoo. The carrier contains ingredients with similar physical properties in shampoo and can be used in amounts ranging from 0% to a maximum of 20%.

Toothpaste consists of abrasives, surfactants, foaming agents, humectants, sweeteners, fresheners, preservatives, and antibacterial agents that combat bacteria in the oral cavity. When this antibacterial composition is used as a preservative in toothpaste and an antibacterial agent against oral bacteria, it can effectively eradicate oral bacteria such as Porphyromonas gingivalis, Steroptococcus mutan and Fusobacterium nucleatum, which are the causative agents of periodontitis and cavities. You can. Porphyromonas gingivalis is a scary bacterium that is also associated with rheumatoid arthritis, Alzheimer's, arteriosclerosis, and macular degeneration.

Glycerin is usually used as a humectant that absorbs moisture while making the toothpaste gel. Methyl laurate, ethyl laurate, methyl myristate, and ethyl myristate, which are used as carriers of the antibacterial composition of the present invention, are used as a humectant instead of glycerin. It can also be used as .

In addition, the antibacterial composition of the present invention can be used as an alternative to a preservative and a cavity prevention antibacterial agent. The appropriate contents of the first antibacterial ingredient, the second antibacterial ingredient and sapienic acid stabilizer, and antioxidant are 0.001 to 3%, 0.001 to 3%, and 0.1 to 3%, respectively, based on the total weight of toothpaste. Since the liquid carrier must maintain the gel state of the toothpaste, it can be used to meet the viscosity standards of toothpaste within the range of 0 to 10%.

Mouthwash is a product used to eliminate bad breath. It consists of ingredients that absorb odor, antibacterial ingredients that remove bacteria in the mouth, and fragrances. Bad breath is mainly caused by the decomposition of food by bacteria living in the oral cavity, so antibacterial ingredients are necessary.

Nitrogen and sulfur compounds, which are the main causes of bad breath, are better absorbed by lipophilic substances than hydrophilic substances. Accordingly, essence oil is widely used in mouthwash, and oil pulling, which has been traditionally used to remove toxins, also uses oil as an absorbent. In this respect, this antibacterial composition, which is an oil component and has antibacterial properties, can be effectively used as a mouthwash. Sapienic acid, an antibacterial ingredient, has excellent antibacterial properties against oral bacteria such as Porphyromonas gingivalis and Fusobacterium nucleatum, making it a good ingredient for preventing bad breath.

As an antibacterial composition of a mouthwash, the appropriate contents of the first antibacterial ingredient, the second antibacterial ingredient and sapienic acid stabilizer, antioxidant, and carrier are 0.001 to 5%, 0.001 to 5%, and 0.1 to 5%, respectively, based on the total weight of the mouthwash. It is 0~50%.

The main purpose of hand sanitizer is to eradicate bacteria on hands, so it is a product that can be used with only antibacterial agents and no other ingredients. This antibacterial composition, which consists of a first antibacterial ingredient, a second antibacterial ingredient and sapienic acid stabilizer, an antioxidant, and a carrier, can be used as a hand sanitizer by itself without adding any other ingredients except fragrance.

Cleansers used for devices and hands in medical institutions must be able to eradicate Staphylococcus aureus, which is resistant to antibiotics. Antibiotic-resistant Staphylococcus aureus is a bacterium that is a social problem due to the high frequency of infection, mainly in medical institutions.

As can be seen in the examples to be described later, the antibacterial composition of the present invention has an excellent antibacterial effect even against methicillin-resistant Staphylococcus aureus, so it can be used in medical institutions' devices and hand sanitizers. The appropriate content is 0.001 to 5% of the first antibacterial ingredient, 0.001 to 5% of the second antibacterial ingredient and sapienic acid stabilizer, 0.1 to 5% of the antioxidant, and 0 to 50% of the carrier. Ethanol can be mainly used as a carrier for its low viscosity and quick drying after application.

Hereinafter, the present invention will be described in more detail through examples. However, the scope of the present invention is not limited to the examples.

<Example 1: Preparation of sapienic acid>

Put 0.3 mol of petroleum acid and 100 ppm of Grubbs-Hoveyda second generation metathesis catalyst into a pressure reactor, supply ethylene gas at room temperature and 150 psi atmospheric pressure, and metathesize for 4 hours, then separate 6-heptenoic acid in a 0.1-1 torr thin film evaporator. did. In the same way, 0.3 mol of 4-tetradecenoic acid was placed in a pressure reactor, metathesized with ethylene, and separated using a thin film evaporator to obtain 1-undeeic acid.

Take 0.2 mol of 6-heptenoic acid and 0.1 mol of 1-undecene prepared above, put them in a glass reactor, add 200 ppm of cis-selective Grubbs-Hoveyda second generation metathesis catalyst, supply nitrogen, and discharge ethylene gas as a by-product. Cross-metathesis reaction was performed at 40°C. After 6 hours, the reaction was stopped and distilled under reduced pressure twice in a thin film evaporator to obtain 17.5 g of sapienic acid.

<Example 2>

Sapienic acid prepared in Example 1 and commercially available lauric acid were obtained for eight types of Gram-positive, negative, and spore-forming bacteria and yeast commonly found in the human body, and the minimum growth inhibitory concentration (MIC) was measured (Table 1). MIC is obtained by adding fatty acid to bacteria with a colony forming unit of ¹ It was determined to be the minimum concentration at which no abnormal growth occurred.

The MIC of sapienic acid against the eight types of bacteria investigated was all below 250 ㎍/㎖, and except for two types, the MIC was lower than that of C12 lauric acid, a saturated fatty acid, showing better antibacterial activity.

Lauric acid showed excellent antibacterial properties against Propionibacterium acnes (MIC 7.8 ㎍/㎖), the causative agent of acne, and Fuzobacterium nucleatium (MIC 3.9 ㎍/㎖), which causes gum diseases such as plaque, and was superior to sapienic acid. . The reason why sapienic acid, an unsaturated fatty acid, and lauric acid, a saturated fatty acid, have better antibacterial properties against different bacteria is because their antibacterial mechanisms are slightly different. Therefore, this antibacterial composition, which consists of lauric acid and sapienic acid as the key first antibacterial ingredients, can effectively combat various bacteria living in the human body.

Table 1. Minimum growth inhibitory concentration of lauric acid and sapienic acid for 8 types of bacteria (㎍/㎖) Lauric acid (C12:0) sapienic acid
(C16:1) Habitat/Species Germ skin Staphylococcus aureus 500 250 Staphylococcus epidermidis 500 125 Propionibacterium acnes 7.8 15.6 oral Porphyromonas
Gingivalis 125 62.5 Fusobacterium nucleatum 3.9 7.8 Life surroundings Nocadia asteroides 31.3 15.6 /spore formation bacillus
cereus 250 62.5 /leaven Candida albicans 500 125

<Comparative Example 1>

In the same manner as in Example 2, the MICs of five types of saturated and unsaturated fatty acids for four types of bacteria were examined and compared with lauric acid and sapienic acid, which are antibacterial ingredients of the present invention (Table 2).

Capric acid, a C10 saturated fatty acid with two fewer carbons than lauric acid, had the same MIC as lauric acid for all five species of bacteria, while C16 palmitic acid, which has four more carbons, had a concentration of 1000 ㎍ only against Staphylococcus epidermidis. /ml showed antibacterial activity, but no antibacterial activity was observed against other bacteria. And C18 stearic acid, which has a longer carbon length, was found to have no antibacterial properties against all four types of bacteria. From this, it can be seen that among the saturated fatty acids contained in sebum, C12 lauric acid has the greatest antibacterial activity, and that saturated fatty acids with a longer molecular length have virtually no antibacterial activity.

In the case of unsaturated fatty acids, unsaturated fatty acids below C16 rarely exist in animals and plants, and mainly contain C18, so the MIC was measured for C18:1 oleic acid, which has one double bond, and C18:2 linoleic acid, which has two double bonds. As a result, oleic acid did not show antibacterial effect against four types of bacteria, and linoleic acid showed antibacterial activity comparable to sapienic acid against two types of bacteria except for two types of staphylococci.

From the above results, it can be seen that lauric acid among saturated fatty acids and sapienic acid among unsaturated fatty acids have the best antibacterial properties against various bacteria that can infect the human body, so the antibacterial agent can be composed of only these two ingredients. If other fatty acids are added, it may actually be harmful due to rancidity. Although C18:2 linoleic acid shows antibacterial properties similar to sapienic acid against some bacteria, it has a greater potential for rancidity due to polyunsaturation, which may adversely affect the efficacy of antibacterial agents.

Table 2. MIC of C10-C18 saturated and unsaturated fatty acids (㎍/㎖) Germ Capric acid (C10:0) Lauric acid (C12:0) palmitic acid
(C16:0) sapienic acid
(C16:1) Stearic acid (C18:0) oleic acid
(C18:1) linoleic acid
(C18:2) Staphylococcus aureus 500 500 N ^* 250 N N N Staphylococcus epidermidis 500 500 1000 125 N N N Nocadia asteroides 31.3 31.3 N 15.6 N N 31.3 Candida albicans 500 500 N 125 N N 125

* N: means no antibacterial properties

<Example 3>

Among the C12-C18 monoglycerides used as antibacterial ingredients and sapienic acid stabilizers of this antibacterial composition, the MIC of glycerol monolaurate was measured and compared with the MICs of lauric acid and sapienic acid (Table 3).

For the five types of bacteria investigated, the antibacterial activity of glycerol monolaurate, its glycerol ester compound, was greater than that of C12 lauric acid (Staphylococcus aureus, Staphylococcus epidermidis, Bacillus cereus, Candida albicans) or the same (no Cadia asteroides). Glycerol monolaurate had a lower MIC against Staphylococcus aureus, Staphylococcus epidermidis, and Candida albicans compared to sapienic acid. Glycerol monolaurate, which is used to chemically stabilize sapienic acid, has a bacterial group with a lower MIC than the antibacterial ingredients lauric acid and sapienic acid, so glycerol monolaurate is virtually an antibacterial ingredient. However, for Nocadia asteroides and Bacillus cereus, the MIC is higher than sapienic acid, so a higher concentration is needed to stop the activity of these bacteria.

Considering the results of Example 2, lauric acid and sapienic acid, which are the antibacterial ingredients of this antibacterial composition, and glycerol monolaurate, which is used as an antibacterial ingredient and sapienic acid stabilizer, have different effects on specific bacteria among eight types of bacteria. It has the lowest MIC. As summarized in Table 4, lauric acid is effective against Propionibacterium acnes and Puzobacterium nucleatum, sapienic acid is effective against Porphyromonas gingivalis, Nocadia asteroides and Bacillus cereus, and glycerol monolaurate is effective against Propionibacterium acnes and Puzobacterium nucleatum. Staphylococcus aureus, Staphylococcus epidermidis, and Candida albicans each have the lowest MICs.

Therefore, when lauric acid, sapienic acid, and glycerol monolaurate are used together in an appropriate ratio, eight types of bacteria can be eradicated most efficiently. In theory, the activity of the above eight types of bacteria can be stopped with a mixture consisting of 7.8 μg/ml of lauric acid, 62.5 μg/ml of sapienic acid, and 31.3 μg/ml of glycerol monolaurate. These are very small amounts, equivalent to 7.8×10 ^-4 %, 0.0069% and 0.0031% respectively by weight percentage.

Table 3. MIC of glycerol monolaurate (μg/ml) Germ Lauric acid sapienic acid Glycerol Monolaurate Staphylococcus aureus 500 250 31.3 Staphylococcus epidermidis 500 125 31.3 Nocadia asteroides 31.3 15.6 31.3 bacillus cereus 250 62.5 125 Candida albicans 500 125 31.3

Table 4. Fatty acid substances with the lowest MIC for eight types of bacteria and their MIC (㎍/㎖) Lauric acid sapienic acid glycerol
monolaurate Habitat/Species Germ skin Staphylococcus aureus - - 31.3 Staphylococcus epidermidis - - 31.3 Propionibacterium acnes 7.8 - - oral Porphyromonas
Gingivalis - 62.5 - Fusobacterium nucleatum 3.9 - - Life surroundings Nocadia asteroides - 15.6 - /spore formation bacillus
cereus - 62.5 - /leaven Candida albicans - - 31.3

<Example 4>

To see to what extent the antibacterial composition's antibacterial composition and sapienic acid stabilizer slow down the oxidation rate of sapienic acid, an unsaturated fatty acid, sapienic acid and the antibacterial ingredient and sapienic acid stabilizer were added to 100 ml of toluene in a glass column, and an air bubble was placed at the bottom of the column. An accelerated oxidation test was conducted at 25°C while blowing at a flow rate of ml/min. The amounts of sapienic acid and sapienic acid stabilizer used, as well as the remaining amount of sapienic acid over time, are summarized in Table 5. Here, the remaining amount of sapienic acid was analyzed by GC, and the weight of the remaining sapienic acid was expressed as a percentage compared to the weight of the initial sapienic acid.

When no unsaturated fatty acid stabilizer was added, about 2.7% of sapienic acid was oxidized after 4 weeks, and the remaining amount was 97.3%. When 5g of glycerol monolaurate was added and an oxidation acceleration test was performed, the oxidation rate slowed down and 99.6% of sapienic acid remained after 4 weeks. When 2g of each of the three types of monoglycerides was added and tested, the same occurred after 4 weeks. 99.7% of sapienic acid remained. Through this, it can be seen that C12-18 monoglyceride used to chemically stabilize sapienic acid, an antibacterial component of this antibacterial composition, has the function of slowing down the oxidation rate.

Table 5. Accelerated oxidation test conditions and results of sapienic acid Unsaturated fatty acid stabilizer Sapienic acid input amount (g) Sapienic acid remaining amount (%) ingredient Input amount (g) 1 week 2 weeks 3 weeks 4 weeks - - 5 100 99.5 98.1 97.3 glycerol
monolaurate 5 5 100 100 99.8 99.6 glycerol
monomyristate 2 5 100 100 99.9 99.7 glycerol
monopalmitate 2 glycerol
monostearate 2

<Example 5>

In order to see the antibacterial effect of this antibacterial composition on bacteria living on human skin, a skin care base product was made with several ingredients commonly used in skin care products as shown in Table 6, and the first antibacterial product was added based on the weight of the base product. Ingredients include 0.1% sapienic acid and 0.5% lauric acid, 0.2% glycerol monolaurate and 0.2% glycerol monostearate as the second antibacterial ingredient and sapienic acid stabilizer, 0.5% tocopherol and 0.5% methionine as an anti-acid agent, and 0.5% methionine as a carrier. After adding 5% ethanol and 2% ethyl myristate, they were mixed in a vortex mixer to complete a skin care product containing an antibacterial composition.

Take 500 μg of the above parent product, add 500 μg of bacterial suspension containing 1 × 10 ⁶ cfu/ml of Staphylococcus aureus and 1 × 10 ⁶ cfu/ml of Propionibacterium acnes obtained by culture, and mix in a vortex mixer. After mixing, it was cultured at 25°C.

100 μg of the culture medium containing the skin care base product was taken at intervals of 1 hr, 2 hr, 3 hr, and 4 hr, then diluted to various concentrations and cultured in tryptic soy agar medium at 37°C for 24 hours, and then the number of bacterial colonies was determined. was examined under a microscope to obtain the bacterial death curve over time shown in Figure 1.

In this figure showing the number of viable bacteria in Log ₁₀ (cfu/ml), it can be seen that the skin care product containing this antibacterial composition can eradicate Staphylococcus aureus and Propionibacterium acnes within 1 hour. there is.

Table 6. Skincare parent product ingredient table Distilled water 1,2-hexanediol glycerol Hirualenic acid lactic acid squalane ceramide Spices weight
(g) 1.0 0.5 2.0 0.3 0.3 0.5 0.7 0.1

<Example 6>

A parent mouthwash product consisting only of xylitol as a flavoring agent and this antibacterial composition was prepared with the composition shown in Table 7. To 500 μg of this, 500 μg of a bacterial suspension containing 1 × 10 ⁶ cfu/ml of Porphyromonas gingivalis and 1 × 10 ⁶ cfu/ml of Puzobacterium nucleatum was added, mixed, and cultured at 25°C. Afterwards, the culture medium was collected at intervals of 5, 10, 15, and 20 minutes, and the number of surviving bacteria was examined in the same manner as in Example 4.

As shown in Figure 2, the number of oral bacteria Porphyromonas gingivalis and Fuzobacterium nucleatum in the oral cavity was reduced to a value close to 0 within 5 minutes by this antibacterial composition.

Table 7. Composition of mouthwash parent product sapienic acid Lauric acid Glycerol Monolaurate glycerol
monopalmitate taurine cysteine methyl
laurate ethanol xylitol Distilled water weight
percent
(%) 0.2 0.2 0.3 0.2 0.3 0.3 0.5 15.0 0.4 82.6

<Example 7>

By weight percentage, sapienic acid 0.3% and lauric acid 0.3% as the first antibacterial ingredient, glycerol monomyristate 0.5% as the second antibacterial ingredient and sapienic acid stabilizer, glutathione 0.5% as the antioxidant, and ethyl laurate 1% and ethanol as the carrier. A base detergent product consisting of 30% and 67.4% distilled water as a diluent was prepared and its antibacterial properties were tested against methicillin-resistant Staphylococcus aureus by the method of Example 5. As a result of carefully measuring the number of surviving bacteria over time, the number of bacteria decreased to close to 0 within 5 minutes, similar to Figure 2.

Staphylococcus aureus, which is resistant to antibiotics, is a problematic bacteria that is mainly infected in hospitals where patients are hospitalized. Since the detergent made from this antibacterial composition shows excellent antibacterial properties against these bacteria, it can be used as a detergent for cleaning the hands of medical personnel and medical devices.

As described above, although the present invention has been described using limited examples, the present invention is not limited thereto, and the technical idea of the present invention will be described below by those skilled in the art to which the present invention pertains. Various modifications and variations will be possible within the scope of the claimed scope without damaging its essence.

Claims (15)

An antibacterial composition consisting of a first antibacterial ingredient composed of sapienic acid and lauric acid, a second antibacterial ingredient composed of C12-C18 monoglyceride, a sapienic acid stabilizer, an antioxidant, and a carrier. ,
All components of the composition consist only of substances secreted by the human body or nutrients necessary for the human body,
The composition is an antibacterial composition that has bactericidal properties against bacteria, mold, or yeast found on human skin and oral cavity. According to paragraph 1,
The antibacterial composition includes common Staphylococcus aureus, antibiotic-resistant Staphylococcus aureus, Staphylococcus epidermidis, Propionibacterium acnes, Porphyromonas gingivalis, Fusobacterium nucleatum, Nocadia asteroides, Bacillus candida, and An antibacterial composition characterized by having bactericidal properties against Candida albicans. According to paragraph 1,
The sapienic acid is obtained by direct cross-metathesis of petroselinic acid and 4-tetradecenoic acid or by metathesis of petroselinic acid and 4-tetradecenoic acid with ethylene, respectively. An antibacterial composition prepared by cross-metathesis of 6-heptenoic acid and 1-undecene. According to paragraph 1,
The second antibacterial ingredient and sapienic acid stabilizer is any selected from glycerol monolaurate, glycerol monomyristate, glycerol monopalmitate, and glycerol monostearate. An antibacterial composition characterized by one or more than two. According to paragraph 1,
An antibacterial composition, characterized in that the antioxidant is any one or two or more selected from tocopherol, methionine, taurine, glutathione, and cysteine. According to paragraph 1,
The carrier is used to control, dissolve, and transport the concentration of the first antibacterial ingredient, the second antibacterial ingredient and sapienic acid stabilizer, and the antioxidant,
An antibacterial composition, characterized in that the carrier is any one or two or more selected from methyl laurate, ethyl laurate, methyl myristate, ethyl myristate and ethanol. According to paragraph 1,
An antibacterial composition, characterized in that the weight ratio of the sapienic acid to the lauric acid is 5:95 to 95:5. According to paragraph 1,
The composition is an antibacterial composition that is used in skin care products, cosmetics such as skin lotion, household goods such as toothpaste and shampoo, mouthwash, and hand sanitizer. According to paragraph 1,
The composition is an antibacterial composition that is used as a preservative to prevent products used in the human body, such as cosmetics, household goods, mouthwash, and hand sanitizers, from spoiling. According to clause 8,
The skin care product contains 0.001 to 5% of the first antibacterial ingredient, 0.001 to 5% of the second antibacterial ingredient and sapienic acid stabilizer, 0.1 to 5% of antioxidant, and 0 to 60% of carrier based on the total weight of the skin care product. Characterized by an antibacterial composition. According to clause 8,
The skin lotion is characterized in that it contains 0.001-5% of the first antibacterial ingredient, 0.001-5% of the second antibacterial ingredient and sapienic acid stabilizer, 0.1-5% of antioxidant, and 0-40% of carrier based on the total weight of the skin lotion. Antibacterial composition. According to clause 8,
The toothpaste is antibacterial, characterized in that it contains 0.001-3% of the first antibacterial ingredient, 0.001-3% of the second antibacterial ingredient and sapienic acid stabilizer, 0.1-3% of antioxidant, and 0-10% of carrier based on the total weight of the toothpaste. Composition. According to clause 8,
The shampoo is an antibacterial agent characterized in that it contains 0.001-3% of the first antibacterial ingredient, 0.001-3% of the second antibacterial ingredient and sapienic acid stabilizer, 0.1-3% of antioxidant, and 0-20% of carrier based on the total weight of the shampoo. Composition. According to clause 8,
The mouthwash is characterized in that it contains 0.001-5% of the first antibacterial ingredient, 0.001-5% of the second antibacterial ingredient and sapienic acid stabilizer, 0.1-5% of antioxidant, and 0-50% of carrier based on the total weight of the mouthwash. Antibacterial composition. According to clause 8,
The hand sanitizer is characterized in that it contains 0.001-5% of the first antibacterial ingredient, 0.001-5% of the second antibacterial ingredient and sapienic acid stabilizer, 0.1-5% of antioxidant, and 0-50% of carrier based on the total weight of the hand sanitizer. Antibacterial composition.